Date
Details
Price
Change
Source
7/17/2025
Listed
$3,750,000
—
MLS
Disclaimer: Historical sales information is derived from public records provided by the county offices. Information is not guaranteed and should be independently verified.
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1/55
$3,750,000
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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
Full Property Details
Full Property Details for 139 Main St
General
- Price: $3,750,000
- Taxes: $20,280 (2025)
- Status: Active
- Type: Single Family
- Source: CCI
- MLS ID: 22602196
- Updated: 5/14/2026
- Added to Site: 304 day(s) ago
Interior
- Number of Rooms: 11
- Interior Features: Linen Closet
- Fireplace: Yes
- Number of Fireplaces: 2
- Fireplace(s): Wood Burning
- Appliances: Dishwasher, Washer, Range Hood, Refrigerator, Gas Range, Microwave, Electric Dryer, Electric Water Heater
- Flooring: Hardwood, Tile
Rooms
Bathrooms
- Total Bathrooms: 7
- Full Bathrooms: 6
- Half Bathrooms: 1
- Primary Bathroom: Private Full Bath
Bedrooms
- Total Bedrooms: 5
- Primary Bedroom: Ceiling Fan(s), Second
- Bedroom 3: Second Level
- Bedroom 4: Second Level
- Bedroom 5: Second Level
Other Rooms
- Living Room: First Level
- Kitchen: Kitchen, Recessed Lighting, First Level
- Dining Room: Built-in Features, Dining Room, Second Level
Exterior
- Exterior Features: Outdoor Shower, Garden
- Deck/Patio: Patio, Porch
Parking
- Total Spaces: 4
Location
- County: Dukes
- Driving Directions: Main Street Vineyard Haven. Property is located on the right just after Owen Park.
Heating & Cooling
- Cooling Type: Central Air
Utilities
- Sewer: Septic Tank
Structural Information
- Architectural Style: Antique, Tudor
- Construction: Stucco
- Exterior Const.: Stucco
- Basement Desc.: Interior Entry
- Roof: Asphalt, Shingle, Pitched
- Stories/Levels: 3
- Square Feet: 4,372
- Sq. Ft. Source: Tax Bill
- Year Built: 1840
- Property Condition: Updated/Remodeled, Actual
Lot Features
- Lot Size (Acres): 0.54
- Lot Size (Sq. Ft.): 23,522
- Lot Size Source: Field Card
- Street/Road Desc.: Paved
- Zoning: R25
- Fencing (Description): Fenced, Partial
Water Features
- Water View: Yes
Financial Considerations
- Price Per Sq. Ft.: $857
- Assessment Amount: $2,516,700
- Land Assmt: $1,481,100
- Tax Amount: $20,280
- Tax Year: 2025
Disclosures and Reports
- Special Conditions: None
- Property ID: TISB M:0006C B:00000 L:030.1
Listed by Portfolio Properties, Leslie C Floyd
We Value Your Privacy
We Value Your Privacy
We Value Your Privacy
Listing agent
— 139 Main St —
Leslie C Floyd
Portfolio Properties
NMLS#: 1598647Get Pre-Approved Today
Schools
Schools serving 139 Main St
School Districts:Tisbury School District, Martha's Vineyard School District
| Name | Grades | Distance |
|---|---|---|
Tisbury Elementary School 40 West William Street, Tisbury, MA 02568 | PK-8 | 0.5 mi |
Marthas Vineyard Regional High School 100 Edgartown-Vineyard Haven R, Oak Bluffs, MA 02557 | 9-12 | 2.8 mi |
Disclaimer:
School attendance boundaries provided by ATTOM Data Solutions and are for reference only. Contact the school directly to verify enrollment eligibility.
Price & Sales History for 139 Main St
Tax History
Tax History for 139 Main St
Year
Property Taxes
Change
Tax Assessment
Change
2025
$20,281
-4%
$2,679,100
1%
2024
$21,064
17%
$2,639,600
8%
2023
$17,947
11%
$2,451,800
32%
2022
$16,189
-7%
$1,860,817
-2%
2021
$17,450
-5%
$1,902,900
-3%
2020
$18,390
2%
$1,971,100
—
2019
$18,039
23%
$1,967,200
27%
2018
$14,654
-10%
$1,550,700
-13%
2017
$16,323
31%
$1,791,800
32%
2016
$12,426
-18%
$1,356,500
-20%
2015
$15,169
32%
$1,700,600
24%
2014
$11,533
7%
$1,374,600
9%
2013
$10,739
—
$1,266,400
—
Disclaimer: Historical tax information is derived from public records provided by the county offices. Information is not guaranteed and should be independently verified.
Estimate the Cost
Estimate the Cost for 139 Main St
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- Single Family
- Active
- Updated 1 day ago
- 3Beds
- 4Total Baths
- 3,426Sq. Ft.
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- Single Family
- Active
- Updated 3 days ago
- 4Beds
- 5Total Baths
- 3,804Sq. Ft.
- Condo
- Active
- Updated 18 hours ago
- 2Beds
- 2Total Baths
- 1,144Sq. Ft.
- Single Family
- Active
- Updated 2 days ago
- 3Beds
- 2Total Baths
- 1,417Sq. Ft.
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- Single Family
- Active
- Updated 2 days ago
- 3Beds
- 1Total Bath
- 1,086Sq. Ft.
- Single Family
- Active
- Updated 1 day ago
- 3Beds
- 2Total Baths
- 1,763Sq. Ft.
- Single Family
- Active
- Updated 2 days ago
- 4Beds
- 2Total Baths
- 1,758Sq. Ft.
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- Single Family
- Closed
- Updated 7 days ago
- 4Beds
- 4Total Baths
- 3,327Sq. Ft.
139 Main Street, Tisbury, MA 02568 (MLS# 22602196) is a Single Family property with 5 bedrooms, 6 full bathrooms and 1 partial bathroom. 139 Main Street is currently listed for $3,750,000 and was received on July 17, 2025. Want to learn more about 139 Main Street? Do you have questions about finding other Single Family real estate for sale in Vineyard Haven? You can browse all Vineyard Haven real estate or contact a Coldwell Banker agent to request more information.