Dukes County, MA Homes

/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
/29
$64,000 total monthly price
- 4 Beds
- 7 Baths
- 3,600 Sq Ft
- House for Rent
385 Barnes Rd Ob534, Oak Bluffs, MA 02557

THIS IS A WEEKLY SUMMER RENTAL ONLY.THE WEEKLY PRICE IN AUGUST IS $18,000. PER WEEK.SEE WEB SITE FOR ADDITIONAL WEEKLY PRICING. This is a beautiful waterfront home with a pool on the Lagoon. Enter through the impressive foyer with water views over the pool and lawn. There is a large living room with cathedral ceilings and dining area on the main level. There is a gourmet kitchen with eat-in

Karen Overtoom Karen M. Overtoom R.E.

385 Barnes Rd Ob534, Oak Bluffs, MA 02557
/18
$995,000 Sold Nov 06, 2025

2 Flamingo Dr, Edgartown, MA 02539
- 3 Beds
- 1 Bath
- 990 Sq Ft
- Built 1983
Last Sold Summary
- 5% Below List Price
- $1,005/SF
- 5 Days On Market
Current Estimated Value $1,069,326

Last Listing Agent Sean Federowicz Landmarks at TODAY Real Estate

2 Flamingo Dr, Edgartown, MA 02539

/30
Est $1,810,839 Not Listed For Sale
- 3 Beds
- 3 Baths
- 2,046 Sq Ft
8 Harpoon Hollow, Aquinnah, MA 02535

8 Harpoon Hollow, Aquinnah, MA 02535

/37
$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
/20
$20,000 total monthly price
- 3 Beds
- 3 Baths
- House for Rent
40 Hidden Cove Rd, Oak Bluffs, MA 02557

THIS IS A WEEKLY SUMMER RENTAL ONLY.SEE WEB SITE FOR WEEKLY PRICING. Welcome to "Shangri-la" A beautiful townhouse condominium end unit with magnificent views. Located midway between Oak Bluffs and Edgartown. You can enjoy the beautiful pool or one of the close local beaches. You will want to sit and enjoy the water views on the deck. The townhouse has a great living room with views and bedrooms

Karen Overtoom Karen M. Overtoom R.E.

40 Hidden Cove Rd, Oak Bluffs, MA 02557
/44
$1,890,000 Sold Aug 29, 2025

1 Thames Ct, Edgartown, MA 02539
- 4 Beds
- 3 Baths
- 3,270 Sq Ft
- Built 1981
Last Sold Summary
- $578/SF
- 38 Days On Market
Current Estimated Value $2,163,428

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

1 Thames Ct, Edgartown, MA 02539

/30
Est $2,482,768 Not Listed For Sale
- 4 Beds
- 2.5 Baths
- 2,404 Sq Ft
10 Gerts Way, Edgartown, MA 02539

10 Gerts Way, Edgartown, MA 02539

/49
$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
/29
$34,000 total monthly price
- 4 Beds
- 2.5 Baths
- 2,300 Sq Ft
- House for Rent
15 Loon Lane Ch203, Chilmark, MA 02535

THIS IS A WEEKLY SUMMER RENTAL ONLY.THE WEEKLY PRICE IN AUGUST IS $8,500. PER WEEK.SEE WEB SITE FOR ADDITIONAL WEEKLY PRICING. Modern 4 bedroom home completed in 2019, in Menemsha. Located on a quiet road with waterviews from the upstairs bedrooms also offers views of the famous Menemsha sunsets from the deck. Sustainably harvested flooring features silky smooth and buttery hard wood floors from

Karen Overtoom Karen M. Overtoom R.E.

15 Loon Lane Ch203, Chilmark, MA 02535
/32
$899,000 Sold Jul 11, 2025

8 Rock Ave, Oak Bluffs, MA 02557
- 3 Beds
- 1.5 Baths
- 955 Sq Ft
- Built 1871
Last Sold Summary
- $941/SF
- 6 Days On Market
Current Estimated Value $898,936

Last Listing Agent Marilyn Moses Ocean Park Realty Inc

8 Rock Ave, Oak Bluffs, MA 02557

/39
Est $3,232,931 Not Listed For Sale
- 5 Beds
- 4.5 Baths
- 4,239 Sq Ft
18 S Pond Rd, Vineyard Haven, MA 02568

18 S Pond Rd, Vineyard Haven, MA 02568

/36
$1,495,000
- 4 Beds
- 2 Baths
- 1,332 Sq Ft
40 Scotchmans Ln, Vineyard Haven, MA 02568

A home with history, built in the early 1800s this dwelling was originally built on a local farm and moved to its present location in the 1920's. The structure sits nestled amongst mature plantings and out buildings facing the Mill Brook. The studio and covered patio offer opportunities to entertain, relax and reflect. This 3.76 parcel was created from a larger parcel by the owner (see attached

Jim Osmundsen Donnelly + Co.

40 Scotchmans Ln, Vineyard Haven, MA 02568
/25
$24,000 total monthly price
- 3 Beds
- 2 Baths
- 1,257 Sq Ft
- House for Rent
5 Laurel Ave, Oak Bluffs, MA 02557

THIS IS A WEEKLY SUMMER RENTAL ONLY.THE WEEKLY PRICE IN AUGUST IS $6,500. PER WEEK.SEE WEB SITE FOR ADDITIONAL WEEKLY PRICING. Wonderful, fully redecorated Gingerbread house on East Chop, just minutes from the excitement of Oak Bluffs. There are three bedrooms and two full baths. The interior is clean and crisp, with beach cottage décor and beautiful bamboo floors. Entertainment options include

Karen Overtoom Karen M. Overtoom R.E.

5 Laurel Ave, Oak Bluffs, MA 02557
/56
$7,926,400 Sold Apr 28, 2025

32 Boldwater Rd, Edgartown, MA 02539
- 5 Beds
- 4.5 Baths
- 4,520 Sq Ft
- Built 1990
Last Sold Summary
- 7% Below List Price
- $1,754/SF
- 205 Days On Market
Last Listing Agent Robert Kenney Tea Lane Associates

32 Boldwater Rd, Edgartown, MA 02539

/29
Est $1,992,577 Not Listed For Sale
- 3 Beds
- 2 Baths
- 1,750 Sq Ft
165 W Tisbury Rd, Edgartown, MA 02539

165 W Tisbury Rd, Edgartown, MA 02539

/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
/30
$20,000 total monthly price
- 4 Beds
- 2 Baths
- 1,920 Sq Ft
- House for Rent
291 Barnes Rd Ob516, Oak Bluffs, MA 02557

THIS IS A WEEKLY SUMMER RENTAL ONLY.SEE WEB SITE FOR WEEKLY PRICING. Feel the ocean breezes from this classic waterfront home. There are four bedrooms, an open living room and dining room that open up to large deck overlooking beautiful views across the Lagoon. Walking path to private sandy beach. BOAT MOORING INCLUDED.

Karen Overtoom Karen M. Overtoom R.E.

291 Barnes Rd Ob516, Oak Bluffs, MA 02557
/34
$980,000 Sold Mar 26, 2025

11 Fairway Dr, Oak Bluffs, MA 02557
- 2 Beds
- 1 Bath
- 1,608 Sq Ft
- Built 1969
Last Sold Summary
- 18% Below List Price
- $609/SF
- 191 Days On Market
Current Estimated Value $1,040,446

Last Listing Agent Sandra Grymes Martha's Vineyard Island-Wide Realty

11 Fairway Dr, Oak Bluffs, MA 02557

/36
Est $2,309,579 Not Listed For Sale
- 6 Beds
- 3.5 Baths
- 2,705 Sq Ft
9 Heather Trail, Vineyard Haven, MA 02568

9 Heather Trail, Vineyard Haven, MA 02568

/31
$12,500,000
- 6 Beds
- 4 Baths
- 4,876 Sq Ft
44 Forest Rd, Vineyard Haven, MA 02568

Quintessential Seven Gates waterfront compound offering outstanding views and immediate beachfront access. This exceptional Martha’s Vineyard retreat includes a main residence and barn, thoughtfully designed and built by South Mountain Company. Immaculately maintained, both structures are virtually turn-key.The interiors showcase rich detail, the highest level of craftsmanship, and elegant

Bill Rossi Studio Realty

44 Forest Rd, Vineyard Haven, MA 02568
/14
$14,200 total monthly price
- 3 Beds
- 2 Baths
- 1,500 Sq Ft
- House for Rent
59 Prospect Ave Ob502, Oak Bluffs, MA 02557

THIS IS A WEEKLY SUMMER RENTAL ONLY. SEE WEB SITE FOR WEEKLY PRICING. This immaculate home is located in a quiet neighborhood that is just a bike ride's distance from several lovely beaches as well as the center of Oak Bluffs. The home offers open living spaces, generously proportioned sunny bedrooms and is well equipped.

Karen Overtoom Karen M. Overtoom R.E.

59 Prospect Ave Ob502, Oak Bluffs, MA 02557
/32
$1,250,000 Sold Nov 12, 2025

1054 State Rd, Vineyard Haven, MA 02568
- 6 Beds
- 2 Baths
- 1,845 Sq Ft
- Built 1881
Last Sold Summary
- 16% Below List Price
- $678/SF
- 60 Days On Market
Last Listing Agent Stephanie Roache Donnelly + Co.

1054 State Rd, 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

/7
$2,850,000
- Land
- 1.52 Acres
- $1,881,064 per Acre
39 Slough Cove Rd Unit 12.2 (part of), Edgartown, MA 02539

NEWLY LISTED | Build Your Katama Dream. Set in one of Martha’s Vineyard’s most sought-after locations, this newly created 1.5-acre parcel offers a rare opportunity to build your custom island retreat in the heart of Katama. Perfectly sited near the pristine shores of South Beach, the level and conforming R60 lot provides endless potential for a main residence and an outdoor oasis designed to your

Fran Agnoli The Agency

39 Slough Cove Rd Unit 12.2 (part of), Edgartown, MA 02539
/29
$18,000 total monthly price
- 4 Beds
- 2.5 Baths
- 2,027 Sq Ft
- House for Rent
12 Cottle Lane Ed341, Edgartown, MA 02539

THIS IS A WEEKLY SUMMER RENTAL ONLY.THE WEEKLY PRICE IN AUGUST IS $4,500. PER WEEK.SEE WEB SITE FOR ADDITIONAL WEEKLY PRICING. This four bedroom Victorian home is located close to the Edgartown Village for shopping, theater or restaurants. Walk to Fulton Street Beach. All new appliances have been added recently as well as a number of room AC units throughout the house.

Karen Overtoom Karen M. Overtoom R.E.

12 Cottle Lane Ed341, Edgartown, MA 02539
/31
$3,750,000 Sold Oct 31, 2025

29 Oxcart Rd, Aquinnah, MA 02535
- 3 Beds
- 2 Baths
- 1,274 Sq Ft
- Built 2009
Last Sold Summary
- 11% Below List Price
- $2,943/SF
- 380 Days On Market
Current Estimated Value $3,588,191

Last Listing Agent Michelle Kelly Tea Lane Associates

29 Oxcart Rd, Aquinnah, MA 02535

/14
Est $1,918,907 Not Listed For Sale
- 3 Beds
- 1.5 Baths
- 1,519 Sq Ft
2 Lexington Ave, Edgartown, MA 02539

2 Lexington Ave, Edgartown, MA 02539

/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
/40
$16,400 total monthly price
- 3 Beds
- 2 Baths
- 2,200 Sq Ft
- House for Rent
20 Katama Bay Rd Ed350, Edgartown, MA 02539

THIS IS A WEEKLY SUMMER RENTAL ONLY.THE WEEKLY PRICE IN AUGUST IS $4,100. PER WEEK.SEE WEB SITE FOR ADDITIONAL WEEKLY PRICING. Lovely Edgartown Bay Road area. This 3 bedroom newly decorated home is very close to South Beach. Easy access to town. Large grassy yard for the kids to play on.

Karen Overtoom Karen M. Overtoom R.E.

20 Katama Bay Rd Ed350, Edgartown, MA 02539
/42
$15,725,000 Sold Oct 22, 2025

111 N Water St, Edgartown, MA 02539
- 6 Beds
- 4.5 Baths
- 3,606 Sq Ft
- Built 1850
Last Sold Summary
- 5% Below List Price
- $4,361/SF
- 41 Days On Market
Last Listing Agent Wendy Harman Compass

111 N Water St, Edgartown, MA 02539

/26
Est $1,987,420 Not Listed For Sale
- 3 Beds
- 2 Baths
- 1,862 Sq Ft
82 South Rd, Chilmark, MA 02535

82 South Rd, Chilmark, MA 02535

/6
$3,895,000
- Land
- 0.53 Acre
- $7,349,057 per Acre
44 Plantingfield Way Unit 2, Edgartown, MA 02539

PRIME 0.5-ACRE BUILDING OPPORTUNITY WITH GRANDFATHERED GUEST HOUSE RIGHTS - Exceptional half-acre parcel offering a rare opportunity in a highly desirable location. This level, expansive lot provides an ideal foundation for a custom home, supported by ample frontage, favorable topography, and strong surrounding property values. A key advantage of this property is its grandfathered right to

David Dickinson Compass | Point B

44 Plantingfield Way Unit 2, Edgartown, MA 02539
/31
$50,000 total monthly price
- 5 Beds
- 5 Baths
- 2,975 Sq Ft
- House for Rent
17 Edgartown Bay Rd Ed328, Edgartown, MA 02539

THIS IS A WEEKLY SUMMER RENTAL ONLY.THE WEEKLY PRICE IN AUGUST IS $12,500. PER WEEK.SEE WEB SITE FOR ADDITIONAL WEEKLY PRICING. Private Beach, Waterfront, Mooring and Dock!! Spend your days looking at beautiful Katama Bay. Dock your boat or relax at your private beach. This large Classic Vineyard Home sleeps 10, has two living rooms, protected porch area and a really great front yard leading to

Karen Overtoom Karen M. Overtoom R.E.

17 Edgartown Bay Rd Ed328, Edgartown, MA 02539
/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

/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

/4
$1,875,000
- Land
- 0.56 Acre
- $3,348,214 per Acre
11A Duarte Cir, Edgartown, MA 02539

Nestled in the HEART OF KATAMA, this ready-to-build unique deep lot offers the opportunity to create your DREAM COMPOUND just minutes to Edgartown Center & South Beach. Set back on a pristine cul-de-sac this property provides unparalleled privacy for a home in Katama with a country vibe. The SIX BEDROOM COMPOUND allows a MAIN HOUSE, GUEST HOUSE, GARAGE and has amble space for outdoor entertaining

David White OwnerEntry.com

11A Duarte Cir, Edgartown, MA 02539
/30
$20,000 total monthly price
- 4 Beds
- 3 Baths
- 2,226 Sq Ft
- House for Rent
54 Schoolhouse Road Ed330, Edgartown, MA 02539

THIS IS A WEEKLY SUMMER RENTAL ONLY.THE WEEKLY PRICE IN AUGUST IS $5,000. PER WEEK.SEE WEB SITE FOR ADDITIONAL WEEKLY PRICING. Perfectly located close to South Beach and Edgartown is this absolutely wonderful 3 bedroom home with a separate guest quarters that has one twin bed and one full bed, kitchenette and bath. The main house has a formal dining room right off of the kitchen, a bright sunny

Karen Overtoom Karen M. Overtoom R.E.

54 Schoolhouse Road Ed330, Edgartown, MA 02539
/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

/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

Showing Results 201 - 240, Page 6 of 18

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