Top 10 Most Expensive Home Sales of 2021

We’ve told you about the most expensive sales on both the South Fork and the North Fork, now let’s take a look at the biggest sales on Shelter Island in 2021.

The 16,000 square foot home at 10 Lari Lane on Shelter Island overlooks Coecles Harbor.Brian Bailey for Gary DePersia/Corcoran

1) 10 Lari Lane, Shelter Island | $11.575 million

A single sale on Shelter Island exceeded $10 million. This gated waterfront resort on 3.25 acres boasts 325 feet of Coecles Harbor. The 16,000 square foot home overlooks a private dock and private beach was designed by famed architect Val Florio, as well as a three-car shed, two-story pool house, and heated infinity gunite pool with spa raised . Corcoran’s brokers handled both sides of the deal. Gary DePersia listed the home in April 2021 for $2.5 million less than previously offered with another agency. Susan Breitenbach brought in the buyer, which closed in September.

Known as the Four Seasons, the home at 7 Apple Orchard Lane was the second highest sale of 2021.

2) 7 Apple Orchard Lane, Shelter Island | $9.1 million

Known as the Four Seas, the 1.5-acre property in Shorewood looks west across Peconic Bay and offers 150 feet of private beach. The classic 10,000-square-foot gambrel-style home, built by late Hamptons builder Ben Krupinski, sold in March. There is also a 50 foot waterfront heated gunite pool and framed hot tub and a 150 foot private dock. Corcoran’s Peter McCracken and Gary DePersia had the list, last asking for $9.95 million. Penelope Moore of Saunders & Associates brought in the buyer.

This Tudor style home in Dering Harbor has been exclusively listed by Dering Harbor Real Estate.Courtesy of Dering Harbor Real Estate

3) 16 Harbor Lane, Dering Harbor | $6.5 million

The only home in the tiny village of Dering Harbor to make the list, this 3,800 square foot home overlooks the harbor. It is a little known address on the small island. The saleswoman, Martha Baker, former fashion director at New York magazine, fought to get a permit for a conservatory in the 1990s while fixing up the old Tudor house, all the way to the Supreme Court. Now a landscaper and author, she’s parted ways with the well-appointed home, which sits on a 0.72-acre lot that includes 125 feet of beach frontage, a deep-water dock, a large back lawn with room for a swimming pool, as well as a detached garage for two cars. It was offered exclusively by John Catrambone at Dering Harbor Real Estate at $6.3 million and he sold it for another $200,000 on November 3.

The CeeJack team at Compass listed 40B Stearn’s Point Road in May and its buyer closed in November.Courtesy of Compass

4) 40B Stearn’s Point Road, Shelter Island Heights | $6 million

A one-of-a-kind centerpiece with breathtaking views, this home also includes access to Crescent Beach and a shared dock. The 5,800 square foot home is perched atop the cliffs on 3.87 acres with a “modern and vintage” vibe, according to the listing. It features original 1920s woodwork, while famed architect/designer Michael Haverland reimagined the home by adding a modern wing with a luxury master suite and maximizing multi-level views. The home was listed with the Cee Scott Brown and Jack Pearson of the CeeJack team at Compass for 6.75 million in May. They also replaced the buyer, which closed on November 1.

The large home at 189A Ram Island Drive overlooks a pool and Gardiner’s Bay.Courtesy of Daniel Gale Sotheby’s International Realty

5) 189 Ram Island Drive, Shelter Island | $4.995 million

This 5,500 square foot custom built home at the end of Ram Island Drive offers stunning views of Gardiner’s Bay. The 1.3-acre property also delights with a gunite pool, manicured gardens, 122 feet of sandy beach, and a separate guest suite above the independent two-car garage. It was traded in March and Daniel Gale Sotheby’s International Realty represented both sides of the listing. Collapse

The property located at 30 Little Ram Island Drive offers a 70 foot long dock in Coecles Harbor.Courtesy of Dering Harbor Real Estate

6) 30 Little Ram Island Drive, Shelter Island | $4.9 million and
15 Montclair Ave, Shelter Island Heights | $4.9 million

Tied for fifth place are two addresses, one on Coecles Harbor and one on West Neck Harbor. The house at 30 Little Ram Island Drive is a traditional clapboard house that sits on 1.82 acres with frontage on Coecles Harbour. The property offers 185 feet of shoreline and the 3,783 square foot home enjoys water views from almost every room. There is also a tennis court, a swimming pool, a guest house and a 70 foot long dock. Penelope Moore of Saunders & Associates had co-exclusivity with John Catrambone of Dering Harbor Real Estate, with the latter bringing the buyer to close on April 21.

The house at 15, avenue Montclair, an open list, sold in November.Courtesy of Douglas Elliman

As for 15 Montclair Avenue, a 4,900-square-foot cobblestone Gambrel-style home sits on half an acre with 200 feet of loose waterfront, stairs to a private beach, and a private dock. An open listing, Corcoran’s Margot Reutter represented the buyer and Georgiana B. Ketcham Real Estate also received credit when the property sold on Nov. 15.

Courtesy of Daniel Gale Sotheby’s International Realty

7) 1 Wheeler Road, Shelter Island Heights | $4.7 million

This estate offers 600 feet of frontage on West Neck Creek at the mouth of West Neck Harbor. The 3,700 square foot colonial-style clapboard home sits on 2.8 acres with a deep-water dock, guest cottage, and barn with a two-car garage/woodshop. Debra Von Brook-Binder of Daniel Gale Sotheby’s International Realty had the listing. Angelo Piccozzi of Dering Harbor Real Estate brought in the buyer, who closed on December 10.

The two-acre property includes a boat basin, one of three on the island.Courtesy of Saunders & Associates

8) 7 Lari Lane, Shelter Island | $3.75 million

This traditional 4,300 square foot home, set on two acres, boasts over 285 feet of waterfront on Coecles Harbor. The centerpiece of the property is the protected boat basin, one of only three on Shelter Island, which features a fully equipped dock with intricate stonework. Penelope Moore of Saunders & Associates filled in for the seller, while Michaela and Paulina Keszler of Douglas Elliman brought in the buyer. The exchange took place at the end of September.

The house at 18 Tuthill Lane on Ram Island was built in 1930.Courtesy of Saunders & Associates

9) 18-20 Tuthill Drive, Shelter Island | $3.5 million and
12 Peconic Avenue, Shelter Island Heights | $3.5 million

There was a tie for eighth place. Neighboring waterfront lots, one with an 1,800 square foot home and another vacant, at 18 and 20 Tuthill Drive on Ram Island traded for $3.25 million and $250,000 respectively in September. Totaling 1.06 acres, the plots offer a stone wall, over 150 feet of waterfront and a garage with a studio above. Mr. Wein Realty represented the listings and Penelope Moore of Saunders brought the buyer. The 4,000 square foot traditional home at 12 Peconic Avenue on a 1.1 acre property with a sandy road to Crab Creek and a waterfront pool, sold in April. Moore replaced both the ad and the buyer.

The waterfront house at 12 Peconic Avenue includes a path to Crab Creek.Courtesy of Saunders & Associates
The property for sale at 2 Cobbetts Lane includes a pond and beachfront plot.

10) 2 Cobbetts Lane, Shelter Island | $3.495 million

This 3,500 square foot Greek Revival replica, however, offers stunning views of Dering Harbor. Sitting on over two acres, the property features a pond and includes a separate beachfront parcel. Donald Dunning and Debra Von Brook-Binder of Daniel Gale Sotheby’s International Realty were on the listing side, while Brook- Binder also brought the buyer to the transaction in September.

A waterfront pool at 13A Westmoreland Drive overlooks West Neck Bay.Courtesy of Corcoran

Shelter Island Honorable Mention
13A Westmoreland Drive, Shelter Island Heights | $3.26 million

If we hadn’t counted Dering Harbor on the list, this house would have taken 10th place. This waterfront home is located on a private road near the end of a cul-de-sac that sold out in March. Situated on a peninsula overlooking West Neck Bay, the 3,800 square foot traditional style home offers a waterfront saltwater pool and deep water dock with water and electricity. Theresa Andrew of Corcoran represented the seller. The buyer’s agent was Hally Dinkel, then with Brown Harris Stevens who has since joined Corcoran.

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