Dukes County, MA Homes

/42
$10,995,000 Pending
- 7 Beds
- 3.5 Baths
- 2,957 Sq Ft
117 N Water St, Edgartown, MA 02539

Classic Captain's Home With Deep Water Dock On Edggatown Harbor - Located on prestigious North Water Street in the heart of historic Edgartown Village, this premier harbor front home combines the best of in-town and waterfront living, with deep water dock. On the harbor front side of the home, there are 2 decks with panoramic views across the harbor. There are a total of 7 Bedrooms making the

Wendy Harman

Compass

(508) 715-6592

117 N Water St, Edgartown, MA 02539
/21
$7,000 total monthly price
- 4 Beds
- 3.5 Baths
- 3,000 Sq Ft
- House for Rent
27 Beach Plum Ln, Chilmark, MA 02535

weekly rental rate negotiable, cost $400-$975 per night depending on season and month 3 night min stay The "Grapevine" is located on a private road next door to the Beach Plum Inn, It was completely rebuilt . it has 3 generous size bedrooms all with private baths, 2 of the bedrooms are located on the second floor, 1 bedroom is located on the first floor as well as the Open concept living with a

Bryan Hummel Commonwealth Realty Group

27 Beach Plum Ln, Chilmark, MA 02535
/44
$1,900,000 Sold Feb 07, 2025

28 Roger's Way, Oak Bluffs, MA 02557
- 3 Beds
- 3.5 Baths
- 2,420 Sq Ft
- Built 2024
Last Sold Summary
- 10% Below List Price
- $785/SF
- 563 Days On Market
Current Estimated Value $1,666,501

Last Listing Agent Michele Casavant Vineyard Village Realty

28 Roger's Way, Oak Bluffs, MA 02557

/5
Not Listed For Sale
0 Bridle Path Rd, Vineyard Haven, MA 02568

0 Bridle Path Rd, Vineyard Haven, MA 02568

/22
$1,199,000
- 2 Beds
- 1 Bath
- 742 Sq Ft
47 Winemack St, Oak Bluffs, MA 02557

Oak Bluffs -East Chop-Close to the ocean. Two cottages on one lot. Stay in one and rent the other, the possibilities are great with this amazing opportunity to own close to the beach and just a mile to Oak Bluffs center. The front house is two bedrooms 1 bath: freshly painted with new flooring. The second home nestled in the back of the lot is an open floor plan with one bedroom, one bath, and a

Lisa Lucier

Anchor Realty of MV

(508) 403-9601

47 Winemack St, Oak Bluffs, MA 02557
/21
$9,500 total monthly price
- 4 Beds
- 2 Baths
- 1,579 Sq Ft
- House for Rent
155 Skiff Ave, Vineyard Haven, MA 02568

**SUMMER RENTAL ONLY** RATE IS WEEKLY** Enjoy the serenity of a four bedroom, two full bathroom peaceful oasis complete with private in-ground pool. Close to lively dining and boutiques of downtown Vineyard Haven. Unwind at neighborhood beaches; Eastville, Owen Park, Tashmoo beaches all just a few minutes drive from your vacation retreat.This lovely home spread over 1600ft of living area provides

Allison Cameron Parry Douglas Elliman Real Estate - Nantucket

155 Skiff Ave, Vineyard Haven, MA 02568
/46
$3,120,000 Sold Sep 16, 2025

140 Pond Rd, Vineyard Haven, MA 02568
- 4 Beds
- 3 Baths
- 3,669 Sq Ft
- Built 1993
Last Sold Summary
- 10% Below List Price
- $850/SF
- 84 Days On Market
Current Estimated Value $4,101,962

Last Listing Agent Jon Hartzband Martha's Vineyard Island-Wide Realty

140 Pond Rd, Vineyard Haven, MA 02568

/5
Est $546,446 Not Listed For Sale
- 2 Beds
- 1 Bath
- 708 Sq Ft
1 Carroll Ln, Chilmark, MA 02535

1 Carroll Ln, Chilmark, MA 02535

/42
$1,498,000 Pending
- 3 Beds
- 4 Baths
- 2,105 Sq Ft
10 Peases Point Way N, Edgartown, MA 02539

ICONIC EDGARTOWN VILLAGE BEAUTY with elevated style just one block from Main Street! Recent renovations and upgrades give this 1840's classic a fresh and modern vibe for easy maintenance in-town living. Gracious bluestone terrace bordered with hydrangeas provides a private and serene setting for outdoor living and entertaining. Other notable features include: 3-minute walk to the heart of Main

Wendy Harman

Compass

(508) 691-7503

10 Peases Point Way N, Edgartown, MA 02539
/41
$13,500 total monthly price
- 5 Beds
- 5.5 Baths
- 3,000 Sq Ft
- House for Rent
14 Bernard Cir, Vineyard Haven, MA 02568

** SUMMER WEEKLY RATE ** Private and luxurious BRAND NEW contemporary chic 5 BED 5.5 BATH home perfectly situated close to downtown Vineyard Haven yet set amongst a rural and peaceful WEST CHOP adjacent neighborhood. Indulge and unwind in the PRIVATE HEATED SALTWATER IN-GROUND POOL surrounded by opulent outdoor living and dining area highlighted by covered al-fresco kitchen, BBQ grill and bar -

Allison Cameron Parry Douglas Elliman Real Estate - Nantucket

14 Bernard Cir, Vineyard Haven, MA 02568
/3
$105,000 Sold Sep 05, 2025

00 Eliot Ave Unit 17, Chilmark, MA 02535
- Land
- 0.7 Acre
- $150,000 per Acre
Last Sold Summary
- 5% Below List Price
- 29 Days On Market
Last Listing Agent Julianna Flanders Flanders Real Estate

00 Eliot Ave Unit 17, Chilmark, MA 02535

/42
Not Listed For Sale
- 3 Beds
- 3.5 Baths
- 2,417 Sq Ft
16 Fisherman's Knot Rd, Edgartown, MA 02539

16 Fisherman's Knot Rd, Edgartown, MA 02539

/27
$1,615,000
- 3 Beds
- 2.5 Baths
- 1,740 Sq Ft
27 Chapde Ln, Tisbury, MA 02568

Classic Style Meets Timeless Charm - Located at the end of a lightly traveled lane and surrounded by stunning gardens and stone retaining walls, this residence provides a modern and spacious environment for comfortable island living. The home welcomes you with an open and bright layout, featuring sleek finishes and an abundance of natural light. The gourmet kitchen is a chef's delight that

Wendy Harman

Compass

(774) 515-4591

27 Chapde Ln, Tisbury, MA 02568
/41
$8,750 total monthly price
- 4 Beds
- 2.5 Baths
- 1,811 Sq Ft
- House for Rent
11 High Meadow Ln, Vineyard Haven, MA 02568

**SUMMER WEEKLY RATE ** INQUIRE FOR LONG TERM OFFSEASON RATE**Discover the perfect summer retreat in this beautifully updated Meadow View Farms home. Nestled on a private hilltop and minutes from beaches, bike paths, Farm Neck Gand Downtown Oak Bluffs, this home offers a serene escape close to the island’s best attractions. 4 spacious bedrooms, first floor primary ensuite, shared secondary floor

Allison Cameron Parry Douglas Elliman Real Estate - Nantucket

11 High Meadow Ln, Vineyard Haven, MA 02568
/2
$10,189,494 Sold Nov 03, 2025

55 King Point Way, Edgartown, MA 02539
- 4 Beds
- 8 Baths
- 9,900 Sq Ft
- Built 2021
Last Sold Summary
- $1,029/SF
- 0 Days On Market
Last Listing Agent LINK Email Cache LINK

55 King Point Way, Edgartown, MA 02539

/44
Est $3,868,500 Not Listed For Sale
- 4 Beds
- 2.5 Baths
- 2,736 Sq Ft
74 & 75 Jeremiah Way, Edgartown, MA 02539

74 & 75 Jeremiah Way, Edgartown, MA 02539

/4
$6,295,000
- Land
- 0.5 Acre
- $12,590,000 per Acre
3 Somerset Ln, Edgartown, MA 02539

COMING SOON: LUXURY ISLAND LIVING AT SOMERSET - Construction is underway at Three Somerset Lane, part of an exclusive enclave of five luxury homes between Edgartown Village and South Beach. Developed by Stanmar, owner of Winnetu Resorts, Somerset blends modern coastal design with island charm. Designed by Dudley Cannada and built by Adam Moran Construction, this 4-bedroom, 5.5-bath home offers

Wendy Harman

Compass

(508) 419-9057

3 Somerset Ln, Edgartown, MA 02539
/27
$21,700 total monthly price
- 5 Beds
- 3 Baths
- 2,168 Sq Ft
- House for Rent
97 3rd St N, Edgartown, MA 02539

YOUR VINEYARD ESCAPE AWAITS! This sizable vintage rental with water views of Sengekontacket Pond and beyond is ideal for your island getaway. Boasting multiple levels of living and porches that take advantage of views, the main floor is awash in seaside tones. Display a raw bar on the center island and top off beverages in the kitchen before relaxing in the sunroom as you enjoy the painterly sky

Fine Homes Group Keller Williams Realty Boston-Metro | Back Bay

97 3rd St N, Edgartown, MA 02539
/30
$1,550,000 Sold Oct 16, 2025

251 State Rd, Vineyard Haven, MA 02568
- 3 Beds
- 2 Baths
- 1,986 Sq Ft
- Built 1986
Last Sold Summary
- 9% Below List Price
- $780/SF
- 114 Days On Market
Last Listing Agent Meg Bodnar Tea Lane Associates

251 State Rd, Vineyard Haven, MA 02568

/19
Est $940,918 Not Listed For Sale
- 3 Beds
- 1.5 Baths
- 984 Sq Ft
9 Webaqua Rd, Oak Bluffs, MA 02557

9 Webaqua Rd, Oak Bluffs, MA 02557

/29
$1,395,000 Pending
- 4 Beds
- 2 Baths
- 2,184 Sq Ft
42 Road To the Plains, Edgartown, MA 02539

Classic Colonial - Located between Edgartown Village and Katama, this classically styled colonial features plenty of traditional charm as well as a world of possibilities for renovations and/or expansion. The main entrance opens up to a center staircase flanked by a formal Living Room and Dining Room and there is also a kitchen with breakfast bar PLUS a first-floor bedroom and full bath. The

Wendy Harman

Compass

(508) 978-3864

42 Road To the Plains, Edgartown, MA 02539
/22
$20,000 total monthly price
- 5 Beds
- 3 Baths
- 3,000 Sq Ft
- House for Rent
55 Samoset Ave, Oak Bluffs, MA 02557

Modernized 5 bed, 3 full bath Victorian in the heart of Downtown Oak Bluffs. Steps to restaurants, shopping, harbor, ferries and beaches. Accommodates 10 guests. Easy breezy outdoor living, dining, bluestone patio and BBQ grill. Relax on the covered porch surrounded by a lush flower garden or unwind in the outdoor shower. Updated stone and stainless kitchen. Formal dining for eight. A/C, WIFI and

Allison Cameron Parry Douglas Elliman Real Estate - Nantucket

55 Samoset Ave, Oak Bluffs, MA 02557
/29
$2,250,000 Sold Dec 27, 2024

47 Stonebridge Rd, West Tisbury, MA 02568
- 4 Beds
- 3 Baths
- 1,705 Sq Ft
- Built 1976
Last Sold Summary
- 1% Above List Price
- $1,320/SF
- 5 Days On Market
Last Listing Agent Mark Jenkins Wallace & Co. Sotheby's International Realty

47 Stonebridge Rd, West Tisbury, MA 02568

/3
Est $1,602,776 Not Listed For Sale
- 4 Beds
- 2.5 Baths
- 2,329 Sq Ft
18 Towanticut Ave, Oak Bluffs, MA 02557

18 Towanticut Ave, Oak Bluffs, MA 02557

/23
$8,995,000
- 11 Beds
- 8.5 Baths
- 6,289 Sq Ft
1 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 this 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

(508) 715-8610

1 Louis Field Rd, Edgartown, MA 02539
/29
$11,000 total monthly price
- 4 Beds
- 2 Baths
- 1,750 Sq Ft
- House for Rent
29 Mercier Way, Edgartown, MA 02539

**SUMMER RATE$ 9,500-$11,000 WEEKLY** Freshly remodeled 4 bed, 2 full bath coastal cape with all new furnishings, flawless finishes, large private yard, close to South Beach, bike path and downtown Edgartown. Large family room with vaulted ceiling and large TV , gorgeous kitchen with all new stainless appliances, vaulted ceilings, sky lights, custom blue stone countertop, island eatery, and wine

Allison Cameron Parry Douglas Elliman Real Estate - Nantucket

29 Mercier Way, Edgartown, MA 02539
/29
$1,970,000 Sold Jun 26, 2025

493 Katama Rd Unit E2, Edgartown, MA 02539
- 3 Beds
- 2.5 Baths
- 1,410 Sq Ft
- Built 1973
Last Sold Summary
- 2% Below List Price
- $1,397/SF
- 0 Days On Market
Last Listing Agent Bonnie Pierce Wallace & Co. Sotheby's

493 Katama Rd Unit E2, Edgartown, MA 02539

/36
Est $2,690,292 Not Listed For Sale
- 3 Beds
- 3.5 Baths
- 3,470 Sq Ft
28 Woodhaven Dr, Edgartown, MA 02539

28 Woodhaven Dr, Edgartown, MA 02539

/25
$1,650,000
- 6 Beds
- 3.5 Baths
- 1,616 Sq Ft
34 Massasoit Ave, Oak Bluffs, MA 02557

Downtown Oak Bluffs located in the Copeland District this Victorian home combines historic charm with modern comfort. Offering 6 spacious bedrooms and 3.5 bathrooms, this home provides ample living space for family and guests. Also making an ideal rental property Sleeping 12 comfortably just a block to the restaurants and shops of Circuit Ave. and a couple of blocks to the beach it's the perfect

Lisa Lucier

Anchor Realty of Martha's Vineyard

(508) 299-5240

34 Massasoit Ave, Oak Bluffs, MA 02557
/30
$28,500 total monthly price
- 9 Beds
- 6.5 Baths
- 3,500 Sq Ft
- House for Rent
9 Tuckernuck Ave, Oak Bluffs, MA 02557

**SHORT TERM ONLY - WEEKLY RATE ADVERTISED ** Water view Victorian fronting Waban Park, steps to Inkwell Beach. Newly restored 9-bed, 6+ bath Main and Guest House houses 18 guests. Internet, A/C and cable TV. Coastal chic interior with all new furnishings. Large open floor plan, ample gathering and relaxation spaces. Dining for 10, Wet Bar, gourmet kitchen, gas range, stainless appliances and

Allison Cameron Parry Douglas Elliman Real Estate - Nantucket

9 Tuckernuck Ave, Oak Bluffs, MA 02557
/18
$4,250,000 Sold Sep 09, 2025

420 Lamberts Cove Rd, Vineyard Haven, MA 02568
- 5 Beds
- 3 Baths
- 4,125 Sq Ft
- Built 1900
Last Sold Summary
- 5% Below List Price
- $1,030/SF
- 21 Days On Market
Last Listing Agent Alyssa Halisky Wallace & Co. Sotheby's International Realty

420 Lamberts Cove Rd, Vineyard Haven, MA 02568

/21
Est $1,086,293 Not Listed For Sale
- 3 Beds
- 2 Baths
- 1,176 Sq Ft
10 Lagoon Rd, Oak Bluffs, MA 02557

10 Lagoon Rd, Oak Bluffs, MA 02557

/37
$9,995,000
- 6 Beds
- 7.5 Baths
- 7,205 Sq Ft
25 Lelands Path, Edgartown, MA 02539

Casual Elegance On Katama Bay - Welcome to 25 Leland’s Path on Katama Bay, a stunning property that embodies the perfect blend of casual elegance and serene waterfront living on Chappquiddick. This magnificent home offers over 7,200 square feet of living space, six bedrooms, all with en suite baths, and a three-room Owner's Suite with sweeping water views and a private second-floor deck. The

Wendy Harman

Compass

(508) 625-9706

25 Lelands Path, Edgartown, MA 02539
/20
$6,000 total monthly price
- 2 Beds
- 2 Baths
- 1,152 Sq Ft
- House for Rent
11 Hammett Ln, Chilmark, MA 02535

** WEEKLY SUMMER RATE** Welcome to 11 Hammett Lane in Chilmark, up-island on beautiful Martha's Vineyard. This sweet private cottage is designer done with gorgeous furnishings, comfortable touches, and a nod to all things local. Affectionately named 'The Blueberry House' by the original owners, this 2 bedroom, 2 bath, 2 story home with outdoor shower will quickly find a place in your heart. Prime

Allison Cameron Parry Douglas Elliman Real Estate - Nantucket

11 Hammett Ln, Chilmark, MA 02535
/2
$3,300,000 Sold Dec 09, 2025

1 Muskoday Way, Edgartown, MA 02539
- 3 Beds
- 2 Baths
- 2,194 Sq Ft
- Built 1972
Last Sold Summary
- $1,504/SF
- 0 Days On Market
Last Listing Agent LINK Email Cache LINK

1 Muskoday Way, Edgartown, MA 02539

/37
Est $3,667,078 Not Listed For Sale
- 3 Beds
- 5 Baths
- 4,417 Sq Ft
149 Litchfield Rd, Edgartown, MA 02539

149 Litchfield Rd, Edgartown, MA 02539

/41
$5,750,000
- 4 Beds
- 4.5 Baths
- 3,643 Sq Ft
4 Somerset Ln, Edgartown, MA 02539

EXPERIENCE BAREFOOT ELEGANCE AT SOMERSET. Welcome to 4 Somerset Lane, a newly completed luxury residence in Edgartown’s exclusive Somerset enclave—perfectly positioned between the charm of Edgartown Village and the surf and sand of South Beach. Developed by Stanmar, owners of the renowned Winnetu Oceanside Resort, this exceptional home embodies the essence of modern coastal living—combining

Wendy Harman

Compass

(508) 715-9594

4 Somerset Ln, Edgartown, MA 02539
/10
$20,000 total monthly price
- 5 Beds
- 3 Baths
- 2,352 Sq Ft
- House for Rent
55 Samoset Ave Unit 1, Oak Bluffs, MA 02557

THIS PROPERTY IS A WEEKLY RENTAL PROPERTY!! Newly renovated, Great for Family Gatherings, Corporate Retreats, Central Air & Heat, very close to Circuit Ave and Beach, 5 Bedrooms, 3 full baths, galley kitchen, new appliances, dining room, family room, Flat Screen TV, FREE Wifi, washer & dryer, bay window breakfast nook, Oak and Pine wood flooring, outdoor shower, wrap around porch, blue stone

Karen Overtoom Karen M. Overtoom R.E.

55 Samoset Ave Unit 1, Oak Bluffs, MA 02557
/48
$4,750,000 Sold Nov 21, 2025

36 Crocker Dr, Edgartown, MA 02539
- 3 Beds
- 3.5 Baths
- 4,131 Sq Ft
- Built 2024
Last Sold Summary
- 14% Below List Price
- $1,150/SF
- 84 Days On Market
Last Listing Agent Stephanie Roache Donnelly + Co.

36 Crocker Dr, Edgartown, MA 02539

/26
Est $3,604,891 Not Listed For Sale
- 4 Beds
- 5.5 Baths
- 3,916 Sq Ft
53 Pinehurst Rd, Edgartown, MA 02539

53 Pinehurst Rd, Edgartown, MA 02539

Showing Results 1 - 40, Page 1 of 18

Massachusetts Dukes County

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