Tisbury, MA Homes

/7
$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
/26
$50,000 total monthly price
- 4 Beds
- 3 Baths
- 3,237 Sq Ft
- House for Rent
29 Naushon Rd Wt142, West Tisbury, MA 02575

THIS IS A WEEKLY SUMMER RENTAL ONLY.THE WEEKLY PRICE IN AUGUST IS $12,500. PER WEEK.SEE WEB SITE FOR ADDITIONAL WEEKLY PRICING. Waterfront home in spectacular location overlooking the Vineyard Sound and the Elizabeth Islands. This casual and comfortable single level 4 BR 3 bath home has central air and heat. Enjoy summer star-studded skies from your patio or through skylights in each bedroom.

Karen Overtoom Karen M. Overtoom R.E.

29 Naushon Rd Wt142, West Tisbury, MA 02575
/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

/34
Est $1,627,852 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

/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
/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
/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

/19
Not Listed For Sale
- 4 Beds
- 2.5 Baths
- 1,714 Sq Ft
43 Look St, Vineyard Haven, MA 02568

43 Look St, Vineyard Haven, MA 02568

/3
$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
/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 $1,036,850

Last Listing Agent LINK Email Cache LINK

5 Johns Way, Oak Bluffs, MA 02557

/18
Est $1,841,150 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

/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
/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 $1,202,757

Last Listing Agent LINK Email Cache LINK

17 Front St, Oak Bluffs, MA 02557

/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

/26
$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! Discover 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 solarium or sunroom, a cheerful

Idalyn Macchia Gilstad Wallace & Co. Sotheby's

22 Oklahoma Ave, Vineyard Haven, MA 02568
/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
/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

/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

/36
$2,900,000
- 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
/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
/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

/48
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

/12
$899,000 Pending
- 2 Beds
- 2 Baths
- 1,232 Sq Ft
8 Hitchings Cir, Oak Bluffs, MA 02557

Nestled in a quiet Oak Bluffs neighborhood, less than a mile from the harbor, beaches, shops, and restaurants, this Cape-style home offers the perfect balance of convenience and tranquility. The interior features an open kitchen and living room, plenty of space for guests, and a full unfinished basement. The two bedroom Title V septic system has passed inspection. Outside, the property features a

Peyton Wallace Studio Realty

8 Hitchings Cir, Oak Bluffs, MA 02557
/18
$10,000 total monthly price
- 3 Beds
- 2 Baths
- 1,439 Sq Ft
- House for Rent
24 Nat's Farm Lane Wt113, West Tisbury, MA 02575

THIS IS A WEEKLY SUMMER RENTAL ONLY.THE WEEKLY PRICE IN AUGUST IS $2,500. PER WEEK.SEE WEB SITE FOR ADDITIONAL WEEKLY PRICING. Charming three bedroom home located in a private neighborhood close to bike path, walking trails and public tennis courts. Just a short drive to Lambert's Cove Beach, West Tisbury Village and down island restaurants and shops.Amenities include High definition TV, wifi

Karen Overtoom Karen M. Overtoom R.E.

24 Nat's Farm Lane Wt113, 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 $970,344

Last Listing Agent Marilyn Moses Ocean Park Realty Inc

4 Quail Run Unit 2, Oak Bluffs, MA 02557

/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

/9
$4,995,000 Pending
- 5 Beds
- 6.5 Baths
- 4,216 Sq Ft
64 Crowell Ln, Tisbury, MA 02568

Welcome to your Vineyard Dream in the heart of West Chop! Built by Novo Builds, a renowned construction company that is recognized for their innovative designs and high-quality craftsmanship. Novo Builds is set to enhance the landscape of this iconic island with their latest development.This stunning new build offers the perfect blend of modern luxury and coastal charm, making it an ideal

Joe & Nicole Holland Vineyard Dream Realty LLC

64 Crowell Ln, Tisbury, MA 02568
/39
$46,000 total monthly price
- 6 Beds
- 4.5 Baths
- 3,800 Sq Ft
- House for Rent
99 Pond Road Wt104, West Tisbury, MA 02575

THIS IS A WEEKLY RENTAL NOT A MONTHLY!!!!! Beautiful bright sunny home with open concept living. Main floor features a gourmet kitchen with stainless appliances, breakfast bar and formal dining table to seat 10. Large glass sliders open up to expansive views of the deck, pool and pasture beyond. Also on the main level is a separate living area with large screen TV, powder room, and den with twin

Karen Overtoom Karen M. Overtoom R.E.

99 Pond Road Wt104, 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 $1,757,793

Last Listing Agent Michele Moore Island Real Estate

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

/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

/10
$4,500,000
- 15 Beds
- 12.5 Baths
- 7,250 Sq Ft
11 Macs Ln, Tisbury, MA 02568

A unique opportunity to own a one of a kind property complete with fourteen bedrooms, flanked with large picture windows and water views from all three living levels. Currently being run as a state licensed, private pay, assisted living facility. In addition to the fourteen bedrooms and twelve full baths and one half bath, in the main building, there is a private owners apartment on the first

Madelyn Silvia Wallace & Co. Sotheby's

11 Macs Ln, Tisbury, MA 02568
/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
/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

/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

/58
$4,695,000 Pending
- 5 Beds
- 5.5 Baths
- 4,003 Sq Ft
97 Longview Rd, Vineyard Haven, MA 02568

This beautifully designed post-and-beam home features stunning views of the Vineyard Sound, Elizabeth Islands, and unforgettable sunsets. Surrounded by beautiful stone walls and perfectly sited on 2.2 acres, this serene property offers a combination of luxury and comfort, exuding tranquility and timeless charm. The main home spans three spacious levels, all opening onto generous decks ideal for

Stephanie Roache Donnelly + Co

97 Longview Rd, Vineyard Haven, MA 02568
/41
$14,500 total monthly price
- 5 Beds
- 5.5 Baths
- 3,392 Sq Ft
- House for Rent
76 School House Lane Wt101, West Tisbury, MA 02575

THIS IS A WEEKLY RENTAL NOT A MONTHLY!!!! An elegant, whimsical house full of color, quality and artistic touches. The grounds are sumptuous, nature at its apotheosis. There is gentle movement in the landscape with flowering trees and shrubs everywhere replete with a babbling brook flowing into a pond bordering the garden behind the house. The stonework is finely crafted with balanced proportions

Karen Overtoom Karen M. Overtoom R.E.

76 School House Lane Wt101, West Tisbury, MA 02575
/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

/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

Showing Results 121 - 160, Page 4 of 18

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