luxury properties for sale Smithtown, United States

Step back in time with this remarkable all-brick estate built in 1905, gracefully set on 8.95 scenic acres along the river. Rich in old-world character and elegant architectural detail, the residence offers 6 bedrooms, 6.5 baths, a grand ballroom with an impressive stone fireplace, and exquisite custom millwork throughout. An additional 4.5 acres of protected wetlands across the river enhance the property’s privacy and natural beauty.

Nestled on 2.5 private acres in the picturesque Village of Nissequogue, this beautifully remodeled Colonial offers a rare opportunity to enjoy peaceful country-style living with seasonal water views of the Nissequogue River in one of Long Island’s most sought-after communities. This well-maintained home features numerous updates, including a newer roof, siding, driveway, eat-in kitchen, and hardwood flooring throughout the first floor. The interior was freshly painted in March 2026, creating a bright and welcoming atmosphere. The spacious den is highlighted by a cozy wood-burning fireplace with a stove insert, perfect for relaxing on cooler evenings. Updated bathrooms add modern comfort, while the full basement and attached two-car garage provide ample storage and functionality. Enjoy tranquil outdoor living from the rear patio, where partial river views can be appreciated during the summer months. The backyard is surrounded by mature trees, offering privacy, serenity, and a peaceful natural setting. Ideally located near local beaches, hiking and nature trails, fine dining, shopping, and Stony Brook University and Medical Center. This exceptional property combines scenic beauty, modern updates, and convenient access to area amenities. Smithtown Schools

Auction of Swan Manor, Stanford White's masterpiece in NY. 22,000 sq. ft., sea view, 14 bedrooms. Bids from $6 million, bids until September 9. Nissequogue, Long Island Sound, NY

Welcome to 17 Dorfer Lane, a spacious, beautifully maintained Colonial Home on a quiet street in a picturesque Nesconset neighborhood. The Parklike Grounds offer beauty and privacy for the discerning buyer. This four bedroom, two-and-a-half bath home represents a unique opportunity for Multi-Generational Living in a premier setting. Featuring generous living space, this home has an appealing layout consisting of formal dining room with butler’s pantry and living room, and oversized kitchen work space, eating area and den with wood-burning fireplace combine into a lovely great room perfect for entertaining or everyday living. Upstairs is the primary suite featuring a huge bathroom with soaking tub and walk-in shower, and a walk-in closet. Three additional oversized bedrooms and full bath complete the second floor. Basement with outside entrance presents opportunities for multi-generational living. Step out the sliding doors to a priveate and generously proportioned backyard anchored by a large stone patio with wood-burning fireplace and don’t miss a chance to practice your golf swing and putting on your own private practice net and putting green. All this and there is plenty of yard for leftover for other recreational activities.

Set on .61 acres of flat, beautifully landscaped property in the Hamlet of St. James, this well maintained center-hall Colonial combines timeless charm with spacious living and thoughtful recent updates throughout. The formal living room, dining room, and oversized den are filled with warmth and character, featuring wide-plank pine flooring and generous entertaining space. The den is anchored by a charming wood-burning fireplace, creating the perfect setting for cozy evenings and gatherings. The sun-filled kitchen offers oak cabinetry and is centered around a large island, with a bright breakfast area and sliding doors that open to the backyard oasis. The spacious primary suite provides a peaceful retreat with a walk-in closet and a recently renovated spa-like bath featuring an oversized shower and double-sink vanity. Three additional bedrooms offer wall-to-wall carpeting over hardwood flooring and include custom closet systems. Additional highlights include a large unfinished basement ideal for storage or future finishing, recent updates to the roof, central air conditioning, and bathrooms, offering comfort and peace of mind for years to come. Step outside to your private fully fenced resort-style backyard, complete with an inground saltwater pool and paver patio perfect for summer entertaining, relaxing weekends, and outdoor living at its finest. Nearby is local shopping, area beaches, fine dining, and Stony Brook University and Medical Center. Smithtown Schools.

Classic Colonial home offering spacious, and comfortable living . The expansive living room and beautiful wood floors throughout the home create a warm and inviting atmosphere. The eat-in kitchen flows seamlessly into the den, featuring a cozy wood-burning fireplace—perfect for everyday living and entertaining. The primary bedroom boasts an updated marble en-suite bath, while the additional bathrooms have also been tastefully renovated with quality finishes. In addition there are 3 nicely sized bedrooms on the second floor. The recently remodeled basement features durable luxury vinyl plank flooring and an outside entrance, providing versatile space for recreation, or a home office.. Step outside to enjoy the backyard deck with retractable awning, ideal for relaxing or hosting gatherings. Conveniently located near local shopping, the Long Island Rail Road, area beaches, fine dining, and Stony Brook University, and Stony Brook University Medical Center, this home offers the perfect combination of comfort, and accessibility. Smithtown Schools

238 Woodlawn Avenue, Saint James, NY 11780

Stunning updated Colonial located in the Smithtown School District. Bright, Open & Inviting! Exceptional Home Combines Elegance and Modern Updates. Resort-style Backyard with Heated Pool. Every Detail has been Thoughtfully Designed for Comfort and Enjoyment! This could be Your New Home!!

Set on 1.25 beautifully maintained, level acres within the highly desirable community of St. James, this exceptional property offers the perfect balance of space, privacy, and versatility — with a rare equestrian component that elevates it beyond the ordinary! The impeccably maintained Center Hall Colonial features 4 bedrooms and 2.5 baths with a gracious, flowing floor plan designed for both comfortable everyday living and effortless entertaining. Rich wood floors flow throughout the home, complemented by tasteful neutral decor and abundant natural light. The custom updated eat-in kitchen is thoughtfully appointed with stainless steel appliances, granite countertops, and a charming dinette area overlooking the expansive property — creating a seamless indoor-outdoor connection. Formal living and dining rooms provide an elegant gathering space, while the warm and inviting den has a wood burning fireplace and offers a cozy retreat. The primary bedroom features a private ensuite bath, and three additional generously sized bedrooms complete the second level. Updated windows and bathrooms, central air conditioning, a full finished basement with outside entry, and a two-car garage enhance everyday convenience. Additional improvements include low-maintenance vinyl siding, and a generator transfer switch for added peace of mind. Pride of ownership is evident throughout. For those seeking additional flexibility, the property is thoughtfully equipped for equestrian use. A center aisle working barn includes four 12x10 matted breeding stalls, 50-amp electric service, water, heat and ventilation fans, loft exhaust system, and phone lines. Outdoor amenities feature a riding ring with lighting, sprinkler system for dust control, paddock and grazing areas, wash rack, and full secondary fencing. The grounds provide a private and versatile environment suitable for training, conditioning, or leisure riding — all within the comfort of your own property. Ideally located close to transportation, shopping, and restaurants, as well as Stony Brook University and Stony Brook Hospital, and just minutes from the beaches of the Long Island Sound, this offering delivers both tranquility and everyday convenience — ideal for the discerning buyer seeking a private, turnkey home and “one of a kind” property.

Waterfront – Set along 243’ of pristine Long Island Sound frontage, this extraordinary waterfront estate offers a truly rare combination of sweeping unobstructed water views, direct access to a sandy beach, and beautifully manicured level grounds with no high bluff — creating an unparalleled coastal setting rarely found on the North Shore. Privately nestled at the end of a private cul-de-sac on 2 lush acres, this over 7,000 square foot custom residence plus an unbelievable entertainment lower level is surrounded by magnificent specimen plantings, manicured gardens, and expansive Ipe Brazilian walnut decking designed to embrace the breathtaking waterfront backdrop from every angle. Nearly every room captures stunning water views, creating a seamless connection to the shoreline while filling the home with natural light and tranquility. Custom built with uncompromising quality and craftsmanship, the residence showcases high-end custom finishes, exquisite detailed moldings, elegant designer touches, and only the finest materials and systems throughout. Sophisticated yet inviting, the home offers an exceptional blend of refined luxury and relaxed coastal living. Every detail has been thoughtfully curated with no expense spared. Designed for both grand-scale entertaining and intimate everyday living, the property offers exceptional indoor and outdoor gathering spaces where unforgettable memories are waiting to be made. Enjoy breathtaking sunsets over the Long Island Sound with unobstructed views stretching to Connecticut, all from the privacy of your own extraordinary waterfront retreat. Ideally located approximately 60 miles from Manhattan and moments from fine dining, shopping, marinas, Stony Brook University, and Stony Brook University Hospital, the property offers a rare blend of private coastal living and everyday convenience A true private oasis, this remarkable estate offers the feeling of being worlds away while enjoying the beauty, serenity, and prestige of luxury waterfront living at its absolute finest.

Welcome to 16 Sussex Lane, a beautifully renovated, move-in ready home located in the Incorporated Village of Lake Grove. This exceptional residence features four spacious bedrooms and three full bathrooms, a charming country kitchen, three newly renovated baths, a warm and inviting family room with a beautiful fireplace, and a versatile bonus room perfect for a home office, playroom, or guest space. No detail has been overlooked, and the owners have spared no expense in updating this home. Recent improvements include a brand-new roof, new leaders and gutters, new electrical outlets throughout, fresh interior paint, and countless additional upgrades Step outside to an entertainer's dream backyard featuring a spacious deck, elegant pavers, and a heated pool—perfect for relaxing or entertaining. This meticulously maintained home truly has too many upgrades to list and must be seen to be fully appreciated.

Nestled on a quiet cul-de-sac in the conveniently located M Section, this beautifully maintained Cambridge style Colonial, built in 1965, sits on a spacious .4 acre lot, featuring meticulously maintained grounds that offer both privacy and tranquility. This 3 bedroom, 2 1/2 bath home offers many of the most desired features including, but not limited to, a bright and inviting eat in kitchen with two large sky lights and access to the laundry room and garage, a dining room with space to entertain any large gathering, a comfortable family room for tv watching or relaxing and an additional bonus room to use as a space for guests, an office or a quiet library. The home is complimented by beautiful hardwood floors, CAC, walk up attic space, a 200 amp electrical panel, a generator hookup and 2 large backyard gazebos for outdoor living and enjoyment, to list a few. One of the special features of this home and very rare for this neighborhood, is a FULL BASEMENT, with a custom wet bar, cedar wall, ample storage and a great space for entertaining. This home has so much to offer. Located in the award winning Three Village School District and moments away from Stony Brook University Hospital, LIRR, Stony Brook Village, shopping, restaurants, kayaking, biking, parks and beaches. This is one you won’t want to miss!

Welcome to this magnificent custom Colonial nestled at the end of a private cul-de-sac in Lake Grove. Set on an expansive .62-acre property, and this exceptional home blends elegance, comfort, and resort-style living. A grand entry foyer with marble floors, soaring vaulted ceilings and custom moldings, welcomes you into the beautifully appointed sun-filled interiors. The spacious gourmet kitchen features cherry cabinetry, granite countertops, center island, premium stainless-steel appliances and sliding glass doors that opens seamlessly to the outdoor deck creating an easy transition to a private backyard setting ideal for relaxing, entertaining, or enjoying the natural surroundings. This stunning residence offers 4 bedrooms, 2.5 baths, including an oversized first-floor primary en-suite with private deck access, spa-like bath, and generous out-fitted closets. The decorative staircase leads to the second level featuring 3 bedrooms and a full bath. Additional highlights include hardwood floors, fireplace, full basement with outside entrance, and a 3-car attached garage. Step outside to your private backyard oasis featuring custom pavers, deck, gazebo, and an in-ground pool (as is), all backing serene Pine Barrens Preserve for ultimate privacy. A rare opportunity to own an extraordinary home in a premier cul-de-sac location.

Nestled in a beach community with access to a private beach (dues required), this beautifully crafted coastal residence offers the perfect blend of luxury, comfort, and modern convenience. Featuring a timeless cedar shingle exterior and stunning water views from multiple balconies, this exceptional home was thoughtfully designed with high-end finishes throughout. The open and airy living spaces showcase vaulted ceilings, white oak flooring, and motorized shades in the living room, kitchen, and dinette area. A wood-burning fireplace creates a warm and inviting focal point, while custom cabinetry, a Cooper farmhouse sink, induction stove and premium details elevate the chef’s kitchen. Step outside to enjoy the spacious deck with retractable awning, outdoor shower, sprinkler system, and beautifully designed exterior spaces ideal for entertaining. The third-floor primary suite is a true retreat, complete with a private balcony overlooking the water, en suite bath, and custom maple-finished closets with maple drawers. Additional luxury features include radiant heated tile flooring on the first floor, heat pump systems servicing the main and third floors, smart thermostats, Ring doorbell system, Kohler generator, recessed hinges, European magnetic door strikes, and sprinkler protection for third-floor exit access. Additional highlights include a two car garage, U-shaped driveway, and excellent proximity to local amenities. Enjoy easy access to Long Beach Town Park, located nearby, just 0.6 miles from Smithtown Bay Yacht Club, approximately 6 miles to the Long Island Rail Road station in St. James. A rare opportunity to enjoy refined coastal living with luxury finishes, smart-home features, and breathtaking surroundings.

This Spacious Colonial set on 0.20 acres, plus the additional adjacent 0.12-acre lot included in the sale, offers exceptional outdoor space and future potential. The home features a large living room with a bright bay window, a formal dining room, and an eat-in kitchen with classic oak cabinetry. Accessibility is thoughtfully incorporated with a handicap ramp leading to the rear entrance and a motorized chair lift providing easy access to the second floor. Upstairs, the primary bedroom includes a walk-in closet and private ensuite bath, complemented by three additional generously sized bedrooms—ideal for family or guests. Recent Improvements Include a new roof and updated siding and windows. The fenced backyard provides privacy and space for outdoor enjoyment, while the extra lot adds versatility. Tucked Away on a peaceful dead-end street, this home offers the perfect balance of privacy and convenience, with close proximity to shopping, the local beach, fine dining and Stony Brook University and Medical Center. Three Village Schools.

Discover the perfect blend of charm, comfort, and convenience in this beautifully maintained 4-bedroom, 2.5-bath Center Hall Colonial, ideally positioned on a serene 0.60-acre property off a cul-de-sac in Old Stony Brook’s sought-after Quaker Hill neighborhood. This inviting home offers an exceptional lifestyle both inside and out. Step through the welcoming foyer into sun-filled living spaces, including a spacious living room, elegant formal dining room with butler’s pantry, and a warm, character-rich den featuring a wood-burning stove/fireplace, an ideal setting for cozy evenings or effortless entertaining. The open kitchen serves as the heart of the home, boasting quartz countertops, stainless steel appliances, and a charming breakfast nook that overlooks the property. The expansive, fully fenced backyard is your private retreat, complete with a wood deck and sparkling salt water in-ground pool—perfect for summer gatherings, relaxation, and outdoor enjoyment. A full basement provides abundant storage and flexible recreation space. Located just minutes from local shops, SUNY Stony Brook, West Meadow Beach, and the train station, this home offers unmatched convenience in one of the area’s most desirable settings. Classic architecture, modern updates, and a prime location come together to create a truly exceptional opportunity.

Set on nearly a half an acre on a tree-lined street, this beautifully reimagined East Northport colonial pairs timeless architecture with sophisticated modern living. Extensively renovated over the past four years, the home offers a rare blend of elevated design, effortless functionality and turnkey comfort. At the center of the home, a stunning designer kitchen serves as both a showpiece and gathering place, anchored by an oversized quartz island, soft close cabinetry, stainless steel appliances, and refined finishes throughout. The kitchen opens seamlessly to expansive living and dining spaces, with a coveted open flow rarely found in a traditional colonial, while a laundry room and powder room complete the main level. The primary suite is a true retreat, highlighted by a spa-like bath with an oversized 6’x6’ walk-in shower, soaking tub, and double vanity. An adjoining private sitting room or dressing retreat enhances the suite’s sense of luxury and flexibility. Two additional bedrooms and a beautifully renovated bath complete the second level. Outside, a flat, fully fenced backyard creates an exceptional setting for entertaining and effortless indoor-outdoor living. Impeccably maintained and thoughtfully curated throughout, this is a home of exceptional comfort, quality, and understated luxury.

Featuring the lovely 3,300-square-foot prior Spring Briar Model Home with soaring ceilings, spacious rooms, and beautiful hardwood floors. A standout feature is the 600-square-foot bonus room, offering endless possibilities—perfect for a home office, professional workspace, gym, media room, or playroom. The expansive parking area provides added convenience and could accommodate clients or visitors, making this property ideal for a home-based business or office (subject to local zoning). This home offers exceptional space, flexibility, and potential to fit a variety of lifestyles and needs. Perfect location with proximity to highways, shopping, restaurants, museums and Stony Brook University/Hospital. Situated in the renown Three Village School District.

Exceptional care and pride of ownership define this impeccably maintained 4-bedroom, 2.5-bath Colonial, where every space has been thoughtfully maintained for comfortable everyday living. The inviting main level features a formal living room, elegant dining room, a warm and welcoming den with a wood-burning fireplace and direct access to the backyard, and a spacious eat-in kitchen overlooking the beautifully landscaped property. Upstairs, the primary suite offers a walk-in closet and private en-suite bath, while three additional generously sized bedrooms are served by a spacious full hall bath, creating a floor plan that is both functional and comfortable. Surrounded by mature landscaping, the backyard is a private oasis with an in-ground pool, offering the perfect setting for quiet mornings with coffee, relaxing afternoons, and effortless outdoor entertaining. Ideally situated in East Northport, this home offers the ideal combination of privacy and convenience with easy access to parks, shopping, dining, transportation, and everyday amenities. Beautifully cared for inside and out, this is a home where meticulous maintenance and pride of ownership are evident at every turn. Elwood SD

Rare opportunity to own a completely renovated home situated on 1.5 flat, private acres at the end of a cul-de-sac, offering exceptional privacy and a serene setting. This move-in ready residence has been thoughtfully updated from top to bottom using premium, low-maintenance materials and designer finishes throughout. Features include light oak hardwood flooring, modern glass staircase railings, fresh paint, and a stunning eat-in kitchen with custom light oak cabinetry, quartz countertops, stainless steel appliances, a statement hood, and views of the expansive backyard. The spacious family room offers a wood-burning fireplace, while a designated mudroom area provides convenient access to the oversized 2-car garage. The private primary suite is set apart from the additional bedrooms and features vaulted ceilings, a newly renovated bath, and a custom oversized closet. Two additional bathrooms have also been beautifully renovated. Extensive improvements include new heating and cooling systems, Hardie Board siding with premium Azek exterior trim, a new roof, gutters, driveway, 200-amp electric service, and in-ground sprinklers in both the front and rear yards. Mature landscaping has been enhanced with new plantings, creating a picturesque outdoor setting. Truly nothing to do but unpack and enjoy this meticulously updated home where quality craftsmanship and premium, low-maintenance materials were thoughtfully selected throughout. Don’t miss this rare offering!

Set on two private acres in the Village of Old Field, this beautifully maintained Cape Cod offers a rare blend of charm, space, and thoughtful updates. With four bedrooms and two and a half baths, the home features hardwood floors, classic crown molding, and a warm, inviting layout. The eat in kitchen is equipped with stainless steel appliances and overlooks the backyard. A bluestone screened porch provides the perfect setting to enjoy the surrounding property in every season. Recent improvements include new plumbing lines, a roof just 10 years young, central air and Anderson windows. Set on expansive grounds, the property also features a horse stable, making it ideal for equestrian enthusiasts or those seeking a lifestyle with room to roam. Located just moments from West Meadow Beach and within the highly regarded Three Village School District, this is a special offering in Old Field that combines timeless character with modern updates in a truly serene setting.

GREAT OPPOUTUNITY! Four bedroom, 2 full Bath Colonial with attached in-law suite or legal rental apartment. Set on resort-style property boasting in ground heated salt water pool with waterfall, hot tub and large Patio with wood Awning. The pool house has full bath and washer /dryer and second floor storage. Main house has Living room, formal dining room, oversized family room, eat in Kitchen, full bath and 1st floor laundry room. Four bedrooms and new full bath complete the second floor. Separate in-law suite or legal apartment with separate entrance, eat in kitchen, sun drenched dining room/living room and full Bath with sliding doors to deck. 3 Zone Gas heat, 2 zone CAC, circular driveway and much more.

This magnificent home seamlessly blends grandeur with versatility for multi-generational living or private guest accommodations. Set on exquisitely landscaped grounds, the property unveils a true country club-inspired retreat. Inside, the home showcases a chef’s kitchen flowing into a sunlit den with fireplace that invites warmth and connection. Formal living room, formal dining room, butler’s pantry and wet bar. 9 ft. ceilings and gleaming hardwood floors throughout. With a primary suite offering spacious closets and lavish full bath, Additionally 3 generously appointed bedrooms, 1 full bath and a half bath, every detail is designed for comfort and luxury. Attached to the main home is an exquisite accessory apartment featuring living room with cathedral ceilings, full bath and kitchenette. A dedicated professional basement office space provides an ideal work-from-home environment with privacy and distinction. Beautiful pergola with paver surround create a resort-like ambiance, anchored by a stunning in-ground pool with waterfall, slide and diving board. Wrap-around decking extends the living space outdoors, offering serene views and a seamless indoor-outdoor lifestyle.

Magnificently reimagined and meticulously renovated, this approximately 5,500 square foott residence in the sought-after Northport Bay Estates community delivers an extraordinary lifestyle inside and out. Offering six bedrooms, four full baths, and a generously scaled floor plan purpose-built for entertaining, the home has been transformed by years of thoughtful upgrades throughout. Hardwood floors flow throughout, and the chef's kitchen anchors the interior with premium stainless steel appliances and an open connection to the great room. A dedicated home gym rounds out the interior amenities. Outside, the property is a world unto itself: a heated in-ground pool with waterfall and hot tub is the centerpiece of a resort-caliber backyard finished with premium wood fencing, landscape and architectural exterior lighting, and lush mature grounds. The fully finished and conditioned pool house is a standout — a freestanding structure with interior and exterior lounge spaces and a full wet bar and bath, ideal for summer entertaining. An outdoor kitchen with natural gas BBQ under an open overhead trellis extends the living space further, while a basketball court adds to the recreational offering. The two-car garage has been fully renovated and features finished, conditioned loft office space above. Premium gutters and a completely refreshed exterior complete the picture. Private beach rights and mooring rights included with HOA.