Dukes, MA Homes

/40
$1,899,000
- 4 Beds
- 3.5 Baths
- 2,061 Sq Ft
174 Middle Rd, Chilmark, MA 02535

Nestled in the heart of Chilmark, this four-bedroom home offers a blend of comfort, convenience, and timeless Vineyard charm. Thoughtfully designed with distinct, well-proportioned rooms, the home centers around an expansive, sunlit, eat-in kitchen featuring dual ovens, elegant granite countertops, and extensive custom cherry wood built-ins that combine beauty and practicality. The welcoming

Sheila Morse Island Real Estate

174 Middle Rd, 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
/35
$1,837,500 Sold Apr 18, 2025
- 1,654 Sq Ft
- $1111/SF
- 182 Days On Market
- 4 Beds
- 3 Baths
- Built 1984
55 Charles Neck Way, Vineyard Haven, MA 02568

LONG POINT BEACH RETREAT. Privately set on 1.6 acres in the highly-coveted Long Point area of West Tisbury, this reverse style beach house is an idyllic island retreat. The open-designed Great Room features vaulted ceilings and a wall of sliding glass doors that open out to an expansive deck, perfect for indoor-outdoor summer living and entertaining. There are also screened porches on both

Wendy Harman Compass | Point B

55 Charles Neck Way, Vineyard Haven, MA 02568

/36
Est $1,636,556 Not Listed For Sale
- 4 Beds
- 3 Baths
- 1,144 Sq Ft
323 Lamberts Cove Rd, Vineyard Haven, MA 02568

323 Lamberts Cove Rd, Vineyard Haven, MA 02568

/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
/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
/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

/17
Est $1,422,592 Not Listed For Sale
- 3 Beds
- 3 Baths
- 1,800 Sq Ft
2 Pond View Farm Rd, Vineyard Haven, MA 02568

2 Pond View Farm Rd, Vineyard Haven, MA 02568

/26
$1,597,500
- 3 Beds
- 2 Baths
- 1,400 Sq Ft
190 Longview Rd, Vineyard Haven, MA 02568

Ask listing office. This property is in West Tisbury, 02575 NOT Tisbury 02568

Kathleen Kendrick Kathleen Kendrick

190 Longview Rd, Vineyard Haven, MA 02568
/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
/30
$1,175,000 Sold Mar 20, 2025
- 1,389 Sq Ft
- $846/SF
- 173 Days On Market
- 3 Beds
- 2 Baths
- Built 1988
12 W Farm Rd, West Tisbury, MA 02575

Welcome to 12 West Farm Road, a delightful classic cape nestled among beautiful mature evergreens in the Coffins Field neighborhood of West Tisbury. This well-kept home features 3 bedrooms and 2 bathrooms, offering 1,389 square feet of cozy and inviting living space. Skylighted ceilings and an open first-floor living/cooking/dining area combination provide a spacious feeling for everyday

Carson Crissman Compass | Point B

12 W Farm Rd, West Tisbury, MA 02575

/30
Est $1,535,358 Not Listed For Sale
- 3 Beds
- 2 Baths
- 1,464 Sq Ft
88 Hopps Farm Rd, Vineyard Haven, MA 02568

88 Hopps Farm Rd, Vineyard Haven, MA 02568

/36
$1,495,000
- 4 Beds
- 2 Baths
- 1,332 Sq Ft
40 Scotchmans Ln, Vineyard Haven, MA 02568

A home with history, built in the early 1800s this dwelling was originally built on a local farm and moved to its present location in the 1920's. The structure sits nestled amongst mature plantings and out buildings facing the Mill Brook. The studio and covered patio offer opportunities to entertain, relax and reflect. This 3.76 parcel was created from a larger parcel by the owner (see attached

Jim Osmundsen Donnelly + Co.

40 Scotchmans Ln, 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
/22
$1,115,000 Sold Mar 14, 2025
- 1,286 Sq Ft
- $867/SF
- 212 Days On Market
- 2 Beds
- 1 Bath
- Built 1955
496 Lamberts Cove Rd, Vineyard Haven, MA 02568

Two peaceful acres on coveted Lamberts Cove Road with access to Lamberts Cove Beach and proximity to West Tisbury Center and Conservation Land. This property boasts mature plantings, various trees, and much Mother Nature offers, including a small pond. The home has been completely renovated and enjoys hardwood floors, skylights, a wood stove, and other special features such as antique

Stephanie Roache Donnelly + Co

496 Lamberts Cove Rd, Vineyard Haven, MA 02568

/33
Est $1,896,538 Not Listed For Sale
- 5 Beds
- 3.5 Baths
- 2,508 Sq Ft
163 Charles Neck Way, Vineyard Haven, MA 02568

163 Charles Neck Way, Vineyard Haven, MA 02568

/46
$6,750,000
- 3 Beds
- 3 Baths
- 3,432 Sq Ft
44 Cencelle St, Chilmark, MA 02535

This private 21-acre Chilmark estate with ocean views, tucked away in the rolling hills and farmlands of Chilmark, offers sweeping ocean views to the south and a rare sense of seclusion and serenity. At the heart of the property is a striking modern style home, thoughtfully designed to bring the outdoors in. Expansive walls of glass flood the interior with natural light and frame panoramic views

Meg Bodnar Tea Lane Associates

44 Cencelle St, Chilmark, MA 02535
/19
$17,600 per month
- 4 Beds
- 2 Baths
- 1,584 Sq Ft
- House for Rent
50 Carls Way, West Tisbury, MA 02575

THIS IS A WEEKLY SUMMER RENTAL ONLY.THE WEEKLY PRICE IN AUGUST IS $4,400. PER WEEK.SEE WEB SITE FOR ADDITIONAL WEEKLY PRICING. Looking for that perfect setting with a water view? This is the one!!This cute cape is privately set with a water view and direct water access to Town Pond. You can dock your canoes and kyacks here and access Tisbury Great Pond and then right out to the beach. There are

Karen Overtoom Karen M. Overtoom R.E.

50 Carls Way, West Tisbury, MA 02575
/17
$1,300,000 Sold Mar 03, 2025
- 1,241 Sq Ft
- $1048/SF
- 4 Days On Market
- 2 Beds
- 2 Baths
- Built 2018
22 Briarwood Ln, Vineyard Haven, MA 02568

This Recently Constructed Carriage House in Vineyard Haven is the epitome of thoughtful planning with custom details and exceptional finishes throughout. The sunny second level has an open floor living and kitchen area with vaulted ceilings. Highlights include a farmer’s sink, quartz countertops, pull out kitchen cabinets and self-closing drawers. There are two bedrooms, one is ensuite and the

Carol Shore Donnelly + Co

22 Briarwood Ln, Vineyard Haven, MA 02568

/41
Est $4,069,861 Not Listed For Sale
- 5 Beds
- 6 Baths
- 4,521 Sq Ft
89 Pond Rd, Vineyard Haven, MA 02568

89 Pond Rd, Vineyard Haven, MA 02568

/49
$6,490,000
- 6 Beds
- 8 Baths
- 5,660 Sq Ft
60 Meetinghouse Rd, Chilmark, MA 02535

This spectacular and bright modern american farmhouse is perfectly sited to capture the varied scenic beauty that surrounds the farm. Built in 2021 with great attention to detail and materials, this home was created around gatherings and community with ample space for the extended family. The land has been lovingly curated into a place which can grow, generate and support those who want to have

Jim Feiner Feiner Real Estate

60 Meetinghouse Rd, Chilmark, MA 02535
/21
$8,000 per month
- 1 Bed
- 1 Bath
- 936 Sq Ft
- House for Rent
10 James Pond Way, West Tisbury, MA 02575

THIS IS A WEEKLY SUMMER RENTAL ONLY.THE WEEKLY PRICE IN AUGUST IS $2,000. PER WEEK.SEE WEB SITE FOR ADDITIONAL WEEKLY PRICING. This spacious and well appointed one bedroom guest house has a cozy living area and kitchen which opens up to a large second story deck with outdoor furniture, table and chairs where you can enjoy dining amidst the trees. One A/C unit is in the bedroom along with a

Karen Overtoom Karen M. Overtoom R.E.

10 James Pond Way, West Tisbury, MA 02575
/45
$990,000 Sold Feb 19, 2025
- 1,618 Sq Ft
- $612/SF
- 145 Days On Market
- 3 Beds
- 2 Baths
- Built 1999
5 Rock Pond Rd, Vineyard Haven, MA 02568

Fantastic opportunity to own a South Mountain designed and built home in the coveted Island Co-Housing community. House #5 sits back from the community road with a great side yard, patio and outdoor shower.3 Large Bedrooms include a downstairs master w/ensuite bath off the living room area with a mid-way access leading to a private patio. The entryway opens on the kitchen, with thick shaker style

Kerry Quinlan-Potter Breakwater MV

5 Rock Pond Rd, Vineyard Haven, MA 02568

/20
Est $1,337,713 Not Listed For Sale
- 3 Beds
- 2 Baths
- 1,730 Sq Ft
225 Longview Rd, Vineyard Haven, MA 02568

225 Longview Rd, Vineyard Haven, MA 02568

/26
$1,985,000
- Land
- 3.58 Acres
- $554,469 per Acre
4 Cedar Ln Unit 2.2, Chilmark, MA 02535

Premier Build-Ready Lot with Private Beach AccessGet to know Stonewall Association, one of Chilmark’s most sought-after enclaves on the South Shore. This sunny, build-ready parcel offers a rare opportunity to own land with deeded private access to Stonewall Beach—a beloved destination for swimming, surfing, excellent fishing and summer memories. Set on beautifully contoured land with southern

Jill Napior Tea Lane Associates

4 Cedar Ln Unit 2.2, Chilmark, MA 02535
/29
$10,900 per month
- 3 Beds
- 1 Bath
- 936 Sq Ft
- House for Rent
58 Forest Rd Wt140, West Tisbury, MA 02575

THIS IS A WEEKLY SUMMER RENTAL ONLY.THE WEEKLY PRICE IN AUGUST IS $2,725.. PER WEEK.SEE WEB SITE FOR ADDITIONAL WEEKLY PRICING. This charming rustic home is set within Seven Gates Farm in West Tisbury. Walk down your own path to a beautiful private association beach. There are shared tennis courts and miles of walking trails.

Karen Overtoom Karen M. Overtoom R.E.

58 Forest Rd Wt140, West Tisbury, MA 02575
/2
$1,600,000 Sold Feb 04, 2025
- Land
- 3.60 Acres
- $444,444 per Acre
- 0 Days On Market
493 South Rd, Chilmark, MA 02535

Lovely pastoral lot within walking distance of beach and center of town.Perc test completed, septic being designed and well to be drilled shortly.Includes conservation restricted lot which consists of 10.6 acres.Build the home of your dreams in this amazing location.

Julianna Flanders Flanders Real Estate

493 South Rd, Chilmark, MA 02535

/2
Est $2,311,716 Not Listed For Sale
- 4 Beds
- 4 Baths
- 3,269 Sq Ft
59 Field View Ln, Vineyard Haven, MA 02568

59 Field View Ln, Vineyard Haven, MA 02568

/12
$1,325,000
- Land
- 4.12 Acres
- $321,602 per Acre
25 Plum Bush Point Rd Unit 6, West Tisbury, MA 02568

This beautiful wooded 4.12 acre parcel of land is peaceful, serene and ready to build. The well is installed, boundaries staked, perc test approved for a five-bedroom home and a septic plan designed. This is an opportunity to realize your vision and build a home that reflects your lifestyle. The large, flat building envelope offers many siting possibilities and, should you choose, the property

Abby Rabinovitz Tea Lane Associates

25 Plum Bush Point Rd Unit 6, West Tisbury, MA 02568
/20
$12,000 per month
- 3 Beds
- 1 Bath
- 1,068 Sq Ft
- House for Rent
76 Ben Chase Rd Wt136, West Tisbury, MA 02575

Experience a wonderful glimpse of country living in the peaceful, quiet setting of Serene Pond Cottage! This charming Martha's Vineyard retreat features a cozy interior with ample natural light, a private deck where you can take your breakfast and coffee, and a tree-lined backyard to enjoy on lazy summer days. Comfortable three bedroom single story home with one brand new renovated full bath with

Karen Overtoom Karen M. Overtoom R.E.

76 Ben Chase Rd Wt136, West Tisbury, MA 02575
/49
$1,750,000 Sold Jan 31, 2025
- 2,548 Sq Ft
- $687/SF
- 186 Days On Market
- 4 Beds
- 3 Baths
- Built 1984
75 Skiffs Ln, Vineyard Haven, MA 02568

Located on a beautiful, private 2.6 acre lot, this well-maintained home is move-in ready and awaiting your personal touch! Pool, manicured yard, plentiful parking, attached garage, large basement, outdoor shower and many more features make this spacious family home versatile and accommodating to your needs. You're able to enjoy the patio and pool with a built in fire pit during the summer months

Kelly Mercier Match Point Properties

75 Skiffs Ln, Vineyard Haven, MA 02568

/43
Not Listed For Sale
- 4 Beds
- 3.5 Baths
- 2,674 Sq Ft
39 Sarita Walker Rd, Vineyard Haven, MA 02568

39 Sarita Walker Rd, Vineyard Haven, MA 02568

/76
$3,995,000
- 5 Beds
- 3 Baths
- 2,791 Sq Ft
20 James Pond Way, Vineyard Haven, MA 02568

Nestled on a serene 4.5-acre parcel of land off Lambert's Cove Road, this exquisite property offers unparalleled privacy, views and direct access to James Pond and beyond to the Land Bank's Lambert's Cove Beach property. In addition to the custom heated Gunite pool, the expansive yard provides space for many outdoor activities while relishing the tranquility of the location. The residence

Sheila Morse Island Real Estate

20 James Pond Way, Vineyard Haven, MA 02568
/22
$20,000 per month
- 4 Beds
- 2.5 Baths
- 2,400 Sq Ft
- House for Rent
709 Old County Rd Wt134, West Tisbury, MA 02575

THIS IS A WEEKLY SUMMER RENTAL ONLY. The weekly price in August is $5,000. per week. See website for additional weekly pricing. Mill Pond House is a completely restored 1890s farmhouse on the old Mill Pond in historic West Tisbury. Remodeled by the present owner, an interior designer, it is beautifully appointed with antiques and charming accessories. An old pine floor and columns add to the

Karen Overtoom Karen M. Overtoom R.E.

709 Old County Rd Wt134, West Tisbury, MA 02575
/31
$2,525,000 Sold Jan 17, 2025
- 3,310 Sq Ft
- $763/SF
- 80 Days On Market
- 4 Beds
- 4 Baths
- Built 1991
106 Panhandle Rd, Vineyard Haven, MA 02568

With easy access to the West Tisbury Village, this lovely 4 bedroom, 3.5 bath home is privately sited on 1.4 acres overlooking a protected pasture. Many nice features include open living spaces, a well equipped kitchen with stainless steel appliances, a center island and granite. The sun-filled great room with oversized windows offer peaceful views of the meadow, a cathedral ceiling and sliders

Brenda Galligan Karen M. Overtoom R.E.

106 Panhandle Rd, Vineyard Haven, MA 02568

/41
Not Listed For Sale
- 3 Beds
- 2 Baths
- 1,598 Sq Ft
566 Scrubby Neck Rd, Vineyard Haven, MA 02568

566 Scrubby Neck Rd, Vineyard Haven, MA 02568

/35
$13,000,000
- 5 Beds
- 5 Baths
- 3,758 Sq Ft
6 Wakeman Rd, Chilmark, MA 02535

A 1930s-built home that has been remarkably updated to retain its historic charm while incorporating sophisticated and modern amenities. The house overlooks the Chilmark Great Pond and the Atlantic Ocean beyond. The Main House includes 3 bedrooms, 3 beautifully renovated bathrooms, a walk-in closet, a Pantry, a Library/Media room, a full basement, Outdoor showers, and a screened-in porch. The

Julianna Flanders Flanders Real Estate

6 Wakeman Rd, Chilmark, MA 02535
/19
$30,000 per month
- 5 Beds
- 4 Baths
- 3,600 Sq Ft
- House for Rent
37 Sachem Cir, West Tisbury, MA 02575

THIS IS A WEEKLY SUMMER RENTAL ONLY.THE WEEKLY PRICE IN AUGUST IS $7,500. PER WEEK.SEE WEB SITE FOR ADDITIONAL WEEKLY PRICING. Lovely pastoral setting with an elegant farm house and guest house. Abutting Land Bank property on two sides. Quiet privacy, yet just minutes to Lambert’s Cove Beach. The four bedroom house and separate guest house are impeccably decorated and the floor plan lends itself

Karen Overtoom Karen M. Overtoom R.E.

37 Sachem Cir, West Tisbury, MA 02575
/39
$2,895,000 Sold Jan 10, 2025
- 4,239 Sq Ft
- $683/SF
- 341 Days On Market
- 5 Beds
- 5 Baths
- Built 1999
18 S Pond Rd, Vineyard Haven, MA 02568

DEEP BOTTOM POND: 5-bedroom custom home with heated Pebbletec pool and exclusive association access to Tisbury Great Pond. This spacious layout features two primary suites, two guest rooms, and a third private guest suite. Perfect for entertaining, the open floor plan centers around the kitchen, dining, and living areas. The dramatic living room has cathedral ceilings, floor-to-ceiling windows, a

Rose Ryley Sandpiper Realty

18 S Pond Rd, Vineyard Haven, MA 02568

/15
Est $2,665,610 Not Listed For Sale
- 1 Bed
- 1 Bath
- 512 Sq Ft
119 Old Thumb Point Rd, Vineyard Haven, MA 02568

119 Old Thumb Point Rd, Vineyard Haven, MA 02568

Showing Results 81 - 120, Page 3 of 18

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