4,283

Oak Bluffs, MA Homes

Section Image
  • 11 By the Woods, Chilmark, MA 02535
    11 By the Woods, Chilmark, MA 02535
    11 By the Woods, Chilmark, MA 02535
    /35

    $2,850,000

    • 4 Beds
    • 3 Baths
    • 2,967 Sq Ft

    11 By the Woods, Chilmark, MA 02535

    Dreamlike Chilmark retreat on 4.5+/- acres overlooking the Chilmark Pond & Atlantic Ocean beyond. Uniquely designed with European and medieval history in mind. The House has 3 bedrooms, 3 bathrooms, an atrium dining area, a two-story library, a kitchen, and a pantry/wet bar. Charming garden and plantings surround the home.A must-see to appreciate all the special touches throughout the Main

    Julianna Flanders Flanders Real Estate

    11 By the Woods, Chilmark, MA 02535
  • 40 Sweet William Way, West Tisbury, MA 02575
    40 Sweet William Way, West Tisbury, MA 02575
    40 Sweet William Way, West Tisbury, MA 02575
    /42

    $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
  • 37 Vineyard Meadow Farms Rd, West Tisbury, MA 02568
    37 Vineyard Meadow Farms Rd, West Tisbury, MA 02568
    /2

    $1,700,000 Sold Oct 20, 2025

    • 1,803 Sq Ft
    • $943/SF
    • 0 Days On Market
    • 5 Beds
    • 3 Baths
    • Built 1982

    37 Vineyard Meadow Farms Rd, West Tisbury, MA 02568

    Not Listed in LINK

    LINK Email Cache LINK

    37 Vineyard Meadow Farms Rd, West Tisbury, MA 02568
    • 8 Coffins Field Rd, Edgartown, MA 02539
      8 Coffins Field Rd, Edgartown, MA 02539
      8 Coffins Field Rd, Edgartown, MA 02539
      /48

      Est $2,869,894 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
  • 55 Old House Way, West Tisbury, MA 02575
    55 Old House Way, West Tisbury, MA 02575
    55 Old House Way, West Tisbury, MA 02575
    /65

    $2,690,000

    • 6 Beds
    • 4 Baths
    • 2,618 Sq Ft

    55 Old House Way, West Tisbury, MA 02575

    Lambert’s Cove/West Tisbury- custom-built contemporary farmhouse style. 4 bedrooms & 3 bathrooms in Main & 2 bedrooms & 1 bath Guest Cottage on 3 acres in a private neighborhood. Enter Main house from the covered porch -matching custom arch doors lead you to either the mudroom/laundry room-kitchen entry, or the living room. The kitchen has Mexican tiled floor & granite counters with

    Leslie Graham Anchor Realty of Martha's Vineyard

    55 Old House Way, West Tisbury, MA 02575
  • 37 Mempremagog Ave Vh410, Tisbury, MA 02568
    37 Mempremagog Ave Vh410, Tisbury, MA 02568
    37 Mempremagog Ave Vh410, Tisbury, MA 02568
    /28

    $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
  • 49 Cobbs Hill Rd Unit 24.3, Chilmark, MA 02535
    49 Cobbs Hill Rd Unit 24.3, Chilmark, MA 02535
    49 Cobbs Hill Rd Unit 24.3, Chilmark, MA 02535
    /9

    $1,500,000 Sold Oct 20, 2025

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

    49 Cobbs Hill Rd Unit 24.3, Chilmark, MA 02535

    3.9-acre parcel in a very distinguished Chilmark neighborhood. The property comes with deeded access to Tisbury Great Pond via the boat landing just 1/3 of a mile away. From there the Atlantic Ocean is just a boat ride away.

    Mark Jenkins Wallace & Co. Sotheby's

    49 Cobbs Hill Rd Unit 24.3, Chilmark, MA 02535
    • 670 State Rd, Vineyard Haven, MA 02568
      670 State Rd, Vineyard Haven, MA 02568
      670 State Rd, Vineyard Haven, MA 02568
      /49

      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
  • 20 Brook Hollow Rd, Vineyard Haven, MA 02568
    20 Brook Hollow Rd, Vineyard Haven, MA 02568
    20 Brook Hollow Rd, Vineyard Haven, MA 02568
    /50

    $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
  • 6 Trails End Ch241, Chilmark, MA 02535
    6 Trails End Ch241, Chilmark, MA 02535
    6 Trails End Ch241, Chilmark, MA 02535
    /26

    $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
  • 0 Quansoo Beach Lot Unit 50 43710, Chilmark, MA 02535
    0 Quansoo Beach Lot Unit 50 43710, Chilmark, MA 02535
    0 Quansoo Beach Lot Unit 50 43710, Chilmark, MA 02535
    /16

    $475,000 Sold Oct 20, 2025

    • Land
    • 0 Acre
    • 11 Days On Market

    0 Quansoo Beach Lot Unit 50 43710, Chilmark, MA 02535

    Spectacular beach lot at Quansoo. This is the ultimate amenity. Ownership provides access to one of the most stunning beaches on the entire eastern seaboard. On one side is the majestic Atlantic Ocean and on the other the calm waters of Tisbury Great Pond where kids can catch crabs and play safely as you watch. Skip the lines and crowds at other beaches - come and go as you please for sun, sand,

    Mark Jenkins Wallace & Co. Sotheby's

    0 Quansoo Beach Lot Unit 50 43710, Chilmark, MA 02535
    • 4 Tilton Rd, Chilmark, MA 02535
      4 Tilton Rd, Chilmark, MA 02535
      4 Tilton Rd, Chilmark, MA 02535
      /75

      Est $3,405,343 Not Listed For Sale

      • 4 Beds
      • 2 Baths
      • 1,362 Sq Ft

      4 Tilton Rd, Chilmark, MA 02535

      4 Tilton Rd, Chilmark, MA 02535
  • 34 Ebens Ln Unit 20 and 22, Chilmark, MA 02535
    34 Ebens Ln Unit 20 and 22, Chilmark, MA 02535
    34 Ebens Ln Unit 20 and 22, Chilmark, MA 02535
    /21

    $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
  • 224 N Rd Ch248, Chilmark, MA 02535
    224 N Rd Ch248, Chilmark, MA 02535
    224 N Rd Ch248, Chilmark, MA 02535
    /3

    $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
  • 32 MacHipscat Trail, Vineyard Haven, MA 02568
    32 MacHipscat Trail, Vineyard Haven, MA 02568
    32 MacHipscat Trail, Vineyard Haven, MA 02568
    /19

    $1,330,000 Sold Oct 17, 2025

    • 1,404 Sq Ft
    • $947/SF
    • 112 Days On Market
    • 3 Beds
    • 1.5 Baths
    • Built 1983

    32 MacHipscat Trail, Vineyard Haven, MA 02568

    This Cape Style home privately sited on 1.89 acres at the end of a cul-de-sac abutting conservation land with many walking trails. Nice features include spacious living spaces that include a well equipped kitchen with custom cherry cabinets, dining room, living room with fireplace, wood stove and french doors that lead you out to a private patio and backyard. Second floor offers two guest

    Brenda Galligan Karen M. Overtoom R.E.

    32 MacHipscat Trail, Vineyard Haven, MA 02568
    • 7 the Aerie, Chilmark, MA 02535
      7 the Aerie, Chilmark, MA 02535
      7 the Aerie, Chilmark, MA 02535
      /31

      Est $2,241,450 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
  • 25 Coffins Field Rd, Edgartown, MA 02539
    25 Coffins Field Rd, Edgartown, MA 02539
    25 Coffins Field Rd, Edgartown, MA 02539
    /4

    $1,100,000

    • Land
    • 1 Acre
    • $1,100,000 per Acre

    25 Coffins Field Rd, Edgartown, MA 02539

    3 bedroom or 1 bedroom per 15,000 sq ft whichever is greater

    Casandra Hyland Landmarks at TODAY Real Estate

    25 Coffins Field Rd, Edgartown, MA 02539
  • 2 Strikers Way Ch211, Chilmark, MA 02535
    2 Strikers Way Ch211, Chilmark, MA 02535
    2 Strikers Way Ch211, Chilmark, MA 02535
    /33

    $22,000 total monthly price

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

    2 Strikers Way Ch211, 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. 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

    Karen Overtoom Karen M. Overtoom R.E.

    2 Strikers Way Ch211, Chilmark, MA 02535
  • 251 State Rd, Vineyard Haven, MA 02568
    251 State Rd, Vineyard Haven, MA 02568
    251 State Rd, Vineyard Haven, MA 02568
    /30

    $1,550,000 Sold Oct 16, 2025

    • 1,986 Sq Ft
    • $780/SF
    • 114 Days On Market
    • 3 Beds
    • 2 Baths
    • Built 1986

    251 State Rd, Vineyard Haven, MA 02568

    This private and pastoral year-round home with fine craftsmanship and loads of character is a classic up-island refuge, yet in a location that is central on the island and convenient to town. Abutting Land Bank property, the charming home features an open living and dining room with wide plank floors and beams flowing into the kitchen, all surrounding a central brick fireplace. An expansive

    Meg Bodnar Tea Lane Associates

    251 State Rd, Vineyard Haven, MA 02568
    • 225 Great Plains Rd, Vineyard Haven, MA 02568
      225 Great Plains Rd, Vineyard Haven, MA 02568
      225 Great Plains Rd, Vineyard Haven, MA 02568
      /36

      Est $2,466,989 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
  • 25 Coffins Field Rd Unit 18, Edgartown, MA 02539
    25 Coffins Field Rd Unit 18, Edgartown, MA 02539
    25 Coffins Field Rd Unit 18, Edgartown, MA 02539
    /13

    $1,100,000 Open House 12/11

    • Land
    • 1 Acre
    • $1,100,000 per Acre

    25 Coffins Field Rd Unit 18, Edgartown, MA 02539

    One-Acre Lot in a Peaceful Edgartown Neighborhood. Build your island dream home on this spacious one acre lot, nestled in a quiet, centrally located Edgartown neighborhood. Enjoy the best of both worlds-a tranquil setting that's just minutes from town, beaches, and all the Vineyard's favorite spots.This 3-bedroom lot offers excellent potential. Per the Board of Health, an enhanced septic

    Casandra Hyland Landmarks at TODAY Real Estate

    25 Coffins Field Rd Unit 18, Edgartown, MA 02539
  • 31 S Ridge Rd Ch218, Chilmark, MA 02535
    31 S Ridge Rd Ch218, Chilmark, MA 02535
    31 S Ridge Rd Ch218, Chilmark, MA 02535
    /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
  • 25 Osprey Ln, Chilmark, MA 02535
    25 Osprey Ln, Chilmark, MA 02535
    25 Osprey Ln, Chilmark, MA 02535
    /37

    $7,289,000 Sold Oct 15, 2025

    • 3,777 Sq Ft
    • $1,930/SF
    • 77 Days On Market
    • 4 Beds
    • 5 Baths
    • Built 1988

    25 Osprey Ln, Chilmark, MA 02535

    Spectacular views from one of the most sought after private enclaves on Chilmark's South Shore. This lovely home was built to take advantage of this magical location. Just steps to the shared dock on the shores of Upper Chilmark Pond and minutes to the extraordinary deeded Atlantic Beach front. The homeowners worked with world renowned architects, Crissman & Solomon, along with revolutionary

    Deb Hancock Hancock Real Estate

    25 Osprey Ln, Chilmark, MA 02535
    • 84 Christiantown Rd, Vineyard Haven, MA 02568
      84 Christiantown Rd, Vineyard Haven, MA 02568
      84 Christiantown Rd, Vineyard Haven, MA 02568
      /34

      Est $1,535,030 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
  • 25 Vineyard Meadow Farms Rd, West Tisbury, MA 02575
    25 Vineyard Meadow Farms Rd, West Tisbury, MA 02575
    25 Vineyard Meadow Farms Rd, West Tisbury, MA 02575
    /18

    $1,100,000

    • 2 Beds
    • 2 Baths
    • 1,583 Sq Ft

    25 Vineyard Meadow Farms Rd, West Tisbury, MA 02575

    Prime Martha’s Vineyard location! Nestled on 1.4 acres in the sought-after Vineyard Meadow Farms neighborhood, this property offers an exceptional combination of privacy, convenience, and potential. Ideally situated in West Tisbury, close to Edgartown and Vineyard Haven, residents enjoy easy access to local shops, restaurants, and amenities, as well as the island’s most beautiful

    Maranda Post Compass | The O'Hanlon Group

    25 Vineyard Meadow Farms Rd, West Tisbury, MA 02575
  • 384 Middle Rd Ch222, Chilmark, MA 02535
    384 Middle Rd Ch222, Chilmark, MA 02535
    384 Middle Rd Ch222, Chilmark, MA 02535
    /31

    $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
  • 25 N Vine Ln Unit 70.3, West Tisbury, MA 02568
    25 N Vine Ln Unit 70.3, West Tisbury, MA 02568
    25 N Vine Ln Unit 70.3, West Tisbury, MA 02568
    /9

    $900,000 Sold Oct 10, 2025

    • Land
    • 3.73 Acres
    • $241,287 per Acre
    • 462 Days On Market

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

    Resident's of West Tisbury have access to Lambert's Cove Beach by right. Exceptional opportunity in West Tisbury! This 3.73-acre parcel offers peace and privacy on a quiet dead-end road, moments from Sepiessa, Tiah’s Cove, and Long Point. This property is a blank canvas for your MV Dream Home — Possibilities include Main House, Barn, Garage, and possibly more with proper permits. Pool and Pool

    Janna O'Loughlin Portfolio Real Estate, Inc.

    25 N Vine Ln Unit 70.3, West Tisbury, MA 02568
    • 9 Heather Trail, Vineyard Haven, MA 02568
      9 Heather Trail, Vineyard Haven, MA 02568
      9 Heather Trail, Vineyard Haven, MA 02568
      /36

      Est $2,202,915 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
  • 46 Tercel Ln, Chilmark, MA 02535
    46 Tercel Ln, Chilmark, MA 02535
    46 Tercel Ln, Chilmark, MA 02535
    /17

    $1,650,000

    • 2 Beds
    • 1 Bath
    • 716 Sq Ft

    46 Tercel Ln, Chilmark, MA 02535

    Nestled on a serene 3.32-acre parcel between North Road and Tabor House in Chilmark, this property blends privacy, charm, and great potential. A sweet 2 bedroom guest house--beautifully maintained and offering excellent rental income--sits amid rolling stone walls and mature trees, creating a peaceful woodland setting. Recent updates include a new roof, siding, and HVAC system, ensuring comfort

    Stacy Ickes Donnelly + Co.

    46 Tercel Ln, Chilmark, MA 02535
  • 36 Henry Hough Lane Ch206, Chilmark, MA 02535
    36 Henry Hough Lane Ch206, Chilmark, MA 02535
    36 Henry Hough Lane Ch206, Chilmark, MA 02535
    /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
  • 24 Alex Way, Vineyard Haven, MA 02568
    24 Alex Way, Vineyard Haven, MA 02568
    24 Alex Way, Vineyard Haven, MA 02568
    /34

    $2,175,000 Sold Oct 10, 2025

    • 2,879 Sq Ft
    • $755/SF
    • 89 Days On Market
    • 3 Beds
    • 2.5 Baths
    • Built 1985

    24 Alex Way, Vineyard Haven, MA 02568

    24 Alex Way is an opportunity to embrace the extraordinary Elias and Langmuir legacy which dramatically changed a 140 acre rural West Tisbury landscape in 1972 into the Nat's Farm community of 26 home sites. The home overlooks the 56 acres that Nat's Farm donated to Sheriff's Meadow Foundation and the incomparable Misty Meadows Equine Learning Center and homes along Elias Lane. Jane Langmuir,

    Elissa Lash Tea Lane Associates

    24 Alex Way, Vineyard Haven, MA 02568
    • 29 Brook Hollow Rd, Vineyard Haven, MA 02568
      29 Brook Hollow Rd, Vineyard Haven, MA 02568
      29 Brook Hollow Rd, Vineyard Haven, MA 02568
      /18

      Est $1,717,310 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
  • 46 Tiercel Ln, Chilmark, MA 02535
    46 Tiercel Ln, Chilmark, MA 02535
    46 Tiercel Ln, Chilmark, MA 02535
    /20

    $1,650,000

    • 2 Beds
    • 1 Bath
    • 716 Sq Ft

    46 Tiercel Ln, Chilmark, MA 02535

    Nestled on a serene 3.32-acre parcel between North Road and Tabor House in Chilmark, this property blends privacy, charm, and great potential. A sweet 2 bedroom guest house—beautifully maintained and offering excellent rental income—sits amid rolling stone walls and mature trees, creating a peaceful woodland setting.Recent updates include a new roof, siding, and HVAC system, ensuring

    Stacy Ickes Donnelly + Co

    46 Tiercel Ln, Chilmark, MA 02535
  • 44 Flanders Ln, Chilmark, MA 02535
    44 Flanders Ln, Chilmark, MA 02535
    44 Flanders Ln, 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
  • 25 N Vine Ln, West Tisbury, MA 02568
    25 N Vine Ln, West Tisbury, MA 02568
    25 N Vine Ln, West Tisbury, MA 02568
    /12

    $900,000 Sold Oct 10, 2025

    • Land
    • 3.83 Acres
    • $234,987 per Acre
    • 458 Days On Market

    25 N Vine Ln, West Tisbury, MA 02568

    Exceptional opportunity in West Tisbury! This 3.73-acre parcel offers peace and privacy on a quiet dead-end road, moments from Sepiessa, Tiah's Cove, and Long Point beaches. This property is a blank canvas for your MV Dream Home -- Possibilities include Main House, Guest House, Barn, Garage, and more with proper permits. Pool/Pool House possible by special permit. Electric, phone, and cable on

    Janna O'Loughlin Portfolio Properties

    25 N Vine Ln, West Tisbury, MA 02568
    • 31 Music St, Vineyard Haven, MA 02568
      31 Music St, Vineyard Haven, MA 02568
      31 Music St, Vineyard Haven, MA 02568
      /16

      Est $1,178,414 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
  • 105 Stoney Hill Rd, Vineyard Haven, MA 02568
    105 Stoney Hill Rd, Vineyard Haven, MA 02568
    105 Stoney Hill Rd, Vineyard Haven, MA 02568
    /44

    $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
  • 29 Cemetery Rd Ch216, Chilmark, MA 02535
    29 Cemetery Rd Ch216, Chilmark, MA 02535
    29 Cemetery Rd Ch216, Chilmark, MA 02535
    /32

    $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
  • 51 Skiffs Ln, Vineyard Haven, MA 02568
    51 Skiffs Ln, Vineyard Haven, MA 02568
    51 Skiffs Ln, Vineyard Haven, MA 02568
    /45

    $1,700,000 Sold Oct 08, 2025

    • 3,213 Sq Ft
    • $529/SF
    • 52 Days On Market
    • 7 Beds
    • 4.5 Baths
    • Built 1979

    51 Skiffs Ln, Vineyard Haven, MA 02568

    Roomy, 5 bedroom, 3.5 bath home warmed by walls of knotty pine and sited on a 3-acre parcel with nicely cleared areas around the house bringing in the sunlight and enticing you outside for games, gardening and relaxation on the expansive deck. There is a wood-burning brick fireplace in the living room to gather around on chilly nights - and a full, dry basement great for kids games on rainy days

    Candy DaRosa Feiner Real Estate

    51 Skiffs Ln, Vineyard Haven, MA 02568
    • 10 Briarwood Ln, Vineyard Haven, MA 02568
      10 Briarwood Ln, Vineyard Haven, MA 02568
      10 Briarwood Ln, Vineyard Haven, MA 02568
      /17

      Est $1,085,887 Not Listed For Sale

      • 3 Beds
      • 2 Baths
      • 934 Sq Ft

      10 Briarwood Ln, Vineyard Haven, MA 02568

      10 Briarwood Ln, Vineyard Haven, MA 02568

Showing Results 41 - 80, Page 2 of 18

Massachusetts Dukes County Oak Bluffs

Real Estate & Homes

How to Buy a Home How to Finance a Home How to Sell a Home

Find More Real Estate & Homes for Sale by State

Top Cities with Homes For Sale

Top Counties with Homes For Sale

More Real Estate For Sale Near Me

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