Hamptons Summer 2020 Rentals

Tim Davis

The Hamptons Luxury Market Leader

S U M M E R R E N TA L S 2 0 2 0

Tim Davis

Lic. Assoc. RE Broker Regional Brokerage Advisor East End 631.702.9211 | tgdavis@corcoran.com

Welcome to our Luxury Portfolio of properties Summer 2020 Rentals Edition. Throughout these beautiful pages, you will find short term and long-term opportunities in all locations and price ranges. Being easily accessible to the world has made the Hamptons lifestyle experience more achievable to a larger audience than ever before. Scroll through the following pages and imagine your dreamy summer Hamptons experience. The cool blue water of the ocean, big sky views of open space, bays, creek, ponds and lush lawns of massive estates will captivate and awe. For those looking for the “inside scoop,� view our local guide complete with attractions and restaurants, plus a bit of history for those keen to know more.

This truly is a place like no other.

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SOUTHAMPTON OCEANFRONT 9 BEDROOMS | 12.5 BATHROOMS | 8 ACRES PRICE UPON REQUEST | WEB ID# 836505 The opportunity has presented itself to rent a world class ocean and bayfront estate on one of the world’s preeminent streets, Meadow Lane, located in Southampton Village’s premier estate area.

You will find the home comes complete with every bit of allure and exclusivity that you would expect from one of the Hamptons’ most sought after properties. Sited on 8 acres, the property is comprised of a recently renovated 18,000 SF+/- residence with 9 bedrooms, 12 full and 1 half bathrooms, separate guest and staff quarters, a game room, and gym along with a heated pool, tennis court and three car garage. With 500+ feet of ocean frontage and a dock on Shinnecock Bay, this double waterfront property has the best of both worlds. Whether you are looking to paddle board on the bay or swim in the ocean, here you can have it all. With several outdoor entertaining areas, panoramic water views, and direct, private ocean access, 700 Meadow Lane in Southampton is the perfect setting for a discerning individual to enjoy summer to the fullest. This unique and elegant property offers every feature and amenity one could wish for including Fleetwood windows and doors, the finest selection of marble and Bulgarian limestone, large pool and spa, reflecting pool, tennis court, and private boardwalk to the beach.

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SOUTHAMPTON OCEANFRONT 10 BEDROOMS | 12 BATHROOMS | 4 ACRES PRICE UPON REQUEST | WEB ID# 18-2360 A spectacular modern beach house recently completed, designed and executed by world famous architect Peter Marino is available for rent. The 13,000 square foot limestone residence on two levels is positioned on over 4 acres with 200 feet of white-sand frontage. Superb Ocean to Shinecock Bay views from most of the principal rooms which include a massive double-height living room with a glass bridge connecting the two upper bedroom wings and recreation areas of the house. The outdoor spaces are outstanding as are the Oceanside swimming pool and bayside dining terrace overlooking the sunken tennis court.

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WATER MILL 8 BEDROOMS | 7.5 BATHROOMS | 2.13 ACRES JUNE 150K | JULY 250K | AUG 350K | MD-LD 750K | WEB ID# 105958 Water Mill residence sited on over 2.1 acres on a quiet cul-de-sac is centrally located to village and ocean beaches. This new traditional is fresh and chic with sunlit double height living room which opens to the outdoor entertaining areas. The home also features a library/media room with adjoining powder room, den with fireplace, formal dining room and large eat-in kitchen, with seven bedrooms including the master bedroom suite with gas fireplace and first floor guest suite there is ample room for guests. The lower level boasts a 10 seat theater, game room with pool table and wet bar, wine cellar and room for staff. Outside you find dining terraces, outdoor grill, swimming pool, pool house and all-weather tennis court. Retreat to the pool house to enjoy the lounging room with fireplace, play room, powder room and outdoor shower.

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SOUTHAMPTON 8 BEDROOMS | 10.5 BATHROOMS | 2.25 ACRES JULY 325K | AUG 325K | 675K MD-LD | 225K 2 WEEKS | WEB ID# 43987105958 A truly unique Southampton traditional in one of the most sought-after locations in Southampton Village. This 8 bedroom home was built with great attention to detail and a clear aesthetic sensibility to the architectural history of our time. Every room is large and open with gorgeous light in very comfortable spaces. The 2.25 acres in the estate section of Southampton’s Village has mature landscaping with a gorgeous pool and a sunken tennis court which will complete your enjoyment of this very special Southampton property.

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SOUTHAMPTON PONDFRONT 7 BEDROOMS | 8 BATHROOMS | 2.4 ACRES 650K MD-LD | WEB ID# 101857 Atlantic Ocean views and west facing pond frontage is the setting for this spectacular luxury summer rental. The first time ever available for rent, this home in pristine condition is located within the coveted Murray Compound and just a few houses from the Atlantic Ocean. The stylish and sleek contemporary residence of over 8,500 square feet was originally designed by architect Preston T. Phillips for Ford Motor heiress Elena Ford. The home offers grand comfortable rooms with soaring ceilings and beautiful interior spaces for seaside living and the ultimate Hamptons lifestyle. An ideal floor plan with generous principal rooms includes 7 bedrooms and 10 bathrooms on two floors. The glorious living spaces open to the expansive west facing terraces, swimming pool, dining pavilion, an expansive lawn along Wickapogue Pond.

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SOUTHAMPTON OCEANFRONT 12 BEDROOMS | 12 BATHROOMS | 8.2 ACRES AUG-LD $575,000 | WEB ID# 92566 Atlantic Ocean views and west facing pond frontage is the setting for this spectacular luxury summer rental. The first time ever available for rent, this home in pristine condition is located within the coveted Murray Compound and just a few houses from the Atlantic Ocean. The stylish and sleek contemporary residence of over 8,500 square feet was originally designed by architect Preston T. Phillips for Ford Motor heiress Elena Ford. The home offers grand comfortable rooms with soaring ceilings and beautiful interior spaces for seaside living and the ultimate Hamptons lifestyle. An ideal floor plan with generous principal rooms includes 7 bedrooms and 10 bathrooms on two floors. The glorious living spaces open to the expansive west facing terraces, swimming pool, dining pavilion, an expansive lawn along Wickapogue Pond.

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SOUTHAMPTON 9 BEDROOMS | 10.5 BATHROOMS | 2.21 ACRES AUG 350K | JULY/AUG 550K | WEB ID# 55023 Located along Gin Lane and set back behind tall privet hedges is this wonderful estate section oasis.

A sprawling floor plan makes for luxurious seaside living and generous room for family, friends and entertaining. This chic styled home with a good feeling boasts principal rooms with vaulted ceilings allowing for great light and a sense of air and space. Nine bedrooms and ten and a half bathrooms located in separate wings afford great privacy. The living room, library, media room, office and spectacular kitchen all open to the courtyard terrace and 60-foot swimming pool. Outside amongst the 2.2 acres of beautiful landscape you will find a tennis pavilion, tennis court, two car garage, and outdoor shower. Ocean beaches within a short distance. Undoubtedly one of the top addresses in all of the Hamptons.

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AMAGANSETT 6 BEDROOMS | 8.5 BATHROOMS | 1.1 ACRES July $265K | AUG-LD $300K | JULY/AUG-LD $525K WEB ID# 18-2360 Located on bucolic Further Lane East, south of Further Lane. The house was designed and built

by Fox-Nahem Associates whose award winning work has appeared in publications worldwide.

Featuring custom designed furniture as well as vintage pieces and artwork by some of the 20th century’s most renowned designers and artists. All of the rooms are sumptuously comfortable yet friendly. No detail has been overlooked. The Oceanfront home consists of 6 bedrooms (including 2 masters, staff room, and 8 1/2 baths. Each bedroom has a full bath en-suite with separate TV/music system and mini fridge. The ocean-facing master suite has a private terrace with a fantastic ocean view, sitting area, large walk-in closet, aerated soaking tub, and oversized steam/shower. There is a home gym, large laundry facility, parking for 8 cars, and a fully equipped kitchen completely outfitted for all kinds of entertaining. The very private pool area, which is removed from the main house, has a 55’ pool with double heater and ozone non-chlorinated, filter system. There is a 400 sq ft open cabana with fireplace, plus a separate enclosed pool house with full bath, A/C, W/D, and kitchen. In addition there is a beautiful stocked koi pond with a running stream. A beautiful private grass path leads down to the dunes, ending at the secluded ocean beach.

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SOUTHAMPTON OCEANFRONT 6 BEDROOMS | 6 BATHROOMS | 2.21 ACRES 350K JULY | 375K AUGUST | 725K JULY/AUGUST | WEB ID# 105958 Located in a coveted Water Mill location with western sunset views of a scenic pond, open fields, and the Atlantic ocean, this spacious home features an ideal floor plan for all of the seasons the Hamptons has to offer. Some of the bonus elements include seven bedrooms, eight and a half bathrooms with a wonderful master suite, four fireplaces, a media/screening room, screened in porch and convenient elevator. The exqui-sitely furnished living spaces open up to extensive terracing overlooking lawns, gardens and the 50 foot heated saltwater pool and spa. The last compelling prime feature is the deeded access to a pristine white sand Atlantic Ocean beach which is just a blink away.

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AMAGANSETT

4 BEDROOMS | 4.5 BATHROOMS | 0.8 ACRES MD-LD $360K | July $130K | AUG-LD $160K | JUNE-JULY $210K | WEB ID# 18-2361 Dreamy super chic beach house with grass path to gorgeous ocean beach. This totally renovated, new, oceanfront hideaway is located on highly sought after private lane, south of Further Lane.

Designed by AD100 Designer Joe Nahem, this adorable mid-century home is set on a park-like shy acre +/- . For those looking for the ultimate in casual, laid- back, beach lifestyle, this property delivers. With four bedrooms, five and a half baths, state of the art kitchen, Sonos sound system, long gunite heated pool, new European-wood deck , two masters (one with soaking tub & separate shower, other with Steam shower and fitted all with Waterworks fixtures), and a lower level gym with terrace space. The main living space with wood clad, cathedral ceilings & antique barn wood walls has stunning new & mid-century vintage furniture and lighting, with pieces by Wendell Castle, Eero Saarinen, Kerstin Horlin-Holmquiste. 20th century art by masters like Jim Dine, Gregory Crewdson & Roy Lichtenstein. There is also a private, fully furnished roof deck and 4th bedroom with separate entrance can be used as a den. This property is super private and the all new landscaping is complimented by majestic old mature trees.

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SOUTHAMPTON VILLAGE

6 BEDROOMS | 6.5 BATHROOMS | 2.47 ACRES | MD-LD $350,000 | WEB ID# 64721 Pondfront residence with ocean views and deeded access to private ocean beach. Comfortable contemporary beach house with great light and views ideally located within a private enclave. Six bedrooms six and a half baths. Great room with fireplace, dining room and chefs kitchen. Terrific waterside pool with expansive decking and Har-Tru tennis court.

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SOUTHAMPTON

7 BEDROOMS | 6.5 BATHROOMS | .6 ACRES MD-LD $500,000 | WEB ID# 67441 Enjoy your summer stay in this traditional village home which has recently been completed. Open floor plan offers plenty of sunlight and principle opens to terrace and pool area. The elegant master suite with private sundeck and spacious bath is one of seven bedrooms. Just a few of the amenities include walk-out gym, wine room, swimming pool and pool house.

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SOUTHAMPTON VILLAGE 6 BEDROOMS | 6.5 BATHROOMS 1.4 ACRES | $325,000 | WEB ID# 77271

Summer on the ocean along exclusive Gin Lane when you rent this stunning Southampton estate home sited on 1.4 manicured acres spanning 250’ of pristine sandy beach. Available for various time frames during Summer 2018, this 10,000 SF palatial resort-like beach house includes six bedrooms, six full bathrooms and one half baths, two chef’s kitchens, pizza oven, dining room, two full bars and a gym featuring an indoor spa and sauna. Ocean breezes waft over a swimming pool, tennis court and extensive Oceanside decking with built in BBQ. Additional amenities include bocci and basketball courts, a roof deck and terrace. Although the village of Southampton is merely a short bike ride away, with so much going on at the fabulous beach property and heroic ocean views you may never want to leave.

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QUOGUE

6 BEDROOMS | 6.5 BATHROOMS | 1.58 ACRES MAY-LD 395K | MD-LD 350K The Post Summer Cottage re-imagined with additions and thoughtful expansions has been restored/ rebuilt with all of the modern amenities one expects to find in a home for today’s lifestyle. Nearly 6,000 square feet of living spaces on three floors include a first floor with rooms that are perfectly proportioned and positioned for optimal living experiences. From the movie-set country kitchen with adjoining dining porch, to the library, dining, living and gathering rooms with three fireplaces, this home impresses at every turn. The second floor with five bedrooms including a beautiful master suite with vaulted ceiling embodies “live who you are” perfectly on so many levels. Don’t forget the third floor bunk room and bath for those four season sleep overs. Outside among tall privet hedges and layers of evergreen border plantings lies the best private tennis court in Quogue Village. Enjoy lounging by the 44 foot pool, spa with terrace and relish in those lazy summer afternoons dining alfresco at the pool pavilion. Tasteful, beautiful and only what one would expect with having worldrenowned decorator/designer Alexa Hampton be the conductor of this superb orchestration.

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SOUTHAMPTON

6 BEDROOMS | 6.5 BATHROOMS | 2.53 ACRES AUG-LD $250,000 | WEB ID# 73906 Old world charm and style in this three story shingle style residence. Large veranda, period details, original moldings and beautiful mantels. Ideal master suite, five guest suites, plus several staff rooms. Living room, dining room, country kitchen, sunroom, library, and play room. Outdoors the 2.5 acres of privacy and lovely garden areas include north/south tennis court, inground heated pool and pool house.

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SOUTHAMPTON

9 BEDROOMS | 7 BATHROOMS 1.24 ACRES | $225,000 AUGUST | WEB ID# 60445 This 9 bedroom, 7 bathroom beach house has a well designed floor plan for relaxation and entertaining. Located well within a compound, this property offers your own ocean beach accessjust in front of the lush green lawn and flower gardens. There are water views from many rooms and many balconies from which to hear the sounds of the waves. A large covered porch leads you to your heated gunite pool and tennis court. Decorated in colorful beach colors and tasteful art, this home offers you the perfect vacation spot for your Summer in the Hamptons.

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WATER MILL

8 BEDROOMS | 8.5 BATHROOMS | 1.25 ACRES MD-LD $450,000 | JULY $175,000 | AUG-LD $225,000 WEB ID# 135631 This brand new construction by Breskin development located in Watermill exudes luxury with eight bedrooms, eight full bathrooms, a finished 2,960 +/- square foot lower level, heated pool and spa, sunken tennis court, and pool house. As you enter the grand first floor you will find the great room, dining room, junior master suite, private den, and the expansive eat-in custom kitchen. The second floor consists of four guest suites and the luxurious master suite with walk-in closets and a spa-like bathroom with Cuiffo custom waterfall double vanity and soaking tub. The finished lower level includes a game room, home gym, media room, sauna and powder room. The two additional guest/staff rooms share a full bath. In addition to the heated 20Ă—50 pool and spa, this home has a professional sized, sunken tennis court with basketball area, a 450 +/- square foot pool house includes a half bath and changing room, kitchenette and wet bar, and a Nana door bi-fold window allowing inside/outside entertaining with exterior bar. This property has everything one needs for a one of a kind summer vacation.

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SOUTHAMPTON VILLAGE

9 BEDROOMS | 6.5 BATHROOMS | 1.00 ACRE JULY $150,000 | JULY 2 WEEKS $100,000 | JULY $175,000 | AUG 2 WEEKS $125,000 | WEB ID# 132758 In the heart of the village, conveniently located between beaches and Main Street shops and restaurants, this beautifully renovated farmhouse has every modern amenity, including a separate guest house. The main house has three stories with an eat-in kitchen, large living room, dining room and family/TV room. There is also a beautiful covered outdoor patio and dining space that look out onto the swimming pool and mature landscaping and flower garden. The second floor boasts a lovely master suite with a spacious bathroom. There are five more guest rooms in the main house, including two on the third floor. The guest house has its own entrance as well as an additional three bedrooms and two more bathrooms. In addition to this, there is yet another full kitchen and a gym.

This is a fabulous opportunity to rent a classic, updated home in a prime location.

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SOUTHAMPTON

6 BEDROOMS | 7 BATHROOMS | 1 ACRES JULY 170K | AUG 185k | WEB ID# 60953 Within the Southampton estate section, private path to Halsey Neck Beach and with gated entry stands this nearly 8000 square feet shingled post modern designed by Michael Conroy architect and interiors by Marshall Watson. Six bedrooms with a deluxe master suite with sundeck. Generous living and entertaining spaces with modern conveniences of Crestron system, Sonos, and 4k also including a screened porch with fireplace, outdoor living room with fireplace, private gardens and meticulous landscapes, sumptuous inground 25x 45 swimming pool and 12Ă—12 spa with waterfall, 3 car garage, distant pond views and ocean breezes.

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SOUTHAMPTON

7 BEDROOMS | 7.5 BATHROOMS | 2.67 ACRES $185,000 July | $185,000 AUG-LD First Offering of a wonderful summer rental on First Neck Lane with 2.6 lovely landscaped acres for your family and guests to enjoy this Summer. Shingle style with three finished levels including a third floor sun porch with ocean views. Deep first floor sun porches and two decks with southern and western views, six bedrooms, eight full baths, four fireplaces and separate staff quarters. An eat in kitchen with breakfast area is ideal for lazy weekend brunches as is the outdoor alfresco dining patio. The living room and formal dining room spill out onto the large screened/enclosed side porches and rose garden. On the premises is a 40’ oval gunite heated pool with terrace and pool house with an additional private garden and stone patio. This home has updated farmhouse charm and elegance, nearby clubs, close proximity to the Atlantic Ocean and Southampton’s finest “World’s Best” beaches.

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SOUTHAMPTON

5 BEDROOMS | 5 BATHROOMS | 1 ACRES JUNE/JULY 135K | JULY 100K | 2 WEEKS 50K | WEB ID# 47517 Sequestered down a tree lined driveway you will find this waterfront oasis fronting on Lake Agawam with wonderful sunsets, secret gardens and an ideal summer house with waterside pool within close proximity to Southampton’s village center, Main Street and Jobs Lane. This home has five bedrooms and five and half baths. Sunlit interiors boasting ideal public rooms for entertaining spill out onto the large deck, terrace waterside lawn and pool.

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SOUTHAMPTON

9 BEDROOMS | 10 BATHROOMS | 2.03 ACRES AUG (2 weeks) $130,000 | WEB ID# 106485 Exceptional home with stunning European Flair is available for rent for two weeks. Contemporary elegance includes a grand foyer with a dual staircases and windows overlooking the grounds, two over-sized and separate living rooms, both accessing special areas of the garden, a very hip sun lounge, a large formal dining room with open balcony and library above, a TV/media room and a new gourmet state-of-the-art kitchen with a large, sunny and inviting informal dining area. There are nine en-suite bedrooms, and guest rooms in a separate wing. The master suite is very private and luxurious with 2 baths and 2 dressing rooms, a study and is surrounded by windows overlooking the grounds. All principal rooms have access to the stone patio surrounded by beautifully landscaped and private grounds. There is a heated swimming pool and a tennis court. Additional rooms include a staff area, a second catering kitchen, a professionally equipped gymnasium and virtual golf practice area. A very capable staff manages the daily routines at the house including housekeeping, grounds and pool care. Beautiful and a truly relaxing environment, this fabulous home will delight even the most discerning.

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SOUTHAMPTON

5 BEDROOMS | 5.5 BATHROOMS | 1.00 ACRE MD-LD $129,000 | July $64K | AUG-LD $74K | JULY-AUG $89K SHORT TERM $38K | BI-WEEKLY (SUMMER) $35K | WEB ID# 44964 You will be enchanted by the sound of the ocean when you arrive at this special five bedroom home with beautiful pool area and a tennis court. A well-appointed home with library, den, and living space for relaxing as well as entertaining during the Hamptons summer season. Don’t miss this opportunity to be by the beach and in the Village of Southampton just a short distance to Main Street and Jobs Lane.

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SAG HARBOR

3 BEDROOMS | 4.5 BATHROOMS | 3.4 ACRES JUNE/JULY 95K | AUGUST 80K | WEB ID# 73599 | WEB ID# 44964 An idyllic west facing waterfront setting with a “great lawn” and privacy situated on 3.4 +/- acres with 366 +/- sq. ft. of frontage on Noyac Creek. A chic and stylish three-bedroom, four and one-half bath contemporary home with a private deep-water dock completely renovated with interiors by renowned New York architect David Mann. On the homes upper level, the living room, den, dining area and eat-in kitchen benefit from an open plan that permits these rooms to flow seamlessly into one another while affording each of them beautiful views of the creek and of Morton Wildlife Refuge beyond. Three water view balconies off of the living room, master bedroom and screen porch enhance the effect of the surroundings. The lower level enjoys a large living/rec room with kitchenette beside the heated 46’ pool and two large en-suite bedrooms also opening directly onto the pool and side gardens with extensive stonework. Available for the first time.

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SOUTHAMPTON

5 BEDROOMS | 5.5 BATHROOMS | .30 ACRES JULY $85,000 | WEB ID# 133835 | WEB ID# 44964 Located in one of the most prestigious neighborhoods of Southampton Village, this Traditional home offers 5 Spacious bedrooms, En Suite Master with high end finishes, Large Open Eat in Kitchen with Cathedral Ceilings, Full finished lower level offers a gym, Temp Controlled Wine Cellar, and a state of the art Home Theatre. Outdoors offer lush landscaping, Outdoor fireplace, and an In-Ground Gunite Heated Pool. Minutes to the Village and ocean Beaches.

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EAST HAMPTON

4 BEDROOMS | 4.5 BATHROOMS | .40 ACRES AUG-LD $65,000 | WEB ID# 135263 Enjoy the month of August in this impeccable, newly renovated gem on Gould Street, very close to the village of East hampton. With 4 en suite bedrooms and an open floor plan, this home will not disappoint. The professional grade kitchen expands into the dining area and a TV/ Den while at the same time you can view the lush backyard through a wall of French doors. The lower level has just been completed to include an ensuite bedroom, additional entertainment space and gym.

Entertaining is seamless and backyard enjoyment easy with the addition of a poolside cabana with all the amenities.

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WATER MILL

5 BEDROOMS | 5.5 BATHROOMS | 1.1 ACRES August $50K 2Wks| WEB ID# 373125 First offering of a beautiful quiet country home with a private path to the Meyers Pond/Mecox Bay estuary. In perfect condition and just several years old, this one level home with an ideal floorplan boasts a high-ceilinged living room, formal Dining room, modern kitchen A master suite with two bathrooms, four additional bedrooms and a library/den. The south facing home opens to the covered terrace, swimming pool and established landscape. A superior rental by all standards.

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SOUTHAMPTON

9 BEDROOMS | 7.5 BATHROOMS | 1.80 ACRES MD-LD $450,000 | WEB ID# 545166 This classic shingle style residence on 1.8 +/- acres in Southampton Village is only steps away from the world class Southampton beaches. Ideal for a full summer rental, this completely renovated residence across three levels includes nine bedrooms, 6.5 baths, a gracious entry parlor, sitting rooms, living room, an enormous eat-in kitchen, a screened-in breakfast porch, and a dining room.

Elegant and comfortable, superbly-proportioned for entertaining and relaxing, indoors as well as outside, you may also enjoy the heated 50’x20’ Gunite pool.

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Bridgehampton

Reaching deeply north into the South Fork and positioned between Water Mill to the west and Sagaponack to the east, Bridgehampton has a name that begs for even more geographical clarification. This one is easy: The bridge in Bridgehampton refers to a bridge built across Sagg Pond by Ezekiel Sandford in 1686. Bridgehampton is undeniably the essence of posh, and for many Hamptonites, the summer simply does not end until the occurrence of the Hamptons Classic, one of the largest outdoor horse shows in the country. Perhaps Bridgehampton is even better known for the $43.5 million property rented by Beyonce and Jay-Z — and for Madonna causing a stir when she was accused of buying a parcel for a “tree farm,” adjacent to her horse farm, that was widely viewed as a bid for privacy, not agriculture. Perhaps she commiserated with another Bridgehampton resident, fashion designer Isaac Mizrahi, who designed a leather handbag named for the hamlet.

History Located in the town of Southampton, Bridgehampton was founded in 1640, but one of its most notable historical footnotes happened a century and half later, when a notorious criminal with a magnanimous streak and literary bent, the counterfeiter Stephen Burroughs, helped found the hamlet’s first library. A more complete story of Bridgehampton can be found at the Bridgehampton Museum, which contains such artifacts as 1,300 historical photographs, 300 historical books and Bibles, and collections of letters, ledgers, datebooks, textiles, and decorative arts. Bridgehampton also boasts the Children’s Museum of the East End, which attracts nearly 75,000 visitors annually, and the Dan Flavin Art Institute, a converted farmhouse that contains the late artist’s mesmerizing fluorescent works. And given the primacy of the Hamptons Classic, horse farms and other equestrian sites abound, from boarding and training at Billington Stables to elder care at Amaryllis Farm Equine Rescue.

Dine & Shop Busy all year round, Bobby Van’s is that rare national chain restaurant (seven in New York, two in D.C.) that has become identified with the Hamptons. The menu has a few surprises, reaching beyond the standard steakhouse fare of steaks, chops, clams, and shrimp cocktail to offer such choices as Icelandic cod and a Spanish octopus salad. Meanwhile, Almond, a French-influenced bistro, is truly a Hamptons institution and a community builder, serving up artists’ and writers’ nights along with escargot and Le Grand Macaroni & Cheese with prosciutto and preserved summer truffles. And topping out the top three is Topping Rose House. One of the few luxury hotels in the Hamptons, the venue pulled off a big coup last year by enlisting no less than Jean-Georges Vongerichten to run its restaurant. Meanwhile, good shopping is happening on Main Street, where the usual suspects — J. Crew, Theory, Club Monaco — give way to more local boutiques.

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east hampton

When people refer to East Hampton, they likely mean East Hampton the village, as opposed to East Hampton the town, the latter of which contains East Hampton village as well as the villages and hamlets of Montauk, Northwest Harbor, Springs, Wainscott, Amagansett, and a part of Sag Harbor. (Note: Every village and hamlet in the Hamptons lies either in the town of East Hampton or in the town of Southampton, its neighbor to the west and south.) So, with that bit of geography and terminology in place, when people refer to East Hampton, they are also referring to a world of money, a place where the words privilege and exclusivity come up well short. Some of the sites in East Hampton are synonymous with ultra-elite society: The Maidstone, Georgica Pond, and the infamous Grey Gardens, all iconic, capture the village’s exaggerated prestige. But East Hampton is also a picturesque resort of natural beauty, and the quality of its white sand beaches is undeniable.

history & culture Puritan settlers, a famous witchcraft trial, and meticulous regulation are all part of an East Hampton legacy of do’s and don’ts. The size of homes and the number of beach parking passes are sharply limited. A hilarious assessment by the late “Little” Edie Bouvier Beale, the eccentric subject of the campy documentary Grey Gardens (1976), is well known for its quirky but deadly accuracy: “They can get you in East Hampton for wearing red shoes on a Thursday.” Established in 1891, the Maidstone Club is so picky about its membership that even George Plimpton and Diana Ross were denied membership (even though the latter’s billionaire husband was a member). The scenic lagoon of Georgica Pond played summer host to President Bill Clinton (at the home of Steven Spielberg, no less), and its residents have included Martha Stewart and Calvin Klein. If rigorous attention to maintaining the flavor of East Hampton is perhaps off-putting to visitors, locals reap the benefits of sky-high property values and its shingle-style architectural history.

dine & shop Point one: Nick & Tony’s on Main Street is the East Hampton dining institution. For those not in the know, when The New York Times six years ago offered that the most coveted real estate in the Hamptons was a choice table in the eatery’s front room, the message was indisputable. 1770 House Restaurant, East Hampton Grill, and the Palm are also must-do’s on Main Street. For burgers, baked clams, steamers, and lobster rolls, a more casual gastronomic experience can be had on the pretty patio at Bostwick’s Chowder House. International brands are represented by Ralph Lauren (and Lauren’s daughter’s confectionery, Dylan’s Candy Bar), Lululemon, J. Crew, Vilebrequin, and Audemars Piguet (the watchmaker); some shops are open only for the season.

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ha mpton bays

Tucked away in the town of Southampton, the hamlet of Hampton Bays is bordered on the west by Flanders and East Quogue (and several ample county parks), and on the east by Shinnecock Hills. As its name suggests, the remainder of its boundaries are watery: the Peconic River, as well as numerous inlets, waterways, coves, and bays. Its beauty owes in part to its fragility: It was the New England Hurricane of 1938 that carved up the hamlet in this peculiar way, leaving the Shinnecock Inlet in its wake. That long and variegated coast grants commercial and casual fisherman plenty of access, and Hampton Bays is a thriving fishing port, second in the state behind Montauk. In terms of living here, the hamlet’s real estate is modestly priced compared to the better-known villages and hamlets in the Hamptons, but home values are rising, and the enclave is widely considered a shrewd investment.

history & culture Hampton Bays has played catch-up to the other, more popular Hamptons. In the 18th century, in a much smaller version, it was the dubious “star” of a sprinkling of hamlets that together made up Good Ground. The 11 hamlets were combined in 1922 and given the name Hampton Bays to appeal to the summer tourism trade. As with many places in the Hamptons, geography dictates, or at least inspires, the culture. Because Hampton Bays is blessed with so many protected bodies of water, it’s a haven for watersports and boating enthusiasts — there’s windsurfing, paddleboarding, and sailing aplenty.

And the hamlet’s spirit has a high-minded, crunchy flavor best represented by the Ecological Culture Initiative, a 501(c) (3) nonprofit that focuses on environmental stewardship, pedestrian-friendliness, eco-tourism, historical preservation, and other efforts that connect to the area’s original Good Ground moniker. The organization’s concurrent goal is to keep generic, suburban sprawl at bay (no pun intended).

dine & shop The most popular eateries are dotted along Montauk Highway, which runs east to west. Villa Paul, housed in a historic building, is beloved for its Italian menu; try the homemade ravioli with spinach and meat, or the veal Caprina with mozzarella and prosciutto in white wine sauce with capers. Then there’s 1 North, a classic steakhouse featuring surf-n-turf sliders and a 24-ounce porterhouse. And Cowfish boasts a gorgeous setting, Sunday brunch (French toast with three types of berries), sushi (try the Tumbleweed: spicy lobster and avocado), and Block Island swordfish for lunch. Also on Montauk Highway is the Hampton Bays Shopping Center (clothing), anchored by Macy’s. On the cooler side of the spectrum is the Hampton Music and Arts Shop, a full-service music store carrying new and vintage instruments and sheet music; the folks will also service your instrument.

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southampton

The elite village of Southampton shares its name with the town of Southampton, which also encompasses Quogue, Sagaponack, North Haven, and other tony villages, and more than a dozen posh hamlets, including Westhampton, Water Mill, Bridgehampton, and North Sea. (Hamptons terminology: Villages are incorporated; hamlets are not. Every village and hamlet in the Hamptons lies either in the town of Southampton or in the town of East Hampton, its neighbor to the east and north. That ends the geography lesson.) What Southampton village offers is a lesson on where the action is on Long Island’s southern fork. It is also the most developed and densely populated spot, as well as the most diverse. Therefore, Southampton is the most cosmopolitan place to buy a home in the Hamptons, and the village is arguably connected to the most illustrious names, including Ford, Vanderbilt, and Du Pont.

history & culture Named for an English earl and settled in 1640, Southampton takes pride in its long-recorded history. Accounts suggest that the early settlers enjoyed an amicable relationship with the Shinnecock Native Americans, who helped the Europeans settle. By the early 20th century, Southampton established itself as a premier summer resort and became a magnet for the superrich, über-powerful, and supremely successful, and the village boasts some of the most architecturally and historically significant (as well as the most expensive) estates in the country. Boldfaced names who have called the village home include Calvin Klein, Tory Burch, Ian Schrager, Brooke Shields, author Tom Wolfe, and legendary modern artist Roy Lichtenstein. Those culturally pedigreed names signal Southampton’s thriving cultural scene. Galleries abound, and the Southampton Cultural Center is a hub of visual and performing arts (including the Center Stage Theater), as well as educational opportunities.

dine & shop Southampton has a bustling Main Street for dining and retail therapy, with the Hamptons outpost of the chic Sant Ambroeus (its other elevated locales include Soho, the West Village, and Palm Beach), sending locals into rapturous praise for the crudo and the spaghetti alla chitarra. Snacking options are plentiful: Stop calorie-counting at the Village Gourmet Cheese Shoppe or the Fudge Company, and stock up on the toothsome craft creations from Tate’s Bake Shop (everything from chocolate chip pies to gluten-free bars). Back at home, those massive estates need lots of wall space to fill, so fortunately there’s the Tripoli Gallery and Arthur T. Kalaher Fine Art right in town, as well as the Mark Humphrey Gallery, which has exhibited such artists as Lichtenstein, Alex Katz, Donald Baechler, Helen Frankenthaler, and Ross Bleckner (the gallery is also your best bet for custom framing). And since this is one of the most Hamptons-ish Hamptons, yes, there is a J. Crew on Main Street.

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westha mpton beach

Shaped like an upside-down cork that’s been split at the fat end — that is, the wide coastal end — tiny, casual Westhampton Beach has lots of shoreline, and a population of around 2,000. Incorporated as a village in 1928, it’s located in the town of Southampton, with Westhampton to the east and Quiogue to the west. Of course, as its name would indicate, its key draws are the spectacular white strands along Dune Road. Cupsogue Beach County Park wins raves for its beauty, lack of crowds, and soft sands, while people looking for a non-party scene favor Pike’s Beach for the same reasons — and find the lack of vendors a blessing. Still others are attached to Roger’s Beach, noting its friendly lifeguard community, wooden benches, and snack bar. The prospective homeowner can do some serious bodysurfing from the prized sands off Dune Road and then find a noticeably democratic array of housing, from gorgeously imposing estates to condos to modest beach cottages.

history & culture The best place to learn about the history of the village is the Westhampton Beach Historical Society, which also serves the communities of Westhampton, Westhampton Dunes, Remsenburg, Quiogue, and Eastport. More than a single building, the campus consists of the historic Tuthill House Museum, the Foster-Meeker Heritage Center, the Meeker Carriage House and Privy, and the Thurston Raynor Milk House. The Foster-Meeker House, which is being restored, dates from 1735 and is considered the oldest house in Westhampton Beach. The event that most impacted the village’s story happened less than 100 years ago, when the Great New England Hurricane of 1938 destroyed homes, submerged the downtown, and carved the Shinnecock Inlet. On a happier note, the cultural venue that put Westhampton on the map in a different way is the Westhampton Beach Performing Arts Center, which dates from 1932 and hosts musical performers of all genres as well as standup comedy. The village also boasts the indie Hampton Arts Cinema.

dine & shop A cluster of eateries is located on and around Main Street between Mitchell Street and Beach Road. Included are such sources of comfort food as the Post Stop Café, with its pretty porch; Eckert’s Luncheonette, crowd-pleasing for its midcentury ambiance; and Beach Bakery Grand Café, which serves up a hearty breakfast and tasty pastries. Shock Ice Cream satisfies with its portions and is more inventive with flavors and presentations than it needs to be, since it has little competition in a laidback downtown. For sunsets and seafood, John Scott’s Surf Shack on Dune is the ticket. Like the dining scene, shopping options aren’t pretentious or particularly posh. But you’ll find a few jewelry stores, Impulse for men’s apparel, and on the distaff side, the Mint Clothing Boutique and the Lynn Stoller Collection, a consignment shop a stone’s throw from the local Corcoran office.

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sag harbor

Given its historical significance and unique position — it is located in both East Hampton and Southampton — Sag Harbor captures the soul and spirit of the Hamptons. Sag Harbor’s central business district (the whole of which earned a spot on the National Register of Historic Places) was so key to the whaling industry of the late 18th and 19th centuries that it scored a mention in Moby Dick. Thus the village became a magnet for merchants and entrepreneurs — and culture. A perfect place for the creative class centuries before the term existed, Sag Harbor has enjoyed a bustling commercial and artistic atmosphere since its founding. Such an environment has resulted in a year-round lifestyle. Between that and its irregular coastline, which allows many properties to boast water views, Sag Harbor (which also features the calm waters of familyfriendly Havens Beach) is one of the most desirable addresses in the Hamptons.

history & culture Settled in the early 1700s, Sag Harbor’s historical bona fides are many. It served as a stage for the American Revolutionary War, with one of its hills becoming a battleground that saw British casualties and the capture of 90 British soldiers. Long Island’s first custom house was built in Sag Harbor, and the harbor itself played a role in the War of 1812. And so on. As the first port of entry of the U.S., Sag Harbor emerged as a hotbed of social vitality and thriving interaction where various kinds of people — soldiers, seamen, merchants, and artistic types — freely mixed. John Steinbeck was perhaps the village’s most famous literary resident of the 20th century; novelist E.L. Doctorow (Ragtime) and Pulitzer Prize-winning playwright Lanford Wilson also lived here. Sag Harbor’s well-respected nonprofit Bay Street Theater, founded in 1991, continues to nurture the town’s arts-and-letters reputation, as do the readings at Canio’s Books, which has been around since 1980.

dine & shop No two ways about it: Sag Harbor has a thriving Main Street, and several dining venues come up again and again among the locals. Wölffer Kitchen bills itself and its sibling in Amagansett as “the first winery-owned restaurants on the East End,” and this spot has won devotees for its seasonal cuisine, community vibe, and selection of wines, ciders, and spirits. Page at 63 Main prides itself on local oysters and its sautéed veal piccata, as well as its more virtuous vegan vegetable grain bowl.

BLT chef Laurent Tourondel has the low-key LT Burger, and the Neapolitan pies at the year-old Sag Pizza have been greeted with open arms. With Sag Harbor known for charm and taste, it’s small wonder that Main Street has at least two homewares shops that win raves: Fishers Home Furnishings and In Home.

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montauk

Located at the very tip of the South Fork of Long Island, the nearly 20 square miles of Montauk represent the easternmost spot in New York state. As such, Montauk feels like the end of the earth. It’s a place of enviable natural beauty, including six state parks. With a narrower range of temperature variation than similarly situated towns, it experiences comparatively warm winters, and its recorded summer averages don’t crack the 80-degree mark. Praised for its beaches, which rank among the best in the Hamptons, the hamlet has been home to such famous denizens as Andy Warhol, musician Rufus Wainwright, and Pulitzer Prize-winning playwright Edward Albee. It’s an exclusive place, but with a vibe that’s more casual and closer to nature than the more westerly Hamptons. And in terms of scenic appeal, Montauk’s dunes and sunsets give it the biggest wow factor of all the towns of East Hampton.

history & culture George Washington, Amistad — and something called Leisurama. Historically speaking, Montauk has a lot of texture and pedigree, making its mark in each century of the nation’s history. Montauk Point Light, which stands as a symbol of that pedigree, was approved for construction in 1792 under President George Washington; as such, it was the first public works structure built by the new U.S. government (visitors welcome). Nearly 50 years later, slaves who had taken over the Spanish ship La Amistad briefly disembarked near Montauk Point. And in the 1960s, a slew of prefab homes branded Leisurama were plunked down in Montauk to represent the typical American house. These days, people come to Montauk for the same reasons they did midcentury: to kick off their shoes, take to the trails over the grassy dunes, fish either onshore or offshore, and head out on the water on a sailing charter or sunset cruise.

dine & shop Montauk is synonymous with fishing and sportfishing, and you would be smart to come here to savor the fruits of those labors that end up on your plate. Menu favorites include the local fluke and all manner of tuna poke and tartare (Crow’s Nest features both fish, as well as a Mediterranean-infused menu). Proximity to the coast of Maine means that lobster platters and lobster rolls are ubiquitous, from Duryea’s Lobster Deck and Red Hook Lobster Pound to a place that’s literally called The Lobster Roll Restaurant. At Bird on the Roof, you can shop and eat — the place is as popular for its beachwear as it is for its pancakes. Gosman’s Dock is another excellent place to mix dining and shopping: Have a waterside meal or frozen drink at Gosman’s Seafood Restaurant, Gosman’s Clam Bar, or Gosman’s Topside, then bust out your wallet at Homeport for gifts, accessories, and furniture.

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amagansett

Marilyn Monroe and Arthur Miller lived here. In the late 1950s, the most famous couple in America would escape to their small converted windmill home, where the famous playwright would write and the legendary actress would prepare for Some Like It Hot. Perhaps no other Long Island village or hamlet wears its mystique better than these 6.6 square miles in East Hampton dropped between the ultra-exclusive Maidstone Club and Montauk. After all, post-Marilyn and Miller, other residents of Amagansett have included the likes of Bill and Hillary Clinton, Paul McCartney, Jerry Seinfeld, and Billy Joel.

Further Lane, which unwinds through East Hampton and continues east into Amagansett parallel to the beach, is one of the best addresses in the Hamptons, with locals able to recite by heart the sale prices of various mansions — since the owners are often famous.

history & culture The earliest settlers — who never could have imagined that their rustic adopted home would become world-renowned — were English and Dutch descendants who found the area inhabited by the Montaukett. The rich history of the hamlet, which was established in 1680, is safeguarded by the Amagansett Historical Association, the grounds of which includes structures from the 18th and 19th centuries. With special emphasis on the period from 1725 to 1925, the association houses carriages, furnishings, letters, and early photographs. Also located in Amagansett is the East Hampton Historical Society, which looks after seven historical buildings, including a farmhouse dating from 1680, a preserved shingled house from 1720 on Main Street, and the East Hampton Town Marine Museum.

dine & shop Goods and services are plentiful on Montauk Highway/Main Street, which is abuzz with a few new restaurants that debuted for the 2019 season. Coche Comedor, from the same owners and executive chef as Nick and Tony’s in East Hampton, serves up tasty Mexican, while Morty’s Oyster Stand offers local and far-flung varieties, plus spicy poached shrimp and a $34 lobster roll. Sotto Sopra features Italian cuisine that’s a step above; the Northern Italian menu is courtesy of its Michelin-starred executive chef, Josh Salvi. Homeowners will become familiar with the Bayberry House & Garden Center, and sunbathers heading to Indian Wells Beach will want to stock up at Brent’s General Store and Amber Waves Farm.

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quogue

Surfers, literary folks, lovers of historic homes, and seekers of peace and quiet will find much to enjoy among the endless dunes and tall grasses of Quogue. There are fewer than 1,000 residents holed up in the 5 square miles of this high-status Southampton village. Locals cherish the legacy of Quogue’s literary cache, which includes midcentury legend Arthur Laurents, who wrote the books for the musicals West Side Story and Gypsy as well the screenplays for The Way We Were and The Turning Point. If it’s the time of life when you want to take a notepad to the dunes to pen the Great American Novel after you strip off your wetsuit, quiet Quogue just might be the perfect place.

history & culture Quogue has a long, sleepy history, dating from its 1659 purchase from the Montauk tribe. Coastal farmlands eventually gave way to a resort atmosphere, when shingle-style homes were erected by prominent families. Nearly 250 structures, built over the past several centuries, helped the Quogue Historic District land a spot on the National Register of Historic Places in 2016. Excitement comes in the form of tasty waves and nature pursuits: Though the East End of Long Island isn’t as identified with hanging ten as, say, the North Shore of Oahu, Quogue homeowners know that local and visiting surfers alike enthuse over one of the world’s best right-hand breaks. Though Quogue has been referred to as the un-Hamptons, it’s still a pretty exclusive place; it can take years to break in to the family-friendly Surf Club. The bald eagles, falcons, foxes, and owls of the Quogue Wildlife Preserve are less discerning; the 7 miles of trails are open 365 days a year.

dine & shop Membership is also tight at the Quogue Beach Club, but there’s always the refuge of the gorgeous and comfy Quogue Club at Hallock House, the 5-year-old inn designed by the beloved Alexa Hampton. With a wine list courtesy of sommelier Joseph Reinis and a farm-fresh menu by the inn’s founding executive chef, Matt Birnstill, Quogue residents may want to look into a membership after an overnight and dinner (dining is available to members and hotel guests). Far more casual is Beth’s Café, Quogue’s version of the country-cute spot that’s an essential go-to for any Hamptons town. Open for breakfast and lunch, this is the place to get your gluten-free pancakes or huevos rancheros on, or to wash down your crab cake sandwich with a Peanut Stallion smoothie. Given Quogue’s small size, locals spill over into East Quogue and Westhampton Beach to eat and browse, though the Quogue Shop is the closest resource for local gifts, menswear, totes, beach art, and even dog collars.

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sagaponack

One of the poshest villages in the Hamptons, Sagaponack is situated in the town of Southampton between Bridgehampton and Wainscott. The tiny, roughly triangular land mass checks in at only 4.7 square miles, yet it possesses some of the most valuable real estate in the nation; indeed, its ZIP Code routinely ranks as the costliest in America, so it’s not the place to look for a bargain. The roster of boldfaced names of current and former residents reads like the guest list of the country’s most exalted dinner party: Caroline Kennedy, Lloyd Blankfein, Truman Capote, Billy Joel, Kurt Vonnegut, Jimmy Fallon, cartoonist Charles Addams, actor Roy Scheider. Sagaponack’s Daniels Lane, which runs parallel to the coast (and Sagg Main Beach and Gibson Beach) just might be the priciest street in America. Sagaponack is indelibly connected, somewhat infamously, with billionaire Ira Rennert, who scandalized locals when he built arguably the biggest home in America; the main house alone (and there are other buildings) measures 66,000 square feet.

history & culture Sagaponack’s earliest settlers in the mid-17th century were potato farmers, and some of the estates of today’s billionaires were constructed on former potato farms. The Sagaponack Historic District, which nabbed a spot on the National Register of Historic Places, is a source of local pride — and participation. Fully 131 buildings and sites uphold the standard; they include the post office, 17th-century homes, 18th- century residences in the Federal and Greek Revival styles, plus bungalows and examples of the boxy, anti-Victorian Foursquare style that appeared after the turn of the 20th century. Most contributing buildings on the Historic District’s inventory be found on or near Main Street; for example, Kurt Vonnegut owned the home at 620 Main, which was built around 1740.

dine & shop Despite its coveted real estate, Sagaponack never really let go of its rural character. As in other Hamptons villages and hamlets, Montauk Highway represents the main commercial thoroughfare, though this stretch is sedate compared to the action in Sag Harbor, East Hampton, and Bridgehampton. Most of what you need can be found here and on Main Street, which runs perpendicular to Montauk Highway. Loaves & Fishes does prepared food well — blue fish salad, brownie pudding, along with shrimp, scallop, and feta stew. South of Loaves & Fishes is Pike Farms and the Sagaponack farmers market (cauliflower, beets, snap beans, berries). And Wölffer Estate Vineyard (entrance on Sagg Road) boasts several award-winning labels.

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WAT E R M I L L

Located in the town of Southampton and encircled by such well-known Hamptons names as Sagaponack, Bridgehampton, and the Southampton village, Water Mill oozes prestige and star power — in its low-key way. Its 12 square miles contain some of the costliest real estate in the country; Jennifer Lopez owns an estate here, and Richard Gere is a famous former resident. Geographically, Water Mill runs along a bit of Long Island’s southern shore (with some of the most soughtafter homes on Flying Point Beach), encircles Mecox Bay (with numerous watery fingers reaching into the hamlet in all directions), and meanders nearly to the North Shore.

history & culture An actual water mill was the hamlet’s raison d’être: The original 40 acres were designated for the mill in 1644. The two-story shingle-style water mill (purportedly the state’s first) was in operation for three centuries, and now serves as a museum (and selfie magnet). Water Mill is a scenic place where the land and the paintbrush have long coexisted. The hamlet boasts an impressive artistic pedigree, with the 34,400-square-foot Parrish Art Museum attesting to the area’s identity as a haven for painters. More than a century old, the museum has commanded this Herzog & de Meuron-designed facility since 2012. It contains more than 3,000 pieces, including a peerless collection of works by the American Impressionist William Merritt Chase (1849-1916). A more eclectic space is the Water Mill Center, which is devoted to collaborations between visual and performing artists, scientists, and anyone who wants to learn and explore. The venue offers meditation, tours, a library, and peaceful gardens.

dine & shop A stone’s throw away from the Parrish Art Museum is the family-owned Duck Walk Vineyards, with 30 acres of sauvignon blanc grapevines; and Hank’s Pumpkintown, which offers apple picking and pumpkin doughnuts. Dining go-tos include Calissa, featuring a Greek-influenced menu of mezze, grilled octopus, and branzino; and Bistro Ete, with its French coastal cuisine capped off by Foie Gras Fridays. Suki Zuki, serving sushi and robata grill dishes, is a hot spot. For coffee, quick bites, and takeout, locals and visitors on their way to the beach hit the Deli at Water Mill. And the Hampton Coffee Co., which features a coffee of the month, is particularly eco- and community-minded: In addition to offering beloved muffins and artisanal, small-batch Arabica coffee, this little family-owned business uses biodegradable cups and straws, ships with UPS Carbon Neutral, and employs (and will demonstrate) solar panels.

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