101

Recently Sold Oak Bluffs Homes

Section Image
  • 48 Brewster Ave, Oak Bluffs, MA 02557
    48 Brewster Ave, Oak Bluffs, MA 02557
    48 Brewster Ave, Oak Bluffs, MA 02557
    /26

    $1,450,000 Sold Sep 12, 2025

    • 3,352 Sq Ft
    • $433/SF
    • 8 Days On Market
    • 5 Beds
    • 3 Baths
    • Built 1975

    48 Brewster Ave, Oak Bluffs, MA 02557

    EAST CHOP - LOCATION- LOCATION . A RENOVATOR'S DREAM - A 5 bedroom multi-level home with an approved Title 5 septic system for 5 bedrooms - and just 1/2 mile to the harbor and town center. One lot from the East Chop Association Tennis Club. "You can change your house - but not your neighborhood" and this is a very special neighborhood. House needs much TLC - to be sold AS IS. Priced well

    Patti Dean Wiggy's Pond Real Estate

    48 Brewster Ave, Oak Bluffs, MA 02557
  • 21 Rock Ave, Oak Bluffs, MA 02557
    21 Rock Ave, Oak Bluffs, MA 02557
    21 Rock Ave, Oak Bluffs, MA 02557
    /21

    $500,000 Sold Sep 12, 2025

    • 604 Sq Ft
    • $828/SF
    • 58 Days On Market
    • 1 Bed
    • 1 Bath
    • Built 1870

    21 Rock Ave, Oak Bluffs, MA 02557

    Experience the charm of 21 Rock Avenue, nestled in the Historic Martha's Vineyard Camp Meeting Association. This year-round cottage features 1 bedroom and 1 bath, and is just moments away from Oak Bluffs Harbor, ferry ports, sandy beaches, art galleries, and delightful restaurants. Recent exterior enhancements include cedar fencing, refreshed house trim, new paint, and an upgraded roof. Please

    Marilyn Moses Ocean Park Realty Inc

    21 Rock Ave, Oak Bluffs, MA 02557
  • 25 Oak Ave, Oak Bluffs, MA 02557
    25 Oak Ave, Oak Bluffs, MA 02557
    25 Oak Ave, Oak Bluffs, MA 02557
    /40

    $650,000 Sold Sep 10, 2025

    • 759 Sq Ft
    • $856/SF
    • 251 Days On Market
    • 2 Beds
    • 0.5 Baths
    • Built 1900

    25 Oak Ave, Oak Bluffs, MA 02557

    WALK TO THE HARBOR from this level 10,100 sq.ft. quarter acre lot set down a winding avenue off New York Avenue. Currently there's a very cute Victorian Era two story cottage which could be renovated. Alternatively, you have the choice to add on to the existing building or build a new FIVE (5) BEDROOM home - Possibly more than FIVE (5) bedrooms as it’s not in a Board of Health area of concern -

    Alisan Lohan-Conway Alisan Lohan-Conway Properties

    25 Oak Ave, Oak Bluffs, MA 02557
  • 2 Upper Douglas Ln, Oak Bluffs, MA 02557
    2 Upper Douglas Ln, Oak Bluffs, MA 02557
    2 Upper Douglas Ln, Oak Bluffs, MA 02557
    /20

    $1,295,000 Sold Sep 05, 2025

    • 1,584 Sq Ft
    • $818/SF
    • 5 Days On Market
    • 4 Beds
    • 2 Baths
    • Built 1988

    2 Upper Douglas Ln, Oak Bluffs, MA 02557

    Are you still looking for a year-round, island home for your family and only finding homes that are either not in your price range or are badly in need of renovation? Look no further because all that work has been done for you with this property. Just move in and enjoy the convenient location -- close to town, schools, hospital and public transportation. This low-maintenance, 4 bedroom, 2 bath

    Lynn Buder Sandpiper Realty

    2 Upper Douglas Ln, Oak Bluffs, MA 02557
  • 11 Onondaga Ave, Vineyard Haven, MA 02568
    11 Onondaga Ave, Vineyard Haven, MA 02568
    11 Onondaga Ave, Vineyard Haven, MA 02568
    /29

    $991,500 Sold Sep 04, 2025

    • 1,996 Sq Ft
    • $497/SF
    • 21 Days On Market
    • 3 Beds
    • 2.5 Baths
    • Built 1996

    11 Onondaga Ave, Vineyard Haven, MA 02568

    Comfortable Island Home on a Quiet Dead-End Road in Oak Bluffs:Welcome to 11 Onondaga Avenue, the second home on the left on a short, quiet dead-end road in a well-established Oak Bluffs neighborhood enjoyed by both year-round and seasonal residents. This well-cared-for 3-bedroom, 2.5-bathroom home offers space, comfort, and a truly inviting island lifestyle—just a short walk to the Oak

    Rene Ben David Ocean Park Realty Inc

    11 Onondaga Ave, Vineyard Haven, MA 02568
  • 21 Norris Ave, Vineyard Haven, MA 02568
    21 Norris Ave, Vineyard Haven, MA 02568
    21 Norris Ave, Vineyard Haven, MA 02568
    /16

    $800,000 Sold Sep 04, 2025

    • 1,086 Sq Ft
    • $737/SF
    • 16 Days On Market
    • 2 Beds
    • 1 Bath
    • Built 1948

    21 Norris Ave, Vineyard Haven, MA 02568

    An Exciting Opportunity for First-Time Buyers or Island Investors.This long-time family homestead offers a rare chance to own a piece of Oak Bluffs at a price point that invites possibility. Set in a quiet, residential neighborhood, the location is just a 25–30 minute walk to the center of town, where you’ll find shopping, restaurants, grocery stores, banks, the ferry terminal, beautiful

    Rene Ben David Ocean Park Realty Inc

    21 Norris Ave, Vineyard Haven, MA 02568
  • 26 Box Turtle Ln, Oak Bluffs, MA 02557
    26 Box Turtle Ln, Oak Bluffs, MA 02557
    26 Box Turtle Ln, Oak Bluffs, MA 02557
    /30

    $1,995,000 Sold Aug 29, 2025

    • 2,891 Sq Ft
    • $690/SF
    • 5 Days On Market
    • 4 Beds
    • 3.5 Baths
    • Built 1980

    26 Box Turtle Ln, Oak Bluffs, MA 02557

    This delightful home is on a scenic lot nestled within the Sengekontacket Association. Every room in the home is filled with natural light and beautiful views. It is a very short walking distance to the community boat dock and kayaking, as well as the walking trails of Sengy.Updated in 2008 by the architect owner, this home has 3 bedrooms in the main house and a lovely bedroom and bathroom in

    Jayne Isford Ocean Park Realty Inc

    26 Box Turtle Ln, Oak Bluffs, MA 02557
  • 12 Martha's Park Rd, Oak Bluffs, MA 02557
    12 Martha's Park Rd, Oak Bluffs, MA 02557
    12 Martha's Park Rd, Oak Bluffs, MA 02557
    /23

    $1,800,000 Sold Aug 26, 2025

    • 1,351 Sq Ft
    • $1,332/SF
    • 0 Days On Market
    • 4 Beds
    • 1.5 Baths
    • Built 1910

    12 Martha's Park Rd, Oak Bluffs, MA 02557

    Harthaven Cottage - This magical cottage, tucked away just 2/10's of a mile from the private association beach, is waiting for you to call it your own. A covered porch welcomes you. Once inside, you begin to take in the charming details of this classic 3-season home. There are cathedral ceilings with exposes painted beams. Home features 4 bedrooms, 1 1/2 baths and outdoor shower. Both bathrooms

    Michele Moore Island Real Estate

    12 Martha's Park Rd, Oak Bluffs, MA 02557
  • 14 High Meadow Ln, Oak Bluffs, MA 02557
    14 High Meadow Ln, Oak Bluffs, MA 02557
    14 High Meadow Ln, Oak Bluffs, MA 02557
    /19

    $1,449,000 Sold Aug 19, 2025

    • 2,284 Sq Ft
    • $634/SF
    • 263 Days On Market
    • 3 Beds
    • 3 Baths
    • Built 1987

    14 High Meadow Ln, Oak Bluffs, MA 02557

    MEADOW VIEW FARM/OAK BLUFFS - Owned by the same family for over 30 years, this sun-drenched, contemporary reverse-style home is located in Meadow View Farms. Well-maintained over those years, this 3 bedroom, 2 full and 2 half baths multi-level home has so much to offer and boundless potential. The second-level features a bright, open floor plan with cathedral ceilings and 3 sliding doors that

    Michele Moore Island Real Estate

    14 High Meadow Ln, Oak Bluffs, MA 02557
  • 35 E Side Rd, Oak Bluffs, MA 02557
    35 E Side Rd, Oak Bluffs, MA 02557
    35 E Side Rd, Oak Bluffs, MA 02557
    /41

    $1,310,000 Sold Aug 18, 2025

    • 1,964 Sq Ft
    • $667/SF
    • 0 Days On Market
    • 3 Beds
    • 2 Baths
    • Built 1965

    35 E Side Rd, Oak Bluffs, MA 02557

    Close to the Lagoon - This three-bedroom, two-bath home sits on an oversized corner lot and has been lovingly maintained over the years. Recent upgrades include the addition of mini splits, interior painting, and lighting. The sunroom provides additional year-round living space and the wraparound deck is ideal for summer use. Bring your vision to the partially finished lower level where

    Kristin Buck Donnelly + Co

    35 E Side Rd, Oak Bluffs, MA 02557
  • 34 Tower Ridge Rd, Oak Bluffs, MA 02568
    34 Tower Ridge Rd, Oak Bluffs, MA 02568
    34 Tower Ridge Rd, Oak Bluffs, MA 02568
    /36

    $1,765,000 Sold Aug 18, 2025

    • 2,450 Sq Ft
    • $720/SF
    • 25 Days On Market
    • 4 Beds
    • 3.5 Baths
    • Built 1988

    34 Tower Ridge Rd, Oak Bluffs, MA 02568

    Nestled on a beautifully landscaped lot with lush gardens and mature trees, 34 Tower Ridge offers the perfect blend of privacy and convenience. Ideally located just minutes from downtown Oak Bluffs and the Farm Neck Golf Course, this well-maintained property is suited for comfortable year-round living or as a serene Island retreat. Inside, the bright and open layout features an updated kitchen

    Katie Donahue Sandpiper Realty

    34 Tower Ridge Rd, Oak Bluffs, MA 02568
  • 35 Vineyard Avenue Extension, Oak Bluffs, MA 02568
    35 Vineyard Avenue Extension, Oak Bluffs, MA 02568
    35 Vineyard Avenue Extension, Oak Bluffs, MA 02568
    /4

    $1,350,000 Sold Aug 15, 2025

    • 1,864 Sq Ft
    • $724/SF
    • 12 Days On Market
    • 3 Beds
    • 2 Baths
    • Built 1970

    35 Vineyard Avenue Extension, Oak Bluffs, MA 02568

    Charming Home Steps from Lagoon Pond - This three bedroom, two bath home is just 550 feet from the sandy shores and calm waters of Lagoon Pond, perfect for swimming, boating and shell fishing. Ideal for both year-round living or vacationing, the home offers an open floor plan, a private primary suite with a walk-in closet and en-suite bath, two guest bedrooms plus a den/office. The finished

    Lesley Heidt Sandpiper Realty Inc

    35 Vineyard Avenue Extension, Oak Bluffs, MA 02568
  • 35 Tuckernuck Ave, Oak Bluffs, MA 02557
    35 Tuckernuck Ave, Oak Bluffs, MA 02557
    35 Tuckernuck Ave, Oak Bluffs, MA 02557
    /34

    $1,633,000 Sold Aug 14, 2025

    • 1,918 Sq Ft
    • $851/SF
    • 66 Days On Market
    • 5 Beds
    • 2 Baths
    • Built 1870

    35 Tuckernuck Ave, Oak Bluffs, MA 02557

    Location, Location, Location! Welcome to your dream retreat in the charming historic area of Oak Bluffs. Walk to Inkwell beach, ferries, restaurants and dining. Sited across the street from Waban Park, this delightful home offers an inviting blend of comfort and convenience.As you step inside, you'll immediately appreciate the spacious layout featuring well-appointed living areas, a

    Jennifer DaSilva Compass | Point B

    35 Tuckernuck Ave, Oak Bluffs, MA 02557
  • 249 County Rd, Oak Bluffs, MA 02557
    249 County Rd, Oak Bluffs, MA 02557
    249 County Rd, Oak Bluffs, MA 02557
    /18

    $980,000 Sold Aug 11, 2025

    • 1,401 Sq Ft
    • $700/SF
    • 64 Days On Market
    • 1 Bed
    • 2 Baths
    • Built 2005

    249 County Rd, Oak Bluffs, MA 02557

    This charming Cape-style home is ideally located just over a mile from downtown Oak Bluffs, offering the perfect blend of relaxed living and convenience. The open and inviting layout features spacious first-floor living areas, complemented by high ceilings and wood floors. A versatile second-story loft space provides an additional nook, perfect for a home office. Fronting the bike bath, enjoy

    Katherine Donahue Sandpiper Realty Inc

    249 County Rd, Oak Bluffs, MA 02557
  • 119 Alpine Ave, Oak Bluffs, MA 02557
    119 Alpine Ave, Oak Bluffs, MA 02557
    119 Alpine Ave, Oak Bluffs, MA 02557
    /21

    $910,000 Sold Aug 08, 2025

    • 1,935 Sq Ft
    • $470/SF
    • 149 Days On Market
    • 1 Bed
    • 3.5 Baths
    • Built 1994

    119 Alpine Ave, Oak Bluffs, MA 02557

    Oak Bluffs Residence with guest house. Centrally located in Oak Bluffs, this property offers the rare opportunity to own a home in a prime residential location complemented with a detached cabin. The main house features, on the first floor, an inviting living/dining area, functional kitchen, and sun-filled parlor room with stunning floor-to-ceiling windows providing plenty of natural light and

    Michael Schweikert Ocean Park Realty Inc

    119 Alpine Ave, Oak Bluffs, MA 02557
  • 26 Tia Anna Ln, Oak Bluffs, MA 02557
    26 Tia Anna Ln, Oak Bluffs, MA 02557
    26 Tia Anna Ln, Oak Bluffs, MA 02557
    /41

    $1,850,000 Sold Aug 04, 2025

    • 2,210 Sq Ft
    • $837/SF
    • 22 Days On Market
    • 3 Beds
    • 3 Baths
    • Built 1980

    26 Tia Anna Ln, Oak Bluffs, MA 02557

    Welcome to 26 Tia Anna Lane! This exquisite residence is immaculate, stylish, and fully renovated, ready to welcome its new owners! Situated on a beautifully landscaped 0.30-acre lot adorned with vibrant plantings, the home boasts pristine conditions both inside and out, featuring newer Hardi Plank siding. The inviting farmer's porch, complete with Mahogany decking, sets the tone for this

    Marilyn Moses Ocean Park Realty Inc

    26 Tia Anna Ln, Oak Bluffs, MA 02557
  • 130 Wing Rd, Oak Bluffs, MA 02557
    130 Wing Rd, Oak Bluffs, MA 02557
    130 Wing Rd, Oak Bluffs, MA 02557
    /22

    $1,000,000 Sold Jul 31, 2025

    • 768 Sq Ft
    • $1,302/SF
    • 96 Days On Market
    • 2 Beds
    • 1 Bath
    • Built 1960

    130 Wing Rd, Oak Bluffs, MA 02557

    This well-maintained property is beautifully landscaped with gardens and generous lawn areas, offering incredible potential for growth and development. Conveniently located close to downtown Oak Bluffs, this property offers easy access to essential amenities and tourist destinations, whether you're driving, biking or relying on public transportation to restaurants, shops, beaches, bike paths and

    Lynn Buder Sandpiper Realty Inc

    130 Wing Rd, Oak Bluffs, MA 02557
  • 5 Temahigan Ave Unit 4-139-0, Oak Bluffs, MA 02568
    5 Temahigan Ave Unit 4-139-0, Oak Bluffs, MA 02568
    /2

    $595,000 Sold Jul 14, 2025

    • Land
    • 0.27 Acre
    • $2,228,464 per Acre
    • 103 Days On Market

    5 Temahigan Ave Unit 4-139-0, Oak Bluffs, MA 02568

    With the potential to have up to seven bedrooms, this lot is a BARGAIN. This is a exceptional Vineyard location, convenient to beaches, a bike path and both downtown Oak Bluffs and Vineyard Haven. This lot is located in an area of very substantial homes . Your future house can possibly have up to seven bedrooms and have up to three floors. Recently appraised at $850,000.00, this property at

    Ed Charter Arrowhead Homes

    5 Temahigan Ave Unit 4-139-0, Oak Bluffs, MA 02568
  • 8 Rock Ave, Oak Bluffs, MA 02557
    8 Rock Ave, Oak Bluffs, MA 02557
    8 Rock Ave, Oak Bluffs, MA 02557
    /32

    $899,000 Sold Jul 11, 2025

    • 955 Sq Ft
    • $941/SF
    • 6 Days On Market
    • 3 Beds
    • 1.5 Baths
    • Built 1871

    8 Rock Ave, Oak Bluffs, MA 02557

    Experience the charm of this exquisitely renovated Victorian Gingerbread Cottage, nestled within the historic Martha's Vineyard Camp Meeting Association. Just moments away from Oak Bluffs Harbor, ferry terminals, art galleries, restaurants, public beaches, and vibrant shopping areas, this cottage offers an unparalleled location next to all of Oak Bluffs' picturesque parks.This rare gem

    Marilyn Moses Ocean Park Realty Inc

    8 Rock Ave, Oak Bluffs, MA 02557
  • 128 Manchester Ave, Oak Bluffs, MA 02568
    128 Manchester Ave, Oak Bluffs, MA 02568
    128 Manchester Ave, Oak Bluffs, MA 02568
    /22

    $975,000 Sold Jul 07, 2025

    • 940 Sq Ft
    • $1,037/SF
    • 61 Days On Market
    • 1 Bed
    • 2 Baths
    • Built 2025

    128 Manchester Ave, Oak Bluffs, MA 02568

    This delightful, modern cape-style home features thoughtful and impressive finish details. The covered porch welcomes you into the home where you will find well-appointed spaces. The kitchen has stainless appliances including a 5-burner gas range with pot filler, an LG French-door refrigerator and dishwasher. The kitchen area is finished with shiplap. There is an open dining and living area with

    Michele Moore Island Real Estate

    128 Manchester Ave, Oak Bluffs, MA 02568
  • 1 Cottage Park, Oak Bluffs, MA 02557
    1 Cottage Park, Oak Bluffs, MA 02557
    1 Cottage Park, Oak Bluffs, MA 02557
    /26

    $885,000 Sold Jul 01, 2025

    • 987 Sq Ft
    • $897/SF
    • 29 Days On Market
    • 3 Beds
    • 2.5 Baths
    • Built 1869

    1 Cottage Park, Oak Bluffs, MA 02557

    The Star Spangled Manor, a beautifully restored gem nestled in the heart of Oak Bluffs within the historic Martha's Vineyard Camp Meeting Association. Located on a pedestrian street, you'll be mere steps away from the shops and restaurants of Circuit Ave., Ocean Park, and the Oak Bluffs beaches. This cherished three-bedroom, three-bathroom cottage seamlessly blends vintage charm with modern

    Diana Gilmore Island Real Estate

    1 Cottage Park, Oak Bluffs, MA 02557
  • 10 Kims Way, Oak Bluffs, MA 02557
    10 Kims Way, Oak Bluffs, MA 02557
    10 Kims Way, Oak Bluffs, MA 02557
    /29

    $1,100,000 Sold Jun 27, 2025

    • 1,976 Sq Ft
    • $557/SF
    • 9 Days On Market
    • 4 Beds
    • 2.5 Baths
    • Built 1985

    10 Kims Way, Oak Bluffs, MA 02557

    Located under a mile from downtown Oak Bluffs, this well-maintained 4-bedroom home includes a 3-bedroom main house and a 1-bedroom basement apartment. Recent upgrades include a new roof, Title V septic system, electric service, and town water connection. The first floor features a spacious living/dining area, kitchen, half bath, and a cozy den. Upstairs are 3 bedrooms and a full bath. The

    Michael Schweikert Ocean Park Realty Inc

    10 Kims Way, Oak Bluffs, MA 02557
  • 10 Kims Way, Oak Bluffs, MA 02568
    10 Kims Way, Oak Bluffs, MA 02568
    10 Kims Way, Oak Bluffs, MA 02568
    /32

    $1,100,000 Sold Jun 27, 2025

    • 1,976 Sq Ft
    • $557/SF
    • 156 Days On Market
    • 4 Beds
    • 2.5 Baths
    • Built 1985

    10 Kims Way, Oak Bluffs, MA 02568

    Located under a mile from downtown Oak Bluffs, this well-maintained 4-bedroom home includes a 3-bedroom main house and a 1-bedroom basement apartment. Recent upgrades include a new roof, Title V septic system, electric service, and town water connection. The first floor features a spacious living/dining area, kitchen, half bath, and a cozy den. Upstairs are 3 bedrooms and a full bath. The

    Michael Schweikert Ocean Park Realty, Inc.

    10 Kims Way, Oak Bluffs, MA 02568
  • 9 Goode St, Oak Bluffs, MA 02557
    9 Goode St, Oak Bluffs, MA 02557
    9 Goode St, Oak Bluffs, MA 02557
    /56

    $1,699,000 Sold Jun 20, 2025

    • 2,954 Sq Ft
    • $575/SF
    • 314 Days On Market
    • 4 Beds
    • 4.5 Baths
    • Built 1900

    9 Goode St, Oak Bluffs, MA 02557

    Welcome to your dream home, located on a very quiet street in Oak Bluffs, yet just a short walk to downtown & the elementary school. This prime location offers the perfect blend of serenity and convenience. This well appointed home features 4 bedrooms and 4.5 bathrooms. Included in this is a 1-bedroom, 1-bathroom apartment attached to the home, providing a perfect space for guest accommodation.

    Grace Hagerty Grace Hagerty Real Estate Inc

    9 Goode St, Oak Bluffs, MA 02557
  • 2 Fisk Ave, Oak Bluffs, MA 02557
    2 Fisk Ave, Oak Bluffs, MA 02557
    2 Fisk Ave, Oak Bluffs, MA 02557
    /17

    $700,000 Sold Jun 20, 2025

    • 725 Sq Ft
    • $966/SF
    • 111 Days On Market
    • 3 Beds
    • 1 Bath
    • Built 1870

    2 Fisk Ave, Oak Bluffs, MA 02557

    Gingerbread Cottage full of character and personality! Part of Martha's Vineyard Camp Meeting Association, this Oak Bluffs seasonal antique with beautiful trim and scrollwork sits on a lovely little avenue. The cottage features charming period details, a covered front porch with rocking chairs & upper balcony. Step inside the unique front door into a cozy living room enhanced by beamed ceiling,

    Julie Walker Century 21 North East

    2 Fisk Ave, Oak Bluffs, MA 02557
  • 6 Martha's Park Rd, Oak Bluffs, MA 02557
    6 Martha's Park Rd, Oak Bluffs, MA 02557
    6 Martha's Park Rd, Oak Bluffs, MA 02557
    /42

    $2,400,000 Sold Jun 05, 2025

    • 3,200 Sq Ft
    • $750/SF
    • 49 Days On Market
    • 3 Beds
    • 4.5 Baths
    • Built 2014

    6 Martha's Park Rd, Oak Bluffs, MA 02557

    Must see stunning “reverse” layout (kitchen and main living spaces upstairs for the views) contemporary home with breathtaking water views and a thoughtfully designed layout in the exclusive Harthaven community! This spacious property features open kitchen concept with marble counter tops and stainless steel appliances, comfortable living areas, a bonus room (with full bathroom), food prep,

    Jennifer B. DaSilva Compass

    6 Martha's Park Rd, Oak Bluffs, MA 02557
  • 60 Prospect Ave, Oak Bluffs, MA 02557
    60 Prospect Ave, Oak Bluffs, MA 02557
    60 Prospect Ave, Oak Bluffs, MA 02557
    /28

    $1,270,000 Sold May 23, 2025

    • 2,192 Sq Ft
    • $579/SF
    • 57 Days On Market
    • 3 Beds
    • 2 Baths
    • Built 1940

    60 Prospect Ave, Oak Bluffs, MA 02557

    OAK BLUFFS ~ APPROVED 4 BEDROOM SEPTIC IN PLACE - This home LIVES LARGE and offers 3 Distinct Structures situated on a BEAUTIFUL landscaped .34 Acre private lot ~EASY WALK or BIKE RIDE to OAK BLUFFS HARBOR, Town, Sandy Beaches, Ferry Ports and Town Parks! Tastefully renovated SPACIOUS Split-Level Home featuring a lovely and functional open floor plan. The main level displays beautiful hardwood

    Marilyn Moses Ocean Park Realty Inc

    60 Prospect Ave, Oak Bluffs, MA 02557
  • 51 Rural Cir, Oak Bluffs, MA 02557
    51 Rural Cir, Oak Bluffs, MA 02557
    51 Rural Cir, Oak Bluffs, MA 02557
    /24

    $665,000 Sold May 23, 2025

    • 806 Sq Ft
    • $825/SF
    • 171 Days On Market
    • 3 Beds
    • 1.5 Baths
    • Built 1876

    51 Rural Cir, Oak Bluffs, MA 02557

    The Spirit of '76 is a lovely Campground cottage nestled into the landscape for privacy and shade. Just a couple of blocks to the beach, town center, shops, and restaurants. A fabulous wrap around porch with various seating areas. Built in 1876 this wonderful throwback of yesteryear features some original furnishings included in the sale. With a classic front parlor, dining room, and kitchen, a

    Lisa Lucier Anchor Realty of Martha's Vineyard

    51 Rural Cir, Oak Bluffs, MA 02557
  • 2 E Side Road & 60 Bay View Ave, Oak Bluffs, MA 02557
    2 E Side Road & 60 Bay View Ave, Oak Bluffs, MA 02557
    2 E Side Road & 60 Bay View Ave, Oak Bluffs, MA 02557
    /27

    $1,600,000 Sold May 22, 2025

    • 1,594 Sq Ft
    • $1,004/SF
    • 532 Days On Market
    • 3 Beds
    • 2 Baths
    • Built 1933

    2 E Side Road & 60 Bay View Ave, Oak Bluffs, MA 02557

    Stunning sunsets await. This quintessential bungalow style Vineyard home has been lovingly maintained and enjoyed by the same family for close to 100 years. Built in 1933, the main house includes three bedrooms, two full baths and hardwood floors throughout. The spacious living area boasts high ceilings, stone fireplace, and expansive water views. Summer days and nights are well spent under the

    Carol Shore Donnelly + Co

    2 E Side Road & 60 Bay View Ave, Oak Bluffs, MA 02557
  • 12 Tamarack Ln, Oak Bluffs, MA 02536
    12 Tamarack Ln, Oak Bluffs, MA 02536
    12 Tamarack Ln, Oak Bluffs, MA 02536
    /36

    $5,500,000 Sold May 20, 2025

    • 3,262 Sq Ft
    • $1,686/SF
    • 295 Days On Market
    • 4 Beds
    • 4.5 Baths
    • Built 1984

    12 Tamarack Ln, Oak Bluffs, MA 02536

    This bright and sunny home has a spectacular waterview overlooking the Eighth Fairway of Farm Neck Golf Course, Sengekontacket Pond and Nantucket Sound. Professionaly designed landscaping with perennial beds and charming brick courtyard add to its ambiance. Included are Farm Neck Golf Club stockholder membership (meaning immediate entry into golf membership), tennis and dock & mooring privileges.

    Betsy Kessler Rutledge Properties

    12 Tamarack Ln, Oak Bluffs, MA 02536
  • 51 Head of the Pond Rd, Vineyard Haven, MA 02568
    51 Head of the Pond Rd, Vineyard Haven, MA 02568
    51 Head of the Pond Rd, Vineyard Haven, MA 02568
    /45

    $1,225,000 Sold May 19, 2025

    • 1,725 Sq Ft
    • $710/SF
    • 338 Days On Market
    • 3 Beds
    • 2 Baths
    • Built 1986

    51 Head of the Pond Rd, Vineyard Haven, MA 02568

    Iron Hill, Centrally located with convenient access to Island villages. 3 Bedroom, 2 Bath Ranch on 1.5+ acres. An empty canvas with limitless possibilities. Mature landscaping designed for privacy, aesthetics, and low maintenance. Paved private road access, with generous setback for residence. Bike path, Bus stop, State Forest, & Walking Trails nearby. Association covenants allow up to two

    Bruce Stuart Bruce Stuart and Associates

    51 Head of the Pond Rd, Vineyard Haven, MA 02568
  • 33 Clay Ave, Oak Bluffs, MA 02557
    33 Clay Ave, Oak Bluffs, MA 02557
    33 Clay Ave, Oak Bluffs, MA 02557
    /26

    $1,665,000 Sold May 02, 2025

    • 2,408 Sq Ft
    • $691/SF
    • 300 Days On Market
    • 3 Beds
    • 3 Baths
    • Built 1986

    33 Clay Ave, Oak Bluffs, MA 02557

    East Chop - Tucked away on a quiet tree-lined street, you will find this contemporary three-bedroom home. A distinctive floor plan provides ample living spaces on all three levels. The expansive outdoor deck and large yard expand the living space and are the perfect places to enjoy the quiet setting. The unique layout and five-bedroom septic allows easy reconfiguration. A fantastic opportunity to

    Katherine Donahue Sandpiper Realty Inc

    33 Clay Ave, Oak Bluffs, MA 02557
  • 10 Nunes Way, Oak Bluffs, MA 02557
    10 Nunes Way, Oak Bluffs, MA 02557
    10 Nunes Way, Oak Bluffs, MA 02557
    /32

    $1,100,000 Sold May 01, 2025

    • 1,680 Sq Ft
    • $655/SF
    • 172 Days On Market
    • 2 Beds
    • 3.5 Baths
    • Built 2003

    10 Nunes Way, Oak Bluffs, MA 02557

    On approximately .40 of an acre this 21 year old home has much to offer. In a very convenient location close to theFarm Neck golf course, O.B. elementary school, and a land bank conservation property - the 72 acre Tradewinds Field Reserve dog park. Two decks provide summertime fun and the walk out basement with bath offers an opportunity to finish off more living space. An excellent floor plan

    Neal Stiller Cronigs Real Estate

    10 Nunes Way, Oak Bluffs, MA 02557
  • 9 Forest Cir, Oak Bluffs, MA 02557
    9 Forest Cir, Oak Bluffs, MA 02557
    9 Forest Cir, Oak Bluffs, MA 02557
    /20

    $675,000 Sold Apr 23, 2025

    • 508 Sq Ft
    • $1,329/SF
    • 298 Days On Market
    • 2 Beds
    • 1.5 Baths
    • Built 1868

    9 Forest Cir, Oak Bluffs, MA 02557

    The Size will Surprise~ Cloud Nine~ Located on a quiet hidden circle with 14 enchanting cottages in the Historic Martha's Vineyard Camp Meeting Association. Steps to Circuit Avenue, beaches, shops, ferries, and restaurants. This YEAR ROUND RENOVATED Charming Cottage is FULLY INSULATED with spray foam and in 2022 Brennan and Co. installed a Daikin Multi Position Air Handler with thermostat to

    Marilyn Moses Ocean Park Realty Inc

    9 Forest Cir, Oak Bluffs, MA 02557
  • 4 Quail Run Unit 17, Oak Bluffs, MA 02557
    4 Quail Run Unit 17, Oak Bluffs, MA 02557
    4 Quail Run Unit 17, Oak Bluffs, MA 02557
    /49

    $865,000 Sold Apr 17, 2025

    • 1,208 Sq Ft
    • $716/SF
    • 70 Days On Market
    • 2 Beds
    • 2 Baths
    • Built 1972

    4 Quail Run Unit 17, Oak Bluffs, MA 02557

    LUXURIOUS LIFESTYLE AMENITIES: RENOVATED TOWNHOUSE WITH TENNIS, PICKLEBALL + BOATING ACCESS. Welcome to this beautifully renovated 2-bedroom, 2-bathroom townhouse located in the exclusive Sengekontacket community. This nicely appointed property offers a perfect blend of comfort and convenience, making it an ideal choice for year-round living or as a rental investment opportunity.Spanning 1,208

    Wendy Harman Compass | Point B

    4 Quail Run Unit 17, Oak Bluffs, MA 02557
  • 4 Quail Run Rd Unit 17, Edgartown, MA 02539
    4 Quail Run Rd Unit 17, Edgartown, MA 02539
    4 Quail Run Rd Unit 17, Edgartown, MA 02539
    /42

    $865,000 Sold Apr 17, 2025

    • 1,208 Sq Ft
    • $716/SF
    • 2 Days On Market
    • 2 Beds
    • 2 Baths
    • Built 1972

    4 Quail Run Rd Unit 17, Edgartown, MA 02539

    Luxurious Lifestyle Amenities: Renovated Townhouse With Tennis, Pickleball + Boating Access - This nicely appointed condominium in the exclusive Sengekontacket community offers a perfect blend of comfort and convenience. It features two walls of sliding glass doors that lead out to an expansive 288-square foot deck. The property was updated in 2023 with new Pella® sliding glass doors, new

    Wendy Harman Compass

    4 Quail Run Rd Unit 17, Edgartown, MA 02539
  • 56 Narragansett Ave Unit 3A, Oak Bluffs, MA 02557
    56 Narragansett Ave Unit 3A, Oak Bluffs, MA 02557
    56 Narragansett Ave Unit 3A, Oak Bluffs, MA 02557
    /14

    $640,000 Sold Apr 11, 2025

    • 647 Sq Ft
    • $989/SF
    • 178 Days On Market
    • 2 Beds
    • 1 Bath
    • Built 1880

    56 Narragansett Ave Unit 3A, Oak Bluffs, MA 02557

    OAK BLUFFS REAL ESTATE OPPORTUNITY~Explore this spacious first-floor condo, complete with two bedrooms and a full bath. Perfectly located just a leisurely stroll from the beach, a variety of restaurants, charming campgrounds, coffee shops, and the harbor with ferry access. Boasting coveted B1 zoning, this property offers an outstanding opportunity for savvy investors. Its potential as a rental

    Marilyn Moses Ocean Park Realty Inc

    56 Narragansett Ave Unit 3A, Oak Bluffs, MA 02557
  • 0 Concord Ave, Oak Bluffs, MA 02568
    0 Concord Ave, Oak Bluffs, MA 02568
    0 Concord Ave, Oak Bluffs, MA 02568
    /8

    $390,000 Sold Apr 01, 2025

    • Land
    • 0.25 Acre
    • $1,558,753 per Acre
    • 83 Days On Market

    0 Concord Ave, Oak Bluffs, MA 02568

    GROVEDALE BUILD YOUR DREAM OPPORTUNITY - Along a quiet country lane and close to all Oak Bluffs has to offer, this level lot is located in a neighborhood of nicely landscaped homes. The pride of ownership is apparent in this locale. There are not many opportunites like this left on Martha's Vineyard.

    Leslie C. Floyd Portfolio Real Estate, Inc.

    0 Concord Ave, Oak Bluffs, MA 02568
  • 11 Fairway Dr, Oak Bluffs, MA 02557
    11 Fairway Dr, Oak Bluffs, MA 02557
    11 Fairway Dr, Oak Bluffs, MA 02557
    /34

    $980,000 Sold Mar 26, 2025

    • 1,608 Sq Ft
    • $609/SF
    • 191 Days On Market
    • 2 Beds
    • 1 Bath
    • Built 1969

    11 Fairway Dr, Oak Bluffs, MA 02557

    In the well established residential neighborhood of Sea Glen, turn in onto the second street on the right. At the soft curve of the road, just on the other side of the low natural stone wall, the land gently slopes down toward the house where you will find this understated rustic one level home nestled in the midst of lovely seasonal flower beds surrounding the house with mature trees along the

    Sandra Grymes Martha's Vineyard Island-Wide Realty

    11 Fairway Dr, Oak Bluffs, MA 02557
  • 41 Towanticut Ave, Oak Bluffs, MA 02557
    41 Towanticut Ave, Oak Bluffs, MA 02557
    41 Towanticut Ave, Oak Bluffs, MA 02557
    /34

    $1,136,250 Sold Mar 19, 2025

    • 1,152 Sq Ft
    • $986/SF
    • 239 Days On Market
    • 3 Beds
    • 2 Baths
    • Built 1999

    41 Towanticut Ave, Oak Bluffs, MA 02557

    What a wonderful opportunity to own a Contemporary Ranch style home on this beautiful Island of Martha’s Vineyard. It is well maintained with three bedrooms, two full baths, central a/c, and a full unfinished basement. Ideal location in a very quiet neighborhood, just a short distance to bike path, Town, ferry, restaurants, beaches, shops all that you could ask for. Living room is light, bright

    JoJo Lambert Island Home Realty Inc.

    41 Towanticut Ave, Oak Bluffs, MA 02557

Showing Results 1 - 40, Page 1 of 3

Massachusetts Dukes County Marthas Vineyard Oak Bluffs

Recently Sold Real Estate & Homes in Oak Bluffs, Marthas Vineyard

Learn more about living in Oak Bluffs

Frequently Asked Questions

What is the average time to sell a house in Oak Bluffs, MA?
The houses for sale in Oak Bluffs, MA spend an average of 103 days on the market.
What is the number of active homes for sale in Oak Bluffs, MA?
There are 63 active homes for sale in Oak Bluffs, MA.

Home Trends in Oak Bluffs, MA

On average, homes in Oak Bluffs, Marthas Vineyard sell after 103 days on the market compared to the national average of 52 days. The median sale price for homes in Oak Bluffs, Marthas Vineyard over the last 12 months is $1,295,000, up 15% from the median home sale price over the previous 12 months.

Housing Trends

Median Sale Price
$1,295,000
Median Single Family Sale Price
$1,590,000
Median 2 Bedroom Sale Price
$1,490,000
Median 1 Bedroom Sale Price
$1,495,000
Average Price Per Sq Ft
$1,119
Number of Homes for Sale
63
Last 12 months Home Sales
136
Months of Supply
5.60
Median List Price
$1,575,000
Median Change From 1st List Price
7%
Median Home Sale Price YoY Change
15%
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 © 2025 CoStar Group