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$1,200,000
4 Beds 3 Baths 1009232 MLS
Welcome to 27 Winslow Lane... a Stunning Brookfield colonial with fresh updates and thoughtfully designed touches..........This home features a large entry foyer w/ an abundance of natural light, a generously sized formal living room, a formal dining room that opens into an updated EIK w/ gorgeous white cabinetry, Marble stone countertops and SS appliances, an inviting family room w/ built in cabinetry and wood burning fireplace. Upstairs you will find a primary ensuite w/ oversized WIC and a full double vanity bathroom, 3 additional spacious bedrooms and a newly finished full hall bathroom, the basement is finished also allowing for additional living space and ample storage!! Step out back to your Private Resort like country club yard and enjoy the Heated IG Pool, outdoor Kitchen area w/ BBQ, Pizza Oven, Beverage Refrigerator & A meticulously designed expansive paver patio! Additional features include.... Outside entertainment w/ lighting and sound system, Smart home w/ heat/AC, outdoor lighting, alarm system and more all easily controlled w/ an app! CAC (2 Zones – 2023), Oil Heat (3 Zones), 200 AMP Electric, Hardwood Flooring & Custom moldings throughout, Home surveillance/Security System, IGS (9 Zones) & flowerbeds with drip lines for easy gardening, Craftsman style porch columns w stone base, Vinyl Cedar Impression Shakes, Updated Anderson Windows, Custom paver Driveway, All this and so much more situated on over 1/3 of an acre of professionally landscaped property.... An absolutely gorgeous home in a beautiful neighborhood that will not last!

27 Winslow Lane, Smithtown

$1,200,000
3 Beds 3 Baths 1006718 MLS
Welcome to your private 1.09-acre retreat, offering the perfect blend of comfort, space, and outdoor living. This beautifully maintained home features wood flooring throughout the main living areas, with tile flooring in the foyer, bathrooms, and laundry room for added durability and convenience. The spacious primary suite is conveniently located on the first floor and includes a walk-in closet and a private en-suite bathroom that features radiant heated floors. An additional first-floor guest bathroom provides added convenience for family and visitors. The large den offers a warm and inviting atmosphere centered around a cozy fireplace, making it the perfect place to relax year-round. The expansive kitchen is designed for both everyday living and entertaining, featuring abundant cabinet storage and generous workspace. Adjacent to the kitchen, the dining room impresses with cathedral ceilings accented by stunning wood beams, creating a bright and elegant setting for gatherings. The laundry room comes complete with a washer and dryer and is neatly enclosed with bifold doors. This room also boasts a radiant heated floor. Upstairs, recent renovations have added modern functionality and charm, including custom built-in shelving in one room and a dedicated built-in TV entertainment area in another. The upstairs bathroom has been tastefully updated with subway tile and a sleek glass partition. Step outside to discover an entertainer's paradise. The backyard showcases a massive 40' x 21' composite deck, ideal for hosting large gatherings, barbecues, and outdoor dining. Beyond the deck, you'll find an expansive 42' x 49' pool area featuring a beautiful L-shaped pool, creating a resort-like setting right at home. The property also includes a large storage shed and is surrounded by a secluded, private yard that offers tranquility and plenty of room to enjoy the outdoors. Set on an impressive 1.09-acre lot, this exceptional property combines spacious indoor living with incredible outdoor amenities, making it the perfect place to call home.

30 Landing Meadow Road, Smithtown

$989,000
3 Beds 3 Baths 1003638 MLS
Welcome to this beautifully maintained, sprawling ranch nestled on a spectacular country club property at the end of a cul-de-sac. Designed for seamless modern living, this sun-drenched home features 3 spacious bedrooms, 3 full baths, and an effortless, flowing layout. The main level boasts a bright, inviting living room, a formal dining room, and a classic tile kitchen. Unwind in the cozy den, anchored by a charming wood-burning fireplace equipped with a brand-new chimney insert (2025). The Ultimate Primary Retreat, this luxurious primary suite serves as your own private sanctuary, highlighted by a dramatic atrium addition. Featuring floor-to-ceiling windows, this breathtaking space offers panoramic views of the magnificent backyard. Step outside into a vacation-at-home paradise, complete with meticulously landscaped grounds, a sparkling in-ground pool, a serene koi pond, and a tranquil, cascading waterfall. Roof & Structure (2025): Brand-new roof, upgraded insulation, floorboards, and 4 stunning, light-flooding skylights. Finished Basement (2024–2025): Fully finished lower level maximizing your entertaining and living space, complete with a commercial-grade industrial dehumidifier. Drainage & Landscaping (2022–2023): New driveway, robust retaining walls, property drains along the tree line, a French drain system, and a new sump pump. Power & Utilities: New backup generator (2023), underground propane tank, and a certified cesspool with overflow system. Premium Extras: High-end Anderson windows throughout and an updated front door. With its pristine infrastructure and resort-style backyard, this turnkey property perfectly blends premium suburban comfort with your own private vacation destination.

10 S Lot Road, Smithtown

$1,499,999
5 Beds 4 Baths 1005485 MLS
Welcome to 48 River Heights Drive where a tree lined street meets a true custom masterpiece in beautiful North Smithtown. This luxurious 4,800 sq ft home offers 5 bedrooms, 4 baths, a private office, and an incredible blend of high-end design, comfort, and functionality. Custom built, expanded, and fully renovated by the current owner, this home features Brazilian cherry and hardwood oak floors, Pella windows and doors, crown molding, a 400 amp electric service, 4-zone HVAC, central vacuum, full security system, indoor/outdoor Sonos audio, and smart wiring throughout. The heart of the home is the impressive 27x27 chef’s eat-in kitchen with custom cherry cabinetry, granite countertops, natural stone backsplash, a massive 13x5 granite island, high-end appliances, 2 dishwashers, 2 sinks, double ovens, and a butler’s pantry with additional refrigerator/freezer, sink, storage, and heated floors. The kitchen flows into a palatial 40x20 great room with a natural gas fireplace, built-ins, oversized sliders, and beautiful views of the backyard oasis. The 900 sq ft primary suite is a true retreat with soaring 13 ft ceilings, a spa-like bath, oversized shower, jacuzzi tub, double granite vanities, and a custom walk-in closet. Additional highlights include a second-floor dream laundry room with 2 washers, 2 gas dryers, granite folding counters, a custom office, spacious bedrooms, custom baths, and a newly finished basement completed in 2025. Set on a flat and private .52-acre property, the backyard is an entertainer’s dream with an in-ground pool, brand-new liner, granite coping, Italian porcelain pavers, sitting wall, gas fire pit, architectural columns, lighting, and beautiful outdoor living space. Located in the Smithtown Central School District and close to beaches, parks, golf, marinas, restaurants, and shops, this turnkey home offers luxury living inside and out.

48 River Heights Drive, Smithtown

$995,000
7 Beds 3 Baths 1001866 MLS
Calling all land lovers! Step into this beautiful Smithtown home exclusively located in the Village of the Branch! This move-in ready ranch carries 7 bedrooms & 3 full bathrooms with a brick walkway to the entrance, a wrap around driveway & a 2 car attached garage nestled on a whole 1 acre of beautiful land. Part the Smithtown School District, it is zoned for Mt. Pleasant Elementary School, Great Hollow Middle School & Smithtown High School West. With many newly renovated updates, this home is designed for both everyday living & entertaining. The remodeled kitchen is complete with 2 islands, stainless steel appliances, abundant cabinetry & an open flow ideal for gatherings. The high ceilings in the fireplace living room provide a spacious area to create memories in. Located next to the kitchen there is an additional fireplace in the bedroom that has an attached bathroom as well. A washer & dryer is installed into the laundry room, with a sink & exit to the 2 car garage. The home carries hardwood floors throughout. The remodeled bathrooms, new vinyl siding, new roof, & new gas burner throughout the home create a lovely cozy atmosphere. Step out on to the deck & enjoy the expansive backyard on flat land. A newly constructed spacious shed within a beautiful view supports endless possibilities for recreation or your own private retreat. With generous living space, thoughtful upgrades, & an amazing location, this exceptional ranch surely offers a place to call home. There are plenty of reasons to fall in love with this exceptional & rare opportunity right in the heart of Smithtown's Village of the Branch!

80 Mount Pleasant Road, Smithtown

$850,000
4 Beds 4 Baths 983050 MLS
Welcome to this beautifully maintained Colonial-style home, ideally located on a quiet cul-de-sac block in Smithtown, offering a desirable blend of privacy and accessibility and just moments from Robert A. Brady Park, Miller's Pond, and Blydenburgh County Park. This spacious residence features 4 bedrooms, 4 full bathrooms, a 2-car garage, and a fully finished basement with a separate outside entrance, providing exceptional flexibility and potential for a variety of living arrangements, recreation space, or extended use options with proper permits. The main level offers a well-designed layout including a formal living room with bay windows and dining room accented with elegant chair rail detailing, along with a comfortable den featuring a wood-burning fireplace and direct access to the garage. Hardwood flooring extends throughout much of the home, adding warmth and timeless appeal. The kitchen was thoughtfully updated approximately six years ago and features quartz countertops, stainless steel appliances, and tile backsplash. A standout extension enhances the space with a vaulted ceiling, two skylights, a bay windows, and expansive windows that fill the area with natural light, along with direct access to the backyard. This bright and airy setting is ideal for both everyday living and entertaining, with seamless flow to a Trex deck overlooking the yard. Upstairs, all four bedrooms are generously sized, including a primary suite with its own en-suite bathroom, offering a comfortable and private retreat. The backyard is designed for enjoyment, featuring a beautiful in-ground pool with built-in lighting, surrounded by a paver pool deck. The pool is equipped with a durable 28-gauge, 20-year liner that is approximately three years old, adding long-term value and peace of mind. Additional highlights include a covered front porch, a new blacktop driveway with paver border, and a generator hookup for added convenience. Blending thoughtful updates, generous living space, and a prime location near local parks and outdoor amenities, this home presents an exceptional opportunity to enjoy both comfort and lifestyle in Smithtown.

8 Whisper Lane, Smithtown

$1,250,000
5 Beds 4 Baths 975603 MLS
Welcome to this stately and impressive Colonial, ideally situated in one of Smithtown's most sought after and picturesque neighborhoods. This exceptional property offers a rare opportunity to create a custom luxury home in a truly premier setting. Boasting generous living space the home features a traditional and functional layout with a spacious Living Room, Dining Room, and inviting Den-perfect for everyday living and entertaining. The Kitchen with its Brazilian granite countertops offers generous space and serves as the perfect canvas to design the heart of your dream home. A beautiful feature of the home is a 280 ft expansive SunRoom extension, complete with hot tub, providing a unique space to unwind and relax all year long while overlooking the yard. Upstairs are 5 well appointed bedrooms including the Primary Bedroom with a huge ensuite full bathroom as well as an additional 1/2 bath. The backyard features a newly renovated 20x40 inground pool with new liner and all new coping (1 year old), and approx 3 year old filter, trex decking for low maintenance outdoor living, a beautiful pavillion to entertain under, and a gazebo. A 2 car garage, a young roof, an above ground 550 gallon oil tank, a 4 zone in-ground sprinklers, a tranquil rock waterfall, lightning rods and an expansive stone wall all around the front of the property. With its grand scale, coveted Smithtown location and proximity to the water, this is a rare find for someone to create a truly exceptional home in a prestigious neighborhood.

2 Three Pond Road, Smithtown

$2,599,000
6 Beds 8 Baths 952372 MLS
Paradise on the Nissequogue River with 65 feet of waterfront, ideal for canoeing, kayaking, and serene relaxation. This impressive 5,500+ sq ft contemporary with traditional accents offers 15 rooms and two fully separate living quarters, each with its own basement—perfect for extended or multi-generational living. Both residences feature updated granite eat-in kitchens with wood cabinetry and stainless-steel appliances, formal dining rooms, living and sitting rooms, and spacious primary suites with baths. Additional living space includes two additional bedrooms and a full bath, plus a lower-level spacious guest suite, entertainment rooms, abundant storage, and outside separate entrance (OSE) with its own designated parking. Set on 1.09 beautifully landscaped acres with specimen trees, brick patios, decks and exterior lighting, a spectacular salt water heated gunite in-ground pool (approx. 43’ x 25’) with waterfall, spa, lighting, and natural rock diving board—perfectly positioned to capture sweeping river views. Enjoy evenings by the wood-burning fire pit, surrounded by nautical wildlife and breathtaking sunsets. Located in the highly sought-after Smithtown community, close to fine dining, boutique shopping, theatre, mall, Caleb Smith Preserve, Sunken Meadow Park, beaches, golf, and Smithtown schools. Smithtown offers a blend of tranquil suburban life, historic charm and easy access to parkways and the LIRR/NYC. Additional Features: 2-car garage, North Wing: electric heat exchanger, CAC, heat/AC, South Wing: 3 mini-splits, 5-ton compressor, oil burner, forced hot air/CAC, 60-panel solar system (shared by both wings), In-ground sprinklers, Central vacuum, Two propane tanks, Two fireplaces (one gas, one wood-burning), Two separate hot water heaters, Additional electric panels, Laundry room with slop sink and storage, Brick patio with built-in BBQ

2 Riverview Terrace, Smithtown

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Listings courtesy of OneKey® MLS as distributed by MLS GRID. Based on information submitted to the MLS GRID as of . All data is obtained from various sources and may not have been verified by broker or MLS GRID. Supplied Open House Information is subject to change without notice. All information should be independently reviewed and verified for accuracy. Properties may or may not be listed by the office/agent presenting the information.

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