Tisbury, MA Homes

/27
$1,150,000
- 2 Beds
- 2.5 Baths
- 1,500 Sq Ft
70 Carol Ln, Oak Bluffs, MA 02557

Charming Renovated Ranch in the Heart of Oak Bluffs Discover the perfect blend of comfort, convenience, and coastal charm in this beautifully renovated ranch home, ideally located in a central Oak Bluffs neighborhood close to everything down-Island. Set on a spacious 1/3-acre lot, this property offers both privacy and proximity — just minutes from the Oak Bluffs School, town center, and all the

Lisa Lucier

Anchor Realty of Martha's Vineyard

(508) 456-5742

70 Carol Ln, Oak Bluffs, MA 02557
/3
$1,500 total monthly price
- 1 Bed
- 1 Bath
- House for Rent
7 Pacific Ave, Oak Bluffs, MA 02568

Property Id: 2328998Walk to beach town and bus, mellow home , friendly , gardens .Owner retired preschool teacher and renovator. One big dog .Not cannabis or overnight guests please. Students and foreigners welcome.

7 Pacific Ave, Oak Bluffs, MA 02568
/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 $1,653,559

Last Listing Agent Michele Casavant Vineyard Village Realty

28 Roger's Way, Oak Bluffs, MA 02557

/2
Est $2,489,601 Not Listed For Sale
- 6 Beds
- 4.5 Baths
- 3,035 Sq Ft
23 Oak Ln, Vineyard Haven, MA 02568

23 Oak Ln, Vineyard Haven, MA 02568

/7
$700,000 Pending
- Land
- 0.1 Acre
- $7,000,000 per Acre
0 Massasoit Ave, Oak Bluffs, MA 02557

Commercial Land Downtown Oak Bluffs on Circuit Avenue. Explore the many potentials this commercial land has to offer in the desirable location in the heart of Oak Bluffs.

Lisa Lucier

Anchor Realty of MV

(508) 978-2876

0 Massasoit Ave, 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
/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
Current Estimated Value $1,603,863

Last Listing Agent Meg Bodnar Tea Lane Associates

251 State Rd, Vineyard Haven, MA 02568

/15
Not Listed For Sale
- 3 Beds
- 1 Bath
- 816 Sq Ft
9 Leslie Ln, Oak Bluffs, MA 02568

9 Leslie Ln, Oak Bluffs, 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
/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
/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

/15
Est $2,168,722 Not Listed For Sale
- 3 Beds
- 3.5 Baths
- 1,852 Sq Ft
13 Holly Bear Ln, Edgartown, MA 02539

13 Holly Bear Ln, Edgartown, MA 02539

/2
$1,650,000 Pending
- 6 Beds
- 3.5 Baths
- 1,617 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 MV

(508) 299-5240

34 Massasoit Ave, Oak Bluffs, MA 02557
/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
/38
$2,860,000 Sold Mar 10, 2025

49 William St, Vineyard Haven, MA 02568
- 5 Beds
- 4.5 Baths
- 3,752 Sq Ft
- Built 1836
Last Sold Summary
- 12% Below List Price
- $762/SF
- 290 Days On Market
Last Listing Agent Alyssa Halisky Wallace & Co. Sotheby's International Realty

49 William St, Vineyard Haven, MA 02568

/3
Est $1,616,357 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

/26
$1,999,000
- 3 Beds
- 3.5 Baths
- 2,453 Sq Ft
34 Davis St, Tisbury, MA 02568

NEW CONSTRUCTION – Designed by Outlands Design and built by McElhinney Construction, this home exemplifies modern coastal design. 34 Davis Street delivers the perfect balance of sophistication and relaxed island living. Positioned to offer both privacy and proximity to the Island’s harbors, shops, and beaches. Spread across two thoughtfully designed levels, the interiors are bathed in natural

Andrew McElhinney Compass LLC

34 Davis St, Tisbury, MA 02568
/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
/2
$1,700,000 Sold Oct 20, 2025

37 Vineyard Meadow Farms Rd, West Tisbury, MA 02568
- 5 Beds
- 3 Baths
- 1,803 Sq Ft
- Built 1982
Last Sold Summary
- $943/SF
- 0 Days On Market
Last Listing Agent LINK Email Cache LINK

37 Vineyard Meadow Farms Rd, West Tisbury, MA 02568

/36
Est $2,676,608 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

/28
$1,799,000
- 4 Beds
- 2.5 Baths
- 3,268 Sq Ft
7 Upper Meadow Ln, Oak Bluffs, MA 02557

Meadowview Farms -- This home is ideal for those who love to host lively gatherings! Set at the end of a quiet cul-de-sac, this spacious Colonial offers over 3,200 sq ft designed for comfortable living and easy entertaining. The home features four bedrooms and 2.5 baths, including a primary suite with walk-in closets and private bath. The main living area flows from a living room with fireplace

Lesley Heidt Sandpiper Realty Inc

7 Upper Meadow Ln, Oak Bluffs, MA 02557
/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
/26
$1,800,000 Sold Oct 15, 2025

82 Skiff Ave, Tisbury, MA 02568
- 3 Beds
- 3.5 Baths
- 1,913 Sq Ft
- Built 2020
Last Sold Summary
- 10% Below List Price
- $941/SF
- 128 Days On Market
Current Estimated Value $1,646,192

Last Listing Agent Lenny Altieri Premier Properties

82 Skiff Ave, Tisbury, MA 02568

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

0 Bridle Path Rd, Vineyard Haven, MA 02568

/30
$1,999,000
- 4 Beds
- 3 Baths
- 2,730 Sq Ft
5 Pine Tree Ln, Vineyard Haven, MA 02568

Blending 1920s charm with modern luxury, this beautifully renovated home is tucked away in the sought-after West Chop area of Vineyard Haven. Just steps from the neighborhood beach on the pristine shores of Vineyard Sound, this elegant seaside retreat offers the perfect mix of historic character and contemporary comfort. Inside, a thoughtfully designed floor plan welcomes you with generous living

Alyssa Halisky Wallace & Co. Sotheby's International Realty

5 Pine Tree Ln, Vineyard Haven, MA 02568
/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
/19
$750,000 Sold Nov 07, 2025

41 Trinity Park, Oak Bluffs, MA 02557
- 4 Beds
- 1 Bath
- 1,154 Sq Ft
- Built 1867
Last Sold Summary
- 6% Below List Price
- $650/SF
- 14 Days On Market
Last Listing Agent Stacy Ickes Donnelly + Co.

41 Trinity Park, Oak Bluffs, MA 02557

/38
Est $1,025,579 Not Listed For Sale
- 3 Beds
- 1 Bath
- 1,120 Sq Ft
287 County Rd, Vineyard Haven, MA 02568

287 County Rd, Vineyard Haven, MA 02568

/35
$1,870,000 Pending
- 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
/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
/19
$1,110,000 Sold May 08, 2025

31 9th St N, Edgartown, MA 02539
- 2 Beds
- 1.5 Baths
- 1,275 Sq Ft
- Built 1972
Last Sold Summary
- 7% Below List Price
- $871/SF
- 45 Days On Market
Current Estimated Value $1,133,932

Last Listing Agent Alyssa Halisky Wallace & Co. Sotheby's

31 9th St N, Edgartown, MA 02539

/17
Est $1,565,237 Not Listed For Sale
- 3 Beds
- 3 Baths
- 2,298 Sq Ft
19 Quantapog Rd, Vineyard Haven, MA 02568

19 Quantapog Rd, Vineyard Haven, MA 02568

/50
$1,900,000
- 4 Beds
- 3 Baths
- 2,056 Sq Ft
20 Brook Hollow Rd, Vineyard Haven, MA 02568

This spacious custom designed home is well sited to offer maximum privacy in the lush area of Long View. A short bike ride to Lambert's Cove beach, it's also about a 20-minute walk down a quiet private road. The home lays out well for family and extended guests with a roomy living room boasting vaulted ceilings and large windows. The house is designed to have an intimate relationship with the

Jim Feiner Feiner Real Estate

20 Brook Hollow Rd, Vineyard Haven, MA 02568
/8
$17,500 total monthly price
- 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 relaxing

Karen Overtoom Karen M. Overtoom R.E.

550 Chappaquonsett Rd Vh424 Unit 1, Tisbury, MA 02568
/31
$1,325,000 Sold Jun 30, 2025

191 Spring Hill Rd, Vineyard Haven, MA 02568
- 5 Beds
- 4 Baths
- 2,292 Sq Ft
- Built 1992
Last Sold Summary
- 5% Below List Price
- $578/SF
- 10 Days On Market
Current Estimated Value $1,258,388

Last Listing Agent Madelyn Silvia Wallace & Co. Sotheby's

191 Spring Hill Rd, Vineyard Haven, MA 02568

/12
Est $1,268,189 Not Listed For Sale
- 4 Beds
- 2 Baths
- 1,997 Sq Ft
3 Carole Ave, Vineyard Haven, MA 02568

3 Carole Ave, Vineyard Haven, MA 02568

/37
$1,750,000 Under Contract
- 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
/10
$8,500 total monthly price
- 3 Beds
- 2 Baths
- House for Rent
29 Bea Lane Wt160 Unit 1, West Tisbury, MA 02575

THIS IS A WEEKLY RENTAL PROPERTY!! Red Farm, Off Lambert's Cove Road West Tisbury. This newly built Contemporary Home is privately sited overlooking a peaceful meadow and wooded setting. The spacious floor plan features an open living, dining and a well equipped chef's kitchen, cathedral ceilings, wood floors and sliders that lead to a nicely landscaped yard. Three spacious bedrooms, the primary

Karen Overtoom Karen M. Overtoom R.E.

29 Bea Lane Wt160 Unit 1, West Tisbury, MA 02575
/26
$1,600,000 Sold Nov 07, 2025

96 Pondview Dr, Oak Bluffs, MA 02536
- 4 Beds
- 2.5 Baths
- 2,115 Sq Ft
- Built 2004
Last Sold Summary
- 1% Below List Price
- $757/SF
- 35 Days On Market
Last Listing Agent Doug Burke Cronigs Real Estate

96 Pondview Dr, Oak Bluffs, MA 02536

/13
Est $1,241,679 Not Listed For Sale
- 3 Beds
- 2 Baths
- 1,428 Sq Ft
33 Menahan St, Vineyard Haven, MA 02568

33 Menahan St, Vineyard Haven, MA 02568

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