Oak Bluffs, MA Homes

• 

  

  

  /32

  $2,250,000

  • 4 Beds
  • 2.5 Baths
  • 2,522 Sq Ft

  29 Old Nursery Ln, Chilmark, MA 02535

  Modern Cape style home located off Tea Lane could be your special Chilmark retreat. This four bedroom, 2.5 bathroom home needs some updating but is in good condition. Living room with fireplace, dining area and family room provide space for living. Attached two bay garage allows for storage and projects. Wood working area in the basement is a plus. Enjoy the outdoors via the screened porch, large

  Julianna Flanders Flanders Real Estate

  29 Old Nursery Ln, Chilmark, MA 02535
• 

  

  

  /42

  $19,000 per month

  • 6 Beds
  • 6.5 Baths
  • 6,950 Sq Ft
  • House for Rent

  40 Sweet William Way, West Tisbury, MA 02575

  THIS PROPERTY IS A WEEKLY RENTAL PROPERTY! This stunning home is situated right in the heart of West Tisbury, yet set back enough for a completely private feel. On a property that encompasses 10 acres with your own private pond, you will feel the stress melt away as soon as you get to this luxury vacation home. Keys to private Quansoo Beach Association come with the house. Spend your days on the

  Karen Overtoom Karen M. Overtoom R.E.

  40 Sweet William Way, 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 $1,666,764

  Last Listing Agent Lisa Da Silva Signal House Group

  10 Red Pony Rd, West Tisbury, MA 02568
• 

  

  

  /34

  Est $1,556,989 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

  • 11% Above List Price
  • $964/SF
  • 59 Days On Market

  • Last Sold Price $1,400,000
  • May 20, 2024

  Last Listing Agent Candy DaRosa Feiner Real Estate
• 

  

  

  /53

  $6,750,000

  • 5 Beds
  • 3.5 Baths
  • 4,050 Sq Ft

  78 Hammett Rd, Chilmark, MA 02535

  Wonderful elevated Chilmark north shore 3.8 acre secure waterfront property with dramatic year round sunset water views to the Gay Head Lighthouse and Elizabeth Islands. The Vineyard Sound expanse enjoys peaceful sailing, fishing and other boating activity to enhance the ocean splendor. The 5 bedroom 3 1/2 bath 4,050 sq ft home is literally in move-in condition. Architect designed and built by

  Robert Kenney Tea Lane Associates

  78 Hammett Rd, Chilmark, MA 02535
• 

  

  /28

  $32,000 per month

  • 4 Beds
  • 4 Baths
  • 3,200 Sq Ft
  • House for Rent

  37 Mempremagog Ave Vh410, Tisbury, MA 02568

  THIS IS A WEEKLY SUMMER RENTAL ONLY.THE WEEKLY PRICE IN AUGUST IS $8,200. PER WEEK.SEE WEB SITE FOR ADDITIONAL WEEKLY PRICING. Fabulous custom designed and decorated four bedroom home is located in a wooded setting that offers total privacy and is with-in walking distance to a private association beach. And yet is only 3 miles from downtown Vineyard Haven. This lovely home offers a gourmet eat-in

  Karen Overtoom Karen M. Overtoom R.E.

  37 Mempremagog Ave Vh410, Tisbury, MA 02568
• 

  

  /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
• 

  

  /39

  Est $3,309,782 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

  • 14% Above List Price
  • $683/SF
  • 341 Days On Market

  • Last Sold Price $2,895,000
  • Jan 10, 2025

  Last Listing Agent Rose Ryley Wallace & Co. Sotheby's
• 

  

  /6

  $1,575,000

  • 2 Beds
  • 1 Bath
  • 924 Sq Ft

  47 Quenames Rd, Chilmark, MA 02535

  On a beautiful 3.02-acre parcel in Chilmark, 47 Quenames Road offers privacy, outstanding value, and excellent potential. The year-round 2-bedroom home features first-floor living, an open floorplan with living and dining space, a kitchen remodeled in 2023, two bedrooms, and a full bath with tub. A new roof (2023) and outdoor deck with bluestone patio area overlooks the lawn and the natural

  Dawn Bellante Sandpiper Realty, Inc.

  47 Quenames Rd, Chilmark, MA 02535
• 

  

  /26

  $50,700 per month

  • 4 Beds
  • 3 Baths
  • 2,346 Sq Ft
  • House for Rent

  6 Trails End Ch241, Chilmark, MA 02535

  THIS IS A WEEKLY SUMMER RENTAL ONLY.THE WEEKLY PRICE IN AUGUST IS $12,675. PER WEEK.SEE WEB SITE FOR ADDITIONAL WEEKLY PRICING. Set atop a hill you will find this wonderful 4 bedroom home with distant views and a wonderful lap pool. Enjoy your days on the large deck or take a swim in the pool. This great vacation home is tastefully decorated and is located on one level with plenty of space for

  Karen Overtoom Karen M. Overtoom R.E.

  6 Trails End Ch241, Chilmark, MA 02535
• 

  

  /20

  $1,150,000 Sold Jun 13, 2025

  46 Old Coach Rd, Vineyard Haven, MA 02568

  • 3 Beds
  • 2 Baths
  • 1,374 Sq Ft
  • Built 1981

  Last Sold Summary

  • 10% Below List Price
  • $837/SF
  • 43 Days On Market

  Current Estimated Value $1,283,412

  Last Listing Agent Lisa Gilberto C McManus Realty Group

  46 Old Coach Rd, Vineyard Haven, MA 02568
• 

  

  /26

  Est $1,935,899 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

  • 6% Above List Price
  • $983/SF
  • 10 Days On Market

  • Last Sold Price $1,830,000
  • Dec 05, 2024

  Last Listing Agent Meg Bodnar Tea Lane Associates
• 

  

  /36

  $1,390,000

  • 4 Beds
  • 2 Baths
  • 1,332 Sq Ft

  40 Scotchmans Ln, Vineyard Haven, MA 02568

  A home with history, built in the early 1800s this dwelling was originally built on a local farm and moved to its present location in the 1920's. The structure sits nestled amongst mature plantings and out buildings facing the Mill Brook. The studio and covered patio offer opportunities to entertain, relax and reflect. This 3.76 parcel was created from a larger parcel by the owner (see attached

  Jim Osmundsen Donnelly + Co.

  40 Scotchmans Ln, Vineyard Haven, MA 02568
• 

  

  /3

  $13,200 per month

  • 2 Beds
  • 2 Baths
  • 1,344 Sq Ft
  • House for Rent

  224 N Rd Ch248, Chilmark, MA 02535

  THIS PROPERTY IS A WEEKLY RENTAL PROPERTY!! A modern summer retreat is nestled high on a knoll off North Rd in picturesque Chilmark. Here in this stunning contemporary ranch you will find the upmost in Luxury. Each room is exciting, charming and has a simplistic yet artistic style. The entire house is accented with beautiful light pine flooring that pairs perfectly with the expansive main room.

  Karen Overtoom Karen M. Overtoom R.E.

  224 N Rd Ch248, Chilmark, MA 02535
• 

  /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
• 

  

  /18

  Est $1,774,865 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

  • 6% Above List Price
  • $683/SF
  • 52 Days On Market

  • Last Sold Price $1,680,000
  • Oct 26, 2023

  Last Listing Agent Peyton Wallace Studio Realty
• 

  

  /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
• 

  

  /33

  $22,000 per month

  • 3 Beds
  • 2.5 Baths
  • 2,800 Sq Ft
  • House for Rent

  2 Strikers Way Ch211, Chilmark, MA 02535

  SEE WEB SITE FOR ADDITIONAL WEEKLY PRICING. Just a short distance from Chilmark Store, this newly remodeled home features 3 bedrooms and 2 1/2 baths. High end finishes with a beachy island feel. The master is located on the first floor with en-suit bath. Fully equipped kitchen with a Cuisinart 14-cup programmable drip coffee maker with glass carafe. There is a coffee grinder provided in the

  Karen Overtoom Karen M. Overtoom R.E.

  2 Strikers Way Ch211, Chilmark, MA 02535
• 

  /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
• 

  

  /16

  Est $1,242,402 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

  • 10% Above List Price
  • $978/SF
  • 0 Days On Market

  • Last Sold Price $1,125,000
  • Feb 29, 2024

  Last Listing Agent LINK Email Cache LINK
• 

  

  /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
• 

  

  /20

  $16,800 per month

  • 3 Beds
  • 2 Baths
  • 1,638 Sq Ft
  • House for Rent

  31 S Ridge Rd Ch218, Chilmark, MA 02535

  THIS IS A WEEKLY SUMMER RENTAL ONLY.THE WEEKLY PRICE IN AUGUST IS $4,200. PER WEEK.SEE WEB SITE FOR ADDITIONAL WEEKLY PRICING. Set high on a hill in picturesque Chilmark is this absolutely wonderful 3 bedroom home with a finished walk out that has a sofa bed. Each bedroom has a window A/C unit. The grounds are beautiful. Wonderful screen porch for your morning coffee or sit in the back yard and

  Karen Overtoom Karen M. Overtoom R.E.

  31 S Ridge Rd Ch218, Chilmark, MA 02535
• 

  /2

  $3,772,500 Sold May 29, 2025

  3 Tennis Ln, Chilmark, MA 02535

  • 4 Beds
  • 4.5 Baths
  • 3,234 Sq Ft
  • Built 1999

  Last Sold Summary

  • 3% Below List Price
  • $1,167/SF
  • 0 Days On Market

  Last Listing Agent Candy DaRosa Feiner Real Estate

  3 Tennis Ln, Chilmark, MA 02535
• 

  

  /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

  • $1,032/SF
  • 11 Days On Market

  • Last Sold Price $2,300,000
  • Nov 08, 2024

  Last Listing Agent Rebecca V Conroy Conroy & Company R.E., Inc.
• 

  

  /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
• 

  

  /31

  $40,000 per month

  • 6 Beds
  • 6 Baths
  • 3,960 Sq Ft
  • House for Rent

  384 Middle Rd Ch222, Chilmark, MA 02535

  THIS IS A WEEKLY SUMMER RENTAL ONLY.THE WEEKLY PRICE IN AUGUST IS $10,000. PER WEEK.SEE WEB SITE FOR ADDITIONAL WEEKLY PRICING. This gracious Vineyard elongated Cape overlooks the Keith Farm and the Atlantic Ocean beyond. The gourmet kitchen has just been beautifully renovated and is a dream. The living areas are all decorated with charm and all have views. The separate main house, with four

  Karen Overtoom Karen M. Overtoom R.E.

  384 Middle Rd Ch222, Chilmark, MA 02535
• 

  

  /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
• 

  

  /36

  Est $1,670,275 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

  Last Sold Summary

  • 1% Below List Price
  • $1,473/SF
  • 331 Days On Market

  • Last Sold Price $1,685,000
  • Aug 29, 2023

  Last Listing Agent Diana Gilmore Island Real Estate
• 

  

  /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
• 

  

  /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
• 

  

  /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 $1,240,755

  Last Listing Agent Candy DaRosa Feiner Real Estate

  34 Pine Ln, Vineyard Haven, MA 02568
• 

  

  /31

  Est $2,610,171 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

  • 3% Above List Price
  • $763/SF
  • 80 Days On Market

  • Last Sold Price $2,525,000
  • Jan 17, 2025

  Last Listing Agent Brenda Galligan Karen M. Overtoom R.E.
• 

  

  /40

  $1,895,000

  • 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
• 

  

  /19

  $24,000 per month

  • 4 Beds
  • 4 Baths
  • 2,000 Sq Ft
  • House for Rent

  44 Flanders Ln, Chilmark, MA 02535

  THIS IS A WEEKLY SUMMER RENTAL ONLY.!! SEE WEB SITE FOR WEEKLY PRICING. This house sits up the hill and looks toward Menemsha. It is private and protected by the trees. Visit town to watch sunsets in Menemsha, dine in one of the places to eat there or take in a day at the beach.Access to and parking for beautiful private association beach.

  Karen Overtoom Karen M. Overtoom R.E.

  44 Flanders Ln, 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 $1,993,418

  Last Listing Agent Elissa Lash Tea Lane Associates

  10 N Abels Hill Rd, Chilmark, MA 02535
• 

  

  /35

  Est $2,066,306 Not Listed For Sale

  159 Charles Neck Way, Vineyard Haven, MA 02568

  • 4 Beds
  • 3 Baths
  • 1,995 Sq Ft
  • Built 2003

  159 Charles Neck Way, Vineyard Haven, MA 02568

  Last Sold Summary

  • 4% Above List Price
  • $1,000/SF
  • 47 Days On Market

  • Last Sold Price $1,995,000
  • Nov 15, 2024

  Last Listing Agent Wendy Harman Compass
• 

  

  /25

  $7,300,000

  • 5 Beds
  • 5.5 Baths
  • 3,539 Sq Ft

  65 Carl's Way, West Tisbury, MA 02568

  Stylized Private Waterfront Retreat close to townperched along the tranquil shores of the beloved Tisbury Great Pond, this stunning Hutker-designed waterfront home is a seamless blend of coastal elegance and timeless island charm. Designed to capture the essence of Vineyard living, the home features intimate water views, sun-drenched interiors, and carefully curated finishes

  Jill Napior Tea Lane Associates

  65 Carl's Way, West Tisbury, MA 02568
• 

  

  /32

  $36,000 per month

  • 3 Beds
  • 3.5 Baths
  • 2,600 Sq Ft
  • House for Rent

  29 Cemetery Rd Ch216, Chilmark, MA 02535

  THIS IS A WEEKLY SUMMER RENTAL ONLY.THE WEEKLY PRICE IN AUGUST IS $9,000. PER WEEK.SEE WEB SITE FOR ADDITIONAL WEEKLY PRICING. Fabulous Chilmark home offers two levels of living space. On the first floor there is a fully equipped kitchen open to the dining room, a living room with fireplace, built-ins and sliders to a deck overlooking a meadow and the most incredible water views. There is a half

  Karen Overtoom Karen M. Overtoom R.E.

  29 Cemetery Rd Ch216, Chilmark, MA 02535
• 

  

  /3

  $1,695,000 Sold May 30, 2025

  5 Vincent Rd, Vineyard Haven, MA 02568

  • 2 Beds
  • 2 Baths
  • 1,296 Sq Ft
  • Built 1960

  Last Sold Summary

  • $1,308/SF

  Current Estimated Value $1,480,902

  Last Listing Agent Alisan Lohan-Conway Alisan Lohan-Conway Properties

  5 Vincent Rd, Vineyard Haven, MA 02568
• 

  

  /30

  Est $1,442,846 Not Listed For Sale

  88 Hopps Farm Rd, Vineyard Haven, MA 02568

  • 3 Beds
  • 2 Baths
  • 1,464 Sq Ft
  • Built 1992

  88 Hopps Farm Rd, Vineyard Haven, MA 02568

  Last Sold Summary

  • 8% Above List Price
  • $908/SF
  • 80 Days On Market

  • Last Sold Price $1,330,000
  • Jun 20, 2023

  Last Listing Agent Emma Bryant Landmarks at TODAY Real Estate

Showing Results 41 - 80, Page 2 of 18