Watermill, NY Homes for Rent

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  $35,000 per month

  • 4 Beds
  • 2.5 Baths
  • 2,424 Sq Ft
  • House for Rent

  28 Old Trail Rd, Water Mill, NY 11976

  Summer in the Hamptons Starts Here | August Rental - $40,000 Spend August in effortless Hamptons style at this beautifully appointed 4-bedroom, 2.5-bath retreat, ideally located on quiet Old Trail and just minutes from both Sag Harbor Village and Southampton Village. Designed for relaxed summer living, the home offers bright, open interiors with comfortable gathering spaces, a well-equipped

  Bridget Terry Compass Greater NY LLC

  28 Old Trail Rd, Water Mill, NY 11976
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  $135,000 per month

  • 6 Beds
  • 7 Baths
  • House for Rent

  1 Paumanok Rd, Water Mill, NY 11976

  The property is approximately 6,000 square feet with 6 bedrooms, 6 full bathrooms, and 1 half bath. Four bedrooms are located on the second level, including a primary suite with separate tub and walk-in steam shower with bench, a junior primary suite, and 2 additional bedrooms sharing a Jack-and-Jill bath. The main level includes a TV den with sliding doors that can convert to a 7th bedroom, a

  1 Paumanok Rd, Water Mill, NY 11976
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  $40,000 per month

  • 3 Beds
  • 2.5 Baths
  • 1,871 Sq Ft
  • Condo for Rent

  34 Village Green Dr, Southampton, NY 11968

  Recently built, impeccably designed condominium in Southampton for Best in Class Modern appointed and Easy Luxury living. It is the perfect residence or your "Home Away from Home". You will enjoy the well detailed and appointed finishes, Sub-Zero, Wolfe, Bosche and LG appliances with luxurious woodworking details and moldings throughout. Open floor plan, covering 1,871 square feet of living

  Suzanne Sienkiewicz Nest Seekers International LLC

  34 Village Green Dr, Southampton, NY 11968
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  /22

  $25,000 per month

  • 5 Beds
  • 6 Baths
  • House for Rent

  36 Mill Creek Close, Water Mill, NY 11976

  RENTED June 24th- July 31st!! Open, Bright Contemporary Beach House South of the Highway in Water Mill with 6 bedrooms, and 5.5 bathrooms overlooking a large 27+/- acre Ag. Reserve. All situated on a beautifully landscaped 1.3+/- acre parcel. Two master suites (one upstairs with balcony and one downstairs), a large guest suite/work studio separated from the rest of the home, and a downstairs

  36 Mill Creek Close, Water Mill, NY 11976
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  $90,000 per month

  • 3 Beds
  • 2 Baths
  • 1,933 Sq Ft
  • Condo for Rent

  1 Village Green Dr, Southampton, NY 11968

  Recently built, impeccably designed condominium in Southampton for Best in Class Modern appointed and Easy Luxury living. It is the perfect residence or your "Home Away from Home". You will enjoy the well detailed and appointed finishes, Sub-Zero, Wolfe, Bosche and LG appliances with luxurious woodworking details and moldings throughout. Open floor plan, covering 1,871 square feet of living

  Suzanne Sienkiewicz Nest Seekers International LLC

  1 Village Green Dr, Southampton, NY 11968
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  $45,000 per month

  • 3 Beds
  • 4 Baths
  • House for Rent

  493 Sagaponack Rd, Sagaponack, NY 11962

  This unique property exudes beauty and tranquility in best South of the Highway location. Close to Sagaponack beaches this charming 3 bedroom house has never been offered for rent. Situated on 1.16 acres of beautifully landscaped vistas by renowned landscape designer, Edwina Von Gal, overlooking Sagg Pond.Rental Terms:Two Weeks: $45,000

  493 Sagaponack Rd, Sagaponack, NY 11962
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  $50,000 per month

  • 2 Beds
  • 2 Baths
  • 2,197 Sq Ft
  • House for Rent

  1 Burkeshire Dr, Sag Harbor, NY 11963

  Soak up the perfect Hamptons summer in Sag Harbor w/ your very own private spa experience. The sunny pool house featuring a gunite pool, yoga deck and sauna will melt your cares away upon your arrival, after a day at the beach or after a day strolling through downtown Sag Harbor. The primary bedroom features vaulted ceilings, a skylight, a ceiling fan a king size bed and in wall speakers. The

  Zachariah Zaleski Douglas Elliman Real Estate

  1 Burkeshire Dr, Sag Harbor, NY 11963
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  $70,000 per month

  • 3 Beds
  • 4 Baths
  • House for Rent

  308 Towd Point Rd, Southampton, NY 11968

  WATERFRONT COMPOUND WITH POOL! Swim, fish, or launch the kayak, paddle board or sunfish sailboat(included) from this waterside haven! Located on Davis Creek, this Towd Point Beach Rental has unobstructed views of the harbor and beyond to Conscience Point National Wildlife Refuge. Featuring a cottage-style main house with three bedrooms and two bathrooms and a modern-barn style pool house that

  308 Towd Point Rd, Southampton, NY 11968
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  $45,000 per month

  • 2 Beds
  • 2 Baths
  • 1,025 Sq Ft
  • House for Rent

  10 Henry St, Southampton, NY 11968

  Southampton Village Gem in mint condition with beautiful gardens, mature landscaping and Gunite pool. This home and property are turn key. It offers 1025 square feet of entertaining space between the main residence and the fabulous pool house. The home and property are wonderfully appointed and located on a quiet lane in Southampton Village just moments from the shops and ocean beaches.

  Beth Marano Corcoran

  10 Henry St, Southampton, NY 11968
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  /23

  $155,000 per month

  • 5 Beds
  • 5 Baths
  • House for Rent

  1366 Scuttle Hole Rd, Water Mill, NY 11976

  This spectacular and multifaceted dream home in Water Mill is now available for rent for summer 2026. Located in the heart of Hampton's horse country, this property offers a host of entertaining activities for a summer full of memories. Highlights of the first floor include a large entry foyer, a double-height living room with two-sided fireplace, a spacious chef's kitchen with high-end

  1366 Scuttle Hole Rd, Water Mill, NY 11976
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  $30,000 per month

  • 4 Beds
  • 3 Baths
  • 1,825 Sq Ft
  • House for Rent

  286 Towd Point Rd, Southampton, NY 11968

  Welcome to your tranquil summer haven. Where hiking, biking, kayaking, fishing and stunning water views await. Immerse yourself in the sound of nature. Just in time for summer. Completely remodeled new kitchen and bathrooms. This home boasts 4 beds and 3 full bathrooms, one being the primary suite. Ductless AC Units in all bedrooms and living space and water views from every room and a Gas

  Linda Jolly Douglas Elliman Real Estate

  286 Towd Point Rd, Southampton, NY 11968
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  /29

  $100,000 per month

  • 7 Beds
  • 8 Baths
  • House for Rent

  50 Rosko Ln, Southampton, NY 11968

  Welcome to 50 Rosko Lane in The Fields, Southampton's premier luxury enclave. This west-facing new construction offers abundant natural light, and over 6,000 sq. ft. of beautifully designed living space. With 7 bedrooms, 7 baths, and a finished lower level, the home balances refined Hamptons style with modern comfort. The airy main level showcases soaring ceilings, wide-plank floors, and a chef's

  50 Rosko Ln, Southampton, NY 11968
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  /23

  $18,000 per month

  • 3 Beds
  • 2 Baths
  • 1,600 Sq Ft
  • House for Rent

  10 Cedar Ave, Southampton, NY 11968

  This beautiful mid-century modern high ranch is located near bay beaches, restaurants, golf courses, marinas, and farm stands in Southampton North. Available for the US OPEN. The top floor features a primary bedroom and bath, a living room, and a kitchen, all complemented by a wraparound terrace. The ground level includes two guest bedrooms and an additional full bath. The heated inground pool

  Robert Florio Daniel Gale Sothebys Intl Rlty

  10 Cedar Ave, Southampton, NY 11968
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  $30,000 per month

  • 4 Beds
  • 4 Baths
  • House for Rent

  17 Bayview Rd, Southampton, NY 11968

  This Southampton beach house blends playful coastal personality with relaxed Hamptons living. Located in Bay View Oaks, a waterfront community with private beach access, deeded rights to Peconic Bay, and a boat launch, the home sits in a quiet setting within Bay View Oaks, just 10 minutes from both Sag Harbor and Southampton Villages. Inside, the home features high ceilings, light-filled rooms,

  17 Bayview Rd, Southampton, NY 11968
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  $45,000 per month

  • 3 Beds
  • 2 Baths
  • 1,596 Sq Ft
  • House for Rent

  9 Helens Ln, Southampton, NY 11968

  Southampton Cove Retreat – Renovated 3BR with Water Views & Deck Just renovated! This stunning 3-bedroom, 2-bath home offers an open floor plan with brand-new floors and modern bathrooms. The spacious great room flows seamlessly to a large deck, perfect for entertaining or relaxing while enjoying serene water views. A bonus room on the first floor has a separate kitchenette and laundry. Located

  Nancy Pearson Sothebys Int'l Realty Hamptons

  9 Helens Ln, Southampton, NY 11968
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  $55,000 per month

  • 3 Beds
  • 4 Baths
  • House for Rent

  114 Narod Blvd, Water Mill, NY 11976

  Spend your summer in a coveted South of the Highway Mecox waterfront community, surrounded by $5 to $10 million homes and tucked away on a quiet one way lane just moments from Mecox Bay and the ocean beaches. This stylish 3 to 4 bedroom retreat offers classic Hamptons interiors with an eat in kitchen that flows seamlessly into a dramatic living room with soaring cathedral ceilings and abundant

  114 Narod Blvd, Water Mill, NY 11976
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  $30,000 per month

  • 3 Beds
  • 3 Baths
  • 1,904 Sq Ft
  • House for Rent

  1008 Middle Line Hwy, Sag Harbor, NY 11963

  Welcome to the Sag Harbor escape everyone is searching for — and almost no one finds. Set behind gates on 3.6 acres of pristine, private grounds, this beautifully designed Hamptons retreat offers the rare combination of total privacy, resort-style outdoor living, and effortless access to everything Sag Harbor is loved for. It’s peaceful, spacious, and completely turnkey — the kind of place guests

  Elizabeth Cordova Alata Douglas Elliman Real Estate

  1008 Middle Line Hwy, Sag Harbor, NY 11963
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  $195,000 per month

  • 5 Beds
  • 4 Baths
  • House for Rent

  51 Seascape Ln, Sagaponack, NY 11962

  Modern, cool and comfortable. Set on a private acre just five minutes from beautiful Sagaponack ocean beaches. Perfect refuge with indoor and outdoor space for rest or to work from home with hi-speed internet, and full house generator. The open-style kitchen has a six-burner Samsung gas stove, Meile dishwasher, and Sub-Zero fridge. It opens to a comfortable living room with gas fireplace, and a

  51 Seascape Ln, Sagaponack, NY 11962
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  $50,000 per month

  • 6 Beds
  • 6 Baths
  • 3,520 Sq Ft
  • House for Rent

  78 Mecox Rd, Water Mill, NY 11976

  Great house for entertaining and close to all the Villages in a central location. South of the highway and close to the beach.

  Nancy Pearson Sothebys Int'l Realty Hamptons

  78 Mecox Rd, Water Mill, NY 11976
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  $150,000 per month

  • 7 Beds
  • 8 Baths
  • House for Rent

  39 Marylea Dr, Southampton, NY 11968

  This beautiful village estate section home was built in 1880 and completely renovated in 1998. Features 6,000+/- sq. ft. of living space, including a formal Living room, a sunroom, a formal dining room, a large, eat in, gourmet kitchen, 7 main bedrooms including a 1st and 2nd floor master suite, 7 1/2 baths, large sunroom, beautiful outdoor terraces leading to 2.0+/- acres of gardens with mature

  39 Marylea Dr, Southampton, NY 11968
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  /20

  $30,000 per month

  • 3 Beds
  • 2.5 Baths
  • 1,612 Sq Ft
  • Condo for Rent

  50 Hubbard Ln Unit 117, Southampton, NY 11968

  Escape to your ultimate summer retreat at Southampton Commons, where resort-style living meets effortless elegance. This fully renovated corner condo offers an unbeatable location just a stone’s throw from the community's luxurious amenities—dive into one of two sparkling pools, soak in the hot tub, stay active at the gym, or challenge friends to a match on the tennis or pickleball courts.

  Sean Gray Compass Greater NY LLC

  50 Hubbard Ln Unit 117, Southampton, NY 11968
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  /31

  $50,000 per month

  • 4 Beds
  • 3 Baths
  • House for Rent

  2629 Montauk Hwy, Bridgehampton, NY 11932

  This Bridgehampton South classic country farmhouse nestled far off the road on a deep flag lot a 1/4 of a mile to town. This charming house is surrounded by hydrangea in a very private .53-acre parcel. A heated salt-water Gunite pool with a sunning level provides for luxurious sunbathing and a private back deck is partially shaded for evening grilling, and dining alfresco. The large custom chef's

  2629 Montauk Hwy, Bridgehampton, NY 11932
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  /20

  $7,000 per month

  • 4 Beds
  • 3.5 Baths
  • 2,000 Sq Ft
  • Property for Rent

  9 Pine Tree Rd, Southampton, NY 11968

  Available: Short-term and Fully Furnished Welcome to 9 Pine Tree Road—a newly reimagined Hamptons retreat set within one of Southampton North’s most coveted waterfront communities, just moments from a private, residents-only beach. This exceptional four-bedroom, two-and-a-half-bath home has been fully transformed through a brand-new designer renovation, offering a refined blend of modern style,

  Brody Lluis R New York

  9 Pine Tree Rd, Southampton, NY 11968
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  $15,000 per month

  • 3 Beds
  • 4 Baths
  • House for Rent

  74 Fordham Rd, Southampton, NY 11968

  Also available: Two weeks: Jun 1 - Jun 25 $15K, Two weeks: Sep 9 - Sep 30 $20KAs featured in Hampton Cottages and Gardens, located on a quiet Village lane, this exquisite three bedroom three bath plus powder room oasis on one level provides maximum privacy yet is in close proximity to Village shops, restaurants and famous ocean beaches. From entering the home, the foyer leads into the

  74 Fordham Rd, Southampton, NY 11968
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  $72,000 per month

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

  4 Carriage Ln, Southampton, NY 11968

  FLEXIBLE WEEKS AVAILABLE! **Just 3 miles from Shinnecock Hills Golf Course. 1 Mile to Main Street. 2 Miles to Beach. Completely redesigned and newly rebuilt, this home sits on an expansive .3 acre with spectacular views located in a private cut de sac in the Dunes of Southampton. This coastal chic home features almost 3000 square feet of interior living space plus an outdoor lounge and dining

  Patricia Pascullo Salegna Douglas Elliman Real Estate

  4 Carriage Ln, Southampton, NY 11968
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  /22

  $10,000 per month

  • 5 Beds
  • 2 Baths
  • House for Rent

  465 Blank Ln, Water Mill, NY 11976

  The pastoral areas around the house make you relax, there are 3 wings- the master ensuite, the middle entertaining area with kitchen, dining room 2 small bedrooms with their own office area and a third 2 bedroom / bath wing. Very peaceful. 10 minutes to ocean and bay beaches. [[Rental Registration # RP241674]] EH RR #: RP241674Rental Terms:September: $10,000

  465 Blank Ln, Water Mill, NY 11976
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  $20,000 per month

  • 2 Beds
  • 2.5 Baths
  • 1,229 Sq Ft
  • Condo for Rent

  50 Hubbard Ln Unit 14, Southampton, NY 11968

  Enter into this immaculate 2 bedroom 2 1/2 bath adorable condo. You're greeted with double-height ceilings. To the right you have a small room for reading or work space. Gourmet Kitchen with all the amenities for entertaining. Oversized cozy living room with fire place for those chilly nights. Steps leading to the primary bedroom ensuite along with a secondary bedroom ensuite. This community

  Linda Kouzoujian Corcoran

  50 Hubbard Ln Unit 14, Southampton, NY 11968
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  $70,000 per month

  • 8 Beds
  • 9 Baths
  • House for Rent

  111 S Main St, Southampton, NY 11968

  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

  111 S Main St, Southampton, NY 11968
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  /22

  $35,000 per month

  • 4 Beds
  • 3 Baths
  • 2,372 Sq Ft
  • House for Rent

  17 Underhill Dr, Southampton, NY 11968

  Welcome to your new stylish home at 17 Underhill Rd, Southampton, located in the heart of Suffolk County's sought-after Southampton community. This spacious residence offers 4 bedrooms and 3 bathrooms, along with 2 bonus rooms that can serve as a home office or gym, providing ample space for comfortable living and productivity. Experience the epitome of luxury living, just a stone's throw away

  Todd Jacobs Exit Realty Everyday

  17 Underhill Dr, Southampton, NY 11968
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  $75,000 per month

  • 4 Beds
  • 4 Baths
  • House for Rent

  25 Meadowgrass Ln, Southampton, NY 11968

  Ideally located in Southampton Village, this classic traditional offers easy summer living just minutes from ocean beaches and the village center. Set on a beautifully landscaped property, the home features a heated gunite pool and a spacious deck designed for relaxed outdoor entertaining. The main level includes open living with a fireplace, kitchen and dining areas, and a flexible den or guest

  25 Meadowgrass Ln, Southampton, NY 11968
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  $84,000 per month

  • 3 Beds
  • 2 Baths
  • 1,434 Sq Ft
  • House for Rent

  3 Meadowgrass Ln, Southampton, NY 11968

  The Ultimate Four-Season Retreat in Southampton Village: 3 Meadowgrass Ln Discover the rare opportunity to secure a home that excels across every season. Located moments from Southampton Village center and world-class Ocean Beaches, this charming cedar-shingled residence at 3 Meadowgrass Ln is available for Summer, Winter, and Year-Round terms. The property offers the quintessential Hamptons

  Elizabeth Cordova Alata Douglas Elliman Real Estate

  3 Meadowgrass Ln, Southampton, NY 11968
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  $60,000 per month

  • 4 Beds
  • 5 Baths
  • House for Rent

  135 Meeting House Ln, Southampton, NY 11968

  Charming Southampton Village home retains many of its original features, built-in 1870, including wood floors along with more recent additions and upgrades completed in 2020. This 4 bedroom, 4.5 bath house is in the most desirable location in the heart of Southampton Village, a few short blocks to all shops and restaurants as well as the beach! Spacious entertaining areas, library and home office

  135 Meeting House Ln, Southampton, NY 11968
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  $70,000 per month

  • 3 Beds
  • 5 Baths
  • 2,600 Sq Ft
  • House for Rent

  24 Jennings Ave, Southampton, NY 11968

  Location! Location! Available for US Open and August-LD! Just two short blocks from Southampton village's charming restaurants and shops and a short distance to the train and jitney stop, this pristinely kept traditional home offers a luxurious escape. Relax by the heated, gunite pool amidst manicured, flowering gardens or enjoy the spacious living areas inside, including a living room with two

  Dawn Litel-Murphy Corcoran

  24 Jennings Ave, Southampton, NY 11968
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  $120,000 per month

  • 5 Beds
  • 5 Baths
  • House for Rent

  9 Sea Farm Ct, Bridgehampton, NY 11932

  Tucked within the private Sea Farm community, this updated post-modern home near Bridgehampton Village features bright, open living with dramatic ceiling heights and bright living spaces. Positioned on a half-acre bordering reserve, the property is set in serene, park-like surroundings. The 5,200-square-foot layout includes four bedrooms, with a main-level primary suite. Soaring windows fill the

  9 Sea Farm Ct, Bridgehampton, NY 11932
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  $48,000 per month

  • 4 Beds
  • 3 Baths
  • 2,452 Sq Ft
  • House for Rent

  167 Tuckahoe Ln, Southampton, NY 11968

  Southampton Retreat - Tucked away on 1.29 ultra-private acres in the heart of Southampton, this elegant 4-bedroom, 3-bath retreat is surrounded by world-class golf courses and pristine bay beaches. Designed for effortless entertaining, the home features sun-filled living spaces and a resort-style Gunite heated pool. Stylishly appointed throughout, it's the perfect Hamptons escape for Summer 2026

  Beth Marano Corcoran

  167 Tuckahoe Ln, Southampton, NY 11968
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  $190,000 per month

  • 5 Beds
  • 6 Baths
  • House for Rent

  53 Hidden Cove Ct, Southampton, NY 11968

  This light filled, airy, modern home has an open layout and is within walking distance to Peconic Bay. Located at the end of a very quiet dead end street, the house offers an expansive mahogany deck overlooking a 40X20 gunite pool with electric safety cover and deco turf tennis court surrounded by professional landscaping. A great entertaining home with a rolling lawn for outside play, it offers

  53 Hidden Cove Ct, Southampton, NY 11968
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  $20,000 per month

  • 3 Beds
  • 2.5 Baths
  • 1,500 Sq Ft
  • Condo for Rent

  10 Leland Ln Unit 19, Southampton, NY 11968

  Southampton Village: Minutes to Beach and Main Street. This Unit features 3 full bedrooms with 2.5 Bathrooms bright Living room, and a Dining room looking over the outdoor patio and the tree-lined view. Furniture and appliances are high-end and new. The unit is steps away from the pool and the tennis-pickle ball courts. This complex offers a wide variety of relaxation and a community feel. First

  Frances Ventura Licata Ventura Realty Inc

  10 Leland Ln Unit 19, Southampton, NY 11968
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  $90,000 per month

  • 4 Beds
  • 5 Baths
  • House for Rent

  20 Underhill Dr, Southampton, NY 11968

  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

  20 Underhill Dr, Southampton, NY 11968
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  /15

  $150,000 per month

  • 6 Beds
  • 6.5 Baths
  • 6,000 Sq Ft
  • House for Rent

  94 Merchants Path, Sagaponack, NY 11962

  Solid, quality 2019 new build (with a plethora of upgrades) tucked behind Wolffer Estate in Sagaponack. No expense was spared in the design, construction, or furnishing of this massive 6 bedroom, 6.5 bath home brimming with five-star amenities. Monthly rental price shown.

  Matthew Melinger Brown Harris Stevens Hamptons

  94 Merchants Path, Sagaponack, NY 11962
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  /50

  $150,000 per month

  • 9 Beds
  • 13 Baths
  • House for Rent

  59 First Neck Ln, Southampton, NY 11968

  Exceptional home located in one of the most desirable streets in the Southampton Estate Section. The home just went through an immaculate renovation and the elegant floor plan includes a grand foyer with windows overlooking the grounds, two oversized and separate living rooms, both accessing terraces and areas of the garden, a beautiful den off the pool, an elegant formal dining room, a TV/media

  59 First Neck Ln, Southampton, NY 11968

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