4,264

Oak Bluffs, MA Homes

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  • /46

    $6,250,000

    • 5 Beds
    • 2.5 Baths
    • 2,269 Sq Ft

    34 Edys Island Way, Chilmark, MA 02535

    Waterfront house and guest house with a private dock on Menemsha Pond. This location is in the heart of Menemsha, a waterfront enclave within walking distance of this classic Harbor. Built and cared for over four generations by an Island legacy family, this property is unique among Island estates for its combination of privacy yet convenience, seclusion yet expansive views. The property is only a

    Jill Napior Tea Lane Associates

    34 Edys Island Way, Chilmark, MA 02535
  • /2

    $10,000 Per Month

    • 6 Beds
    • 3.5 Baths
    • 2,100 Sq Ft
    • House for Rent

    15 Crowell Lane Wt119, West Tisbury, MA 02575

    THIS IS A WEEKLY RENTAL NOT A MONTHLY!!!!!!!Seven Gates Farm. This property has three ponds, overlooks rolling meadows and is very charming. Located in Seven Gates Farm association, the property affords access to association tennis and two miles of private beach as well as miles of walking trails. Bookings for tennis are available at the office for a slight fee.There is a $25 trash charge per

    Karen Overtoom Karen M. Overtoom R.E.

    15 Crowell Lane Wt119, West Tisbury, MA 02575
  • /2

    $1,595,000

    Sold Jul 01, 2025

    10 Red Pony Rd, West Tisbury, MA 02568

    • 2 Beds
    • 1.5 Baths
    • 1,176 Sq Ft
    • Built 1998

    Last Sold Summary

    • $1,356/SF

    Current Estimated Value $1,623,840

    Last Listing Agent Lisa Da Silva Signal House Group at Compass

    10 Red Pony Rd, West Tisbury, MA 02568
    • /2

      Est $2,396,685

      Not Listed For Sale

      23 Oak Ln, Vineyard Haven, MA 02568

      • 6 Beds
      • 5 Baths
      • 3,035 Sq Ft
      • Built 2007
      23 Oak Ln, Vineyard Haven, MA 02568

  • /27

    $1,800,000

    • 3 Beds
    • 3 Baths
    • 2,293 Sq Ft

    10 Trotters Ln, West Tisbury, MA 02575

    Centrally located and surrounded by lush landscaping, this inviting cape offers three bedrooms and three full baths. Warm, mellow wood floors, tiled bathrooms and a spacious living area anchored by a cozy fireplace. The full basement provides ample storage or expansion potential, while a versatile bonus room on the second level is perfect as an art studio, home office or guest overflow.

    Rebecca V Conroy Conroy & Company R.E., Inc.

    10 Trotters Ln, West Tisbury, MA 02575
  • /25

    $13,600 Per Month

    • 2 Beds
    • 2 Baths
    • 792 Sq Ft
    • House for Rent

    64 Bartimus Luce Road Wt125, West Tisbury, MA 02575

    THIS IS A WEEKLY RENTAL NOT A MONTHLY!!!!!!!!!!Idyllic location right above a sandy private beach on the North Shore. This beach cottage affords views of the Sound and the Elizabeth Islands with a front row seat on unrivaled sunsets. It is rustic and cozy with a large screened porch overlooking the view. Have a getaway like in days of yore when life was simple and the beach at your doorstep.Take

    Karen Overtoom Karen M. Overtoom R.E.

    64 Bartimus Luce Road Wt125, West Tisbury, MA 02575
  • /7

    $375,000

    Sold Apr 06, 2026

    99 Cygnet Way Unit 103, Chilmark, MA 02535

    • Land
    • 8,712 Sq Ft
    • $1,875,000 per Acre

    Last Sold Summary

    • 6% Below List Price
    • 120 Days On Market

    Last Listing Agent Russell Maloney Russell Maloney Real Estate

    99 Cygnet Way Unit 103, Chilmark, MA 02535
    • /34

      Est $1,587,563

      Not Listed For Sale

      84 Christiantown Rd, Vineyard Haven, MA 02568

      • 3 Beds
      • 2 Baths
      • 1,452 Sq Ft
      • Built 2018
      84 Christiantown Rd, Vineyard Haven, MA 02568

      Last Sold Summary

      • 59 Days On Market

  • /26

    $1,299,000

    Pending
    • 3 Beds
    • 1 Bath
    • 1,150 Sq Ft

    9 Galway Rd, Vineyard Haven, MA 02568

    Tucked away off Old County Road in West Tisbury, this 3 bedroom 1 bath cape home has been owned by the same family for years. Sitting on 1.6 acres in a quiet area that is centrally located on the Island for easy access to up or down Island towns. Short walk to bike path and state forest. West Tisbury residents have access to the lovely Lambert's Cove Beach, with purchased sticker. Included on

    Julianna Flanders Flanders Real Estate

    9 Galway Rd, Vineyard Haven, MA 02568
  • /8

    $8,250 Per Month

    • 7 Beds
    • 5 Baths
    • 3,528 Sq Ft
    • House for Rent

    227 S Gate Rd Wt120, West Tisbury, MA 02575

    THIS PROPERTY IS A WEEKLY PROPERTY!! Set on 12 acres of peaceful woods, meadows, stone walls and its own pond, this charming 18th century 4 bedroom farmhouse and 3 bedroom rustic barn sleeps 12 and is perfect for larger groups wanting peace and tranquility all within a short distance to private swimming beaches. The setting, on exclusive Seven Gates Farm, offers miles of sandy trails through open

    Karen Overtoom Karen M. Overtoom R.E.

    227 S Gate Rd Wt120, West Tisbury, MA 02575
  • /2

    $900,000

    Sold Sep 17, 2025

    00 Quenames Rd Unit 30-02, Chilmark, MA 02535

    • Land
    • 3.05 Acres
    • $295,082 per Acre

    Last Sold Summary

    • 10% Below List Price
    • 83 Days On Market

    Last Listing Agent Candy DaRosa Feiner Real Estate

    00 Quenames Rd Unit 30-02, Chilmark, MA 02535
    • /39

      Est $3,277,697

      Not Listed For Sale

      18 S Pond Rd, Vineyard Haven, MA 02568

      • 5 Beds
      • 4.5 Baths
      • 4,239 Sq Ft
      • Built 1999
      18 S Pond Rd, Vineyard Haven, MA 02568

      Last Sold Summary

      • 341 Days On Market

  • /52

    $5,295,000

    • 4 Beds
    • 3 Baths
    • 3,432 Sq Ft

    44 Cencelle St, Chilmark, MA 02535

    This private 17-acre Chilmark estate with ocean views, tucked away in the rolling hills and farmlands of Chilmark, offers sweeping ocean views to the south and a rare sense of seclusion and serenity. At the heart of the property is a striking modern style home, thoughtfully designed to bring the outdoors in. Expansive walls of glass flood the interior with natural light and frame panoramic views

    Meg Bodnar Tea Lane Associates

    44 Cencelle St, Chilmark, MA 02535
  • /35

    $22,000 Per Month

    • 4 Beds
    • 2 Baths
    • 2,290 Sq Ft
    • House for Rent

    36 Henry Hough Lane Ch206, Chilmark, MA 02535

    THIS IS A WEEKLY SUMMER RENTAL ONLY.THE WEEKLY PRICE IN AUGUST IS $5,500. PER WEEK.SEE WEB SITE FOR ADDITIONAL WEEKLY PRICING. Water views, 3 acres and stone walls. At the end of a lane, enjoy the privacy offered by 49 acres of conservation land complete with walking trails. This house is a short distance from Lucy Vincent beach, as well as from Menemsha and Squibnocket. This spacious four

    Karen Overtoom Karen M. Overtoom R.E.

    36 Henry Hough Lane Ch206, Chilmark, MA 02535
  • /22

    $4,250,000

    Sold Sep 09, 2025

    420 Lamberts Cove Rd, Vineyard Haven, MA 02568

    • 7 Beds
    • 6 Baths
    • 4,125 Sq Ft
    • Built 1900

    Last Sold Summary

    • 5% Below List Price
    • $1,030/SF
    • 21 Days On Market

    Last Listing Agent Alyssa Halisky Wallace & Co. Sotheby's

    420 Lamberts Cove Rd, Vineyard Haven, MA 02568
    • /26

      Est $2,011,420

      Not Listed For Sale

      82 South Rd, Chilmark, MA 02535

      • 3 Beds
      • 2 Baths
      • 1,862 Sq Ft
      • Built 1960
      82 South Rd, Chilmark, MA 02535

      Last Sold Summary

      • 10 Days On Market

  • /31

    $12,500,000

    Pending
    • 6 Beds
    • 4 Baths
    • 4,876 Sq Ft

    44 Forest Rd, Vineyard Haven, MA 02568

    Quintessential Seven Gates waterfront compound offering outstanding views and immediate beachfront access. This exceptional Martha’s Vineyard retreat includes a main residence and barn, thoughtfully designed and built by South Mountain Company. Immaculately maintained, both structures are virtually turn-key.The interiors showcase rich detail, the highest level of craftsmanship, and elegant

    Bill Rossi Studio Realty

    44 Forest Rd, Vineyard Haven, MA 02568
  • /17

    $17,600 Per Month

    • 4 Beds
    • 4 Baths
    • 2,676 Sq Ft
    • House for Rent

    40 Summer Cir, West Tisbury, MA 02575

    THIS IS A WEEKLY SUMMER RENTAL ONLY.THE WEEKLY PRICE IN AUGUST IS $4,400. PER WEEK.SEE WEB SITE FOR ADDITIONAL WEEKLY PRICING. This beautiful tasteful modern home has many charming elements. The bright open airy floor plan offers a generous kitchen, welcoming dining room and living room surrounded by windows and decks with an outdoor table and extra seating. An "upside down" house with the living

    Karen Overtoom Karen M. Overtoom R.E.

    40 Summer Cir, West Tisbury, MA 02575
  • /2

    $60,000

    Sold Jul 01, 2025

    0 North Rd Unit 40 43533, Aquinnah, MA 02535

    • Land
    • 0 Sq Ft

    Last Sold Summary

    Last Listing Agent Mark Jenkins Wallace & Co. Sotheby's

    0 North Rd Unit 40 43533, Aquinnah, MA 02535
    • /18

      Est $1,803,588

      Not Listed For Sale

      29 Brook Hollow Rd, Vineyard Haven, MA 02568

      • 4 Beds
      • 2.5 Baths
      • 2,461 Sq Ft
      • Built 1994
      29 Brook Hollow Rd, Vineyard Haven, MA 02568

      Last Sold Summary

      • 52 Days On Market

  • /13

    $1,645,000

    • Land
    • 3.32 Acres
    • $495,482 per Acre

    26 Flint Hill Rd, West Tisbury, MA 02575

    Stop Searching. Start Building. You've toured dozens of homes. Nothing feels right. What if your dream home on Martha's Vineyard simply hasn't been built yet? This rare 3.32-acre West Tisbury hilltop is the blank canvas you've been waiting for. Glacial boulders, open pasture, and cathedral oaks with Land Bank-preserved Arrowhead Farm and protected Rodgers Path land on two sides— a setting no

    Dawn Bellante Sandpiper Realty, Inc.

    26 Flint Hill Rd, West Tisbury, MA 02575
  • /8

    $18,000 Per Month

    • 3 Beds
    • 2.5 Baths
    • House for Rent

    71 Bartmus Luce Road Wt154, West Tisbury, MA 02575

    THIS IS A WEEKLY SUMMER RENTAL ONLY.THE WEEKLY PRICE IN AUGUST IS $5,000. PER WEEK.SEE WEB SITE FOR ADDITIONAL WEEKLY PRICING. Finest Views on the Island!! This house is set high on a hill surrounded by nature. The expansive views from the front of this house are spectacular. Enjoy the large deck or the screened porch and gaze upon one of the most amazing Vineyard Views available. It is a short

    Karen Overtoom Karen M. Overtoom R.E.

    71 Bartmus Luce Road Wt154, West Tisbury, MA 02575
  • /9

    $1,500,000

    Sold Oct 20, 2025

    49 Cobbs Hill Rd Unit 24.3, Chilmark, MA 02535

    • Land
    • 3.9 Acres
    • $384,615 per Acre

    Last Sold Summary

    Last Listing Agent Mark Jenkins Wallace & Co. Sotheby's

    49 Cobbs Hill Rd Unit 24.3, Chilmark, MA 02535
    • /16

      Est $1,232,999

      Not Listed For Sale

      31 Music St, Vineyard Haven, MA 02568

      • 3 Beds
      • 1.5 Baths
      • 1,150 Sq Ft
      • Built 1817
      31 Music St, Vineyard Haven, MA 02568

      Last Sold Summary

      • 0 Days On Market

  • /48

    $5,850,000

    • 6 Beds
    • 6.5 Baths
    • 3,608 Sq Ft

    9 Ridge Hill Rd, Chilmark, MA 02535

    Set on three beautifully landscaped acres, this exceptional six-bedroom property offers a seamless blend of modern farmhouse design and timeless Vineyard appeal. The estate features a five-bedroom, five and a half bathroom main residence, along with a one-bedroom guest suite above a two-car barn and 16' x 40' swimming pool. This thoughtfully designed post and beam main home was featured in

    Alexis Holden Tea Lane Associates

    9 Ridge Hill Rd, Chilmark, MA 02535
  • /22

    $3,000 Per Month

    • 4 Beds
    • 2.5 Baths
    • 2,703 Sq Ft
    • House for Rent

    41 Oak Lane Wt147, West Tisbury, MA 02575

    THIS IS A WEEKLY SUMMER RENTAL ONLY.THE WEEKLY PRICE IN AUGUST IS $3,200. PER WEEK.SEE WEB SITE FOR ADDITIONAL WEEKLY PRICING. Inside the front entrance is a large open living room with a comfortable L-shaped couch facing the floor to ceiling windows which look out onto the spacious tree lined back yard and a wall mounted flat screen television. Off the open concept living/dining room is a large

    Karen Overtoom Karen M. Overtoom R.E.

    41 Oak Lane Wt147, West Tisbury, MA 02575
  • /29

    $1,075,000

    Sold Feb 26, 2026

    34 Pine Ln, Vineyard Haven, MA 02568

    • 3 Beds
    • 2 Baths
    • 1,120 Sq Ft
    • Built 1984

    Last Sold Summary

    • 14% Below List Price
    • $960/SF
    • 93 Days On Market

    Current Estimated Value $1,160,612

    Last Listing Agent Candy DaRosa Feiner Real Estate

    34 Pine Ln, Vineyard Haven, MA 02568
    • /23

      Not Listed For Sale

      51 Blueberry Ridge Ln, Chilmark, MA 02535

      • 6 Beds
      • 3.5 Baths
      • 2,229 Sq Ft
      • Built 1989
      51 Blueberry Ridge Ln, Chilmark, MA 02535

      Last Sold Summary

      • 11 Days On Market

  • /37

    $1,795,000

    $50K PRICE DROP
    • 5 Beds
    • 3 Baths
    • 2,552 Sq Ft

    10 Danls Way, West Tisbury, MA 02575

    Historic West Tisbury Farmhouse with Guest Cottage Set on 1.27 acres in the heart of West Tisbury, this four-bedroom farmhouse and separate one-bedroom guest cottage offer a rare opportunity to create a quintessential Martha’s Vineyard family compound. Ideally located near Alley’s General Store, 7a Foods, and North Tisbury Village, the property also provides convenient access to beaches and

    Emma Bryant Studio Realty

    10 Danls Way, West Tisbury, MA 02575
  • /9

    $10,800 Per Month

    • 4 Beds
    • 2 Baths
    • 702 Sq Ft
    • House for Rent

    141 N Rd Ch202, Chilmark, MA 02535

    THIS IS A WEEKLY SUMMER RENTAL ONLY.THE WEEKLY PRICE IN AUGUST IS $2,700. PER WEEK.SEE WEB SITE FOR ADDITIONAL WEEKLY PRICING. Chilmark Cottage Perfection!!! You will love this quaint Vineyard Style Cottage that has been meticulously designed to include all the amenities one could imagine. This vintage charmer really boasts a lot of Style. Inside you will find really beautiful hardwood floors, a

    Karen Overtoom Karen M. Overtoom R.E.

    141 N Rd Ch202, Chilmark, MA 02535
  • /22

    $1,607,000

    Sold Jul 10, 2025

    10 N Abels Hill Rd, Chilmark, MA 02535

    • 4 Beds
    • 3 Baths
    • 2,850 Sq Ft
    • Built 1978

    Last Sold Summary

    • 39% Below List Price
    • $564/SF
    • 354 Days On Market

    Current Estimated Value $2,176,121

    Last Listing Agent Elissa Lash Tea Lane Associates

    10 N Abels Hill Rd, Chilmark, MA 02535
    • /2

      Est $1,717,360

      Not Listed For Sale

      323 Lamberts Cove Rd, Vineyard Haven, MA 02568

      • 4 Beds
      • 3 Baths
      • 1,144 Sq Ft
      • Built 1900
      323 Lamberts Cove Rd, Vineyard Haven, MA 02568

  • /38

    $16,000,000

    • Land
    • 46 Acres
    • $347,826 per Acre

    0, 36, 38 Black Point Rd Unit 11, 9-02, 9-01, 058-, Chilmark, MA 02535

    Forty six extraordinary acres on Black Point Pond with easy access to Black Point sandy ocean beach. Magical expansive views of meadows, pond and ocean. This estate-sized property abuts 140 acres of Sheriff’s Meadow conservation land, offering exceptional privacy. A simple 1041 square foot two bedroom seasonal home sits on one lot with two detached studios alongside. Close to nature, this home

    Abby Rabinovitz Tea Lane Associates

    0, 36, 38 Black Point Rd Unit 11, 9-02, 9-01, 058-, Chilmark, MA 02535
  • /8

    $4,500 Per Month

    • 2 Beds
    • 2 Baths
    • 1,393 Sq Ft
    • House for Rent

    33 Menemsha Inn Rd Ch223 3, Chilmark, MA 02535

    THIS IS A WEEKLY RENTAL PROPERTY!! This spacious two bedroom home is filled with classic Vineyard charm. Each room features spectacular views overlooking Vineyard Sound, as well as stellar sunsets in the evening. Close to Menemsha Village and public beach as well as access to Lucy Vincent and Squibnocket beaches.

    Karen Overtoom Karen M. Overtoom R.E.

    33 Menemsha Inn Rd Ch223 3, Chilmark, MA 02535
  • /22

    $1,000,000

    Sold Jun 03, 2026

    31 North Rd, Chilmark, MA 02535

    • 2 Beds
    • 1 Bath
    • 576 Sq Ft
    • Built 1970

    Last Sold Summary

    • 17% Below List Price
    • $1,736/SF
    • 9 Days On Market

    Current Estimated Value $1,101,183

    Last Listing Agent Russell Maloney Russell Maloney Real Estate

    31 North Rd, Chilmark, MA 02535
    • /31

      Est $2,561,468

      Not Listed For Sale

      106 Panhandle Rd, Vineyard Haven, MA 02568

      • 4 Beds
      • 3.5 Baths
      • 3,310 Sq Ft
      • Built 1991
      106 Panhandle Rd, Vineyard Haven, MA 02568

      Last Sold Summary

      • 80 Days On Market

  • /40

    $1,795,000

    $104K PRICE DROP
    • 4 Beds
    • 3.5 Baths
    • 2,061 Sq Ft

    174 Middle Rd, Chilmark, MA 02535

    Nestled in the heart of Chilmark, this four-bedroom home offers a blend of comfort, convenience, and timeless Vineyard charm. Thoughtfully designed with distinct, well-proportioned rooms, the home centers around an expansive, sunlit, eat-in kitchen featuring dual ovens, elegant granite countertops, and extensive custom cherry wood built-ins that combine beauty and practicality. The welcoming

    Sheila Morse Island Real Estate

    174 Middle Rd, Chilmark, MA 02535
  • /21

    $8,000 Per Month

    • 1 Bed
    • 1 Bath
    • 936 Sq Ft
    • House for Rent

    10 James Pond Way, West Tisbury, MA 02575

    THIS IS A WEEKLY SUMMER RENTAL ONLY.THE WEEKLY PRICE IN AUGUST IS $2,000. PER WEEK.SEE WEB SITE FOR ADDITIONAL WEEKLY PRICING. This spacious and well appointed one bedroom guest house has a cozy living area and kitchen which opens up to a large second story deck with outdoor furniture, table and chairs where you can enjoy dining amidst the trees. One A/C unit is in the bedroom along with a

    Karen Overtoom Karen M. Overtoom R.E.

    10 James Pond Way, West Tisbury, MA 02575
  • /2

    $1,500,000

    Sold Aug 13, 2025

    82 Christiantown Rd Unit R, West Tisbury, MA 02575

    • Land
    • 7.42 Acres
    • $202,156 per Acre

    Last Sold Summary

    • 0 Days On Market

    Last Listing Agent LINK Email Cache LINK

    82 Christiantown Rd Unit R, West Tisbury, MA 02575
    • /20

      Est $1,253,621

      Not Listed For Sale

      46 Old Coach Rd, Vineyard Haven, MA 02568

      • 3 Beds
      • 2 Baths
      • 1,374 Sq Ft
      • Built 1981
      46 Old Coach Rd, Vineyard Haven, MA 02568

      Last Sold Summary

      • 43 Days On Market

Showing Results 41 - 80, Page 2 of 18

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