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On a tranquil street, less than a half mile from the Atlantic Ocean and near the center of the village, this updated Southampton classic offers 5 bedrooms, 5 and a half baths, CAC and heated pool all on 1 private acre. Find a combination of classic Hamptons charm with bright contemporary accents & amenities. Also available Thanksgiving and Christmas weeks for $25K Weekly Rental Terms: September: $35,000 October: $35,000
…By Sotheby's International Realty - Southampton Brokerage
Convenient to town and bay beaches, this recently renovated home is picture perfect. Features 3 bedrooms, 2 baths, living area, current kitchen, and a crisp decor. Outside entertaining under a pergola. A great Hampton's vacation home. Available year round for $110,000. [[Rental Registration # Rp250475]] EH RR #: Rp250475 Rental Terms: Other / Short Term - Year Round: $115,000 July: $30,000 August - Labor Day: $35,000 June/July: $45,000 Memorial Day - Labor Day: $75,000 July - Labor Day: $65,000 June: $15,000
…By Sotheby's International Realty - Bridgehampton Brokerage
A Stunning Coastal Retreat - Bask in breathtaking ocean views and crisp sea air from this exceptional East Hampton rental. Located between Montauk and Amagansett, this sun-drenched 3+ bedroom, 4-bath home offers effortless coastal living. Enjoy panoramic Atlantic views from every room, an open and airy floor plan, and a walking path to the ocean. Whether savoring sunrise coffee on the expansive deck or unwinding to the soothing sound of the waves, this home is the perfect Hamptons getaway. Located minutes from world-class beaches, shopping, and dining, this centrally positioned gem is a rare find. Rent your dream seaside escape today! [[Rental Registration # Pending]] EH RR #: 23-1168 Rental Terms: July - Labor Day: $150,000
…By Sotheby's International Realty - East Hampton Brokerage
This newly renovated modern in the Dunes with a new pool has four bedrooms and 4 bathrooms. The first floor has a bright and open kitchen and living room with a fireplace overlooking a deck with a heated pool, three bedrooms and two bathrooms. The second floor has the master bedroom and bathroom, a loft with two additional trundle beds, and a guest bathroom. There is a beautiful collection of contemporary art work throughout the house. [[Rental Registration # 23-259]] EH RR #: 23-259 Rental Terms: Memorial Day - Labor Day: $170,000 September: $42,500 August - Labor Day: $75,000 July: $65,000 July - Labor Day: $135,000
…By Sotheby's International Realty - Bridgehampton Brokerage
Tucked away on a quiet dead-end street among private, wooded acre lots, this light-filled Hamptons home offers the perfect summer escape with space to relax, gather, and entertain. Enjoy long summer days by the 20' x 40' heated pool, surrounded by peaceful natural surroundings and room to spread out. Inside, the main living area features soaring vaulted ceilings and an open-concept layout that flows into the eat-in kitchen with island seating-ideal for family meals or hosting guests. Sliding doors lead seamlessly to the deck, creating effortless indoor-outdoor living for summer dining and lounging. The primary en-suite bedroom and two first-floor guest bedrooms all feature king-sized beds, vaulted ceilings and generous closet space. The lower level is designed for fun and flexibility, with a spacious recreation and lounge area complete with wet bar, ping pong, foosball, accessory kitchen, TV area, full bath, office, and an additional king-size guest bedroom with bonus bunk beds. Two sliding glass doors open directly to the patio and pool area, making it easy to move from games indoors to poolside afternoons outside. Located just 2 miles from beautiful West Landing Beach, and conveniently positioned between the vibrant villages of Westhampton Beach and Southampton for shopping and dining. Hampton Bays is especially loved for its exceptional waterfront restaurants, relaxed coastal charm, and easy access to both the bay and world-class ocean beaches. [[Rental Registration # RP260404]] EH RR #: RP260404 Rental Terms: August - Labor Day: $37,000 Other / Short Term - 6/15/2026 - 7/14/2026: $30,000 August: $30,000 June: $18,000
…By Sotheby's International Realty - Southampton Brokerage
Rental Reg# 22-396 expires 4/4/24 Also available Aug $40K Stately 5,800 square foot, 5 bedroom, 5.5 bath home on 2 acres surrounded by lush old growth beech forest. House is centered on an expansive and open floor plan perfect for gathering and entertaining and featuring large living and dining rooms, chefs kitchen, and sunny den. Large primary bedrooms on ground level and second floor. Multi-level exterior features deck off living area, overlooking extremely private and beautifully landscaped heated pool and patio. Perfect for an after-beach swim and barbecue. Less than 10 minutes from the center of Amagansett Village, shops, restaurants and ocean beaches. EH RR #: 22-396 Rental Terms: July: $52,500 Other / Short Term - July 15 - Sep 4: $77,000 July - Labor Day: $118,000 August - Labor Day: $54,000
…By Sotheby's International Realty - East Hampton Brokerage
Located in the beautiful beachfront community of Clearwater Beach, this charming 3 bedroom, 2 bathroom saltbox has been newly refreshed and is available for seasonal or year-round rental. Mature privacy plantings, lush gardens, a pool, patios and a deck provide ample opportunities for outdoor entertainment. This property is located a short distance to the private Clearwater Beach marina with a lifeguarded beach, grilling stations, playground, bocce ball court and the perfect location to enjoy incredible sunsets. [[Rental Registration # 26-1175]] EH RR #: 26-1175 Rental Terms: August - Labor Day: $32,000 June: $12,000 July: $28,000 Other / Short Term - Year Round: $96,000 May: $10,000 Winter Season: $44,000 Per Month Memorial Day - Labor Day: $72,000 July - Labor Day: $55,000
…By Sotheby's International Realty - East Hampton Brokerage
Totally renovated with the finest historic details, offering spacious, light-filled double parlors, a grand chef's entertaining kitchen fully opens to an expansive porch with built in heating for chilly nights, a private dining patio, gunite pool, spa, poolhouse bar, powder room & outdoor grotto shower. Three floors offer 5+ bedrooms, 7 baths, luxe library, butler's pantry, 7 fireplaces, viewing balcony decks on the 2nd floor. Perfect entertaining home in the heart of Sag Harbor village, close to theater, restaurants and marina. [[Rental Registration # landlordrequested]] EH RR #: landlord requested Rental Terms: Other / Short Term - Year Round: $550,000 Winter Season: $270,000 Per Month Memorial Day - Labor Day: $325,000
…By Sotheby's International Realty - Bridgehampton Brokerage
Built just a few years ago and newly furnished for the 2026 summer season, this Westhampton retreat offers the comfort and style of a new-construction home. Bright, airy, and effortlessly beachy, the open-concept floor plan features an eat-in kitchen with a center island, spacious dining area, media room, and seamless indoor-outdoor living that opens to the deck and pool area.The home comfortably accommodates family and guests with a king-size primary suite, a queen-size en-suite bedroom, and two additional guest bedrooms-one furnished with a king bed and the other with a full bed and pull-out sofa. Outside, the flat, sun-drenched yard is designed for effortless summer living, with plenty of space for lawn games, entertaining, and lounging poolside from morning through sunset. Ideally located just minutes from the shops, restaurants, and village charm of Westhampton Beach, with easy access to Southampton Town's renowned ocean beaches, this is the perfect setting for an unforgettable Hamptons summer. [[Rental Registration # RA260729]] EH RR #: RA260729 Rental Terms: October: $12,000 Other / Short Term - 7/12/2027 - 8/13/2027: $38,000 Two Weeks: $16,000 November: $8,000
…By Sotheby's International Realty - Southampton Brokerage
A stone's throw from the heart of East Hampton Village, this fully renovated and thoughtfully designed home offers the perfect Hamptons escape. Privately set behind mature landscaping and a gated entry, this new rental delivers a rare combination of charm, convenience, and turnkey ease. Inside features two well-proportioned bedrooms and two full baths, complemented by a spacious living room and eat-in kitchen. Outdoors, enjoy a private yard ideal for relaxing or entertaining after a day at the beach. Minutes to village shops, dining, and the area's most desirable ocean beaches. [[Rental Registration # RR-26-353]] EH RR #: RR-26-353 Rental Terms: June/July: $25,000 July - Labor Day: $38,000 August - Labor Day: $28,000 July: $16,000 Memorial Day - Labor Day: $45,000
…By Sotheby's International Realty - Bridgehampton Brokerage
Recently Remodeled Colonial Home on 2 Acres of Property Overlooking the Nissequogue River with Rocking Chair Front Porch. Many Updates Include New Roof, Siding, Driveway, & Eat In Kitchen. Freshly Painted in March 2026 with Refinished Wood Flooring. Den w Wood Burning Fireplace, Updated Bathrooms, Full Basement, 2 Car Garage. Rear Yard is Surrounded by Mature Trees and is Tranquil and Serene. Nearby are Local Beaches, Hiking Trails, Fine Dining, Local Shopping, and Stony Brook University and Medical Center. Smithtown Schools.
…By Daniel Gale Sotheby's International Realty
A perfect village summer retreat awaits at this new 3 bedroom, 2.5 bath home right in the heart of East Hampton's village. High end kitchen, sophisticated and well appointed baths, plus three well proportioned bedrooms. There is also a large upstairs den that can double as a bedroom. Gorgeous yard and winning location make this one a real delight. Rental Terms: July: $32,000 Other / Short Term - June: $15,000 August - Labor Day: $35,000 Memorial Day - Labor Day: $80,000
…By Sotheby's International Realty - East Hampton Brokerage
Located on a quiet street around the corner from a private bay beach, and short walk, ride or drive to the village, this light-filled, minimalist, stylish home offers the perfect choice for your summer getaway. With 3 bedrooms and 3 bathrooms, the house offers ample space for families. The main floor includes a guest bedroom and bathroom, while the upper floor hosts the primary suite and an additional guest bedroom and bathroom. The chef's kitchen features stainless steel appliances, a massive island and dining table for entertaining and family meals. The deck overlooks manicured grounds, perfect for outdoor entertaining and morning coffee listening to birdsong. The lower level provides a TV lounge, air hockey table, a laundry facility, and an extra bathroom for added convenience. Whether you're planning a peaceful retreat or an active vacation, this home serves as the ultimate base for all your vacation plans and village fun. Available June 25th to Sept 7th. $50,000 [[Rental Registration # inprogress]] EH RR #: R-25-0006 Rental Terms: August - Labor Day: $35,000
…By Sotheby's International Realty - Southampton Brokerage
This newer construction is a rare find. The inside features high-end, custom furnishings rarely available in a rental at this price. Gorgeous architecture, interior design and mature landscaping will impress. The 7 Bedroom home (all with ensuite baths) spans 5800 feet above ground, plus 2550 feet of finished lower level. The First floor features a dramatic 2-story foyer, 2 spacious living rooms, a chef's kitchen, bar area. There is a Junior Primary, and a mudroom with pool bath. The Second Floor features a Primary suite with terrace, fireplace, and luxurious white marble bath. There are 4 additional ensuite bedrooms and a second laundry. The lower level offers expansive entertainment space, including a theater, living room, and playroom with ping pong. There is a 7th ensuite bedroom with 2 queen beds. Outside, a South-facing large terrace with overlooks a beautifully landscaped, 1-acre property, with farm views. The yard is private and includes a 40' pool, new sunken hot tub and generous patio space for entertaining. The house sits in a very quiet cul de sac of newer homes, 2 miles to Southampton Village, with Southampton beaches just beyond. The property is a short bike ride or walk to the Southampton Rec Center (SYS) which offers a fantastic children's camp, tennis, gym, basketball, track, yoga, and pilates. Its also 1.5 miles to Towd Point Beach, one of the Hamptons prettiest bay beaches. [[Rental Registration # RP230864]] EH RR #: RP230864 Rental Terms: April: $15,000 February: $15,000 Other / Short Term - 1/1/2027 - 4/30/2027: $60,000 November: $25,000 September: $45,000 October: $30,000 January: $15,000 March: $15,000 Winter Season: $90,000 Per Month
…By Sotheby's International Realty - Bridgehampton Brokerage
Discover waterfront living at its finest within this extraordinary all custom home. The mesmerizing panoramic views flow seamlessly throughout with spontaneous access to the private wide sandy beach. Set on the shores of iconic Gardiner's Bay, this property provides a beach access staircase, gated marina, lifeguarded beach and spectacular direct sunsets that fill the evening sky. Widely regarded as one of East Hampton's premier waterfront properties, this extraordinary home delivers an unparalleled coastal lifestyle. Designed for effortless luxury, the beautifully appointed five-bedroom residence combines elegant interiors with continuous water and beach views throughout. The spacious interior holds living room with stone fireplace, a formal water view dining area, also with fireplace. Additionally, a lovely sitting area with fireplace is situated off a chef's dream kitchen. Thoughtfuly designed, it has an open wall space over the kitchen counter for effortless serving indoor and outdoor dining and to invite in the waterviews. The professional appliances include a full size Sub Zero refrigerator & freezer unit, a Wolf stove, two dishwashers, ice maker and many other amenities. There are five ensuite bedrooms on various separate wings including a lavish primary bedroom with fireplace and private access to its own expansive waterfront deck with forever views. Also included are a zen-like massage and exercise room and a large entertaining room with fun activities including billiards, bar, ping pong with an oversized flat screen. The three level expansive decking provides various vantage point choices to view the surrounding water views and meandering beach. Just steps from the sand to create memories of swimming, sunsets, kayaking, boating, or deep relaxation by the shore. Experience an unparalleled beachfront lifestyle moments from waterfront restaurants and the charm of East Hampton Village. [[Rental Registration # 22-101]] EH RR #: 22-101 Rental Terms: Memorial Day - Labor Day: $450,000 November: $40,000
…By Sotheby's International Realty - East Hampton Brokerage
Set within the natural beauty of the Lloyd Neck peninsula, this striking post-modern home offers a sophisticated yet wonderfully relaxed lifestyle. Designed to embrace its setting, the home is bright and airy, with an open floor plan, soaring ceilings, and walls of windows that beautifully frame the surrounding landscape. At the heart of the home is an updated kitchen featuring top-of-the line stainless appliances including an 8-burner Viking stove, and a combination of generous cabinetry and open shelving. Just off the kitchen, a spacious den provides the perfect setting for casual entertaining, movie nights or simply unwinding at the end of the day. The spacious vaulted ceiling primary retreat has access to a private balcony, an ideal spot for morning coffee or quiet relaxation, and an updated and generously sized en-suite bath with a luxurious freestanding soaking tub and glass-enclosed shower. The spectacular grounds feature an expansive deck and in-ground pool which create a private resort-like setting for summer enjoyment. Nature lovers can enjoy nearby Target Rock National Wildlife Refuge and Caumsett State Park. This is a wonderful opportunity to enjoy the North Shore lifestyle.
…By Daniel Gale Sotheby's International Realty
This modern Bayfront masterpiece designed by renowned architect Robert Barnes, perfectly situated on a Dune for panoramic water and meadow views, instantly captivates. The dramatic walls of glass invite in continuous water views throughout with stunning exterior environs. On 1.16+/- acres of complete privacy, it is enveloped by 10+/- acres of pastoral meadows with spectacular evening sunsets and sunrises. The terraced structure holds a dramatic floating second story creating a bridged covered patio with flowing natural light overlooking a 50' saltwater pool. The huge stone outdoor fireplace and pool house complete a perfect setting for memorable gatherings. Exquisitely landscaped grounds abound in the tranquility of nature. Designed by Thomas Balsley, delight in the splendor of a stone pond, exquisite gardens, specimen plantings and native grasses. The interior separation of space was well planned for privacy with various wings. The primary bedroom suite and water view balcony are located on a private level with four guest bedrooms on separate wings. A custom chef's dream kitchen with Subzero and Wolf appliances has a curvature design featuring oversized windows to maximize the extraordinary surrounding views. Additionally, there is a library and media room. The 500+/- square foot waterside deck extends from kitchen along entire length of the living room to primary suite. Immediate beach access provides a meandering sandy shore for therapeutic waters of iconic Gardiner's Bay. Experience inspiring waterfront living at its very finest. EH RR #: 25-831 Rental Terms: July - Labor Day: $270,000 August: $135,000 July: $135,000 June: $85,000
…By Sotheby's International Realty - East Hampton Brokerage
Discover the finest rental that Quogue Village has to offer. A Contemporary with Zen vibes, offering 5 bedrooms, 5.5 baths an open floor plan that opens to a dining room to entertain over 10 guests. Chef's kitchen has 2 ranges, a 4-burner gas range and a Viking 6 burner gas range, sub-zero refrigerator, 2 dishwashers, and of course, a wine refrigerator. To top it?off, an island with seating for 6 adds more entertaining space. First floor ensuite bedroom, second floor, primary ensuite with private balcony, designer bathroom with soaking tub, walk-in shower. The fully furnished lower level offers media room, full scale gym, and wet bar. Outside enjoy the heated Gunite pool, tennis, and a hard court with basketball hoop. the 16x16 gazebo offers a fireplace for those special evenings in the Hamptons. Option to rent "mini moke" for those drives to the exclusive Quogue Village Beach. What a spectacular summer in Quogue. Available July 2026 only
…By Daniel Gale Sotheby's International Realty
2026 Rates: NO AVAILABILITY New Modern Farmhouse Completed in 2021 and located in the heart Hog's Neck in Southold Hamlet. This home features an impressive 20 x 50 heated pool with electric cover, out door shower and sprawling paver patio. The interior is open and airy with Chef's Kitchen outfitted with Thermador appliances, large living room with built in shelving, gas fireplace and formal dining room. All four bedrooms are located on the second level: 1 Primary En-suite, 1 Junior Suite, 2 Guest Bedrooms and Full Hallway Bathroom. You will enjoy being within close proximity to Goose Creek, South Harbor Park Beach and Southold's vibrant business district!
…By Daniel Gale Sotheby's International Realty
This picturesque traditional on East Hampton Village's Osborne Lane is now available for two weeks at summer's end. Just doors away from Newtown Lane and the heart of village attractions, this lovely home offers a wonderful combination of summer charm and local convenience. Highlights of the first floor include a large entry foyer, a double-height living room with wood burning fireplace, a spacious chef's kitchen with high-end appliances and center island, a stylish dining room, a separate den, a screened-in porch, a half bath, and the primary bedroom with a gas fireplace, two walk-in closets, and an en suite marble bath. The second floor includes three large guest rooms, each with its own en suite bath. The lower level has been finished and offers another living space with TV, wet bar, and wine refrigerator, a gym outfitted with Peleton, Pilates, and free weight equipment, a bonus room, and additional full bath. The backyard is highlighted by a large gunite pool surrounded by bluestone, an expansive lawn, tall evergreens providing ample privacy, a hot tub, and extra decking and patio space - both ideal for entertaining. This exceptional property affords a wonderful sense of warmth and enjoyment while remaining close to world-class restaurants, shops, transportation, and beautiful ocean beaches. [[Rental Registration # 24-941]] EH RR #: 24-941 Rental Terms: Two Weeks: $75,000
…By Sotheby's International Realty - East Hampton Brokerage
Experience the best of Southampton Village living from this beautifully renovated Gin Lane estate rental, ideally located south of the highway just one block from the ocean. Set on 4 lush acres at the corner of Little Plains Road and iconic Gin Lane, this private summer retreat offers timeless Hamptons style, expansive entertaining spaces, and exceptional proximity to the beach, village boutiques, and renowned restaurants. Recently renovated in 2020, the 8-bedroom, 6-bath traditional residence spans approximately 5,800 +/- sq. ft. and features a bright open-concept layout designed for effortless summer living. Interior highlights include a spacious living room with fireplace, great room with open dining area, updated chef's kitchen with staff area, den/office, first-floor primary suite, and multiple gathering spaces ideal for entertaining guests or extended stays. Outdoor amenities include a heated 40' x 20' Gunite pool, expansive west-facing patio ideal for outdoor dining and entertaining, covered porch, mature landscaping, attached 2-car garage, and sweeping manicured lawns set across 4 private acres. Offering exceptional privacy in a premier Southampton Village location, the property is moments from ocean beaches, world-class shopping, and acclaimed village restaurants. Perfectly suited for Hamptons summer rentals, extended seasonal stays, or year-round living, this Southampton Village estate combines location, scale, privacy, and classic Hamptons charm in one of the area's most coveted ocean-block settings. Rental Terms: Other / Short Term - Year Round: $500,000
…By Sotheby's International Realty - Southampton Brokerage
Also available Year Round and Winter months Rental Reg # 22-834, Exp 5/23/24 [[Rental Registration # 26-664]] EH RR #: 26-664 Rental Terms: Other / Short Term - Year Round: $185,000 August - Labor Day: $50,000
…By Sotheby's International Realty - East Hampton Brokerage
Perched along one of the most sought-after stretches of Georgica Beach, this oceanfront property on impeccable West End Road offers an extraordinary Hamptons lifestyle with sweeping views of the ocean and Georgica Pond and timeless character. The beautiful shingle-style residence spans about 4,500 square feet and includes five ensuite bedrooms and two staff rooms off the kitchen with a jack and jill bathroom. The kitchen features generous quartz work surfaces and professional-grade stainless steel appliances, making it ideal for entertaining or relaxed seaside living. Just beyond a Dutch door lies an oceanfront outdoor dining space to host one-of-a-kind summer dinners. A private boardwalk leads directly to one of the best surfing spots in the Hamptons. The property also features a heated gunite pool and pool house. Inside, the home embodies style, warmth, and old-world charm. Architectural details such as exposed beams, wide-plank floors, and rustic sliding barn doors create a welcoming and character-filled atmosphere. A separate guest house with lodge like style offers 2 ensuite bedrooms and privacy from the main house. Just outside a glass door is a patio with ample seating and a barbecue area. With its privacy, secluded feel, artistic charm, and unforgettable views of ocean and pond, this special Georgica Beach residence offers a rare opportunity to experience refined coastal living in an idyllic Hamptons setting. Rental Terms: August - Labor Day: $325,000 July: $325,000 July - Labor Day: $600,000
…By Sotheby's International Realty - East Hampton Brokerage
Offered as a Year Round Rental (NO PETS)! Welcome to 435 Lupton Point Road, a beautifully appointed coastal residence tucked within a private Mattituck waterfront community offering direct water access to Deep Hole Creek and a private dock. Spanning approximately 2,700 square feet, this thoughtfully designed home features a spacious open floor plan ideal for both everyday living and entertaining. At the heart of the home is a chef’s kitchen, complete with generous counter space and seamless flow into the dining and living areas. A wood-burning fireplace anchors the living room, creating a warm and inviting atmosphere year-round. The home offers four well-proportioned bedrooms, two and a half bathrooms, and a dedicated home office, providing flexibility for remote work or guests. Natural light fills the interiors, enhancing the home’s airy coastal feel. Step outside and enjoy the rare convenience of water access with a private dock, perfect for boating, kayaking, or simply enjoying the peaceful creekside setting. The property’s location offers the best of North Fork living—just minutes from Love Lane’s shops, cafes, and farm stands, as well as New Suffolk Beach, making it an ideal full-time residence or weekend retreat. A unique opportunity to enjoy privacy, water access, and timeless North Fork charm in one exceptional offering. NO PETS
…By Daniel Gale Sotheby's International Realty
Convenience at its best. Newly constructed and first time available for rent. This pristine traditional home is located in the heart of Southampton village. The main floor has an open layout with lots of natural light. Gourmet kitchen, living room with fireplace, wet bar and dining area. There is a first floor en-suite bedroom. Second level has 2 guest bedrooms with a shared bath, master suite and laundry room. Lower level has a sitting area, bedroom and bathroom. There is a heated gunite pool, out door fireplace, outdoor pool bath and detached one car garage. Rental Terms: August - Labor Day: $135,000 July: $120,000 Memorial Day - Labor Day: $245,000 July - Labor Day: $230,000
…By Sotheby's International Realty - Bridgehampton Brokerage
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