luxury real estate for rent Sag Harbor, United States

2025 Rates: June $30,000, July $60,000, July-August $125,000 and August-Labor Day $65,000. This stunning two-story home sits on 3.44 acres of beautiful lawns and trees, featuring a circular driveway and a double-arched covered porch with bluestone patio. Inside, the foyer opens to a light filled dining room and great room with 10 foot coffered ceilings, exquisite details, and an elegant chef's kitchen equipped with Crownpoint custom cabinetry and top -of-the-line Wolf and Sub-Zero appliances. French doors lead to a covered porch overlooking the pool and yard. The second floor has 3 bedrooms each with a private bath and 9 foot ceilings. A separate staircase leads to a den with pull out sofa, wet-bar with ref/freezer and it's own full bath. Additional features include a full house generator, alarm system, and two smart tv's. This home is close proximity to Wades Beach and Mashomack Preserve.

Here's the perfect home for year-round living or summer enjoyment! Sited on a beautifully landscaped 1+/- acre in the Northwest Woods that's convenient to East Hampton Village and bay beaches, this lovely property boasts 4 bedrooms, 2.5 baths, and much more. The living room and dining area with cathedral ceilings and skylights create a bright and airy space with wood burning fireplace and glass doors opening to the heated pool and entertaining deck. The house also boasts a generous eat in kitchen and first floor primary suite with 3 guest bedrooms upstairs and a full basement. The perfectly positioned heated pool has an electric pool cover and is surrounded by spacious decking set among flowering shrubs and mature trees to create an ideal spot for relaxing or entertaining. The house also comes with a generator to set your mind at ease should a storm or accident cause a power disruption. Nicely location close to Three Mile Harbor and bay beaches, and short drive into the Village of East Hampton. [[Rental Registration # 22-1276]] EH RR #: 22-1276 Rental Terms: Winter Season: $25,000 Per Month

A welcoming first floor with beautiful natural light from the giant sliders welcoming you to the deck with a large and heated pool. Enjoy the privacy protected by lush green trees and bring relaxation to the next level. Upstairs you will find two good sized bedrooms with a shared bathroom. With the outdoor oasis, you likely won't be spending too much time indoors, but if you choose to you will be as comfortable as ever. Washer and dryer are available in the basement so you never have to leave this gorgeous set up!

Newly renovated 1900's classic full of period charm in prime East Hampton Village location, short distance to Main Street and Jitney. Living room with fireplace, formal dining room, dream entertaining kitchen, sunroom and new screened porch overlooking private gardens with lush, mature plantings, inviting garden entertaining & private, fenced pool. Large primary suite with balcony and luxury bath, 3 additional guest bedrooms. Central air conditioning. Rental Terms: Winter Season: $45,000 Per Month August: $75,000 Other / Short Term - Dec: $15,000

Introducing a beautifully updated 3 bed, 2 bath home, quietly nestled on .45 acres. This residence features a spacious living room perfect for relaxation, a modern, well-equipped kitchen, a cozy den/bonus room for added versatility, and brand new baths. The home also includes a beautiful sunroom that opens up to the backyard, where you'll find spacious patio areas, pool with a brand-new liner, hot tub, an outdoor shower, and a serene sauna-ideal for enjoying the outdoors year-round. A partly finished basement and large shed offers additional space for storage or recreational use. Ideally located just minutes from Sag Harbor, Southampton, and Bridgehampton, this home provides convenient access to world-class ocean and bay beaches, as well as renowned local shopping and dining. A perfect Hamptons retreat combining comfort, privacy, and prime location.

This 3 Bedroom, 2 bathroom, modern home is the perfect centrally located Hamptons getaway! A private home nestled into a quiet and friendly neighborhood in close proximity to bay beaches, a few marinas, great hiking trails, and amazing waterfront restaurants.

Welcome to your new sanctuary! This beautifully designed split-level home offers 4 spacious bedrooms and 3 modern bathrooms, perfect for families or those seeking extra space. As you enter, a few steps past the kitchen you'll be greeted by a bright and airy living area that flows seamlessly into the dining space and back into the kitchen, ideal for entertaining. The kitchen is fully equipped with contemporary appliances and ample storage, making meal prep a breeze. Upstairs, you'll find generously sized bedrooms with large windows, providing plenty of natural light. The primary suite features an en-suite bathroom for added privacy. Head downstairs to discover a cozy family room, perfect for movie nights or playtime. An additional bedroom and bathroom on this level adds convenience for guests and separation for those staying over. The large backyard is perfect for summer barbecues, gardening, or simply enjoying the outdoors. There's plenty of room for kids to play or for pets to roam freely. Located just moments away from Maidstone Beach, this home is close to parks, schools, and shopping as well, making it a perfect place to call home for the summer. Don't miss out on this gem-schedule a tour today!

This just renovated ranch centrally located in Springs offers and incredible stay to its guests. An outdoor shower to cool down from the beach just down the road, a large lawn space for hanging in the evening, and a wonderful deck with a grill to bbq. Thats not all, the inside of this house is immaculate and the layout phenomenal. You will never want to leave this modern gem.

Enjoy this Waterfront rental just steps to Goose Creek beach. Easy water access to Goose Creek from this private location, perfect for kayaking and paddle boarding. Features include 3 bedrooms including second floor primary en-suite with water views, 2 additional guest bedrooms, 2 additional guest baths and plenty of living space overlooking Goose Creek. Spacious bright kitchen, dining area with doors to waterside deck where you will experience beautiful sunsets. The perfect retreat for your summer fun or any other time of the year. Close to all North Fork amenities. Permit # 1023

Welcome to your dream retreat! This distinctive older home boasts five thoughtfully designed levels, offering an abundance of space and character. Each floor presents a unique ambiance, perfect for both relaxation and entertaining. Key Features: Private Primary Suite: Enjoy the ultimate sanctuary with a spacious primary suite, complete with a cozy sitting area, ample closet space, and an en-suite bathroom for your convenience. Open Living Areas: The main living level features large windows that fill the space with natural light, showcasing beautiful architectural details and providing stunning views of the surrounding landscape. Versatile Spaces: With multiple levels, you'll find areas perfect for a home office, gym, or guest suite-tailor the spaces to suit your lifestyle. Outdoor Oasis: Step outside to discover your own private paradise! The swimming pool is ideal for summer gatherings, while the surrounding patio provides a serene setting for lounging or alfresco dining. Charming Details: Original hardwood floors, intricate moldings, and vintage fixtures add a touch of history and charm throughout the home. This property is just minutes away from a private HOA beach, local amenities, and parks. Don't miss your chance to rent this unique home that combines character, comfort, and a fabulous outdoor space for the summer of 2025!

Live in the heart of the action with this beautiful, newly renovated 2-bedroom, 1-bathroom apartment in Greenport Village. This furnished and fully-equipped haven is perfect for anyone seeking a convenient and comfortable place to call home. Available for Seasonal Rent; July $6k, August $6k and Year Round Rent; $3,500

Cedar Shake Ranch home on Goose Creek, ready for renters starting September 2022! Fully renovated, 4-bed, 2.5-bath. White & bright kitchen, living room, and dining, all in an open floor plan, perfect for entertaining. Move seamlessly through living space and out the sliding glass doors to a well-designed outdoor oasis. Built into a ipe deck is a heated swimming pool with lounge chairs and other seating areas surround. Plus, an outdoor shower and a big grassy yard with beautiful landscape, offering plenty of room for lawn games like badminton or corn hole. From the pool deck enjoy serene views of the water and wildlife. Kayak or stand up paddle board from the private dock or ride your bike to South Harbor Park beach or Croteaux Vineyards. Fully equipped home office/den space and exercise area with a Peloton bike in the basement. Available: Sept(not incl LBD):$12k, Oct:$8k, Nov 2022-April 2023:$4k/mo, May 2023(not incl MD):$8k, May 25, 2023 - end of June 2023:$18k, July 2023:$25k

Classic contemporary style New Construction in the heart of Greenport Village. This 2900+ sqft offering features 4 wide white oak hardwood floors throughout w/ inviting Great Room, eat-in Kitchen and Junior Suite bedroom on Main Level. The second floor features an cozy additional den/media room with two generously sized guest bedrooms sharing a full bathroom, laundry, ample storage, a primary ensuite bedroom with walk-in closet and large walk-in shower. In addition to the 1st and 2nd floors is a partially finished basement with separate outdoor access already in place or as lower level gym or media room. For those looking for tremendous value and as central Greenport Village location, this is an absolute must see.

2024 Rates: September $15,000 and October $10,000. This property is a stunning waterfront home located on West Cove in the exclusive Nassau Point area. Offering breathtaking views of the Great Peconic Bay, Robins Island, and New Suffolk, this home exudes charm and sophistication. The main level boasts two spacious great rooms, an enclosed three-season room, an eat-in kitchen, a dining room, and a primary en-suite bedroom. The finished basement includes two additional bedrooms, a full bathroom, and a media room, while the second floor features two more bedrooms and another full bathroom. The property's grounds are beautifully landscaped and elevated, with a mahogany deck, stone patio, outdoor dining area, and stairs leading to a raised platform beach with a pergola, providing easy access to the Bay for a refreshing dip.

Summer 2024 Rates: May24-June30 $20K, July2-Aug1 $30K, Aug2-Sept3 $35K, Sept4-Oct4 $15K: Rare new construction on a quiet side street in Greenport Village, this modern luxury home is the perfect base to explore the beaches, wineries, and farm-to-table dining of the North Fork. Walking distance to downtown Greenport and a short drive from all the major North Fork sights. Or just whittle away your days enjoying the amenities of your luxurious home retreat. Lounge in your heated saltwater pool while sipping a cold drink. Curl up with a book in front of your gas fireplace. Catch up on sleep surrounded by plush bedding on your memory foam mattress. Immerse yourself in the low-key North Fork lifestyle at your private Greenport Getaway.

Relax and enjoy this beautifully appointed bay front house w/ private beach and stunning views of Orient Harbor, Bug Light and Shelter Island. Moor your boat in the bay; kayak, swim, fish or chill on the decks and porches. Basement game room w/ Ping-Pong, TV and games. Conveniently located near shopping, restaurants, ferries, farm stands, vineyards.

Situated in a charming and serene neighborhood in Greenport and located just minutes from both Greenport Village and Southold Town Beach, this recently updated Cape offers 1,500 sq. ft. with 4-bedrooms, 2-baths and a spacious living area that flows seamlessly into a bright and airy eat-in kitchen. A full, unfinished basement leads out to an expansive, fenced backyard, and the attached 1-car garage and driveway capable of accommodating 2 additional vehicles ensures sufficient parking for tenants. Don't overlook the opportunity to rent this gem! Please note that the reported square footage is an approximation as the Town of Southold does not have records of the square footage for the second half story.

Looking for a resort like retreat just outside of bustling Greenport Village? Look no further! This 6 bedroom, 4.5 bathroom stunner offers everything you could ask for and more. From 3 en-suite bedrooms to an open floor-plan with high-end appliances and a killer in-ground pool/hot tub combo, this property serves as the ideal summer rental. This rare offering is also just a short walk to a sugar sand bay beach, close proximity to Islands End Golf Course, local wineries, farm stands and much more!, Additional information: Appearance:Pristine,Interior Features:Guest Quarters

Vacation at this spectacular, completely renovated 4 en suite bedroom home this summer located in the desirable Fleet's Neck neighborhood with 2 gorgeous beaches moments away! Entertain in the open concept living area featuring a large island overlooking the family and dining area, perfect for large gatherings. The first floor features 2 bedrooms with 2 full baths with glass sliders leading out to the deck. Downstairs has 2 more ensuite bedrooms with glass sliders leading out to a patio. Soak up the sun and relax by the saltwater pool, rinse of the sand with the spacious outside shower or enjoy the patio where there is plenty of room to entertain throughout any time of the day. Available April: $12,000, May: $17,500, June: $22,500, July: $35,000, August - LBD: $40,000 and Memorial Day - LBD: $95,000