Dukes, MA Homes

/42
$2,125,000
- 3 Beds
- 4 Baths
- 2,558 Sq Ft
35 Tower Ridge Rd, Oak Bluffs, MA 02557

Thoughtfully designed post-and-beam home that blends character with modern comfort and flexible living in Tower Ridge. The open-concept main floor features spacious gathering areas, while the finished basement offers a quiet retreat for work, relaxation, or play. The outdoor living space is just as inviting, with an oversized deck overlooking mature plantings and a generous side yard--perfect for

Katherine Donahue Sandpiper Realty Inc

35 Tower Ridge Rd, Oak Bluffs, MA 02557
/26
$18,000 per month
- 3 Beds
- 2.5 Baths
- 2,400 Sq Ft
- House for Rent
40 Lighthouse Rd, Aquinnah, MA 02535

Great water view property in Aquinnah - this immaculate contemporary has that unique combination of a beautifully designed and constructed, year-round home, AND an outstanding view of the Sound and Elizabeth Islands. Not only is the water view property packed with many custom details, but the home's layout is perfect for relaxed living - with a fantastic kitchen open to the dining and living

Karen Overtoom Karen M. Overtoom R.E.

40 Lighthouse Rd, Aquinnah, MA 02535
/13
$776,500 Sold Mar 05, 2025
- 768 Sq Ft
- $1011/SF
- 17 Days On Market
- 2 Beds
- 1 Bath
- Built 1968
32 Clark Ave, Vineyard Haven, MA 02568

This two bedroom year-round home will afford you all the opportunities Vineyard Haven has to offer. This private lot is bursting with lilacs, forsythia, wisteria, raspberry canes, a mock orange bush and a peach tree. The home boasts natural light, cathedral ceilings, a comfortable kitchen and living area with two bedrooms and one full bath. There is a mudroom and a handsome, fully enclosed front

Diana Gilmore Island Real Estate

32 Clark Ave, Vineyard Haven, MA 02568

/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

/40
$1,890,000
- 5 Beds
- 3 Baths
- 2,704 Sq Ft
11 Huckleberry Hill Ln, Edgartown, MA 02539

Turn-Key 5-Bedroom Home with Legal Apartment Near Edgartown Village — Set back from the road and less than a mile from Main Street, this spacious and stylish Edgartown property offers an ideal blend of privacy, comfort, and investment potential. The main home features four well-proportioned bedrooms—including one conveniently located on the first floor—and an open kitchen and dining area designed

Jennifer O'hanlon Compass

11 Huckleberry Hill Ln, Edgartown, MA 02539
/15
$40,000 per month
- 6 Beds
- 3 Baths
- 1,704 Sq Ft
- House for Rent
120 Eastville Ave Ob520, Oak Bluffs, MA 02557

THIS IS A SUMMER RENTAL ONLY. Watch the boats come and go from the harbor while you picnic and relax on your beach. This fabulous waterfront three bedroom main house and three bedroom guest house also offers your own dock and mooring.

Karen Overtoom Karen M. Overtoom R.E.

120 Eastville Ave Ob520, Oak Bluffs, MA 02557
/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

/22
Not Listed For Sale
- 4 Beds
- 3 Baths
- 1,250 Sq Ft
33 Summer St, Vineyard Haven, MA 02568

33 Summer St, Vineyard Haven, MA 02568

/20
$910,000
- 2 Beds
- 1 Bath
- 834 Sq Ft
21 Clay Pit Rd, Edgartown, MA 02539

EDGARTOWN COTTAGE ON A COUNTRY LANE - Nestled on a spacious .56-acre lot in the Lily Pond District, this charming 2-bedroom, 1-bath cottage offers a rare opportunity to create your own Island haven. Renovate or build to suit just a short distance from all that Edgartown village has to offer — shops, restaurants, harbor, and beaches — you’ll enjoy both privacy and convenience in one of the

Leslie C. Floyd Portfolio Real Estate, Inc.

21 Clay Pit Rd, Edgartown, MA 02539
/15
$30,000 per month
- 3 Beds
- 3 Baths
- 2,888 Sq Ft
- House for Rent
101 Peasepoint Way Ed324, Edgartown, MA 02539

THIS IS A SUMMER RENTAL ONLY. This grand and stately home is located in Starbuck Point in Edgartown. The home is elegantly furnished with traditional charm . The Captain's house is surrounded by neatly manicured lawns and the ocean is at the end of the street. It is a five minute walk to the Edgartown Village and Harbor for shopping, dining or theater.

Karen Overtoom Karen M. Overtoom R.E.

101 Peasepoint Way Ed324, Edgartown, MA 02539
/10
$550,000 Sold Feb 28, 2025
- Land
- 0.33 Acre
- $1,666,667 per Acre
- 70 Days On Market
0 Shawanue Ave Unit 42704, Oak Bluffs, MA 02557

Secluded lot in a prime Oak Bluffs location, offering both privacy and convenience. Just moments from public access points to the sandy shores of Lagoon Pond and the vibrant downtown area, this property provides the perfect setting for your dream home. With engineering plans already in place for a 2-bedroom residence, you have the opportunity to create a custom-built home tailored to your vision.

Alyssa Halisky Wallace & Co. Sotheby's

0 Shawanue Ave Unit 42704, Oak Bluffs, MA 02557

/44
Est $4,915,949 Not Listed For Sale
- 6 Beds
- 7 Baths
- 5,034 Sq Ft
59 Hagerty Dr, Vineyard Haven, MA 02568

59 Hagerty Dr, Vineyard Haven, MA 02568

/14
$3,995,000
- 4 Beds
- 4 Baths
- 3,270 Sq Ft
160 Katama Rd, Edgartown, MA 02539

Gorgeous post-and-beam home built by a respected contractor. This spacious house plus detached guest quarters is on the outskirts of the village conveniently located on the way to South Beach. The property is at the end of a long driveway off Katama Road and is private and quiet. Upon arrival, you are greeted by beautiful landscaping with large beds of hydrangeas. There are 3 bedrooms in the main

Bonnie Pierce Wallace & Co. Sotheby's

160 Katama Rd, Edgartown, MA 02539
/13
$27,000 per month
- 4 Beds
- 3.5 Baths
- 1,962 Sq Ft
- House for Rent
20 Bay Lot Circle Ed323, Edgartown, MA 02539

THIS IS A SUMMER RENTAL ONLY. Vacation by the beach in a relaxed contemporary home offering fabulous panoramic views of Edgartown Harbor, Chappiquidick, Katama Bay and South Beach. Our Katama Bay home is located off of Edgartown Bay Road at the quiet cul-de-sac,close to the beaches and boat launch access. For those who love the ocean breezes and sandy beaches, there is great sunbathing,

Karen Overtoom Karen M. Overtoom R.E.

20 Bay Lot Circle Ed323, Edgartown, MA 02539
/52
$2,470,000 Sold Feb 28, 2025
- 2,351 Sq Ft
- $1051/SF
- 180 Days On Market
- 4 Beds
- 4 Baths
- Built 1760
2 Green Ave, Edgartown, MA 02539

CHARMING VINTAGE HOME IN THE HEART OF EDGARTOWN VILLAGE. Nestled within lush perennial gardens and surrounded by hedges and a classic picket fence, the Charles W. Crowell House is a delightful antique home that captures the essence of a bygone era. With its origins dating back to 1760, the home boasts beams crafted from trees that once grew on the property. These timeless timbers are prominently

Wendy Harman Compass | Point B

2 Green Ave, Edgartown, MA 02539

/15
Est $1,197,123 Not Listed For Sale
- 3 Beds
- 2 Baths
- 966 Sq Ft
73 Leonard Cir, Vineyard Haven, MA 02568

73 Leonard Cir, Vineyard Haven, MA 02568

/33
$8,995,000
- 11 Beds
- 9 Baths
- 9,678 Sq Ft
5 Louis Field Rd, Edgartown, MA 02539

SWEETENED WATER FARM ESTATE. Located just one mile from the heart of historic Edgartown Village, this compound in Sweetened Water Farm presents a rare opportunity to become the next steward of an extraordinary Martha’s Vineyard estate. Privately sited on 4.6 acres of exquisitely cultivated gardens, this remarkable property has been featured in several publications celebrating the island’s most

Wendy Harman Compass | Point B

5 Louis Field Rd, Edgartown, MA 02539
/12
$12,500 per month
- 3 Beds
- 2 Baths
- 1,800 Sq Ft
- House for Rent
138 South Rd, Chilmark, MA 02535

THIS IS A SUMMER RENTAL ONLY. This newly remodeled 3 bedroom 2 bath has a spacious master bedroom suite, cozy sun room and updated kitchen. It has a great yard with garden landscaping, a perfect spot for outdoor dining. 1.5 miles from Alley's store. 3.3 miles to Lucy Vincent Beach.The bathrooms are fully remodeled. An easy, comfortable house in a central location. Three ceiling fans and 3

Karen Overtoom Karen M. Overtoom R.E.

138 South Rd, Chilmark, MA 02535
/10
$550,000 Sold Feb 28, 2025
- Land
- 0.33 Acre
- $1,666,667 per Acre
- 70 Days On Market
0 Shawanue Ave Unit 32400336, Oak Bluffs, MA 02557

Secluded lot in a prime Oak Bluffs location, offering both privacy and convenience. Just moments from public access points to the sandy shores of Lagoon Pond and the vibrant downtown area, this property provides the perfect setting for your dream home. With engineering plans already in place for a 2-bedroom residence, you have the opportunity to create a custom-built home tailored to your vision.

Alyssa Halisky Wallace & Co. Sotheby's International Realty

0 Shawanue Ave Unit 32400336, Oak Bluffs, MA 02557

/16
Est $1,625,480 Not Listed For Sale
- 2 Beds
- 2 Baths
- 1,380 Sq Ft
44 Jeremiah Rd, Edgartown, MA 02539

44 Jeremiah Rd, Edgartown, MA 02539

/39
$1,695,000
- 3 Beds
- 4 Baths
- 3,027 Sq Ft
110 Clover Hill Dr, Vineyard Haven, MA 02568

Perfect Location just minutes from Downtown and the ferry terminal, this updated home offers flexible living with three bedrooms and four bathrooms and additional interior exterior living areas to enjoy. It has a private lower level apartment large fenced in yard and a detached garage for boat/car storage. Many renovations have been completed. Seven new mini-splits (7), bathrooms renovated, back

Janna O'Loughlin Portfolio Real Estate, Inc.

110 Clover Hill Dr, Vineyard Haven, MA 02568
/13
$14,000 per month
- 3 Beds
- 2 Baths
- 1,800 Sq Ft
- House for Rent
88 Quenames Rd, Chilmark, MA 02535

THIS IS A SUMMER RENTAL ONLY. This bright and cheerful, wooded retreat is truly tranquil, yet just a little over a mile from West Tisbury village, with its General Store (Alley's), Farmer's Market, Artisan's Festivals and Flea Market. This home has been recently updated by its new owners. They have chosen the loveliest colors and simple, appropriate cottage touches. There is a new expansive deck

Karen Overtoom Karen M. Overtoom R.E.

88 Quenames Rd, Chilmark, MA 02535
/3
$750,000 Sold Feb 27, 2025
- 1,100 Sq Ft
- $682/SF
- 0 Days On Market
- 1 Bath
- Built 2021
2 Union St Unit A, Tisbury, MA 02568

Commercial Condo Not listed in LINK

LINK Email Cache LINK

2 Union St Unit A, Tisbury, 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

/41
$1,850,000
- 4 Beds
- 3 Baths
- 2,068 Sq Ft
4 Hye Ln, Edgartown, MA 02539

Pristine and superbly maintained, this two bedroom home and two bedroom guest house has tremendous upside potential and a substantial rental history. This property is tied to town sewer and will allow for up to 7 bedrooms. Two additional bedrooms in the main house are possible within the existing footprint with appropriate town approvals.There is an additional 668 sq. ft.of finished space in the

Lynn Buder Sandpiper Realty Inc

4 Hye Ln, Edgartown, MA 02539
/8
$56,000 per month
- 4 Beds
- 2.5 Baths
- 3,000 Sq Ft
- House for Rent
337 Barnes Rd Ob526, Oak Bluffs, MA 02557

THIS IS A SUMMER RENTAL ONLY. This home offers a spacious open floor plan providing a comfortable yet elegant retreat, truly an upscale surprise, perfect for relaxing or entertaining. With an expansive mahogany wraparound deck, sweeping views and a screened-in porch, enjoying the evening sunsets while grilling and dining al fresco or try a nearby bistro or 5 star restaurant----the choice is

Karen Overtoom Karen M. Overtoom R.E.

337 Barnes Rd Ob526, Oak Bluffs, MA 02557
/23
$1,575,000 Sold Feb 25, 2025
- 4,306 Sq Ft
- $366/SF
- 3 Days On Market
- 4 Beds
- 6 Baths
- Built 1980
79 Watcha Path, Edgartown, MA 02539

The spacious home is located in a peaceful private setting on a quiet road. This house is directly across the road from 138 acres of protected land owned by Sheriffs Meadow Foundation. Perfectly situated on 3 beautiful open and slightly forested acres of land, you will find this open concept home that might have the opportunity for further bedroom expansion. Current septic is 6 Bedrooms.

Robin Perschel Feiner Real Estate

79 Watcha Path, Edgartown, MA 02539

/25
Not Listed For Sale
- 4 Beds
- 2 Baths
- 1,826 Sq Ft
7 Curtis Ln, Edgartown, MA 02539

7 Curtis Ln, Edgartown, MA 02539

/4
$425,000
- Land
- 0.23 Acre
- $1,847,826 per Acre
0 Heather Ln Unit 11 43465, Oak Bluffs, MA 02568

Lovely untouched piece of land waiting for you to create your own special island retreat. Property, being sold "AS IS", is nestled on a quiet dead end road off of DeBettencourt Place in Oak Bluffs. Conveniently located within walking distance to downtown OB, OB Ferry, beaches, parks, arts district and more... Included on the "Sea View Bluffs Subdivision Plan of Land" and recorded with Dukes

Rosemary Byrd Ocean Park Realty Inc

0 Heather Ln Unit 11 43465, Oak Bluffs, MA 02568
/8
$12,000 per month
- 3 Beds
- 1.5 Baths
- 820 Sq Ft
- House for Rent
8 Beach Plum Path Ob525, Oak Bluffs, MA 02557

THIS IS A SUMMER RENTAL ONLY. This irresistible home is a 3-minute walk away from a deeded, sandy, sheltered beach and only a 5-minute drive to the center of Oak Bluffs and all the fun activities that Circuit Avenue has to offer. The casual getaway has wonderful ambiance enhanced by its soaring ceilings, a wood-burning fireplace, and delightful furnishings.

Karen Overtoom Karen M. Overtoom R.E.

8 Beach Plum Path Ob525, Oak Bluffs, MA 02557
/34
$8,250,000 Sold Feb 21, 2025
- 3,596 Sq Ft
- $2294/SF
- 95 Days On Market
- 4 Beds
- 5 Baths
- Built 1978
93 Edgartown Bay Rd, Edgartown, MA 02539

Waterfront home located on Edgartown Bay Road, one of Martha’s Vineyard’s most desirable streets. This four-bedroom, four-and-a half bath Katama Bay property boasts an open floor plan that offers spectacular natural light and flows seamlessly. The first floor features a large family room overlooking Katama Bay and the Atlantic Ocean. The renovated chef's kitchen opens to the family room, dining

Jarrett Hurwitz Keller Williams Realty

93 Edgartown Bay Rd, Edgartown, MA 02539

/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

/32
$4,075,000 Open Sun 1PM - 3PM
- 4 Beds
- 3.5 Baths
- 2,861 Sq Ft
39 Sengekontacket Rd, Edgartown, MA 02539

SPECTACULAR WATERFRONT home with stunning water views from every room and completely renovated in 2014. Situated in a private location in the Sengekontacket Association, this is an exceptional property in a rare setting. In addition to the breathtaking water view of Major's Cove and of Felix Neck throughout the home, the front of the property faces serene pastoral views. This home offers four

Jayne Isford Ocean Park Realty, Inc.

39 Sengekontacket Rd, Edgartown, MA 02539
/12
$13,200 per month
- 3 Beds
- 2 Baths
- 1,400 Sq Ft
- House for Rent
8 Lobsterville Rd, Aquinnah, MA 02535

Uniquely designed, 3-bedroom, 2 full bath contemporary home, divided between three floors and set upon an acre of lush grounds with waterviews overlooking Vineyard Sound and the Elizabeth Islands. Privacy enhanced with large tracts of conservation land nearby and walking distance to Lobsterville Beach.

Karen Overtoom Karen M. Overtoom R.E.

8 Lobsterville Rd, Aquinnah, MA 02535
/24
$1,055,000 Sold Feb 21, 2025
- 875 Sq Ft
- $1206/SF
- 115 Days On Market
- 3 Beds
- 1 Bath
- Built 1870
18 Brunswick Ave, Vineyard Haven, MA 02568

Embrace the history and character of this delightful 1870's Oak Bluffs cottage. Formerly the Laura Thomas Smith House, it was relocated from the Vineyard Highlands area, nestled in a quaint neighborhood close to the center of town and the harbor. It was documented in a 1978 Oak Bluffs Historical Survey and has been in the same family for 98 years. This cottage features a sun-filled living room,

Cheri Mason LandVest MV

18 Brunswick Ave, 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

/21
$650,000
- 2 Beds
- 1 Bath
- 725 Sq Ft
124 Skiff Ave Unit A-11, Vineyard Haven, MA 02568

Outstanding year-round, two-bedroom condo on the ground level with dedicated parking, and close to the ferry, shops, and restaurants on Main Street, Vineyard Haven. The common grounds feature colorful landscaping, picnic tables, grills, and a swimming pool with a distant peek at the Lagoon. This unit has been delightfully renovated, featuring new hardwood floors, an updated bathroom, updated

Stephanie Roache Donnelly + Co.

124 Skiff Ave Unit A-11, Vineyard Haven, MA 02568
/8
$7,900 per month
- 3 Beds
- 2.5 Baths
- 2,107 Sq Ft
- House for Rent
2 Paddock Cir, Chilmark, MA 02535

Karen Overtoom Karen M. Overtoom R.E.

2 Paddock Cir, Chilmark, MA 02535
/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

/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

Showing Results 401 - 440, Page 11 of 18

Massachusetts Dukes County Marthas Vineyard

How to Buy a Home How to Finance a Home How to Sell a Home

Find More Real Estate & Homes for Sale by State

Top Cities with Homes For Sale

Top Counties with Homes For Sale

More Real Estate For Sale Near Me

Homes in Nearby Neighborhoods

Homes in Nearby Cities

Homes in Nearby Counties

Homes in Nearby Zip Codes

Disclaimer: Certain information contained herein is derived from information provided by parties other than Homes.com. All information provided is deemed reliable, but is not guaranteed to be accurate and should be independently verified.

Homes.com Licensing Information

§ 442-H New York Standard Operating Procedures

New York Fair Housing Notice

TREC: Information about brokerage services, Consumer protection notice

California DRE #01937601

Contact Homes.com Brokerage