Dukes, MA Homes in ZIP Code 02568

/22
$1,250,000
- 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
/8
$17,500 per month
- 8 Beds
- 4.5 Baths
- 3,876 Sq Ft
- House for Rent
550 Chappaquonsett Rd Vh424 Unit 1, Tisbury, MA 02568

THIS PROPERTY IS A WEEKLY RENTAL PROPERTY!!!!!! Classic vineyard cottage with large open indoor and outdoor spaces to choose from while you and your family create memories to last a lifetime. Enjoy creating appetizers or three course meals in the newly renovated kitchen, bask in the light filled sun room or one of several covered porches while you take in the smell of fresh ocean air and

Karen Overtoom Karen M. Overtoom R.E.

550 Chappaquonsett Rd Vh424 Unit 1, Tisbury, MA 02568
/31
$1,325,000 Sold Jun 30, 2025
- 2,292 Sq Ft
- $578/SF
- 10 Days On Market
- 5 Beds
- 4 Baths
- Built 1992
191 Spring Hill Rd, Vineyard Haven, MA 02568

This pristine cape-style home is located in the heart of Vineyard Haven. This home features five bedrooms, four bathrooms, a beautifully landscaped yard, and an energy-efficient solar panel system installed by South Mountain Company. The functional and efficient floor plan with an open kitchen, living, and dining concept, makes entertaining family and guests seamless, with easy access to the

Madelyn Silvia Wallace & Co. Sotheby's

191 Spring Hill Rd, Vineyard Haven, MA 02568

/4
Est $2,968,039 Not Listed For Sale
- 4 Beds
- 3 Baths
- 2,789 Sq Ft
188 Pond Rd, Vineyard Haven, MA 02568

188 Pond Rd, Vineyard Haven, MA 02568

/28
$1,950,000
- 4 Beds
- 2.5 Baths
- 3,268 Sq Ft
7 Upper Meadow Ln, Oak Bluffs, MA 02557

Tucked at the end of a quiet cul-de-sac in the desirable Meadow View Farms neighborhood, this spacious Colonial offers over 3,200 square feet of comfortable and inviting living space. This home is ideal for those who love to host lively gatherings while providing comfortable accommodations for all. Inside, you'll find four well-sized bedrooms and two and a half baths, including a generous primary

Lesley Heidt Sandpiper Realty Inc

7 Upper Meadow Ln, Oak Bluffs, MA 02557
/8
$6,000 per month
- 4 Beds
- 2.5 Baths
- 2,000 Sq Ft
- House for Rent
33 Kennebago Ave Vh414, Tisbury, MA 02568

THIS PROPERTY IS A WEEKLY RENTAL PROPERTY!! This beautiful home has lots of open space for cooking, yard activities or just plain relaxing. Private association beach overlooking the Elizabethan Islands. Plan a sunset picnic on the beach or plan in the morning to see the rays of sun break on the water.

Karen Overtoom Karen M. Overtoom R.E.

33 Kennebago Ave Vh414, Tisbury, MA 02568
/34
$1,050,000 Sold Jun 30, 2025
- 1,606 Sq Ft
- $654/SF
- 45 Days On Market
- 4 Beds
- 2 Baths
- Built 1977
160 Bernard Cir, Vineyard Haven, MA 02568

Charming, four bedroom home with impressive rental history, new roof and septic in 2021/2022. Being offered turn-key, fully furnished with coastal decor, ready to move in and enjoy. Soaring cathedral ceilings highlight the open floor plan of the main living area on the second floor. Granite counters, stainless steel appliances and a center island in the kitchen leads to the dining area with

Dawn Bellante-Holand Sandpiper Realty

160 Bernard Cir, Vineyard Haven, MA 02568

/34
Est $2,551,353 Not Listed For Sale
- 5 Beds
- 3.5 Baths
- 1 Sq Ft
248 Pond Rd, Vineyard Haven, MA 02568

248 Pond Rd, Vineyard Haven, MA 02568

/41
$3,600,000
- 3 Beds
- 4 Baths
- 2,500 Sq Ft
27 Clambelly Rd, Chilmark, MA 02535

A place of serenity tucked in the woods of Chilmark. Complete renovation 2017/2018, large fenced in back yard with exquisite fish pond with waterfall and lighting. Kitchen has concrete countertops, sub zero refrigerator, Wolf Oven & Speed Oven. Large open formal dining area and open formal sitting area with fireplace. Beautiful reclaimed wood flooring. LED lighting throughout house, Media

Julianna Flanders Flanders Real Estate

27 Clambelly Rd, Chilmark, MA 02535
/12
$6,180 per month
- 3 Beds
- 3.5 Baths
- 1,872 Sq Ft
- House for Rent
44 Music St Wt153, West Tisbury, MA 02575

PLEASE TAKE NOTE!!!!!THIS IS A WEEKLY SUMMER RENTAL NOT A MONTHLY RENTAL. THE PRICE ON THIS LISTING IS A WEEkLY PRICE!!!!!!!

Karen Overtoom Karen M. Overtoom R.E.

44 Music St Wt153, West Tisbury, MA 02575
/29
$1,100,000 Sold Jun 27, 2025
- 1,976 Sq Ft
- $557/SF
- 9 Days On Market
- 4 Beds
- 3 Baths
- Built 1985
10 Kims Way, Oak Bluffs, MA 02557

Located under a mile from downtown Oak Bluffs, this well-maintained 4-bedroom home includes a 3-bedroom main house and a 1-bedroom basement apartment. Recent upgrades include a new roof, Title V septic system, electric service, and town water connection. The first floor features a spacious living/dining area, kitchen, half bath, and a cozy den. Upstairs are 3 bedrooms and a full bath. The

Michael Schweikert Ocean Park Realty Inc

10 Kims Way, Oak Bluffs, MA 02557

/25
Est $2,093,611 Not Listed For Sale
- 5 Beds
- 3 Baths
- 3,636 Sq Ft
131 Shubael Weeks Path, Vineyard Haven, MA 02568

131 Shubael Weeks Path, Vineyard Haven, MA 02568

/47
$2,675,000
- 6 Beds
- 5 Baths
- 2,970 Sq Ft
128 & 136 Spring St, Vineyard Haven, MA 02568

A Rare Compound Opportunity in the Heart of Vineyard Haven - 128 & 136 Spring Street—two adjacent properties being sold together to create a unique, flexible compound just moments from the Tisbury School and downtown Vineyard Haven. With a spacious main residence and a separate guest house, this rare combination presents a compelling opportunity for multigenerational living, seasonal enjoyment,

David Dickinson Compass | Point B

128 & 136 Spring St, Vineyard Haven, MA 02568
/12
$15,000 per month
- 5 Beds
- 6.5 Baths
- 4,137 Sq Ft
- House for Rent
41 Naushon Rd Wt116, Aquinnah, MA 02575

Stunning water views from this expansive beachfront estate in Makonikey off Lambert's Cove Rd. Enjoy the large living area with comfortable couches, floor to ceiling windows and french doors for seamless indoor to outdoor living and dining. There is a fully equipped kitchen. Some folks will enjoy the treadmill and elliptical while watching boats pass by or even play squash in the indoor squash

Karen Overtoom Karen M. Overtoom R.E.

41 Naushon Rd Wt116, Aquinnah, MA 02575
/32
$1,100,000 Sold Jun 27, 2025
- 1,976 Sq Ft
- $557/SF
- 156 Days On Market
- 4 Beds
- 2.5 Baths
- Built 1985
10 Kims Way, Oak Bluffs, MA 02568

Located under a mile from downtown Oak Bluffs, this well-maintained 4-bedroom home includes a 3-bedroom main house and a 1-bedroom basement apartment. Recent upgrades include a new roof, Title V septic system, electric service, and town water connection. The first floor features a spacious living/dining area, kitchen, half bath, and a cozy den. Upstairs are 3 bedrooms and a full bath. The

Michael Schweikert Ocean Park Realty, Inc.

10 Kims Way, Oak Bluffs, MA 02568

/2
Est $1,376,724 Not Listed For Sale
- 3 Beds
- 3 Baths
- 1,400 Sq Ft
45 Pine Tree Ln, Vineyard Haven, MA 02568

45 Pine Tree Ln, Vineyard Haven, MA 02568

/42
$2,675,000
- 6 Beds
- 4.5 Baths
- 2,970 Sq Ft
128 W Spring St, Vineyard Haven, MA 02568

A Rare Compound Opportunity in the Heart of Vineyard Haven - 128 & 136 Spring Street - Two adjacent properties being sold together create a flexible compound just moments from downtown Vineyard Haven. The 4-bedroom, 2-1/2 bath main house also includes a separate, 1-bedroom in-law/nanny apartment with a full bath. The guest house has 1 bedroom and 1 bath, with a 4-bedroom septic system allowing

David Dickinson Compass

128 W Spring St, Vineyard Haven, MA 02568
/8
$8,250 per month
- 7 Beds
- 5 Baths
- 3,528 Sq Ft
- House for Rent
227 S Gate Rd Wt120, West Tisbury, MA 02575

THIS PROPERTY IS A WEEKLY PROPERTY!! Set on 12 acres of peaceful woods, meadows, stone walls and its own pond, this charming 18th century 4 bedroom farmhouse and 3 bedroom rustic barn sleeps 12 and is perfect for larger groups wanting peace and tranquility all within a short distance to private swimming beaches. The setting, on exclusive Seven Gates Farm, offers miles of sandy trails through

Karen Overtoom Karen M. Overtoom R.E.

227 S Gate Rd Wt120, West Tisbury, MA 02575
/29
$1,925,000 Sold Jun 24, 2025
- 2,378 Sq Ft
- $810/SF
- 0 Days On Market
- 3 Beds
- 3 Baths
- Built 1928
21 William St, Vineyard Haven, MA 02568

Nestled at the quiet end of William Street, just moments from the lively charm of downtown Vineyard Haven, this delightful 3-bedroom home offers the perfect blend of comfort and convenience. The spacious primary suite is thoughtfully located on the main level, providing both privacy and ease of living. Inside, an open and airy floor plan combines timeless character with modern touches—ideal for

Laura Finney Wallace & Co. Sotheby's

21 William St, Vineyard Haven, MA 02568

/36
Est $2,321,551 Not Listed For Sale
- 4 Beds
- 3 Baths
- 2,436 Sq Ft
377 State Rd, Vineyard Haven, MA 02568

377 State Rd, Vineyard Haven, MA 02568

/39
$3,299,000
- 3 Beds
- 3.5 Baths
- 3,082 Sq Ft
53 Stoney Hill Rd, Vineyard Haven, MA 02568

Nestled in one of the island’s most sought-after locations, this exceptional property offers refined coastal living with access to the famed Lambert’s Cove Beach yet a short drive to VH.Thoughtfully designed, it features 3 spacious bedrooms each with an en suite bath, providing comfort and privacy for all. Primary suite is a true retreat with a brand new luxurious bathroom. At the heart of the

Jennifer B. DaSilva Compass

53 Stoney Hill Rd, Vineyard Haven, MA 02568
/8
$18,500 per month
- 4 Beds
- 3.5 Baths
- 1,714 Sq Ft
- House for Rent
4 Windy Way Wt143, West Tisbury, MA 02575

THIS PROPERTY IS A WEEKLY RENTAL PROPERTY!! The 3.3 acre private setting is most picturesque with its positioning in private Upper Makonikey , the long circular driveway , its grassy lawn, and rolling landscape fields . Only a short distance away is over 3,000 feet of PRIVATE sandy association Beaches , directly below , with two nearby parking lot access-ways . Nestled onto this promontory is a

Karen Overtoom Karen M. Overtoom R.E.

4 Windy Way Wt143, West Tisbury, MA 02575
/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

/14
Est $2,704,037 Not Listed For Sale
- 3 Beds
- 3 Baths
- 2,926 Sq Ft
30 Pond Ln, Vineyard Haven, MA 02568

30 Pond Ln, Vineyard Haven, MA 02568

/40
$1,925,000
- 4 Beds
- 4 Baths
- 3,927 Sq Ft
44 Tiffany Dr, Oak Bluffs, MA 02557

Nestled within the desirable Lagoon Estates development and set on a beautifully wooded 1.38-acre lot abutting Land Bank property, this expansive and sun-filled home offers versatile living space and a flexible floor plan. The main house features generously sized rooms enhanced by large windows that flood the interior with natural light. The kitchen boasts white cabinetry, a wall-mounted

Nora Jardin Island Real Estate

44 Tiffany Dr, Oak Bluffs, MA 02557
/8
$4,800 per month
- 3 Beds
- 3 Baths
- 3,279 Sq Ft
- House for Rent
165 Christiantown Rd, West Tisbury, MA 02575

THIS PROPERTY IS A WEEKLY PROPERTY!! The home is set on six beautifully landscaped acres with original stone walls. It is located in private historic Christiantown on the North Shore, a short distance from both Lambert’s Cove Beach and Cedar Tree Neck Wildlife Reserve. Cedar Tree is a habitat with tumbling streams and freshwater ponds, sandy beaches and rocky cliffs, tall oaks and cool beech

Karen Overtoom Karen M. Overtoom R.E.

165 Christiantown Rd, West Tisbury, MA 02575
/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

/36
Est $1,288,385 Not Listed For Sale
- 4 Beds
- 2 Baths
- 1,780 Sq Ft
16 Rock Pond Rd, Vineyard Haven, MA 02568

16 Rock Pond Rd, Vineyard Haven, MA 02568

/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
/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
/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

/40
Est $1,844,798 Not Listed For Sale
- 4 Beds
- 2.5 Baths
- 1 Sq Ft
179 Main St, Vineyard Haven, MA 02568

179 Main St, Vineyard Haven, MA 02568

/56
$2,189,000
- 5 Beds
- 3.5 Baths
- 3,587 Sq Ft
23 Crowell Ln, Vineyard Haven, MA 02568

WEST CHOP! Farmhouse charm and comfortable elegance define this very spacious 5 Bedroom, 3,200 s/f home that is set on just over an acre on a private wooded lot. Hear the ferry, spot the osprey, and unwind on the back deck. This is your invitation to island living! The home welcomes you with an expansive front porch that overlooks a mature landscape that is framed with a stone wall and beautiful

Sheila Morse Island Real Estate

23 Crowell Ln, Vineyard Haven, MA 02568
/27
$18,840 per month
- 3 Beds
- 2.5 Baths
- House for Rent
21 William St Vh430, Tisbury, MA 02568

THIS IS A WEEKLY SUMMER RENTAL ONLY.THE WEEKLY PRICE IN AUGUST IS $4,710. PER WEEK.SEE WEB SITE FOR ADDITIONAL WEEKLY PRICING. Lovely elegant home with wonderful art and furnishings. Once you step in the front door you will fall in love with this lovely home. Each room is a delight. Large nicely appointed kitchen with easy access to a beautiful dining room. A formal living room is next to a less

Karen Overtoom Karen M. Overtoom R.E.

21 William St Vh430, Tisbury, MA 02568
/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

/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

/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
/25
$10,800 per month
- 2 Beds
- 4 Baths
- 1,800 Sq Ft
- House for Rent
256 Sandpiper Lane Vh417, Tisbury, MA 02568

THIS IS A WEEKLY SUMMER RENTAL ONLY.THE WEEKLY PRICE IN AUGUST IS $2,700. PER WEEK.SEE WEB SITE FOR ADDITIONAL WEEKLY PRICING. This well appointed condo will make you feel comfortable and at home the moment you walk in. Swimming, kayaking, tennis, walking trails, and shopping are all at your finger tips. Mink Meadows Golf Course is just a stroll down the street as well. Enjoy all the Island has

Karen Overtoom Karen M. Overtoom R.E.

256 Sandpiper Lane Vh417, Tisbury, MA 02568
/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

/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

Showing Results 41 - 80, Page 2 of 18

Massachusetts Dukes County Vineyard Haven 02568

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