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
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
North Haven
$100,000
North Haven, NY
Rental
Bedrooms: 6
Bathrooms: 5.5
Web ID: 754738
Luxury and comfort await you. This six bedroom villa is designed for both indoor and outdoor living and an active waterfront lifestyle. Moor your boat just yards away in the bay, or lounge by the unique, wrap around pool. There's also a full spa with sauna and steam shower, gorgeous chef's kitchen, and intimate covered patios for relaxing and entertaining. The views over the bay at sunset are absolutely breathtaking, and the lush grounds filled with flowering trees and shrubs are reminiscent of the tuscan countryside. A private chef is available for an additional cost. Listing ID: 754738
MD - LD Rental: $275,000
July Rental: $100,000
July / Aug Rental: $250,000
August - LD Rental: $125,000
Year Round: $500,000
Korine M Konzet
(631) 537-4323
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
January Rental: $15,000
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
November Rental: $15,000
December Rental: $15,000
Year Round: $330,000
Amelia M Doggwiler
(631) 204-2426
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
2765 Deerfield Road
$100,000
Sag Harbor, NY
Rental
Bedrooms: 5
Bathrooms: 6
Web ID: 736834
Enjoy this chic and sophisticated property with all it has to offer. The house has 5 very generous bedrooms, new bathrooms and beautiful new kitchen, formal dining room, 2 large main floor common areas with direct access to the heated pool . The second floor features a primary ensuite bedroom with a balcony, as well as 4 guest suites, 3 of which are also ensuite with private balconies. There is also a lovely loft study/office. The 2.43 acres surround the Har-Tru tennis court, extensive decking, swimming pool and pool house, all with great views of Noyac Golf Course. A truly great Hamptons rental in the Sag Harbor area.
July Rental: $100,000
July / Aug Rental: $225,000
August Rental: $125,000
August - LD Rental: $125,000
Andrea L Ackerman
(631) 537-4340
Elizabeth A Phenis
(631) 537-4357
13 Meadow Court
$100,000
Bridgehampton, NY
Rental
Bedrooms: 8
Bathrooms: 8.5
Web ID: 738862
13 Meadow Court. In the heart of Bridgehampton horse and wine country close to Main Street and ocean beaches, this newly built 8 bedroom, 8 1/2 bath magnificent home is available for a summer of luxury and casual entertaining both inside and out, by the Gunite pool and spa. The first floor graciously flows from the eat-in-kitchen with grand island, wet bar,formal dining, 2 living areas, baby grand piano, impressive 2 story entry, and a first floor master. The second floor has 5 spacious en-suite bedrooms including a master suite wing with a master bath that ranks with some of the most elegant. The lower level boasts a gym, 3 living area and 2 additional bedrooms and a bath. Fabulous opportunity for a summer to remember.
MD - LD Rental: $275,000
June Rental: $50,000
July Rental: $100,000
July / Aug Rental: $225,000
August - LD Rental: $125,000
Christopher J Burnside
(516) 521-6007
Aubri Peele
(631) 252-5434
128 Halsey Street
$100,000
Village of Southampton, NY
Rental
Bedrooms: 4
Bathrooms: 4
Web ID: 876611
Designer Southampton Village cottage only a few blocks from the village center, ocean beaches and all of Southampton's exceptional amenities. Built in 2021, this brand-new home offers 4 bedrooms and 4 bathrooms, 3,100 +/- sf of interior living space over 3 levels on 0.23+/- acre. This comfortable, architecturally exciting home was designed by Kelly Shauger, principal of Eave + Arbor Architecture Design. The interior showcases a warm color palette with soothing hues setting the tone for a relaxing summer escape. The open floor plan includes a living room and dining room leading into the gorgeous gourmet kitchen. Fit for a true epicurean chef, it is equipped with top-of-the-line appliances and stunning cabinetry. Wrapped in an elegant package, all the bells and whistles are present. The exceptional custom woodwork, along with stunning reclaimed wide-plank wood flooring, flow throughout the home. Completing the first floor are a butler's pantry, well-outfitted mudroom, spacious...
June Rental: $60,000
August - LD Rental: $100,000
John P Vitello
(631) 204-2407
115 Toylsome Lane
$100,000
Village of Southampton, NY
Rental
Bedrooms: 5
Bathrooms: 5.5
Web ID: 885554
Tucked away and less than a mile from the ocean and located in a most prestigious area of Southampton Village, this stunning 5 bedroom home offers everything you will need. First floor features a large, open style gourmet eat-in kitchen kitchen with double height ceilings and plenty of light. Living room features chic modern design, fireplace and plenty of seating and a formal dining room which is both warm and private. The first floor master bedroom includes a luxurious marble bath and powder room. The second floor includes 3 en-suite guest bedrooms and a laundry room. The finished basement includes a den with a flat screen TV, wine room, a 5th en-suite guest bedroom, gym and 9 seat movie theater. Outdoor amenities include heated gunite pool, pellet stove for grilling and lush landscaping from front to back. A must see! Listing ID: 885554
July Rental: $100,000
Two Week Rental: $50,000
Donna L Landry
(631) 725-5573
Gertrud Hoertnagl-Pereira
(631) 204-2425
East Hampton
$99,000
East Hampton, NY
Rental
Bedrooms: 6
Bathrooms: 4.5
Web ID: 880431
Rental Reg. # 23-425. Built in 1990 and renovated to perfection, this home is ready for summer 2025. From Memorial Day through Labor Day, you can be the lucky tenant if you act fast.There are 6 Bedrooms , 4 1/2 baths, a first floor master, heated pool and even a tesla wall connector in the 2 car garage. With all the bells and whistles and proximity to town and beaches, summer could not be enjoyed in a better place. Also available for winter 2024-2025 ...Hurry.... Listing ID: 880431
MD - LD Rental: $245,000
June Rental: $50,000
July Rental: $99,000
July / Aug Rental: $195,000
Winter Rental: $45,000
Mary Ellen McGuire
(631) 537-4324
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