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An exceptional residence awaits at 6 Cedarfield Terrace, nestled within the prestigious Point of Woods at Berry Hill community in Saint James. Surrounded by Head of the Harbor and Nissequogue, this distinguished enclave offers a refined setting with scale, convenience, and tranquility. Masterfully reimagined, this 5 bedroom, 4 full bathroom residence encompasses approximately 4,000 square feet of sophisticated living space on a builder’s acre lot. Sun filled interiors showcase warm white oak floors, soaring ceilings, new windows, a new roof and siding, and elevated finishes throughout. The first-floor primary suite offers a true hotel-like experience, featuring dramatic vaulted ceilings, two walk-in closets, and a beautifully appointed luxurious bathroom. A private guest wing near the garage provides a secluded retreat for guests, a home office, or flexible living space. At the heart of the home, a stunning chef’s kitchen features skylights, a center island, spacious eat-in area, and walk-in pantry. Upstairs, a spectacular loft with soaring ceilings, exposed wood beams, white oak floors, generous closet space, two additional bedrooms, and a full bathroom creates a versatile setting for a playroom, media room, or additional living area. A gracious, extended driveway welcomes you to the property, while the 9-foot-ceiling basement spanning 1,678 square feet and perfectly situated two-car garage provide exceptional functionality and abundant storage. Located within the highly regarded Smithtown School District, with coveted lower Saint James taxes and an enviable Head of the Harbor location. Just minutes from Stony Brook Village’s renowned restaurants and shops, and close to Stony Brook University Hospital, the property offers unparalleled convenience. Enjoy easy access to Stony Brook Beach, West Meadow Beach, and the scenic waterfront of the North Shore, perfectly complementing this exceptional coastal lifestyle.

5 Beds ⋅ 4 Baths ⋅ 1062232 MLS

An exceptional residence awaits at 6 Cedarfield Terrace, nestled within the prestigious Point of Woods at Berry Hill community in Saint James. Surrounded by Head of the Harbor and Nissequogue, this distinguished enclave offers a refined setting with scale, convenience, and tranquility. Masterfully reimagined, this 5 bedroom, 4 full bathroom residence encompasses approximately 4,000 square feet of sophisticated living space on a builder’s acre lot. Sun filled interiors showcase warm white oak floors, soaring ceilings, new windows, a new roof and siding, and elevated finishes throughout. The first-floor primary suite offers a true hotel-like experience, featuring dramatic vaulted ceilings, two walk-in closets, and a beautifully appointed luxurious bathroom. A private guest wing near the garage provides a secluded retreat for guests, a home office, or flexible living space. At the heart of the home, a stunning chef’s kitchen features skylights, a center island, spacious eat-in area, and walk-in pantry. Upstairs, a spectacular loft with soaring ceilings, exposed wood beams, white oak floors, generous closet space, two additional bedrooms, and a full bathroom creates a versatile setting for a playroom, media room, or additional living area. A gracious, extended driveway welcomes you to the property, while the 9-foot-ceiling basement spanning 1,678 square feet and perfectly situated two-car garage provide exceptional functionality and abundant storage. Located within the highly regarded Smithtown School District, with coveted lower Saint James taxes and an enviable Head of the Harbor location. Just minutes from Stony Brook Village’s renowned restaurants and shops, and close to Stony Brook University Hospital, the property offers unparalleled convenience. Enjoy easy access to Stony Brook Beach, West Meadow Beach, and the scenic waterfront of the North Shore, perfectly complementing this exceptional coastal lifestyle.

6 Cedarfield Terrace, Saint James

$6,899,000

Experience An Exceptional Waterfront Retreat Where Timeless Brick Architecture Meets Newly Reimagined Luxury. Completely Renovated In 2026, This Luxurious Residence Offers A Striking Expression Of Modern Luxury In The Coveted Incorporated Village Of Nissequogue. A Magnificent Waterfront Brick Masterpiece Set On Approximately 5 Acres, This 9300 Square Foot Residence Features 6 Bedrooms And 6.5 Bathrooms, Pairing Dramatic Architectural Scale With Beautifully Renewed Spaces For Every Day Living And Entertaining. At The Heart Of The Home, A Spectacular New Gourmet Kitchen Features A Beautiful Statement Quartz Island, Farmhouse Sink, Stainless Wolf Appliances, And Wine Refrigerator. From Casual Mornings To Celebratory Gatherings, This Inviting Space Brings Style And Function Together. The Magnificent Great Room, Distinguished By Soaring 22-Foot Ceilings, Creates An Unforgettable Setting For Entertaining On A Grand Scale, While Five Fireplaces Add Warmth And Character Throughout The Residence. The Primary Suite Is A Private Oasis Featuring A Gracious Sitting Room, Fireplace, Expansive Closets, And A Walk-Out Balcony To Capture The Most Beautiful Sunsets - Truly A Peaceful Retreat For Relaxation And Quiet Moments. The Newly Finished Lower Level Adds An Extraordinary Dimension To The Home, Featuring A Luxurious Kitchen, Bar, Full Bathroom, Den, Office, Theater Room, Two Gyms And An Outside Entrance. A Spacious 4-Car Garage, Geothermal Heating And Cooling System, And A Full-House Generator Further Enhance The Home's Comfort, Convenience And Functionality. The Waterfront Grounds Offer A Stunning Setting For Outdoor Living, Highlighted By Lush Lawns And Pristine Landscaping, An Impressive Poolhouse Complete With Bar, Entertaining Space And Full Bathroom, And A Heated And Saltwater In-Ground Pool. Approximately Five Acres And 280 Feet Of Water Frontage Provide An Expansive Backdrop For Relaxed Afternoons And Memorable Summer Gatherings, As Well As Incredible Panoramic Views Of The Long Island Sound. An Extensive 2026 Transformation Brings A Fresh, Cohesive Vision To This Palatial Residence, Delivering A Rare Opportunity To Enjoy Waterfront Luxury Living In One Of Long Island's Most Sought-After North Shore Villages!

6 Beds ⋅ 7 Baths ⋅ 1059832 MLS

Experience An Exceptional Waterfront Retreat Where Timeless Brick Architecture Meets Newly Reimagined Luxury. Completely Renovated In 2026, This Luxurious Residence Offers A Striking Expression Of Modern Luxury In The Coveted Incorporated Village Of Nissequogue. A Magnificent Waterfront Brick Masterpiece Set On Approximately 5 Acres, This 9300 Square Foot Residence Features 6 Bedrooms And 6.5 Bathrooms, Pairing Dramatic Architectural Scale With Beautifully Renewed Spaces For Every Day Living And Entertaining. At The Heart Of The Home, A Spectacular New Gourmet Kitchen Features A Beautiful Statement Quartz Island, Farmhouse Sink, Stainless Wolf Appliances, And Wine Refrigerator. From Casual Mornings To Celebratory Gatherings, This Inviting Space Brings Style And Function Together. The Magnificent Great Room, Distinguished By Soaring 22-Foot Ceilings, Creates An Unforgettable Setting For Entertaining On A Grand Scale, While Five Fireplaces Add Warmth And Character Throughout The Residence. The Primary Suite Is A Private Oasis Featuring A Gracious Sitting Room, Fireplace, Expansive Closets, And A Walk-Out Balcony To Capture The Most Beautiful Sunsets - Truly A Peaceful Retreat For Relaxation And Quiet Moments. The Newly Finished Lower Level Adds An Extraordinary Dimension To The Home, Featuring A Luxurious Kitchen, Bar, Full Bathroom, Den, Office, Theater Room, Two Gyms And An Outside Entrance. A Spacious 4-Car Garage, Geothermal Heating And Cooling System, And A Full-House Generator Further Enhance The Home's Comfort, Convenience And Functionality. The Waterfront Grounds Offer A Stunning Setting For Outdoor Living, Highlighted By Lush Lawns And Pristine Landscaping, An Impressive Poolhouse Complete With Bar, Entertaining Space And Full Bathroom, And A Heated And Saltwater In-Ground Pool. Approximately Five Acres And 280 Feet Of Water Frontage Provide An Expansive Backdrop For Relaxed Afternoons And Memorable Summer Gatherings, As Well As Incredible Panoramic Views Of The Long Island Sound. An Extensive 2026 Transformation Brings A Fresh, Cohesive Vision To This Palatial Residence, Delivering A Rare Opportunity To Enjoy Waterfront Luxury Living In One Of Long Island's Most Sought-After North Shore Villages!

1 Hunters Way, Nissequogue

$979,000

Classic Center Hall Colonial in Head of the Harbor, Welcome to this charming 4-bedroom, 2.5-bath Center Hall Colonial, ideally situated on 2.19 acres in the Head of the Harbor area of St. James, NY. Built in 1963, this well-maintained home offers timeless character, spacious living, and an exceptional location. Step inside to discover beautiful wood floors and classic wood doors, adding warmth and character throughout the home. Marvin windows provide quality, natural light, and lasting appeal. The property features a cedar deck, perfect for relaxing outdoors or entertaining while enjoying the privacy and expansive grounds. A detached shed provides additional storage, while the two-car garage offers convenient parking and workspace. The full unfinished basement provides abundant storage and flexible space for future use—whether you envision a recreation area, workshop, home gym, or additional living space. The home's location is a true highlight, with convenient access to the LIRR, St. James town, local shopping and dining, and the beautiful North Shore beaches. The property offers a rare combination of space, privacy, character, and convenience. Roof is 12years old, Oil Burner 5 years old, Cedar Deck 5 years old . A rare opportunity to own a spacious Colonial on over two acres in one of St. James' most private locations. Bring your vision and make this special property your own.

4 Beds ⋅ 3 Baths ⋅ 1057272 MLS

Classic Center Hall Colonial in Head of the Harbor, Welcome to this charming 4-bedroom, 2.5-bath Center Hall Colonial, ideally situated on 2.19 acres in the Head of the Harbor area of St. James, NY. Built in 1963, this well-maintained home offers timeless character, spacious living, and an exceptional location. Step inside to discover beautiful wood floors and classic wood doors, adding warmth and character throughout the home. Marvin windows provide quality, natural light, and lasting appeal. The property features a cedar deck, perfect for relaxing outdoors or entertaining while enjoying the privacy and expansive grounds. A detached shed provides additional storage, while the two-car garage offers convenient parking and workspace. The full unfinished basement provides abundant storage and flexible space for future use—whether you envision a recreation area, workshop, home gym, or additional living space. The home's location is a true highlight, with convenient access to the LIRR, St. James town, local shopping and dining, and the beautiful North Shore beaches. The property offers a rare combination of space, privacy, character, and convenience. Roof is 12years old, Oil Burner 5 years old, Cedar Deck 5 years old . A rare opportunity to own a spacious Colonial on over two acres in one of St. James' most private locations. Bring your vision and make this special property your own.

3 Gate Road, Head Of Harbor

$2,300,000

Some properties are simply new. Others are part of a story. Welcome to 595 Moriches Road, where a residence just three years young sits upon 2.6 private acres in a setting rich with Nissequogue history. At the corner of Moriches Road and Cordwood Path, striking stone pillars and wrought-iron gates remain as an intriguing piece of the land’s past, a reminder of the grand estates and history that have long shaped this storied area. Set beyond this glimpse of the past is something entirely different: a beautifully designed modern residence created for today’s way of living. Privately positioned amid mature natural surroundings, the home offers an impressive sense of space and serenity, with generous living areas and exciting possibilities for additional living space. There is something especially compelling about a property where old and new exist side by side. Here, the conveniences of a three-year-young residence meet the character of land with a story still waiting to be fully uncovered. A modern residence. 2.6 peaceful acres. A touch of Nissequogue history. And an opportunity to become the next chapter in the story of 595 Moriches Road.

3 Beds ⋅ 3 Baths ⋅ 1057363 MLS

Some properties are simply new. Others are part of a story. Welcome to 595 Moriches Road, where a residence just three years young sits upon 2.6 private acres in a setting rich with Nissequogue history. At the corner of Moriches Road and Cordwood Path, striking stone pillars and wrought-iron gates remain as an intriguing piece of the land’s past, a reminder of the grand estates and history that have long shaped this storied area. Set beyond this glimpse of the past is something entirely different: a beautifully designed modern residence created for today’s way of living. Privately positioned amid mature natural surroundings, the home offers an impressive sense of space and serenity, with generous living areas and exciting possibilities for additional living space. There is something especially compelling about a property where old and new exist side by side. Here, the conveniences of a three-year-young residence meet the character of land with a story still waiting to be fully uncovered. A modern residence. 2.6 peaceful acres. A touch of Nissequogue history. And an opportunity to become the next chapter in the story of 595 Moriches Road.

595 Moriches Road, Nissequogue

$799,000

Dutch Colonial, 4 bed, 2.5 bath, 1/2 acre, very long driveway capable of storing a motorhome, or up to 12 cars, Smithtown school district, quiet street, set back on lot, close to Smith Haven mall, many shops, easy access to major roads, near hospitals, fenced yard, warm country setting, large yard, room for pool,

4 Beds ⋅ 3 Baths ⋅ 1057367 MLS

Dutch Colonial, 4 bed, 2.5 bath, 1/2 acre, very long driveway capable of storing a motorhome, or up to 12 cars, Smithtown school district, quiet street, set back on lot, close to Smith Haven mall, many shops, easy access to major roads, near hospitals, fenced yard, warm country setting, large yard, room for pool,

14 King Arthurs Court, Saint James

$1,300,000

Welcome to a home where timeless Colonial charm meets comfortable, modern living in the community of St. James. Beautifully designed for both everyday living and effortless entertaining, this exceptional residence offers an abundance of space, amenities, and possibilities. The inviting main level offers generously sized living areas and a formal dining room, creating an elegant setting for dinners, celebrations, and memorable gatherings. Upstairs, you'll find comfortable primary suite and 3 additional bedrooms and downstairs has a layout that allows for the 5th bedroom to serve as a private guest suite, home office, or additional living space to suit your lifestyle. with half Bath The fully finished basement takes the living space to another level, offering endless possibilities for recreation, a home theater, gym, playroom, office, or entertaining area. Whether you're hosting or enjoying a quiet night at home, there's room for it all. Then step outside and discover your own private backyard oasis. The heated , saltwater in ground pool with mood lighting sets the stage for unforgettable summers—spend sunny afternoons poolside, entertaining under the stars, or simply enjoy your own private retreat at the end of the day. Thoughtful features including central air conditioning, gas heat, an in-ground sprinkler system, a generator and a new roof and much more add comfort, convenience, and peace of mind. This is more than just a house—it's a place to gather, entertain, relax, and create memories for years to come. From the spacious interior to the spectacular outdoor setting, this St. James Colonial offers the space, versatility, and lifestyle you've been waiting for.

5 Beds ⋅ 4 Baths ⋅ 1053983 MLS

Welcome to a home where timeless Colonial charm meets comfortable, modern living in the community of St. James. Beautifully designed for both everyday living and effortless entertaining, this exceptional residence offers an abundance of space, amenities, and possibilities. The inviting main level offers generously sized living areas and a formal dining room, creating an elegant setting for dinners, celebrations, and memorable gatherings. Upstairs, you'll find comfortable primary suite and 3 additional bedrooms and downstairs has a layout that allows for the 5th bedroom to serve as a private guest suite, home office, or additional living space to suit your lifestyle. with half Bath The fully finished basement takes the living space to another level, offering endless possibilities for recreation, a home theater, gym, playroom, office, or entertaining area. Whether you're hosting or enjoying a quiet night at home, there's room for it all. Then step outside and discover your own private backyard oasis. The heated , saltwater in ground pool with mood lighting sets the stage for unforgettable summers—spend sunny afternoons poolside, entertaining under the stars, or simply enjoy your own private retreat at the end of the day. Thoughtful features including central air conditioning, gas heat, an in-ground sprinkler system, a generator and a new roof and much more add comfort, convenience, and peace of mind. This is more than just a house—it's a place to gather, entertain, relax, and create memories for years to come. From the spacious interior to the spectacular outdoor setting, this St. James Colonial offers the space, versatility, and lifestyle you've been waiting for.

6 Patricks Way, Saint James

$1,999,000

A Rare Waterfront Sanctuary in the Village of Head of the Harbor. For the first time since it was built more than half a century ago, this remarkable waterfront property is being offered for sale. Privately set on 2.75 acres overlooking Stony Brook Harbor, 89 Harbor Road has remained under its original ownership since its creation and is defined by privacy, natural beauty and an extraordinary connection to the surrounding landscape. With 200 feet of waterfront, sweeping views extend across the pristine harbor toward Nissequogue, and Long Island Sound beyond, while private steps lead directly to the beach and water below, where a substantial stone riprap revetment protects the shoreline. A long and winding drive passes through a wooded landscape, leading to a broad opening with a light-filled residence framed by majestic oaks and a backdrop of water and sky. Upon arrival, there is an immediate sense of having left the hustle and bustle of the outside world behind—a peaceful sanctuary where the landscape, changing tides and natural beauty of the harbor become part of everyday life. Designed by architect Geysa Sarkany, the approximately 4,600-square-foot residence was conceived around its remarkable setting. The home was designed to look outward, with walls of glass creating a seamless connection between the interiors and the water and landscape beyond. Beneath this openness is a home of substantial construction, engineered and built with solidity and permanence. From the principal living spaces, kitchen and covered deck, the architecture continually draws the eye outward, framing individual views of the sky, shoreline and ever-changing harbor. Thoughtfully placed windows and glass, cypress siding and natural materials further connect the architecture to its surroundings, while 5 bedrooms and 3.5 baths across three levels provide substantial living space. Here, no two days on the harbor are quite the same. The tides rise and recede, revealing winding channels and broad tidal flats. Herons wander the shoreline while ospreys and eagles soar overhead, and sailboats, kayaks and paddleboarders quietly pass below. Summer brings long evenings on the covered deck and breathtaking sunsets over the water, as the sky and harbor take on an ever-changing palette of color and texture. In autumn, the marsh grasses turn from green to gold, while the shifting light and changing winds transform the landscape. The connection to the waterfront extends beyond the views, with direct beach and harbor access for kayaking, paddleboarding and sailing—making the water an integral part of life here. Lovingly maintained and thoughtfully updated over the years, great care has been taken to retain the home’s architectural character and its remarkable connection to the surrounding landscape. It presents a rare opportunity for its next owner to continue its story—whether embracing the home as it is or thoughtfully making it their own. While the setting feels a world away from everyday life, it is within the Smithtown School District and only minutes from Stony Brook Village, Stony Brook University and Stony Brook University Hospital, along with local restaurants, shopping, Avalon Nature Preserve and Harmony Vineyards—offering an exceptional balance of privacy, natural beauty and convenience. The combination of acreage, privacy, substantial waterfront, elevation, direct beach access and expansive views across a pristine harbor presents a remarkable setting—an opportunity to live surrounded by natural beauty, within an ecosystem and landscape that change with every tide and season. A property offering this combination of features rarely becomes available.

5 Beds ⋅ 4 Baths ⋅ 1054624 MLS

A Rare Waterfront Sanctuary in the Village of Head of the Harbor. For the first time since it was built more than half a century ago, this remarkable waterfront property is being offered for sale. Privately set on 2.75 acres overlooking Stony Brook Harbor, 89 Harbor Road has remained under its original ownership since its creation and is defined by privacy, natural beauty and an extraordinary connection to the surrounding landscape. With 200 feet of waterfront, sweeping views extend across the pristine harbor toward Nissequogue, and Long Island Sound beyond, while private steps lead directly to the beach and water below, where a substantial stone riprap revetment protects the shoreline. A long and winding drive passes through a wooded landscape, leading to a broad opening with a light-filled residence framed by majestic oaks and a backdrop of water and sky. Upon arrival, there is an immediate sense of having left the hustle and bustle of the outside world behind—a peaceful sanctuary where the landscape, changing tides and natural beauty of the harbor become part of everyday life. Designed by architect Geysa Sarkany, the approximately 4,600-square-foot residence was conceived around its remarkable setting. The home was designed to look outward, with walls of glass creating a seamless connection between the interiors and the water and landscape beyond. Beneath this openness is a home of substantial construction, engineered and built with solidity and permanence. From the principal living spaces, kitchen and covered deck, the architecture continually draws the eye outward, framing individual views of the sky, shoreline and ever-changing harbor. Thoughtfully placed windows and glass, cypress siding and natural materials further connect the architecture to its surroundings, while 5 bedrooms and 3.5 baths across three levels provide substantial living space. Here, no two days on the harbor are quite the same. The tides rise and recede, revealing winding channels and broad tidal flats. Herons wander the shoreline while ospreys and eagles soar overhead, and sailboats, kayaks and paddleboarders quietly pass below. Summer brings long evenings on the covered deck and breathtaking sunsets over the water, as the sky and harbor take on an ever-changing palette of color and texture. In autumn, the marsh grasses turn from green to gold, while the shifting light and changing winds transform the landscape. The connection to the waterfront extends beyond the views, with direct beach and harbor access for kayaking, paddleboarding and sailing—making the water an integral part of life here. Lovingly maintained and thoughtfully updated over the years, great care has been taken to retain the home’s architectural character and its remarkable connection to the surrounding landscape. It presents a rare opportunity for its next owner to continue its story—whether embracing the home as it is or thoughtfully making it their own. While the setting feels a world away from everyday life, it is within the Smithtown School District and only minutes from Stony Brook Village, Stony Brook University and Stony Brook University Hospital, along with local restaurants, shopping, Avalon Nature Preserve and Harmony Vineyards—offering an exceptional balance of privacy, natural beauty and convenience. The combination of acreage, privacy, substantial waterfront, elevation, direct beach access and expansive views across a pristine harbor presents a remarkable setting—an opportunity to live surrounded by natural beauty, within an ecosystem and landscape that change with every tide and season. A property offering this combination of features rarely becomes available.

89 Harbor Road, Head Of Harbor

$639,900

Fairfield at Saint James 55+ Community - rarely available 3 bedroom, 2.5 bath! Bright and spacious unit, ready for you to call home! Master bedroom on 1st floor with en-suite bath. 2 large bedrooms upstairs with a full bath. Kitchen updated with Quartz counters and soft close cabinetry & SS Appliances. Slider door to patio off of dining area. Motorized Shades in Dining room and Living Room. Motorized awning over patio. 3 Solar Tubes provide natural light. Driveway with parking for 2 cars and attached one-car garage with automatic opener. Electric Heat with Multiple Zones. Lots of storage! Low Monthly Common Charge of $405 includes: Grounds Care, Pool, Snow Removal. Gated Community with a Clubhouse, Recreation Room, Indoor and Outdoor Heated Pools, Tennis Courts and a Walking Trail around the community!

3 Beds ⋅ 3 Baths ⋅ 1047276 MLS

Fairfield at Saint James 55+ Community - rarely available 3 bedroom, 2.5 bath! Bright and spacious unit, ready for you to call home! Master bedroom on 1st floor with en-suite bath. 2 large bedrooms upstairs with a full bath. Kitchen updated with Quartz counters and soft close cabinetry & SS Appliances. Slider door to patio off of dining area. Motorized Shades in Dining room and Living Room. Motorized awning over patio. 3 Solar Tubes provide natural light. Driveway with parking for 2 cars and attached one-car garage with automatic opener. Electric Heat with Multiple Zones. Lots of storage! Low Monthly Common Charge of $405 includes: Grounds Care, Pool, Snow Removal. Gated Community with a Clubhouse, Recreation Room, Indoor and Outdoor Heated Pools, Tennis Courts and a Walking Trail around the community!

1102 Gotham Path, Saint James

$1,449,999

****LOCATION LOCATION ******Brand-new luxury construction in the heart of St. James beautifully designed 4-bedroom, 3-bath home offering high-end finishes, thoughtful craftsmanship and modern living throughout. Set within a private, tucked-away neighborhood with only two points of access, this exceptional residence offers a sense of privacy while remaining close to the Village of Head of the Harbor and all that St. James has to offer. The home features an inviting front porch, spacious interiors, a full basement. Outdoor spaces are equally impressive with a patio, professionally designed landscape beds and spacious side yard. Conveniently located within the Smithtown Central School District and close to St. James Elementary, Nesaquake Middle School and Smithtown High School East. Current property data places St. James Elementary approximately 0.4 mile away, Nesaquake Middle School approximately 1.5 miles away and Smithtown High School East approximately 1.3 miles away. Ideally situated in the heart of desirable St. James, offering the perfect blend of North Shore charm, history and convenience. Enjoy close proximity to the historic St. James village center, local shops and dining, the landmark St. James General Store, and the St. James LIRR station. Nearby Head of the Harbor, Stony Brook Harbor, scenic beaches, parks and waterfront destinations complete an exceptional lifestyle in one of the North Shore’s most distinctive communities. ******“Photos shown are renderings for illustrative purposes only and are subject to change. Final construction, finishes, materials, landscaping, colors, fixtures and other details may vary from those depicted. Renderings are not intended to be a representation or guarantee of final completion. Buyer to verify all features, specifications and finishes with builder/seller.”****

4 Beds ⋅ 3 Baths ⋅ 1054875 MLS

****LOCATION LOCATION ******Brand-new luxury construction in the heart of St. James beautifully designed 4-bedroom, 3-bath home offering high-end finishes, thoughtful craftsmanship and modern living throughout. Set within a private, tucked-away neighborhood with only two points of access, this exceptional residence offers a sense of privacy while remaining close to the Village of Head of the Harbor and all that St. James has to offer. The home features an inviting front porch, spacious interiors, a full basement. Outdoor spaces are equally impressive with a patio, professionally designed landscape beds and spacious side yard. Conveniently located within the Smithtown Central School District and close to St. James Elementary, Nesaquake Middle School and Smithtown High School East. Current property data places St. James Elementary approximately 0.4 mile away, Nesaquake Middle School approximately 1.5 miles away and Smithtown High School East approximately 1.3 miles away. Ideally situated in the heart of desirable St. James, offering the perfect blend of North Shore charm, history and convenience. Enjoy close proximity to the historic St. James village center, local shops and dining, the landmark St. James General Store, and the St. James LIRR station. Nearby Head of the Harbor, Stony Brook Harbor, scenic beaches, parks and waterfront destinations complete an exceptional lifestyle in one of the North Shore’s most distinctive communities. ******“Photos shown are renderings for illustrative purposes only and are subject to change. Final construction, finishes, materials, landscaping, colors, fixtures and other details may vary from those depicted. Renderings are not intended to be a representation or guarantee of final completion. Buyer to verify all features, specifications and finishes with builder/seller.”****

20 Overton Pass, Saint James

$1,449,999

**** LOCATION LOCATION LOCATION***** Nestled in the heart of the desirable Saint James, this brand-new luxury construction offers the perfect blend of North Shore charm, history, and convenience. This beautifully designed 4-bedroom, 3-bath home boasts high-end finishes, including a chef’s kitchen with a center island, a stone fireplace, luxury chandeliers, wide plank white oak flooring, thoughtful craftsmanship, and modern living throughout. Set within a private, tucked-away neighborhood with only two points of access, this exceptional residence provides a sense of privacy while still being close to the Village of Head of the Harbor and all that St. James has to offer. The inviting front porch, spacious interiors, and full basement with tremendous potential make this home truly special. An attached two-car garage with direct interior access adds to its convenience. Outdoor spaces are equally impressive, featuring a patio, professionally designed landscape beds, and a beautifully constructed retaining wall with stone stairs to the back yard. Conveniently located within the Smithtown Central School District, this home is close to St. James Elementary, Nesaquake Middle School, and Smithtown High School East. It’s also close to the historic St. James village center, local shops and dining, the landmark St. James General Store, and the St. James LIRR station. Nearby, you’ll find Head of the Harbor, Stony Brook Harbor, scenic beaches, parks, and waterfront destinations, making it an exceptional lifestyle in one of the North Shore’s most distinctive communities. *****“Photos shown are renderings for illustrative purposes only and are subject to change. Final construction, finishes, materials, landscaping, colors, fixtures and other details may vary from those depicted. Renderings are not intended to be a representation or guarantee of final completion. Buyer to verify all features, specifications and finishes with builder/seller.”***

4 Beds ⋅ 3 Baths ⋅ 1053682 MLS

**** LOCATION LOCATION LOCATION***** Nestled in the heart of the desirable Saint James, this brand-new luxury construction offers the perfect blend of North Shore charm, history, and convenience. This beautifully designed 4-bedroom, 3-bath home boasts high-end finishes, including a chef’s kitchen with a center island, a stone fireplace, luxury chandeliers, wide plank white oak flooring, thoughtful craftsmanship, and modern living throughout. Set within a private, tucked-away neighborhood with only two points of access, this exceptional residence provides a sense of privacy while still being close to the Village of Head of the Harbor and all that St. James has to offer. The inviting front porch, spacious interiors, and full basement with tremendous potential make this home truly special. An attached two-car garage with direct interior access adds to its convenience. Outdoor spaces are equally impressive, featuring a patio, professionally designed landscape beds, and a beautifully constructed retaining wall with stone stairs to the back yard. Conveniently located within the Smithtown Central School District, this home is close to St. James Elementary, Nesaquake Middle School, and Smithtown High School East. It’s also close to the historic St. James village center, local shops and dining, the landmark St. James General Store, and the St. James LIRR station. Nearby, you’ll find Head of the Harbor, Stony Brook Harbor, scenic beaches, parks, and waterfront destinations, making it an exceptional lifestyle in one of the North Shore’s most distinctive communities. *****“Photos shown are renderings for illustrative purposes only and are subject to change. Final construction, finishes, materials, landscaping, colors, fixtures and other details may vary from those depicted. Renderings are not intended to be a representation or guarantee of final completion. Buyer to verify all features, specifications and finishes with builder/seller.”***

18 Overton Pass, Saint James

$698,000

Welcome to this spacious high ranch, beautifully situated on a generous quarter-acre in the desirable Hamlet of St. James. A paver-stone driveway and matching front walkway provide excellent curb appeal, while the expansive driveway offers ample parking for multiple vehicles. Inside, you’ll find a freshly painted home featuring hardwood floors throughout the main level. The first floor offers a spacious living room and dining room with vaulted ceilings, creating an open and inviting atmosphere. The thoughtfully designed layout is ideal for multigenerational living, with three bedrooms and a remodeled bathroom on the main floor. The bathroom features an oversized walk-in shower with a glass enclosure, a wood vanity, and convenient access from both the primary bedroom and the hallway. The lower level includes two additional bedrooms, a full bath, and a large recreation room. It also offers a private entrance, providing flexibility for extended family, guests, or additional living space. The updated kitchen features recently remodeled cabinetry and new flooring, and opens directly to a spacious composite deck overlooking the private rear yard—perfect for outdoor dining, entertaining, or relaxing. With its versatile layout, generous property, vaulted ceilings, and excellent indoor-outdoor living spaces, this home offers comfort and flexibility. Conveniently located near local shopping, fine dining, area beaches, LIRR and Stony Brook University and Medical Center. Smithtown Schools

5 Beds ⋅ 2 Baths ⋅ 1053418 MLS

Welcome to this spacious high ranch, beautifully situated on a generous quarter-acre in the desirable Hamlet of St. James. A paver-stone driveway and matching front walkway provide excellent curb appeal, while the expansive driveway offers ample parking for multiple vehicles. Inside, you’ll find a freshly painted home featuring hardwood floors throughout the main level. The first floor offers a spacious living room and dining room with vaulted ceilings, creating an open and inviting atmosphere. The thoughtfully designed layout is ideal for multigenerational living, with three bedrooms and a remodeled bathroom on the main floor. The bathroom features an oversized walk-in shower with a glass enclosure, a wood vanity, and convenient access from both the primary bedroom and the hallway. The lower level includes two additional bedrooms, a full bath, and a large recreation room. It also offers a private entrance, providing flexibility for extended family, guests, or additional living space. The updated kitchen features recently remodeled cabinetry and new flooring, and opens directly to a spacious composite deck overlooking the private rear yard—perfect for outdoor dining, entertaining, or relaxing. With its versatile layout, generous property, vaulted ceilings, and excellent indoor-outdoor living spaces, this home offers comfort and flexibility. Conveniently located near local shopping, fine dining, area beaches, LIRR and Stony Brook University and Medical Center. Smithtown Schools

16 Arlington Avenue, Saint James

$724,900

The Charming Covered Porch Welcomes You to this 4 Bedroom New England Style Cape Home. This Home has been Lovingly Maintained by its Original Owners. There are all Wood Floors on the first level as well as the Staircase, except for the kitchen. The Formal Dining Room is Perfect for Holiday Gatherings with Family and Friends. The Bath was Recently Renovated with Fresh Paint, New Flooring, Toilet and Vanity. The Eat in Kitchen has a New Gas Stove and a Door that Leads to the Deck and the Back Yard. The Primary Bedroom could be on the first level of the Home or the Largest Bedroom Upstairs. The laundry is in the Basement and the Washer is less than 6 month's old. Relax and Enjoy Entertaining or a BBQ on the Rear Deck. The Oversized Spacious Flat Yard is Fully Fenced for Pets or Play and it is Very Private Surrounded by Trees. The Shed has a Light and the Huge Carport is Great for Additional Storage or a Car Collection. The Driveway is also Spacious and can Accommodate at Least 6 Vehicles. There are All Andersen Windows, Fans, Natural Gas Heat & Hot Water System (approx 12 yrs. old) Gutter Guards and 150 Amp Electric Service. The Roof is approximately 10 years old, Architectural Style Shingles and was Re-Insulated with New Plywood when it was installed. Located in Saint James it is Close to Schools, Stony Brook University and Hospital, Smith Haven Mall, Boutique Shops, Supermarkets, Local North Shore Beaches for Swimming, Boating and Festivals. It's Close to All Major Roads as well as the LIRR. Nearby is the New Centennial Park, an Ice Cream Parlor and Fine Dining Restaurants, all that makes St. James a Desirable and Wonderful Place to Live!

4 Beds ⋅ 1 Baths ⋅ 1053499 MLS

The Charming Covered Porch Welcomes You to this 4 Bedroom New England Style Cape Home. This Home has been Lovingly Maintained by its Original Owners. There are all Wood Floors on the first level as well as the Staircase, except for the kitchen. The Formal Dining Room is Perfect for Holiday Gatherings with Family and Friends. The Bath was Recently Renovated with Fresh Paint, New Flooring, Toilet and Vanity. The Eat in Kitchen has a New Gas Stove and a Door that Leads to the Deck and the Back Yard. The Primary Bedroom could be on the first level of the Home or the Largest Bedroom Upstairs. The laundry is in the Basement and the Washer is less than 6 month's old. Relax and Enjoy Entertaining or a BBQ on the Rear Deck. The Oversized Spacious Flat Yard is Fully Fenced for Pets or Play and it is Very Private Surrounded by Trees. The Shed has a Light and the Huge Carport is Great for Additional Storage or a Car Collection. The Driveway is also Spacious and can Accommodate at Least 6 Vehicles. There are All Andersen Windows, Fans, Natural Gas Heat & Hot Water System (approx 12 yrs. old) Gutter Guards and 150 Amp Electric Service. The Roof is approximately 10 years old, Architectural Style Shingles and was Re-Insulated with New Plywood when it was installed. Located in Saint James it is Close to Schools, Stony Brook University and Hospital, Smith Haven Mall, Boutique Shops, Supermarkets, Local North Shore Beaches for Swimming, Boating and Festivals. It's Close to All Major Roads as well as the LIRR. Nearby is the New Centennial Park, an Ice Cream Parlor and Fine Dining Restaurants, all that makes St. James a Desirable and Wonderful Place to Live!

240 Washington Avenue, Saint James

$3,575,000

Nestled on two private acres in the Incorporated Village of Nissequogue, this extraordinary estate offers beautifully reimagined living space where luxury, comfort, and timeless design come together. The home underwent a remarkable architectural transformation, completely reimagining the interior and exterior while preserving the character and presence of an established North Shore estate. Every detail was thoughtfully redesigned with an emphasis on exceptional craftsmanship, modern functionality, and elegant living. Rich white oak floors, custom stone surfaces, and exquisite finishes create an atmosphere that is both sophisticated and inviting. Designed for everyday living and exceptional entertaining, the chef’s kitchen features an expansive custom pantry that functions like a second kitchen, built-in wine storage, and a beautifully appointed wet bar. The dramatic great room, highlighted by soaring ceilings and a gas fireplace, serves as the heart of the home, while a separate entertainment room featuring a wood-burning fireplace with easy access to convert to gas provides additional space for gathering and celebrating. Offering six bedrooms and seven baths, including two luxurious suite options with spa-inspired baths, heated floors, generous walk-in closets, and refined finishes, the home provides exceptional flexibility and comfort. A distinctive spiral staircase leads to a charming tower overlooking the estate, creating a truly unique architectural feature. Beautifully integrated infrastructure and modern systems complement the home’s exceptional design, providing the comfort, efficiency, and functionality expected in a residence of this caliber. Outside, a heated saltwater pool with stadium steps and bench seating is surrounded by an expansive paver patio, creating the perfect setting for outdoor entertaining. Mature trees and thoughtfully designed landscaping enhance the privacy and beauty of the level two-acre property. A grandfathered horseshoe driveway with dual Belgian block entrances welcomes you home, a highly sought-after feature in Nissequogue’s renowned horse country. Located less than a mile from two beaches, including one with deeded access, this exceptional property offers a rare opportunity to enjoy luxury North Shore living in one of Long Island’s most renowned communities.

6 Beds ⋅ 7 Baths ⋅ 1048898 MLS

Nestled on two private acres in the Incorporated Village of Nissequogue, this extraordinary estate offers beautifully reimagined living space where luxury, comfort, and timeless design come together. The home underwent a remarkable architectural transformation, completely reimagining the interior and exterior while preserving the character and presence of an established North Shore estate. Every detail was thoughtfully redesigned with an emphasis on exceptional craftsmanship, modern functionality, and elegant living. Rich white oak floors, custom stone surfaces, and exquisite finishes create an atmosphere that is both sophisticated and inviting. Designed for everyday living and exceptional entertaining, the chef’s kitchen features an expansive custom pantry that functions like a second kitchen, built-in wine storage, and a beautifully appointed wet bar. The dramatic great room, highlighted by soaring ceilings and a gas fireplace, serves as the heart of the home, while a separate entertainment room featuring a wood-burning fireplace with easy access to convert to gas provides additional space for gathering and celebrating. Offering six bedrooms and seven baths, including two luxurious suite options with spa-inspired baths, heated floors, generous walk-in closets, and refined finishes, the home provides exceptional flexibility and comfort. A distinctive spiral staircase leads to a charming tower overlooking the estate, creating a truly unique architectural feature. Beautifully integrated infrastructure and modern systems complement the home’s exceptional design, providing the comfort, efficiency, and functionality expected in a residence of this caliber. Outside, a heated saltwater pool with stadium steps and bench seating is surrounded by an expansive paver patio, creating the perfect setting for outdoor entertaining. Mature trees and thoughtfully designed landscaping enhance the privacy and beauty of the level two-acre property. A grandfathered horseshoe driveway with dual Belgian block entrances welcomes you home, a highly sought-after feature in Nissequogue’s renowned horse country. Located less than a mile from two beaches, including one with deeded access, this exceptional property offers a rare opportunity to enjoy luxury North Shore living in one of Long Island’s most renowned communities.

523 Long Beach Road, Nissequogue

$2,448,000

AN ADDRESS WORTH SAYING YES TO! There are certain streets that make you slow down before you ever reach the house. Swan Place is one of them. Tucked within the coveted Village of Nissequogue, the approach winds past estate-like homes beneath a canopy of mature trees, quietly setting the tone for what awaits. Set on two naturally beautiful and private acres, this is a home with presence, but also one that feels remarkably warm once inside. The sense of occasion begins the moment you step inside. A dramatic two-story foyer is anchored by a grand curved staircase, its sweeping wood balustrade gracefully arcing above the entry and continuing into an elevated, bridge like balcony overlooking the marble floor below. Beyond, the home opens to a spectacular two to three story Great Room, where soaring ceilings, architectural detail and walls of natural light create a space that feels impressive yet inviting. It is a beautiful first impression, sophisticated in design, and unmistakably special. It is a grand introduction, but one that still feels wonderfully livable, the kind of entrance that reminds you immediately that this is no ordinary home. The kitchen was designed for the way a home like this is meant to be enjoyed, open, welcoming, and always connected to what is happening around it. An impressive, oversized center island anchors the space, surrounded by recently renovated designer cabinetry and premium appliances, with plenty of room for everything from morning coffee to a house full of guests. Completely open to the soaring great room on one side and the spectacular, glass filled sunroom, the kitchen becomes the natural gathering place of the home. Sunlight pours in from every direction, while expansive views of the property create an effortless flow from cooking to conversation to the outdoors beyond. Privately positioned on the first floor, the primary suite feels like a retreat of its own. Generous yet intimate, it features a fireside sitting room, beautifully designed dressing spaces and a spa inspired marble bath. French doors open to a private deck with the hot tub just steps away, a wonderfully peaceful escape any time of the day. Additional rooms on the main level offer wonderful flexibility easily imagined as guest quarters, an au pair suite, private offices, or whatever life happens to require. The upper levels unfold with a wonderful sense of privacy and possibility, offering four beautifully proportioned guest bedrooms along with two additional lounging spaces, perfect for quiet reading, late night conversation, a media retreat or simply giving family and guests a place of their own. But the best surprise is found one level higher on the rooftop deck, where the treetops open to spectacular views toward the harbor and Long Island Sound. It is the kind of unexpected perch made for morning coffee, an evening glass of wine, or simply watching the sky change at the end of the day. Outside is where this property becomes something incredibly special. The grounds feel more like a private retreat than a backyard. A heated Gunite pool, framed in stone and brought to life by three cascading waterfalls, creates a wonderfully serene, spa like setting. Expansive decking, a hot tub, outdoor kitchen and two acres of mature landscape provide plenty of places to entertain, and just as many places to disappear with a book and enjoy the quiet. Then there are the unexpected spaces. A tucked-away bonus room above the three-car garage feels like a hidden discovery within the home, an ideal private lounge, game room, studio, or escape, complete with its own Juliet balcony. Life in Nissequogue has always been about having room to breathe. Beaches, boating, the harbor, parks, and the villages of the North Shore are all part of everyday life here, while New York City and the Hamptons remain within reach. 9 Swan Place is an address worth seeing. WHEN THE HOUSE, THE SETTING & THE VALUE ALL SAY YES

7 Beds ⋅ 7 Baths ⋅ 1047513 MLS

AN ADDRESS WORTH SAYING YES TO! There are certain streets that make you slow down before you ever reach the house. Swan Place is one of them. Tucked within the coveted Village of Nissequogue, the approach winds past estate-like homes beneath a canopy of mature trees, quietly setting the tone for what awaits. Set on two naturally beautiful and private acres, this is a home with presence, but also one that feels remarkably warm once inside. The sense of occasion begins the moment you step inside. A dramatic two-story foyer is anchored by a grand curved staircase, its sweeping wood balustrade gracefully arcing above the entry and continuing into an elevated, bridge like balcony overlooking the marble floor below. Beyond, the home opens to a spectacular two to three story Great Room, where soaring ceilings, architectural detail and walls of natural light create a space that feels impressive yet inviting. It is a beautiful first impression, sophisticated in design, and unmistakably special. It is a grand introduction, but one that still feels wonderfully livable, the kind of entrance that reminds you immediately that this is no ordinary home. The kitchen was designed for the way a home like this is meant to be enjoyed, open, welcoming, and always connected to what is happening around it. An impressive, oversized center island anchors the space, surrounded by recently renovated designer cabinetry and premium appliances, with plenty of room for everything from morning coffee to a house full of guests. Completely open to the soaring great room on one side and the spectacular, glass filled sunroom, the kitchen becomes the natural gathering place of the home. Sunlight pours in from every direction, while expansive views of the property create an effortless flow from cooking to conversation to the outdoors beyond. Privately positioned on the first floor, the primary suite feels like a retreat of its own. Generous yet intimate, it features a fireside sitting room, beautifully designed dressing spaces and a spa inspired marble bath. French doors open to a private deck with the hot tub just steps away, a wonderfully peaceful escape any time of the day. Additional rooms on the main level offer wonderful flexibility easily imagined as guest quarters, an au pair suite, private offices, or whatever life happens to require. The upper levels unfold with a wonderful sense of privacy and possibility, offering four beautifully proportioned guest bedrooms along with two additional lounging spaces, perfect for quiet reading, late night conversation, a media retreat or simply giving family and guests a place of their own. But the best surprise is found one level higher on the rooftop deck, where the treetops open to spectacular views toward the harbor and Long Island Sound. It is the kind of unexpected perch made for morning coffee, an evening glass of wine, or simply watching the sky change at the end of the day. Outside is where this property becomes something incredibly special. The grounds feel more like a private retreat than a backyard. A heated Gunite pool, framed in stone and brought to life by three cascading waterfalls, creates a wonderfully serene, spa like setting. Expansive decking, a hot tub, outdoor kitchen and two acres of mature landscape provide plenty of places to entertain, and just as many places to disappear with a book and enjoy the quiet. Then there are the unexpected spaces. A tucked-away bonus room above the three-car garage feels like a hidden discovery within the home, an ideal private lounge, game room, studio, or escape, complete with its own Juliet balcony. Life in Nissequogue has always been about having room to breathe. Beaches, boating, the harbor, parks, and the villages of the North Shore are all part of everyday life here, while New York City and the Hamptons remain within reach. 9 Swan Place is an address worth seeing. WHEN THE HOUSE, THE SETTING & THE VALUE ALL SAY YES

9 Swan Place, Saint James

$1,649,000

Welcome to 4 Holly Lane in Nissequogue, an impressive estate style residence set behind a sweeping circular driveway and surrounded by beautifully manicured grounds, mature trees, and expansive lawns. Step inside to a dramatic two story foyer that introduces a bright, spacious interior featuring hardwood floors, elegant formal living and dining rooms, and a stunning great room with soaring ceilings and a floor to ceiling stone fireplace. The well appointed kitchen offers abundant cabinetry and counter space, stainless steel appliances, and a sun filled breakfast area overlooking the backyard. A bright sunroom provides seamless access to the home’s exceptional outdoor entertaining spaces. Upstairs, the expansive primary suite features vaulted ceilings, a window lined sitting area, and a generous en-suite bath with dual vanities and soaking tub\. Additional spacious bedrooms and a large bonus room provide tremendous flexibility for today’s lifestyle. Outside is where this property truly shines. An expansive paver patio, fire feature, multiple entertaining areas, sprawling lawn, and mature landscaping create a private setting designed for gatherings and relaxation\. An impressive detached accessory building offers a warm lodge inspired interior complete with lounge space, kitchenette, bath, and additional recreational space. With oversized garage areas, extensive storage, remarkable grounds, and incredible versatility throughout, 4 Holly Lane offers an exceptional combination of space, privacy, character, and indoor outdoor living in Nissequogue.

3 Beds ⋅ 4 Baths ⋅ 1048497 MLS

Welcome to 4 Holly Lane in Nissequogue, an impressive estate style residence set behind a sweeping circular driveway and surrounded by beautifully manicured grounds, mature trees, and expansive lawns. Step inside to a dramatic two story foyer that introduces a bright, spacious interior featuring hardwood floors, elegant formal living and dining rooms, and a stunning great room with soaring ceilings and a floor to ceiling stone fireplace. The well appointed kitchen offers abundant cabinetry and counter space, stainless steel appliances, and a sun filled breakfast area overlooking the backyard. A bright sunroom provides seamless access to the home’s exceptional outdoor entertaining spaces. Upstairs, the expansive primary suite features vaulted ceilings, a window lined sitting area, and a generous en-suite bath with dual vanities and soaking tub\. Additional spacious bedrooms and a large bonus room provide tremendous flexibility for today’s lifestyle. Outside is where this property truly shines. An expansive paver patio, fire feature, multiple entertaining areas, sprawling lawn, and mature landscaping create a private setting designed for gatherings and relaxation\. An impressive detached accessory building offers a warm lodge inspired interior complete with lounge space, kitchenette, bath, and additional recreational space. With oversized garage areas, extensive storage, remarkable grounds, and incredible versatility throughout, 4 Holly Lane offers an exceptional combination of space, privacy, character, and indoor outdoor living in Nissequogue.

4 Holly Lane

$1,599,000

Welcome to 29 Farm Road....nestled in the prestigious Village of Head of the Harbor, where secluded, private & tranquil living awaits! This stunning, beautifully maintained Expanded Ranch features a grand entry foyer, spacious EIK w/ granite countertops, center island, SS appliances, and picturesque views of the surrounding landscape, a warm and inviting Great Room w/ Stone FP and vaulted ceilings w/ 2 skylights and 4 slider doors leading to the wrap around deck, a gorgeous formal dining room, powder room. The 1st floor features 3 spacious bedrooms, including a luxurious Primary Bedroom Ensuite w/ private access to the extensive wrap-around porch, WIC, and primary bath w/ double vanity sink, bathtub, and separate shower. Bedroom 2 features a WIC, chair rail molding, and an ensuite bathroom w/ spa tub. Bedroom 3 offers a private loft space and skylight, and a main floor office space w/ French doors, plus an additional full bath completing the main level. The versatile loft is ideal as a recreation room, home gym, or flex space, with convenient attic access. The lower level offers exceptional flexibility and features a 4th Bedroom (perfect for guests or an in-law suite), a Summer Kitchen w/ quartz countertops, oversized family room, 2 separate gym rooms, full bath, laundry room, ample storage, direct access to the two-car garage, and sliders leading to your own private, resort-like backyard retreat! Additional features include.... CAC (2 zones), Oil Heat (4 zones - burner 2016), 200-amp electric, IGS System (8 zones - redone in 2026), inground saltwater heated pool (Liner - 2025), Whole House Inside & Outside KeyOS wireless app-controlled stereo system, and a portable generator with transfer switch hookup. Surrounded by nature, with an abundance of natural light, oversized windows, and skylights that create a bright, airy, and inviting atmosphere throughout. This exceptional home truly has it all! All this and much more... Set on over 2+ acres of beautiful and secluded property (very private), you do not want to miss this rare opportunity!

4 Beds ⋅ 4 Baths ⋅ 1047851 MLS

Welcome to 29 Farm Road....nestled in the prestigious Village of Head of the Harbor, where secluded, private & tranquil living awaits! This stunning, beautifully maintained Expanded Ranch features a grand entry foyer, spacious EIK w/ granite countertops, center island, SS appliances, and picturesque views of the surrounding landscape, a warm and inviting Great Room w/ Stone FP and vaulted ceilings w/ 2 skylights and 4 slider doors leading to the wrap around deck, a gorgeous formal dining room, powder room. The 1st floor features 3 spacious bedrooms, including a luxurious Primary Bedroom Ensuite w/ private access to the extensive wrap-around porch, WIC, and primary bath w/ double vanity sink, bathtub, and separate shower. Bedroom 2 features a WIC, chair rail molding, and an ensuite bathroom w/ spa tub. Bedroom 3 offers a private loft space and skylight, and a main floor office space w/ French doors, plus an additional full bath completing the main level. The versatile loft is ideal as a recreation room, home gym, or flex space, with convenient attic access. The lower level offers exceptional flexibility and features a 4th Bedroom (perfect for guests or an in-law suite), a Summer Kitchen w/ quartz countertops, oversized family room, 2 separate gym rooms, full bath, laundry room, ample storage, direct access to the two-car garage, and sliders leading to your own private, resort-like backyard retreat! Additional features include.... CAC (2 zones), Oil Heat (4 zones - burner 2016), 200-amp electric, IGS System (8 zones - redone in 2026), inground saltwater heated pool (Liner - 2025), Whole House Inside & Outside KeyOS wireless app-controlled stereo system, and a portable generator with transfer switch hookup. Surrounded by nature, with an abundance of natural light, oversized windows, and skylights that create a bright, airy, and inviting atmosphere throughout. This exceptional home truly has it all! All this and much more... Set on over 2+ acres of beautiful and secluded property (very private), you do not want to miss this rare opportunity!

29 Farm Road, Saint James

$3,699,000

A Rare Opportunity to Create Your Custom Estate on Long Island Opportunities like this are exceptionally rare on Long Island. Set within one of the area’s most prestigious and private villages, this extraordinary new-construction estate offers the space, privacy and ability to customize that are increasingly difficult to find. Privately positioned on a breathtaking 2.35-acre wooded property with an additional one-acre private driveway, this impressive 7,000+ square-foot residence has been thoughtfully designed to combine timeless architecture with today’s most sought-after luxury amenities. Construction has progressed to the point where private tours can now be scheduled, while still offering the opportunity to personalize select finishes and make this remarkable home your own. A sweeping asphalt and stone driveway with cobblestone edging leads to the grand two-story traditional residence and oversized three-car garage. Inside, dramatic proportions immediately set the home apart, with a 20'6" two-story foyer and family room, 10-foot ceilings on the main level, a full 10-foot walk-out basement, and an elevator servicing all floors. The main level is designed for both everyday luxury and effortless entertaining. A spectacular chef’s kitchen features high-end Subzero separate refrigerator and freezer and Wolf appliances; subzero wine cabinetry and wet bar sub-zero, custom cabinetry with wood buildins, granite or quartz countertops, an expansive center island with prep sink, and radiant-heated porcelain floors. The soaring two-story family room is centered around a modern linear gas fireplace and coffered ceiling, while the formal dining room features custom built-ins and elegant millwork. A highly desirable **first-floor en suite** provides exceptional flexibility and convenience. The home also features a primary en suite wing along with 3 additional en-suite bedrooms, wide White Oak flooring, custom closet systems, radiant-heated floors, **two saunas and two steam showers**. Spa-inspired baths with premium Kohler fixtures complete the experience. Outdoor living is equally impressive. A covered rear porch with its own gas fireplace creates a beautiful setting for year-round entertaining, while a dedicated exterior-access full bathroom is ideal for a future pool. An in-ground pool is optional and may be customized to the buyer’s vision. The full 10-foot walk-out basement, complete with a full bathroom and outside entrance, offers tremendous possibilities for additional recreation, fitness, entertainment or guest space. Behind the beauty is equally impressive construction and infrastructure, including engineered wood-web floor joists, 400-amp electric service, natural gas, public water and seven oversized drywells. The home is also designed to accommodate a future generator and pool. Throughout the residence, wide White Oak hardwood floors, substantial moldings, custom millwork and an extra-wide staircase with open railings reflect the level of craftsmanship invested in every detail. More than a new home, this is an opportunity rarely available on Long Island: a newly built 7,000+ square-foot custom estate on exceptional acreage within an exclusive village — offering privacy, scale, luxury and the chance to make the finishing touches uniquely your own. *3D Reality Tours shown are examples of the builder’s previous work and are intended to demonstrate quality and craftsmanship; they do not depict this exact home.

5 Beds ⋅ 8 Baths ⋅ 1037676 MLS

A Rare Opportunity to Create Your Custom Estate on Long Island Opportunities like this are exceptionally rare on Long Island. Set within one of the area’s most prestigious and private villages, this extraordinary new-construction estate offers the space, privacy and ability to customize that are increasingly difficult to find. Privately positioned on a breathtaking 2.35-acre wooded property with an additional one-acre private driveway, this impressive 7,000+ square-foot residence has been thoughtfully designed to combine timeless architecture with today’s most sought-after luxury amenities. Construction has progressed to the point where private tours can now be scheduled, while still offering the opportunity to personalize select finishes and make this remarkable home your own. A sweeping asphalt and stone driveway with cobblestone edging leads to the grand two-story traditional residence and oversized three-car garage. Inside, dramatic proportions immediately set the home apart, with a 20'6" two-story foyer and family room, 10-foot ceilings on the main level, a full 10-foot walk-out basement, and an elevator servicing all floors. The main level is designed for both everyday luxury and effortless entertaining. A spectacular chef’s kitchen features high-end Subzero separate refrigerator and freezer and Wolf appliances; subzero wine cabinetry and wet bar sub-zero, custom cabinetry with wood buildins, granite or quartz countertops, an expansive center island with prep sink, and radiant-heated porcelain floors. The soaring two-story family room is centered around a modern linear gas fireplace and coffered ceiling, while the formal dining room features custom built-ins and elegant millwork. A highly desirable **first-floor en suite** provides exceptional flexibility and convenience. The home also features a primary en suite wing along with 3 additional en-suite bedrooms, wide White Oak flooring, custom closet systems, radiant-heated floors, **two saunas and two steam showers**. Spa-inspired baths with premium Kohler fixtures complete the experience. Outdoor living is equally impressive. A covered rear porch with its own gas fireplace creates a beautiful setting for year-round entertaining, while a dedicated exterior-access full bathroom is ideal for a future pool. An in-ground pool is optional and may be customized to the buyer’s vision. The full 10-foot walk-out basement, complete with a full bathroom and outside entrance, offers tremendous possibilities for additional recreation, fitness, entertainment or guest space. Behind the beauty is equally impressive construction and infrastructure, including engineered wood-web floor joists, 400-amp electric service, natural gas, public water and seven oversized drywells. The home is also designed to accommodate a future generator and pool. Throughout the residence, wide White Oak hardwood floors, substantial moldings, custom millwork and an extra-wide staircase with open railings reflect the level of craftsmanship invested in every detail. More than a new home, this is an opportunity rarely available on Long Island: a newly built 7,000+ square-foot custom estate on exceptional acreage within an exclusive village — offering privacy, scale, luxury and the chance to make the finishing touches uniquely your own. *3D Reality Tours shown are examples of the builder’s previous work and are intended to demonstrate quality and craftsmanship; they do not depict this exact home.

550 Moriches Road, Head Of Harbor

$1,500,000

Elegant and Unique Colonial set on 2 Beautifully Landscaped Acres in the highly Sought After Village of Head of the Harbor. This Spacious Home Offers 3/4 Bedrooms. 3 Traditional Bedrooms Plus a Versatile Bonus Room That Can Easily Function as a 4th Bedroom. Generous-Size Principal Rooms Create an Inviting Layout for Everyday Living and Entertaining. The Home Features a Warm and Welcoming Living Room, a Formal Dining Room, and a Charming Den Highlighted by a Stunning Stone Fireplace. A Separate Study/Home Office Further Enhances This Home’s Valuable Versatility. The Updated Eat in Kitchen Provides Excellent Workspace and Views of the Serene Property. Additional Features Include: 2.5 Baths, Central Air Conditioning, a Full Finished Basement, 2 Car Garage, an Unfinished Walk-Up Attic with Vaulted Ceilings (see floorplan for dimensions), Spacious Deck Overlooking the Picturesque Grounds, Separate Hot Water Heater, Crown Molding, Numerous Updates, and a Comfortable, Functional Floor Plan Enhancing this Home’s Appeal. Set in a Premier North Shore Village Known for Privacy, Natural Beauty, and Convenience, this Property offers an Exceptional Lifestyle Opportunity.

3 Beds ⋅ 3 Baths ⋅ 1040036 MLS

Elegant and Unique Colonial set on 2 Beautifully Landscaped Acres in the highly Sought After Village of Head of the Harbor. This Spacious Home Offers 3/4 Bedrooms. 3 Traditional Bedrooms Plus a Versatile Bonus Room That Can Easily Function as a 4th Bedroom. Generous-Size Principal Rooms Create an Inviting Layout for Everyday Living and Entertaining. The Home Features a Warm and Welcoming Living Room, a Formal Dining Room, and a Charming Den Highlighted by a Stunning Stone Fireplace. A Separate Study/Home Office Further Enhances This Home’s Valuable Versatility. The Updated Eat in Kitchen Provides Excellent Workspace and Views of the Serene Property. Additional Features Include: 2.5 Baths, Central Air Conditioning, a Full Finished Basement, 2 Car Garage, an Unfinished Walk-Up Attic with Vaulted Ceilings (see floorplan for dimensions), Spacious Deck Overlooking the Picturesque Grounds, Separate Hot Water Heater, Crown Molding, Numerous Updates, and a Comfortable, Functional Floor Plan Enhancing this Home’s Appeal. Set in a Premier North Shore Village Known for Privacy, Natural Beauty, and Convenience, this Property offers an Exceptional Lifestyle Opportunity.

1 Valleywood Court W, Head Of Harbor

$749,990

Situated on a dead end street, nearly an acre of property in the heart of St. James, this unique 3-bedroom ranch offers space, versatility, and an incredible opportunity for horse lovers! The property is zoned for up to two horses and features a fully functional 12' x 26' barn with electricity—a standout feature! The property also includes an oversized 18' x 23' garage, providing plenty of additional space for vehicles, storage, a workshop, hobbies, or equipment. Inside, you'll find a charming and inviting home featuring a renovated kitchen, beautiful hardwood floors, and a stunning floor-to-ceiling indoor/outdoor fireplace that brings warmth and character to the living space. Enjoy the privacy and possibilities that come with having nearly an acre of land, all while being conveniently located in the heart of St. James. Whether you're an equestrian, need room for your hobbies and toys, or simply dream of having more property, this is a rare opportunity you won't want to miss!

3 Beds ⋅ 1 Baths ⋅ 1041719 MLS

Situated on a dead end street, nearly an acre of property in the heart of St. James, this unique 3-bedroom ranch offers space, versatility, and an incredible opportunity for horse lovers! The property is zoned for up to two horses and features a fully functional 12' x 26' barn with electricity—a standout feature! The property also includes an oversized 18' x 23' garage, providing plenty of additional space for vehicles, storage, a workshop, hobbies, or equipment. Inside, you'll find a charming and inviting home featuring a renovated kitchen, beautiful hardwood floors, and a stunning floor-to-ceiling indoor/outdoor fireplace that brings warmth and character to the living space. Enjoy the privacy and possibilities that come with having nearly an acre of land, all while being conveniently located in the heart of St. James. Whether you're an equestrian, need room for your hobbies and toys, or simply dream of having more property, this is a rare opportunity you won't want to miss!

4 Sunny Road, Saint James

$1,950,000

Welcome to 38 Riverview Terrace, an exceptional custom-built Colonial offering five bedrooms, three full bathrooms and one half bath, with an extensive array of high end finishes, entertainment spaces and resort-style outdoor amenities. A grand foyer welcomes you with wainscoting, chandelier and stunning maple hardwood flooring that continues throughout the first floor. The main level features an elegant formal dining room and a spacious den anchored by a wood-burning fireplace. The expansive eat-in chef’s kitchen is designed for both cooking and entertaining, featuring a large 7'10" center island, quartz countertops throughout, skylights, a breakfast area and modern farmhouse sink. High-end Sub-Zero and Wolf appliances include an eight-burner Wolf range with double ovens, a massive custom hood with pot filler, an additional wall oven, warming drawer, built-in microwave, ice maker and wine cooler. Radiant heated flooring completes the kitchen. A powder room with radiant heated flooring is conveniently located on the main level for guests, along with a dedicated first-floor laundry room. Upstairs, the spacious primary suite features an impressive custom walk-in closet and spa-inspired bath with a soaking tub, radiant heated flooring and heated towel rack. Four additional bedrooms and beautifully appointed bathrooms provide plenty of space throughout the home. Skylights throughout bring an abundance of natural light into the residence. The finished lower level is designed for recreation and entertainment, offering an expansive recreation area with a wet bar and dedicated media room/home theater with its own home entertainment system. The home is wired for seven televisions, while a Sonos sound system with outdoor speakers extends the entertainment outdoors. The backyard offers private country club style amenities, beginning with a spectacular heated in-ground pool with cascading waterfall surrounded by expansive armortec paving stones. Professionally landscaped grounds and dramatic landscape lighting create a beautiful setting for outdoor entertaining. A fully equipped outdoor kitchen with built-in grill, pergola and pavilion provide additional gathering spaces, while a pickleball court and basketball court offer recreation right at home. An attached two car garage completes this extensively appointed Smithtown residence, offering exceptional indoor and outdoor living with amenities designed for entertaining, recreation and everyday enjoyment.

5 Beds ⋅ 4 Baths ⋅ 1039294 MLS

Welcome to 38 Riverview Terrace, an exceptional custom-built Colonial offering five bedrooms, three full bathrooms and one half bath, with an extensive array of high end finishes, entertainment spaces and resort-style outdoor amenities. A grand foyer welcomes you with wainscoting, chandelier and stunning maple hardwood flooring that continues throughout the first floor. The main level features an elegant formal dining room and a spacious den anchored by a wood-burning fireplace. The expansive eat-in chef’s kitchen is designed for both cooking and entertaining, featuring a large 7'10" center island, quartz countertops throughout, skylights, a breakfast area and modern farmhouse sink. High-end Sub-Zero and Wolf appliances include an eight-burner Wolf range with double ovens, a massive custom hood with pot filler, an additional wall oven, warming drawer, built-in microwave, ice maker and wine cooler. Radiant heated flooring completes the kitchen. A powder room with radiant heated flooring is conveniently located on the main level for guests, along with a dedicated first-floor laundry room. Upstairs, the spacious primary suite features an impressive custom walk-in closet and spa-inspired bath with a soaking tub, radiant heated flooring and heated towel rack. Four additional bedrooms and beautifully appointed bathrooms provide plenty of space throughout the home. Skylights throughout bring an abundance of natural light into the residence. The finished lower level is designed for recreation and entertainment, offering an expansive recreation area with a wet bar and dedicated media room/home theater with its own home entertainment system. The home is wired for seven televisions, while a Sonos sound system with outdoor speakers extends the entertainment outdoors. The backyard offers private country club style amenities, beginning with a spectacular heated in-ground pool with cascading waterfall surrounded by expansive armortec paving stones. Professionally landscaped grounds and dramatic landscape lighting create a beautiful setting for outdoor entertaining. A fully equipped outdoor kitchen with built-in grill, pergola and pavilion provide additional gathering spaces, while a pickleball court and basketball court offer recreation right at home. An attached two car garage completes this extensively appointed Smithtown residence, offering exceptional indoor and outdoor living with amenities designed for entertaining, recreation and everyday enjoyment.

38 Riverview Terrace, Smithtown

$1,249,000

A Coastal Setting That Makes Every Day Feel Like an Escape. Set on 1.74 beautifully private acres in a private beach community, this distinctive 4-bedroom, 3-bath home captures the relaxed rhythm of coastal living, surrounded by water views and beautiful natural surroundings, with easy access to town beaches and the marina. The property extends to Stony Brook Harbor, creating a peaceful natural backdrop, while mature plantings, gardens and a rare gunite in-ground pool enhance the sense of privacy and connection to the landscape. Inside, a light and bright open floor plan is defined by oversized windows and walls of glass that frame the surrounding beauty and bring nature into nearly every living space. The impressive great room takes full advantage of the setting with a dramatic wall of windows, vaulted ceilings and a stone wood-burning fireplace. Open to the dining room, this inviting space also features sliders to an expansive, updated Trex deck—a wonderful place for outdoor dining, entertaining or simply enjoying the views of Stony Brook Harbor. The spacious eat-in kitchen offers generous counter space, granite countertops, updated stainless steel appliances and a wonderful dinette area overlooking the pool and lush natural property. The primary bedroom suite provides a private retreat with a beautifully appointed ensuite bath featuring tumbled marble, a double vanity with granite counters, Jacuzzi tub and oversized shower with dual shower heads and multiple body sprays. Two additional generously sized bedrooms and a full bath with a custom vanity and granite countertop complete the second floor. Adding exceptional versatility, first-floor guest quarters with a separate private entrance and covered patio features a bedroom, full bathroom and living area, providing a comfortable and private space for guests or additional living space. The finished lower level offers even more room to gather and entertain, with wood floors, a comfortable den, wet bar and separate entry with direct access to the outdoors. Outdoors, the peaceful setting takes center stage. The rare gunite in-ground pool, surrounded by stone patios and complemented by a convenient changing room, creates an inviting place to spend summer days, entertain or simply relax amid the beautiful gardens and natural coastal plantings. Updated vinyl siding, a carport and ample driveway parking add everyday convenience. More than simply a home near the water, this is a property that embraces the character and ease of coastal living. With privacy, harbor views and the natural beauty of its 1.74-acre setting, every season offers another reason to enjoy being here—a coastal retreat that feels wonderfully removed from everyday life!

4 Beds ⋅ 3 Baths ⋅ 1038256 MLS

A Coastal Setting That Makes Every Day Feel Like an Escape. Set on 1.74 beautifully private acres in a private beach community, this distinctive 4-bedroom, 3-bath home captures the relaxed rhythm of coastal living, surrounded by water views and beautiful natural surroundings, with easy access to town beaches and the marina. The property extends to Stony Brook Harbor, creating a peaceful natural backdrop, while mature plantings, gardens and a rare gunite in-ground pool enhance the sense of privacy and connection to the landscape. Inside, a light and bright open floor plan is defined by oversized windows and walls of glass that frame the surrounding beauty and bring nature into nearly every living space. The impressive great room takes full advantage of the setting with a dramatic wall of windows, vaulted ceilings and a stone wood-burning fireplace. Open to the dining room, this inviting space also features sliders to an expansive, updated Trex deck—a wonderful place for outdoor dining, entertaining or simply enjoying the views of Stony Brook Harbor. The spacious eat-in kitchen offers generous counter space, granite countertops, updated stainless steel appliances and a wonderful dinette area overlooking the pool and lush natural property. The primary bedroom suite provides a private retreat with a beautifully appointed ensuite bath featuring tumbled marble, a double vanity with granite counters, Jacuzzi tub and oversized shower with dual shower heads and multiple body sprays. Two additional generously sized bedrooms and a full bath with a custom vanity and granite countertop complete the second floor. Adding exceptional versatility, first-floor guest quarters with a separate private entrance and covered patio features a bedroom, full bathroom and living area, providing a comfortable and private space for guests or additional living space. The finished lower level offers even more room to gather and entertain, with wood floors, a comfortable den, wet bar and separate entry with direct access to the outdoors. Outdoors, the peaceful setting takes center stage. The rare gunite in-ground pool, surrounded by stone patios and complemented by a convenient changing room, creates an inviting place to spend summer days, entertain or simply relax amid the beautiful gardens and natural coastal plantings. Updated vinyl siding, a carport and ample driveway parking add everyday convenience. More than simply a home near the water, this is a property that embraces the character and ease of coastal living. With privacy, harbor views and the natural beauty of its 1.74-acre setting, every season offers another reason to enjoy being here—a coastal retreat that feels wonderfully removed from everyday life!

588 E. Long Beach Road, Nissequogue

$1,419,999

Welcome to 21 Wilderness Road, an exceptional Colonial set on two private acres in the Village of Nissequogue, where timeless design and thoughtful updates come together in a private, serene setting. Offering 4 bedrooms and 4 bathrooms, this residence delivers generous living spaces, refined finishes, and effortless everyday comfort. Hardwood floors, detailed crown molding, and an inviting floor plan create a warm yet elegant atmosphere throughout. The updated kitchen is appointed with granite countertops, abundant cabinetry, and flows seamlessly into the main living areas, making it ideal for both entertaining and everyday living. A fireside sitting area offers the perfect place to gather, while a dedicated home office provides the flexibility to function as a fifth bedroom, guest suite, or private study. One of the home’s most desirable features is its private deeded access to the pristine Long Island Sound, where scenic water views and shoreline access offer an exceptional coastal lifestyle. Along with Additional highlights include, LOW TAXES, Horse property, an oversized two-car garage with attic storage, a newer Peerless boiler with a Riello burner, and an indirect hot water system for added efficiency. This home is surrounded by natural beauty, yet exceptionally connected, this residence is moments from boating, Nissequogue Golf Club, Stony Brook University and charming villages of St. James.

4 Beds ⋅ 4 Baths ⋅ 1027742 MLS

Welcome to 21 Wilderness Road, an exceptional Colonial set on two private acres in the Village of Nissequogue, where timeless design and thoughtful updates come together in a private, serene setting. Offering 4 bedrooms and 4 bathrooms, this residence delivers generous living spaces, refined finishes, and effortless everyday comfort. Hardwood floors, detailed crown molding, and an inviting floor plan create a warm yet elegant atmosphere throughout. The updated kitchen is appointed with granite countertops, abundant cabinetry, and flows seamlessly into the main living areas, making it ideal for both entertaining and everyday living. A fireside sitting area offers the perfect place to gather, while a dedicated home office provides the flexibility to function as a fifth bedroom, guest suite, or private study. One of the home’s most desirable features is its private deeded access to the pristine Long Island Sound, where scenic water views and shoreline access offer an exceptional coastal lifestyle. Along with Additional highlights include, LOW TAXES, Horse property, an oversized two-car garage with attic storage, a newer Peerless boiler with a Riello burner, and an indirect hot water system for added efficiency. This home is surrounded by natural beauty, yet exceptionally connected, this residence is moments from boating, Nissequogue Golf Club, Stony Brook University and charming villages of St. James.

21 Wilderness Road, Nissequogue

$2,299,000

Welcome to 301 Old Mill Road, a masterfully crafted custom-built new construction nestled on a private lot backing directly to protected preserve land, offering exceptional privacy in the heart of Saint James. Designed with extraordinary attention to detail, this exceptional 6-bedroom, 4-bath residence blends timeless architecture with refined modern luxury, showcasing soaring ceilings, elegant living spaces, thoughtfully curated finishes, distinctive copper roof accents, and impeccable craftsmanship throughout. Additional highlights include a gourmet chef’s kitchen and an expansive lower level with 9-foot ceilings and egress, offering endless possibilities. Every detail reflects quality, comfort, and thoughtful design, creating a truly one-of-a-kind home that must be experienced in person. Available color upgrade through builder.

6 Beds ⋅ 4 Baths ⋅ 1019623 MLS

Welcome to 301 Old Mill Road, a masterfully crafted custom-built new construction nestled on a private lot backing directly to protected preserve land, offering exceptional privacy in the heart of Saint James. Designed with extraordinary attention to detail, this exceptional 6-bedroom, 4-bath residence blends timeless architecture with refined modern luxury, showcasing soaring ceilings, elegant living spaces, thoughtfully curated finishes, distinctive copper roof accents, and impeccable craftsmanship throughout. Additional highlights include a gourmet chef’s kitchen and an expansive lower level with 9-foot ceilings and egress, offering endless possibilities. Every detail reflects quality, comfort, and thoughtful design, creating a truly one-of-a-kind home that must be experienced in person. Available color upgrade through builder.

301 Old Mill Road, Saint James

$1,150,000

Nestled on 2.5 private acres in the picturesque Village of Nissequogue, this beautifully remodeled Colonial offers a rare opportunity to enjoy peaceful country-style living with seasonal water views of the Nissequogue River in one of Long Island’s most sought-after communities. This well-maintained home features numerous updates, including a newer roof, siding, driveway, eat-in kitchen, and hardwood flooring throughout the first floor. The interior was freshly painted in March 2026, creating a bright and welcoming atmosphere. The spacious den is highlighted by a cozy wood-burning fireplace with a stove insert, perfect for relaxing on cooler evenings. Updated bathrooms add modern comfort, while the full basement and attached two-car garage provide ample storage and functionality. Enjoy tranquil outdoor living from the rear patio, where partial river views can be appreciated during the summer months. The backyard is surrounded by mature trees, offering privacy, serenity, and a peaceful natural setting. Ideally located near local beaches, hiking and nature trails, fine dining, shopping, and Stony Brook University and Medical Center. This exceptional property combines scenic beauty, modern updates, and convenient access to area amenities. Smithtown Schools

5 Beds ⋅ 3 Baths ⋅ 1011636 MLS

Nestled on 2.5 private acres in the picturesque Village of Nissequogue, this beautifully remodeled Colonial offers a rare opportunity to enjoy peaceful country-style living with seasonal water views of the Nissequogue River in one of Long Island’s most sought-after communities. This well-maintained home features numerous updates, including a newer roof, siding, driveway, eat-in kitchen, and hardwood flooring throughout the first floor. The interior was freshly painted in March 2026, creating a bright and welcoming atmosphere. The spacious den is highlighted by a cozy wood-burning fireplace with a stove insert, perfect for relaxing on cooler evenings. Updated bathrooms add modern comfort, while the full basement and attached two-car garage provide ample storage and functionality. Enjoy tranquil outdoor living from the rear patio, where partial river views can be appreciated during the summer months. The backyard is surrounded by mature trees, offering privacy, serenity, and a peaceful natural setting. Ideally located near local beaches, hiking and nature trails, fine dining, shopping, and Stony Brook University and Medical Center. This exceptional property combines scenic beauty, modern updates, and convenient access to area amenities. Smithtown Schools

451 River Road, Nissequogue

$1,625,000

Built in 2010 by Quality Features Inc. to a specification meaningfully above the base community standard, this is a 4,610-square-foot colonial on three above-grade levels with a full walk-out basement, three-car attached garage, and a build quality that is visible in every room: oak, marble, and porcelain floors throughout; custom millwork and moldings on every level; Wolf appliances and granite counters in the kitchen; three gas fireplaces, including one anchoring the Lynx outdoor kitchen on the rear terrace; a whole-house generator sized for a home this large; and a residential three-stop elevator serving all levels. The home is fully ADA-compliant and handicapped accessible, engineered into the original build from the foundation up, not retrofitted as an afterthought. The entry foyer establishes the scale immediately — two-story ceiling, custom staircase, hardwood flooring, millwork that carries through the entire main level. The kitchen is organized around Wolf cooking equipment, Sub-Zero-class refrigeration, granite counters, and custom cabinetry built to ceiling height. The rear of the house opens to the pond from the kitchen and main living areas — the sightline was designed deliberately, so the view is part of the daily experience of the home, not reserved for the terrace. Two gas fireplaces on the upper levels; the third anchors the outdoor Lynx kitchen, which turns the rear terrace into a four-season entertaining space with the pond as a backdrop. The lower level is a finished, walk-out floor in its own right. It houses an endless pool and resistance swim system, a dedicated spa room, and a full bathroom — with natural light, grade-level access to the rear yard, and direct sightlines to the pond. This is not a converted storage space. It is a fourth functional level with a specific purpose. Four bedrooms, seven full baths and one half bath. Every bedroom has a private bath. The primary suite is pond-facing on the upper floor. Ten total rooms. The three-stop elevator eliminates the vertical movement problem that makes most three-story homes harder to live in than they look on paper — groceries, luggage, laundry, and daily circulation across levels all become straightforward. The accessible design and flexible floor plan make this home genuinely adaptable across any configuration of use. Hamlet Estates is a gated community of approximately 85 homes with 24-hour guard-staffed entry, a 9,300-square-foot clubhouse, resort-style pool and spa, lighted tennis courts, full fitness center, basketball court, bocce, playground, lakeside putting green, and two community lakes with paddle boats. The pond this home sits on is one of them — a community amenity that 38 Hamlet Woods has exclusive proximity to. HOA common charges apply.

4 Beds ⋅ 8 Baths ⋅ 1008427 MLS

Built in 2010 by Quality Features Inc. to a specification meaningfully above the base community standard, this is a 4,610-square-foot colonial on three above-grade levels with a full walk-out basement, three-car attached garage, and a build quality that is visible in every room: oak, marble, and porcelain floors throughout; custom millwork and moldings on every level; Wolf appliances and granite counters in the kitchen; three gas fireplaces, including one anchoring the Lynx outdoor kitchen on the rear terrace; a whole-house generator sized for a home this large; and a residential three-stop elevator serving all levels. The home is fully ADA-compliant and handicapped accessible, engineered into the original build from the foundation up, not retrofitted as an afterthought. The entry foyer establishes the scale immediately — two-story ceiling, custom staircase, hardwood flooring, millwork that carries through the entire main level. The kitchen is organized around Wolf cooking equipment, Sub-Zero-class refrigeration, granite counters, and custom cabinetry built to ceiling height. The rear of the house opens to the pond from the kitchen and main living areas — the sightline was designed deliberately, so the view is part of the daily experience of the home, not reserved for the terrace. Two gas fireplaces on the upper levels; the third anchors the outdoor Lynx kitchen, which turns the rear terrace into a four-season entertaining space with the pond as a backdrop. The lower level is a finished, walk-out floor in its own right. It houses an endless pool and resistance swim system, a dedicated spa room, and a full bathroom — with natural light, grade-level access to the rear yard, and direct sightlines to the pond. This is not a converted storage space. It is a fourth functional level with a specific purpose. Four bedrooms, seven full baths and one half bath. Every bedroom has a private bath. The primary suite is pond-facing on the upper floor. Ten total rooms. The three-stop elevator eliminates the vertical movement problem that makes most three-story homes harder to live in than they look on paper — groceries, luggage, laundry, and daily circulation across levels all become straightforward. The accessible design and flexible floor plan make this home genuinely adaptable across any configuration of use. Hamlet Estates is a gated community of approximately 85 homes with 24-hour guard-staffed entry, a 9,300-square-foot clubhouse, resort-style pool and spa, lighted tennis courts, full fitness center, basketball court, bocce, playground, lakeside putting green, and two community lakes with paddle boats. The pond this home sits on is one of them — a community amenity that 38 Hamlet Woods has exclusive proximity to. HOA common charges apply.

38 Hamlet Woods Drive, Saint James

$4,999,000

8.42 Acres with LI Sound water frontage and beautiful views. Please reach out to agent for more information regarding building and possible subdivision. Land being sold as is. Updated Survey expected shortly.

993093 MLS

8.42 Acres with LI Sound water frontage and beautiful views. Please reach out to agent for more information regarding building and possible subdivision. Land being sold as is. Updated Survey expected shortly.

Boney Lane, Nissequogue

$6,400,000

Waterfront – Set along 243’ of pristine Long Island Sound frontage, this extraordinary waterfront estate offers a truly rare combination of sweeping unobstructed water views, direct access to a sandy beach, and beautifully manicured level grounds with no high bluff — creating an unparalleled coastal setting rarely found on the North Shore. Privately nestled at the end of a private cul-de-sac on 2 lush acres, this over 7,000 square foot custom residence plus an unbelievable entertainment lower level is surrounded by magnificent specimen plantings, manicured gardens, and expansive Ipe Brazilian walnut decking designed to embrace the breathtaking waterfront backdrop from every angle. Nearly every room captures stunning water views, creating a seamless connection to the shoreline while filling the home with natural light and tranquility. Custom built with uncompromising quality and craftsmanship, the residence showcases high-end custom finishes, exquisite detailed moldings, elegant designer touches, and only the finest materials and systems throughout. Sophisticated yet inviting, the home offers an exceptional blend of refined luxury and relaxed coastal living. Every detail has been thoughtfully curated with no expense spared. Designed for both grand-scale entertaining and intimate everyday living, the property offers exceptional indoor and outdoor gathering spaces where unforgettable memories are waiting to be made. Enjoy breathtaking sunsets over the Long Island Sound with unobstructed views stretching to Connecticut, all from the privacy of your own extraordinary waterfront retreat. Ideally located approximately 60 miles from Manhattan and moments from fine dining, shopping, marinas, Stony Brook University, and Stony Brook University Hospital, the property offers a rare blend of private coastal living and everyday convenience A true private oasis, this remarkable estate offers the feeling of being worlds away while enjoying the beauty, serenity, and prestige of luxury waterfront living at its absolute finest.

5 Beds ⋅ 10 Baths ⋅ 000034 MLS

Waterfront – Set along 243’ of pristine Long Island Sound frontage, this extraordinary waterfront estate offers a truly rare combination of sweeping unobstructed water views, direct access to a sandy beach, and beautifully manicured level grounds with no high bluff — creating an unparalleled coastal setting rarely found on the North Shore. Privately nestled at the end of a private cul-de-sac on 2 lush acres, this over 7,000 square foot custom residence plus an unbelievable entertainment lower level is surrounded by magnificent specimen plantings, manicured gardens, and expansive Ipe Brazilian walnut decking designed to embrace the breathtaking waterfront backdrop from every angle. Nearly every room captures stunning water views, creating a seamless connection to the shoreline while filling the home with natural light and tranquility. Custom built with uncompromising quality and craftsmanship, the residence showcases high-end custom finishes, exquisite detailed moldings, elegant designer touches, and only the finest materials and systems throughout. Sophisticated yet inviting, the home offers an exceptional blend of refined luxury and relaxed coastal living. Every detail has been thoughtfully curated with no expense spared. Designed for both grand-scale entertaining and intimate everyday living, the property offers exceptional indoor and outdoor gathering spaces where unforgettable memories are waiting to be made. Enjoy breathtaking sunsets over the Long Island Sound with unobstructed views stretching to Connecticut, all from the privacy of your own extraordinary waterfront retreat. Ideally located approximately 60 miles from Manhattan and moments from fine dining, shopping, marinas, Stony Brook University, and Stony Brook University Hospital, the property offers a rare blend of private coastal living and everyday convenience A true private oasis, this remarkable estate offers the feeling of being worlds away while enjoying the beauty, serenity, and prestige of luxury waterfront living at its absolute finest.

6 Pheasant Run, Nissequogue

$2,650,000

SELLER MOTIVATED! Welcome to this exceptional new construction estate nestled on 2 private acres in the heart of Nissequogue, one of Long Island’s most prestigious Gold Coast communities. This stunning residence offers exclusive beach access and is conveniently located just 3 miles from the Saint James and Smithtown LIRR stations, providing easy access to New York City. Designed with timeless elegance and modern sophistication, this custom-built home features a sun-drenched open floor plan with soaring ceilings, oversized windows, wide-plank white oak flooring, graceful arched doorways, and two gas fireplaces adorned with custom stonework. The gourmet chef’s kitchen is the centerpiece of the home, showcasing custom cabinetry, premium Thermador appliances, an oversized center island, a butler’s pantry, and a formal dining room complete with dual wine refrigerators perfect for entertaining on any scale. Offering 6 bedrooms and 5.5 bathrooms, including luxurious primary suites on both the main and upper levels, every detail has been thoughtfully curated with elevated designer finishes. Each bathroom offers its own distinctive character, featuring custom vanities, exquisite tile selections, elegant stonework, and beautifully designed walk-in showers that create a spa-like experience. Designer lighting and crystal-inspired hardware add warmth, sophistication, and refined detail throughout. The grand upstairs primary suite boasts vaulted ceilings, dual walk-in closets, and a spa-inspired bath featuring a soaking tub and oversized glass-enclosed shower. Additional amenities include a full basement, 2.5-car garage, and a private tree-lined setting surrounded by protected nature preserves. A rare opportunity to own a remarkable luxury residence that seamlessly blends modern design, superior craftsmanship, and the tranquility of North Shore living.

6 Beds ⋅ 6 Baths ⋅ 999556 MLS

SELLER MOTIVATED! Welcome to this exceptional new construction estate nestled on 2 private acres in the heart of Nissequogue, one of Long Island’s most prestigious Gold Coast communities. This stunning residence offers exclusive beach access and is conveniently located just 3 miles from the Saint James and Smithtown LIRR stations, providing easy access to New York City. Designed with timeless elegance and modern sophistication, this custom-built home features a sun-drenched open floor plan with soaring ceilings, oversized windows, wide-plank white oak flooring, graceful arched doorways, and two gas fireplaces adorned with custom stonework. The gourmet chef’s kitchen is the centerpiece of the home, showcasing custom cabinetry, premium Thermador appliances, an oversized center island, a butler’s pantry, and a formal dining room complete with dual wine refrigerators perfect for entertaining on any scale. Offering 6 bedrooms and 5.5 bathrooms, including luxurious primary suites on both the main and upper levels, every detail has been thoughtfully curated with elevated designer finishes. Each bathroom offers its own distinctive character, featuring custom vanities, exquisite tile selections, elegant stonework, and beautifully designed walk-in showers that create a spa-like experience. Designer lighting and crystal-inspired hardware add warmth, sophistication, and refined detail throughout. The grand upstairs primary suite boasts vaulted ceilings, dual walk-in closets, and a spa-inspired bath featuring a soaking tub and oversized glass-enclosed shower. Additional amenities include a full basement, 2.5-car garage, and a private tree-lined setting surrounded by protected nature preserves. A rare opportunity to own a remarkable luxury residence that seamlessly blends modern design, superior craftsmanship, and the tranquility of North Shore living.

9 Wilderness Road, Nissequogue

$10,800,000

The great statesman, Daniel Webster, (January 18, 1782-October 24 1852) famously remarked, “Long Island Sound is our American Mediterranean.” Indeed, it is. Summerwind. This waterfront enclave, nestled along a uniquely picturesque stretch of Long Island Sound, boasts epic sunrise and sunset views. With architecture and design by world-renowned CetraRuddy Architects, the carefully curated plan demonstrates timeless elegance and understated luxury. The exterior, clad in white stucco and trimmed in fossilized Atlantic shell stone, is complemented by a striking clay tile roof; a design painstakingly supervised by Ludowici’s renowned Master color specialists. Double 11-foot-tall iron entry doors open into the 50-foot-long entrance hall; its intricately carved, painted wood ceilings, soaring to a height of 24-feet, make an indelible first impression. The antique black and white marble and European smoked oak herringbone floors throughout exude Old World charm, and the hand-forged iron balusters and intricately hand-carved rails of the staircase add a touch of whimsy. Entertaining is a delight in the banquet-sized dining room, where a 17th-century Louis XIII limestone mantel takes center stage, complemented by a wet bar, wine refrigeration, and seating for up to 24 guests. The kitchen is the heart of the home and a chef's dream, featuring a raised fireplace hearth finished with 300-year-old French clay tiles, ideal for wood-fired cooking. The expansive custom cabinetry with brass Waterworks hardware provides abundant storage, with a suite of top-of-the-line Wolf and Sub-Zero appliances. The library boasts a dazzling 1920s Baccarat chandelier and a wood-burning fireplace framed by a meticulously carved stone mantel from Orvieto, Italy, circa 1710. The sunken music room, framed by an entire wall of windows, overlooks Long Island Sound, offering the best interior perch for the most epic golden sunsets. The south-facing Moroccan-themed conservatory is bathed in sunlight from the early morning until mid-afternoon, making for very satisfied plants overwintering in this warm, happy space. By evening, the soft glow of a Murano fixture circa 1940 transforms the room into a moody gathering place. Each of five bedrooms offers en suite baths and outdoor space overlooking the breathtaking Long Island Sound. (Two of the five bedrooms have wood-burning fireplaces). An extraordinarily appointed lounge, inspired by Ralph Lauren’s legendary Polo Bar, defines the lower level of the home. Additional amenities here include a soundproof screening room, full wet bar, a professionally audio-tuned listening lounge for vinyl buffs, fitness room with traditional and infrared sauna, expansive laundry room, 3-car garage, and another en suite bedroom, ensuring every need is met in this exceptional home. The grounds of this very private property include a treillaged rose garden, a stone fire pit, Italian wrought iron day beds, a full outdoor kitchen by Hestan, and a private beach with retractable access stairs. Situated equidistant between Long Beach and Short Beach on Long Island's tony North Shore, any and all aquatic activities are readily available, including nearby docking and mooring rights. Other featured local attractions include the beloved Saint James General Store (a fixture on the National Register of Historic Places), Harmony Vineyards, Avalon Nature Preserve, canoeing and kayaking on the Nissequogue River, equestrian facilities, a private golf club, and boating on Long Island Sound. Broker/Owner.

5 Beds ⋅ 8 Baths ⋅ 996747 MLS

The great statesman, Daniel Webster, (January 18, 1782-October 24 1852) famously remarked, “Long Island Sound is our American Mediterranean.” Indeed, it is. Summerwind. This waterfront enclave, nestled along a uniquely picturesque stretch of Long Island Sound, boasts epic sunrise and sunset views. With architecture and design by world-renowned CetraRuddy Architects, the carefully curated plan demonstrates timeless elegance and understated luxury. The exterior, clad in white stucco and trimmed in fossilized Atlantic shell stone, is complemented by a striking clay tile roof; a design painstakingly supervised by Ludowici’s renowned Master color specialists. Double 11-foot-tall iron entry doors open into the 50-foot-long entrance hall; its intricately carved, painted wood ceilings, soaring to a height of 24-feet, make an indelible first impression. The antique black and white marble and European smoked oak herringbone floors throughout exude Old World charm, and the hand-forged iron balusters and intricately hand-carved rails of the staircase add a touch of whimsy. Entertaining is a delight in the banquet-sized dining room, where a 17th-century Louis XIII limestone mantel takes center stage, complemented by a wet bar, wine refrigeration, and seating for up to 24 guests. The kitchen is the heart of the home and a chef's dream, featuring a raised fireplace hearth finished with 300-year-old French clay tiles, ideal for wood-fired cooking. The expansive custom cabinetry with brass Waterworks hardware provides abundant storage, with a suite of top-of-the-line Wolf and Sub-Zero appliances. The library boasts a dazzling 1920s Baccarat chandelier and a wood-burning fireplace framed by a meticulously carved stone mantel from Orvieto, Italy, circa 1710. The sunken music room, framed by an entire wall of windows, overlooks Long Island Sound, offering the best interior perch for the most epic golden sunsets. The south-facing Moroccan-themed conservatory is bathed in sunlight from the early morning until mid-afternoon, making for very satisfied plants overwintering in this warm, happy space. By evening, the soft glow of a Murano fixture circa 1940 transforms the room into a moody gathering place. Each of five bedrooms offers en suite baths and outdoor space overlooking the breathtaking Long Island Sound. (Two of the five bedrooms have wood-burning fireplaces). An extraordinarily appointed lounge, inspired by Ralph Lauren’s legendary Polo Bar, defines the lower level of the home. Additional amenities here include a soundproof screening room, full wet bar, a professionally audio-tuned listening lounge for vinyl buffs, fitness room with traditional and infrared sauna, expansive laundry room, 3-car garage, and another en suite bedroom, ensuring every need is met in this exceptional home. The grounds of this very private property include a treillaged rose garden, a stone fire pit, Italian wrought iron day beds, a full outdoor kitchen by Hestan, and a private beach with retractable access stairs. Situated equidistant between Long Beach and Short Beach on Long Island's tony North Shore, any and all aquatic activities are readily available, including nearby docking and mooring rights. Other featured local attractions include the beloved Saint James General Store (a fixture on the National Register of Historic Places), Harmony Vineyards, Avalon Nature Preserve, canoeing and kayaking on the Nissequogue River, equestrian facilities, a private golf club, and boating on Long Island Sound. Broker/Owner.

Nissequogue

$1,999,999

Welcome to this spacious 5-bedroom, 5-bath Colonial set on 1.70 acres in the desirable Head of the Harbor section of Saint James. This 4,788 sq ft home features a functional layout with a first-floor bedroom and full bath, formal dining room, living room, and an open kitchen with granite countertops, center island, and eat-in area leading to a large family room with fireplace. The second level includes a primary suite with walk-in closets and a private bath, along with additional generously sized bedrooms. Additional highlights include hardwood flooring, crown molding, high ceilings, central air, and natural gas heating. The full finished basement offers additional living space with a lavatory. Exterior features include a 3-car garage, private driveway, and an in-ground pool. Conveniently located near major roadways, shopping, and Smithtown schools.

5 Beds ⋅ 5 Baths ⋅ 992489 MLS

Welcome to this spacious 5-bedroom, 5-bath Colonial set on 1.70 acres in the desirable Head of the Harbor section of Saint James. This 4,788 sq ft home features a functional layout with a first-floor bedroom and full bath, formal dining room, living room, and an open kitchen with granite countertops, center island, and eat-in area leading to a large family room with fireplace. The second level includes a primary suite with walk-in closets and a private bath, along with additional generously sized bedrooms. Additional highlights include hardwood flooring, crown molding, high ceilings, central air, and natural gas heating. The full finished basement offers additional living space with a lavatory. Exterior features include a 3-car garage, private driveway, and an in-ground pool. Conveniently located near major roadways, shopping, and Smithtown schools.

2 Deepwells Lane, Saint James