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$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
$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
$1,495,000
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
$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
$1,495,000
5 Beds ⋅ 2 Baths ⋅ 1002100 MLS
Investors or primary owner dream, could be your beautiful summer home or rental with 5BR/2BT ready for a Full-Sized Pool w/ beautiful private yard and location. Situated on more than half an acre (.55 acres) home features 5 bedrooms, 2 baths w/ office, updated kitchen, living/dining room, laundry and full basement. DESIRABLE LOCATION: No car is necessary, as you’re walking distance to the Village and Hampton Jitney. Walking distance & 4 block from the main street, which includes features such as a Hampton Jitney stop, restaurants, delis & various shops. HOME FEATURES: 5 bedrooms and 2 bathrooms with open living area, huge property ready for a beautiful pool, w/ spacious outdoor sitting areas. INSIDE FEATURES: Beautiful kitchen, dining and living room area, dining room table with large living room area. Kitchen/Dining Room area transition to an outdoor deck sitting area. • Master Bedroom –King bed, includes walk-in closet, full jack and Jill bath. • Bedroom (2) – Queen bed, includes spacious closet. • Bedroom (3) – Queen bed, includes spacious closet. • Bedroom (4) – Twin bed w/ trundle, spacious closet. • Bonus Rooms: bedroom and Office. BACKYARD FEATURES: Huge (fenced-in) backyard ready for entertainment space: • Private Pool: can be an 18 by 40 high-end heated salt & natural mineral pool w/ 8-foot-deep end. This could be an entertainment and leisure pool. • Large patio ready for an outdoor Fireplace. • Large Deck: Featuring a 6-seater outdoor dining table w/ Propane BBQ Grill and a small (4) seater wicker sofa. • Property Landscaping: Beautiful Private landscaped and spacious backyard for entertaining.

248 County Rd 39, Southampton
$2,295,000
7 Beds ⋅ 6 Baths ⋅ 865275 MLS
OWNER MOTIVATER!!!!! Any reasonable offer will be considered.

251 Sebonac Road, Southampton

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.