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Hamptons.com
December 7, 2021

Historic Shelter Island Waterfront Farmhouse on 22.95 Acres

David Lion Rattinerby David Lion Rattiner
in Real Estate
Home Real Estate
81-82 South Midway Road, Shelter Island, NY 11964

 

81-82 South Midway Road, Shelter Island, NY 11964
Saunders Exclusive: $14,995,000

 

When it comes to Hamptons real estate, it’s all about the land. You simply cannot find better dirt anywhere in the world than the land that exists on the East End. Typically, if you are looking to buy a property out here, anything over an acre is considered a lot, but Penelope Moore has a listing located at 81-82 South Midway Road on Shelter Island, that consists of a tremendous 22.95 acres in a setting that is so magical and so historical, it’s hard to believe.

 

81-82 South Midway Road, Shelter Island, NY 11964

 

“It’s all really, really fascinating in terms of its history,” Penelope explains. “In 1698, George Havens came to Shelter Island and bought one thousand acres from Nathanial Sylvester II whose father claimed ownership of Shelter Island. This property was part of those thousand acres. Over the last 271 years there have only been two other families there, the Tuthills and the Robbs who are its current owners.”

 

The pre-Revolutionary War, wood shingled colonial which was built circa 1750 is named “Kemah”, a Shinnecock word meaning “in the face of the wind” because of its prevailing southwest breezes. With two separate waterfront lots, there are 17.35 elevated acres with 385 +/- feet on Great Fresh Pond to the north side, and over 5.6 acres of meadow with 596 +/- feet on Peconic Bay looking south toward Bridgehampton.

 

Obadiah Havens, who was a member of the Provincial Government and 1st Lieutenant of the Militia during the Revolutionary War, once lived at Kemah. During the British occupation of Shelter Island and the East End, Obadiah fled to Connecticut to continue his work as a Patriot from there.

 

“Kemah was vital to Native Americans who accessed fresh drinking water on Fresh Pond,” Moore said. “From where Midway Road is now, they graded and then constructed a large berm, which is still visible today, to protect the freshwater from saltwater intrusion. They also dug a channel where canoes were kept hidden from other tribes.”

 

The patriarch of the family who currently owns the property, John Donald Robb was a “true renaissance man.” Moore said, “He bought Kemah during the Great Depression while his wife was on a cruise. From the 1930s through the 1950s, Robb traveled throughout the world interviewing and recording the chants of indigenous people. The 3000 plus field recordings are now in an archive bearing his name at the University of New Mexico. Without his keen interest, the songs he recorded would have been forever lost.” Also a composer, Robb’s music studio, affectionately called “the chicken coop” is still there on the property. “He and his wife Hattie thrived at Kemah,” Moore said, “they had thirty sheep that grazed in the fields. He shorn their wool, dyed it with pigments from fruit and berries on the property, then wove blankets and sweaters using the spinning wheels that are still in the house.”

 

It is the ultimate historic house on an incredible amount of land

 

The two-story barn built in 1886, where the sheep were housed, is magnificent and completely unique to Shelter Island. It has thick wooden plank floors with large beams that run up to two lofts with doors on all sides of the structure. “If someone wanted to build a main house from the barn, they could create something spectacular,” Moore said.

 

Some homes say that they are historic, but on Shelter Island, the history is brought to a whole other level. It is the ultimate historic estate on an incredible amount of land. Penelope goes on to explain, “In many ways the property is like a mini version of Sylvester Manor, it’s just so magical. When you walk the property today, because the foliage has dropped with the winter and there are no leaves on the trees, you can really see the contours and what you are getting with the land. Few properties epitomize the history of the East End of Long Island the way that Kemah does,” Moore said. “When you walk through the grounds, in the barn and in the home, and then gaze out onto the water, there is a real sense that this land has seen countless historic events and great people over its nearly 300 years.”

 

81-82 South Midway Road, Shelter Island, NY 11964

 

This is a must-see property. It is just an unbelievable amount of land to own, it’s truly your own fairy tale world on Shelter Island.

 

PENELOPE A. MOORE
Licensed Associate Real Estate Broker
[email protected]
Cell: (917) 208-5519

 

For more information, visit www.hamptonsrealestate.com.

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Bay Street Theater: The Beatles’ White Album Live! With the Moondogs

Bay Street Theater: The Beatles’ White Album Live! With the Moondogs

  • 🎄 This Weekend in the Hamptons 🎶✨⁠
⁠
🎷 Hamptons JazzFest Presents: NYC Spirits⁠
📅 Fri, Dec 19 | ⏰ 6:30–9pm⁠
📍 Masonic Temple, Sag Harbor⁠
An evening of world-class jazz⁠
⁠
🎻 Candlelight: Christmas Carols on Strings⁠
📅 Sat, Dec 20 | ⏰ 6–7pm⁠
📍 Guild Hall, East Hampton⁠
A magical concert where music and visuals meet⁠
⁠
🍷 Winter Wonderland at Wölffer Estate Vineyard⁠
📅 Sun, Dec 21 | ⏰ 11am–2pm⁠
📍 Sagaponack⁠
Festive drinks, cozy firepits & family fun⁠
⁠
🕎 Pop-Up Chanukah: Eitan Levine⁠
📅 Sun, Dec 21 | ⏰ 5–7pm⁠
📍 Guild Hall, East Hampton⁠
Comedy, community & a menorah lighting⁠
⁠
🚂 The Polar Express⁠
📅 Sat, Dec 20 – Sun, Dec 21⁠
📍 Southampton Playhouse⁠
A holiday classic on the big screen⁠
⁠
❄️ Igloos by the Sea at Gurney’s⁠
📅 Fri, Dec 19 – Mon, Dec 20 | ⏰ 5pm & 7pm⁠
📍 Montauk⁠
Heated oceanfront igloos with festive bites & cocktails⁠
⁠
📚 Light, Sand and Sea Book Signing⁠
📅 Sat, Dec 20 | ⏰ 5–8pm⁠
📍 Baker House 1650, East Hampton⁠
A Hamptons-centered book celebrating local artists⁠
⁠
🎶 Consonance Music Ensemble at Marders⁠
📅 Sat, Dec 20 | ⏰ 1–3pm⁠
📍 Bridgehampton⁠
Holiday shopping with live music⁠
⁠
👉 Click the link in bio for more events⁠
⁠
#hamptons #guildhall #holidays #hanukkah #booksigning igloos livemusic winterwonderland wolffer
  • The Southampton Playhouse, located at 43 Hill Street in Southampton, has quickly reestablished itself as one of the East End’s most vibrant cultural spaces. After an extensive renovation and a reimagining of its mission, the beloved historic theater is once again bringing people together through film, conversation, and community.⁠
⁠
Under the leadership of Executive Director Maria A. Ruiz Botsacos and Artistic Director Eric Kohn, the Playhouse has evolved into a dynamic hybrid of state-of-the-art cinema and community arts hub—offering everything from IMAX blockbusters and 35mm classics to live performances, themed series, and exclusive talks with filmmakers.⁠
⁠
Read the full interview at Hamptons.com (Link in Bio)⁠
.⁠
.⁠
.⁠
.⁠
#southampton #southamptonplayhouse #hamptons #film
  • On Saturday, December 13th @heartofthehamptons held their annual Polar Bear Plunge at Coopers beach in Southampton. 

The whole community came together for treats and plunged for a great cause ❄️

#polarbearplunge #coopersbeach #southampton #heartofthehamptons
  • HamptonsFilm announced that the 34th annual edition of the Hamptons International Film Festival will take place October 2-12, 2026. The 11-day festival will feature screenings and events across the Hamptons.⁠
⁠
HamptonsFilm announced that the 34th annual edition of the Hamptons International Film Festival will take place October 2-12, 2026. The 11-day festival will feature screenings and events across the Hamptons.⁠
⁠
The festival will begin accepting submissions via FilmFreeway in February. ⁠
⁠
“As we look ahead to the 34th edition of the Hamptons International Film Festival, we’re excited to continue to bring audiences eleven days of screenings and events across the East End,” said David Nugent, Chief Creative Officer of HamptonsFilm. “Each year, our filmmakers and audiences inspire us to grow, experiment, and celebrate bold new voices in cinema. With submissions opening in February and an exciting slate of year-round programs, from our Screenwriters Lab to SummerDocs and our beloved outdoor screenings, we can’t wait to welcome everyone back this October.”⁠
⁠
⁠
Read the full article at Hamptons.com (Link in Bio)

#hamptonsfilm #filmfestival
  • Check out the Top Hamptons Events This Weekend!

Hampton Ballet Theatre School’s 16th Annual Nutcracker at Guild Hall
When: Fri, Dec 12 – Sun, Dec 14, 2025 • 7pm, 12pm & 5pm
Where: Guild Hall, 158 Main Street, East Hampton, NY
Get into the holiday season with a timeless ballet!

Polar Bear Plunge in Southampton
When: Sat, Dec 13, 2025 • 9am–11am
Where: Coopers Beach, 268 Meadow Lane, Southampton, NY
Celebrate 22 years of getting freezing for a reason! 

Holiday Tour of the Inns
When: Sat, Dec 13, 2025 • 1pm–4pm
Where: East Hampton, NY
Enjoy festive décor and treats across East Hampton’s charming inns.

A Holiday Moment in The Hamptons
When: Sat, Dec 13, 2025 • 2pm–6pm
Where: 26 Montauk Highway, Amagansett, NY
Walk through the evergreens and enjoy cocoa, cider & treats benefiting the Eleanor Whitmore Early Childhood Center.

Amagansett Life-Saving Station’s 3rd Annual Tree Lighting & Toy Drive
When: Sat, Dec 13, 2025 • 4pm–5:30pm
Where: 160 Atlantic Ave, Amagansett, NY
Arts & crafts, cookies, hot chocolate, music — and bring an unwrapped gift for the Kiwanis Toy Drive!

A Christmas Carol: A Live Radio Play — Hampton Theatre Company
When: Fri, Dec 12 – Sun, Dec 14, 2025 • 7pm & 2:30pm
Where: Quogue Community Hall, 125 Jessup Ave, Quogue, NY
A festive classic returns for one weekend only!

Pop-Up Chanukah at Herrick Park
When: Sun, Dec 14, 2025 • 4pm–6pm
Where: Herrick Park, 67 Newtown Ln, East Hampton, NY
Celebrate with songs, donuts, gifts for kids, a dreidel drop & the lighting of the public menorah.

Breakfast with Santa at The Hampton Maid
When: Sun, Dec 14, 2025 • 8am–1pm
Where: 259 E Montauk Hwy, Hampton Bays, NY

Montauk Holiday Concert
When: Sun, Dec 14, 2025 • 3pm & 4pm
Where: Saint Therese of Lisieux, 67 S Essex St, Montauk, NY
Enjoy holiday classics!

Santa Selfies with Birds of Prey
When: Sat, Dec 13, 2025 • 1pm–3pm
Where: Marders, 120 Snake Hollow Rd, Bridgehampton, NY
Meet rescue birds from the Evelyn Alexander Wildlife Center!

Gifts & Carols at the Nathaniel Rogers House
When: Sat, Dec 13, 2025 • 4pm–6pm
Where: 2539 Montauk Hwy, Bridgehampton, NY
Sing along with the Dickens Carolers!

For all event details, see the link in bio. 

#hamptons
  • Saunders & Associates once again demonstrated its commitment to the East End community with the 12th Annual Thanksgiving Donation Drive, which this year reached a record-breaking milestone. ⁠
⁠
Coinciding with Giving Tuesday, the campaign raised an impressive $62,000 for Hamptons food pantries—making it the most successful drive to date and significantly expanding support for local families during the holiday season.⁠
⁠
As the Hamptons’ leading real estate brokerage, Saunders & Associates’ annual Thanksgiving Donation Drive underscores the firm’s longstanding commitment to supporting the Hamptons community all year long.⁠
⁠
Read the full article at Hamptons.com (Link in Bio)⁠
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#hamptons #saunders #community #foodpantries
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