Dukes, MA Homes

/43
$1,895,000
- 3 Beds
- 4 Baths
- 2,512 Sq Ft
10 Bridge Ln, Vineyard Haven, MA 02568

This thoughtfully designed post and beam home blends craftsmanship with character, featuring artistic touches throughout that make it truly one-of-a-kind. The kitchen flows beautifully between the main living areas and an inviting dining space surrounded by windows offering access to one of several outdoor decks for effortless indoor-outdoor living. On the first floor, the primary suite includes

Jill Napior Tea Lane Associates

10 Bridge Ln, Vineyard Haven, MA 02568
/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
/74
$3,284,500 Sold May 23, 2025
- 3,085 Sq Ft
- $1065/SF
- 657 Days On Market
- 6 Beds
- 6 Baths
- Built 2024
9 Hollow Way, Edgartown, MA 02539

EDGARTOWN - NEW CONSTRUCTION with POOL - 6 Bedrooms...in Two Structures.....Plus a 31'6" x 14' heated saltwater pool! 5 Bedroom Main House with 4.5 Bathrooms. Detached 1 bedroom w/Full Bathroom over a Two (2) car garage. Main house has a lovely open floor plan with a large kitchen w/Bosch Stainless Steel Appliances, beautiful Soapstone Island and Carrara Marble counters, a dining room,

Alisan Lohan-Conway Alisan Lohan-Conway Properties

9 Hollow Way, Edgartown, MA 02539

/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

/37
$1,995,000
- 4 Beds
- 3 Baths
- 3,058 Sq Ft
2 Farm Path, Oak Bluffs, MA 02557

"Turn-key" offering! This custom cape design with a delightful farmer's porch provides ample opportunities to entertain. Set upon nearly an acre of level and landscaped land with irrigation, it abuts the State Forrest, has an open floor plan with cathedral ceilings and skylights. The three bedroom main, has A/C, a finished basement rec room, a large rear deck that spills forth onto a large yard

Sean Federowicz Landmarks at TODAY Real Estate

2 Farm Path, Oak Bluffs, MA 02557
/26
$50,000 per month
- 4 Beds
- 3 Baths
- 3,237 Sq Ft
- House for Rent
29 Naushon Rd Wt142, West Tisbury, MA 02575

THIS IS A WEEKLY SUMMER RENTAL ONLY.THE WEEKLY PRICE IN AUGUST IS $12,500. PER WEEK.SEE WEB SITE FOR ADDITIONAL WEEKLY PRICING. Waterfront home in spectacular location overlooking the Vineyard Sound and the Elizabeth Islands. This casual and comfortable single level 4 BR 3 bath home has central air and heat. Enjoy summer star-studded skies from your patio or through skylights in each bedroom.

Karen Overtoom Karen M. Overtoom R.E.

29 Naushon Rd Wt142, West Tisbury, MA 02575
/37
$1,835,000 Sold May 23, 2025
- 2,391 Sq Ft
- $767/SF
- 59 Days On Market
- 4 Beds
- 4 Baths
- Built 2001
41 Smith Hollow Dr, Edgartown, MA 02539

Discover this exquisite, contemporary home nestled in the heart of Edgartown's Smith Hollow, conveniently located just off the bike path and mere minutes from the lively Edgartown Village. Situated in a welcoming, family-oriented neighborhood, this stylish residence boasts a bright and airy open floor plan.The Great Room captivates with its soaring cathedral wood ceiling and robust timber accent

Marilyn Moses Ocean Park Realty Inc

41 Smith Hollow Dr, Edgartown, MA 02539

/19
Not Listed For Sale
- 4 Beds
- 3 Baths
- 1,714 Sq Ft
43 Look St, Vineyard Haven, MA 02568

43 Look St, Vineyard Haven, MA 02568

/30
$2,195,000
- 4 Beds
- 3 Baths
- 2,730 Sq Ft
5 Pine Tree Ln, Vineyard Haven, MA 02568

Blending 1920s charm with modern luxury, this beautifully renovated home is tucked away in the sought-after West Chop area of Vineyard Haven. Just steps from the neighborhood beach on the pristine shores of Vineyard Sound, this elegant seaside retreat offers the perfect mix of historic character and contemporary comfort. Inside, a thoughtfully designed floor plan welcomes you with generous living

Alyssa Halisky Wallace & Co. Sotheby's International Realty

5 Pine Tree Ln, Vineyard Haven, 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
/28
$1,270,000 Sold May 23, 2025
- 2,192 Sq Ft
- $579/SF
- 57 Days On Market
- 3 Beds
- 2 Baths
- Built 1940
60 Prospect Ave, Oak Bluffs, MA 02557

OAK BLUFFS ~ APPROVED 4 BEDROOM SEPTIC IN PLACE - This home LIVES LARGE and offers 3 Distinct Structures situated on a BEAUTIFUL landscaped .34 Acre private lot ~EASY WALK or BIKE RIDE to OAK BLUFFS HARBOR, Town, Sandy Beaches, Ferry Ports and Town Parks! Tastefully renovated SPACIOUS Split-Level Home featuring a lovely and functional open floor plan. The main level displays beautiful hardwood

Marilyn Moses Ocean Park Realty Inc

60 Prospect Ave, Oak Bluffs, MA 02557

/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

/24
$2,150,000
- 2 Beds
- 2.5 Baths
- 2,137 Sq Ft
30 Franklin Ave, Oak Bluffs, MA 02568

Welcome to your dream home! This stunning new construction boasts a coastal feel throughout and is situated on a spacious corner lot. Inside, you'll find luxurious finishes, including Thermador appliances and quartz countertops in the gourmet kitchen including a large pantry with beverage refrigerator. The elegance continues with white oak floors throughout the home. With 2 bedrooms and 2.5

Stacy Ickes Donnelly + Co.

30 Franklin Ave, Oak Bluffs, MA 02568
/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
/24
$665,000 Sold May 23, 2025
- 806 Sq Ft
- $825/SF
- 171 Days On Market
- 3 Beds
- 2 Baths
- Built 1876
51 Rural Cir, Oak Bluffs, MA 02557

The Spirit of '76 is a lovely Campground cottage nestled into the landscape for privacy and shade. Just a couple of blocks to the beach, town center, shops, and restaurants. A fabulous wrap around porch with various seating areas. Built in 1876 this wonderful throwback of yesteryear features some original furnishings included in the sale. With a classic front parlor, dining room, and kitchen, a

Lisa Lucier Anchor Realty of Martha's Vineyard

51 Rural Cir, Oak Bluffs, MA 02557

/25
Est $1,519,332 Not Listed For Sale
- 5 Beds
- 3 Baths
- 2,287 Sq Ft
101 Dunham Ave, Vineyard Haven, MA 02568

101 Dunham Ave, Vineyard Haven, MA 02568

/24
$2,095,000
- 4 Beds
- 4 Baths
- 2,413 Sq Ft
46 Red Buoy Ln, Tisbury, MA 02568

Nestled in Vineyard Haven, 46 Red Buoy Lane is an exquisite and sophisticated home completed in 2022. This residence offers 4 bedrooms and 3.5 bathrooms and spans a generous 1,816 square feet. The property's unique offering of a one-bedroom apartment in the basement is noteworthy, providing an additional 597 square feet of living space. The main level boasts a thoughtfully designed floor plan

Andrew McElhinney Compass LLC

46 Red Buoy Ln, Tisbury, 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
/27
$1,600,000 Sold May 22, 2025
- 1,594 Sq Ft
- $1004/SF
- 532 Days On Market
- 3 Beds
- 2 Baths
- Built 1933
2 E Side Road & 60 Bay View Ave, Oak Bluffs, MA 02557

Stunning sunsets await. This quintessential bungalow style Vineyard home has been lovingly maintained and enjoyed by the same family for close to 100 years. Built in 1933, the main house includes three bedrooms, two full baths and hardwood floors throughout. The spacious living area boasts high ceilings, stone fireplace, and expansive water views. Summer days and nights are well spent under the

Carol Shore Donnelly + Co

2 E Side Road & 60 Bay View Ave, Oak Bluffs, MA 02557

/48
Est $1,457,177 Not Listed For Sale
- 6 Beds
- 5.5 Baths
- 2,417 Sq Ft
152 Main St, Vineyard Haven, MA 02568

152 Main St, Vineyard Haven, MA 02568

/26
$2,150,000 New Construction
- 2 Beds
- 3 Baths
- 2,137 Sq Ft
30 Franklin Ave, Oak Bluffs, MA 02568

Welcome to your dream home! This stunning new construction boasts a coastal feel throughout and is situated on a spacious corner lot. Inside, you'll find luxurious finishes, including Thermador appliances and quartz countertops in the gourmet kitchen including a large pantry with beverage refrigerator. The elegance continues with white oak floors throughout the home. With 2 bedrooms and 2.5

Stacy Ickes Donnelly + Co

30 Franklin Ave, Oak Bluffs, MA 02568
/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
/13
$1,195,000 Sold May 22, 2025
- 1,110 Sq Ft
- $1077/SF
- 8 Days On Market
- 3 Beds
- 2 Baths
- Built 2006
34 10th St S, Edgartown, MA 02539

This charming 3 bedroom, 2 bathroom ranch-style Edgartown home offers comfortable single-level living with classic Vineyard appeal. The layout includes a dedicated living room, and an open kitchen and dining area. The primary suite features a private bath, while two additional bedrooms share a full bathroom. Outside, the property provides deck overlooking the yard for enjoying the outdoors.

Rose Ryley Sandpiper Realty Inc

34 10th St S, Edgartown, MA 02539

/11
Est $1,007,586 Not Listed For Sale
- 3 Beds
- 1 Bath
- 1,180 Sq Ft
36 Park Ave, Vineyard Haven, MA 02568

36 Park Ave, Vineyard Haven, MA 02568

/41
$2,590,000 Pending
- 4 Beds
- 4 Baths
- 3,052 Sq Ft
27 Watcha Path, Edgartown, MA 02539

STYLISH VINEYARD LIVING WITH EXCEPTIONAL OUTDOOR AMENITIES. This beautifully landscaped coastal-style home is set on three acres just off the bike path, offering easy access to all Island towns. The highlight? A heated salt water pool surrounded by expansive decking and outdoor gathering spaces—an ideal setup for Vineyard summers. Thoughtfully updated by the current owners, the home features four

Jen O'Hanlon Compass | The O'Hanlon Group

27 Watcha Path, 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
/36
$5,500,000 Sold May 20, 2025
- 3,262 Sq Ft
- $1686/SF
- 295 Days On Market
- 4 Beds
- 5 Baths
- Built 1984
12 Tamarack Ln, Oak Bluffs, MA 02536

This bright and sunny home has a spectacular waterview overlooking the Eighth Fairway of Farm Neck Golf Course, Sengekontacket Pond and Nantucket Sound. Professionaly designed landscaping with perennial beds and charming brick courtyard add to its ambiance. Included are Farm Neck Golf Club stockholder membership (meaning immediate entry into golf membership), tennis and dock & mooring privileges.

Betsy Kessler Rutledge Properties

12 Tamarack Ln, Oak Bluffs, MA 02536

/31
Est $1,461,908 Not Listed For Sale
- 3 Beds
- 2 Baths
- 1,999 Sq Ft
48 Puritan Dr, Vineyard Haven, MA 02568

48 Puritan Dr, Vineyard Haven, MA 02568

/41
$1,995,000 Under Contract
- 3 Beds
- 3 Baths
- 2,210 Sq Ft
26 Tia Anna Ln, Oak Bluffs, MA 02557

Welcome to 26 Tia Anna Lane! This exquisite residence is immaculate, stylish, and fully renovated, ready to welcome its new owners! Situated on a beautifully landscaped 0.30-acre lot adorned with vibrant plantings, the home boasts pristine conditions both inside and out, featuring newer Hardi Plank siding. The inviting farmer's porch, complete with Mahogany decking, sets the tone for this

Marilyn Moses Ocean Park Realty Inc

26 Tia Anna Ln, Oak Bluffs, MA 02557
/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
/45
$1,225,000 Sold May 19, 2025
- 1,725 Sq Ft
- $710/SF
- 338 Days On Market
- 3 Beds
- 2 Baths
- Built 1986
51 Head of the Pond Rd, Vineyard Haven, MA 02568

Iron Hill, Centrally located with convenient access to Island villages. 3 Bedroom, 2 Bath Ranch on 1.5+ acres. An empty canvas with limitless possibilities. Mature landscaping designed for privacy, aesthetics, and low maintenance. Paved private road access, with generous setback for residence. Bike path, Bus stop, State Forest, & Walking Trails nearby. Association covenants allow up to two

Bruce Stuart Bruce Stuart and Associates

51 Head of the Pond Rd, Vineyard Haven, MA 02568

/14
Est $1,503,222 Not Listed For Sale
- 3 Beds
- 2 Baths
- 2,717 Sq Ft
13 Saddle Club Rd, Edgartown, MA 02539

13 Saddle Club Rd, Edgartown, MA 02539

/6
$1,149,000
- 3 Beds
- 2 Baths
- 960 Sq Ft
67 12th St S, Edgartown, MA 02539

This ranch style 3 bedroom home centrally located in a quiet neighborhood is close to the bike path with easy access to town and beaches. Sited on a 12,000 square foot parcel with a spacious privately enclosed yard and mature gardens. First floor includes an efficient galley kitchen with a quaint dining area. The living room leads out to a cozy front porch. There is also a spacious side deck that

Brenda Galligan Karen M. Overtoom R.E.

67 12th St S, Edgartown, MA 02539
/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
/18
$1,200,000 Sold May 19, 2025
- 2,080 Sq Ft
- $577/SF
- 590 Days On Market
- 3 Beds
- 2 Baths
- Built 1972
193 Franklin Terrace, Vineyard Haven, MA 02568

Perched on a sunny sloping lot, this 3-bedroom, 2-bath year-round home in a quiet established neighborhood is walking distance to the heart of town and close to everything. Septic can accommodate 4 bedrooms. Deck with grilling area and outdoor shower looking over the landscaped side yard. On the main level, open kitchen with a large island. On the lower level, 3 bedrooms, 2 have walkout access. A

Claire Callagy Compass

193 Franklin Terrace, Vineyard Haven, MA 02568

/20
Est $1,725,885 Not Listed For Sale
- 4 Beds
- 3 Baths
- 1,240 Sq Ft
11 Pine Tree Ln, Vineyard Haven, MA 02568

11 Pine Tree Ln, Vineyard Haven, MA 02568

/8
$695,000
- Land
- 0.29 Acre
- $2,396,552 per Acre
37 Double Ox Rd, Oak Bluffs, MA 02557

This is your opportunity to get in on the ground floor of Lagoon Ridge, a stunning, new development. Several homes are already in place. This beautiful, wooded Lot is located down meandering, newly paved roads, just .4 mile from Barnes Road and the Lagoon. For the outdoor enthusiast, walk and ride the numerous hiking and biking trails that traverse the abutting conservation lands. All utility

Lynn Buder Sandpiper Realty Inc

37 Double Ox Rd, Oak Bluffs, MA 02557
/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
/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

/47
Est $2,356,806 Not Listed For Sale
- 6 Beds
- 4 Baths
- 3,627 Sq Ft
24 Peacegate Way, Vineyard Haven, MA 02568

24 Peacegate Way, Vineyard Haven, MA 02568

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