Vineyard Haven, MA Homes

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  $5,325,000

  • 6 Beds
  • 4 Baths
  • 2,890 Sq Ft

  4 Canonicus Ave, Oak Bluffs, MA 02557

  With a striking presence overlooking Nantucket Sound and just moments from the vibrant pulse of downtown, this distinctive compound is infused with a laid-back West Coast spirit while honoring the vintage charm of Oak Bluffs. Airy and effortlessly elegant, the four-bedroom main house has been masterfully updated, introducing refined, contemporary comforts, designed for every season. Tucked to the

  Katherine Donahue Sandpiper Realty Inc

  4 Canonicus Ave, Oak Bluffs, MA 02557
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  /8

  $6,000 total monthly price

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

  33 Kennebago Ave Vh414, Tisbury, MA 02568

  THIS PROPERTY IS A WEEKLY RENTAL PROPERTY!! This beautiful home has lots of open space for cooking, yard activities or just plain relaxing. Private association beach overlooking the Elizabethan Islands. Plan a sunset picnic on the beach or plan in the morning to see the rays of sun break on the water.

  Karen Overtoom Karen M. Overtoom R.E.

  33 Kennebago Ave Vh414, Tisbury, MA 02568
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  $1,050,000 Sold Jun 30, 2025

  160 Bernard Cir, Vineyard Haven, MA 02568

  • 4 Beds
  • 2 Baths
  • 1,606 Sq Ft
  • Built 1977

  Last Sold Summary

  • 12% Below List Price
  • $654/SF
  • 45 Days On Market

  Current Estimated Value $1,091,009

  Last Listing Agent Dawn Bellante-Holand Sandpiper Realty

  160 Bernard Cir, Vineyard Haven, MA 02568
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  Est $1,013,552 Not Listed For Sale

  • 2 Beds
  • 1 Bath
  • 1,024 Sq Ft

  51 Manchester Ave, Vineyard Haven, MA 02568

  51 Manchester Ave, Vineyard Haven, MA 02568
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  /14

  $835,000

  • 2 Beds
  • 1 Bath
  • 768 Sq Ft

  51 Lantern Ln, Vineyard Haven, MA 02568

  Find your sweet spot in this charming starter home, ideally located on a quiet street yet within an effortless walk of everything. Forget the car and get your steps in! You're a short jaunt to essentials like Cronig's Market and Shirley's Hardware, AND local favorites including The Maker, Black Dog Cafe, Island Fresh Pizza, Pie Chicks, and Island Adventures Mini Golf. Also within walking distance

  Idalyn Macchia Gilstad Wallace & Co. Sotheby's International Realty

  51 Lantern Ln, Vineyard Haven, MA 02568
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  /12

  $15,000 total monthly price

  • 5 Beds
  • 6.5 Baths
  • 4,137 Sq Ft
  • House for Rent

  41 Naushon Rd Wt116, Aquinnah, MA 02575

  Stunning water views from this expansive beachfront estate in Makonikey off Lambert's Cove Rd. Enjoy the large living area with comfortable couches, floor to ceiling windows and french doors for seamless indoor to outdoor living and dining. There is a fully equipped kitchen. Some folks will enjoy the treadmill and elliptical while watching boats pass by or even play squash in the indoor squash

  Karen Overtoom Karen M. Overtoom R.E.

  41 Naushon Rd Wt116, Aquinnah, MA 02575
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  /21

  $982,000 Sold Dec 19, 2025

  25 Windy Hill Rd, Oak Bluffs, MA 02557

  • 3 Beds
  • 1 Bath
  • 980 Sq Ft
  • Built 1971

  Last Sold Summary

  • 1% Below List Price
  • $1,002/SF
  • 10 Days On Market

  Last Listing Agent Rene Jackson Island Real Estate

  25 Windy Hill Rd, Oak Bluffs, MA 02557
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  /25

  Est $2,104,866 Not Listed For Sale

  • 5 Beds
  • 3 Baths
  • 3,636 Sq Ft

  131 Shubael Weeks Path, Vineyard Haven, MA 02568

  131 Shubael Weeks Path, Vineyard Haven, MA 02568
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  /15

  $625,000

  • 2 Beds
  • 1 Bath
  • 704 Sq Ft

  124 Skiff Ave Unit C-12, Vineyard Haven, MA 02568

  MOVE RIGHT IN! This sunny end unit is being offered furnished! Spacious living area opens to an eat-in kitchen with a new Bosch dishwasher. Bedroom number one has a queen bed. Bedroom two has two single beds. Conveniently located within close proximity to Main Street shops, the ferry and bus terminal, and the scenic bike path that extends across the island. At the bottom of the hill you will find

  Rene Jackson Island Real Estate

  124 Skiff Ave Unit C-12, Vineyard Haven, MA 02568
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  $18,500 total monthly price

  • 4 Beds
  • 3.5 Baths
  • 1,714 Sq Ft
  • House for Rent

  4 Windy Way Wt143, West Tisbury, MA 02575

  THIS PROPERTY IS A WEEKLY RENTAL PROPERTY!! The 3.3 acre private setting is most picturesque with its positioning in private Upper Makonikey , the long circular driveway , its grassy lawn, and rolling landscape fields . Only a short distance away is over 3,000 feet of PRIVATE sandy association Beaches , directly below , with two nearby parking lot access-ways . Nestled onto this promontory is a

  Karen Overtoom Karen M. Overtoom R.E.

  4 Windy Way Wt143, West Tisbury, MA 02575
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  /4

  $1,350,000 Sold Aug 15, 2025

  35 Vineyard Avenue Extension, Oak Bluffs, MA 02568

  • 3 Beds
  • 2 Baths
  • 1,864 Sq Ft
  • Built 1970

  Last Sold Summary

  • 7% Below List Price
  • $724/SF
  • 12 Days On Market

  Last Listing Agent Lesley Heidt Sandpiper Realty Inc

  35 Vineyard Avenue Extension, Oak Bluffs, MA 02568
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  /2

  Est $1,809,681 Not Listed For Sale

  • 3 Beds
  • 2.5 Baths
  • 2,102 Sq Ft

  26 Old Coach Rd, Vineyard Haven, MA 02568

  26 Old Coach Rd, Vineyard Haven, MA 02568
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  $1,193,000

  • 3 Beds
  • 1.5 Baths
  • 1,040 Sq Ft

  50 Lantern Ln, Vineyard Haven, MA 02568

  *NOTE: The seller is offering a $25,000 credit towards the required septic upgrade. Nestled in a quiet enclave on Lantern Lane, this charming 3-bedroom, 2-bath home offers the perfect blend of comfort, convenience, and island charm. Located just moments from the heart of Vineyard Haven, you'll enjoy easy access to shops, restaurants, and the ferry. The interior of the home features a bright and

  Madelyn Silvia Wallace & Co. Sotheby's International Realty

  50 Lantern Ln, Vineyard Haven, MA 02568
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  $4,800 total monthly price

  • 3 Beds
  • 3 Baths
  • 3,279 Sq Ft
  • House for Rent

  165 Christiantown Rd, West Tisbury, MA 02575

  THIS PROPERTY IS A WEEKLY PROPERTY!! The home is set on six beautifully landscaped acres with original stone walls. It is located in private historic Christiantown on the North Shore, a short distance from both Lambert’s Cove Beach and Cedar Tree Neck Wildlife Reserve. Cedar Tree is a habitat with tumbling streams and freshwater ponds, sandy beaches and rocky cliffs, tall oaks and cool beech

  Karen Overtoom Karen M. Overtoom R.E.

  165 Christiantown Rd, West Tisbury, MA 02575
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  $776,500 Sold Mar 05, 2025

  32 Clark Ave, Vineyard Haven, MA 02568

  • 2 Beds
  • 1 Bath
  • 768 Sq Ft
  • Built 1968

  Last Sold Summary

  • 7% Below List Price
  • $1,011/SF
  • 17 Days On Market

  Current Estimated Value $789,751

  Last Listing Agent Diana Gilmore Island Real Estate

  32 Clark Ave, Vineyard Haven, MA 02568
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  Est $1,789,848 Not Listed For Sale

  • 3 Beds
  • 2.5 Baths
  • 2,576 Sq Ft

  38 Edgewood Dr, Edgartown, MA 02539

  38 Edgewood Dr, Edgartown, MA 02539
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  $1,250,000

  • 3 Beds
  • 2 Baths
  • 1,196 Sq Ft

  112 3rd St N, Edgartown, MA 02568

  Nestled on a lush and private parcel close to The Boulevard, this contemporary three-bedroom, two-bath residence offers the perfect blend of style and comfortable living. Highlights include a gas fireplace, wood floors, an expansive deck to relax on, and established gardens. There’s even a shed to store all your summer gear. Enjoy this oasis as is or use as a foundation for future

  Kristin Buck Donnelly + Co.

  112 3rd St N, Edgartown, MA 02568
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  $18,840 total monthly price

  • 3 Beds
  • 2.5 Baths
  • House for Rent

  21 William St Vh430, Tisbury, MA 02568

  THIS IS A WEEKLY SUMMER RENTAL ONLY.THE WEEKLY PRICE IN AUGUST IS $4,710. PER WEEK.SEE WEB SITE FOR ADDITIONAL WEEKLY PRICING. Lovely elegant home with wonderful art and furnishings. Once you step in the front door you will fall in love with this lovely home. Each room is a delight. Large nicely appointed kitchen with easy access to a beautiful dining room. A formal living room is next to a less

  Karen Overtoom Karen M. Overtoom R.E.

  21 William St Vh430, Tisbury, MA 02568
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  $700,500 Sold May 07, 2025

  72 Windsor Dr Unit 99.71, Edgartown, MA 02539

  • Land
  • 0.55 Acre
  • $1,273,636 per Acre

  Last Sold Summary

  • 3% Above List Price
  • 0 Days On Market

  Last Listing Agent Jim Joyce Carroll & Vincent R.E.

  72 Windsor Dr Unit 99.71, Edgartown, MA 02539
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  /2

  Est $1,388,663 Not Listed For Sale

  • 3 Beds
  • 3 Baths
  • 1,400 Sq Ft

  45 Pine Tree Ln, Vineyard Haven, MA 02568

  45 Pine Tree Ln, Vineyard Haven, MA 02568
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  $849,000

  • 1 Bed
  • 1 Bath
  • 803 Sq Ft

  26 Winthrop Ave, Oak Bluffs, MA 02557

  Hidden behind a wall of vegetation on Winthrop Avenue this is a little 'oasis' of a piece of land. One bedroom house situated on a 1/3 Acre, 14,810 sq.ft. level lot. One side of the property is lush with vegetation and the opposite side is clear. It is one lot in total and may not be subdivided. The existing house has been lived in year round. Only .6 of a mile to Oak Bluffs Harbor and .5 mile

  Alisan Lohan-Conway Alisan Lohan-Conway Properties

  26 Winthrop Ave, Oak Bluffs, MA 02557
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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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  $1,067,000 Sold Sep 26, 2025

  112 W Spring St, Vineyard Haven, MA 02568

  • 3 Beds
  • 2.5 Baths
  • 1,503 Sq Ft
  • Built 2000

  Last Sold Summary

  • 7% Below List Price
  • $710/SF
  • 95 Days On Market

  Current Estimated Value $1,101,318

  Last Listing Agent Katherine Donahue Sandpiper Realty Inc

  112 W Spring St, Vineyard Haven, MA 02568
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  Est $2,360,766 Not Listed For Sale

  • 4 Beds
  • 2.5 Baths
  • 2,436 Sq Ft

  377 State Rd, Vineyard Haven, MA 02568

  377 State Rd, Vineyard Haven, MA 02568
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  $475,000

  • Land
  • 0.52 Acre
  • $913,462 per Acre

  36 Boylston Dr, Edgartown, MA 02539

  Buildable lot in an established Edgartown neighborhood. Approvals are in hand for the construction of a single-family residential structure not to exceed 3 bedrooms and not to exceed 1,850 square feet of heated living area (screened porches, patios, etc are not included in this square footage). Note that this property cannot be used as a seasonal home or short-term rental. Septic plan has been

  Mark Jenkins Wallace & Co. Sotheby's International Realty

  36 Boylston Dr, Edgartown, MA 02539
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  $10,000 total monthly price

  • 3 Beds
  • 1.5 Baths
  • 1,144 Sq Ft
  • House for Rent

  100 Franklin Terrace Vh411, Tisbury, MA 02568

  THIS IS A WEEKLY SUMMER RENTAL ONLY.THE WEEKLY PRICE IN AUGUST IS $2,500. PER WEEK.SEE WEB SITE FOR ADDITIONAL WEEKLY PRICING. This charming 3 bedroom home offers open living, dining and kitchen space that open to a screened-in porch and patio. You are located in a peaceful setting yet with-in walking distance to Lake Tashmoo, town beaches, and the Vineyard Haven Village for dining, shopping and

  Karen Overtoom Karen M. Overtoom R.E.

  100 Franklin Terrace Vh411, Tisbury, MA 02568
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  $1,125,000 Sold Oct 28, 2025

  140 Longview Rd, Vineyard Haven, MA 02568

  • 3 Beds
  • 1.5 Baths
  • 1,432 Sq Ft
  • Built 1964

  Last Sold Summary

  • 13% Below List Price
  • $786/SF
  • 97 Days On Market

  Last Listing Agent Candy DaRosa Feiner Real Estate

  140 Longview Rd, Vineyard Haven, MA 02568
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  Est $2,512,811 Not Listed For Sale

  • 3 Beds
  • 2.5 Baths
  • 1,657 Sq Ft

  21 Old Oklahoma Rd, Vineyard Haven, MA 02568

  21 Old Oklahoma Rd, Vineyard Haven, MA 02568
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  $1,575,000 Pending

  • 5 Beds
  • 3.5 Baths
  • 2,436 Sq Ft

  128 W Spring St, Vineyard Haven, MA 02568

  128 Spring Street—just moments from the Tisbury School and downtown Vineyard Haven. Built in 2013 and sited on an ample 1/4-acre lot, the house features four bedrooms and two-and-a-half bathrooms, along with a separate first floor one-bedroom in-law apartment complete with a full bath—ideal for extended family, guests, or added rental flexibility. The central location offers convenience to

  David Dickinson Compass

  128 W Spring St, Vineyard Haven, MA 02568
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  /25

  $10,800 total monthly price

  • 2 Beds
  • 4 Baths
  • 1,800 Sq Ft
  • House for Rent

  256 Sandpiper Lane Vh417, Tisbury, MA 02568

  THIS IS A WEEKLY SUMMER RENTAL ONLY.THE WEEKLY PRICE IN AUGUST IS $2,700. PER WEEK.SEE WEB SITE FOR ADDITIONAL WEEKLY PRICING. This well appointed condo will make you feel comfortable and at home the moment you walk in. Swimming, kayaking, tennis, walking trails, and shopping are all at your finger tips. Mink Meadows Golf Course is just a stroll down the street as well. Enjoy all the Island has

  Karen Overtoom Karen M. Overtoom R.E.

  256 Sandpiper Lane Vh417, Tisbury, MA 02568
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  $1,865,000 Sold Dec 04, 2025

  71 Netock Ave, Oak Bluffs, MA 02557

  • 4 Beds
  • 5 Baths
  • 2,820 Sq Ft
  • Built 1982

  Last Sold Summary

  • 7% Below List Price
  • $661/SF
  • 11 Days On Market

  Last Listing Agent Ellen Valentgas Sotheby's International Realty

  71 Netock Ave, Oak Bluffs, MA 02557
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  /36

  Est $1,294,940 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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  /20

  $3,495,000

  • 4 Beds
  • 3 Baths
  • 1,696 Sq Ft

  10 Fowler Ave, Edgartown, MA 02539

  Edgartown Waterfront - Enjoy sweeping water views and direct access to Sengekontacket Pond from this beautiful coastal retreat. Completely renovated in 2024, this four-bedroom, three-bath home blends classic Vineyard charm with modern coastal design and offers 95 feet of pond frontage with a private mooring. The open-concept living space is filled with natural light and features Thermador

  Andrew McElhinney Compass LLC

  10 Fowler Ave, Edgartown, MA 02539
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  /15

  $7,500 total monthly price

  • 2 Beds
  • 1 Bath
  • 800 Sq Ft
  • House for Rent

  83 Ashtons Way, Vineyard Haven, MA 02568

  THIS IS A WEEKLY SUMMER RENTAL ONLY.THE WEEKLY PRICE IN AUGUST IS $1,875. PER WEEK.SEE WEB SITE FOR ADDITIONAL WEEKLY PRICING. This two bedroom cottage is set in a private setting in the woods, just a short distance to downtown Vineyard Haven. Sleeps four comfortably, open living space, deck and outside shower. If rented with the main house, access to private association beach and golf would be

  Karen Overtoom Karen M. Overtoom R.E.

  83 Ashtons Way, Vineyard Haven, MA 02568
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  /2

  $2,380,000 Sold Jan 21, 2025

  41 Bold Meadow Rd, Edgartown, MA 02539

  • 4 Beds
  • 3 Baths
  • 2,770 Sq Ft
  • Built 2012

  Last Sold Summary

  • 7% Below List Price
  • $859/SF
  • 94 Days On Market

  Current Estimated Value $2,460,492

  Last Listing Agent Emma Kennedy Sandpiper Realty Inc

  41 Bold Meadow Rd, Edgartown, MA 02539
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  /40

  Est $1,849,834 Not Listed For Sale

  • 4 Beds
  • 2.5 Baths
  • 1 Sq Ft

  179 Main St, Vineyard Haven, MA 02568

  179 Main St, Vineyard Haven, MA 02568
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  $700,000 Pending

  • Land
  • 0.26 Acre
  • $2,738,654 per Acre

  2 Hope's Way Unit 31, Oak Bluffs, MA 02557

  ESTEEMED BUILDER READY to BREAK GROUND! Purchase this exceptional lot in Lagoon Ridge and start designing and building your dream 3BR + home today! Execute a BUILDING CONTRACT or choose your own builder... Call for details and schedule a tour! Welcome to Oak Bluffs’ newest and most sought-after neighborhood, where you can construct your 3-bedroom home on a lofty setting, 95 feet above Lagoon

  Marilyn Moses Ocean Park Realty Inc

  2 Hope's Way Unit 31, Oak Bluffs, MA 02557
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  /34

  $25,000 total monthly price

  • 4 Beds
  • 3.5 Baths
  • 2,334 Sq Ft
  • House for Rent

  100 Connie's Way Vh401, Tisbury, MA 02568

  THIS IS A WEEKLY SUMMER RENTAL ONLY.THE WEEKLY PRICE IN AUGUST IS $6,250. PER WEEK.SEE WEB SITE FOR ADDITIONAL WEEKLY PRICING. Located in Mink Meadows Association, this wonderful four bedroom, three full and one half bath home has many nice features that include a large eat-in kitchen/family room, a more formal living room with fireplace, dining room and den. Televisions in every bedroom, living

  Karen Overtoom Karen M. Overtoom R.E.

  100 Connie's Way Vh401, Tisbury, MA 02568
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  $1,100,000 Sold Jun 27, 2025

  10 Kims Way, Oak Bluffs, MA 02568

  • 4 Beds
  • 2.5 Baths
  • 1,976 Sq Ft
  • Built 1985

  Last Sold Summary

  • 12% Below List Price
  • $557/SF
  • 156 Days On Market

  Last Listing Agent Michael Schweikert Ocean Park Realty, Inc.

  10 Kims Way, Oak Bluffs, MA 02568
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  Est $1,210,459 Not Listed For Sale

  • 4 Beds
  • 2 Baths
  • 1,368 Sq Ft

  29 Dunham Ave, Vineyard Haven, MA 02568

  29 Dunham Ave, Vineyard Haven, MA 02568

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