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Hamptons.com
October 13, 2025

An Elevated Enclave with Pool & Tennis

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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LOCAL EVENTS

Events

07
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07
Nov

Pizza & Pajama Night at Children’s Museum of the East End (CMEE)

November 7 @ 10:00 AM - November 7 @ 06:30 PM
376 Bridgehampton-Sag Harbor Turnpike, Bridgehampton, NY 11932
07
Nov
07
Nov
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07
Nov

Stretching for Seniors w/ Monica

November 7 @ 02:30 PM - November 7 @ 03:30 PM
One Ocean Yoga - 760 Montauk Highway (The Mill Center, above Goldberg's)
07
Nov
07
Nov
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07
Nov

Aperitivo – Sunset Cocktail Hour

November 7 @ 05:00 PM - November 7 @ 08:00 PM
The Baker House 1650
07
Nov
07
Nov
-
28
Nov

Sip a Stray Dog Martini at Calissa to Support Tyler’s Rescue From 11/7-11/28

November 7 @ 05:00 PM - November 28 @ 11:30 PM
Calissa Watermill - 1020 Montauk Hwy, Water Mill, NY 11976
07
Nov
07
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07
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Knowledge Friday with Bonnie Cannon

November 7 @ 06:00 PM - November 7 @ 07:30 PM
The Church, 48 Madison Street, Sag Harbor, NY 11963
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REVIEW: “Vanya and Sonia and Masha and Spike” Delivers Total Entertainment at the Southampton Cultural Center

REVIEW: "Vanya and Sonia and Masha and Spike" Delivers Total Entertainment at the Southampton Cultural Center

  • ✨ Top Hamptons Events This Weekend: November 7–9, 2025 ✨⁠
⁠
🍸 Sip a Stray Dog Martini at Calissa to Support Tyler’s Rescue⁠
📅 Fridays, Nov 7–28 | ⏰ 5pm–11:30pm⁠
📍 Calissa Hamptons, Water Mill⁠
Enjoy a Stray Dog Martini and support Tyler’s Rescue, a foster-based dog rescue in the Hamptons.⁠
🔗 Link in Bio⁠
⁠
🦅 Birds of Prey at Marders⁠
📅 Sat, Nov 8 | ⏰ 1–3pm⁠
📍 Marders, Bridgehampton⁠
Meet the rescue Birds of Prey from the Evelyn Alexander Wildlife Center!⁠
🔗 Link in Bio⁠
⁠
🍷 From Harvest to Harbor With Wölffer Estate Vineyard⁠
📅 Fri, Nov 7 | ⏰ 7–9pm⁠
📍 Le Bilboquet, Sag Harbor⁠
A five-course dinner paired with Wölffer Estate vintages hosted by Winemaker Roman Roth.⁠
🔗 Link in Bio⁠
⁠
🎨 Artisans’ Market: A Celebration of Craft and Creativity⁠
📅 Sat–Sun, Nov 8–9 | ⏰ 11am–4pm⁠
📍 The Remsenburg Academy⁠
Shop handcrafted jewelry, ceramics, stained glass, and more!⁠
🔗 Link in Bio⁠
⁠
🍽️ Long Island Restaurant Week: Fall Edition⁠
📅 Thurs–Sun, Nov 6–9 | ⏰ 12pm–12am⁠
📍 Various Restaurants⁠
Dine local and discover new favorites during Fall Restaurant Week!⁠
🔗 Link in Bio⁠
⁠
🎤 Bowie Station at The Stephen Talkhouse⁠
📅 Sat, Nov 8 | ⏰ 8pm⁠
📍 Amagansett⁠
Step back in time with the ultimate Bowie tribute band!⁠
🔗 Link in Bio⁠
⁠
🎭 The Met: Live In HD – La Bohéme⁠
📅 Sat, Nov 8 | ⏰ 1–5pm⁠
📍 Guild Hall, East Hampton⁠
Opera in the Hamptons—see the world’s most beloved opera on screen!⁠
🔗 Link in Bio⁠
⁠
📚 Author Talk with Lance Richardson⁠
📅 Sat, Nov 8 | ⏰ 3–4:30pm⁠
📍 East Hampton Library⁠
Hear about the making of Peter Matthiessen’s biography.⁠
🔗 Link in Bio⁠
⁠
🎷 Poetry and Jazz in Bridgehampton⁠
📅 Sat, Nov 8 | ⏰ 6:30–8pm⁠
📍 The Center, Bridgehampton⁠
An evening of poetry, music, and art with Alexis Pauline Gumbs.⁠
🔗 Link in Bio⁠
⁠
🥾 Montauk Point State Park Hike⁠
📅 Sat, Nov 8 | ⏰ 10am–12pm⁠
📍 Montauk Point State Park⁠
Take a relaxed, scenic hike through Montauk’s beautiful trails.⁠
🔗 Link in Bio⁠
⁠
🤠 Line Dancing in East Hampton⁠
📅 Sat, Nov 8 | ⏰ 6–9pm⁠
📍 The Clubhouse, East Hampton⁠
Grab your boots and get ready to line dance!⁠
🔗 Link in Bio⁠
⁠
#hamptons #weekend #hike #wolffer #restaurantweek #poetry #jazz #books #linedancing
  • Artists and brothers Steven and William Ladd brought their National Scrollathon to LongHouse Reserve on October 25th. The East Hampton community participated in art-making workshops, allowing their creativity to flow and producing a variety of pieces that will be assembled into a single, permanent artwork.⁠
⁠
The Scrollathon is a large-scale, inclusive, and ongoing project by the Ladd brothers, inspired by the ancient scroll as a form of communication. Using found and upcycled materials, participants engage with others as they create art objects that connect them both to their own experiences and to the wider world. Each participant makes one scroll to keep and one or more to contribute to the collective sculpture.⁠
⁠
@longhousereserve @stevenandwilliam⁠

📸: @jessicadalenephotography 
⁠
Check out the full gallery at Hamptons.com (Link in Bio)⁠
.⁠
.⁠
.⁠
.⁠
#nationalscrollathon #longhousereserve #hamptons
  • On Sunday, October 19th, the Tyler Valcich Memorial Classic Car Show returned to the Amagansett Firehouse (439 Main Street, Amagansett, NY) for a day filled with live music, raffles, vendors, awards, and train rides for kids.⁠
⁠
Participants were invited to drive, push, pull, or tow their car, boat, truck, or motorcycle to the event and enjoy a fun day admiring the impressive lineup of vehicles. The afternoon concluded with a car cruise to Montauk, a scenic parade of classic cars. Proceeds benefited The Tyler Project, an organization dedicated to raising awareness about mental health and cyberbullying through counseling, educational services, and community programs. @tylerprojectorg⁠
⁠
Check out the full gallery at Hamptons.com ⁠
⁠
📸: Photography by Richard Lewin⁠
⁠
#carshow #community #amagansett #tylerproject
  • A few minutes past Amagansett Village, in that quiet pocket between the ocean and the bay, the new estate built by Bluefin, 137 Cross Highway to Devon, has intrigued me since the moment I saw it — a rare combination of proximity to the Village, craftsmanship, and design integrity in one of the most desirable areas on the East End. ⁠
⁠
Real-savvy Hamptons people know that Amagansett North is a quiet kind of magic—close enough to feel the Village’s heartbeat, far enough to hear the birds. If you think 137 Cross Highway to Devon is out of the way, then you don’t know Amagansett.⁠
⁠
Four minutes to Amber Waves, under five to Balsam Farms and the Village, and less than ten to the ocean at Atlantic Avenue Beach.⁠
⁠
Location, of course, is the headline anyway. The essentials—farm stands, ocean and bay beaches, golf and racquet clubs, coffee, restaurants, provisions—are so close they become afterthoughts: grab greens at Balsam, seafood at Stuarts, swing back for a baguette at Amber Waves, be home before the ice melts. It’s the rare setup where everyday errands feel like part of the vacation.⁠
⁠
@romainehamptons @sarahminardire⁠
@hamptonsrealestate⁠
⁠
Read the full article at Hamptons.com (Link in Bio)⁠
⁠
#hamptonsrealestate #hamptons #amagansett
  • @paddlediva and @wychs_bloom inaugural Witches Paddle on Wednesday, October 29 at Paddle Diva was a huge success. 

A portion of the proceeds benefited the Surfrider Foundation’s Eastern Long Island Chapter. @surfridereasternlongisland 

#witches  #witchespaddle #halloween #paddleboarding #hamptons
  • Little Lucy’s 24th Annual Halloween Pet Parade pumpkin👻

#halloween #halloweencostume #petcostume #halloweenpetcostume #hamptons
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    • Shelter Island, South Ferry
    • Southampton, 39A to Montauk Hwy Merge
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