Martha's Vineyard, MA Homes

/21
$1,159,999
- 3 Beds
- 2 Baths
- 1,428 Sq Ft
9 Bayview Ave, Oak Bluffs, MA 02568

Oak Bluffs Charmer – Welcome to 9 Bayview Avenue, a 3-bedroom, 2-bath home tucked away on a quiet road in Oak Bluffs. Sited on a level 10,050 sq. ft. lot, this property offers 1,428 sq. ft. of light-filled living space. The main level features a spacious living room, kitchen, and dining area, along with a first-floor bedroom and full bath. Upstairs, two comfortable bedrooms share a full bathroom,

Andrew McElhinney Compass LLC

9 Bayview Ave, Oak Bluffs, MA 02568
/9
$10,800 total monthly price
- 4 Beds
- 2 Baths
- 702 Sq Ft
- House for Rent
141 N Rd Ch202, Chilmark, MA 02535

THIS IS A WEEKLY SUMMER RENTAL ONLY.THE WEEKLY PRICE IN AUGUST IS $2,700. PER WEEK.SEE WEB SITE FOR ADDITIONAL WEEKLY PRICING. Chilmark Cottage Perfection!!! You will love this quaint Vineyard Style Cottage that has been meticulously designed to include all the amenities one could imagine. This vintage charmer really boasts a lot of Style. Inside you will find really beautiful hardwood floors, a

Karen Overtoom Karen M. Overtoom R.E.

141 N Rd Ch202, Chilmark, MA 02535
/138
$4,800,000 Sold Sep 24, 2025
- 4,167 Sq Ft
- $1,152/SF
- 50 Days On Market
- 4 Beds
- 4.5 Baths
- Built 2020
264 Katama Rd, Edgartown, MA 02539

EDGARTOWN - KATAMA - A MUST SEE! Summer living at its best. A wonderful property, a luxury oasis, a retreat & personal playground, situated equidistant between South Beach & Downtown Edgartown, within walking distance to The Field Club. This prestigious location offers a perfect blend of classic Vineyard charm & modern sophistication. Main house features a dramatic, double-height entrance

Alisan Lohan-Conway Alisan Lohan-Conway Properties

264 Katama Rd, Edgartown, MA 02539

/12
Not Listed For Sale
- 6 Beds
- 4.5 Baths
- 2,892 Sq Ft
9 Dunes Rd, Edgartown, MA 02539

9 Dunes Rd, Edgartown, MA 02539

/6
$1,595,000
- Land
- 3.2 Acres
- $498,438 per Acre
9 Beach Pebble Rd, Vineyard Haven, MA 02568

Vacant land in West Tisbury's Makonikey Community with access to the beautiful Lower Makonikey Association beach. This rare offering spans over 3 acres, with a 1.4-acre area providing the ideal location for a substantial residence in keeping with the distinguished homes that define this exclusive neighborhood. This property presents a unique opportunity to create an exceptional island retreat.

Cassie Bradley Wallace & Co. Sotheby's International Realty

9 Beach Pebble Rd, Vineyard Haven, MA 02568
/21
$13,000 total monthly price
- 4 Beds
- 3 Baths
- 2,500 Sq Ft
- House for Rent
14 Pulpit Rock Rd, Oak Bluffs, MA 02557

PRICES ARE WEEKLY NOT MONTHLY. Located in Waterview Farms, this four bedroom home features a private beach on Sengekontacket Pond, private dock access to Land Bank boat launch and several walking trails. Just minutes to Farm Neck Golf Course, beaches and town.

Karen Overtoom Karen M. Overtoom R.E.

14 Pulpit Rock Rd, Oak Bluffs, MA 02557
/25
$3,925,000 Sold Sep 24, 2025
- 3,954 Sq Ft
- $993/SF
- 4 Days On Market
- 8 Beds
- 4.5 Baths
- Built 1730
966 Main St, Vineyard Haven, MA 02568

Nestled along the iconic Main Street of West Chop, this classic gem offers a rare opportunity to own a piece of Martha's Vineyard's rich heritage. Built with timeless elegance and enhanced with modern comforts, this distinguished residence boasts 8 bedrooms, 4 1/2 bathrooms, and captivating views of the Vineyard Sound, ensuring an unparalleled island living experience.Immerse yourself in the

Grant Rudolph Viewpoints

966 Main St, Vineyard Haven, MA 02568

/18
Est $994,992 Not Listed For Sale
- 2 Beds
- 1 Bath
- 1 Sq Ft
10 Canterbury Ln, Vineyard Haven, MA 02568

10 Canterbury Ln, Vineyard Haven, MA 02568

/4
$445,000
- Land
- 0.56 Acre
- $794,643 per Acre
5 Candle Maker Cir Unit 1.331, Edgartown, MA 02539

Located on a quiet cul-de-sac in a private Edgartown neighborhood, this half-acre parcel offers the perfect setting for your Martha's Vineyard home. Centrally located, the property provides easy access to the bike path and State Forest walking trails. With the recent Massachusetts Affordable Homes Act, this lot is now buildable and will include an approved 3-bedroom septic plan. The site allows

Alyssa Halisky Wallace & Co. Sotheby's

5 Candle Maker Cir Unit 1.331, Edgartown, MA 02539
/26
$18,000 total monthly price
- 3 Beds
- 2.5 Baths
- 2,400 Sq Ft
- House for Rent
40 Lighthouse Rd, Aquinnah, MA 02535

Great water view property in Aquinnah - this immaculate contemporary has that unique combination of a beautifully designed and constructed, year-round home, AND an outstanding view of the Sound and Elizabeth Islands. Not only is the water view property packed with many custom details, but the home's layout is perfect for relaxed living - with a fantastic kitchen open to the dining and living

Karen Overtoom Karen M. Overtoom R.E.

40 Lighthouse Rd, Aquinnah, MA 02535
/17
$1,790,000 Sold Sep 23, 2025
- Land
- 3.3 Acres
- $542,424 per Acre
- 77 Days On Market
32 Stonewall Rd Unit 2.1, Chilmark, MA 02535

South shore beachy living in Stonewall Association with private parking and access to a lovely swim and surf beach in a beloved area of Chilmark. There are second floor water views over Squibnocket Point and the Atlantic Ocean. This lot is fully engineered and ready to be built on! Single-family dwelling, plus a detached bedroom and accessory buildings, permitted according to the Chilmark

Jill Napior Tea Lane Associates

32 Stonewall Rd Unit 2.1, Chilmark, MA 02535

/32
Est $1,276,286 Not Listed For Sale
- 3 Beds
- 1 Bath
- 1,118 Sq Ft
58 Hagerty Dr, Vineyard Haven, MA 02568

58 Hagerty Dr, Vineyard Haven, MA 02568

/27
$1,800,000
- 3 Beds
- 3 Baths
- 2,293 Sq Ft
10 Trotters Ln, West Tisbury, MA 02575

Centrally located and surrounded by lush landscaping, this inviting cape offers three bedrooms and three full baths. Warm, mellow wood floors, tiled bathrooms and a spacious living area anchored by a cozy fireplace. The full basement provides ample storage or expansion potential, while a versatile bonus room on the second level is perfect as an art studio, home office or guest overflow.

Rebecca V Conroy Conroy & Company R.E., Inc.

10 Trotters Ln, West Tisbury, MA 02575
/8
$7,900 total monthly price
- 3 Beds
- 2.5 Baths
- 2,107 Sq Ft
- House for Rent
2 Paddock Cir, Chilmark, MA 02535

Karen Overtoom Karen M. Overtoom R.E.

2 Paddock Cir, Chilmark, MA 02535
/35
$1,500,000 Sold Sep 22, 2025
- 2,336 Sq Ft
- $642/SF
- 277 Days On Market
- 4 Beds
- 3.5 Baths
- Built 1980
8 Schoolhouse Village, Oak Bluffs, MA 02557

Located in a desirable Oak Bluffs neighborhood, surrounded by mature plantings and attractive, colorful landscaping, this property offers a pleasantly appointed 3-bedroom, 2.5-bath home and a recently renovated 1-bedroom, 1-bath apartment above the 2-car garage. The first floor features a spacious living room with a pellet stove and a fabulous great room with a wood-burning stove. French doors

Stephanie Roache Donnelly + Co.

8 Schoolhouse Village, Oak Bluffs, MA 02557

/35
Est $3,092,686 Not Listed For Sale
- 4 Beds
- 3.5 Baths
- 2,407 Sq Ft
5 Hillman Dr, Edgartown, MA 02539

5 Hillman Dr, Edgartown, MA 02539

/18
$1,500,000
- 3 Beds
- 2 Baths
- 1,188 Sq Ft
8 Court St, Edgartown, MA 02539

Nestled in Katama, this vacation home offers easy access to South Beach, Edgartown Great Pond/Wilson's Landing, and Edgartown Village. The property includes three bedrooms, two baths, a cozy living room with a fireplace, a kitchen, and a sunroom/dining area--ready for your personal touch. An excellent opportunity for a relaxed Island lifestyle, second home, or vacation rental.

Emma Kennedy Sandpiper Realty Inc

8 Court St, Edgartown, MA 02539
/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
/34
$2,001,001 Sold Sep 19, 2025
- 1,746 Sq Ft
- $1,146/SF
- 116 Days On Market
- 2 Beds
- 1.5 Baths
- Built 1985
17 Sutton's Way, Edgartown, MA 02539

Set on a beautifully landscaped half-acre in Katama, this thoughtfully reimagined ranch is just a short bike ride to South Beach or downtown Edgartown. The main house features 2 bedrooms, 1.5 baths, and a bright, open layout with a fully renovated kitchen (2020) showcasing quartz countertops, stainless appliances, and a serene coastal palette. The full bath was tastefully updated in 2024 with

Carson Crissman Compass | Point B

17 Sutton's Way, Edgartown, MA 02539

/42
Est $4,152,272 Not Listed For Sale
- 4 Beds
- 3.5 Baths
- 3,467 Sq Ft
8 Jennifer Way, Edgartown, MA 02539

8 Jennifer Way, Edgartown, MA 02539

/51
$9,795,000
- 6 Beds
- 7 Baths
- 6,135 Sq Ft
52 S Summer St, Edgartown, MA 02539

The historic Captain Ellsworth West House is a landmark property in the very heart of downtown Edgartown, offering an extraordinary combination of history, charm, and modern luxury. Just steps from Edgartown’s celebrated restaurants, galleries, shops, and harbor, this rare estate provides both the convenience of in-town living and the privacy of a graciously designed compound. The main residence

Alyssa Halisky Wallace & Co. Sotheby's

52 S Summer St, Edgartown, MA 02539
/30
$5,800,000 Sold Sep 19, 2025
- 5,104 Sq Ft
- $1,136/SF
- 81 Days On Market
- 5 Beds
- 7 Baths
- Built 2021
10 Puwal Ln, Edgartown, MA 02539

KATAMA COMPOUND WITH POOL - TURNKEY & READY FOR USE THIS SUMMER! In an enclave of luxury homes in Katama, this 2021-built 5 bedroom, 5 bathroom property with three half-baths is being delivered turnkey with fine furnishings and most artwork. The home has everything the modern buyer wants, including two primary bedroom suites (one upstairs, one downstairs), all bedrooms with ensuite bathrooms, two

Mark Jenkins Wallace & Co. Sotheby's

10 Puwal Ln, Edgartown, MA 02539

/35
Est $2,034,014 Not Listed For Sale
- 4 Beds
- 3 Baths
- 1,995 Sq Ft
159 Charles Neck Way, Vineyard Haven, MA 02568

159 Charles Neck Way, Vineyard Haven, MA 02568

/21
$1,950,000
- 3 Beds
- 2 Baths
- 2,237 Sq Ft
10 Duende Ln, Edgartown, MA 02539

Experience the quintessential Martha's Vineyard lifestyle at this charming residence perfectly nestled in a private yet convenient Katama location. This inviting 3-bedroom plus loft, 2-bathroom home is situated on a .52-acre lot, providing ample privacy and outdoor enjoyment. Step inside the light-filled interior featuring multiple windows and skylights that invite the sunshine in. Convenience is

Idalyn Macchia Gilstad Wallace & Co. Sotheby's

10 Duende Ln, Edgartown, MA 02539
/40
$6,689,025 Sold Sep 19, 2025
- 5,166 Sq Ft
- $1,295/SF
- 122 Days On Market
- 6 Beds
- 7 Baths
- Built 1947
74 Turkeyland Cove Rd, Edgartown, MA 02539

This distinguished Edgartown Great Pond compound presents an exceptional collection of features and amenities. Situated within a highly desirable, secluded enclave on Turkeyland Cove, the 4.8-acre property includes two residences, a bespoke private in-ground swimming pool, approximately 400 feet of waterfront, outstanding water views, and a private beach lot on the Atlantic Ocean. The principal

Peyton Wallace Studio Realty

74 Turkeyland Cove Rd, Edgartown, MA 02539

/18
Est $1,184,786 Not Listed For Sale
- 3 Beds
- 2 Baths
- 1,038 Sq Ft
5 Windsor Dr, Edgartown, MA 02539

5 Windsor Dr, Edgartown, MA 02539

/40
$1,985,000
- 6 Beds
- 2.5 Baths
- 2,836 Sq Ft
36 Smith Hollow Dr, Edgartown, MA 02539

Tucked away behind association common land, this year-round compound offers the perfect blend of privacy, space, and flexibility. The post-and-beam main house features four bedrooms and combines timeless character with functional design, ideal for everyday living or seasonal enjoyment. A separate two-bedroom guest house with a welcoming farmer's porch is thoughtfully sited to ensure privacy and

Katherine Donahue Sandpiper Realty Inc

36 Smith Hollow Dr, Edgartown, MA 02539
/24
$3,300,000 Sold Sep 18, 2025
- 3,793 Sq Ft
- $870/SF
- 139 Days On Market
- 4 Beds
- 6 Baths
- Built 1960
28 Crocker Dr, Edgartown, MA 02539

This beautifully renovated Katama retreat blends refined design, luxury amenities, and flexible living. The main house offers three bedrooms, including a peaceful primary suite with private deck, a second en suite, and a cozy bunkroom. The octagonal living room, skylit dining room with gas fireplace, and chef’s kitchen with quartz counters and high-end appliances are perfect for entertaining.

Jennifer O'hanlon Compass

28 Crocker Dr, Edgartown, MA 02539

/41
Est $1,815,061 Not Listed For Sale
- 3 Beds
- 3 Baths
- 1,803 Sq Ft
7 Tar Barrel Rd, Aquinnah, MA 02535

7 Tar Barrel Rd, Aquinnah, MA 02535

/31
$1,150,000
- 2 Beds
- 1 Bath
- 1,040 Sq Ft
73 & 0 Old Country Ln, Vineyard Haven, MA 02568

Charming 2-bedroom, 1-bath ranch house in Vineyard Haven, in town—just minutes from shops, restaurants, and schools. This well-maintained property offers a functional layout with a bright living area, a cozy kitchen overlooking the backyard, two comfortable bedrooms, and a full bathroom. The house has a full basement with ample room for storage and projects. This home is situated on two lots,

Julianna Flanders Flanders Real Estate

73 & 0 Old Country Ln, Vineyard Haven, MA 02568
/46
$3,120,000 Sold Sep 16, 2025
- 3,669 Sq Ft
- $850/SF
- 84 Days On Market
- 4 Beds
- 3 Baths
- Built 1993
140 Pond Rd, Vineyard Haven, MA 02568

Welcome to this beautifully updated and privately situated home in one of West Tisbury’s most desirable associations. Residents enjoy exclusive access to tennis courts, walking trails, horse pastures and Tisbury Great Pond. Designed for both comfort and luxury, this spacious 4+ bedroom, 3 bathroom property is ideal as a year-round residence or upscale vacation retreat.The first floor

Jon Hartzband Martha's Vineyard Island-Wide Realty

140 Pond Rd, Vineyard Haven, MA 02568

/22
Est $1,053,648 Not Listed For Sale
- 3 Beds
- 2 Baths
- 1,025 Sq Ft
10 Saddle Club Rd, Edgartown, MA 02539

10 Saddle Club Rd, Edgartown, MA 02539

/48
$1,595,000
- 5 Beds
- 4 Baths
- 2,516 Sq Ft
651 State Rd, Vineyard Haven, MA 02568

Fabulous multi-building compound offered in West Tisbury. Well maintained main house dating to 1880 has many features common to classic older homes but has been updated to provide comfort and year-round livability. Bright and cozy there are lots of rooms and spaces to provide for a larger group of individuals with a total of 4 bedrooms in the main house and a partially finished walk-out

Jim Feiner Feiner Real Estate

651 State Rd, Vineyard Haven, MA 02568
/15
$1,450,000 Sold Sep 16, 2025
- 1,495 Sq Ft
- $970/SF
- 302 Days On Market
- 3 Beds
- 2 Baths
- Built 1986
6 Gerts Way, Edgartown, MA 02539

In the heart of Katama, close to south beach and all that the area has to offer, is this traditional 3 bedroom cape with updates. The bright kitchen and dining area offer a modern space, perfect for entertaining. A vaulted ceiling makes the living room light and bright. Three bedrooms, one downstairs and two upstairs, share bathrooms on each level. An outdoor shower, screened porch and outdoor

Kathleen Dawson Donnelly + Co.

6 Gerts Way, Edgartown, MA 02539

/32
Est $1,104,871 Not Listed For Sale
- 3 Beds
- 2 Baths
- 1,429 Sq Ft
10 Elm St, Vineyard Haven, MA 02568

10 Elm St, Vineyard Haven, MA 02568

/34
$3,250,000
- 4 Beds
- 3 Baths
- 1,728 Sq Ft
6 Brewster Ave, Oak Bluffs, MA 02557

Enjoy sweeping ocean views from this beautifully updated East Chop Victorian, complete with a timeless guest cottage. Thoughtfully renovated in 2010, the main residence seamlessly blends historic character with modern comfort. The kitchen and bathrooms have been stylishly updated while preserving the home's original charm and character. The guest cottage, tucked to the rear of the property,

Katherine Donahue Sandpiper Realty Inc

6 Brewster Ave, Oak Bluffs, MA 02557
/21
$500,000 Sold Sep 12, 2025
- 604 Sq Ft
- $828/SF
- 58 Days On Market
- 1 Bed
- 1 Bath
- Built 1870
21 Rock Ave, Oak Bluffs, MA 02557

Experience the charm of 21 Rock Avenue, nestled in the Historic Martha's Vineyard Camp Meeting Association. This year-round cottage features 1 bedroom and 1 bath, and is just moments away from Oak Bluffs Harbor, ferry ports, sandy beaches, art galleries, and delightful restaurants. Recent exterior enhancements include cedar fencing, refreshed house trim, new paint, and an upgraded roof. Please

Marilyn Moses Ocean Park Realty Inc

21 Rock Ave, Oak Bluffs, MA 02557

/30
Est $1,410,218 Not Listed For Sale
- 3 Beds
- 2 Baths
- 1,464 Sq Ft
88 Hopps Farm Rd, Vineyard Haven, MA 02568

88 Hopps Farm Rd, Vineyard Haven, MA 02568

/28
$7,450,000
- 5 Beds
- 4.5 Baths
- 5,000 Sq Ft
7 Clay Pit Ln, Aquinnah, MA 02535

Stunning waterfront home with panoramic waterviews. The home was designed by Hutker Associates, built by Andrew Flake, and landscaped by Michael Van Valkenburgh - three of the most renowned names in Martha's Vineyard home creation. Little wonder it was featured on the cover of Beautiful Home magazine and has been included in several other home design magazines and books. The 5000 sq ft house

Mark Jenkins Wallace & Co. Sotheby's

7 Clay Pit Ln, Aquinnah, MA 02535
/2
$3,500,000 Sold Sep 12, 2025
- 3,656 Sq Ft
- $957/SF
- 0 Days On Market
- 8 Beds
- 3 Baths
- Built 1974
214 State Rd, Vineyard Haven, MA 02568

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214 State Rd, Vineyard Haven, MA 02568

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