Top 10 Priciest North Fork Home Sales of 2021

Top North Fork Sales
Courtesy photos

While Behind The Hedges reported the top 21 most expensive home sales in the Hamptons several weeks back, let’s now take a look at the North Fork.

“While you may be reading reports on inventory shortages for homes clear across the country, nowhere is it as severe as it is on our beautiful North Fork,” Judi Desiderio, the CEO of Town & Country Real Estate, said in her recent year-end homes sales report. There were 569 sales in 2021, down 1.04% from 2020, but the total home sales volume was up 20.24% to $552,687,174.  

Unlike on the South Fork where sales are traditionally much higher, Town & Country’s report shows that there were only two sales above $5 million all year and a total of 37 above $2 million. 

Here are the top 10 priciest home sales on the North Fork, excluding Shelter Island (look for that article coming up!):


845 Maple Lane, SoutholdCourtesy of The Corcoran Group

1) 845 Maple Lane, Southold | $7 million  

A five-acre compound, sold in February by Philip Stanton, a founding member of the Blue Man Group, and his wife, Jennifer Stanton, tops the list of the most expensive residential sales for 2021. The 4,565-square-foot home, which the couple called “Bliss House,” sits on 482 feet of waterfront on Town Creek and boasts a deep water dock with access to the bay. Originally built in 1860, the home has been extensively renovated. In addition to a grand eat-in kitchen with a fireplace, an enclosed porch, a sunroom and a living room with a fireplace, there are five-plus bedrooms and five-and-a-half baths. A heated saltwater pool and spa are complemented by a pool house with a bathroom and cabana changing area. The vast property also holds two large barns, fire pits and outdoor seating. The sale included acreage that consisted of three separate lots all comprising a bit over five acres. Sheri Winter Parker of the Corcoran Group represented the seller. Jessica Vertullo of Compass was the buyer’s agent. 

1780 Jackson Street, New SuffolkCourtesy of Daniel Gale Sotheby’s International Realty

2) 1780 Jackson Street, New Suffolk | $6.5 million 

This cape-style home, which overlooks Robins Island Cove, traded in September with Donielle Cardinale of Daniel Gale Sotheby’s International Realty representing both sides of the deal. The 6,000-square-foot home was designed to ensure a bay view from nearly every room. While it was built in 2006, it features a brand new kitchen. The open living room leads to a bayfront balcony and the lower level walk-out allows access to the pool and private beach. The 0.98-acre lot also boasts a rarely-seen six-car garage. The property originally went on the market in September of 2020 for $7.2 million. In June of 2021, the price was adjusted to $6.895 million and went into contract the very next month. 

1505 Naugles Drive, MattituckCourtesy of NOFO Real Estate

3) 1505 Naugles Drive, Mattituck | $4.25 million &
65 Soundview Avenue, Mattituck | $4.25 million 

There was a tie for the third spot as two homes on the Long Island Sound in Mattituck each sold for $4.25 million. The custom built home at 1505 Naugles Drive traded in September, while 65 Soundview Avenue closed in mid-December. Both involved NOFO Real Estate, a North Fork-based brokerage that was number one in terms of sales volume for Mattituck in 2021. 

The Naugles Drive property’s 5,700-square-foot home offers sweeping views of the Long Island Sound. The one-acre property, which includes a saltwater freeform pool surrounded by a patio and private dock, was asking $4.795 million. Susan Orioli represented the seller. The buyer was represented by Randy Katakofsky of Douglas Elliman Real Estate. 

65 Soundview Avenue, MattituckCourtesy of Compass

The house on Soundview Avenue is perched above the Sound with a large private beach and expansive views from the 1.2-acre property. The four-bedroom, four-bath home also boasts a walk-out basement. A bonus is a waterside infinity pool with a waterfall. Bridget Elkin of Compass, the number one producing agent across all brokerages on the North Fork as cited in WSJ/Real Trends 2021 Rankings, represented the seller and Alexis Meadows of NOFO Real Estate represented the buyer.

825 Stephensons Road, OrientCourtesy Town Country Real Estate

4) 825 Stephensons Road, Orient | $4.17 million 

Back in May, one of the most iconic homes, which can be easily seen when entering the hamlet on the Orient Causeway, traded for $4.17 million. It first went on the market in June of 2020 for $4.775 million and was taken off the market in September of that year. It was listed again in April of 2021 for the same price and quickly found a buyer, who closed on May 26. 

“This home, in particular, dates back to 1868 and was part of a large family compound located just over the causeway in a private estate enclave known as ‘The Hill’ set on five acres with 475 feet of private beachfront on the Long Island Sound,” explained Lori Feilen of Town & Country Real Estate, who represented both sides of the deal. The home, which underwent extensive restoration, offers 180-degree views from every room and multi-level decks.

2740 Deep Hole Drive, MattituckCourtesy of Excelsior Realty

5) 2740 Deep Hole Drive, Mattituck | $4.1 million 

Located on a creek with bay access, this 3,700-square-foot home has lots of coastal charm. “With its rich architectural design by Samuels and Steelman and custom craftsmanship of the highest quality by Burger Construction, this is a superb location for summer getaways or permanent residency,” according to the listing. At least one person agreed. The four-bedroom, 4.5-bath house with a private dock sold in November. Douglas Cabral of Excelsior Realty in Bohemia repped the seller and Joseph DiVello of Century 21 Alberton Realty in Southold brought the buyer. 

725 Terry Lane, SoutholdCourtesy of Daniel Gale Sotheby’s International Realty

6) 725 Terry Lane, Southold | $3.85 million 

Billed as a “lux cedar shake beach house” on 0.66 of an acre, this home boasts 100 feet of frontage on Southold Bay. The 4,000-square-foot, three-level home featured a newly renovated, white kitchen with high-end appliances and wood plank floors. The open floor plan provides breathtaking water views through walls of glass. With 2,500 feet of ipe decking with a cable wire rail and a seaside hot tub, outdoor living is a breeze. Carol Szynaka and Mariah Mills of Daniel Gale Sotheby’s International Realty were on both sides of the deal. 

63875 Route 48, GreenportCourtesy of Brown Harris Stevens

7) 63875 Route 48, Greenport | $3.585 million 

This architecturally significant contemporary home sold quietly in May, exclusively listed with Rachel Louise Rushforth-Worrell of Brown Harris Steven’s Sag Harbor office. Found on an ultra-private 2.71 acres, the Brown Harris Stevens listing says it mixes “a Napa Valley vibe with the beauty and natural environment of its stunning setting; overlooking the Long Island Sound.” An Ira Glass design, it was built in 2005. The cedar-clad 5,500-square-foot home was reimagined with a modern aesthetic by the designer/builder Lucy Barnes. There is an emphasis on separate living spaces afforded by three wings with separate courtyards. The property includes access to a 93-foot sandy beach down a rustic path, a 70-foot-by-16-foot saltwater pool and a tennis/basketball court. 

1000 Sound Beach Drive, MattituckCourtesy of NOFO Real Estate

8) 1000 Sound Beach Drive, Mattituck | $3.55 million 

Located on the Sound, the 0.71-acre parcel includes 100 feet of waterfront. The home’s main level offers water views from the living room and entertainment area and an expansive primary bedroom with a private deck. The beach level boasts an additional living room, a kitchen, a second master bedroom and a guest ensuite. Susan Orioli of NOFO Real Estate represented the seller and worked with the buyer when it closed in November. The original list price was $3.65 million. 

4875 Nassau Point Road, CutchogueCourtesy of North Fork Real Estate

9) 4875 Nassau Point Road, Cutchogue | $3.5 million 

This home provides 180-degree views of the bay from its perch, as well as 200 feet of private beach. The main house has five bedrooms, including two ensuites on the main level and a master suite on the water with a private balcony and Jacuzzi. The 1.75-acre property has a heated pool, plus a pool house/garage with a half-bath. The deal closed in July. Nicci Fitzgerald of North Fork Real Estate was the listing agent. Lisa Gillooly, then with Corcoran, represented the buyers. 

14990 Oregon Road, CutchogueCourtesy of the Corcoran Group

10) 14990 Oregon Road, Cutchogue | $3.4 million

Last on our top 10 list is this 3.68-property in the heart of the wine country that includes vines and vineyard views. The 3,585-square-foot home offers a chef’s kitchen, four bedrooms, two laundry rooms and a sunroom that leads to a 40-foot-by-25-foot heated gunite pool. A wine cellar is also, appropriately, included in this home. The 3.68-acre property also boasts an eight-car garage with an apartment that features a fireplace and a large agricultural barn surrounded by land with development rights that have been sold. Sheri Winter Parker of Corcoran repped both sides in the deal that closed in July.

This article will be updated online if necessary.