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$1,185,000
1 Beds ⋅ 1 Baths ⋅ 73521487 MLS
THE BEST SEAT IN TOWN! This one-bedroom, one-bathroom condo offers incomparable, panoramic views of Vineyard Sound and the open ocean beyond, across the green expanse of Ocean Park with the Steamship Authority dock in the distance. Door to door, the ferry dock is 392 yards away. This perfect pied-a-terre is convenient to long stretches of beach, numerous shops, great and varied restaurants and the vibrant life of Oak Bluffs in the summertime. A completely renovated and updated Unit with high end finishes including solid mahogany doors and mahogany counter top center island. The property is beautifully landscaped and can be enjoyed year-round. It includes a coveted, off-street parking space. From the French doors in the Unit, you walk out onto a private, second floor, 7' x 21' porch with a front row seat to watch the Oak Bluffs fireworks, band concerts in the gazebo and all the summer festivities on Ocean Park. This is a rare opportunity to own a genuine piece of American history.

61 Ocean Avenue Unit 4, Oak Bluffs

Listing courtesy of Listing Agent: Buder Team from Listing Office: Sandpiper Realty, Inc..
$905,000
2 Beds ⋅ 1 Baths ⋅ 73520554 MLS
Tucked away on a quiet side street just 0.7 miles from Circuit Avenue, this charming Oak Bluffs cottage offers the rare combination of privacy and proximity to town.The original two-bedroom, one-bath home was thoughtfully expanded to include a bright great room that opens directly to a large fenced yard -- ideal for outdoor dining, pets, or simply enjoying Vineyard summers. The property is enhanced by mature, thoughtfully curated plantings including Japanese maple, cherry, and magnolia, creating a peaceful, garden-like setting with seasonal color and texture.A separate storage shed with its own small deck presents exciting potential for a studio, home office, creative space, or even a future sauna.A comfortable year-round residence, vacation retreat, or investment opportunity close to beaches, ferries, restaurants, and all that downtown Oak Bluffs has to offer -- without the noise of being in the middle of it.

22 Firehouse, Oak Bluffs

Listing courtesy of Listing Agent: Jen O'Hanlon from Listing Office: Compass.
$1,035,000
3 Beds ⋅ 2 Baths ⋅ 73552744 MLS
Located within the historic Martha’s Vineyard Camp Meeting Association, this rare double-lot property combines classic Campground charm with modern comfort. Two-car off-street parking—an exceptional Campground amenity—adds convenience, while Oak Bluffs Harbor, beaches, ferries, shops, and restaurants are just moments away. The 1,135-square-foot home features painted wood floors, abundant natural light, vintage details, and flexible living spaces for gathering, guests, or a home office. Unlike many Campground cottages, it is fully winterized with a four-zone heat pump system providing efficient heating and air conditioning, plus a propane on-demand water heater. Significant improvements include updated electrical and lighting, newer appliances, kitchen built-ins, foundation work, and a sealed, dry crawlspace. Outside, the fenced yard, expanded brick patio, shade sails, cooling fan, outdoor television, and large storage shed create a private retreat rarely found in the Campground.

21 Butler Avenue Unit 1, Oak Bluffs

Listing courtesy of Listing Agent: Jen O'Hanlon from Listing Office: Compass.
$1,275,000
3 Beds ⋅ 1 Baths ⋅ 73556029 MLS
PRIME LOCATION! LESS THAN A 5-MINUTE WALK TO OAK BLUFFS HARBOR! Beautifully Renovated in Oak Bluffs! This move-in ready home at 9 Brunswick Ave has been thoughtfully & extensively UPDATED INSIDE AND OUT. Enjoy peace of mind w/ NEW septic system, siding, windows, water line from the street, & upgraded electrical & plumbing. Interior boasts new flooring, insulation, fresh paint, a stylishly renovated kitchen, and efficient new heat/AC systems for year-round comfort. Recently installed professionally landscaped grounds offer curb appeal & outdoor enjoyment, complete w/ shower & patio furniture for al fresco dining & relaxing. Also included are ALL FURNISHINGS & handy owner’s shed for extra storage. An exceptional value just moments from downtown Oak Bluffs and Beaches. 5 minute walk to HARBOR. AIRBNB HISTORY $89,000 already booked Summer '26!

9 Brunswick, Oak Bluffs

Listing courtesy of Listing Agent: Alice Pierce from Listing Office: Coldwell Banker Realty - Hingham.
$1,885,000
5 Beds ⋅ 4 Baths ⋅ 73529614 MLS
Craving the ultimate Martha's Vineyard escape? Discover a hidden architectural gem in the serene Tower Ridge community, across the street from Farm Neck Golf Club & Cafe! This striking contemporary home perfectly blends sophisticated design with the tranquil beauty of an expansive, private lot. Step inside to experience a breathtaking layout defined by soaring cathedral ceilings and an abundance of natural light. The floor plan flows effortlessly, extended by a beautifully finished lower level with a bespoke media room/private lounge and 2 more bedrooms. Outside, your personal resort awaits: host elegant summer soirées on the sprawling wood deck, unwind within the peaceful screened porch, or enjoy the quintessential luxury of a crisp outdoor shower. Complete with an attached garage, this property offers unmatched privacy and style. Don't miss this rare opportunity to own a piece of island paradise—schedule your private tour today!

18 Puritan Dr, Oak Bluffs

Listing courtesy of Listing Agent: Jennifer DaSilva from Listing Office: Compass.
$1,687,500
3 Beds ⋅ 3 Baths ⋅ 73484865 MLS
Nestled on a rare, oversized 1.5-acre lot, this spacious 3-bed/2-bath contemporary home offers a perfect blend of privacy and coastal convenience. Perched elegantly upon a gentle rise, the residence is bathed in natural light and framed by a beautifully landscaped lawn with mature plantings. The interior is designed for both comfort and scale. An expansive front living room has soaring cathedral ceilings and floor-to-ceiling windows that invite the outdoors in. The heart of the home features a family room with a cozy fireplace and a kitchen equipped with a convenient wet bar. The formal dining room opens via sliders to a fir deck, perfect for alfresco entertaining. The first floor is anchored by a generous primary suite featuring a large walk-in closet. Finally, a spacious laundry/mudroom provides direct access to the two-car garage. Upstairs, a versatile second-floor loft overlooks the family room ideal for a home office or additional lounge, flanked by two bright guest bedrooms.

103 Meadow View Road, Oak Bluffs

Listing courtesy of Listing Agent: Karen M. Overtoom from Listing Office: Karen M. Overtoom R.E..
$1,050,000
3 Beds ⋅ 2 Baths ⋅ 73471135 MLS
Charming, custom-built, 3-bedroom, 1.5-bath Oak Bluffs home on a quiet circle, offering a peaceful setting with convenient access to down-island attractions, year-round ferries, and miles of ancient way trails through acres of conservation land. Well-maintained with many decorative details, features include a large primary bedroom, a convenient first-floor bedroom, and an open kitchen dining area flowing to a spacious wooden deck and outdoor shower—perfect for indoor-outdoor living. Beautifully maintained with wood floors, skylights, and natural light throughout, this move-in-ready home blends comfort, character, and charm. The floor plan offers privacy between the 3 oversized bedrooms. Ideal for year-round living or a seasonal retreat. 4 bedroom septic system in place invites expansion.

12 Wheelhouse Way, Oak Bluffs

Listing courtesy of Listing Agent: Dawn Bellante from Listing Office: Sandpiper Realty, Inc..
$2,775,000
3 Beds ⋅ 3 Baths ⋅ 73462129 MLS
A rare offering on iconic Ocean Park. This beautifully renovated Victorian cottage sits in the heart of historic Oak Bluffs with unencumbered views of Ocean Park and Vineyard Sound. Completely rebuilt in 2024, this 3-bedroom, home blends classic Vineyard charm with modern comforts, featuring a welcoming wraparound porch, a beach-stone wood-burning fireplace, new kitchen, baths, windows, doors and basement with stylish finishes throughout. Originally crafted in the Victorian era and thoughtfully restored for contemporary living, this home enjoys an unbeatable setting and is steps to beaches, ferries, restaurants, galleries, and all the conveniences of downtown Oak Bluffs.Whether cherished as a year-round residence summer retreat, or a high-demand rental, this Ocean Park home offers exceptional walkability and an unrivaled island lifestyle in one of Oak Bluffs’ most coveted locations. This listing is for Parcel One of the current Deed. The assessed value is yet to be properly recorded.

33 Ocean Ave, Oak Bluffs

Listing courtesy of Listing Agent: Marcia Garvey from Listing Office: Donnelly + Co..
$1,195,000
3 Beds ⋅ 2 Baths ⋅ 73503165 MLS
Oak Bluffs- Fully renovated and just completed, this three-bedroom, two-bath home is ready for immediate occupancy! Ideally located just moments from downtown Oak Bluffs and the vibrant harborfront, you’ll enjoy easy access to shops, dining, beaches, and ferry connections. Featuring modern updates throughout, this home offers the perfect blend of comfort and convenience.

10 Winthrop Avenue, Oak Bluffs

Listing courtesy of Listing Agent: Katie Donahue & Rachel Serwa Group from Listing Office: Sandpiper Realty, Inc..
$2,875,000
3 Beds ⋅ 2 Baths ⋅ 73499885 MLS
Total sale for the property was $2,950,000 with $75,000 assigned to furnishings package. Your Vineyard summer begins the moment you arrive. This rare, fully furnished waterfront retreat offers 175' of private shorefront on Lagoon Pond — one of Martha's Vineyard's most coveted settings. Taken to the studs in 2022 and reimagined by architect Ramsay Gourd, this bright coastal escape features soaring vaulted ceilings, white shiplap, and painted beams. Glass sliders open to bluestone terraces where water views take center stage. The open kitchen offers custom cabinetry, stainless appliances, and casual dining perfect for summer entertaining. Two additional bedrooms with cathedral ceilings share a glass-shower bath. Outside: mahogany shower, rolling lawns, and hydrangea beds complete the quintessential Vineyard setting. Turnkey and move-in ready — kayaks included. Strong rental history with 2026 leases in place. 4-bedroom septic. Lot is elevated out of flood plain with sweeping view

309 Barnes Road, Oak Bluffs

Listing courtesy of Listing Agent: Dawn Bellante from Listing Office: Sandpiper Realty, Inc..
$1,187,500
4 Beds ⋅ 2 Baths ⋅ 73472030 MLS
Nestled in a quiet Oak Bluffs neighborhood, this charming, sun-filled four-bedroom, two-bath home sits on a spacious corner lot and offers an ideal opportunity for both seasonal and year-round living. The home features a functional layout with a cozy wood burning stove and abundant natural light throughout. The main level offers a spacious living area open to a kitchen, both with wide plank flooring, as well as two comfortable bedrooms and access to a screened-in porch, perfect for relaxing summer evenings. Upstairs, you’ll find two extra large bedrooms and a shared bath, providing flexible space for family and guests.The enclosed backyard is well suited for gardening, entertaining, or simply enjoying the outdoors, while the nearby Lagoon town landing offers easy access for kayaking, canoeing, or launching a small boat. Ideally located walking distance to the Lagoon, less than one mile to Farm Neck, and under two miles to the heart of Circuit Ave and all Oak Bluffs has to offer.

54 Columbian, Oak Bluffs

Listing courtesy of Listing Agent: Marcia Garvey from Listing Office: Donnelly + Co..
$750,000
2 Beds ⋅ 1 Baths ⋅ 73504275 MLS
Tucked away on a quiet no-thru street near the Tabernacle and Trinity Park, this meticulously maintained year-round Martha’s Vineyard Camp Meeting Association cottage blends charm and convenience. Thoughtful 2023 updates—including a new kitchen with stainless steel appliances, refreshed bathroom, upgraded insulation and electrical, three mini-splits, onsite laundry, spiral staircase, and new roof—enhance comfort while preserving character. An insulated attic adds valuable storage. Wide-plank pumpkin pine floors and abundant natural light create a warm interior that flows to multiple outdoor seating areas, garden, and an outdoor shower. Moments from Oak Bluffs Harbor, ferries, shops, and restaurants, this move-in-ready retreat offers quintessential island living.

1 Pease Avenue, Oak Bluffs

Listing courtesy of Listing Agent: Katie Donahue & Rachel Serwa Group from Listing Office: Sandpiper Realty, Inc..
$2,450,000
6 Beds ⋅ 3 Baths ⋅ 73514966 MLS
Oak Bluffs | East Chop - Tucked away on a quiet lane just moments from the iconic East Chop Lighthouse and breathtaking bluff views, this timeless retreat invites you to embrace the slower pace of island life. The stately five-bedroom main residence is rich in character and nostalgic charm, thoughtfully updated to enhance comfort for year-round living. Tucked privately at the rear of the property, a separate one-bedroom guest house offers flexibility and modern conveniences ideal for today’s lifestyle. Set on a generous, level parcel with an existing seven-bedroom septic system, the property presents exceptional opportunities for future expansion, customization, or the creation of a true multi-generational compound. Located in the heart of East Chop, a cherished community known for its neighborly spirit, you're just minutes from the harbor and vibrant downtown Oak Bluffs. A rare offering that honors tradition while embracing the possibilities ahead.

16 Atlantic Avenue, Oak Bluffs

Listing courtesy of Listing Agent: Katie Donahue & Rachel Serwa Group from Listing Office: Sandpiper Realty, Inc..
$1,235,000
2 Beds ⋅ 1 Baths ⋅ 73483140 MLS
Single Story Bungalow — Turnkey & Walkable Lifestyle! Welcome to this beautifully updated home offering effortless single-level living and a bright, open layout designed for comfort and functionality. Turnkey and thoughtfully renovated, the property seamlessly blends classic charm with modern upgrades throughout. The updated kitchen features contemporary cabinetry, sleek countertops, and modern appliances, while the renovated bathroom, showcase stylish finishes and quality craftsmanship. New or refinished flooring flows throughout the home, complemented by fresh interior and exterior paint and upgraded lighting and fixtures that create a clean, cohesive feel. This beautifully designed 2-bedroom, 1-bath home offers comfort, functionality, and inviting spaces both inside and out. A spacious mudroom provides the perfect drop zone for coats, shoes, and everyday essentials, keeping the main living areas organized and clutter-free.

56 Garvin St., Oak Bluffs

Listing courtesy of Listing Agent: Casandra Hyland from Listing Office: Sandpiper Realty, Inc..
$1,625,000
4 Beds ⋅ 3 Baths ⋅ 73468842 MLS
Meadowview Farms — This home is ideal for those who love to host lively gatherings! Set at the end of a quiet cul-de-sac, this spacious Colonial offers over 3,200 sq ft designed for comfortable living and easy entertaining. The home features four bedrooms and 2.5 baths, including a primary suite with walk-in closets and private bath. The main living area flows from a living room with fireplace into the kitchen and dining space, while a large screened-in porch creates an exceptional setting for gatherings and outdoor enjoyment. A huge second-floor bonus room provides flexible space for media, recreation, or home office use. Additional highlights include a full basement, attached two-car garage, landscaped lot, association tennis courts, and convenient access to the bike path. Just minutes to Farm Neck Golf Club and all that Oak Bluffs has to offer.

7 Upper Meadow Ln, Oak Bluffs

Listing courtesy of Listing Agent: Lesley Heidt from Listing Office: Sandpiper Realty, Inc..
$3,050,000
7 Beds ⋅ 5 Baths ⋅ 73470490 MLS
An exceptional chance to own one of the few five-unit apartment buildings available on Martha’s Vineyard. Ideally located within a short walk to Oak Bluffs Center, the Harbor, ferry service, and public beaches, this property offers both convenience and strong income potential. The building includes five well-maintained apartments with a total of 7 bedrooms and has been thoughtfully renovated and consistently cared for over the years. There are two two-bedroom apartments and three one-bedroom apartments. With ample on-site parking, this property is easy to manage and highly attractive to year-round and seasonal tenants alike. Tenants-in-place notice required to be shown.

35 New York Avenue, Oak Bluffs

Listing courtesy of Listing Agent: Emma Kennedy from Listing Office: Sandpiper Realty, Inc..
$1,850,000
4 Beds ⋅ 3 Baths ⋅ 73473424 MLS
Impressive four-bedroom home with a distinctive floor plan that combines privacy, comfort, and convenience in one of Oak Bluffs’ most desirable locations. The main living area, filled with natural light and soaring ceiling, offers an open layout that is warm and inviting. A third floor den and exterior decks on all levels provide ample living space both indoors and out. Set within the sought-after Meadow View Farms community, residents enjoy access to beautifully maintained common meadows, as well as association tennis and pickleball courts. The neighborhood’s peaceful setting fosters a true sense of community, while its prime location, just off the bike path, places Farm Neck Golf Club and all downtown attractions, within easy reach.

7 South Meadow Lane, Oak Bluffs

Listing courtesy of Listing Agent: Katie Donahue & Rachel Serwa Group from Listing Office: Sandpiper Realty, Inc..
$2,900,000
4 Beds ⋅ 5 Baths ⋅ 73472628 MLS
Tucked away in a serene setting, this beautifully designed custom home offers the ultimate in privacy, comfort, and luxury living. The first floor features a spacious open-concept design, seamlessly blending the dining room, kitchen, wet bar, and living area-perfect for entertaining or relaxing with the family. Home chefs will fall in love with the gourmet kitchen complete with custom cabinetry, high-end appliances, stunning granite countertops and generous counter space for cooking and hosting in style. Outdoor enthusiasts will appreciate private access to over 200 acres of trails right from your back yard. Renovation 2019 please see list of updates in documents.

63 Bayes Hill Rd, Oak Bluffs

Listing courtesy of Listing Agent: Casandra Hyland from Listing Office: Sandpiper Realty, Inc..
$782,000
2 Beds ⋅ 1 Baths ⋅ 73454444 MLS
An unbeatable location ~ just a short distance to the harbor, beaches, ferry ports, the public library, and all the vibrant attractions of Oak Bluffs. This 2-bedroom, 1-bathroom ranch-style home is sited on a 10,454 sf level lot with a detached garage/shed. The property offers one-floor living, a convenient location, and great potential. The main living area includes an open living and dining room. The kitchen is at the back of the house with the mudroom and side entrance beyond. Enjoy the beautiful natural light in the spacious sun room at the front of the house with French doors leading to the side yard. The property offers charm and potential in a sought-after location. Several updates were completed in 2010 such as a new roof, windows, and siding (see full list in documents section). The property is being sold “AS IS”. There are 2 existing cesspools on site that failed inspection. Per the Oak Bluffs Wastewater Department, the property can tie into Town sewer.

24 School Street, Oak Bluffs

Listing courtesy of Listing Agent: Stephanie Roache from Listing Office: Donnelly + Co..
$1,530,000
3 Beds ⋅ 2 Baths ⋅ 73377083 MLS
Bright, Open Living Steps from the Lagoon!This sun-filled 3-bedroom, 2-bath home offers easy single-level living with a spacious, open-concept layout—ideal for entertaining and everyday comfort. A welcoming sitting area flows into the living room, dining space, and modern kitchen. A separate home office/den adds flexibility to this 2,015 sq ft home. Set on a generous 11,000 sq ft corner lot, sliding glass doors lead from the living area to a deck overlooking a beautifully landscaped yard—perfect for outdoor living. A detached two-car garage provides added storage and convenience. Ideally located across from Lagoon Pond, enjoy west-facing views of the water and Vineyard Haven Harbor. Whether you’re sipping morning coffee, kayaking, clamming, or soaking in sunsets, this location offers the best of coastal life. Ideal as a year-round home, serene retreat, or vacation rental. Carefree coastal living at its best—just steps from the water.

48 Vineyard Avenue Extension, Oak Bluffs

Listing courtesy of Listing Agent: Susie Pimpton-Wallo from Listing Office: Compass.
$2,250,000
4 Beds ⋅ 4 Baths ⋅ 73368855 MLS
Perched on a hill, this waterfront house encompasses three levels of living. Thoughtfully designed and well cared for, this home provides calming water views and direct access to Wiggy’s freshwater Pond from almost every room. The main level boasts a kitchen fitted with high-end appliances and opens to the dining room, deck, and airy living room with exposed beams, a gas fireplace, and large windows throughout, offering an abundance of natural light. The first-floor primary has an ensuite bath, a walk-in closet with generous shelving, and direct access to the deck. Upstairs is the second bedroom with ensuite bath and walk in closet. The versatile loft space overlooks the living room and is a perfect spot for a home office, play area, or reading nook. The lower level includes two guest bedrooms, full bathroom, laundry room, additional storage and a family room that opens to the stone patio and outdoor shower. Association includes access to dock, clubhouse, tennis/ pickleball and more!

10 Wood Duck, Oak Bluffs

Listing courtesy of Listing Agent: Marcia Garvey from Listing Office: Donnelly + Co..
$1,865,000
4 Beds ⋅ 5 Baths ⋅ 73442473 MLS
On the doorstep of vibrant Oak Bluffs, discover this exquisitely renovated four bedroom home with separate office or studio space, all ensconced in professionally landscaped grounds. Blending modern comfort with timeless island charm, the house features wide plank white oak floors, beautiful ceiling height and natural light, an open-concept living-dining space with a new kitchen, a first-floor primary bedroom with ensuite bath, powder room, and laundry room. Upstairs are three additional spacious bedrooms and two full baths. A new roof, siding, and central air enhance comfort. Outside, enjoy a large back deck, welcoming porch, and an expansive yard with irrigation, a new sod lawn, evergreen and privet hedge borders, plus a classic Vineyard must-have: an outdoor shower. Ideally located near charming Oak Bluffs with its whimsical gingerbread cottages, Flying Horses Carousel, harborfront, shops, dining, and nearby Oak Bluffs Town and Jetties beaches. Buyers and agents please verify all.

71 Netock Ave, Oak Bluffs

Listing courtesy of Listing Agent: Ellen Valentgas from Listing Office: Sotheby's International Realty.
$825,000
3 Beds ⋅ 2 Baths ⋅ 73440678 MLS
Charming sunlit three-bedroom, two-bath home on a quarter-acre lot with a full unfinished basement offering excellent potential. The three-bedroom septic system has passed inspection (recommended pumping being done). The interior features wood floors throughout and an open-concept living, kitchen, and dining area, perfect for relaxed island living. The primary bedroom includes a full bath, while two guest bedrooms share a second full bath. Enjoy the enclosed backyard, ideal for gardening or outdoor entertaining. Launch a kayak, canoe or small boat from the nearby town landing at the end of Hudson Avenue. Less than a mile from Farm Neck Golf Course, a half mile to the bike path, and two miles from downtown Oak Bluffs. Oak Bluffs School is an easy bike ride away. Interior photographs to follow.

69 Summit Avenue, Oak Bluffs

Listing courtesy of Listing Agent: Susie Pimpton-Wallo from Listing Office: Compass.
$750,000
4 Beds ⋅ 1 Baths ⋅ 73424612 MLS
Step back in time with this quintessential Martha’s Vineyard Campground Cottage, nestled in the heart of Wesleyan Grove. The cottage captures the spirit of the Island’s rich history, with its storybook architecture, vibrant community setting, and proximity to all that Oak Bluffs has to offer. The cottage features classic Victorian-era details, starting with its inviting front porch. The 4-bedroom, 1-bath cottage welcomes you with soaring ceilings offering beautiful natural light. Outside, the fenced in back yard provides additional space for family and guests to gather and enjoy the unique atmosphere of the neighborhood. The property offers the rare opportunity to own a piece of Vineyard history—the perfect summer retreat. Located on Trinity Park, overlooking the Tabernacle, and just steps from Oak Bluffs harbor, beaches, shops, and dining, this cottage places you at the center of Island life while preserving the tranquility of a close-knit historic community.

41 Trinity Park, Oak Bluffs

Listing courtesy of Listing Agent: Stacy Ickes from Listing Office: Donnelly + Co..
$2,100,000
3 Beds ⋅ 2 Baths ⋅ 73355326 MLS
Tucked away on one of Oak Bluffs' most sought-after streets, Fairview on Greenleaf Avenue offers an extraordinary location with stunning views of Sunset Lake, Oak Bluffs Harbor, and Nantucket Sound. From the highest point on Greenleaf, enjoy vibrant sunrises and a front-row seat to the town's iconic fireworks.This home blends classic Vineyard character with thoughtful design by Island architect Jaime Weisman. Lovingly maintained by one family for over 27 years, it now awaits its next chapter.Fairview includes three bedrooms, a finished basement for flexible living or work space, and a multipurpose outbuilding that functions as both shed and garage. With off-street parking and a generous yard, the property offers convenience and charm. Just steps from the heart of Oak Bluffs—Illumination Night, Tabernacle concerts, Ocean Park strolls—yet still a private, serene retreat.A rare chance to own a home with incredible views, historic charm, and space to make it your own.

22 Greenleaf Avenue, Oak Bluffs

Listing courtesy of Listing Agent: Jen O'Hanlon from Listing Office: Compass.
$1,000,000
2 Beds ⋅ 1 Baths ⋅ 73407604 MLS
Welcome to an inviting single-story ranch nestled in the heart of Oak Bluffs. This cozy and charming home offers a comfortable living space and is set on a generous, water view landscaped lot with mature trees and natural privacy. Inside, the home features a functional layout with a mix of wood and carpet flooring, a cozy wood-burning fireplace, and abundant natural light throughout.The classic ranch design includes a seamless flow between living, dining, and kitchen spaces—ideal for both everyday living and seasonal retreats. Enjoy the outdoors from the wood deck or rinse off in the outdoor shower after a day at the beach.A detached garage provides added storage and parking convenience.With electric baseboard heat, wood shingle siding, and a gable roof, the home reflects timeless Vineyard style and solid craftsmanship.Located minutes from downtown OB, local beaches and ferry access, this home presents an ideal opportunity for seasonal or year-round residents.Home is being sold 'as is'

13 County Road, Oak Bluffs

Listing courtesy of Listing Agent: Jennifer DaSilva from Listing Office: Compass.
$1,500,000
4 Beds ⋅ 4 Baths ⋅ 73310926 MLS
Located in a desirable Oak Bluffs neighborhood, surrounded by mature plantings and attractive, colorful landscaping, this property offers a pleasantly appointed 3-bedroom, 2.5-bath home and a recently renovated 1-bedroom, 1-bath apartment above the 2-car garage. The first floor features a spacious living room with a pellet stove and a fabulous great room with a wood-burning stove. French doors lead to a large deck, perfect for outdoor entertaining. The open kitchen and dining room are at the back of the house and enjoy direct deck access. There is a half bath off the living room. The primary suite with a full bath, and 2 additional bedrooms that share a full bath, complete the second floor. An exceptional feature of this property is the apartment with a comfortable living space and a private entrance and deck. Easy access to the bike path, YMCA, high school, state forest, and centrally located to all the down-island towns! Seller will only sell to a year-round resident.

8 School House Village, Oak Bluffs

Listing courtesy of Listing Agent: Stephanie Roache from Listing Office: Donnelly + Co..
$1,633,000
5 Beds ⋅ 2 Baths ⋅ 73362245 MLS
Location, Location, Location! Welcome to your dream retreat in the charming historic area of Oak Bluffs. Walk to Inkwell beach, ferries, restaurants and dining. Sited across the street from Waban Park, this delightful home offers an inviting blend of comfort and convenience.As you step inside, you'll immediately appreciate the spacious layout featuring well-appointed living areas, a generous covered porch and lovely historic details.The living areas are perfect for both cozy family gatherings and entertaining guests. Large windows with architectural shutters throughout the home invite abundant natural light, creating a warm and welcoming atmosphere. Outside boasts an outdoor shower, patio area and a garage! Situated in a highly sought-after neighborhood, this property combines an ideal location, this home offers the best of both worlds.With its open layout and inviting design, this wonderful residence is more than just a home, it's a lifestyle.(Home is being sold as-is).

35 Tuckernuck Ave, Oak Bluffs

Listing courtesy of Listing Agent: Jennifer DaSilva from Listing Office: Compass.
$700,000
3 Beds ⋅ 1 Baths ⋅ 73326193 MLS
Gingerbread Cottage full of character and personality! Part of Martha's Vineyard Camp Meeting Association, this Oak Bluffs seasonal antique with beautiful trim and scrollwork sits on a lovely little avenue. The cottage features charming period details, a covered front porch with rocking chairs & upper balcony. Step inside the unique front door into a cozy living room enhanced by beamed ceiling, painted wood floors & lovely shutters. First floor bedroom, full bath & laundry. The kitchen offers access to private courtyard with stone patio for outdoor dining & storage shed. Second floor includes front bedroom with access to the private balcony & a 3rd bedroom. Too many updates to list! Ask agent! Home is just steps from historic Trinity Park & the Tabernacle, which offers community events & activities for all ages! Prime location near Circuit Ave in the heart of Oak Bluffs gives easy walkable access to beaches, restaurants, ice cream, shopping, arcade, ferries & island transportation!

2 Fisk Ave, Oak Bluffs

Listing courtesy of Listing Agent: Julie Walker from Listing Office: Century 21 North East.
$2,400,000
3 Beds ⋅ 5 Baths ⋅ 73342446 MLS
Must see stunning “reverse” layout (kitchen and main living spaces upstairs for the views) contemporary home with breathtaking water views and a thoughtfully designed layout in the exclusive Harthaven community! This spacious property features open kitchen concept with marble counter tops and stainless steel appliances, comfortable living areas, a bonus room (with full bathroom), food prep, dining and 2 queen Murphy beds, perfect for guests. Enjoy exclusive access to a private community beach and boat dock and community tennis / pickleball courts, enhancing the home's resort-style living experience. Landscaped grounds with irrigation, outdoor enclosed shower, 2 pea gravel fire-pit areas, bocce ball court, two decks with water views, hot tub, gas grill connection off the kitchen area and ample parking. Primary bedroom has deck, walk-in closet and steam shower. Located just a short distance from downtown Oak Bluffs and right on the bike path - don't miss this exceptional coastal retreat!

6 Martha's Park Road, Oak Bluffs

Listing courtesy of Listing Agent: Jennifer DaSilva from Listing Office: Compass.

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