5 Pine Tree Lane, Tisbury, MA 02568
Property image
Property image
PENDING
3D VIEW

$1,999,000

  • 4 Beds
  • 3 Baths
  • 2,730 sqft

5 Pine Tree Lane, Tisbury, MA 02568

Est. Mortgage $11,926/mo*
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Home Highlights

Single-Family Home
Built in 1927
$732/sqft
Open Parking

Local Information

  • Map ViewExplore the area around 5 Pine Tree Lane.
  • Schools1 Preschool School1 Elementary School1 Middle School1 High School
  • Shop & Eat
-- mins to
Commute Destination

About this House

What's unique:Stylish finishesOutdoor showerConvenient laundryNewly landscaped backyardStunning mahogany deckGenerous living spaces
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. 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. With close proximity to downtown Vineyard Haven and the beaches of Vineyard Sound, this exceptional home captures the essence of island living. 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.
Last check for updates: about 18 hours ago
Listing courtesy of Alyssa M Halisky, (508) 525-2584
Wallace & Co. Sotheby's International Realty
Source: CCIMLS, MLS#22603526
Also Listed on MLS PIN, MLS PIN, MLS PIN, MLS PIN, CCIMLS, LINK, LINK.

Home Details for 5 Pine Tree Lane

Interior Features

Interior Details
Basement: FinishedNumber of Rooms: 11
Beds & Baths
Number of Bedrooms: 4Number of Bathrooms: 3Number of Bathrooms (full): 3
Appliances & Utilities
Appliances: Dishwasher, Electric Range, Refrigerator, Range Hood, Washer, Electric, Tankless Water HeaterDishwasherLaundry: Electric DryerRefrigeratorWasher
Heating & Cooling
Has CoolingAir Conditioning: Central Air
Fireplace & Spa
Number of Fireplaces: 1
Windows, Doors, Floors & Walls
Flooring: Hardwood, Wood, Tile
Levels, Entrance, & Accessibility
Stories: 3Floors: Hardwood, Wood, Tile

Exterior Features

Exterior Home Features
Roof: AsphaltPatio / Porch: Deck, PorchFencing: PartialExterior: Outdoor Shower, Underground Sprinkler SystemNo Private Pool
Parking & Garage
No GarageNo Attached GarageHas Open ParkingParking Spaces: 3Parking: Driveway,Gravel
Frontage
Not on Waterfront

Days on Market

Cumulative Days on Market: 60Days on Market: 70

Property Information

Year Built
Year Built: 1927
Property Type / Style
Property Type: ResidentialProperty Subtype: Single Family Residence
Building
Construction Materials: Shingle SidingDoes Not Include Home Warranty
Property Information
Parcel Number: TISB M:0004F B:00000 L:00001

Price & Status

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

Active Status

MLS Status: Pending

Media

Location

Direction & Address
City: Vineyard Haven

Agent Information

Listing Agent
Listing ID: 22603526

Building

Building Area
Building Area: 2730 Square Feet

HOA

No HOA

Lot Information

Lot Area: 7840.8 sqft

Listing Info

Special Conditions: None

Miscellaneous

BasementMls Number: 22603526Showing Requirements: Appointment Required, Call Listing Agent

Around this home

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

Sourced by Trulia users. 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. "
    0
    Flag
  • 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 . "
    3
    Flag
  • 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. 🙏💜✝️💜🙏"
    0
    Flag
  • Peter G.
    "The Mink Meadows community is like being up island. quiet, private, easy access to market and so much more. "
    1
    Flag
  • 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! "
    1
    Flag
  • 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. "
    0
    Flag
  • 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."
    1
    Flag
  • 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"
    0
    Flag
  • wbaxter
    "Excellent location, just a short walk to the steamship, downtown, beach, schools and more!"
    0
    Flag
  • 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!!"
    1
    Flag
  • 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."
    0
    Flag

Market trends in Tisbury

Last updated August 2026
Buyer'sMarketSeller'sMarket
Avg. sale price
—
Sale-to-List Price
—
Price per sq ft
—
Available listings
56
1MoM

Home Value

Trulia Estimate
$1.88M
Since last month
Increased$27K (+1.4%)
Since last year
Decreased$222K (-10.6%)
Since last sale
Increased$831K (+79.2%)
Learn more about this home's value by checking out its Trulia Estimate, the value of nearby homes, and how much similar homes have sold for.

Trulia Estimate

The of this home's value increased by +194% in the last 10 years
MonthEstimated value
2026
September 2026$1.88M
August 2026$1.85M
July 2026$1.93M
June 2026$1.78M
May 2026$1.94M
April 2026$1.9M
March 2026$1.92M
February 2026$1.87M
January 2026$1.87M
2025
2024
2023
2022
2021
2020
2019
2018
2017
2016

Comparable sales

These are recently sold homes that have a similar location or other similar features to this home, like bedrooms, bathrooms, and square footage. Get a sense of the expected prices in the area by viewing these homes.
Address
Distance
Property Type
Sold Price
Sold Date
Bed
Bath
Sqft
28 Pine Tree Ln, Tisbury, MA
0.06
Single-Family Home
$1,910,000
04/03/26
5
3.5
3,250
30 Daggett Ave, Tisbury, MA
0.47
Single-Family Home
$2,195,000
08/19/26
4
2.5
2,390
113 Leonard Cir, Tisbury, MA
0.39
Single-Family Home
$1,000,000
03/31/26
4
2
1,306
36 Tashmoo Ave, Tisbury, MA
0.62
Single-Family Home
$2,637,500
12/12/25
4
3
2,770
119 N William St, Tisbury, MA
0.52
Single-Family Home
$917,500
08/31/26
3
1.5
1,395
37 Old Hedge Row, Tisbury, MA
0.78
Single-Family Home
$1,680,000
09/16/26
4
2.5
2,329
22 Clark Ave, Tisbury, MA
0.45
Single-Family Home
$946,500
03/11/26
3
1
1,008
151 Tashmoo Ave, Tisbury, MA
0.77
Single-Family Home
$2,000,000
05/28/26
4
3.5
2,690
151 W Tashmoo Ave, Vineyard Haven, MA
0.77
Single-Family Home
$2,000,000
05/28/26
4
3.5
2,690
208 Irene's Way, Tisbury, MA
1.22
Single-Family Home
$1,160,000
01/05/26
4
3
2,961

Nearby home prices

Get a sense of expected prices in the area by checking the value of nearby homes.
Address
Distance
Price
Bed
Bath
Sqft
Status
537 Main St, Tisbury, MA 02568
0.02
$1,288,100
4
2
1,792
Off Market
11 Pine Tree Ln, Tisbury, MA 02568
0.02
$1,834,800
4
3
2,480
Off Market
4 Oak Tree Ln, Tisbury, MA 02568
0.03
$1,134,800
2
1
994
Off Market
536 Main St, Tisbury, MA 02568
0.03
$1,004,000
2
1
1,002
Off Market
52 Pine Tree Ln, Vineyard Haven, MA 02568
0.03
-
-
-
-
Off Market
6 Oak Tree Ln, Tisbury, MA 02568
0.03
$1,291,600
3
2
1,227
Off Market
20 Pine Tree Ln, Tisbury, MA 02568
0.04
$1,371,900
6
3
1,631
Off Market
10 Holly Tree Ln, Tisbury, MA 02568
0.04
$1,137,300
3
2
1,432
Off Market
23 Pine Tree Ln, Tisbury, MA 02568
0.04
$1,489,300
3
1
1,232
Off Market
527 Main St, Tisbury, MA 02568
0.04
$1,376,000
4
2
1,608
Off Market
7 Holly Tree Ln, Tisbury, MA 02568
0.04
$1,183,600
3
3
1,424
Off Market
Holly Tree Ln, Vineyard Haven, MA 02568
0.04
-
-
-
-
Off Market
5 Holly Tree Ln, Vineyard Haven, MA 02568
0.05
-
-
-
-
Off Market
16 Oak Tree Ln, Tisbury, MA 02568
0.05
$1,622,600
4
1.5
1,642
Off Market
528 Main Street, Tisbury, MA 02568
0.05
$1,600,000
4
4
2,334
For Sale
12 Grove Ave, Tisbury, MA 02568
0.06
$1,105,300
2
2
1,287
Off Market
28 Pine Tree Ln, Tisbury, MA 02568
0.06
$1,910,000
5
3.5
3,250
Recently Sold
22 Grove Ave, Tisbury, MA 02568
0.06
$1,678,300
6
3
2,022
Off Market
564 Main St, Tisbury, MA 02568
0.06
$1,080,700
2
2
1,148
Off Market
15 Holly Tree Ln, Tisbury, MA 02568
0.07
$1,855,100
5
3
2,076
Off Market

Price and Tax history

DateEventPrice
Sep 11, 2026
Source: MLS PIN #73480830
Pending
$1,999,000
Aug 25, 2026
Source: LINK #43291
Contingent
$1,999,000
Jul 1, 2026
Source: LINK #43291
PendingToActive
$1,999,000
Jun 26, 2026
Source: MLS PIN #73516062
Pending
$1,999,000
Jun 11, 2026
Source: LINK #43291
Contingent
$1,999,000

LGBTQ Local Legal Protections

Alyssa M Halisky, Wallace & Co. Sotheby's International Realty
Agent Phone: (508) 525-2584
All data relating to real estate for sale on this page comes from the Broker Reciprocity (BR) of the Cape Cod & Islands Multiple Listing Service, Inc. Detailed information about real estate listings held by brokerage firms other than CC&I Assoc. of REALTORS®, Inc. includes the name of the listing company. Neither the listing company nor CC&I Assoc. of REALTORS®, Inc. shall be responsible for any typographical errors, misinformation, misprints and shall be held totally harmless. The Broker providing this data believes it to be correct, but advises interested parties to confirm any item before relying on it in a purchase decision. This site was last updated 2026-09-29 12:06:14 PDT. All properties are subject to prior sale, changes, or withdrawal. Copyright 2026© Cape Cod & Islands Multiple Listing Service, Inc. All rights reserved.

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Frequently asked questions about 5 Pine Tree Lane

  • What is the estimated monthly payment for 5 Pine Tree Lane?
    Based on a $1,999,000 list price with 20% down at today's rates, the estimated monthly payment for 5 Pine Tree Lane in Tisbury, MA is approximately $12,268 (about $11,360 principal & interest, $833 property taxes, and $75 homeowner's insurance). This is an estimate. Actual payment depends on your loan terms.
  • What do residents say about Tisbury?
    Residents describe Tisbury, MA as well-kept, walkable to grocery stores, and quiet. See homes for sale in Tisbury, MA.
  • What are the closest schools to 5 Pine Tree Lane?
    The closest schools to 5 Pine Tree Lane in Tisbury, MA are Martha's Vineyard Regional High School (rated 6/10), Tisbury Elementary School (Pre-K/Middle, rated 4/10).
  • What is 5 Pine Tree Lane estimated to be worth?
    Trulia's estimated value for 5 Pine Tree Lane in Tisbury, MA is $1,877,100.
  • Does 5 Pine Tree Lane have air conditioning?
    Yes, 5 Pine Tree Lane in Tisbury, MA has air conditioning.
  • Does 5 Pine Tree Lane have laundry facilities?
    Yes, 5 Pine Tree Lane in Tisbury, MA has laundry facilities.
5 Pine Tree Lane, 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 CCIMLS on Jul 21, 2026. The MLS # for this home is MLS# 22603526.