Tisbury, MA Homes

/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
/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

/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
$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
/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

/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
/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
/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

/27
$1,200,000
- 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
/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
/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

/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

/6
$700,000
- 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 Martha's Vineyard

(508) 978-2876

0 Massasoit Ave, 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
/23
$1,175,000 Sold Dec 20, 2024

180 Main St Unit 30, Vineyard Haven, MA 02568
- 2 Beds
- 2 Baths
- 1,300 Sq Ft
- Built 1860
Last Sold Summary
- 13% Below List Price
- $904/SF
- 96 Days On Market
Current Estimated Value $1,180,973

Last Listing Agent Sean Federowicz Landmarks at TODAY Real Estate

180 Main St Unit 30, 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

/34
$3,250,000
- 4 Beds
- 3 Baths
- 1,728 Sq Ft
6 Brewster Ave, Oak Bluffs, MA 02557

Enjoy sweeping ocean views from this beautifully updated East Chop Victorian, complete with a timeless guest cottage. Thoughtfully renovated in 2010, the main residence seamlessly blends historic character with modern comfort. The kitchen and bathrooms have been stylishly updated while preserving the home's original charm and character. The guest cottage, tucked to the rear of the property,

Katherine Donahue Sandpiper Realty Inc

6 Brewster 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
/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

/38
Est $1,047,737 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

/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
/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
/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

/17
Est $1,573,311 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

/16
$1,495,000
- 1 Bed
- 1 Bath
- 650 Sq Ft
47 E East Chop Dr Unit 5, Oak Bluffs, MA 02557

East Chop Waterfront Luxury Cond -- This 1-BR, 1st floor, waterfront condominium, the ''Captain's Quarters'', features outstanding water views of the harbor and sound beyond, private entrance, cathedral ceilings and is just steps from the tennis club, beaches, restaurants, ferries to the mainland and downtown. In pristine condition, the unit includes new kitchen with Bosch appliances, living

Perry Patterson MV Luxury Homes, LLC

47 E East Chop Dr Unit 5, Oak Bluffs, MA 02557
/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
/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
Last Listing Agent Lenny Altieri Premier Properties

82 Skiff Ave, Tisbury, MA 02568

/12
Est $1,277,876 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

/18
$1,100,000
- 2 Beds
- 2 Baths
- 1,583 Sq Ft
25 Vineyard Meadow Farms Rd, West Tisbury, MA 02575

Prime Martha’s Vineyard location! Nestled on 1.4 acres in the sought-after Vineyard Meadow Farms neighborhood, this property offers an exceptional combination of privacy, convenience, and potential. Ideally situated in West Tisbury, close to Edgartown and Vineyard Haven, residents enjoy easy access to local shops, restaurants, and amenities, as well as the island’s most beautiful

Maranda Post Compass | The O'Hanlon Group

25 Vineyard Meadow Farms Rd, West Tisbury, MA 02575
/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
/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

/13
Est $1,272,457 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

/4
$625,000
- Land
- 0.34 Acre
- $1,815,277 per Acre
0-A California Ave Unit Part lot 79, Oak Bluffs, MA 02568

Oak Bluffs Buildable Lot – Prime Location. This flat 2-bedroom building lot is ideally located just moments from the Hudson Avenue access to scenic Lagoon Pond, with easy access to both Farm Neck Golf Club and downtown Oak Bluffs. Situated in a neighborhood of newly constructed homes, this lot presents an excellent opportunity to become part of a growing community in Oak Bluffs. According to the

Andrew McElhinney Compass LLC

0-A California Ave Unit Part lot 79, Oak Bluffs, MA 02568
/8
$11,800 total monthly price
- 4 Beds
- 4 Baths
- 2,612 Sq Ft
- House for Rent
46 Buttonwood Farm Rd Unit 1, West Tisbury, MA 02575

THIS IS A WEEKLY RENTAL PROPERTY!! Beautifully updated contemporary home with impeccably landscaped lawns and gardens, a swimming pond and hot tub with two outdoor showers - one enclosed and one open to the hot tub and patio area on the side of the house. Gorgeous back deck with outdoor dining accessible through sliding glass doors from the dining room. Inside, enjoy the fully equipped and

Karen Overtoom Karen M. Overtoom R.E.

46 Buttonwood Farm Rd Unit 1, West Tisbury, MA 02575
/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 $1,137,743

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

31 9th St N, Edgartown, MA 02539

/14
Est $1,014,872 Not Listed For Sale
- 2 Beds
- 1 Bath
- 1,024 Sq Ft
51 Manchester Ave, Vineyard Haven, MA 02568

51 Manchester Ave, Vineyard Haven, MA 02568

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