Village Of Sag Harbor
$15,000
Village of Sag Harbor, NY
Rental
Bedrooms: 2
Bathrooms: 1
Web ID: 758745
WONDERFUL Sag Harbor Village Gem. Moments from Main Street, this light-filled 2 bedroom, 2 bath has a spacious eat-in kitchen, private yard and two parlors. This property is located on one of Sag Harbor's best streets, close to the Village's wealth of amenities, restaurants, shops and marinas.
January Rental: $5,000
February Rental: $5,000
March Rental: $5,000
April Rental: $5,000
July Rental: $15,000
August - LD Rental: $25,000
September Rental: $7,500
October Rental: $5,000
November Rental: $5,000
December Rental: $5,000
Short Term Weekly: $20,000
Kimberly Kakerbeck
(631) 537-4351
Southampton
$35,000
Southampton, NY
Rental
Bedrooms: 3
Bathrooms: 2.5
Web ID: 907271
RR# RP230478. Stunning is the single word to describe this unbelievable Southampton Commons 3 bedroom, 2.5 bath condo. The present owner completely gutted this unit when purchased in 2020 and transformed it into something totally exceptional and certainly unique. There is an additional room that is set up presently as an office to make your time here seamless or it can be converted to another bedroom (3rd bedroom). The chef's kitchen has all high-end stainless steel Wolf appliances, including a Wolf induction cooktop, plus marble countertops. The decor is quite dramatic, including a gorgeous chandelier over the dining room table, plus a cozy den with a steam fireplace. Too many special amenities to list. The back patio is set up for entertaining and relaxing. Included on the patio are attractive faux hedges in planters on either side of the patio and a 48' XO propane barbecue you must...
MD - LD Rental: $75,000
June Rental: $25,000
July Rental: $35,000
July / Aug Rental: $60,000
August - LD Rental: $35,000
John P Vitello
(631) 204-2407
Southampton
$35,000
Southampton, NY
Rental
Bedrooms: 2
Bathrooms: 2.5
Web ID: 755150
RR#: RP230549 Southampton condo for sports lovers with new tennis courts and pool! Close to Village with 2 bedrooms and 2.5 bathrooms. Updated kitchen and bathrooms, newly furnished, plus a private patio for outdoor dining. The community also offers pickle ball and a small driving range for the golf lover. Close to Village beaches. Listing ID#: 755150
MD - LD Rental: $40,000
July / Aug Rental: $35,000
Year Round: $55,000
Gertrud Hoertnagl-Pereira
(631) 204-2425
Southampton
$33,000
Southampton, NY
Rental
Bedrooms: 2
Bathrooms: 2.5
Web ID: 908771
RR#240204. Enjoy your summer in this spacious end unit condominium close to the Southampton Village center, shops, restaurants, and beaches. The first floor boasts a bright and light-filled kitchen and living room with dining area, and a newly renovated powder room. Sliders from the living room lead to a sunny patio, inviting for outdoor entertaining and lounging. The second floor features a generous sized primary bedroom and bathroom suit, a guest bedroom and a bath. The condo also has a loft on the third floor for over flowing guests. Amenities at the condo development include two heated pools, tennis and pickleball courts, and a club house. Listing ID: 908771
MD - LD Rental: $40,000
July / Aug Rental: $33,000
Gertrud Hoertnagl-Pereira
(631) 204-2425
Village Of Southampton
$75,000
Village of Southampton, NY
Rental
Bedrooms: 6
Bathrooms: 6.5
Web ID: 736551
The perfect Hamptons getaway in the Estate section of Southampton Village only 3 blocks from Little Plains Beach and walking/biking distance to the Village. Impeccably decorated with a sophisticated palette, the house is bright, spacious and perfect for entertaining. The first floor has an en-suite junior primary, the second floor has 4 spacious en-suite bedrooms and the basement has a great game and entertaining room, full gym, laundry, staff quarters and access to the outdoors where you can find a heated gunite pool, jacuzzi and pool house with full entertaining facilities and bar. Property is private with lovely landscaping. Listing ID: 736551
January Rental: $25,000
February Rental: $25,000
March Rental: $25,000
April Rental: $25,000
May Rental: $35,000
June Rental: $75,000
September Rental: $150,000
November Rental: $25,000
December Rental: $25,000
Two Week Rental: $40,000
Lillian A Holtzclaw
(631) 204-2430
Springs
$40,000
Springs, NY
Rental
Bedrooms: 4
Bathrooms: 2.5
Web ID: 755164
Rental Registration #: 23-114. Newly renovated 4 BR/ 2.5 bathroom in desirable Lions Head Association with private marina and bay beach access. Clean, spare living spaces with double height ceilings, multiple skylights, and enormous sliders allowing abundant light and views to Hog Creek. Ample decking for outdoor entertaining and a brand new heated gunite saltwater pool. Listing ID 755164
July Rental: $40,000
August - LD Rental: $40,000
Philip Judson
(631) 771-5328
Village Of Sag Harbor
$140,000
Village of Sag Harbor, NY
Rental
Bedrooms: 7
Bathrooms: 7.5
Web ID: 736094
Located on a beautifully landscaped parcel which is just shy of an acre, in the heart of Sag Harbor's historic district, this Federal-style house dates back to 1750 and has been beautifully restored and updated with every modern amenity. The peaceful and private retreat, only seconds from wonderful shops and restaurants, boasts century old boxwoods, an allee of cherry trees, a gunite pool, bluestone terrace and pool house. The principal rooms include a lovely living room, bonus room and library, gracious dining room overlooking the garden and a gourmet chefs kitchen with 2 Bosch dishwashers, a Viking range, a SubZero refrigerator and wine cooler. The private rooms include an exquisite master suite with fireplace, cathedral ceilings and spa bathroom plus two en-suite guest bedrooms, a new private en-suite guest bedroom with queen bed, sitting area and bathroom, as well as a maid's room with separate egress and two additional...
Custom Rental: $235,000
MD - LD Rental: $425,000
June Rental: $95,000
July Rental: $140,000
July / Aug Rental: $335,000
August - LD Rental: $195,000
Ext. Season: $160,000
Stacy Pennebaker
(516) 532-5765
Linley Pennebaker Hagen
(631) 725-5583
Bridgehampton
$350,000
Bridgehampton, NY
Rental
Bedrooms: 5
Bathrooms: 5
Web ID: 735474
Beautifully crafted and furnished two-story traditional is privately situated on a 1.1-acre with water views. Tailor-made for gracious Hamptons living, with impeccable attention to detail evident at every turn. Covered porches, large living room and dining area, Epicurean kitchen, five bedrooms and five baths. Adorned with two fireplaces and hardwood floors. Central air conditioning, two-car garage, outdoor shower and a sparkling heated Gunite pool. Close proximity to the ocean. Available seasonal or year round.
MD - LD Rental: $350,000
Year Round: $400,000
Mary Ellen McGuire
(631) 537-4324
Susan L Ratcliffe
(631) 537-4327
Village Of Southampton
$55,000
Village of Southampton, NY
Rental
Bedrooms: 5
Bathrooms: 3
Web ID: 737148
Privately located, this recently upgraded and immaculate traditional offers 5 bedrooms and 3 baths, living room, dining area off the eat-in kitchen and a large informal entertaining room/ sunroom which leads out to the pool and lushly-landscaped property. Ample room for enjoying the sun and proximity to village shops and Southampton Village beaches. Listing ID: 737148
June Rental: $35,000
July Rental: $55,000
July / Aug Rental: $115,000
August - LD Rental: $65,000
Christine Sullivan Witker
(631) 204-2403
East Hampton
$90,000
East Hampton, NY
Rental
Bedrooms: 4
Bathrooms: 2.5
Web ID: 759065
Rental Reg. # 22-1174. Spend a perfect summer or year in this clean and pristine 2000 square foot four bedroom, two and one-half bathroom, updated open-plan contemporary with central air conditioning, hot tub and heated pool. New deck and baths in 2021. New kitchen and landscaping in 2024. Located on a quiet block in the near northwest, this home is convenient to both Town and bay and ocean beaches. Update for 2024. Listing ID: 759065
November Rental: $4,000
December Rental: $6,000
Year Round: $90,000
Margaret Turner
(631) 771-5314
Water Mill
$200,000
Water Mill, NY
Rental
Bedrooms: 6
Bathrooms: 9
Web ID: 754361
RP#230019. This beautiful gated high-end Villa features 6 bedrooms, 9 baths, cathedral ceilings entrance and living room with wall to ceiling glass doors with automatic shades; formal dining room, extra-large gourmet kitchen with top-of-the-line appliances, several seating areas, large heated gunite pool, pool house, gym, and a finished basement. House has been just upgraded and refreshed and has an elevator for the three levels. Located on 2.7 park like acres including all-weather tennis court. Golf cart included for trips to private ocean beach. Available August 2025 Listing ID: 754361
August - LD Rental: $200,000
Two Week Rental: $100,000
Short Term Weekly: $35,000
Amelia M Doggwiler
(631) 204-2426
Village Of Southampton
$450,000
Village of Southampton, NY
Rental
Bedrooms: 5
Bathrooms: 5.5
Web ID: 908437
This exquisite Southampton Village rental, moments from Coopers and Halsey Neck Ocean beaches, seamlessly blends modern amenities with farmhouse charm, creating an inviting and luxurious living experience. Built in 2022, fully furnished (including a grand piano), and stunning. This modern farmhouse is sited on over an acre, features a pool, pool house, a fully equipped barn set up as an incredible entertainment area, and an intricately designed landscape creating a true oasis in the Village, near world-class Southampton Main Street amenities. The property offers 5 bedrooms and 6.5 baths in total, providing ample space for comfortable living, 7,500+/- square feet. Open interiors with rich hardwood flooring throughout, coffered ceilings, gorgeous wall paneling and simply faultless interior design. The great room includes a chef's kitchen, dining area, living room, and a charming breakfast nook with a wet bar. Smart home technology enhances convenience, with features like a Lutron lighting...
MD - LD Rental: $450,000
Christopher J Burnside
(516) 521-6007
Aubri Peele
(631) 252-5434
Village Of Southampton
$200,000
Village of Southampton, NY
Rental
Bedrooms: 8
Bathrooms: 8.5
Web ID: 736485
This park-like beauty has private and serene water views from these eight bedrooms, eight- and one-half bath traditional residence, which includes a first-floor primary bedroom. Decorated with style and sophistication by Greg McKenzie Design. Eat-in gourmet chef's kitchen, living room with wood burning fireplace, dining and an enclosed sunroom. All this on over two waterfront acres in the estate section of Southampton Village, heated 40x20 gunite pool with jacuzzi, patios, two gazing ponds and your very own dock that leads out to Shinnecock Bay. Available for summer and extended season 2025. Other periods upon request. ID: 736485
June Rental: $100,000
July Rental: $200,000
July / Aug Rental: $400,000
August - LD Rental: $200,000
Amelia M Doggwiler
(631) 204-2426
John P Vitello
(631) 204-2407
Village Of Southampton
$80,000
Village of Southampton, NY
Rental
Bedrooms: 5
Bathrooms: 4
Web ID: 735460
A wonderful south of the highway location in the Village estate area. The immaculate and stylish five-bedroom house features a living room with fireplace and beamed cathedral ceiling, handsome library/media room, dramatic dining room with curved glass wall, four baths and sauna/steam bath. Master suite with cathedral ceiling fireplace and steam bath. Two of the 5 bedrooms are located on the walk-out lower level with media extra sitting room. Central air conditioning and new Sonos sound system. The landscaped one-acre grounds feature rolling lawns and a courtyard with heated swimming pool, Jacuzzi, gazebo and studio above garage. Minutes to Coopers Beach. Listing ID: 735460
MD - LD Rental: $195,000
June Rental: $40,000
June/July Rental: $115,000
July Rental: $80,000
July / Aug Rental: $165,000
August - LD Rental: $90,000
September Rental: $40,000
December Rental: $20,000
Winter Rental: $140,000
Year Round: $295,000
Christine Sullivan Witker
(631) 204-2403
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
Tuckahoe
$9,000
Tuckahoe, NY
Rental
Web ID: 898665
Available for lease with a 5/1/23 occupancy date. $32 per s/f. 16,000 s/f or 5 3,200 s/f units still available of the 22,400 s/f total on main level. 22,000 s/f lower level with lift. Listing ID: 898665
Alyssa Bashaw
(631) 204-2428
Village Of Southampton
$30,000
Village of Southampton, NY
Rental
Bedrooms: 3
Bathrooms: 3
Web ID: 835449
Let this lovely completely renovated 3 bedroom townhouse home be your summer retreat. First floor consists of an open floor plan, kitchen/dining/living area, 1 bedroom with 2 twin beds, full bath and sliders open to a lovely patio. Second floor features gorgeous master bedroom and bath, en-suite guest bedroom and washer/dryer. Amenities include a heated saltwater pool and 2 professionally paved tennis/paddle ball courts. Close to all Southampton Village restaurants, shopping and Cooper's beach. This hotel-like accommodations make this townhouse a must see. Listing ID: 835449
July / Aug Rental: $50,000
August - LD Rental: $30,000
Gertrud Hoertnagl-Pereira
(631) 204-2425
Village Of Southampton
$35,000
Village of Southampton, NY
Rental
Bedrooms: 3
Bathrooms: 2
Web ID: 755008
Ideally located in Southampton Village, this lovely summer rental is a short distance from Village restaurants and shopping and is also very close to the most beautiful ocean beaches on the east coast. The home has three bedrooms and two updated full baths and is tastefully decorated and fully equipped. There is a heated gunite pool, plenty of outdoor entertaining space and community tennis is available within a short stroll from the house. It's the ideal summer getaway! Updated for 2020. Listing ID: 755008.
June Rental: $25,000
July Rental: $35,000
August - LD Rental: $45,000
Astrid Pillay
(631) 771-5312
Marie McCullough
(631) 204-2420
Sag Harbor
$10,000
Sag Harbor, NY
Rental
Bedrooms: 4
Bathrooms: 4.5
Web ID: 908778
Moments from all that Sag Harbor Village has to offer, this luxuriously chic home features 4 bedrooms, 4 1/2 bathrooms, an inviting floorplan, heated saltwater gunite pool, and huge, private backyard. The entire home has been newly decorated in a Hamptons chic style. 1500sf of finished lower level space further enhances the enjoyment of the home. The beautifully landscaped and ultra private backyard allows plenty of space for lazing by the pool or entertaining with your outdoor kitchen for a perfect Hamptons summer. . Listing ID:908778
November Rental: $10,000
December Rental: $10,000
Jeanne Galante
(631) 903-6184
East Hampton
$50,000
East Hampton, NY
Rental
Bedrooms: 4
Bathrooms: 4.5
Web ID: 735593
Rental Registration #: 24 - 0,773 - Two-story traditional situated in a lovely woodland setting offers four ensuite bedrooms (including primary with fireplace) plus a sleeping loft, and four and one-half baths. Living room with fireplace, formal dining room, and well-appointed kitchen. Comfort is a priority with three-zone heat and air-conditioning. The private 1.47+/- acre property borders a 21+/- acre reserve and is one-half mile from the beach. 20'x 40' heated vinyl pool with bluestone trim, an outdoor shower and extensive decks round out this offering. Listing ID: 735593
MD - LD Rental: $120,000
June Rental: $25,000
June/July Rental: $65,000
July Rental: $50,000
July / Aug Rental: $100,000
August - LD Rental: $55,000
Year Round: $175,000
JB Jose B DosSantos
(631) 903-6147
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