Dukes, MA Homes

/29
$4,500,000
- 5 Beds
- 6 Baths
- 5,598 Sq Ft
71 Stoney Hill Rd, Vineyard Haven, MA 02568

A combination of luxury, comfort, and natural beauty, this expansive custom, 6,000+ square foot, five bedroom, post and beam home is sited on more than seven acres of land, surrounded by more than 200 acres of Land Bank property. From the moment you step inside, you'll be captivated by the attention to detail and the high-end finishes throughout. The open concept layout allows for seamless flow

Sheila Morse Island Real Estate

71 Stoney Hill Rd, Vineyard Haven, MA 02568
/39
$46,000 per month
- 6 Beds
- 4.5 Baths
- 3,800 Sq Ft
- House for Rent
99 Pond Road Wt104, West Tisbury, MA 02575

THIS IS A WEEKLY RENTAL NOT A MONTHLY!!!!! Beautiful bright sunny home with open concept living. Main floor features a gourmet kitchen with stainless appliances, breakfast bar and formal dining table to seat 10. Large glass sliders open up to expansive views of the deck, pool and pasture beyond. Also on the main level is a separate living area with large screen TV, powder room, and den with twin

Karen Overtoom Karen M. Overtoom R.E.

99 Pond Road Wt104, West Tisbury, MA 02575
/42
$865,000 Sold Apr 17, 2025
- 1,208 Sq Ft
- $716/SF
- 2 Days On Market
- 2 Beds
- 2 Baths
- Built 1972
4 Quail Run Rd Unit 17, Edgartown, MA 02539

Luxurious Lifestyle Amenities: Renovated Townhouse With Tennis, Pickleball + Boating Access - This nicely appointed condominium in the exclusive Sengekontacket community offers a perfect blend of comfort and convenience. It features two walls of sliding glass doors that lead out to an expansive 288-square foot deck. The property was updated in 2023 with new Pella® sliding glass doors, new

Wendy Harman Compass

4 Quail Run Rd Unit 17, Edgartown, MA 02539

/33
Est $2,082,075 Not Listed For Sale
- 4 Beds
- 2 Baths
- 1,400 Sq Ft
119 Herring Creek Rd, Edgartown, MA 02539

119 Herring Creek Rd, Edgartown, MA 02539

/40
$1,925,000
- 4 Beds
- 4 Baths
- 3,927 Sq Ft
44 Tiffany Dr, Oak Bluffs, MA 02557

Nestled within the desirable Lagoon Estates development and set on a beautifully wooded 1.38-acre lot abutting Land Bank property, this expansive and sun-filled home offers versatile living space and a flexible floor plan. The main house features generously sized rooms enhanced by large windows that flood the interior with natural light. The kitchen boasts white cabinetry, a wall-mounted

Nora Jardin Island Real Estate

44 Tiffany Dr, Oak Bluffs, MA 02557
/34
$12,000 per month
- 3 Beds
- 2.5 Baths
- 2,240 Sq Ft
- House for Rent
267 Great Plains Road Wt117, West Tisbury, MA 02575

THIS IS A WEEKLY SUMMER RENTAL ONLY.THE WEEKLY PRICE IN AUGUST IS $4,000. PER WEEK.SEE WEB SITE FOR ADDITIONAL WEEKLY PRICING. Large spacious home with open concept living and dining area. This house has gorgeous hardwood floors throughout, separate media room, and loads of natural sunlight. It also features an exceptionally large master bedroom with en-suite bath, and private deck. There is

Karen Overtoom Karen M. Overtoom R.E.

267 Great Plains Road Wt117, West Tisbury, MA 02575
/29
$1,662,000 Sold Apr 16, 2025
- 1,794 Sq Ft
- $926/SF
- 0 Days On Market
- 3 Beds
- 2 Baths
- Built 2010
395 Edgartown - West Tisbury Rd, Edgartown, MA 02539

Exceptional turnkey year round home opportunity in Edgartown! Relaxing clean updated three bedroom two bath two story Cape Cod style home built by Squash Meadow Construction. Open concept kitchen with stainless steel appliances, dining, living room, sunroom/office nook with high cathedral ceiling. Abundant bright natural light with modern transom windows and skylights. A perfectly designed home

Janna O'Loughlin Portfolio Real Estate, Inc.

395 Edgartown - West Tisbury Rd, Edgartown, MA 02539

/37
Est $2,296,409 Not Listed For Sale
- 3 Beds
- 2 Baths
- 2,097 Sq Ft
24 Pulpit Ln, Edgartown, MA 02539

24 Pulpit Ln, Edgartown, MA 02539

/22
$1,749,000
- 3 Beds
- 2 Baths
- 1,324 Sq Ft
76 Norton Orchard Rd, Edgartown, MA 02539

Conveniently located near downtown Edgartown and the Edgartown Golf Course, this well-maintained three-bedroom, two-bathroom home offers endless potential. The first floor includes a comfortable living room, dining area, kitchen, and a full bathroom. Upstairs, you will find three bedrooms and another full bathroom. There is an unfinished basement which has the laundry and utilities. The property

Jarrett Hurwitz Keller Williams Realty

76 Norton Orchard Rd, Edgartown, MA 02539
/18
$10,000 per month
- 3 Beds
- 2 Baths
- 1,439 Sq Ft
- House for Rent
24 Nat's Farm Lane Wt113, West Tisbury, MA 02575

THIS IS A WEEKLY SUMMER RENTAL ONLY.THE WEEKLY PRICE IN AUGUST IS $2,500. PER WEEK.SEE WEB SITE FOR ADDITIONAL WEEKLY PRICING. Charming three bedroom home located in a private neighborhood close to bike path, walking trails and public tennis courts. Just a short drive to Lambert's Cove Beach, West Tisbury Village and down island restaurants and shops.Amenities include High definition TV, wifi

Karen Overtoom Karen M. Overtoom R.E.

24 Nat's Farm Lane Wt113, West Tisbury, MA 02575
/11
$749,000 Sold Apr 14, 2025
- 240 Sq Ft
- $3121/SF
- 0 Days On Market
- 1 Bed
- 1 Bath
- Built 1980
488 Lighthouse Rd, Aquinnah, MA 02535

This is truly a once-in-a-lifetime opportunity…Step back in time, and away from any stress, into this magical beach shack in the dunes in Aquinnah with deeded walking path to Dog Fish Bar beach. As you follow a boardwalk toward the Sound, hidden away in the coastal brush, you’ll find this sweet little retreat with one cheery open room including kitchen, built-in bed and storage, and a

Meg Bodnar Tea Lane Associates

488 Lighthouse Rd, Aquinnah, MA 02535

/52
Not Listed For Sale
- 6 Beds
- 9 Baths
- 4,962 Sq Ft
31 Eel Pond Ln, Edgartown, MA 02539

31 Eel Pond Ln, Edgartown, MA 02539

/114
$6,900,000
- 7 Beds
- 6 Baths
- 4,730 Sq Ft
180 Pilot Hill Farm Rd, Vineyard Haven, MA 02568

A storybook sanctuary in Pilot Hill. For the first time in 37 years, one of the rarest and most beautiful properties within Pilot Hill Farm is being offered for sale.Set on nearly eight acres, this unique estate includes a thoughtfully renovated antique farmhouse and several distinctive outbuildings: a pool, guest house, an art studio, and a carriage house with room for three cars, plus a

Alexis Holden Tea Lane Associates

180 Pilot Hill Farm Rd, Vineyard Haven, MA 02568
/9
$19,000 per month
- 6 Beds
- 2.5 Baths
- 2,155 Sq Ft
- House for Rent
17 Umbagog Ave Wt109, West Tisbury, MA 02575

THIS IS A WEEKLY SUMMER RENTAL ONLY.THE WEEKLY PRICE IN AUGUST IS $4,750. PER WEEK.SEE WEB SITE FOR ADDITIONAL WEEKLY PRICING. This three story home is located in a very desirable area off of Lambert's Cove Road, Makonikey, with access to a private association beach and walking trails. There are four plus bedrooms and bright and open living spaces that lead out to a deck and a screened-in porch.

Karen Overtoom Karen M. Overtoom R.E.

17 Umbagog Ave Wt109, West Tisbury, MA 02575
/14
$640,000 Sold Apr 11, 2025
- 647 Sq Ft
- $989/SF
- 178 Days On Market
- 2 Beds
- 1 Bath
- Built 1880
56 Narragansett Ave Unit 3A, Oak Bluffs, MA 02557

OAK BLUFFS REAL ESTATE OPPORTUNITY~Explore this spacious first-floor condo, complete with two bedrooms and a full bath. Perfectly located just a leisurely stroll from the beach, a variety of restaurants, charming campgrounds, coffee shops, and the harbor with ferry access. Boasting coveted B1 zoning, this property offers an outstanding opportunity for savvy investors. Its potential as a rental

Marilyn Moses Ocean Park Realty Inc

56 Narragansett Ave Unit 3A, Oak Bluffs, MA 02557

/33
Est $4,914,185 Not Listed For Sale
- 4 Beds
- 4 Baths
- 2,807 Sq Ft
62 S Water St, Edgartown, MA 02539

62 S Water St, Edgartown, MA 02539

/4
$675,000
- Land
- 0.22 Acre
- $3,068,182 per Acre
0-B California Ave Unit Part lot 79, Oak Bluffs, MA 02568

Oak Bluffs Buildable Lot – Prime LocationThis flat 3-bedroom building lot is ideally located just moments from the Hudson Avenue access to scenic Lagoon Pond, with easy access to both Farm Neck Golf Club and downtown Oak Bluffs. Situated in a neighborhood of newly constructed homes, this lot presents an excellent opportunity to become part of a growing community in Oak Bluffs. According to

Andrew McElhinney Compass LLC

0-B California Ave Unit Part lot 79, Oak Bluffs, MA 02568
/25
$13,600 per month
- 2 Beds
- 2 Baths
- 792 Sq Ft
- House for Rent
64 Bartimus Luce Road Wt125, West Tisbury, MA 02575

THIS IS A WEEKLY RENTAL NOT A MONTHLY!!!!!!!!!!Idyllic location right above a sandy private beach on the North Shore. This beach cottage affords views of the Sound and the Elizabeth Islands with a front row seat on unrivaled sunsets. It is rustic and cozy with a large screened porch overlooking the view. Have a getaway like in days of yore when life was simple and the beach at your doorstep.Take

Karen Overtoom Karen M. Overtoom R.E.

64 Bartimus Luce Road Wt125, West Tisbury, MA 02575
/22
$1,150,000 Sold Apr 11, 2025
- 1,264 Sq Ft
- $910/SF
- 216 Days On Market
- 3 Beds
- 2 Baths
- Built 1983
41 Old County Rd, Vineyard Haven, MA 02568

Let your imagination run wild with this peaceful, pastoral property centrally located between down and up-island. This home is perfectly sited on just over 2 acres and is ready for your vision. The cape-style main house features a spacious wrap around deck and an open floor plan on the first level. The entire home is outfitted with hardwood floors. According to the West Tisbury Board of Health,

Jared Bicknell Compass | The O'Hanlon Group

41 Old County Rd, Vineyard Haven, MA 02568

/42
Est $3,518,854 Not Listed For Sale
- 4 Beds
- 4 Baths
- 2,090 Sq Ft
16 Mill St, Edgartown, MA 02539

16 Mill St, Edgartown, MA 02539

/4
$625,000
- Land
- 0.34 Acre
- $1,838,235 per Acre
0-A California Ave Unit Part lot 79, Oak Bluffs, MA 02568

Oak Bluffs Buildable Lot – Prime Location. This flat 2-bedroom building lot is ideally located just moments from the Hudson Avenue access to scenic Lagoon Pond, with easy access to both Farm Neck Golf Club and downtown Oak Bluffs. Situated in a neighborhood of newly constructed homes, this lot presents an excellent opportunity to become part of a growing community in Oak Bluffs. According to the

Andrew McElhinney Compass LLC

0-A California Ave Unit Part lot 79, Oak Bluffs, MA 02568
/41
$14,500 per month
- 5 Beds
- 5.5 Baths
- 3,392 Sq Ft
- House for Rent
76 School House Lane Wt101, West Tisbury, MA 02575

THIS IS A WEEKLY RENTAL NOT A MONTHLY!!!! An elegant, whimsical house full of color, quality and artistic touches. The grounds are sumptuous, nature at its apotheosis. There is gentle movement in the landscape with flowering trees and shrubs everywhere replete with a babbling brook flowing into a pond bordering the garden behind the house. The stonework is finely crafted with balanced

Karen Overtoom Karen M. Overtoom R.E.

76 School House Lane Wt101, West Tisbury, MA 02575
/20
$4,565,000 Sold Apr 11, 2025
- 5,063 Sq Ft
- $902/SF
- 109 Days On Market
- 6 Beds
- 6 Baths
- Built 2024
61 Division Rd, Edgartown, MA 02539

KATAMA - CONSTRUCTION IN PROGRESS - This elegant 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 boasts

Jennifer DaSilva Compass | Point B

61 Division Rd, Edgartown, MA 02539

/36
Est $1,991,513 Not Listed For Sale
- 3 Beds
- 2 Baths
- 2,200 Sq Ft
2 Fishermans Knot Rd, Edgartown, MA 02539

2 Fishermans Knot Rd, Edgartown, MA 02539

/8
$1,350,000
- Land
- 1.62 Acres
- $833,333 per Acre
44 Iron Hill Rd Unit 1.7, 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 Unit 1.7, Oak Bluffs, MA 02557
/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
/43
$1,675,000 Sold Apr 04, 2025
- 2,094 Sq Ft
- $800/SF
- 276 Days On Market
- 3 Beds
- 3 Baths
- Built 1994
7 N Bog Rd, Edgartown, MA 02539

A private magical setting. Enjoy your morning coffee overlooking a splendid Koi pond surrounded by mature trees, shrubs and perennials. Truly an oasis of nature. This location, on a quiet side street just off the Edgartown/West Tisbury road, is close to town, South Beach and Morning Glory Farm. A beautifully custom built Post and Beam home has been artfuly crafted with a variety of hardwoods

Robin Perschel Feiner Real Estate

7 N Bog Rd, Edgartown, MA 02539

/29
Est $2,288,675 Not Listed For Sale
- 3 Beds
- 2 Baths
- 1,552 Sq Ft
22 Kitts Field Cir, Edgartown, MA 02539

22 Kitts Field Cir, Edgartown, MA 02539

/10
$350,000
- Land
- 0.00 Acre
0 Moshup Trail Unit 32500206, Aquinnah, MA 02535

Enjoy coveted access to one of Martha's Vineyard's most stunning sandy beaches, located just off Moshup Trail in Aquinnah. This secluded beach is shared with only seven other members, ensuring a peaceful and private coastal experience. Located near Aquinnah's iconic ''Painted House,'' the property includes use of a private gated parking area and a picturesque stretch of shoreline perfect for

Alyssa Halisky Wallace & Co. Sotheby's International Realty

0 Moshup Trail Unit 32500206, Aquinnah, MA 02535
/21
$11,000 per month
- 2 Beds
- 1.5 Baths
- 800 Sq Ft
- House for Rent
55 Dr Fisher Rd Unit 1, West Tisbury, MA 02575

THIS IS A SUMMER RENTAL ONLY. Nestled on a quiet country lane, this charming two BR guest house will enchant you with its inviting character and custom features throughout. From the cathedral living area and newly furnished interior to the covered front porch and expansive deck, this lovely cottage has it all. Privately situated , yet convenient to the village, bike path and local

Karen Overtoom Karen M. Overtoom R.E.

55 Dr Fisher Rd Unit 1, West Tisbury, MA 02575
/39
$2,803,000 Sold Apr 04, 2025
- 2,254 Sq Ft
- $1244/SF
- 360 Days On Market
- 3 Beds
- 2.5 Baths
- Built 1986
1 Marchants Path, Edgartown, MA 02539

Elegant colonial on lush 1/2 acre parcel near downtown Edgartown offered fully turnkey. Three spacious bedrooms, two full and one-half bathrooms, and over 2,250 sqft of living space. Double height main living/dining with sliding glass doors to outdoor living, new Velux skylights and gas fireplace. Newly refreshed gourmet kitchen with all stainless appliances, quartz countertops, island eatery and

Allison Cameron Parry Douglas Elliman Real Estate - Nantucket

1 Marchants Path, Edgartown, MA 02539

/77
Est $1,009,862 Not Listed For Sale
- 3 Beds
- 1 Bath
- 1,040 Sq Ft
14 Cottage St, Vineyard Haven, MA 02568

14 Cottage St, Vineyard Haven, MA 02568

/10
$350,000
- Land
- 1.26 Acres
- $277,778 per Acre
0 Moshup Trail Unit 27 & 146 43498, Aquinnah, MA 02535

Enjoy coveted access to one of Martha's Vineyard’s most stunning sandy beaches, located just off Moshup Trail in Aquinnah. This secluded beach is shared with only seven other members, ensuring a peaceful and private coastal experience. Located near Aquinnah’s iconic “Painted House,” the property includes use of a private gated parking area and a picturesque stretch of shoreline perfect for

Alyssa Halisky Wallace & Co. Sotheby's

0 Moshup Trail Unit 27 & 146 43498, Aquinnah, MA 02535
/22
$10,000 per month
- 3 Beds
- 1.5 Baths
- 1,500 Sq Ft
- House for Rent
21 Leona Lane Wt115, West Tisbury, MA 02575

THIS IS A SUMMER RENTAL ONLY. This very charming post & beam home is the perfect getaway for those who appreciate West Tisbury's rural character. The home is very nicely furnished and equipped, has a lovely, big yard, and the location, adjacent to the bike path, is central to up-Island shopping and the fantastic sandy beaches of Lambert's Cove and Long Point Reservation. There is no land line

Karen Overtoom Karen M. Overtoom R.E.

21 Leona Lane Wt115, West Tisbury, MA 02575
/8
$390,000 Sold Apr 01, 2025
- Land
- 0.25 Acre
- $1,560,000 per Acre
- 83 Days On Market
0 Concord Ave, Oak Bluffs, MA 02568

GROVEDALE BUILD YOUR DREAM OPPORTUNITY - Along a quiet country lane and close to all Oak Bluffs has to offer, this level lot is located in a neighborhood of nicely landscaped homes. The pride of ownership is apparent in this locale. There are not many opportunites like this left on Martha's Vineyard.

Leslie C. Floyd Portfolio Real Estate, Inc.

0 Concord Ave, Oak Bluffs, MA 02568

/29
Est $3,993,870 Not Listed For Sale
- 4 Beds
- 2.5 Baths
- 2,408 Sq Ft
26 Morse St, Edgartown, MA 02539

26 Morse St, Edgartown, MA 02539

/25
$1,295,000
- 3 Beds
- 2 Baths
- 1,432 Sq Ft
140 Longview Rd, Vineyard Haven, MA 02568

Nestled in the hills of Longview, less than 1 mile from beautiful Lambert's Cove Beach, this 3-bedroom retreat is a cozy year-round home or an airy summer getaway - whatever your needs might be. The vaulted ceilings throughout the home allow it to live much larger than its square footage - and the expansive front deck stretches the living space all through the spring, summer and even fall

Candy DaRosa Feiner Real Estate

140 Longview Rd, Vineyard Haven, MA 02568
/15
$21,000 per month
- 6 Beds
- 2 Baths
- 1,700 Sq Ft
- House for Rent
12 John Wesley Ave Ob519, Oak Bluffs, MA 02557

THIS IS A SUMMER RENTAL ONLY. EAST CHOP LOCATION!! Located across from the historic Baptist Temple Town Park. This charming 1885 Victorian cottage is original to days gone by and a significant part of the Vineyard Highlands. Six bedrooms and two full bathrooms allow for friends and family to visit along with a cozy, bright vintage kitchen. This is a house of distinctive "Carpenter Gothic"

Karen Overtoom Karen M. Overtoom R.E.

12 John Wesley Ave Ob519, Oak Bluffs, MA 02557
/38
$1,875,000 Sold Apr 01, 2025
- 3,841 Sq Ft
- $488/SF
- 24 Days On Market
- 5 Beds
- 5 Baths
- Built 1994
83 Dolan Ave, Vineyard Haven, MA 02568

Beautiful Cape style home renovated over the years with an open floor plan, five bedrooms including a first-floor primary with en-suite, and a nicely finished walk-out lower level. There is a 7-bedroom septic system for additional bedrooms and a special permit for the apartment. Manicured yard with mature plantings providing excellent privacy. In-ground heated pool with blue stone patio and lots

Courtney Marek Sandpiper Realty

83 Dolan Ave, Vineyard Haven, MA 02568

/8
Not Listed For Sale
- 2 Beds
16 Forever Wild Way, Edgartown, MA 02539

16 Forever Wild Way, Edgartown, MA 02539

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