LevelSecond
5 Pine Tree Lane, Tisbury MA 02568
Tisbury, MA 02568 • Vineyard Haven
$1,999,000
Est. $11,134/month
Estimate assumptions
20% down, a 30-year loan at 6.5%, and $200/month estimated insurance.
Includes the supplied property-tax and HOA inputs; missing inputs contribute $0. HOA fees with an unspecified frequency are treated as monthly. PMI and closing costs are excluded.
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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
Market Insights
Property Timeline
Status: Active under contract
Aug 28, 2026
Active → Active Under Contract
Pending Sale
Aug 24, 2026
Offer accepted, sale pending
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 |
|---|---|---|---|---|---|
| 08/28/2026 | 📋 Status: Active under contract | - | - | - | Active → Active Under Contract |
| 08/24/2026 | ⏳ Pending Sale | - | - | - | Offer accepted, sale pending |
| 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
Lead Paint
None
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)
196 days
Property Overview
Property Type
Single Family Residence
Listing Type
Sale Pending
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
FeaturesCountertops - Stone/Granite/Solid, Kitchen Island, Stainless Steel Appliances
LevelFirst
LevelFirst
FeaturesFlooring - Hardwood, Slider
LevelFirst
LevelFirst
LevelBasement
Display Options
Outdoor Areas
Patio & porchPorch, Deck - Wood
Room Markers
OOffice (1)
KKitchen (1)
BRBedroom (5)
BABathroom (4)
DDining (1)
LLiving (2)
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 information not available for this location.
Monthly Payment Calculator
Monthly Payment
$0
Principal, interest, taxes & insurance
Loan Amount
$0
After down payment
Total Interest
$0
Over life of loan
Total Cost
$0
Including down payment
%
Down: $0
%
Monthly Payment Breakdown
Principal & Interest
$0
Property Tax
$826
Homeowners Insurance
$200
PMI (if <20% down)
$0
Loan Summary
Total of 360 payments
$0
Total principal paid
$0
Total interest paid
$0
Rate Impact
-0.5% Rate
$0/mo
Save $0/mo
Current Rate
$0/mo
+0.5% Rate
$0/mo
Cost $0/mo
Payment Over Time
Year 1
95% Interest
Year 15
50/50
Year 30
95% Principal
* Estimates only. Actual payments may vary. Consult with a lender for accurate figures.
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
Sep 11, 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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