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28 Grovedale Road, Oak Bluffs
$1,700,000
3 Beds ⋅ 4 Baths ⋅ 73540119 MLS
GORGEOUS NEWER CONSTRUCTION (2023), contemporary farmhouse style home w/ classic wrap around porch & designed w/ Vineyard charm & modern comfort. And yet still there is opportunity to add value to this open concept home, w/ high ceilings, 3 en-suite BRs, laundry on each level, hardwoods throughout. Well designed, fully poured unfinished basement w/ high ceilings, wide open & w/ a separate entrance for an in-law or ADU. 1st FL en suite BR & a common half bath at the foyer entry. Large kitchen w/ full appliances & a 10’ stone topped island for large gatherings. Gas fireplace in the family room, sliders to rear yard, a well-designed mudroom area w/ 1st FL laundry, large overflow pantry & a built in bench seating area. The 2nd FL offers 2 en-suite BRs, w/ a large common area. Close to the Lagoon & Sailing Camp Park.Short ride downtown- ideal for year round occupancy and/ or high season rentals. House related plans, professional photos, interior, exterior & aerial video avail upon request.

28 Grovedale Road, Oak Bluffs

Listing courtesy of Listing Agent: Dave White from Listing Office: OwnerEntry.com.
312 East Chop Drive, Oak Bluffs
$2,050,000
3 Beds ⋅ 4 Baths ⋅ 73529130 MLS
“The Doll House” is a landmark East Chop waterfront retreat overlooking Crystal Lake with sweeping views of Vineyard Sound. Originally a charming fishing cottage, this iconic property has been thoughtfully renovated and meticulously maintained, blending timeless Vineyard character with modern comfort. Surrounded by lush hydrangea and perennial gardens, the property boasts nearly 150 feet of Crystal Lake frontage, offering swimming, kayaking, and paddleboarding from your backyard. The main house features a welcoming sun porch, living room with a stone fireplace, light-filled primary bedroom with water views, and an updated kitchen and dining area with brick floors and a built-in window seat. French doors open to a spacious lawn and a charming former boathouse converted into a unique dining pavilion. Additional highlights include a rooftop deck with panoramic water views, guest cottage, outdoor shower, garage with office, and garden shed. A quintessential Martha’s Vineyard waterfront esc

312 East Chop Drive, Oak Bluffs

Listing courtesy of Listing Agent: Alyssa Halisky from Listing Office: Wallace & Co. Sotheby's International Realty.
385 Barnes Road, Oak Bluffs
$5,028,000
3 Beds ⋅ 7 Baths ⋅ 73496934 MLS
Set along 125 feet of private Lagoon frontage, this beautifully designed home offers over 5,400 sq. ft. of light-filled living space across three levels. High ceilings, skylights, and walls of glass capture sweeping water views, while a decorative stone fireplace anchors the main living area. The chef’s kitchen features stainless appliances, stone counters, custom cabinetry, and a large island, complemented by a wet bar and casual dining area. Three ensuite bedrooms include a primary suite with water views, a sitting area, walk-in closet, pool access, and a spa-like bath. The walk-out lower level offers a game room, media area, kitchenette, wine storage, and bonus room. Outdoors, enjoy a heated pool, spa, bluestone terrace, and direct access to calm waters for swimming, boating, and some of the best steamers, littleneck, and cherry stones on the Island. Offered furnished with strong rental history.

385 Barnes Road, Oak Bluffs

Listing courtesy of Listing Agent: Stephanie Roache from Listing Office: Donnelly + Co..
8 Paddock Rd, Oak Bluffs
$5,300,000
4 Beds ⋅ 6 Baths ⋅ 73499730 MLS
Refined Vineyard living in The Preserve. Set on a knoll overlooking the pond and sweeping grasslands, this exceptional home blends classic coastal architecture with modern luxury. The expansive great room showcases cathedral ceilings, rich millwork, and abundant natural light, with three sets of French doors opening to a bluestone patio with multiple sitting areas and a heated saltwater pool. The chef’s kitchen flows seamlessly into the dining and living spaces. One wing offers an inviting lounge and a luxurious primary suite with spa-like bath and dressing room, while the opposite wing features three guest bedrooms, each with ensuite baths and walk-in closets. Additional highlights include a proper mudroom and a finished lower level with media room, full bath, and storage. Surrounded by mature landscaping, with easy access to trails, the bike path and Farm Neck Golf Club. The Preserve is a private enclave of luxury homes and is arguably one of Oak Bluffs most exclusive neighborhoods.

8 Paddock Rd, Oak Bluffs

Listing courtesy of Listing Agent: Lesley Heidt from Listing Office: Sandpiper Realty, Inc..
3 Hidden Cove Rd, Oak Bluffs
$2,150,000
4 Beds ⋅ 4 Baths ⋅ 73500165 MLS
Hidden Cove Gem with Serene Pond Views And Coveted Water Access - Located in the desirable Hidden Cove enclave—a 65+ acre water-access community—this inviting contemporary home offers privacy and high-end finishes with direct access to Sengekontacket Pond and Nantucket Sound. Community amenities include a private boat dock, walking trails, pickleball and tennis, all near Oak Bluffs. The sun-filled interior features a living room with vaulted ceilings, a wood-burning fireplace, and floor-to-ceiling windows. The chef’s kitchen is appointed with stone countertops and Dacor® appliances. The second-floor primary suite boasts a private balcony with pond views and a stylish en suite bath. The garden level provides additional bedrooms and a bonus space with a Murphy bed. Outside, enjoy a bluestone terrace and two levels of decks overlooking a private yard. This move-in-ready home is offered fully furnished with over $80,000 in 2026 summer rental income already secured.

3 Hidden Cove Rd, Oak Bluffs

Listing courtesy of Listing Agent: Wendy Harman from Listing Office: Compass.
26 Sea Glen Road, Oak Bluffs
$1,390,000
4 Beds ⋅ 3 Baths ⋅ 73500318 MLS
Nestled in a desirable neighborhood, this beautifully maintained cape style home offers a rare blend of charm, flexibility and convenience in a serene island setting. Thoughtfully appointed throughout, the home welcomes you with an open living room that flows effortlessly into a bright dining area, where French doors open to a private stone patio—creating an inviting connection between indoor comfort and outdoor living. The first floor also includes a bedroom with a full bath, offering ideal flexibility for guests or remote work. Upstairs, two spacious bedrooms share an updated tile bath, providing comfortable accommodations with timeless appeal. The detached studio is a great bonus offering a living area, modern kitchenette and full bath! A spiral staircase leads to an additional upper-level space, offering even more versatility for guests, creative use or a private retreat. Strong rental history!

26 Sea Glen Road, Oak Bluffs

Listing courtesy of Listing Agent: Jennifer DaSilva from Listing Office: Compass.
82 Pennsylvania Avenue, Oak Bluffs
$1,250,000
3 Beds ⋅ 2 Baths ⋅ 73545719 MLS
Discover the charm of this inviting single-story ranch with a large, finished basement, perfect as a vacation retreat or year-round home. Extensively renovated, this charming 3-bedroom, 1.5-bath home offers comfort and effortless living. The finished basement adds nearly another 1000 SF of living space with a spacious TV room and game area for extra entertainment, while the welcoming back deck and enclosed outdoor shower make it easy to unwind after a day at the beach. Recently installed solar panels add significant energy efficiency. Set on a landscaped corner lot, the home is close to Lagoon Pond, where you can swim, shellfish, boat, and take in unforgettable sunsets. The location is close to Farm Neck Golf Club and downtown Oak Bluffs, with easy access to Island beaches, dining, and attractions. With strong rental bookings for 2026, this home is also a smart investment opportunity.

82 Pennsylvania Avenue, Oak Bluffs

Listing courtesy of Listing Agent: Emma Kennedy from Listing Office: Sandpiper Realty, Inc..
3 Kims Way, Oak Bluffs
$1,188,000
3 Beds ⋅ 2 Baths ⋅ 73478102 MLS
Recently updated Oak Bluffs ranch-style home ideally located near Downtown and Oak Bluffs Harbor. Step inside to discover vaulted ceilings and an airy open floor plan that seamlessly connects the living room, dining area, and a spacious kitchen featuring granite countertops and updated appliances. The private primary suite is thoughtfully positioned off the main living area and offers a full bath with in-suite laundry, plus its own separate exterior entrance, perfect for added privacy or guest flexibility. Two additional guest bedrooms and a full hall bath complete the interior layout. Outdoor living is equally inviting, with a charming front deck featuring built-in bench seating, a stone patio for entertaining, and a convenient storage shed. Recent upgrades include a new roof, updated flooring, and energy-efficient mini-split systems for heating and cooling. Move-in ready and perfectly suited for enjoying the Vineyard lifestyle.

3 Kims Way, Oak Bluffs

Listing courtesy of Listing Agent: Alyssa Halisky from Listing Office: Wallace & Co. Sotheby's International Realty.
61 Ocean Avenue Unit 4, Oak Bluffs
$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..
27 Laurel Avenue, Oak Bluffs
$1,375,000
3 Beds ⋅ 3 Baths ⋅ 73540741 MLS
Located in exclusive East Chop, this sun-filled 3BR Cottage blends authentic Martha’s Vineyard charm with modern coastal living. Immaculate, fully furnished, and turn-key, this property presents a phenomenal island retreat or a lucrative investment with fantastic rental potential.The main home pairs classic character with upgraded 200-amp electric, featuring bright spaces, a large kitchen, and inviting living areas. Step outside to an expansive Trex deck, manicured corner lot, and the quintessential outdoor shower. A standout feature is the separate detached bonus room: a spectacular flex space with a kitchenette and beautiful full bath—perfect for guest privacy or extended family gatherings.Unbeatable location just minutes to Oak Bluffs town center, the ferry, Marinelli Beach..

27 Laurel Avenue, Oak Bluffs

Listing courtesy of Listing Agent: Lisa Sheehan from Listing Office: .
22 Firehouse, Oak Bluffs
$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.
21 Butler Avenue Unit 1, Oak Bluffs
$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.
9 Brunswick, Oak Bluffs
$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.
18 Puritan Dr, Oak Bluffs
$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.
103 Meadow View Road, Oak Bluffs
$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..
12 Wheelhouse Way, Oak Bluffs
$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..
33 Ocean Ave, Oak Bluffs
$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..
10 Winthrop Avenue, Oak Bluffs
$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..
309 Barnes Road, Oak Bluffs
$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..
54 Columbian, Oak Bluffs
$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..
1 Pease Avenue, Oak Bluffs
$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..
16 Atlantic Avenue, Oak Bluffs
$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..
56 Garvin St., Oak Bluffs
$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..
7 Upper Meadow Ln, Oak Bluffs
$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..
35 New York Avenue, Oak Bluffs
$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..
7 South Meadow Lane, Oak Bluffs
$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..
63 Bayes Hill Rd, Oak Bluffs
$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..
24 School Street, Oak Bluffs
$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..
48 Vineyard Avenue Extension, Oak Bluffs
$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.
10 Wood Duck, Oak Bluffs
$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..

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.

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