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

Move Right in to this inviting, expanded Cape Cod home showcasing numerous updates from 2010 to the present. The formal living and dining rooms offer refined elegance with recessed lighting, crown molding, and raised panel detailing. The living room features a charming wood-burning fireplace, while the dining room includes a cozy window seat—perfect for gatherings and everyday comfort. The first floor was completely remodeled in 2010, featuring new sheetrock, insulation, moldings, and main flooring throughout. A first-floor bedroom with nearby full bath provides flexibility and could easily be enclosed to create a private space ideal for multigenerational living. The kitchen is equipped with wood cabinetry and stainless steel appliances, blending style and functionality. Upstairs, you’ll find two generously sized bedrooms with wall-to-wall carpeting, along with a beautifully updated bathroom. The finished basement adds valuable recreational space, perfect for entertaining, and additional storage space. The home is heated by natural gas, adding both convenience and comfort during colder months. Step outside to a backyard retreat featuring a large pavilion, an in-ground heated swimming pool, and a paver patio—ideal for outdoor enjoyment. Recent updates include a new roof, new front and rear pavers, a new driveway, central air conditioning, a remodeled upstairs bathroom, and a new pool liner and filter. Nearby is the local shopping district, fine dining, local beaches and Stony Brook University and Medical Center. Smithtown Schools.

238 Woodlawn Avenue, Saint James, NY 11780

Set gracefully on 2 private, level acres in the prestigious Village of Nissequogue, this architecturally distinctive 4-bedroom, 4 full bath, 2 half bath residence is a remarkable expression of refined luxury and timeless sophistication. Designed for the buyer with truly discerning taste, the home showcases bespoke details, dramatic architectural elements, and exquisite custom updates throughout—seamlessly blending elegance with elevated comfort. A striking entry introduces the home’s signature curved archways, rich hardwood flooring, and an airy, light-filled floor plan ideal for both grand entertaining and intimate everyday living. At the heart of the residence is a breathtaking great room featuring soaring vaulted wood ceilings, a magnificent floor-to-ceiling stone fireplace, and a beautiful custom wood spiral staircase leading to an enchanting loft library—an extraordinary architectural centerpiece that exudes artistry and refinement. Updated windows throughout the home invite natural light while framing picturesque views of the surrounding grounds. The chef’s kitchen is thoughtfully appointed with high-end stainless steel appliances, double ovens, custom cabinetry, and a dramatic wall of picture windows overlooking the lush property. Flowing seamlessly from the kitchen, an elegant den with a gas fireplace and wet bar provides a refined and inviting space for sophisticated gatherings and relaxed entertaining. A truly exceptional highlight of the home is the spectacular solarium—an extraordinary space designed for year-round entertaining. Enclosed in walls of glass and bathed in natural light, this stunning retreat features a spa pool and radiant heated floors, creating a private resort-like atmosphere in every season. Whether hosting intimate evenings or lively gatherings, this space offers an unparalleled indoor-outdoor living experience. The primary bedroom suite provides a serene and luxurious retreat with generous proportions and a beautifully appointed bath. Three additional bedrooms are equally well-designed, complemented by four full baths and two powder rooms featuring elevated finishes. A full finished basement with outside entry and guest quarters offers exceptional flexibility for extended guests, recreation, or private workspace. Outdoors, the estate-like setting offers total privacy, paver patios, mature landscaping, and a stunning in-ground pool for resort-style living. Additional premium amenities include gas heat, a full-house Generac generator, whole-house water filtration system, updated windows, and a two-car garage—plus much more. An extraordinary offering defined by architectural distinction, luxurious detail, and uncompromising quality, this exceptional residence has been thoughtfully curated to provide a lifestyle of elevated comfort, timeless sophistication, and refined luxury at every turn.

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.

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

Amazing opportunity to purchase 2 acres of land in desirable Nissequogue Village with approved plans for an 8500 square foot structure including a 3 car garage. Architect will be giving plans to the new owner, all you need to do is hire a builder! All the planning and leg work is already been done. Whether your an end user who wants to build and customize your dream home or an investor looking to make a BIG profit this is a fantastic opportunity! GPS

Amazing opportunity to purchase 2 acres of land in desirable Nissequogue Village with approved plans for an 8500 square-foot structure including a 3 car garage. Architect will be giving the plans to the new owner, all you need to do is hire a builder! All the planning and leg work has already been done. Whether your an end user who wants to build and customize your home or an investor looking to make a BIG profit, this is a fantastic opportunity! 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.

Set on a beautifully landscaped .63-acre property along a picturesque tree-lined street, this expansive 5-bedroom, 3.5-bath home offers an impressive amount of living space combined with extensive updates throughout. Designed with comfort and functionality in mind, the home features a bright, open feel with generously sized rooms, a flowing layout, and incredible flexibility for today’s lifestyle. From the spacious interior living areas to the beautifully maintained outdoor space, this home offers room to spread out, entertain, and enjoy for years to come. Inside, gleaming wood floors and a light-filled flowing floor plan create an inviting atmosphere. The spacious den is rich with character, featuring vaulted wood ceilings with exposed beams and sliders leading to the back deck — an ideal setting for outdoor dining, grilling, and gatherings. Formal living and dining rooms provide elegant entertaining spaces, while the large eat-in kitchen offers abundant wood cabinetry, ample counter space, vaulted ceilings with two skylights, and a sun-filled dinette area overlooking the property. The primary suite features a private ensuite bath, while the flexible layout offers additional bedrooms and comfortable living space throughout. The lower level of this home is incredibly spacious and offers exceptional versatility, featuring a large great room that is perfect for cozy nights or entertaining, highlighted by a beautiful floor-to-ceiling stone wood-burning fireplace, updated Andersen bay window, and door leading to the backyard and outdoor entertaining space. This level also includes a convenient powder room, laundry room, additional living space, two bedrooms, and a full bath nearby — offering excellent potential for guest accommodations, multigenerational living, or a private guest retreat. Additional updates include Andersen windows, gas heat, updated roof (2020), owned solar panels (2019), Rheem central air, and an updated cesspool. The fully fenced level property features inground sprinklers, patio space, and a built-in storage shed. Ideally located close to shopping, restaurants, Long Island Sound beaches, Stony Brook University, and Stony Brook University Hospital, this exceptional home offers space, versatility, and modern updates in a highly convenient location. A property with so much to offer both inside and out.

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.

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.

Welcome To This Sun Drenched, Unique Renovated Property In The Sought After Village Of Nissequogue. Boasting Contemporary Charm And Sophistication This 4 Bedrooms, 3.5 Baths, New Stainless Steel Appliances, Chef's Kitchen, New Floors Throughout And A Heated In-Ground Geated Pool Makes For Perfect Relaxation And Entertaining. 2 Fireplaces, Cathedral Ceilings And Two Roof-Top Decks. Walk Out Finished Basement. This Home Offers Turn Key Easy Living With Attention To Detail In Every Corner And Picturesque Views Of The Nissequogue River. Not To Be Missed! Google Maps, Waze

This charming 3 bedroom, 2 full bath ranch has been lovingly maintained and offers comfortable living with a warm, inviting feel throughout. Hardwood floors extend throughout the home while the den with a wood burning fireplace creates the perfect space to relax or gather with guests. Additional highlights include central air conditioning, oil heat, and a full basement offering generous space for recreation, hobbies, and storage. Conveniently located less than a mile from the LIRR and close to a variety of shopping, dining, and everyday conveniences, this home offers both comfort and accessibility in one appealing package.

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!

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.

Elegant and inviting expanded ranch featuring numerous recent updates and spacious living throughout. Expanded in 2009, the home offers generously sized bedrooms and a layout designed for both comfortable living and entertaining Upon entering, you are welcomed by a spacious formal dining room highlighted by a large picture window that fills the space with natural light. Just beyond, the stunning great room features pegged hardwood flooring, a cozy wood-burning fireplace, and custom built-in bookshelves, creating the perfect gathering space. Recently remodeled in 2024, the kitchen boasts white cabinetry, quartz countertops, stainless steel appliances, and a sunny breakfast nook ideal for casual dining. The private primary suite offers a vaulted ceiling with high hats, a walk-in closet, and its own full bath. Two additional oversized bedrooms share a beautifully maintained full bathroom. Additional features include a partially finished basement, new central air conditioning, a new cesspool, updated heating system, and many new or replaced windows throughout the home. Outside, the fully fenced backyard creates a private retreat complete with an in-ground pool featuring a new liner and new heater — perfect for relaxing or entertaining all summer long. Ideally located near area shopping, fine dining, local beaches, and Stony Brook University and Medical Center. Smithtown Schools

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.

Picture-perfect Center Hall Yablonski Colonial set on a flat, meticulously landscaped acre. This mint-plus residence showcases major renovations, blending timeless style with modern efficiency. The home boasts a new roof with leaf-proof gutters, new James Hardy siding, new windows and doors, all new bathrooms, new or refinished floors throughout, and new air conditioning. Designed for both elegant entertaining and everyday living, the home offers generously sized gathering rooms with new ceiling lights, hardwood floors on the first and second floors, a gourmet remodeled kitchen, and a warm, inviting den anchored by a wood-burning fireplace, a large bank of windows overlooking the back yard, and a sliding door to the young deck. Laundry has been moved to the main floor in a newly created mud room with external access to the driveway, as well as a walk-in pantry with sink. The finished lower level has new waterproof LVT flooring and provides exceptional additional space for recreation, media, workshop, work/craft space, storage, and hosting guests. Plumbing exists to add an additional full bathroom. An attached two-car garage adds convenience, including new electric garage heater, new Race Deck garage flooring, new garage doors, and a new 2nd electrical panel, while the fully fenced backyard serves as a private outdoor retreat. Enjoy a spacious new deck overlooking the spectacular 26' x 46' in-ground pool, complete with a waterfall feature, new heater, new loop-lock cover, and recent liner—ideal for summer entertaining. A new 10’ x 16’ shed with electricity can be used as a garden shed or as a pool house. Perfectly positioned near shopping, dining, wineries, beaches, and the LIRR, this exceptional property offers comfort, style, and convenience in one beautiful package.