luxury properties for sale Shelter Island, United States

Dating back to the original 1871 layout of the Shelter Island Grove and Camp Meeting Association, Spring Garden Avenue is celebrated for its organic, rolling streetscapes and preserved 19th-century architecture. 5 Spring Garden Avenue is an authentic 1880 Victorian residence that embodies the classic style of the era, from its steeply pitched rooflines to its expansive exterior woodwork. The interior layout is expansive and true to its vintage, characterized by distinctive octagonal rooms on both the first and second floors. With five bedrooms, a sprawling third-floor attic loft, and a substantial footprint of covered decks and porches, the home offers a generous canvas within a historic setting. A significant structural update was completed in 2008, replacing the older foundation with a new poured concrete basement and structural footings, alongside the installation of a new roof. Featuring full access to the Shelter Island Heights Association tennis courts and beach club, this property represents an authentic piece of island history.

This storybook circa 1858 cottage captures the very essence of North Fork living: cozy, charming, and effortlessly inviting. Rich in history and timeless appeal, this beautifully preserved home blends the simplicity of a bygone era with thoughtful modern updates, creating a warm and welcoming retreat. Inside, random-width wide plank flooring adds authentic character throughout. The first floor offers a spacious primary bedroom, a second bedroom or home office, an inviting living room, formal dining room, and an eat-in kitchen with a convenient laundry area. Upstairs, two additional bedrooms and a half bath provide comfortable accommodations. Architectural details enhance the home's enduring charm, from the welcoming semi-wraparound covered front porch to the side deck with a new retractable awning overlooking beautifully landscaped gardens. A pergola with a slate patio creates the perfect setting for outdoor dining, entertaining, or simply relaxing on a summer evening. Adding to the property's appeal is a detached 2-car garage and a delightful artist's or hobby studio, complete with its own pergola-covered sitting area nestled among lush gardens. Privately tucked behind a classic white picket fence, the beautifully landscaped .5-acre property is an exceptional outdoor sanctuary. The backyard features a heated free-form Gunite pool with a cascading waterfall, a pool shed with deck, two additional storage sheds, mature trees, and an abundance of seasonal flowering plantings, creating a peaceful and private oasis. Ideally located just minutes from pristine beaches, golf courses, marinas, renowned wineries and breweries, county parks, farm stands, Hampton Jitney and popular local eateries. This special property also enjoys close proximity to Historic Greenport, where waterfront dining, boutique shopping, and galleries await. The backyard abuts a nature preserve that leads to Marion Lake County Park. Nothing can be built behind it. Whether you're enjoying a quiet morning coffee on the porch, spending the afternoon poolside, or entertaining friends after a day at the beach, this one-of-a-kind North Fork treasure offers the perfect blend of historic character, modern comfort, and relaxed coastal living.

A rare opportunity to own an early 20th-century Adirondack-style cottage in Greenport, ideally situated just 0.12 miles from a beautiful Sound beach and only one mile from the heart of Greenport Village. This charming cottage showcases many of the home’s original details starting with a screened-in front porch spanning the full width of the facade, creating a welcoming indoor/outdoor retreat. Inside, the open floor plan includes a living/dining room with a wood-burning stove, an eat-in kitchen, full bath, laundry, and access to a rear deck. The second floor offers a cozy loft-style bedroom. Two additional accessory structures, each with electricity and water, provide flexible space for a home office, studio, or creative workspace. Surrounded by trees creating privacy and offering open vineyard views, this distinctive cottage compound captures the relaxed character and timeless appeal of the North Fork.

Wake up to endless views of the Peconic Bay — sunlight glimmering off the water, birds gliding over the nearby nature preserve, and the calm rhythm of the deep-water inlet just beyond your deck. This sweet beach cottage captures everything that makes summer on the North Fork unforgettable. With 3 comfortable bedrooms, 2 baths, and an open, easy-flow layout connecting the living, dining, kitchen, and entertainment nook, it’s made for barefoot mornings and breezy afternoons with friends. Step outside to a spacious wraparound deck and 130 feet of pristine waterfront — perfect for soaking in the sun, launching a kayak, or simply taking in the view. Secluded yet steps to the private sandy association beach, this is a rare slice of coastal paradise where summer never really ends.

Introducing Goose Creek - an exceptional 7.45 acre waterfront estate offering privacy, timeless architecture, and extraordinary Hamptons living. Set along an impressive 827 feet of waterfront, Goose Creek captures breathtaking views across Georgica Pond to the Atlantic Ocean. A long, private winding driveway leads through beautifully landscaped grounds, creating a sense of arrival and seclusion rarely found in the Hamptons. Lush rolling lawns and mature specimen plantings surround the property, offering a truly serene and park-like setting. A dramatic double-height foyer opens to a formal dining room with fireplace, while the adjacent chef's kitchen and breakfast area flow naturally into the spacious family room. French doors lead directly to a screened porch and expansive covered porch, creating effortless transitions between interior spaces and the surrounding landscape. The first floor also features an elegant library with fireplace, gracious living room, sunroom with a full wet bar, ideal for entertaining, and a private en-suite bedroom suitable for guests or staff. Upstairs, five en-suite bedrooms provide exceptional privacy, including a luxurious primary suite with a generous walk-in closet, spa-like bath with double vanity, soaking tub and shower, separate sitting room with fireplace, and private balcony overlooking the spectacular waterfront landscape. The finished lower level expands the home's lifestyle offerings with an open recreation area, home theater, gym with steam shower, seventh bedroom, and the potential to create an eighth bedroom. Outside, the grounds are designed for both relaxation and entertaining, featuring a detached three-car garage, pool house, and heated Gunite pool overlooking Georgica Pond. Adding to the estate's exceptional appeal is the potential for subdivision, offering the possibility of creating a second waterfront estate with space for an additional residence, pool, pool house, and tennis court. Goose Creek represents a rare opportunity to acquire a significant waterfront property in the Hamptons-combining scale, privacy, architectural pedigree, resort-style amenities, and extraordinary future potential.

Presenting a rare opportunity in the tiny village of New Suffolk. This slice of paradise is situated on the easterly side of West Creek along Grathwohl Road. This move in ready home is an oasis, consisting of the main house, beautifully appointed inground pool, pool house, outdoor kitchen and offered with this amazing property is a private guest cottage that can be used as overflow for family and friends or as an income generator. In the main house, you will find high end finishes and a true chefs kitchen (Wolf, Sub Zero etc). A finished game room below, three bedrooms on the second floor including the primary suite. The guest house, also tastefully cozy with two bedrooms, one on the main level, another on the second. Living room, eat-in kitchen, laundry and dry basement. Together, this offering represents in many ways the essence of the North Fork with its beauty, privacy and location. This is an exceptional opportunity.

Between the shoreline and the fairways is where you'll find Stonegate Estates at Cameron Court, Old Lyme's newest luxury development conveniently set close to White Sands beach. Embrace upscale living in these carefully crafted custom homes. The Ashton is the first offering and framing is complete. This home has a flexible floor plan, open flow, and smart design. A total of 8 lots remain available, including select premium lots overlooking the Black Hall Golf Course. Other plans available, whether you're looking to build your perfect home style, from one-level ranch to farmhouse to colonial design. Enjoy this opportunity to bring your design dreams to life! Old Lyme has award winning schools, a deep appreciation for the arts and activities for the woods or water! Conveniently set 2 hours from Boston and NYC.

Nestled in the pastoral countryside of Old Lyme and close to the sandy beaches, 2 Rowland Road offers an extraordinarily rare opportunity to finish restoring a landmark 1824 Colonial estate spanning over 4,000 square feet. Blending timeless historic provenance with substantial modern additions, this sprawling home is primed for a buyer with a vision to create a masterpiece. The main residence retains authentic period charm, featuring 4 original fireplaces, gorgeous wide-plank wood flooring, and stately woodwork throughout. At the heart of the main level sits an expansive commercial-grade chef's kitchen-outfitted with custom cabinetry, a Traulsen commercial refrigerator with separate beverage fridge, 6-burner Wolf cooktop, Miele oven with warming drawer, and Bosch dishwasher. The impressive primary suite boasts a dedicated library/office space, an attached solarium and custom built-ins.