39

Oak Bluffs Homes for Sale

Section Image Section Image
  • 70 Carol Ln, Oak Bluffs, MA 02557
    70 Carol Ln, Oak Bluffs, MA 02557
    70 Carol Ln, Oak Bluffs, MA 02557
    /27

    $1,150,000

    • 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
  • 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
  • 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
  • 63 Bayes Hill Rd, Oak Bluffs, MA 02557
    63 Bayes Hill Rd, Oak Bluffs, MA 02557
    63 Bayes Hill Rd, Oak Bluffs, MA 02557
    /36

    $2,900,000

    • 4 Beds
    • 5 Baths
    • 5,165 Sq Ft

    63 Bayes Hill Rd, Oak Bluffs, MA 02557

    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,

    Casandra Hyland Sandpiper Realty, Inc.

    63 Bayes Hill Rd, 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 -- 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

    Lesley Heidt Sandpiper Realty Inc

    7 Upper Meadow Ln, 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
    /23

    $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 FarmsThis bright and charming four-bedroom home sits on almost an acre of land with endless possibilities and impressive touches throughout.The farmer's porch overlooks an expansive front lawn and offers a warm welcome. The open first floor is sunny with cathedral ceilings and gas fireplace with stonework. The kitchen features granite countertops, Wolf

    Kate Burnside Portfolio Properties

    4 High Meadow Ln, Oak Bluffs, MA 02557
  • 35 Double Ox Rd, Oak Bluffs, MA 02557
    35 Double Ox Rd, Oak Bluffs, MA 02557
    35 Double Ox Rd, Oak Bluffs, MA 02557
    /9

    $2,250,000

    • 3 Beds
    • 3.5 Baths
    • 2,475 Sq Ft

    35 Double Ox Rd, Oak Bluffs, MA 02557

    Would you love to live or vacation in a brand-new home on Martha’s Vineyard?We have the LOCATION, REPUTABLE LONG-STANDING BUILDER & PROVEN TRACK RECORD!Come take a tour of the newest home under construction in the Lagoon Ridge neighborhood.Easy to show – Call now! To be built with lot purchase$700,000 and building contract $1,550,000.This 3-bedroom dream home is set in an elevated

    Marilyn Moses Ocean Park Realty Inc

    35 Double Ox Rd, Oak Bluffs, MA 02557
  • 33 Ocean Ave, Oak Bluffs, MA 02557
    33 Ocean Ave, Oak Bluffs, MA 02557
    33 Ocean Ave, Oak Bluffs, MA 02557
    /30

    $2,950,000

    • 3 Beds
    • 2.5 Baths
    • 1,845 Sq Ft

    33 Ocean Ave, Oak Bluffs, MA 02557

    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

    Marcia Sullivan Garvey Donnelly + Co.

    33 Ocean 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
  • 4 Canonicus Ave, Oak Bluffs, MA 02557
    4 Canonicus Ave, Oak Bluffs, MA 02557
    4 Canonicus Ave, Oak Bluffs, MA 02557
    /36

    $5,325,000

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

    4 Canonicus Ave, Oak Bluffs, MA 02557

    Overlooking Nantucket Sound and just steps from the vibrant heart of downtown Oak Bluffs, this distinctive compound blends laid-back West Coast style with classic island charm. The light-filled four-bedroom main house has been thoughtfully updated with modern, year-round comforts. Privately set at the rear, the guest house known as The Nest offers a peaceful retreat with a private deck, outdoor

    Katie Donahue & Rachel Serwa Group Sandpiper Realty, Inc.

    4 Canonicus Ave, 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
  • 24 School St, Oak Bluffs, MA 02557
    24 School St, Oak Bluffs, MA 02557
    24 School St, Oak Bluffs, MA 02557
    /25

    $799,000

    • 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
  • 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
  • 24 Towanticut Ave Unit 188, Oak Bluffs, MA 02568
    24 Towanticut Ave Unit 188, Oak Bluffs, MA 02568
    24 Towanticut Ave Unit 188, Oak Bluffs, MA 02568
    /3

    $857,000

    • Land
    • 0.39 Acre
    • $2,209,902 per Acre

    24 Towanticut Ave Unit 188, Oak Bluffs, MA 02568

    OAK BLUFFS - A Rare Opportunity to purchase an Eight (8) Bedroom lot. This already cleared, oversized lot, 16,895sq.ft., (more than 1/3 acre) comes with an Approved Eight (8) Bedroom Septic Design, ready to build. Exceptional potential for a spacious custom home, family compound, or a rental property. Utilities are available by the lot, which significantly reduces development costs and time.

    Alisan Lohan-Conway Alisan Lohan-Conway Properties

    24 Towanticut Ave Unit 188, 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
  • 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

    Michael Schweikert Ocean Park Realty Inc

    28 Barling Ave, Vineyard Haven, MA 02568
  • 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
  • 12 Wheelhouse Way, Oak Bluffs, MA 02557
    12 Wheelhouse Way, Oak Bluffs, MA 02557
    12 Wheelhouse Way, Oak Bluffs, MA 02557
    /19

    $1,095,000

    • 3 Beds
    • 1.5 Baths
    • 1,487 Sq Ft

    12 Wheelhouse Way, Oak Bluffs, MA 02557

    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, charming town centers and year-round ferries. 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.

    Dawn Bellante Sandpiper Realty, Inc.

    12 Wheelhouse Way, Oak Bluffs, MA 02557
  • 54 Columbian Ave, Oak Bluffs, MA 02557
    54 Columbian Ave, Oak Bluffs, MA 02557
    54 Columbian Ave, Oak Bluffs, MA 02557
    /14

    $1,295,000

    • 4 Beds
    • 2 Baths
    • 1,764 Sq Ft

    54 Columbian Ave, Oak Bluffs, MA 02557

    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

    Katrina Lima Donnelly + Co

    54 Columbian Ave, Oak Bluffs, MA 02557
  • 35 New York Ave, Oak Bluffs, MA 02568
    35 New York Ave, Oak Bluffs, MA 02568
    35 New York Ave, Oak Bluffs, MA 02568
    /24

    $3,500,000

    • 7 Beds
    • 5 Baths
    • 3,880 Sq Ft

    35 New York Ave, Oak Bluffs, MA 02568

    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

    Emma Kennedy Sandpiper Realty, Inc.

    35 New York Ave, Oak Bluffs, MA 02568
  • 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
  • 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
  • 112 Dukes County Ave, Oak Bluffs, MA 02557
    112 Dukes County Ave, Oak Bluffs, MA 02557
    112 Dukes County Ave, Oak Bluffs, MA 02557
    /8

    $599,000 Coming Soon

    • Land
    • 0.07 Acre
    • $8,557,143 per Acre

    112 Dukes County Ave, Oak Bluffs, MA 02557

    COMING SOON! Downtown Oak Bluffs B1-zoned parcel offering a rare mixed-use development opportunity in one of Martha's Vineyard's most iconic and active locations. Conveniently located near Inkwell Beach, Oak Bluffs Harbor, the Steamship Authority, day-trip ferry services, Circuit Avenue, and Ocean Park. This level lot includes an existing poured concrete foundation and Martha's Vineyard

    Rose Ryley Wallace & Co. Sotheby's International Realty

    112 Dukes County Ave, Oak Bluffs, MA 02557
  • 9 Brunswick Ave, Oak Bluffs, MA 02557
    9 Brunswick Ave, Oak Bluffs, MA 02557
    9 Brunswick Ave, Oak Bluffs, MA 02557
    /40

    $1,295,000

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

    9 Brunswick Ave, Oak Bluffs, MA 02557

    PRIME LOCATION! 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 stylishly renovated kitchen, and efficient new

    Alice Pierce Coldwell Banker Realty - Martha's Vineyard

    9 Brunswick Ave, Oak Bluffs, MA 02557
  • 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
  • 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
  • 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
  • 0 Pennsylvania Ave Unit 43914, Oak Bluffs, MA 02568
    0 Pennsylvania Ave Unit 43914, Oak Bluffs, MA 02568
    /2

    $1,250,000

    • 1 Bed
    • 1 Bath
    • 855 Sq Ft

    0 Pennsylvania Ave Unit 43914, Oak Bluffs, MA 02568

    Unique new construction opportunity on Pennsylvania Ave in Oak Bluffs! Offered preconstruction so there is the ability to customize, this modern carriage house includes a spacious 1-bedroom apartment (855 sq ft with full kitchen, living room and bathroom) above a 2-car garage. Ideal for year round or seasonal residents, or businesses seeking to solve workforce housing needs along with secure

    Peyton Wallace Studio Realty

    0 Pennsylvania Ave Unit 43914, Oak Bluffs, MA 02568
  • 2 Hope's Way, Oak Bluffs, MA 02557
    2 Hope's Way, Oak Bluffs, MA 02557
    2 Hope's Way, Oak Bluffs, MA 02557
    /3

    $2,100,000

    • 3 Beds
    • 3.5 Baths
    • 2,019 Sq Ft

    2 Hope's Way, Oak Bluffs, MA 02557

    ESTEEMED BUILDER READY to BREAK GROUND! Purchase this exceptional lot in Lagoon Ridge and start building your ISLAND DREAM 3 BR 3.5 home today! Purchase lot ($700,000)& Execute a BUILDING CONTRACT ($1,400,000 )or choose your own builder... Call for details and schedule a tour! Welcome to Oak Bluffs’ newest and most sought-after neighborhood, where you can construct your 3-bedroom home on a lofty

    Marilyn Moses Ocean Park Realty Inc

    2 Hope's Way, Oak Bluffs, MA 02557
  • 50 Canonicus Ave, Oak Bluffs, MA 02557
    50 Canonicus Ave, Oak Bluffs, MA 02557
    50 Canonicus Ave, Oak Bluffs, MA 02557
    /22

    $925,000

    • 2 Beds
    • 0.5 Baths
    • 953 Sq Ft

    50 Canonicus Ave, Oak Bluffs, MA 02557

    Rare Opportunity to Be in a Special Location and Neighborhood! Loved by generations, this quintessential Vineyard cottage has been in the same family since its creation in 1900. Step back in time and enjoy easy cottage living of yesteryear with modern updates including newer windows and electrical. Nestled under mature trees and just .3 mile to Inkwell Beach, join this close-knit neighborhood and

    Michele Moore Island Real Estate

    50 Canonicus Ave, Oak Bluffs, MA 02557
  • 35 Double Ox Rd Unit 42, Oak Bluffs, MA 02557
    35 Double Ox Rd Unit 42, Oak Bluffs, MA 02557
    35 Double Ox Rd Unit 42, Oak Bluffs, MA 02557
    /8

    $700,000

    • Land
    • 0.26 Acre
    • $2,670,736 per Acre

    35 Double Ox Rd Unit 42, Oak Bluffs, MA 02557

    Welcome to Lagoon Ridge.....Oak Bluffs’ newest and most sought-after neighborhood! Build your 3 bedroom dream home on this lofty setting, 95 feet above Lagoon Pond, featuring sweeping sky views, colorful sunsets, and refreshing salty sea breezes. This exceptional building lot is among the last of the remaining opportunities in this thriving new community. Utilities are already at the site,

    Marilyn Moses Ocean Park Realty Inc

    35 Double Ox Rd Unit 42, Oak Bluffs, MA 02557
  • 113 Dukes County Ave Unit Multi-Family, Oak Bluffs, MA 02557
    113 Dukes County Ave Unit Multi-Family, Oak Bluffs, MA 02557
    113 Dukes County Ave Unit Multi-Family, Oak Bluffs, MA 02557
    /42

    $2,289,000

    • 4 Beds
    • 3.5 Baths
    • 1,900 Sq Ft

    113 Dukes County Ave Unit Multi-Family, Oak Bluffs, MA 02557

    UNIQUE IN-TOWN INVESTMENT opportunity in the heart of Oak Bluffs. This COMMERCIALLY ZONED B1 property offers flexibility and a strong existing rental history. Built in 2017, the MULTI-FAMILY building combines modern efficiency with an unbeatable location — just a short stroll to Oak Bluffs harbor, the Inkwell Beach, art galleries, shopping on Circuit Avenue, restaurants, the Historic Flying

    Grace Hagerty Grace Hagerty Real Estate Inc

    113 Dukes County Ave Unit Multi-Family, Oak Bluffs, MA 02557
  • 5 Seth's Path, Oak Bluffs, MA 02557
    5 Seth's Path, Oak Bluffs, MA 02557
    5 Seth's Path, Oak Bluffs, MA 02557
    /20

    $1,450,000

    • 3 Beds
    • 2 Baths
    • 1,428 Sq Ft

    5 Seth's Path, Oak Bluffs, MA 02557

    Desirable picturesque Deer Run location. Just steps from the bike path, this centrally located home is a perfect island retreat. You can enjoy the multi level deck and patio overlooking a wonderful in ground pool. The large lot provides for plenty of room for gardening or games and backs up to an idyllic open field. This house is perfectly set back off of the small cul de sac. Wonderful

    Robin Perschel Feiner Real Estate

    5 Seth's Path, Oak Bluffs, MA 02557
  • 101 Tradewinds Rd, Oak Bluffs, MA 02557
    101 Tradewinds Rd, Oak Bluffs, MA 02557
    101 Tradewinds Rd, Oak Bluffs, MA 02557
    /59

    $1,435,000

    • 3 Beds
    • 1.5 Baths
    • 1,456 Sq Ft

    101 Tradewinds Rd, Oak Bluffs, MA 02557

    Set on just over half an acre near downtown Oak Bluffs abutting permanently preserved acres by Land Bank - a rare find in central Oak Bluffs! This home blends classic Midcentury architectural character with abundant natural light from floor-to-ceiling windows and soaring post-and-beam ceilings creating a warm and inviting space. The interior features hardwood floors in the dramatic great room

    Nya Clarke Martha's Vineyard Island-Wide Realty

    101 Tradewinds Rd, Oak Bluffs, MA 02557
  • 56 Holmes Hole Rd, Oak Bluffs, MA 02568
    56 Holmes Hole Rd, Oak Bluffs, MA 02568
    /2

    $674,000

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

    56 Holmes Hole Rd, 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, Oak Bluffs, MA 02568
  • 0 Eastville Ave Unit 147.2 / 3 / 4 / 5 /6, Oak Bluffs, MA 02568
    0 Eastville Ave Unit 147.2 / 3 / 4 / 5 /6, Oak Bluffs, MA 02568
    0 Eastville Ave Unit 147.2 / 3 / 4 / 5 /6, Oak Bluffs, MA 02568
    /12

    $4,400,000

    • Land
    • 4.8 Acres
    • $916,667 per Acre

    0 Eastville Ave Unit 147.2 / 3 / 4 / 5 /6, Oak Bluffs, MA 02568

    EXISTING FIVE (5) LOT SUBDIVISION IN OAK BLUFFS. THESE LOTS ARE ALREADY SUBDIVIDED. Almost 5 Acres of wooded, level land within half a mile of Eastville Beach, Doug's Cove Preserve (4.6 acres of Land Bank Property) and less than a mile to Oak Bluffs Harbor. NEW Shared Use Path runs along Eastville Avenue, when finished will link Vineyard Haven and Oak Bluffs for walking and cycling. Septic

    Alisan Lohan-Conway Alisan Lohan-Conway Properties

    0 Eastville Ave Unit 147.2 / 3 / 4 / 5 /6, 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
    /34

    $1,295,000

    • 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 & 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

    Alice Pierce Coldwell Banker Realty - Hingham

    9 Brunswick Ave, Oak Bluffs, MA 02557
  • 0 Heather Ln Unit 11 43465, Oak Bluffs, MA 02568
    0 Heather Ln Unit 11 43465, Oak Bluffs, MA 02568
    0 Heather Ln Unit 11 43465, Oak Bluffs, MA 02568
    /4

    $425,000

    • Land
    • 0.23 Acre
    • $1,845,419 per Acre

    0 Heather Ln Unit 11 43465, Oak Bluffs, MA 02568

    Lovely untouched piece of land waiting for you to create your own special island retreat. Property, being sold "AS IS", is nestled on a quiet dead end road off of DeBettencourt Place in Oak Bluffs. Conveniently located within walking distance to downtown OB, OB Ferry, beaches, parks, arts district and more... Included on the "Sea View Bluffs Subdivision Plan of Land" and recorded with

    Rosemary Byrd Ocean Park Realty Inc

    0 Heather Ln Unit 11 43465, Oak Bluffs, MA 02568
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 $1,333,333. If you put a 20% down payment of $266,700 and had a 30-year fixed mortgage with an interest rate of 6.31%, your estimated principal and interest payment would be $6,610 a month plus property taxes, HOA fees, home insurance, PMI, and utilities. Using the 28% rule, you would need to make at least $283K 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, 02539, 02575, 02535 and 02540.
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, Falmouth Village and Teaticket.

Home Trends in Oak Bluffs, MA

On average, homes in Oak Bluffs, Marthas Vineyard sell after 88 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 $1,100,000, down 8% from the median home sale price over the previous 12 months.

Housing Trends

Median Sale Price
$1,100,000
Median Single Family Sale Price
$1,475,000
Median 2 Bedroom Sale Price
$941,000
Median 1 Bedroom Sale Price
$560,000
Average Price Per Sq Ft
$922
Number of Homes for Sale
28
Last 12 months Home Sales
135
Months of Supply
2.50
Median List Price
$1,333,333
Median Change From 1st List Price
7%
Median Home Sale Price YoY Change
-8%
How to Buy a Home How to Finance a Home How to Sell a Home

Disclaimer: Certain information contained herein is derived from information provided by parties other than Homes.com. All information provided is deemed reliable, but is not guaranteed to be accurate and should be independently verified.

Homes.com Licensing Information

§ 442-H New York Standard Operating Procedures

New York Fair Housing Notice

TREC: Information about brokerage services, Consumer protection notice

California DRE #01937601

Contact Homes.com Brokerage

Copyright © 2026 CoStar Group