Oak Bluffs Homes with Cape Style

Welcome to Oak Bluffs, a charming gem nestled in Dukes County, Massachusetts, on the picturesque Martha's Vineyard. Known for its vibrant community and stunning coastal beauty, Oak Bluffs is a delightful blend of history, culture, and natural wonder. This enchanting town boasts a rich maritime heritage, with colorful gingerbread cottages that line the streets, creating a whimsical atmosphere that beckons visitors and residents alike.

One of the most appealing aspects of Oak Bluffs is its diverse real estate offerings, particularly the captivating Cape-style homes. These iconic residences, characterized by their steeply pitched roofs and symmetrical facades, are perfect for those seeking a slice of New England charm. The Cape-style homes in Oak Bluffs often feature cozy interiors, inviting living spaces, and delightful outdoor areas, making them ideal for both year-round living and summer escapes.

Imagine waking up in your Cape-style home, just a short distance from the stunning beaches and vibrant nightlife that Oak Bluffs has to offer. Spend your days lounging on the sandy shores, exploring the scenic bike paths, or indulging in the local culinary delights at charming restaurants. The town's rich cultural scene, highlighted by art galleries, theaters, and seasonal festivals, ensures there’s always something exciting happening.

Whether you’re looking for a family home or a serene retreat, Oak Bluffs offers a unique lifestyle that beautifully balances relaxation and adventure. Discover the magic of Cape-style living in this idyllic coastal town, where every day feels like a vacation!

Newest Oak Bluffs Homes with Cape Style

$839,000

1 Beds ⋅ 1 Baths ⋅ 73548644 MLS

This little gem is waiting to be polished. Hidden behind a wall of vegetation on Winthrop Avenue, an 'oasis', with lots of potential. Existing one bedroom, two story house situated on a 1/3 Acre of land, a 14,810 sq.ft. level lot. Land is large enough for a house and guest house when meeting ZBA requirements, or build a new house and leave existing structure as an Accessory Dwelling Unit when in compliance Massachusetts ADU regulation - 760 CMR 71.00. Only .6 of a mile to Oak Bluffs Harbor and .5 mile to the top of Circuit Avenue! Title 5 Certification in place. Lot is in Zone II and will allow a total of two bedrooms with upgrade to an advanced treatment system. Just one house from Wesleyan Park or stroll to Harbor and Town. Empty and easy to show.

26 Winthrop Ave, Oak Bluffs

$2,800,000

4 Beds ⋅ 5 Baths ⋅ 73527128 MLS

Tucked away in a serene setting and set on a private 1.38-acres, this beautifully renovated 4BR/4.5BA Cape offers over 4,000 sq ft. of living space with pleanty of room for a backyard pool. The seller will escrow $50K towards a pool at closing depending on the offer. The property has been thoughtfully renovated with two new kitchens, 4.5 new bathrooms, 4-bedrooms (two ensuite), and all new appliances and windows. Its floor plan is great for entertaining and flows family and guests from an oversized living room with fireplace into the dining room, gourmet kitchen and an inviting family room with cathedral ceiling and propane stove. First floor includes an ensuite bedroom and large screened in porch. The 1-bedroom apartment above the 2-car garage includes living/dining/kitchen area, washer/dryer, and heat/AC. The property includes a full basement, spacious rear patio and deck, outdoor shower and is large enough for an in-ground pool. Assessed value does not reflect extensive 2026 renovations. Furnishings in the photos have been virtually staged.

44 Tiffany Dr, Oak Bluffs

$1,995,000

3 Beds ⋅ 3 Baths ⋅ 73511961 MLS

Welcome to 33 Vineyard Avenue in Oak Bluffs, Martha's Vineyard. This fully gut renovated property encompassing 3B/2Ba in total featuring a 2BR/2BA primary home plus a distinctly separate attached 1BR/1BA ADU suite - offering flexible, move-in ready living or investment potential in a prime in-town location. The main residence in the primary showcases a light-filled interior, wood floors, beamwork, and refined finishes throughout. Open living flows to a gourmet kitchen with suede-finish stone counters, Bosch appliances, dining bar, and walk-in pantry. Upstairs offers two spacious bedrooms, a skylit bath with glass and stone shower, and a private balcony. Enjoy multiple outdoor spaces including a covered porch and side deck. The 1b/1ba ADU secondary suite provides a private entrance, parking, and utilities--ideal for guests or rental income. Featuring open living, oak floors, a stylish kitchen with stone counters and Bosch propane oven, plus a bedroom and full bath.

33 Vineyard Ave, Oak Bluffs

$1,495,000

4 Beds ⋅ 3 Baths ⋅ 73500318 MLS

Nestled in a desirable neighborhood, this beautifully maintained cape style home offers a rare blend of charm, flexibility and convenience in a serene island setting. Thoughtfully appointed throughout, the home welcomes you with an open living room that flows effortlessly into a bright dining area, where French doors open to a private stone patio—creating an inviting connection between indoor comfort and outdoor living. The first floor also includes a bedroom with a full bath, offering ideal flexibility for guests or remote work. Upstairs, two spacious bedrooms share an updated tile bath, providing comfortable accommodations with timeless appeal. The detached studio is a great bonus offering a living area, modern kitchenette and full bath! A spiral staircase leads to an additional upper-level space, offering even more versatility for guests, creative use or a private retreat. Strong rental history!

26 Sea Glen Road, Oak Bluffs

$5,450,000

4 Beds ⋅ 6 Baths ⋅ 73499730 MLS

Refined Vineyard living in The Preserve. Set on a knoll overlooking the pond and sweeping grasslands, this exceptional home blends classic coastal architecture with modern luxury. The expansive great room showcases cathedral ceilings, rich millwork, and abundant natural light, with three sets of French doors opening to a bluestone patio with multiple sitting areas and a heated saltwater pool. The chef’s kitchen flows seamlessly into the dining and living spaces. One wing offers an inviting lounge and a luxurious primary suite with spa-like bath and dressing room, while the opposite wing features three guest bedrooms, each with ensuite baths and walk-in closets. Additional highlights include a proper mudroom and a finished lower level with media room, full bath, and storage. Surrounded by mature landscaping, with easy access to trails, the bike path and Farm Neck Golf Club. The Preserve is a private enclave of luxury homes and is arguably one of Oak Bluffs most exclusive neighborhoods.

8 Paddock Rd, Oak Bluffs

$5,295,000

3 Beds ⋅ 7 Baths ⋅ 73496934 MLS

Set along 125 feet of private Lagoon frontage, this beautifully designed home offers over 5,400 sq. ft. of light-filled living space across three levels. High ceilings, skylights, and walls of glass capture sweeping water views, while a decorative stone fireplace anchors the main living area. The chef’s kitchen features stainless appliances, stone counters, custom cabinetry, and a large island, complemented by a wet bar and casual dining area. Three ensuite bedrooms include a primary suite with water views, a sitting area, walk-in closet, pool access, and a spa-like bath. The walk-out lower level offers a game room, media area, kitchenette, wine storage, and bonus room. Outdoors, enjoy a heated pool, spa, bluestone terrace, and direct access to calm waters for swimming, boating, and some of the best steamers, littleneck, and cherry stones on the Island. Offered furnished with strong rental history.

385 Barnes Road, Oak Bluffs

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