Oak Bluffs Condos for Sale

Oak Bluffs Condos for Sale

Welcome to Oak Bluffs, a picturesque gem nestled on Martha's Vineyard in Dukes County, Massachusetts. Known for its vibrant arts scene, stunning beaches, and charming Victorian architecture, Oak Bluffs offers a unique blend of coastal living and small-town charm. The town is famous for its colorful gingerbread cottages and the historic carousel, making it a delightful destination for both residents and visitors alike.

As you explore the enchanting streets of Oak Bluffs, you’ll discover an array of boutique shops, cozy cafes, and delectable dining options that cater to every palate. The local beaches, including the beautiful Inkwell Beach, provide the perfect backdrop for sunbathing, swimming, and enjoying breathtaking sunsets over the Atlantic Ocean. With a thriving community spirit and a calendar packed with events, from summer fairs to art exhibitions, Oak Bluffs is a place where life feels vibrant and full of possibilities.

For those looking to make Oak Bluffs their home, there’s an exciting opportunity to explore condos for sale in this idyllic setting. These condos offer a perfect blend of comfort and convenience, often featuring modern amenities, stunning views, and easy access to the town’s attractions. Whether you’re seeking a cozy retreat for summer getaways or a year-round residence, Oak Bluffs condos provide an ideal solution for enjoying all the beauty and charm that this coastal paradise has to offer. Embrace the lifestyle you’ve always dreamed of in Oak Bluffs, where every day feels like a vacation!

Newest Oak Bluffs Condos for Sale

$869,000
1 Beds ⋅ 1 Baths ⋅ 22602409 MLS
In the heart of Downtown Oak Bluffs walk to everything from this Circuit Avenue location Unit #5 comes with an amazing roof top deck that is only shared with one other condo (#4). This well appointed sleeps 4 with custom wood features and a staircase to the roof top deck. This condo packs a lot in with a full kitchen, living and dining area,, large bedroom with alcove, a sleep nook, a tiled bathroom with tub shower enclosed shower. You're in the middle of it all with this great location, steps away from restaurants, shops, beaches and transportation, yet you have easy access to a peaceful deck where you'll have panoramic views overlooking the town of Oak Bluffs and the surrounding waters. Enjoy watching the boats in the harbor or having diner under the stars, Leave the car behind you don't need it.

37 Circuit Avenue, Oak Bluffs
$899,000
2 Beds ⋅ 1 Baths ⋅ 22602411 MLS
In the heart of Downtown Oak Bluffs this Restless Winds Penthouse condominium Unit #4 on 2nd floor comes with an amazing roof top deck that is only shared with one other condo (#5). This spacious unit just under 1,000 sq. ft. has a nautical feel with custom wood features and a ships ladder leading to the roof top deck. This condo packs a lot in with a full kitchen, living and dining area, a guest bedroom, a tiled bathroom with glass enclosed shower, and a large primary bedroom that's over 16'x21'. You're in the middle of it all with this great location, steps away from restaurants, shops, beaches and transportation, yet you have easy access to a peaceful deck where you'll have panoramic views overlooking the town of Oak Bluffs and the surrounding waters. Enjoy watching the boats in the harbor or having diner under the stars, Leave the car behind you don't need it.

37 Circuit Avenue, Oak Bluffs
$1,595,000
3 Beds ⋅ 4 Baths ⋅ 22603277 MLS
Enjoy timeless summers at this Hidden Cove condo, where days begin with a paddle on Sengekontacket Pond, afternoons are spent between the pool and tennis courts, and evenings end on the deck after a day spent exploring the island. This three-bedroom unit has distant water views and offers an easy, multi-level floor plan with open living spaces, a private primary suite, two guest bedrooms, a detached garage, and exclusive access to Hidden Cove's sought-after amenities, including a private boat launch. Just minutes from Oak Bluffs, Farm Neck Golf Club, beaches, and the bike path, this is a place where generations return to create the kind of Martha's Vineyard summers that never go out of style.

40 Hidden Cove Road, Oak Bluffs
$1,075,000
3 Beds ⋅ 2 Baths ⋅ 73552744 MLS
Located within the historic Martha’s Vineyard Camp Meeting Association, this rare double-lot property combines classic Campground charm with modern comfort. Two-car off-street parking—an exceptional Campground amenity—adds convenience, while Oak Bluffs Harbor, beaches, ferries, shops, and restaurants are just moments away. The 1,135-square-foot home features painted wood floors, abundant natural light, vintage details, and flexible living spaces for gathering, guests, or a home office. Unlike many Campground cottages, it is fully winterized with a four-zone heat pump system providing efficient heating and air conditioning, plus a propane on-demand water heater. Significant improvements include updated electrical and lighting, newer appliances, kitchen built-ins, foundation work, and a sealed, dry crawlspace. Outside, the fenced yard, expanded brick patio, shade sails, cooling fan, outdoor television, and large storage shed create a private retreat rarely found in the Campground.

21 Butler Avenue Unit 1, Oak Bluffs
$1,595,000
3 Beds ⋅ 4 Baths ⋅ 22603277 MLS
Enjoy timeless summers at this Hidden Cove condo, where days begin with a paddle on Sengekontacket Pond, afternoons are spent between the pool and tennis courts, and evenings end on the deck after a day spent exploring the island. This three-bedroom unit has distant water views and offers an easy, multi-level floor plan with open living spaces, a private primary suite, two guest bedrooms, a detached garage, and exclusive access to Hidden Cove's sought-after amenities, including a private boat launch. Just minutes from Oak Bluffs, Farm Neck Golf Club, beaches, and the bike path, this is a place where generations return to create the kind of Martha's Vineyard summers that never go out of style.

40 Hidden Cove Road, Oak Bluffs
$899,000
2 Beds ⋅ 1 Baths ⋅ 22602411 MLS
In the heart of Downtown Oak Bluffs this Restless Winds Penthouse condominium Unit #4 on 2nd floor comes with an amazing roof top deck that is only shared with one other condo (#5). This spacious unit just under 1,000 sq. ft. has a nautical feel with custom wood features and a ships ladder leading to the roof top deck. This condo packs a lot in with a full kitchen, living and dining area, a guest bedroom, a tiled bathroom with glass enclosed shower, and a large primary bedroom that's over 16'x21'. You're in the middle of it all with this great location, steps away from restaurants, shops, beaches and transportation, yet you have easy access to a peaceful deck where you'll have panoramic views overlooking the town of Oak Bluffs and the surrounding waters. Enjoy watching the boats in the harbor or having diner under the stars, Leave the car behind you don't need it.

37 Circuit Avenue, Oak Bluffs
$869,000
1 Beds ⋅ 1 Baths ⋅ 22602409 MLS
In the heart of Downtown Oak Bluffs walk to everything from this Circuit Avenue location Unit #5 comes with an amazing roof top deck that is only shared with one other condo (#4). This well appointed sleeps 4 with custom wood features and a staircase to the roof top deck. This condo packs a lot in with a full kitchen, living and dining area,, large bedroom with alcove, a sleep nook, a tiled bathroom with tub shower enclosed shower. You're in the middle of it all with this great location, steps away from restaurants, shops, beaches and transportation, yet you have easy access to a peaceful deck where you'll have panoramic views overlooking the town of Oak Bluffs and the surrounding waters. Enjoy watching the boats in the harbor or having diner under the stars, Leave the car behind you don't need it.

37 Circuit Avenue, Oak Bluffs
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