5 Bedrooms
4.5 Bathrooms
4,263 Fin. SQFT
Canal & 120ft Bulkhead
Swimming Pool
2-Car Garage
EXPERIENCE THE BEST OF THE EAST END
Experience the best of the East End from this waterfront retreat in Hampton Bays’ exclusive Old Harbor Colony. Set on a quiet street with beautiful water views, 20 Oak Lane offers a rare blend of space, light, and true boating lifestyle—just minutes to ocean beaches, waterfront dining, and everything the Hamptons have to offer. With over 4,200 square feet of interior living space plus a two-car garage, five bedrooms (including two primary suites), four full baths, and one half bath, the home offers exceptional flexibility for family, guests, and entertaining. The waterfront setting is at the heart of the property. Step outside to a private backyard oasis featuring a recently relined pool (2024), expansive deck, broad lawn, and approximately 120 feet of composite bulkhead. The substantial waterfront provides exceptional dockage capacity for multiple boats or larger vessels, making the property particularly well suited to serious boaters. From your backyard, head out across Shinnecock Bay toward Shinnecock Inlet and the Atlantic Ocean beyond. Spend a morning fishing offshore, cruise the surrounding waterways, visit waterfront restaurants by boat, or enjoy an evening on the water before returning home to your own dock. The pool and deck create a natural gathering place throughout the summer, with plenty of room for outdoor dining, lounging, grilling, and entertaining.
Inside, cathedral ceilings and abundant natural light define the main living spaces. The spacious kitchen offers extensive cabinetry, generous island prep space, a stove plus two wall ovens, and direct access to the deck and pool. Multiple living areas provide considerable flexibility. The family room features a gas fireplace, while the living room has a traditional wood-burning fireplace. A sunroom opens directly to the deck and pool, creating an easy connection between indoor and outdoor living. A main-level bedroom and full bath provide convenient accommodations for guests or anyone who prefers to avoid stairs. The home also includes another spacious primary suite, while an additional primary suite upstairs creates a private, elevated retreat with its own living area, mini-kitchen, walk-in closet, large ensuite bath, and private deck overlooking the water. A large recreation room provides still more living space for games, television, exercise, or hobbies. Two additional bedrooms with cathedral ceilings and a shared Jack-and-Jill bath complete the upper level. Beyond the property itself, Old Harbor Colony offers a quiet residential waterfront setting while keeping the best of Hampton Bays close at hand. Ponquogue Beach and the Atlantic Ocean are only minutes away, and Hampton Bays is known for its boating opportunities, marinas, restaurants, beaches, and access to both Shinnecock and Peconic bays. Whether you’re boating from your backyard, entertaining around the pool, or enjoying summer evenings overlooking the water, 20 Oak Lane combines substantial living space with the exceptional waterfront access that defines the Hamptons lifestyle.
PHOTOS
FLOOR PLANS
ABOUT OLD HARBOR COLONY
Old Harbor Colony is a close-knit, waterfront community located just minutes from ocean beaches, marinas, and the vibrant heart of Hampton Bays, offering convenient access to dining, shopping, and a wide range of recreational activities. The neighborhood is known for its quiet streets, well-maintained homes, and welcoming atmosphere, creating a sense of ease and privacy that’s increasingly rare on the East End.
A defining feature of the community is its charming rustic red barn, a gathering place where residents come together for seasonal events, including a popular summer lobster and steak dinner, holiday celebrations, and other neighborhood traditions that foster genuine connection. Community members also enjoy access to a private residents-only beach located off Canal Way Circle, providing a peaceful spot to relax by the water or launch kayaks and paddleboards.
With many homes offering waterfront views or canal access, Old Harbor Colony is especially appealing for those who enjoy boating, kayaking, and life on the water, with easy access to open bays and the ocean beyond. The homeowners association is active yet unobtrusive, with a modest annual fee that helps preserve the community’s character and shared amenities. In Old Harbor Colony, you’ll find more than just a desirable location — you’ll discover a relaxed, neighborly lifestyle rooted in coastal living, tranquility, and a strong sense of community.
ABOUT THE HAMPTON BAYS AND NEARBY AREAS
Hampton Bays is a picturesque coastal community on Long Island’s South Fork, celebrated for its waterfront charm, scenic canals, and miles of beautiful beaches, including the iconic stretches along Dune Road. Residents and visitors enjoy a vibrant mix of dining, shopping, and local culture, making it an ideal location for a summer retreat or full-time East End residence.
The area boasts a selection of elegant to casual waterfront restaurants, including Oaklands Restaurant & Marina (waterfront, seafood & sunset views), Edgewater Restaurant (Italian fare with bay views), and Sunday’s on the Bay (dining by the water). In town, residents can enjoy New York‑style pizza and Italian fare at Uncle Joe’s Pizza & Restaurant or Francesca’s Pizza & Restaurant, island‑inspired cuisine at RUMBA Island Inspired Cuisine & Rum Bar, hearty pub food at Buckley’s Inn Between, and much more from the area’s vibrant dining scene. Other local favorites include Canal Cafe (marina views and casual fare) and 1 North Steakhouse, a standout destination for steak lovers on the East End. For shopping and leisure, Hampton Bays offers three supermarkets — King Kullen, Stop & Shop, and Wild By Nature — as well as Hampton Fruit & Vegetable for fresh produce, Scotto’s Italian Deli & Meat Market, quaint antique shops, Ace Hardware, and Macy’s, blending small-town charm with everyday convenience.
Hampton Bays places you within convenient reach of the Hamptons’ most celebrated destinations. A drive east brings you to Southampton and East Hampton, where boutique shopping, art galleries, and renowned restaurants offer a taste of upscale coastal living. From curated home décor to high-end fashion and gourmet dining, these towns complement the relaxed pace of Hampton Bays perfectly. For a scenic escape, Montauk Point is also easily accessible, offering iconic ocean views, lighthouse walks, and fresh seafood along the shore. Living in Hampton Bays allows you to enjoy a peaceful waterfront retreat while remaining close to the cultural, culinary, and recreational highlights of the wider East End.
Just a scenic drive north from Hampton Bays lies Long Island’s celebrated North Fork wine region, home to more than 40 vineyards and wineries set along gently rolling farmland and peaceful country roads. The North Fork stretches roughly 30 miles from Riverhead to Orient Point, offering opportunities to explore charming tasting rooms, enjoy wine flights paired with local fare, and discover boutique producers crafting everything from crisp chardonnays to rich merlots. Visiting the North Fork makes for a rewarding day trip from Hampton Bays, balancing seaside living with relaxed vineyard experiences and leisurely afternoons sipping local wine in one of the East End’s most picturesque regions.
With its combination of coastal beauty, waterfront dining, charming shops, and recreational opportunities, Hampton Bays provides an engaging and relaxing lifestyle. From exploring the beaches and marinas to enjoying local flavors and hidden treasures, the community captures the quintessential East End experience in a vibrant yet serene setting. It’s also not far to Southampton and East Hampton, and about an hour to Montauk Point, which is a beautiful destination for a day trip.
CONTACT US
To schedule a viewing or ask questions feel free to call (703) 944-8141 or send an email to move@dcregionrealestate.com.
Disclosure: One of the parties with a financial interest in this property is a licensed real estate agent in the states of Virginia & Maryland as well as the District of Columbia.