1) 10 Lari Lane, Shelter Island | $11.575 million
Only one sale on Shelter Island reached above $10 million. This waterfront gated compound set on 3.25 acres boasts 325-feet on Coecles Harbor. The 16,000-square-foot home overlooks a private dock and a private beach was designed by noted architect Val Florio, plus there is a three-car carriage house, a two-story pool house and an infinity-edged heated gunite pool with raised spa. Corcoran 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 the buyer, who closed in September.
2) 7 Apple Orchard Lane, Shelter Island | $9.1 million
Known as Four Seas, the 1.5-acre property in Shorewood looks west across the Peconic Bay and offers 150 feet of private beach. The classic gambrel-style, 10,000-square-foot home, built by the late Hamptons builder Ben Krupinski, sold in March. There is also a waterside, 50-foot heated gunite pool and hot tub framed by a 150-foot private dock. Peter McCracken and Gary DePersia of Corcoran had the listing, last asking $9.95 million. Penelope Moore of Saunders & Associates brought the buyer.
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 somewhat well-known address on the small island. The seller, Martha Baker, a former fashion director at New York magazine, famously fought for a permit for a veranda during the 1990s while fixing up the old Tudor home, all the way to the Supreme Court. Now a landscape designer and author, she has parted ways with the well-appointed home, which sits on a 0.72-acre lot that includes 125 feet of beach frontage, a deepwater dock, a large back lawn with room for a pool, as well as a two-car detached garage. It was offered exclusively by John Catrambone at Dering Harbor Real Estate at $6.3 million and he sold it for $200,000 more on November 3.
4) 40B Stearn’s Point Road, Shelter Island Heights | $6 million
A one-of-a-kind showpiece with jaw-dropping views, this house also comes with access to Crescent Beach and a shared dock. The 5,800-square-foot home is perched atop the bluffs on 3.87 acres with “a modern meets vintage” vibe, according to the listing. It features original 1920s woodwork, while noted architect/designer Michael Haverland reimagined the home by adding a modern wing with a luxe primary suite and maximizing the views from multiple levels. 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 repped the buyer, who closed on November 1.
5) 102 Peconic Avenue, Shelter Island | $5 million
In an off-market transaction, a Nantucket-style beach house with views of the Great Peconic Bay and the shorelines of both the North and South Forks sold in early December. The 1.2-acre property includes a 3,500-square-foot house, a guest cottage, waterside pool and 200 feet of sandy beach. Michael Brennan of Douglas Elliman Real Estate represented both sides of the deal.
6) 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 sweeping 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 detached two-car garage. It traded in March and Daniel Gale Sotheby’s International Realty represented both sides of the listing.
7) 30 Little Ram Island Drive, Shelter Island | $4.9 million &
15 Montclair Avenue, Shelter Island Heights | $4.9 million
Tying for seventh place are two addresses, one on Coecles Harbor and one on West Neck Harbor. The home at 30 Little Ram Island Drive is a shingled traditional that sits on 1.82 acres with frontage on Coecles Harbor. The property offers 185 feet of shoreline and the 3,783-square-foot home enjoys water views from nearly every room. There is also a tennis court, a pool, a guest house and a 70-foot long dock. Penelope Moore of Saunders & Associates had the co-exclusive with John Catrambone of Dering Harbor Real Estate, with the latter bringing the buyer to close on April 21.
As for 15 Montclair Avenue, a shingle Gambrel-style, 4,900-square-foot home sits on a half-acre with 200 feet of bulk-headed waterfront, staircases leading to a private beach and a private dock. An open listing, Margot Reutter of Corcoran represented the buyer and Georgiana B. Ketcham Real Estate also received credit when the property sold on November 15.
8) 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 shingled-style home sits on 2.8 acres with a deepwater dock, a guest cottage and a 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 the buyer, who closed on December 10.
9) 7 Lari Lane, Shelter Island | $3.75 million
This traditional, 4,300-square-foot home, sited 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 has a fully equipped dock with intricate stonework. Penelope Moore of Saunders & Associates repped the seller, while Michaela and Paulina Keszler of Douglas Elliman brought the buyer. The trade occurred in late September.
10) 18-20 Tuthill Drive, Shelter Island | $3.5 million &
12 Peconic Avenue, Shelter Island Heights | $3.5 million
There was a tie for ninth place. Neighboring waterfront lots, one with a 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 parcels offer a stone bulkhead, more than 150 feet of beachfront and a garage with a studio above. M. 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 path down to Crab Creek and a waterside pool, sold in April. Moore repped both the listing and the buyer.
Shelter Island Honorable Mention
2 Cobbetts Lane, Shelter Island | $3.495 million
This 3,500-square-foot Greek Revival replica has sweeping views of Dering Harbor. Sitting on two-plus acres, the property boasts 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 when it traded in September.
13A Westmoreland Drive, Shelter Island Heights | $3.26 million
If we had not counted Dering Harbor on the list, this home would have taken the 10th spot. This waterfront home is located on a private road near the end of a cul-de-sac that sold in March. Located on a peninsula with views of West Neck Bay, the 3,800-square-foot traditional-style home offers a waterside saltwater pool and a deepwater 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.
Editor’s Note: This article was updated on February 5 to include a listing that has not yet come through the deed transactions.