Dukes, MA Homes

/3
$110,000
- Land
- 0.70 Acre
- $157,143 per Acre
00 Eliot Ave Unit 17, Chilmark, MA 02535

Enjoy access to beautiful Stonewall Beach located in Chilmark. It has great swimming and fishing!This is not a buildable lot.

Julianna Flanders Flanders Real Estate

00 Eliot Ave Unit 17, Chilmark, MA 02535
/35
$22,000 per month
- 4 Beds
- 2 Baths
- 2,290 Sq Ft
- House for Rent
36 Henry Hough Lane Ch206, Chilmark, MA 02535

THIS IS A WEEKLY SUMMER RENTAL ONLY.THE WEEKLY PRICE IN AUGUST IS $5,500. PER WEEK.SEE WEB SITE FOR ADDITIONAL WEEKLY PRICING. Water views, 3 acres and stone walls. At the end of a lane, enjoy the privacy offered by 49 acres of conservation land complete with walking trails. This house is a short distance from Lucy Vincent beach, as well as from Menemsha and Squibnocket. This spacious four

Karen Overtoom Karen M. Overtoom R.E.

36 Henry Hough Lane Ch206, Chilmark, MA 02535
/13
$1,195,000 Sold May 22, 2025
- 1,110 Sq Ft
- $1077/SF
- 8 Days On Market
- 3 Beds
- 2 Baths
- Built 2006
34 10th St S, Edgartown, MA 02539

This charming 3 bedroom, 2 bathroom ranch-style Edgartown home offers comfortable single-level living with classic Vineyard appeal. The layout includes a dedicated living room, and an open kitchen and dining area. The primary suite features a private bath, while two additional bedrooms share a full bathroom. Outside, the property provides deck overlooking the yard for enjoying the outdoors.

Rose Ryley Sandpiper Realty Inc

34 10th St S, Edgartown, MA 02539

/10
Est $2,470,681 Not Listed For Sale
- 5 Beds
- 4 Baths
- 2,398 Sq Ft
87 Bellevue Ave, Vineyard Haven, MA 02568

87 Bellevue Ave, Vineyard Haven, MA 02568

/26
$3,695,000
- Land
- 7 Acres
- $551,493 per Acre
32 Stonewall Road and 4 Cedar Ln Unit 2.1 and 2.2, Chilmark, MA 02535

Discover an exceptional opportunity with this rare combination of two abutting parcels spanning more than 6 acres in a coveted location offering water views and Atlantic Ocean private beach access. Surfers and fishermen delight in this location! The Stonewall Association is a beloved area of Chilmark in a supreme location for easy Chilmark living close to the Chilmark Store, the Chilmark

Jill Napior Tea Lane Associates

32 Stonewall Road and 4 Cedar Ln Unit 2.1 and 2.2, Chilmark, MA 02535
/29
$34,000 per month
- 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
/36
$5,500,000 Sold May 20, 2025
- 3,262 Sq Ft
- $1686/SF
- 295 Days On Market
- 4 Beds
- 5 Baths
- Built 1984
12 Tamarack Ln, Oak Bluffs, MA 02536

This bright and sunny home has a spectacular waterview overlooking the Eighth Fairway of Farm Neck Golf Course, Sengekontacket Pond and Nantucket Sound. Professionaly designed landscaping with perennial beds and charming brick courtyard add to its ambiance. Included are Farm Neck Golf Club stockholder membership (meaning immediate entry into golf membership), tennis and dock & mooring privileges.

Betsy Kessler Rutledge Properties

12 Tamarack Ln, Oak Bluffs, MA 02536

/36
Est $2,520,452 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

/8
$3,200,000
- Land
- 19 Acres
- $165,803 per Acre
32 Edgartown - West Tisbury Rd Unit 81, West Tisbury, MA 02575

A Rare Offering in West Tisbury — Over 19 Acres of OpportunityAn exceptional opportunity to own just over 19 acres in the heart of rural West Tisbury. This expansive parcel offers tremendous flexibility, with potential for multiple dwellings or subdivision into a thoughtfully designed niche development. Ideally situated near all island towns, the property is also just minutes from the

Jill Napior Tea Lane Associates

32 Edgartown - West Tisbury Rd Unit 81, West Tisbury, MA 02575
/20
$20,000 per month
- 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
/45
$1,225,000 Sold May 19, 2025
- 1,725 Sq Ft
- $710/SF
- 338 Days On Market
- 3 Beds
- 2 Baths
- Built 1986
51 Head of the Pond Rd, Vineyard Haven, MA 02568

Iron Hill, Centrally located with convenient access to Island villages. 3 Bedroom, 2 Bath Ranch on 1.5+ acres. An empty canvas with limitless possibilities. Mature landscaping designed for privacy, aesthetics, and low maintenance. Paved private road access, with generous setback for residence. Bike path, Bus stop, State Forest, & Walking Trails nearby. Association covenants allow up to two

Bruce Stuart Bruce Stuart and Associates

51 Head of the Pond Rd, Vineyard Haven, MA 02568

/39
Est $6,712,733 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

/33
$1,350,000
- 3 Beds
- 3 Baths
- 1,900 Sq Ft
145 Sandpiper Ln Unit 10, Vineyard Haven, MA 02568

Enjoy effortless island living in this beautifully renovated 3-bedroom, 2.5-bath condo, tucked within a quiet and well-maintained association. Thoughtfully updated with modern finishes and quality craftsmanship, this spacious unit offers comfort, style, and functionality. The open-concept living area features a cozy wood pellet fireplace, perfect for cooler evenings, and flows seamlessly into a

Emily Flake Viewpoints

145 Sandpiper Ln Unit 10, Vineyard Haven, MA 02568
/29
$64,000 per month
- 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
$1,850,000 Sold May 19, 2025
- 1,428 Sq Ft
- $1296/SF
- 158 Days On Market
- 3 Beds
- 2.5 Baths
- Built 1982
18 Katama Dr, Edgartown, MA 02539

Ocean views - Nestled on a quiet corner lot, this classic beach house offers a reverse floor plan and distant views of the Atlantic Ocean over the Katama Plain . The upper level features the common living space including the dining area, kitchen, living room with fireplace, and large powder room. The lower level is where you find the more private spaces, including the primary bedroom suite plus

Bonnie Pierce Wallace & Co. Sotheby's International Realty

18 Katama Dr, Edgartown, MA 02539

/34
Est $1,628,990 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

/13
$6,750,000
- Land
- 2.11 Acres
- $3,199,052 per Acre
5 Atlantic Dr Unit 5.2, Edgartown, MA 02539

Located in one of Katama’s most coveted neighborhoods, this 2.11-acre parcel offers stunning ocean views and a direct path to South Beach. Surrounded by high-end homes and just minutes from Edgartown Village, it’s an ideal setting for a custom-built retreat with room for a four bedroom residence with pool and views over the dunes. A rare opportunity to own in this prestigious coastal enclave.

Deb Levin Studio Realty

5 Atlantic Dr Unit 5.2, Edgartown, MA 02539
/25
$24,000 per month
- 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
$1,200,000 Sold May 19, 2025
- 2,080 Sq Ft
- $577/SF
- 590 Days On Market
- 3 Beds
- 2 Baths
- Built 1972
193 Franklin Terrace, Vineyard Haven, MA 02568

Perched on a sunny sloping lot, this 3-bedroom, 2-bath year-round home in a quiet established neighborhood is walking distance to the heart of town and close to everything. Septic can accommodate 4 bedrooms. Deck with grilling area and outdoor shower looking over the landscaped side yard. On the main level, open kitchen with a large island. On the lower level, 3 bedrooms, 2 have walkout access. A

Claire Callagy Compass

193 Franklin Terrace, Vineyard Haven, MA 02568

/30
Est $1,840,649 Not Listed For Sale
- 3 Beds
- 3 Baths
- 2,046 Sq Ft
8 Harpoon Hollow, Aquinnah, MA 02535

8 Harpoon Hollow, Aquinnah, MA 02535

/26
$1,700,000
- 2 Beds
- 0.5 Baths
- 601 Sq Ft
108 Bay View Ave, Edgartown, MA 02539

Enchanting 2-bed waterfront cottage in Edgartown's coveted Chappaquiddick neighborhood, Martha's Vineyard. Exuding coastal charm, it features old boat masts as columns, decor from washed-up treasures, and a historic silo from Sweetened Water Farm, rebuilt as a unique bedroom wing. The silo hosts a cozy bedroom on the first level and a second bedroom on the upper level, offering breathtaking

Derick Freitas Amaral & Associates Real Estate

108 Bay View Ave, Edgartown, MA 02539
/30
$20,000 per month
- 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
/26
$1,850,000 Sold May 14, 2025
- 2,610 Sq Ft
- $709/SF
- 8 Days On Market
- 5 Beds
- 4 Baths
- Built 1986
137 Charles Neck Way, Vineyard Haven, MA 02568

Fantastic opportunity to buy a two house compound in West Tisbury close to Long Point Beach access. A perfect investment, rental income generator or to host extended family and guests.Two well built houses on 1.6 acres, that have been impeccably maintained by the original owner. Offering a total of 5 bedrooms, 4 bathrooms, 2 outdoor showers and 2 garages. There is a charming garden shed and low

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

137 Charles Neck Way, Vineyard Haven, MA 02568

/30
Est $2,481,221 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

/26
$1,700,000
- Land
- 0.96 Acre
- $1,770,833 per Acre
108 Bay View, Edgartown, MA 02539

Enchanting 2-bed waterfront cottage in Edgartown's coveted Chappaquiddick neighborhood, Martha's Vineyard. Exuding coastal charm, it features old boat masts as columns, decor from washed-up treasures, and a historic silo from Sweetened Water Farm, rebuilt as a unique bedroom wing. The silo hosts a cozy bedroom on the first level and a second bedroom on the upper level, offering breathtaking

Derick Freitas Amaral & Associates RE

108 Bay View, Edgartown, MA 02539
/14
$14,200 per month
- 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
/39
$4,762,500 Sold May 14, 2025
- 5,103 Sq Ft
- $933/SF
- 411 Days On Market
- 6 Beds
- 6 Baths
- Built 2024
69 Division Rd, Edgartown, MA 02539

Welcome to BRAND NEW CONSTRUCTION!! This gorgeous home sits on a spacious lot in a new 5 home luxury private enclave with breathtaking views of the surrounding pastures. The property offers privacy, a serene and picturesque setting, perfect for those seeking tranquility and natural beauty yet a convenient 1.6 mile distance to Edgartown Village. With meticulous attention to detail, this home

Jennifer DaSilva Compass | Point B

69 Division Rd, Edgartown, MA 02539

/29
Est $2,030,599 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

/13
$1,150,000
- Land
- 2.02 Acres
- $569,307 per Acre
00 Old Field Rd, Aquinnah, MA 02535

The nearby roar of the Atlantic can be heard from this pristine two-acre building opportunity in Aquinnah, ideally located at the end of Old Field Road with easy access from Moshup Trail. A storybook walking path through woods and fields over an easement bordering a majestic beetlebung grove and over a bubbling stream, leads directly to the entrance of cherished Philbin Beach. A thoughtfully

Katherine Donahue Sandpiper Realty Inc

00 Old Field Rd, Aquinnah, MA 02535
/28
$38,000 per month
- 4 Beds
- 3.5 Baths
- 3,000 Sq Ft
- House for Rent
17 Otis Bassett Rd, West Tisbury, MA 02575

THIS IS A WEEKLY RENTAL NOT MONTHLY. AUGUST WEEKLY IS $9,500. SEE OUR WEB SITE FOR WEEKLY PRICING!!!!!Are you looking for the perfect back yard Oasis? Well here it is!! Surrounding a large pool you will be able to relax on the expansive deck areas that include plenty of space for gathering. Inside is an amazing kitchen with every amenity you could want. Coffee lovers will appreciate a regular

Karen Overtoom Karen M. Overtoom R.E.

17 Otis Bassett Rd, West Tisbury, MA 02575
/6
$4,200,000 Sold May 09, 2025
- 3,600 Sq Ft
- $1167/SF
- 11 Days On Market
- 4 Beds
- 4 Baths
- Built 2024
20 Mill Hill Rd, Edgartown, MA 02539

NEW CONSTRUCTION, with POOL, walking distance to EDGARTOWN VILLAGE! Approx. 3,600 square feet of open living space. The Great Room has a dramatic Two Story wall of glass, (sliders and an oversized second story window) that overlooks the 14 x 30 foot IN GROUND POOL. In addition to the dramatic Great Room there is a first floor den/lounge area, a first floor primary-en-suite with views to the pool,

Michele Casavant Vineyard Village Realty

20 Mill Hill Rd, Edgartown, MA 02539

/36
Est $2,245,934 Not Listed For Sale
- 6 Beds
- 4 Baths
- 2,705 Sq Ft
9 Heather Trail, Vineyard Haven, MA 02568

9 Heather Trail, Vineyard Haven, MA 02568

/21
$1,675,000
- 3 Beds
- 2 Baths
- 1,562 Sq Ft
111 Charles Neck Way, Vineyard Haven, MA 02568

Tucked away on 1.6 wooded acres in West Tisbury, this classic Cape-style home offers both privacy and convenience, with easy access to the charm of Up-Island and the amenities of Down-Island. Located on a paved road near Long Point Beach, it also includes coveted access to Lambert's Cove Beach. The bright, open interior features a living and dining area with a wood-burning fireplace, a kitchen

Emma Kennedy Sandpiper Realty Inc

111 Charles Neck Way, Vineyard Haven, MA 02568
/8
$18,000 per month
- 3 Beds
- 2.5 Baths
- House for Rent
71 Bartmus Luce Road Wt154, West Tisbury, MA 02575

THIS IS A WEEKLY SUMMER RENTAL ONLY.THE WEEKLY PRICE IN AUGUST IS $5,000. PER WEEK.SEE WEB SITE FOR ADDITIONAL WEEKLY PRICING. Finest Views on the Island!! This house is set high on a hill surrounded by nature. The expansive views from the front of this house are spectacular. Enjoy the large deck or the screened porch and gaze upon one of the most amazing Vineyard Views available. It is a short

Karen Overtoom Karen M. Overtoom R.E.

71 Bartmus Luce Road Wt154, West Tisbury, MA 02575
/19
$1,110,000 Sold May 08, 2025
- 1,275 Sq Ft
- $871/SF
- 45 Days On Market
- 2 Beds
- 2 Baths
- Built 1972
31 9th St N, Edgartown, MA 02539

Nestled among the trees near the Sengekontacket Pond, this distinctive contemporary home offers privacy while being conveniently close to Downtown Edgartown and the picturesque trails at Felix Neck Sanctuary. Designed by architect Robert Orr, this multi-level residence showcases unique architectural details and striking angled ceilings.The main living area is bathed in natural light, surrounded

Alyssa Halisky Wallace & Co. Sotheby's

31 9th St N, Edgartown, MA 02539

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

43 Look St, Vineyard Haven, MA 02568

/35
$2,010,900
- 4 Beds
- 5 Baths
- 2,518 Sq Ft
32 Norton Orchard Rd, Edgartown, MA 02539

Discover this Edgartown gem! Enjoy a refreshed interior with new flooring, a bright updated bathroom, and modern LED lighting throughout. The kitchen boasts elegant dark green granite countertops. A solid foundation provides peace of mind. The property offers easy access to a nearby restaurant, apartments, and a clothing store, enhancing your daily convenience. **SELLER ASSISTED BY POA. DO NOT

Derek Greene The Greene Realty Group

32 Norton Orchard Rd, Edgartown, MA 02539
/22
$3,000 per month
- 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
/6
$700,500 Sold May 07, 2025
- Land
- 0.55 Acre
- $1,273,636 per Acre
- 0 Days On Market
72 Windsor Dr Unit 99.71, Edgartown, MA 02539

Level building lot ready for your new home ideas. Area of well cared for homes both year round and seasonal use. Bike path at end of street allows easy travel to all down island towns. Ask about a new home package or work with your own builder. Perc test has been done and confirmed it is a 4 bedroom lot with a standard septic design.

Jim Joyce Carroll & Vincent R.E.

72 Windsor Dr Unit 99.71, Edgartown, MA 02539

/14
Est $2,001,334 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

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