Dukes, MA Homes

/41
$9,495,000
- 4 Beds
- 6 Baths
- 4,605 Sq Ft
29 Slough Cove Rd, Edgartown, MA 02539

LUXURIOUS COUNTRY ESTATE IN KATAMA. Sited at the end of a long private drive, amid a bucolic 1.5-acre meadow setting with stone retaining walls and lush perennial gardens, this elegant country estate, designed by noted architect Patrick Ahearn, offers the epitome of luxurious living in Katama. The home’s timeless and charming character is highlighted by thoughtful, top-notch architectural details

Wendy Harman

Compass

(508) 274-5363

29 Slough Cove Rd, Edgartown, MA 02539
/26
$18,000 per month
- 7 Beds
- 1.5 Baths
- 2,900 Sq Ft
- House for Rent
39 N Neck Rd, Edgartown, MA 02539

Historic Quaint Waterfront Cottage with spectacular 180 degree views of Edgartown Harbor, Oak Bluffs, Cape Cod and Cape Poge, Over 200 feet of secluded, completely private beach, The back yard abuts the fairways and club house of the ''Royal Ancient Chappaquiddick Links'' Private Golf Course. (You must pay dues to play golf), Great outdoor shower. You can see the fireworks (in 5 locations at

Charles Petitti Coldwell Banker Realty - Newton

39 N Neck Rd, Edgartown, MA 02539
/31
$1,325,000 Sold Jun 30, 2025
- 2,292 Sq Ft
- $578/SF
- 10 Days On Market
- 5 Beds
- 4 Baths
- Built 1992
191 Spring Hill Rd, Vineyard Haven, MA 02568

This pristine cape-style home is located in the heart of Vineyard Haven. This home features five bedrooms, four bathrooms, a beautifully landscaped yard, and an energy-efficient solar panel system installed by South Mountain Company. The functional and efficient floor plan with an open kitchen, living, and dining concept, makes entertaining family and guests seamless, with easy access to the

Madelyn Silvia Wallace & Co. Sotheby's

191 Spring Hill Rd, Vineyard Haven, 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

/37
$9,995,000
- 6 Beds
- 7.5 Baths
- 7,205 Sq Ft
25 Lelands Path, Edgartown, MA 02539

Casual Elegance On Katama Bay - Welcome to 25 Leland’s Path on Katama Bay, a stunning property that embodies the perfect blend of casual elegance and serene waterfront living on Chappquiddick. This magnificent home offers over 7,200 square feet of living space, six bedrooms, all with en suite baths, and a three-room Owner's Suite with sweeping water views and a private second-floor deck. The

Wendy Harman

Compass

(508) 274-5363

25 Lelands Path, 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
/34
$1,050,000 Sold Jun 30, 2025
- 1,606 Sq Ft
- $654/SF
- 45 Days On Market
- 4 Beds
- 2 Baths
- Built 1977
160 Bernard Cir, Vineyard Haven, MA 02568

Charming, four bedroom home with impressive rental history, new roof and septic in 2021/2022. Being offered turn-key, fully furnished with coastal decor, ready to move in and enjoy. Soaring cathedral ceilings highlight the open floor plan of the main living area on the second floor. Granite counters, stainless steel appliances and a center island in the kitchen leads to the dining area with

Dawn Bellante-Holand Sandpiper Realty

160 Bernard Cir, Vineyard Haven, MA 02568

/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

/27
$1,170,000
- 3 Beds
- 2 Baths
- 1,512 Sq Ft
62 Jernegan Ave, Edgartown, MA 02539

Charming 3-Bedroom, 2-Bath Ranch in Edgartown – Spacious, Private, and Conveniently Located Discover this inviting 3-bedroom, 2 full bath ranch-style home set on a generous .5 acre lot in a quiet, private area of Edgartown. Featuring an open-concept layout, this home offers seamless flow between the living, dining, and kitchen spaces—ideal for both everyday living and entertaining. The spacious

Nicholas Silvestri

Keller Williams Realty Evolution

(508) 290-4981

62 Jernegan Ave, Edgartown, MA 02539
/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
$1,100,000 Sold Jun 27, 2025
- 1,976 Sq Ft
- $557/SF
- 9 Days On Market
- 4 Beds
- 3 Baths
- Built 1985
10 Kims Way, Oak Bluffs, MA 02557

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 02557

/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

/42
$5,995,000 Open Sun 1:30PM - 3:30PM
- 3 Beds
- 6 Baths
- 3,608 Sq Ft
385 Barnes Rd, Vineyard Haven, MA 02568

Indulge in luxurious living at this exquisite waterfront retreat featuring a private 125-foot sandy beach. Over 5,400 sq ft on three floors blend elegance with indoor-outdoor living. The grand foyer leads to dramatic interiors with high ceilings and floor-to-ceiling windows showcasing stunning water views. Highlights include a striking stone fireplace, custom built-ins, gourmet kitchen with stone

Wendy Harman

Compass

(508) 274-5363

385 Barnes Rd, Vineyard Haven, MA 02568
/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
/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

/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
$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
$1,970,000 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

/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

/50
$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
/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
/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

/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
/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

/36
Est $1,735,729 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
/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

/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
/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

/36
Est $3,937,092 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
/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

/20
Est $1,575,031 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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