Vineyard Haven, MA Homes

/31
$5,995,000
- 3 Beds
- 3 Baths
- 2,234 Sq Ft
43 Sengekontacket Rd, Oak Bluffs, MA 02557

Breathtaking property at the tip of a prominent peninsula on Sengekontacket Pond's western shoreline. Set beautifully at high elevation above the shore, this charming home and guest cottage includes jaw-dropping views of the pond, barrier dunes and Nantucket Sound. Direct from the property take your whaler or other watercraft out into the sound and beyond for endless recreational pursuits. Aside

Peyton Wallace Studio Realty

43 Sengekontacket Rd, Oak Bluffs, MA 02557
/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
/3
$665,000 Sold Mar 06, 2026

2 Hope's Way Unit 31, Oak Bluffs, MA 02557
- Land
- 0.26 Acre
- $2,601,721 per Acre
Last Sold Summary
- 5% Below List Price
- 37 Days On Market
Last Listing Agent Marilyn Moses Ocean Park Realty Inc

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

/34
Est $1,624,842 Not Listed For Sale

84 Christiantown Rd, Vineyard Haven, MA 02568
- 3 Beds
- 2 Baths
- 1,452 Sq Ft
- Built 2018
84 Christiantown Rd, Vineyard Haven, MA 02568

Last Sold Summary
- 16% Above List Price
- $964/SF
- 59 Days On Market
Last Sold Price $1,400,000

Last Listing Agent Candy DaRosa Feiner Real Estate

/9
$1,395,000
- 0.5 Baths
- 1,283 Sq Ft
4 Lagoon Pond Rd, Vineyard Haven, MA 02568

Located at the five corners, this rare commercial property presents an opportunity to set your future business venture up for success. This prime location captures the attention of every single vehicle disembarking the Vineyard Haven Ferry! There are 2.5 parking spots included. Please note that the bike shop business is not for sale. This offering is solely for the real estate. The sellers

Jarrett Hurwitz Keller Williams Realty

4 Lagoon Pond Rd, Vineyard Haven, MA 02568
/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
/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 $973,783

Last Listing Agent LINK Email Cache LINK

5 Johns Way, Oak Bluffs, MA 02557

/19
Not Listed For Sale

43 Look St, Vineyard Haven, MA 02568
- 4 Beds
- 2.5 Baths
- 1,714 Sq Ft
- Built 1900
43 Look St, Vineyard Haven, MA 02568

Last Sold Summary
- $592/SF
- 19 Days On Market
Last Sold Price $1,015,000

Last Listing Agent Andrew McElhinney Compass LLC

/36
$2,900,000 Pending
- 4 Beds
- 5 Baths
- 5,165 Sq Ft
63 Bayes Hill Rd, Oak Bluffs, MA 02557

Tucked away in a serene setting, this beautifully designed custom home offers the ultimate in privacy, comfort, and luxury living. The first floor features a spacious open-concept design, seamlessly blending the dining room, kitchen, wet bar, and living area-perfect for entertaining or relaxing with the family. Home chefs will fall in love with the gourmet kitchen complete with custom cabinetry,

Casandra Hyland Sandpiper Realty, Inc.

63 Bayes Hill Rd, Oak Bluffs, MA 02557
/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
/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 $1,187,062

Last Listing Agent LINK Email Cache LINK

17 Front St, Oak Bluffs, MA 02557

/18
Est $1,772,244 Not Listed For Sale

29 Brook Hollow Rd, Vineyard Haven, MA 02568
- 4 Beds
- 2.5 Baths
- 2,461 Sq Ft
- Built 1994
29 Brook Hollow Rd, Vineyard Haven, MA 02568

Last Sold Summary
- 5% Above List Price
- $683/SF
- 52 Days On Market
Last Sold Price $1,680,000

Last Listing Agent Peyton Wallace Studio Realty

/21
$895,000 Coming Soon
- 3 Beds
- 1 Bath
- 931 Sq Ft
22 Montgomery Square, Oak Bluffs, MA 02557

COMING SOON 3/13 along with new photos..Located in the heart of Wesleyan Grove within the historic Martha's Vineyard Camp Meeting Association, this enchanting year-round Victorian cottage captures the timeless charm and vibrant spirit of Oak Bluffs living. Just steps from lively Circuit Avenue, picturesque Oak Bluffs Harbor, and sandy beaches, the location offers the very best of in-town

Marilyn Moses Ocean Park Realty, Inc.

22 Montgomery Square, Oak Bluffs, MA 02557
/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
/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 $1,190,858

Last Listing Agent LINK Email Cache LINK

57 Colonial Dr, Vineyard Haven, MA 02568

/25
Est $1,487,780 Not Listed For Sale

101 Dunham Ave, Vineyard Haven, MA 02568
- 5 Beds
- 3 Baths
- 2,287 Sq Ft
- Built 1982
101 Dunham Ave, Vineyard Haven, MA 02568

Last Sold Summary
- 24% Above List Price
- $525/SF
- 0 Days On Market
Last Sold Price $1,200,000

Last Listing Agent LINK Email Cache LINK

/21
$1,445,000
- 4 Beds
- 2.5 Baths
- 1,738 Sq Ft
22 Oklahoma Ave, Vineyard Haven, MA 02568

3 BEDROOM HOUSE + 1 BEDROOM APARTMENT! A rare opportunity in a convenient Vineyard Haven neighborhood. This move-in ready property features a 3 BR, 1.5 BA main house plus a legal 1 BR, 1 BA accessory apartment, offering the perfect setup for multi-generational living or a high-demand rental to offset your mortgage. The main house features a stunning sun-room, a cheerful efficient kitchen, and a

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

22 Oklahoma Ave, Vineyard Haven, MA 02568
/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
/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
Current Estimated Value $1,702,500

Last Listing Agent Hope O'Brien Compass Massachusetts, LLC

36 Ferro Way, Tisbury, MA 02568

/35
Est $2,768,259 Not Listed For Sale

89 Main St, Vineyard Haven, MA 02568
- 4 Beds
- 5 Baths
- 2,728 Sq Ft
- Built 1830
89 Main St, Vineyard Haven, MA 02568

Last Sold Summary
- 9% Above List Price
- $935/SF
- 445 Days On Market
Last Sold Price $2,550,000

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

/8
$475,000
- Land
- 0.52 Acre
- $913,462 per Acre
36 Boylston Dr Unit 1.329, 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

36 Boylston Dr Unit 1.329, Edgartown, MA 02539
/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
/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 $1,031,641

Last Listing Agent Marilyn Moses Ocean Park Realty Inc

4 Quail Run Unit 2, Oak Bluffs, MA 02557

/48
Est $1,515,631 Not Listed For Sale

152 Main St, Vineyard Haven, MA 02568
- 6 Beds
- 5.5 Baths
- 2,417 Sq Ft
- Built 1720
152 Main St, Vineyard Haven, MA 02568

Last Sold Summary
- 17% Above List Price
- $538/SF
- 370 Days On Market
Last Sold Price $1,300,000

Last Listing Agent Elise Ryan LandVest MV

/17
$725,000 Pending
- 2 Beds
- 2 Baths
- 1,068 Sq Ft
181 Circuit Ave, Oak Bluffs, MA 02557

Location, location, location!! This chic, turnkey cottage has been completely renovated! Park your car, drop your bags and walk to everything - beaches, shops, restaurants, parks and the ferry! Enjoy the front deck, backyard patio or saunter across to Veira Park. Perfect family getaway or a great investment property with strong rental income history! Enjoy this adorable home all year around!

Jennifer B. DaSilva Compass

181 Circuit Ave, Oak Bluffs, MA 02557
/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
/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 $1,783,480

Last Listing Agent Michele Moore Island Real Estate

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

/31
Est $1,418,757 Not Listed For Sale

48 Puritan Dr, Vineyard Haven, MA 02568
- 3 Beds
- 2 Baths
- 1,999 Sq Ft
- Built 1985
48 Puritan Dr, Vineyard Haven, MA 02568

Last Sold Summary
- 26% Above List Price
- $565/SF
- 25 Days On Market
Last Sold Price $1,130,000

Last Listing Agent Jennifer B. DaSilva Compass

/3
$857,000
- Land
- 0.39 Acre
- $2,209,902 per Acre
24 Towanticut Ave Unit 188, Oak Bluffs, MA 02568

OAK BLUFFS - A Rare Opportunity to purchase an Eight (8) Bedroom lot. This already cleared, oversized lot, 16,895sq.ft., (more than 1/3 acre) comes with an Approved Eight (8) Bedroom Septic Design, ready to build. Exceptional potential for a spacious custom home, family compound, or a rental property. Utilities are available by the lot, which significantly reduces development costs and time.

Alisan Lohan-Conway Alisan Lohan-Conway Properties

24 Towanticut Ave Unit 188, Oak Bluffs, MA 02568
/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
/12
$860,000 Sold Feb 09, 2026

8 Hitchings Cir, Oak Bluffs, MA 02557
- 2 Beds
- 2 Baths
- 1,232 Sq Ft
- Built 1985
Last Sold Summary
- 6% Below List Price
- $698/SF
- 22 Days On Market
Last Listing Agent Peyton Wallace Studio Realty

8 Hitchings Cir, Oak Bluffs, MA 02557

/14
Est $1,460,572 Not Listed For Sale

13 Saddle Club Rd, Edgartown, MA 02539
- 3 Beds
- 2 Baths
- 2,717 Sq Ft
- Built 1988
13 Saddle Club Rd, Edgartown, MA 02539

Last Sold Summary
- 17% Above List Price
- $460/SF
- 43 Days On Market
Last Sold Price $1,250,000

Last Listing Agent Reciprocal Agent Reciprocal Office

/23
$1,099,000 Pending
- 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
/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 $1,727,247

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

126 Border Rd, Vineyard Haven, MA 02568

/20
Est $1,796,577 Not Listed For Sale

11 Pine Tree Ln, Vineyard Haven, MA 02568
- 4 Beds
- 3 Baths
- 1,240 Sq Ft
- Built 1960
11 Pine Tree Ln, Vineyard Haven, MA 02568

Last Sold Summary
- 6% Above List Price
- $1,371/SF
- 74 Days On Market
Last Sold Price $1,700,000

Last Listing Agent Carol Shore Donnelly + Co.

/12
$1,495,000
- 4 Beds
- 4 Baths
- 2,304 Sq Ft
33 Alyssa Ln, Vineyard Haven, MA 02568

Country Living so close to Town! Lovely 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
/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
Current Estimated Value $862,879

Last Listing Agent Susie Wallo Compass

69 Summit Ave, Vineyard Haven, MA 02568

/27
Est $947,770 Not Listed For Sale

84 Pine Tree Rd, Vineyard Haven, MA 02568
- 3 Beds
- 1 Bath
- 1,116 Sq Ft
- Built 1980
84 Pine Tree Rd, Vineyard Haven, MA 02568

Last Sold Summary
- 14% Above List Price
- $743/SF
- 66 Days On Market
Last Sold Price $829,000

Last Listing Agent Michele Moore Island Real Estate

/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
/40
$650,000 Sold Sep 10, 2025

25 Oak Ave, Oak Bluffs, MA 02557
- 2 Beds
- 0.5 Baths
- 759 Sq Ft
- Built 1900
Last Sold Summary
- 4% Below List Price
- $856/SF
- 251 Days On Market
Current Estimated Value $774,585

Last Listing Agent Alisan Lohan-Conway Alisan Lohan-Conway Properties

25 Oak Ave, Oak Bluffs, MA 02557

Showing Results 121 - 160, Page 4 of 18

Massachusetts Dukes County Vineyard Haven

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