Dukes, MA Homes

/39
$2,745,000
- 3 Beds
- 2 Baths
- 1,350 Sq Ft
31 The Blvd, Edgartown, MA 02539

Waterfront Charmer on Sengekontacket Pond - Perched on the shoreline, this contemporary cottage is enveloped by stone walls, lush gardens, and stunning water views. Inside, a bright, airy living space features an open dining area and a well-appointed kitchen. The all-white interior is complemented by hardwood floors, vaulted ceilings, skylights, air conditioning, and ceiling fans. Three sliding

Wendy Harman

Compass

(508) 301-9323

31 The Blvd, Edgartown, MA 02539
/12
$6,180 per month
- 3 Beds
- 3.5 Baths
- 1,872 Sq Ft
- House for Rent
44 Music St Wt153, West Tisbury, MA 02575

PLEASE TAKE NOTE!!!!!THIS IS A WEEKLY SUMMER RENTAL NOT A MONTHLY RENTAL. THE PRICE ON THIS LISTING IS A WEEkLY PRICE!!!!!!!

Karen Overtoom Karen M. Overtoom R.E.

44 Music St Wt153, West Tisbury, MA 02575
/32
$1,100,000 Sold Jun 27, 2025
- 1,976 Sq Ft
- $557/SF
- 156 Days On Market
- 4 Beds
- 2.5 Baths
- Built 1985
10 Kims Way, Oak Bluffs, MA 02568

Located under a mile from downtown Oak Bluffs, this well-maintained 4-bedroom home includes a 3-bedroom main house and a 1-bedroom basement apartment. Recent upgrades include a new roof, Title V septic system, electric service, and town water connection. The first floor features a spacious living/dining area, kitchen, half bath, and a cozy den. Upstairs are 3 bedrooms and a full bath. The

Michael Schweikert Ocean Park Realty, Inc.

10 Kims Way, Oak Bluffs, MA 02568

/20
Est $1,495,511 Not Listed For Sale
- 2 Beds
- 1 Bath
- 1,084 Sq Ft
20 Oakdale Dr, Edgartown, MA 02539

20 Oakdale Dr, Edgartown, MA 02539

/27
$1,695,000
- 3 Beds
- 2.5 Baths
- 1,740 Sq Ft
27 Chapde Ln, Tisbury, MA 02568

Classic Style Meets Timeless Charm - Located at the end of a lightly traveled lane and surrounded by stunning gardens and stone retaining walls, this residence provides a modern and spacious environment for comfortable island living. The home welcomes you with an open and bright layout, featuring sleek finishes and an abundance of natural light. The gourmet kitchen is a chef's delight that

Wendy Harman

Compass

(508) 691-8993

27 Chapde Ln, Tisbury, MA 02568
/12
$15,000 per month
- 5 Beds
- 6.5 Baths
- 4,137 Sq Ft
- House for Rent
41 Naushon Rd Wt116, Aquinnah, MA 02575

Stunning water views from this expansive beachfront estate in Makonikey off Lambert's Cove Rd. Enjoy the large living area with comfortable couches, floor to ceiling windows and french doors for seamless indoor to outdoor living and dining. There is a fully equipped kitchen. Some folks will enjoy the treadmill and elliptical while watching boats pass by or even play squash in the indoor squash

Karen Overtoom Karen M. Overtoom R.E.

41 Naushon Rd Wt116, Aquinnah, MA 02575
/29
$1,970,000 Sold Jun 26, 2025
- 1,410 Sq Ft
- $1397/SF
- 0 Days On Market
- 3 Beds
- 3 Baths
- Built 1973
493 Katama Rd Unit E2, Edgartown, MA 02539

Welcome to your dream getaway—a beautifully renovated 3-level townhouse boasting breathtaking waterviews of Katama Bay and the Atlantic Ocean. Every inch of this townhouse has been thoughtfully reimagined with the relaxed charm of a beach house.As part of the Mattakesett resort, you’ll enjoy access to a wealth of amenities including tennis courts, swimming pools, a fitness center, on-site

Bonnie Pierce Wallace & Co. Sotheby's

493 Katama Rd Unit E2, Edgartown, MA 02539

/32
Est $1,940,724 Not Listed For Sale
- 3 Beds
- 2 Baths
- 1,448 Sq Ft
81 Washque Ave, Edgartown, MA 02539

81 Washque Ave, Edgartown, MA 02539

/42
$5,750,000
- 4 Beds
- 4.5 Baths
- 3,643 Sq Ft
4 Somerset Ln, Edgartown, MA 02539

New Construction: Reimagined Island Living At Somerset. Located in Katama, Somerset is an exclusive five-home luxury enclave perfectly located between Edgartown Village and South Beach -- and developed by Stanmar, owners of the Winnetu Oceanside Resort. The home sites have been designed to maximize outdoor living and entertaining around a spacious and private yard with expansive lawns and room

Wendy Harman

Compass

(508) 715-9594

4 Somerset Ln, Edgartown, MA 02539
/11
$20,000 per month
- 4 Beds
- 4.5 Baths
- 2,306 Sq Ft
- House for Rent
3 E Pasture Ln, Aquinnah, MA 02535

THIS PROPERTY IS A WEEKLY RENTAL PROPERTY!! Breathtaking water views from this contemporary home located on Menemsha Pond and recently renovated with new kitchen and baths. This four bedroom retreat offers the perfect place to come during the summer months or even enjoy during the shoulder season while sitting by the fire with a warm cup of your favorite hot beverage. PLEASE TAKE NOTE!!!!!THIS IS

Karen Overtoom Karen M. Overtoom R.E.

3 E Pasture Ln, Aquinnah, MA 02535
/22
$1,299,000 Sold Jun 25, 2025
- 1,512 Sq Ft
- $859/SF
- 77 Days On Market
- 3 Beds
- 2 Baths
- Built 1984
2 Boylston Dr, Edgartown, MA 02539

Edgartown: MOVE IN READY! Stylish 3-bedroom 2 bath home with inviting and charming floor plan integrates comfort and function. Cathedral ceilings with skylight and 2 sets of sliders providing natural light and a bright open floor plan.Updated kitchen with breakfast bar and dining area. 1st Floor bedroom. Full bathroom and spacious living room perfect for gatherings and relaxing. There is

Martha Smith C McManus Realty Group

2 Boylston Dr, Edgartown, MA 02539

/31
Est $3,145,737 Not Listed For Sale
- 4 Beds
- 3 Baths
- 2,300 Sq Ft
68 Meeting House Rd, Chilmark, MA 02535

68 Meeting House Rd, Chilmark, MA 02535

/32
$985,000
- 2 Beds
- 1 Bath
- 990 Sq Ft
37 Circuit Ave Unit 4, Oak Bluffs, MA 02557

Downtown Oak Bluffs Located right in the heart of town. Unit #4 A penthouse condo with a semi-private rooftop deck (shared with unit 5 only). This spacious condo has a panoramic view of the town and surrounding waters sitting high above it all with outdoor seating and separate entrances from either condo. This solid deck adds a whole other dimension to this already desirable unit.The interior

Lisa Lucier

Anchor Realty of Martha's Vineyard

(508) 514-5238

37 Circuit Ave Unit 4, Oak Bluffs, MA 02557
/8
$8,250 per month
- 7 Beds
- 5 Baths
- 3,528 Sq Ft
- House for Rent
227 S Gate Rd Wt120, West Tisbury, MA 02575

THIS PROPERTY IS A WEEKLY PROPERTY!! Set on 12 acres of peaceful woods, meadows, stone walls and its own pond, this charming 18th century 4 bedroom farmhouse and 3 bedroom rustic barn sleeps 12 and is perfect for larger groups wanting peace and tranquility all within a short distance to private swimming beaches. The setting, on exclusive Seven Gates Farm, offers miles of sandy trails through

Karen Overtoom Karen M. Overtoom R.E.

227 S Gate Rd Wt120, West Tisbury, MA 02575
/29
$1,925,000 Sold Jun 24, 2025
- 2,378 Sq Ft
- $810/SF
- 0 Days On Market
- 3 Beds
- 3 Baths
- Built 1928
21 William St, Vineyard Haven, MA 02568

Nestled at the quiet end of William Street, just moments from the lively charm of downtown Vineyard Haven, this delightful 3-bedroom home offers the perfect blend of comfort and convenience. The spacious primary suite is thoughtfully located on the main level, providing both privacy and ease of living. Inside, an open and airy floor plan combines timeless character with modern touches—ideal for

Laura Finney Wallace & Co. Sotheby's

21 William St, Vineyard Haven, MA 02568

/7
Not Listed For Sale
- 4 Beds
53 N Neck Rd, Edgartown, MA 02539

53 N Neck Rd, Edgartown, MA 02539

/38
$4,195,000
- 3 Beds
- 4 Baths
- 3,426 Sq Ft
96 Hammett Ln, Chilmark, MA 02535

This beautifully designed and built Post & Beam style home is tastefully thought out and meticulously maintained. The open living, dining and kitchen feature custom built-ins, a wood burning fireplace and a fabulous gourmet kitchen with Wolfe 8 burner professional style stove, Sub Zero refrigerator, Boshe dishwasher soapstone counters and a butlers pantry with extra cupboards, shelving and a wine

Brenda Galligan Karen M. Overtoom R.E.

96 Hammett Ln, Chilmark, MA 02535
/8
$18,500 per month
- 4 Beds
- 3.5 Baths
- 1,714 Sq Ft
- House for Rent
4 Windy Way Wt143, West Tisbury, MA 02575

THIS PROPERTY IS A WEEKLY RENTAL PROPERTY!! The 3.3 acre private setting is most picturesque with its positioning in private Upper Makonikey , the long circular driveway , its grassy lawn, and rolling landscape fields . Only a short distance away is over 3,000 feet of PRIVATE sandy association Beaches , directly below , with two nearby parking lot access-ways . Nestled onto this promontory is a

Karen Overtoom Karen M. Overtoom R.E.

4 Windy Way Wt143, West Tisbury, MA 02575
/26
$1,000,000 Sold Jun 24, 2025
- 1,202 Sq Ft
- $832/SF
- 254 Days On Market
- 2 Beds
- 2 Baths
- Built 1987
17 Meetinghouse Village Way, Edgartown, MA 02539

KATAMA CONDOMINIUM IN MEETINGHOUSE VILLAGE - A bright and sunny center unit with an open floor plan, vaulted ceilings, skylights, and windows that fill the space with natural light. This home is in excellent condition, showing the pride of ownership. The wide-open kitchen with a breakfast bar offers a wonderful space for cooking and entertaining. Accommodations include a first-floor bedroom with

Leslie C. Floyd Portfolio Real Estate, Inc.

17 Meetinghouse Village Way, Edgartown, MA 02539

/14
Est $5,464,361 Not Listed For Sale
- 4 Beds
- 3 Baths
- 3,193 Sq Ft
100 Meetinghouse Way, Edgartown, MA 02539

100 Meetinghouse Way, Edgartown, MA 02539

/21
$3,250,000
- 4 Beds
- 3 Baths
- 2,758 Sq Ft
382 Lighthouse Rd, Aquinnah, MA 02535

Spacious contemporary set high off Lighthouse Road with unobstructed, amazing water views of the Vineyard Sound and Elizabeth Islands. Open concept design with soaring ceilings and modern architecture. A retreat for all seasons this house is fully insulated, heated and has central air. A center island in the kitchen ensures the cook of the family does not miss out on the amazing sunsets. Ground

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

382 Lighthouse Rd, Aquinnah, MA 02535
/2
$10,000 per month
- 6 Beds
- 3.5 Baths
- 2,100 Sq Ft
- House for Rent
15 Crowell Lane Wt119, West Tisbury, MA 02575

THIS IS A WEEKLY RENTAL NOT A MONTHLY!!!!!!!Seven Gates Farm. This property has three ponds, overlooks rolling meadows and is very charming. Located in Seven Gates Farm association, the property affords access to association tennis and two miles of private beach as well as miles of walking trails. Bookings for tennis are available at the office for a slight fee.There is a $25 trash charge per

Karen Overtoom Karen M. Overtoom R.E.

15 Crowell Lane Wt119, West Tisbury, MA 02575
/7
$600,000 Sold Jun 23, 2025
- Land
- 0.50 Acre
- $1,200,000 per Acre
- 4 Days On Market
27 7th St N Unit 198, Edgartown, MA 02539

This .5-acre lot is located in a favorable Edgartown neighborhood with proximity to the bike path, public transportation, and close to town. The property has been staked and perc tested, and will support 2 bedrooms with a standard Title V septic system or 3 bedrooms with an advanced treatment system. Information should be verified by the Edgartown Board of Health Department. Embrace the unique

Stephanie Roache Donnelly + Co

27 7th St N Unit 198, Edgartown, MA 02539

/2
Est $1,376,724 Not Listed For Sale
- 3 Beds
- 3 Baths
- 1,400 Sq Ft
45 Pine Tree Ln, Vineyard Haven, MA 02568

45 Pine Tree Ln, Vineyard Haven, MA 02568

/41
$3,600,000
- 3 Beds
- 4 Baths
- 2,500 Sq Ft
27 Clambelly Rd, Chilmark, MA 02535

A place of serenity tucked in the woods of Chilmark. Complete renovation 2017/2018, large fenced in back yard with exquisite fish pond with waterfall and lighting. Kitchen has concrete countertops, sub zero refrigerator, Wolf Oven & Speed Oven. Large open formal dining area and open formal sitting area with fireplace. Beautiful reclaimed wood flooring. LED lighting throughout house, Media

Julianna Flanders Flanders Real Estate

27 Clambelly Rd, Chilmark, MA 02535
/8
$4,800 per month
- 3 Beds
- 3 Baths
- 3,279 Sq Ft
- House for Rent
165 Christiantown Rd, West Tisbury, MA 02575

THIS PROPERTY IS A WEEKLY PROPERTY!! The home is set on six beautifully landscaped acres with original stone walls. It is located in private historic Christiantown on the North Shore, a short distance from both Lambert’s Cove Beach and Cedar Tree Neck Wildlife Reserve. Cedar Tree is a habitat with tumbling streams and freshwater ponds, sandy beaches and rocky cliffs, tall oaks and cool beech

Karen Overtoom Karen M. Overtoom R.E.

165 Christiantown Rd, West Tisbury, MA 02575
/6
$600,000 Sold Jun 23, 2025
- Land
- 0.50 Acre
- $1,200,000 per Acre
- 4 Days On Market
27 7th St N, Edgartown, MA 02539

This .5-acre lot is located in a very favorable Edgartown neighborhood with proximity to the bike path, public transportation, and close to town. The property has been staked and perc tested, and will support 2 bedrooms with a standard Title V septic system or 3 bedrooms with an advanced treatment system. Information should be verified by the Edgartown Board of Health Department. Embrace the

Stephanie Roache Donnelly + Co.

27 7th St N, Edgartown, MA 02539

/36
Est $1,729,259 Not Listed For Sale
- 4 Beds
- 3 Baths
- 2,122 Sq Ft
62 Whalers Walk, Edgartown, MA 02539

62 Whalers Walk, Edgartown, MA 02539

/52
$3,950,000
- 5 Beds
- 7 Baths
- 4,372 Sq Ft
139 Main St, Vineyard Haven, MA 02568

Nestled just two blocks from Vineyard Haven’s working harbor, 139 Main Street is a quietly grand in-town property with the feel of a private estate. Once two separate addresses—now gracefully combined into a single half-acre parcel—this home offers rare space, privacy, and timeless character in one of the island’s most approachable villages.From the moment you step through the welcoming

Leslie C. Floyd Portfolio Real Estate, Inc.

139 Main St, Vineyard Haven, MA 02568
/8
$19,000 per month
- 5 Beds
- 5 Baths
- 3,137 Sq Ft
- House for Rent
19 Morse St, Edgartown, MA 02539

THIS PROPERTY IS A WEEKLY RENTAL PROPERTY!! Newly renovated historical home in the heart of Edgartown Village, close to Fuller Street & Lighthouse Beaches. Beautifully designed interior with open gourmet kitchen and pickled hardwood floors, marble countertops, top of the line appliances and a large center island. Cozy family room with fireplace, formal living room, office/den and a full bath all

Karen Overtoom Karen M. Overtoom R.E.

19 Morse St, Edgartown, MA 02539
/47
$1,595,500 Sold Jun 23, 2025
- 1,822 Sq Ft
- $876/SF
- 73 Days On Market
- 5 Beds
- 3 Baths
- Built 2003
21 Coffins Field Rd, Edgartown, MA 02539

EDGARTOWN SOUTH SHORE BEACH HOUSE. Imagine a countryside abode with nearby access to a pristine south shore stretch of beach and less than 6 miles to Edgartown Village and Harbor. Architect-designed as a low-key getaway, this delightful five bedroom year-round home has three full bathrooms plus a freestanding outdoor shower, decks, screened-in porch and is comfortably sited in an established well

Helena Kirschenbaum Studio Realty

21 Coffins Field Rd, Edgartown, MA 02539

/36
Est $2,321,551 Not Listed For Sale
- 4 Beds
- 3 Baths
- 2,436 Sq Ft
377 State Rd, Vineyard Haven, MA 02568

377 State Rd, Vineyard Haven, MA 02568

/15
$2,770,000
- 3 Beds
- 2 Baths
- 1,540 Sq Ft
5 Ocean View Farm Rd, Chilmark, MA 02535

Designed by the famous mid century architect Andrew Geller, this contemporary home is situated at the top of the parcel with ocean views and a glimpse of Chilmark pond. There is ample open space to accommodate family and friends and overlooks the large meadow which follows the stone wall to South Road. Access to walking trails, and Lucy Vincent Beach is a short distance away.

Natalie Conroy Conroy & Company R.E., Inc.

5 Ocean View Farm Rd, Chilmark, MA 02535
/8
$4,500 per month
- 2 Beds
- 2 Baths
- 1,393 Sq Ft
- House for Rent
33 Menemsha Inn Rd Ch223 3, Chilmark, MA 02535

THIS IS A WEEKLY RENTAL PROPERTY!! This spacious two bedroom home is filled with classic Vineyard charm. Each room features spectacular views overlooking Vineyard Sound, as well as stellar sunsets in the evening. Close to Menemsha Village and public beach as well as access to Lucy Vincent and Squibnocket beaches.

Karen Overtoom Karen M. Overtoom R.E.

33 Menemsha Inn Rd Ch223 3, Chilmark, MA 02535
/25
$949,000 Sold Jun 23, 2025
- 1,012 Sq Ft
- $938/SF
- 49 Days On Market
- 3 Beds
- 1.5 Baths
- Built 1986
345 Franklin St, Vineyard Haven, MA 02568

Charming Cape-style home in Vineyard Haven, ideally located just minutes from Downtown and Owen Little Beach. This well-maintained property sits on a 0.26-acre lot, offering a private back deck, a spacious yard, and an outdoor shower perfect for after beach days. The home boasts 3 bedrooms and 1.5 bathrooms, with a thoughtful layout that includes a bedroom on the first floor and two on the

Alyssa Halisky Wallace & Co. Sotheby's International Realty

345 Franklin St, Vineyard Haven, MA 02568

/36
Est $3,864,042 Not Listed For Sale
- 6 Beds
- 4.5 Baths
- 3,902 Sq Ft
94 Marthas Rd, Edgartown, MA 02539

94 Marthas Rd, Edgartown, MA 02539

/47
$2,675,000
- 6 Beds
- 5 Baths
- 2,970 Sq Ft
128 & 136 Spring St, Vineyard Haven, MA 02568

A Rare Compound Opportunity in the Heart of Vineyard Haven - 128 & 136 Spring Street—two adjacent properties being sold together to create a unique, flexible compound just moments from the Tisbury School and downtown Vineyard Haven. With a spacious main residence and a separate guest house, this rare combination presents a compelling opportunity for multigenerational living, seasonal enjoyment,

David Dickinson Compass | Point B

128 & 136 Spring St, Vineyard Haven, MA 02568
/8
$8,000 per month
- 4 Beds
- 4.5 Baths
- 3,600 Sq Ft
- House for Rent
56 Chilmark Rd, Chilmark, MA 02535

THIS PROPERTY IS A WEEKLY RENTAL PROPERTY!! This slice of paradise in the coveted Seven Gates Association gives you access to two miles of private beach just half a mile away, with tennis courts also nearby and 1000 acres of conservation land. The house is exquisitely crafted, well maintained and beautifully landscaped. Views of Harlock's pond are visible from the kitchen, living area and

Karen Overtoom Karen M. Overtoom R.E.

56 Chilmark Rd, Chilmark, MA 02535
/56
$1,699,000 Sold Jun 20, 2025
- 2,954 Sq Ft
- $575/SF
- 314 Days On Market
- 4 Beds
- 5 Baths
- Built 1900
9 Goode St, Oak Bluffs, MA 02557

Welcome to your dream home, located on a very quiet street in Oak Bluffs, yet just a short walk to downtown & the elementary school. This prime location offers the perfect blend of serenity and convenience. This well appointed home features 4 bedrooms and 4.5 bathrooms. Included in this is a 1-bedroom, 1-bathroom apartment attached to the home, providing a perfect space for guest accommodation.

Grace Hagerty Grace Hagerty Real Estate Inc

9 Goode St, Oak Bluffs, MA 02557

/20
Est $1,577,431 Not Listed For Sale
- 4 Beds
- 2 Baths
- 1,532 Sq Ft
39 Prices Way, Edgartown, MA 02539

39 Prices Way, Edgartown, MA 02539

Showing Results 81 - 120, Page 3 of 18

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