Refine Search
Sort by
20 Hidden Cove, Oak Bluffs
$1,595,000
4 Beds ⋅ 3 Baths ⋅ 73577547 MLS
Set within the sought-after Hidden Cove community, a 65-acre private enclave with direct access to Sengekontacket Pond, this contemporary retreat offers an exceptional Martha’s Vineyard lifestyle. Residents enjoy a private community boat dock, scenic walking trails, pickleball and tennis courts, all just moments from Oak Bluffs and Edgartown.Set on a private, wooded lot, the home blends classic Vineyard character with relaxed coastal living. Cedar siding, an expansive wood deck, screened porch, and outdoor shower create inviting spaces for everything from quiet mornings to long summer evenings and post-beach afternoons.Inside, the home unfolds around a striking two-sided gas and wood-burning fireplace, with large windows bringing the surrounding landscape indoors. Four bedrooms offer comfortable space for family and guests, while a finished lower level adds exceptional versatility — currently configured as a media room and home office, with an unfinished portion ready to become a private gym, wine cellar, or whatever you envision.With water access, exceptional community amenities, and a private setting close to the Island’s favorite towns, Hidden Cove offers a rare combination of active outdoor living, privacy, and quintessential Vineyard ease.

20 Hidden Cove, Oak Bluffs

14 High Meadow Ln, Oak Bluffs
$1,750,000
3 Beds ⋅ 3 Baths ⋅ 73577549 MLS
Welcome to this sun-drenched, reverse contemporary-style home located in the lovely Meadow View Farms community! This multi-level home has boundless potential. The second level features a bright, open floor plan with cathedral ceilings, living, dining, and kitchen areas, and 3 sliding doors that take you outside to the upper deck. Open the sliders to the expansive deck and you will almost double the living space on the upper level. There is also a powder room on the upper level. The main floor features the primary suite with bath, walk-in closet, air conditioning, and sliders that open to the first-floor deck; that level offers 2 more spacious bedrooms and a shared bath. Venture downstairs to the above-grade lower level and enjoy the family room, reading nook, and bonus room. There is also a large storage/utility room with a second powder room. Like every true island home, there is an outdoor shower. Plenty of additional storage is under the deck. Solar panels were added in the fall of 2023. With 3 floors of living space and an expansive portion of the land behind it, this property offers so much potential for the next owners. Meadow View Farms Association is a neighborhood less than 2 miles from downtown Oak Bluffs featuring paved roads, tennis courts, and pastoral meadow views. Strong year-round rental history! The home is being sold "as is".

14 High Meadow Ln, Oak Bluffs

no property photo
$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

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

no property photo
$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

no property photo
$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

no property photo
$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

no property photo
$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

no property photo
$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

no property photo
$1,255,000
3 Beds ⋅ 2 Baths ⋅ 22603967 MLS
Charming Oak Bluffs Ranch on a Peaceful Cul-de-Sac Welcome to this inviting 3-bedroom, 1.5-bath ranch-style home nestled on a generous .35-acre lot at the end of a peaceful cul-de-sac in Oak Bluffs, Massachusetts. Ideally located near the beach and town center, this property offers a wonderful blend of privacy, convenience, and classic island living. The comfortable single-level layout features three bedrooms and one-and-a-half baths, offering plenty of space for family, guests, or a relaxing Martha's Vineyard getaway. Step outside onto the sunny deck, an ideal spot for morning coffee, outdoor dining, or unwinding after a day at the beach. The lovely, spacious yard provides plenty of room for outdoor enjoyment, while the storage shed is perfect for beach equipment, bicycles, gardening tools, and seasonal belongings. Set on a quiet cul-de-sac with a desirable .35-acre lot, this home combines the tranquility of a residential setting with the convenience of being close to Oak Bluffs beaches, restaurants, shops, and the town center. A wonderful opportunity to create your own island retreat in one of Martha's Vineyard's most beloved communities.

11 Stanley Street, Oak Bluffs

no property photo
$1,095,000
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

no property photo
$1,745,000
2 Beds ⋅ 1 Baths ⋅ 22603245 MLS
Wake up to breathtaking ocean views and the soothing rhythm of waves from this charming two-bedroom oceanfront cottage on East Chop. Set on approximately .21 acres of waterfront property with more than 50 feet of shoreline, this special retreat offers a rare opportunity to own a true piece of the island's coastline. Positioned directly on the water, the cottage captures the beauty of the ever-changing ocean from sunrise through sunset. Inside, the cozy two-bedroom cottage offers an inviting island escape with an intimate connection to its spectacular surroundings. Step outside and experience the salt air, gentle sea breezes, and the unmistakable magic of waterfront living. Whether you're enjoying your morning coffee while watching the boats pass, gathering with family and friends, or simply listening to the waves from your own waterfront property, this is a place designed to create lasting Martha's Vineyard memories. A rare East Chop opportunity—over 50 feet of oceanfront, .21 acres of waterfront land, and an enchanting two-bedroom cottage in an extraordinary setting. Just imagine what you could build with proper permitting on this special lot.

11 Beach Road, Oak Bluffs

no property photo
$849,000
1 Beds ⋅ 1 Baths ⋅ 22602409 MLS
In-Town Oak Bluffs Condo with Panoramic Water Views Experience the best of island living in this charming in-town Oak Bluffs condo, offering just under 800 square feet of comfortable and versatile living space. The condo features one generously sized bedroom plus a separate sleep nook, offering flexibility for guests, a home office, or additional sleeping accommodations. The nook could potentially be configured as a second bedroom, subject to applicable requirements and approvals. A true highlight is the rooftop deck shared with just one other unit (# 4 also for Sale). This exceptional outdoor space provides panoramic water views across Nantucket Sound and Oak Bluffs Harbor, creating a spectacular setting for morning coffee, afternoon relaxation, or enjoying the beautiful island sunsets. Ideally situated in the heart of Oak Bluffs, this property places you within easy reach of the harbor, beaches, restaurants, shops, and the vibrant energy of Oak Bluffs center. Whether you're seeking a Martha's Vineyard getaway, investment opportunity, or your own in-town retreat. A special island property with the convenience of in-town living and a rooftop view that truly sets it apart.

37 Circuit Avenue, Oak Bluffs

no property photo
$785,000
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

no property photo
$1,695,000
3 Beds ⋅ 3 Baths ⋅ 22603165 MLS
Welcome to 33 Vineyard Avenue in Oak Bluffs, Martha's Vineyard. This fully gut renovated property 3B/2Ba in total features a 2BR/2BA primary home plus a distinctly separate attached 1BR/1BA ADU suite - offering flexible, move-in ready living or investment potential in a prime in-town location. The main residence in the primary showcases a light-filled interior, wood floors, beamwork, and refined finishes throughout. Open living flows to a gourmet kitchen with suede-finish stone counters, Bosch appliances, dining bar, and walk-in pantry. Upstairs offers two spacious bedrooms, a skylit bath with glass and stone shower, and a private balcony. Enjoy multiple outdoor spaces including a covered porch and side deck. The 1b/1ba ADU secondary suite provides a private entrance, parking, and utilities--ideal for guests or rental income. Featuring open living, oak floors, a stylish kitchen with stone counters and Bosch propane oven, plus a bedroom and full bath. Sliding doors open to a deck and patio with manicured lawn. Moments to downtown, beaches and ferries.

33 Vineyard Avenue, Oak Bluffs

no property photo
$879,000
2 Beds ⋅ 1 Baths ⋅ 22602411 MLS
Intown Oak Bluffs Condo with Panoramic Rooftop Views Discover the charm of island living in this exceptional 2-bedroom, 1-bath condo in the heart of Oak Bluffs. Just under 1,000 square feet, this comfortable residence combines character, comfort, and an unbeatable in-town location. Step inside to an inviting custom wood interior that gives the home a distinctive coastal-island feel. Thoughtfully designed spaces provide the perfect setting for relaxing after a day at the beach, enjoying morning coffee, or entertaining family and friends. One of the condo's true highlights is the semi-private rooftop deck, shared exclusively with Unit 5 (Also for Sale). This extraordinary outdoor space offers a breathtaking panoramic view of the Atlantic Ocean, Nantucket Sound, and Oak Bluffs Harbor — an incredible vantage point for morning sunrises, afternoon breezes, and spectacular island sunsets. Located within easy reach of the best of Oak Bluffs, you can stroll to the harbor, beaches, restaurants, shops, and all the vibrant energy that makes this beloved Martha's Vineyard village so special. A rare opportunity to own a distinctive island retreat with exceptional rooftop views in the heart of OB

37 Circuit Avenue, Oak Bluffs

7 Ploughshare Lane, Oak Bluffs
$1,499,000
3 Beds ⋅ 3 Baths ⋅ 73527741 MLS
Nestled in a quiet cul-de-sac within the coveted Hidden Cove neighborhood, this delightful property offers an exceptional Island lifestyle. The association delivers rare water access via a private dock on Sengekontacket Pond, plus newly resurfaced tennis and pickleball courts. The open-concept layout flows seamlessly from the fireplaced living room and kitchen through the dining area to an expansive screened porch — ideal for entertaining on warm summer evenings. A welcoming front porch provides additional outdoor living space. The main level is completed by a gracious primary suite with a full bath and a convenient half bath. The walk-out lower level features two additional bedrooms, a full bath, and laundry. A one-car garage offers excellent storage for your car, kayaks, or beach gear. Perfectly positioned between Edgartown and Oak Bluffs. Additional bedrooms possible with septic upgrade per BOH

7 Ploughshare Lane, Oak Bluffs

33 Vineyard Ave, Oak Bluffs
$1,695,000
3 Beds ⋅ 3 Baths ⋅ 73511961 MLS
Welcome to 33 Vineyard Avenue in Oak Bluffs, Martha's Vineyard. This fully gut renovated property encompassing 3B/2Ba in total featuring a 2BR/2BA primary home plus a distinctly separate attached 1BR/1BA ADU suite - offering flexible, move-in ready living or investment potential in a prime in-town location. The main residence in the primary showcases a light-filled interior, wood floors, beamwork, and refined finishes throughout. Open living flows to a gourmet kitchen with suede-finish stone counters, Bosch appliances, dining bar, and walk-in pantry. Upstairs offers two spacious bedrooms, a skylit bath with glass and stone shower, and a private balcony. Enjoy multiple outdoor spaces including a covered porch and side deck. The 1b/1ba ADU secondary suite provides a private entrance, parking, and utilities--ideal for guests or rental income. Featuring open living, oak floors, a stylish kitchen with stone counters and Bosch propane oven, plus a bedroom and full bath.

33 Vineyard Ave, Oak Bluffs

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.