Dukes, MA Homes

/91
$1,895,000 Open Fri 10AM - 12PM
- 3 Beds
- 3 Baths
- 1,406 Sq Ft
17 John Wesley Ave, Vineyard Haven, MA 02568

Welcome to this year-round East Chop Victorian Gingerbread home, close to Oak Bluffs Harbor, Jetty Beach, and downtown. The amazing wrap-around porch is perfectly designed for spending lazy summers with friends and family. Many a party has been hosted on this generous porch, made more enticing by an open-plan first floor with a large kitchen, living room, and dining area. The first floor

kyle Neyer Tea Lane Associates

17 John Wesley Ave, Vineyard Haven, MA 02568
/40
$32,500 per month
- 6 Beds
- 4.5 Baths
- 3,222 Sq Ft
- House for Rent
100 Connie's Way &83 Ashtonw Vh408, Tisbury, MA 02568

THIS IS A WEEKLY SUMMER RENTAL ONLY.THE WEEKLY PRICE IN AUGUST IS $5,000. PER WEEK.SEE WEB SITE FOR ADDITIONAL WEEKLY PRICING. Located in Mink Meadows Association, this wonderful four bedroom, three full and one half bath home has many nice features that include a large eat-in kitchen/family room, a more formal living room with fireplace, dining room and den. Televisions in every bedroom, living

Karen Overtoom Karen M. Overtoom R.E.

100 Connie's Way &83 Ashtonw Vh408, Tisbury, MA 02568
/47
$1,595,500 Sold Jun 23, 2025
- 1,822 Sq Ft
- $876/SF
- 73 Days On Market
- 5 Beds
- 3 Baths
- Built 2003
21 Coffins Field Rd, Edgartown, MA 02539

EDGARTOWN SOUTH SHORE BEACH HOUSE. Imagine a countryside abode with nearby access to a pristine south shore stretch of beach and less than 6 miles to Edgartown Village and Harbor. Architect-designed as a low-key getaway, this delightful five bedroom year-round home has three full bathrooms plus a freestanding outdoor shower, decks, screened-in porch and is comfortably sited in an established well

Helena Kirschenbaum Studio Realty

21 Coffins Field Rd, Edgartown, MA 02539

/27
Est $1,373,100 Not Listed For Sale
- 3 Beds
- 3 Baths
- 2,228 Sq Ft
24 Alyssa Ln, Vineyard Haven, MA 02568

24 Alyssa Ln, Vineyard Haven, MA 02568

/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
/17
$12,000 per month
- 3 Beds
- 2 Baths
- 1,750 Sq Ft
- House for Rent
223 Sandpiper Lane Vh405, Tisbury, MA 02568

THIS IS A WEEKLY SUMMER RENTAL ONLY.THE WEEKLY PRICE IN AUGUST IS $3,000. PER WEEK.SEE WEB SITE FOR ADDITIONAL WEEKLY PRICING. This three bedroom two bath condo is just a short walk to association tennis, pool and the beach. Comfortable easy summer living with outdoor shower, spacious deck, and central AC for those really hot August days!Amenities include Direct TV DVD set up. There is an open

Karen Overtoom Karen M. Overtoom R.E.

223 Sandpiper Lane Vh405, Tisbury, MA 02568
/25
$949,000 Sold Jun 23, 2025
- 1,012 Sq Ft
- $938/SF
- 49 Days On Market
- 3 Beds
- 1.5 Baths
- Built 1986
345 Franklin St, Vineyard Haven, MA 02568

Charming Cape-style home in Vineyard Haven, ideally located just minutes from Downtown and Owen Little Beach. This well-maintained property sits on a 0.26-acre lot, offering a private back deck, a spacious yard, and an outdoor shower perfect for after beach days. The home boasts 3 bedrooms and 1.5 bathrooms, with a thoughtful layout that includes a bedroom on the first floor and two on the

Alyssa Halisky Wallace & Co. Sotheby's International Realty

345 Franklin St, Vineyard Haven, MA 02568

/16
Not Listed For Sale
- 3 Beds
- 1.5 Baths
- 1,275 Sq Ft
26 Chappaquiddick Ave, Vineyard Haven, MA 02568

26 Chappaquiddick Ave, Vineyard Haven, MA 02568

/62
$1,995,000
- 4 Beds
- 2 Baths
- 2,462 Sq Ft
129 Beach Rd, Tisbury, MA 02568

Unique, waterfront property with amazing, 180 degree views of the lagoon from one side of the property, and the Vineyard Haven Harbor on the north side of the property. Zoned both residential and commercial, rarely does such a unique property become available. Elevated above Beach Road and the lagoon, there are 2 structures on the property. The first, sited on the lagoon with private access,

Michele Moore Island Real Estate

129 Beach Rd, Tisbury, MA 02568
/34
$25,000 per month
- 4 Beds
- 3.5 Baths
- 2,334 Sq Ft
- House for Rent
100 Connie's Way Vh401, Tisbury, MA 02568

THIS IS A WEEKLY SUMMER RENTAL ONLY.THE WEEKLY PRICE IN AUGUST IS $6,250. PER WEEK.SEE WEB SITE FOR ADDITIONAL WEEKLY PRICING. Located in Mink Meadows Association, this wonderful four bedroom, three full and one half bath home has many nice features that include a large eat-in kitchen/family room, a more formal living room with fireplace, dining room and den. Televisions in every bedroom, living

Karen Overtoom Karen M. Overtoom R.E.

100 Connie's Way Vh401, Tisbury, MA 02568
/56
$1,699,000 Sold Jun 20, 2025
- 2,954 Sq Ft
- $575/SF
- 314 Days On Market
- 4 Beds
- 5 Baths
- Built 1900
9 Goode St, Oak Bluffs, MA 02557

Welcome to your dream home, located on a very quiet street in Oak Bluffs, yet just a short walk to downtown & the elementary school. This prime location offers the perfect blend of serenity and convenience. This well appointed home features 4 bedrooms and 4.5 bathrooms. Included in this is a 1-bedroom, 1-bathroom apartment attached to the home, providing a perfect space for guest accommodation.

Grace Hagerty Grace Hagerty Real Estate Inc

9 Goode St, Oak Bluffs, MA 02557

/23
Est $2,907,034 Not Listed For Sale
- 4 Beds
- 3.5 Baths
- 3,252 Sq Ft
5 Bold Meadow Cir, Edgartown, MA 02539

5 Bold Meadow Cir, Edgartown, MA 02539

/21
$1,795,000
- 3 Beds
- 4 Baths
- 2,312 Sq Ft
7 Candlemaker Cir, Edgartown, MA 02539

3 bedroom 2.5 bath main house consisting of 2 separate living spaces. First unit has 1st floor with livingroom, kitchen and bathroom. The second floor has an additional livingroom with two bedrooms. The second unit has 1st floor living area with kitchenette and bathroom, bedroom is in basement with walkout egress. 2 Car Garage has a permitted finished living space above with livingroom, full

Roy Cutrer Jr Laer Realty Partners

7 Candlemaker Cir, Edgartown, MA 02539
/20
$20,000 per month
- 3 Beds
- 3 Baths
- House for Rent
40 Hidden Cove Rd, Oak Bluffs, MA 02557

THIS IS A WEEKLY SUMMER RENTAL ONLY.SEE WEB SITE FOR WEEKLY PRICING. Welcome to "Shangri-la" A beautiful townhouse condominium end unit with magnificent views. Located midway between Oak Bluffs and Edgartown. You can enjoy the beautiful pool or one of the close local beaches. You will want to sit and enjoy the water views on the deck. The townhouse has a great living room with views and bedrooms

Karen Overtoom Karen M. Overtoom R.E.

40 Hidden Cove Rd, Oak Bluffs, MA 02557
/17
$700,000 Sold Jun 20, 2025
- 725 Sq Ft
- $966/SF
- 111 Days On Market
- 3 Beds
- 1 Bath
- Built 1870
2 Fisk Ave, Oak Bluffs, MA 02557

Gingerbread Cottage full of character and personality! Part of Martha's Vineyard Camp Meeting Association, this Oak Bluffs seasonal antique with beautiful trim and scrollwork sits on a lovely little avenue. The cottage features charming period details, a covered front porch with rocking chairs & upper balcony. Step inside the unique front door into a cozy living room enhanced by beamed ceiling,

Julie Walker Century 21 North East

2 Fisk Ave, Oak Bluffs, MA 02557

/22
Est $2,812,863 Not Listed For Sale
- 4 Beds
- 4 Baths
- 3,050 Sq Ft
23 Majors Cove Ln, Edgartown, MA 02539

23 Majors Cove Ln, Edgartown, MA 02539

/3
$1,795,000
- 3 Beds
- 3.5 Baths
- 2,311 Sq Ft
7 Candle Maker Cir, Edgartown, MA 02539

3 bedroom 2.5 bath main house consisting of 2 separate living spaces. First unit has 1st floor with livingroom, kitchen and bathroom. The second floor has an additional livingroom with two bedrooms. The second unit has 1st floor living area with kitchenette and bathroom, bedroom is in basement with walkout egress. 2 Car Garage has a permitted finished living space above with livingroom, full

Roy Cutrer LAER Realty Partners

7 Candle Maker Cir, Edgartown, MA 02539
/29
$64,000 per month
- 4 Beds
- 7 Baths
- 3,600 Sq Ft
- House for Rent
385 Barnes Rd Ob534, Oak Bluffs, MA 02557

THIS IS A WEEKLY SUMMER RENTAL ONLY.THE WEEKLY PRICE IN AUGUST IS $18,000. PER WEEK.SEE WEB SITE FOR ADDITIONAL WEEKLY PRICING. This is a beautiful waterfront home with a pool on the Lagoon. Enter through the impressive foyer with water views over the pool and lawn. There is a large living room with cathedral ceilings and dining area on the main level. There is a gourmet kitchen with eat-in

Karen Overtoom Karen M. Overtoom R.E.

385 Barnes Rd Ob534, Oak Bluffs, MA 02557
/30
$1,525,000 Sold Jun 18, 2025
- 2,016 Sq Ft
- $756/SF
- 110 Days On Market
- 4 Beds
- 3 Baths
- Built 1967
54 Lake St, Vineyard Haven, MA 02568

Welcome to this delightful 4-bedroom, 3-bathroom home, perfectly situated in a highly desirable location where convenience meets tranquility. Just a short stroll from town, restaurants, Tashmoo Landing, and tennis courts, this property offers the ideal combination of lifestyle and leisure.Step onto the covered front porch and into a warm, inviting space featuring two living rooms—one on each

Jon Hartzband Martha's Vineyard Island-Wide Realty

54 Lake St, Vineyard Haven, MA 02568

/32
Est $4,888,183 Not Listed For Sale
- 5 Beds
- 8 Baths
- 5,305 Sq Ft
225 Bigelow Rd, Vineyard Haven, MA 02568

225 Bigelow Rd, Vineyard Haven, MA 02568

/45
$1,899,000
- 4 Beds
- 3 Baths
- 2,127 Sq Ft
5 Bayes Hill Cir, Vineyard Haven, MA 02568

On a quiet cul-de-sac in the Bayes Hill neighborhood is this spacious traditional Colonial-style home adorned with charm. As you enter the home from the idyllic covered porch, you are welcomed into the foyer. The home is filled with intimate spaces while offering the opportunity for larger parties to gather. The living room has built-in shelving that flank the gas fireplace and it is connected to

Rene Jackson Island Real Estate

5 Bayes Hill Cir, Vineyard Haven, MA 02568
/25
$24,000 per month
- 3 Beds
- 2 Baths
- 1,257 Sq Ft
- House for Rent
5 Laurel Ave, Oak Bluffs, MA 02557

THIS IS A WEEKLY SUMMER RENTAL ONLY.THE WEEKLY PRICE IN AUGUST IS $6,500. PER WEEK.SEE WEB SITE FOR ADDITIONAL WEEKLY PRICING. Wonderful, fully redecorated Gingerbread house on East Chop, just minutes from the excitement of Oak Bluffs. There are three bedrooms and two full baths. The interior is clean and crisp, with beach cottage decor and beautiful bamboo floors. Entertainment options include

Karen Overtoom Karen M. Overtoom R.E.

5 Laurel Ave, Oak Bluffs, MA 02557
/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

/19
Est $1,353,179 Not Listed For Sale
- 3 Beds
- 2 Baths
- 1,520 Sq Ft
46 Windsor Dr, Edgartown, MA 02539

46 Windsor Dr, Edgartown, MA 02539

/27
$1,795,000
- 3 Beds
- 2.5 Baths
- 2,236 Sq Ft
71 6th St N, Edgartown, MA 02539

Classic three-bedroom farmhouse offers the perfect blend of island charm and laid-back comfort. Located within walking distance to scenic Sengekontacket Pond, it’s an ideal retreat for nature lovers, kayakers, or anyone looking to enjoy the Vineyard lifestyle. The home features a welcoming front porch and back deck—perfect spaces to relax, dine, or entertain outdoors. Inside, you'll find a warm

Erin Leighton Compass

71 6th St N, Edgartown, MA 02539
/30
$20,000 per month
- 4 Beds
- 2 Baths
- 1,920 Sq Ft
- House for Rent
291 Barnes Rd Ob516, Oak Bluffs, MA 02557

THIS IS A WEEKLY SUMMER RENTAL ONLY.SEE WEB SITE FOR WEEKLY PRICING. Feel the ocean breezes from this classic waterfront home. There are four bedrooms, an open living room and dining room that open up to large deck overlooking beautiful views across the Lagoon. Walking path to private sandy beach. BOAT MOORING INCLUDED.

Karen Overtoom Karen M. Overtoom R.E.

291 Barnes Rd Ob516, Oak Bluffs, MA 02557
/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

/34
Est $1,390,350 Not Listed For Sale
- 4 Beds
- 1 Bath
- 1,640 Sq Ft
125 Skiff Ave, Vineyard Haven, MA 02568

125 Skiff Ave, Vineyard Haven, MA 02568

/23
$1,790,000
- 2 Beds
- 1 Bath
- 600 Sq Ft
11 Beach Rd, Oak Bluffs, MA 02557

Oak Bluffs: Waterfront Property at Vineyard Haven Outer Harbor**This is an exceptional opportunity to acquire a stunning white sandy beach property on Vineyard Haven Harbor. This charming Island cottage boasts breathtaking panoramic views of the harbor and sound, showcasing magnificent sunsets each evening over the West Chop Peninsula. You can enjoy the lively boating scene, with yachts from

Alan Schweikert Ocean Park Realty Inc

11 Beach Rd, Oak Bluffs, MA 02557
/14
$14,200 per month
- 3 Beds
- 2 Baths
- 1,500 Sq Ft
- House for Rent
59 Prospect Ave Ob502, Oak Bluffs, MA 02557

THIS IS A WEEKLY SUMMER RENTAL ONLY. SEE WEB SITE FOR WEEKLY PRICING. This immaculate home is located in a quiet neighborhood that is just a bike ride's distance from several lovely beaches as well as the center of Oak Bluffs. The home offers open living spaces, generously proportioned sunny bedrooms and is well equipped.

Karen Overtoom Karen M. Overtoom R.E.

59 Prospect Ave Ob502, Oak Bluffs, MA 02557
/31
$1,750,000 Sold Jun 06, 2025
- 1,850 Sq Ft
- $946/SF
- 226 Days On Market
- 3 Beds
- 2 Baths
- Built 1981
97 Snake Hollow, Vineyard Haven, MA 02568

Nestled in a private neighborhood in Vineyard Haven conveniently located to the ferry and town for plenty of shopping and dining, this renovated home is move-in ready and sited on 1.5 generous acres. There are two entrances to the home. The most operational is off the side deck where you enter the fabulous must-have mudroom. Offering separation from the main part of the home is a dramatic

Stephanie Roache Donnelly + Co.

97 Snake Hollow, Vineyard Haven, MA 02568

/10
Est $2,470,681 Not Listed For Sale
- 5 Beds
- 4 Baths
- 2,398 Sq Ft
87 Bellevue Ave, Vineyard Haven, MA 02568

87 Bellevue Ave, Vineyard Haven, MA 02568

/81
$1,785,000
- 4 Beds
- 4 Baths
- 2,194 Sq Ft
209 Cove Rd, Vineyard Haven, MA 02568

Wonderful Tashmoo Wood Association - West Chop. Welcome to this spacious and inviting home in the wonderful Tashmoo Wood Community. Rarely does a Single Family Home come on the market in this Private Association. This four (4) bedroom home, nestled on a private 1 acre lot with a tree lined driveway, abuts common land, is adjacent to Mink Meadows Golf Course and offers the ultimate in the

Alisan Lohan-Conway Alisan Lohan-Conway Properties

209 Cove 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
/42
$2,400,000 Sold Jun 05, 2025
- 3,200 Sq Ft
- $750/SF
- 49 Days On Market
- 3 Beds
- 4.5 Baths
- Built 2014
6 Martha's Park Rd, Oak Bluffs, MA 02557

Must see stunning “reverse” layout (kitchen and main living spaces upstairs for the views) contemporary home with breathtaking water views and a thoughtfully designed layout in the exclusive Harthaven community! This spacious property features open kitchen concept with marble counter tops and stainless steel appliances, comfortable living areas, a bonus room (with full bathroom), food prep,

Jennifer B. DaSilva Compass

6 Martha's Park Rd, Oak Bluffs, MA 02557

/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

/39
$1,895,000
- 5 Beds
- 3 Baths
- 2,432 Sq Ft
32 Flamingo Dr, Edgartown, MA 02539

This well-maintained country farmhouse is centrally located and is situated on just over one acre of land. A circular driveway welcomes you to the home with plenty of parking. There is a garden storage shed, irrigation system, playground, fire pit with outdoor seating, and wraparound covered porch. The rear entry door from the kitchen leads to the outdoor shower and spacious sunny deck. The first

Skip Dostal, Jr Martha's Vineyard Real Estate

32 Flamingo Dr, Edgartown, MA 02539
/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
/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

/39
Est $6,712,733 Not Listed For Sale
- 5 Beds
- 6 Baths
- 6,546 Sq Ft
103 Main St, Vineyard Haven, MA 02568

103 Main St, Vineyard Haven, MA 02568

Showing Results 81 - 120, Page 3 of 18

Massachusetts Dukes County Tisbury

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