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I'm Andrew Goldberg, a Boston real estate advisor specializing in first-time buyers across Greater Boston. I guide you A to Z—from first search to closing day.

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Commonwealth Standard Realty Advisors

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Equal Housing Opportunity. Information deemed reliable but not guaranteed.

  1. Home
  2. Listings
  3. 5 Pine Tree Lane, Tisbury, MA 02568
Active
179 Days on market
5 Pine Tree Lane Tisbury — Photo 1 of 24

5 Pine Tree Lane Tisbury — Photo 1 of 24

$1,999,000

5 Pine Tree Lane, Tisbury, MA 02568

Tisbury, MA 02568 — Vineyard Haven

Beds

4

Baths

3

SqFt

2,730

Style

Single Family

Built

1927

Blending 1920s charm with modern luxury, this beautifully renovated home is tucked into the coveted West Chop area of Vineyard Haven. Just steps from a neighborhood beach on the pristine shores of Vineyard Sound, it offers an elegant mix of historic character and contemporary comfort. A thoughtfully designed layout features generous living spaces centered around a chef’s kitchen with custom cabinetry, high-end appliances, and refined finishes. Open living and dining areas flow seamlessly, enhanced by updated systems and central air. Upstairs, the serene primary suite includes a spa-like tile bath with soaking tub, while two guest bedrooms share a stylish full bath with laundry. Nautical details like a compass rose stained-glass window add charm. The finished lower level provides a large additional bedroom and flexible living space. Outside, a mahogany deck overlooks the newly landscaped yard with outdoor shower and entertaining areas. Just minutes from downtown Vineyard Haven.

Immersive Experience

Virtual Tour

Market Value Analysis

This Property
Size (SqFt) →Price →
This Property$732/sqft
Local Avg (Tisbury)$1250/sqft
41% BelowMarket Average

* Analysis is based on 20 actively listed and recently sold comparable properties strictly within Tisbury, MA.

Property Details

Financials

Original Price$1,999,000
Annual Taxes$9,913.12

Parking

Garage0
Off-Street3

Interior Specifications

Total Rooms11
Fireplaces1
FlooringWood, Tile
BasementNone

Climate & Utilities

HeatingCentral, Forced Air
CoolingCentral Air
WaterPublic
SewerPrivate Sewer

Building & Exterior

ConstructionFrame
RoofShingle
FoundationConcrete Perimeter
ZoningR25

Property & Lot

Acres0.18
SqFt Lot7,800
Lot FeaturesCorner Lot

Amenities & Appliances

Tankless Water Heater • Range • Dishwasher • Refrigerator • Washer • Dryer

Neighborhood

Public Transportation • Shopping • Walk/Jog Trails • Golf • Bike Path • Conservation Area

Geography

Floorplan Breakdown

Structural Layout

Second
Master BedroomBedroom 2Bedroom 3Bathroom 2Bathroom 3
First
Living RoomDining RoomKitchenBathroom 1
Basement
Bedroom 4
Living Room
Lvl First
Dining Room
Lvl First

Flooring - Hardwood, Slider

Kitchen
Lvl First

Countertops - Stone/Granite/Solid, Kitchen Island, Stainless Steel Appliances

Master Bedroom
Lvl Second

Bathroom - Full, Walk-In Closet(s)

Bedroom 2
Lvl Second
Bedroom 3
Lvl Second
Bedroom 4
Lvl Basement
Bathroom 1
Lvl First
Bathroom 2
Lvl Second
Bathroom 3
Lvl Second

Property History

Listed
$1,999,000

May 11, 2026

MLS® 73516062

Listed
$1,999,000

Feb 27, 2026

MLS® 73480830

Expired
$1,999,999

Dec 31, 2025

MLS® 73410635

Listed
$1,999,999

Jul 29, 2025

MLS® 73410635

Population

9,412

U.S. Census Bureau, ACS 2024 5-Year Estimates (B01003)

Median Household Income

$115K

U.S. Census Bureau, ACS 2024 5-Year Estimates (B19013)

Renter-Occupied Homes

21.5%

U.S. Census Bureau, ACS 2024 5-Year Estimates (B25003)

New Construction Permits — Dukes County

164 housing units permitted in the last 12 months (+80% vs the prior 12 months) — 35 in 5+ unit buildings

U.S. Census Bureau, Building Permits Survey (through Jun '26)

ADU Potential

Massachusetts allows one accessory dwelling unit by right in single-family zoning districts statewide (M.G.L. c. 40A §3; 760 CMR 71.00, effective Feb 2025). Estimated maximum ADU size for this property: 900 sq ft (the lesser of 900 sq ft or half the 2,730 sq ft principal dwelling). Lot size: 7,800 sq ft.

Based on listing data, which indicates the property type — not the zoning district. Local dimensional, septic (Title 5), and historic-district requirements still apply. Not legal advice — verify with the municipality.

Full Tisbury, MA market report ZIP 02568 market data
Listing Provided By

Listing Agent: Alyssa Halisky

Listing Office: Provided by MLS PIN

MLS® Number: 73480830

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