luxury house with terrace for rent Greenport, United States

Offered July $35,000; Aug $35,000; Sept $25,000; Oct $20,000. Elegantly renovated and exceptionally spacious, this contemporary retreat is nestled within a parklike setting of sweeping lawns, lush gardens, and mature landscaping that affords remarkable privacy. Refined outdoor amenities include a heated gunite pool, outdoor shower, firepit, and walking path to abutting Island’s End Golf & Country Club. The main house and annex are filled with natural light, featuring soaring ceilings, oversized windows, and glass doors that open seamlessly to two expansive decks for effortless indoor-outdoor living. A generous poolside patio offers additional space for lounging and entertaining, while the decks provide inviting areas for alfresco dining, grilling, and relaxation. Bedrooms are thoughtfully positioned to ensure comfort and privacy for guests. Peaceful and secluded, yet just moments from Greenport Village, Seps Farm Stand, and sound and bay beaches, this home is impeccably suited for gracious North Fork entertaining.

A stunning architectural jewel in Pandion, this freshly built, never-before-lived-in residence is both design-forward and deeply inspiring. Clad in arctic pine tongue-and-groove and corten steel, its twisted gable form captivates from every angle, while exterior decking invites you to soak in the surrounding natural beauty. The design/build owner's home draws inspiration from exposure to Frank Gehry's artist friends' homes in Venice, California. Founded in 2003 by Alexandra Hayden, Octave Studio is known for creating intuitively designed spaces that balance comfort and creativity, honoring the architecture and natural surroundings while reflecting each client's unique spirit. Curate | Build is Shelter Island's premier general contractor, known for high-end residential construction and renovations that blend timeless design, modern function, and uncompromising craftsmanship. The plywood-finished walls pay homage to Sea Ranch and early Gehry Venice architecture, creating a warm yet modern atmosphere that balances precision with artistry. Inside, radiant Indian black limestone floors anchor the soaring, cathedral-height living space centered around a wood-burning fireplace. The kitchen is as stylish as it is functional, featuring a Wolf range, Thermador under-counter fridge-freezer, and a separate beverage fridge. The primary bedroom includes an ensuite bathroom with Beton Ciré waxed gray walls. A guest bedroom and an additional full bath complete the main floor. Upstairs, a vaulted loft offers a lounge and media area, desk space, and a peekaboo window framing bay views. The lower level features a concrete-floored laundry room with a full-size fridge-freezer. Smart Lutron lighting and shades throughout the home add effortless modern convenience. Set on 1.5 acres moments to Mashomac, a 2600 acre preserve, the property provides a serene natural setting that enhances the home's sculptural presence. Residents enjoy access to a Boat House-exclusive to just three homes within the HOA-complete with a living area, bathrooms, outdoor shower, and dock with a dedicated boat slip accommodating up to a 28-foot powerboat. Please note: beam and draft information must be provided to ensure vessel compatibility. The community also features a deco-turf tennis court with bathroom and locker. [[Rental Registration # RP2025]] EH RR #: RP 2025 Rental Terms: July - Labor Day: $62,500

Discover the perfect island getaway in this spacious 4-bedroom, 2-bathroom home tucked away on a large, serene lot. Surrounded by mature landscaping, the property features a generous front porch overlooking a peaceful pond—an ideal spot for morning coffee or sunset relaxation. Inside, the home offers a bright and inviting layout with a well-appointed kitchen complete with a center island, perfect for entertaining. Additional conveniences include an in-unit laundry room, mudroom, and a flexible bonus space great for a home office or playroom. A two-car garage provides ample storage and parking options. Located just minutes from Route 114 and South Ferry, the home offers easy access to all the island’s main destinations. Wades Beach is only 1.5 miles away, making beach days effortless. Guests also enjoy seasonal access (July 4th–Labor Day) to the Coecles Harbor Marina pool for added summer enjoyment. This peaceful retreat combines comfort, privacy, and convenience—ideal for your next stay on Shelter Island.

Offered Sept $8,000. Enjoy the ease of summer on the North Fork in this classic 1910 hilltop home overlooking Orient Bay and Long Island Sound. A three-sided wraparound porch extends the main living spaces outdoors through multiple glass doors, creating a seamless indoor-outdoor flow filled with light and salt breezes. Inside, the home offers inviting spaces for gathering, including a spacious living room with a wood-burning fireplace, a formal dining room, and a generous eat-in kitchen with a butler’s pantry. A TV room/bedroom and full bath complete the ground floor. Upstairs are five bedrooms, including a primary bedroom with a private balcony and half bath, along with a full bath for the four additional bedrooms. The private grounds include an in-ground pool. Latham’s Farm Stand and Orient Village are just a short walk away. September is an ideal time to enjoy this peaceful, timeless retreat.

Authentic 1770 Cottage in the heart of Orient Village. Lovingly restored & maintained Village home on beautifully landscaped lot, offering private grounds & distant views of sunsets over the bay. Furnished in period antiques, screened-in porch off kitchen, first floor bedroom. Walk to amenities, bay beach, Yacht Club, marina, farm stand & Jitney. Offered Sept 3-Oct 3 for $8,000. Permit #0091.

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!

Settle into summer on the North Fork in this beautifully maintained and updated 4 bedroom, 3 full bath home located in the Angel Shores community of Southold. The layout is ideal for entertaining or just enjoying the lazy days of summer. This special home offers a 1st floor bedroom and full bath, along with a 2nd story spacious primary en-suite and 2 additional bedrooms to comfortably accommodate guests. Angel Shores is known for its sandy Peconic Bay beach, just a short stroll down the road, perfect for easy beach days and watching sunsets by the water. The home is also conveniently close to Southold’s wineries, farm stands, and village amenities, putting the best of the North Fork right at your fingertips. 2026 Availability: June 16-June 30th $7,000, July $23,000, August $25,000 August-Labor Day $27,500. Permit # 0956

Summer is here, and this home has vacation written all over it. Enjoy spectacular sunset water views of the Long Island Sound from the spacious wrap-around deck or from the bright, open-concept living spaces inside. Perfect for entertaining, the layout features 4 bedrooms and 2 full bathrooms, offering a beautiful oasis for relaxation and togetherness. The lifestyle here is effortless: Kenny's Beach access is just steps away (.02 miles) for swimming in the Sound, complemented by a refreshing outdoor shower back at the house. Plus, you can leave the car behind and stroll down the road (.03 miles) to grab lunch or dinner at the hot new local restaurant, Little Fish. Let's get you set up in the perfect summer getaway—inquire today! Availability: June 15-June 30th $10K | July $35K | August $30K

Welcome to 54 Bay View Drive East, Sag Harbor, where modern luxury meets waterfront living. This stunning, award-winning modern estate is a boater's paradise, boasting a deep water dock and breathtaking sunset views over Sag Harbor Cove. With 4 bedrooms, 4.5 modern baths, and 3100 square feet of sleek living space, this home offers the epitome of waterfront elegance. A primary suite on the first floor and an additional secondary primary bedroom suite on the second floor with endless water views complement this unique offering. Enjoy the convenience of a water view Chef's kitchen, multi-level decks, and a heated Gunite infinity pool. The property features geothermal heating and cooling, ensuring comfort with minimal environmental impact. Custom fixtures from Italy and an outdoor wood-burning pizza oven add distinctive charm. Located near Sag Harbor's amenities, a 10 min walk to Long Beach, and the Shelter Island Ferry, this home offers a unique summer retreat. Don't miss the opportunity to experience waterfront luxury at its finest. [[Rental Registration # 251021]] EH RR #: 251021 Rental Terms: August: $185,000 August - Labor Day: $225,000

New Kitchen Renovation!! Modern waterfront residence with expansive yard and private dock near Long Beach. Enjoy long summer days sailing, kayaking, swimming or swinging in the yard and followed by family bbqs. Great location with proximity to Sag Harbor village restaurants and shops and private outdoor oasis. Revel in spectacular sunset views from the wrap around deck with comfortable seating that is also perfect for outdoor dining and entertaining. Rental Reg. # RP201766 - Reg. Expires 6/07/2023 EH RR #: RP201766 Rental Terms: Other / Short Term - Year Round: $375,000

Step into the season with a top-to-bottom Spring refresh-brand new mattresses, crisp bedding and towels, a sparkling new kitchen stove, a sizzling barbecue, and a fresh coat of paint. Watch the sunsets dance across the water and feel the cool breezes that make every evening unforgettable. With a sandy entrance to Sag Harbor Cove for a refreshing dip and an outdoor shower to rinse off, it's the perfect blend of charm and modern comfort. This gem is priced right and ready for your best summer yet-just unpack and start making memories! [[Rental Registration # RA240090]] EH RR #: RA240090 Rental Terms: September: $10,000

Discover the perfect Fall getaway in this stunning artist's home in Sag Harbor, now available from Sept 8th - Oct 5th 2026. Ideally situated between Sag Harbor Village and Long Beach, this immaculate 4-bedroom, 3.5-bathroom residence is a true oasis, featuring a well-curated collection of art within a sophisticated monochromatic interior. Built in 2018, this contemporary farmhouse beautifully balances exceptional style and comfort. An open-plan kitchen, dining, and living area seamlessly transitions to the 32' x 16' heated gunite pool, surrounded by a bluestone patio with multiple entertaining and lounging areas. A well-thought-out setting for summer gatherings or long days by the poolside. For the art enthusiast, a well-stocked library of art and design books can be found in the first-floor lounge. On the second floor, you will find four well-appointed bedrooms, including two that feature ensuite bathrooms, as well as an additional full bathroom. To enhance your stay, the dedicated laundry room features two washers and dryers for your convenience after days at the beach. Minutes from both Long Beach and Sag Harbor Village, you can also enjoy fresh, local produce from Serene Green Farm Stand, conveniently located at the end of Parkway Drive. [[Rental Registration # RP230356]] EH RR #: RP230356 Rental Terms: October: $18,000 July: $60,000 July - Labor Day: $135,000 Other / Short Term - 12/23/2026 - 1/31/2027: $30,000 September: $12,000 August - Labor Day: $75,000

Situated on one of the largest lot in Sag Harbor Village at 2 builders acres, this furnished 3,000 sq. ft. Colonial offers 5 bedrooms or converted home office, 2.5 baths, outdoor shower, CAC, finished basement with play room, gym, large heated gunite pool, hot tub, all on a manicured property with organic garden, fire pit, and lovely outdoor dining. Within a short distance to the village center and its restaurants, shopping and entertainment. Store your catamaran, paddle boards and kayak at Havens Beach, or enjoy sailing at the Breakwater Yacht Club.ond largest lot in Sag Harbor Village at 2 builders acres, this furnished 3,000 sq. ft. Colonial offers 5 bedrooms or converted home office, 2.5 baths, outdoor shower, CAC, finished basement with play room, gym, large heated gunite pool, hot tub, all on a manicured property with organic garden, fire pit, and lovely outdoor dining. Within a short distance to the village center and its restaurants, shopping and entertainment. Store your catamaran, paddle boards and kayak at Havens Beach, or enjoy sailing at the Breakwater Yacht Club. Rental Terms: May: $20,000 September: $38,000

Welcome to 4 Scrimshaw Drive, located in the sought-after Whalebone Landing community, where summer feels calm, private, and effortlessly beautiful. Enjoy the private bay beach and tennis courts just moments away, and quick access to the boutiques, restaurants, and harbors of both Southampton and Sag Harbor. Designed for luxury summer living, this home features a heated gunite pool, sun-filled interiors, and three levels of finished living space ideal for both relaxation and entertaining. Coastal-inspired details throughout the home create a natural sense of ease and timeless Hamptons elegance. With convenient proximity to the U.S. Open PGA at Shinnecock Hills Golf Club in June 2026, this residence offers a refined retreat for those seeking to experience the very best of the Hamptons with style, privacy, and comfort.

Located just 2 blocks from Sammy's Beach, in East Hampton, unwind at this stunning original Mid-Century home. This freshly renovated two story, three bedroom, two bath house was built with oak floors, cedar clad walls and ceiling, and antique details for a luxurious yet charming feel.It features a double height living area with floor to ceiling windows, wood burning stove, and integrated fully equipped kitchen and dining areas. Sliding glass doors lead to the expansive wraparound deck with Barbecue, dining and lounge areas, outdoor shower, and the large yard with seating and a fire-pit. The bedrooms are generously proportioned with 2 king and 1 queen beds, and upstairs there is a dedicated office and work out area with its own walkout balcony.Though quiet and elegant in nature, the home is modern where it counts. It features two large flatscreen TVs, 1 GB wi-fi and unlimited music and sound capabilities in every room. Enjoy long days on the beach, paddle board or kayak in Three Mile Harbor, or hikes through the nearby 116 acre Sammys Beach Nature preserve. Conveniently located 2 blocks from Sammys Beach, 7 minutes to East Hampton Village and only 10 minutes from Sag Harbor, the home is a true East End escape. [[Rental Registration # Pending]] Rental Terms: February: $2,975 July - Labor Day: $39,000 September: $4,500 June: $9,900 April: $2,975 March: $2,975 November: $3,200 Other / Short Term - Dec: $3,200 October: $3,200 August - Labor Day: $22,000 Memorial Day - Labor Day: $49,000 August: $18,000 January: $2,975 July: $18,000 May: $3,975

Escape to the serene charm of New Suffolk this summer with this beautiful rental property! Offering ample space for all, this delightful home boasts 5 bedrooms and 3 bathrooms, ensuring everyone's comfort. Step outside onto the expansive wrap-around patio, perfect for summer evenings and al fresco dining. An outdoor shower provides a refreshing touch after a day at the beach, and the large, lush yard offers plenty of space for recreation and relaxation. Whether you're a culinary enthusiast grilling up a feast or simply enjoying the company of loved ones in the spacious kitchen, this home is designed for entertaining and creating lasting memories. Nestled in the coveted New Suffolk community, you'll be just moments away from the area's most stunning beaches. Embrace the quintessential summer lifestyle in this lovely retreat, where comfort and convenience meet coastal charm.

Freshly reimagined with impeccable style and high-end finishes, this five-bedroom, four-bath retreat delivers the best of summer living in the Hamptons. Completely renovated and fully designer-decorated, every inch of this home reflects a polished, curated aesthetic-where form meets function in all the right ways. Enter into a sleek, sunlit kitchen outfitted with top-of-the-line appliances and striking design elements, opening to a chic dining area and a dramatic double-height living room anchored by a fireplace. All main living spaces flow effortlessly to the expansive deck-perfect for entertaining, lounging, or dining al fresco. The first-floor ensuite primary bedroom (California king) opens directly to the deck and pool area, while a stylish twin guest bedroom and full bath complete the main level. Upstairs, two additional guest rooms (California king and queen) share a well-appointed full bath. The newly finished lower level expands the living space with a cool, casual lounge, wet bar, state-of-the-art media room, fifth bedroom, and full bath-perfect for guests or movie nights. Outside, enjoy a heated in-ground pool, generous lawn, and half basketball court. There is a gym/ workout area in the detached garage for a dedicated, workout experience. Ideally located in Bridgehampton, just minutes from the village and moments from Sag Harbor, this turnkey rental blends sophisticated design with summer-ready amenities in one unforgettable package. [[Rental Registration # RA251101]] EH RR #: RA251101 Rental Terms: Other / Short Term - Year Round: $260,000

Great home for entertaining. Very attractive contemporary in country setting. Five bedroom, four bath home in Water Mill with heated gunite pool plus entertainment room in lower lever. [[Rental Registration # RP201246]] EH RR #: RP250236 Rental Terms: June: $35,000 August - Labor Day: $70,000 July: $60,000 July - Labor Day: $125,000 Memorial Day - Labor Day: $150,000 September: $30,000

Also available: June for $35K; June/July for $125K Enjoy the beauty of this recently renovated five bedroom, five-and-a-half bath traditional in Bridgehampton's horse country. This 4,500+/- square foot home sits on a beautifully manicured full acre with open lawns and a 20' x 40' gunite pool. A large double-height foyer and beautiful staircase greet you as you enter the home while a chef's kitchen and spacious, nicely appointed primary suites on both levels are just some of the other amenities featured in this summer oasis. Close proximity to town, shops, restaurants and beaches complete this spectacular property. Reach out now to secure this wonderful home for summer 2023. Rental Reg #: RP230579 EH RR #: (RP251002) Rental Terms: July: $110,000 June: $50,000 August - Labor Day: $135,000

Enjoy August in this sweet, cozy, updated home with pool. Chef's kitchen, open floorplan with 3 bedrooms, and 2 baths, this home is close to bay beaches. [[Rental Registration # 26-1149]] EH RR #: 26-1149 Rental Terms: Two Weeks: $10,000

Experience the epitome of coastal living just steps from the serene shores of Towd Point Beach. Featuring newly refinished white oak flooring, farmhouse kitchen, Central A/C, BBQ slate patio & deck, hammock, outdoor shower, large lawn and bloom filled gardens. And of course easy access to the beautiful Towd Point beach for swimming and stunning sunsets. Kayaks included and Pet Friendly too! [[Rental Registration # RP260737]] EH RR #: RP260737 Rental Terms: May: $8,000 Two Weeks: $8,000 June: $12,000 August: $19,000 July: $17,000

Beautifully and stylishly renovated cape in East Hampton Springs is offered for summer. This sunny and cozy home offers a bedroom on the first floor, two on the second. Great deck with hot tub and a large green lawn. Close to Maidstone Beach, Springs General Store, and restaurants and coffee shops. [[Rental Registration # 25-1018]] EH RR #: 25-1018 Rental Terms: September: $8,000 August - Labor Day: $17,000 Memorial Day - Labor Day: $38,000 July - Labor Day: $30,000 July: $17,000

So much charm! This fully restored farm house is conveniently located just East of Love Lane and is set far back from the Main Rd offering a quiet country setting as it abuts preserved land to the East. The home has been recently restored and offers EIK, 1st Flr Master Bedroom w/ attached full bath. Living room and dining flow into one another creating an open floor plan. 2nd floor includes 3 additional bedrooms and full bathroom. Exterior features large wrap around deck off of Master Bedroom overlooking rear yard. Look no further for a North Fork year round rental!

Newly renovated in 2018, this bright and airy four-bedroom home is set on a full acre bordering a private preserve, offering rare tranquility and uninterrupted natural views in the heart of Water Mill. The home is filled with natural light throughout, featuring an open-concept kitchen and living space designed for easy summer living and seamless entertaining. The primary suite opens directly to the outdoor deck, creating a true indoor-outdoor lifestyle. Outside, enjoy expansive, fully fenced grounds, a sparkling in-ground pool, and the privacy that comes with backing onto preserved land. Privacy with just sun, space, and calm. Ideally located minutes from ocean beaches, Southampton, and Bridgehampton villages, and top restaurants, this home delivers both convenience and escape. A clean, modern Hamptons rental that actually feels like a getaway. Available August through Labor Day. [[Rental Registration # RP260066]] EH RR #: RP260066 Rental Terms: Other / Short Term - Year Round: $125,000 Memorial Day - Labor Day: $85,000