Oak Bluffs, MA Homes

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  $2,725,000

  • Land
  • 7.6 Acres
  • $358,553 per Acre

  34 Ebens Ln Unit 20 and 22, Chilmark, MA 02535

  This rare two-lot offering off Middle Road in Chilmark presents a private sanctuary abutting approximately 50 acres of conservation land. The gently rolling landscape is accented by ancient stone walls and striking glacial boulders, creating a setting of timeless Vineyard character. Ideal for a generational compound or two distinct residences, the property offers both serenity and convenience —

  Peyton Wallace Studio Realty

  34 Ebens Ln Unit 20 and 22, Chilmark, MA 02535
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  $19,000 total monthly price

  • 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
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  $1,250,000 Sold Nov 12, 2025

  1054 State Rd, Vineyard Haven, MA 02568

  • 6 Beds
  • 2 Baths
  • 1,845 Sq Ft
  • Built 1881

  Last Sold Summary

  • 16% Below List Price
  • $678/SF
  • 60 Days On Market

  Last Listing Agent Stephanie Roache Donnelly + Co.

  1054 State Rd, Vineyard Haven, MA 02568
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  Est $1,179,160 Not Listed For Sale

  • 4 Beds
  • 2 Baths
  • 1,780 Sq Ft

  16 Rock Pond Rd, Vineyard Haven, MA 02568

  16 Rock Pond Rd, Vineyard Haven, MA 02568
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  $1,900,000

  • 4 Beds
  • 3 Baths
  • 2,056 Sq Ft

  20 Brook Hollow Rd, Vineyard Haven, MA 02568

  This spacious custom designed home is well sited to offer maximum privacy in the lush area of Long View. A short bike ride to Lambert's Cove beach, it's also about a 20-minute walk down a quiet private road. The home lays out well for family and extended guests with a roomy living room boasting vaulted ceilings and large windows. The house is designed to have an intimate relationship with the

  Jim Feiner Feiner Real Estate

  20 Brook Hollow Rd, Vineyard Haven, MA 02568
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  $32,000 total monthly price

  • 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
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  $990,000 Sold Feb 19, 2025

  5 Rock Pond Rd, Vineyard Haven, MA 02568

  • 3 Beds
  • 2 Baths
  • 1,618 Sq Ft
  • Built 1999

  Last Sold Summary

  • 14% Below List Price
  • $612/SF
  • 145 Days On Market

  Current Estimated Value $1,051,364

  Last Listing Agent Kerry Quinlan-Potter Breakwater MV

  5 Rock Pond Rd, Vineyard Haven, MA 02568
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  Est $3,136,932 Not Listed For Sale

  • 6 Beds
  • 3.5 Baths
  • 3,440 Sq Ft

  8 Coffins Field Rd, Edgartown, MA 02539

  8 Coffins Field Rd, Edgartown, MA 02539
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  $1,449,000 Pending

  • Land
  • 3.9 Acres
  • $371,538 per Acre

  34 Ebens Ln, Chilmark, MA 02535

  Settled high on a peaceful ridge this 3.9-acre property is being offered with a long-term lease for 2.5 acres of prime restricted agricultural farmland abutting the property and the Tiasquam River. With the river running along the edge of the property this area is ideal for growing flowers, vegetables, and/or arbors. The land may also be used for grazing and housing livestock along with any

  Thomas Wallace Wallace & Co. Sotheby's

  34 Ebens Ln, Chilmark, MA 02535
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  $50,700 total monthly price

  • 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
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  $1,600,000 Sold Feb 04, 2025

  493 South Rd, Chilmark, MA 02535

  • Land
  • 3.6 Acres
  • $444,444 per Acre

  Last Sold Summary

  • 0 Days On Market

  Last Listing Agent Julianna Flanders Flanders Real Estate

  493 South Rd, Chilmark, MA 02535
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  Not Listed For Sale

  • 4 Beds
  • 3.5 Baths
  • 2,092 Sq Ft

  670 State Rd, Vineyard Haven, MA 02568

  670 State Rd, Vineyard Haven, MA 02568
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  /2

  $799,000

  • Land
  • 0.92 Acre
  • $870,181 per Acre

  22 Bramble Path Unit 214, West Tisbury, MA 02568

  Flat building lot centrally located in West Tisbury. A perc test has been completed which supports a four bedroom Title Five septic system. It is the Buyers responsibility to install utilities, well and septic.

  Michele Casavant Vineyard Village Realty

  22 Bramble Path Unit 214, West Tisbury, MA 02568
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  $13,200 total monthly price

  • 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
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  $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 $1,626,116

  Last Listing Agent Lisa Da Silva Compass | Point B

  10 Red Pony Rd, West Tisbury, MA 02568
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  /31

  Est $2,285,216 Not Listed For Sale

  • 3 Beds
  • 1.5 Baths
  • 1,386 Sq Ft

  7 the Aerie, Chilmark, MA 02535

  7 the Aerie, Chilmark, MA 02535
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  $19,500,000

  • 7 Beds
  • 5.5 Baths
  • 3,344 Sq Ft

  104 & 111 Old Herring Creek Rd, West Tisbury, MA 02535

  This beautiful 2-parcel compound totals 9.5-acre of land and 600 feet of private Vineyard Sound beach. There is a renovated 4-bedroom beach cottage on one of the parcels which includes all modern amenities and offers spectacular views from almost every room. The second parcel has an older 3-bedroom home located high on a ridge. Both parcels offer wonderful walking paths to the sandy beach below.

  Thomas Leclair Landvest MV

  104 & 111 Old Herring Creek Rd, West Tisbury, MA 02535
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  $22,000 total monthly price

  • 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
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  $1,150,000 Sold Jan 15, 2025

  1 Rock Pond Rd, Vineyard Haven, MA 02568

  • 4 Beds
  • 2 Baths
  • 1,818 Sq Ft
  • Built 1999

  Last Sold Summary

  • $633/SF
  • 0 Days On Market

  Current Estimated Value $1,178,762

  Last Listing Agent LINK Email Cache LINK

  1 Rock Pond Rd, Vineyard Haven, MA 02568
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  Est $2,445,864 Not Listed For Sale

  • 4 Beds
  • 3.5 Baths
  • 2,791 Sq Ft

  225 Great Plains Rd, Vineyard Haven, MA 02568

  225 Great Plains Rd, Vineyard Haven, MA 02568
• 

  

  /23

  $6,500,000

  • 6 Beds
  • 5.5 Baths
  • 4,753 Sq Ft

  16 Red Coat Hill Rd, Vineyard Haven, MA 02568

  Private West Tisbury Oasis – Modern Luxury on 4.85 AcresBuilt by the highly regarded Novo Builds and designed by acclaimed architect Zander Auerbach, this newly constructed estate in the heart of West Tisbury offers the perfect blend of architectural sophistication, privacy, and resort-style amenities. Set on 4.85 acres, the main residence spans 3,806 square feet with an additional

  Joe & Nicole Holland Vineyard Dream Realty LLC

  16 Red Coat Hill Rd, Vineyard Haven, MA 02568
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  /20

  $16,800 total monthly price

  • 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
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  $1,650,000 Sold Jan 07, 2025

  3 Danls Way, Vineyard Haven, MA 02568

  • 3 Beds
  • 2 Baths
  • 2,146 Sq Ft
  • Built 1982

  Last Sold Summary

  • 28% Below List Price
  • $769/SF
  • 202 Days On Market

  Current Estimated Value $1,815,727

  Last Listing Agent Marilyn Moses Ocean Park Realty Inc

  3 Danls Way, Vineyard Haven, MA 02568
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  Est $1,631,068 Not Listed For Sale

  • 3 Beds
  • 2 Baths
  • 1,452 Sq Ft

  84 Christiantown Rd, Vineyard Haven, MA 02568

  84 Christiantown Rd, Vineyard Haven, MA 02568
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  $4,950,000

  • 5 Beds
  • 4.5 Baths
  • 3,413 Sq Ft

  124 Old Farm Rd Unit 122, 116, Chilmark, MA 02535

  An incomparable setting in Chilmark, a beautifully renovated 5-bedroom home, stunning landscape and hardscape, all on three separate building lots totaling almost 14 acres - this is Allerton farm. The historic house has been expanded with new additions to create a thoroughly modern residence that nevertheless retains a charm that could not be achieved without technical expertise, attention to

  Mark Jenkins Wallace & Co. Sotheby's International Realty

  124 Old Farm Rd Unit 122, 116, Chilmark, MA 02535
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  $40,000 total monthly price

  • 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
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  $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 $1,233,069

  Last Listing Agent Lisa Gilberto C McManus Realty Group

  46 Old Coach Rd, Vineyard Haven, MA 02568
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  Est $2,282,590 Not Listed For Sale

  • 6 Beds
  • 3.5 Baths
  • 2,705 Sq Ft

  9 Heather Trail, Vineyard Haven, MA 02568

  9 Heather Trail, Vineyard Haven, MA 02568
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  /7

  $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-Holand Sandpiper Realty

  47 Quenames Rd, Chilmark, MA 02535
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  /35

  $22,000 total monthly price

  • 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
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  $900,000 Sold Sep 17, 2025

  45 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

  45 Quenames Rd Unit 30-02, Chilmark, MA 02535
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  /26

  Est $2,032,807 Not Listed For Sale

  • 3 Beds
  • 2 Baths
  • 1,862 Sq Ft

  82 South Rd, Chilmark, MA 02535

  82 South Rd, Chilmark, MA 02535
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  /36

  $4,950,000

  • 5 Beds
  • 4 Baths
  • 3,413 Sq Ft

  122 Old Farm Rd, Chilmark, MA 02535

  An incomparable setting in Chilmark, a beautifully renovated 5-bedroom home, stunning landscape and hardscape, all on three separate building lots totaling almost 14 acres - this is Allerton farm. The historic house has been expanded with new additions to create a thoroughly modern residence that nevertheless retains a charm that could not be achieved without technical expertise, attention to

  Mark Jenkins Wallace & Co. Sotheby's

  122 Old Farm Rd, Chilmark, MA 02535
• 

  

  /19

  $24,000 total monthly price

  • 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
• 

  

  /17

  $1,300,000 Sold Mar 03, 2025

  22 Briarwood Ln, Vineyard Haven, MA 02568

  • 2 Beds
  • 2 Baths
  • 1,241 Sq Ft
  • Built 2018

  Last Sold Summary

  • 4% Below List Price
  • $1,048/SF
  • 4 Days On Market

  Current Estimated Value $1,161,794

  Last Listing Agent Carol Shore Donnelly + Co

  22 Briarwood Ln, Vineyard Haven, MA 02568
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  Est $1,890,232 Not Listed For Sale

  • 4 Beds
  • 2.5 Baths
  • 2,461 Sq Ft

  29 Brook Hollow Rd, Vineyard Haven, MA 02568

  29 Brook Hollow Rd, Vineyard Haven, MA 02568
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  $1,650,000

  • 4 Beds
  • 2.5 Baths
  • 1,815 Sq Ft

  105 Stoney Hill Rd, Vineyard Haven, MA 02568

  Welcome to 105 Stoney Hill Road, a serene retreat tucked in the heart of West Tisbury. This inviting Vineyard property combines comfort, thoughtful design, and practical amenities across 1,815 square feet of living space. The main level welcomes you with soaring ceilings and a natural flow. The living room features engineered hickory plank hardwood, while pine flooring carries warmth throughout

  Lisa Da Silva Compass | Point B

  105 Stoney Hill Rd, Vineyard Haven, MA 02568
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  $36,000 total monthly price

  • 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
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  /2

  $60,000 Sold Jul 01, 2025

  0 North Rd Unit 40 43533, Aquinnah, MA 02535

  • Land
  • 0 Acre

  Last Sold Summary

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

  0 North Rd Unit 40 43533, Aquinnah, MA 02535
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  /16

  Est $1,260,734 Not Listed For Sale

  • 3 Beds
  • 1.5 Baths
  • 1,150 Sq Ft

  31 Music St, Vineyard Haven, MA 02568

  31 Music St, Vineyard Haven, MA 02568

Showing Results 41 - 80, Page 2 of 18