Oak Bluffs, MA Homes

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  /79

  $1,845,000

  • 5 Beds
  • 3 Baths
  • 2,552 Sq Ft

  10 Danls Way, West Tisbury, MA 02575

  HOUSE + GUEST HOUSE:Historic 4-Bedroom 2-Bathroom Main House & 1-Bedroom 1-Bathroom Cottage. Located on a lush 1.27 acres and just a short distance from Alley's General Store, 7a Foods + North Tisbury, this property has all the makings of a perfect family compound. With plenty of space for lawn games and gardens and no shortage of history & charm. There has been so much care put into its

  Emma Kiley Bryant Landmarks at TODAY Real Estate

  10 Danls Way, West Tisbury, MA 02575
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  /2

  $10,000 total monthly price

  • 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
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  /44

  $8,178,500 Sold Oct 27, 2025

  94 Menemsha Inn Rd, Chilmark, MA 02535

  • 6 Beds
  • 4.5 Baths
  • 4,104 Sq Ft
  • Built 2001

  Last Sold Summary

  • 3% Below List Price
  • $1,993/SF
  • 38 Days On Market

  Last Listing Agent Julianna Flanders Flanders Real Estate

  94 Menemsha Inn Rd, Chilmark, MA 02535
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  /41

  Not Listed For Sale

  • 3 Beds
  • 2 Baths
  • 1,598 Sq Ft

  566 Scrubby Neck Rd, Vineyard Haven, MA 02568

  566 Scrubby Neck Rd, Vineyard Haven, MA 02568
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  /39

  $3,500,000

  • 3 Beds
  • 4 Baths
  • 2,500 Sq Ft

  27 Clambelly Rd, Chilmark, MA 02535

  A place of serenity tucked in the woods of Chilmark. Complete renovation 2017/2018, large fenced in back yard with exquisite fish pond with waterfall and lighting. Kitchen has concrete countertops, sub zero refrigerator, Wolf Oven & Speed Oven. Large open formal dining area and open formal sitting area with fireplace. Beautiful reclaimed wood flooring. LED lighting throughout house, Media

  Julianna Flanders Flanders Real Estate

  27 Clambelly Rd, Chilmark, MA 02535
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  /25

  $13,600 total monthly price

  • 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
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  /34

  $2,475,000 Sold Sep 05, 2025

  31 N Slope Ln, Chilmark, MA 02535

  • 4 Beds
  • 3.5 Baths
  • 2,300 Sq Ft
  • Built 1983

  Last Sold Summary

  • 15% Below List Price
  • $1,076/SF
  • 117 Days On Market

  Current Estimated Value $2,576,026

  Last Listing Agent Bill Rossi Studio Realty

  31 N Slope Ln, Chilmark, MA 02535
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  /13

  Est $4,410,745 Not Listed For Sale

  • 3 Beds
  • 2 Baths
  • 1,300 Sq Ft

  144 Pond View Farm Rd, Vineyard Haven, MA 02568

  144 Pond View Farm Rd, Vineyard Haven, MA 02568
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  /2

  $799,000

  • Land
  • 0.91 Acre
  • $878,022 per Acre

  22 Bramble Path, West Tisbury, MA 02568

  Flat building lot centrally located in West Tisbury. A perc test has been done that supports a four bedroom title five system. It is the buyers responsibility to install utilities, well and septic.

  Michele Casavant Vineyard Village Realty

  22 Bramble Path, West Tisbury, MA 02568
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  /18

  $10,000 total monthly price

  • 3 Beds
  • 2 Baths
  • 1,439 Sq Ft
  • House for Rent

  24 Nat's Farm Lane Wt113, West Tisbury, MA 02575

  THIS IS A WEEKLY SUMMER RENTAL ONLY.THE WEEKLY PRICE IN AUGUST IS $2,500. PER WEEK.SEE WEB SITE FOR ADDITIONAL WEEKLY PRICING. Charming three bedroom home located in a private neighborhood close to bike path, walking trails and public tennis courts. Just a short drive to Lambert's Cove Beach, West Tisbury Village and down island restaurants and shops.Amenities include High definition TV, wifi

  Karen Overtoom Karen M. Overtoom R.E.

  24 Nat's Farm Lane Wt113, West Tisbury, MA 02575
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  /51

  $4,850,000 Sold Dec 05, 2025

  49 Gosnold's Way, Chilmark, MA 02535

  • 5 Beds
  • 3.5 Baths
  • 4,044 Sq Ft
  • Built 2003

  Last Sold Summary

  • 8% Below List Price
  • $1,199/SF
  • 115 Days On Market

  Last Listing Agent Meg Bodnar Tea Lane Associates

  49 Gosnold's Way, Chilmark, MA 02535
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  /42

  Est $1,910,025 Not Listed For Sale

  • 4 Beds
  • 5 Baths
  • 2,172 Sq Ft

  44 Music St, Vineyard Haven, MA 02568

  44 Music St, Vineyard Haven, MA 02568
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  /60

  $14,000,000

  • 6 Beds
  • 7 Baths
  • 6,967 Sq Ft

  8 Snail Rd, Chilmark, MA 02535

  This exceptional Martha's Vineyard estate promises unmatched privacy and breathtaking views of the Atlantic Ocean and Chilmark Pond. Masterfully designed by acclaimed architect Rick Sundberg and built by renowned island builder Andrew Flake, this three-parcel property seamlessly blends modern sophistication with the timeless charm of the Vineyard. Upon entering, you are greeted by soaring

  Alyssa Halisky Wallace & Co. Sotheby's

  8 Snail Rd, Chilmark, MA 02535
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  /39

  $46,000 total monthly price

  • 6 Beds
  • 4.5 Baths
  • 3,800 Sq Ft
  • House for Rent

  99 Pond Road Wt104, West Tisbury, MA 02575

  THIS IS A WEEKLY RENTAL NOT A MONTHLY!!!!! Beautiful bright sunny home with open concept living. Main floor features a gourmet kitchen with stainless appliances, breakfast bar and formal dining table to seat 10. Large glass sliders open up to expansive views of the deck, pool and pasture beyond. Also on the main level is a separate living area with large screen TV, powder room, and den with twin

  Karen Overtoom Karen M. Overtoom R.E.

  99 Pond Road Wt104, West Tisbury, MA 02575
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  /19

  $1,330,000 Sold Oct 17, 2025

  32 MacHipscat Trail, Vineyard Haven, MA 02568

  • 3 Beds
  • 1.5 Baths
  • 1,404 Sq Ft
  • Built 1983

  Last Sold Summary

  • 11% Below List Price
  • $947/SF
  • 112 Days On Market

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

  32 MacHipscat Trail, Vineyard Haven, MA 02568
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  /23

  Est $2,072,460 Not Listed For Sale

  • 2 Beds
  • 2 Baths
  • 1,370 Sq Ft

  50 Campbell Rd, Vineyard Haven, MA 02568

  50 Campbell Rd, Vineyard Haven, MA 02568
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  /42

  $7,950,000

  • 5 Beds
  • 7 Baths
  • 4,531 Sq Ft

  85 Reservoir Rd, Vineyard Haven, MA 02568

  Nestled within Seven Gates Farm, one of Martha's Vineyard's most storied and scenic communities, this 26.5-acre estate offers a beautifully renovated farmhouse that seamlessly blends modern comforts with historic charm. Surrounded by ancient stone walls, mature trees, and lush gardens, the property includes a charming guest house, scenic walking paths, and a peaceful hilltop retreat with a stone

  Alyssa Halisky Wallace & Co. Sotheby's

  85 Reservoir Rd, Vineyard Haven, MA 02568
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  /34

  $12,000 total monthly price

  • 3 Beds
  • 2.5 Baths
  • 2,240 Sq Ft
  • House for Rent

  267 Great Plains Road Wt117, West Tisbury, MA 02575

  THIS IS A WEEKLY SUMMER RENTAL ONLY.THE WEEKLY PRICE IN AUGUST IS $4,000. PER WEEK.SEE WEB SITE FOR ADDITIONAL WEEKLY PRICING. Large spacious home with open concept living and dining area. This house has gorgeous hardwood floors throughout, separate media room, and loads of natural sunlight. It also features an exceptionally large master bedroom with en-suite bath, and private deck. There is

  Karen Overtoom Karen M. Overtoom R.E.

  267 Great Plains Road Wt117, West Tisbury, MA 02575
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  /12

  $1,250,000 Sold Oct 23, 2025

  25 Plum Bush Point Rd Unit 6, West Tisbury, MA 02568

  • Land
  • 4.12 Acres
  • $303,398 per Acre

  Last Sold Summary

  • 6% Below List Price
  • 127 Days On Market

  Last Listing Agent Abby Rabinovitz Tea Lane Associates

  25 Plum Bush Point Rd Unit 6, West Tisbury, MA 02568
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  /6

  Est $2,967,988 Not Listed For Sale

  • 4 Beds
  • 3 Baths
  • 1,935 Sq Ft

  71 Runner Rd, Vineyard Haven, MA 02568

  71 Runner Rd, Vineyard Haven, MA 02568
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  /11

  $1,575,000

  • 2 Beds
  • 1 Bath
  • 896 Sq Ft

  45 Quenames Rd, Chilmark, MA 02535

  Set on a serene 3.02-acre parcel in Chilmark, 45 Quenames Road offers privacy, charm, and excellent potential. In a sunny clearing among mature trees, the maintained 2-bedroom house features first-floor living, an open kitchen and living area, two spacious bedrooms, a full bath with shower, an enormous three-season screened porch, a large outdoor shower, kitchen gardens, and a potting area with

  Dawn Bellante-Holand Sandpiper Realty

  45 Quenames Rd, Chilmark, MA 02535
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  /41

  $14,500 total monthly price

  • 5 Beds
  • 5.5 Baths
  • 3,392 Sq Ft
  • House for Rent

  76 School House Lane Wt101, West Tisbury, MA 02575

  THIS IS A WEEKLY RENTAL NOT A MONTHLY!!!! An elegant, whimsical house full of color, quality and artistic touches. The grounds are sumptuous, nature at its apotheosis. There is gentle movement in the landscape with flowering trees and shrubs everywhere replete with a babbling brook flowing into a pond bordering the garden behind the house. The stonework is finely crafted with balanced proportions

  Karen Overtoom Karen M. Overtoom R.E.

  76 School House Lane Wt101, West Tisbury, MA 02575
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  /24

  $1,200,180 Sold Aug 12, 2025

  110 Otis Bassett Rd, Vineyard Haven, MA 02568

  • 3 Beds
  • 1 Bath
  • 1,144 Sq Ft
  • Built 1972

  Last Sold Summary

  • $1,049/SF
  • 13 Days On Market

  Current Estimated Value $1,132,881

  Last Listing Agent Jen O'Hanlon Compass | The O'Hanlon Group

  110 Otis Bassett Rd, Vineyard Haven, MA 02568
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  /11

  Est $1,681,352 Not Listed For Sale

  • 3 Beds
  • 2 Baths
  • 1,562 Sq Ft

  111 Charles Neck Way, Vineyard Haven, MA 02568

  111 Charles Neck Way, Vineyard Haven, MA 02568
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  /55

  $4,450,000

  • 6 Beds
  • 4.5 Baths
  • 2,960 Sq Ft

  104 Pond View Farm Rd, Vineyard Haven, MA 02568

  An exceptional Waterfront Compound on Tisbury Great Pond. Located across the Tisbury Great Pond from the exclusive Blue Heron Farm, this remarkable waterfront property offers a rare opportunity to own a serene compound with two homes and a private permitted dock—ideal for boating to the Atlantic barrier beach, fishing, kayaking, and enjoying the peaceful beauty of the pond. Both the main house

  Alexis Holden Tea Lane Associates

  104 Pond View Farm Rd, Vineyard Haven, MA 02568
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  /22

  $3,000 total monthly price

  • 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
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  /21

  $435,000 Sold Aug 26, 2025

  0 Beach Lot Quansoo Unit 22503743, Chilmark, MA 02535

  • Land
  • 0.1 Acre
  • $4,350,000 per Acre

  Last Sold Summary

  • 3% Below List Price
  • 20 Days On Market

  Last Listing Agent Emma Bryant Landmarks at TODAY Real Estate

  0 Beach Lot Quansoo Unit 22503743, Chilmark, MA 02535
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  /31

  Est $1,201,327 Not Listed For Sale

  • 1 Bed
  • 1.5 Baths
  • 855 Sq Ft

  16 Elias Ln, Vineyard Haven, MA 02568

  16 Elias Ln, Vineyard Haven, MA 02568
• 

  

  /30

  $2,395,000

  • 4 Beds
  • 3 Baths
  • 1,918 Sq Ft

  25 Fulling Mill Rd, Chilmark, MA 02535

  Perched atop Fulling Mill Hill this distinctive contemporary main house plus guest house offers mid-century charm and a serene retreat set on 3.3 acres of mature oak and beech forest and bordered by an ancient stone wall. Designed by renowned Yale School of Architecture Dean Paul Mitarachi, the main house features a striking circular entryway framed by mature Asiatic gardens. Step inside to

  Tom Wallace Wallace & Co. Sotheby's International Realty

  25 Fulling Mill Rd, Chilmark, MA 02535
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  /9

  $10,800 total monthly price

  • 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
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  /9

  $900,000 Sold Oct 10, 2025

  25 N Vine Ln Unit 70.3, West Tisbury, MA 02568

  • Land
  • 3.73 Acres
  • $241,287 per Acre

  Last Sold Summary

  • 33% Below List Price
  • 462 Days On Market

  Last Listing Agent Janna O'Loughlin Portfolio Properties

  25 N Vine Ln Unit 70.3, West Tisbury, MA 02568
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  /26

  Est $1,050,477 Not Listed For Sale

  • 1 Bed
  • 1 Bath
  • 1,182 Sq Ft

  4 Elias Ln, Vineyard Haven, MA 02568

  4 Elias Ln, Vineyard Haven, MA 02568
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  /16

  $3,200,000

  • 4 Beds
  • 3 Baths
  • 2,346 Sq Ft

  6 Trails End, Chilmark, MA 02535

  Step into timeless mid-century modern style and comfort in this single-level, 4-bedroom, 3-bathroom home located in the heart of Chilmark. This home features an open layout with large glass panel doors that lead to a sun-drenched deck, heated in-ground pool, and grassy lawn. This home is offered completely furnished with a well-equipped kitchen, large living room with wood burning fireplace,

  Russell Maloney Russell Maloney Real Estate

  6 Trails End, Chilmark, MA 02535
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  /8

  $7,900 total monthly price

  • 3 Beds
  • 2.5 Baths
  • 2,107 Sq Ft
  • House for Rent

  2 Paddock Cir, Chilmark, MA 02535

  Karen Overtoom Karen M. Overtoom R.E.

  2 Paddock Cir, Chilmark, MA 02535
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  /44

  $37,000,000 Sold Jul 10, 2025

  41 Cobbs Hill Rd, Chilmark, MA 02535

  • 8 Beds
  • 5.5 Baths
  • 7,846 Sq Ft
  • Built 1993

  Last Sold Summary

  • 5% Below List Price
  • $4,716/SF
  • 39 Days On Market

  Last Listing Agent Brian Dougherty Corcoran Property Advisors

  41 Cobbs Hill Rd, Chilmark, MA 02535
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  /28

  Est $1,287,619 Not Listed For Sale

  • 4 Beds
  • 2 Baths
  • 1,536 Sq Ft

  175 Oak Ln, Vineyard Haven, MA 02568

  175 Oak Ln, Vineyard Haven, MA 02568
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  /37

  $1,195,000

  • 4 Beds
  • 2 Baths
  • 2,059 Sq Ft

  4 Rock Pond Rd, Vineyard Haven, MA 02568

  4 Bedroom ++ home, has room for your family and your in-home business. This is the home that has it all. An abundance of light, space and potential. A large Atrium off the living room invites in the light and warmth of outside, creating an oasis of possibilities-The expansive open living-kitchen-dining area has space for all to gather, the wood stove and kitchen bringing warmth and sunlight

  Kerry Quinlan-Potter Breakwater MV

  4 Rock Pond Rd, Vineyard Haven, MA 02568
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  /43

  $2,100,000 Sold Nov 25, 2025

  6 Tabor Hills, Chilmark, MA 02535

  • 4 Beds
  • 3 Baths
  • 1,968 Sq Ft
  • Built 1993

  Last Sold Summary

  • 11% Below List Price
  • $1,067/SF
  • 50 Days On Market

  Last Listing Agent Dawn Bellante Sandpiper Realty Inc

  6 Tabor Hills, Chilmark, MA 02535
• 

  

  /23

  Est $1,901,859 Not Listed For Sale

  • 5 Beds
  • 2.5 Baths
  • 3,026 Sq Ft

  171 Otis Bassett Rd, Vineyard Haven, MA 02568

  171 Otis Bassett Rd, Vineyard Haven, MA 02568
• 

  

  /40

  $2,995,000

  • 4 Beds
  • 3.5 Baths
  • 2,515 Sq Ft

  300 North Rd, Chilmark, MA 02535

  Winding tree lined driveway off North Rd brings you to this commanding, custom designed residence built by a top tier island builder. This home is set on over 4 private acres of rolling meadows and big sky views. Main living space is all on one level which includes primary bedroom with en-suite bath, large living area with fireplace, bright sunroom or second living room, custom kitchen and two

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

  300 North Rd, Chilmark, MA 02535

Showing Results 121 - 160, Page 4 of 18