60 Hamptons Rentals

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Sag Harbor
$465,000

Sag Harbor, NY
Rental
Bedrooms: 5
Bathrooms: 6
Web ID: 867985

Beautiful Bucolic Waterfront -- Best Sunsets in the Hamptons. Overlooking Noyack Bay, this newly constructed, triple-mint, modern manor boasts breathtaking water views and stunning sunsets. The soaring floor to ceiling windows, expansive decking, heated gunite waterside pool, plush outdoor furniture, cozy fire pit, outdoor shower and Lynx professional grill, adorn the waterside veranda, creating a grand and sumptuous Hamptons experience. So, too, this property has a rare and coveted private deep water dock for backyard paddle boarding, kayaking or...bring your own boat. Ideal for entertaining, this home is appointed with an Il Forno pizza oven, sous vide technology, an outdoor herb garden and an enviable array of Japanese chef's knives, surely to fascinate the boldest of home chef's. With rich oak, warm walnut and modern steel finishes this property exudes serenity and grace and is sure to impress. Impeccably decorated and beautifully appointed, this modern retreat is mired among majestic...

April Rental: $35,000
May Rental: $35,000
MD - LD Rental: $465,000
October Rental: $35,000
Two Week Rental: $105,000

Cynthia R. Barrett
(631) 537-4322

Village Of Sag Harbor
$250,000

Village of Sag Harbor, NY
Rental
Bedrooms: 4
Bathrooms: 4.5
Web ID: 906568

Over a half of an acre of a topographically ideal, usable lot in the Village. A real pool, 20x40 feet! Plenty of room in the spacious, rolling backyard. Sun drenched and designed for easy low maintenance, open living, showcased by an open, airy, eat in kitchen with plenty of space to entertain. Amenities abound in this transitional masterpiece - too many to list. Located in the heart of Sag Harbor Village, less than a quarter mile to all - Havens Beach, Long Wharf, Bay Street, Sag Harbor Cinema.

MD - LD Rental: $250,000
Year Round: $280,000

Elizabeth A. Phenis
(631) 537-4357

Andrea L. Ackerman
(631) 537-4340

Village Of Sag Harbor
$240,000

Village of Sag Harbor, NY
Rental
Bedrooms: 5
Bathrooms: 5
Web ID: 738713

Retreat to this gorgeous Sag Harbor Village newly built summer house on a quaint avenue in the heart of the historic district. The open floor plan is light and bright and provides 5 comfortable bedrooms and 5 luxurious bathrooms so there is room for everyone. Top of the line details throughout the home are complimented by tasteful new furnishings in a modern beach house theme. Gourmet kitchen with center island and solid stone counters. There is also a large finished basement with media room. Outside enjoy the sparkling heated pool and fresh landscape. Central air, hardwood floors, and 1 car garage.

MD - LD Rental: $240,000
Year Round: $280,000

Kimberly Kakerbeck
(631) 537-4351

Andrea L. Ackerman
(631) 537-4340

Village Of Sag Harbor
$150,000

Village of Sag Harbor, NY
Rental
Bedrooms: 4
Bathrooms: 3
Web ID: 903810

Looking for Sag Harbor school year? This lovely home is dab in middle of the school and Mashashimuet Park. Open light filled home offering 4 bedrooms, 4 baths just moment away from downtown Sag Harbor Village. Enjoy this conveniently located family friendly home this coming season. Listing ID:903810

Custom Rental: $150,000

Kimberly Kakerbeck
(631) 537-4351

156 Main Street
$150,000

Village of Sag Harbor, NY
Rental
Bedrooms: 5
Bathrooms: 6.5
Web ID: 902781

Four level historic house at 156 Main Street has been completely renovated (2023) and is offered for rent. In the heart of Sag Harbor Village this beautiful compound which includes a separate lower level with kitchen, two bathrooms and its own entrance. One of several 'Captain's' houses dating back to 1806, this Sag Harbor classic offers twin parlors plus a large modern kitchen with dining area on the first floor. Three bedrooms including the master on the second floor and a third-floor bedroom suite with kitchenette. Elaborate brick and bluestone terrace with built in barbecue grill and outdoor furniture and dining tables. Heated gunite swimming pool with hot tub plus pool house with sink, refrigerator and full bath. Expertly decorated and furnished, experience the sensational design and craftmanship of this total renovation. Listing ID:902781

Custom Rental: $225,000
MD - LD Rental: $350,000
July Rental: $150,000
July / Aug Rental: $275,000
August - LD Rental: $150,000
Short Term Weekly: $20,000

Roxanne A. Briggs
(631) 903-6121

Peter M. Turino
(631) 903-6115

Village Of Sag Harbor
$135,000

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...

Ext. Season: $135,000

Stacy Pennebaker
(516) 532-5765

Linley Pennebaker Hagen
(631) 725-5583

Village Of Sag Harbor
$110,000

Village of Sag Harbor, NY
Rental
Bedrooms: 5
Bathrooms: 4.5
Web ID: 898592

On coveted Glover Street in the heart of Sag Harbor Village is this beautifully and recently completed custom residence with designer decorated interiors by Mitchell Gold. With water views, this property is moments to the Main Street shopping, Long Wharf, and some of the most famous restaurants In the Hamptons. This 5 bedroom 5 1/2 bath house offers a first floor as well as a second floor primary suite with a fireplace. There is a formal living room with a fireplace as well as a large family room with another fireplace, all open to the professionally outfitted kitchen and dining areas. The glassed in porch offers the 4th fireplace, for cozy relaxation, cocktails or entertaining. The lower level is finished with radiant heated floors, gym, living space, wet bar, movie theater and bedroom with full and half baths and 2nd laundry. ...

August - LD Rental: $110,000
Year Round: $400,000

Andrea L. Ackerman
(631) 537-4340

Elizabeth A. Phenis
(631) 537-4357

Sag Harbor
$100,000

Sag Harbor, NY
Rental
Bedrooms: 3
Bathrooms: 3
Web ID: 876339

RP 201418 This perfectly renovated 3 bedroom 3 bathroom home has it all. It is equipped with a new kitchen and bathrooms. In addition, it is outfitted with chic and modern furniture. Located close to the waterfront community near Long Beach in Sag Harbor and a short distance to Sag Harbor Village.This property features a fenced in backyard with heated pool, security system, central A/C and Sonos sound system for listening indoors or out by the pool. This home offers an open floorplan with a bright and airy kitchen leading into a sitting and dining area. It also has a fully finished basement with an extra common area living space. The added bonus for this home is its close proximity to water for paddle boarding, launching boats and kayaking. Listing ID: 876339

Year Round: $100,000

David Tenenbaum
(631) 771-5322

Kimberly Kakerbeck
(631) 537-4351

11 Carver Street
$100,000

Village of Sag Harbor, NY
Rental
Bedrooms: 5
Bathrooms: 5.5
Web ID: 910809

Welcome to 11 Carver Street in Sag Harbor Village. This just completed new contemporary was built to impress. Located prominently in Sag Harbor Village just minutes to Main St. The thoughtfully designed 4,400 square foot home over three levels features 5 bedrooms, 5 full baths, 2 half baths, finished lower level and includes a cabana pool house and detached garage. Exquisite details and finishes throughout. The living room offers dramatic 16' ceilings, with plenty of natural light flowing through the glass sliding doors and gas fireplace. Gourmet chef's kitchen includes Bertazzoni appliances, 36' range, custom Miralys cabinetry, two dishwashers, Caesar stone countertops and tremendous views of the pool. The first-floor primary boasts spacious room with king bed, modern primary bathroom with Italian porcelain floors, floating vanity, 63'' soaking tub and walk-in rain shower. The two additional guest suites are ensuite that complete the main level. Upstairs ascend to your second...

January Rental: $15,000
February Rental: $15,000
March Rental: $15,000
April Rental: $15,000
July Rental: $100,000
September Rental: $50,000
October Rental: $15,000
November Rental: $15,000
December Rental: $15,000

Maria Pashby Dual Lic
(631) 537-4330

Joanna Pashby Dual Lic
(631) 537-4346

Sag Harbor
$90,000

Sag Harbor, NY
Rental
Bedrooms: 5
Bathrooms: 4.5
Web ID: 876286

RR#:201499 Spend summer in the Hamptons at a quiet cul-de-sac in Sag Harbor at this 5-bedroom, 5.5 bathroom countryside estate that enjoys equal amounts of privacy and access to the Hamptons' nearby beaches, golf, dining, and shopping. A thoughtfully decorated, elegant decor blends with rustic accents to create a sophisticated, welcoming atmosphere. The master suite features a marble bath with air jet tub and separate shower. The finished lower level of the home includes a gym, home theatre, jacuzzi bath and steam shower. Outdoors, a sunken 40x18 gunite swimming pool, hot tub, outdoor shower, screened porch, covered dining veranda and vine-covered pergola with fire pit await amid lush landscaping and plenty of room for relaxing and entertaining. So close to reserve, trails to fresh water Trout Pond, marinas, secluded bay inlets and Foster Memorial Long Beach for paddle boarding and kayaking while Sag Harbor Village is...

July Rental: $90,000

Cynthia R. Barrett
(631) 537-4322

2 Sage Street
$90,000

Village of Sag Harbor, NY
Rental
Bedrooms: 4
Bathrooms: 3.5
Web ID: 861430

This Pristine 4 bedroom, 3 1/2 bath townhouse is set within the historical building and grounds of The Watchcase Condominium. The 3000+ sq ft home w/ 1000+ sq ft terrace offers the full condominium amenities available to its residents and guests. From the Sage Street entrance, the open-plan chef's kitchen offers a casual & sunny dining spot, leading to a formal, marble-accented dining area and then directly onto the private roof terrace. Original Steven Gambrel kitchen and bathroom details inspired by the historical factory building pepper the home, whilst a neutral & sophisticated color palette is layered with the combined textures of luxurious designer furnishings, curated antiques, and art, creating an effortlessly chic & sophisticated home. The private elevator offers convenient access to every floor, from the garage to the three upper living levels. Sonos speakers, Smart TVs, high-end bed linens, and Egyptian cotton towels offer luxury details, with...

MD - LD Rental: $230,000
July Rental: $90,000
July / Aug Rental: $195,000

Village Of Sag Harbor
$80,000

Village of Sag Harbor, NY
Rental
Bedrooms: 5
Bathrooms: 4
Web ID: 736852

Circa 1830 and completely restored in 2015, this stunning, beautifully appointed home is just a short stroll to Main Street restaurants and shops. The first floor offers the fully outfitted chef's kitchen, a separate formal dining room, a very spacious living room and a quiet office. The laundry is conveniently located off the kitchen in the sun/mud room. Upstairs, you find the primary ensuite bedroom with gas fireplace and two additional bedrooms with a full bathroom. An added bonus is the third floor media and game room. The lushly landscaped garden offers privacy at the heated salt water pool and patio complete with a terrace dining area. A separate, nicely furnished pool cabana with a full bathroom and loft offers additional living space and an oversized outdoor shower. This home is elegant and gracious but at the same time inviting and comfortable. Listing ID: 736852

July Rental: $80,000
July / Aug Rental: $165,000
August - LD Rental: $95,000

Maureen J. Geary
(631) 903-6167

16 Bittersweet Lane
$80,000

Sag Harbor, NY
Rental
Bedrooms: 5
Bathrooms: 4.5
Web ID: 909698

AVAILABLE JULY, 2024 (open to first two weeks of Aug-inquire for pricing). Located off a quaint private road this stately +/- 4,790 square foot 5 bedroom, 4.5 bath home makes for a fabulous retreat that can be enjoyed 365 days a year. Boasting a free-flowing, versatile floor plan that feels 'just right,' guests are met with a stunning double height entry hall giving way to a two-story great room accented by soaring ceilings and partial bay views. Prime for entertaining yet spacious enough to offer privacy for one and all, no detail was spared in this masterful build. Standout features include two primary bedroom suites (one upstairs, one downstairs), three guest bedrooms, gourmet kitchen, 800 square foot bonus room, screened in porch, palatial deck leading to a heated pool, Har-tru tennis court, bay views from the 2nd floor, and private access to a secluded bay front beach with the ability...

July Rental: $80,000

Sag Harbor
$78,000

Sag Harbor, NY
Rental
Bedrooms: 4
Bathrooms: 3
Web ID: 736928

This lovely 3,000 sqft recently renovated with high quality finishes and beautifully and professionally decorated house offers 4 bedrooms, 4.5 baths, sited on a full acre. Additional amenities are heated gunite free from pool surrounded by a beautiful lounge outdoor area, 2 car garage, full finished basement with TV room, billiard, soccer table game and Central Air Condition. Have to be seen to appreciate it. Available summer 2021Listing ID: 736928

Custom Rental: $32,000
May Rental: $24,000
June Rental: $32,000
July Rental: $78,000
August Rental: $78,000
Winter Rental: $36,000
Short Term Weekly: $20,000

Cynthia R. Barrett
(631) 537-4322

Sag Harbor
$78,000

Sag Harbor, NY
Rental
Bedrooms: 3
Bathrooms: 2
Web ID: 756508

This private and recently renovated architectural marvel on nearly 3 acres, and adjacent to preserve, will surprise and delight you with its charm and unique setting. Entering the first floor of this 3 story home you will find a spacious living room with 2 bedrooms and bath -- up to the 2nd floor where you'll love the open living/dining and kitchen area with fireplace as well as a convenient deck looking out to the beautifully landscaped grounds and oversized pool. From here you can enjoy year round sunsets from home, pool or hot tub! The master suite and bath on the 3rd floor are divine and also include a cozy deck with distant water views of Peconic Bay. There are koi ponds with waterfall to enchant you and nearby walking trails for the nature lover in you. New furnishings plus great mid-century to modern art will add to your great...

Year Round: $78,000

Richard Finder
(631) 702-7511

Maureen J. Geary
(631) 903-6167

Village Of Sag Harbor
$75,000

Village of Sag Harbor, NY
Rental
Bedrooms: 4
Bathrooms: 5.5
Web ID: 738081

This renovated Federal style offers beautiful details and elegant furnishings throughout. Features include four bedrooms; five and one-half baths; living room with fireplace; lovely eat-in kitchen with slate floor; library and screened porch. Sited on a very private, landscaped, just shy of an acre lot, with a separate guest cottage with living room, kitchen and bath and a swimming pool for summer relaxation. Available May 26th - June 30th $40km June 30th - July 20th $50k, August 18 - September 4th $45k. Listing ID: 738081

June Rental: $35,000
July Rental: $75,000
Winter Rental: $5,700

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