Dukes, MA Homes

/35
$2,850,000
- 4 Beds
- 3 Baths
- 2,967 Sq Ft
11 By the Woods, Chilmark, MA 02535

Dreamlike Chilmark retreat on 4.5+/- acres overlooking the Chilmark Pond & Atlantic Ocean beyond. Uniquely designed with European and medieval history in mind. The House has 3 bedrooms, 3 bathrooms, an atrium dining area, a two-story library, a kitchen, and a pantry/wet bar. Charming garden and plantings surround the home.A must-see to appreciate all the special touches throughout the Main House,

Julianna Flanders Flanders Real Estate

11 By the Woods, Chilmark, MA 02535
/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
/20
$821,000 Sold Jun 17, 2025
- Land
- 1.40 Acres
- $586,429 per Acre
- 0 Days On Market
168 Charles Neck Way Unit 49, Vineyard Haven, MA 02568

Large 1.4 Acre Corner lot in Vineyard Meadow Farms South side of West Tisbury Road. Private, flat, level parcel, paved dead end road with no unnecessary through traffic. Six bedrooms, a 3,000SF Main House, a 2,000SF detached/attached Secondary Building allowed per the Town. Pool allowed with standard Special permit. Centrally located to all Island Towns. Great neighborhood. Great location with

Janna O'Loughlin Portfolio Real Estate, Inc.

168 Charles Neck Way Unit 49, Vineyard Haven, MA 02568

/48
Est $2,960,910 Not Listed For Sale
- 6 Beds
- 3.5 Baths
- 3,440 Sq Ft
8 Coffins Field Rd, Edgartown, MA 02539

8 Coffins Field Rd, Edgartown, MA 02539

/13
$2,950,000
- 1 Bed
- 1 Bath
- 726 Sq Ft
18 Allen Farm Rd, Chilmark, MA 02535

Located in the agricultural heartland of Chilmark one mile from Lucy Vincent Beach this private 2.36 acre property has a charming 1 + bedroom cottage with screened porch, brick patio and outside shower. There is a large building zone located between the eighty and one hundred foot contour with exciting architectural options, especially for solar designs. The cottage is offered fully furnished,

Patty Kendall Kendall & Kendall

18 Allen Farm Rd, Chilmark, MA 02535
/42
$19,000 per month
- 6 Beds
- 6.5 Baths
- 6,950 Sq Ft
- House for Rent
40 Sweet William Way, West Tisbury, MA 02575

THIS PROPERTY IS A WEEKLY RENTAL PROPERTY! This stunning home is situated right in the heart of West Tisbury, yet set back enough for a completely private feel. On a property that encompasses 10 acres with your own private pond, you will feel the stress melt away as soon as you get to this luxury vacation home. Keys to private Quansoo Beach Association come with the house. Spend your days on the

Karen Overtoom Karen M. Overtoom R.E.

40 Sweet William Way, West Tisbury, MA 02575
/18
$1,219,000 Sold Jun 16, 2025
- 1,512 Sq Ft
- $806/SF
- 99 Days On Market
- 3 Beds
- 2 Baths
- Built 1986
108 Charles Neck Way, Vineyard Haven, MA 02568

This charming reverse-style home is ideally located near Long Point Beach and offers a perfect blend of comfort and functionality for year-round living or seasonal getaways. The first floor features three spacious bedrooms, a full bath, and a convenient laundry room. On the second floor, you'll find soaring cathedral ceilings and an open-concept living area, complete with a cozy living room,

Alyssa Halisky Wallace & Co. Sotheby's

108 Charles Neck Way, Vineyard Haven, MA 02568

/49
Not Listed For Sale
- 4 Beds
- 4 Baths
- 2,092 Sq Ft
670 State Rd, Vineyard Haven, MA 02568

670 State Rd, Vineyard Haven, MA 02568

/34
$2,895,000
- 4 Beds
- 4 Baths
- 2,300 Sq Ft
31 N Slope Ln, Chilmark, MA 02535

Located on a private lane along North Road in the heart of Chilmark, this hilltop four bedroom home was perfectly sited to enjoy fantastic water views of Vineyard Sound toward the Elizabeth Islands. Built in 1983 and lived in seasonally, this home has been meticulously cared for. There is a new forced air HVAC system, and recently upgraded electrical. In addition, there are three working

Bill Rossi Studio Realty

31 N Slope Ln, Chilmark, MA 02535
/28
$32,000 per month
- 4 Beds
- 4 Baths
- 3,200 Sq Ft
- House for Rent
37 Mempremagog Ave Vh410, Tisbury, MA 02568

THIS IS A WEEKLY SUMMER RENTAL ONLY.THE WEEKLY PRICE IN AUGUST IS $8,200. PER WEEK.SEE WEB SITE FOR ADDITIONAL WEEKLY PRICING. Fabulous custom designed and decorated four bedroom home is located in a wooded setting that offers total privacy and is with-in walking distance to a private association beach. And yet is only 3 miles from downtown Vineyard Haven. This lovely home offers a gourmet eat-in

Karen Overtoom Karen M. Overtoom R.E.

37 Mempremagog Ave Vh410, Tisbury, MA 02568
/20
$1,150,000 Sold Jun 13, 2025
- 1,374 Sq Ft
- $837/SF
- 43 Days On Market
- 3 Beds
- 2 Baths
- Built 1981
46 Old Coach Rd, Vineyard Haven, MA 02568

Charming and Spacious 3-Bedroom Cape with large Loft and Deck Welcome to your dream West Tisbury home! This comfortable and spacious 3-bedroom, 2-bath Cape boasts a thoughtfully designed floor plan perfect for comfortable living. The first-floor features two bedrooms and a full bath, ideal for use as sleeping quarters or a home office. Moving to the second floor, discover privacy with a third

Lisa Gilberto C McManus Realty Group

46 Old Coach Rd, Vineyard Haven, MA 02568

/75
Est $4,011,141 Not Listed For Sale
- 4 Beds
- 2 Baths
- 1,362 Sq Ft
4 Tilton Rd, Chilmark, MA 02535

4 Tilton Rd, Chilmark, MA 02535

/46
$3,500,000
- 4 Beds
- 3 Baths
- 2,383 Sq Ft
100 Gosnolds Way, Chilmark, MA 02535

Well designed and maintained home, situated on 5 acres in a private, desirable neighborhood. Open floor plan with high ceilings that allows a lot of great light into house. The screened in porch is perfect for family dinners or relaxing. Nice water views of Vineyard Sound & the Elizabeth Islands. Short walk to the Brickyard Beach on the North Shore, rights are included with property, where

Julianna Flanders Flanders Real Estate

100 Gosnolds Way, Chilmark, MA 02535
/3
$13,200 per month
- 2 Beds
- 2 Baths
- 1,344 Sq Ft
- House for Rent
224 N Rd Ch248, Chilmark, MA 02535

THIS PROPERTY IS A WEEKLY RENTAL PROPERTY!! A modern summer retreat is nestled high on a knoll off North Rd in picturesque Chilmark. Here in this stunning contemporary ranch you will find the upmost in Luxury. Each room is exciting, charming and has a simplistic yet artistic style. The entire house is accented with beautiful light pine flooring that pairs perfectly with the expansive main room.

Karen Overtoom Karen M. Overtoom R.E.

224 N Rd Ch248, Chilmark, MA 02535
/3
$1,695,000 Sold May 30, 2025
- 1,296 Sq Ft
- $1308/SF
- 2 Beds
- 2 Baths
- Built 1960
5 Vincent Rd, Vineyard Haven, MA 02568

NOT LISTED IN LINK

Alisan Lohan-Conway Alisan Lohan-Conway Properties

5 Vincent Rd, Vineyard Haven, MA 02568

/31
Est $2,432,400 Not Listed For Sale
- 3 Beds
- 2 Baths
- 1,386 Sq Ft
7 the Aerie, Chilmark, MA 02535

7 the Aerie, Chilmark, MA 02535

/46
$3,476,000 Pending
- 4 Beds
- 3 Baths
- 3,669 Sq Ft
140 Pond Rd, Vineyard Haven, MA 02568

Welcome to this beautifully updated and privately situated home in one of West Tisbury’s most desirable associations. Residents enjoy exclusive access to tennis courts, walking trails, horse pastures and Tisbury Great Pond. Designed for both comfort and luxury, this spacious 4+ bedroom, 3 bathroom property is ideal as a year-round residence or upscale vacation retreat.The first floor

Jon Hartzband Martha's Vineyard Island-Wide Realty

140 Pond Rd, Vineyard Haven, MA 02568
/26
$50,700 per month
- 4 Beds
- 3 Baths
- 2,346 Sq Ft
- House for Rent
6 Trails End Ch241, Chilmark, MA 02535

THIS IS A WEEKLY SUMMER RENTAL ONLY.THE WEEKLY PRICE IN AUGUST IS $12,675. PER WEEK.SEE WEB SITE FOR ADDITIONAL WEEKLY PRICING. Set atop a hill you will find this wonderful 4 bedroom home with distant views and a wonderful lap pool. Enjoy your days on the large deck or take a swim in the pool. This great vacation home is tastefully decorated and is located on one level with plenty of space for

Karen Overtoom Karen M. Overtoom R.E.

6 Trails End Ch241, Chilmark, MA 02535
/15
$1,150,000 Sold May 30, 2025
- 1,338 Sq Ft
- $859/SF
- 48 Days On Market
- 4 Beds
- 2 Baths
- Built 1966
14 Galway Rd, Vineyard Haven, MA 02568

Welcome to 14 Galway Road, West Tisbury. The home and property have been lovingly maintained and used by the same family since the home was built. It offers an open eat-in kitchen/living room design with a masonry fireplace. On the first floor are two bedrooms, one full bathroom, a linen closet, and hidden washer and dryer along the hallway. The stairway brings you to a second floor which

Michele Casavant Vineyard Village Realty

14 Galway Rd, Vineyard Haven, MA 02568

/36
Est $2,520,452 Not Listed For Sale
- 4 Beds
- 3.5 Baths
- 2,791 Sq Ft
225 Great Plains Rd, Vineyard Haven, MA 02568

225 Great Plains Rd, Vineyard Haven, MA 02568

/28
$2,950,000 Under Contract
- 3 Beds
- 2 Baths
- 1,524 Sq Ft
10 Molly's Ln, Chilmark, MA 02535

The Salt Shack merges historic preservation with modern updates in Menemsha. Designed by husband-and-wife luxury boutique design firm, Morgan Studio, the renovation of this 100-year-old ocean view cottage preserves its charm and historical integrity while incorporating contemporary design elements to enhance both comfort and aesthetics. Nestled behind Menemsha Pond, the cottage boasts a prime

Peyton Wallace Studio Realty

10 Molly's Ln, Chilmark, MA 02535
/19
$24,000 per month
- 4 Beds
- 4 Baths
- 2,000 Sq Ft
- House for Rent
44 Flanders Ln, Chilmark, MA 02535

THIS IS A WEEKLY SUMMER RENTAL ONLY.!! SEE WEB SITE FOR WEEKLY PRICING. This house sits up the hill and looks toward Menemsha. It is private and protected by the trees. Visit town to watch sunsets in Menemsha, dine in one of the places to eat there or take in a day at the beach.Access to and parking for beautiful private association beach.

Karen Overtoom Karen M. Overtoom R.E.

44 Flanders Ln, Chilmark, MA 02535
/32
$1,050,000 Sold May 29, 2025
- 1,701 Sq Ft
- $617/SF
- 28 Days On Market
- 4 Beds
- 2 Baths
- Built 1960
10 Rumpus Ridge Rd, Chilmark, MA 02535

Discover this inviting two-unit property in the heart of Chilmark! Ideally situated near Chilmark General Store, Squibnocket, Menemsha, and the pristine shores of Lucy Vincent Beach, this home offers both convenience and charm. Thoughtfully updated for year-round comfort, the property features a new metal roof, new siding, solar panels, mini-split AC, and more. The main-level residence offers

Peyton Wallace Studio Realty

10 Rumpus Ridge Rd, Chilmark, MA 02535

/34
Est $1,628,990 Not Listed For Sale
- 3 Beds
- 2 Baths
- 1,452 Sq Ft
84 Christiantown Rd, Vineyard Haven, MA 02568

84 Christiantown Rd, Vineyard Haven, MA 02568

/32
$2,250,000
- 4 Beds
- 3 Baths
- 2,522 Sq Ft
29 Old Nursery Ln, Chilmark, MA 02535

Modern Cape style home located off Tea Lane could be your special Chilmark retreat. This four bedroom, 2.5 bathroom home needs some updating but is in good condition. Living room with fireplace, dining area and family room provide space for living. Attached two bay garage allows for storage and projects. Wood working area in the basement is a plus. Enjoy the outdoors via the screened porch, large

Julianna Flanders Flanders Real Estate

29 Old Nursery Ln, Chilmark, MA 02535
/31
$40,000 per month
- 6 Beds
- 6 Baths
- 3,960 Sq Ft
- House for Rent
384 Middle Rd Ch222, Chilmark, MA 02535

THIS IS A WEEKLY SUMMER RENTAL ONLY.THE WEEKLY PRICE IN AUGUST IS $10,000. PER WEEK.SEE WEB SITE FOR ADDITIONAL WEEKLY PRICING. This gracious Vineyard elongated Cape overlooks the Keith Farm and the Atlantic Ocean beyond. The gourmet kitchen has just been beautifully renovated and is a dream. The living areas are all decorated with charm and all have views. The separate main house, with four

Karen Overtoom Karen M. Overtoom R.E.

384 Middle Rd Ch222, Chilmark, MA 02535
/26
$1,850,000 Sold May 14, 2025
- 2,610 Sq Ft
- $709/SF
- 8 Days On Market
- 5 Beds
- 4 Baths
- Built 1986
137 Charles Neck Way, Vineyard Haven, MA 02568

Fantastic opportunity to buy a two house compound in West Tisbury close to Long Point Beach access. A perfect investment, rental income generator or to host extended family and guests.Two well built houses on 1.6 acres, that have been impeccably maintained by the original owner. Offering a total of 5 bedrooms, 4 bathrooms, 2 outdoor showers and 2 garages. There is a charming garden shed and low

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

137 Charles Neck Way, Vineyard Haven, MA 02568

/36
Est $2,245,934 Not Listed For Sale
- 6 Beds
- 4 Baths
- 2,705 Sq Ft
9 Heather Trail, Vineyard Haven, MA 02568

9 Heather Trail, Vineyard Haven, MA 02568

/7
$650,000
- Land
- 0.20 Acre
- $3,250,000 per Acre
00 Hancock Beach Lot Unit 73, Chilmark, MA 02535

Spectacular Hancock beach lot on the Atlantic Ocean. Ownership of this lot allows you access to one of the world's most beautiful beaches, plenty of parking and away from the crowds. It is a most enjoyable spot to spend a relaxing day on the Vineyard, sunbathing, fishing, kayaking, canoeing, etc. as you also gain access to Chilmark Pond. Any property on the Vineyard would be greatly enhanced by

Deb Hancock Hancock Real Estate

00 Hancock Beach Lot Unit 73, Chilmark, MA 02535
/20
$16,800 per month
- 3 Beds
- 2 Baths
- 1,638 Sq Ft
- House for Rent
31 S Ridge Rd Ch218, Chilmark, MA 02535

THIS IS A WEEKLY SUMMER RENTAL ONLY.THE WEEKLY PRICE IN AUGUST IS $4,200. PER WEEK.SEE WEB SITE FOR ADDITIONAL WEEKLY PRICING. Set high on a hill in picturesque Chilmark is this absolutely wonderful 3 bedroom home with a finished walk out that has a sofa bed. Each bedroom has a window A/C unit. The grounds are beautiful. Wonderful screen porch for your morning coffee or sit in the back yard and

Karen Overtoom Karen M. Overtoom R.E.

31 S Ridge Rd Ch218, Chilmark, MA 02535
/13
$2,050,000 Sold May 01, 2025
- 1,007 Sq Ft
- $2036/SF
- 0 Days On Market
- 2 Beds
- 1 Bath
- Built 2016
16 Red Coat Hill Rd, Vineyard Haven, MA 02568

Exquisite West Tisbury Property: A Unique Opportunity.Discover the allure of a truly exceptional property nestled on 4.85 stunning acres in the serene locale of West Tisbury. This opportunity is not one to be missed, as it combines elegance, foresight, and sustainability in perfect harmony.The home is adorned with beautiful beams throughout, with nickelboard and shiplap covering the walls and

Joe & Nicole Holland Vineyard Dream Realty LLC

16 Red Coat Hill Rd, Vineyard Haven, MA 02568

/18
Est $1,863,909 Not Listed For Sale
- 4 Beds
- 3 Baths
- 2,461 Sq Ft
29 Brook Hollow Rd, Vineyard Haven, MA 02568

29 Brook Hollow Rd, Vineyard Haven, MA 02568

/26
$3,695,000
- Land
- 7 Acres
- $551,493 per Acre
32 Stonewall Road and 4 Cedar Ln Unit 2.1 and 2.2, Chilmark, MA 02535

Discover an exceptional opportunity with this rare combination of two abutting parcels spanning more than 6 acres in a coveted location offering water views and Atlantic Ocean private beach access. Surfers and fishermen delight in this location! The Stonewall Association is a beloved area of Chilmark in a supreme location for easy Chilmark living close to the Chilmark Store, the Chilmark

Jill Napior Tea Lane Associates

32 Stonewall Road and 4 Cedar Ln Unit 2.1 and 2.2, Chilmark, MA 02535
/32
$36,000 per month
- 3 Beds
- 3.5 Baths
- 2,600 Sq Ft
- House for Rent
29 Cemetery Rd Ch216, Chilmark, MA 02535

THIS IS A WEEKLY SUMMER RENTAL ONLY.THE WEEKLY PRICE IN AUGUST IS $9,000. PER WEEK.SEE WEB SITE FOR ADDITIONAL WEEKLY PRICING. Fabulous Chilmark home offers two levels of living space. On the first floor there is a fully equipped kitchen open to the dining room, a living room with fireplace, built-ins and sliders to a deck overlooking a meadow and the most incredible water views. There is a half

Karen Overtoom Karen M. Overtoom R.E.

29 Cemetery Rd Ch216, Chilmark, MA 02535
/50
$3,000,000 Sold Apr 29, 2025
- 3,311 Sq Ft
- $906/SF
- 3 Beds
- 3 Baths
- Built 2000
34 S Pond Rd, Vineyard Haven, MA 02568

Stunning Deep Bottom Pond property with an oversized 3.77-acre lot surrounded by Mother Nature’s beauty, with exclusive association access to Tisbury Great Pond and private tennis courts. This beautiful home is lovingly maintained and ready for immediate occupancy. Through the welcoming grand foyer, a cathedral-ceiling living room with a fabulous wood-burning fireplace, and slider doors leading

Stephanie Roache Donnelly + Co

34 S Pond Rd, Vineyard Haven, MA 02568

/16
Est $1,345,870 Not Listed For Sale
- 3 Beds
- 2 Baths
- 1,150 Sq Ft
31 Music St, Vineyard Haven, MA 02568

31 Music St, Vineyard Haven, MA 02568

/8
$3,200,000
- Land
- 19 Acres
- $165,803 per Acre
32 Edgartown - West Tisbury Rd Unit 81, West Tisbury, MA 02575

A Rare Offering in West Tisbury — Over 19 Acres of OpportunityAn exceptional opportunity to own just over 19 acres in the heart of rural West Tisbury. This expansive parcel offers tremendous flexibility, with potential for multiple dwellings or subdivision into a thoughtfully designed niche development. Ideally situated near all island towns, the property is also just minutes from the

Jill Napior Tea Lane Associates

32 Edgartown - West Tisbury Rd Unit 81, West Tisbury, MA 02575
/33
$22,000 per month
- 3 Beds
- 2.5 Baths
- 2,800 Sq Ft
- House for Rent
2 Strikers Way Ch211, 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. Just a short distance from Chilmark Store, this newly remodeled home features 3 bedrooms and 2 1/2 baths. High end finishes with a beachy island feel. The master is located on the first floor with en-suit bath. Fully equipped kitchen with a Cuisinart 14-cup programmable

Karen Overtoom Karen M. Overtoom R.E.

2 Strikers Way Ch211, 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

/17
Est $1,082,396 Not Listed For Sale
- 3 Beds
- 2 Baths
- 934 Sq Ft
10 Briarwood Ln, Vineyard Haven, MA 02568

10 Briarwood Ln, Vineyard Haven, MA 02568

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