Vineyard Haven, MA Homes

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  $1,799,000

  • 4 Beds
  • 2.5 Baths
  • 3,268 Sq Ft

  7 Upper Meadow Ln, Oak Bluffs, MA 02557

  Meadowview Farms -- This home is ideal for those who love to host lively gatherings! Set at the end of a quiet cul-de-sac, this spacious Colonial offers over 3,200 sq ft designed for comfortable living and easy entertaining. The home features four bedrooms and 2.5 baths, including a primary suite with walk-in closets and private bath. The main living area flows from a living room with fireplace

  Lesley Heidt Sandpiper Realty Inc

  7 Upper Meadow Ln, Oak Bluffs, MA 02557
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  /21

  $8,000 total monthly price

  • 1 Bed
  • 1 Bath
  • 936 Sq Ft
  • House for Rent

  10 James Pond Way, West Tisbury, MA 02575

  THIS IS A WEEKLY SUMMER RENTAL ONLY.THE WEEKLY PRICE IN AUGUST IS $2,000. PER WEEK.SEE WEB SITE FOR ADDITIONAL WEEKLY PRICING. This spacious and well appointed one bedroom guest house has a cozy living area and kitchen which opens up to a large second story deck with outdoor furniture, table and chairs where you can enjoy dining amidst the trees. One A/C unit is in the bedroom along with a

  Karen Overtoom Karen M. Overtoom R.E.

  10 James Pond Way, West Tisbury, MA 02575
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  /42

  $865,000 Sold Apr 17, 2025

  4 Quail Run Rd Unit 17, Edgartown, MA 02539

  • 2 Beds
  • 2 Baths
  • 1,208 Sq Ft
  • Built 1972

  Last Sold Summary

  • 1% Below List Price
  • $716/SF
  • 2 Days On Market

  Last Listing Agent Wendy Harman Compass

  4 Quail Run Rd Unit 17, Edgartown, MA 02539
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  /25

  Est $1,562,510 Not Listed For Sale

  • 5 Beds
  • 3 Baths
  • 2,287 Sq Ft

  101 Dunham Ave, Vineyard Haven, MA 02568

  101 Dunham Ave, Vineyard Haven, MA 02568
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  /29

  $1,200,000 Pending

  • 3 Beds
  • 2 Baths
  • 1,120 Sq Ft

  34 Pine Ln, Vineyard Haven, MA 02568

  One level living! This ranch-style home has a great layout and some sweet, unexpected features. The living spaces are opened up to each other allowing the wall of sliders in the living room to flood the rooms with light - and these sliders give access out to the deck with serene views of the woodlands beyond; where Stoney Hill Path bounds the entire south side of the property. The primary suite

  Candy DaRosa Feiner Real Estate

  34 Pine Ln, Vineyard Haven, MA 02568
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  /20

  $12,000 total monthly price

  • 3 Beds
  • 1 Bath
  • 1,068 Sq Ft
  • House for Rent

  76 Ben Chase Rd Wt136, West Tisbury, MA 02575

  Experience a wonderful glimpse of country living in the peaceful, quiet setting of Serene Pond Cottage! This charming Martha's Vineyard retreat features a cozy interior with ample natural light, a private deck where you can take your breakfast and coffee, and a tree-lined backyard to enjoy on lazy summer days. Comfortable three bedroom single story home with one brand new renovated full bath with

  Karen Overtoom Karen M. Overtoom R.E.

  76 Ben Chase Rd Wt136, West Tisbury, MA 02575
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  /30

  $1,525,000 Sold Jun 18, 2025

  54 Lake St, Vineyard Haven, MA 02568

  • 4 Beds
  • 3 Baths
  • 2,016 Sq Ft
  • Built 1967

  Last Sold Summary

  • 12% Below List Price
  • $756/SF
  • 110 Days On Market

  Current Estimated Value $1,523,983

  Last Listing Agent Jon Hartzband Martha's Vineyard Island-Wide Realty

  54 Lake St, Vineyard Haven, MA 02568
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  /35

  Est $2,779,375 Not Listed For Sale

  • 4 Beds
  • 5 Baths
  • 2,728 Sq Ft

  89 Main St, Vineyard Haven, MA 02568

  89 Main St, Vineyard Haven, MA 02568
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  /23

  $1,090,000

  • 3 Beds
  • 2 Baths
  • 1,232 Sq Ft

  54 Towanticut Ave, Oak Bluffs, MA 02568

  Living is Easy in this 3-bedroom 2 bath air-conditioned Ranch located 1 mile from the Center of Oak Bluffs. Features include a spacious living room with a wood-burning fireplace, an updated kitchen with granite countertops and stainless-steel appliances. The dining area has sliders leading to a spacious deck and outdoor shower overlooking the yard space with plenty of room for gardens, pets or

  JoJo Lambert Island Home Realty Inc.

  54 Towanticut Ave, Oak Bluffs, MA 02568
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  /19

  $30,000 total monthly price

  • 5 Beds
  • 4 Baths
  • 3,600 Sq Ft
  • House for Rent

  37 Sachem Cir, West Tisbury, MA 02575

  THIS IS A WEEKLY SUMMER RENTAL ONLY.THE WEEKLY PRICE IN AUGUST IS $7,500. PER WEEK.SEE WEB SITE FOR ADDITIONAL WEEKLY PRICING. Lovely pastoral setting with an elegant farm house and guest house. Abutting Land Bank property on two sides. Quiet privacy, yet just minutes to Lambert’s Cove Beach. The four bedroom house and separate guest house are impeccably decorated and the floor plan lends itself

  Karen Overtoom Karen M. Overtoom R.E.

  37 Sachem Cir, West Tisbury, MA 02575
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  /2

  $880,000 Sold Oct 17, 2025

  5 Johns Way, Oak Bluffs, MA 02557

  • 3 Beds
  • 2 Baths
  • 1,365 Sq Ft
  • Built 1987

  Last Sold Summary

  • $645/SF
  • 0 Days On Market

  Current Estimated Value $1,036,850

  Last Listing Agent LINK Email Cache LINK

  5 Johns Way, Oak Bluffs, MA 02557
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  Est $1,518,324 Not Listed For Sale

  • 6 Beds
  • 5.5 Baths
  • 2,417 Sq Ft

  152 Main St, Vineyard Haven, MA 02568

  152 Main St, Vineyard Haven, MA 02568
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  /23

  $1,099,000 Under Contract

  • 4 Beds
  • 2 Baths
  • 1,306 Sq Ft

  113 Leonard Cir, Vineyard Haven, MA 02568

  This charming four-bedroom Cape features an updated, open-concept design seamlessly connecting the living, kitchen, and dining areas. The first floor includes a bright, well-lit bedroom and an updated shared bathroom. Upstairs, the three additional bedrooms boast soaring cathedral ceilings that maximize natural light, creating a bright and cheerful atmosphere. A shared bath with a shower and

  Alyson Parker Karen M. Overtoom R.E.

  113 Leonard Cir, Vineyard Haven, MA 02568
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  /9

  $19,000 total monthly price

  • 6 Beds
  • 2.5 Baths
  • 2,155 Sq Ft
  • House for Rent

  17 Umbagog Ave Wt109, West Tisbury, MA 02575

  THIS IS A WEEKLY SUMMER RENTAL ONLY.THE WEEKLY PRICE IN AUGUST IS $4,750. PER WEEK.SEE WEB SITE FOR ADDITIONAL WEEKLY PRICING. This three story home is located in a very desirable area off of Lambert's Cove Road, Makonikey, with access to a private association beach and walking trails. There are four plus bedrooms and bright and open living spaces that lead out to a deck and a screened-in porch.

  Karen Overtoom Karen M. Overtoom R.E.

  17 Umbagog Ave Wt109, West Tisbury, MA 02575
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  /2

  $1,100,000 Sold Jun 17, 2025

  17 Front St, Oak Bluffs, MA 02557

  • 2 Beds
  • 2 Baths
  • 2,912 Sq Ft
  • Built 1989

  Last Sold Summary

  • $378/SF
  • 0 Days On Market

  Current Estimated Value $1,202,757

  Last Listing Agent LINK Email Cache LINK

  17 Front St, Oak Bluffs, MA 02557
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  /31

  Est $1,455,662 Not Listed For Sale

  • 3 Beds
  • 2 Baths
  • 1,999 Sq Ft

  48 Puritan Dr, Vineyard Haven, MA 02568

  48 Puritan Dr, Vineyard Haven, MA 02568
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  /12

  $1,495,000 Open House 1/27

  • 3 Beds
  • 4 Baths
  • 2,304 Sq Ft

  33 Alyssa Ln, Vineyard Haven, MA 02568

  Country Living so close to Town! Lovely 3/4 Bedroom 2,304sq ft. Colonial Cape perched on a rise on Alyssa Lane off West Spring Street. Open Kitchen with handcrafted side cabinets and Island with stool seating. Dining, sitting, entertainment area with sliders open to a generous front to back side deck. Living room with propane fired wood stove and half bath also on the first floor. Interior stairs

  Stephanie Burke Portfolio Properties

  33 Alyssa Ln, Vineyard Haven, MA 02568
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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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  /2

  $1,390,000 Sold Jul 22, 2025

  57 Colonial Dr, Vineyard Haven, MA 02568

  • 3 Beds
  • 2 Baths
  • 1,299 Sq Ft
  • Built 1984

  Last Sold Summary

  • $1,070/SF
  • 0 Days On Market

  Current Estimated Value $1,125,215

  Last Listing Agent LINK Email Cache LINK

  57 Colonial Dr, Vineyard Haven, MA 02568
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  /14

  Est $1,455,134 Not Listed For Sale

  • 3 Beds
  • 2 Baths
  • 2,717 Sq Ft

  13 Saddle Club Rd, Edgartown, MA 02539

  13 Saddle Club Rd, Edgartown, MA 02539
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  /54

  $1,830,000

  • 4 Beds
  • 4 Baths
  • 1,600 Sq Ft

  12 & 14 Maple Ave, Oak Bluffs, MA 02557

  Two Historic Oak Bluffs Cottages - Prime Location - Deeded Separately Perched atop a gentle hill, surrounded by lush, established gardens in one of the island's most storied neighborhoods, these two charming 1909 twin cottages offer a rare opportunity to own a piece of local history--just a short distance to the harbor, downtown, and the beloved Winston's takeout. Built at a time when automobiles

  Leslie Floyd Portfolio Properties

  12 & 14 Maple Ave, Oak Bluffs, MA 02557
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  $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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  /27

  $1,560,000 Sold Jan 15, 2026

  36 Ferro Way, Tisbury, MA 02568

  • 5 Beds
  • 3.5 Baths
  • 4,032 Sq Ft
  • Built 2020

  Last Sold Summary

  • 4% Below List Price
  • $387/SF
  • 33 Days On Market

  Last Listing Agent Hope O'Brien Compass Massachusetts, LLC

  36 Ferro Way, Tisbury, MA 02568
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  /20

  Est $1,768,098 Not Listed For Sale

  • 4 Beds
  • 3 Baths
  • 1,240 Sq Ft

  11 Pine Tree Ln, Vineyard Haven, MA 02568

  11 Pine Tree Ln, Vineyard Haven, MA 02568
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  /30

  $999,000

  • 2 Beds
  • 1 Bath
  • 1,232 Sq Ft

  28 Barling Ave, Vineyard Haven, MA 02568

  Oak Bluffs: Home Sweet HomeSituated on over a quarter acre of beautifully landscaped, level grounds with colorful perennial plantings and mature trees, this sun-filled ranch offers a perfect blend of comfort and charm. The open kitchen, dining, and living areas feature cathedral ceilings, classic vertical knotty pine walls, and a cozy brick fireplace. Enjoy a convenient first-floor bedroom

  Michael Schweikert Ocean Park Realty Inc

  28 Barling Ave, 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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  /30

  $1,050,000 Sold Oct 06, 2025

  4 Quail Run Unit 2, Oak Bluffs, MA 02557

  • 2 Beds
  • 1.5 Baths
  • 1,323 Sq Ft
  • Built 1972

  Last Sold Summary

  • 11% Below List Price
  • $794/SF
  • 62 Days On Market

  Current Estimated Value $970,344

  Last Listing Agent Marilyn Moses Ocean Park Realty Inc

  4 Quail Run Unit 2, Oak Bluffs, MA 02557
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  /27

  Est $957,203 Not Listed For Sale

  • 3 Beds
  • 1 Bath
  • 1,116 Sq Ft

  84 Pine Tree Rd, Vineyard Haven, MA 02568

  84 Pine Tree Rd, Vineyard Haven, MA 02568
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  /33

  $925,000 Pending

  • 3 Beds
  • 2.5 Baths
  • 987 Sq Ft

  1 Cottage Park, Oak Bluffs, MA 02557

  The Star Spangled Manor, a beautifully restored gem nestled in the heart of Oak Bluffs within the historic Martha's Vineyard Camp Meeting Association. Located on a pedestrian street, you'll be mere steps away from the shops and restaurants of Circuit Ave., Ocean Park, and the Oak Bluffs beaches. This cherished three-bedroom, three-bathroom cottage seamlessly blends vintage charm with modern

  Diana Gilmore Island Real Estate

  1 Cottage Park, Oak Bluffs, MA 02557
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  /35

  $112,000 total monthly price

  • 6 Beds
  • 9 Baths
  • 5,732 Sq Ft
  • House for Rent

  31 Lamberts Cove Road Vh434, Tisbury, MA 02568

  Karen Overtoom Karen M. Overtoom R.E.

  31 Lamberts Cove Road Vh434, Tisbury, MA 02568
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  /23

  $1,800,000 Sold Aug 26, 2025

  12 Martha's Park Rd, Oak Bluffs, MA 02557

  • 4 Beds
  • 1.5 Baths
  • 1,351 Sq Ft
  • Built 1910

  Last Sold Summary

  • 1% Below List Price
  • $1,332/SF
  • 0 Days On Market

  Current Estimated Value $1,757,793

  Last Listing Agent Michele Moore Island Real Estate

  12 Martha's Park Rd, Oak Bluffs, MA 02557
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  Est $2,491,900 Not Listed For Sale

  • 6 Beds
  • 4 Baths
  • 3,627 Sq Ft

  24 Peacegate Way, Vineyard Haven, MA 02568

  24 Peacegate Way, Vineyard Haven, MA 02568
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  /35

  $1,150,000

  • 3 Beds
  • 2 Baths
  • 1,328 Sq Ft

  96 Dunham Ave, Vineyard Haven, MA 02568

  This attractive colonial style home is located in a terrific neighborhood. Just a short distance to the center of town with nearly 1/2 acre of rolling treed land. The features include a cathedral ceiling over the kitchen and dining room. A large fireplace highlights the living room. From upstairs you can look over the balcony to the dining area and kitchen below. The first floor bedroom with has

  Peter Cronig Cronigs Real Estate

  96 Dunham Ave, Vineyard Haven, MA 02568
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  /45

  $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 $1,045,307

  Last Listing Agent Kerry Quinlan-Potter Breakwater MV

  5 Rock Pond Rd, Vineyard Haven, MA 02568
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  /17

  Est $1,348,387 Not Listed For Sale

  • 3 Beds
  • 2 Baths
  • 1,503 Sq Ft

  165 Weaver Ln, Vineyard Haven, MA 02568

  165 Weaver Ln, Vineyard Haven, MA 02568
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  /30

  $1,999,000

  • 4 Beds
  • 3 Baths
  • 2,730 Sq Ft

  5 Pine Tree Ln, Vineyard Haven, MA 02568

  Blending 1920s charm with modern luxury, this beautifully renovated home is tucked away in the sought-after West Chop area of Vineyard Haven. Just steps from the neighborhood beach on the pristine shores of Vineyard Sound, this elegant seaside retreat offers the perfect mix of historic character and contemporary comfort. Inside, a thoughtfully designed floor plan welcomes you with generous living

  Alyssa Halisky Wallace & Co. Sotheby's International Realty

  5 Pine Tree Ln, Vineyard Haven, MA 02568
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  /31

  $1,685,000 Sold Oct 09, 2025

  126 Border Rd, Vineyard Haven, MA 02568

  • 3 Beds
  • 3 Baths
  • 2,251 Sq Ft
  • Built 1979

  Last Sold Summary

  • 16% Below List Price
  • $749/SF
  • 337 Days On Market

  Current Estimated Value $1,678,092

  Last Listing Agent Natalie Conroy Conroy & Company R.E., Inc.

  126 Border Rd, Vineyard Haven, MA 02568
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  /21

  Est $1,498,188 Not Listed For Sale

  • 4 Beds
  • 3 Baths
  • 2,066 Sq Ft

  23 Anthiers Way, Edgartown, MA 02539

  23 Anthiers Way, Edgartown, MA 02539
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  /20

  $640,000

  • 1 Bed
  • 1 Bath
  • 354 Sq Ft

  2 Lincoln Ave, Oak Bluffs, MA 02568

  Nestled in the heart of the historic Martha’s Vineyard Camp Meeting Association, this beautifully updated suite cottage offers the rare opportunity for year-round living in Oak Bluffs’ campground community. Fully renovated in 2023, including kitchen, bath, floors and winterization, the home seamlessly blends classic Vineyard charm with modern comfort — featuring upgraded systems and finishes that

  Stacy Ickes Donnelly + Co

  2 Lincoln Ave, Oak Bluffs, MA 02568
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  /2

  $825,000 Sold Dec 03, 2025

  69 Summit Ave, Vineyard Haven, MA 02568

  • 3 Beds
  • 2 Baths
  • 1,248 Sq Ft
  • Built 1998

  Last Sold Summary

  • $661/SF
  • 1 Day On Market

  Last Listing Agent Susie Wallo Compass

  69 Summit Ave, Vineyard Haven, MA 02568

Showing Results 121 - 160, Page 4 of 18