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Oak Bluffs Homes for Sale

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  • 47 Winemack St, Oak Bluffs, MA 02557
    47 Winemack St, Oak Bluffs, MA 02557
    47 Winemack St, Oak Bluffs, MA 02557
    /22

    $1,199,000

    • 2 Beds
    • 1 Bath
    • 742 Sq Ft

    47 Winemack St, Oak Bluffs, MA 02557

    Oak Bluffs -East Chop-Close to the ocean. Two 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

    Agent Photo

    Lisa Lucier

    Anchor Realty of MV

    (508) 403-9601

    47 Winemack St, Oak Bluffs, MA 02557
  • 34 Massasoit Ave, Oak Bluffs, MA 02557
    34 Massasoit Ave, Oak Bluffs, MA 02557
    34 Massasoit Ave, Oak Bluffs, MA 02557
    /25

    $1,650,000

    • 6 Beds
    • 3.5 Baths
    • 1,616 Sq Ft

    34 Massasoit Ave, Oak Bluffs, MA 02557

    Downtown Oak Bluffs located in the Copeland District this Victorian home combines historic charm with modern comfort. Offering 6 spacious bedrooms and 3.5 bathrooms, this home provides ample living space for family and guests. Also making an ideal rental property Sleeping 12 comfortably just a block to the restaurants and shops of Circuit Ave. and a couple of blocks to the beach it's the perfect

    Agent Photo

    Lisa Lucier

    Anchor Realty of Martha's Vineyard

    (508) 299-5240

    34 Massasoit Ave, Oak Bluffs, MA 02557
  • 70 Carol Ln, Oak Bluffs, MA 02557
    70 Carol Ln, Oak Bluffs, MA 02557
    70 Carol Ln, Oak Bluffs, MA 02557
    /27

    $1,200,000

    • 2 Beds
    • 2.5 Baths
    • 1,500 Sq Ft

    70 Carol Ln, Oak Bluffs, MA 02557

    Charming Renovated Ranch in the Heart of Oak Bluffs Discover the perfect blend of comfort, convenience, and coastal charm in this beautifully renovated ranch home, ideally located in a central Oak Bluffs neighborhood close to everything down-Island. Set on a spacious 1/3-acre lot, this property offers both privacy and proximity — just minutes from the Oak Bluffs School, town center, and all the

    Agent Photo

    Lisa Lucier

    Anchor Realty of Martha's Vineyard

    (508) 456-5742

    70 Carol Ln, Oak Bluffs, MA 02557
  • 0 Massasoit Ave, Oak Bluffs, MA 02557
    0 Massasoit Ave, Oak Bluffs, MA 02557
    0 Massasoit Ave, Oak Bluffs, MA 02557
    /6

    $700,000

    • Land
    • 0.1 Acre
    • $7,000,000 per Acre

    0 Massasoit Ave, Oak Bluffs, MA 02557

    Commercial Land Downtown Oak Bluffs on Circuit Avenue. Explore the many potentials this commercial land has to offer in the desirable location in the heart of Oak Bluffs.

    Agent Photo

    Lisa Lucier

    Anchor Realty of Martha's Vineyard

    (508) 978-2876

    0 Massasoit Ave, Oak Bluffs, MA 02557
  • 6 Brewster Ave, Oak Bluffs, MA 02557
    6 Brewster Ave, Oak Bluffs, MA 02557
    6 Brewster Ave, Oak Bluffs, MA 02557
    /34

    $3,250,000

    • 4 Beds
    • 3 Baths
    • 1,728 Sq Ft

    6 Brewster Ave, Oak Bluffs, MA 02557

    Enjoy sweeping ocean views from this beautifully updated East Chop Victorian, complete with a timeless guest cottage. Thoughtfully renovated in 2010, the main residence seamlessly blends historic character with modern comfort. The kitchen and bathrooms have been stylishly updated while preserving the home's original charm and character. The guest cottage, tucked to the rear of the property,

    Katherine Donahue Sandpiper Realty Inc

    6 Brewster Ave, Oak Bluffs, MA 02557
  • 21 Island Inn Rd Unit 39G, Oak Bluffs, MA 02568
    21 Island Inn Rd Unit 39G, Oak Bluffs, MA 02568
    21 Island Inn Rd Unit 39G, Oak Bluffs, MA 02568
    /32

    $560,000

    • 1 Bed
    • 1.5 Baths
    • 590 Sq Ft

    21 Island Inn Rd Unit 39G, Oak Bluffs, MA 02568

    Own a piece of the Vineyard dream with a fully furnished, beautifully updated condo perfectly designed for comfort and vacation living at the Island Inn Country Club in Oak Bluffs. The location is just off Beach Road, a short distance to beaches, downtown Circuit Ave, and a lovely drive along Beach Road to Edgartown Village. The bike path, public transportation, and a popular restaurant with live

    Diana Gilmore Island Real Estate

    21 Island Inn Rd Unit 39G, Oak Bluffs, MA 02568
  • 47 E East Chop Dr Unit 5, Oak Bluffs, MA 02557
    47 E East Chop Dr Unit 5, Oak Bluffs, MA 02557
    47 E East Chop Dr Unit 5, Oak Bluffs, MA 02557
    /16

    $1,495,000

    • 1 Bed
    • 1 Bath
    • 650 Sq Ft

    47 E East Chop Dr Unit 5, Oak Bluffs, MA 02557

    East Chop Waterfront Luxury Cond -- This 1-BR, 1st floor, waterfront condominium, the ''Captain's Quarters'', features outstanding water views of the harbor and sound beyond, private entrance, cathedral ceilings and is just steps from the tennis club, beaches, restaurants, ferries to the mainland and downtown. In pristine condition, the unit includes new kitchen with Bosch appliances, living

    Perry Patterson MV Luxury Homes, LLC

    47 E East Chop Dr Unit 5, Oak Bluffs, MA 02557
  • 0-A California Ave Unit Part lot 79, Oak Bluffs, MA 02568
    0-A California Ave Unit Part lot 79, Oak Bluffs, MA 02568
    0-A California Ave Unit Part lot 79, Oak Bluffs, MA 02568
    /4

    $625,000

    • Land
    • 0.34 Acre
    • $1,815,277 per Acre

    0-A California Ave Unit Part lot 79, Oak Bluffs, MA 02568

    Oak Bluffs Buildable Lot – Prime Location. This flat 2-bedroom building lot is ideally located just moments from the Hudson Avenue access to scenic Lagoon Pond, with easy access to both Farm Neck Golf Club and downtown Oak Bluffs. Situated in a neighborhood of newly constructed homes, this lot presents an excellent opportunity to become part of a growing community in Oak Bluffs. According to the

    Andrew McElhinney Compass LLC

    0-A California Ave Unit Part lot 79, Oak Bluffs, MA 02568
  • 15 Tamarack Ln, Oak Bluffs, MA 02557
    15 Tamarack Ln, Oak Bluffs, MA 02557
    15 Tamarack Ln, Oak Bluffs, MA 02557
    /43

    $4,999,000

    • 6 Beds
    • 5.5 Baths
    • 3,214 Sq Ft

    15 Tamarack Ln, Oak Bluffs, MA 02557

    FARM NECK: The original 1780 Farm House was tastefully restored in 1985 to honor the land and legacy of Farm Neck. This serene 3.7 acre oasis of rolling greenery with a variety of mature trees and lots of natural privacy has an up Island feel with the down Island convenience to fine dining, shopping, ferry, airport, bike paths and includes Stockholder Membership in the popular Farm Neck Golf

    Michael Schweikert Ocean Park Realty, Inc.

    15 Tamarack Ln, Oak Bluffs, MA 02557
  • 4 Canonicus Ave, Oak Bluffs, MA 02557
    4 Canonicus Ave, Oak Bluffs, MA 02557
    4 Canonicus Ave, Oak Bluffs, MA 02557
    /39

    $5,325,000

    • 6 Beds
    • 4 Baths
    • 2,890 Sq Ft

    4 Canonicus Ave, Oak Bluffs, MA 02557

    With a striking presence overlooking Nantucket Sound and just moments from the vibrant pulse of downtown, this distinctive compound is infused with a laid-back West Coast spirit while honoring the vintage charm of Oak Bluffs. Airy and effortlessly elegant, the four-bedroom main house has been masterfully updated, introducing refined, contemporary comforts, designed for every season. Tucked to the

    Katherine Donahue Sandpiper Realty Inc

    4 Canonicus Ave, Oak Bluffs, MA 02557
  • 26 Winthrop Ave, Oak Bluffs, MA 02557
    26 Winthrop Ave, Oak Bluffs, MA 02557
    26 Winthrop Ave, Oak Bluffs, MA 02557
    /49

    $849,000

    • 1 Bed
    • 1 Bath
    • 803 Sq Ft

    26 Winthrop Ave, Oak Bluffs, MA 02557

    Hidden behind a wall of vegetation on Winthrop Avenue this is a little 'oasis' of a piece of land. One bedroom house situated on a 1/3 Acre, 14,810 sq.ft. level lot. One side of the property is lush with vegetation and the opposite side is clear. It is one lot in total and may not be subdivided. The existing house has been lived in year round. Only .6 of a mile to Oak Bluffs Harbor and .5 mile

    Alisan Lohan-Conway Alisan Lohan-Conway Properties

    26 Winthrop Ave, Oak Bluffs, MA 02557
  • 4 High Meadow Ln, Oak Bluffs, MA 02557
    4 High Meadow Ln, Oak Bluffs, MA 02557
    4 High Meadow Ln, Oak Bluffs, MA 02557
    /33

    $2,260,000

    • 4 Beds
    • 3.5 Baths
    • 2,810 Sq Ft

    4 High Meadow Ln, Oak Bluffs, MA 02557

    Classic Post & Beam set in Meadow View Farms - This stunning and solidly built four-bedroom home sits on almost an acre of land with endless possibilities and impressive touches throughout. A farmer’s porch stretches the full length of the home offering a warm welcome and a shady spot to relax overlooking the expansive front lawn. The light-filled, open first floor boasts cathedral ceilings, and

    Kate Burnside Portfolio Real Estate, Inc.

    4 High Meadow Ln, Oak Bluffs, MA 02557
  • 47 E Chop Dr Unit 4, Oak Bluffs, MA 02568
    47 E Chop Dr Unit 4, Oak Bluffs, MA 02568
    47 E Chop Dr Unit 4, Oak Bluffs, MA 02568
    /12

    $1,995,000

    • 2 Beds
    • 1 Bath
    • 879 Sq Ft

    47 E Chop Dr Unit 4, Oak Bluffs, MA 02568

    East Chop Harbor Front Luxury Condominiums -- This 2-bedroom, 2nd floor, waterfront condominium, the ''Tivoli'', features outstanding water views of the harbor and the sound beyond all the way to Chappaquiddick. Located just steps from the tennis club, beaches, restaurants, ferries to the mainland and downtown, this unit includes new kitchen with Bosch appliances, living and dining areas and a

    Perry Patterson MV Luxury Homes, LLC

    47 E Chop Dr Unit 4, Oak Bluffs, MA 02568
  • 8 Hitchings Cir, Oak Bluffs, MA 02557
    8 Hitchings Cir, Oak Bluffs, MA 02557
    8 Hitchings Cir, Oak Bluffs, MA 02557
    /12

    $899,000

    • 2 Beds
    • 2 Baths
    • 1,232 Sq Ft

    8 Hitchings Cir, Oak Bluffs, MA 02557

    Nestled in a quiet Oak Bluffs neighborhood, less than a mile from the harbor, beaches, shops, and restaurants, this Cape-style home offers the perfect balance of convenience and tranquility. The interior features an open kitchen and living room, plenty of space for guests, and a full unfinished basement. The two bedroom Title V septic system has passed inspection. Outside, the property features a

    Peyton Wallace Studio Realty

    8 Hitchings Cir, Oak Bluffs, MA 02557
  • 60R Carol Ln, Oak Bluffs, MA 02557
    60R Carol Ln, Oak Bluffs, MA 02557
    60R Carol Ln, Oak Bluffs, MA 02557
    /14

    $799,000

    • 2 Beds
    • 1 Bath
    • 624 Sq Ft

    60R Carol Ln, Oak Bluffs, MA 02557

    Charming Ranch-Style Cottage nestled on an 8,438 sq ft lot, this cozy ranch-style cottage offers easy, single-story living, ideal for those seeking the simplicity and charm of island life. The bright and open-concept kitchen and living area features a breakfast bar, creating a warm and welcoming space for everyday living or entertaining. The home includes two comfortable bedrooms and one full

    Nora Jardin Island Real Estate

    60R Carol Ln, Oak Bluffs, MA 02557
  • 7 Upper Meadow Ln, Oak Bluffs, MA 02557
    7 Upper Meadow Ln, Oak Bluffs, MA 02557
    7 Upper Meadow Ln, Oak Bluffs, MA 02557
    /28

    $1,799,000

    • 4 Beds
    • 2.5 Baths
    • 3,268 Sq Ft

    7 Upper Meadow Ln, Oak Bluffs, MA 02557

    Meadowview Farms - Tucked at the end of a quiet cul-de-sac, this spacious Colonial offers more than 3,200 square feet of comfortable living space. This home is ideal for those who love to host lively gatherings while providing ample accommodations. Inside, you'll find four well-sized bedrooms and two and a half baths, including a generous primary suite with double walk-in closets and a private

    Lesley Heidt Sandpiper Realty Inc

    7 Upper Meadow Ln, Oak Bluffs, MA 02557
  • 47 E Chop Dr Unit 2, Oak Bluffs, MA 02568
    47 E Chop Dr Unit 2, Oak Bluffs, MA 02568
    47 E Chop Dr Unit 2, Oak Bluffs, MA 02568
    /13

    $1,495,000

    • 1 Bed
    • 1 Bath
    • 736 Sq Ft

    47 E Chop Dr Unit 2, Oak Bluffs, MA 02568

    East Chop Water Front Luxury Condominium -- This 1-bedroom, waterfront condominium, ''Cottage City'', features outstanding water views of the harbor and sound beyond, a cozy propane fireplace and is just steps from the tennis club, beaches, restaurants, ferries to the mainland and downtown. In pristine condition, this 1st-floor unit includes new kitchen with Bosch appliances, living room with

    Perry Patterson MV Luxury Homes, LLC

    47 E Chop Dr Unit 2, Oak Bluffs, MA 02568
  • 54 Towanticut Ave, Oak Bluffs, MA 02568
    54 Towanticut Ave, Oak Bluffs, MA 02568
    54 Towanticut Ave, Oak Bluffs, MA 02568
    /23

    $1,090,000

    • 3 Beds
    • 2 Baths
    • 1,232 Sq Ft

    54 Towanticut Ave, Oak Bluffs, MA 02568

    Living is Easy in this 3-bedroom 2 bath air-conditioned Ranch located 1 mile from the Center of Oak Bluffs. Features include a spacious living room with a wood-burning fireplace, an updated kitchen with granite countertops and stainless-steel appliances. The dining area has sliders leading to a spacious deck and outdoor shower overlooking the yard space with plenty of room for gardens, pets or

    JoJo Lambert Island Home Realty Inc.

    54 Towanticut Ave, Oak Bluffs, MA 02568
  • 12 & 14 Maple Ave, Oak Bluffs, MA 02557
    12 & 14 Maple Ave, Oak Bluffs, MA 02557
    12 & 14 Maple Ave, Oak Bluffs, MA 02557
    /54

    $1,830,000

    • 4 Beds
    • 4 Baths
    • 1,600 Sq Ft

    12 & 14 Maple Ave, Oak Bluffs, MA 02557

    Two Historic Oak Bluffs Cottages - Prime Location - Deeded Separately Perched atop a gentle hill, surrounded by lush, established gardens in one of the island's most storied neighborhoods, these two charming 1909 twin cottages offer a rare opportunity to own a piece of local history--just a short distance to the harbor, downtown, and the beloved Winston's takeout. Built at a time when automobiles

    Leslie Floyd Portfolio Properties

    12 & 14 Maple Ave, Oak Bluffs, MA 02557
  • 47 E Chop Dr Unit 3, Oak Bluffs, MA 02568
    47 E Chop Dr Unit 3, Oak Bluffs, MA 02568
    47 E Chop Dr Unit 3, Oak Bluffs, MA 02568
    /17

    $1,995,000

    • 2 Beds
    • 1 Bath
    • 802 Sq Ft

    47 E Chop Dr Unit 3, Oak Bluffs, MA 02568

    East Chop Water Front Luxury Condominiums -- This 2BR, waterfront condominium, the ''Highlands'', features outstanding water views of the harbor, the sound and the Cape beyond and is just steps from the tennis club, beaches, restaurants, ferries to the mainland and downtown. In pristine condition, this 2nd floor unit includes new kitchen with Bosch appliances, living and dining areas and a

    Perry Patterson MV Luxury Homes, LLC

    47 E Chop Dr Unit 3, Oak Bluffs, MA 02568
  • 28 Barling Ave, Vineyard Haven, MA 02568
    28 Barling Ave, Vineyard Haven, MA 02568
    28 Barling Ave, Vineyard Haven, MA 02568
    /30

    $999,000

    • 2 Beds
    • 1 Bath
    • 1,232 Sq Ft

    28 Barling Ave, Vineyard Haven, MA 02568

    Oak Bluffs: Home Sweet HomeSituated on over a quarter acre of beautifully landscaped, level grounds with colorful perennial plantings and mature trees, this sun-filled ranch offers a perfect blend of comfort and charm. The open kitchen, dining, and living areas feature cathedral ceilings, classic vertical knotty pine walls, and a cozy brick fireplace. Enjoy a convenient first-floor bedroom

    Alan Schweikert Ocean Park Realty Inc

    28 Barling Ave, Vineyard Haven, MA 02568
  • 0 Barnes Rd Unit 32400334, Oak Bluffs, MA 02557
    0 Barnes Rd Unit 32400334, Oak Bluffs, MA 02557
    0 Barnes Rd Unit 32400334, Oak Bluffs, MA 02557
    /11

    $495,000

    • Land
    • 0.23 Acre
    • $2,152,174 per Acre

    0 Barnes Rd Unit 32400334, Oak Bluffs, MA 02557

    Located in the heart of Oak Bluffs, this land offering abuts a protected Town park and is within close proximity to the various public access points to the sandy shoreline of Lagoon Pond. With engineering in place for a 1 bedroom home, embrace the unique opportunity to build your own custom residence. Whether you envision a cozy cottage, a modern retreat, or a traditional island dwelling, the

    Alyssa Halisky Wallace & Co. Sotheby's International Realty

    0 Barnes Rd Unit 32400334, Oak Bluffs, MA 02557
  • 2 Lincoln Ave, Oak Bluffs, MA 02568
    2 Lincoln Ave, Oak Bluffs, MA 02568
    2 Lincoln Ave, Oak Bluffs, MA 02568
    /20

    $640,000

    • 1 Bed
    • 1 Bath
    • 354 Sq Ft

    2 Lincoln Ave, Oak Bluffs, MA 02568

    Nestled in the heart of the historic Martha’s Vineyard Camp Meeting Association, this beautifully updated suite cottage offers the rare opportunity for year-round living in Oak Bluffs’ campground community. Fully renovated in 2023, including kitchen, bath, floors and winterization, the home seamlessly blends classic Vineyard charm with modern comfort — featuring upgraded systems and finishes that

    Stacy Ickes Donnelly + Co

    2 Lincoln Ave, Oak Bluffs, MA 02568
  • 47 Tiffany Dr, Oak Bluffs, MA 02557
    47 Tiffany Dr, Oak Bluffs, MA 02557
    47 Tiffany Dr, Oak Bluffs, MA 02557
    /47

    $2,499,000 Pre-Foreclosure

    • 4 Beds
    • 2.5 Baths
    • 2,544 Sq Ft

    47 Tiffany Dr, Oak Bluffs, MA 02557

    Your private oasis with a POOL awaits in this beautifully updated Lagoon Hills retreat on over 1.5 acres. Enjoy a carefree, single-level lifestyle featuring an open-concept kitchen and dining area, spacious living room, office and exercise room — all thoughtfully designed for comfort and flow. Step outside to a stunning backyard anchored by a sparkling pool, surrounded by decks, patios, and lush

    Jennifer DaSilva Compass | Point B

    47 Tiffany Dr, Oak Bluffs, MA 02557
  • 2 Farm Path, Oak Bluffs, MA 02557
    2 Farm Path, Oak Bluffs, MA 02557
    2 Farm Path, Oak Bluffs, MA 02557
    /37

    $1,750,000

    • 4 Beds
    • 3 Baths
    • 3,058 Sq Ft

    2 Farm Path, Oak Bluffs, MA 02557

    "Turn-key" offering! This custom cape design with a delightful farmer's porch provides ample opportunities to entertain. Set upon nearly an acre of level and landscaped land with irrigation, it abuts the State Forrest, has an open floor plan with cathedral ceilings and skylights. The three bedroom main, has A/C, a finished basement rec room, a large rear deck that spills forth onto a large yard

    Sean Federowicz Landmarks at TODAY Real Estate

    2 Farm Path, Oak Bluffs, MA 02557
  • 400 Barnes Rd, Vineyard Haven, MA 02568
    400 Barnes Rd, Vineyard Haven, MA 02568
    400 Barnes Rd, Vineyard Haven, MA 02568
    /45

    $6,395,000

    • 6 Beds
    • 5.5 Baths
    • 7,000 Sq Ft

    400 Barnes Rd, Vineyard Haven, MA 02568

    Experience the quiet elegance of this rare Asian-inspired contemporary estate set on 2.42 acres in a prime Oak Bluffs location. Tucked behind a long private drive and surrounded by 234 acres of Southern Woodlands conservation land offering biking and hiking, this expansive property offers unparalleled privacy just minutes from Featherstone Center for the Arts, Farm Neck Golf Club and the island’s

    Jennifer DaSilva Compass | Point B

    400 Barnes Rd, Vineyard Haven, MA 02568
  • 24 School St, Oak Bluffs, MA 02557
    24 School St, Oak Bluffs, MA 02557
    24 School St, Oak Bluffs, MA 02557
    /26

    $875,000

    • 2 Beds
    • 1 Bath
    • 861 Sq Ft

    24 School St, Oak Bluffs, MA 02557

    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

    Stephanie Roache Donnelly + Co.

    24 School St, Oak Bluffs, MA 02557
  • 150 E Chop Dr, Oak Bluffs, MA 02557
    150 E Chop Dr, Oak Bluffs, MA 02557
    150 E Chop Dr, Oak Bluffs, MA 02557
    /41

    $8,900,000 Pre-Foreclosure

    • 8 Beds
    • 9 Baths
    • 8,560 Sq Ft

    150 E Chop Dr, Oak Bluffs, MA 02557

    Big Bluff. The crown jewel of East Chop. Timeless elegance and unmatched craftsmanship on the shores of Martha’s Vineyard. Renowned architect M. Hutker and preeminent builder J.G.Early teamed up to create this magnificent waterfront estate. 8,500 Sq. ft. of pure luxury. Open-concept living with large picture windows, a chef’s kitchen with island, high-end appliances, wet bar, and sunlit breakfast

    Moira Lown Coldwell Banker Realty - Wellesley

    150 E Chop Dr, Oak Bluffs, MA 02557
  • 22 Paddock Rd Unit 85, Oak Bluffs, MA 02568
    22 Paddock Rd Unit 85, Oak Bluffs, MA 02568
    22 Paddock Rd Unit 85, Oak Bluffs, MA 02568
    /6

    $1,795,000

    • Land
    • 1.87 Acres
    • $961,435 per Acre

    22 Paddock Rd Unit 85, Oak Bluffs, MA 02568

    THE PRESERVE at THE WOODLANDS ~ OAK BLUFFS COVETED COMMUNITY of architecturally designed residences. Live in ONE of the most sought-after locations in Oak Bluffs that is conveniently located to town, beaches, harbor, ferry ports, and Farm Neck Golf & Tennis Club. This is a RARE OFFERING to purchase one of the last remaining building lots and develop a family compound. There are underground

    Marilyn Moses Ocean Park Realty Inc

    22 Paddock Rd Unit 85, Oak Bluffs, MA 02568
  • 0-B California Ave Unit Part lot 79, Oak Bluffs, MA 02568
    0-B California Ave Unit Part lot 79, Oak Bluffs, MA 02568
    0-B California Ave Unit Part lot 79, Oak Bluffs, MA 02568
    /4

    $675,000

    • Land
    • 0.23 Acre
    • $2,941,176 per Acre

    0-B California Ave Unit Part lot 79, Oak Bluffs, MA 02568

    Oak Bluffs Buildable Lot – Prime LocationThis flat 3-bedroom building lot is ideally located just moments from the Hudson Avenue access to scenic Lagoon Pond, with easy access to both Farm Neck Golf Club and downtown Oak Bluffs. Situated in a neighborhood of newly constructed homes, this lot presents an excellent opportunity to become part of a growing community in Oak Bluffs. According to

    Andrew McElhinney Compass LLC

    0-B California Ave Unit Part lot 79, Oak Bluffs, MA 02568
  • 9 Brunswick Ave, Oak Bluffs, MA 02557
    9 Brunswick Ave, Oak Bluffs, MA 02557
    9 Brunswick Ave, Oak Bluffs, MA 02557
    /21

    $1,395,000

    • 3 Beds
    • 1 Bath
    • 1,033 Sq Ft

    9 Brunswick Ave, Oak Bluffs, MA 02557

    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 and extensively UPDATED INSIDE AND OUT. Enjoy peace of mind with a NEW septic system, siding, windows, water line from the street, and upgraded electrical and plumbing. The interior boasts new flooring, insulation, fresh paint, a

    Alice Pierce Coldwell Banker Realty - Hingham

    9 Brunswick Ave, Oak Bluffs, MA 02557
  • 0 Barnes Rd Unit 59 42701, Oak Bluffs, MA 02557
    0 Barnes Rd Unit 59 42701, Oak Bluffs, MA 02557
    0 Barnes Rd Unit 59 42701, Oak Bluffs, MA 02557
    /11

    $495,000

    • Land
    • 0.23 Acre
    • $2,152,174 per Acre

    0 Barnes Rd Unit 59 42701, Oak Bluffs, MA 02557

    Located in the heart of Oak Bluffs, this land offering abuts a protected Town park and is within close proximity to the various public access points to the sandy shoreline of Lagoon Pond. With engineering in place for a 1 bedroom home, embrace the unique opportunity to build your own custom residence. Whether you envision a cozy cottage, a modern retreat, or a traditional island dwelling, the

    Alyssa Halisky Wallace & Co. Sotheby's

    0 Barnes Rd Unit 59 42701, Oak Bluffs, MA 02557
  • 60 -R Carol Ln, Oak Bluffs, MA 02557
    60 -R Carol Ln, Oak Bluffs, MA 02557
    60 -R Carol Ln, Oak Bluffs, MA 02557
    /15

    $799,000

    • 2 Beds
    • 1 Bath
    • 624 Sq Ft

    60 -R Carol Ln, Oak Bluffs, MA 02557

    Charming Ranch-Style Cottage nestled on an 8,438 sq ft lot, this cozy ranch-style cottage offers easy, single-story living, ideal for those seeking the simplicity and charm of island life. The bright and open-concept kitchen and living area features a breakfast bar, creating a warm and welcoming space for everyday living or entertaining. The home includes two comfortable bedrooms and one full

    Sheila Morse Island Real Estate

    60 -R Carol Ln, Oak Bluffs, MA 02557
  • 47 E Chop Dr Unit 1, Oak Bluffs, MA 02568
    47 E Chop Dr Unit 1, Oak Bluffs, MA 02568
    47 E Chop Dr Unit 1, Oak Bluffs, MA 02568
    /12

    $1,495,000

    • 1 Bed
    • 1 Bath
    • 731 Sq Ft

    47 E Chop Dr Unit 1, Oak Bluffs, MA 02568

    East Chop Water Front Luxury Condominium -- This 1-bedroom, 1st floor, waterfront condominium, ''Oak Bluffs'', features outstanding water views of the harbor and sound beyond. Located just steps from the tennis club, beaches, restaurants, ferries to the mainland and downtown, this unit includes new kitchen with Bosch appliances, living room, dining area and a private covered front porch

    Perry Patterson MV Luxury Homes, LLC

    47 E Chop Dr Unit 1, Oak Bluffs, MA 02568
  • 7 S Meadow Ln, Oak Bluffs, MA 02557
    7 S Meadow Ln, Oak Bluffs, MA 02557
    7 S Meadow Ln, Oak Bluffs, MA 02557
    /38

    $1,825,000

    • 4 Beds
    • 3 Baths
    • 3,142 Sq Ft

    7 S Meadow Ln, Oak Bluffs, MA 02557

    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

    Katherine Donahue Sandpiper Realty Inc

    7 S Meadow Ln, Oak Bluffs, MA 02557
  • 34 Windemere Rd, Oak Bluffs, MA 02557
    34 Windemere Rd, Oak Bluffs, MA 02557
    34 Windemere Rd, Oak Bluffs, MA 02557
    /44

    $2,700,000

    • 4 Beds
    • 3 Baths
    • 1,399 Sq Ft

    34 Windemere Rd, Oak Bluffs, MA 02557

    Perfect opportunity to own a Beautiful Beach Cottage with access to Lagoon. Totally renovated in 2019. It has been designed for relaxed living and memorable entertaining. There are 3 seating areas on the deck, to enjoy dining outside, experiencing incredible waterviews and lovely sky reflections of sunsets. Beautifully landscaped, with seasonal flowers, and Butterfly flowering bushes. Easement to

    JoJo Lambert Island Home Realty Inc.

    34 Windemere Rd, Oak Bluffs, MA 02557
  • 111 Eastville Ave, Oak Bluffs, MA 02557
    111 Eastville Ave, Oak Bluffs, MA 02557
    111 Eastville Ave, Oak Bluffs, MA 02557
    /44

    $2,599,000

    • 6 Beds
    • 4 Baths
    • 2,400 Sq Ft

    111 Eastville Ave, Oak Bluffs, MA 02557

    PRICE REDUCTION! Just steps from the beach and minutes to downtown Oak Bluffs and Vineyard Haven, this fully furnished, turnkey coastal home offers an unbeatable location and a proven rental history. Set on an oversized lot just two parcels from the beach, the residence features six bedrooms and four bathrooms, providing generous space for family, friends, or guests. Enjoy sweeping 180 water

    Ed Charter Arrowhead Homes

    111 Eastville Ave, Oak Bluffs, MA 02557
  • 56 Holmes Hole Rd Unit 10, Oak Bluffs, MA 02568
    56 Holmes Hole Rd Unit 10, Oak Bluffs, MA 02568
    /2

    $674,000

    • Land
    • 0.49 Acre
    • $1,375,510 per Acre

    56 Holmes Hole Rd Unit 10, Oak Bluffs, MA 02568

    Presenting a unique opportunity to acquire a wooded level lot located on Holmes Hole Road in Oak Bluffs, encompassing a .49-acre parcel situated within a Residential Urban (RU) zoning district. This property offers a serene environment ideal for constructing a home while remaining conveniently close to the town's amenities. There is potential for developing a 3-bedroom residence utilizing either

    Marilyn Moses Ocean Park Realty Inc

    56 Holmes Hole Rd Unit 10, Oak Bluffs, MA 02568
  • 47 E Chop Dr, Oak Bluffs, MA 02568
    47 E Chop Dr, Oak Bluffs, MA 02568
    47 E Chop Dr, Oak Bluffs, MA 02568
    /39

    $10,500,000

    • 8 Beds
    • 6 Baths
    • 3,888 Sq Ft

    47 E Chop Dr, Oak Bluffs, MA 02568

    East Chop waterfront - Enjoy the ultimate in waterfront living experiences at this coveted East Chop location, with its spectacular waterviews and easy access to beach, tennis, dock/slips, and a wide range of harbor amenities. It offers a variety of multi-functional uses including -- 1.) Use it as a residential home or family compound, or live in a portion and rent a portion, 2.) Use it as its

    Perry Patterson MV Luxury Homes, LLC

    47 E Chop Dr, Oak Bluffs, MA 02568
  • 267 Barnes Rd, Oak Bluffs, MA 02557
    267 Barnes Rd, Oak Bluffs, MA 02557
    267 Barnes Rd, Oak Bluffs, MA 02557
    /68

    $4,395,000

    • 3 Beds
    • 5.5 Baths
    • 4,046 Sq Ft

    267 Barnes Rd, Oak Bluffs, MA 02557

    Live the Dream on Martha’s Vineyard! Whether you're seeking a year-round residence or a seasonal escape, this is a once-in-a-lifetime opportunity to own a piece of paradise. Step into a world of coastal luxury with 163 feet of pristine Lagoon frontage, complete with your own private sandy beach. Nestled on 1.25 acres of lush, landscaped paradise, this rare gem offers sweeping lawns, panoramic

    Stephanie Roache Donnelly + Co

    267 Barnes Rd, Oak Bluffs, MA 02557

Showing Results 1 - 40, Page 1 of 2

Massachusetts Dukes County Marthas Vineyard Oak Bluffs

Real Estate & Homes for Sale in Oak Bluffs, Marthas Vineyard

Why Live in Oak Bluffs
Oak Bluffs, located in the northeast of Martha’s Vineyard, is renowned for its whimsical gingerbread houses and historical significance as a summer haven for Black Americans. This down-island town is a bustling port of entry during the summer season, where tourists disembark from ferry boats and explore attractions like Circuit Avenue, known for its T-shirts and fresh doughnuts. The town features gray-shingled beach houses overlooking the Nantucket Sound, and the commercial district offers pizza parlors, ice cream shops, and clothing stores. Oak Bluffs is home to the oldest platform carousel in the U.S., the Flying Horses Carousel, and hosts the Martha’s Vineyard African American Film Festival and a fireworks show every August. The Ritz Café provides nightlife with live music and karaoke, while the Sweet Life Café offers upscale dining year-round. Ocean Park, with its rolling hills and Victorian homes, and the Martha’s Vineyard Camp Meeting Association, with its brightly colored gingerbread houses, are notable landmarks. The town also has gray-shingled beach cottages, Cape Cods, and farmhouses. Martha’s Vineyard Regional High School, a highly rated institution, serves the island’s students. Health care is accessible at Mass General Brigham Martha’s Vineyard Hospital, which offers comprehensive services. Residents and visitors can enjoy sandy pathways along the Nantucket Sound, beaches like Inkwell Beach, and a skate park near the high school. Oak Bluffs is 10 minutes from Vineyard Haven, 15 minutes from Edgartown, and 15 minutes from Martha’s Vineyard Airport.
Learn more about living in Oak Bluffs

Frequently Asked Questions

Is Oak Bluffs a good place to live?
Oak Bluffs is a good place to live. Oak Bluffs is considered very car-dependent and somewhat bikeable. Oak Bluffs is a neighborhood with a crime score of 1, making it safer than the average neighborhood in the U.S. Oak Bluffs has 5 parks for recreational activities. It is sparse in population with 1.6 people per acre and a median age of 49. The average household income is $133,511 which is above the national average. College graduates make up 46.9% of residents. A majority of residents in Oak Bluffs are home owners, with 26.7% of residents renting and 73.3% of residents owning their home. A local real estate agent serving Oak Bluffs can help you decide if this neighborhood is the right one for you. Learn more on our Oak Bluffs neighborhood guide.
Is Oak Bluffs, MA a safe neighborhood?
Oak Bluffs, MA is safer than the average neighborhood in the United States. It received a crime score of 1 out of 10.
How much do you need to make to afford a house in Oak Bluffs?
The median home price in Oak Bluffs is $1,460,000. If you put a 20% down payment of $292,000 and had a 30-year fixed mortgage with an interest rate of 6.21%, your estimated principal and interest payment would be $7,160 a month plus property taxes, HOA fees, home insurance, PMI, and utilities. Using the 28% rule, you would need to make at least $307K a year to afford the median home price in Oak Bluffs. Learn how much home you can afford with our Home Affordability Calculator. The average household income in Oak Bluffs is $134K.
What are the best public schools in Oak Bluffs?
The best public schools that serve Oak Bluffs are:
What are the best private schools in Oak Bluffs?
The best private schools that serve Oak Bluffs are:
What are the most popular zip codes in Oak Bluffs, Marthas Vineyard, MA?
The most popular zip codes in Oak Bluffs, Marthas Vineyard, MA include 02568, 02536, 02539, 02575 and 02535.
What are the most popular neighborhoods near Oak Bluffs, Marthas Vineyard, MA?
The most popular neighborhoods near Oak Bluffs, Marthas Vineyard, MA are Vineyard Haven, Edgartown, West Tisbury, Woods Hole and Falmouth Village.

Home Trends in Oak Bluffs, MA

On average, homes in Oak Bluffs, Marthas Vineyard sell after 92 days on the market compared to the national average of 53 days. The median sale price for homes in Oak Bluffs, Marthas Vineyard over the last 12 months is $1,118,125, down 7% from the median home sale price over the previous 12 months.

Housing Trends

Median Sale Price
$1,118,125
Median Single Family Sale Price
$1,475,000
Median 2 Bedroom Sale Price
$1,050,000
Median 1 Bedroom Sale Price
$1,495,000
Average Price Per Sq Ft
$1,094
Number of Homes for Sale
48
Last 12 months Home Sales
138
Months of Supply
4.20
Median List Price
$1,460,000
Median Change From 1st List Price
7%
Median Home Sale Price YoY Change
-7%
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