5 Pine Tree Ln, Tisbury, MA 02568
FOR SALE

5 Pine Tree Ln
Tisbury, MA 02568

  • 4 Beds
  • 3 Baths
  • 2,730 sqft

$1,999,000

Original price: $1,999,999
Est. Mortgage $10,692/mo*

$1,999,000

Original price: $1,999,999
Est. Mortgage $10,692/mo*
4 Beds
3 Baths
2,730 sqft

Local Information

Map showing home location
© Google
-- mins to
Commute Destination

Description

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 spaces. At the heart of the home is a chef’s kitchen featuring custom cabinetry, high-end appliances, and stylish finishes—perfect for both everyday living and entertaining. The open-concept living and dining areas flow seamlessly, enhanced by updated systems and central air conditioning for year-round comfort. Upstairs, the primary suite provides a serene escape with a spa-like tile bath and soaking tub. Two additional guest bedrooms share a beautifully appointed full bath that also includes convenient laundry. Unique details like a compass rose stained glass window add a distinctive nautical touch. The finished lower level offers even more living space, including a large bedroom—ideal for guests or extended family. Outdoors, a stunning mahogany deck overlooks the newly landscaped backyard, complete with an outdoor shower and perfect areas for entertaining. With close proximity to downtown Vineyard Haven and the beaches of Vineyard Sound, this exceptional home captures the essence of island living—timeless, refined, and move-in ready.

Home Highlights

Parking
No Info
Outdoor
No Info
A/C
Heating only
HOA
None
Price/Sqft
$732
Listed
180+ days ago

Home Details for 5 Pine Tree Ln

Interior Features

Interior Details
Basement: Finished lower level with family room and large bedroom. Utility closet.Number of Rooms: 11
Beds & Baths
Number of Bedrooms: 4Number of Bathrooms: 3Number of Bathrooms (full): 3
Dimensions and Layout
Living Area: 2730 Square Feet
Appliances & Utilities
Utilities: CblAppliances: Stove: Bosch Induction Oven & Stovetop, Washer: Electrolux Front Loading Washer
Heating & Cooling
Heating: Heat PumpNo CoolingHas HeatingHeating Fuel: Heat Pump
Fireplace & Spa
Fireplace: 1
Windows, Doors, Floors & Walls
Flooring: 3
Levels, Entrance, & Accessibility
Floors: 3
View
Has a ViewView: None, Res

Exterior Features

Exterior Home Features
Other Structures: Outdoor ShowerExterior: Deck, Porch, Garden, DdBch, PubBchFoundation: Full foundation with finished basementGarden
Parking & Garage
No CarportNo GarageNo Attached GarageParking: Private driveway
Frontage
Frontage Type: NoneNot on Waterfront
Water & Sewer
Sewer: Septic Tank

Days on Market

Days on Market: 180+

Property Information

Year Built
Year Built: 1927Year Renovated: 2024
Property Type / Style
Property Type: ResidentialProperty Subtype: Single Family Residence

Price & Status

Price
List Price: $1,999,000Price Per Sqft: $732

Active Status

MLS Status: A

Location

Direction & Address
City: Vineyard Haven

Agent Information

Listing Agent
Listing ID: 43291

Building

Building Area
Building Area: 2730 Square Feet

Lot Information

Lot Area: 7797.24 sqft

Offer

Listing Agreement Type: E

Miscellaneous

BasementMls Number: 43291
Last check for updates: about 11 hours ago
Listing courtesy of Alyssa Halisky
Wallace & Co. Sotheby's
Source: LINK, MLS#43291
Also Listed on MLS PIN, MLS PIN, LINK.

Price History for 5 Pine Tree Ln

DatePriceEventSource
02/27/2026$1,999,000PriceChange
MLS PIN #73480830
10/01/2025$1,999,999PriceChange
MLS PIN #73410635
09/18/2025$1,999,000PriceChange
Martha's Vineyard MLS #32400203
07/15/2025$2,195,000PriceChange
Martha's Vineyard MLS #32400203
05/17/2025$2,395,000Listed For SaleLINK #43291
01/31/2025$2,490,000ListingRemovedLINK #42345
09/02/2024$2,490,000PriceChange
Martha's Vineyard MLS #32400203
07/31/2024$2,590,000Listed For SaleLINK #42345
07/19/2024$2,590,000ListingRemovedLINK #42204
06/24/2024$2,590,000Listed For SaleLINK #42204
04/28/2023$1,050,000Sold
LINK #40535
03/10/2023$1,100,000PendingLINK #40535
03/02/2023$1,100,000Listed For SaleLINK #40535
06/03/1998$50,000Sold
N/A

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Property Tax and Assessment

Year2025
Tax$7,896
Assessment$1,043,100
Home facts updated by county records

Comparable Sales for 5 Pine Tree Ln

Address
Distance
Property Type
Sold Price
Sold Date
Bed
Bath
Sqft
0.06
Single-Family Home
$1,910,000
04/03/26
5
3.5
3,250
0.32
Single-Family Home
$1,050,000
06/30/25
4
2
1,606
0.38
Single-Family Home
$1,000,000
03/31/26
4
2
1,306
0.62
Single-Family Home
$2,637,500
12/12/25
4
3
2,770
0.48
Single-Family Home
$949,000
06/23/25
3
1.5
1,012
0.60
Single-Family Home
$1,164,000
08/12/25
3
2
1,650
0.55
Single-Family Home
$929,000
08/18/25
3
1.5
1,286
0.49
Single-Family Home
$2,100,000
08/27/25
3
3.5
3,310
0.45
Single-Family Home
$946,500
03/11/26
3
1
1,008

Assigned Schools

These are the assigned schools for 5 Pine Tree Ln.
The GreatSchools Rating compares schools on a variety of school quality indicators including test scores, college readiness, equity and more. Learn more.

What Locals Say about Tisbury

At least 26 Trulia users voted on each feature.
  • 87 % Say yards are well-kept

  • 80 % Say it's walkable to grocery stores

  • 78 % Say kids play outside

  • 77 % Say people would walk alone at night

  • 75 % Say it's quiet

  • 72 % Say it's dog friendly

  • 72 % Say it's walkable to restaurants

  • 71 % Say there's holiday spirit

  • 70 % Say there's wildlife

  • 68 % Say car is needed

  • 64 % Say they plan to stay for at least 5 years

  • 63 % Say there are sidewalks

  • 61 % Say parking is easy

  • 53 % Say there are community events

  • 44 % Say neighbors are friendly

  • 39 % Say streets are well-lit

Learn more about our methodology.
  • Trulia User
    "It’s great, I think any dog owner would enjoy this town for their pup. No dog park that I’m aware of, but there is one in a neighboring town. "
  • Kellyjeanmarie33
    "This is the most wonderful place to exist. You are immersed in nature yet close to town and all of its amenities. The beaches are walking distance. The neighborhood is safe. We never lock our doors. The schools are incredible. The community is living and accepting . "
  • Kellyjeanmarie33
    "This is the most wonderful and magical place to be. Full of Natural Beauty. Immersion in Nature is Constant. The Ocean and the Forest are All Around You. We are Blessed to be Here Each Day. 🙏💜✝️💜🙏"
  • Peter G.
    "The Mink Meadows community is like being up island. quiet, private, easy access to market and so much more. "
  • Meesh
    "In the winter the tourists leave and the island gets quiet. It stays relatively warm due to the Gulf Stream pulling warm water north to insulate the Sound and even though the trees loose their leaves, all the moisture creates the perfect conditions for incredibly beautiful sea-foam green lichen and mosses to cover every organic surface. Therefore, the blissful hue saturates the fog and mist; enveloping every road and path throughout the island. It’s the perfect place to forget the Internet for awhile and relish in getting purposefully lost! Enjoy it with friends or better yet, enjoy the solitude; listen to the wind whistle through the trees, hear the waves crash into the shore, and forget about everything but the moment you’re experiencing right then and now! "
  • Jeannine L.
    "The town of Tisbury on Martha's Vineyard is a community with much to offer families with children, couples, and retirees. In addition to the beaches,there are a lot of recreational activities including golf, tennis, biking, fishing, and water sports. During the day the downtown is bustling. The location is also ideal for those who want to be nearby the ferry. The Steanship ferry out of Vineyard Haven runs throughout the year. "
  • Pfred00
    "This community has a great mix of full time and summer residents, so it never feels deserted. Lady Slipper Way is part of the Spring Hill Association, a cul de sac like small community, with fully paved roads and moderate homes. Walking distance to town, tennis and Lake Tashmoo."
  • Bob B.
    "Always something to do on the Vineyard check it out you will want to live here I did and I want to move back"
  • wbaxter
    "Excellent location, just a short walk to the steamship, downtown, beach, schools and more!"
  • Pfred00
    "Have vacationed in MV for more than 10 years. While it has faced a rise in visitors, given its Presidential spotlight, it remains a wonderful place to vacation!!"
  • Robert B.
    "Perfect place to live when you want to get away from it all. Vacation or year round I know of knowhere else I'd rather live. So I'm planning on moving back."

LGBTQ Local Legal Protections

Alyssa Halisky, Wallace & Co. Sotheby's
© 2026 LINK, All Rights Reserved. Data last updated: 2026-05-07 18:08:41 PDT. Some properties may no longer be for sale if they have gone under contract, have sold, or are no longer being offered for sale since the last update.
5 Pine Tree Ln, Tisbury, MA 02568 is a 4 bedroom, 3 bathroom, 2,730 sqft single-family home built in 1927. This property is currently available for sale and was listed by LINK on May 17, 2025. The MLS # for this home is MLS# 43291.