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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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Yizkor Memorial Service

October 14 @ 11:00 AM - October 14 @ 01:00 PM
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October 14 @ 03:30 PM - October 14 @ 05:30 PM
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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

  • Sag Harbor resident, actor, writer, and teacher Josh Pais has spent decades exploring what it means to be fully present—on screen and in life. Known for his roles in Joker, Ray Donovan, the original Teenage Mutant Ninja Turtles, and many others, he has more than 150 film and television credits to his name. He has now turned his focus inward with his new memoir, Lose Your Mind: The Path to Creative Invincibility, which was released on September 30, 2025.⁠
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Drawing on his years of experience as founder of the Committed Impulse training method, Josh offers readers a bold invitation to release self-judgment, lean into all feelings, and connect with the spontaneous energy that fuels authentic creativity. His message—both playful and profound—challenges the myth of “good” and “bad” emotions and instead celebrates the full spectrum of human experience.⁠
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Josh will visit Sag Harbor for a reading and book signing this Sunday, October 12th from 4:00–5:30 p.m. at Grenning Gallery (26 Main Street, Sag Harbor). ⁠
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📸: Commune Media⁠
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Read the full interview at Hamptons.com (Link in Bio)⁠
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#hamptons #joshpais #book #sagharbor #author #actor
  • @linamxn at the Sag Harbor Music Festival! @sagharbormusic 

The four day festival kept the music going over 4 days at various stages in Sag Harbor. 

#sagharbormusicfestival #sagharbor #hamptons #livemusic #linamaxine #local
  • Grab your furry friend and take a stroll to Main Beach with ARF!

Check out the Top Hamptons Events This Weekend!

🐾 ARF’s Stroll to the Sea Dog Walk
📅 When: Saturday, October 11, 2025 | 9AM–12PM
📍 Where: Mulford Farm, 10 James Lane, East Hampton, NY

Enjoy vendors, contests, and giveaways before strolling to Main Beach.

🥣 Chowdah Chowdown
📅 When: Saturday, October 11, 2025 | 12PM–3PM
📍 Where: Springs Tavern and Grill, 15 Fort Pond Blvd, East Hampton, NY

All-you-can-eat chowder and soup from 20 local chefs, plus live music and a mocktail bar — all to benefit the Springs Food Pantry!

🍺 SagtoberFest
📅 When: Sat, Oct 11 – Sun, Oct 12, 2025 | 12PM–8PM
📍 Where: Kidd Squid, 11 Spring St, Sag Harbor, NY

Celebrate Oktoberfest Sag Harbor–style! Enjoy bratwurst, pretzels, oysters, pumpkin stew, and live music by Jon Divello, Woody Boley, Greg McMullen & Jake Lear.

🎬 33rd Hamptons International Film Festival
📅 When: Thurs, Oct 9 – Mon, Oct 13, 2025 | 9AM–10PM
📍 Where: Various Locations

The 33rd edition of HIFF brings a world-class lineup of narrative and documentary films, features, and shorts from around the globe. 

🍪 Levain Bakery: Book Talk & Signing
📅 When: Saturday, October 11, 2025 | 12PM–1PM
📍 Where: BookHampton, 41 Main Street, East Hampton, NY

Meet Levain Bakery cofounders Pam Weekes & Connie McDonald and grab their new book.

🌿 26th Annual Long Pond Greenbelt Celebration
📅 When: Saturday, October 11, 2025 | 10AM–1PM
📍 Where: SOFO Museum, 377 Bridgehampton–Sag Harbor Tpk, Bridgehampton, NY

Enjoy games, crafts, guided walks, face painting, and ice cream!

🎉 CMEE’s Big Birthday Bash!
📅 When: Saturday, October 11, 2025 | 10AM–12PM
📍 Where: SOFO, 376 Bridgehampton–Sag Harbor Tpk, Bridgehampton, NY

Join for crafts, treats, dance, and play!

🛋️ Hub Home Grand Opening Party & Open House
📅 When: Friday, October 10, 2025 | 6PM–9PM
📍 Where: HUB Home, 2183 Montauk Hwy, Bridgehampton, NY

Celebrate the grand opening of HUB Home, a curated consignment shop with luxury furnishings, art, and décor.

Check out more events at Hamptons.com (Link in Bio)
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#hamptons #arf #community #stephentalkhouse #dining #hamptonsfilmfestival
  • The 33rd Hamptons International Film Festival kicked off last Friday with the U.S. premiere of A24’s Eternity starring Elizabeth Olsen, Miles Teller, and Callum Turner.⁠
⁠
Elizabeth Olsen attended the premiere on Friday, and on Saturday sat down with IndieWire’s Editorial Director Kate Erbland at the Sag Harbor Cinema as a part of the festival’s “A Conversation With” series. Later that day, the second “A Conversation With” took place as Ethan Hawke and moderator Alison Stewart talked about Blue Moon, as well as Hawke’s filmography. ⁠
⁠
Sydney Sweeney received the festival’s Achievement in Acting Award following the U.S. premiere of her film Christy in East Hampton. ⁠
⁠
Notable Guests included: Alessandro Nivola, Alec Baldwin, Amanda Peet, Tonatiuh, Miriam Shor, Lois Smith, Tim Blake Nelson, Mareille Enos, Bob Balaban, E. Jean Carroll, Roberta Kaplan, Ellen Barkin, Bernie Telsie, Bill Condon.⁠
⁠
📸: Jess Dalene⁠
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Check out the full gallery at Hamptons.com (Link in Bio)⁠
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#hiff #hamptonsinternationalfilmfestival #film #elizabetholsen #sydneysweeney #hamptons #hamptonsfilm⁠
  • When: Fri, Oct 3rd – Sun, Oct 5th, 2025
8am – 5pm

Where: Levain Bakery, 354 Montauk Hwy, Wainscott, NY

Levain Bakery is introducing a new cookie for a limited time: Peanut Butter Dark Chocolate Chip – a decadent mix of creamy and chunky peanut butter with rich dark chocolate chunks. Originally created to celebrate the opening of Levain’s Beverly Hills Bakery, this indulgent new flavor will now be available for just three days only, October 3–5, at all retail bakery locations.

To make the weekend even sweeter, guests who purchase a cookie will receive a Levain Bakery mini tote (while supplies last), a fan-favorite collectible sure to go quickly.

#levain #levainbakery #cookie #minitote #tote #hamptons
  • From world premieres at the Hamptons International Film Festival to SouthamptonFest! ⁠
⁠
Check out the Top Hamptons Events This Weekend!⁠
⁠
🎬 33rd Hamptons International Film Festival⁠
📅 Oct 3 – 13, 2025 | 9AM – 10PM⁠
📍 Various Locations⁠
A global lineup of films, shorts & documentaries.⁠
⁠
🍪 Levain Bakery⁠
📅 Oct 3 – 5, 2025 | 8AM – 5PM⁠
📍 354 Montauk Hwy, Wainscott⁠
Try the Peanut Butter Dark Chocolate Chip cookie + snag a mini tote (while supplies last).⁠
⁠
🎉 13th Annual SouthamptonFest⁠
📅 Oct 3 – 5, 2025 | 10AM – 7PM⁠
📍 Southampton Village⁠
Arts, culture, food & family fun all weekend long!⁠
⁠
🎶 SpringsFest⁠
📅 Oct 4, 2025⁠
📍 1 Parsons Pl, East Hampton⁠
Live music, raffles, crafts, blacksmith demos & more.⁠
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💃 Salsa Social @ The Clubhouse Hamptons⁠
📅 Oct 4, 2025 | 9PM – 11:30PM⁠
📍 East Hampton⁠
Dance the night away w/ DJ Chile & more!⁠
⁠
🐚 34th Annual Largest Clam Contest⁠
📅 Oct 5, 2025 | 12PM – 3PM⁠
📍 Amagansett Life Saving Station⁠
Taste clam chowder, clam pies & cheer on the winners!⁠
⁠
🎷 East Meets West Jazz Jam Session⁠
📅 Oct 5, 2025 | 2PM – 5PM⁠
📍 Southampton Cultural Center⁠
Free community jazz jam – all are welcome.⁠
⁠
🌕 Full Hunter’s Super Moon Hike⁠
📅 Oct 6, 2025 | 6:30PM – 7:30PM⁠
📍 SOFO Museum Parking Lot⁠
Guided evening hike under the moonlight.⁠
⁠
✨ Which event are you most excited for?⁠
⁠
Check out more events at Hamptons.com (Link in Bio)⁠
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#hamptons #hamptonsinternationalfilfestival #hiff #jazz #fullmoon #hike #film #levainbakery #community
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