Oak Bluffs Homes with Cottage Style

Welcome to Oak Bluffs, a picturesque gem nestled on Martha's Vineyard in Dukes County, Massachusetts. Known for its vibrant community and stunning coastal views, Oak Bluffs is a delightful blend of charming history and modern living. This enchanting town is famous for its colorful gingerbread cottages, which add a whimsical touch to the landscape and reflect the rich heritage of summer vacationing on the island.

As you explore Oak Bluffs, you'll discover a variety of homes that embody the quintessential cottage style. These quaint dwellings, often adorned with intricate woodwork and cheerful colors, invite you to embrace the relaxed island lifestyle. Imagine waking up in a cozy cottage with the gentle sound of waves lapping at the shore, just a short stroll away from the beautiful beaches and bustling harbor.

Oak Bluffs is not just about stunning homes; it’s a community that thrives on its vibrant culture. The town offers a lively array of restaurants, shops, and art galleries, ensuring there’s always something to explore. Enjoy a leisurely bike ride along the scenic paths, or take a ferry ride to nearby islands. The local farmers' market is a must-visit, showcasing the best of Martha's Vineyard's fresh produce and artisanal goods.

Whether you're seeking a summer retreat or a year-round residence, Oak Bluffs’ cottage-style homes provide the perfect sanctuary. With their charm and character, these homes are a testament to the town's rich history and a gateway to a lifestyle filled with sun, sea, and community. Come experience the magic of Oak Bluffs—your dream cottage awaits!

Newest Oak Bluffs Homes with Cottage Style

$1,745,000

2 Beds ⋅ 1 Baths ⋅ 22603245 MLS

Oceanfront Cottage on .21 acre of waterfront property and over 50ft of shoreline on East Chop.Wake up to breathtaking ocean views and the soothing sound of waves from this charming two-bedroom oceanfront cottage. Perfectly positioned along the shoreline, this inviting coastal retreat offers the rare opportunity to own a slice of waterfront paradise.Designed for relaxed seaside living, the home features a bright, open living area filled with natural light, a eat-in kitchen, and two comfortable bedrooms that provide a peaceful escape after a day by the water. Expansive windows frame spectacular ocean vistas, while a spacious open porch is ideal for morning coffee, sunset dinners, or simply enjoying the ever-changing seascape.Whether you're looking for a vacation getaway, or an investment property, this cottage offers timeless coastal charm in an unbeatable location. Just imagine what you could build on this magnificent property.

11 Beach Road, Oak Bluffs

$1,575,000

3 Beds ⋅ 3 Baths ⋅ 73540741 MLS

Located in exclusive East Chop, this sun-filled 3BR Cottage blends authentic Martha’s Vineyard charm with modern coastal living. Immaculate, fully furnished, and turn-key, this property presents a phenomenal island retreat or a lucrative investment with fantastic rental potential.The main home pairs classic character with upgraded 200-amp electric, featuring bright spaces, a large kitchen, and inviting living areas. Step outside to an expansive Trex deck, manicured corner lot, and the quintessential outdoor shower. A standout feature is the separate detached bonus room: a spectacular flex space with a kitchenette and beautiful full bath—perfect for guest privacy or extended family gatherings.Unbeatable location just minutes to Oak Bluffs town center, the ferry, Marinelli Beach..

27 Laurel Avenue, Oak Bluffs

$1,199,000

3 Beds ⋅ 2 Baths ⋅ 22602630 MLS

Oak Bluffs -East Chop-Close to the beach. Two Year-round cottages on one lot. Stay in one and rent the other, the possibilities are great with this amazing opportunity to own close to the beach and just a mile to Oak Bluffs center. The front house is two bedrooms 1 bath: freshly painted with new flooring. The second home nestled in the back of the lot is an open floor plan with one bedroom, one bath, and a separate utility room. Recent upgrades includes new roofs, new electrical service in front house, and a new 3-bedroom title 5 septic system.

47 Winemack Street, Oak Bluffs

$825,000

2 Beds ⋅ 1 Baths ⋅ 73522647 MLS

Located under a mile from the heart of downtown Oak Bluffs, this charming property offers endless potential in a highly convenient location. Set on a level lot, the home is ready for its next chapter — whether as a summer getaway or year-round residence. Enjoy easy access to town, beaches, ferries, restaurants, and shops while creating your own vision in this classic Island setting.

19 Perkins Avenue, Oak Bluffs

$899,000

2 Beds ⋅ 1 Baths ⋅ 22505096 MLS

Rare Opportunity to Be in a Special Location and Neighborhood! Loved by generations, this quintessential Vineyard cottage has been in the same family since its creation in 1900. Step back in time and enjoy easy cottage living of yesteryear with modern updates including newer windows and electrical. Nestled under mature trees and just .3 mile to Inkwell Beach, join this close-knit neighborhood and make this house your island home. Close to the beach, town, bike path, and more, this home sits in a special location. It is also part of both the Cottage City and Copeland Districts. The property is over 100 years old but not on the MACRIS registry. Buyers should research the process for making major renovations.Home is being sold ''as is''. Septic is a functioning cesspool but it will need to be upgraded. Basic engineering is being completed and a septic plan is being drawn up. It will be the Buyer's responsibility to have the plan approved and complete the installation as part of the overall plan for the property. Buyers should consult an architect about the process for completing major renovations.

50 Canonicus Avenue, Oak Bluffs

Start Your Search

The property listing data and information, or the Images, set forth herein were provided to MLS Property Information Network, Inc. from third party sources, including sellers, lessors, landlords and public records, and were compiled by MLS Property Information Network, Inc. The property listing data and information, and the Images, are for the personal, non commercial use of consumers having a good faith interest in purchasing, leasing or renting listed properties of the type displayed to them and may not be used for any purpose other than to identify prospective properties which such consumers may have a good faith interest in purchasing, leasing or renting. MLS Property Information Network, Inc. and its subscribers disclaim any and all representations and warranties as to the accuracy of the property listing data and information, or as to the accuracy of any of the Images, set forth herein.