A vacant oceanfront property, one of four that overlook the surfer’s haven of Ditch Plains Beach and once the site of the East Deck Motel, traded last week. Yielding $9 million, it’s the highest-priced one-acre oceanfront lot ever sold in Montauk.
Erica Grossman at Douglas Elliman and Hedgerow Exclusive Properties represented the listing, part of the On the Break development at one of the East Coast’s most iconic surfing spots. Hedgerow, a Bridgehampton-based brokerage, brought the undisclosed buyer to the deal.
“This sale is testament to the fact the high-end market is heating up,” Grossman tells Behind The Hedges. “In Montauk, this land sale, offering the chance to create a rare masterpiece on the ocean, shows that buyers with vision and those who are paying attention to opportunity in the market are getting serious.”
In 2021, the vacant 1.2-acre parcel at 46 Deforest Road, another of these On the Break lots, sold for $8.1 million. Another comparable sale is that of 260 Old Montauk Highway, a 1.5-acre oceanfront parcel, which sold for $9.5 million in 2019, the equivalent to $6 million per acre.
Grossman explains that the Hamptons real estate market is shifting. “Since the election, I’ve observed there to be more market activity and buzz in general across the South Fork, with several oceanfront and other ultra-luxury properties recently going into contract. It’s an exciting time to see that strength building in the market,” she says.
Heath Freeman’s On the Break Development is the seller and also owns the adjacent lots at 42 and 40 Deforest Road. Freeman is the president and founding partner of New York-based Alden Global Capital, is also the force behind EHP Hospitality Group, which owns EHP Resort & Marina in East Hampton and Shagwong Boat Club, among other entities.
Under the limited liability company, 40 Deforest Road LLC, the development firm purchased 44 Deforest Road in 2021 for $6.45 million. Though there were plans to develop a 5,400-square-foot, eight-bedroom home with panoramic ocean views, 92 feet of ocean frontage and a waterfront pool and spa, it remained vacant. The last ask for the property, known as Casa Encantada | On The Break, was $12.95 million, before it traded at $9 million on Thursday, Dec. 19.
“Nestled in one of the most iconic surf destinations on the East Coast, On The Break oceanfront properties offer an unparalleled setting,” Grossman says. “With a premier surf break and an expansive stretch of ocean frontage, these homes redefine luxury living in Ditch Plains. Each property spans a full acre and features direct, private access to the ocean—an exceptional rarity in this coveted location. Boasting stunning, unobstructed views along the Montauk coastline, the homes are designed to maximize the beauty of their surroundings while delivering unmatched sophistication.”
Award-winning architect Boris Baranovich designed the residences, two of them built by luxury Hamptons builder Hobbs Inc., which Grossman says “showcase exceptional build quality and thoughtful design. From spacious interiors to high-end finishes, each home includes features such as three-car garages, multiple bedrooms and bathrooms, expansive decks, fireplaces, hot tubs, and pools.”
She continues, “On The Break properties are truly a masterpiece of modern coastal living, offering the ultimate combination of luxury, comfort, and breathtaking natural beauty.”
While 2024 was a slow year for oceanfront sales throughout the South Fork, Grossman feels, “this oceanfront sale, and recent others, collectively signal an improvement in the high-end oceanfront market. This is an exciting sale for Montauk, and we’ve also seen recent listings on Meadow Lane in Southampton and on Surfside Drive in Bridgehampton go into contract, along with a flurry of activity on other oceanfront homes throughout the East End. We’re entering 2025 with great momentum in the oceanfront market.”
They are also expecting strong interest in oceanfront rentals. On the heels of this sale, they are also announcing a unique, record-breaking rental offering in Montauk for summer 2025: 40 and 42 Deforest are available together as a compound for $1.5 million for Memorial Day through Labor Day.
“Asking $1.5 million, this compound rental opportunity is debuting as the priciest rental for the 2025 season in Montauk, and it presents an unmatched opportunity to spend the summer in the highly sought after Ditch Plains area,” says Grossman. “It’s the most exciting place to be for individuals who adore Montauk, its vibrant cultural scene and amazing restaurants, relish oceanfront living and entertaining family and friends, and have a passion for surfing and/or beach days and evenings.
And, if available, the oceanfront compound will be listed together for $39.95 million,
Casa Amor | On The Break, the estate 42 Deforest Road, is the first of two modern homes set amidst the natural landscape just off the iconic surfing destination. Set on a full acre, the 5,100-square-foot home, offers 90 feet of direct ocean frontage. The open-concept home provides plenty of room for guests. Sliding glass doors lead out onto the deck overlooking the 20-by-40-foot unite pool and spa. There’s also a screened porch and an oceanside sunken fire pit.
The second-level primary suite features a fireplace, spacious bathroom, dressing room with multiple closets and a private waterside terrace. Three additional en suite bedrooms are located in this section of the second floor, with another two bedrooms accessed via a secondary staircase completing the level.
The house at 40 Deforest Road, the corner lot, holds a 4,800-square-foot house with six bedrooms. A grand double-height entry foyer leads to a main level with two sitting areas, a formal dining and a chef’s kitchen. Glass doors open to an expansive deck that spans nearly the width of the home for plenty of room to entertain overlooking the ocean. Steps away is the 20-by-30-foot unite pool with a sun shelf and spa.
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