luxury real estate for sale Head of the Harbor, United States

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

Elegant North Shore, waterfront, gilded-age family residence. Enjoy the water resort lifestyle! The notable Astor family commissioned, The Mallows, by world-renowned architect Charles Platt. 4.1 acres of sprawling grounds and 300ft of waterfront in the prominent Head of the Harbor. Walking distance to the yacht club and the vibrant village of Stony Brook within the Three Village School District. Luxurious amenities; elevator, library, glass conservatory, 14 fireplaces and a separately accessed 3 bedroom guest cottage w/kitchen. Work, play, and entertain, with ample bonus rooms, guest suites, offices and even a 2nd kitchen! Endless outdoor recreation at the water's edge including a tennis court, heated salt-water pool, limestone patio, play castle, hot-tub, gazebo, vegetable gardens, chicken coop and 20+ car cobblestone circular driveway with separate service access. Extend the day with West-facing sunset waterfront views. Private and easily accessible to NYC and Hamptons. Harbor Road to Emmet Drive, driveway on left

Welcome to 523 Long Beach Rd, Nissequogue, a luxurious home with over 8500 sq. ft. of living space, including 6 bedrooms, 5.5 baths, and a 3-car garage. Enjoy top-of-the-line appliances in the kitchen, custom trim work, and applied molding detail throughout. Entertain guests in the formal dining room or cozy living room. The master suite features his and her walk-in closets, a soaking tub, and a 84 Vanity. State-of-the-art speakers and custom lighting in the kitchen and living areas create the perfect ambiance. The exterior features Azek sheet panels and Hardi Artisan siding, roof over patio leading to a beautiful in-ground heated pool. Too much to list. Ask for full amenities sheet! *** Floor plans do not show 850 sq ft 3 car garage being built***

Welcome to 523 Long Beach Rd, Nissequogue, a luxurious home with over 8500 sq. ft. of living space, including 6 bedrooms, 5.5 baths, and a 3-car garage. Enjoy top-of-the-line appliances in the kitchen, custom trim work, and applied molding detail throughout. Entertain guests in the formal dining room or cozy living room. The master suite features his and her walk-in closets, a soaking tub, and a 84 Vanity. State-of-the-art speakers and custom lighting in the kitchen and living areas create the perfect ambiance. The exterior features Azek sheet panels and Hardi Artisan siding, roof over patio leading to a beautiful in-ground heated pool. Too much to list. Ask for full amenities sheet! *** Floor plans do not show 850 sq ft 3 car garage being built*** GPS

Set in the heart of Stony Brook Village, this charming two bedroom cottage offers a rare blend of character, comfort, and location. Thoughtfully maintained and tastefully updated, the home features a warm and inviting interior anchored by a cozy wood burning fireplace and accented by wide plank wood floors that add timeless appeal. The kitchen has been updated with granite countertops and stainless steel appliances, while the baths and major systems have been carefully improved to support easy, everyday living. A sun filled den with walls of windows overlooks the backyard and features sliders that open to two separate outdoor sitting areas, creating an effortless connection between indoors and out. Outside, the fenced backyard feels like a hidden little escape, with sweet tucked away spots to sip your morning coffee, unwind at the end of the day, or gather with friends on a warm evening. A paver driveway adds to the home’s storybook charm. Perfectly positioned near local parkland, Stony Brook Harbor, the Village, and its historic surroundings, this is an opportunity to enjoy one of the area’s most beloved settings in a home that feels both special and approachable.

Welcome to Fairfield at St James. This 55+ community features low taxes and green spaces with parkland, sidewalks and pond, plus Clubhouse with library, fitness center, billards room, indoor pool, 2 outdoor pools, tennis court and pickle ball. This move-in ready 2 bedroom, 2 bath, Dover Model, opens to a large front to back space with coat closet, Dining area and Living Room with sliding glass door to the patio that fill the room with natural light.

Welcome to this spacious Colonial home, gracefully set on .55 acres of level, park-like property. Inside, you’ll find generously sized rooms enhanced by hardwood flooring. The large, sun-filled eat-in kitchen features warm wood cabinetry, Corian countertops, and stainless steel appliances—perfectly designed for both everyday living and entertaining. An inviting den with a stunning stone, wood-burning fireplace and custom built-in cabinetry creates a cozy and sophisticated gathering space. Even the thoughtfully designed laundry room elevates daily living, transforming routine tasks into an effortless and enjoyable experience. The primary suite offers a private retreat with an en-suite bath and a walk-in closet, while three additional bedrooms provide comfortable accommodations for family or guests. Recent improvements include newer roof, hot water heater and new pool liner. Step outside to a tranquil fenced backyard with built in pool ideal for quiet relaxation or gracious entertaining in a serene, natural setting. This spacious and welcoming home seamlessly blends comfort, functionality, and modern updates. Nearby is the local shopping district, fine dining, town beaches, and Stony Brook University and Medical Center. Smithtown Schools

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!

This Stony Brook Village gem blends historic character with thoughtful updates. Originally built in 1820, the home has been completely renovated with full insulation, updated plumbing and heating, new bathrooms, a beautifully renovated kitchen, and an in-ground sprinkler system. Custom period moldings and finish details throughout preserve the home’s charm while adding warmth and character. A delightful south-facing front porch welcomes you in. The first floor offers a formal living room, office, full bath, formal dining room, spacious eat-in kitchen, pantry, and laundry room. Upstairs are two generous bedrooms and a full bath. Additional space includes a walk-up attic and an unfinished basement. A standout feature of the property is the large detached barn, currently undergoing significant improvements including new structural joists and rafters. New windows and board-and-batten siding on the front will be completed shortly. The barn already has new electric and plumbing in place and offers wonderful potential for a future apartment. A separate portion of the space could easily become a two-story home office or art studio filled with natural sunlight. Set along a sidewalk that leads directly to the heart of Stony Brook Village, this is a rare opportunity to own an updated, period home in a highly desirable location.

Welcome to this exceptional Old Stony Brook gem, located North of 25A on a well kept 0.57 acre property. This inviting Ranch offers 3 Bedrooms, 1.5 Baths, featuring a comfortable Living Room and a Dining Room with a charming Fireplace - perfect for everyday living and entertainment. The newer, Grand Kitchen is a true highlight, showcasing Granite Countertops, Viking Stainless Steel Appliances and Breakfast Nook. Additional features include a full unfinished basement offering endless potential, a welcoming Front Porch, and a sprawling Fenced Backyard with Pavers patio ideal for outdoor enjoyment. Conveniently located near Shops, SUNY Stony Brook, and Train Station, this home combines classic charm, modern amenities and an unbeatable location.

The Oaks at Stony Brook offers carefree ranch-style living in a desirable 55+ community of 45 homes, ideally located near shopping, dining, and everyday conveniences. High ceilings and an open floor plan create a bright, airy atmosphere throughout the main living areas. The spacious living room and dining room combination flows effortlessly into the large kitchen, which features wood cabinetry, granite countertops, and stainless steel appliances. A gas fireplace adds warmth and charm to the living room, making it an inviting space for relaxing or entertaining. The primary suite is generously sized and features a tray ceiling, a walk-in closet, and an additional closet for extra storage. The en-suite bath includes a jetted soaking tub, double vanity, and glass-enclosed shower. The second bedroom features laminate flooring and is conveniently located next to a full bath with a soaking tub with shower. Additional living and storage space can be found in the full, partially finished basement, ideal for recreation, hobbies, or a home office. Gas heat, first-floor laundry, and a two-car garage add to the home’s comfort and convenience. The nearby clubhouse, pool, tennis court and pickleball court complete the lifestyle, offering excellent amenities for active adult living.

INVESTOR OPPORTUNITY - DRIVE-BY VIEWING ONLY - DO NOT WALK PROPERTY The Enclave by Edaward P Mellon-Rare opportunity to acquire a double lot totaling 0.3 acres in a prime Stony Brook location. This property is being sold strictly AS-IS. Absolutely no access to interior or grounds permitted. Drive-by viewing only. This well-positioned double lot offers convenient proximity to transportation (0.5 miles to train station), schools (1 mile), and hospital (1.5 miles). Cash buyers or investors with renovation/construction experience preferred. Seller makes no representations or warranties regarding the condition of the property. All inspections and due diligence are the responsibility of the buyer.

68 Knolls Drive, Stony Brook, NY 11790

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.

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.

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.

You’re very close. This just needs tightening, flow, and a bit more polish while keeping your tone: Set within the sought after Soundview Beach Association in Stony Brook, this three bedroom, two bath contemporary offers a lifestyle that feels like a getaway without ever leaving home. Residents enjoy a true waterfront community setting with access to beach, pavilion, boat ramp, and playground. The home is bright and welcoming, with hardwood floors and an open floor plan designed for easy living. Two bedrooms are located on the main level, while the primary suite is privately set upstairs, accessed by a spiral staircase that adds architectural interest. The backyard offers a private inground pool which sets the stage for summer living. Additional features include central air conditioning, gas heating, and a whole house generator for added comfort and peace of mind. Located within the Three Village School District and moments from the shoreline, this is an opportunity to enjoy coastal living in one of Stony Brook’s most established waterfront communities.

Located in the highly desirable Old Field South neighborhood, this sophisticated, fully renovated residence showcases exceptional craftsmanship, high-end finishes, and a flexible, thoughtfully designed floor plan. Expansive living spaces with vaulted ceilings are ideal for both everyday living and entertaining, featuring an elegant living room with a fireplace, a formal dining room, two generously sized dens, and a heated, sun-drenched solarium enhanced by new floor to ceiling windows and skylights. The gourmet eat-in kitchen is beautifully appointed with custom natural cherry cabinetry, honed quartzite countertops, and premium appliances, including a Wolf double oven, Wolf cooktop and Sub-Zero refrigerator. The serene primary suite offers seasonal water views of Long Island Sound, complemented by two walk-in closets and a luxurious spa-inspired bath with a soaking tub, walk-in shower, custom cabinetry, leathered granite countertops, and radiant heated floors. Outdoor living is equally impressive, with a private, professionally landscaped backyard featuring a heated saltwater pool and an expansive bluestone patio. Thoughtful landscape lighting highlights specimen trees and lush plantings throughout the property. Handcrafted natural cherry cabinets compliment rooms throughout the residence. Additional amenities include three newly renovated bathrooms, rift and quartered, wide plank white oak flooring throughout, a partially finished basement, three-zone central air conditioning, a newer architectural roof, and more. Ideally located less than one mile from West Meadow Beach and Nature Preserve, this home represents a rare opportunity to own a property of this caliber. Property Owners Association dues are $100/year. Taxes being professionally grieved.

Welcome to this beautifully maintained 4 bedroom, 2 bath expanded Cape offering the perfect blend of charm, comfort, and future potential. Hardwood floors flow throughout the home, while the light filled, remodeled kitchen serves as the heart of the home with stylish updates and an inviting atmosphere. The first floor primary bedroom provides convenient single level living, complemented by a stunning renovated bath featuring double sinks, a separate shower, and a luxurious soaking tub. Two fireplaces add warmth and character, creating cozy gathering spaces throughout the home. Enjoy morning coffee or evening relaxation in the three season room overlooking the serene backyard, offering a peaceful retreat surrounded by nature. Additional highlights include a new roof, CAC, whole house water filtration system, and an electric vehicle charging station. A truly unique feature of this home is the approximately 1,000 square feet of unfinished attic space on the second floor, presenting an incredible opportunity to create a grand primary suite, recreation room, home office, or whatever best suits your lifestyle. The full basement provides even more flexible space for recreation, hobbies, and abundant storage. Lovingly cared for and thoughtfully updated, this home offers exceptional value, versatility, and room to grow. Located in the highly desirable Old Field South neighborhood and part of Three Village Schools. Close to West Meadow Beach.

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.

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!!

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.

Welcome to this beautifully renovated custom Center Hall Colonial, ideally located north of 25A and just minutes from West Meadow Beach. Set on a private, professionally landscaped .77-acre property, this exceptional home was extensively updated in 2016 with timeless finishes and superior craftsmanship throughout. Once inside, discover stunning 5-inch Rift and Quarter Sawn White Oak flooring, Andersen windows and sliding doors, new cedar shingle siding with Azek trim, and the added peace of mind of a whole-house Kohler generator. This home is also energy efficient throughout! The heart of the home is the chef's dream kitchen, featuring custom maple cabinetry, leathered granite countertops, an oversized center island, a commercial-grade 6-burner range with hood, double wall ovens, two dishwashers, dual sinks, and a spacious walk-in pantry. Designed with entertaining in mind, the open floor plan offers elegant formal living and dining rooms, along with an expansive family room complete with a marble-appointed full bath, private side entrance, and sliding doors leading to the backyard oasis. Upstairs, the luxurious primary suite features soaring vaulted ceilings, celestial windows, a generous walk-in closet, and a beautifully designed spa-inspired bath. Three additional bedrooms, a convenient second-floor laundry room, and a renovated hall bath with vaulted ceilings and a soaking tub complete the upper level. The finished lower level provides flexible living space, including a private office or fifth bedroom. Outside, enjoy your own peaceful retreat with fully fenced in yard with lush landscaping, a tranquil pond and waterfall, and an expansive deck with built-in seating—perfect for relaxing or entertaining. This home is thoughtfully prepared for a growing family, having been extensively childproofed for added peace of mind. All childproofing features and mechanisms can be left for a buyer, offering a move-in ready environment for little ones. This one-of-a-kind property combines luxury, comfort, and an unbeatable location. Don't miss the opportunity to make it yours!

A striking custom residence inspired by the warmth and elegance of a Tuscan villa, this exceptional home is a showcase of thoughtful design and fine craftsmanship. Soaring 19-foot ceilings and expansive, light-filled rooms create a sense of openness, while rich cherry floors and a marble gas fireplace add depth and sophistication. At the heart of the home, an impressive gourmet kitchen features a rustic hand-hewn oak ceiling, blending old-world character with modern function. The primary suite offers a private retreat, complemented by an additional bedroom and well-appointed baths. Radiant heat throughout ensures year-round comfort, while Andersen windows enhance both efficiency and natural light. An elegant staircase makes a memorable architectural statement, and every detail reflects quality construction and timeless design. The grounds are equally captivating. Professionally designed with exotic specimen plantings, custom stonework, and winding walkways, the property unfolds into a private outdoor sanctuary. A covered portico overlooks a circular fountain with bronze figure, creating a serene focal point. Beyond, a custom saltwater, heated pool is surrounded by striking stonework and lush gardens, offering exceptional privacy. A separate 1.5-story cottage, thoughtfully converted from a barn, offers exceptional flexibility. Complete with a main-level office, full bath, loft space, and snack bar area, it is ideal for a private home office or studio. A rare offering where architectural beauty, craftsmanship, and lifestyle come together seamlessly.