5-Bedroom Rentals in Suffolk County, NY

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  $22,000 per month

  • 5 Beds
  • 2 Baths
  • 3,000 Sq Ft
  • House for Rent

  45 Budds Pond Rd, Southold, NY 11971

  Available for two week rentals! Escape to your dream Southold summer in this spacious 5-bedroom, 2-bathroom home boasting an in-ground heated pool and convenient dock space. Bathed in natural light and surrounded by lush gardens, this home offers ample space for entertaining and ensuring guests feel right at home. Spend sunny afternoons basking by the pool under the awning or take a leisurely

  Mackenzie Needham Daniel Gale Sothebys Intl Rlty

  45 Budds Pond Rd, Southold, NY 11971
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  /20

  $40,000 per month

  • 5 Beds
  • 5 Baths
  • House for Rent

  146 Westminster Rd, Water Mill, NY 11976

  A gem in one of the most lovely serene sections in Water Mill. This very secluded traditional home sits on a semi-circular lot, south of the highway looking out onto Mecox Bay with a private dock across the street. There are four bedrooms plus two rooms that can be converted into bedrooms. There are four full bathrooms, two Jacuzzis, steam shower, a library, two living rooms, a sunroom, a large

  146 Westminster Rd, Water Mill, NY 11976
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  /23

  $25,000 per month

  • 5 Beds
  • 7 Baths
  • 3,500 Sq Ft
  • House for Rent

  495 N Parish Dr, Southold, NY 11971

  Southold, North Fork.Experience the beauty of seasonal living on Southold Bay. This newly renovated contemporary bayfront estate home invites you to bask in its light and bright ambiance, perfect for relaxation and rejuvenation. With its Zen-inspired organic design, you’ll find comfort and privacy combined with the conveniences of modern life.Nestled near the Southold Yacht Club, just moments

  Nicholas Planamento William Raveis New York LLC

  495 N Parish Dr, Southold, NY 11971
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  /20

  $85,000 per month

  • 5 Beds
  • 6 Baths
  • House for Rent

  54 Bridgefield Rd, Bridgehampton, NY 11932

  Escape to this immaculate traditional sanctuary nestled amidst a 10-acre private vineyard in the tranquil southern enclave. Secluded at the end of a private road, enjoy unparalleled peace and privacy. Elegant decor meets beachside comfort, with an open double-height great room boasting a fireplace, creating a warm and inviting atmosphere. Prepare culinary delights in the gourmet chef's kitchen,

  54 Bridgefield Rd, Bridgehampton, NY 11932
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  $16,000 per month

  • 5 Beds
  • 3 Baths
  • 2,500 Sq Ft
  • House for Rent

  215 Kouros Rd, New Suffolk, NY 11956

  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

  Mackenzie Needham Daniel Gale Sothebys Intl Rlty

  215 Kouros Rd, New Suffolk, NY 11956
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  /17

  $5,500 per month

  • 5 Beds
  • 3 Baths
  • 2,000 Sq Ft
  • House for Rent

  15 Newfoundland Ave, Huntington, NY 11743

  Welcome to this spacious 5-bedroom, 3 full-baths Hi-ranch in the desirable Huntington neighborhood! With an abundance of natural light, hardwood flooring, cathedral ceiling, skylights, large eat-in- kitchen & a second sitting room perfect for relaxing with a book or having game night. Enjoy the generous size bedrooms, including a primary en suite with updated bathrooms. You'll love relaxing on

  15 Newfoundland Ave, Huntington, NY 11743
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  $25,000 per month

  • 5 Beds
  • 3 Baths
  • 3,000 Sq Ft
  • House for Rent

  370 Fishermans Beach Rd, Cutchogue, NY 11935

  Available in 2025: August-LD for 2-3 weeks (dates are flexible) 25K (for 2 weeks). Spend your summer in this stunning five-bedroom retreat on Nassau Point. With 150 feet of waterfront access and just a quick 3-minute stroll to the pristine sands of Fisherman’s Beach, this property is ideal for both boating enthusiasts and beach lovers. The house features elegant furnishings, modern fixtures, and

  Natalie Hough Daniel Gale Sothebys Intl Rlty

  370 Fishermans Beach Rd, Cutchogue, NY 11935
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  /15

  $4,700 per month

  • 5 Beds
  • 2 Baths
  • 1,500 Sq Ft
  • House for Rent

  122 Erlanger Blvd, North Babylon, NY 11703

  Spacious 5 Bedroom, 2 Bath Home in Prime North Babylon/Deer Park Location!Welcome home to this beautifully updated and expansive 5-bedroom, 2-bathroom rental nestled in a quiet, family-friendly neighborhood near Deer Park and North Babylon, NY. This home offers the perfect blend of comfort, space, and convenience — ideal for growing families, professionals, or anyone looking for a

  122 Erlanger Blvd, North Babylon, NY 11703
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  $150,000 per month

  • 7 Beds
  • 10 Baths
  • 9,909 Sq Ft
  • House for Rent

  150 Water Mill Towd Rd, Water Mill, NY 11976

  Aug 18 to Sept 17 - $150,000 / Aug 18 to Sept 1 - $100,000 / Sept 4 to Sept 17 - $95,000. Escape to Hamptons horse country in this remarkable Water Mill Estate, offering an unparalleled lifestyle with a pool, pool house and tennis court, overlooking open land, polo fields and stables. The custom-built home features an impressive entryway, a great room and living room with fireplaces, formal

  Enzo Morabito Douglas Elliman Real Estate

  150 Water Mill Towd Rd, Water Mill, NY 11976
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  /20

  $34,210 per month

  • 6 Beds
  • 6 Baths
  • 3,874 Sq Ft
  • Condo for Rent

  13 Brander Pkwy Unit ID1014115P, Shelter Island, NY 11964

  Welcome to Sandpoint, an exclusive Shelter Island retreat recently built on 1.4 acres, just a stone's throw from a sandy beach and across from a 12-acre preserve. This stunning home features five bedrooms, including two master suites and one room with twin beds. Sunlit and spacious, the heart of the home is a well-equipped kitchen with an oversized island overlooking a large pool and landscaped

  13 Brander Pkwy Unit ID1014115P, Shelter Island, NY 11964
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  /15

  $4,625 per month

  • 6 Beds
  • 2 Baths
  • 1,800 Sq Ft
  • House for Rent

  Unlisted Address

  Spacious 6 bedroom Colonial with 2 full baths, Brand new sparkling wood floors on second floor, New Washer & dryer included, Wide driveway for ample parking, fenced in back yard, Shed, Tenant to pay all utilities and maintain grounds, Pet friendly with restriction, Middle Country School District.

  Gina Amen American Real Estate Assoc Inc

  Unlisted Address
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  /20

  $12,180 per month

  • 5 Beds
  • 3 Baths
  • 2,808 Sq Ft
  • Condo for Rent

  25 Glendale Dr Unit ID1026170P, Montauk, NY 11954

  Welcome to Glendale, a stunning 2,800 sqft colonial-style home nestled on a private road in Montauk. This spacious residence features five bedrooms and three and a half bathrooms, offering a bright and airy interior with hardwood floors. Enjoy two comfortable living rooms, one with a stone fireplace, and a cook's country kitchen with a Basque dining table that seats 12 guests. The main level

  25 Glendale Dr Unit ID1026170P, Montauk, NY 11954
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  $195,000 per month

  • 5 Beds
  • 4.5 Baths
  • 5,055 Sq Ft
  • House for Rent

  52 Sandy Hollow Rd, Southampton, NY 11968

  Welcome to your dream rental in the heart of Southampton! This stunning 5-bedroom, 4.5-bathroom home spans an impressive 5,000 square feet, providing ample space for relaxation and entertainment. With a beautifully heated gunite pool in the backyard, you can enjoy refreshing swims and sun-soaked afternoons right at home. In addition to the spacious living areas, the property features a versatile

  Clare Ambrose Au Dela Real Estate LLC

  52 Sandy Hollow Rd, Southampton, NY 11968
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  /20

  $19,140 per month

  • 6 Beds
  • 4 Baths
  • 3,400 Sq Ft
  • Condo for Rent

  1653 Millstone Rd Unit ID401720P, Sag Harbor, NY 11963

  Welcome to Meadowood Manor, a luxurious home located in the heart of Sag Harbor. This exquisite residence offers a selection of amenities including a saltwater pool, hot tub, outdoor shower, and a private full basketball and tennis court. Inside, the open floor concept with an expansive living space and fully stocked kitchen is perfect for lounging. With six luxurious bedrooms, this home provides

  1653 Millstone Rd Unit ID401720P, Sag Harbor, NY 11963
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  $55,000 per month

  • 5 Beds
  • 3.5 Baths
  • 2,296 Sq Ft
  • House for Rent

  552 Dune Rd, Westhampton Beach, NY 11978

  Perched along Dune Road, this delightful two-story home captures stunning sunrises and sunsets with sweeping bay views visible from nearly every room. The residence offers five bedrooms and three and a half bathrooms, blending comfort with coastal allure. On the main level, an airy living space features a warm fireplace, accompanied by a primary bedroom with its own en-suite bathroom, a fully

  Lisa Semeraro Kerrigan Country Realty

  552 Dune Rd, Westhampton Beach, NY 11978
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  /20

  $170,000 per month

  • 5 Beds
  • 5 Baths
  • House for Rent

  121 Harvest Ln, Southampton, NY 11968

  Located within one mile of Southampton Village's renowned Main Street shops and dining, and just a short stretch further to the white sandy beaches of the Atlantic Ocean and Coopers Beach (rated #1 in the USA), this 6,000+ sq. ft. traditional home offers the ideal Hamptons summer lifestyle. Spread across three levels, this five-bedroom residence features a gracious entry hall leading to a sunlit

  121 Harvest Ln, Southampton, NY 11968
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  $50,000 per month

  • 5 Beds
  • 3 Baths
  • 2,540 Sq Ft
  • House for Rent

  5 Lakewood Ln, Quogue, NY 11959

  SUNNY QUOGUE VILLAGE RENTAL. This fresh contemporary home on secluded Lakewood Lane has everything you need for summer fun in Quogue. The bright and airy open floor plan includes a state of the art kitchen, a spacious living room with fireplace, five bedrooms and three baths, and a new gym, all positioned with easy access to outdoor entertainment. With the large heated pool and pool deck, the

  Amanda Murray Corcoran

  5 Lakewood Ln, Quogue, NY 11959
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  /20

  $60,000 per month

  • 6 Beds
  • 7 Baths
  • House for Rent

  69 Gould St, East Hampton, NY 11937

  Look no further. Enjoy your summer in this fresh and sleek, six bedroom, five and a half bath retreat, close to the village of East Hampton. This idyllic home offers an en-suite bedroom on the main level, a formal living room, cozy gathering room with wood burning fireplace, that flows seamlessly into the professional kitchen, and dining area. The second floor boasts a generous master suite

  69 Gould St, East Hampton, NY 11937
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  /7

  $220,000 per month

  • 5 Beds
  • 6 Baths
  • 5,800 Sq Ft
  • House for Rent

  93 Hog Creek Ln, East Hampton, NY 11937

  Clearwater Modern FarmhouseThis newly constructed sprawling farmhouse style home was built in 2023 on a double lot in Clearwater Beach. With almost 6,000 sqft of finished space throughout the home, it has five bedrooms, four full baths and two half baths. The first floor consists of a large chef's kitchen with two stoves, two dishwashers, ice maker & beverage fridge and a fully stocked pantry

  Jessica Fingleton Au Dela Real Estate LLC

  93 Hog Creek Ln, East Hampton, NY 11937
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  /20

  $20,000 per month

  • 5 Beds
  • 3 Baths
  • House for Rent

  131 Lewis Rd, East Quogue, NY 11942

  Location, location, location. Five bedrooms, three baths, on-suite first-floor primary, gourmet kitchen with breakfast bar, conveniently located across the street from the park, walk to town, minutes from the Hampton Jitney, exquisitely decorated, beach vibes, sundrenched deck, electric awning and inground pool-your vacation home starts here. [[Rental Registration # RP250284]]

  131 Lewis Rd, East Quogue, NY 11942
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  $35,000 per month

  • 6 Beds
  • 6.5 Baths
  • 8,627 Sq Ft
  • House for Rent

  233 N Magee St, Southampton, NY 11968

  Step into a home where artistry meets architecture, where light dances across carefully curated designer finishes, and where every space is crafted for inspired living. The Interiors designed by a notable creative mind, this 8,627 square-foot contemporary sanctuary is a rare opportunity to experience luxury as an art form. This six-bedroom, six-and-a-half-bath home is more than just a place

  Priscilla Holloway Douglas Elliman Real Estate

  233 N Magee St, Southampton, NY 11968
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  /20

  $175,000 per month

  • 5 Beds
  • 5 Baths
  • House for Rent

  21 Shrubland Rd, Southampton, NY 11968

  This Southampton waterfront property is navigable to great Peconic Bay. This 4,200 square foot Post Modern is set on 2.1 acres. Five bedrooms (3 are en suite), 4.5 baths, true gourmet cook's kitchen, with a great room opening onto mahogany deck for summer dining and entertaining. Outside this Hamptons home you will find a heated gunite pool, path to Cold Spring Pond for easy fishing, swimming,

  21 Shrubland Rd, Southampton, NY 11968
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  $125,000 per month

  • 5 Beds
  • 5 Baths
  • 3,500 Sq Ft
  • House for Rent

  11 Oneck Rd, Westhampton Beach, NY 11978

  Welcome to your summer 2025 rental! This architecturally classic 5 bedroom, 5 bathroom residence, sprawling across 3,500 square feet, is a perfect blend of Hamptons charm and artistic ambience. Spend time in the thoughtfully renovated kitchen, featuring sleek countertops and top-of-the-line appliances complete with double oven and wine fridge perfect for culinary adventures and entertaining. The

  Dana Bartel Compass Greater NY LLC

  11 Oneck Rd, Westhampton Beach, NY 11978
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  /20

  $125,000 per month

  • 5 Beds
  • 4 Baths
  • House for Rent

  40 Poxabogue Pond Rd, Sagaponack, NY 11937

  Escape to this serene Sagaponack home, perfectly located just moments from world-class beaches, golf courses, and renowned wineries. Set on nearly two acres with over 200 feet of private pond frontage, this home offers breathtaking water views and ultimate tranquility, bordered by a 17-acre agricultural reserve. Inside, the main floor features a spacious eat-in kitchen with a fireplace, a

  40 Poxabogue Pond Rd, Sagaponack, NY 11937
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  $80,000 per month

  • 6 Beds
  • 3 Baths
  • 4,200 Sq Ft
  • House for Rent

  45 Sandra Rd, East Hampton, NY 11937

  This newly rebuilt six-bedroom, three-bath home in East Hampton seamlessly blends modern luxury with timeless craftsmanship, featuring original post-and-beam construction that adds warmth and character. Designed to accommodate up to 12 guests, the residence offers a sophisticated yet inviting atmosphere with soaring ceilings, exposed wood beams, and high-end finishes throughout. Three king

  Joseph Van Asco Douglas Elliman Real Estate

  45 Sandra Rd, East Hampton, NY 11937
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  /20

  $65,000 per month

  • 6 Beds
  • 7 Baths
  • House for Rent

  32 S Beach Rd, Southampton, NY 11968

  Bayfront Shinnecock Hills contemporary has waterviews and beach access. Open floor plan with beautiful interior spaces with soaring ceilings and large windows that bring in light and summer breezes. Living room with fireplace, well-equipped kitchen, and game room with pool table and ping pong. Master suite has its own viewing deck and master bath is equipped with marble Jacuzzi. Four

  32 S Beach Rd, Southampton, NY 11968
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  $250,000 per month

  • 9 Beds
  • 8.5 Baths
  • 9,000 Sq Ft
  • House for Rent

  70 Winding Way, Water Mill, NY 11976

  May 19 - July 13 - $250,000 / June $150,000 / July 1 - July 14 - $125,000 Welcome to this stunning 9,000 sq. ft. villa in Southampton, ideally located on a quiet street and tranquil cul-de-sac in Water Mill, overlooking a beautiful vineyard. This luxurious home provides an exceptional lifestyle with 9 bedrooms and 8.5 bathrooms, making it the perfect retreat for those seeking a lavish

  Charisse Chassen Brown Harris Stevens Hamptons

  70 Winding Way, Water Mill, NY 11976
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  /20

  $20,000 per month

  • 5 Beds
  • 6 Baths
  • House for Rent

  7 Bridge Hill Ln, Bridgehampton, NY 11932

  This recently updated and expanded traditional home is on a secluded flag lot equidistant from the Village of Bridgehampton with its restaurants and ocean beaches and the Village of Sag Harbor with its own array of restaurants, marinas, and bay beaches. This is a fabulous spot for your Hamptons Vacation. After seeing the lush grounds bordering a reserve, you may not want to venture inside, but

  7 Bridge Hill Ln, Bridgehampton, NY 11932
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  $40,000 per month

  • 6 Beds
  • 7.5 Baths
  • 4,900 Sq Ft
  • House for Rent

  146 Coopers Farm Rd, Southampton, NY 11968

  This stunning Southampton Village residence exudes timeless elegance and charm, starting with a striking double-height foyer that ushers you into a space of effortless sophistication. The open-concept layout features a gourmet kitchen with custom cabinetry and top-of-the-line appliances, a formal dining area, and a spacious living room centered around a cozy fireplace. A first-floor junior master

  Lynne Leahy Nest Seekers International LLC

  146 Coopers Farm Rd, Southampton, NY 11968
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  /20

  $90,000 per month

  • 7 Beds
  • 7 Baths
  • House for Rent

  268 Madison St, Sag Harbor, NY 11963

  Set in a prime location this spacious, light-filled home sits on one of the largest lots in the Historic District of Sag Harbor. Located in a quiet, private setting just ten minutes from the village shops and restaurants, the property is a perfect summer compound in the middle of all that the Hamptons has to offer. The open-plan first floor offers a large kitchen, a dining area with a table that

  268 Madison St, Sag Harbor, NY 11963
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  $40,000 per month

  • 5 Beds
  • 5 Baths
  • 3,600 Sq Ft
  • House for Rent

  38 Bridle Path, Westhampton Beach, NY 11978

  Well appointed traditional 5 bedroom Hamptons home. Located in the private community of Bridle Path, just minutes from Village of Westhampton Beach shops, restaurants and Dune Road beaches. Beautifully furnished with a coastal aesthetic and attention to detail in every room. The main floor offers 2 bedrooms & 2 full bathrooms, including a spacious primary suite with private access to the pool

  Allison Galasso Kerrigan Country Realty

  38 Bridle Path, Westhampton Beach, NY 11978
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  /20

  $85,000 per month

  • 5 Beds
  • 6 Baths
  • House for Rent

  40 Edwards Ave, East Hampton, NY 11937

  A gorgeous contemporary 5 bedroom, 4.5 bath, designer decorated home will be the perfect backdrop for you to spend this summer in The Hamptons. Set at the end of a dead-end street, it is a haven set only moments to both Amagansett and East Hampton Villages. Fenced-in and landscaped grounds with a heated gunite pool, outdoor kitchen and covered porch for outdoor dining provides all that you need

  40 Edwards Ave, East Hampton, NY 11937
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  $65,000 per month

  • 5 Beds
  • 3.5 Baths
  • 2,763 Sq Ft
  • House for Rent

  1920 The Strand, East Marion, NY 11939

  Serene, private, and tranquil oasis perfect for those looking to relax, unwind and unplug. A beautifully landscaped property overlooking the Long Island Sound with private beach access and breathtaking views from all levels of the home. Ground Level has 4 B/R's, 2 Baths, Laundry Room and Family Room which opens to Deck, Pool, and Bluff. Enjoy majestic sunsets from an additional deck perched at

  Elena Ermogenous Century 21 Unique Realty

  1920 The Strand, East Marion, NY 11939
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  /20

  $150,000 per month

  • 5 Beds
  • 5 Baths
  • House for Rent

  130 Harvest Ln, Southampton, NY 11968

  set on a lush half acre this stunning pristine Post Modern features southwestern sun exposure for all day sun exposure and stunning sunsets. 4,899 square feet defines 4/5 bedrooms/4.5 baths, meticulous cooks kitchen features wolf, subzero, bosch, miele and scottsman stainless appliances. Double height greatroom/dining area features an oversized wood burning fireplace. Covered back porch is set up

  130 Harvest Ln, Southampton, NY 11968
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  $180,000 per month

  • 5 Beds
  • 5 Baths
  • 4,026 Sq Ft
  • House for Rent

  2 Little Neck Rd, Southampton, NY 11968

  Nestled in the heart of Southampton, this exquisite residence epitomizes coastal elegance and luxurious living. Boasting 5 spacious bedrooms and 5 beautifully appointed baths, every inch of this home is thoughtfully crafted to blend comfort with sophisticated style. The gourmet kitchen, outfitted with state-of-the-art appliances, effortlessly opens into sun-drenched dining and living spaces,

  Louis Bougatsos Coldwell Banker Reliable R E

  2 Little Neck Rd, Southampton, NY 11968
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  /20

  $50,000 per month

  • 5 Beds
  • 6 Baths
  • House for Rent

  151 N Ferry Rd, Shelter Island, NY 11964

  This stunning 5 bedroom, 4.5 bath home has 6 acres and easy access to Dering Harbor Marina, the Shelter Island Yacht Club, Town dock, ferry, tennis, shops and restaurants in picturesque Shelter Island Heights. The house has first and second floor verandas, a center hall foyer, flanked by the living and dining rooms with a family-room, fireplace, powder room, marble and stainless kitchen and mud

  151 N Ferry Rd, Shelter Island, NY 11964
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  $40,000 per month

  • 5 Beds
  • 5.5 Baths
  • 4,000 Sq Ft
  • House for Rent

  61 Peconic Ave, Sag Harbor, NY 11963

  Envision your perfect summer unfolding in this exquisite and expansive residence nestled within Shelter Island’s prestigious Silver Beach area. Recently completely renovated from the ground up in 2024, this home boasts a captivating blend of elegance and modernity. Step inside to discover a meticulously designed floor plan featuring dual primary suites, one conveniently located on the ground

  Michael Brennan Douglas Elliman Real Estate

  61 Peconic Ave, Sag Harbor, NY 11963
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  /20

  $105,000 per month

  • 5 Beds
  • 6 Baths
  • House for Rent

  1194 Sagg Rd, Sagaponack, NY 11962

  This secluded enclave is set on two beautifully landscaped acres down a long private driveway and abuts a 20 acre reserve, creating a stunning summer oasis. There are 4 bedrooms and 4-1/2 baths in the main house and 1 bedroom and bath in the guest cottage. This contemporary home has a beautiful flow, you enter into the foyer with the sweeping stairs to the second floor bedroom level. To the right

  1194 Sagg Rd, Sagaponack, NY 11962
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  /39

  $40,000 per month

  • 6 Beds
  • 7.5 Baths
  • 7,000 Sq Ft
  • House for Rent

  89 Old Canoe Place Rd, Hampton Bays, NY 11946

  Tucked away on a lush, one-acre lot in Shinnecock Hills, this exquisite 6-bedroom, 7.5-bath estate epitomizes luxury living just moments from Southampton Village and the vibrant offerings of Hampton Bays. Surrounded by beautiful Ocean and Bay beaches, the outdoor space is an entertainer’s dream, featuring a heated saltwater gunite pool and a sprawling bluestone patio—ideal for relaxing in the sun

  Maida Srdanovic Compass Greater NY LLC

  89 Old Canoe Place Rd, Hampton Bays, NY 11946
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  /20

  $95,000 per month

  • 6 Beds
  • 5 Baths
  • House for Rent

  249 Roses Grove Rd, Water Mill, NY 11976

  Recently updated 6 bedroom / 4.5 bathroom house with an oversized diving pool and a private tennis court centrally located on lush 4 acres in Water Mill at 249 Roses Grove Road. The soaring living room and a fully stocked Poggenpohl kitchen open up into a wonderfully set up oversized deck & pool surrounded by lush greenery and hidden from the road at the end of a 150 foot driveway. All house

  249 Roses Grove Rd, Water Mill, NY 11976

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