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$879,000
4 Beds ⋅ 3 Baths ⋅ 1015936 MLS
Four Bedroom Two and Half Bath Brookfield Colonial with Two Car Attached Garage, Covered Front Porch, 16x32' Inground Pool & Paver Patio, with Fenced Rear Yard. Natural Gas Heat, 150 Amp Electric, Hardwood Floors, Tile & Wall-to-Wall Carpet. Step Down Rear Den with Woodburning Fireplace W/ Stove Insert. Updated Eat-in-Kitchen with Granite Tops & Stainless-Steel Appliances, Gas Cooktop. Formal Dining Room with Two Built-Ins & Hardwood Floors. Large Formal Living Room, Second Floor has Primary Bedroom with Two Closets, Makeup Area & Attached Updated En-Suite Bath. Updated Full Hall Bath & Three Bedrooms with Hardwood Floors. Belgian Block Lined Blacktop Driveway & Paver Front Walkway. Thru Wall AC Units. Inground Sprinklers, Shed & Gazebo are a Gift.

23 Hurtin Boulevard, Smithtown
$768,000
3 Beds ⋅ 3 Baths ⋅ 1013242 MLS
Move right in...76 Burlington Boulevard offers timeless modern comfort on one of Smithtown's most tranquil and sought-after neighborhoods in the Smithtown school district. This impeccably updated 3-bedroom, 3-full-bath residence showcases rich hardwood flooring throughout the spacious living room, formal dining room, and inviting family room, creating warm spaces for everyday living and entertaining. The thoughtfully designed layout is complemented by a very expansive, beautifully finished, lower level with designer tile flooring, offering exceptional flexibility and space for a media room, home office, play room, fitness studio, or guest retreat. A detached two-car garage with a low maintenance, long cement driveway and beautifully maintained property complete this exceptional offering. Ideally located just a few blocks from the vibrant shops, restaurants, cafes and everyday conveniences of downtown Smithtown, this home offers the perfect blend of tranquility and accessibility. Whether you're a growing family searching for a move-in-ready home or looking to downsize without sacrificing quality, space, or style, 76 Burlington Boulevard presents a rare opportunity to enjoy refined living in one of Smithtown's most sought-after locations.

76 Burlington Boulevard, Smithtown
$762,990
3 Beds ⋅ 2 Baths ⋅ 1015455 MLS
Disclaimer: Agent Owned Property Note: Some listing photos have been virtually staged 28 Dartmouth Drive sits in College Estates, one of Smithtown's most established neighborhoods. Quiet streets, strong neighbors, and one of Long Island's top-rated school districts right outside your door. The home has been thoughtfully maintained and strategically updated where it counts. The home received a full house-wide plumbing replacement and renovated primary bath in 2024, followed by a new furnace and water heater in 2025. While most homes in this price range and era are carrying decades-old systems, this one is not. The home is on natural gas service throughout. Inside, the main floor flows from a formal living room into a separate dining room, den, and eat-in kitchen, well-proportioned spaces filled with natural light from original Anderson windows. The south-facing front of the home draws sun through the main living spaces for most of the day. Hardwood floors and handcrafted wood finishes run throughout, giving the home a warmth and character that's hard to manufacture. Central air keeps things comfortable year round. A bonus room off the main living area works equally well as a home office or extra bedroom. The finished basement adds close to 1,000 square feet of additional space, suited for a home gym, media room, extended family setup, or serious storage. A Cambridge paver stoop greets you at the front entry and a one-car garage rounds out the package. The backyard is private and generous. A quarter-acre lot enclosed by mature trees with one beautiful old anchor tree at the center that gives the space a presence most yards don't have. Minutes to town beaches on the Nissequogue River, Avalon Nature Preserve, Stony Brook University Hospital, downtown Smithtown, and Port Jefferson village. Quick access to the LIE, Route 347, and the St. James LIRR station. Smithtown East school district.

28 Dartmouth Drive, Smithtown
$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
$679,000
3 Beds ⋅ 2 Baths ⋅ 1012925 MLS
Welcome to this beautifully renovated 3-bedroom, 1.5-bath ranch nestled in Smithtown and located within the Hauppauge School District. This move-in-ready home features an open-concept layout and was extensively updated in 2024. The stunning new kitchen is equipped with JennAir appliances and a Frigidaire Professional refrigerator, while Anderson windows provide abundant natural light throughout. A versatile bonus room offers endless possibilities. Additional updates include gas conversion, dual heating options, natural gas heat, and an energy-efficient heat pump system. A new roof with solar panels, and a partially finished basement that provides additional living, recreation, or storage space. The cesspool is approximately 5 years young. Conveniently located near shopping, restaurants, parks, transportation, and all that Smithtown has to offer, this home combines modern updates, energy efficiency, and everyday convenience in one exceptional package. Don’t miss the opportunity to make this turnkey home your own. Low Taxes!!! With star exemption: $10,567

39 Tanglewood Drive, Smithtown
$775,000
3 Beds ⋅ 3 Baths ⋅ 1014086 MLS
***Located in the desirable Smithtown Pines area and within the Hauppauge School District, this spacious 3-bedroom, 3-full-bath ranch is set high on a picturesque half-acre property and offers tremendous potential for customization.Spacious 3-bedroom, 3-full-bath ranch offers incredible potential and a flexible floor plan ready for your personal touch. Featuring vaulted ceilings and an open-concept layout, the kitchen flows seamlessly into the living room, where a fireplace serves as the centerpiece of the space. The home also offers a formal dining room and a separate family room, providing plenty of room for everyday living and entertaining. The full finished basement with outside separate entrance (OSE) adds valuable additional living space and presents endless possibilities for recreation, a home office, guest accommodations, or extended family. Set on a generous, elevated lot, the property boasts both an attached 2-car garage and a detached 2-car garage—an uncommon feature ideal for car enthusiasts, hobbyists, or those seeking ample storage and workspace. Create your dream residence in a desirable setting with great bones, abundant space, and exceptional potential. Bring your vision and make this property truly your own.

61 Ledgewood Drive, Smithtown
$499,999
3 Beds ⋅ 1 Baths ⋅ 1012679 MLS
Where can you find 1/2 AN ACRE OF FLAT PROPERTY at this price? Amazing opportunity to own a 3 bedroom, 1 bath ranch in a beautiful neighborhood in Smithtown! Perfect location - mid block on a quiet tree-lined street. 1 car garage, central air conditioning, full basement and private, park-like property that is hard to find! Come make this home your very own! Smithtown School District. Home sold as-is.

33 Summit Drive, Smithtown
$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
$680,000
3 Beds ⋅ 2 Baths ⋅ 1009540 MLS
Step into a piece of Smithtown history with this charming Colonial, where timeless character and thoughtful updates come together beautifully. Nestled on a picturesque half-acre property in North Smithtown, this 3-bedroom, 2-bath home offers warmth, personality, and the kind of craftsmanship that is hard to find. Inside, you’ll find an inviting foyer and living room highlighted by a cozy wood-burning fireplace and charming architectural details throughout. The formal dining room features beautiful built-in cabinetry and a bay window with stained glass accents. The country-style kitchen flows seamlessly into a comfortable den, creating the perfect gathering space for everyday living and entertaining. Stainless steel appliances and abundant natural light enhance the home’s welcoming feel. The main level also offers an additional room currently used as a home office, which could also serve as a laundry room, or flex room to suit a variety of needs. Three bedrooms are located on the second floor, and two full bathrooms provide convenience, with one located on each level. Recent updates and improvements include a gas conversion, newer burner, 200-amp electric service, and three split units that provide both heating and cooling. Outside, enjoy a private setting with mature landscaping, a fully fenced yard, a spacious driveway with brick accents, and curb appeal that perfectly complements the home’s historic character. A rare opportunity to own a home filled with charm, warmth, and modern conveniences. Conveniently located near Sweetbriar Nature Center, Landing Avenue Park, and the shops, restaurants, and amenities of Smithtown’s vibrant East Main Street. Taxes totaling $6,157.90 annually.

4 Landing Meadow Road, Smithtown
$749,999
3 Beds ⋅ 2 Baths ⋅ 1011658 MLS
Welcome to this beautifully renovated ranch that offers the perfect blend of comfort, style, and convenience. Featuring 3 bedrooms and 2 full bathrooms, this move-in-ready home showcases gleaming hardwood floors, an updated interior, and an inviting layout designed for everyday living and entertaining. The fully finished basement provides valuable additional living space, ideal for a family room, home office, gym, or guest area. Step outside to your private backyard oasis, complete with a pool, perfect for relaxing summer days and hosting gatherings with family and friends. Conveniently located near Smithtown's beautiful parks, beaches, shopping, dining, and major transportation routes, this home offers the lifestyle you've been looking for in one of Long Island's most desirable communities. A rare opportunity to make this move-in-ready Smithtown gem your own.

12 Sandalwood Drive, Smithtown
$899,000
3 Beds ⋅ 3 Baths ⋅ 1011789 MLS
Fall in Love with this Beautiful, Warm and Charming L Ranch Set on Private Cul de Sac, Spacious Rooms, Hardwood Floors throughout, All Andersens, Stone WoodBurning Fireplace, Custom Moldings and Recessed Lighting, Custom EIK and Built-Ins, Main Level Laundry, Huge Finished Basement, Economical Gas Hot Water Heating (4 Zones, 7 Years), HW Heater- 5 Years, Newer Roofing- One Layer-2 Years; Close to All Conveniences! Property Tax with Basic Star $15,231

7 Carrie Court, Smithtown
$1,099,999
5 Beds ⋅ 4 Baths ⋅ 1005651 MLS
Welcome to 54 Sandy Hollow, a beautifully maintained Brookfield Colonial located within the highly regarded Commack School District. This spacious home offers 5 bedrooms and 3.5 baths, featuring an open and versatile floor plan designed for both everyday living and entertaining. The heart of the home is the impressive kitchen, complete with a large eat-in area, expansive granite island, abundant cabinetry, and soaring ceilings that create a bright and inviting atmosphere. The flexible layout includes two primary suites—one conveniently located on the main level and another on the second floor—providing excellent options for extended living arrangements or guest accommodations. A partially finished basement offers additional living space, storage, and endless possibilities to suit your needs. The attached two-car garage adds convenience and functionality. Step outside to your own private backyard retreat, featuring a heated gunite in-ground swimming pool, generous outdoor living space, and mature landscaping that provides exceptional privacy. Perfect for relaxation or entertaining, this backyard oasis offers the comfort and tranquility you have been searching for. Conveniently located near shopping, dining, parks, and major transportation routes, this is a wonderful opportunity to enjoy all that Commack has to offer. Natural gas service and a whole-house generator provide efficiency, reliability, and peace of mind

54 Sandy Hollow Drive, Smithtown
$799,000
5 Beds ⋅ 2 Baths ⋅ 1002706 MLS
Welcome to this beautifully maintained move in ready Hi-ranch, nestled in the desirable Sherbrooke Drive section of Smithtown. This home offers 2800 sq. ft. of living space with 11 rooms and exceptional versatility. RARE BONUS: Legal Garage Conversion to a gorgeous suite that includes a bedroom, living room, walk in closet, bathroom, summer kitchen & two separate entrances! In addition, new separate ductless AC/heating unit for the suite. Just think of the possibilities you can utilize this addition for. The main level of this home offers huge kitchen with chef's Garland oven, full dining room, sun drenched living room, 3 bedrooms and bathroom, with hard wood oak under all carpeting. The lower level boasts a massive den with a working, wood burning, brick fireplace & additional room with a large closet (office/bedroom) Backyard has an exceptionally expansive deck with details such as built in benches and more. Large attic with easy access provides additional storage space. Must see this exceptional home to truly appreciate.

4 Sherbrooke Drive, Smithtown
$619,000
4 Beds ⋅ 3 Baths ⋅ 1011307 MLS
Location, Location, Location!! Opportunity knocks in the sought-after Forestwood section of Smithtown, one of the area's most coveted enclaves, set on a large lot. This 4-bedroom, 2.5-bath split ranch sits on a generous .60-acre corner lot and is available for the first time in over two decades. Offering approximately 1,612 square feet of living space, an attached garage, a wood-burning fireplace, and a full basement. Sold as-is, it is original throughout and ready for a buyer with vision to restore, reimagine, and build instant equity in a neighborhood where renovated homes command top dollar.

14 Mark Drive, Smithtown
$1,185,000
5 Beds ⋅ 3 Baths ⋅ 1010498 MLS
Welcome to your private retreat, where comfort, space, and timeless charm come together! Set on a beautifully landscaped .71 acre property, this spacious 5 bedroom, 2.5 bath home in the heart of Smithtown, nestled in the beautiful Forestwood section, offers the perfect blend of elegance, functionality, and outdoor living. Featuring gleaming hardwood floors throughout and a thoughtfully designed layout ideal for both everyday living and entertaining. The heart of the home is the beautiful eat-in-kitchen, featuring granite countertops, tons of cabinetry, and plenty of room for casual meals and conversation. For larger gatherings, the formal dining room provides a warm and inviting setting for holidays and special occasions. Relax in the spacious living room, unwind by the wood-burning fireplace in the cozy den, or enjoy movie nights and game days in the separate oversized family room. With five generously sized bedrooms, there’s plenty of space for family, guests, or a home office. Step outside and discover your own backyard oasis. Multiple decks extend the living space outdoors, creating the perfect setting for barbecues, celebrations, or quiet evenings under the stars. The inground freshwater pool invites you to enjoy summer days in style, while the lush gardens, colorful flowers, and mature plantings add beauty and tranquility year round. An amazing standout feature is the large 2 car barn in the backyard, ideal for hobbyists, gardeners, workshop space, extra storage, or parking additional vehicles. This incredible property offers the rare combination of indoor comfort, outdoor enjoyment, and versatile space, all in a setting that feels both welcoming and private. IGS, CAC, 150 Amps

28 Cygnet Drive, Smithtown
$735,000
3 Beds ⋅ 1 Baths ⋅ 1007779 MLS
Welcome to this charming 3-bedroom ranch nestled on a desirable block and backing directly to a peaceful greenbelt, offering added privacy. This home features an eat-in kitchen, formal dining room, spacious family room, and full basement providing additional recreation space. Additional features are central air and natural gas. Enjoy the fully fenced backyard, perfect for outdoor gatherings. A wonderful opportunity to own a home in a sought-after location! Low. Low. taxes. Conveniently located near shopping, parks, restaurants, and transportation.

43 Dale Lane, Smithtown
$500,000
3 Beds ⋅ 1 Baths ⋅ 1000285 MLS
This 3-bedroom, 1-bath ranch is located in the Smithtown Pines. This charming home has a living room, an eat-in kitchen, a den with a laundry closet, an office, three bedrooms, and a bathroom. Full unfinished basement. Other features are: 100 amp electrical service, one-car garage, central air, and flat.74 acres. This home is being sold in as-is condition with all contents of the home included. CASH ONLY DEAL. Probate Listing. Great opportunity in Smithtown Pines to make this house into your home. Smithtown Schools. Close to shops, restaurants, and an easy commute to highways.

20 Croft Lane, Smithtown
$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
$789,000
4 Beds ⋅ 3 Baths ⋅ 1002364 MLS
Welcome to this beautifully expanded Colonial nestled in the highly sought after College Section of Smithtown. This spacious 4 bedroom, 2.5 bath home offers the perfect blend of classic charm and modern updates. Step inside to discover gleaming hardwood floors, generously sized living spaces, and updated bathrooms designed with todays buyer in mind. The 372 square foot primary suite addition provides a wonderful retreat offering additional space and comfort rarely found in homes of this style. The thoughtfully designed floor plan is ideal for both everyday living and entertaining. A brand new roof (2025) and a young gas burner (2018) are just some of the improvements that provide peace of mind. Situated on .24 acre, enjoy a private backyard setting perfect for relaxing, gardening or hosting outdoor gatherings. A one car-garage, a full unfinished basement and muture landscaping complete the package . Located in one of Smithtowns most desired neighborhoods , this home offers convenient access to parks, shopping, restaurants, transportation all in Smithtown School District. With its spacious layout, desirable updates, and exceptional location, this is an opportunity you won't want to miss.

61 Hofstra Drive, Smithtown
$599,000
3 Beds ⋅ 2 Baths ⋅ 1008241 MLS
Charming and beautifully restored, this home seamlessly blends the character of its 1918 origins with today's modern conveniences. Taken down to the studs and completely renovated just four years ago, everything is like new while preserving its timeless curb appeal and old-world charm. Driveway repaved in 2023. Step inside to a bright, sun-filled interior featuring luxury vinyl flooring, central air conditioning, quartz countertops, stainless steel appliances, and an abundance of cabinetry. The spacious living room offers the perfect place to relax or entertain, while large windows flood the home with natural light. The first floor features a convenient bedroom and full bath, ideal for guests or one-level living. Upstairs, you'll find two additional bedrooms and another full bath. Enjoy outdoor living on the wood patio, perfect for morning coffee or evening gatherings. Conveniently located within walking distance to train station, shopping, restaurants, and all that Smithtown has to offer. A rare opportunity to own a fully renovated home with historic charm and modern style.

5 Hawkins Avenue, Smithtown
$780,000
3 Beds ⋅ 2 Baths ⋅ 996702 MLS
Don't miss out on this unique, fully updated 3-bedroom 2-full bath ranch property in the heart of Smithtown! Located on a private country lane, the landscaping and overall curb appeal of this property makes heads turn! Positioned only a few hundred yards from Main Street, you'll enjoy accessability to shops, eateries, the library, and Smithtown Historical Society grounds without even starting your car. Whether you are enjoying morning coffee made at your custom coffee station, or entertaining friends while preparing a meal in your outdoor kitchen, this home is made for relaxing and sharing good times with the people most important to you. For added convenience, you'll find the Smithtown train station to NYC only 1 mile away, Stony Brook University 5 miles, and pristine beaches only a 10 minute drive.

5 Judges Lane, Smithtown
$800,000
4 Beds ⋅ 3 Baths ⋅ 986502 MLS
.Welcome to this classic Smithtown Colonial set on a beautiful .66-acre property surrounded by mature trees and a peaceful, private setting. This 4-bedroom, 2.5-bath home offers generous living space, timeless charm, and plenty of opportunity to make it your own. A welcoming front porch leads inside to a spacious layout featuring a bright living room, formal gathering spaces, hardwood floors, and an updated kitchen with white cabinetry, stone-style countertops, stainless steel appliances, and a clean, modern feel. Upstairs, the home offers comfortable bedrooms with great natural light, including hardwood flooring in select rooms. The large property gives you room to relax, garden, entertain, or create the backyard you have been dreaming about. Located in the heart of Smithtown, close to parks, shops, dining, schools, and major roadways, this home combines privacy, convenience, and long-term potential in one of Smithtown’s most established neighborhoods. A tax grievance has been filed, offering potential savings for the next owner.

23 Whitney Gate, Smithtown
$849,900
4 Beds ⋅ 2 Baths ⋅ 1006953 MLS
Spacious 4/5 Bedroom Hi Ranch on Beautiful .52 Acres Flat Usable Yard. Lovely Landscape Framed with Trees and Greenery, Your Own Parklike Oasis with Heated In Ground Pool (New Heater and Liner). Hardwood Floors, Custom Moldings/Trim, Updated EIK/Granite and SS Appliances, Many Updated Windows, Recessed Lighting, Updated Single Layer Roofing, Newer Cesspool, New Bluestone Entry and Railing, Newer Heating System, In Ground Sprinklers, Outside Lighting, Circular Drive, Property Tax with Basic Star $11,726.08

118 Ledgewood Drive, 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
$899,000
4 Beds ⋅ 3 Baths ⋅ 1005004 MLS
Welcome to 17 Leslie Lane...a Beautifully updated Colonial Splanch nestled in a tree-lined neighborhood in Smithtown with Commack SD, this spacious home features 4 possibly 5 bedrooms and 2.5 Baths..Large Entry Foyer, Formal Dining Room, Expansive Kitchen with large Island..and Sitting/Den area with Fireplace and steps up to a Large Living Room, Gas Cooking and Heat, CAC. Hardwood Floors, Step outside to a Private Backyard with paver patio complete with a Salt Water/ Heated In-ground pool. This home has it all...all while conveniently located near shopping, restaurants, and Parks...make this your forever home!!

17 Leslie Lane, 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
$749,990
4 Beds ⋅ 2 Baths ⋅ 1002604 MLS
Welcome to 3 Bradley Court, a charming 4-bedroom, 2-bathroom Hi-Ranch residence nestled perfectly in a picturesque cul-de-sac in the Smithtown North section of Smithtown, NY. This home boasts an updated roof, windows, and vinyl siding, ensuring durability and low maintenance for years to come. Step inside to find gleaming hardwood floors throughout, creating a warm and inviting ambiance. The house comes with a spacious one-car garage, offering ample storage and convenience. The property's crown jewel is undoubtedly its expansive backyard. Imagine the joy of outdoor gatherings, barbecues, or simply enjoying a quiet cup of coffee on a sunny morning. The yard is equipped with an in-ground sprinkler system, keeping your green space lush and vibrant with minimal effort. Living in Smithtown North, you'll be a stone's throw away from the Smithtown Landing Country Club. Whether you're a golf enthusiast or simply enjoy a leisurely brunch, this local amenity adds to the charm of the area. The home is serviced by a 200-amp electrical service, providing ample power for all your appliances and devices. With taxes under $12,500, this residence offers value and comfort in one of Smithtown's most sought-after neighborhoods. Roof is only 9 years old.

3 Bradley Court, Smithtown
$1,200,000
3 Beds ⋅ 1 Baths ⋅ 1004569 MLS
Two Adjacent Lots in Sought-After Smithtown Pines on Over 2 Scenic Acres! Each lot is over 1 acre each. Lot 60 is vacant flat land. Lot 61 has a Well-maintained Retro Style Ranch home where buyers can enjoy the it's vintage charm w/ 3 Beds & 1.5 Baths w/ Full Basement w/Outside Entrance. Boasting Hardwood Floors throughout alongside a Bonus Recreational Room w/High ceilings surrounded in Knotty Pine Wood w/interior access to 1 Car Attached Garage. Rare Opportunity for Smart Builders/Investors w/ 3 Options: 1) Combine both lots & create one massive estate 2) Separate lots & create 2 luxury homes 3) Keep existing home & turn the 2nd acre into the backyard everyone wishes they had w/ pool, tennis court, guest house, etc. Request to view New Surveys. Lots are Taxed Separately. Being Sold Together.

37 Winston Drive, Smithtown
$549,999
3 Beds ⋅ 1 Baths ⋅ 1004798 MLS
Welcome to 27 Lindner Place, Smithtown! This completely move-in ready and fully updated 3-bedroom, 1-bath home offers the perfect blend of modern updates, comfort, and property space. Featuring a brand new kitchen with stylish finishes, updated interior throughout, and a spacious layout, this home is ready for its next owner to move right in and enjoy. Situated on a rare half-acre property, the oversized lot provides endless possibilities for entertaining, expansion, outdoor living, or simply enjoying your own private space. Even better, this home offers incredibly low taxes for the area, adding exceptional value and affordability. Conveniently located near shopping, parks, restaurants, and major roadways while still offering the charm and privacy of Smithtown living. Do not miss this opportunity to own your piece of Smithtown!

27 Lindner Place, Smithtown
$825,000
4 Beds ⋅ 3 Baths ⋅ 1004022 MLS
Tucked behind a classic front porch, this Craftsman-style colonial offers the perfect blend of timeless charm and modern peace of mind. Nearly rebuilt from the ground up in 2004—with updated framing, electrical, plumbing, insulation, and drywall—it lives like a newer home wrapped in character. A cozy den featuring Patagonian rosewood floors and a high end Jotul wood-burning stove overlooks the yard, creating a warm, inviting retreat. The second floor offers convenient hallway laundry and a primary suite with a newly renovated bathroom. A permanent staircase leads to a finished third-floor fourth bedroom—ideal for guests, work/office, or flexible living. Additional highlights include a finished basement with outside entrance, rear deck with retractable awning overlooking a flat/usable fenced yard, two-zone central air, 200-amp electric, solar panels, and efficient natural gas heating. Located just 0.3 miles from Smithtown Main Street, you’ll enjoy easy access to local restaurants, shops, LIRR, Brady Park, Millers Pond, and everyday conveniences while coming home to a peaceful residential setting. A rare blend of craftsmanship, smart upgrades, and location-driven lifestyle. Smithtown school district. Taxes 14,028.

75 Elm Avenue, Smithtown

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.