Oak Bluffs Homes for Sale

Welcome to Oak Bluffs, a picturesque gem nestled on Martha’s Vineyard in Dukes County, Massachusetts. This charming town is renowned for its stunning beaches, vibrant arts scene, and rich history. With its iconic gingerbread cottages and quaint Victorian architecture, Oak Bluffs offers a unique blend of coastal charm and modern amenities, making it a perfect destination for families, retirees, and anyone seeking a serene escape.

Oak Bluffs boasts a lively atmosphere, with an array of shops, restaurants, and recreational activities. Spend your days lounging on the beautiful beaches, exploring the scenic bike paths, or taking a leisurely stroll through the historic Oak Bluffs Camp Meeting Association. Don’t miss the iconic Flying Horses Carousel, the oldest operating carousel in the United States, which is sure to delight visitors of all ages.

For those considering making Oak Bluffs their home, the real estate market is thriving, with a variety of homes for sale to suit every lifestyle. From charming cottages and oceanfront properties to luxurious estates, there’s something for everyone. Whether you're searching for a cozy retreat or a spacious family home, Oak Bluffs offers a diverse selection of properties that capture the essence of island living.

With its welcoming community, breathtaking landscapes, and endless recreational opportunities, Oak Bluffs is not just a place to live; it’s a lifestyle. Discover your dream home in this enchanting town and experience all that Oak Bluffs has to offer. Your perfect island retreat awaits!

Newest Oak Bluffs Homes for Sale

$4,395,000

3 Beds ⋅ 6 Baths ⋅ 73572956 MLS

Set along 163 feet of Lagoon frontage with its own sandy beach, 267 Barnes Road offers a fresh, contemporary take on waterfront living in Oak Bluffs. Set on 1.25 acres, the 4,046-square-foot home balances privacy with comfortable spaces for entertaining or relaxing. Oversized windows bring Lagoon views into nearly every room. The main level features soaring ceilings, a wood-burning fireplace, wet bar, and an eat-in kitchen opening to a sunny patio. A separate two-room wing with full bath and private deck offers flexible space for an office, den, studio, or guest accommodations. Upstairs, the primary suite includes a fireplace, walk-in closets, ensuite bath, and Lagoon-facing deck. Two additional ensuite bedrooms open to a wraparound deck and 3-season porch. The refinished 2,000-square-foot walk-out lower level includes a full bath, laundry, and space for a gym, media room, or additional living area. Offered fully furnished, this waterfront retreat is ready to enjoy. Whether you are hosting a full house or savoring a quiet weekend, the Lagoon becomes your backdrop: sunrise coffees, afternoon swims, and sunset gatherings right at the water’s edge.

267 Barnes Road, Oak Bluffs

$2,678,000

4 Beds ⋅ 4 Baths ⋅ 22604054 MLS

Due to ongoing construction, the property may pose safety risks. Entry is at your own risk, and access is permitted only when accompanied by a licensed real estate agent. The agent of the buyer must be present at all buyer-client showings, inspections, and walkthroughs unless otherwise agreed to in advance by the listing agent.

31 Temahigan Avenue, Oak Bluffs

$2,995,000

5 Beds ⋅ 2 Baths ⋅ 22604007 MLS

WATERFRONT WITH DOCK - Nestled along the sparkling shores of Vineyard Haven Harbor, this waterfront cottage presents a rare opportunity to own a piece of Martha's Vineyard history. Originally part of the iconic Mary Guerin Inn, the home blends timeless Vineyard charm with an exceptional setting featuring a private sandy beach, deep-water dock, and sweeping views of the harbor, the Cape, and Nantucket Sound. The home offers five bedrooms, one full bathroom, and one half bathroom, with an open concept living and dining area where walls of windows capture the harbor views and abundant natural light. The kitchen is ideally positioned for effortless indoor and outdoor entertaining. Rich in character, the home retains many original architectural details while benefiting from thoughtful updates, including all new windows, a new roof, beautiful mahogany porches, and new cedar shingles. Whether enjoyed as a treasured family retreat or reimagined into your dream waterfront escape, the possibilities are endless. Enjoy water views from virtually every room as the home's spectacular waterfront setting seamlessly extends to your private sandy beach and deep-water dock.

27 Beach Road, Oak Bluffs

$1,095,000

3 Beds ⋅ 2 Baths ⋅ 22603994 MLS

Located at the southern end of Winemack Street, this inviting 3-bedroom, 2-bath Oak Bluffs home offers a quiet residential setting in a neighborhood of both year-round and seasonal homes, while remaining remarkably close to everything Oak Bluffs has to offer. Just approximately 1.2 miles from downtown, you'll enjoy convenient access to the ferries, Oak Bluffs Harbor, beaches, shopping, restaurants, and all the attractions that make this area of Martha's Vineyard so special. Martha's Vineyard Hospital is also just a short two-minute drive away. Built in 1988, the home offers approximately 1,456 square feet of living area, with prefinished wood flooring in the living room and bedrooms. The roof is approximately 10 years old, and recent improvements have focused primarily on the basement, where the space has been transformed to expand the home's usable living and recreational area. Whether you envision a TV room, game room, home office, exercise area, or a combination of uses, there are plenty of possibilities. A newly completed "doghouse"-style exterior basement entry provides convenient direct access to the lower level. The first and second floors would benefit from a little TLC and personal touches to brighten and refresh the space, providing a great opportunity for the next owner to make the home their own. Outside, the property offers a small, manageable yard with off-street parking, along with a classic Vineyard outdoor shower—a favorite feature after a day at the beach and something many consider a must-have for Island living. Set on a 5,000-square-foot lot, the property offers the best of both worlds—a quieter location at the Eastville side of Winemack Street while still being just minutes from downtown Oak Bluffs. Title 5 System failed, Seller is offering a credit at closing to help with costs (to be determined). Prequalification letter from your lending source or proof of funds required. Owner and tenants currently occupy the home; 24-hour notice for showings is preferred.

2 Winemack Street, Oak Bluffs

$1,255,000

3 Beds ⋅ 2 Baths ⋅ 22603967 MLS

Nestled on a cul-de-sac is this sweet 3 bedroom ranch. Located on a .34 acre lot with plenty of room to expand this solid home and still have enough space for an ADU on this spacious lot. Well maintained over the years with recent upgrades including, roof, siding, new insulation, flooring and paint. Natural light floods the house from the bank of windows in the living room to the sliding glass doors in the dining area leading to the deck. A spacious garden shed with a front porch and electricity complete the yard. Plenty of room for a nice pool to make those summer days extra special.

11 Stanley Street, Oak Bluffs

$1,225,000

1 Beds ⋅ 2 Baths ⋅ 22603763 MLS

This charming Cape-style home is set on a beautifully landscaped lot filled with colorful blooming perennials, offering a peaceful setting just off the bike path. Ideally located, it's only a short ride to the town center and ferry, making it an excellent year-round residence, vacation getaway, or proven income-producing investment. The home features a bright, open-concept kitchen, dining, and living area with beautiful hardwood floors that create a warm and inviting atmosphere. A first-floor den, complete with a daybed, provides flexible space for two additional overnight guests, while a full bathroom on the main level adds convenience. Sliding glass doors from the dining area open to a spacious deck overlooking the beautifully landscaped gardens, creating the perfect setting for outdoor dining, entertaining, or simply relaxing. Additional outdoor amenities include a hot tub and an outdoor shower, allowing you to fully enjoy the Vineyard lifestyle. Upstairs, you'll find a spacious primary bedroom, a large open loft that can serve as an additional living or sleeping area, and a second full bathroom. Adding even more value, the home is equipped with transferable solar panels .

323 County 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

$1,100,000

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

$849,000

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

$5,495,000

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

$794,000

2 Beds ⋅ 1 Baths ⋅ 22603182 MLS

Charming Oak Bluffs Retreat Near Town Tucked away down a quiet lane just moments from downtown Oak Bluffs, this charming home offers the perfect blend of simplicity, comfort, and convenience. Set on just over 8,400 square feet, the property provides easy, single-story living in a sought-after Oak Bluffs neighborhood. The bright, open-concept interior features a welcoming living area and kitchen with a breakfast bar, ample storage, and a stackable washer and dryer. Two comfortable bedrooms and a full bath complete the home. Step outside and enjoy seamless indoor-outdoor living from the expansive wrap-around deck—perfect for morning coffee, afternoon lounging, or entertaining friends. After a day at the beach, rinse off in the quintessential Vineyard outdoor shower. A spacious barn-style shed provides abundant storage and could easily serve as a workshop, studio, or she-shed. Conveniently located near downtown Oak Bluffs, the Lagoon, bike path, Martha's Vineyard Hospital, public library, and more, this adorable home is an ideal opportunity to create your own Vineyard retreat. 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

$1,295,000

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

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