luxury houses with pool for rent New York, United States (page 4)

The peacefulness and serenity of a summer on the East End awaits you in this fully renovated Southampton home. Offering breathtaking views of Peconic Bay and Bullhead Beach, this four bedroom home features 3 over-sized bedrooms each with their own private bath, an open concept main floor with a brand new kitchen, dining room, and a massive great room with vaulted ceilings, gas fireplace and wet bar. Outdoor amenities include a 20'x 40' custom inground pool surrounded by an oversized deck with lush landscaping throughout. If golf is your game, this home literally is surrounded by the top three courses on Long Island (Shinnecock Hills, Southampton and National) Luxury shopping and world class dining are both minutes away in the village of Southampton. This home is the perfect escape from hectic city life, yet it is conveniently located for those in need of a quick return to the hustle and bustle of greater New York City. [[Rental Registration # RP260397]] EH RR #: RP260397 Rental Terms: Memorial Day - Labor Day: $110,000 July: $45,000 August: $45,000 July - Labor Day: $90,000 June: $25,000 August - Labor Day: $50,000

This spectacular Sagaponack estate offers the best of Hamptons luxury lifestyle. Designed by a renowned interior designer, the graciously appointed interior flows easily to an outdoor living/dining patio, heated gunite pool, hot tub, tennis court, and exquisitely landscaped garden and lawn. The main floor has a living room, great room open to eat-in kitchen, formal dining room, butler's pantry, powder room, and en-suite bedroom. Upstairs has an additional primary suite, and three bedrooms ensuite with a sitting room and three bathrooms. The lower level includes a large luxury bedroom with an excavated, landscaped window well, a den/media room/exercise room and a staff bedroom and bathroom. Amenities include a fully enclosed lot with driveway gate, an attached garage, ample outdoor parking, double laundry room, speaker system, Wi-Fi, and security system. [[Rental Registration # 20251042]] EH RR #: 20251042 Rental Terms: Two Weeks: $120,000 June: $135,000 July: $195,000 June/July: $295,000 Other / Short Term - Year Round: $850,000 Memorial Day - Labor Day: $500,000 August - Labor Day: $225,000

With an extraordinary 345 feet of beachfront on Gardiners Bay, this one-of-a kind waterfront compound, set on 2.5 private gated acres, offers two distinct modern homes, each thoughtfully positioned to maximize breathtaking water views from nearly every room. The main residence is a study in exquisite minimalism, dramatic design, and thoughtfully curated artwork. The great room with massive wall-to-ceiling sliding glass doors is the central gathering place of the home, combining the living, dining, kitchen, and den areas in a seamless flow, all overlooking the sweeping water views. The living room area has multiple couches, a wood-burning fireplace, and a backgammon nook. The dining area features a single-piece, hand-carved bleached walnut dining table, custom crafted by Field & Co., and artisan chairs and benches for seating. The kitchen is a chef's dream suite of Gaggenau appliances and a separate butler's pantry. An intimate den space with a large television and wraparound banquette offers a quiet retreat. Just outside, the stone patio wraps around the great room and has an outdoor grilling station and a large spa for soaking and gazing across the bay. The western wing of the residence provides two ensuite guest bedrooms, a powder room, and a waterfront primary bedroom suite, complete with a sumptuous bathroom featuring a soaking tub, rain shower, vanity, and radiant heat flooring. The finished lower level has a cutting-edge media room with three tiers of lounge seating, a concession area, and an amazing powder room. The lower level includes a fitness studio with a sauna and cold plunge tub, an artist studio/office, and a well-equipped laundry room. A short distance across the rolling lawn, accented with lush landscaping, is the beautifully renovated guest residence. This home offers expansive waterfront views, sun-filled living spaces, a well-outfitted kitchen, lofted lounge areas, and a primary ensuite bedroom with a striking shower that opens to the outdoors. A second full bathroom serves the extended length, infinity edge swimming pool facing the bay. Close by, an elevated pavilion offers seating overlooking the shoreline, ideal for morning coffee or enjoying magnificent sunsets. And two private staircases descend directly from the residences to the bay beach, for days of swimming, paddleboarding, and strolls along the water's edge. This unique East Hampton compound offers an exceptional combination of luxury, stunning architecture, privacy, and breathtaking waterfront views - a truly rare opportunity to enjoy the Hamptons summertime lifestyle. Available for rent during Fall 2026, Winter 2027, Spring 2027 and Summer 2027. [[Rental Registration # RP26-773]] EH RR #: RP26-773 Rental Terms: Memorial Day - Labor Day: $575,000 March: $50,000 May: $75,000 July - Labor Day: $475,000 January: $50,000 Two Weeks: $125,000 April: $50,000 July: $250,000 February: $50,000 June: $100,000 June/July: $325,000 August - Labor Day: $250,000 Other / Short Term - Dec: $50,000

Now updated with Mesh Network 500 internet service throughout the house, this stylish and bright four bedroom, three bath home in the near Northwest area of East Hampton is available for summer 2024. Recently renovated kitchen and bathrooms. Crisp furnishings and finished lower level with workout area, den, bathroom, and glass walkout to pool area. Lovely private grounds with expansive new mahogany decking complete with upscale teak furniture and heated pool. A perfect summer retreat. Quiet and very desirable street convenient to East Hampton Village. [[Rental Registration # 22-1582]] EH RR #: 24-1334 Rental Terms: July: $40,000 August - Labor Day: $40,000 June: $25,000 Memorial Day - Labor Day: $100,000

Ideally situated South of the Highway in Bridgehampton, this exceptional rental offers the quintessential Hamptons lifestyle on a beautifully cleared, one-acre parcel. Tucked away on a quiet cul-de-sac, the property offers a rare combination of privacy, tranquility, and convenience, just moments from ocean beaches, horse farms, world-class dining, shopping, and everything the Hamptons has to offer. The light-filled residence is designed for effortless summer living and year-round enjoyment, with generous spaces for relaxing and entertaining. A welcoming living room with fireplace, updated kitchen and dining area, which flows seamlessly to a grand oversized screened-in porch. The first floor also features a comfortable junior primary bedroom, and a dedicated home office area overlooking the pool. Upstairs, the gracious, private primary suite is joined by two additional guest bedrooms, providing comfortable accommodations for family and guests. Outside, a heated gunite pool with fencing takes center stage amid mature landscaping and expansive, fully cleared grounds. There is abundant room to lounge poolside, dine al fresco, entertain, or simply enjoy the serenity of the property. Additional amenities include a two-car garage and generous parking. With its coveted South-of-the-Highway location, peaceful setting, spacious interiors, resort-style pool, and proximity to the ocean, this is a distinctive opportunity to experience Bridgehampton at its best. Available as a summer or year-round rental. [[Rental Registration # RP230864]] EH RR #: RP230864 Rental Terms: Other / Short Term - Year Round: $250,000 June: $35,000 August - Labor Day: $75,000 Memorial Day - Labor Day: $175,000 July: $65,000

Set amid the pastoral beauty of Water Mill's horse country, the home named Casa Mia is a charming three-bedroom, two-and-a-half-bath residence surrounded by lush gardens and sweeping views across neighboring farm fields. The approximately 2,000-square-foot home blends relaxed Hamptons living with thoughtful design and a distinctive sense of place. Interiors have been carefully updated, including a renovated kitchen and refreshed primary and guest baths. Shiplap detailing, transom windows and abundant natural light lend warmth and character throughout, while a media den offers an inviting space to unwind. The main-level primary suite provides ease and privacy, while additional bedrooms are located upstairs. A dramatic double-height art studio with cathedral ceilings and skylights adds an unexpected architectural element and an inspiring space for creative pursuits. Outdoors, the property unfolds as a private garden sanctuary. Stone paths and walls wind through mature specimen plantings, including Cryptomeria, Hinoki cypress, Japanese snowbell and umbrella pine. A nine-foot cocktail pool is tucked into the landscape, while a refurbished deck provides an ideal setting for outdoor dining, morning coffee or evenings overlooking the neighboring horse farm and spectacular western sunsets. Central air conditioning on the main level, mini-splits upstairs, updated windows and sliders, and generous lower-level storage complete the home. Peaceful yet distinctly Hamptons, Casa Lana offers an intimate Water Mill retreat where gardens, farmland and relaxed indoor-outdoor living come together beautifully. [[Rental Registration # RP261554]] EH RR #: RP261554 Rental Terms: August: $35,000 July: $30,000

Experience the private island ambience from this three story modern design by renowned architectural award recipient. Perfectly sited for panoramic waterfront views and stunning direct sunsets, it has a private path for spontaneous access to a secluded meandering beach. The open interior hold five bedrooms including two primary suites, seven bathrooms, a waterside enclosed porch, media room, gym, sauna, cold plunge ice bath and massage room. Walls of glass exhibit continuous water views throughout while inviting in soothing coastal air. The water view salt water pool has multiple surrounding decks, covered porches and pool house with bath. Various additional gathering areas include a fire pit with seating quietly nestled in a dune by the Bay. A private marina, waterfront restaurants and the charm of East Hampton Village are moments away. A magical setting, this is waterfront living at its finest. [[Rental Registration # 24-1446]] EH RR #: 24-1446 Rental Terms: Other / Short Term - Short-Term: $125,000 November: $50,000 October: $50,000

Unfold your zen at this ingeniously all custom waterfront design with spectacular panoramic views and stunning direct sunsets. A long gated driveway meanders through the secluded 2 acres bordered by specimen trees for maximum privacy. The interior glass courtyard separates the primary suite, guest rooms and common areas providing privacy, views to amaze and dramatic direct sunsets from most every room. The 50' infinity pool at the water's edge creates a seamlessly endless water view effect that is simply stunning. Surrounded by various patios for gathering with a viewing platform for spontaneous water access to paddle board, kayak or boat with two outdoor showers afterwards. Continuous water views flow throughout the spacious eclectic design with 4 ensuite bedrooms, den, professional chefs kitchen with large butlers pantry, water view dining, sumptuous 85' screen media room with adjacent kitchenette, full gym, infrared sauna and billiards. Floor to ceiling walls of glass disappear to invite in the coastal breezes and seamlessly combine this private setting with its serene interiors. Experience waterfront living at its finest. [[Rental Registration # 26-396]] EH RR #: 26-396 Rental Terms: Two Weeks: $190,000 November: $55,000 October: $55,000 Other / Short Term - Dec: $55,000

Rental Reg. # RP220705 exp. 9/1/24 Also Available: August 16 - September 2 for $250,000 This highly designed new construction--a designer's own home--offers every amenity. The magnificent 11,000+/- sq. ft. estate spans 2+/- lush acres, but feels like it sits on 50 acres, with panoramic reserve views to the West. Enjoy spectacular farm vistas and sunsets every day. It is unique--as the largest and closest field-view estate just outside Bridgehampton Village. The property is a 1/2 mile to some of the Hamptons best restaurants (including Topping Rose, Almond and Pierres), boutiques and shopping. The backyard is nothing short of a resort. The home offers a 50' heated gunite pool, hot tub, and sunken all-weather tennis court. The outdoor terrace stretches the entire length of the house with two covered porches, a state-of-the-art outdoor kitchen, firepit and new outdoor furniture ensuring everyone will relax in comfort. As well, you will be amazed by the thoughtfulness of the interior design. It comes lovingly appointed by Katie White Interiors, replete with gorgeous, hand-selected furniture and artwork that offer elegance, yet a comfortable modern and beachy vibe. The open concept living areas include the living room and great room, eat-in kitchen with Subzero/Wolf appliances (2 full fridge/freezers), a breakfast area, and multiple glass doors that open to an expansive stone terrace and covered porches. There is a highly designed formal dining room, One of the two primary suites is on the first floor (or can be furnished as an enormous office). A mudroom, with laundry and full pool bath round out the first floor. An architectural free-floating modern staircase leads upstairs, where a second luxurious primary suite features a generous balcony with outdoor furniture for lounging any time of day. Four additional ensuite bedrooms, two of which share a large balcony, are also on this level, along with a laundry room. The finished lower level provides large media/recreation space, a gym, and two additional bedrooms. The house has a state-of-the-art sound system and comfort controls. [[Rental Registration # RP220705]] EH RR #: RP220705 Rental Terms: July: $350,000 June/July: $500,000 Other / Short Term - Year Round: $1,300,000 July - Labor Day: $700,000 August - Labor Day: $400,000 June: $200,000

Experience the best of Village living in this recently renovated, impeccably maintained estate, ideally located just moments from renowned restaurants, boutique shopping, and ocean beaches. Set behind mature specimen trees and surrounded by lush lawns and vibrant gardens, the property offers exceptional privacy and a true resort-like setting. Designed for both entertaining and comfortable everyday living, the home features a dramatic two-story entry and great room, formal and casual dining areas, and a chef's kitchen with double Sub-Zero refrigerators and a large center island. Additional highlights include two spacious family rooms, seven bedrooms, and seven-and-a-half baths, including separate staff quarters. Enjoy an array of premium amenities, including a fully equipped gym, home office/library, detached two-car garage, and an oversized heated saltwater Gunite pool. Outdoor living is elevated with an expansive slate patio, a new covered poolside lounge complete with a gas fireplace, and an outdoor shower, creating the perfect summer retreat. Rental Terms: July: $145,000 Memorial Day - Labor Day: $375,000 August - Labor Day: $185,000 July - Labor Day: $300,000 Other / Short Term - Year Round: $450,000

Moments from the heart of Sag Harbor Village, this exceptional designer residence offers a rare opportunity to experience a seamless blend of modern sophistication and timeless coastal living. Privately sited on a beautifully landscaped 0.47± acre, the property delivers a serene and elevated summer retreat in one of the Hamptons' most desirable locations. Spanning approximately 4,500± square feet, the home is thoughtfully designed with expansive, light-filled interiors and an effortless flow throughout. The main level features a gracious open-concept layout, anchored by a beautifully appointed chef's kitchen with premium appliances and custom finishes. Adjacent living and dining spaces are designed for both relaxed living and refined entertaining, complemented by a separate lounge with fireplace that provides an intimate setting for quieter moments. The second level is highlighted by a well-proportioned primary suite offering a private sitting area and spa-inspired bath, creating a true retreat within the home. Additional guest bedrooms are generously sized and finished with the same attention to detail, offering comfort and flexibility for a variety of living arrangements. The outdoor setting is equally compelling, with meticulously maintained grounds that create a sense of privacy and calm. A heated pool is surrounded by expansive lounging and entertaining areas, ideal for enjoying the full Hamptons lifestyle-from sun-filled afternoons to evening gatherings under the stars. A fully finished lower level enhances the offering, providing additional space for recreation, media, or wellness use-thoughtfully designed to support both relaxation and entertainment. Ideally located just minutes from Sag Harbor Village, the property offers convenient access to renowned dining, boutique shopping, marinas, and local beaches, while maintaining a peaceful residential setting. An exceptional rental offering defined by design, comfort, and location-crafted for a sophisticated Hamptons summer experience. Rental Terms: May: $35,000 June: $40,000 Other / Short Term - Year Round: $265,000 August: $87,500 September: $30,000 July: $85,000

A stylish, gorgeous construction designed by award-winning architect James Merril. Set on an acre, this 5- 5-bedroom home has every desirable amenity. The primary bedroom has a terrace and a beautiful bathroom with a shower and a separate bathtub. The 4 guest rooms are all spacious and light-filled. Downstairs, there is an open living room and a den/ 5th bedroom with a full bath. An exquisite gourmet kitchen has all the bells and whistles, from a 6-burner Viking with a grill to a double Sub-Zero Fridge, wine fridge, double sinks, and dishwashers; it also has its own breakfast area. There is a formal dining area with a fireplace that is magnificent. The sunny Living Room shares the same dual-sided open fireplace. A lower-level gym. Many French doors open to the deck that has a gorgeous outdoor dining area- and a shaded lounge area with a 32' by 15' ft. heated pool. A path to the dock on the bay, which is a divine protected sanctuary, that accesses the big open bay. There is a lower basement level with a 2-car garage. The front of the house has a great veranda, all set on a quiet and charming high-end street in the Village of Sag Harbor. Rental Terms: Other / Short Term - Year Round: $450,000 Memorial Day - Labor Day: $375,000 September: $25,000 July - Labor Day: $300,000 October: $25,000 November: $20,000 June: $60,000

Traditional Luxury Getaway Minutes from East Hampton Village & Ocean Beaches Welcome to Handsome Hills, your perfect escape in the Hamptons! This stunning 5-bedroom, 4-bath home is designed for comfort, relaxation, and making unforgettable memories. Nestled in a peaceful neighborhood just minutes from East Hampton Village and the area's best ocean beaches, this home is the perfect retreat for families and friends looking to unwind in style. Inside, You'll Love: A spacious and beautifully decorated interior with plenty of room to spread out. A first-floor primary suite with a private bath and direct access to the outdoor hot tub. A custom eat-in kitchen featuring stainless steel appliances, perfect for cooking up delicious meals. A formal dining room for elegant dinners and special gatherings. A cozy den for quiet reading or morning coffee. A grand living room with a floor-to-ceiling fireplace, perfect for gathering and relaxing. A fully finished lower level with a movie screen, comfy lounge, pool table, bar, poker table, and dart board - entertainment for everyone! Outdoor Living at Its Best: A heated pool and hot tub for ultimate relaxation. A spacious deck with a grilling station and outdoor dining table for alfresco meals. A hammock to soak up the sun or enjoy an afternoon nap. 2 Kayaks to enjoy a paddle on nearby Georgica Pond. A private outdoor shower, perfect after a dip in the pool or a day at the beach. A large fenced-in yard in a quiet, bike-friendly neighborhood. More to Love: A large garage to store bikes, surfboards, and beach gear. Pet-friendly-your well-behaved fur babies are considered! Concierge touch-celebrating a special occasion? Send your pre-ordered items ahead, and we'll set them up before your arrival. Whether you're here to relax, explore, or celebrate, let us welcome you to your home away from home. [[Rental Registration # 23-1270]] EH RR #: 23-1270 Rental Terms: July: $59,000 Memorial Day - Labor Day: $125,000 June/July: $75,000 August - Labor Day: $65,000 July - Labor Day: $109,000 June: $25,000 Other / Short Term - Weekly: $15,000

5BR/ 6.5 BA w/ Tennis on 5 + acres with Pool, Hot Tub, Sauna & Basket Ball Court! Open plan living / dining room / Kitchen and so much more! Escape Out East to Sag Harbor! Live the good life on this remarkable, 5.4 acre gated compound. There's no doubt you'll fall in love with the Hamptons, as you enjoy a peaceful stay at this private retreat! This stunning contemporary home sleeps 12, with five en-suite bedrooms, including three primary suites, one on the first level with a sauna and a private deck. The sun-filled open concept living room features a cathedral ceiling, skylights, a gas-burning fireplace, and an open dining room with French doors leading to a covered porch. The spectacular state of the art kitchen features Subzero and Wolf appliances as well as a miele and nespresso machines. Additional highlights include a fully finished lower level with ping pong and pool tables, tennis ball machine office set up and an additional queen pull out bed. You and your guests will love the convenience of the 7 smart TVs, 5 separate Sonos zones inside and a 6th outside, the Mesh wifi system (gigabyte internet) by Optimum, and the Samsung dryer and washer. In the sun-filled study guests will find a fully functioning office setup complete with a laser printer and IMac computer. Additional features include top of the line mattresses on each of the beds, a peloton bike and brand new furniture throughout. The north wing master suite features a wood burning fireplace, a private study, a jacuzzi tub and a double shower. In the south wing primary suite, you will find 20 foot ceilings, a surround sound system, an additional gas burning fireplace, soaking tub and a double rain head shower. Step outside for some fresh air and enjoy beautiful views of the large grounds featuring a heated gunite pool plus a 10 seat hot tub, a new secluded and lighted tennis court, with separate covered entertaining space as well as a fire pit area. Guests can enjoy the use of adult and children's bicycles, beach chairs, a paddleboard and even a kayak. The home is surrounded by miles of nature preserve trail systems and private ponds to discover. Prepare to fall in love with the Hamptons lifestyle, as you experience it at its very best! This property is a 5 minute drive to Sag Harbor's Main Street and 7 minutes to East Hampton. [[Rental Registration # RR-25-1159]] EH RR #: RR-25-1159 Rental Terms: Other / Short Term - Year Round: $500,000 Memorial Day - Labor Day: $295,000 July - Labor Day: $225,000 July: $125,000 June: $85,000 August - Labor Day: $135,000

Be one of the first to enjoy this beautifully renovated compound set on over half an acre in the heart of Southampton Village, now offered as a rental, with all new furnishings from Home Nature, Serena & Lily and CB2. Just moments from the iconic Gin Lane beaches and charming village shops, the main residence welcomes with a lovely entry foyer featuring a wood-burning fireplace on one side, and the den on the other. The foyer leads to the dining area and then over sized living room with fireplace, dine-in chef's kitchen, and powder room. The family room that has informal dining table as well opens fully onto the outdoor deck. Upstairs, you'll find a spacious primary suite (king bed) with a private office and three additional en-suite bedrooms ( 1 king and 2 queen beds). Downstairs, the French doors to the back deck, making indoor-outdoor living easy, open to lovely views of well-tended gardens and heated Gunite pool. The guesthouse provides exceptional flexibility with its living room, dining area, kitchenette, full bath and laundry, and upstairs two additional bedrooms with full bath. One room has two twins that can become a king, and the other a day bed with an office. The guesthouse back terrace overlooks the expanse of the long rear yard. This offering combines functionality and location, a true "get" in the Hamptons--less than 1/3 mile to Little Plains Beach and 1/2 mile to Southampton's Main Street. [[Rental Registration # N/A]] EH RR #: N/A Rental Terms: July: $135,000

PLEASE NOTE: This property is available for US Open dates June 15th- June 22nd. Beautifully renovated Gambrel on 1.17 acres +/- bordering two reserves. This custom classic includes 3 Master suites, one downstairs and 2 upstairs master suites up. Main floor has a living room with vaulted ceiling, dining room, library/office, open kitchen to lounge / dining area and many possibilities for outdoor dining accessed from kitchen and living room. Upstairs there is a large secondary gathering room, outdoor lounging and dining on deck and 5 guest rooms.The lower level has a separate staff room,full bathroom and super-sized playroom with wet bar, bathroom, rock climbing wall, gym and more bunk beds.. A new heated salt water gunite pool is surrounded by beautifully landscaped grounds, built in BBQ, many outdoor decks and a putting green. Private flag lot with farm field views and 3 fireplaces. Stunning!!! [[Rental Registration # RP260815]] EH RR #: RP260815 Rental Terms: August: $225,000 July: $225,000 Other / Short Term - 7/1/2027 - 8/31/2026: $450,000

Rental Registration # Pending Also available: Aug 1st - 31st '24 $55k, Sept 1st - Sept 30th '24 $20k Located deep at the end of a private driveway on a shy 2 acres holds this beautiful renovated contemporary with extraordinarily unique design features. The open flow interior with dramatic height ceilings and continuous expanses of glass provide fantastic abundant natural light throughout. The gourmet kitchen and dining area glide effortlessly to the spacious sun room oasis. The living room has a gas fireplace and wet bar for entertaining. The separate guest wing, perfectly situated for privacy, holds a second primary bedroom with bath and two additional bedrooms each en-suite with baths. The expansive primary suite occupies the entire second floor with over-sized primary bath and walk in closet. To complete this perfect outdoor lifestyle is expansive mahogany decking, new heated gunite pool, and north south tennis court. In addition, there is a 3 car detached garage. This unique offering is located moments to East Hampton Village and Ocean beaches. Also available 09/06/2022 - 09/30/2022 for $20K. EH RR #: 26-389 Rental Terms: August - Labor Day: $65,000 Memorial Day - Labor Day: $160,000 July: $65,000 June: $35,000 June/July: $95,000 Other / Short Term - Year Round: $220,000 July - Labor Day: $125,000

This bright and spacious post-modern house features 4 bedrooms, 3.5 baths, oversized windows, vaulted ceilings, reading loft, cathedral kitchen with stainless steel appliances and copper countertops. Outside, enjoy a new entertainment patio featuring a 65" smart tv, Sonos sound system, sauna, private pool, hot tub, outdoor shower, and cold dip barrel! Nestled on a quiet cul-de-sac with surrounding beautiful landscape along a nature preserve for ultimate privacy, yet located just steps from East Hampton village shopping, ocean beaches, the train station, and restaurants. Your perfect summer getaway awaits! [[Rental Registration # 26-307]] EH RR #: 26-307 Rental Terms: June: $38,000 July: $33,000 Other / Short Term - Year Round: $250,000

Exquisite New Construction | 6 Bedrooms | 6.5 Bathrooms | 5,500+ Sq. Ft. | Resort-Style Amenities Nestled on meticulously landscaped grounds in a prime Hamptons location, this stunning, newly constructed residence offers the perfect blend of contemporary elegance and effortless indoor-outdoor living. Spanning three luminous levels, the home is just moments from pristine beaches, Sag Harbor's charming Main Street, and the vibrant energy of Bridgehampton-making it an idyllic retreat for both relaxation and entertaining. Grand & Light-Filled Living Spaces A soaring entryway bathed in natural light welcomes you into an expansive open-concept layout, where sleek modern design meets unparalleled functionality. The chef's dream kitchen boasts dual oversized islands, premium appliances, and a seamless flow into the dining and living areas, anchored by a cozy fireplace. Floor-to-ceiling sliding glass doors blur the lines between indoors and out, opening to a sprawling deck designed for alfresco dining, sunset grilling, and tranquil lounging-all overlooking the lush, private grounds. The main level also features a sun-drenched den with high ceilings, a full bath, and a chic powder room, offering flexibility for guests or a home office. Luxurious Upper-Level Retreat Ascend to the second floor, where four generously sized en-suite bedrooms provide serene sanctuaries for family and guests. The primary suite is a true haven, complete with a private balcony and a spa-inspired bathroom featuring designer finishes. An additional office/media room and a spacious laundry room add convenience to this level. Entertainer's Paradise - Lower Level & Outdoor Oasis The fully finished lower level is an entertainer's delight, featuring two additional bedrooms, a family room with a kitchenette, a full bath, and a second laundry area-ideal for guests or extended stays. A state-of-the-art home theater promises cinematic nights in. Sliding glass doors from every room lead directly to the resort-style backyard. Outside, paradise awaits: - 20x40 heated gunite pool surrounded by expansive lounge areas - Professional-grade pickleball court for friendly competition - Covered outdoor kitchen & dining pavilion for gourmet grilling and gatherings - Cedar-enclosed outdoor shower & dressing room for post-beach or poolside refreshment Premier Amenities & Sustainable Living Additional highlights include a two-car garage and solar power integration, blending modern convenience with eco-conscious living. A Rare Hamptons Gem Designed for those who seek both luxury and livability, this home effortlessly balances sophistication with comfort. Whether as a year-round residence or a seasonal escape, 130 Highview is a must-see property that defines Hamptons living at its finest. Schedule your private tour today-this is one you won't want to miss." [[Rental Registration # RP261343]] EH RR #: RP261343 Rental Terms: Other / Short Term - 9/9/2026 - 9/30/2026: $30,000 April: $20,000 November: $20,000 July: $120,000 May: $45,000 June: $60,000 January: $20,000 August - Labor Day: $140,000 February: $20,000 October: $25,000 March: $20,000 August: $120,000 Memorial Day - Labor Day: $300,000

Brand new furnishings await the discerning tenant at 18 Spring Pond located in a quiet, private community. The 2 story home offers a heated, gunite swimming pool and community tennis court. The house is freshly painted, updated and boasts brand new furnishings including pool lounges. Great open floor plan from the kitchen to indoor and outdoor entertaining spaces. There is a junior en-suite bedroom on the first floor in addition to a powder room. The second floor holds the private primate suite with floor to ceiling windows overlooking the private property. There is a private balcony, shower bath, walk in closet and an adjacent den that can serve for relaxation, working. There is a third en-suite guest room with two twin beds and the laundry room on the second floor. [[Rental Registration # RP260246]] EH RR #: RP260246 Rental Terms: Other / Short Term - Dec: $15,000 April: $15,000 July: $40,000 September: $18,000 March: $10,000 November: $10,000 June/July: $60,000 May: $15,000 January: $10,000 October: $10,000 February: $10,000 Winter Season: $60,000 Per Month

Newly renovated eight-bedroom home located on South Main Street, just a short distance to the village and ocean beaches. The home includes a completely updated eat-in kitchen with top-of-the-line appliances, formal dining room, living room, den, sunroom and a beautiful outdoor living room. All six bedrooms have been renovated and all have their own en suite bathroom. The property, which is nearly an acre +/-, includes a heated gunite pool, large patio area great for entertaining, a large lawn and lovely landscaping. A must-see rental! Rental Terms: August: $75,000

Enjoy the ultimate blend of convenience and Hamptons charm in this exceptional rental opportunity.This beautifully updated 4-bedroom, 2-bath village rental is perfectly designed for comfort, convenience, and summer living. The home features a bright and welcoming living room, dedicated dining room, charming eat-in kitchen, and a first-floor primary ensuite that opens to the rear yard. Outside, enjoy a private oasis complete with a patio for outdoor dining and lounging and an in-ground heated pool-perfect for relaxing after a day at the beach.Situated in an enviable in-town village location, this property offers effortless access to the very best of East Hampton, including premier shopping, restaurants, beaches, and more. . Rental Terms: July: $55,000 October: $14,000

Available, year-round! Flex start date of Sept 15,2026 or Oct 1, 2026. Nestled in the hamlet of North Haven, just minutes from the heart of Sag Harbor Village, this exceptional Hamptons retreat embodies refined luxury and timeless design. Thoughtfully crafted with bespoke finishes throughout, the residence offers four bedrooms and five baths, including two first-floor ensuite guest rooms. The elegant interior features a chef's kitchen with generous dining space, a dramatic great room and four tranquil bedrooms (all en-suite) designed for comfort and privacy. Outdoors, an expansive bluestone terrace provides the perfect setting for entertaining, overlooking a serene gunite pool surrounded by beautifully curated gardens. A sweeping circular driveway and lush landscaping create a sense of seclusion, while the property's prime location places you moments from Sag Harbor's renowned beaches, acclaimed restaurants, and charming boutiques. [[Rental Registration # RP#R-2024-0011]] EH RR #: RP# R-2024-0011 Rental Terms: Other / Short Term - Year Round: $215,000

Tucked away on a quiet cul-de-sac in Springs, 24 Lilla Lane offers the perfect blend of privacy, comfort, and style. Bordering the 165-acre Jacob's Farm Preserve and just moments from Louse Point and the beloved Springs General Store, this charming home is ideally situated for enjoying all that Springs has to offer. The gracious living room features vaulted ceilings and a fireplace, creating a warm and inviting gathering space that opens beautifully to a large deck and heated pool overlooking protected woodlands. Crisp, clean, and thoughtfully styled throughout, the home offers three bedrooms and two-and-a-half baths along with generous living space designed for both relaxation and entertaining. An exceptional gym with top-of-the-line equipment adds a rare luxury, while the finished lower level provides the perfect separate space for working from home, movie nights, or additional gathering space. Quiet, charming, and surrounded by nature, this is an ideal Springs rental retreat. [[Rental Registration # Pending]] Rental Terms: August: $35,000

Bright and open home offers an inviting living space complimented by vaulted ceilings over sized windows and sliding glass doors. A perfect environment for socializing and gathering. The home is designer decorated with a mix of contemporary and country farmhouse beachy furnishings. Muted greys & blues are found throughout the home. The centrally air conditioned home features an open concept with the kitchen opening up to the living room and dining area. Professional appliances and every imaginable kitchen gadget needed for a gourmet chef. The Carrera marble island is a perfect gathering spot for morning coffee. There is a farm table with seating for 8. Each of the bedrooms has comfy beds with brand new linens including comforters with 100% high thread count cotton duvet covers. The home is supplied with bath towels and separate pool towels. There is a lower level media room for watching your favorite movie and huge indoor recreation area that includes a hockey/soccer rink and some toys. Step out of the sliding backdoors onto a deck which overlooks the pool. The backyard of the home looks onto a private 50 acre reserve where you will find running and hiking trails. The deck is well equipped with dining areas, seating, lounge chairs and gas BBQ. Additional accessories will include beach chairs, umbrellas and coolers for beach. 3 bedrooms , 3 bathrooms Finished Basement with TV room/Playroom/Hockey Soccer Rink Open kitchen/living/dining space with vaulted ceilings Bright open sunny home Fully equipped gourmet kitchen Central A/C Heated Natural Salt Water Pool Located on quiet cul de sac in private community 4 miles to Ocean Beach 2 miles to downtown Bridgehampton 3 miles to downtown Sag Harbor Keyless Entry System Private VIP Concierge Services Available during Summer Season Bedroom One: King Bed with ensuite bathroom Bedroom Two: Queen Bed with shared bathroom Bedroom Three: Two sets of bunkbeds, four twin beds with shared bathroom. [[Rental Registration # RP230214]] EH RR #: RP230214 Rental Terms: June: $25,000 Memorial Day - Labor Day: $110,000 July: $45,000 August - Labor Day: $55,000