Shelter Island Homes with Colonial Style

Welcome to Shelter Island, a hidden gem nestled in the heart of Suffolk County, New York. This enchanting island, surrounded by the pristine waters of Peconic Bay and Gardiners Bay, offers a serene escape from the hustle and bustle of mainland life. With its lush landscapes, charming waterfront views, and a close-knit community, Shelter Island is the perfect place to call home, especially for those who appreciate the timeless elegance of Colonial-style architecture.

Colonial homes on Shelter Island are a delightful nod to the past, characterized by their symmetrical designs, gabled roofs, and classic brick or wood exteriors. These homes often feature spacious interiors, adorned with period details such as hardwood floors, crown moldings, and inviting fireplaces, which create a warm and welcoming atmosphere. Many of these residences also boast expansive yards, perfect for outdoor entertaining or simply enjoying the tranquil surroundings.

Living in Shelter Island means embracing a lifestyle rich in natural beauty and recreational opportunities. Residents can explore miles of scenic trails, pristine beaches, and picturesque parks, all while enjoying the island's laid-back charm. The vibrant local community hosts various events throughout the year, from farmers' markets to art shows, ensuring there's always something to engage with.

Whether you’re seeking a serene retreat or a family home steeped in history, Shelter Island’s Colonial-style residences offer the perfect blend of classic appeal and modern convenience. Discover your dream home in this idyllic setting and experience the unique charm that Shelter Island has to offer!

Newest Shelter Island Homes with Colonial Style

$3,795,000

5 Beds ⋅ 5 Baths ⋅ 1016596 MLS

Nestled within Shelter Island’s highly sought-after Shorewood Farms community, this exceptional waterfront beach house offers the perfect coastal retreat. Enjoy breathtaking views across Mabel’s Creek and the South Fork, with a sandy beach just steps from your door. As a resident of Shorewood Farms, you’ll also enjoy exclusive access to a private association beach and tennis courts, enhancing the relaxed waterfront lifestyle. Designed for both entertaining and everyday enjoyment, the property features two private docks ideal for boating, paddleboarding, and kayaking, along with a spacious waterside deck overlooking the sparkling water. The first floor has a large waterfront room that opens directly onto the deck, complemented by 4 generously sized bedrooms and 4 full bathrooms. Upstairs, soaring cathedral ceilings frame an open-concept great room encompassing the living, dining, and kitchen areas. Walls of glass capture stunning panoramic water views, creating a light-filled and inviting gathering space. Privately situated off the great room, the expansive primary suite offers a large walk-in closet and a spa-inspired bathroom. Completing the property is a detached 2-car garage with a finished upper level, providing the perfect space for recreation, a home office, artist’s studio, or additional guest accommodations. A rare opportunity to enjoy waterfront living with private docks, beach access, tennis, and some of Shelter Island’s most captivating water views.

5 Sea Gull Road, Shelter Island

$2,350,000

4 Beds ⋅ 4 Baths ⋅ 991700 MLS

Welcome to your dream getaway where modern luxury meets laid-back coastal charm. This Newly renovated 4 Bedroom 3.5 Bathroom home offers perfect blend of style & tranquility, just moments from beaches, marinas and all that island has to offer. Designer Kitchen with Quartz countertops. custom soft close cabinetry with center island & high end appliances. Located on first floor Primary Bedroom with en-suite, cathedral ceiling and french doors to balcony. 3 additional Bedrooms each with an en-suite. Sunken Den, Sitting Room & office. 5" White Oak hardwood flooring throughout first and second level. Recessed lighting, Level 5 finished walls. Central air, Gas propane heat. Hardie Board siding. Upgraded 200 amp electric. 1 Car garage. Inground gunite pool ( optional ) .50 acre. Experience the best of island living in this beautiful renovated coastal retreat. Completion date July 2026. Still time to pick your colors and more

5 Marc Street, Shelter Island

$2,485,000

6 Beds ⋅ 4 Baths ⋅ 978923 MLS

Nestled on a full acre in the heart of Shelter Island, this exceptional island retreat offers the perfect blend of relaxed elegance and modern comfort. The main residence features an airy open-concept design ideal for both everyday living and entertaining. A chef’s kitchen anchors the home, seamlessly flowing into the dining and living areas, where a dramatic vaulted ceiling fills the space with natural light and a sense of grandeur. The main home includes four spacious bedrooms and three full baths, offering comfortable accommodations for residents and guests. An attached two-car garage provides convenience, with a versatile bonus room above—perfect for a media room, studio, or additional lounge space. Just across the yard, a charming private cottage offers two bedrooms, a full bath, a living room, and a kitchenette—ideal for guests or a private retreat. Outdoor living is equally inviting. The kitchen opens to a generous deck designed for effortless entertaining, overlooking beautifully landscaped grounds. Enjoy warm summer days by the heated gunite pool, relax around the firepit area, and take in the peaceful surroundings of this southwest-facing property. Across the street, access to West Neck Creek makes kayaking and paddleboarding effortless, offering a true water-lover’s escape. A rare opportunity that captures the essence of coastal living on Shelter Island—where comfort, style, and exceptional indoor-outdoor spaces come together in a truly special setting

14 Freds Lane, Shelter Island

Start Your Search

Listings courtesy of OneKey® MLS as distributed by MLS GRID. Based on information submitted to the MLS GRID as of . All data is obtained from various sources and may not have been verified by broker or MLS GRID. Supplied Open House Information is subject to change without notice. All information should be independently reviewed and verified for accuracy. Properties may or may not be listed by the office/agent presenting the information.