680 Falmouth Rd.
Rte. 28 Mashpee, MA 02649

Phone:

508-989-1943


$3,750,000
139 Main Street
Vineyard Haven, MA 02568
MLS# 22602196
5 beds  |  7 baths  |  4372 sqft


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Property Description
Nestled just two blocks from Vineyard Haven's working harbor, 139 Main Street is a quietly grand in-town property with the feel of a private estate. Once two separate addresses--now gracefully combined into a single half-acre parcel--this home offers rare space, privacy, and timeless character in one of the island's most approachable villages. From the moment you step through the welcoming vestibule, it's clear this is a home with stories to tell. Wood plank floors, rich woodwork, and generously proportioned rooms speak to its heritage, while thoughtful updates have introduced an easy, understated luxury throughout. The kitchen has been beautifully remodeled with custom cabinetry and stone countertops. Light pours through oversized windows into gracious living and dining spaces, with a fireplace adding warmth and character to the living room. Upstairs, the primary suite offers garden views and a peaceful retreat, while guest bedrooms retain period charm with airy, sunlit appeal. Outside, the grounds feel secluded and mature--a private world behind an original wrought iron gate. Paths wind through perennial gardens and wide lawns, while a porch and flagstone patio invite lingering

Details
Maps
Documents
Contract Info
List Price/SqFt: 857.73
Status: Active
Original List Price: 3950000
List Price: $3,750,000
Current Price: $3,750,000
List Date: 2025-07-17
Legal and Taxes
Town: Vineyard Haven
Village: Vineyard Haven
Estimated Annual Taxes: 20280
Building Assessments: 1035600
Other Assessments: 0
Total Assessment: 2516700
Title Reference - Book: 1244
Title Reference - Page: 0236
Underground Fuel Tank: Unknown
Flood Ins Required: No
Lead Base Paint: Unknown
Asbestos: Unknown
Elevation Certificate: No
Mass Use Code: 109 - Residential, multiple houses
Street #: 139
Street Name: Main
Street Suffix: Street
County: Dukes
State: MA
Zip Code: 02568
Tax ID: TISB M:0006C B:00000 L:030.1
Tax Year: 2025
General Property Info
Region: Dukes County
School District: Martha's Vineyard
Zoning: R25
Property Sub-Type: Single Family Residence
Renovated: Yes
Year Renovated: 2023
Stories: 3
Total Rooms: 11
Field Card SqFt: 0
Additional Finished Space: 4372
Additional SqFt Source: Tax Bill
Basement: Yes
Baths - Half: 1
Association: No
Private Dock: No
Private Pool: No
Lot Size SqFt: 23522
Leased Land: No
Lot Size Source: Field Card
Acres: 0.54
Garage: No
# of Parking Spaces: 4
Year Round: Yes
Separate Living Qtrs: Yes
Golf Course Front: No
Golf Course View: No
Waterfront: No
Waterview: Yes
Water Body View: Vineyard Sound
Waterview Type: Ocean
Miles to Beach: 0 - .1
Fireplace: Yes
# Fireplaces: 2
Property Includes Recording Devices: No
Year Built: 1840
Total Finished Space: 4372
Bedrooms - Total: 5
Baths - Full: 6
Baths - Total: 7
Remarks & Misc
Public Remarks: Nestled just two blocks from Vineyard Haven's working harbor, 139 Main Street is a quietly grand in-town property with the feel of a private estate. Once two separate addresses--now gracefully combined into a single half-acre parcel--this home offers rare space, privacy, and timeless character in one of the island's most approachable villages. From the moment you step through the welcoming vestibule, it's clear this is a home with stories to tell. Wood plank floors, rich woodwork, and generously proportioned rooms speak to its heritage, while thoughtful updates have introduced an easy, understated luxury throughout. The kitchen has been beautifully remodeled with custom cabinetry and stone countertops. Light pours through oversized windows into gracious living and dining spaces, with a fireplace adding warmth and character to the living room. Upstairs, the primary suite offers garden views and a peaceful retreat, while guest bedrooms retain period charm with airy, sunlit appeal. Outside, the grounds feel secluded and mature--a private world behind an original wrought iron gate. Paths wind through perennial gardens and wide lawns, while a porch and flagstone patio invite lingering
Directions to Property: Main Street Vineyard Haven. Property is located on the right just after Owen Park.
Street Description
Paved: 1
Special Listing Cond
None: 1
Lot Features
Gentle Sloping: 1
Year Built Desc
Actual: 1
Basement Description
Interior Access: 1
Walk-Out Access: 1
Parking Features
Driveway: 1
Off Street: 1
Waterview Direction
North: 1
Architectural Style
Antique: 1
Tudor: 1
Baths Per Level
Baths - Level 1: 1
Baths - Level 2: 4
Baths - Level 3: 1
Sep Living Qtrs Info
Baths - Full: 1
Beds: 1
Baths - Total: 1
Foundation Details
Concrete Perimeter: 1
Poured: 1
Slab: 1
Stone: 1
Convenient To
Conservation Area: 1
Golf Course: 1
In Town Location: 1
Medical Facility: 1
Public Tennis: 1
School: 1
Shopping: 1
Floors
Hardwood: 1
Tile: 1
Sewer
Septic Tank: Title V Grade Level
Separate Living Qtrs
Detached: 1
Fencing
Fenced: 1
Partial: 1
Roof Description
Asphalt: 1
Pitched: 1
Shingle: 1
Siding Description
Stucco: 1
Primary Bedroom
Primary Bedroom: 1
Primary Bedroom Level: Second Floor
Ceiling Fan: 1
Flooring: Wood
Private Full Bath: 1
Heating
Forced Air: 1
Heat Pump: 1
Bedroom 2
Bedroom 2: 1
Bedroom 2 Level: Second Floor
Ceiling Fan: 1
Closet: 1
Flooring: Wood
Office/Sitting Area: 1
Shared Full Bath: 1
Cooling
Central Air: 1
Bedroom 3
Bedroom 3: 1
Bedroom 3 Level: Second Floor
Ceiling Fan: 1
Flooring: Wood
Office/Sitting Area: 1
Shared Full Bath: 1
Fuel Type
Electric: 1
Propane: 1
Solar: 1
Bedroom 4
Bedroom 4: 1
Bedroom 4 Level: Second Floor
Closet: 1
Flooring: Wood
Private Full Bath: 1
Water
Public: 1
Hot Water
Water Heater: 1
Foyer
Foyer: 1
Foyer Level: First Floor
Closet: 1
Flooring: Wood
Hot Water Source
Electric: 1
Living/Dining Combo
No: 1
Living Room
Living Room: 1
Living Room Level: First Floor
Beamed Ceilings: 1
Fireplace: Wood Burning
Dining Room
Dining Room: 1
Dining Room Level: Second Floor
Bay/Bow Windows: 1
Built-Ins: 1
Kitchen
Eat-in Kitchen: 1
Kitchen: 1
Kitchen Level: First Floor
Countertops: Other
Recessed Lighting: 1
Other Room 1
Room Type: Den
Level: First Floor
Exterior Features
Garden: 1
Outdoor Shower: 1
Private Yard: 1
Underground Sprinkler System: 1
Appliances
Dishwasher: 1
Electric Dryer: 1
Gas Range: 1
Microwave: 1
Range Hood: 1
Refrigerator: 1
Washer: 1
Interior Features
Attic Storage: 1
Linen Closet: 1
Patio And Porch Features
Patio: 1
Porch: 1
DPR Eligibility
DPR Eligible: No
Property Features
Street Description: Paved
Special Listing Cond: None
Architectural Style: Antique; Tudor
Year Built Desc: Actual
Basement Description: Interior Access; Walk-Out Access
Foundation Details: Concrete Perimeter; Poured; Slab; Stone
Lot Features: Gentle Sloping
Parking Features: Driveway; Off Street
Separate Living Qtrs: Detached
Convenient To: Conservation Area; Golf Course; In Town Location; Medical Facility; Public Tennis; School; Shopping
Waterview Direction: North
Primary Bedroom: Primary Bedroom; Ceiling Fan; Private Full Bath
Bedroom 2: Bedroom 2; Ceiling Fan; Closet; Office/Sitting Area; Shared Full Bath
Bedroom 3: Bedroom 3; Ceiling Fan; Office/Sitting Area; Shared Full Bath
Bedroom 4: Bedroom 4; Closet; Private Full Bath
Foyer: Foyer; Closet
Living Room: Living Room; Beamed Ceilings
Dining Room: Dining Room; Bay/Bow Windows; Built-Ins
Kitchen: Kitchen; Eat-in Kitchen; Recessed Lighting
Appliances: Dishwasher; Electric Dryer; Gas Range; Microwave; Range Hood; Refrigerator; Washer
Floors: Hardwood; Tile
Interior Features: Attic Storage; Linen Closet
Patio And Porch Features: Patio; Porch
Exterior Features: Garden; Outdoor Shower; Private Yard; Underground Sprinkler System
Fencing: Fenced; Partial
Roof Description: Asphalt; Pitched; Shingle
Siding Description: Stucco
Heating: Forced Air; Heat Pump
Cooling: Central Air
Fuel Type: Electric; Propane; Solar
Water: Public
Hot Water: Water Heater
Hot Water Source: Electric

IDX
Listing Office: Portfolio Properties
Listing Agent: Leslie C Floyd

Last Updated: May - 18 - 2026

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