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271 Flying Point Road
$90,000

Village of Southampton, NY
Rental
Bedrooms: 4
Bathrooms: 4
Web ID: 868902

Located South of the Highway in Southampton Village, 'THE WAVE' is a sprawling, updated and turnkey modern home that is the ideal retreat for year-round Hamptons living. With a southern exposure providing an abundance of natural light, the bright, open living spaces are ideal for entertaining. The 4 bedroom, 4 bath home benefits from oversized panels of glass that look out over the 1.30+/- acre park-like grounds, soaring ceiling heights, second floor balcony, radiant heated bluestone floors and a covered loggia. There is an impressive 2 story pool house, outdoor shower, 64' heated gunite pool, a 2 car garage and a Zen vibe that nothing can compare to. The grounds are manicured to perfection and feature a thoughtfully-designed landscape featuring mature trees and plants and room for tennis. All within very close proximity to the Hampton Jitney, the ocean and heart of the village. Listing ID:868902

August - LD Rental: $90,000

John P Vitello
(631) 204-2407

28 Bowden Square
$28,000

Village of Southampton, NY
Rental
Bedrooms: 3
Bathrooms: 2.5
Web ID: 885760

Classic cedar shingle cottage with stylish modern updates. Historic Southampton Village setting. Just a few blocks to Main Street's restaurants and shopping and convenient to train station and beaches. Gourmet cook's kitchen, new expanded bedrooms, breakfast terrace, herb garden and secluded English gardens around private south facing brick patio with heated pool and outside shower. Listing ID:885760

August Rental: $22,000
August - LD Rental: $28,000

Robert M Lohman
(631) 204-2404

28 Mill Hill Lane
$40,000

Village of East Hampton, NY
Rental
Bedrooms: 2
Bathrooms: 2
Web ID: 899340

Now available for year-round, winter 2024/25 and the summer season 2025, this house is an absolute jewel. On a quaint Village street, desired by many. 2 bedrooms, 2 bathrooms. Short distance to ocean and the center of the Village. Listing ID: 899340

June Rental: $25,000
July Rental: $40,000
August - LD Rental: $45,000

Timothy R O'Connor
(631) 771-5321

Jeffrey C Carter
(631) 771-5323

28 Parkway Drive
$85,000

Sag Harbor, NY
Rental
Bedrooms: 4
Bathrooms: 3.5
Web ID: 877646

RR#:RP230356 Newly AVAILABLE for July & August through Labor Day 2025. Conveniently situated between Sag Harbor Village and Long Beach, this immaculate 4 bedroom, 3 1/2 bathroom home, is an oasis of well curated art, blended with a sophisticated and monochromatic Interior style, in harmony with the simple proportions of this 2018 built CONTEMPORARY FARMHOUSE. An open plan kitchen, dining and living space flow perfectly to a 32' x 16' gunite heated pool, surrounded with a bluestone patio, perfect for entertaining and relaxing poolside. A first floor meditation room can double as an office . 4 comfortable bedrooms, 2 ensuite and a full 3rd bathroom complete the sunny 2nd Floor. Double washer and dryers located in a dedicated laundry room, add ease to your stay. Minutes to Long Beach and Sag Harbor, with the convenience of Serene Green Farm Stand, offering local produce is literally...

July Rental: $85,000
August - LD Rental: $95,000

29 Diane Drive
$35,000

East Hampton, NY
Rental
Bedrooms: 4
Bathrooms: 3
Web ID: 908014

Complete renovation and newly decorated 4 bed, 3 bath, contemporary, on .81 acres, in coveted East Hampton Oaks Association, Northwest Woods w/community tennis. Open floor plan smart home with hardwood floor, central air and plenty of natural light. Main level offers family sitting area, living room w/fireplace open to dining room and kitchen with all new high end stainless steel appliances plus full bath. Upper level offers primary ensuite bedroom w/private terrace plus three well appointed guest bedrooms and shared bath. Large wide side/back deck surrounds the 20x40 heated pool.

July Rental: $35,000
July / Aug Rental: $70,000
August Rental: $35,000
September Rental: $20,000
October Rental: $20,000

Dennis Gallagher
(631) 771-5309

3 Hayseed Way
$45,000

East Hampton, NY
Rental
Bedrooms: 4
Bathrooms: 4.5
Web ID: 899308

Rental Reg. # 22-249 Enjoy summer in the Hamptons in this 2-story cedar-shingle farmhouse in East Hampton's desirable Dune Alpin community. A covered front porch welcomes you through to an airy entry foyer. The common spaces flow through living, dining and open concept kitchen and family rooms. The living room has a gas fireplace, ceiling-to-floor windows, French doors, and 11' ceilings. The dining room also connects both the living room and eat-in kitchen. The open concept kitchen and family room features high-end appliances, Caesarstone countertops, and large seating area with wood burning fireplace. The first floor en-suite primary bedroom has large windows, 2 closets, and a luxe bath. A garage and powder room complete the first level. Upstairs, a skylit gallery leads to 2 bedroom suites both with baths and large closets. The second floor also has a large second primary bedroom with multiple closets and ensuite bath. A laundry...

April Rental: $10,000
May Rental: $15,000
MD - LD Rental: $135,000
June Rental: $20,000
June/July Rental: $65,000
July Rental: $45,000
August - LD Rental: $60,000
Winter Rental: $9,500

Todd J Buchanan,
(631) 771-5326

30 Clinton Academy Lane
$30,000

Amagansett, NY
Rental
Bedrooms: 3
Bathrooms: 2
Web ID: 887915

Amagansett Dunes Summer Rental Reg. # 24-1002 Amazing Value at the Beach! Enjoy this charming and private beach house location at 30 Clinton Academy in the desirable Amagansett Dunes where the beautiful sandy ocean beach is yours only seconds away, right at the end of the street! Offering three spacious bedrooms, two baths plus the large den with a pullout for guest overflow. Nice space for entertaining too with its open kitchen-living areas that lead to a large addition with a dining area and a work station offering lovely views of the natural dunes enhanced with native song birds. This is a great place to de-stress and relax yet it's close to the ocean, village shops and restaurants as well as transportation to NY. Listing ID#:887915

MD - LD Rental: $75,000
July Rental: $30,000
July / Aug Rental: $60,000
August - LD Rental: $35,000

James J MacMillan
(631) 267-7171

3029 Mitchell Road
$50,000

Village of Westhampton Beach, NY
Rental
Bedrooms: 2
Bathrooms: 3.5
Web ID: 899296

This canal front Westhampton Beach Village condominium has just been completely renovated. Enjoy water views, use of a boat slip and the heated pool. The bright, open floor plan offers plenty natural light and is beautifully decorated with a minimal sensibility. The perfect summer rental with 2 plus bedrooms, 3 and one-half baths, and a lovely deck overlooking the canal. On the second floor are the two primary bedrooms each with its own bathroom. The lower level has a large second living space, a full bath, and sliding glass doors leading to a lovely patio and the condominium grounds lush with greenery. Ideally located in the heart of the Village near Main Street. Listing ID#899296

July / Aug Rental: $50,000

Gayle Osman Lopata
(631) 288-5124

31 Diane Drive
$40,000

East Hampton, NY
Rental
Bedrooms: 3
Bathrooms: 2.5
Web ID: 743733

Rental Registration # 22-604. Spacious, Modern living. Full renovation completed in 2020. Located 1.5 miles from East Hampton Village and ocean beaches. In sought after East Hampton Oaks community. Private, crisp, and immaculate one floor home offers living room with wood burning fireplace, family and dining rooms, luxury galley kitchen, primary plus 2 additional guest bedrooms, 2.5 baths and laundry. Contemporary kitchen design is fully equipped with Sub-Zero, Bosche and Wolfe appliances and opens, partially, to all main living areas. Primary is ensuite with king bed, walk in closet and opens to teak deck, pool and outdoor shower. Guest bedrooms 1 & 2 offer Queen and Twin beds with shared full bath. Outdoor living space includes teak deck, professional grill, dining for 8, wood burning fireplace with seating, both overlooking the 18' x 36' gunite pool with auto closing cover and a private outdoor shower. Front facing porch is off...

June Rental: $20,000
July Rental: $40,000
July / Aug Rental: $80,000
August Rental: $40,000
September Rental: $25,000

Dennis Gallagher
(631) 771-5309

31 Hartley Boulevard
$30,000

Springs, NY
Rental
Bedrooms: 4
Bathrooms: 4
Web ID: 908423

RR24-58. Located in East Hampton, this perfect summer contemporary home with elegant and stylish new furnishings has it all! Be the first to enjoy this spacious home featuring 4 bedrooms and 4 baths. The expansive and bright living room, with 17 foot high vaulted ceilings, large glass windows and a wood burning fireplace flow seamlessly to a den and eat-in kitchen with stainless steel appliances. A guest bedroom and a renovated full bath completes the first level. On the second level is the primary bedroom with en suite bathroom and walk-in closet, 2 additional guest bedrooms and a full bath. Hardwood flooring throughout the house. Privacy is ensured in the beautiful and lush mature landscaped backyard surrounded by specimen trees and mature plantings, as well as a heated pool with outdoor firepit patio area. Amenities include solar panels, which produce a wallet-friendly power supply....

July Rental: $30,000
August - LD Rental: $35,000

Cristina Matos
(631) 204-2408

31 Meredith Avenue
$50,000

Village of Sag Harbor, NY
Rental
Bedrooms: 4
Bathrooms: 4.5
Web ID: 901804

This newly constructed 4-bedroom, 4.5-bath house in Sag Harbor is only one year old. With 2,153+/- sf of open concept living space, the first floor features a fireplace, spacious primary ensuite, chef's kitchen with a dining area, stainless steel appliances, and sliding glass doors leading to the patio, which overlooks the heated gunite pool and manicured grounds. The second floor includes three ensuite bedrooms and a sitting area. The lower level, with a separate staircase, hosts a lounge area with a pool table, laundry, and a full bath. Only 1.2 miles to Sag Harbor Village, about four football fields away from a private sandy beach, or halfway between the two is Havens Beach. Listing ID:901804

MD - LD Rental: $125,000
July Rental: $50,000
July / Aug Rental: $85,000
August - LD Rental: $55,000

Shannan M North
(631) 903-6174

Roxanne A Briggs
(631) 903-6121

31 Pond View Drive
$72,000

Wading River, NY
Rental
Bedrooms: 4
Bathrooms: 2.5
Web ID: 909709

Spacious four bedroom and 2 1/2 bath home available for year round in the beautiful area of Wading River! Minutes to a Bay beach and sweet town. The new owner has refreshed the home with all new paint, high hat lighting, wood floors throughout! There is a large living room, dining room, large eat in kitchen and den/TV room with fireplace along with a 1/2 bath all on the first floor. Upstairs you will find a nice en-suite primary bedroom with walk in closet, along with three additional bedrooms and another full bath. Outside there is a large deck and nice yard all in a lovely, quiet neighborhood! There is a full unfinished basement and two car garage. Washer and dryer on main level. Oil heat.

Year Round: $72,000

Margaret Turner
(631) 771-5314

316 Deerfield Road
$175,000

Water Mill, NY
Rental
Bedrooms: 6
Bathrooms: 7.5
Web ID: 736995

RP240310 - This custom-built estate offers striking panoramic water views across Mill Pond with 700 feet of waterfront on 2+ bucolic acres. The 8000+/- sq. ft. modern beauty consists of 6 bedrooms, 8 baths, custom crafted and light flooded with 30 ft. ceilings, and full access overlooking the pond, The indoor/outdoor pavilion completely opens with folding glass walls to the heated Gunite pool and spa. The family room with bar and fireplace are adjacent to the paneled study. A top-of-the line chef's kitchen and large prep kitchen add to the unique quality of this extraordinary house. The spacious first floor master suite offers dual baths, giant custom closets and a sliding glass door providing private access to the grounds. Additionally, a second master suite and 3 more en-suite bedrooms with terraces are separated by a gallery on the upper level. The lower level includes a light-filled...

January Rental: $10,000
February Rental: $10,000
March Rental: $10,000
April Rental: $10,000
July Rental: $175,000
July / Aug Rental: $425,000
August - LD Rental: $195,000
November Rental: $10,000
December Rental: $12,500
Two Week Rental: $85,000

Andrea L Ackerman
(631) 537-4340

Elizabeth A Phenis
(631) 537-4357

32 Sag Harbor Road
$20,000

East Hampton, NY
Rental
Bedrooms: 3
Bathrooms: 2
Web ID: 736615

Rental Registration #:24-872 - This East Hampton cottage, near village and ocean beaches, offers three second floor bedrooms, two full bathrooms, a sunny living room, an adjacent eat in kitchen, and a finished basement. Set on a beautifully and privately landscaped half acre adjacent to farmland, and just a mile to Main Street. Ocean beach is less than two miles away. The back deck is furnished with chaise lounges, Weber grill, and outdoor dining table for six. Other amenities include outdoor shower, air conditioning, flat screen TVs, Wi-Fi, and premium cable. Listing ID: 736615

MD - LD Rental: $55,000
July Rental: $20,000
July / Aug Rental: $50,000
August - LD Rental: $30,000

Jeanne Hutson
(631) 903-6144

327 Georgica Road
$250,000

East Hampton, NY
Rental
Bedrooms: 7
Bathrooms: 7.5
Web ID: 897770

In the world class destination of the Hamptons is this classic gabled traditional on over 1.3 gorgeous acres in the coveted Georgica enclave of East Hampton Village offering a fortunate tenant a rare opportunity. Newly designer decorated, painted and floors done, this South of the highway jewel should not be overlooked. With elements of size and construction that could not be duplicated again on this parcel, a 7-bedroom, 8,000 SF+/-, residence, on 3 levels of finely articulated living space, down a long driveway, and sequestered behind a gated entry, brings the combination of masterful construction, exquisite finishes, copious amenities and a sensible floor plan that has become the hallmark of fine East End design. Newly refinished oak floors welcome all into a grand entrance that fans out to find the living room and formal dining room, both warmed by their own fireplaces. The expansive kitchen and family room...

MD - LD Rental: $565,000
July Rental: $250,000
July / Aug Rental: $515,000
August Rental: $300,000
August - LD Rental: $300,000

Andrea L Ackerman
(631) 537-4340

Elizabeth A Phenis
(631) 537-4357

33 Horseshoe Drive
$65,000

East Hampton, NY
Rental
Bedrooms: 6
Bathrooms: 5.5
Web ID: 759373

Rental Registration #: 24-914.Owners have transformed this 6 bedroom 5.5 bath house into a family paradise. Stephen Saint-Onge has designed the home with simple elegance yet sophisticated glamour. The flow is perfect for summer living with an open first floor plan that makes entertaining easy. The living room with fireplace flows into the dining area which is open to the chef's kitchen and family room with bar. There are floor to ceiling accordion glass doors that lead to the outside deck with its' outdoor dining area. A few steps down is the brick patio and oversized pool. First floor has master bedroom and a bathroom with a soaking tub and steam shower. Additionally, two guest bedrooms share a bathroom. Upstairs from the entry hall there are two bedrooms and a bathroom. And a second staircase leads to an en suite bedroom....

MD - LD Rental: $165,000
June Rental: $40,000
July Rental: $65,000
July / Aug Rental: $135,000
August - LD Rental: $75,000

Leslie Hillel
(631) 771-5311

Philip Judson
(631) 771-5328

340 Wainscott Harbor Road
$55,000

Sagaponack, NY
Rental
Bedrooms: 4
Bathrooms: 4.5
Web ID: 867563

RR#: RP230740 Fabulous Sagaponack location, recently renovated, close to everything Hamptons! This 4 bedroom, 4.5 bath home offers wonderful entertaining space with open concept great room, dining, kitchen, and bar. Take your pick of 2 Primary bedrooms, both ensuite; one on the main floor, one upstairs with its own private deck. The 2 additional bedrooms/2 baths are also located on the upper floor. Other features include a den/media room, a separate office on the main floor for your WFH days, and a screened-in porch. Enjoy a full day of sun from late morning until sunset in this gorgeous, very private West-facing backyard showcasing stunning landscaping, heated pool, outdoor shower, deck, patio and perfect sunsets. World-renowned Sagg Main beach, Sag Harbor Village and East Hampton are 4 miles away, Bridgehampton under 3 miles, and 1 mile from Wolffer Estate Vineyard. Perfect Hamptons summer rental! Listing ID:867563

MD - LD Rental: $140,000
June Rental: $25,000
July Rental: $55,000
July / Aug Rental: $115,000
August Rental: $60,000
August - LD Rental: $65,000

Sarah Ferguson
(631) 903-6124

Kimberly Kakerbeck
(631) 537-4351

35 West Neck Road
$24,000

North Sea, NY
Rental
Bedrooms: 3
Bathrooms: 2
Web ID: 912623

RR# RP230837. Completely renovated, crisp and bright this adorable home features 3 bedrooms and 2 full baths. Great kitchen with an open floor plan flowing to the living room and den with a flat screen TV providing multiple areas to relax and entertain. Spacious backyard with mature landscaping. Close to Southampton Village's best restaurants and ocean beaches makes this a perfect Hamptons vacation getaway. Listing ID: 912623

May Rental: $8,000
MD - LD Rental: $57,000
June Rental: $11,000
July Rental: $24,000
August Rental: $24,000

Cristina Matos
(631) 204-2408

355 Midway Road
$18,000

Southold, NY
Rental
Bedrooms: 3
Bathrooms: 3
Web ID: 888811

This impeccable modern 3 bedroom, 3 bath home in Southold's coveted Cedar Beach district offers privacy, water views and a private neighborhood beach. The open plan includes a kitchen, dining area, den/office, and living room with fireplace. Sliding doors open to the bluestone patio with a gas grill and plenty of room for entertaining and sunning. The three bedrooms, including the primary suite, all have water views. A private beach is nearby and there's easy access to renowned North Fork wineries, farm stands, restaurants and shops. This home has everything needed for an exceptional East End retreat. Listing ID #888811

MD - LD Rental: $45,000
June Rental: $8,000
July Rental: $18,000
August - LD Rental: $20,000
September Rental: $8,000
Winter Rental: $6,000

Marianne Collins
(631) 734-2957

36 John Street
$80,000

Village of Sag Harbor, NY
Rental
Bedrooms: 3
Bathrooms: 5
Web ID: 913469

Ideally located on the tranquil waters of Upper Sag Harbor Cove with a private dock and waterside pool, this Sag Harbor Village summer house is only one block to the Main St sidewalk for direct access to restaurants, shopping, and Long Wharf. The magic happens outside where sunsets can be enjoyed from the patio furnished with ample seating, umbrellas, and gas grill. This beautiful traditional home is bathed in natural sunlight from an abundance of sliding glass doors on 2 levels. The open floor plan boasts a large kitchen with granite counters, 4 burner Wolf range, rolling butcher block island, wine fridge, and stainless steel appliances. It leads to the living room with a big comfortable sectional sofa and dining for 4. The first level primary suite with tile bathroom and stall shower has views over the pool and the water beyond. A convenient den with ensuite bathroom and access...

August - LD Rental: $80,000

Clare J Tenkarian
(631) 725-5586

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