Above $1 Million Smithtown NY Real Estate, Homes, Condos for Sale

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

$1,399,000

4 Beds ⋅ 4 Baths ⋅ 1041795 MLS

Architecturally distinctive private equestrian estate featuring handcrafted vaulted wood ceilings throughout and refined natural stone detailing. Guest suite with private bath, Situated within an idyllic, 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.

Smithtown

$1,099,988

5 Beds ⋅ 4 Baths ⋅ 1039816 MLS

Welcome to this spacious 3,800-square-foot Colonial home, featuring a versatile split-level layout with 5–6 bedrooms and 4 full bathrooms, offering plenty of room for an extended or growing family. The home features a possible mother-daughter setup with proper permits, providing flexibility for multigenerational living. Step through the large walk-in entry into a bright and welcoming interior filled with an abundance of natural light and impressive high ceilings. The first floor features 2 generous bedrooms, 2 large living rooms, 2 full bathrooms, a kitchenette, and a laundry room, along with an attached 3-car garage. The second floor offers a formal living room with a wood-burning fireplace and a possible private office, providing an elegant and flexible space for entertaining or working from home. The third floor showcases an additional dining room, a large eat-in kitchen, and 4 bedrooms, including a primary bedroom with a private full bathroom and its own deck. The home's flexible layout provides plenty of space to accommodate a variety of living arrangements. Additional highlights include hardwood floors, high ceilings, central air, an attic for extra storage, a covered porch, a back deck with a Jacuzzi, and a private driveway. Situated on a generous 19,602-square-foot lot, the property also features an updated roof (2019) and low taxes. This unique home offers exceptional space, versatility, and comfort, with plenty of room to make it your own.

23 Colonial 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

$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

$1,199,999

4 Beds ⋅ 3 Baths ⋅ 1031008 MLS

Once-in-a-lifetime opportunity to own this spectacular custom-built Colonial, completed in 2022 and perfectly positioned on an incredibly private three-quarter-acre property within the highly desirable Smithtown School District. Tucked away at the end of a long private driveway, this exceptional estate offers the perfect combination of luxury, privacy, and resort-style living. A sprawling blacktop driveway with elegant Belgian block edging provides parking for multiple vehicles, boats, RVs, and recreational toys, while custom stone retaining walls, professionally manicured landscaping, a one-car detached garage with electric, cedar impression siding, and a cultured stone facade create breathtaking curb appeal. The backyard is truly a private resort, featuring a stunning custom in-ground swimming pool with a dramatic waterfall, natural stone diving rock, expansive Cambridge-style paver patios, multiple entertaining areas, and beautifully landscaped grounds designed for unforgettable gatherings. A welcoming covered front porch leads to a grand entry highlighted by gleaming hardwood floors, custom crown molding, decorative wall moldings, modern lighting, solid one-piece interior doors, and exceptional craftsmanship throughout. The elegant formal living room is flooded with natural light and showcases a spectacular cultured stone gas fireplace accented by custom sconces and recessed lighting. The heart of the home is the magnificent eat-in chef’s kitchen, thoughtfully designed for both everyday living and entertaining guests, featuring quartz countertops, an oversized breakfast bar illuminated by designer globe pendant lighting, custom cabinetry with under-cabinet lighting, a decorative tile backsplash, premium stainless steel Bertazzoni refrigerator, Bertazzoni gas range, built-in microwave, dishwasher, recessed lighting, surround sound, and sliding glass doors leading directly to the backyard oasis. Whether preparing a quiet dinner or hosting large gatherings, this kitchen is sure to impress. Custom blinds throughout the home add style and privacy. The flexible first-floor layout includes a spacious fourth bedroom or home office with direct access to a beautifully appointed Jack-and-Jill full bathroom featuring a white vanity and glass-enclosed shower, making it ideal for guests or remote work.. Soaring 9-foot ceilings throughout the first and second floors create an open, airy feel. Upstairs, the luxurious primary suite serves as a true retreat with recessed lighting, ceiling fan, custom crown molding, abundant natural light, a spa-inspired bathroom featuring a double vanity, oversized glass-enclosed shower with designer tile, recessed lighting, and an incredible custom walk-in closet complete with built-in cabinetry, drawers, shelving, bench seating, and abundant hanging space. Two additional generously sized bedrooms offer spacious closets and share a beautifully finished hallway bathroom with a glass tub and shower enclosure. A convenient second-floor laundry room includes front-loading Electrolux washer and dryer. The impressive wood staircase with custom metal balusters adds another level of sophistication. The ground-level bonus space offers endless possibilities with high ceilings, a private entrance, abundant natural light, and flexible living space ideal for a den, media room, home gym, office, guest quarters, or extended family. Additional amenities include a walk-up attic for storage, in-ground sprinklers, an alarm system, exterior security cameras, two-zone central air conditioning, surround sound, and countless custom upgrades throughout. Every inch of this extraordinary home has been thoughtfully designed with quality finishes, timeless style, and exceptional attention to detail, creating a rare opportunity to own one of the finest newer construction homes in the highly sought-after Smithtown School District.

79 Oakside Road, Smithtown

$1,299,000

4 Beds ⋅ 3 Baths ⋅ 1030904 MLS

This Pristine Dream Home, Nestled on a Meandering Wooded Street in the Pines, is Ensconced in a Peaceful, Perennial Paradise! The Lushly Landscaped & Lovingly Tended Property, as Meticulous Outside as the Home is Inside, Compels you to Linger on the Covered Porch or Back Patios, just to drink in the View! Inside, a Grand Foyer Shines with its Soaring Ceiling, Stunning Imported Crystal Chandelier & Exquisite Custom Millwork, here & throughout the Home. Attention to Fine Detail is Evident in each room, from the Elegant Formal Dining Room with Custom Window Seat to the Chef's Kitchen with new Stainless Appliances and Family Room w/ Garden Views for Summer & Fireplace for cozy Winters. The Radiant Heated Floors on this Floor Welcome the Colder Seasons! Ascend the Open Staircase to the Bedroom floor with it's Generous Landing & Lovely, Spacious Rooms. Look forward to beginning & ending each day, when your Primary Bedroom is your personal Suite Escape. The New Custom Designed EnSuite is Resplendent in Marble with Tasteful Accents that Highlight the Soaking Tub & Glass Enclosed Shower in the Most Beautiful Way! This Home's Beauty is not only Seen, it's Felt...from the minute it beckons you in, you know you'll want to stay. If you need more reasons to stay, here they are: The "Forever Slate" Metal Roof w/ Transferable Lifetime Warranty (home & shed), All New Andersen Windows (20 Yr Transferable Warranty), Whole House Generator, Whole House Water Filter System, 2 Zone Lennox Elite Central Air, Bosch High Efficiency Boiler & Tankless Water Heater, Electric Car Charger, Owned Solar Panels, Central Vacuum. Move-In Ready! The Season is Ideal to Enjoy All this Home has to Offer, Indoors & Out. Relax in the Garden & Entertain on the Patios, before the Autumn Colors & Snowfall Holidays begin. Isn't it Time to Stop Dreaming and Start Living the Dream? Your Best Long Island Life Awaits!

35 Pine Ridge Drive, 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

$1,699,000

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

$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

$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

$1,374,000

4 Beds ⋅ 3 Baths ⋅ 1014247 MLS

Welcome to one of the most impressive properties to hit the market in The Pines. Set on a private half-acre of beautifully manicured grounds, this extraordinary contemporary ranch offers a perfect blend of luxury, comfort, and resort-style living—all in a beautifully landscaped, private setting. A long paved driveway leads to a spacious two-car garage and a grand entry foyer with soaring vaulted ceilings that create an unforgettable first impression. Inside, rich hardwood floors, custom moldings, skylights, and high-hat lighting create a warm, elegant ambiance, while central air conditioning throughout ensures year-round comfort. The sun-filled living room, highlighted by a stunning stone fireplace and skylights, features vaulted ceilings that enhance the open, airy feel. The formal dining room sets the stage for unforgettable gatherings. At the heart of the home is a breathtaking chef’s kitchen—boasting a massive granite island, farmhouse sink, custom cabinetry, premium Thermador appliances, and a bright dining area with a tray ceiling and a bow window overlooking the backyard oasis. Sliding glass doors open to a covered Trex porch, a patio, and a pool area—perfect for entertaining or unwinding. The luxurious primary suite is a true retreat—featuring a spa-inspired bath with vaulted ceilings, a jetted shower, and a spacious walk-in closet. The home also includes 2.5 baths, a wet bar with a wine cooler, a mudroom with abundant storage, California closets, and a finished lower level with heating, air conditioning, egress windows, and a large walk-in closet. And then, there’s the backyard. This is your private resort—complete with a spectacular 40-by-20 heated pool, rock waterfall, integrated spa, and complete privacy thanks to specimen plantings, landscape lighting, and PVC fencing. With a covered Trex porch, oversized storage shed, and a commercial-grade Generac whole-house generator, this home is a haven of comfort and convenience. Move-in ready and impeccably maintained—this is a rare opportunity to own a slice of paradise. Don’t miss out—this dream home won’t last long! Note 1 Bedroom Converted to a TV Room

6 Averly Place, Smithtown

$1,675,000

4 Beds ⋅ 6 Baths ⋅ 1017188 MLS

Welcome to 3 Salt Hay Way, an exceptional custom-built residence where timeless architecture, refined craftsmanship, and resort-inspired living come together in one of Smithtown's most picturesque settings. This extraordinary estate offers a rare blend of privacy, elegance, and everyday luxury. Designed for both grand entertaining and comfortable living, this magnificent residence showcases elegant formal and informal dining areas, a welcoming sitting room, a den anchored by a wood-burning fireplace and custom bar, a private home office, and two beautifully finished lower levels featuring a custom home theater and expansive recreation space. At the heart of the home is a stunning chef's kitchen complemented by a separate prep kitchen, creating the perfect setting for effortless entertaining while keeping the main living spaces pristine. Completing the home are four spacious bedrooms, four full bathrooms, and two half bathrooms, anchored by a luxurious primary suite featuring a spa-inspired bath with a soaking tub, separate water closet, makeup vanity, and an impressive custom walk-in closet. Additional features include exquisite architectural millwork, high-end custom finishes, select smart home technology, a central vacuum system, custom closet systems throughout, a whole-house generator, abundant storage, and an attached two-car garage. The resort-style backyard is equally impressive. Professionally landscaped grounds showcase dramatic landscape lighting, a tranquil Zen garden, an outdoor fireplace, a fully equipped outdoor kitchen with a built-in grill, elegant water features, and a spectacular heated in-ground pool while creating an exceptional setting for entertaining or quiet relaxation. Offering an exceptional combination of luxury, craftsmanship, and thoughtful design, 3 Salt Hay Way is a residence that must be experienced to be fully appreciated.

3 Salt Hay Way, Smithtown

$1,299,000

3 Beds ⋅ 4 Baths ⋅ 1010163 MLS

A rare opportunity to own this exceptional 3 bedroom, 4 bath Ranch situated on a beautifully landscaped property in the coveted Smithtown Pines neighborhood. Meticulously renovated throughout, this turnkey home showcases refined craftsmanship, spacious sun filled interiors, and an effortless flow designed for everyday living and elegant entertaining. The kitchen serves as the heart of the home and features quartz countertops, a center island, stainless steel appliances, and ample cabinetry, providing both style and functionality. Updated bathrooms throughout the home offer modern finishes and a clean, refreshed feel. The fully finished basement provides a versatile living space, ideal for recreation, media, home office, additional bedrooms, or extended guest accommodations. The spectacular outdoor setting is truly a standout feature. A heated free form in ground pool with a cascading waterfall is surrounded by lush landscaping, extensive landscape lighting, and multiple areas for relaxation and gathering. The impressive gazebo is equipped with a built in kitchen, TV and cozy fireplace, creating the perfect setting for entertaining guests or enjoying quiet evenings at home. Every detail has been thoughtfully designed to provide a private vacation like retreat right in your own backyard. Meticulously maintained and move-in ready, this exceptional property offers the perfect combination of sophisticated indoor living and unparalleled outdoor amenities in one of Smithtown's most desirable neighborhoods. Just unpack and start enjoying the lifestyle you deserve.

109 Shirley Court, Smithtown

$1,099,999

4 Beds ⋅ 3 Baths ⋅ 1014077 MLS

Welcome to this beautifully updated 4 bedroom, 2.5 bath Colonial, nestled at the end of quiet dead-end street in the desirable Town of Smithtown. From the moment you arrive, the newly paved circular driveway, manicured grounds, and exceptional curb appeal set the stage for what awaits inside. Step through the front door into a stunning open foyer where natural light and elegant design create an immediate sense of warmth and sophistication. Rich hardwood floors flow throughout the home, leading you into a custom designed kitchen featuring quartz countertops, glass tile flooring, abundant cabinetry, and thoughtful finishes that make both everyday living and entertaining a pleasure. A newly renovated powder room off the kitchen has direct access to the yard, perfect for guests enjoying the outdoor amenities. Convenience meets luxury with a spacious mudroom, pantry, and laundry room off the two car garage. A living room, family room with wood burning fireplace and formal dining room complete the layout of the first floor. Upstairs, skylights bathe the landing in natural light, creating a bright and welcoming second floor space. . Four generously sized bedrooms offer comfort and privacy, including a serene primary suite complete with an updated en-suite bath with heated floors, skylight, electric fireplace and two spacious closets. The fully finished basement provides exceptional additional living space and includes a cedar closet for storage and wet bar. Recent updates include a brand new tankless hot water heater, offering efficiency and peace of mind. Outside, prepare to be captivated by an exquisitely landscaped backyard designed for both relaxation and entertaining. Multi level grounds with charming gazebos, a built in heated pool, pool house, two storage sheds and a nine zone sprinkler system combine to create a resort like setting you will never want to leave. Whether hosting summer gatherings or enjoying a quiet evening under the stars, this outdoor oasis is truly unforgettable. A rare opportunity to own a meticulously and thoughtfully updated home in Smithtown.

17 Lower Road, Smithtown

$1,099,999

5 Beds ⋅ 4 Baths ⋅ 1005651 MLS

Welcome to 54 Sandy Hollow, a beautifully maintained Brookfield Colonial located within the highly regarded Commack School District. This spacious home offers 5 bedrooms and 3.5 baths, featuring an open and versatile floor plan designed for both everyday living and entertaining. The heart of the home is the impressive kitchen, complete with a large eat-in area, expansive granite island, abundant cabinetry, and soaring ceilings that create a bright and inviting atmosphere. The flexible layout includes two primary suites—one conveniently located on the main level and another on the second floor—providing excellent options for extended living arrangements or guest accommodations. A partially finished basement offers additional living space, storage, and endless possibilities to suit your needs. The attached two-car garage adds convenience and functionality. Step outside to your own private backyard retreat, featuring a heated gunite in-ground swimming pool, generous outdoor living space, and mature landscaping that provides exceptional privacy. Perfect for relaxation or entertaining, this backyard oasis offers the comfort and tranquility you have been searching for. Conveniently located near shopping, dining, parks, and major transportation routes, this is a wonderful opportunity to enjoy all that Commack has to offer. Natural gas service and a whole-house generator provide efficiency, reliability, and peace of mind

54 Sandy Hollow Drive, Smithtown

$1,185,000

5 Beds ⋅ 3 Baths ⋅ 1010498 MLS

Welcome to your private retreat, where comfort, space, and timeless charm come together! Set on a beautifully landscaped .71 acre property, this spacious 5 bedroom, 2.5 bath home in the heart of Smithtown, nestled in the beautiful Forestwood section, offers the perfect blend of elegance, functionality, and outdoor living. Featuring gleaming hardwood floors throughout and a thoughtfully designed layout ideal for both everyday living and entertaining. The heart of the home is the beautiful eat-in-kitchen, featuring granite countertops, tons of cabinetry, and plenty of room for casual meals and conversation. For larger gatherings, the formal dining room provides a warm and inviting setting for holidays and special occasions. Relax in the spacious living room, unwind by the wood-burning fireplace in the cozy den, or enjoy movie nights and game days in the separate oversized family room. With five generously sized bedrooms, there’s plenty of space for family, guests, or a home office. Step outside and discover your own backyard oasis. Multiple decks extend the living space outdoors, creating the perfect setting for barbecues, celebrations, or quiet evenings under the stars. The inground freshwater pool invites you to enjoy summer days in style, while the lush gardens, colorful flowers, and mature plantings add beauty and tranquility year round. An amazing standout feature is the large 2 car barn in the backyard, ideal for hobbyists, gardeners, workshop space, extra storage, or parking additional vehicles. This incredible property offers the rare combination of indoor comfort, outdoor enjoyment, and versatile space, all in a setting that feels both welcoming and private. IGS, CAC, 150 Amps

28 Cygnet Drive, 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

$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

$1,200,000

4 Beds ⋅ 3 Baths ⋅ 1009232 MLS

Welcome to 27 Winslow Lane... a Stunning Brookfield colonial with fresh updates and thoughtfully designed touches..........This home features a large entry foyer w/ an abundance of natural light, a generously sized formal living room, a formal dining room that opens into an updated EIK w/ gorgeous white cabinetry, Marble stone countertops and SS appliances, an inviting family room w/ built in cabinetry and wood burning fireplace. Upstairs you will find a primary ensuite w/ oversized WIC and a full double vanity bathroom, 3 additional spacious bedrooms and a newly finished full hall bathroom, the basement is finished also allowing for additional living space and ample storage!! Step out back to your Private Resort like country club yard and enjoy the Heated IG Pool, outdoor Kitchen area w/ BBQ, Pizza Oven, Beverage Refrigerator & A meticulously designed expansive paver patio! Additional features include.... Outside entertainment w/ lighting and sound system, Smart home w/ heat/AC, outdoor lighting, alarm system and more all easily controlled w/ an app! CAC (2 Zones – 2023), Oil Heat (3 Zones), 200 AMP Electric, Hardwood Flooring & Custom moldings throughout, Home surveillance/Security System, IGS (9 Zones) & flowerbeds with drip lines for easy gardening, Craftsman style porch columns w stone base, Vinyl Cedar Impression Shakes, Updated Anderson Windows, Custom paver Driveway, All this and so much more situated on over 1/3 of an acre of professionally landscaped property.... An absolutely gorgeous home in a beautiful neighborhood that will not last!

27 Winslow Lane, Smithtown

$1,200,000

3 Beds ⋅ 3 Baths ⋅ 1006718 MLS

Welcome to your private 1.09-acre retreat, offering the perfect blend of comfort, space, and outdoor living. This beautifully maintained home features wood flooring throughout the main living areas, with tile flooring in the foyer, bathrooms, and laundry room for added durability and convenience. The spacious primary suite is conveniently located on the first floor and includes a walk-in closet and a private en-suite bathroom that features radiant heated floors. An additional first-floor guest bathroom provides added convenience for family and visitors. The large den offers a warm and inviting atmosphere centered around a cozy fireplace, making it the perfect place to relax year-round. The expansive kitchen is designed for both everyday living and entertaining, featuring abundant cabinet storage and generous workspace. Adjacent to the kitchen, the dining room impresses with cathedral ceilings accented by stunning wood beams, creating a bright and elegant setting for gatherings. The laundry room comes complete with a washer and dryer and is neatly enclosed with bifold doors. This room also boasts a radiant heated floor. Upstairs, recent renovations have added modern functionality and charm, including custom built-in shelving in one room and a dedicated built-in TV entertainment area in another. The upstairs bathroom has been tastefully updated with subway tile and a sleek glass partition. Step outside to discover an entertainer's paradise. The backyard showcases a massive 40' x 21' composite deck, ideal for hosting large gatherings, barbecues, and outdoor dining. Beyond the deck, you'll find an expansive 42' x 49' pool area featuring a beautiful L-shaped pool, creating a resort-like setting right at home. The property also includes a large storage shed and is surrounded by a secluded, private yard that offers tranquility and plenty of room to enjoy the outdoors. Set on an impressive 1.09-acre lot, this exceptional property combines spacious indoor living with incredible outdoor amenities, making it the perfect place to call home.

30 Landing Meadow Road, Smithtown

$1,499,999

5 Beds ⋅ 4 Baths ⋅ 1005485 MLS

Welcome to 48 River Heights Drive where a tree lined street meets a true custom masterpiece in beautiful North Smithtown. This luxurious 4,800 sq ft home offers 5 bedrooms, 4 baths, a private office, and an incredible blend of high-end design, comfort, and functionality. Custom built, expanded, and fully renovated by the current owner, this home features Brazilian cherry and hardwood oak floors, Pella windows and doors, crown molding, a 400 amp electric service, 4-zone HVAC, central vacuum, full security system, indoor/outdoor Sonos audio, and smart wiring throughout. The heart of the home is the impressive 27x27 chef’s eat-in kitchen with custom cherry cabinetry, granite countertops, natural stone backsplash, a massive 13x5 granite island, high-end appliances, 2 dishwashers, 2 sinks, double ovens, and a butler’s pantry with additional refrigerator/freezer, sink, storage, and heated floors. The kitchen flows into a palatial 40x20 great room with a natural gas fireplace, built-ins, oversized sliders, and beautiful views of the backyard oasis. The 900 sq ft primary suite is a true retreat with soaring 13 ft ceilings, a spa-like bath, oversized shower, jacuzzi tub, double granite vanities, and a custom walk-in closet. Additional highlights include a second-floor dream laundry room with 2 washers, 2 gas dryers, granite folding counters, a custom office, spacious bedrooms, custom baths, and a newly finished basement completed in 2025. Set on a flat and private .52-acre property, the backyard is an entertainer’s dream with an in-ground pool, brand-new liner, granite coping, Italian porcelain pavers, sitting wall, gas fire pit, architectural columns, lighting, and beautiful outdoor living space. Located in the Smithtown Central School District and close to beaches, parks, golf, marinas, restaurants, and shops, this turnkey home offers luxury living inside and out.

48 River Heights Drive, Smithtown

$1,200,000

3 Beds ⋅ 1 Baths ⋅ 1004569 MLS

Two Adjacent Lots in Sought-After Smithtown Pines on Over 2 Scenic Acres! Each lot is over 1 acre each. Lot 60 is vacant flat land. Lot 61 has a Well-maintained Retro Style Ranch home where buyers can enjoy the it's vintage charm w/ 3 Beds & 1.5 Baths w/ Full Basement w/Outside Entrance. Boasting Hardwood Floors throughout alongside a Bonus Recreational Room w/High ceilings surrounded in Knotty Pine Wood w/interior access to 1 Car Attached Garage. Rare Opportunity for Smart Builders/Investors w/ 3 Options: 1) Combine both lots & create one massive estate 2) Separate lots & create 2 luxury homes 3) Keep existing home & turn the 2nd acre into the backyard everyone wishes they had w/ pool, tennis court, guest house, etc. Request to view New Surveys. Lots are Taxed Separately. Being Sold Together.

37 Winston Drive, Smithtown

$1,250,000

5 Beds ⋅ 4 Baths ⋅ 975603 MLS

Welcome to this stately and impressive Colonial, ideally situated in one of Smithtown's most sought after and picturesque neighborhoods. This exceptional property offers a rare opportunity to create a custom luxury home in a truly premier setting. Boasting generous living space the home features a traditional and functional layout with a spacious Living Room, Dining Room, and inviting Den-perfect for everyday living and entertaining. The Kitchen with its Brazilian granite countertops offers generous space and serves as the perfect canvas to design the heart of your dream home. A beautiful feature of the home is a 280 ft expansive SunRoom extension, complete with hot tub, providing a unique space to unwind and relax all year long while overlooking the yard. Upstairs are 5 well appointed bedrooms including the Primary Bedroom with a huge ensuite full bathroom as well as an additional 1/2 bath. The backyard features a newly renovated 20x40 inground pool with new liner and all new coping (1 year old), and approx 3 year old filter, trex decking for low maintenance outdoor living, a beautiful pavillion to entertain under, and a gazebo. A 2 car garage, a young roof, an above ground 550 gallon oil tank, a 4 zone in-ground sprinklers, a tranquil rock waterfall, lightning rods and an expansive stone wall all around the front of the property. With its grand scale, coveted Smithtown location and proximity to the water, this is a rare find for someone to create a truly exceptional home in a prestigious neighborhood.

2 Three Pond Road, 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

$1,300,000

944827 MLS

This property is located at the intersection of 25A and Rose street, Smithtown, NY. At this intersection there is a traffic control light. This property is located a half mile north of St Catherine Hospital. This location is 3 blocks from the Smithtown Landing Country Club. Across the street from the building there is a CVS and a Teachers Federal Credit Union.

1217 25A N, Smithtown

$1,550,000

4 Beds ⋅ 4 Baths ⋅ LP1439479 MLS

Last Home To Be Built In This Cul-de-sac. 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 Show~ Purchaser To Pay Customary Builders Fees. Prices Are Subject To Change-, Additional information: Appearance:To BeBuilt

6 Keystone Court, 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

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