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Hamptons.com
May 23, 2026

An Elevated Enclave with Pool & Tennis

445
VIEWS
Hamptons.comby Hamptons.com
in Real Estate, Trending
Home Real Estate

2587 Deerfield Road, Sag Harbor, NY 11963
Saunders Exclusive: $4,495,000
View Listing

 

 

At the end of a long drive lined with beach grass, past the gated entry, this architecturally inspired Hamptons enclave reveals itself as a private, peaceful retreat. Designed for year-round luxury living and seamless entertaining, the property offers two distinct living and gathering spaces, 5 bedrooms, 6.5 baths, large gunite pool, tennis court, and an oversized 4-car garage. A central specimen tree anchors the front grounds, creating a sense of calm as the home rises gracefully among mature trees. 

Inside, the double-height entry foyer makes an immediate statement with floating stairs leading to the second level, while the first floor unfolds in bright, airy living spaces wrapped in floor-to-ceiling sliding glass doors. These open to the sunny poolside dining patio and multiple points of access to the manicured outdoor grounds.The sunken living room, anchored by a wood-burning fireplace, features three walls of glass that flood the space with natural light and frame serene views of the surrounding landscape.

A separate den/media room with pocket doors overlooks the tennis court and enjoys its own patio-perfect for private lounging or casual entertaining. At the home’s heart is a large eat-in kitchen with premium appliances, custom cabinetry, and a built-in service counter/bar. An adjoining dining area is ideal for hosting gatherings, while the mudroom/laundry room conveniently connects to an outdoor kitchen and a separate dining patio.

Outdoors, specimen trees and seasonal plantings bloom throughout the year. The poolside patio is bright, tranquil, and inviting, while a stone path meanders through lush grounds to the tennis court with half-court basketball. On the main second level, each ensuite bedroom boasts modern baths, soaring pitched ceilings, and clerestory windows that bring in abundant natural light and enhance the home’s passive-solar design.

Additionally, two of the bedrooms have private balconies. A glass-walled skybridge-a striking architectural feature-connects the main residence to a separate living and recreation wing above the garage.

Outfitted with dark hardwood floors, this area includes a media lounge and wet bar and is equally suited for entertaining or unwinding in style. Two well-sized bedrooms and the recreation wing open to a distinctive scalloped balcony, perfect for enjoying morning coffee or evening stargazing.

Below, the spacious 4-car garage provides ample storage for cars and watersport gear, along with a versatile home office or gym. Every space, inside and out, of this Hamptons retreat is imbued with inspiration and architectural verve, offering comfort, sophistication, and thoughtful details at every turn. Perfectly positioned in a quiet coastal community near picturesque bay beaches, restaurants in Noyac and elevated luxury in Sag Harbor Village, and the Hamptons’ famed oceanfront beyond. 

 


ELLIOT PEGG
Licensed Real Estate Salesperson
[email protected]
Cell: 631-644-6636

 


VINCENT HORCASITAS
Licensed Associate Real Estate Broker
[email protected]
Cell: (516) 768-7330

 

For more info, click here.

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TRENDING

The Hamptons’ biggest family event returns to the Children’s Museum of the East End (CMEE) as it hosts the 16th Annual Family Fair. This year’s theme—Endless Summer—promises a joyful morning filled with arts & crafts, water play, live entertainment, food trucks, candy, and more.

16th Annual Family Fair to Benefit CMEE Returns July 18

The Hamptons’ biggest family event returns to the Children’s Museum of the East End (CMEE) as it hosts the 16th Annual Family Fair. This year’s theme—Endless Summer—promises a joyful morning filled with arts & crafts, water play, live entertainment, food trucks, candy, and more.

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Over the past week, there were 25 Listings that went into contract from Westhampton to Montauk.




Compared to this same week last year (2025), there were 25 Listings that went into contract, which is NO CHANGE, year over year.




This same week in 2024, there were 30 Listings that went into contract.

Compared to this past week, there was a DECREASE of 17%.

Hamptons Real Estate Market Data – Week of 7/​7/2026

Over the past week, there were 25 Listings that went into contract from Westhampton to Montauk.

Compared to this same week last year (2025), there were 25 Listings that went into contract, which is NO CHANGE, year over year.

This same week in 2024, there were 30 Listings that went into contract.

Compared to this past week, there was a DECREASE of 17%.

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East Hampton Village and The Baker House 1650 share a similar story - a generational escape, shaped with respect, and elevated by modern comfort.




Every inch of the property is an homage to the timeless luxury of life in the Hamptons - an invitation to stillness. There is no gimmick or kitsch; it is simply a venerated space with an enviable vantage for experiencing East Hampton Village. Credit the state-of-the-art spa for why the boutique hotel looks so chic at age 376. The perfect destination to revitalize after a long day on the beach or night at the Talkhouse.

An Emblem of East Hampton Elegance, Baker House 1650

East Hampton Village and The Baker House 1650 share a similar story – a generational escape, shaped with respect, and elevated by modern comfort.

Every inch of the property is an homage to the timeless luxury of life in the Hamptons – an invitation to stillness. There is no gimmick or kitsch; it is simply a venerated space with an enviable vantage for experiencing East Hampton Village. Credit the state-of-the-art spa for why the boutique hotel looks so chic at age 376. The perfect destination to revitalize after a long day on the beach or night at the Talkhouse.

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Effortless Luxury, Elevated Living in Bridgehampton

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  • We visited Gigi’s at Gurneys to check out what’s on the menu this summer. Looking for fresh fish and lobster with sublime views of the ocean? Run, don’t walk.
@gigismontauk @gurneysresorts
  • Last week, Stacey Bendet held a stunning poolside celebration at her Watermill home, signaling the official start of the summer season. DJ Jordan Emanuel from Bravo’s Summer House kept the energy high while guests sipped on LALO cocktails and Wölffer’s iconic wines. Guests were treated to custom bikini charms by Dorne, lymphatic massages, games of beer pong, and a Farmers Daughter pop-up.⁠
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Check out the full gallery at Hamptons.com (Link in Bio)⁠
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#hamptons #aliceandolivia #summer #poolside
  • There are restaurants that simply serve a meal, and then there are restaurants that create an unbelievable memory and experience. Lulu Kitchen & Bar in Sag Harbor is the latter. I recently stopped in for lunch with my co-worker, Val, and from the moment we walked through the door, it was clear why this has become one of the Hamptons’ most celebrated dining destinations.

One of Lulu’s defining features is its commitment to wood-fired cooking. Nearly everything is prepared over a live fire using actual wooden logs, giving the food a distinctive depth of flavor that is difficult to replicate. You can actually see the flames working behind the scenes, adding to the experience.

Lulu also features a fantastic bar with an impressive selection of local craft beers alongside outstanding international offerings, making it just as appealing for an afternoon drink as it is for a full meal.
  • @fellinicoffee pop-up at the @themaidstonehotel serving delicious coffee Friday through Sunday ☕️

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From stunning contemporary pieces to unforgettable creative talent, this is a must-visit for any art lover. 
On view now through July 12. #fineart #art #artist #hamptons
  • Stopped by at @themontaukgeneral where we talked to the owner @kidiament about the stores best selling merchandise
#Matcha #montaukgeneralstore #hamptons
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    • Long Island Aquarium | Penguins
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