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$649,000
4 Beds ⋅ 3 Baths ⋅ 1047272 MLS
Opportunity Awaits in Smithtown! Situated on an expansive 0.75-acre property, this 4-bedroom, 3-bathroom home offers approximately 2,632 square feet of living space, generous room sizes, and a fireplace. The property requires extensive renovation and clean-out, presenting an ideal opportunity for an investor, contractor, or buyer ready to restore and transform the home. With its substantial footprint, impressive lot size, and desirable Smithtown location, this property offers tremendous potential for the right buyer. Bring your contractor and your vision! Property is being sold strictly AS-IS and will not be delivered broom-clean. The buyer will be responsible for removing all personal property, contents, and debris remaining at the property after closing. Buyers should perform their own due diligence regarding the property’s condition, permitted uses, and financing eligibility.

31 Ridge Road, Smithtown
$689,000
3 Beds ⋅ 1 Baths ⋅ 1046648 MLS
Move right into this beautifully updated Ranch where pride of ownership is evident throughout! Extensively renovated with comfort, efficiency and low-maintenance living in mind, this home features a beautifully updated kitchen with quartz countertops, gas cooking and modern appliances, along with updated electrical, plumbing and heating systems. Central air, motorized blinds and a reverse-osmosis drinking water system add to the home's comfort and convenience. Major exterior improvements include newer roof, siding and gutters, bluestone front steps and walkway, PVC fencing, inground sprinklers and an updated driveway. The insulated and finished garage offers additional versatility and is equipped with a subpanel suitable for electric vehicle charging. Additional electric service extends to the shed, while natural gas is also available for the dryer and outdoor BBQ. Thoughtful improvements inside and out make this a truly turn-key home—just unpack and enjoy all this house has to offer!

8 Gedney Avenue, Smithtown
$3,699,000
5 Beds ⋅ 8 Baths ⋅ 1037676 MLS
A Rare Opportunity to Create Your Custom Estate on Long Island Opportunities like this are exceptionally rare on Long Island. Set within one of the area’s most prestigious and private villages, this extraordinary new-construction estate offers the space, privacy and ability to customize that are increasingly difficult to find. Privately positioned on a breathtaking 2.35-acre wooded property with an additional one-acre private driveway, this impressive 7,000+ square-foot residence has been thoughtfully designed to combine timeless architecture with today’s most sought-after luxury amenities. Construction has progressed to the point where private tours can now be scheduled, while still offering the opportunity to personalize select finishes and make this remarkable home your own. A sweeping asphalt and stone driveway with cobblestone edging leads to the grand two-story traditional residence and oversized three-car garage. Inside, dramatic proportions immediately set the home apart, with a 20'6" two-story foyer and family room, 10-foot ceilings on the main level, a full 10-foot walk-out basement, and an elevator servicing all floors. The main level is designed for both everyday luxury and effortless entertaining. A spectacular chef’s kitchen features high-end Subzero separate refrigerator and freezer and Wolf appliances; subzero wine cabinetry and wet bar sub-zero, custom cabinetry with wood buildins, granite or quartz countertops, an expansive center island with prep sink, and radiant-heated porcelain floors. The soaring two-story family room is centered around a modern linear gas fireplace and coffered ceiling, while the formal dining room features custom built-ins and elegant millwork. A highly desirable **first-floor en suite** provides exceptional flexibility and convenience. The home also features a primary en suite wing along with 3 additional en-suite bedrooms, wide White Oak flooring, custom closet systems, radiant-heated floors, **two saunas and two steam showers**. Spa-inspired baths with premium Kohler fixtures complete the experience. Outdoor living is equally impressive. A covered rear porch with its own gas fireplace creates a beautiful setting for year-round entertaining, while a dedicated exterior-access full bathroom is ideal for a future pool. An in-ground pool is optional and may be customized to the buyer’s vision. The full 10-foot walk-out basement, complete with a full bathroom and outside entrance, offers tremendous possibilities for additional recreation, fitness, entertainment or guest space. Behind the beauty is equally impressive construction and infrastructure, including engineered wood-web floor joists, 400-amp electric service, natural gas, public water and seven oversized drywells. The home is also designed to accommodate a future generator and pool. Throughout the residence, wide White Oak hardwood floors, substantial moldings, custom millwork and an extra-wide staircase with open railings reflect the level of craftsmanship invested in every detail. More than a new home, this is an opportunity rarely available on Long Island: a newly built 7,000+ square-foot custom estate on exceptional acreage within an exclusive village — offering privacy, scale, luxury and the chance to make the finishing touches uniquely your own. *3D Reality Tours shown are examples of the builder’s previous work and are intended to demonstrate quality and craftsmanship; they do not depict this exact home.

550 Moriches Road, Head Of Harbor
$799,000
3 Beds ⋅ 3 Baths ⋅ 1026187 MLS
Magnificent Colonial features Entry foyer, Living rm, formal Dining rm currently used as a den, Eat in kitchen with Stainless steel appliances & plenty of cabinets, Laundry area with bonus closet space, 1st floor full bathroom. Bonus area on 1st floor currently used as a 4th bedrrom. 2nd floor features Large primary bedroom suite with a full bathroom & 2 additional s pacious bedrooms and 3rd updated Full baths. A Partial full basement with 2 crawl areas also. Backyard with mature trees for privacy.

21 Sailer Street, Saint James
$850,000
4 Beds ⋅ 3 Baths ⋅ 1044068 MLS
Beautiful Updated Colonial in a Quiet, Friendly Neighborhood This spacious Colonial home features a fully updated kitchen with a center island, seamlessly opening into a generous formal dining room and an airy living room. A warm and inviting family room with a brick fireplace adds charm and comfort, along with a convenient half bath on the main level. A slider door leads out to a large deck overlooking a fully fenced backyard, complete with an inground pool and slide — perfect for summer fun and entertaining. Upstairs, you’ll find the home’s private living spaces, while the property sits on a quiet, friendly, and picturesque street, close to all shopping, major highways, and transit options for easy commuting.

14 Format Lane, Smithtown
$759,000
4 Beds ⋅ 4 Baths ⋅ 1042725 MLS
Welcome to 23 Dale Lane! This well-maintained 4BR, 3.5BA multi-level home on .25 acre offers exceptional versatility for comfortable single-family or multigenerational living. The inviting entrance foyer leads upstairs to the living room, dining room and eat-in kitchen overlooking the lower-level den, featuring a wood-burning fireplace and sliding glass doors to a Trex deck and inviting in-ground pool. A powder room, laundry and utility rooms complete this level. Upstairs features a spacious primary ensuite with walk-in closet, two additional bedrooms and full bath. An open staircase off the entrance foyer leads to the lower level that offers a fourth ensuite bedroom, providing privacy and flexibility for guests or multigenerational living a versatile office, storage and recreation area with cabinetry, sink and private outside entrance. PVC fencing adds privacy. First and Second Level 1957 Sq. Feet and Lower Level with outside entrance 774 Sq. Feet Come see for yourself and fall in love!

23 Dale Lane, Smithtown
$759,900
4 Beds ⋅ 3 Baths ⋅ 1043024 MLS
Welcome to this spacious 4 bedroom with 2.5 baths Raised Ranch offering plenty of room to enjoy. This home boasts beautiful hardwood floors and a wood burning fireplace creating a warm and inviting atmosphere. The home features year-round comfort with gas heating and central A/C. The lower level has additional living space for entertainment with an outside entrance. The garage was converted to additional versatile living space. Step outside to your own backyard retreat featuring a deck and above ground pool which is perfect for relaxing on summer days. Ideally located in close proximity to Gaynor Park, schools, Lake Ave shopping and the train station for your convenience. This is a true dream to call home!

49 McKinley Street, Saint James
$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
$1,500,000
3 Beds ⋅ 3 Baths ⋅ 1040036 MLS
Elegant and Unique Colonial set on 2 Beautifully Landscaped Acres in the highly Sought After Village of Head of the Harbor. This Spacious Home Offers 3/4 Bedrooms. 3 Traditional Bedrooms Plus a Versatile Bonus Room That Can Easily Function as a 4th Bedroom. Generous-Size Principal Rooms Create an Inviting Layout for Everyday Living and Entertaining. The Home Features a Warm and Welcoming Living Room, a Formal Dining Room, and a Charming Den Highlighted by a Stunning Stone Fireplace. A Separate Study/Home Office Further Enhances This Home’s Valuable Versatility. The Updated Eat in Kitchen Provides Excellent Workspace and Views of the Serene Property. Additional Features Include: 2.5 Baths, Central Air Conditioning, a Full Finished Basement, 2 Car Garage, an Unfinished Walk-Up Attic with Vaulted Ceilings (see floorplan for dimensions), Spacious Deck Overlooking the Picturesque Grounds, Separate Hot Water Heater, Crown Molding, Numerous Updates, and a Comfortable, Functional Floor Plan Enhancing this Home’s Appeal. Set in a Premier North Shore Village Known for Privacy, Natural Beauty, and Convenience, this Property offers an Exceptional Lifestyle Opportunity.

1 Valleywood Court W, Head Of Harbor
$999,000
4 Beds ⋅ 4 Baths ⋅ 1041490 MLS
Great Cul De Sac Setting for this Center Hall Colonial, Spacious Rooms, Large Windows, Hardwood Floors, Hi Hats, Vaulted Bathrooms, Radiant Heat, Full Finished Basement, Refreshing Salt Lagoon Water Heated(Propane) Pool with Hot Tub, Central Vacuum, 200 Amp, Inground Sprinklers-8z, Fireplace and MORE !

11 Raphael Boulevard, Nesconset
$749,900
4 Beds ⋅ 3 Baths ⋅ 1042067 MLS
Located in the sought-after area of Smithtown with only one prior owner- this spacious 4-bedroom, 2.5-bath Colonial offers plenty of room to live, work, and entertain. Featuring beautiful hardwood flooring throughout, this home boasts a 2-car attached garage with two new electric doors. En-suite master offers a walk-in closet and tremendous space. The den is warm and inviting with a wood-burning fireplace, while newer windows throughout provide added comfort and efficiency. The first-floor laundry room includes a new washer and dryer for added convenience. Two high-efficiency ductless AC systems on the first floor provide cooling in the warmer months and supplemental heat when needed. The basement offers a large, versatile space with excellent storage potential. Near all shops and mins away from the LIRR-A wonderful opportunity to make this spacious Smithtown Colonial your next home!

22 Sheppard Lane Unit #B, Smithtown
$1,350,000
4 Beds ⋅ 4 Baths ⋅ 1041795 MLS
Spacious home on an equestrian estate (Horse property has small barn and tack room.) featuring handcrafted vaulted wood ceilings throughout and refined natural stone detailing. Guest suite with private bath, Situated within a private wooded landscape, surrounded by timeless natural beauty. Beautifully positioned windows frame breathtaking scenic views, with a private barn enjoying panoramic views. Three generous driveways and an impressive circular driveway enhance the estate-like setting. A truly exceptional property offering privacy, natural beauty, and timeless architectural character.

135 Oakside Drive, Smithtown
$749,990
3 Beds ⋅ 1 Baths ⋅ 1041719 MLS
Situated on a dead end street, nearly an acre of property in the heart of St. James, this unique 3-bedroom ranch offers space, versatility, and an incredible opportunity for horse lovers! The property is zoned for up to two horses and features a fully functional 12' x 26' barn with electricity—a standout feature! The property also includes an oversized 18' x 23' garage, providing plenty of additional space for vehicles, storage, a workshop, hobbies, or equipment. Inside, you'll find a charming and inviting home featuring a renovated kitchen, beautiful hardwood floors, and a stunning floor-to-ceiling indoor/outdoor fireplace that brings warmth and character to the living space. Enjoy the privacy and possibilities that come with having nearly an acre of land, all while being conveniently located in the heart of St. James. Whether you're an equestrian, need room for your hobbies and toys, or simply dream of having more property, this is a rare opportunity you won't want to miss!

4 Sunny Road, Saint James
$829,000
3 Beds ⋅ 4 Baths ⋅ 1041063 MLS
Welcome to 23 Willow Ridge Drive, A RARE CORNER, END UNIT in the desirable Willow Ridge community! Beautifully maintained and thoughtfully appointed, this exceptional home offers 3 bedrooms and 3.5 baths with an impressive blend of style, comfort, and convenience. The beautiful white kitchen features Thermador appliances, granite countertops, and heated floors, creating an inviting space for both everyday living and entertaining. Two gas fireplaces add warmth and character throughout the home. Upstairs, the newly updated primary bathroom offers a luxurious retreat with a free-standing Jacuzzi tub and heated floors. A conveniently located second-floor washer and dryer makes laundry a breeze, while two cedar closets provide thoughtful storage and a central vacuum system adds ease to everyday home maintenance. Enjoy seamless indoor-outdoor living from the first-floor balcony overlooking the spacious backyard—an ideal setting for relaxing or entertaining. A natural gas barbecue connection and convenient walk-out access make outdoor gatherings effortless. Exquisite custom blinds and beautiful lighting fixtures, including a stunning chandelier, add an elegant finishing touch throughout the home. The freshly painted interior create a clean, move in ready feel. Residents of Willow Ridge enjoy exceptional community amenities, including a heated pool, recreation room, and tennis and pickleball courts. With its desirable corner end-unit location, beautiful updates, luxurious details, and outstanding amenities, 23 Willow Ridge Drive is truly a special place to call home. Don’t miss the opportunity to make this exceptional property yours!

23 Willow Ridge Drive, Smithtown
$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
$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
$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
$1,395,000
4 Beds ⋅ 3 Baths ⋅ 1038256 MLS
A Coastal Setting That Makes Every Day Feel Like an Escape. Set on 1.74 beautifully private acres in a private beach community, this distinctive 4-bedroom, 3-bath home captures the relaxed rhythm of coastal living, surrounded by water views and beautiful natural surroundings, with easy access to town beaches and the marina. The property extends to Stony Brook Harbor, creating a peaceful natural backdrop, while mature plantings, gardens and a rare gunite in-ground pool enhance the sense of privacy and connection to the landscape. Inside, a light and bright open floor plan is defined by oversized windows and walls of glass that frame the surrounding beauty and bring nature into nearly every living space. The impressive great room takes full advantage of the setting with a dramatic wall of windows, vaulted ceilings and a stone wood-burning fireplace. Open to the dining room, this inviting space also features sliders to an expansive, updated Trex deck—a wonderful place for outdoor dining, entertaining or simply enjoying the views of Stony Brook Harbor. The spacious eat-in kitchen offers generous counter space, granite countertops, updated stainless steel appliances and a wonderful dinette area overlooking the pool and lush natural property. The primary bedroom suite provides a private retreat with a beautifully appointed ensuite bath featuring tumbled marble, a double vanity with granite counters, Jacuzzi tub and oversized shower with dual shower heads and multiple body sprays. Two additional generously sized bedrooms and a full bath with a custom vanity and granite countertop complete the second floor. Adding exceptional versatility, first-floor guest quarters with a separate private entrance and covered patio features a bedroom, full bathroom and living area, providing a comfortable and private space for guests or additional living space. The finished lower level offers even more room to gather and entertain, with wood floors, a comfortable den, wet bar and separate entry with direct access to the outdoors. Outdoors, the peaceful setting takes center stage. The rare gunite in-ground pool, surrounded by stone patios and complemented by a convenient changing room, creates an inviting place to spend summer days, entertain or simply relax amid the beautiful gardens and natural coastal plantings. Updated vinyl siding, a carport and ample driveway parking add everyday convenience. More than simply a home near the water, this is a property that embraces the character and ease of coastal living. With privacy, harbor views and the natural beauty of its 1.74-acre setting, every season offers another reason to enjoy being here—a coastal retreat that feels wonderfully removed from everyday life.

588 E. Long Beach Road, Nissequogue
$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
$1,498,000
5 Beds ⋅ 5 Baths ⋅ 1033980 MLS
Built in 2018, this custom Colonial offers approximately 4,300 square feet of thoughtfully designed living space on a beautifully landscaped 0.53-acre property within the prestigious gated community of Hamlet Estates in Saint James. Combining quality construction, modern energy-efficient design, and an exceptional floor plan, the residence features five bedrooms, four full bathrooms, one half bath, a three-car attached garage, and spacious interiors designed for comfortable everyday living and entertaining. The welcoming entry leads to bright, open living spaces highlighted by a dramatic family room with cathedral ceilings, creating an impressive sense of volume and natural light. Formal living and dining areas, a home office, and a first-floor guest suite provide flexibility for today's lifestyle, while the thoughtfully designed layout accommodates both daily living and large gatherings. The gourmet eat-in kitchen is appointed with custom cabinetry, granite countertops, stainless steel appliances, and generous workspace, making it equally suited for casual meals and entertaining. The adjoining family room serves as the heart of the home, while the expansive paved patio and professionally landscaped backyard offer serene views of a picturesque lake, creating a tranquil backdrop for seamless indoor-outdoor living. The primary suite offers a private retreat complete with a spa-inspired bath featuring a Jacuzzi tub, while a second primary-style suite on the first floor enhances the home's versatility for multigenerational living or long-term guests. The remaining bedrooms are generously sized and well served by the home's four-and-a-half-bath layout. Additional highlights include a full basement with approximately 10-foot ceilings offering exceptional finishing potential, ENERGY STAR-qualified construction and mechanical systems, insulated windows and doors, smart thermostat technology, central air conditioning, natural gas heating, central vacuum system and an attached three-car garage. These features combine to provide both long-term efficiency and modern comfort. Hamlet Estates is an exclusive gated community offering 24-hour guard-staffed security and an outstanding collection of resort-style amenities, including a clubhouse, outdoor swimming pool, fitness center, sauna, tennis courts, basketball court, putting green, paddle boats, and beautifully maintained common grounds. Residents also benefit from the highly regarded Smithtown Central School District, making this one of the area's premier luxury communities. HOA common charges apply.

29 Hamlet Woods Drive, Saint James
$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
$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
$635,000
3 Beds ⋅ 2 Baths ⋅ 1029446 MLS
Charming Ranch on Oversized Lot in Desirable St. James! Welcome home to this warm and inviting 3-bedroom, 2-bathroom Ranch nestled on an oversized property in the heart of St. James. Offering the ease of single-level living paired with incredible expansive outdoor space, this home is perfect for both relaxed daily living and effortless entertaining. Features Main Level with Bright, fluid layout featuring three comfortable bedrooms and one full bathroom. Finished Basement: with Additional finished space and 2nd Full Bathroom. Outdoor Oasis is Set on an unusually deep/large lot. Limitless potential for a pool, outdoor kitchen, or garden expansion. Prime St. James Location: Enjoy proximity to local shops, dining, top-rated schools, and convenient LIRR access. Don’t miss this rare combination of prime St. James property.

101 Lake Avenue, Saint James
$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
$699,999
3 Beds ⋅ 1 Baths ⋅ 1030650 MLS
Well maintained cozy ranch on tree lined street in Smithtown on .63 property with a detached garage. This home offers a formal living room, dining room, den, eat in kitchen, w/propane cooking as well as 3 bedrooms and 1 full bathroom. There are Anderson windows, hardwood floors in Living room.

42 Pineacre Drive, Smithtown
$800,000
4 Beds ⋅ 3 Baths ⋅ 1030391 MLS
Sprawling Smithtown Ranch on .52 Acre with Gunite Pool & 3-Car Garage! Space, flexibility and a backyard built for summer living come together in this distinctive 4-bedroom, 2.5-bath home set on a beautiful .52-acre property in the desirable Smithtown School District. Offering the ease and open feel of ranch-style living with a thoughtfully designed split-level bedroom wing, this home provides an exceptional layout for both everyday living and entertaining. A welcoming foyer opens to generously sized living spaces, including a formal living room, formal dining room, expansive den and a separate home office—ideal for working from home or creating a quiet flex space. The eat-in kitchen features granite countertops, stainless steel appliances and direct access to the deck, backyard and pool, making indoor-outdoor entertaining easy. Just a few steps above the main living area are four bedrooms and two full baths, creating separation and privacy without sacrificing the convenience of a ranch-style layout. The spacious primary suite features walk-in closets and a private bath with a sunken tub. The partially finished basement provides additional flexible space along with plenty of storage. Outside is where this property truly shines. Enjoy more than half an acre with a gunite inground pool and waterfall feature, a spacious deck for outdoor dining and entertaining, and an inground sprinkler system. A circular driveway and rare 3-car attached garage provide abundant parking and storage. Gas heat, central air conditioning and public sewer add to the home's everyday comfort and convenience. If you've been searching for generous living space, a private backyard retreat and an exceptionally versatile layout in the Smithtown School District, 29 Ivy Hill Drive deserves a closer look.

29 Ivy Hill Drive, Smithtown

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