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
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/12
$5,500 per month
- 3 Beds
- 2 Baths
- 2,200 Sq Ft
- House for Rent
2 Fishermans Knot Rd Ed309 Unit 1, Edgartown, MA 02539

THIS PROPERTY IS A WEEKLY VACATION RENTAL PROPERTY. The home’s timeless interior offers a sitting room with a wood-burning fireplace, a hallway opening to a large, bright, modern kitchen featuring a Viking range and large dining table. Ample counter space and a wall of built-ins are the perfect complement to family and friends that enjoy cooking together. A gas grill and outdoor seating are only

Karen Overtoom Karen M. Overtoom R.E.

2 Fishermans Knot Rd Ed309 Unit 1, Edgartown, MA 02539
/45
$5,250,000 Sold Jul 02, 2025
- 2,869 Sq Ft
- $1830/SF
- 37 Days On Market
- 3 Beds
- 5 Baths
- Built 1988
14 Katama Farm S, Edgartown, MA 02539

Katama Farm South - En route to this stellar location, enjoy scenic views while passing iconic Katama Farm. Less than a half-mile drive or a quarter mile walk from South Beach, this dynamic compound, which includes a spacious post and beam home and two-story barn, is privately situated on a large, beautifully landscaped, 1.6-acre parcel of land. The home is nearly 3,000sf in size and the multiple

Courtney Marek Sandpiper Realty

14 Katama Farm S, Edgartown, MA 02539

/12
Est $1,307,200 Not Listed For Sale
- 4 Beds
- 2 Baths
- 1,997 Sq Ft
3 Carole Ave, Vineyard Haven, MA 02568

3 Carole Ave, Vineyard Haven, MA 02568

/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
/10
$8,500 per month
- 3 Beds
- 2 Baths
- House for Rent
29 Bea Lane Wt160 Unit 1, West Tisbury, MA 02575

THIS IS A WEEKLY RENTAL PROPERTY!! Red Farm, Off Lambert's Cove Road West Tisbury. This newly built Contemporary Home is privately sited overlooking a peaceful meadow and wooded setting. The spacious floor plan features an open living, dining and a well equipped chef's kitchen, cathedral ceilings, wood floors and sliders that lead to a nicely landscaped yard. Three spacious bedrooms, the primary

Karen Overtoom Karen M. Overtoom R.E.

29 Bea Lane Wt160 Unit 1, West Tisbury, MA 02575
/19
$850,000 Sold Jul 02, 2025
- 481 Sq Ft
- $1767/SF
- 33 Days On Market
- 1 Bed
- 1 Bath
- Built 1920
68 Winter St, Edgartown, MA 02539

Welcome to 68 Winter Street, a highly sought-after community of six, one bedroom condos located in Edgartown Village. Enjoy seasonal or year-round living at this sophisticated, garden level pied-a-terre. Elegant and well-appointed throughout, this stylish condo features open living with a nicely equipped kitchen, soaring ceilings, crown modeling, over-sized windows, and wood floors. Spacious

Michele Moore Island Real Estate

68 Winter St, Edgartown, MA 02539

/13
Est $1,290,190 Not Listed For Sale
- 3 Beds
- 2 Baths
- 1,428 Sq Ft
33 Menahan St, Vineyard Haven, MA 02568

33 Menahan St, Vineyard Haven, MA 02568

/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
/8
$16,000 per month
- 7 Beds
- 3.5 Baths
- 4,000 Sq Ft
- House for Rent
5 Wauwompauque Trail Unit 1 CH213, Chilmark, MA 02535

THIS PROPERTY IS A WEEKLY RENTAL PROPERTY!! Expansive home in North Abels Hill association with water views, private association beach and tennis. Centrally air conditioned, this family home has been well appointed with a large living room featuring fireplaces at both ends, a formal dining room, a first floor primary bedroom with en suite as well as a second floor primary bedroom with en suite.

Karen Overtoom Karen M. Overtoom R.E.

5 Wauwompauque Trail Unit 1 CH213, Chilmark, MA 02535
/48
$5,250,000 Sold Jul 02, 2025
- 2,869 Sq Ft
- $1830/SF
- 54 Days On Market
- 3 Beds
- 4.5 Baths
- Built 1988
14 Katama Farm Rd N, Edgartown, MA 02539

Katama Farm South - En route to this stellar location, enjoy scenic pastoral views while passing iconic Katama Farm. A quarter mile from South Beach, this dynamic compound, which includes a spacious post and beam home and two-story barn, is privately situated on a large, beautifully landscaped, 1.6-acre parcel of land. The home is nearly 3,000 sf in size and the multiple outdoor living spaces

Courtney Marek Sandpiper Realty Inc

14 Katama Farm Rd N, Edgartown, MA 02539

/30
Est $2,500,413 Not Listed For Sale
- 3 Beds
- 3 Baths
- 2,555 Sq Ft
10 Crow Hollow Rd, Vineyard Haven, MA 02568

10 Crow Hollow Rd, Vineyard Haven, MA 02568

/42
$5,995,000 Open House 8/03
- 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
/8
$3,300 per month
- 3 Beds
- 2 Baths
- 1,196 Sq Ft
- House for Rent
849 State Rd Unit 1, Aquinnah, MA 02535

THIS PROPERTY IS A WEEKLY RENTAL PROPERTY!! Charming three bedroom cottage set on a hill overlooking a tranquil meadow just 1 & 1/2 miles to Aquinnah Cliffs. Enjoy access to both Philbin and Lobsterville beaches. There is a front and back porch with rocking chairs to take in the landscape and enjoy the breeze. This sunny property is easily accessible as well as peaceful and relaxing. Owner is

Karen Overtoom Karen M. Overtoom R.E.

849 State Rd Unit 1, Aquinnah, MA 02535
/36
$1,950,000 Sold Jul 02, 2025
- 2,691 Sq Ft
- $725/SF
- 30 Days On Market
- 4 Beds
- 2.5 Baths
- Built 1976
51 Black Brook Crossing Rd, West Tisbury, MA 02568

This charming 4 bed/2.5 bath Cape style home is set in a perfect setting, carefully sited on 1 acre bordered by a beautiful stone wall with mature plantings. Newly renovated kitchen with plenty of cabinets and storage, quartz counters and dining room with sliders to a screened-in porch. There is a den and living room with access to a spacious deck. The Great Room features cathedral ceilings,

Brenda Galligan Karen M. Overtoom R.E.

51 Black Brook Crossing Rd, West Tisbury, MA 02568

/4
Est $3,318,936 Not Listed For Sale
- 4 Beds
- 3 Baths
- 2,789 Sq Ft
188 Pond Rd, Vineyard Haven, MA 02568

188 Pond Rd, Vineyard Haven, MA 02568

/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
/8
$11,800 per month
- 4 Beds
- 4 Baths
- 2,612 Sq Ft
- House for Rent
46 Buttonwood Farm Rd Unit 1, West Tisbury, MA 02575

THIS IS A WEEKLY RENTAL PROPERTY!! Beautifully updated contemporary home with impeccably landscaped lawns and gardens, a swimming pond and hot tub with two outdoor showers - one enclosed and one open to the hot tub and patio area on the side of the house. Gorgeous back deck with outdoor dining accessible through sliding glass doors from the dining room. Inside, enjoy the fully equipped and

Karen Overtoom Karen M. Overtoom R.E.

46 Buttonwood Farm Rd Unit 1, West Tisbury, MA 02575
/2
$1,595,000 Sold Jul 01, 2025
- 1,176 Sq Ft
- $1356/SF
- 2 Beds
- 2 Baths
- Built 1998
10 Red Pony Rd, West Tisbury, MA 02568

Pastoral and perfect. Room to grow or just move in.

Lisa Da silva Compass | Point B

10 Red Pony Rd, West Tisbury, MA 02568

/34
Est $2,551,353 Not Listed For Sale
- 5 Beds
- 3.5 Baths
- 1 Sq Ft
248 Pond Rd, Vineyard Haven, MA 02568

248 Pond Rd, Vineyard Haven, MA 02568

/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
/8
$17,500 per month
- 8 Beds
- 4.5 Baths
- 3,876 Sq Ft
- House for Rent
550 Chappaquonsett Rd Vh424 Unit 1, Tisbury, MA 02568

THIS PROPERTY IS A WEEKLY RENTAL PROPERTY!!!!!! Classic vineyard cottage with large open indoor and outdoor spaces to choose from while you and your family create memories to last a lifetime. Enjoy creating appetizers or three course meals in the newly renovated kitchen, bask in the light filled sun room or one of several covered porches while you take in the smell of fresh ocean air and

Karen Overtoom Karen M. Overtoom R.E.

550 Chappaquonsett Rd Vh424 Unit 1, Tisbury, MA 02568
/32
$3,925,000 Sold Jul 01, 2025
- 5,603 Sq Ft
- $701/SF
- 238 Days On Market
- 6 Beds
- 7 Baths
- Built 1995
140 Merry Farm Rd, Vineyard Haven, MA 02568

Site of the original Rainbow Farm, this 8.05-acre parcel is one of the most beautiful pieces of land in West Tisbury. The warm and convivial 5,000 sq ft home with its 4 bedrooms looks out onto a setting that is as if from a bygone era, the vast fields stretching into the distance. The spring-fed pond is a centerpiece of the pastoral view. The home itself has many surprising and charming design

Mark Jenkins Wallace & Co. Sotheby's

140 Merry Farm Rd, Vineyard Haven, MA 02568

/25
Est $2,062,294 Not Listed For Sale
- 5 Beds
- 3 Baths
- 3,636 Sq Ft
131 Shubael Weeks Path, Vineyard Haven, MA 02568

131 Shubael Weeks Path, Vineyard Haven, MA 02568

/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
/8
$6,000 per month
- 4 Beds
- 2.5 Baths
- 2,000 Sq Ft
- House for Rent
33 Kennebago Ave Vh414, Tisbury, MA 02568

THIS PROPERTY IS A WEEKLY RENTAL PROPERTY!! This beautiful home has lots of open space for cooking, yard activities or just plain relaxing. Private association beach overlooking the Elizabethan Islands. Plan a sunset picnic on the beach or plan in the morning to see the rays of sun break on the water.

Karen Overtoom Karen M. Overtoom R.E.

33 Kennebago Ave Vh414, Tisbury, MA 02568
/6
$430,000 Sold Jun 30, 2025
- Land
- 1.40 Acres
- $307,143 per Acre
- 0 Days On Market
0 Quansoo Beach Lot Unit 48 43513, Chilmark, MA 02535

Not listed in LINK.

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0 Quansoo Beach Lot Unit 48 43513, Chilmark, MA 02535

/43
Est $4,627,484 Not Listed For Sale
- 4 Beds
- 3.5 Baths
- 2,932 Sq Ft
12 Norton St, Edgartown, MA 02539

12 Norton St, Edgartown, MA 02539

/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
/4
$6,000 per month
- 3 Beds
- 2 Baths
- 1,608 Sq Ft
- House for Rent
836 State Rd, Aquinnah, MA 02535

THIS PROPERTY IS A WEEKLY RENTAL PROPERTY!! Windy Knoll is a 3BR, 2Bath home located in Aquinnah on a secluded lot off State Road with 160 degree views of the Atlantic Ocean. Approximately 1 mile to Philbin Beach similar distance to Moshup Beach and Lobsterville beach. Take the bike ferry over to Menemsha and enjoy sunset on the beach. Outdoor shower with multiple shower heads to wash off the

Karen Overtoom Karen M. Overtoom R.E.

836 State Rd, Aquinnah, MA 02535
/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

/79
Not Listed For Sale
- 6 Beds
- 3 Baths
- 2,604 Sq Ft
260 South Rd, Chilmark, MA 02535

260 South Rd, Chilmark, MA 02535

/24
$935,000
- 1 Bed
- 1 Bath
- 797 Sq Ft
37 Circuit Ave Unit 5, Oak Bluffs, MA 02557

Downtown Oak Bluffs centrally located in the heart of Oak Bluffs. Steps from ferries, shops, restaurants and beaches from this penthouse condo. Escape the hustle and bustle on your semi private rooftop deck shared only with (unit 4 also for sale). Panoramic views of the Nantucket and Vineyard Sounds await you while you relax on the deck or enjoy dinner al fresco. The condo features all wood

Lisa Lucier

Anchor Realty of MV

(508) 422-4131

37 Circuit Ave Unit 5, Oak Bluffs, MA 02557
/8
$13,600 per month
- 2 Beds
- 2 Baths
- 1,967 Sq Ft
- Condo for Rent
1 Meetinghouse Village Way Unit 1 ED335, Edgartown, MA 02539

THIS PROPERTY IS A WEEKLY RENTAL PROPERTY!! Enjoy this well appointed and immaculately clean two bedroom condo located just steps from the association pool and a short drive to South Beach with its gorgeous white sands. An open living room, kitchen and dining room with walk-out access to the deck and back yard offer plenty of gathering spaces to enjoy your company over meals, snacks and games

Karen Overtoom Karen M. Overtoom R.E.

1 Meetinghouse Village Way Unit 1 ED335, Edgartown, MA 02539
/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

/35
Est $7,370,865 Not Listed For Sale
- 5 Beds
- 5.5 Baths
- 5,207 Sq Ft
93 S Water St, Edgartown, MA 02539

93 S Water St, Edgartown, MA 02539

/26
$2,795,000
- 3 Beds
- 3 Baths
- 2,750 Sq Ft
109 Herring Creek Rd, Edgartown, MA 02539

Coastal Retreat In Katama - Located in the heart of Katama, with the iconic Katama Airfield and the sandy shores of South Beach nearby, this contemporary coastal retreat is ideal for enjoying all the best of Katama. The reverse-style contemporary features a sunny, open-designed floor plan with vaulted ceilings that seamlessly combine an inviting Living Room with gas fireplace, a Game Room with

Wendy Harman

Compass

(508) 274-5363

109 Herring Creek 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
/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

/16
Not Listed For Sale
- 5 Beds
- 3 Baths
- 1,640 Sq Ft
201 Upper Main St, Edgartown, MA 02539

201 Upper Main St, Edgartown, MA 02539

Showing Results 41 - 80, Page 2 of 18

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