Tisbury, MA Homes

/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
/34
$25,000 total monthly price
- 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
/42
$1,700,000 Sold Nov 03, 2025
- 2,558 Sq Ft
- $665/SF
- 118 Days On Market
- 3 Beds
- 4 Baths
- Built 1986
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

/40
Est $1,720,934 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

/26
$1,950,000 Pending
- 5 Beds
- 3 Baths
- 1,916 Sq Ft
14 Rebekahs Way, Vineyard Haven, MA 02568

Affectionately referred to as ‘The Treehouse', this property encompasses all the elements of a modern, sophisticated residence while providing the warmth and comfort of a private retreat. Professionally designed by Hutker Architects, this four-bedroom home, with a den/potential fifth bedroom, is sited in a private area, conveniently located with easy access to grocery store, pharmacy, and post

Sheila Morse Island Real Estate

14 Rebekahs Way, Vineyard Haven, MA 02568
/17
$12,000 total monthly price
- 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
/28
$1,260,000 Sold Nov 03, 2025
- 1,820 Sq Ft
- $692/SF
- 182 Days On Market
- 4 Beds
- 2 Baths
- Built 2002
11 Flamingo Dr, Edgartown, MA 02539

Located in the Dodger's Hole subdivision is this inviting four bedrooms plus office, two-bathroom cape style home. The property has been well cared for and is a delight to view. Sited on .5 acres of land with a pea stone driveway, wraparound deck, and outdoor shower with new enclosure. The antique garage is a great storage space for lawn equipment, garden supplies or small vehicle. The living

Skip Dostal, Jr Martha's Vineyard Real Estate

11 Flamingo Dr, Edgartown, MA 02539

/48
Est $2,869,894 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

/81
$1,785,000 Pending
- 4 Beds
- 3.5 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
/40
$32,500 total monthly price
- 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
/16
$1,135,000 Sold Oct 31, 2025
- 1,344 Sq Ft
- $844/SF
- 10 Days On Market
- 3 Beds
- 2 Baths
- Built 2002
30 Teaberry Ln, Edgartown, MA 02539

Well-maintained three bedroom, 2 bath home on a level .51 acre lot. Primary en-suite and open floor plan offers the best in first-floor living. Large unfinished basement, outdoor shower and recent Title V inspection of the four bedroom septic system. Deck overlooks the spacious backyard with room for a pool. Convenient to shellfishing or kayaking in Sengekontacket, Caroline Tuthill Preserve and

Dawn Bellante-Holand Sandpiper Realty

30 Teaberry Ln, Edgartown, MA 02539

/49
Not Listed For Sale
- 4 Beds
- 3.5 Baths
- 2,092 Sq Ft
670 State Rd, Vineyard Haven, MA 02568

670 State Rd, Vineyard Haven, MA 02568

/23
$1,795,000 Pending
- 4 Beds
- 3 Baths
- 2,038 Sq Ft
25 Hampson Ave, Oak Bluffs, MA 02568

Location is everything. Fantastic Cape in a quiet neighborhood, just a 10-minute walk to harbor and downtown. The first-floor plan includes a spacious living-room that opens to an eat-in kitchen, large Master with full bath, and a second bedroom with a full bath. The second floor has a beautiful large open space area for a media room, study or playroom and 2 more large bedrooms with another full

Lenny Altieri Premier Properties

25 Hampson Ave, Oak Bluffs, MA 02568
/29
$64,000 total monthly price
- 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
/55
$1,100,000 Sold Oct 31, 2025
- 1,900 Sq Ft
- $579/SF
- 91 Days On Market
- 3 Beds
- 2.5 Baths
- Built 1999
145 Sandpiper Ln Unit 10, Vineyard Haven, MA 02568

Enjoy effortless island living in this beautifully renovated 3-bedroom, 2.5-bath condo, tucked within a quiet and well-maintained association. Thoughtfully updated with modern finishes and quality craftsmanship, this spacious unit offers comfort, style, and functionality. The open-concept living area features a cozy wood pellet fireplace, perfect for cooler evenings, and flows seamlessly into a

Emily Flake Viewpoints

145 Sandpiper Ln Unit 10, Vineyard Haven, MA 02568

/35
Est $1,162,460 Not Listed For Sale
- 4 Beds
- 2 Baths
- 1,368 Sq Ft
29 Dunham Ave, Vineyard Haven, MA 02568

29 Dunham Ave, Vineyard Haven, MA 02568

/46
$1,675,000 Under Contract
- 4 Beds
- 2.5 Baths
- 2,127 Sq Ft
5 Bayes Hill Cir, Vineyard Haven, MA 02568

Beautiful Bayes Hill Association! This nicely maintained 4 bedroom colonial-style home, located on a quiet cul-de-sac, is the perfect blend of comfort and charm. A new Red Cedar Shingle Roof, a newer high-efficiency furnace, newer state-of-the-art 75-gallon hot water heater, central air conditioning, 2 car garage and a freshly painted exterior this residence combines modern conveniences with

Rene Jackson Island Real Estate

5 Bayes Hill Cir, Vineyard Haven, MA 02568
/20
$20,000 total monthly price
- 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
/25
$1,125,000 Sold Oct 28, 2025
- 1,432 Sq Ft
- $786/SF
- 97 Days On Market
- 3 Beds
- 1.5 Baths
- Built 1964
140 Longview Rd, Vineyard Haven, MA 02568

Nestled in the hills of Longview, less than 1 mile from beautiful Lambert's Cove Beach, this 3-bedroom retreat is a cozy year-round home or an airy summer getaway - whatever your needs might be. The vaulted ceilings throughout the home allow it to live much larger than its square footage - and the expansive front deck stretches the living space all through the spring, summer and even fall

Candy DaRosa Feiner Real Estate

140 Longview Rd, Vineyard Haven, MA 02568

/23
Est $2,664,048 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

/35
$1,870,000 Under Contract
- 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 Martha's Vineyard R.E.

32 Flamingo Dr, Edgartown, MA 02539
/25
$24,000 total monthly price
- 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
/17
$1,200,000 Sold Oct 28, 2025
- 1,680 Sq Ft
- $714/SF
- 209 Days On Market
- 4 Beds
- 2 Baths
- Built 1987
211 Edgartown Vineyard Haven Rd, Tisbury, MA 02568

MULTIFAMILY OPPORTUNITYA wonderful compound on the outskirts of town. Set nicely back off the Edgartown Road, the existing home has 4/5 comfortable bedrooms and 2 baths on a nice 1-acre parcel with a good sense of privacy. Behind the home is a fire pit, a shed and another septic system already installed that will serve an additional 5 bedrooms! This property is on a trail to the Bare Hill

Jim Feiner Feiner Real Estate

211 Edgartown Vineyard Haven Rd, Tisbury, MA 02568

/32
Est $4,566,360 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

/42
$1,350,000
- 3 Beds
- 2 Baths
- 1,809 Sq Ft
169 Clover Hill Dr, Vineyard Haven, MA 02568

Located on a cul-de-sac in a serene neighborhood, this classic Cape-style home is less than 1.5 miles from Main Street, Vineyard Haven. The location is ideal—close to restaurants, shopping, and the ferry. The three-bedroom home offers a comfortable and functional layout. The first floor features a spacious living room with a wood-burning fireplace, an adjacent dining room, and a fabulous

Stephanie Roache Donnelly + Co.

169 Clover Hill Dr, Vineyard Haven, MA 02568
/30
$20,000 total monthly price
- 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
/39
$1,470,000 Sold Oct 27, 2025
- 1,620 Sq Ft
- $907/SF
- 23 Days On Market
- 3 Beds
- 2.5 Baths
- Built 2007
26 Winne Ave, Vineyard Haven, MA 02568

Welcome to your dream home just a short walk to the lagoon. This home offers easy access for dropping a kayak or taking a refreshing afternoon dip from a public access point. Discover this charming home nestled on a corner lot within a serene neighborhood. This beach home has an updated kitchen and bathrooms. The kitchen is equipped with new appliances and gorgeous quartz countertops, making it a

Joe & Nicole Holland Vineyard Dream Realty LLC

26 Winne Ave, Vineyard Haven, MA 02568

/20
Est $1,723,617 Not Listed For Sale
- 3 Beds
- 2 Baths
- 1,971 Sq Ft
21 Bold Meadow Ln, Edgartown, MA 02539

21 Bold Meadow Ln, Edgartown, MA 02539

/7
$475,000
- Land
- 0.52 Acre
- $913,462 per Acre
36 Boylston Dr, Edgartown, MA 02539

Buildable lot in an established Edgartown neighborhood. Approvals are in hand for the construction of a single-family residential structure not to exceed 3 bedrooms and not to exceed 1,850 square feet of heated living area (screened porches, patios, etc are not included in this square footage). Note that this property cannot be used as a seasonal home or short-term rental. Septic plan has been

Mark Jenkins Wallace & Co. Sotheby's International Realty

36 Boylston Dr, Edgartown, MA 02539
/14
$14,200 total monthly price
- 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
/3
$3,067,050 Sold Oct 22, 2025
- 1,872 Sq Ft
- $1,638/SF
- 0 Days On Market
- 4 Beds
- 3.5 Baths
- Built 1985
114 Park, Oak Bluffs, MA 02557

Not Listed in LINK

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114 Park, Oak Bluffs, MA 02557

/19
Est $1,286,014 Not Listed For Sale
- 3 Beds
- 2 Baths
- 1,520 Sq Ft
46 Windsor Dr, Edgartown, MA 02539

46 Windsor Dr, Edgartown, MA 02539

/8
$475,000
- Land
- 0.52 Acre
- $913,462 per Acre
36 Boylston Dr Unit 1.329, Edgartown, MA 02539

Buildable lot in an established Edgartown neighborhood. Approvals are in hand for the construction of a single-family residential structure not to exceed 3 bedrooms and not to exceed 1,850 square feet of heated living area (screened porches, patios, etc are not included in this square footage). Note that this property cannot be used as a seasonal home or short-term rental. Septic plan has been

Mark Jenkins Wallace & Co. Sotheby's

36 Boylston Dr Unit 1.329, Edgartown, MA 02539
/8
$18,000 total monthly price
- 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
/2
$1,700,000 Sold Oct 20, 2025
- 1,803 Sq Ft
- $943/SF
- 0 Days On Market
- 5 Beds
- 3 Baths
- Built 1982
37 Vineyard Meadow Farms Rd, West Tisbury, MA 02568

Not Listed in LINK

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37 Vineyard Meadow Farms Rd, West Tisbury, MA 02568

/36
Est $2,466,989 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

/32
$560,000
- 1 Bed
- 1.5 Baths
- 590 Sq Ft
21 Island Inn Rd Unit 39G, Oak Bluffs, MA 02568

Own a piece of the Vineyard dream with a fully furnished, beautifully updated condo perfectly designed for comfort and vacation living at the Island Inn Country Club in Oak Bluffs. The location is just off Beach Road, a short distance to beaches, downtown Circuit Ave, and a lovely drive along Beach Road to Edgartown Village. The bike path, public transportation, and a popular restaurant with live

Diana Gilmore Island Real Estate

21 Island Inn Rd Unit 39G, Oak Bluffs, MA 02568
/28
$38,000 total monthly price
- 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
/19
$1,330,000 Sold Oct 17, 2025
- 1,404 Sq Ft
- $947/SF
- 112 Days On Market
- 3 Beds
- 1.5 Baths
- Built 1983
32 MacHipscat Trail, Vineyard Haven, MA 02568

This Cape Style home privately sited on 1.89 acres at the end of a cul-de-sac abutting conservation land with many walking trails. Nice features include spacious living spaces that include a well equipped kitchen with custom cherry cabinets, dining room, living room with fireplace, wood stove and french doors that lead you out to a private patio and backyard. Second floor offers two guest

Brenda Galligan Karen M. Overtoom R.E.

32 MacHipscat Trail, Vineyard Haven, MA 02568

/39
Est $7,234,025 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

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