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$3,995,000
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
$819,000
4 Beds ⋅ 3 Baths ⋅ 1026950 MLS
Contemporary 4-bedroom, 2.5-bath home situated on approximately 0.35 acres in the Smithtown School District. Built in 1967, this spacious residence offers approximately 2,745 square feet of living space, a fireplace, and a partial basement. The generous lot provides ample outdoor space for entertaining, gardening, or recreation. Conveniently located near shopping, restaurants, parks, major roadways, and other everyday amenities. A wonderful opportunity to make this home your own.

12 Kenny Street, Hauppauge
$869,000
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
$725,000
3 Beds ⋅ 2 Baths ⋅ 1026215 MLS
Nestled on an expansive 12,195 sq. ft. fully fenced property in the heart of St. James and located within the highly acclaimed Smithtown School District, this beautifully maintained farmhouse style Cape Cod is the perfect place to call home. Offering 3 spacious bedrooms and 2 full bathrooms, this inviting residence blends timeless charm with thoughtful updates throughout. Beautifully refinished hardwood floors, a sun filled living room with recessed lighting, a formal dining room, and an updated kitchen create a warm and welcoming atmosphere that's ideal for both everyday living and entertaining. Main-floor laundry adds everyday convenience. The second-floor features three generously sized bedrooms, a full bathroom, a huge walk-in closet, and a large walk-up attic, providing exceptional storage and flexibility. A full basement offers even more storage space and endless possibilities. Step outside to enjoy your private fully fenced front and backyard, complete with a newly updated patio perfect for summer barbecues, outdoor gatherings, gardening, or simply relaxing while enjoying the oversized yard. Ideally located just minutes from the St. James LIRR station, shopping, restaurants, parks, and major roadways, this exceptional home offers the perfect combination of charm, space, convenience, and location. Don't miss the opportunity to own this move-in-ready gem in one of Long Island's most sought-after communities.

214 1st Street, Saint James
$999,000
4 Beds ⋅ 3 Baths ⋅ 1020597 MLS
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! Showings by appointment only.

57 Brooksite Drive, Smithtown
$1,589,000
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
$824,000
4 Beds ⋅ 2 Baths ⋅ 1023804 MLS
Welcome to this beautifully renovated Saint James home where no expense has been spared. Every detail has been thoughtfully updated, featuring board and batten siding, Andersen windows, and gorgeous hardwood floors throughout. The designer two tone kitchen showcases vanilla and warm brown shaker wood cabinetry, elegant granite countertops, and stainless steel appliances. Both brand new bathrooms have sleek, modern design. Additional upgrades include In ground sprinklers, brand new central air conditioning, new electrical panels for both the house and pool, and a fully finished basement with outside entrance. Step outside to your private backyard oasis featuring a newly updated in ground pool with brand new liner, pump, filter and beautifully landscaped grounds. Ideally located just minutes from Smith Heaven mall, shopping, dining, parks, and major roadways. This home offers both convenience and an exceptional lifestyle. Situated within the highly regarded Smithtown School District! This truly move in ready home delivers luxury finishes, quality craftsmanship, and incredible value. POTENTIAL MOTHER DAUGHTER SET UP AND BASEMENT WITH OUTSIDE ENTRANCE!

273 Cambon Avenue, Saint James
$1,749,999
5 Beds ⋅ 4 Baths ⋅ 1023719 MLS
Welcome to Plymouth Estates, a 5 lot subdivision in the prestigious neighborhood of Smithtown, NY. This NEW CONSTRUCTION subdivision on a cul-de-sac offers 5 exceptional lots, with 5 bedrooms, 3 full bathrooms, 1 half bathroom, eat-in kitchen with a large center island, granite/quartz countertops, SS Appliances, double wall ovens, wine fridge, gas cooktop, mudroom with pantry, family room with gas fireplace, living room, dining room, office/study, hardwood floors, crown molding, raised panel molding, primary bedroom with en-suite bathroom, large soaking tub, walk-in closets, 4 additional large bedrooms, and laundry room. 2 car garage, full basement with 9ft. ceilings, egress window and 2 entrances. Taxes to be determined. Currently offering two models, The Villager and The Gazebo. Nestled in the heart of Smithtown, This stunning development promises luxurious living and convenient access to various amenities, including shopping, dining, schools, and recreational facilities. With easy access to major transportation routes, commuting and exploring the area is effortless. Enjoy privacy and tranquility in this exceptional newly built development. 200 amp service, 2 zone gas heat, central A/C, 75 gal. hot water heater, central vacuum, system. Don't miss the chance to establish roots in this remarkable neighborhood.

3 Greentree Court, Smithtown
$899,000
3 Beds ⋅ 3 Baths ⋅ 1023162 MLS
Welcome to this beautifully updated home, originally built in 2004 and thoughtfully enhanced with quality improvements throughout just 6 months ago . Taxes currently being grieved. Hearing all offers. Offering the perfect blend of modern updates and timeless comfort, this move-in-ready residence has had virtually everything replaced. Step inside to discover beautifully refinished hardwood floors that add warmth and elegance throughout the home. Enjoy peace of mind with all-new plumbing throughout, a brand-new roof just five months old, and a full suite of appliances that are only three months old. Each of the home's three bathrooms has been exquisitely remodeled just 5 months ago, using premium, top-of-the-line materials, creating luxurious spaces designed for everyday comfort. Additional highlights include in ground sprinklers, 200 amp electric, new high-hat lighting, efficient natural gas heating and hot water, central a/c, new paint, crown molding, along with a spacious two-car detached garage offering exceptional storage, workspace, or room for your favorite hobbies. Nestled on a quiet dead-end street and fully fenced within a highly sought-after school district, this home provides the perfect setting for peaceful living while remaining centrally located to shopping, dining, and the Long Island Rail Road just 1.6 miles away, making daily commuting both easy and convenient. Outdoor enthusiasts will appreciate the abundance of nearby recreational opportunities. Spend weekends exploring the scenic trails, fishing, or cross-country skiing at Caleb Smith State Park Preserve. Enjoy kayaking, river access, and a playground at Landing Avenue Park, or take advantage of the outstanding athletic facilities at Robert A. Brady Park, featuring baseball and softball fields, tennis and basketball courts, volleyball, and a roller hockey rink. With exceptional updates, an unbeatable location, this remarkable home presents a wonderful opportunity to enjoy modern living in an established neighborhood. Simply unpack and start making memories!

38 Hallock Avenue, Smithtown
$1,890,000
4 Beds ⋅ 4 Baths ⋅ 1022986 MLS
Exceptional custom-built estate nestled on over an acre in one of Kings Park’s most prestigious enclaves. Thoughtfully designed with approx. 4,000 sqft. of elegant living space, this residence blends timeless craftsmanship with modern luxury. From gracious entertaining spaces to beautifully appointed bedrooms.

12 Glenridge Lane, Kings Park
$649,000
2 Beds ⋅ 2 Baths ⋅ 1021169 MLS
Ground Floor Unit In Beautiful 55 + Fairfield At St James Community.All New Updated Unit,Move In Ready,Cul de sac Location,Added Privacy,High Ceilings,Natural Light,One Car Attached Garage,Private Patio With Sliding Doors,Primary Suite With Large Closets. Amenities Include Clubhouse, Pool,Tennis Court,And Fitness Center. No Pets Allowed Policy.

1205 Gotham Drive, Saint James
$1,250,000
6 Beds ⋅ 4 Baths ⋅ 1021652 MLS
Located in the in a highly desirable area of Smithtown sits this well maintained colonial…. Over 4000 sq ft of living area containing 6 true bedrooms, 3.5 bathrooms, a home office, a formal dining room, guest quarters (bedroom, full bath, living room) with a separate entrance, A sizable sitting room ( 18x25) containing a wood burning fire place, a separate living room and a wonderful screened in patio that can be accessed through the kitchen and the sitting room…. The landscaping of the home is just perfect!! Multiple sitting areas make it easy and fun to enjoy and entertain. A two car garage with electric car charging station, large driveway, close proximity to Town, LI Railroad and major highways just adds more value to this home.

10 Burham Drive, Smithtown
$2,499,000
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
$999,999
4 Beds ⋅ 3 Baths ⋅ 1017743 MLS
Nestled on a quiet cul-de-sac, this timeless Colonial offers the perfect blend of comfort, elegance, and privacy. Featuring 4 bedrooms and 2.5 baths, the home showcases warm wood flooring, abundant natural light, and a neutral palette throughout. he spacious kitchen is designed for both everyday living and entertaining, offering granite countertops, stainless steel appliances, ample prep space, and a tiered breakfast bar that keeps family and guests connected. Formal dining and living rooms each feature their own fireplace, creating inviting spaces for gatherings and quiet evenings alike. Outside, the private backyard is a true retreat. Backing directly onto parkland, the property enjoys exceptional privacy and features an inground pool surrounded by wrought iron fencing, beautiful paver patios, and multiple seating areas for relaxing or entertaining. Completing the package are a large garage, generous driveway parking, and storybook style curb appeal that makes a wonderful, lasting first impression.

14 Sandpiper Court, Smithtown
$950,000
4 Beds ⋅ 3 Baths ⋅ 1017406 MLS
Nestled on a sprawling and picturesque property in the heart of Smithtown, this whole house renovated in year 2022, 4-bedroom, 3-bathroom residence offers the perfect blend of privacy, space, and country-style living and very close the horse trails at Blydenburgh Park and minutes to Routes 347 & 454. Set on beautifully maintained grounds, the property features its own horse stable and equestrian facilities, making it an exceptional opportunity for horse enthusiasts, hobby farmers, or those seeking a peaceful retreat with endless possibilities. The charming home offers spacious living areas filled with natural light, generously sized bedrooms, and a flexible layout designed for comfortable everyday living. Outside, enjoy expansive open spaces, mature trees, and a tranquil setting rarely found on Long Island. A long private driveway provides ample parking and enhances the estate-like feel of the property. Whether you’re looking to enjoy horseback riding on your own property, simply embrace a lifestyle surrounded by nature, this one-of-a-kind Smithtown offering is not to be missed. Property Highlights: * 4 Bedrooms | 3 Full Bathrooms (2 bedroom 1 full bath on the first floor and 2 bedroom with 1 full bath located on the 2nd floor) * Recent updates: Oil Tank Replacement (2025) , Copper Pipes Installed (2026) * Private Horse Stable & Equestrian Facilities * Expansive Grounds with Open Space * Long Private Driveway with Ample Parking * High-end appliances (Wolf 36” six-burner range with pot filler, 42” paneled Sub-Zero refrigerator/freezer, Bosch ultra-quiet dishwasher, Sharp microwave drawer) * Conveniently Located Near the horse trails at Blydenburgh Park and minutes to Routes 347 & 454, easy access to Major Roadways.

45 Croft Lane, Smithtown
$3,575,000
6 Beds ⋅ 7 Baths ⋅ 1014535 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
$959,990
4 Beds ⋅ 3 Baths ⋅ 1015012 MLS
Welcome to this beautifully renovated Splanch. This move-in-ready home has been extensively updated inside and out, offering modern finishes, quality craftsmanship, and exceptional attention to detail throughout. The heart of the home is the brand-new kitchen, featuring new cabinetry, quartz countertops, a subway tile backsplash, stainless steel appliances, and a spacious 7' x 5' center island perfect for entertaining and everyday living. The home offers a versatile floor plan with a welcoming living room, dining room, and a spacious 13' x 20' room with the potential for a 5th bedroom, home office, or recreational space. The 13' x 15' primary bedroom features a brand-new 9.5' x 7' en-suite bathroom complete with a shower. The main bathroom, approximately 9' x 13', has also been completely renovated with beautiful new finishes and fixtures. A convenient half bath is located near the side outside entrance. The second-floor laundry area adds everyday convenience. Additional interior updates include refinished and stained hardwood floors, new interior doors, recessed lighting throughout, and fresh Benjamin Moore paint. Outside, you'll find impressive curb appeal with a new roof, siding, windows, front walkway, front entry door with sidelights, decorative columns, exterior crown molding accents above the windows, and two new garage doors with an opener. Sliding glass doors lead to a covered rear deck, creating the perfect space for outdoor entertaining. Additional improvements include a new central air conditioning system, upgraded electric, in-ground sprinklers, 6-inch gutters in the front, new converters, and an updated shed featuring a new roof, siding, windows, and electric. This truly turnkey home offers the perfect combination of style and comfort.. Just unpack and enjoy! Photos coming soon!!!

3 Barkley Lane, Nesconset
$950,000
4 Beds ⋅ 3 Baths ⋅ 1009532 MLS
Welcome to 19 Knoll Lane, Smithtown — Where Comfort Meets Elegance Nestled in the heart of Smithtown, this stunning 4-bedroom, 2.5-bath colonial is the home you've been waiting for. From the moment you step inside, you'll be captivated by the thoughtfully designed layout that perfectly balances everyday living with sophisticated entertaining. The spacious formal living room and formal dining room set the stage for memorable gatherings, while the warm and inviting den offers the perfect retreat for quiet evenings at home. The eat-in kitchen is ideal for casual meals and morning coffee alike. Rest easy knowing you're covered year-round with natural gas heat, central air conditioning, and a security system, ensuring comfort and peace of mind in every season. Step outside and discover your own private paradise. Unwind beneath the charming gazebo, host unforgettable evenings around the built-in fire pit, or simply soak in the tranquility of your beautifully appointed backyard. 19 Knoll Lane isn't just a house — it's the lifestyle you deserve. Don't miss your chance to call this exceptional property home!

19 Knoll Lane, Smithtown
$2,049,000
4 Beds ⋅ 4 Baths ⋅ 1014240 MLS
Exceptional Custom Estate in the Heart of St. James Proper, Situated on 1 Acre of Meticulously Maintained & Landscaped Property with a Resort Style Bucolic Yard. A Covered Front Porch leads into a Double Height Entry Foyer. Offering Four Bedrooms, Four Full Baths, a Family Room with Wood Burning Fireplace, Hardwood Floors, Built-ins & Custom Millwork Throughout. Private Den, First Floor Full Bath, Primary Ensuite with Two Walkin Closets, Propane Fireplace, Private Balcony & Custom Private Bath with Shower, Whirlpool Tub, Bidet & More. Three Additional Bedrooms on Second Floor & Brand-New Full Bathroom. Finished Basement 9' Ceilings with Custom Millwork, Outside Entrance, Custom Bar, Office, Full Bath, Movie Theatre & Much More. Bucolic Rear Yard Encompasses a Double Height Paver Patio, Outdoor Kitchen, Rear Awning, 35x35' Saltwater Heated Inground Pool with Waterfall, Covered Entertainment Area, Tennis Court with Pickleball & Basketball. Rear Stadium Lighting, Built-in Fireplace, Elevated Gazebo, Two Car Detached Garage & Rear Pool House Area. Four Car Garage Total. 400 Amp Electric. Two Zones CAC, two 275 Gallon Oil Tank in Basement. Central Vacuum, Low Line Septic, Built-in Fishtank. Mature Landscaping, Landscape Lighting, Architectural Roof, Pool Table & Much More. Must See to Appreciate. All information to be verified independently by Buyer/Agent. Inquire About CO's.

67 Sunny Road, Saint James
$799,000
4 Beds ⋅ 2 Baths ⋅ 1013005 MLS
Welcome To 10 Curlin Lane, A Completely Gut-Renovated 4 Bedroom 2 Full Bathroom Colonial Offering The Perfect Blend Of Modern Design, Comfort, And Convenience In The Heart Of St. James. This Stunning Home Has Been Thoughtfully Redesigned From Top To Bottom With Today’s Buyer In Mind. The Brand-New Kitchen Showcases Elegant White Maple Cabinetry With Crown Moulding And Custom Lighting, Sleek Quartz Countertops, A Custom Tile Backsplash, And Stainless Steel Appliances—Creating A Clean, Sophisticated Space Ideal For Both Everyday Living And Entertaining. Throughout The Home, You’ll Find A Seamless Combination Of Large-Format Tile And Rich Hardwood Flooring, Complemented By Recessed LED Lighting That Enhances The Bright, Open Feel. Both Full Bathrooms Have Been Beautifully Customized With Custom Tile And Quartz Finishes, Delivering A Spa-Like Experience. Major Upgrades Provide Peace Of Mind, Including A New Roof, Cedar Shake Vinyl Siding, Windows, 200 Amp Electric Service And New Heating And Cooling HVAC Systems. Additional Conveniences Include A Stackable Washer/Dryer And Flexible First-Floor Bedroom With Generous Closet Space—Perfect For Guests, Home Office Use, Or Multi-Generational Living, And A Finished Lower Level For Playroom, Media Room, Or Creative Space. Step Outside Through Sliding Doors Off The Dining Area To A Convenient Patio And Fully Fenced Quarter-Acre Backyard With Shed, Offering Ample Space For Outdoor Gatherings, Recreation, Or Future Enhancements. A Single-Car Garage Completes The Package. Ideally Located Less Than A Mile From The St. James LIRR Station And Just Minutes From Shopping, Top Tier Dining, And All The Amenities Of The Smith Haven Mall, This Home Delivers Both Lifestyle And Location. A True Turnkey Opportunity—Simply Unpack And Enjoy.

10 Curlin Lane, Saint James
$649,000
3 Beds ⋅ 2 Baths ⋅ 1012238 MLS
Welcome to this beautiful, totally renovated expanded Cape offering the perfect blend of style, comfort, and functionality! This move-in-ready home features 4 spacious bedrooms, 2 full bathrooms, and a bright, open layout filled with natural light. The updated interior showcases modern finishes throughout, making it easy to simply drop your bags and move right in. Enjoy a full basement with outside entrance, providing endless possibilities for additional living space, storage, or recreation. Outside, you’ll find a detached 2-car garage, a beautiful, oversized side yard perfect for entertaining, gardening, or relaxing, and plenty of outdoor space to enjoy. A true turnkey home, don’t miss this incredible opportunity! Just unpack and start making memories...

44 Elizabeth Avenue, Smithtown
$1,150,000
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
$849,000
4 Beds ⋅ 2 Baths ⋅ 1005767 MLS
Expanded Ranch with Open Floor Plan, Huge Family Room with Pellet Fireplace Insert, 4 Bedrooms, 2 baths, Detached Heated 2 Car Garage, Gunite In Ground Salt Water Pool w/ Loop Loc Cover,150 Amp Service with Transfer Switch for Generator, Desirable Gas Heat, Central Air-5 Years Young, In Ground Sprinklers, Wood Floors, Attic Fan, Large Driveway, Smithtown Schools with HS West, New Stove, Granite Counters, Beautifully Landscaped and MORE !

25 Del Place, Hauppauge
$1,890,000
4 Beds ⋅ 3 Baths ⋅ 1008414 MLS
Welcome to this one-of-a-kind custom estate-quality residence rebuilt in 2018 by a professional contractor as his personal home with attention to detail and premium materials throughout. Situated on a private 1-acre property, this exceptional 4-bedroom, 2 1/2 bath home welcomes you with a striking stone façade and dramatic arched entryway that sets the tone for the extraordinary craftsmanship found throughout. Features include oak hardwood floors, solid hardwood interior doors, custom millwork, marble and tile mosaics, a custom detached 2-car garage with handcrafted garage doors built by the homeowner and features its own electrical panel. The fully finished basement includes an outside entrance, laundry area and epoxy flooring. The large, open kitchen includes custom cabinetry, granite countertops, stainless steel appliances, and custom designed tile work. A breathtaking handcrafted marble fireplace with carved lion statuary serves as the centerpiece of the home and features a heat-circulating system with dedicated venting to the primary suite above. Built with 2x6 construction and blown-in insulation for exceptional energy efficiency, the home was also strategically positioned above grade to promote superior drainage. Smart home features include remote thermostat controls with separate zones in each bedroom and an automatic leak-detection water shutoff system. Extending the living space outdoors, a covered patio overlooks the private grounds and is already pre-wired for cable and has a water line in place, providing a seamless opportunity to create the outdoor kitchen and entertainment area of your dreams. From the handcrafted architectural details to the thoughtful engineering and modern conveniences, no expense was spared in creating this truly exceptional residence. A rare opportunity to own a luxury home unlike anything else on the market.

225 Old Willets Path, Smithtown
$1,699,000
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
$1,626,000
5 Beds ⋅ 3 Baths ⋅ 1010107 MLS
Nestled at the end of a private long drive shared with only 2 other homes and Not directly on Landing, this magnificent custom brick home offering Luxurious living space on a private 1.2 acre setting. features include a dramatic two-story grand entry foyer with two staircases, soaring vaulted ceilings, gourmet chef's kitchen with cherry cabinetry, granite countertops and Viking appliances, especially including Sub-Zero refrigerator, hardwood floors throughout entire house. Master suite with radiant heated floors, spa-inspired primary suite, and beautiful views of preserved land, Designed for elegant entertaining and comfortable living with vaulted veiling and extra-large windows. Three high ceiling attached car garage with potential for double car lift storage. The full basement features high ceilings and a separate outside entrance, offering excellent potential for recreation, home office, gym, workshop or future finished living space. This exceptional residence combines timeless architecture, privacy. quite and premium craftsmanship.

589 Landing Avenue, Smithtown
$4,999,000
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
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
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
$749,000
5 Beds ⋅ 2 Baths ⋅ 956909 MLS
Great Hi Ranch with 2 Sep Living Areas plus Garage, Fenced Yard, Oversize Driveway, Smithtown Schools, Central Air

106 Summit Drive, Smithtown

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