LevelSecond
5 Pine Tree Lane, Tisbury MA 02568
Tisbury, MA 02568 • Vineyard Haven
$1,999,000
Est. $11,134/month
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About this home
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.
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Recently Sold Nearby
Property History
Property Timeline
Listed for Sale
Feb 27, 2026
$1,999,000
Original listing
Agent: Alyssa Halisky
Office: Wallace & Co. Sotheby's International Realty
| Date | Event | Price | Change | $/sqft | Details |
|---|---|---|---|---|---|
| 02/27/2026 | 🏠 Listed for Sale | $1,999,000 | - | - | Original listing |
Tax History
| Year | Taxes | Assessment |
|---|---|---|
| 2026 | $9,913 | $1,336,000 |
Financial Details
Annual Property Tax
$9,913
Tax Year 2026
Assessed Value
$1,336,000
Facts & Features
Central AC
Home Facts
Type
Residential
Style
Single Family Residence
Year Built
1927
Living Area
2,730 sq ft
Lot Size
0.18 acres
Bedrooms
4
Full Baths
3
Total Rooms
11
Interior
Heating
Central, Forced Air
Cooling
Central Air
Flooring
Wood, Tile
Appliances
Tankless Water Heater, Range, Dishwasher, Refrigerator, Washer, Dryer
Fireplace
Living Room
Fireplaces
1
Basement
None
Laundry
Second Floor
Features
None
Exterior
Construction
Frame
Architecture
Colonial Revival
Roof
Shingle
Features
Porch, Deck - Wood, Professional Landscaping, Sprinkler System, Outdoor Shower
Pool
None
Spa
None
Fencing
None
Patio/Porch
Porch, Deck - Wood
Parking
Features
Driveway, Stone/gravel
Total Spaces
3
Utilities
Electric
200+ Amp Service
Water
Public
Sewer
Private Sewer
Gas
None
Other
None
Financial
Annual Tax
$9,913
Assessed Value
$1,336,000
HOA & Community
Fee Includes
None
Amenities
None
Optional Fee Includes
None
MA Disclosures
Seller Disclosures
None
Additional Details
Possession
None
Accepted Financing
None
Structure Type
[]
Sq Ft Source
Measured
Documents
None
County
Dukes
Total market time (incl. prior listings)
147 days
Property Overview
Property Type
Single Family Residence
Listing Type
For Sale
Year Built
1927
Bedrooms
4
Full Bathrooms
3
Living Area
2,730 sq ft
Total Rooms
11
Floor Layout
Interactive room guide
Floor Layout
Finished Area
1,976 sq ft above grade
754 sq ft below grade
LevelSecond
LevelSecond
LevelSecond
FeaturesBathroom - Full, Walk-In Closet(s)
LevelSecond
LevelFirst
FeaturesFlooring - Hardwood, Slider
LevelFirst
FeaturesCountertops - Stone/Granite/Solid, Kitchen Island, Stainless Steel Appliances
LevelFirst
LevelFirst
LevelBasement
Display Options
Outdoor Areas
Patio & porchPorch, Deck - Wood
Room Markers
BABathroom (4)
BRBedroom (5)
DDining (1)
KKitchen (1)
LLiving (2)
OOffice (1)
Conceptual diagram based on MLS room data. It is not to scale and is not a substitute for architectural plans or on-site measurements.
Interior Features
Flooring:
Wood, Tile
Appliances:
Tankless Water Heater, Range, Dishwasher, Refrigerator, Washer, Dryer
Interior Features:
Windows:
Insulated Windows
Basement:
Laundry:
Second Floor
Security:
Construction & Materials
Style:
Colonial Revival
Year Built:
1927
Structure Type:
Exterior Materials:
Frame
Roof:
Shingle
Foundation:
Concrete Perimeter
Heating, Cooling & Utilities
Heating:
Central, Forced Air
Cooling:
Central Air
Hot Water:
Water Source:
Public
Sewer:
Private Sewer
Energy Features:
Exterior & Lot
Exterior Features:
Porch, Deck - Wood, Professional Landscaping, Sprinkler System, Outdoor Shower
Patio & Porch:
Porch, Deck - Wood
Fencing:
Other Structures:
Lot Features:
Corner Lot
Road Surface:
Parking & Garage
Total Parking Spaces:
3
Parking Features:
Driveway, Stone/Gravel
Special Features
Fireplaces:
1
Fireplace Type:
Living Room
Community Amenities:
Public Transportation, Shopping, Walk/Jog Trails, Golf, Bike Path, Conservation Area, Public School
Nearby Schools
School District
Martha's Vineyard School District local
School Safety
2024-25
5.0%
Above Average
5.0%
Suspensions
1.3%
In-School
0.5% below state avg
Elementary Schools
3 schools
Vineyard Montessori School
0.6 mi
Grades PK-08
C+
Tisbury Elementary School
1.3 mi
|
#239 of 352
|
Score: 37.3
Dropped 104 spots from last year
-20.9 below state avg
312 students
Diverse
Diverse Student Body
Grades PK-08
A-
Oak Bluffs Elementary School
2.3 mi
|
#105 of 352
|
Score: 49.0
Improved 16 spots from last year
-9.2 below state avg
402 students
Diverse
Grades PK-08
High Schools
1 school
A-
Martha's Vineyard Regional High School
3.6 mi
|
#95 of 346
|
Score: 60.5
Improved 49 spots from last year
+2.3 above state avg
744 students
Diverse
19 sports
• 1,209 athletes
Strong AP Program
Rising School
Career Tech Programs
College Ready Curriculum
Grades 09-12
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Monthly Payment Breakdown
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Property Tax
$826
Homeowners Insurance
$200
PMI (if <20% down)
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Loan Summary
Total of 360 payments
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Payment Over Time
Year 1
95% Interest
Year 15
50/50
Year 30
95% Principal
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Location
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Neighborhood
Vineyard Haven
5 Pine Tree Lane, Tisbury MA 02568
Tisbury, MA 02568
Listing Information
Listing Agent
Alyssa Halisky
Listing Office
Wallace & Co. Sotheby's International Realty
Office Phone
508-627-3313
Agent MLS ID
CN262458
Office MLS ID
AN9542
Listing Data Updated
Jul 24, 2026 3:05 AM EDT
Listing information is deemed reliable but not guaranteed. Data provided by MLS Property Information Network, Inc. All information should be independently verified.
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