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$674,999
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

$849,000
5 Beds 3 Baths 1040465 MLS
Offered for the first time in 46 years, 24 Gainsborough Road is ready for its next owners! This exceptional 5-bedroom, 2.5-bath Colonial is located in Holbrook’s sought-after New England Village and offers approximately 2,500 square feet of beautifully updated living space. Lovingly owned, meticulously maintained, and thoughtfully improved throughout the years, this home reflects true pride of ownership. Upon entry, the spacious living room flows into the newly renovated kitchen featuring stainless steel appliances, quartz countertops, white cabinetry, abundant storage and counter space, and a designated dining area. A large L-shaped island offers plenty of room to prep, serve, and gather. French doors from the dining area lead to the spacious sunroom with access to the backyard. Off the living room is a full bath, designated laundry room, first-floor primary bedroom with half-bath ensuite, and an additional bedroom. Upstairs offers another spacious primary bedroom with two walk-in closets, a full hall bath, and two additional bedrooms. Freshly painted throughout, the home features numerous updates including luxury vinyl flooring, carpeting, baseboards, crown molding and custom trim work, doors, fixtures, and hardware. Andersen windows, vaulted ceilings, skylights, and recessed lighting create a bright and airy feel. Storage is plentiful with attic space above both the second floor and garage, multiple walk-in and hall closets, and a shed. Additional features include oil heat, new oil tank, whole house fan, wall-mounted A/C units, and public sewers. Situated on a fully fenced .23-acre, park-like property backing a greenbelt, the outdoor space offers added privacy and plenty of room to enjoy. A three-level deck and gardens create an inviting setting for outdoor dining, entertaining, or relaxing. In-ground sprinklers service both the front and back yards. Enjoy all that Holbrook has to offer, with nearby attractions including the country club, shopping, dining, and convenient access to major roadways. Here, pride of ownership truly equals peace of mind. A lovely place to call home!

24 Gainsborough Road, Holbrook

$1,950,000
4 Beds 4 Baths 1039294 MLS
Welcome to 38 Riverview Terrace, an exceptional custom-built Colonial offering five bedrooms, three full bathrooms and one half bath, with an extensive array of high end finishes, entertainment spaces and resort-style outdoor amenities. A grand foyer welcomes you with wainscoting, chandelier and stunning maple hardwood flooring that continues throughout the first floor. The main level features an elegant formal dining room and a spacious den anchored by a wood-burning fireplace. The expansive eat-in chef’s kitchen is designed for both cooking and entertaining, featuring a large 7'10" center island, quartz countertops throughout, skylights, a breakfast area and modern farmhouse sink. High-end Sub-Zero and Wolf appliances include an eight-burner Wolf range with double ovens, a massive custom hood with pot filler, an additional wall oven, warming drawer, built-in microwave, ice maker and wine cooler. Radiant heated flooring completes the kitchen. A powder room with radiant heated flooring is conveniently located on the main level for guests, along with a dedicated first-floor laundry room. Upstairs, the spacious primary suite features an impressive custom walk-in closet and spa-inspired bath with a soaking tub, radiant heated flooring and heated towel rack. Four additional bedrooms and beautifully appointed bathrooms provide plenty of space throughout the home. Skylights throughout bring an abundance of natural light into the residence. The finished lower level is designed for recreation and entertainment, offering an expansive recreation area with a wet bar and dedicated media room/home theater with its own home entertainment system. The home is wired for seven televisions, while a Sonos sound system with outdoor speakers extends the entertainment outdoors. The backyard offers private country club style amenities, beginning with a spectacular heated in-ground pool with cascading waterfall surrounded by expansive armortec paving stones. Professionally landscaped grounds and dramatic landscape lighting create a beautiful setting for outdoor entertaining. A fully equipped outdoor kitchen with built-in grill, pergola and pavilion provide additional gathering spaces, while a pickleball court and basketball court offer recreation right at home. An attached two car garage completes this extensively appointed Smithtown residence, offering exceptional indoor and outdoor living with amenities designed for entertaining, recreation and everyday enjoyment.

38 Riverview Terrace, 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

$1,349,900
5 Beds 3 Baths 1039475 MLS
Luxury Living on a Private Cul-de-Sac Welcome to your dream home! Located in an exclusive 4-lot- subdivision on a private cul-de-sac, this stunning new construction Colonial-style residence offers an ideal blend of modern elegance, high-end finishes, and energy efficiency. With 4 -5 bedrooms and 3 full bathrooms, including an optional first-floor bedroom or office with full bath access, second floor laundry, this home is perfect for multi-generational living or flexible work-from-home needs, Interior Features, Gourmet Eat-in Kitchen featuring designer kitchen cabinetry, Center island with seating Quartz countertops $5,000 appliance package Living Room with soaring vaulted ceilings 9-foot ceilings on the first floor; 8-foot ceilings on the second floor and basement Tray ceilings add architectural elegance 6" White Oak hardwood flooring throughout the first floor and upstairs hallway — buyer’s choice of stain Elegant raised panel molding in the dining room and an upgraded larger molding package throughout Hi-hat recessed lighting package throughout the home Basement: Full-sized egress window for safety and natural light Walls are insulated for comfort and efficiency Full 8-foot ceilings — ideal for finishing or extra storage Systems & Efficiency: High-efficiency windows throughout 200 amp electrical service Electric Heat Pump with 2-zone Central A/C and Heating Built to Energy Star Standards for year-round comfort and lower utility bills Exterior Features: Beautiful cedar shake impression on the front elevation for timeless curb appeal Low-maintenance composite front porch — perfect for morning coffee or relaxing evenings Oversized garage with 8'x7' garage doors and plenty of extra space Asphalt driveway for durability and low maintenance Professionally designed landscaping package includes: Front and rear in-ground sprinklers Sod in the front yard and seeded lawn in the backyard Location Highlights: 2 homes already sold/occupied — join a small, desirable enclave Convenient to Smith Haven Mall, Ronkonkoma train station, parks, shopping, restaurants, and major roadways This thoughtfully designed Colonial is more than just a home — it’s a lifestyle. home in process of being built, If you need to sell your current home, this is a great opportunity—our timeline can accommodate that process, giving you the time you need to sell while preparing for your new home. I

3 Lotto Court, Lake Grove

$769,900
5 Beds 2 Baths 1039213 MLS
Welcome to 4 Halfcircle Drive, a beautifully appointed corner property in Holbrook offering an exceptional blend of indoor comfort and outdoor enjoyment. Set against a beautifully landscaped backdrop, the property features an impressive heated, saltwater in-ground pool, relaxing jacuzzi, charming gazebo, and convenient storage shed, creating an inviting outdoor setting for entertaining and enjoying the seasons. Inside, the spacious layout offers 5 bedrooms and 2 full bathrooms, complemented by a dedicated office/den, eat-in kitchen, formal dining room, and comfortable living room. Windows and siding are approximately 15 years young, adding to the home's appeal. Conveniently located approximately 8 minutes from the Ronkonkoma LIRR station and just minutes from the Long Island Expressway, this property combines a desirable Holbrook location with a versatile interior and an exceptional collection of outdoor amenities. A distinctive opportunity with plenty to appreciate both inside and out.

4 Halfcircle Drive, Holbrook

$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

$799,990
3 Beds 2 Baths 1037737 MLS
Welcome to this beautifully impeccably styled turnkey 3-Bedroom, 2- bath home on.23 acres professionally landscaped property with a 16x32 inground pool, gazebo and beautiful stonework patio. This home offers the perfect blend of modern style and effortless living. Thoughtfully updated throughout this sun-drenched home features a bright open layout which flows seamlessly from the living room into the open dining room, and kitchen. Three generous sized bedrooms- including a large primary bedroom with ample closet space and a beautifully updated full hall bath complete the main level. Enjoy the partially finished lower level with new carpeting which provides additional living space and a full bath. Whether you envision outdoor entertaining in your 16x32 inground pool or simply enjoy the privacy in your serene fenced in backyard- this is truly your next home!

116 Shenandoah Boulevard N, Nesconset

$1,649,000
5 Beds 4 Baths 1037441 MLS
Welcome to this beautiful 5 bedroom 3.5 Bath Colonial perfectly positioned on a quiet cul-de-sac set within Yellow Top Estates, a rare gated enclave of luxury single-family homes. From the covered front porch and beautiful paver and asphalt driveway to the 3-car garage, this home makes an incredible first impression. Enter inside to a dramatic two-story entry foyer with soaring ceilings, beautiful moldings and hardwood floors throughout. The spacious living room features custom built-ins surrounding a gas fireplace, creating the perfect place to gather and relax. The completely renovated kitchen is truly the heart of the home, featuring quartz countertops, a gas range, double ovens, wine fridge and plenty of space for entertaining. A private office or 5th bedroom is perfectly situated away from the main living areas, offering great flexibility for guests or working from home. Upstairs, the spacious primary suite is a true retreat with a beautifully appointed primary bath, including a soaking tub overlooking the backyard. And the backyard is where this home really shines. Designed for resort-style living, it features a freeform saltwater inground pool surrounded by beautiful pavers, an incredible outdoor kitchen with a gas grill, gas pizza oven, granite countertops and an oversized bar ready for summer BBQs and entertaining. A covered Trex deck offers the perfect spot to relax and enjoy the private setting, while a separate hot tub provides the perfect place to unwind and can be enjoyed year-round. Lovingly maintained, thoughtfully updated and ideally located within Yellow Top Estates. Don't miss this special home!

6 Hayloft Court, Smithtown

$829,000
5 Beds 4 Baths 1034957 MLS
Just Listed! One-of-a-Kind 5-Bedroom, 3.5-Bath Home in New England Village, Holbrook! This distinctive home offers spacious living areas, thoughtful updates, and a versatile layout designed for everyday living and entertaining. The first floor features beautiful tile flooring with radiant heat powered by oil, with individual thermostats in each room for customized comfort. The kitchen features granite countertops, an island, under-cabinet lighting, and new appliances, with an open-concept layout that flows seamlessly into the large dining room, featuring a wood-burning fireplace, and family room. Additional first-floor living spaces include a living room and den, along with an additional room that can be utilized as a bedroom, office, or flex space. A full bathroom and laundry room complete the first floor. Mini-split systems, approximately 4 years old, provide additional heating and cooling options. Upstairs, you'll find four generously sized bedrooms and two updated bathrooms featuring radiant heat. The spacious primary bedroom features a unique walk-in closet and a stunning ensuite bathroom with two separate vanities, a large shower with a built-in bench, and radiant-heated floors. A full attic with pull-down stairs provides additional storage. Outside, enjoy a heated semi-inground pool and a private backyard setting with no neighbor directly behind the property. The property also features an in-ground sprinkler system for convenient lawn maintenance. Underground utilities add to the convenience of this unique home. Centrally located near the LIRR, MacArthur Airport, major highways, schools, shopping, parks, and restaurants. Located within the Sachem School District. This exceptional home offers space, versatility, and distinctive features throughout.

73 Springmeadow Drive, Holbrook

$449,990
2 Beds 1 Baths 1035541 MLS
Don't miss this move-in ready 2-bedroom ranch in desirable Lake Grove! Renovated in 2018, this home features an open floor plan, an updated kitchen with stainless steel appliances, recessed lighting, and central air conditioning (2024). Additional updates include a newer dryer (2024) and washer (2026). Set on a spacious lot, this property offers endless possibilities for expansion, creating the perfect opportunity to customize and grow with your needs. Outside, enjoy a 5-zone in-ground sprinkler system, a 10-foot-wide backyard access gate, and a large Shed (less than a year old). Conveniently located near shopping, dining, and major roadways, including Smith Haven Mall, this home combines comfort, convenience, and future potential in one exceptional package. True Taxes: $4,050.46 PLUS Lake Grove Village Tax: $710.91 Excluded from Sale: Ring Cameras

17 Connelly Drive, Lake Grove

$765,000
3 Beds 3 Baths 1036970 MLS
Welcome to Smithtown Pines! I am excited to share this beautifully maintained 3-Bedroom, 2.5-Bathroom Colonial home which was totally rebuilt from the foundation up in 2003 with a full basement. The exterior features a charming covered porch and a deep backyard complete with a large deck and a pond, perfect for outdoor relaxation. Inside, the first floor boasts a Living Room with a dual-sided gas fireplace that opens into the Dining area, which features sliding glass doors. The large Kitchen comes equipped with stainless steel appliances and leads to a convenient Mudroom featuring a stackable washer/dryer, a side entrance, and a half bath. The second floor offers a Primary Bedroom with two large closets and a spacious bathroom featuring a large Tuscan shower, alongside two additional generously sized bedrooms. Additional features include oil heat, an inground sprinkler system, and completed ductwork ready for central air conditioning.

149 Grassy Pond Drive S, Smithtown

$647,000
4 Beds 2 Baths 1035767 MLS
Incredible Opportunity! Welcome to this magnificent, sprawling expanded ranch, ideally situated mid-block in the highly desirable Village of Lake Grove! Completely renovated down to the studs in 2019, this impressive 4-bedroom, 2-bath residence offers an incredible combination of space, updates, versatility, and true one-level living. Set back from the road at the end of a long private driveway with abundant parking, the home immediately makes an impression with beautiful gray vinyl siding and an expansive backyard featuring a custom paver patio, perfect for outdoor entertaining. Step inside to discover a spectacular open-concept floor plan showcasing soaring vaulted ceilings, recessed lighting, skylights, and luxury laminate flooring. The spacious formal living room flows seamlessly into the dining area and beautifully appointed chef’s kitchen featuring white cabinetry, granite countertops, stainless steel appliances, and a large center island. One wing of the home offers three spacious bedrooms and a beautifully appointed full bath with a stand-up glass shower. What truly sets this home apart is its incredibly versatile expanded layout! A convenient mudroom off the kitchen features brand new washer and dryer and connects to the second wing of the home, which offers a spacious fourth bedroom, an additional den/great room, a beautiful spa-like full bath with tub and shower, and its own separate exterior entrance. This incredible additional living space provides tremendous flexibility for a home office, guest accommodations, recreation space, large lot or a variety of lifestyle needs. The home was extensively renovated in 2019 with major improvements including the roof, windows, vinyl siding, insulation, sheetrock, plumbing, electrical system with 200-amp service, doors, moldings, recessed lighting, flooring, kitchen, and baths. Additional features include a full basement with high ceilings and a Navien tankless gas heating system. Location completes the package with convenient access to major roadways, shopping, dining, Stony Brook University, Stony Brook University Hospital, Smith Haven Mall, LIRR transportation, and the growing Station Yards development. Completely renovated, incredibly spacious, and offering an exceptionally versatile layout, this is a tremendous opportunity to own an expanded ranch in the Village of Lake Grove!

899 Hawkins Avenue, Lake Grove

$589,000
2 Beds 3 Baths 1033652 MLS
Spectacular Townhouse Nestled in a private setting in "The Woods" Development in Blue Ribbon Smithtown School District features tasteful renovations throughout - A Decorators delight! Spacious living area perfect for entertaining. This Bright Chef's Kitchen with all the upgrades and stainless steel appliances is a show stopper. Formal Dining Room leads to oversized deck for additional entertaining space. Head upstairs to a luxury primary suite oasis complete with separate sitting room, balcony, walk in closets and ensuite. Additional second bedroom perfect for a home office or guest quarters. Amenities include Outdoor Pool, Fitness room/Gym, Tennis, Library, Clubhouse and plenty of activities for all ages. Woof/Meow - pets welcome!........ Amended Special Assessment Based on the finalized loan terms, the amended special assessment will be: • $470 per month per homeowner • Effective: September 1, 2026 • First Payment Due: September 1, 2026 • The assessment will remain in effect through August 2036, consistent with the 10-year loan term.

5 Jeremy Circle, Nesconset

$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

$799,000
4 Beds 2 Baths 1033876 MLS
Welcome to this newly renovated, expansive ranch nestled in the Village of Lake Grove! Set on an incredible 1.5-acre property with potential for horse enthusiasts, this one-of-a-kind home offers a thoughtfully designed layout that perfectly balances space, comfort, and privacy. The private primary suite is tucked away on its own wing and features a soaring cathedral ceiling, generous closet space, and a beautifully appointed en suite bath, creating a true retreat. A second bedroom on this side of the home offers access to a spacious unfinished attic bonus room—ideal for a playroom, home office, studio, or additional storage. On the opposite wing, two additional bedrooms provide separation and privacy. The heart of the home is the open-concept kitchen, complete with stainless steel appliances, a dining area, and seamless flow into the living spaces. Enjoy cozy evenings by either of the two wood-burning fireplaces, while new luxury vinyl flooring and fresh paint throughout give the home a modern, move-in-ready feel. In addition, a large finished basement with ample room to enjoy and an outside entrance. Additional highlights include a newer roof, brand newer boiler, new bath, central vacuum, in-ground sprinklers, an oversized two-car garage, and a circular driveway that offers convenience and ample parking. 200 amp electric plus 2 sub panels, reverse osmosis water at kitchen sink. Brand new luxury vinyl plank flooring, entire house freshly painted, recessed lighting, hardwood floors in 2 bedrooms. A rare opportunity to own a beautifully updated ranch on a sprawling property with endless possibilities—whether you're dreaming of room to roam, space for horses, or simply enjoying the privacy of this exceptional setting. This is a home you won't want to miss!

117 Hallock Road, Lake Grove

$650,000
3 Beds 3 Baths 1033514 MLS
Welcome to this spacious single-family home nestled on a quiet residential street in Brentwood. Offering approximately 1,774 square feet of living space on a generous 7,405-square-foot lot, this well-maintained home provides plenty of room for comfortable living both inside and out. The home features a finished basement, offering versatile space that can be used as a recreation room, home office, gym, or guest area. Energy-efficient solar panels help reduce utility costs while adding long-term value. Step outside to a spacious backyard with ample room for entertaining, gardening, or creating your own outdoor retreat. Conveniently located near schools, parks, shopping, dining, major roadways, and the Long Island Rail Road, this property offers the perfect combination of comfort, convenience, and efficiency. Don't miss this wonderful opportunity to make this Brentwood home your own.

103 Claywood Drive, Brentwood

$905,000
4 Beds 3 Baths 1032833 MLS
Pristine and sophisticated, this beautifully customized 4-bedroom, 2.5-bath ranch offers a spectacular open-concept design perfect for today's lifestyle. Originally built in the 1960s, the home has been thoughtfully updated over the years to reflect timeless elegance and exceptional craftsmanship. The stunning center island kitchen features a dramatic 7-foot black granite island, Sub-Zero refrigerator, Bosch dishwasher, GE appliances, under-counter microwave, and cooktop. Hardwood floors and custom built-ins enhance the home's warmth and character, while the spacious living and entertaining areas flow seamlessly to the rear deck for effortless indoor-outdoor living. A truly special home that is impeccably maintained and a must see.

22 S Lot Road, 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.