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Hamptons.com
June 7, 2023

4.5 Manicured Acres with a Primary Residence and 2 Cottages …Estate of a Lifetime

Anne Whiteby Anne White
in Real Estate, Trending
Home Real Estate
397 Sagg Main Street, Sagaponack, NY 11962

397 Sagg Main Street, Sagaponack, NY 11962
Saunders Exclusive: $18,900,000
View Listing

 

This extensive and exquisitely crafted multi-home estate is steeped in Sagaponack’s rich history and comes equipped with full approvals and plans from a renowned Hamptons designer. Originally named the Greenridge Cottage, this is truly a statement property epitomizing the Hamptons’ past, present, and future.

397 Sagg Main Street, Sagaponack, NY 11962

With generous acreage, there is ample room for expansion and tennis, and recent renovations have expertly expanded the property to offer 9 bedrooms across the 3 stunning structures-a handsome main home, a large guest home, and a guest cottage.

 

Listing broker John Healey notes that “There is no other property on the market today that encompasses this type of Estate-charm and feel, it is truly one of a kind.”

 

Originally constructed in 1899 by the renowned NY architectural firm of James E Ware & Sons for John G. Deshler’s family, one of the area’s earliest summer residents, this desirable estate is now available for only the second time in its long history.

397 Sagg Main Street, Sagaponack, NY 11962

As Healey explains, “This exemplary Sagaponack Village property should be at the top of any ‘legacy’ investment list one may have today. This Legacy-property will wrap your senses from a simpler time yet ground you to an estate of today.”

 

With 4.5 +/- bucolic acres, privately secluded on the iconic Sagg Main Street, this compound’s approach includes a teak-gated entrance leading to a half-circle driveway and a charming porte-cochère set in front of the house.

397 Sagg Main Street, Sagaponack, NY 11962

The estate boasts unparalleled charm and features a gambrel-roofed main home with a front foyer that leads to a sun-filled open living space complete with a wood-burning fireplace and views of a rolling green lawn bringing the outdoors in.

 

The first floor includes an eat-in kitchen with an open floor plan boasting premium appliances, custom cabinetry, and an inviting breakfast nook with built-in bench seating. Adjacent, a formal dining room is ready for elegant entertaining with convenient service from a rustic, Manhattan-style built-in bar and butler’s pantry.

397 Sagg Main Street, Sagaponack, NY 11962

The sunroom beams with light and open agricultural views from a striking wall of windows and opening to a large patio bookended by two magnificent mature Norwegian oaks.

 

A graceful staircase leads to the second floor, where the spacious en-suite primary bedroom and den feature a fireplace and fully renovated luxe bathroom. Additional bedrooms, a home office, artisan-crafted built-ins, walk-in closets, another fireplace, and a renovated bathroom complete the second floor. The third floor is highlighted by a white wood-paneled living space with two additional bedrooms and a bathroom.

397 Sagg Main Street, Sagaponack, NY 11962

The compound is surrounded by mature landscaping, complemented by a dining gazebo, covered patio, potting shed, cottage, and guest house. The gracefully appointed guest house is highlighted by a charming living room wrapped in built-ins and cathedral ceilings, plus 2 bright bedrooms and a full bath, kitchen, ample living space, fireplaces, patios overlooking the lush grounds, and an attached 2-car garage. The separate cozy guest cottage adds another bedroom, full bath, and attached studio space.

 

A gardener’s dream, the property is complete with an abundance of perennial flowers, manicured hydrangea beds, and a vegetable garden. The expansive estate is conveniently located near farm stands, Bridgehampton Village, and pristine ocean beaches. Ready for immediate move-in, you’ll have the opportunity to live in the luxurious guest home while expanding the main home. Honoring the home’s contribution to Hamptons history, designs by Michael Davis are an extension of the property’s character and charm, elegantly evolving the home into a masterclass of Hamptons luxurious lifestyle.

397 Sagg Main Street, Sagaponack, NY 11962

John Healey concludes “This legacy property will wrap your senses from a simpler time, yet ground you to an estate of today.”

 


JOHN A. HEALEY
Licensed Associate Real Estate Broker
[email protected]
Cell: (631) 774-8672

 

For more information, visit www.hamptonsrealestate.com

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LOCAL EVENTS

Events

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Aug
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Aug
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Aug

50th Annual Hampton Classic Horse Show

August 24 @ 08:00 AM - August 31 @ 05:00 PM
240 Snake Hollow Road Bridgehampton, NY 11932
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24
Aug
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Shinnecock Inlet Walk

August 24 @ 09:00 AM - August 24 @ 11:00 AM
Meet & park at ramp at North side of bridge closest to Coast Guard Station.
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Aug
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24
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50th Anniversary of Jaws Celebration in Montauk

August 24 @ 12:00 PM - August 24 @ 07:00 PM
Shark Bar Montauk - 2167 Montauk Hwy, Montauk, NY 11954
24
Aug
24
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Memories of Gosman’s Dock by The Help

August 24 @ 03:00 PM - August 24 @ 04:30 PM
Montauk Library 871 Montauk Hwy, Montauk NY 11954
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Charter Cruise! by Hamptons Hour x Easy Breeze for Wags & Walks

August 24 @ 03:00 PM - August 24 @ 05:00 PM
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Exhibit Opens with Live Art Performance at The White Room Gallery

Exhibit Opens with Live Art Performance at The White Room Gallery

  • @wagsandwalks @themontaukbeachhouse 

Puppies + Pilates + @montaukila = The Perfect Day

Check out our Events Calendar for more events! (link in bio)

#wagsandwalks #animaladoption #adoptdontshop❤️ #dog #montauk #montaukbeachhouse #montaukila #pilates
  • Check out the Top Hamptons Events This Weekend! ⁠
⁠
✨ 50th Annual Hampton Classic Horse Show⁠
📅 Sun, Aug 24 – Sun, Aug 31, 2025 | 8am–5pm⁠
📍 240 Snake Hollow Rd, Bridgehampton, NY⁠
🐴 One of the largest outdoor horse shows in the U.S., a premier summer destination for competitors & spectators.⁠
⁠
⁠
🎶 Apollo in the Hamptons⁠
📅 Fri, Aug 22, 2025 | 6pm⁠
📍 Si Si, 295 Three Mile Harbor Hog Creek Rd, East Hampton, NY⁠
Experience the essence of the legendary Apollo Theater with DJ Cassidy, Doug E. Fresh & more!⁠
⁠
⁠
🦈 50th Anniversary of JAWS Celebration – Montauk⁠
📅 Sun, Aug 24, 2025 | 12pm–7pm⁠
📍 Shark Bar Montauk, 2167 Montauk Hwy⁠
Screening, live music with Molly Scheider, themed cocktails, shark merch 🦈 — all to benefit Hayground School.⁠
⁠
⁠
😂 Chelsea Handler at WHBPAC⁠
📅 Fri, Aug 22, 2025 | 8pm⁠
📍 WHBPAC, 76 Main St, Westhampton Beach, NY⁠
A night of comedy with Chelsea Handler!⁠
⁠
⁠
🎵 The Knocks at Surf Lodge⁠
📅 Sat, Aug 23, 2025 | 4pm⁠
📍 The Surf Lodge, 183 Edgemere St, Montauk, NY⁠
The Knocks bring their signature groove to the Hamptons.⁠
⁠
⁠
🌅 Generation S.O.S – Live From Water Mill Fundraiser⁠
📅 Sun, Aug 24, 2025 | 5pm–8pm⁠
📍 Water Mill, NY⁠
Featuring Jason Biggs, Luke K, & MC Sophie Sumner.⁠
⁠
⁠
🇬🇷 Mykonos Nights at Calissa⁠
📅 Fri, Aug 22, 2025 | 10pm⁠
📍 Calissa, 1020 Montauk Hwy, Water Mill, NY⁠
End-of-summer vibes with DJs, drinks & dancing.⁠
⁠
⁠
👜🐶 Bark Jacobs by Marc Jacobs at The HUB⁠
📅 Sat, Aug 23, 2025 | 11am–7pm⁠
📍 The HUB, 2183 Montauk Hwy, Bridgehampton, NY⁠
Shop Marc Jacobs & get your pup’s portrait or initials hand-painted on your accessories.⁠
⁠
⁠
🐾 Wags & Walks’ Party Cruise⁠
📅 Sun, Aug 24, 2025 | 3pm–5pm⁠
📍 Easy Breeze Cruises, 462 W Lake Dr, Montauk, NY⁠
Cruise Montauk waters with cocktails & adoptable pups.⁠
⁠
⁠
🎨 5th Annual Celebrating Creatives of Color⁠
📅 Sat, Aug 23, 2025 | 11am–5pm⁠
📍 The Church, 48 Madison St, Sag Harbor, NY⁠
Showcasing artists & authors of color, with works available for sale.⁠
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Check out more events at Hamptons.com (Link in Bio)⁠
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#hamptons #weekend #hamptonsclassic #jaws #montauk #apollotheater⁠
  • The Southampton Animal Shelter Foundation held its “Sweet 16th” Unconditional Love Gala, a premier Hamptons event celebrating compassion, community, and animal welfare at a private estate in Bridgehampton. The Unconditional Love Gala is SASF’s largest fundraiser of the year, with proceeds directly supporting the shelter’s mission to provide care, rehabilitation, and forever homes for homeless animals. ⁠
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Check out the full gallery at Hamptons.com (Link in Bio)⁠
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#animalshelter ⁠
#fundraiser #hamptons #southampton
  • Make sure you check out the sunset music series before the end of August. For more info on dates and times check out the Wölffer website.

#sumsetmusic #winestand #wölffer #rosé
  • Hilary Matt Interiors is a residential design firm started and located in New York City with projects spanning across the country, including in the Hamptons and East End.⁠
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Hilary, principal and founder, is known for a bold aesthetic that is comfortable and livable. She always keeps her clients at the forefront so they can express themselves as individuals through their spaces. After starting out in the fashion industry, Hilary felt a call to interior design where she has been bringing her unique approach and style to every space as the brand continues to grow.⁠
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Hilary spoke more about her background, how each HMI project differs from one another, and why the Hamptons is such a special place to her. She also shared her top 5 interior design tips as inspiration.⁠
⁠
Can you discuss your background and how you got started with interior design?⁠
⁠
HM: I studied business and apparel merchandising. After graduating, my first job was at a women’s contemporary showroom in NYC. I had always loved fashion and wanted to be in the industry. After a year, I realized it wasn’t quite what I expected. I had always been interested in interior design, so I took a leap of faith and accepted a job as an assistant to an interior designer. I was initially nervous to leave fashion, but I figured I could always return. I ended up loving it and worked with her for eight years, learning the ins and outs of the business. I also took classes on weekends and evenings to learn computer programs, scaling, and other essential skills. After leaving that position and having my first son, I started my own company, which has snowballed into what we are today.⁠
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Read the full interview at Hamptons.com (Link in Bio)⁠
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#hilarymatt ⁠
#hilarymattinteriors ⁠
#hamptons ⁠
#interiordesigner⁠
#hamptons lifestyle⁠
#interiorstyling⁠
#design
  • Comedian Des Bishop took the stage at Westhampton Beach Performing Arts Center this week and delivered laugh after laugh. A native New Yorker, Des moved to Ireland in his teenage years, which ultimately inspired his start in comedy and a successful career that has spanned three decades.⁠
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His comedy is full of observational humor and nostalgia, whether it be about his many cross-cultural experiences, an ever-changing societal landscape, and his own personal stories growing up. Des brings energy and a unique perspective to every show, evident at his Westhampton show, the place he has spent all his summers since the 90s.⁠
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Des spoke more about his background, how his experiences have shaped his approach to comedy, his connection with the East End, and his WHBPAC show.⁠
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Can you tell us a bit about your background and how you first got into comedy?⁠
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DB: Well, my background is a little complicated, but the quick version is I grew up in Queens, flunked out of St. Francis Prep at 14, and ended up going to Ireland to boarding school in 1990. It was a crazy, life-changing experience, but it definitely saved my education and ultimately inspired a comedy career that in the early days focused a lot on being an outsider looking in. It’s hard to know if I ever would have tried stand-up if I hadn’t been in Ireland. I got sober at 19 and it was a comedian I knew from that world that pushed me to try stand up. Once I got on stage that was all she wrote. I was addicted.⁠
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Read the full interview at Hamptons.com (Link in Bio)⁠
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#desbishop #comedy #westhampton #whbpac
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