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127 Inlet Road W, Hampton Bays
$2,900,000
1063571 MLS
RARE FIVE-UNIT INVESTMENT COMPOUND & LOW TAXES | HAMPTON BAYS, NY. A rare five-unit compound on 0.80-acre property, in Hampton Bays, featuring a two-story main house and four detached cottages, each separately configured and currently leased. Just locks from the Shinnecock Bay shore line. This exceptional offering features a spacious two-story main house with 4 bedrooms and 4 full bathrooms, plus four detached cottages consisting of three 2-bedroom units and one 1-bedroom unit, each with its own full bathroom. The property also offers 8 parking spaces, providing added convenience for residents. Currently fully occupied, all five residences generate a combined $213,600 in gross annual rental income, with reported annual operating expenses of $36,249 and an estimated net operating income of $177,351. Ideally located near Shinnecock Bay, beautiful beaches, shopping, dining, and recreational amenities, this distinctive property combines the charm of Hamptons coastal living with established rental income and long-term investment potential. An outstanding opportunity for investors seeking a diversified rental portfolio in one of Long Island's desirable East End communities. All information, rental income, expenses, and property uses should be independently verified.

127 Inlet Road W, Hampton Bays

203 Head Of Pond Road, Water Mill
$1,695,000
3 Beds ⋅ 2 Baths ⋅ 1062749 MLS
Water Mill Opportunity - Customize Your Dream Hamptons Retreat! An exceptional opportunity to create your own Hamptons retreat in the coveted hamlet of Water Mill. Home is being sold as is and buyer is to assume completion of the property and all permits. This three-bedroom, two-bathroom residence offers a head start on your vision, with the exterior completed and a swimming pool already in place. The interior remains unfinished, presenting a rare opportunity for the next owner to customize the living spaces, finishes, and details to their personal taste. With the groundwork already established, this property offers the potential to transform an existing structure into a personalized getaway or year-round residence. Enjoy the appeal of Water Mill and the opportunity to bring your vision to life in one of the Hamptons' most desirable locations.

203 Head Of Pond Road, Water Mill

137 Great Hill Road, Southampton
$6,650,000
5 Beds ⋅ 5 Baths ⋅ 1063165 MLS
Set on 6.2 private acres, Cabin in the Woods is a distinctive architectural residence designed by renowned architect Jasmit Singh Rangr of Rangr Studio. With dramatic cantilevered forms, clean architectural lines, natural wood, and expansive glass, the award-winning design balances a striking modern aesthetic with inviting interiors that embrace the tranquil setting. An elongated infinity-edge gunite pool appears to extend into the forest, while a tennis court, spa, and separate structure housing a gym complete the property's impressive outdoor amenities. The 5-bedroom, 4.5-bathroom residence features refined modernist interiors that pair natural materials with understated elegance. At the heart of the home, an open kitchen, dining area, and great room with a fireplace connect to two screened porches and overlook the deck, oversized pool, and surrounding landscape through expansive walls of glass. One screened porch features a fireplace, while the other offers a built-in grill, creating inviting spaces for al fresco dining, entertaining, and relaxation. Two primary suites, each with a private balcony, complement three additional bedrooms and provide a thoughtful separation between private and shared spaces. Combining architectural distinction, extensive outdoor amenities, and exceptional privacy, Cabin in the Woods offers a distinctive approach to Hamptons living, conveniently located near Southampton's beaches, restaurants, golf, and shopping. This listing may include images that have been digitally altered or virtually staged. Original, unedited images are available upon request.

137 Great Hill Road, Southampton

149 Miller Road, Southampton
$1,900,000
3 Beds ⋅ 3 Baths ⋅ 1055974 MLS
The Hamptons Hillcrest Jewel located at 149 Miller Road, ideally situated in the heart of Southampton, is a large irregular lot that offers the perfect blend of convenience, privacy, and opportunity for a second-floor addition. Built in 1963 and set back from the road along a long private driveway, this inviting 3-bedroom, 2½ bath residence is just minutes from Southampton's beautiful beaches, village shops, restaurants, and train station. The home offers comfortable living spaces designed for both everyday living and entertaining, along with a spacious deck overlooking the private grounds. A spacious rear area with a full bath offers excellent potential to be converted in a private primary suite accessing the deck, creating additional living space and enhancing the home’s overall functionality. A finished lower level provides valuable additional space that can be tailored to your needs-whether as a guest area, recreation room, home office, or extended living space. Set on approximately 0.23-acre lot totaling 10,019 square feet, the property offers exceptional depth, outdoor space, and privacy, extending from Miller Road to Hillcrest Avenue. For those envisioning additional living space, the property offers the potential for a second-floor addition. The expansive lot may also offer a various size pool potential with a full-size pool being subject to zoning permitting, variances, and all other applicable approvals. Whether you're seeking a full-time residence, a Hamptons retreat, or an investment opportunity, 149 Miller Road offers a versatile property in a highly desirable Southampton location- with the space, privacy, and potential to make it your own.

149 Miller Road, Southampton

2040 Meadow Lane, Southampton
$24,950,000
6 Beds ⋅ 7 Baths ⋅ 1059111 MLS
Nestled on one of the world's most coveted addresses, Meadow Lane in Southampton, this 6-bedroom, 7-bathroom oceanfront home offers an exceptional Hamptons lifestyle defined by solitude, natural beauty, and effortless access to both ocean and bay. Behind private gates and spanning 167 feet of pristine oceanfront, the property offers an extraordinary sense of seclusion and serenity. Sweeping water views unfold from the grounds and interiors, while spectacular sunsets provide a breathtaking backdrop throughout the day. A private, wooded pathway leads directly to the ocean, creating a rare and intimate connection to the ocean. Whether preserving and enhancing its existing elegance or creating a newly designed home, this property presents an amazing opportunity in Southampton's most desirable location with the room to expand up to 15,000 square feet. Bathed in abundant natural light, the residence offers an atmosphere designed for tranquil living and effortless entertaining. The dramatic living room features soaring double-height ceilings and a wood-burning fireplace, complemented by an enclosed porch and inviting den. Expansive windows frame the surrounding landscape bringing the beauty of the ocean into the home. Enjoy the Outdoors with a heated Gunite swimming pool, sunken Har-Tru tennis court, and an oversize deck with gorgeous ocean views. This is a truly exceptional opportunity to own a oceanfront retreat on Meadow Lane capturing a rare beauty and privilege of life on the ocean and on one of Southampton's most prestigious addresses. this oceanfront retreat captures the timeless beauty, exclusivity, and privilege of life on Meadow Lane.

2040 Meadow Lane, Southampton

1766 Majors Path, Southampton
$5,600,000
6 Beds ⋅ 7 Baths ⋅ 1061138 MLS
SOUTHAMPTON ESTATE WITH POOL AND TENNIS Secluded on four acres in Southampton, this six bedroom estate offers a 6,700+/- sq. ft. home with pool and tennis. This home was renovated and re-designed in 2020. Enter the foyer to open first floor living areas flowing among a living room with fireplace, great room, kitchen with breakfast area and a dining room. On the other side of the foyer is an en-suite bedroom, a laundry room and access to the attached two-car garage with a study and full bath above. The master suite occupies one end of the second floor and features a fireplace in the bedroom, two closets and luxe bath with double vanity, shower and spa tub. The central part of the second floor on either side of a balcony is open to the first floor. At the other end of the second floor are two more en-suite bedrooms with access to a roof deck. There are 2,758+/- sq. ft. in the brand new 2022 renovated finished lower level with includes a guest room, full bath, gym, sauna, wet bar, pool table and large entertaining space with access to the pool and backyard. Outdoors enjoy the spacious deck, patio, pool and spa, and tennis court. Relax and unwind in the peaceful privacy here, or arrive at Southampton Village or ocean beaches in minutes. Bay beaches, Bridgehampton and Sag Harbor are also in easy reach.

1766 Majors Path, Southampton

9 Millfarm Lane, Water Mill
$5,495,000
4 Beds ⋅ 6 Baths ⋅ 1060873 MLS
Millfarm Lane on Reserve Perfectly positioned on Millfarm Lane, one of Water Mill's most desired and consistently appreciating locations, this classic Hamptons traditional home captures the absolute best of Hamptons living. Positioned on a pristine 0.73-acre lot, abutting a 20+ acre forever-protected agricultural reserve. The home's layout is perfectly aligned with a highly coveted southeastern backyard exposure, bathing the primary living spaces in brilliant natural light and guaranteeing maximum, unobstructed sun across the pool during peak summer months. Ready for immediate luxury living today and for generations to come, the home offers 6,530 +/- SF of total living space (including the unfinished lower level with egress that awaits your imagination), 4 bedrooms, 5.5 baths, a fireplace, an attached 2-car garage, and a heated saltwater gunite pool. Thoughtfully expanded and renovated since 2019, the turnkey home is highlighted by 9' ceilings, high-end moldings, and easy indoor-outdoor living and entertaining spaces. Pocket doors connect the spacious living room, which is equally suited as a study, to an inviting gathering room with a wood-burning fireplace and glass doors opening onto the stunning grounds. At the heart of the home, the eat-in kitchen includes a breakfast area, a central island with seating for 4, granite and quartz countertops, and a 5-burner Thermador gas cooktop. The adjoining dining room and outdoor patio offer easy options for dining indoors or out. On the main level, a wing for everyday living can be accessed from the interior and the side entrance, leading to an oversized mudroom with a pantry and nearby storage closets. The well-appointed laundry room offers stone counters, cabinetry, a barn sink, and a desk alcove, while a powder room is directly accessible from the patio. A convenient first-floor junior primary suite includes a walk-in closet and a bath with radiant-heated floors, a shower, and a double vanity. A dedicated staircase leads to a bright media and billiards room with a wet bar, wine and beverage fridge, and full bath. An adjoining attic provides additional storage, and an oversized 2-car garage accommodates fitness, storage, and parking. Upstairs, the primary suite enjoys views across the agricultural reserve and a sunlit bath with a double vanity, shower, and freestanding tub. Two spacious guest bedrooms complete the floor, each with a private bath, one ensuite. Outside, tall privet hedges frame the fully manicured grounds, accented with specimen plantings and landscape lighting. Adding to the classic Hamptons feeling, two expansive bluestone patios connect the home to a heated 20'x40' gunite saltwater pool, and a broad lawn provides room for outdoor gatherings, complemented by a storage shed and a productive vegetable garden. Just 1 mile from the Hampton Jitney, 1.5 miles from Water Mill Square, and 2 miles from Southampton Village, the home puts ocean beaches, boutiques, and fine dining within easy reach in one of the East End's strongest-performing real estate corridors. Broker/Owner.

9 Millfarm Lane, Water Mill

6 Turtle Pond Road, Southampton
$2,700,000
4 Beds ⋅ 3 Baths ⋅ 1054275 MLS
New to the market with ideal location. Perched on a hill and set on nearly an acre, this property offers a great opportunity for investors or end users looking to create something special. With its desirable location, generous property size, and flexible layout, the possibilities are endless. Inside, you'll find high ceilings, generous living spaces, and a versatile configuration featuring 4 bedrooms, 2 full baths, and 1 half bath. The primary suite boasts its own private balcony, adding to the home's appeal. The property includes a pool, 2-car garage, basement, and expansive backyard, offering plenty of space and potential for future enhancements. For boating enthusiasts, the nearby marina provides convenient access to the water and the opportunity to keep your boat close by. The area is surrounded by well-known restaurants and local favorites, while nearby bay beaches, including Towd Point, offer relaxing summer days at the beach and memorable evenings gathered around a bonfire under the stars. Ideally located between Bridgehampton, Sag Harbor, and Southampton, you'll be close to local farm stands, beaches, marinas, dining, and all that the South Fork has to offer. The elevated setting also provides beautiful sunset views. An excellent investment opportunity with nearly an acre of property, this home offers tremendous potential in a central and highly desirable Hamptons location.

6 Turtle Pond Road, Southampton

370 Old Canoe Place Road, Southampton
$2,500,000
4 Beds ⋅ 3 Baths ⋅ 1057007 MLS
Nestled just moments from Southampton Village, this beautifully four-bedroom, two-and-a-half-bath home offers the perfect balance of comfort, style, and location. Set on 1.1 Acre, the property is a private sanctuary ideal for both relaxing and entertaining. Enjoy the sun-drenched 20’ x 40’ heated pool surrounded by lush landscaping, or take in tranquil bay views from the upper-level balconies. Inside, the spacious layout features tasteful updates throughout, including modern baths and a bright, airy kitchen. Whether you’re living year round, hosting summer gatherings or enjoying a peaceful weekend escape, this home delivers. Located just minutes from world-class beaches, restaurants, boutique shopping, theaters, and scenic parks—experience the best of the Hamptons lifestyle.

370 Old Canoe Place Road, Southampton

170 Breese Lane, Southampton
$4,995,000
4 Beds ⋅ 4 Baths ⋅ 1055908 MLS
Located on Breese Lane in Southampton Village, this Neoclassical-style residence is set amidst professionally landscaped grounds with mature plantings and manicured gardens. A stone-covered entry with classic columns leads to a light-filled interior featuring approximately 16-foot ceilings, oversized French doors, and a single-level floor plan. The main living area includes a great room with a wood-burning fireplace and an adjoining dining area overlooking the rear grounds. Numerous French doors provide natural light and direct access to outdoor living spaces. The primary suite features vaulted ceilings, an en suite bath, and French doors opening to the patio and gardens. Two additional guest bedrooms each offer en suite baths. A library with fireplace and loft provides additional living space suitable for a variety of uses. The finished lower level offers more than 2,000 +/- square feet of additional space, including a bedroom, full bath, office, den, and flexible recreation areas. Outdoor amenities include a 10' x 40' heated gunite pool surrounded by mature trees, perennial gardens, and landscaped grounds. Conveniently located near Southampton Village's shopping, restaurants, cultural destinations, and ocean beaches, this property offers village living with access to nearby amenities.

170 Breese Lane, Southampton

32 Sugar Loaf Road, Southampton
$1,725,000
4 Beds ⋅ 3 Baths ⋅ 1053735 MLS
Welcome to this immaculate 4-bedroom, 3 full bath coastal retreat perfectly situated just moments from the ocean, bay beaches, charming villages, and some of the area's most beloved restaurants. Designed for both relaxed living and effortless entertaining, this home offers a spacious, sun-filled layout with beautiful coastal decor throughout. Two fireplaces create warm and inviting gathering spaces, while the finished basement provides additional room for recreation, guests, or a private retreat. Step outside to your own backyard oasis - a beautifully landscaped, quiet setting featuring a heated pool and 6-seat hot tub, perfect for summer evenings under the stars. Whether hosting or unwinding, this outdoor space delivers privacy and serenity.

32 Sugar Loaf Road, Southampton

288 Water Mill Towd Road, Water Mill
$2,750,000
4 Beds ⋅ 4 Baths ⋅ 1053868 MLS
Tucked away at the end of a private driveway on an expansive 2.2-acre wooded flag lot, this secluded Water Mill retreat offers the ultimate Hamptons lifestyle combining privacy with close proximity to town and Towd Point Beach. Inside offers vaulted ceilings with exposed wood beams and architectural warmth. Open-concept living room with wood-burning fireplace complete with wet bar, adjacent dining area and kitchen with multiple sliding glass doors leading to the expansive wrap-around deck. Primary suite on first floor with Jacuzzi tub and separate shower plus additional first floor bedroom (currently set up as a den). Also on first floor is a powder room and dedicated laundry room. Second floor with open landing complete with two en-suite bedrooms plus additional office space. The grounds are surrounded by mature landscaping and lush greenery, offering exceptional tranquility and recreation, including heated pool, all-weather tennis court, hot tub, and outdoor shower. 2,000 sq.ft. partially finished basement plus detached two car garage. Positioned moments from Water Mill's charming hamlet center, premier farm stands, top golf courses, and world-class ocean beaches. Please note chandelier in dining room is not included in the sale.

288 Water Mill Towd Road, Water Mill

40 Knollwood Drive, Southampton
$2,600,000
5 Beds ⋅ 4 Baths ⋅ 1054363 MLS
This beautifully finished five-bedroom, four-bath residence offers approximately 2,800 square feet of thoughtfully designed living space, all within easy reach of ocean and bay beaches, renowned golf courses, and Southampton Village. Designed for effortless indoor-outdoor living, the heart of the home is an open-concept kitchen, dining, and living area featuring premium appliances, elevated finishes, and a custom fireplace. An impressive 16-foot glass slider opens the space completely to the outdoors, where mahogany decking, an expansive patio, a secluded outdoor living area, and professionally landscaped grounds surround the heated gunite pool. The primary suite offers a private retreat with its own sitting area, Juliette balcony, generous walk-in closet, and a spa-inspired bath with double vanity, private water closet, and oversized walk-in shower. Four additional bedrooms, three full baths, and a separate den provide flexibility for guests, work, or additional living space. Oak flooring runs throughout the home, with two laundry areas and a mudroom entry from the spacious two-car garage add everyday functionality. The exterior has been equally considered, with cedar Hamptons-style shingle siding, a new roof, half-round gutters, Andersen windows and doors, mahogany decking, and extensive custom stonework across the patios, walkways, and driveway. The pool equipment has also been newly updated and discreetly positioned within the landscape. Modern infrastructure completes the property, including spray-foam insulation, a gas furnace, Navien hot water system, two-zone HVAC, updated plumbing and gas lines, 200-amp electrical service, nine-zone irrigation, a 1,000-gallon underground propane tank, and both town and well water. An advanced I/A OWTS wastewater system provides additional potential for future expansion. Turnkey and designed for both everyday living and entertaining, 40 Knollwood Drive offers a refined Southampton lifestyle with beaches, golf, and the village all close at hand.

40 Knollwood Drive, Southampton

810 David Whites Lane, Southampton
$2,750,000
3 Beds ⋅ 3 Baths ⋅ 1053107 MLS
Timeless Charm with Beautiful Landscaping & Outdoor Appeal Just minutes from Southampton Village, this beautifully maintained 3-bedroom, 3-full-bath residence exudes timeless English country charm and is surrounded by exceptional natural beauty. Warm and inviting interiors feature exposed beam ceilings, three fireplaces, and thoughtfully curated English country antiques that complement the home's distinctive character and elegance. A sun-filled sunroom with custom, high-end built-ins provides the perfect place to relax, while French doors open to a spacious mahogany deck overlooking the heated pool and impeccably landscaped grounds. A rooftop deck provides the perfect setting to enjoy morning coffee, evening sunsets, or peaceful views of the surrounding landscape. Designed for effortless indoor-outdoor living, the private backyard is a true retreat, featuring a heated pool, expansive entertaining spaces, and lush, professionally landscaped grounds. Adding to the property's unique appeal, a protected reserve directly across the street ensures a peaceful setting and no future development. Blending classic English country style with modern comforts in one of the Hamptons' most sought-after locations, this exceptional home presents a rare opportunity just moments from Southampton Village, ocean beaches, world-class dining, and shopping.

810 David Whites Lane, Southampton

5 William Way, Southampton
$2,700,000
4 Beds ⋅ 4 Baths ⋅ 1053275 MLS
Set south of County Road 39 in Southampton and less than two miles from the Village, this beautifully updated residence offers refined living in a private setting on 0.46 acres. Renovated and thoughtfully enhanced throughout the past decade, the home combines generous living spaces with a serene outdoor retreat. The first floor unfolds from an inviting foyer to a gracious living room with fireplace, den, dining room, and chef's kitchen. A first-floor bedroom and full bath offer added flexibility, while an attached one-car garage provides everyday convenience. Upstairs, the luxurious primary suite is joined by two additional guest bedrooms and a full bath. The finished lower level further expands the living space with a large recreational room, office, full bath, and laundry room. Outside, a freeform heated pool is framed by a stone patio, lush lawn, and mature landscaping, creating a private setting for relaxing and entertaining. A nearby path leads to Southampton Meadows Park -- a 2.5-acre community park complete with amenities including a sunken tennis court, chess table, picnic pavilion, and playground. Ideally located close to Southampton Village, beaches, and the best of the Hamptons, this exceptional property offers a refined year-round retreat. This listing may include images that have been digitally altered or virtually staged. Original, unedited images are available upon request.

5 William Way, Southampton

70 Middle Pond Road Unit #22, Southampton
$2,399,999
5 Beds ⋅ 3 Baths ⋅ 1052698 MLS
Rarely does a Southampton property offer the scale, privacy, and character of a standalone five-bedroom home with the ease of a waterfront community lifestyle. Set within Middle Pond Estates, this exceptional co-op offers approximately 2,500 square feet of living space and an uncommon sense of scale. With a nod to Southampton's rich maritime heritage, the home evokes the spirit of a classic captain's house—spacious, welcoming, and designed for gathering. The thoughtful layout includes five bedrooms, three beautifully renovated baths, a newly completed kitchen renovation, a generous living room, and an impressive great room featuring a fireplace and picturesque views of the beach and pool. Enjoy the best of waterfront living with community amenities including a private beach, scenic saltwater pool, and beautifully maintained grounds. Whether relaxing by the water, entertaining guests, or enjoying the tranquility of the East End, this unique residence offers a rare opportunity to experience Southampton living in a setting that feels truly like home.

70 Middle Pond Road Unit #22, Southampton

1768 Majors Path, Southampton
$4,795,000
6 Beds ⋅ 7 Baths ⋅ 1041882 MLS
Welcome to 1768 Majors Path, an exceptional new-construction estate in Southampton offering a refined interpretation of contemporary Hamptons living. Privately positioned on 1.07 acres, this sophisticated residence features more than 5,500 square feet across three beautifully designed levels, with six bedrooms, seven baths, a heated saltwater Gunite pool, a Tennis Court, an Indoor Red Light Sauna and an attached two-car heated garage. A dramatic double-height foyer introduces the open-concept interior, where timeless architectural details, premium materials, and quality craftsmanship create an elegant yet comfortable atmosphere. The expansive, sun-drenched great room w/ high ceilings & oversized windows, centered around a gas fireplace, flows seamlessly into an additional living area and opens to a beautiful backyard designed for the Hamptons lifestyle. The expansive grounds feature a mahogany deck, a large paved bluestone patio with a gas fireplace and an outdoor kitchen, a heated saltwater Gunite pool, and a private tennis court, creating an ideal setting for relaxation and entertaining. This home has a state-of-the-art chef’s kitchen equipped with premium stainless-steel appliances, generous preparation space, and high-end finishes selected for both beauty and function, with oak Hardwood floors throughout. The second level is highlighted by an oversized primary suite designed as a private retreat, with cathedral ceilings that enhance the sense of space, a gas fireplace, and a private mahogany terrace overlooking the pool and professionally landscaped grounds. Two walk-in closets and a spa-inspired bathroom with a soaking tub complete the suite. Three additional ensuite bedrooms offer privacy and comfort for guests. The finished lower level extends the home’s year-round living and entertaining possibilities with a spacious recreation area, home gym, additional bedroom suite, and laundry room. Located in a peaceful Southampton setting, moments from the water, beautiful beaches, marinas, golf courses, and the celebrated shops, restaurants, and cultural destinations of nearby Hamptons villages, 1768 Majors Path presents a rare opportunity to own a newly constructed luxury home with exceptional amenities in one of the East End’s most desirable destinations.

1768 Majors Path, Southampton

142 Little Fresh Pond Road, Southampton
$1,999,000
4 Beds ⋅ 3 Baths ⋅ 1051253 MLS
Set directly on Little Fresh Pond in Southampton, this distinctive four-bedroom, three-bathroom waterfront residence offers a rare combination of privacy, expansive indoor-outdoor living, and approximately 81 feet of water frontage with a private dock. Situated on .62± acres and thoughtfully renovated and expanded in 2004, the home has been designed to take full advantage of its peaceful setting and connection to the water. The first floor is centered around a sun-filled great room, where expansive sliding glass doors open directly onto more than 1,000± square feet of decking, creating a seamless transition between the interior and the waterfront landscape beyond. The open-concept kitchen is designed for both everyday living and entertaining, featuring an impressive suite of appliances including a Wolf oven, induction range and wok burner, along with Thermador refrigeration, Sub-Zero freezer drawers and an Asko dishwasher. A formal dining room provides a dedicated space for gatherings, while two comfortable bedrooms and a full bathroom complete the main level. Additional features include stainless steel siding, a heated two-car garage, smart Lutron lighting, built-in vacuum system & radiant heat throughout the first-floor living areas, kitchen and primary bathroom. Occupying the second floor, the private primary suite serves as a true retreat. The oversized bedroom opens to its own private balcony, while a dedicated dressing room features two built-in closets. The spacious primary bathroom is appointed with two separate vanities, an oversized soaking tub, steam shower, radiant heated floors and a Toto Washlet. Electric skylights bring additional natural light into the upper level, further enhancing the home's bright and airy atmosphere. The finished lower level adds approximately 840± square feet of versatile living space and includes a fourth bedroom, full bathroom and generous recreation room with direct walkout access. A thoughtfully designed laundry area with ample countertop space and a sink adds functionality to the lower level, while wine storage tucked beneath the stairs provides a practical finishing touch. Outdoor living is an integral part of the property. More than 1,000± square feet of decking, a covered porch and retractable awning provide multiple areas for dining, lounging and entertaining while overlooking Little Fresh Pond. A private dock and walkway lead directly to the water, offering an exceptional setting for enjoying the pond throughout the seasons.

142 Little Fresh Pond Road, Southampton

38 Old Fort Lane, Southampton
$2,750,000
3 Beds ⋅ 3 Baths ⋅ 1049087 MLS
South of the highway on Old Fort Pond with access to Shinnecock Bay, this well-maintained waterfront home offers panoramic water views and spectacular sunrises and sunsets. The light-filled open floor plan features 3 bedrooms, a home office, and spacious living areas designed to take advantage of the waterfront setting. The large kitchen is equipped with stainless steel appliances and opens to a generous great room with walls of sliding glass doors leading to the waterside deck. Enjoy seamless indoor-outdoor living with an expansive lawn overlooking the water and a private dock ideal for boating, fishing, kayaking, and paddleboarding. A first-floor den with a full bath provides additional living space and flexibility for guests. The second-floor primary suite features a private balcony with water views, an en-suite bath, and a Jacuzzi tub. Two additional guest bedrooms and a full bath complete the second level. Conveniently located minutes from Southampton Village, fine dining, shopping, world-class ocean beaches, and all the amenities of the Hamptons. Exclusive waterfront offering with private dock, expansive water views, and easy access to Shinnecock Bay.

38 Old Fort Lane, Southampton

48 Beechwood Drive, Southampton
$2,999,000
4 Beds ⋅ 6 Baths ⋅ 1049950 MLS
Moments from Big Fresh Pond and surrounded by some of Southampton's most beloved nature trails, this beautifully renovated four-bedroom, five-and-a-half-bath residence with a bonus room pairs refined finishes with an easy, thoughtful layout designed for everyday Hamptons living. Step inside to bright, open-concept living and dining spaces defined by 9-foot ceilings and 8-inch wide-plank white oak floors. Sliding glass doors from the dining area open directly to the rear deck, creating a natural connection between the home's main gathering spaces and the outdoors. Just beyond, the eat-in kitchen is beautifully appointed with Sub-Zero and Wolf appliances and offers its own sliding glass doors to the backyard. A powder room and dedicated laundry room complete the main living areas. Privately positioned in its own wing, the first-floor primary suite offers a peaceful retreat with a beautifully appointed spa-like bath featuring radiant heated floors, thoughtful upgrades including a TOTO fixture, and a striking picture window overlooking the grounds. Upstairs, two well-appointed en-suite bedrooms are joined by an additional bedroom and full hall bath, as well as a generously sized bonus room with a closet offering valuable flexibility as a home office, den, playroom, or additional living space. The finished lower level provides even more room for recreation, fitness, or relaxation, while an attached 1.5-car garage adds everyday convenience. Outside, meticulously landscaped grounds create a private retreat centered around a heated pool, covered trellis, multiple patio seating areas, spacious deck, and outdoor shower—an inviting setting for long summer days and evenings under the stars. Thoughtfully renovated and beautifully finished throughout, this exceptional property brings together privacy, comfort, and effortless Hamptons living, with Southampton Village, renowned ocean beaches, dining, shopping, and everything the area has to offer within easy reach.

48 Beechwood Drive, Southampton

422 Montauk Highway, Southampton
$2,200,000
4 Beds ⋅ 3 Baths ⋅ 1049213 MLS
A rare opportunity south of the highway in coveted Shinnecock Hills, this distinctive property offers the perfect canvas for creating an exceptional Hamptons retreat. Set on just shy of an acre surrounded by mature trees, this recently refreshed Contemporary homecombines substantial living space, versatile accommodations and remarkable potential. Approximately 3,000 square feet of living space features a total of 4 bedrooms, 3 bathrooms, soaring cathedral ceilings, custom doors and sliders, a wood-burning fireplace and refined updates throughout. The second-floor primary suite is a private sanctuary with an ensuite bath, private balcony and separate lounge area. Adding an exceptional level of flexibility is a separate two-level guest/in-law suite with its own private entrance and separate kosher kitchen, offering an ideal retreat for extended family and guests-or an inspiring space for a home office, studio or additional living quarters. Thoughtfully designed for modern Hamptons living, the residence also offers two laundry areas, multi-zone HVAC, an attached two-car garage and a full unfinished walkout basement spanning the footprint of the home, presenting significant potential for future expansion and customization. The outdoor experience is equally impressive. An extraordinary 1,800-square-foot, three-level wraparound deck extends dramatically from the interior living spaces, creating an expansive setting for sophisticated entertaining, and effortless summer living. With ample room for a pool and additional opportunities to enhance the grounds, the property invites a truly personalized vision.Ideally positioned just moments from both bay and ocean beaches and minutes from Southampton Village, this is a compelling opportunity to create a distinctive luxury retreat in one of the Hamptons' most coveted locations.

422 Montauk Highway, Southampton

421 Edge of Woods Road, Water Mill
$5,595,000
5 Beds ⋅ 9 Baths ⋅ 1048083 MLS
Privately set at the end of a long driveway on approximately 2.5 acres in Water Mill, this private Water Mill estate combines scale, privacy and resort-style living with convenient access to Southampton Village, ocean beaches, dining and shopping. Built in 2019, the approximately 7,635-square-foot residence offers 5 bedrooms, 8 full baths and 1 half bath across three finished levels, complemented by two separate pool houses and an oversized 3-car garage. The main level is designed for both everyday living and entertaining, with an expansive gourmet kitchen featuring fully integrated Thermador appliances, oversized paneled refrigeration, wine refrigerator and radiant-heated floors, opening to generous living and dining spaces. Three gas fireplaces add warmth throughout the home. Upstairs, two spacious primary suites each feature private balcony access, dual closets, luxurious baths and radiant-heated floors, joined by two additional bedrooms and a dedicated laundry room. The finished lower level provides substantial additional living space with a large recreation area, fifth bedroom and full bath, ideal for guests, fitness, media or play. Outdoors, the property unfolds into a private Hamptons retreat centered around a heated gunite pool, expansive bluestone patios and multiple areas for lounging, dining and entertaining. Two approximately 370-square-foot accessory pool houses further elevate the setting—one with a full kitchen, lounge, and bath, and the second offering flexible finished space well suited for a home office, gym, yoga studio, art studio or playroom. Additional highlights include an owned rooftop solar system, whole-property fiber-optic Wi-Fi coverage extending to the pool and accessory buildings, bedroom blackout shades, and a dedicated elevator bay designed for future installation. A rare combination of privacy, versatility and Hamptons lifestyle in an exceptional Water Mill setting.

421 Edge of Woods Road, Water Mill

601 Water Mill Towd Road, Southampton
$3,200,000
6 Beds ⋅ 2 Baths ⋅ 1034303 MLS
TWO LOTS are being SOLD TOGETHER! 601 WATERMILL TOWD ROAD & 591 WATERMILL TOWD ROAD ARE BEING SOLD TOGETHER! This beautiful, bright six-bedroom, two-full-bath home sits on 1.055a and features a circular driveway, expansive back yard, outdoor shower and charming garden. The entry foyer leads to the sunlit living room featuring a wood burning fireplace, built-ins and dramatic floor-to-ceiling windows. The expansive eat-in kitchen and spacious family room share an open floor plan. Together, they are perfectly designed for dining & entertaining. They boast a wood burning fireplace and 3 sets of french doors which lead out to the oversized deck. A guest bedroom and full bath complete the first floor. The second floor includes the primary bedroom plus 4 additional bedrooms and full bath. 591 WATERMILL TOWD ROAD, A SINGLE & SEPARATE BUILDABLE LOT is included in this sale. The additional, single & separate .355a buildable lot is perfect for a pool, pool house and/or tennis/pickleball court. The possibilities are endless as paradise awaits you in Southampton!

601 Water Mill Towd Road, Southampton

28 Andrew Court, Southampton
$1,525,000
3 Beds ⋅ 3 Baths ⋅ 1046627 MLS
This immaculately maintained and beautifully decorated townhouse at The Courtyards is located just a short drive from Southampton Village, its restaurants, shops, and renowned ocean beaches. The first floor features a bright and open living room, dining area, updated kitchen, full bath, and sliders leading to a private patio with space for outdoor dining, lounging, and a hot tub for relaxing and rewinding. Upstairs, the spacious primary suite includes a large bath with shower and Jacuzzi tub plus a walk-in closet, along with two additional spacious bedrooms and a full bath. The fully finished lower level offers an infrared sauna, exercise area, sectional sofa for relaxing and watching TV, and laundry room. The condo includes a one car garage. The Courtyards community features a heated pool, cabana with changing room, and playground.

28 Andrew Court, Southampton

39 Spring Pond Lane, Southampton
$1,375,000
4 Beds ⋅ 3 Baths ⋅ 1046663 MLS
This contemporary 4-bedroom townhouse offers spacious, light-filled living in one of Southampton's most desirable locations. Designed for both comfort and entertaining, the open-concept living, dining, and kitchen area features double-height ceilings, a dramatic floor-to-ceiling fireplace, and a flowing layout that seamlessly connects the home's main living spaces. The thoughtfully designed layout includes two primary suites-one upstairs with a spacious bath and generous accommodations, and a second on the main level with direct access to the pool area. In total, the home offers four bedrooms and three full baths, providing flexibility for family and guests alike. Additional highlights include hardwood floors throughout, a heated pool, sunny decks, a full-height basement for abundant storage, and an attached two-car garage. Community tennis courts add to the lifestyle amenities. Ideally located just moments from the beaches of Great Peconic Bay, renowned East End golf courses, marinas, and Southampton's award-winning ocean beaches, this bright and well-maintained home presents an exceptional opportunity to enjoy the very best of East End living.

39 Spring Pond Lane, Southampton

493 Sagg Main Street, Sagaponack
$24,995,000
9 Beds ⋅ 13 Baths ⋅ 1045735 MLS
Set along one of the most coveted stretches of Sagaponack South, just moments from the ocean, **493 Sagaponack Main Street is now complete**, presenting a rare opportunity to own a newly constructed estate in the Hamptons’ most exclusive and highest-priced zip code. Sited on 1.9 meticulously designed acres, this 11,369-square-foot residence has been thoughtfully conceived as a seamless blend of classic Hamptons architecture and modern luxury living, where every detail—from scale to finish—feels both timeless and forward. Arriving through a gracious drive, the home reveals a commanding yet elegant presence, with expansive windows and refined cedar-shingle craftsmanship that invite natural light throughout. Inside, a flowing floor plan unfolds across three levels, offering nine bedrooms—including a junior suite on the first level and a private primary suite upstairs—alongside eleven full and three half baths. Designed for both grand entertaining and intimate living, the interiors are complemented by an elevator servicing all levels, as well as a full suite of lifestyle amenities including a golf simulator with lounge area, a state-of-the-art gym, and a spa retreat featuring a large sauna, steam shower, and outdoor plunge pool. Outdoors, the estate transforms into a private resort. A 20×60 heated gunite pool and spa anchor the grounds, accompanied by a beautifully appointed pool house and expansive lounging areas that capture the essence of Hamptons summer living. The sunken tennis court adds another layer of recreation, while curated landscaping frames multiple entertaining zones—from al fresco dining terraces to quiet garden moments—creating a sense of privacy and serenity rarely found this close to the beach. As the day transitions to evening, the property takes on an entirely new character—warm interior lighting glows through oversized windows, landscape lighting softly defines the grounds, and the estate becomes a true showcase of architectural elegance. Whether hosting under the stars or enjoying a quiet weekend escape, every moment here is elevated. **Now fully completed and ready to be experienced,** 493 Sagaponack Main Street is more than a home—it is a statement property, delivering extraordinary scale, an exceptional location, and the rarity of brand-new construction in a market where opportunities of this caliber are nearly nonexistent. For the discerning buyer seeking immediate access to the Hamptons lifestyle at its highest level, this is an address that defines Sagaponack living.

493 Sagg Main Street, Sagaponack

65 Middle Pond Road, Southampton
$5,995,000
7 Beds ⋅ 9 Baths ⋅ 1044683 MLS
South of the Highway in Southampton, this exceptional residence offers panoramic views of Middle Pond and Shinnecock Bay on a beautifully landscaped property designed for year-round enjoyment. A grand foyer welcomes you into a thoughtfully designed home featuring bleached 8-inch red oak floors, 10-foot coffered ceilings, extensive custom millwork, and an indoor-outdoor carved soapstone fireplace. The open layout blends classic architectural details with modern amenities throughout. The chef's kitchen is appointed with 3-inch Pietra Cardoza countertops, a marble backsplash, custom cabinetry, double sinks, an 8-burner Wolf range, a 60-inch Sub-Zero refrigerator, and dual Miele dishwashers. Adjacent living and dining spaces are designed for both everyday living and entertaining, including a spacious great room with a wood-burning fireplace and direct access to the outdoor patio. A first-floor junior suite provides additional accommodations. The second level features a primary suite with a shiplap ceiling, custom walk-in closet, en-suite bath, and library lounge. Three additional guest suites offer private baths, built-in closets, and balconies with multiple water-facing exposures. The finished lower level is designed for recreation and relaxation, featuring a spa area with sauna and steam room, temperature-controlled wine cellar, media room, fitness area, and additional guest suite. Outdoor amenities include a heated Gunite saltwater pool with waterfall, expansive stone patio, layered stone walls, mature landscaping, and a cabana with outdoor kitchenette, bath, and shower. Conveniently located approximately three miles from Southampton Village and ocean beaches, this property presents an opportunity to enjoy Southampton living with water views, privacy, and extensive amenities.

65 Middle Pond Road, Southampton

845 County Road 39, Southampton
$1,559,000
4 Beds ⋅ 3 Baths ⋅ 1045106 MLS
A chic, well-appointed Hamptons cottage offering an easy entry into the Southampton lifestyle. This four-bedroom, two-and-a-half-bath home is set on a generous half-acre with a fully fenced backyard, ample room for a pool, and thoughtfully designed outdoor spaces made for relaxed summer living. Inside, bright, updated interiors feature an open concept living, dining, and kitchen area with hardwood floors, a spacious center island, stone countertops, stainless steel appliances, and an effortless coastal feel. Four comfortable bedrooms and beautifully updated baths provide plenty of room for family and guests, while central air and a dedicated laundry area add everyday convenience. Outdoors, an expansive lawn creates a private backdrop for summer gatherings, with a patio, Jacuzzi, fire pit, outdoor shower, and storage shed already in place, while still leaving plenty of room to make the property your own. Adjacent to Southampton Golf Club and within easy reach of Southampton Village, ocean beaches, dining, shopping, and everything the East End has to offer, the home is equally suited as a year-round residence, weekend escape, or investment property with a strong rental history. Turnkey, inviting, and refreshingly easy - a versatile Southampton home ready to enjoy from day one.

845 County Road 39, Southampton

8 Boathouse Road, Hampton Bays
$2,200,000
11 Beds ⋅ 6 Baths ⋅ 1045061 MLS
NEW! Unique Mid-Century Six-Cottage Compound in Shinnecock Hills First time ever on market opportunity to own an original mid-century cottage compound in the sought-after Shinnecock Hills. Set on a flat 1.16-acre parcel with R-20 zoning, the property consists of six cottages, offering a unique opportunity for investment, rental income, personal use, or a combination of all three. Five of the cottages, each approximately 500 SF, have 2 bedrooms, one bath and open kitchen, dining, living area. One cottage, approximately 800 SF, has one bedroom, one bath and open kitchen, dining, living area. Just a quarter mile from Peconic Bay, with the Town boat launch conveniently located around the corner, the property puts boating, fishing, kayaking, and waterfront recreation within easy reach. Multiple renowned waterfront restaurants along Peconic and Shinnecock Bays are also close by. An exceptional opportunity to own a piece of old-school Hamptons/Poconos style character while enjoying the convenience of being close to Southampton and the area's beaches, restaurants, and marinas. With six cottages on a generous, level parcel, 8 Boat House Road offers flexibility and potential rarely found in Shinnecock Hills. Beat the traffic and enjoy the best of the East End from this unique six-cottage compound.

8 Boathouse Road, Hampton Bays

Listings courtesy of OneKey® MLS as distributed by MLS GRID. Based on information submitted to the MLS GRID as of . All data is obtained from various sources and may not have been verified by broker or MLS GRID. Supplied Open House Information is subject to change without notice. All information should be independently reviewed and verified for accuracy. Properties may or may not be listed by the office/agent presenting the information.

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