Oak Bluffs Real Estate

Welcome to Oak Bluffs, a charming gem nestled on the picturesque Martha's Vineyard in Dukes County, Massachusetts. Known for its vibrant history and stunning coastal beauty, Oak Bluffs offers a unique blend of small-town charm and rich cultural experiences.

This delightful seaside town is famous for its colorful gingerbread cottages, which line the streets and evoke a sense of whimsy and nostalgia. Originally built in the late 19th century as part of a Methodist camp meeting, these homes now serve as a reminder of the town’s historic roots and add to its enchanting atmosphere.

Oak Bluffs is also home to the iconic Flying Horses Carousel, the oldest operating carousel in the United States, where visitors of all ages can enjoy a ride on beautifully carved wooden horses. The town boasts beautiful beaches, such as Inkwell Beach and Joseph Sylvia State Beach, perfect for sunbathing, swimming, and enjoying breathtaking sunsets over the Atlantic.

For those who appreciate the arts, Oak Bluffs offers a vibrant local scene with galleries, craft fairs, and live performances throughout the summer months. The town’s dining options are equally impressive, featuring fresh seafood and local cuisine that will tantalize your taste buds.

With its friendly community, stunning landscapes, and a plethora of activities, Oak Bluffs is not just a destination; it’s a lifestyle. Whether you’re looking to invest in a vacation home or seeking a permanent residence, Oak Bluffs invites you to experience its charm and warmth. Come discover the magic of this coastal paradise!

Newest Listings in Oak Bluffs

$2,200,000

3 Beds ⋅ 3 Baths ⋅ 73576858 MLS

Location, location, location: This 1999 home with all the comforts of the 21st Century is nestled on a landscaped lot within mellow surroundings. And yet … it’s located within mere moments of town, beach, bike path, bus line, parks, recreation, Farm Pond and a Land Bank trail. The situation hardly gets better. The 3BR/2.5BA house features a deep wraparound farmer’s porch, Brazilian cherry floors, an open and flexible layout, recent kitchen and bath updates, a generous 2nd floor bonus room and an attached single-car garage. The poured basement stands ready for your finishing whims. Kick back in your sunny backyard or on your shady porch with the distant peek of Nantucket Sound. Songbirds will serenade you from towering maples and oaks. Pinkletinks will chime in from Farm Pond. It’s no wonder that this abode has been loved – by vacation tenants as well as the owner. Note: This property lies within the jurisdiction of the Cottage City Historic District and Copeland District of the Town of Oak Bluffs. Passed Title 5.

61 Canonicus Ave, Oak Bluffs

$1,755,000

3 Beds ⋅ 3 Baths ⋅ 22604610 MLS

Located on a quiet street in Oak Bluffs, this beautifully expanded Cape offers generous living space plus 700+ square feet of newly finished recreation space above the two-car garage, with a private entrance and second-floor deck. The inviting first floor features a spacious kitchen with center island and abundant counter space, an adjacent dining room with wood stove, and glass doors opening to a wood deck and bluestone patio. Multiple sitting areas, a living room with gas fireplace, and private office provide flexible spaces for relaxing and working. Upstairs, two guest bedrooms share an updated bath, while the spacious primary suite features a walk-in closet and light-filled bath with soaking tub and tiled shower. Radiant-heated floors in the primary bedroom and bath add comfort. Additional amenities include a two-car garage and half basketball court. Conveniently located near Downtown Oak Bluffs and Farm Neck Golf Club, this versatile home offers an ideal setting for relaxed island living and entertaining.

68 Front Street, Oak Bluffs

$1,755,000

3 Beds ⋅ 3 Baths ⋅ 73576389 MLS

Located on a quiet street in Oak Bluffs, this beautifully expanded Cape offers generous living spaces, along with an additional 700+ square feet of newly finished recreation space above the two-car garage, complete with a private entrance and second-floor deck. The inviting first floor is designed for comfortable living and entertaining, featuring a spacious kitchen with a center island and abundant counter space. The adjacent dining room provides a warm gathering space with a wood stove, while glass doors open to a wood deck and bluestone patio for easy indoor-outdoor living. Multiple sitting areas, a living room with a gas fireplace, and a private office offer plenty of room to relax, gather, or work. Upstairs, two guest bedrooms share a recently updated bathroom, while the spacious primary suite features a walk-in closet and a large, light-filled bath with a soaking tub and tiled shower. Radiant-heated floors in the primary bedroom and bathroom provide an added level of comfort. Additional amenities include a two-car garage, versatile recreation space, second-floor deck, and half basketball court. Conveniently located near Downtown Oak Bluffs and Farm Neck Golf Club, this home offers an ideal setting for enjoying all that Martha’s Vineyard has to offer.

68 Front Street, Oak Bluffs

$850,000

22604582 MLS

Build Your Dream Home. Close to town and all that Oak Bluffs has to offer, Roger's Way is a small enclave offering a wonderful opportunity to create your own Vineyard retreat. A paved road leads to 15 Roger's Way, one of the last remaining lots in this desirable neighborhood. A three-bedroom septic system is already installed, and electric access is available at the edge of the property. Bring your vision and create your Vineyard dream home.

15 Roger's Way, Oak Bluffs

$5,000,000

2 Baths ⋅ 73572959 MLS

Location, Location, Location! A once-in-a-lifetime legacy investment opportunity in one of the most desirable and high-visibility locations on Martha’s Vineyard. Priced to sell and positioned for success, 3 Oak Bluffs Ave is prominently situated at the corner of Seaview Ave and Oak Bluffs Ave—you know the spot. This exceptional property places your business directly in the center of it all, with unmatched exposure to both pedestrian and vehicular traffic. Located directly across from Inkwell Beach, Ocean Park, The Steamship Authority and SeaStreak ferry terminals, and Circuit Ave, and just around the corner from Oak Bluffs Harbor, this is a location that simply speaks for itself. And there’s more: the entire on-site parking lot belongs to this property, providing plenty of dedicated parking, with additional parking options available throughout the surrounding area. In a location where parking can be at a premium, this is a significant advantage. Whether you’re looking to relocate an existing business, expand your footprint, or launch your next venture, it’s hard to imagine a better location to bring your vision to life. Put your business at the gateway to Martha’s Vineyard, take advantage of extraordinary visibility and traffic, and position yourself for long-term success. B1 Zoning allows for a variety of commercial uses, offering flexibility for a range of business opportunities. Opportunities of this caliber—and in a location this prominent—rarely come along. This one won’t last. Secure this incredible property and invest in a location that could become the foundation of your next great success.

3 Oak Bluffs Avenue, Oak Bluffs

$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

$389,000

1 Beds ⋅ 2 Baths ⋅ 22604260 MLS

Welcome to Unit 38G at the Island Inn, offering resort-style living in an exceptional Oak Bluffs location just steps from the beach. This desirable ground-floor end unit features a large glass slider opening to the patio, with stairs leading to the heated outdoor pool just a few feet away. Accommodating up to six guests, the unit features one bedroom with a queen bed, a separate sleeping area partially divided by a 4' wall with two single beds, a sofa bed, 1.5 baths, and a small kitchen with a two-burner cooktop. The Island Inn is a seasonal resort community, open April-October, with beautifully maintained grounds, heated pool, three association clay tennis courts, outdoor fire pits, and easy access to downtown Oak Bluffs, beaches, restaurants, shops, ferries, golf, and boating. The popular Noman's outdoor family restaurant is directly next door, offering dining, cocktails, lawn games, live entertainment, and a pet-friendly atmosphere. Gulph Creek Management is conveniently located on site and handles rentals, bookings, cleaning, repairs, and maintenance. Just bring your luggage and enjoy your piece of paradise! Ideal as a Vineyard getaway, investment, or combination of personal use and rental income. Showings during turnovers only, 10AM-3PM. Proof of funds required

21 Island Inn Road, Oak Bluffs

$287,500

1 Beds ⋅ 1 Baths ⋅ 22604264 MLS

Welcome to 27 Island Inn, Unit 9C, an inviting Martha's Vineyard retreat offering the perfect combination of personal enjoyment and rental opportunity. This comfortable studio accommodates up to four guests with two double beds, a full bath, kitchenette with a 2-burner cooktop, cable TV and free WiFi. A unique opportunity is adjoining Unit 10C, a separate 1-bedroom, 1-bath suite accommodating up to four guests with a queen bed, sofa bed, cozy living area, well-equipped kitchenette with 2-burner cooktop, and patio/deck. Units 9C and 10C can be enjoyed separately or together through the adjoining door. Each is being offered for sale separately, with the opportunity to purchase both together—ideal for additional family, guests or expanded rental possibilities. Island Inn is a seasonal resort, open April through October, offering a relaxed, pet-friendly setting with a heated outdoor pool, 3 association clay tennis courts, grilling areas, fire pits and spacious grounds. Directly next door is the popular and pet-friendly Noman's, offering outdoor dining, cocktails, lawn games and entertainment. Ideally located between Oak Bluffs and Edgartown, you're minutes from beaches, golf, shops, restaurants, ferries and Oak Bluffs Harbor. On-site Gulph Creek Management handles virtually every aspect of the rental operation, including bookings, guest coordination, cleaning, repairs and maintenance. Just bring your luggage and enjoy your piece of paradise! Ideal as a Vineyard getaway, investment, or combination of personal use and rental income. Showings during turnovers only, 10AM-3PM. Proof of funds required.

27 Island Inn Road, Oak Bluffs

$310,000

1 Beds ⋅ 1 Baths ⋅ 22604263 MLS

Welcome to 27 Island Inn, Unit 10C, a comfortable one-bedroom, one-bath Martha's Vineyard retreat offering an ideal combination of personal enjoyment and rental opportunity. Accommodating up to four guests, 10C features a queen bedroom, sofa bed, cozy living area, well-equipped kitchenette. A unique feature is the adjoining door to Unit 9C, a studio with two double beds, full bath and kitchenette. Units 9C and 10C are being offered for sale separately, with the opportunity to purchase both together—perfect for extended family, guests, or expanded rental possibilities while still allowing each unit to be used independently. Island Inn is a seasonal resort, open April through October, offering a relaxed, pet-friendly setting with a heated outdoor pool, 3 association clay tennis courts, grilling areas, fire pits and spacious grounds. Directly next door is the popular pet-friendly Noman's, featuring outdoor dining, cocktails, lawn games and entertainment. Ideally located between Oak Bluffs and Edgartown, just minutes from beaches, golf, shops, restaurants, ferries and Oak Bluffs Harbor. On-site Gulph Creek Management handles virtually every aspect of the rental operation, including bookings, guest coordination, cleaning, repairs and maintenance. Just bring your luggage and enjoy your piece of paradise! Ideal as a Vineyard getaway, investment, or combination of personal use and rental income. Showings during turnovers only, 10AM-3PM. Proof of funds required.

27 Island Inn Road, Oak Bluffs

$260,000

1 Beds ⋅ 1 Baths ⋅ 22604259 MLS

Welcome to 27 Island Inn, Unit 25F, a comfortable studio offering the perfect combination of a Martha's Vineyard getaway and rental opportunity. Accommodating up to four guests, this inviting unit features two double beds, one full bath, a convenient kitchenette, cable TV and free WiFi. Island Inn is a seasonal resort, open April through October, offering a relaxed, pet-friendly setting with a heated outdoor pool, 3 association clay tennis courts, grilling areas, fire pits and spacious grounds. Directly next door is the popular pet-friendly Noman's, featuring outdoor dining, cocktails, lawn games and entertainment. Ideally located between Oak Bluffs and Edgartown, just minutes from beaches, golf, shops, restaurants, ferries and Oak Bluffs Harbor. On-site Gulph Creek Management handles virtually every aspect of the rental operation, including bookings, guest coordination, cleaning, repairs and maintenance, making ownership easy and convenient. Just bring your luggage and enjoy your piece of paradise! Ideal as a Vineyard getaway, investment, or combination of personal use and rental income. Showings during turnovers only, 10AM-3PM. Proof of funds required.

33 Island Inn Road, Oak Bluffs

$789,000

73568028 MLS

OAK BLUFFS - EIGHT (8) BEDROOM LOT. This already cleared, oversized lot, 16,895sq.ft., (more than 1/3 acre) comes with an Approved Eight (8) Bedroom Septic Design, ready to build. Exceptional potential for a spacious custom home, family compound, or a rental property. Utilities are available by the lot, which significantly reduces development costs and time. Convenient access from both Towanticut Avenue and Oak Avenue, increases flexibility for design options, access and privacy. Walking distance to Oak Bluffs Harbor, Oak Bluffs Library, Sunset Lake, Campground cottages, shops, restaurants, Oak Bluffs Ferry, beaches and local entertainment. This property is ideal for seasonal enjoyment, multigenerational living, or a strong rental in one of Martha’s Vineyard’s most desirable markets. A chance to acquire a ready to build lot with tons of potential, substantial bedroom capacity, options for two structures, offering long-term and enduring value & BUILDING PERMIT in place for an ADU. This could be yours! Ready to go.

24 Towanticut St, Oak Bluffs

$5,500,000

6 Baths ⋅ 73566891 MLS

Exceptional mixed-use property in the heart of Oak Bluffs thriving high-foot-traffic Circuit Avenue business district. Meticulously renovated and designed by architect Chuck Sullivan, this distinctive building combines sophisticated commercial and residential spaces with outstanding craftsmanship and state-of-the-art systems. The street level is 2,320 sf and offers exceptional flexibility for restaurant-bar and/or retail operators (a commercial kitchen and bar remain intact) and includes three handicapped accessible half baths and a covered rear exterior loading area. A very large newly excavated 1,717 sf basement provides rare clean, dry storage and auxiliary operational space. The second-floor with 1,669 sf, features two residential apartments, totaling six bedrooms and three full baths for income potential or owner flexibility. Formerly housing an A&P grocery store (The Great Atlantic & Pacific Tea Company) and 99-occupancy restaurants, the property presently houses an upscale retailer while retaining its restaurant-bar infrastructure for future use.

53 Circuit Avenue, Oak Bluffs

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