Dukes County, MA Homes

/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
/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
/42
$1,700,000 Sold Nov 03, 2025

35 Tower Ridge Rd, Oak Bluffs, MA 02557
- 3 Beds
- 4 Baths
- 2,558 Sq Ft
- Built 1986
Last Sold Summary
- 20% Below List Price
- $665/SF
- 118 Days On Market
Last Listing Agent Katherine Donahue Sandpiper Realty Inc

35 Tower Ridge Rd, Oak Bluffs, MA 02557

/22
Est $4,493,868 Not Listed For Sale
- 4 Beds
- 3 Baths
- 2,905 Sq Ft
1 Skippers View Ln, Aquinnah, MA 02535

1 Skippers View Ln, Aquinnah, MA 02535

/27
$9,250,000
- 5 Beds
- 7 Baths
- 4,078 Sq Ft
1 Field Club Dr, Edgartown, MA 02539

Nestled in the prestigious Field Club, this extraordinary five-bedroom compound epitomizes luxurious island living. This residence exudes timeless elegance and modern sophistication. Upon entering, the foyer sets the tone with a warm and inviting glow. The main level boasts an open-concept layout, featuring a gourmet chef's kitchen adorned with top-of-the-line appliances, granite countertops, and

Thomas Wallace Wallace & Co. Sotheby's

1 Field Club Dr, Edgartown, MA 02539
/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
/30
$1,995,000 Sold Aug 29, 2025

26 Box Turtle Ln, Oak Bluffs, MA 02557
- 4 Beds
- 3.5 Baths
- 2,891 Sq Ft
- Built 1980
Last Sold Summary
- $690/SF
- 5 Days On Market
Current Estimated Value $2,214,683

Last Listing Agent Jayne Isford Ocean Park Realty Inc

26 Box Turtle Ln, Oak Bluffs, MA 02557

/2
Est $1,809,608 Not Listed For Sale
- 3 Beds
- 2 Baths
- 1,250 Sq Ft
11 Deacon Vincent Way, Edgartown, MA 02539

11 Deacon Vincent Way, Edgartown, MA 02539

/27
$15,500,000
- 6 Beds
- 9 Baths
- 4,820 Sq Ft
68 N Water St, Edgartown, MA 02539

This expansive historic compound in the heart of Edgartown village offers the perfect blend of old-world charm and modern luxury. Just steps away from Edgartown’s finest restaurants and shops, this stunning property has been completely renovated by Stern McCafferty Architecture + Interiors, showcasing a harmonious balance of contemporary design and traditional architectural details. Upon

Thomas Wallace Wallace & Co. Sotheby's

68 N Water St, Edgartown, MA 02539
/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
/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
Last Listing Agent Sean Federowicz Landmarks at TODAY Real Estate

2 Flamingo Dr, Edgartown, MA 02539

/36
Est $2,445,864 Not Listed For Sale
- 4 Beds
- 3.5 Baths
- 2,791 Sq Ft
225 Great Plains Rd, Vineyard Haven, MA 02568

225 Great Plains Rd, Vineyard Haven, MA 02568

/3
$925,000
- 2 Beds
90 17th St N, Edgartown, MA 02539

90 Seventeenth Street NorthEdgartown, MassachusettsFOR SALEHere is a chance for you to own a water view property in Edgartown. Property is located just off the Boulevard on a quiet dead end lane. This property has been in the same family for decades and is now offered for sale. It is a blank canvas for you to create your dream home. Interior has been gutted and is ready for

Theodore Saulnier TAS Real Estate, LLC

90 17th St N, 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
/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 $2,137,544

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

1 Thames Ct, Edgartown, MA 02539

/39
Est $7,053,732 Not Listed For Sale
- 5 Beds
- 6 Baths
- 6,546 Sq Ft
103 Main St, Vineyard Haven, MA 02568

103 Main St, Vineyard Haven, MA 02568

/42
$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, sited on 2.2 acres, this serene property offers luxury and comfort, exuding tranquility and timeless charm. The main home spans three spacious levels with generous decks ideal for outdoor living and entertaining. The upper

Stephanie Roache Donnelly + Co.

97 Longview 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
$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 $939,197

Last Listing Agent Marilyn Moses Ocean Park Realty Inc

8 Rock Ave, Oak Bluffs, MA 02557

/34
Est $1,631,068 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

/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
/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
/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

/30
Est $1,894,663 Not Listed For Sale
- 3 Beds
- 3 Baths
- 2,046 Sq Ft
8 Harpoon Hollow, Aquinnah, MA 02535

8 Harpoon Hollow, Aquinnah, MA 02535

/7
$1,250,000 Pre-Foreclosure
- Land
- 1.62 Acres
- $771,605 per Acre
44 Iron Hill Rd, Oak Bluffs, MA 02557

Drive past bucolic horse pastures and Duartes Pond to a sweet neighborhood near the Alpaca Farm. This property at the end of a cul-de-sac on Iron Hill Road is filled with possibilities. This 1.6-acre lot has 60,000 sq ft+ and can therefore accommodate up to 6 bedrooms with the 10,000 sq ft per bedroom rule. There is a current home on the property is in need of renovations or start fresh and build

Cheri Mason LandVest MV

44 Iron Hill Rd, Oak Bluffs, MA 02557
/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
/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 $1,045,035

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

11 Fairway Dr, Oak Bluffs, MA 02557

/30
Est $2,494,673 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

/38
$4,500,000
- 4 Beds
- 3.5 Baths
- 2,836 Sq Ft
38 Pinehurst Rd, Edgartown, MA 02539

NEWLY BUILT 4-BEDROOM HOME WITH POOL – 10-Minute WALK TO TOWN,Enjoy modern living in this beautifully furnished, recently built 4-bedroom home featuring a heated saltwater pool and a stylish 20' x 30' entertainment barn—all just a short walk to downtown Edgartown.The home offers two floors of bright, elegant living space with 3.5 beautifully designed bathrooms, an open kitchen and family

Michele Casavant Vineyard Village Realty

38 Pinehurst Rd, 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
/30
$1,125,000 Sold Jan 06, 2025

19 Renear St, Vineyard Haven, MA 02568
- 4 Beds
- 3 Baths
- 1,901 Sq Ft
- Built 1985
Last Sold Summary
- 19% Below List Price
- $592/SF
- 109 Days On Market
Current Estimated Value $1,201,241

Last Listing Agent Michael Schweikert Ocean Park Realty, Inc.

19 Renear St, Vineyard Haven, MA 02568

/29
Est $2,077,297 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

/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
/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
/2
$1,695,000 Sold Jan 17, 2025

10 Combra Way, Oak Bluffs, MA 02557
- 3 Beds
- 3.5 Baths
- 2,200 Sq Ft
- Built 2013
Last Sold Summary
- $770/SF
- 13 Days On Market
Current Estimated Value $1,761,642

Last Listing Agent Rose Ryley Sandpiper Realty Inc

10 Combra Way, Oak Bluffs, MA 02557

/36
Est $2,282,590 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

/12
$1,995,000
- 2 Beds
- 1 Bath
- 879 Sq Ft
47 E Chop Dr Unit 4, Oak Bluffs, MA 02568

East Chop Harbor Front Luxury Condominiums -- This 2-bedroom, 2nd floor, waterfront condominium, the ''Tivoli'', features outstanding water views of the harbor and the sound beyond all the way to Chappaquiddick. Located just steps from the tennis club, beaches, restaurants, ferries to the mainland and downtown, this unit includes new kitchen with Bosch appliances, living and dining areas and a

Perry Patterson MV Luxury Homes, LLC

47 E Chop Dr Unit 4, Oak Bluffs, MA 02568
/17
$48,000 total monthly price
- 4 Beds
- 3.5 Baths
- 2,675 Sq Ft
- House for Rent
9 Thaxter Lane Ed310, Edgartown, MA 02539

THIS IS A WEEKLY SUMMER RENTAL ONLY.THE WEEKLY PRICE IN AUGUST IS $14,500. PER WEEK.SEE WEB SITE FOR ADDITIONAL WEEKLY PRICING. Enjoy the pool with this Stunning custom designed and professionally decorated Tri Level contemporary home with open floor plan. Once inside you will be captivated by the dramatic open spaces, soaring ceiling and walls of glass. Located in a high end neighborhood within

Karen Overtoom Karen M. Overtoom R.E.

9 Thaxter Lane Ed310, Edgartown, MA 02539
/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

Showing Results 201 - 240, Page 6 of 18

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