57 Big Fresh Pond Road
$110,000
Southampton, NY
Rental
Bedrooms: 5
Bathrooms: 4
Web ID: 918583
After departing from your dock and floating in your boat during sunset, the pinks, purples and golden hues bounce off the water from Big Fresh Pond. Upon returning, it is beautiful to dine, barbeque, and entertain on the deck with those awesome views. This renovated, multi-level house offers 5 bedrooms, 4 full bathrooms, with an open living plan with fireplace on the main floor and another common entertaining area on the above grade lower level which leads out to the dock. The ponds purity level is high for swimming, fishing and boating. Perched above Big Fresh, this property comes with a boat and bicycles for the total enjoyment of this beautifully natural area.
February Rental: $7,000
March Rental: $7,000
April Rental: $7,000
November Rental: $7,000
December Rental: $7,000
Winter Rental: $28,000
Year Round: $110,000
Andrea L Ackerman
(631) 537-4340
Elizabeth A Phenis
(631) 537-4357
55 Old Town Crossing
$110,000
Village of Southampton, NY
Rental
Bedrooms: 6
Bathrooms: 4.5
Web ID: 904679
Located in the most desirable location between Wyandanch Lane and Little Plains Road, sits this 6 bedroom, 4.5 bathroom classic home spanning 3,620 s/f over 3 levels. With a luxurious open space interior design boasting an abundance of natural light and furnished with meticulous detail. Featuring a captivating and fully-equipped chef's kitchen with state-of-the-art stainless steel appliances, central air conditioning and a music room with equipment for those that want to entertain and play. Outdoors, the spacious backyard features a patio, perfect for entertaining with ease, a beautiful landscape offering mature estate privet hedges with a manicured garden and a 44 x 20 heated gunite pool with outdoor shower. With only a short distance to world class shopping and world famous ocean beaches, this is an opportunity for living the Hamptons life you won't want to miss. Listing ID: 904679
August - LD Rental: $110,000
John P Vitello
(631) 204-2407
312 Ocean Road
$110,000
Bridgehampton, NY
Rental
Bedrooms: 5
Bathrooms: 4.5
Web ID: 755480
Come experience everything the Hamptons has to offer in this gorgeous 5 bedroom, 4.5 bathroom traditional in the estate section of Bridgehampton. This completely restored farmhouse set on .73 acre of picture perfect landscaping and gated entry. It is tastefully decorated with wide-plank floors, 2 fireplaces, a large living room, formal dining room, eat-in kitchen, and breakfast area with french doors leading to the pool. Outback, enjoy the 20x40 heated gunite pool, pool house with the fourth full bath, a back porch and patio, for classic Hamptons entertaining, accessed through the quintessential farm style kitchen. Head down the pristine and famous Ocean Road to world renown white sand ocean beaches and dunes indigenous to the Hamptons or make your way up the street to Bridgehampton's Main Street filled with History, restaurants with abundant outdoor dining and local shops for a magnificent summer get-a-way. Listing ID:755480
Custom Rental: $250,000
July Rental: $110,000
July / Aug Rental: $210,000
August - LD Rental: $110,000
September Rental: $60,000
Cynthia R Barrett
(631) 537-4322
14 Maple Street
$110,000
Village of Southampton, NY
Rental
Bedrooms: 4
Bathrooms: 4
Web ID: 919236
Centrally located Southampton Village homes for rent in the most convenient location imaginable. Fully renovated and restored in 2006, the home provides 21st century dependability within the details of its architectural past. Enter into the unique brick-floored foyer and then onward into its spacious living and dining rooms with bright windows all around. French doors that open onto a deck that overlooks the pool and garden beyond. A new granite kitchen and full bath service the household and pool area. The second floor contains a junior primary suite plus two guest rooms with shared bath. Above, a large primary suite enjoys the full advantage of its quiet third floor perch, where dramatic ceilings rise to the peaks of its Gambrel frame. This charming one-of-a-kind home sits amid banks of hydrangea and lush plantings. You'll appreciate its central air conditioning, two sets of washer/dryers, basketball hoop, gas grill with close proximity...
MD - LD Rental: $110,000
Robert M Lohman
(631) 204-2404
East Hampton
$105,000
East Hampton, NY
Rental
Bedrooms: 5
Bathrooms: 5.5
Web ID: 901160
Rental Reg. # 23-358. On the fringe just outside East Hampton Village, this almost new property was again completely redesigned and is nothing short of perfection. There are 5 large ensuite bedrooms, each with 5 star hotel amenities and bedding with chic modern baths. The public areas consist of a beautiful formal dining room, a true great room filled with sumptuous furnishings and stellar artwork that opens to a professionally equipped kitchen with 2 fridges, 2 dishwashers and secondary butler's pantry. The lower level has a serious gym with the latest model Peloton and a spacious comfortable media room with a 75' TV. There are 3,500 sf at first and second floor plus a1,000 sf lower level. The private and sumptuously landscaped yard has a heated gunite pool, firepit, pergola and a built in BBQ. Sonos sound throughout.Listing ID: 901160
August - LD Rental: $105,000
Jennifer Linick
(631) 771-5310
76 White Street
$105,000
Village of Southampton, NY
Rental
Bedrooms: 5
Bathrooms: 5.5
Web ID: 874521
Located in the heart of Southampton Village, this newly completed designer furnished 5 bedroom, new construction modern farm-style home with a loft like ultra-chic interior and soaring ceilings make this the ultimate summer Hamptons rental. Combined with a fully finished lower level which has a fifth bedroom and media room, the home has 5400sf+- of living space on 3 levels plus a detached one car garage. Enter the home on the first floor and immediately feel the open and beachy design accented with modern finishes. The vaulted ceiling, grand open living area, chic kitchen and loft used as a home office or gym, has two sets of floor to ceiling foldable glass walls that fully open in the front and to the pool area exemplifying the sense of indoor/outdoor living. Prepare a wonderful summer meal in the Sub-zero & Wolf open kitchen complete with a grand...
Custom Rental: $160,000
March Rental: $20,000
April Rental: $20,000
MD - LD Rental: $250,000
July Rental: $105,000
July / Aug Rental: $200,000
August - LD Rental: $105,000
Two Week Rental: $55,000
Year Round: $349,000
Cynthia R Barrett
(631) 537-4322
Wainscott
$104,500
Wainscott, NY
Rental
Bedrooms: 6
Bathrooms: 4.5
Web ID: 737760
Rental Registration #: 24-114 (Feb 2, 2026)• Dynamic great room with two story vaulted ceilings • 1st floor master bedroom suite with fireplace • 6 bedrooms • 4 1/2 bathrooms • 3 fireplaces • Cook's kitchen featuring Wolf stove, Subzero refrigerator and wine refrigerator, Bosh dishwasher and Scotsman ice machine • Covered bluestone patio with ceiling fans and dining and seating area for entertaining with fire pit • 2 washing machines and 2 dryers • Indoor/outdoor sound system • Central air conditioning and heating (Nest Thermostat) • Heated 20 X 40 gunite pool (Jandy pool heater with iPhone control) • Beautiful landscaping including extensive privacy screening • Nest locks and thermostat • Housekeeping, handy-person and chef available on request • Town water connection with top-of-the-line water filtration system; garbage disposal • Dogs allowed with owner permission. Listing ID: 737760
MD - LD Rental: $264,000
June Rental: $82,500
July Rental: $104,500
August - LD Rental: $110,000
Year Round: $440,000
David Blumenfeld
(631) 537-4329
Water Mill
$100,000
Water Mill, NY
Rental
Bedrooms: 5
Bathrooms: 5.5
Web ID: 758247
This 5,000 +/- sf gambrel home on 1+/- acre in the heart of Water Mill is moments away from Bridgehampton Main Street and less than 5 miles away from ocean beaches. This open-concept 5 bedroom, 5.5 bath home is filled with natural light. The first floor features a great room with double-height ceilings, a gourmet eat-in kitchen with stainless steel appliances, a formal dining room, a spacious primary suite, 2 additional bedrooms with a shared bath, and walls of glass leading to the spacious back deck. The second level features 3 ensuites with renovated marble baths. The fully finished basement offers 2 game rooms and ample storage. The grounds feature lush landscaping, a heated pool, and a har-tru tennis court. This exquisite, one-of-a-kind summer rental is not to be missed.
April Rental: $40,000
May Rental: $60,000
MD - LD Rental: $275,000
June Rental: $65,000
July Rental: $100,000
July / Aug Rental: $220,000
August - LD Rental: $120,000
September Rental: $70,000
Christopher J Burnside
(516) 521-6007
Aubri Peele
(631) 252-5434
Village Of Southampton
$100,000
Village of Southampton, NY
Rental
Bedrooms: 5
Bathrooms: 7.5
Web ID: 735873
Oceanfront property with ocean and bay views. Private master bedroom suite with 2 fireplaces, 2 baths, sauna, sitting room, oceanfront and bayfront balconies with gorgeous views. Guest wing with 4 en-suite bedrooms and an additional sauna. Multiple entertaining spaces. Flat screen TVs throughout. Heated gunite pool and hot tub. Listing ID: 735873
Short Term Weekly: $100,000
John P Vitello
(631) 204-2407
Bridgehampton
$100,000
Bridgehampton, NY
Rental
Bedrooms: 5
Bathrooms: 4.5
Web ID: 736789
Conveniently located and close to Bridgehampton Village. You must see this pristine traditional in a great Bridgehampton location. This home features 4100 sq. ft.-4 bedrooms/4.5 baths...Sheek Dining Room, Living Room with Fireplace, Gourmet Kitchen, 2 Master suites, Den, plus finished lower level with den, Game Room, and Wine Cellar. When you need a break from our beautiful beaches, relax by the tastefully furnished pool area and spa. The landscaped grounds set the stage for an enchanted evening of dining under the pergola. It's simply perfect!
July Rental: $100,000
August Rental: $120,000
Two Week Rental: $50,000
Christopher J Burnside
(516) 521-6007
Aubri Peele
(631) 252-5434
Shinnecock Hills
$100,000
Shinnecock Hills, NY
Rental
Bedrooms: 3
Bathrooms: 3
Web ID: 912250
RP# 230614. With stunning views of Shinnecock Bay and the Atlantic ocean, be the first to enjoy this renovated contemporary featuring 3 bedrooms and 2 baths with a seamless open floor plan, new flooring and furnishings. The large living room with fireplace, vaulted ceilings and glass windows throughout inundate the space with a natural light which connects the indoors with the outdoor landscaping and the serenity of all its surroundings. Enjoy the incredible 180 degree panoramic water views in every room. There is also a loft area with a den/office to complete this wonderful home. Enjoy entertaining viewing the water on the south facing deck which is perfect for lounging with family and friends surrounded by nature and all its beauty. Paradise and tranquility, this is the ideal retreat for the perfect Hamptons getaway. Listing ID: 912250
Year Round: $100,000
Cristina Matos
(631) 204-2408
East Hampton
$100,000
East Hampton, NY
Rental
Bedrooms: 5
Bathrooms: 4.5
Web ID: 737540
Rental Reg. # 24-1116. Entering this house is a true pleasure, since it is not only new quality construction, but it is also beautifully designed and newly furnished. The house offers 5 bedrooms, 4-and-a-half baths, living room with fireplace, dining area with French doors opening onto a deck,a sunroom/den, and a kitchen that any cook would enjoy. Other features include a heated gunite pool, master bedroom suites on both floors, natural gas, and town water. Lastly, the location is a major feature, since it is just a short distance from the center of East Hampton Village. Listing ID: 737540
August - LD Rental: $100,000
Short Term Weekly: $25,000
Noel D Mason
(631) 903-6135
Westhampton
$100,000
Westhampton, NY
Rental
Bedrooms: 5
Bathrooms: 4.5
Web ID: 737134
Rental Reg.#: RP200464 One of the premier builders in the Hamptons recently completed this magnificent modern home. Designed by the environmentally responsive firm, CookFox, with glass and wood details that provide open living space, ocean breezes and water views from every room. Amazing sunrise and sunsets can be yours. The home hosts an open living room with fireplace, custom designer kitchen from Henrybuilt of Soho, great room with dining and living area, separate media room, five bedrooms, four and one-half bathrooms and both a dry and a steam sauna. Expansive mahogany decking facing the ocean allows for entertaining and relaxing in the outdoor hot tub. There is also an outdoor dining area with spectacular ocean views. The state-of-the-art four zone heat and central air, and seven-zone sound system can be controlled by your phone or iPad. In addition to summering in the ultimate oceanfront home, experience a bit...
MD - LD Rental: $250,000
July Rental: $100,000
July / Aug Rental: $215,000
August - LD Rental: $120,000
September Rental: $60,000
Lauren A Battista
(631) 288-5534
Sag Harbor
$100,000
Sag Harbor, NY
Rental
Bedrooms: 6
Bathrooms: 5.5
Web ID: 736135
RR# RP241387. Stunning Sag Harbor pristine home on 2 private acres with gunite pool, spa and tennis court. The 6500 s/f home offers elegant, professionally decorated interior spaces. There are 6 bedrooms, including primary suite with fireplace, private balcony, walk-in closets and steam room, 5.5 baths, formal living and dining rooms, large eat-in just renovated chef's kitchen with Viking appliances, media/library room with balcony and a fully-furnished walk-out lower level with gym, ping pong and pool table. The beautiful property features an over-sized (20' x 50') heated gunite pool with spa, tennis court, Kingsley Bates outdoor furniture and designer landscaping. Available winter and summer 2025 or year-round. Any other period upon request. ID: 736135
Custom Rental: $105,000
February Rental: $15,000
March Rental: $15,000
April Rental: $15,000
May Rental: $25,000
MD - LD Rental: $250,000
June Rental: $50,000
July Rental: $100,000
August - LD Rental: $105,000
September Rental: $30,000
Year Round: $330,000
Amelia M Doggwiler
(631) 204-2426
Bridgehampton
$100,000
Bridgehampton, NY
Rental
Bedrooms: 8
Bathrooms: 7.5
Web ID: 738833
Rental Reg # RP201647 On 2.7+/- private acres moments to Bridgehampton's Main Street, is this 5,800+ square feet home of well arrived luxury. The exclusive retreat borders a 23-acre reserve affording true privacy and tranquil views. The interior offers a combination of the best indoor amenities and unsurpassed comfort. There is an oversized kitchen and a great flow between the den, living room and formal dining room. The floor plan includes 8 bedrooms and 7 1/2 baths. The master bedroom has a fireplace, luxurious bath and a private terrace with views of the saline water gunite pool, sunken tennis court and reserve. Plenty of room for guests and/or staff accommodations. Set well back from the road down a long driveway, this property offers privacy and luxury with vast views of fields and sky. Tons of other bells and whistles including stocked gym, wet bar, pool table, ping-pong table, media area...
Two Week Rental: $100,000
David Tenenbaum
(631) 771-5322
East Hampton
$100,000
East Hampton, NY
Rental
Bedrooms: 4
Bathrooms: 4.5
Web ID: 743193
Rental Reg. #24-616. Lovely four bedroom home with heated pool and all the amenities. The house is situated on a quiet cul-de-sac right between the village of East Hampton and Amagansett. All bedrooms are en-suite! The pool has a safety fence, perfect for security. The house is well maintained with a professional kitchen, central air conditioning and landscaped grounds. Listing ID:743193
Year Round: $100,000
Michael Petersohn
(631) 771-5336
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