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$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
$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
$899,000
3 Beds ⋅ 2 Baths ⋅ 1047231 MLS
Welcome to 31 Dehan Street! A lovingly maintained three-bedroom, two-bathroom home with the flexibility for a fourth bedroom, inviting spaces designed for everyday comfort and located in one of the best school districts in town. Inside, hardwood floors flow through warm living areas featuring a wood-burning fireplace, formal dining room, granite countertops, Sub-Zero appliances, central air, and a partially finished basement. Step outside and discover the true showstopper: a beautifully level half-acre surrounded by mature, lush landscaping. Thoughtfully designed for relaxing and entertaining, the backyard offers generous lawn space, an awning, a wide sliding door, and utility connections for a motor home, hot tub, sauna, or Jacuzzi. A two-car attached garage and driveways from both Dehan and Leonard Streets provide exceptional convenience. With Andersen windows, updated mechanicals, and numerous thoughtful improvements, this is a home where comfort, beauty, and possibility come together.

31 Dehan Street, Smithtown
$738,000
3 Beds ⋅ 2 Baths ⋅ 1043090 MLS
WARMTH, COMFORT AND CHARM ON .56 ACRE OF MAGNIFICENT PROPERTY WITH LOW LOW TAXES Welcome to this expanded ranch in the sought after Smithtown School District. This home boasts a large, sunlit family room, hardwood floors, 3/4 bedrooms, a separate office/library room, newly renovated kitchen and baths and a large full finish basement with den, nanny's room, full bath, and storage galore, 2yr Burner Washer and Dryer. The oversized shy 2/3 acre property is a true backyard oasis with 1,000 sq ft of paver patios, a fire-pit, gazebo, pool, shed and PVC fencing. There’s also a separate area with outside entrance, perfect for extended family that come to visit. Taxes with Basic Star $10,515 Gas right on corner on Gilbert. Pool as gift

19 Ridgeley Road, Smithtown
$629,999
3 Beds ⋅ 2 Baths ⋅ 1043462 MLS
Welcome to this well-maintained 3-bedroom, 1.5-bathroom split ranch in Smithtown. The home features hardwood floors throughout and offers a comfortable and versatile layout. The kitchen was updated approximately 15 years ago, and the full bathroom was renovated within the past year. Additional features include a den, garage, fenced-in yard, 200-amp electric service, approximately 15-year-old roof, and an in-ground 5-zone sprinkler system. The fenced yard provides private outdoor space for a variety of uses. Conveniently located in Smithtown, this well-maintained home offers an opportunity to add your own personal touches and make it your own.

6 Sybil Place, Smithtown
$699,999
3 Beds ⋅ 2 Baths ⋅ 1040470 MLS
Location! Location! Location! Welcome to this beautifully refreshed split-level home, where style, comfort, and versatility comes together in one exceptional Smithtown offering. From the moment you arrive, the new driveway and freshly painted interiors with the cathedral ceiling sets the tone for a home that feels polished, inviting, and ready to enjoy. The home opens to a bright and thoughtfully designed layout offering 3 bedrooms and 2 full baths, with comfortable living spaces that transition effortlessly from everyday moments to entertaining family and friends. What truly sets this home apart is its versatile lower level with a separate entrance, creating exciting possibilities for extended living, a private home office, guest space, recreation area, or whatever best complements your lifestyle. Recent improvements add even more value and peace of mind, including a new gas burner and hot water heater, new dishwasher, and new washing machine. Go outside and enter the generous corner plot that provides the perfect backdrop for alfresco dining, summer gatherings, gardening, or simply unwinding at the end of the day. Thoughtfully updated, and filled with possibilities, this home delivers the space and flexibility today’s buyers are looking for, wrapped in a warm and beautifully presented home. With the top-rated Smithtown schools, and a neighborhood close to shopping, dining, highways and close to the train station, this is a special opportunity in Smithtown that deserves to be experienced in person.

23 Riviera Drive, Smithtown
$779,999
4 Beds ⋅ 2 Baths ⋅ 1036685 MLS
Welcome to this newly renovated 4 bedroom, 2 bathroom Expanded Cape home located in a desirable area of Smithtown, NY. The main level boasts a beautiful inviting living room with a bay window, designer molding, recessed lighting, new flooring, and sliders to backyard, an open concept kitchen with stainless steel appliances, dining area with sliders for quick access to backyard, 2 first floor bedrooms, an updated full bathroom and a laundry area. The second floor offers a very spacious, sun drenched primary bedroom with ensuite bathroom, high ceilings with skylights, plenty of closets, and an additional bedroom. The backyard has transformed into an entertainer’s paradise, featuring an in-ground pool with waterfall, an upgraded pool filtration system, in-ground sprinkles, a charming wooden deck, a large garage for storage, two sheds and a spacious workshop space in the back that creates a stunning outdoor space perfect for enjoying the warm summer days. Additional improvements include, a remodeled kitchen, two updated bathrooms, new flooring, recessed lighting and new doors, updated out siding, freshly painted interior walls, tree removals, yard leveling, new landscaping, and new pool filtration system. This property is in a PRIME location of Smithtown. Close to Smithtown LIRR train station, Main Street dining & shopping, Smithtown schools, Blydenburge County park, Caleb Smith State Park, Smithtown library, and many other amenities.

36 Fifty Acre Road S, Smithtown
$725,000
6 Beds ⋅ 2 Baths ⋅ 1038388 MLS
Welcome to this beautifully and completely updated expansive home in renowned Smithtown school district. This home is thoughtfully designed for modern living and multigenerational flexibility. The home features a private separate entry setup, ideal for an in-law suite, or extended family. The interior has been extensively updated with finishes throughout, including beautiful, refinished hardwood floors, and a sophisticated kitchen featuring quartz countertops. The spacious layout provides an abundance of room for entertaining, relaxing, and everyday living. Also, upstairs features two spacious walk-in closets Outside, enjoy multiple patios and decks that create exceptional outdoor living and entertaining spaces. Two separate driveways provide generous parking and added convenience the one driveway is shared adjoining with the neighboring property plus a huge separate private driveway on the other side of the property. In addition, the property is located on almost 1/2 acre. A rare combination of size, style, flexibility, and functionally, this exceptional property is ideal for buyers seeking a move in home with room for everyone.

653 Meadow Road, Smithtown
$679,000
3 Beds ⋅ 2 Baths ⋅ 1034437 MLS
Absolutley beautiful three-bedroom, two full bath cape situated on a generous lot in the heart of Smithtown. This move-in-ready home showcases a newer roof, stylish luxury vinyl plank flooring, a beautifully updated bathroom (2026), and a bright eat-in kitchen designed for both everyday living and entertaining. The flexible floor plan offers three spacious bedrooms and two full baths and a versatile loft space, providing plenty of room for family, guests, or a home office. The attractive board-and-batten vinyl siding adds timeless curb appeal and enhances the home's modern farmhouse charm. The oversized property offers endless possibilities for outdoor entertaining, gardening, recreation, or future expansion. Conveniently located near parks, shopping, restaurants, schools, and transportation, this beautifully updated home combines comfort, style, and convenience and is just waiting for its next owner.

22 South Avenue, Smithtown
$859,990
3 Beds ⋅ 2 Baths ⋅ 1031558 MLS
Set on 1.25 acres backing directly to the Nissequogue River Preserve this Sprawling Ranch offers a setting that is truly special. Protected woodland replaces neighboring homes, offering a peaceful backdrop where wildlife and changing seasons become part of everyday life. Inside, this inviting ranch features 3 bedrooms, 2 full baths, a farmhouse-inspired kitchen with breakfast nook, separate formal dining room, and beautiful hardwood floors throughout. The spacious family room is filled with natural light and anchored by a brick wood-burning fireplace with removable electric insert, while the formal living room showcases exposed wood beams and a wood-burning stove. Just off the primary suite, a sun-filled sitting room provides the perfect retreat to enjoy your morning coffee while taking in views of the surrounding landscape. Outside, enjoy summer days by the fenced 20x40 in-ground pool with a 2-year-old liner, or relax on the wood deck and brick patio surrounded by mature trees and the peaceful sights and sounds of nature. The fully permitted barn with attached carport and covered patio offers incredible versatility with potential uses including equestrian space, workshop, studio, home gym, or a cottage for extended family or rental income with proper permits. Additional features include a brand-new roof with flashed skylights, new gutters, propane service for cooking and laundry dryer, two-car attached garage, and a full unfinished basement with egress window offering even more possibilities. Conveniently located minutes from Blydenburgh County Park, Caleb Smith State Park Preserve, beaches, shopping, dining, and within the highly acclaimed Smithtown School District, this is a rare opportunity to enjoy the peace of a private setting while staying connected to everything Smithtown has to offer.

16 Landing Meadow Road, Smithtown
$699,990
4 Beds ⋅ 2 Baths ⋅ 1031895 MLS
Prime Location with Limitless Potential! ?Welcome to this spacious 4-bedroom home situated in a highly desirable neighborhood within the Smithtown Central School District. Offering a perfect canvas for your vision, this property boasts incredible potential for updates and customization. ?Key Highlights: ?Spacious Layout: 4 generously sized bedrooms ready for your personal touch. ?Prime Location: Minutes from local shopping, dining, parks, and schools. ?Outdoor Space: An expansive, completely flat backyard—ideal for entertaining, play, or adding a pool. ?Bring your vision and make this home your own!

4 Smithtown Crescent, Smithtown
$775,000
3 Beds ⋅ 2 Baths ⋅ 1031716 MLS
WHERE TIMELESS CHARM MEETS EXCEPTIONAL OPPORTUNITY. Discover the warmth, character, and enduring appeal of this beautifully maintained Colonial, ideally situated in one of Smithtown’s most desirable neighborhoods. Rich hardwood floors, an inviting fireplace, and flowing floor plan create an atmosphere that feels instantly like home. Offering three spacious bedrooms and one-and-a-half baths, this residence features a gracious living room with fireplace, Dining room, and eat-in Kitchen. The partially finished basement provides abundant storage while offering potential for additional living space. Step outside and experience a setting that feels straight from the pages of a storybook. Meandering stone pathways weave through mature landscaped gardens, leading to an expansive fenced backyard that invites summer gatherings, outdoor celebrations, or simply peaceful evenings surrounded by nature. Perfectly positioned on a quiet residential street, this exceptional home offers the tranquility buyers seek while remaining just minutes from the Long Island Expressway, Northern State Parkway, shopping, dining, and all that the Town of Smithtown has to offer—including its renowned parks, beaches, and recreational amenities. Whether you’re searching for your forever home or a rare opportunity in one of Long Island’s most sought-after communities, this residence offers the perfect blend of charm, comfort, location, and future potential.

20 Brook Lane, 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
$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

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.