Refine Search
Sort by
38 Landing Meadow Road, Smithtown
$3,995,000
7 Beds ⋅ 6 Baths ⋅ 1022766 MLS
Welcome to 38 Landing Meadow Road, Smithtown. Nestled on almost 23 picturesque and serene waterfront acres overlooking the renowned Nissequogue River this is a truly extraordinary North Shore retreat. Driving down the long private driveway your senses are alive to the possibilities of what is to appear. Surrounded by breathtaking natural beauty, the property includes agricultural land adjoining approx. 60 acres of protected preserve, creating an unmatched sense of privacy and tranquility. Wide open vistas, emerald lawns, magnificent mature trees and the grand nature of this idyllic scene are unmatched. Barns, stables, paddock, workshops, and multiple outbuildings provide endless possibilities for equestrian pursuits, farming, recreation, or creating your own private compound or purpose. This timeless Manor House built in 1828 offers nearly 6,000 square feet of living space, featuring 7 stately and spacious bedrooms and 6 bathrooms. The magnificent Estate is highlighted on the first floor by a warm and opening center hall with access to the rear property and patio, a formal living room, grand den with fireplace and the first floor is side property, den or library with a fireplace, truly formal dining room with a fireplace, an inviting eat-in kitchen designed for everyday living and entertaining and butlers pantry, family room or bedroom with a wet bar and two bathrooms. The charm and character of all of the rooms with so many original details of fireplace mantles and surrounds, stair mouldings and hardwood floors take you to another time. Besides the grand Manor home the property outside has an antique barn of approx. 7,500 square feet which offers the possibility of future use, and a caretakers suite inside. Also on the property is a “bank” barn with four 12x14’ horse stalls, a tack room and hayloft. Besides this barn is another smaller barn also with four 12x12’ horse stalls. On the grand 20 acre land preserve is extensive paddock and other fenced areas. Conveniently located near parks, golf clubs, beaches, wineries, charming villages, museums, and fine dining, this exceptional estate offers a rare opportunity to experience waterfront living at its finest. Walking in to this one-of-a-kind Estate you feel that 38 Landing Meadow Road Smithtown is a rare opportunity where history, nature and endless potential come together. Since the property adjoins multiple land preserve woodlands it ensures a forever-preserved backdrop and an exceptional North Shore lifestyle in which this legacy Estate can be yours and protected.

38 Landing Meadow Road, Smithtown

2 Riverview Terrace, Smithtown
$2,599,000
6 Beds ⋅ 8 Baths ⋅ 952372 MLS
Paradise on the Nissequogue River with 65 feet of waterfront, ideal for canoeing, kayaking, and serene relaxation. This impressive 5,500+ sq ft contemporary with traditional accents offers 15 rooms and two fully separate living quarters, each with its own basement—perfect for extended or multi-generational living. Both residences feature updated granite eat-in kitchens with wood cabinetry and stainless-steel appliances, formal dining rooms, living and sitting rooms, and spacious primary suites with baths. Additional living space includes two additional bedrooms and a full bath, plus a lower-level spacious guest suite, entertainment rooms, abundant storage, and outside separate entrance (OSE) with its own designated parking. Set on 1.09 beautifully landscaped acres with specimen trees, brick patios, decks and exterior lighting, a spectacular salt water heated gunite in-ground pool (approx. 43’ x 25’) with waterfall, spa, lighting, and natural rock diving board—perfectly positioned to capture sweeping river views. Enjoy evenings by the wood-burning fire pit, surrounded by nautical wildlife and breathtaking sunsets. Located in the highly sought-after Smithtown community, close to fine dining, boutique shopping, theatre, mall, Caleb Smith Preserve, Sunken Meadow Park, beaches, golf, and Smithtown schools. Smithtown offers a blend of tranquil suburban life, historic charm and easy access to parkways and the LIRR/NYC. Additional Features: 2-car garage, North Wing: electric heat exchanger, CAC, heat/AC, South Wing: 3 mini-splits, 5-ton compressor, oil burner, forced hot air/CAC, 60-panel solar system (shared by both wings), In-ground sprinklers, Central vacuum, Two propane tanks, Two fireplaces (one gas, one wood-burning), Two separate hot water heaters, Additional electric panels, Laundry room with slop sink and storage, Brick patio with built-in BBQ

2 Riverview Terrace, Smithtown

38 Riverview Terrace, Smithtown
$1,950,000
5 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

225 Old Willets Path, Smithtown
$1,890,000
4 Beds ⋅ 3 Baths ⋅ 1008414 MLS
Welcome to this one-of-a-kind custom estate-quality residence rebuilt in 2018 by a professional contractor as his personal home with attention to detail and premium materials throughout. Situated on a private 1-acre property, this exceptional 4-bedroom, 2 1/2 bath home welcomes you with a striking stone façade and dramatic arched entryway that sets the tone for the extraordinary craftsmanship found throughout. Features include oak hardwood floors, solid hardwood interior doors, custom millwork, marble and tile mosaics, a custom detached 2-car garage with handcrafted garage doors built by the homeowner and features its own electrical panel. The fully finished basement includes an outside entrance, laundry area and epoxy flooring. The large, open kitchen includes custom cabinetry, granite countertops, stainless steel appliances, and custom designed tile work. A breathtaking handcrafted marble fireplace with carved lion statuary serves as the centerpiece of the home and features a heat-circulating system with dedicated venting to the primary suite above. Built with 2x6 construction and blown-in insulation for exceptional energy efficiency, the home was also strategically positioned above grade to promote superior drainage. Smart home features include remote thermostat controls with separate zones in each bedroom and an automatic leak-detection water shutoff system. Extending the living space outdoors, a covered patio overlooks the private grounds and is already pre-wired for cable and has a water line in place, providing a seamless opportunity to create the outdoor kitchen and entertainment area of your dreams. From the handcrafted architectural details to the thoughtful engineering and modern conveniences, no expense was spared in creating this truly exceptional residence. A rare opportunity to own a luxury home unlike anything else on the market.

225 Old Willets Path, Smithtown

3 Greentree Court, Smithtown
$1,749,999
5 Beds ⋅ 4 Baths ⋅ 1023719 MLS
Welcome to Plymouth Estates, a 5 lot subdivision in the prestigious neighborhood of Smithtown, NY. This NEW CONSTRUCTION subdivision on a cul-de-sac offers 5 exceptional lots, with 5 bedrooms, 3 full bathrooms, 1 half bathroom, eat-in kitchen with a large center island, granite/quartz countertops, SS Appliances, double wall ovens, wine fridge, gas cooktop, mudroom with pantry, family room with gas fireplace, living room, dining room, office/study, hardwood floors, crown molding, raised panel molding, primary bedroom with en-suite bathroom, large soaking tub, walk-in closets, 4 additional large bedrooms, and laundry room. 2 car garage, full basement with 9ft. ceilings, egress window and 2 entrances. Taxes to be determined. Currently offering two models, The Villager and The Gazebo. Nestled in the heart of Smithtown, This stunning development promises luxurious living and convenient access to various amenities, including shopping, dining, schools, and recreational facilities. With easy access to major transportation routes, commuting and exploring the area is effortless. Enjoy privacy and tranquility in this exceptional newly built development. 200 amp service, 2 zone gas heat, central A/C, 75 gal. hot water heater, central vacuum, system. Don't miss the chance to establish roots in this remarkable neighborhood.

3 Greentree Court, Smithtown

14 Loft Road, Smithtown
$1,695,000
5 Beds ⋅ 6 Baths ⋅ 1027754 MLS
Experience the pinnacle of luxury living on this sprawling 1.25+ acre equestrian-ready estate. Recently renovated to perfection, this five-bedroom, five-bathroom residence seamlessly blends sophisticated design with modern efficiency, featuring brand-new utilities and owned solar panels. The heart of the home is a dream kitchen, boasting radiant heated floors, a high-end Subzero panel refrigerator, custom cabinetry with integrated inserts, and a spacious walk-in pantry. Entertain with ease in the formal dining room or retreat to the quiet study, complete with floor-to-ceiling custom built-in bookshelves. The primary suite serves as a private sanctuary, featuring an ensuite, with a cozy fireplace, a custom vanity, a bidet, a standalone shower, and a deep soaker tub. Step onto heated floors in both the primary bath and kitchen for year-round comfort. Practicality meets convenience throughout the home, which includes three separate laundry rooms, a fully finished basement, and an oversized three-car garage. Step outside to your own private oasis, where the expansive grounds offer ample space for equestrian pursuits, complemented by a pristine inground pool perfect for summer relaxation. This property offers an unparalleled combination of style, comfort, and sustainable living. Schedule your private tour today.

14 Loft Road, Smithtown

6 Hayloft Court, Smithtown
$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

589 Landing Avenue, Smithtown
$1,626,000
5 Beds ⋅ 3 Baths ⋅ 1010107 MLS
Nestled at the end of a private long drive shared with only 2 other homes and Not directly on Landing, this magnificent custom brick home offering Luxurious living space on a private 1.2 acre setting. features include a dramatic two-story grand entry foyer with two staircases, soaring vaulted ceilings, gourmet chef's kitchen with cherry cabinetry, granite countertops and Viking appliances, especially including Sub-Zero refrigerator, hardwood floors throughout entire house. Master suite with radiant heated floors, spa-inspired primary suite, and beautiful views of preserved land, Designed for elegant entertaining and comfortable living with vaulted veiling and extra-large windows. Three high ceiling attached car garage with potential for double car lift storage. The full basement features high ceilings and a separate outside entrance, offering excellent potential for recreation, home office, gym, workshop or future finished living space. This exceptional residence combines timeless architecture, privacy. quite and premium craftsmanship.

589 Landing Avenue, Smithtown

40 Friendly Road, 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

2 Vistas Circle, Smithtown
$1,499,000
4 Beds ⋅ 4 Baths ⋅ LP1439480 MLS
Serene Location! To Be Built. Please Note That Rendering/Photo Shown Conveys Craftsmanship of Homes Previously Built. Taxes Are Not Known At This Time. Features Include Hardwood Floors, Granite Kitchen Countertops, Choice Of Cabinets With Dove-Tail Draws & Soft Touch Close, 2 Zone Central Air Conditioning, Colonial Base Moldings & So Much More. Some Optional Features Include Venting Out For Stove, A Fireplace, Tray Ceiling Primary Suite, Shadow-box Molding-- Builder Will Build To Suit- Close Distance To Long Island Railroad, Highways, Shopping And More. No Models Available To View~ Purchaser To Pay Customary Builders Fees. Prices Are Subject To Change-, Additional information: Appearance:Tbb,Separate Hotwater Heater:Y

2 Vistas Circle, Smithtown

47 McArthur Lane, Smithtown
$1,399,000
4 Beds ⋅ 3 Baths ⋅ 1055810 MLS
Located in the highly sought-after enclave of Smithtown Pines, this beautifully renovated home delivers the expansive feel of a private upstate retreat right on Long Island. Set within the Hauppauge School District, every detail of this exceptional property has been thoughtfully executed, from the professionally landscaped grounds and impressive masonry work to resort-style backyard. Rich, glowing hardwood floors flow throughout the main level, complemented by a light-filled living room centered around a fireplace with built-in shelving and a formal dining room featuring a statement chandelier and picture window. The custom chef's kitchen serves as the heart of the home, equipped with a waterfall Calcutta quartz center island, Monogram induction cooktop and double ovens, Futuro Italian range hood, Miele under-counter combi-steam oven, Monogram refrigerator and dishwasher, and a built-in Brio water dispenser. Sliding glass doors open to a 600-square-foot deck, structurally reinforce to accomodate a future enclosed room, overlooking the pool, stone gardens, and firepit. The primary suite features plantation shutters and a private ensuite bath with custom cabinetry and a walk-in shower. Primium Pella Series windows and high-end hardware are featured throughout. The finished lower level offers exceptional space for extended living or multi-generational flexibility, with a spacious family room featuring sliders directly to the pool, a generously sized fouth bedroom, a beautifully renovated full bath, and a laundry area concealed behind designer doors. A generous summer kitchen with ample dining space opens direclty to the patio and firepit area, with an adjoining pantry and additional exterior access-perfect for entertaining and effortless poolside living. Outdoors, the fully fenced and updated pool is framed by mature landscaping and dramatic Pennsylvania boulders, with a thoughtfully carved-out area ready for a future hot tub. Stone steps wind through the property, passing a peaceful gazebo before continuing to the upper grounds, where a sports court awaits your personal touch. Approximately half an acre of open lawn provides abundant room for recreation, entertaining, and outdoor activities. The oversized two-car garage includes a dog shower, EV charging, and generator hookup, with additional exterior EV charging capability. Notable updates include a 20-year roof, central air conditioning, a newly completed driveway, 200-amp electrical service, front and rear sprinkler systems, and a boiler and hot water heater approximately three years old. Gas is available at the street for a future conversion.

47 McArthur Lane, Smithtown

16 Argyle Place, Smithtown
$1,395,000
4 Beds ⋅ 3 Baths ⋅ 1060784 MLS
Picture yourself in a large, sprawling ranch situated among majestic trees in the Hamlet of the Pines. A quiet upscale neighborhood in Smithtown. Life is easy with everything conveniently on the first floor (inc.3 Full Bathrooms). Nestled in over 3/4s level completely usable acre. Fast commute minutes from the LIE and Northern State. Anderson windows, solid oak floors throughout. 4 bedrooms in a separate wing including a spectacular primary En-suite and a 2nd En-suite both with full bathrooms. Grill and eat front porch. Awesome back patio. Completely renovated cheerful eat in kitchen. Warm. Sunlight pours in from a skylight, a picture window above the counter. A gas stove, plentiful cabinets and pantry make cooking a breeze. Enormous great room/den, warm and cozy with a romantic Wood Fireplace and Coal Stoves. Keep dry via 2 car garage, basement has more living space.

16 Argyle Place, Smithtown

4 Salt Hay Way, Smithtown
$1,395,000
4 Beds ⋅ 3 Baths ⋅ 1050030 MLS
Set on one serene, private acre surrounded by beautifully landscaped grounds, this distinctive four-bedroom, two-and-a-half-bath residence blends warmth, character and craftsmanship with modern comfort and efficiency. Rich architectural details include hardwood floors, custom millwork, exposed beams and coffered ceilings. The expansive kitchen features custom cabinetry, granite countertops, a center island, professional-style appliances, propane gas cooking and radiant heated floors. The primary suite offers a sitting room, two walk-in closets and a spa-like bathroom. Significant upgrades include high-efficiency heat pump heating and central air, a hybrid heat-pump water heater, whole-house insulation, water filtration and air-purification systems, extensive LED lighting and a generator. A family room with brick fireplace, two-car garage and partially finished basement with a separate heating zone and ample storage complete the interior. Outside, enjoy an in-ground gunite pool, deck, bluestone walkway, seven-zone WiFi sprinkler system, front porch and mature gardens.

4 Salt Hay Way, Smithtown

9 Franciscan Lane, Smithtown
$1,349,000
4 Beds ⋅ 3 Baths ⋅ 1052663 MLS
Welcome to this stately 4-bedroom, 2.5-bath Center Hall Colonial, gracefully positioned within the sought-after White Birch Landing community and Kings Park School District. Built in 2006, this distinguished residence offers an impressive blend of timeless architecture, refined finishes and generous living space. An elegant two-story foyer introduces a light-filled interior appointed with hardwood floors, elegant formal living and dining rooms, and an inviting family room centered around a wood-burning fireplace. The spacious eat-in kitchen features rich wood cabinetry, granite countertops, stainless steel appliances, a center island with seating and a sun-drenched dining area overlooking the grounds. Upstairs, the primary suite serves as a private retreat with a vaulted ceiling, two walk-in closets and a beautifully renovated spa-inspired bath featuring dual vanities, a soaking tub and separate shower. Three additional bedrooms and an updated hall full bathroom complete the second level. Outdoors, the level, fully fenced property is framed by mature landscaping and features an expansive paver patio designed for elegant entertaining and relaxed outdoor living. Additional appointments include a full basement, first-floor laundry, central air conditioning, natural gas heating, in-ground sprinklers, a two-car attached garage and an extended driveway. Residents also enjoy coveted San Remo privileges, offering access to the private waterfront park, boat ramp and recreational water activities along the Nissequogue River. An exceptional offering that brings together timeless style, modern comfort, privacy and a distinctive water infused lifestyle.

9 Franciscan Lane, Smithtown

135 Oakside Drive, Smithtown
$1,298,980
4 Beds ⋅ 4 Baths ⋅ 1041795 MLS
North Smithtown, Nisseaquogue Overlook Private Sanctuary Where Luxury Meets the Countryside Set against a backdrop of natural beauty, this unique residence offers architectural character, privacy, and equestrian capability. .As you approach via the impressive circular driveway—complemented by three generous additional driveways for effortless guest parking and trailer access—the estate-like scale of the property immediately unfolds. Step inside to a dramatic, light-filled interior defined by soaring, handcrafted vaulted wood ceilings and refined natural stone. The windows frame sweeping, views of the surrounding woodlands at every turn, combining sophisticated indoor living and the serene outdoors A private, self-contained guest suite complete with its own bath for multi-generational living.(With Mother daughter permit from the town) The Horse Facilities: The property features a dedicated equestrian setup including an intimate functional small barn and an adjacent tack room with views of the Nissequogue River landscape. This is more than a home; it is an exceptional legacy property offering, seclusion, natural splendor, and timeless craftsmanship. Arrange a showing today.

135 Oakside Drive, Smithtown

10 Burham Drive, Smithtown
$1,250,000
6 Beds ⋅ 4 Baths ⋅ 1021652 MLS
Located in the in a highly desirable area of Smithtown sits this well maintained colonial…. Over 4000 sq ft of living area containing 6 true bedrooms, 3.5 bathrooms, a home office, a formal dining room, guest quarters (bedroom, full bath, living room) with a separate entrance, A sizable sitting room ( 18x25) containing a wood burning fire place, a separate living room and a wonderful screened in patio that can be accessed through the kitchen and the sitting room…. The landscaping of the home is just perfect!! Multiple sitting areas make it easy and fun to enjoy and entertain. A two car garage with electric car charging station, large driveway, close proximity to Town, LI Railroad and major highways just adds more value to this home.

10 Burham Drive, Smithtown

100 Edgewood Avenue, Smithtown
$1,199,999
5 Beds ⋅ 5 Baths ⋅ 1044455 MLS
Two distinct living spaces, one extraordinary property! Tucked down a long, private driveway off of Carrie Court, this home offers 4,198 square feet of living space in the Smithtown School District. The spacious main home and attached second living area each have a separate entrance and driveway, providing generous parking and a flexible layout. Real wood cedar siding, mature landscaping, raised stone flower beds, and custom wood entry details make a memorable first impression. Inside the main home, hardwood floors, crown and door molding, recessed lighting, and skylights set the tone. The formal living room features soaring vaulted ceilings and a dramatic three-sided stone wood-burning fireplace. The chef’s kitchen pairs deep espresso-toned Shaker cabinetry with white upper cabinets, glass-front accents, granite countertops, under-cabinet lighting, stainless steel appliances, a Viking gas cooktop, double ovens, dishwasher, built-in microwave, oversized stainless steel double sink, separate vegetable sink, garbage disposal, breakfast bar, and tile backsplash. It opens to an expansive dining room with vaulted ceilings, upper windows, a wall of windows overlooking the backyard, and French doors leading outside. Plantation shutters grace many of the first-floor windows. First floor also features a spacious den/great room, featuring recessed lighting, beautiful wood floors and custom molding. Upstairs, the primary suite occupies its own level, with bamboo flooring, custom shoji-style closets, a translucent screen wall, and a spa-inspired bath featuring radiant-heated floors, a Jacuzzi soaking tub, and an oversized glass-enclosed shower. A loft with vintage oak flooring, vaulted ceilings, and recessed lighting offers flexible space that could serve as an additional bedroom or home office. Two more bedrooms and a full bath with dual glass vessel sinks complete the upper level. The main home’s at-grade lower level has its own entrance, full bath with a glass-enclosed shower, recessed lighting, and box molding. The attached second living area has a separate entrance, oak flooring, crown molding, recessed lighting, a powder room, and a stunning kitchen with double-height ceilings and clerestory windows. Antique-glazed cream custom cabinetry, Viking gas cooktop, double ovens, farmhouse sink, granite countertops, floor-to-ceiling pantry storage, and a sage-green island with carved corbels make this space exceptional. Its primary suite features vaulted ceilings and a beautifully finished bath with Carrara-style marble, a walk-in shower, built-in seat, and custom vanity. Outside, discover a resort-style backyard with a freeform in-ground pool, Trex decking, estate fencing, outdoor shower, slate and paver patios, and multiple spaces to gather or unwind. Additional features include three-zone heating and air conditioning, a gas-powered Generac whole-house generator, a 300-amp electrical panel, and 13-zone in-ground sprinklers. Town of Smithtown records identify the property as a one-family dwelling with a special exception for separate living quarters. The exception does not transfer to a new owner; a buyer would need to reapply with the Town.

100 Edgewood Avenue, Smithtown

592 Landing Avenue, Smithtown
$1,195,000
5 Beds ⋅ 3 Baths ⋅ 1055906 MLS
Completely Renovated Historic 3 story Colonial on private 1.3 Acre parcel with circular driveway blends a bright modern feel with classic architectural elements to create a showcase for your style. Stately front to back entrance foyer sets the tone. Dual Staircase, High Ceilings, Substantial Moldings, Hardwood Floors and 5 Fireplaces all add to this unique and desirable property. Relax in the knowledge that heating and cooling systems, appliances, roof and windows have been replaced in the last 6 years. Outdoor Patio is perfect for private dining. Detached 2 Car Garage. Barn and Potting Shed (as-is) Direct access to the 93 Acre Arthur H Kunz County Park on the Nissequogue River and minutes from Smithtown Landing Country Club proves to be a rare location. Easy access to shopping, main roadways and beaches! Smithtown School District

592 Landing Avenue, Smithtown

28 S Lot Road, Smithtown
$1,189,000
4 Beds ⋅ 4 Baths ⋅ 1053324 MLS
Welcome to this grand, stately Colonial, beautifully landscaped and set on a private, fenced-in 1/2-acre lot. The property offers an exceptional setting for entertaining and enjoying the outdoors, complete with a gunite pool, charming gazebo, house generator, and two-car garage for added convenience and peace of mind. Inside, the home offers four bedrooms, three full bathrooms, one-half bathroom, a versatile den that can also be used as a home office, and two fireplaces. Beautiful hardwood floors extend throughout the main level, adding warmth and timeless elegance. A spacious formal living room and dining room provide an ideal setting for both everyday living and entertaining. The formal living room features a wood-burning fireplace, creating a warm and inviting atmosphere. The thoughtfully expanded kitchen offers an open and welcoming space for cooking, gathering, and enjoying time with guests, complemented by a beautiful gas fireplace that adds warmth and ambiance. The finished basement provides additional versatile space, along with a private outside entrance and bathroom. Step outside to enjoy a beautifully landscaped retreat designed for relaxation and summer entertaining. The expansive fenced-in grounds provide plenty of space to unwind, gather with guests, and create lasting memories. With its generous floor plan, elegant details, versatile finished space, two-car garage, and exceptional setting, this remarkable Colonial offers comfort, character, and an ideal blend of indoor and outdoor living.

28 S Lot Road, Smithtown

2 Three Pond Road, Smithtown
$1,149,999
4 Beds ⋅ 3 Baths ⋅ 1059779 MLS
Welcome to 2 Three Pond Road.... This Yablonski built Center Hall Colonial is set on 1 Acre of Beautiful Property, located in the "Prestigious Grange Estates" of North Smithtown! Step inside to your grand entry foyer, formal dining room, EIK w/ top-of-the-line Imported Brazilian Stone Granite counter tops, double oven and updated SS appliances, Formal Living room w/ dual sided wood burning fireplace flowing seamlessly into the expansive den, bath powder room, and custom-built sun room w/ exquisite stone walls and built-in hot tub for tranquil relaxation, along w/ easy interior access to your 2 car attached side entry garage... upstairs you have your primary bedroom w/ private bidet and toilet room with separate shower/spa jacuzzi room, 3 additional generously sized bedrooms, Office space and/or 5th bedroom (or WIC potential), and additional full hall bathroom. Step outside to your private resort like back yard w/ mature privacy trees and professionally designed landscaping surrounding, a resort style IG pool w/ a gradual sloped bottom, custom-built pavilion area, gazebo, oversized Trex deck and tranquil waterfall.... creating the perfect setting for peaceful evenings and ultimate relaxation. Additional features include the following…. In Ground 20x40 Pool (Liner 2025) w/ a solar assisted heating system, CAC (1 Zone – 2018), Oil Heat (1 zone), Single Layer 30-year architectural Roof (2018), Hardwood floors throughout, 200 AMP electric, expansive paver driveway beautifully appointed to the side entry 2-car garage… all this and so much more set on a picturesque acre private corner lot w/ exquisite bluestone walling surrounding, cascading Waterfalls and fountains, lush nature and tranquility, you do not want to miss this!

2 Three Pond Road, Smithtown

23 Colonial Drive, Smithtown
$1,099,988
5 Beds ⋅ 4 Baths ⋅ 1039816 MLS
Welcome to this expansive 3,800-square-foot home offering exceptional space and flexibility. With 5–6 bedrooms, 4 full bathrooms, and a 3-car garage, this home is designed to accommodate a variety of living arrangements. The flexible first-floor layout features three bedrooms, two living areas, two full bathrooms, a kitchenette, and laundry, creating an ideal setup for extended or multigenerational living, guests, or those looking for additional private living space. The main living areas offer cathedral ceilings, abundant natural light, and an inviting sense of openness. The spacious primary bedroom features its own private bathroom, walk in closet and access to a deck. Additional highlights include central air, a 2019 roof, a large walk-in entry, hardwood floors, and plenty of storage throughout. Set on approximately .45 acre, the property also offers a covered porch, back deck with Jacuzzi, and outdoor space for relaxing and entertaining. With its generous square footage, multiple living areas, 5–6 bedrooms, 4 full baths, and 3-car garage, this home offers a rare combination of space and versatility. Possible mother-daughter setup with proper permits. Come see the possibilities and envision how this unique home can work for your family.

23 Colonial Drive, Smithtown

14 Sandpiper Court, Smithtown
$989,999
4 Beds ⋅ 3 Baths ⋅ 1017743 MLS
Nestled on a quiet cul-de-sac, this timeless Colonial offers the perfect blend of comfort, elegance, and privacy. Featuring 4 bedrooms and 2.5 baths, the home showcases warm wood flooring, abundant natural light, and a neutral palette throughout. he spacious kitchen is designed for both everyday living and entertaining, offering granite countertops, stainless steel appliances, ample prep space, and a tiered breakfast bar that keeps family and guests connected. Formal dining and living rooms each feature their own fireplace, creating inviting spaces for gatherings and quiet evenings alike. Outside, the private backyard is a true retreat. Backing directly onto parkland, the property enjoys exceptional privacy and features an inground pool surrounded by wrought iron fencing, beautiful paver patios, and multiple seating areas for relaxing or entertaining. Completing the package are a large garage, generous driveway parking, and storybook style curb appeal that makes a wonderful, lasting first impression.

14 Sandpiper Court, Smithtown

57 Brooksite Drive, Smithtown
$959,000
4 Beds ⋅ 3 Baths ⋅ 1020597 MLS
LISTENING TO OFFERS! When opportunity knocks the door must be opened. Welcome to 57 Brooksite Drive. A stunning single unit home in the heart of Smithtown NY sitting on nearly a half an acre of property. Renovated just over 1 year ago this home is being offered to the market at an amazing opportunity to be purchased as turn key as they come. Enjoy the state of the art renovations throughout the property including a finished basement, a first floor master bedroom, and an open concept dining room & kitchen. Spark up the fire and sit with the entire group as you enjoy the fully functional living room fireplace. Walk out your sliding door and gaze at your massive nearly half acre of land where you can host and entertain your friends. Got a project? Your attached garage gives you plenty of space to park your car and sustain your handyman fix. This property needs absolutely nothing except your willingness to enjoy it's perfection. This is a truly ICONIC home!

57 Brooksite Drive, Smithtown

45 Croft Lane, Smithtown
$950,000
4 Beds ⋅ 3 Baths ⋅ 1017406 MLS
Nestled on a sprawling and picturesque property in the heart of Smithtown, this whole house renovated in year 2022, 4-bedroom, 3-bathroom residence offers the perfect blend of privacy, space, and country-style living and very close the horse trails at Blydenburgh Park and minutes to Routes 347 & 454. Set on beautifully maintained grounds, the property features its own horse stable and equestrian facilities, making it an exceptional opportunity for horse enthusiasts, hobby farmers, or those seeking a peaceful retreat with endless possibilities. The charming home offers spacious living areas filled with natural light, generously sized bedrooms, and a flexible layout designed for comfortable everyday living. Outside, enjoy expansive open spaces, mature trees, and a tranquil setting rarely found on Long Island. A long private driveway provides ample parking and enhances the estate-like feel of the property. Whether you’re looking to enjoy horseback riding on your own property, simply embrace a lifestyle surrounded by nature, this one-of-a-kind Smithtown offering is not to be missed. Property Highlights: * 4 Bedrooms | 3 Full Bathrooms (2 bedroom 1 full bath on the first floor and 2 bedroom with 1 full bath located on the 2nd floor) * Recent updates: Oil Tank Replacement (2025) , Copper Pipes Installed (2026) * Private Horse Stable & Equestrian Facilities * Expansive Grounds with Open Space * Long Private Driveway with Ample Parking * High-end appliances (Wolf 36” six-burner range with pot filler, 42” paneled Sub-Zero refrigerator/freezer, Bosch ultra-quiet dishwasher, Sharp microwave drawer) * Conveniently Located Near the horse trails at Blydenburgh Park and minutes to Routes 347 & 454, easy access to Major Roadways.

45 Croft Lane, Smithtown

29 Sandy Hollow Drive, Smithtown
$928,000
4 Beds ⋅ 3 Baths ⋅ 1028029 MLS
Welcome home to this stunning, meticulously maintained Colonial in the renowned Commack school district. Thoughtfully expanded with additional living space, this home offers room to grow, entertain, and unwind in style. Step outside into your own entertainer's paradise — a country club-worthy backyard featuring a sparkling saltwater in-ground pool (complete with a brand-new pump). Inside, quality craftsmanship shines throughout: gleaming hardwood floors, a cozy fireplace, energy-efficient Andersen windows, recessed lighting, and a sun-drenched skylight create a warm, elevated living experience. The spacious basement offers even more flexible space for a home gym, media room, or playroom. Outside, practicality meets curb appeal with a double-wide driveway, electric garage door opener, and three sheds for all your storage needs.

29 Sandy Hollow Drive, Smithtown

22 S Lot Road, 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

31 Sterling Lane, Smithtown
$899,999
4 Beds ⋅ 2 Baths ⋅ 1059410 MLS
Absolutely stunning, turnkey Hi-Ranch in the Smithtown School District, perfectly situated mid-block on a beautiful tree-lined street. Meticulously maintained and thoughtfully updated, this 4-bedroom, 2-full-bath home combines comfortable everyday living with exceptional spaces for entertaining. The heart of the home is the impressive custom kitchen featuring granite countertops, beautiful cabinetry, stainless steel appliances, radiant heated floors and a large center island ideal for entertaining or casual meals. The kitchen flows seamlessly into the dining and living areas, where abundant natural light, hardwood floors and a dramatic cultured-stone accent wall surrounding the wood-burning fireplace create a warm and inviting atmosphere. Downstairs, the spacious and versatile lower level offers tremendous flexibility for a den, family room, home office or guest space, with large sliding glass doors opening directly to a covered patio and your own resort-style backyard. Outside is where this home truly shines. A large second-story composite deck overlooks the heated in-ground pool with waterfall, professionally paved patio areas, pergola and fully fenced yard—creating an incredible setting for summer entertaining, relaxing by the pool or enjoying a quiet evening at home. Additional features include central air conditioning, radiant heated tile floors, a two-car attached garage, large driveway, private laundry area, full attic, storage shed, in-ground sprinkler system, vinyl fencing and more. Move-in ready inside and out, with an incredible backyard and a location that's hard to beat—this is the Smithtown home you've been waiting for.

31 Sterling Lane, Smithtown

24 Frank Street, Smithtown
$899,999
4 Beds ⋅ 3 Baths ⋅ 1058590 MLS
Welcome to 24 Frank Street!! This Spacious center hall colonial features a beautiful open floor plan with a large entry foyer, formal living room (or formal dining area if preferred), Great room w/ wood burning FP, spacious dining area, EIK w/ SS Appliances and Granite Counter tops, 1/2 bath powder room, Laundry Area and access to your heated (+AC Wall unit) attached 2-car attached garage! Upstairs you have a spacious primary bedroom w/ WIC, sitting area and full bathroom, 3 additional spacious bedrooms and full hall bathroom. The partially finished basement features an oversized recreation area w/ brand new carpet and ample storage space! This home is Situated on a professionally landscaped 1/2 acre of flat property with an IG heated pool, oversized paver patio, and Trex deck area w/ Cabana. Additional features include the following… Natural Gas Heat (3 zones – Burner 2022), CAC (1 zone - 2017), 50 Gallon Gas Hot Water tank (2022), 200 AMP Electric, Roof 1 Layer 30 Year Architectural w/ 25-year warranty (2023) – skylights updated same time, Updated Anderson windows/slider doors, IG Sprinkler System (15 Zones), IG Heated Pool (Liner – 2016). All this and so much more on a private .50-acre lot, you do not want to miss this!!

24 Frank Street, Smithtown

19 Knoll Lane, Smithtown
$899,999
4 Beds ⋅ 3 Baths ⋅ 1009532 MLS
Welcome to 19 Knoll Lane, Smithtown — Where Comfort Meets Elegance Nestled in the heart of Smithtown, this stunning 4-bedroom, 2.5-bath colonial is the home you've been waiting for. From the moment you step inside, you'll be captivated by the thoughtfully designed layout that perfectly balances everyday living with sophisticated entertaining. The spacious formal living room and formal dining room set the stage for memorable gatherings, while the warm and inviting den offers the perfect retreat for quiet evenings at home. The eat-in kitchen is ideal for casual meals and morning coffee alike. Rest easy knowing you're covered year-round with natural gas heat, central air conditioning, and a security system, ensuring comfort and peace of mind in every season. Step outside and discover your own private paradise. Unwind beneath the charming gazebo, host unforgettable evenings around the built-in fire pit, or simply soak in the tranquility of your beautifully appointed backyard. 19 Knoll Lane isn't just a house — it's the lifestyle you deserve. Don't miss your chance to call this exceptional property home!

19 Knoll Lane, Smithtown

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.