Surprisingly roomy Cape-style home, centrally located in Oak Bluffs and right across from the bike path. This five-bedroom house offers generously scaled living spaces throughout, including a large living room filled with natural light, an open stairway, a spacious dining room, and an updated kitchen. The first floor features a primary bedroom, a full bath with laundry, and a separate mudroom/back entry. Recent updates include a new kitchen with new appliances, new baths, fresh interior and exterior paint, new lighting, and new flooring and carpet throughout.
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.
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.
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.
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.
Courtesy: Portfolio Properties
508-627-7005
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.
Courtesy: Wallace & Co. Sotheby's International Realty
508-627-3313
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.
Courtesy: Ocean Park Realty, Inc.
508-693-4210
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.
Courtesy: Ocean Park Realty, Inc.
508-693-4210
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.
Courtesy: Ocean Park Realty, Inc.
508-693-4210
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.
Courtesy: Ocean Park Realty, Inc.
508-693-4210
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
Courtesy: Anchor Realty of MV
508-696-7777
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.
Courtesy: Anchor Realty of MV
508-696-7777
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 .
Courtesy: Studio Realty LLC
508-687-2699
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.
Located in the heart of downtown Oak Bluffs, this charming updated home seamlessly blends classic Vineyard character with bright, modern comfort. Greeting you from the street is an expansive wraparound porch framed by vibrant hydrangeas and a cozy second-floor balcony. Step inside to an inviting open layout featuring crisp white paneled walls, exposed painted ceiling beams, and warm hardwood floors that create an airy, light-filled atmosphere. Designed for relaxed coastal living, this partially insulated retreat offers effortless indoor-outdoor flow and functional updates throughout. Enjoy an unbeatable location directly across the street from the neighborhood playgroud and just a short, scenic walk to pristine beaches, local dining, and the ferry terminal. Whether you are seeking a summer sanctuary or an investment property, this home delivers classic island living at its best! Showings on Saturdays 1-3pm only beginning August 1.
Courtesy: Wallace & Co. Sotheby's International Realty
508-627-3313
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.
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.
Courtesy: Anchor Realty of MV
508-696-7777
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.
Courtesy: Island Real Estate
508-693-4800
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.
Set on a private 1.34-acre parcel along a winding paved road in Oak Bluffs, this exceptional to-be-built luxury residence offers the perfect blend of modern sophistication and island charm. The home features over 3,200 square feet of beautifully crafted living space, including a first-floor primary suite, open-concept great room, gourmet kitchen with pantry, and seamless indoor-outdoor living areas. Upstairs are two additional bedroom suites, a loft-style family room/office, dedicated laundry, and flexible bonus room ideal for guests, media, or recreation. A screened porch, covered outdoor living spaces, and attached two-car garage enhance both functionality and lifestyle. Built with high-end finishes and attention to detail throughout, this stunning new construction offering presents an opportunity to own a luxury retreat with easy access to Oak Bluffs' beaches, harbor, restaurants, shops, and all the attractions that make the Vineyard such a sought-after destination.
Courtesy: Anchor Realty of MV
508-696-7777
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.
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
Tucked away in a serene setting and set on a private 1.38-acres, this beautifully renovated 4BR/4.5BA Cape offers over 4,000 sq ft. of living space with pleanty of room for a backyard pool. The property has been thoughtfully renovated with two new kitchens, 4.5 new bathrooms, 4-bedrooms (two ensuite), and all new appliances and windows. Its floor plan is great for entertaining and flows family and guests from an oversized living room with fireplace into the dining room, gourmet kitchen and an inviting family room with cathedral ceiling and propane stove. First floor includes an ensuite bedroom and large screened in porch. The 1-bedroom apartment above the 2-car garage includes living/dining/kitchen area, washer/dryer, and heat/AC. The property includes a full basement, spacious rear patio and deck, outdoor shower and is large enough for an in-ground pool. Assessed value does not reflect extensive 2026 renovations. Furnishings in the photos have been virtually staged.
Nestled within the idyllic and highly coveted setting of Farm Neck Golf Club, 15 Tamarack Lane offers a rare opportunity to own a stunning 3.7 acres in one of Martha’s Vineyard’s most exclusive communities. The property enjoys picturesque views over the 7th fairway and 8th tee box, across to Sengekontacket Pond, creating a peaceful backdrop of lush greens and distant water. The historic five-bedroom main residence, along with a separate one-bedroom carriage house, are rich in character and await a thoughtful renovation or reimagining. Ideally located near the clubhouse, restaurant, tennis courts, and pro shop, the property offers easy access to the Farm Neck lifestyle while remaining just minutes from town, the harbor, and ferry terminal. This is an extraordinary chance to secure a property within the esteemed Farm Neck Golf Club community. Included is a highly sought-after Farm Neck Club Stockholder Membership, enhancing both its prestige and value.
Located under a mile from the heart of downtown Oak Bluffs, this charming property offers endless potential in a highly convenient location. Set on a level lot, the home is ready for its next chapter — whether as a summer getaway or year-round residence. Enjoy easy access to town, beaches, ferries, restaurants, and shops while creating your own vision in this classic Island setting.
Oak Bluffs is located in Massachusetts. Oak Bluffs, Massachusetts has a population of 5,284. Oak Bluffs is more family-centric than the surrounding county with 39.56% of the households containing married families with children. The county average for households married with children is 27.66%.
The median household income in Oak Bluffs, Massachusetts is $94,545. The median household income for the surrounding county is $77,392 compared to the national median of $69,021. The median age of people living in Oak Bluffs is 40.4 years.
The average high temperature in July is 78.9 degrees, with an average low temperature in January of 22.7 degrees. The average rainfall is approximately 47.4 inches per year, with 24 inches of snow per year.
