Smithtown Real Estate

Welcome to Smithtown, New York, a charming town nestled in the heart of Suffolk County on Long Island. Known for its rich history and vibrant community, Smithtown offers the perfect blend of suburban tranquility and urban convenience. With its picturesque landscapes, top-rated schools, and a variety of recreational activities, it’s no wonder that families, young professionals, and retirees alike are drawn to this delightful area.

Smithtown boasts a unique heritage, dating back to the 1600s when it was first settled by the Smith family. Today, remnants of its storied past can be seen in the town’s historic landmarks and charming architecture. The town is renowned for its beautiful parks, including the expansive Blydenburgh County Park, where residents can enjoy hiking, fishing, and picnicking amidst stunning natural scenery.

In addition to its outdoor attractions, Smithtown is home to a vibrant downtown area filled with local shops, cafes, and restaurants that cater to every palate. Whether you’re in the mood for a cozy brunch spot or a lively dinner with friends, you’ll find plenty of options to satisfy your cravings.

Smithtown’s strong sense of community is evident in its numerous events and festivals held throughout the year, fostering connections among residents and creating lasting memories. With easy access to major highways and the Long Island Rail Road, commuting to New York City is a breeze, making it an ideal location for those who work in the city but desire the serenity of suburban living.

Discover the charm of Smithtown, where a warm community spirit and a wealth of amenities await you!

Newest Listings in Smithtown

$997,999

5 Beds ⋅ 4 Baths ⋅ 1045526 MLS

Exceptional Extra-Large, Charming Home with Resort-Style Backyard & Incredible Flexible Living Space...This is a WOW House with lots of character!!! Welcome to this truly special DIAMOND Cape-style, well maintained home, set on beautiful half-acre grounds and offering an impressive blend of quality craftsmanship, modern updates, and exceptional versatility; Quality details continue throughout this home with solid interior doors, hardwood floors in most of home, recessed lighting, and Sonos speakers on the first floor, custom blinds, "50 year roof", clapboard siding with maintenance free shingles, updated electric. This home offers much more than meets the eye, it offers multiple stunning living spaces with an oversized two-car garage, and an incredible backyard retreat ! The MAIN section of this large home features four bedrooms, 2 1/2 baths, and a finished basement with adorable summer kitchen, outside entrance and egress window creating wonderful flexibility for guests, recreation, hobbies, or extended living needs! Adding even more versatility is an ADDITIONAL living area on the main floor featuring another large eat-in kitchen, living room, full bathroom, office, and additional bedroom. Whether used for extended family, guests, a private workspace, or simply additional everyday living space, the possibilities here are endless. The beautifully updated main kitchen is a true highlight, featuring luxurious quartzite countertops, Thermador double ovens, and Bosch appliances overlooking a family room/den with built in shelving and hardwood floors. On the 2nd floor, the primary suite is complemented by a custom-designed closet offering exceptional organization and storage. There are 3 additional bedrooms with skylights and gorgeous full bathroom with mosaic tiles, built-in area in shower and multiple shower heads. Step outside and discover your own private backyard oasis. The custom built salt water, heated in-ground pool features a concrete wall, sun deck, built-in bench seating, and deck jets, creating a resort-like setting for summer entertaining and relaxation. Another feature here is the beautifully built deck providing additional outdoor living space, while the custom outdoor shower is perfect after a swim or simply enjoying the outdoors. The expansive half-acre property also features in-ground sprinklers and a custom shed with chicken run, adding charm and function to the beautifully maintained grounds. Enjoy the lifestyle close to everything you need and want, offering access to beautiful parks with hiking trails. kayaking, beaches, exceptional selection of restaurants, boutiques, LIRR....

351 Forest Lane, Smithtown

$280,000

1 Beds ⋅ 1 Baths ⋅ 1049471 MLS

Fantastic Opportunity to Own! Why rent when you can buy in Smithtown's Award winning School District. This Updated Corner Unit Has Hard Oak Flooring, Granite Countertops, Stainless Appliances, New Wall AC units, Laundry on site and Large Rooms with Plenty of Closet Space ..

355 Route 111 Unit #30 Route 111 Unit #30, Smithtown

$1,199,000

5 Beds ⋅ 4 Baths ⋅ 1049096 MLS

Welcome to this beautiful & Spacious 5 Bedroom Colonial, ideally situated on a cul de sac & offering 3301Sq Ft of living space ,not including the full basement. From the moment you enter you will appriciate the generous room sizes, beautiful oak floors and the comfortable flow throughout this impressive home. The granite Kitchen is designed for both everyday living and entertaining featuring a center island,ample cabinetry,and a covienient butlers pantry. A warm inviting wood burning fireplace creates a perfect setting for relaxing evenings at home. Step outside and discover your own private backyard oasis. Enjoy the oversized paver patio, perfect for outdoor dining and entertaining overlooking the beautiful heated saltwater inground pool. The basement provides valuble additional space and features an outside entrance offering endless possibilties. With aprroximately 3301 sq ft of living space, a Cul de sac location, this home offers the space,comfort and lifestyle you have been looking for !

5 Keystone Court, Smithtown

$1,625,000

5 Beds ⋅ 4 Baths ⋅ 1048862 MLS

Welcome to 40 Friendly Rd. A home that redefines style, comfort, and convenience. This turn-key, fully renovated property combined luxury and functionality flawlessly. The exterior showcases a perfect blend of brick, Azek facade and oversized Andersen windows exuding a modern yet timeless appeal. As you step inside, you are greeted by a two-story entry foyer with a grand chandelier and monorail/glass floating staircase. The open floor layouts on both floors provide a seamless flow from room to room, making it perfect for both entertaining and everyday living. The kitchen is a chef's dream, featuring custom 3/4" solid white oak and black glass cabinets, custom quartz hood, Viking appliances with a 6-burner stove, and a double island set up. The hidden walk-in butler's pantry offers plenty of storage and adds a touch of luxury. Kitchen flows into a vaulted ceiling family room with a large concrete fireplace which leads to an oversized Trex deck perfect for outdoor entertaining. The property boasts five bedrooms and three and a half well-appointed bathrooms. Custom millwork throughout with 9" wide plank wood flooring, 6" base moldings and a large wet bar on the first level. The home is equipped with a tankless Navien system and a York HVAC system, ensuring optimal comfort all year round. The meticulously landscaped outdoor area with 9 sprinkler zones and new sod provides a tranquil retreat, perfect for enjoying the outdoors. This home is located close to 347 allowing easy access to all local amenities. Whether you are looking for recreation, shopping centers or dining options, you'll find it all within easy reach.

40 Friendly Road, Smithtown

$855,000

4 Beds ⋅ 3 Baths ⋅ 1047477 MLS

Welcome to this beautifully appointed 4-bedroom, 2.5-bath Colonial, ideally situated in the highly desirable Royal Woods/Hillside neighborhood and within the acclaimed Smithtown School District. Freshly painted throughout, this inviting home offers a bright, move-in-ready feel from the moment you arrive. Sun-filled interiors showcase beautiful hardwood floors, cathedral ceiling, a charming bay window, and skylights that create an airy and welcoming atmosphere throughout the home. The spacious living area is anchored by a stunning floor-to-ceiling, full-wall granite wood-burning fireplace, creating an impressive focal point that brings warmth, character, and timeless elegance to the space. The well-appointed kitchen features stainless steel appliances just three years old, combining modern convenience with functionality. The spacious primary suite offers a private retreat, complete with a walk-in cedar closet and a full bath. Enjoy year-round comfort with a high-efficiency heat pump installed just one year ago, providing reliable heating and cooling. An oil-fired hot water heating system remains available as an additional heating option. Step outside and discover your own backyard sanctuary. The inviting inground pool features a one-year-old liner, steps, and pump, while the expansive stone-paver patio provides the perfect backdrop for outdoor entertainment, summer gatherings, or simply relaxing in your own peaceful outdoor escape. Ideally located near Smithtown beaches and Smithtown Landing Golf & Country Club, this exceptional home offers a wonderful combination of comfort, style, convenience, and lifestyle. With its spacious interiors, beautiful outdoor setting, and prime location, this is an opportunity not to be missed. Come make this special home your own!

22 Sheryl Crescent, Smithtown

$599,000

3 Beds ⋅ 3 Baths ⋅ 1048419 MLS

Welcome to 6 Valleywood Road in Smithtown. This 3-bedroom, 3-bath ranch offers the convenience of one-level living with nicely sized bedrooms and a functional layout. The basement provides additional space and flexibility, while the outdoor area offers plenty of opportunity to create a space that fits your needs. Located in a great Smithtown location, this home has lots of potential and is ready for you to make it your own.

6 Valleywood Road, Smithtown

$749,990

3 Beds ⋅ 2 Baths ⋅ 1047017 MLS

Welcome to 5 Kenny Street, a charming ranch-style home nestled in the heart of Smithtown. This delightful residence boasts three comfortable bedrooms and two full bathrooms, ensuring ample space for all. Upon arrival, you are greeted by the home's impressive curb appeal, set on a generous .34-acre flat parcel. Inside, discover the hidden treasure of hardwood floors beneath the carpeting, preserved for years and ready to shine. The home is equipped with central air conditioning, an updated heating system, and a modern hot water heater for your comfort. Recessed lighting is throughout the house. The spacious living room invites relaxation, while the separate den, enhanced with a cozy gas fireplace, provides an intimate retreat. The kitchen shines with updated stainless steel appliances, a vaulted ceiling with a skylight, and a convenient formal dining room stands ready for your meals and gatherings. The primary bedroom offers the luxury of an ensuite bathroom. The second full bathroom has a skylit vaulted ceiling. This beautiful home has a two-car garage with electric openers, a partially finished large basement with ample storage, and a laundry area adds to the home's practical appeal. Outside, a low-maintenance Trex deck overlooks the picturesque backyard, an ideal spot for outdoor enjoyment. There is an in ground sprinkler system in the front and back yard. The backyard is very private. This home's location is a gem, with easy access to major highways, public transportation, and shopping venues. Welcome to your future home, where convenience meets charm in Smithtown and within the Smithtown School District.

5 Kenny Street, Smithtown

$759,000

4 Beds ⋅ 2 Baths ⋅ 1046723 MLS

Welcome to this charming home located in Smithtown, within the award-winning Commack School District! This property offers a comfortable and functional layout featuring a formal living room with crown moldings and ceiling fan, formal dining room with built-in cabinetry and wine storage, perfect for entertaining and sliding glass door to exterior. The kitchen is equipped with stainless steel appliances, wood-finish cabinetry, tiled flooring and provides a great space for everyday living. The home offers 4 bedrooms and 2 full bathrooms, providing plenty of space for guests. A full basement, partially finished, adds valuable additional living and storage space and includes a washer and dryer. Additional features include oil heating, two thermostats for temperature control, a one-car garage, expansive rear Trex deck overlooking the backyard—ideal for outdoor relaxation and entertaining. Expansive back yard with mature trees providing natural privacy. The property is being sold AS IS. Don’t miss the opportunity to make this Smithtown home your own!

90 Cornell Drive, Smithtown

$699,999

3 Beds ⋅ 2 Baths ⋅ 1048457 MLS

Welcome to this beautifully maintained split-ranch home nestled in the highly sought-after East Hills Estates of Smithtown. This 3 bedroom, 2 bath, 1 car garage on 0.3 acres home (currently set up as two bedrooms, can be easily put back to three bedrooms) is filled with natural light and is move-in-ready! This residence offers the perfect blend of comfort, style, and functionality. The inviting main level features a bright and airy living room with soaring cathedral ceilings, a cozy gas fireplace, and an open flow into the eat-in kitchen featuring gas range, refrigerator, microwave, dishwasher (2023) and granite countertops, ideal for both everyday living and entertaining. Upstairs, you'll find a spacious primary bedroom with side-by-side double closets, a generously sized second bedroom, and full hall bath. The lower level offers a sun-filled den with abundant natural light, a full bathroom, laundry room and a convenient outside entrance, providing flexible living space perfect for guests, or a home office. 200-amp electric, Andersen windows, a cesspool with overflow (2021), vinyl fencing, separate hot water heater. and whole-house Generac generator. Situated on a tranquil .34-acre level lot, the private backyard is surrounded by mature specimen trees and lush landscaping and pond. With its mint condition, desirable location, and features, this exceptional home offers everything you are looking for.

1 Rutgers Street, Smithtown

$690,000

2 Beds ⋅ 3 Baths ⋅ 1035010 MLS

Welcome to Windcrest at Smithtown, a desirable pet-friendly, gated community offering maintenance-free, resort-style living! This beautifully renovated Brittany model townhome features 2 spacious bedrooms, 2.5 baths, and has been thoughtfully updated throughout. Freshly painted and move-in ready, the home showcases a renovated kitchen with white cabinetry, quartz countertops, and stainless-steel appliances. The renovated bathrooms offer a fresh, modern design, while the expansive primary suite features two custom walk-in closets and a private bath. Custom closet systems have also been added to the second bedroom, linen closet, and the finished basement for exceptional storage and organization. Additional upgrades include Andersen windows & glass door (approximately 4 years old), both furnaces 2024, hot water heater 2023 & Central Air Conditioning 2024 (both HVAC units), a natural gas fireplace with a marble surround and a one-car garage with a 240-volt EV charging outlet. The finished basement provides additional living space with multiple custom closets, while the redesigned private patio creates the perfect outdoor retreat. A private driveway adds additional parking. Enjoy resort-style amenities including a clubhouse with a card room, TV and sitting room with fireplace, outdoor swimming pool, tennis courts, pickleball, fitness center, and a gazebo overlooking a picturesque pond with a fountain. Conveniently located near shopping, dining, MacArthur Airport, and the LIRR, this exceptional home offers low-maintenance living with all the comforts of home.

26 Scarborough Drive, Smithtown

$875,000

3 Beds ⋅ 4 Baths ⋅ 1048487 MLS

Welcome to the Devonshire model at Willow Ridge, an impeccably maintained 3-bedroom, 3 and a half bath corner-unit condominium offering approximately 3,570 square feet of spacious living across three levels. Privately situated in one of the community’s most beautiful locations, this exceptional home overlooks a peaceful wooded area and offers a wonderful combination of privacy, comfort, and resort-style living. The main level features a spacious living room with soaring vaulted ceilings, creating an open and inviting atmosphere, along with a private primary ensuite complete with his-and-hers closets and a recently updated full bathroom. The main level also offers a convenient laundry room located directly off the garage. Step outside to the private balcony overlooking the wooded surroundings, complete with a retractable awning—an ideal spot for morning coffee, outdoor dining, or relaxing. The upper level features two additional generously sized bedrooms and a full bathroom, providing an ideal private space for family, guests, or a home office. The lower level offers additional flexible living space with two bonus rooms/bedrooms and a private patio, perfect for entertaining, recreation, or simply enjoying the tranquil setting. Additional features include gas heat, gas cooking, central air conditioning, and a home that has been lovingly cared for and meticulously maintained. Willow Ridge offers an array of amenities, including an in-ground pool, tennis courts, pickleball courts, and more. This beautifully situated Devonshire model offers generous living space, exceptional privacy, multiple outdoor areas, and the convenience of a premier community—all in desirable Smithtown on Long Island’s North Shore.

53 Willow Ridge Drive, Smithtown

$749,999

4 Beds ⋅ 2 Baths ⋅ 1044596 MLS

Super Clean Home that Features 4 Bedrooms, 1.5 Baths, Hardwood Floors, Anderson Windows thru-out, 2025 New Burner, Whole House water filtration system, Roof 2011, Granite EIK around 2018, Fireplace in Family Room, Pull Down-stairs for attic storage, 200 AMPS Electric, Expanded Driveway plus 2-Car Garage, Natural Gas in street already if you want to convert, Fenced Yard with Deck, Patio, Gardens, Shed for storage, and Low Maintenance yard to maintain. Taxes $12k per year, Need Smithtown Schools, then view this home located close to town.

6 North Avenue, 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.