Oak Bluffs Homes for Sale

Welcome to Oak Bluffs, a charming gem nestled on Martha’s Vineyard in Dukes County, Massachusetts. Known for its vibrant community and stunning coastal views, Oak Bluffs offers a unique blend of picturesque landscapes, rich history, and a lively atmosphere that captivates residents and visitors alike.

As you stroll through the town, you’ll be enchanted by the colorful gingerbread cottages that line the streets, a hallmark of the area’s Victorian architecture. The bustling Oak Bluffs Harbor invites you to enjoy a leisurely afternoon, whether you’re dining at one of the delightful waterfront restaurants or indulging in some of the finest local seafood. With beautiful beaches, serene parks, and a plethora of recreational activities, Oak Bluffs is perfect for families, retirees, and everyone in between.

For those looking to make this idyllic location their home, there are a variety of homes for sale that cater to diverse tastes and lifestyles. From charming cottages with historical significance to modern waterfront properties boasting stunning ocean views, Oak Bluffs has something for everyone. Whether you are seeking a seasonal retreat or a year-round residence, the real estate market here is vibrant and full of potential.

Don’t miss the chance to be part of this enchanting community. Explore the homes for sale in Oak Bluffs today and discover your dream home in this coastal paradise, where every day feels like a vacation!

Newest Oak Bluffs Homes for Sale

$5,995,000

3 Beds ⋅ 3 Baths ⋅ 22603599 MLS

Breathtaking property at the tip of a prominent peninsula on Sengekontacket Pond's western shoreline. Set beautifully at high elevation above the shore, this charming home and guest cottage includes jaw-dropping views of the pond, barrier dunes and Nantucket Sound. Direct from the property take your whaler or other watercraft out into the sound and beyond for endless recreational pursuits. Aside from boating, the swimming and clamming in the immediate waters are sublime. Expansive lawns slope down to the water on three sides of the residence - one of the most enchanting settings on the waterfront on Martha's Vineyard.

43 Sengekontacket Road, Oak Bluffs

$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

$794,000

2 Beds ⋅ 1 Baths ⋅ 22603182 MLS

Tucked away down a quiet lane just moments from downtown Oak Bluffs, sits this charming home. Nestled on just over an 8,400 sq. ft. lot, the property offers compact single-story living, ideal for those seeking simplicity while being close to everything the island. The bright, open concept features a living area and kitchen with breakfast bar. Ample storage and a stackable washer/dryer complete the kitchen. The home has two comfortable bedrooms and one full bath. Enjoy seamless indoor-outdoor living from the expansive wrap-around deck. After a day at the beach, rinse off in the requisite Vineyard amenity, the outdoor shower. A barn-style shed provides an enormous amount of storage or it can be a workshop space/she-shed. Conveniently located near downtown, access to the Lagoon, bike path, the hospital, public library and more, this property offers both practicality and charm in a sought-after Oak Bluffs neighborhood. An adorable home to make your own. The septic system has passed Title V inspection and is certified for two-bedrooms. Located in the R1 zoning district and in Zone 2, the property is subject to 20-foot setbacks on all sides. It is a pre-existing, non-conforming lot, so any additions to the structure will require approval from the Zoning Board of Appeals.

60R Carol Lane, Oak Bluffs

$1,750,000

3 Beds ⋅ 4 Baths ⋅ 22603069 MLS

GORGEOUS NEWER CONSTRUCTION (2023), contemporary farmhouse style home w/ classic wrap around porch & designed w/ Vineyard charm & modern comfort. And yet still there is opportunity to add value to this open concept home, w/ high ceilings, 3 en-suite BRs, laundry on each level, hardwoods throughout. Well designed, fully poured unfinished basement w/ high ceilings, wide open & w/ a separate entrance for an in-law or ADU. 1st FL en suite BR & a common half bath at the foyer entry. Large kitchen w/ full appliances & a 10' stone topped island for large gatherings. Gas fireplace in the family room, sliders to rear yard, a well-designed mudroom area w/ 1st FL laundry, large overflow pantry & a built in bench seating area. The 2nd FL offers 2 en-suite BRs, w/ a large common area. Close to the Lagoon & Sailing Camp Park.Short ride downtown- ideal for year round occupancy and/ or high season rentals. House related plans, professional photos, interior, exterior & aerial video avail upon request.

28 Grovedale Road, 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

$1,755,000

3 Beds ⋅ 3 Baths ⋅ 22602650 MLS

Nestled at the end of a quiet street, this charming and spacious Cape-style home offers both privacy and convenience, just a short distance from the Oak Bluffs School and town center, and walking distance to the Lagoon.Thoughtfully maintained, the sun-filled main level boasts an open floor plan with large windows that frame views of the surrounding property. The generously sized kitchen features abundant counter space and opens to the dining area, with sliding doors leading to a back deck and yard, perfect for entertaining or relaxing. Lovely blue stone patio in the back yard. Radiant heated floors bring cozy comfort to the primary master suite and basement playroom. There is a two car garage with bonus space above. The driveway parking area has lovely stonework in front of the garage. The furnace was replaced in 2020 and the water heater was replaced in 2024.A truly wonderful home.

68 Front Street, Oak Bluffs

$1,349,000

3 Beds ⋅ 2 Baths ⋅ 22602560 MLS

Set on a generous 0.3-acre lot in desirable Oak Bluffs, this property offers exceptional potential just moments from Vineyard Sound. A newly installed 6-bedroom septic system opens the door to a variety of expansion opportunities. The home is thoughtfully designed with two separate living areas, ideal for guests or rental possibilities. The main living space features hardwood floors throughout, a spacious living room with a fireplace, kitchen, sunroom, and a primary bedroom with a full bath. An additional shared living room serves as the central gathering space between the two wings of the home, creating a seamless and functional layout. The secondary living area includes a kitchenette, dining space, guest bedroom, and bathroom. The bathroom is currently unfinished, providing the next owner the opportunity to customize it to their taste. Upstairs, the second level boasts high ceilings, abundant natural light, a guest bedroom, and a private office space. Additional highlights include a two-car garage, a large rear deck, and a private backyard setting. An excellent investment or renovation opportunity in Oak Bluffs, offered as-is.

3 Troy Street, Oak Bluffs

$1,155,000

3 Beds ⋅ 2 Baths ⋅ 22602448 MLS

Recently updated Oak Bluffs ranch-style home ideally located near Downtown and Oak Bluffs Harbor. Step inside to discover vaulted ceilings and an airy open floor plan that seamlessly connects the living room, dining area, and a spacious kitchen featuring granite countertops and updated appliances. The private primary suite is thoughtfully positioned off the main living area and offers a full bath with in-suite laundry, plus its own separate exterior entrance, perfect for added privacy or guest flexibility. Two additional guest bedrooms and a full hall bath complete the interior layout. Outdoor living is equally inviting, with a charming front deck featuring built-in bench seating, a stone patio for entertaining, and a convenient storage shed. Recent upgrades include a new roof, updated flooring, and energy-efficient mini-split systems for heating and cooling. Move-in ready and perfectly suited for enjoying the Vineyard lifestyle.

3 Kims Way, Oak Bluffs

$1,850,000

4 Beds ⋅ 2 Baths ⋅ 73505800 MLS

Quintessential Waterview Farm! Built as a year-round home with the charm of the original cottages, this well-loved retreat awaits its next chapter. The sunny, open floor plan offers two bedrooms and a full bath on each level, with generous gathering spaces throughout. A skylit kitchen is tucked into a corner of the main living area, where a curved wall of glass opens to a deck and private yard. The sunken living room features a fireplace and stairs to a loft seating area. Built in 1978, the home is fully winterized with oil forced-air heat and a partial basement. The south facing half-acre lot abuts an 8-acre forever-wild meadow. A nearby path leads across wildflower fields to the association beach. Set between Farm Neck and Felix Neck, Waterview Farm offers 22 acres of common land, a sandy beach, dock, boat storage, and possible mooring—ready to enjoy now and enhance over time.

22 Old Harbor Lane, Oak Bluffs

$1,155,000

3 Beds ⋅ 2 Baths ⋅ 73478102 MLS

3 Kims Way, Oak Bluffs

$5,225,000

6 Beds ⋅ 4 Baths ⋅ 73472922 MLS

Overlooking Nantucket Sound and just steps from the vibrant heart of downtown Oak Bluffs, this distinctive compound blends laid-back West Coast style with classic island charm. The light-filled four-bedroom main house has been thoughtfully updated with modern, year-round comforts. Privately set at the rear, the guest house known as The Nest offers a peaceful retreat with a private deck, outdoor shower, parking, and mini-split climate control; its upstairs bedroom enjoys views from Farm Pond to Nantucket Sound. Completing the property is the charming Lilac House, a fun open-concept bunk house with a full bath, water-view deck, and private outdoor shower. A wraparound porch captures sweeping ocean views, while beaches, shops, restaurants, Circuit Avenue, and the Harbor are moments away. An established rental history further enhances this rare opportunity in one of Oak Bluffs’ most iconic locations.

4 Canonicus Ave, 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.