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Welcome to Country Pointe! This is a private, gated community in Nesconset. The community offers many amenities including a heated salt-water pool, 2 tennis courts, Bocce, a playground and gym. This townhouse is truly beautiful and has a lovely porch. It was completely renovated with a new kitchen put in 2 years ago. It is an elegant and classic design. The open space and natural light in the home is very inviting. The kitchen has nice appliances and offers gas cooking. There is a table with a window for dining. There is also a dining room area for larger parties. This space is open to the living room for easy entertaining. The living room has sliders going out to the fenced deck. It is a very nice location in the community. The primary bedroom features walk-in-closets and an ensuite bathroom that is so pretty. The 2nd bedroom is also very nice and the hallway bathroom is updated. The laundry is in the common hallway. This home features a added bonus with the full finished basement. There is a den area, a recreation area and a spare room. The ulilties are also here in the storage area. CAC 15 years, Stove brand new, Dishwasher 2 years, Bathrooms 5 years, There is a roof assessment that has been fully paid for.

2 Beds ⋅ 2 Baths ⋅ 1047297 MLS

Welcome to Country Pointe! This is a private, gated community in Nesconset. The community offers many amenities including a heated salt-water pool, 2 tennis courts, Bocce, a playground and gym. This townhouse is truly beautiful and has a lovely porch. It was completely renovated with a new kitchen put in 2 years ago. It is an elegant and classic design. The open space and natural light in the home is very inviting. The kitchen has nice appliances and offers gas cooking. There is a table with a window for dining. There is also a dining room area for larger parties. This space is open to the living room for easy entertaining. The living room has sliders going out to the fenced deck. It is a very nice location in the community. The primary bedroom features walk-in-closets and an ensuite bathroom that is so pretty. The 2nd bedroom is also very nice and the hallway bathroom is updated. The laundry is in the common hallway. This home features a added bonus with the full finished basement. There is a den area, a recreation area and a spare room. The ulilties are also here in the storage area. CAC 15 years, Stove brand new, Dishwasher 2 years, Bathrooms 5 years, There is a roof assessment that has been fully paid for.

107 Deer Valley Drive, Nesconset

$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

$799,000

Magnificent Colonial features Entry foyer, Living rm, formal Dining rm currently used as a den, Eat in kitchen with Stainless steel appliances & plenty of cabinets, Laundry area with bonus closet space, 1st floor full bathroom. Bonus area on 1st floor currently used as a 4th bedrrom. 2nd floor features Large primary bedroom suite with a full bathroom & 2 additional s pacious bedrooms and 3rd updated Full baths. A Partial full basement with 2 crawl areas also. Backyard with mature trees for privacy.

3 Beds ⋅ 3 Baths ⋅ 1026187 MLS

Magnificent Colonial features Entry foyer, Living rm, formal Dining rm currently used as a den, Eat in kitchen with Stainless steel appliances & plenty of cabinets, Laundry area with bonus closet space, 1st floor full bathroom. Bonus area on 1st floor currently used as a 4th bedrrom. 2nd floor features Large primary bedroom suite with a full bathroom & 2 additional s pacious bedrooms and 3rd updated Full baths. A Partial full basement with 2 crawl areas also. Backyard with mature trees for privacy.

21 Sailer Street, Saint James

$779,000

Recently renovated from bottom to top, this beautiful townhouse offers a prime location overlooking the pond in the desirable gated Hidden Ponds community of Smithtown. The bright and inviting open floor plan features high ceilings, plenty of natural light, a fireplace, formal dining room, and sliding doors opening to a private patio with peaceful pond views. Thoughtfully updated throughout with a brand-new kitchen and appliances, three beautifully renovated bathrooms, all-new windows and doors, new flooring and stairs, a new patio door, fresh paint, elegant crown molding, and new bedroom closets. The spacious primary suite offers large windows and a walk-in closet. A private laundry room and attached garage add everyday convenience. Enjoy resort-style amenities including a heated saltwater pool, fitness center, tennis, pickleball, basketball, bocce, shuffleboard, dog run, ping pong, and a renovated clubhouse with a fireplace and kitchen, also available for private gatherings. HOA $391/month. Beautifully updated, move-in ready, and a wonderful opportunity to enjoy the Hidden Ponds lifestyle.

2 Beds ⋅ 3 Baths ⋅ 1044752 MLS

Recently renovated from bottom to top, this beautiful townhouse offers a prime location overlooking the pond in the desirable gated Hidden Ponds community of Smithtown. The bright and inviting open floor plan features high ceilings, plenty of natural light, a fireplace, formal dining room, and sliding doors opening to a private patio with peaceful pond views. Thoughtfully updated throughout with a brand-new kitchen and appliances, three beautifully renovated bathrooms, all-new windows and doors, new flooring and stairs, a new patio door, fresh paint, elegant crown molding, and new bedroom closets. The spacious primary suite offers large windows and a walk-in closet. A private laundry room and attached garage add everyday convenience. Enjoy resort-style amenities including a heated saltwater pool, fitness center, tennis, pickleball, basketball, bocce, shuffleboard, dog run, ping pong, and a renovated clubhouse with a fireplace and kitchen, also available for private gatherings. HOA $391/month. Beautifully updated, move-in ready, and a wonderful opportunity to enjoy the Hidden Ponds lifestyle.

230 Pond View Lane, Smithtown

$710,000

A wonderful opportunity to own the highly sought-after Greenwood model in Country Pointe, featuring two bedrooms, two and a half baths, perfectly positioned with a stand alone patio overlooking lush green space. This well-maintained three-story townhouse offers a one-car attached garage, full unfinished basement, and an inviting open-concept layout. The first level features beautiful hardwood floors throughout, and 9-foot ceilings The spacious living room is highlighted by crown molding and high-hat lighting, while the dining room overlooks the deck and has beautiful views of the rear green space. The inviting kitchen offers maple cabinetry, granite countertops, abundant counter space and storage, and a bright, sun-filled eat-in kitchen area. The second floor has a relaxing and inviting den, providing a versatile space to unwind, read, work from home, or enjoy quiet time. With its generous size and flexible layout, the den could also be converted into a third bedroom to accommodate changing lifestyle needs. The spacious primary bedroom features an en-suite bath and an oversized walk-in closet complete with a custom closet system. A second bedroom provides comfortable accommodations for family or guests and offers excellent flexibility. The full unfinished basement provides generous storage and the opportunity to be finished in the future for additional living space, recreation, or a home office. Enjoy the peaceful setting from your private patio overlooking beautifully landscaped green space. The attached one-car garage adds convenience, with additional community parking located nearby. The community is installing new roofs and gutters which will add significant value and provide peace of mind. Country Pointe offers true resort-style living with 24 hour gated security, heated saltwater pool, clubhouse, fitness center, tennis and pickle ball courts, playground and beautifully maintained grounds. The community is centrally located to area shopping, fine restaurants, local beaches and Stony Brook University and Medical Center. Smithtown Schools.

2 Beds ⋅ 3 Baths ⋅ 1044542 MLS

A wonderful opportunity to own the highly sought-after Greenwood model in Country Pointe, featuring two bedrooms, two and a half baths, perfectly positioned with a stand alone patio overlooking lush green space. This well-maintained three-story townhouse offers a one-car attached garage, full unfinished basement, and an inviting open-concept layout. The first level features beautiful hardwood floors throughout, and 9-foot ceilings The spacious living room is highlighted by crown molding and high-hat lighting, while the dining room overlooks the deck and has beautiful views of the rear green space. The inviting kitchen offers maple cabinetry, granite countertops, abundant counter space and storage, and a bright, sun-filled eat-in kitchen area. The second floor has a relaxing and inviting den, providing a versatile space to unwind, read, work from home, or enjoy quiet time. With its generous size and flexible layout, the den could also be converted into a third bedroom to accommodate changing lifestyle needs. The spacious primary bedroom features an en-suite bath and an oversized walk-in closet complete with a custom closet system. A second bedroom provides comfortable accommodations for family or guests and offers excellent flexibility. The full unfinished basement provides generous storage and the opportunity to be finished in the future for additional living space, recreation, or a home office. Enjoy the peaceful setting from your private patio overlooking beautifully landscaped green space. The attached one-car garage adds convenience, with additional community parking located nearby. The community is installing new roofs and gutters which will add significant value and provide peace of mind. Country Pointe offers true resort-style living with 24 hour gated security, heated saltwater pool, clubhouse, fitness center, tennis and pickle ball courts, playground and beautifully maintained grounds. The community is centrally located to area shopping, fine restaurants, local beaches and Stony Brook University and Medical Center. Smithtown Schools.

29 Avery Court, Nesconset

$569,000

Calling All Investors and buyers looking to customize !!!! Located in the desireable Smithtown School District,this split level home offers- 5 bedrooms 3 bathrooms , a full finished basement with OSE. Endless Potential to renovate,update, or design to your taste!!!! Greatg Opportunity to bring your vision and unlock maximum value in a prime Nesconset location !!!! Home is being sold AS IS !

5 Beds ⋅ 3 Baths ⋅ 1045135 MLS

Calling All Investors and buyers looking to customize !!!! Located in the desireable Smithtown School District,this split level home offers- 5 bedrooms 3 bathrooms , a full finished basement with OSE. Endless Potential to renovate,update, or design to your taste!!!! Greatg Opportunity to bring your vision and unlock maximum value in a prime Nesconset location !!!! Home is being sold AS IS !

14 Roosevelt Avenue, Nesconset

$850,000

Beautiful Updated Colonial in a Quiet, Friendly Neighborhood This spacious Colonial home features a fully updated kitchen with a center island, seamlessly opening into a generous formal dining room and an airy living room. A warm and inviting family room with a brick fireplace adds charm and comfort, along with a convenient half bath on the main level. A slider door leads out to a large deck overlooking a fully fenced backyard, complete with an inground pool and slide — perfect for summer fun and entertaining. Upstairs, you’ll find the home’s private living spaces, while the property sits on a quiet, friendly, and picturesque street, close to all shopping, major highways, and transit options for easy commuting.

4 Beds ⋅ 3 Baths ⋅ 1044068 MLS

Beautiful Updated Colonial in a Quiet, Friendly Neighborhood This spacious Colonial home features a fully updated kitchen with a center island, seamlessly opening into a generous formal dining room and an airy living room. A warm and inviting family room with a brick fireplace adds charm and comfort, along with a convenient half bath on the main level. A slider door leads out to a large deck overlooking a fully fenced backyard, complete with an inground pool and slide — perfect for summer fun and entertaining. Upstairs, you’ll find the home’s private living spaces, while the property sits on a quiet, friendly, and picturesque street, close to all shopping, major highways, and transit options for easy commuting.

14 Format Lane, Smithtown

$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

$999,000

Great Cul De Sac Setting for this Center Hall Colonial, Spacious Rooms, Large Windows, Hardwood Floors, Hi Hats, Vaulted Bathrooms, Radiant Heat, Full Finished Basement, Refreshing Salt Lagoon Water Heated(Propane) Pool with Hot Tub, Central Vacuum, 200 Amp, Inground Sprinklers-8z, Fireplace and MORE !

4 Beds ⋅ 4 Baths ⋅ 1041490 MLS

Great Cul De Sac Setting for this Center Hall Colonial, Spacious Rooms, Large Windows, Hardwood Floors, Hi Hats, Vaulted Bathrooms, Radiant Heat, Full Finished Basement, Refreshing Salt Lagoon Water Heated(Propane) Pool with Hot Tub, Central Vacuum, 200 Amp, Inground Sprinklers-8z, Fireplace and MORE !

11 Raphael Boulevard, Nesconset

$1,298,000

North Smithtown, Nisseaquogue Overlook Section As you approach via the impressive circular driveway—complemented by three generous additional driveways for effortless guest parking and trailer access—the estate-like scale of the property immediately unfolds. Step inside to a light-filled interior defined by handcrafted vaulted wood ceilings and natural stone. The Anderson windows frame sweeping, views of the surrounding woodlands at every turn, combining sophisticated indoor living and the serene outdoors A private, self-contained guest suite complete with its own bath for multi-generational living.(With Mother daughter permit from the town) The Horse Facilities: The property features a dedicated equestrian setup including an intimate functional small barn and an adjacent tack room with views of the Nissequogue River landscape. This is more than a home; it is an exceptional legacy property offering, seclusion, natural splendor, and timeless craftsmanship. Arrange a showing today.

5 Beds ⋅ 4 Baths ⋅ 1041795 MLS

North Smithtown, Nisseaquogue Overlook Section As you approach via the impressive circular driveway—complemented by three generous additional driveways for effortless guest parking and trailer access—the estate-like scale of the property immediately unfolds. Step inside to a light-filled interior defined by handcrafted vaulted wood ceilings and natural stone. The Anderson windows frame sweeping, views of the surrounding woodlands at every turn, combining sophisticated indoor living and the serene outdoors A private, self-contained guest suite complete with its own bath for multi-generational living.(With Mother daughter permit from the town) The Horse Facilities: The property features a dedicated equestrian setup including an intimate functional small barn and an adjacent tack room with views of the Nissequogue River landscape. This is more than a home; it is an exceptional legacy property offering, seclusion, natural splendor, and timeless craftsmanship. Arrange a showing today.

135 Oakside Drive, Smithtown

$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

$674,999

Location! Location! Location! Welcome to this beautifully refreshed split-level home, where style, comfort, and versatility comes together in one Smithtown offering. From the moment you arrive, the new driveway, 3 year old hot water heater and freshly painted interiors with the cathedral ceiling sets the tone for a home that feels polished, inviting, and ready to enjoy. The home opens to a bright and thoughtfully designed layout offering 3 bedrooms and 2 full baths, with comfortable living spaces that transition effortlessly from everyday moments to entertaining family and friends. What truly sets this home apart is its versatile lower level with a separate entrance, creating exciting possibilities for extended living, a private home office, guest space, recreation area, or whatever best complements your lifestyle. Recent improvements add even more value and peace of mind, including a new gas burner and hot water heater, new dishwasher, and new washing machine. Go outside and enter the generous corner plot that provides the perfect backdrop for alfresco dining, summer gatherings, gardening, or simply unwinding at the end of the day. Thoughtfully updated, and filled with possibilities, this home delivers the space and flexibility today’s buyers are looking for, wrapped in a warm and beautifully presented home. With the top-rated Smithtown schools, and a neighborhood close to shopping, dining, highways and close to the train station, this is a special opportunity in Smithtown that deserves to be experienced in person.

3 Beds ⋅ 2 Baths ⋅ 1040470 MLS

Location! Location! Location! Welcome to this beautifully refreshed split-level home, where style, comfort, and versatility comes together in one Smithtown offering. From the moment you arrive, the new driveway, 3 year old hot water heater and freshly painted interiors with the cathedral ceiling sets the tone for a home that feels polished, inviting, and ready to enjoy. The home opens to a bright and thoughtfully designed layout offering 3 bedrooms and 2 full baths, with comfortable living spaces that transition effortlessly from everyday moments to entertaining family and friends. What truly sets this home apart is its versatile lower level with a separate entrance, creating exciting possibilities for extended living, a private home office, guest space, recreation area, or whatever best complements your lifestyle. Recent improvements add even more value and peace of mind, including a new gas burner and hot water heater, new dishwasher, and new washing machine. Go outside and enter the generous corner plot that provides the perfect backdrop for alfresco dining, summer gatherings, gardening, or simply unwinding at the end of the day. Thoughtfully updated, and filled with possibilities, this home delivers the space and flexibility today’s buyers are looking for, wrapped in a warm and beautifully presented home. With the top-rated Smithtown schools, and a neighborhood close to shopping, dining, highways and close to the train station, this is a special opportunity in Smithtown that deserves to be experienced in person.

23 Riviera Drive, Smithtown

$699,999

Welcome to this newly renovated 4 bedroom, 2 bathroom Expanded Cape home, located on a 0.38 Acre lot, in a desirable area of Smithtown, NY. The main level boasts a beautiful inviting living room with a bay window, designer molding, recessed lighting, new flooring, and sliders to backyard, an open concept kitchen with stainless steel appliances, dining area with sliders for quick access to backyard, 2 first floor bedrooms, a brand new full bathroom and a laundry area. The upper level offers a very spacious, sun drenched primary bedroom with ensuite bathroom, high ceilings with skylights, plenty of closets, and a forth bedroom. The HUGE backyard has transformed into an entertainer’s paradise, featuring an in-ground pool with waterfall, new pool filtration system, in-ground sprinkles, two charming wooden decks, a large two car garage for storage, two sheds and a spacious workshop space in the back that creates a stunning outdoor space perfect for enjoying the warm summer days. Additional improvements include, new appliances, new bathroom, new flooring, recessed lighting, new doors, updated stone out siding, freshly painted interior walls, tree removals, yard leveling, new landscaping, and new pool filtration system. This property is in a PRIME location of Smithtown. Close to Smithtown LIRR train station, Main Street dining & shopping, Smithtown schools, Blydenburge County park, Caleb Smith State Park, Smithtown library, and many other amenities.

4 Beds ⋅ 2 Baths ⋅ 1036685 MLS

Welcome to this newly renovated 4 bedroom, 2 bathroom Expanded Cape home, located on a 0.38 Acre lot, in a desirable area of Smithtown, NY. The main level boasts a beautiful inviting living room with a bay window, designer molding, recessed lighting, new flooring, and sliders to backyard, an open concept kitchen with stainless steel appliances, dining area with sliders for quick access to backyard, 2 first floor bedrooms, a brand new full bathroom and a laundry area. The upper level offers a very spacious, sun drenched primary bedroom with ensuite bathroom, high ceilings with skylights, plenty of closets, and a forth bedroom. The HUGE backyard has transformed into an entertainer’s paradise, featuring an in-ground pool with waterfall, new pool filtration system, in-ground sprinkles, two charming wooden decks, a large two car garage for storage, two sheds and a spacious workshop space in the back that creates a stunning outdoor space perfect for enjoying the warm summer days. Additional improvements include, new appliances, new bathroom, new flooring, recessed lighting, new doors, updated stone out siding, freshly painted interior walls, tree removals, yard leveling, new landscaping, and new pool filtration system. This property is in a PRIME location of Smithtown. Close to Smithtown LIRR train station, Main Street dining & shopping, Smithtown schools, Blydenburge County park, Caleb Smith State Park, Smithtown library, and many other amenities.

36 Fifty Acre Road S, 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

$779,990

Welcome to this beautifully impeccably styled turnkey 3-Bedroom, 2- bath home on.23 acres professionally landscaped property with a 16x32 inground pool, gazebo and beautiful stonework patio. This home offers the perfect blend of modern style and effortless living. Thoughtfully updated throughout this sun-drenched home features a bright open layout which flows seamlessly from the living room into the open dining room, and kitchen. Three generous sized bedrooms- including a large primary bedroom with ample closet space and a beautifully updated full hall bath complete the main level. Enjoy the partially finished lower level with new carpeting which provides additional living space and a full bath. Whether you envision outdoor entertaining in your 16x32 inground pool or simply enjoy the privacy in your serene fenced in backyard- this is truly your next home!

3 Beds ⋅ 2 Baths ⋅ 1037737 MLS

Welcome to this beautifully impeccably styled turnkey 3-Bedroom, 2- bath home on.23 acres professionally landscaped property with a 16x32 inground pool, gazebo and beautiful stonework patio. This home offers the perfect blend of modern style and effortless living. Thoughtfully updated throughout this sun-drenched home features a bright open layout which flows seamlessly from the living room into the open dining room, and kitchen. Three generous sized bedrooms- including a large primary bedroom with ample closet space and a beautifully updated full hall bath complete the main level. Enjoy the partially finished lower level with new carpeting which provides additional living space and a full bath. Whether you envision outdoor entertaining in your 16x32 inground pool or simply enjoy the privacy in your serene fenced in backyard- this is truly your next home!

116 Shenandoah Boulevard N, Nesconset

$1,649,000

Welcome to this beautiful 5 bedroom 3.5 Bath Colonial perfectly positioned on a quiet cul-de-sac set within Yellow Top Estates, a rare gated enclave of luxury single-family homes. From the covered front porch and beautiful paver and asphalt driveway to the 3-car garage, this home makes an incredible first impression. Enter inside to a dramatic two-story entry foyer with soaring ceilings, beautiful moldings and hardwood floors throughout. The spacious living room features custom built-ins surrounding a gas fireplace, creating the perfect place to gather and relax. The completely renovated kitchen is truly the heart of the home, featuring quartz countertops, a gas range, double ovens, wine fridge and plenty of space for entertaining. A private office or 5th bedroom is perfectly situated away from the main living areas, offering great flexibility for guests or working from home. Upstairs, the spacious primary suite is a true retreat with a beautifully appointed primary bath, including a soaking tub overlooking the backyard. And the backyard is where this home really shines. Designed for resort-style living, it features a freeform saltwater inground pool surrounded by beautiful pavers, an incredible outdoor kitchen with a gas grill, gas pizza oven, granite countertops and an oversized bar ready for summer BBQs and entertaining. A covered Trex deck offers the perfect spot to relax and enjoy the private setting, while a separate hot tub provides the perfect place to unwind and can be enjoyed year-round. Lovingly maintained, thoughtfully updated and ideally located within Yellow Top Estates. Don't miss this special home!

5 Beds ⋅ 4 Baths ⋅ 1037441 MLS

Welcome to this beautiful 5 bedroom 3.5 Bath Colonial perfectly positioned on a quiet cul-de-sac set within Yellow Top Estates, a rare gated enclave of luxury single-family homes. From the covered front porch and beautiful paver and asphalt driveway to the 3-car garage, this home makes an incredible first impression. Enter inside to a dramatic two-story entry foyer with soaring ceilings, beautiful moldings and hardwood floors throughout. The spacious living room features custom built-ins surrounding a gas fireplace, creating the perfect place to gather and relax. The completely renovated kitchen is truly the heart of the home, featuring quartz countertops, a gas range, double ovens, wine fridge and plenty of space for entertaining. A private office or 5th bedroom is perfectly situated away from the main living areas, offering great flexibility for guests or working from home. Upstairs, the spacious primary suite is a true retreat with a beautifully appointed primary bath, including a soaking tub overlooking the backyard. And the backyard is where this home really shines. Designed for resort-style living, it features a freeform saltwater inground pool surrounded by beautiful pavers, an incredible outdoor kitchen with a gas grill, gas pizza oven, granite countertops and an oversized bar ready for summer BBQs and entertaining. A covered Trex deck offers the perfect spot to relax and enjoy the private setting, while a separate hot tub provides the perfect place to unwind and can be enjoyed year-round. Lovingly maintained, thoughtfully updated and ideally located within Yellow Top Estates. Don't miss this special home!

6 Hayloft Court, Smithtown

$858,000

Converted professional office building in the heart of Smithtown, 2,268 SF, delivered vacant! Charming character combined with a functional office layout — ideal for medical, legal, financial, or general professional use. 1st floor features a conference room, 3 private offices, and a bathroom; 2nd floor offers 3 additional private offices and a bathroom; plus, a finished basement for extra workspace or storage. Ample on-site parking, a rare find in this location. Close to downtown Smithtown shops, restaurants, banks, and municipal services, with easy access to major roadways. Turnkey opportunity for an owner-user or investor — won't last!

1035914 MLS

Converted professional office building in the heart of Smithtown, 2,268 SF, delivered vacant! Charming character combined with a functional office layout — ideal for medical, legal, financial, or general professional use. 1st floor features a conference room, 3 private offices, and a bathroom; 2nd floor offers 3 additional private offices and a bathroom; plus, a finished basement for extra workspace or storage. Ample on-site parking, a rare find in this location. Close to downtown Smithtown shops, restaurants, banks, and municipal services, with easy access to major roadways. Turnkey opportunity for an owner-user or investor — won't last!

20 Manor Road, Smithtown

$12,000,000

Rare and unparalleled opportunity to build your ultimate compound. Boasting 16.8 acres with 2000 feet of direct waterfront along the Long Island Sound in the exclusive, incorporated Village of Nissequogue. This sprawling legacy estate offers a rare combination of absolute privacy and endless coastal possibilities. Enjoy unparalleled, direct beach access via a staircase, allowing you to step off your estate and directly onto the sand to launch a kayak, paddleboard, or stroll the shoreline at sunset. Meandering trails, mature specimen trees, and stone paths complete this magnificent blank canvas. The expansive 11,000+ sq. ft. foundational footprint provides the perfect bones to recreate a world-class, 6-bedroom, 7-bathroom modern masterpiece, complete with structural footprints for both an all-season indoor pool and a sweeping outdoor pool oasis. A stone pathway leads you to the tennis court that is ready to be restored. Located in The Village of Nissequogue, Long Island’s best-kept luxury secret where unparalleled privacy meets pristine coastal living. This incorporated sanctuary offers a tranquil, estate-driven refuge just 50 miles outside Manhattan. Surrounded by StonyBrook Harbor, and the Long Island Sound. Residents also enjoy exclusive access to restricted shorelines like Short Beach and Long Beach, as well as the protected trails of the 150-acre David Weld Sanctuary.

1034543 MLS

Rare and unparalleled opportunity to build your ultimate compound. Boasting 16.8 acres with 2000 feet of direct waterfront along the Long Island Sound in the exclusive, incorporated Village of Nissequogue. This sprawling legacy estate offers a rare combination of absolute privacy and endless coastal possibilities. Enjoy unparalleled, direct beach access via a staircase, allowing you to step off your estate and directly onto the sand to launch a kayak, paddleboard, or stroll the shoreline at sunset. Meandering trails, mature specimen trees, and stone paths complete this magnificent blank canvas. The expansive 11,000+ sq. ft. foundational footprint provides the perfect bones to recreate a world-class, 6-bedroom, 7-bathroom modern masterpiece, complete with structural footprints for both an all-season indoor pool and a sweeping outdoor pool oasis. A stone pathway leads you to the tennis court that is ready to be restored. Located in The Village of Nissequogue, Long Island’s best-kept luxury secret where unparalleled privacy meets pristine coastal living. This incorporated sanctuary offers a tranquil, estate-driven refuge just 50 miles outside Manhattan. Surrounded by StonyBrook Harbor, and the Long Island Sound. Residents also enjoy exclusive access to restricted shorelines like Short Beach and Long Beach, as well as the protected trails of the 150-acre David Weld Sanctuary.

546 Long Beach Road, Nissequogue

708 W Cabot Court Unit #708, Saint James

$499,998

55+gated community of Fairfield at Saint James. The brand new update ranch home offers one car garage, a special primary bedroom with walk in closet and eat in updated kitchen with large window. New appliances only one year new. The club house offers two outdoor pools, a fitness center, an indoor pool, library and much more....

1 Beds ⋅ 1 Baths ⋅ 1034423 MLS

55+gated community of Fairfield at Saint James. The brand new update ranch home offers one car garage, a special primary bedroom with walk in closet and eat in updated kitchen with large window. New appliances only one year new. The club house offers two outdoor pools, a fitness center, an indoor pool, library and much more....

708 W Cabot Court Unit #708, Saint James

$905,000

Pristine and sophisticated, this beautifully customized 4-bedroom, 2.5-bath ranch offers a spectacular open-concept design perfect for today's lifestyle. Originally built in the 1960s, the home has been thoughtfully updated over the years to reflect timeless elegance and exceptional craftsmanship. The stunning center island kitchen features a dramatic 7-foot black granite island, Sub-Zero refrigerator, Bosch dishwasher, GE appliances, under-counter microwave, and cooktop. Hardwood floors and custom built-ins enhance the home's warmth and character, while the spacious living and entertaining areas flow seamlessly to the rear deck for effortless indoor-outdoor living. A truly special home that is impeccably maintained and a must see.

4 Beds ⋅ 3 Baths ⋅ 1032833 MLS

Pristine and sophisticated, this beautifully customized 4-bedroom, 2.5-bath ranch offers a spectacular open-concept design perfect for today's lifestyle. Originally built in the 1960s, the home has been thoughtfully updated over the years to reflect timeless elegance and exceptional craftsmanship. The stunning center island kitchen features a dramatic 7-foot black granite island, Sub-Zero refrigerator, Bosch dishwasher, GE appliances, under-counter microwave, and cooktop. Hardwood floors and custom built-ins enhance the home's warmth and character, while the spacious living and entertaining areas flow seamlessly to the rear deck for effortless indoor-outdoor living. A truly special home that is impeccably maintained and a must see.

22 S Lot Road, Smithtown

$699,999

Well-Maintained Cozy Ranch on a Beautiful Tree-Lined Street in Smithtown Welcome to this charming and well-maintained ranch nestled on a picturesque, tree-lined street in Smithtown, set on a generous .63-acre property with a detached garage. This inviting home offers a comfortable and functional layout featuring a formal living room, formal dining room, cozy den, and an eat-in kitchen with propane cooking. The home offers three bedrooms and one full bathroom, providing plenty of space for comfortable living. Anderson windows and beautiful hardwood floors in the living room add warmth and character to the home. Outside, enjoy the expansive property with plenty of room for outdoor activities, entertaining, gardening, or simply relaxing in your own private setting. The detached garage provides additional storage and convenience. A wonderful opportunity to own a lovingly maintained ranch in a desirable Smithtown location.

3 Beds ⋅ 1 Baths ⋅ 1030650 MLS

Well-Maintained Cozy Ranch on a Beautiful Tree-Lined Street in Smithtown Welcome to this charming and well-maintained ranch nestled on a picturesque, tree-lined street in Smithtown, set on a generous .63-acre property with a detached garage. This inviting home offers a comfortable and functional layout featuring a formal living room, formal dining room, cozy den, and an eat-in kitchen with propane cooking. The home offers three bedrooms and one full bathroom, providing plenty of space for comfortable living. Anderson windows and beautiful hardwood floors in the living room add warmth and character to the home. Outside, enjoy the expansive property with plenty of room for outdoor activities, entertaining, gardening, or simply relaxing in your own private setting. The detached garage provides additional storage and convenience. A wonderful opportunity to own a lovingly maintained ranch in a desirable Smithtown location.

42 Pineacre Drive, Smithtown

$800,000

Sprawling Smithtown Ranch on .52 Acre with Gunite Pool & 3-Car Garage! Space, flexibility and a backyard built for summer living come together in this distinctive 4-bedroom, 2.5-bath home set on a beautiful .52-acre property in the desirable Smithtown Pines area. Offering the ease and open feel of ranch-style living with a thoughtfully designed split-level bedroom wing, this home provides an exceptional layout for both everyday living and entertaining. A welcoming foyer opens to generously sized living spaces, including a formal living room, formal dining room, expansive den and a separate home office—ideal for working from home or creating a quiet flex space. The eat-in kitchen features granite countertops, stainless steel appliances and direct access to the deck, backyard and pool, making indoor-outdoor entertaining easy. Just a few steps above the main living area are four bedrooms and two full baths, creating separation and privacy without sacrificing the convenience of a ranch-style layout. The spacious primary suite features walk-in closets and a private bath with a sunken tub. The partially finished basement provides additional flexible space along with plenty of storage. Enjoy more than half an acre with a gunite inground pool with a waterfall feature, a spacious deck for outdoor dining and entertaining, and an inground sprinkler system. A circular driveway and rare 3-car attached garage provide abundant parking and storage. Gas heat, and full house central air conditioning add to the home's everyday comfort and convenience. If you've been searching for generous living space with a versatile layout in the Smithtown School District, 29 Ivy Hill Drive deserves a closer look.

4 Beds ⋅ 3 Baths ⋅ 1030391 MLS

Sprawling Smithtown Ranch on .52 Acre with Gunite Pool & 3-Car Garage! Space, flexibility and a backyard built for summer living come together in this distinctive 4-bedroom, 2.5-bath home set on a beautiful .52-acre property in the desirable Smithtown Pines area. Offering the ease and open feel of ranch-style living with a thoughtfully designed split-level bedroom wing, this home provides an exceptional layout for both everyday living and entertaining. A welcoming foyer opens to generously sized living spaces, including a formal living room, formal dining room, expansive den and a separate home office—ideal for working from home or creating a quiet flex space. The eat-in kitchen features granite countertops, stainless steel appliances and direct access to the deck, backyard and pool, making indoor-outdoor entertaining easy. Just a few steps above the main living area are four bedrooms and two full baths, creating separation and privacy without sacrificing the convenience of a ranch-style layout. The spacious primary suite features walk-in closets and a private bath with a sunken tub. The partially finished basement provides additional flexible space along with plenty of storage. Enjoy more than half an acre with a gunite inground pool with a waterfall feature, a spacious deck for outdoor dining and entertaining, and an inground sprinkler system. A circular driveway and rare 3-car attached garage provide abundant parking and storage. Gas heat, and full house central air conditioning add to the home's everyday comfort and convenience. If you've been searching for generous living space with a versatile layout in the Smithtown School District, 29 Ivy Hill Drive deserves a closer look.

29 Ivy Hill Drive, Smithtown

$850,000

Exceptional owner-user opportunity in the heart of Smithtown! This well-maintained 1,683 SF professional office building is situated on a 10,890 SF lot with NB (Neighborhood Business) zoning. The first floor is ideal for an owner-occupant, while the income-producing lower-level tenant provides immediate rental income to help offset ownership costs. Conveniently located on Terry Road with easy access to major roadways, shopping, restaurants, and the Smithtown business district. A great opportunity for professional, medical, or service-related businesses seeking to own rather than lease, while benefiting from an existing income stream.

1029963 MLS

Exceptional owner-user opportunity in the heart of Smithtown! This well-maintained 1,683 SF professional office building is situated on a 10,890 SF lot with NB (Neighborhood Business) zoning. The first floor is ideal for an owner-occupant, while the income-producing lower-level tenant provides immediate rental income to help offset ownership costs. Conveniently located on Terry Road with easy access to major roadways, shopping, restaurants, and the Smithtown business district. A great opportunity for professional, medical, or service-related businesses seeking to own rather than lease, while benefiting from an existing income stream.

198 Terry Road, Smithtown

$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

$2,275,000

Tucked away on two acres at the end of a quiet cul-de-sac, in the prestigious enclave of Head of the Harbor, this magnificent five-bedroom, four-bath estate offers an unparalleled blend of modern luxury and serene privacy. The entire residence has undergone a comprehensive transformation over the past six years, resulting in a home that feels brand new while retaining its sophisticated, timeless character. The heart of the home is the stunning new kitchen, designed with a modern aesthetic that features sleek finishes, built-in Sub-zero refrigerator, Wolf oven, Jenn Air cooktop- with an intuitive layout perfect for both daily living and large-scale hosting. The large center island with seating, waterfall-edge quartz countertop and second sink invites entertaining on a grand scale, or just a perfect intimate gathering. The new picture window provides a panoramic view of the pristine outdoor, resort-like grounds. Off the kitchen, enjoy casual meals in the glass-enclosed dining area. The main floor also features a formal dining room, a bedroom and full bathroom, in addition to the entertaining spaces, which include an expansive family room with fireplace and access to the patio, an adjacent living room, and a bright, open sitting room off the kitchen with floor-to-ceiling windows looking out to the parklike property. Each of the four full bathrooms has been exquisitely renovated with designer fixtures, heater floor in the primary suite, and contemporary tiling, providing a spa-like experience in every corner of the house. The home's electric service has been upgraded to 450 amp in 2022, and also has a whole house natural gas generator, providing comfort along with style across the entire living space! Beyond the interior, the property serves as a private sanctuary. A brand-new patio leads to a sparkling pool with all new equipment installed in 2022, creating an outdoor oasis framed by mature trees and fenced-in expansive greenery across the 2 acre property. You will also find a dining pavilion offering shade and comfort, a bar, and a cabana with a changing area, bath and outdoor shower for added convenience. The commitment to quality is evident in the structural upgrades as well, including a new balcony off of the primary suite, new roof and the addition of owned solar panels for exceptional energy efficiency. The lower level reveals a fully finished basement, offering versatile space including a summer kitchen, new full bathroom, home gym, media room and recreation area. With every detail meticulously addressed—from the expansive living spaces to the secluded acreage—this estate represents a rare opportunity to enjoy a turnkey lifestyle in one of the most sought-after locations on the North Shore. This Head of the Harbor home is surrounded by the charm of Nissequogue, Smithtown, Saint James and Stony Brook. Imagine days spent exploring local beaches, enjoying waterfront activities, or unwinding at nearby fine dining establishments, vineyards and local parks. For boating enthusiasts, this lifestyle is a dream come true. Note: please see the attached document for a full list of upgrades to this home!

5 Beds ⋅ 4 Baths ⋅ 1027926 MLS

Tucked away on two acres at the end of a quiet cul-de-sac, in the prestigious enclave of Head of the Harbor, this magnificent five-bedroom, four-bath estate offers an unparalleled blend of modern luxury and serene privacy. The entire residence has undergone a comprehensive transformation over the past six years, resulting in a home that feels brand new while retaining its sophisticated, timeless character. The heart of the home is the stunning new kitchen, designed with a modern aesthetic that features sleek finishes, built-in Sub-zero refrigerator, Wolf oven, Jenn Air cooktop- with an intuitive layout perfect for both daily living and large-scale hosting. The large center island with seating, waterfall-edge quartz countertop and second sink invites entertaining on a grand scale, or just a perfect intimate gathering. The new picture window provides a panoramic view of the pristine outdoor, resort-like grounds. Off the kitchen, enjoy casual meals in the glass-enclosed dining area. The main floor also features a formal dining room, a bedroom and full bathroom, in addition to the entertaining spaces, which include an expansive family room with fireplace and access to the patio, an adjacent living room, and a bright, open sitting room off the kitchen with floor-to-ceiling windows looking out to the parklike property. Each of the four full bathrooms has been exquisitely renovated with designer fixtures, heater floor in the primary suite, and contemporary tiling, providing a spa-like experience in every corner of the house. The home's electric service has been upgraded to 450 amp in 2022, and also has a whole house natural gas generator, providing comfort along with style across the entire living space! Beyond the interior, the property serves as a private sanctuary. A brand-new patio leads to a sparkling pool with all new equipment installed in 2022, creating an outdoor oasis framed by mature trees and fenced-in expansive greenery across the 2 acre property. You will also find a dining pavilion offering shade and comfort, a bar, and a cabana with a changing area, bath and outdoor shower for added convenience. The commitment to quality is evident in the structural upgrades as well, including a new balcony off of the primary suite, new roof and the addition of owned solar panels for exceptional energy efficiency. The lower level reveals a fully finished basement, offering versatile space including a summer kitchen, new full bathroom, home gym, media room and recreation area. With every detail meticulously addressed—from the expansive living spaces to the secluded acreage—this estate represents a rare opportunity to enjoy a turnkey lifestyle in one of the most sought-after locations on the North Shore. This Head of the Harbor home is surrounded by the charm of Nissequogue, Smithtown, Saint James and Stony Brook. Imagine days spent exploring local beaches, enjoying waterfront activities, or unwinding at nearby fine dining establishments, vineyards and local parks. For boating enthusiasts, this lifestyle is a dream come true. Note: please see the attached document for a full list of upgrades to this home!

5 Meadow Gate W, Head Of Harbor

$3,995,000

Welcome to 38 Landing Meadow Road, Smithtown. Nestled on almost 23 picturesque and serene waterfront acres overlooking the renowned Nissequogue River this is a truly extraordinary North Shore retreat. Driving down the long private driveway your senses are alive to the possibilities of what is to appear. Surrounded by breathtaking natural beauty, the property includes agricultural land adjoining approx. 60 acres of protected preserve, creating an unmatched sense of privacy and tranquility. Wide open vistas, emerald lawns, magnificent mature trees and the grand nature of this idyllic scene are unmatched. Barns, stables, paddock, workshops, and multiple outbuildings provide endless possibilities for equestrian pursuits, farming, recreation, or creating your own private compound or purpose. This timeless Manor House built in 1828 offers nearly 6,000 square feet of living space, featuring 7 stately and spacious bedrooms and 6 bathrooms. The magnificent Estate is highlighted on the first floor by a warm and opening center hall with access to the rear property and patio, a formal living room, grand den with fireplace and the first floor is side property, den or library with a fireplace, truly formal dining room with a fireplace, an inviting eat-in kitchen designed for everyday living and entertaining and butlers pantry, family room or bedroom with a wet bar and two bathrooms. The charm and character of all of the rooms with so many original details of fireplace mantles and surrounds, stair mouldings and hardwood floors take you to another time. Besides the grand Manor home the property outside has an antique barn of approx. 7,500 square feet which offers the possibility of future use, and a caretakers suite inside. Also on the property is a “bank” barn with four 12x14’ horse stalls, a tack room and hayloft. Besides this barn is another smaller barn also with four 12x12’ horse stalls. On the grand 20 acre land preserve is extensive paddock and other fenced areas. Conveniently located near parks, golf clubs, beaches, wineries, charming villages, museums, and fine dining, this exceptional estate offers a rare opportunity to experience waterfront living at its finest. Walking in to this one-of-a-kind Estate you feel that 38 Landing Meadow Road Smithtown is a rare opportunity where history, nature and endless potential come together. Since the property adjoins multiple land preserve woodlands it ensures a forever-preserved backdrop and an exceptional North Shore lifestyle in which this legacy Estate can be yours and protected.

7 Beds ⋅ 6 Baths ⋅ 1022766 MLS

Welcome to 38 Landing Meadow Road, Smithtown. Nestled on almost 23 picturesque and serene waterfront acres overlooking the renowned Nissequogue River this is a truly extraordinary North Shore retreat. Driving down the long private driveway your senses are alive to the possibilities of what is to appear. Surrounded by breathtaking natural beauty, the property includes agricultural land adjoining approx. 60 acres of protected preserve, creating an unmatched sense of privacy and tranquility. Wide open vistas, emerald lawns, magnificent mature trees and the grand nature of this idyllic scene are unmatched. Barns, stables, paddock, workshops, and multiple outbuildings provide endless possibilities for equestrian pursuits, farming, recreation, or creating your own private compound or purpose. This timeless Manor House built in 1828 offers nearly 6,000 square feet of living space, featuring 7 stately and spacious bedrooms and 6 bathrooms. The magnificent Estate is highlighted on the first floor by a warm and opening center hall with access to the rear property and patio, a formal living room, grand den with fireplace and the first floor is side property, den or library with a fireplace, truly formal dining room with a fireplace, an inviting eat-in kitchen designed for everyday living and entertaining and butlers pantry, family room or bedroom with a wet bar and two bathrooms. The charm and character of all of the rooms with so many original details of fireplace mantles and surrounds, stair mouldings and hardwood floors take you to another time. Besides the grand Manor home the property outside has an antique barn of approx. 7,500 square feet which offers the possibility of future use, and a caretakers suite inside. Also on the property is a “bank” barn with four 12x14’ horse stalls, a tack room and hayloft. Besides this barn is another smaller barn also with four 12x12’ horse stalls. On the grand 20 acre land preserve is extensive paddock and other fenced areas. Conveniently located near parks, golf clubs, beaches, wineries, charming villages, museums, and fine dining, this exceptional estate offers a rare opportunity to experience waterfront living at its finest. Walking in to this one-of-a-kind Estate you feel that 38 Landing Meadow Road Smithtown is a rare opportunity where history, nature and endless potential come together. Since the property adjoins multiple land preserve woodlands it ensures a forever-preserved backdrop and an exceptional North Shore lifestyle in which this legacy Estate can be yours and protected.

38 Landing Meadow Road, Smithtown

$790,000

Spacious 4-bedroom, 3 bath Center Hall Colonial offering approximately 2,745 square feet of living space set on approximately .35 acre in sought-after Hauppauge neighborhood within the Smithtown School District. A welcoming layout offers a formal living room and dining room along with a comfortable den/family off the kitchen providing plenty of space for both everyday living and entertaining. A fireplace adds warmth and character, while the spacious sunroom extends the living space and overlooks the property. Unique additional features include a greenhouse and sauna, offering even more possibilities. Four generously sized bedrooms provide plenty of room to spread out. The property offers ample outdoor space for entertaining, gardening, and recreation. Well maintained and ready for it's next owner to bring thier own style and vision. Conveniently located near shopping, restaurants, parks, and major roadways.

4 Beds ⋅ 3 Baths ⋅ 1026950 MLS

Spacious 4-bedroom, 3 bath Center Hall Colonial offering approximately 2,745 square feet of living space set on approximately .35 acre in sought-after Hauppauge neighborhood within the Smithtown School District. A welcoming layout offers a formal living room and dining room along with a comfortable den/family off the kitchen providing plenty of space for both everyday living and entertaining. A fireplace adds warmth and character, while the spacious sunroom extends the living space and overlooks the property. Unique additional features include a greenhouse and sauna, offering even more possibilities. Four generously sized bedrooms provide plenty of room to spread out. The property offers ample outdoor space for entertaining, gardening, and recreation. Well maintained and ready for it's next owner to bring thier own style and vision. Conveniently located near shopping, restaurants, parks, and major roadways.

12 Kenny Street, Hauppauge

$869,000

Welcome to this exceptional 4-bedroom, 2.5-bath Splanch located in the prestigious East Hill Estates section of Smithtown. Offering approximately 2,380 square feet of beautifully designed living space, this residence seamlessly blends timeless elegance with everyday comfort. A gracious floor plan features sun-filled living areas, a warm and inviting fireplace, spacious formal and casual gathering spaces, and a well-appointed kitchen designed for both entertaining and daily living. The generous primary suite provides a peaceful retreat, while three additional bedrooms offer flexibility for family, guests, or a home office. Enjoy year-round comfort with an updated HVAC system, providing efficient heating and cooling throughout the home. Step outside to your private backyard oasis featuring a heated in-ground salt water swimming pool, expansive patio with gas BBQ connection , and beautifully landscaped grounds—perfect for outdoor entertaining or relaxing all summer long. Additional highlights include an attached two-car garage, a full basement offering abundant storage and future finishing potential, and pride of ownership throughout. Ideally situated in the award-winning Smithtown Central School District, the home is conveniently located near parks, golf courses, shopping, dining, beaches, major parkways, and the Long Island Rail Road. This is a rare opportunity to own a beautifully maintained home in one of Smithtown’s most sought-after neighborhoods, where classic Colonial charm meets modern comfort.

4 Beds ⋅ 3 Baths ⋅ 1026666 MLS

Welcome to this exceptional 4-bedroom, 2.5-bath Splanch located in the prestigious East Hill Estates section of Smithtown. Offering approximately 2,380 square feet of beautifully designed living space, this residence seamlessly blends timeless elegance with everyday comfort. A gracious floor plan features sun-filled living areas, a warm and inviting fireplace, spacious formal and casual gathering spaces, and a well-appointed kitchen designed for both entertaining and daily living. The generous primary suite provides a peaceful retreat, while three additional bedrooms offer flexibility for family, guests, or a home office. Enjoy year-round comfort with an updated HVAC system, providing efficient heating and cooling throughout the home. Step outside to your private backyard oasis featuring a heated in-ground salt water swimming pool, expansive patio with gas BBQ connection , and beautifully landscaped grounds—perfect for outdoor entertaining or relaxing all summer long. Additional highlights include an attached two-car garage, a full basement offering abundant storage and future finishing potential, and pride of ownership throughout. Ideally situated in the award-winning Smithtown Central School District, the home is conveniently located near parks, golf courses, shopping, dining, beaches, major parkways, and the Long Island Rail Road. This is a rare opportunity to own a beautifully maintained home in one of Smithtown’s most sought-after neighborhoods, where classic Colonial charm meets modern comfort.

6 Navy Drive, Smithtown

$959,000

LISTENING TO OFFERS! When opportunity knocks the door must be opened. Welcome to 57 Brooksite Drive. A stunning single unit home in the heart of Smithtown NY sitting on nearly a half an acre of property. Renovated just over 1 year ago this home is being offered to the market at an amazing opportunity to be purchased as turn key as they come. Enjoy the state of the art renovations throughout the property including a finished basement, a first floor master bedroom, and an open concept dining room & kitchen. Spark up the fire and sit with the entire group as you enjoy the fully functional living room fireplace. Walk out your sliding door and gaze at your massive nearly half acre of land where you can host and entertain your friends. Got a project? Your attached garage gives you plenty of space to park your car and sustain your handyman fix. This property needs absolutely nothing except your willingness to enjoy it's perfection. This is a truly ICONIC home!

4 Beds ⋅ 3 Baths ⋅ 1020597 MLS

LISTENING TO OFFERS! When opportunity knocks the door must be opened. Welcome to 57 Brooksite Drive. A stunning single unit home in the heart of Smithtown NY sitting on nearly a half an acre of property. Renovated just over 1 year ago this home is being offered to the market at an amazing opportunity to be purchased as turn key as they come. Enjoy the state of the art renovations throughout the property including a finished basement, a first floor master bedroom, and an open concept dining room & kitchen. Spark up the fire and sit with the entire group as you enjoy the fully functional living room fireplace. Walk out your sliding door and gaze at your massive nearly half acre of land where you can host and entertain your friends. Got a project? Your attached garage gives you plenty of space to park your car and sustain your handyman fix. This property needs absolutely nothing except your willingness to enjoy it's perfection. This is a truly ICONIC home!

57 Brooksite Drive, Smithtown

$1,589,000

Spectacular 5 BR, 3.5 Bath Post-Modern Colonial in a premier 24hr gated community. This home has been extensively updated with incredible attention to detail. Features include brand-new solid oak hardwood floors throughout the entire house. The spacious kitchen is beautifully updated with a brand-new dishwasher, a high-efficiency exhaust fan, and sleek new countertops with a deep-basin sink. Enjoy a grand open layout, sun-drenched principal rooms, a family room with a fireplace, and a massive primary suite. Pristine 0.41-acre property with a 3-car garage and full basement. Resort-style community amenities include a private clubhouse, sparkling pool, fitness center, and Playground. Smithtown School District. Impeccably maintained with too many updates to list—this turn-key gem feels brand new!

5 Beds ⋅ 4 Baths ⋅ 1024519 MLS

Spectacular 5 BR, 3.5 Bath Post-Modern Colonial in a premier 24hr gated community. This home has been extensively updated with incredible attention to detail. Features include brand-new solid oak hardwood floors throughout the entire house. The spacious kitchen is beautifully updated with a brand-new dishwasher, a high-efficiency exhaust fan, and sleek new countertops with a deep-basin sink. Enjoy a grand open layout, sun-drenched principal rooms, a family room with a fireplace, and a massive primary suite. Pristine 0.41-acre property with a 3-car garage and full basement. Resort-style community amenities include a private clubhouse, sparkling pool, fitness center, and Playground. Smithtown School District. Impeccably maintained with too many updates to list—this turn-key gem feels brand new!

35 Monterrey Drive, Saint James

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