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 afternoons in the dappled shade. A charming one-bedroom guest cottage sits tucked away from the main house, offering flexibility for guests, work-from-home, or rental income. This home has long been cherished by artists, collectors, and careful stewards—each adding their layer to the property’s quiet patina. Just a short stroll to the ferry, shops, restaurants, library, and beach, 139 Main Street is a rare find: a truly in-town retreat that feels a world apart. This expansive main house offers flexible living with six rooms currently used as bedrooms, including a separate guest suite. The property has a 5-bedroom septic system per Title 5.
For sale
$3,750,000
139 Main St, Tisbury, MA 02568
5beds
4,372sqft
Single Family Residence
Built in 1840
0.54 Acres Lot
$3,399,300 Zestimate®
$858/sqft
$-- HOA
What's special
Single half-acre parcelWelcoming vestibuleCustom cabinetryRich woodworkOversized windowsGenerously proportioned roomsStone countertops
- 43 days |
- 472 |
- 37 |
Zillow last checked:
Listing updated:
Listed by:
Leslie C. Floyd 508-221-4643,
Portfolio Properties
Source: LINK,MLS#: 44486
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Facts & features
Interior
Bedrooms & bathrooms
- Bedrooms: 5
- Bathrooms: 7
- Full bathrooms: 6
- 1/2 bathrooms: 1
Heating
- Heat Pump
Appliances
- Included: Stove: Viking, Washer: Yes
Features
- Ins, Irr, MiniSplit, OSh, Floor 1: Gracious living with stunning stone fireplace and dining room with original built-in cupboard and wood plank floors, renovated kitchen with custom cabinetry and stone countertops, large porch, office/den, and half bath. Large windows throughout provide abundant natural light., Floor 2: Primary suite with updated bath and garden views, four additional bedrooms-two with baths ensuite, a full shared hall bath, and two cozy sitting nooks—all filled with period charm and original detailing., Floor 3: Finished attic space with full bath, and expansive mahogany deck offering flexible use as guest rooms, office, or creative studio. Bright and airy with dormer windows and tucked-away charm. One room boasts a fireplace.
- Flooring: Hardwood and tile
- Basement: Unfinished basement with interior access and exterior walk in access ideal for outdoor furniture, bicycle and boat storage. Houses updated systems and utilities.
- Fireplace features: 2 Wood burning
Interior area
- Total structure area: 4,372
- Total interior livable area: 4,372 sqft
Property
Parking
- Parking features: Ample Off Street Parking
Features
- Exterior features: WViews, Deck, Porch, PubBch, Patio
- Has view: Yes
- View description: Harbor, Twn
- Has water view: Yes
- Water view: Harbor
- Frontage type: None
Lot
- Size: 0.54 Acres
- Features: Expansive Yard
Details
- Additional structures: Detached 1-bedroom, 1-bath guest cottage offers privacy and flexibility for guests, work-from-home, or rental income.
- Parcel number: TISBM0006CB00000L0301
- Zoning: R25
Construction
Type & style
- Home type: SingleFamily
- Property subtype: Single Family Residence
Materials
- Foundation: Stone / Brick / Concrete
Condition
- Year built: 1840
- Major remodel year: 2017
Utilities & green energy
- Sewer: Septic Tank
- Water: Town
- Utilities for property: Cbl
Community & HOA
Location
- Region: Tisbury
Financial & listing details
- Price per square foot: $858/sqft
- Tax assessed value: $2,679,100
- Annual tax amount: $21,065
- Date on market: 5/15/2026
- Listing agreement: E
Estimated market value
$3,399,300
$3.23M - $3.57M
$7,564/mo
Price history
| Date | Event | Price |
|---|---|---|
| 5/14/2026 | Listed for sale | $3,750,000$858/sqft |
Source:  CCIMLS #22602196 Report a problem | ||
| 1/2/2026 | Listing removed | $3,750,000$858/sqft |
Source: Martha's Vineyard MLS #32500243 Report a problem | ||
| 8/26/2025 | Price change | $3,750,000-5.1%$858/sqft |
Source: Martha's Vineyard MLS #32500243 Report a problem | ||
| 7/17/2025 | Listed for sale | $3,950,000+125.7%$903/sqft |
Source: LINK #43531 Report a problem | ||
| 3/24/2021 | Listing removed | -- |
Source: Owner Report a problem | ||
| 11/21/2008 | Listing removed | $1,750,000$400/sqft |
Source: Owner Report a problem | ||
| 8/1/2008 | Price change | $1,750,000+6.1%$400/sqft |
Source: Owner Report a problem | ||
| 6/25/2008 | Price change | $1,650,000-5.7%$377/sqft |
Source: Owner Report a problem | ||
| 5/9/2008 | Price change | $1,750,000+99900%$400/sqft |
Source: Owner Report a problem | ||
| 2/26/2008 | Listed for sale | $1,750-99.6% |
Source: Owner Report a problem | ||
| 8/25/1993 | Sold | $393,000$90/sqft |
Source: Public Record Report a problem | ||
Public tax history
| Year | Property taxes | Tax assessment |
|---|---|---|
| 2025 | $20,281 -3.7% | $2,679,100 +1.5% |
| 2024 | $21,064 +17.4% | $2,639,600 +7.7% |
| 2023 | $17,947 +10.9% | $2,451,800 +31.8% |
| 2022 | $16,189 -7.2% | $1,860,817 -2.2% |
| 2021 | $17,450 -5.1% | $1,902,900 -3.5% |
| 2020 | $18,390 +1.9% | $1,971,100 +0.2% |
| 2019 | $18,039 +23.1% | $1,967,200 +26.9% |
| 2018 | $14,654 -10.2% | $1,550,700 -13.5% |
| 2017 | $16,323 +31.4% | $1,791,800 +32.1% |
| 2016 | $12,426 -18.1% | $1,356,500 -20.2% |
| 2015 | $15,169 +31.5% | $1,700,600 +23.7% |
| 2014 | $11,533 +7.4% | $1,374,600 +8.5% |
| 2013 | $10,739 +0.8% | $1,266,400 -4.7% |
| 2012 | $10,649 +15.4% | $1,329,500 +8.3% |
| 2011 | $9,231 -0.4% | $1,227,500 -13% |
| 2010 | $9,272 +9.5% | $1,411,300 -0.3% |
| 2009 | $8,469 +7.9% | $1,416,200 -1% |
| 2008 | $7,851 -0.3% | $1,430,100 +2.3% |
| 2007 | $7,871 +11.9% | $1,398,000 +3.4% |
| 2006 | $7,032 -2.7% | $1,352,300 +9.7% |
| 2005 | $7,227 +24.1% | $1,233,200 +71.4% |
| 2004 | $5,822 +4.7% | $719,600 |
| 2003 | $5,563 +5.6% | $719,600 |
| 2002 | $5,267 -2.5% | $719,600 +78.1% |
| 2000 | $5,401 | $404,000 |
Find assessor info on the county website
Monthly payment
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Climate risks
Neighborhood: 02568
Nearby schools
GreatSchools rating
- 4/10Tisbury Elementary SchoolGrades: PK-8Distance: 0.5 mi
- 6/10Martha's Vineyard Regional High SchoolGrades: 9-12Distance: 2.8 mi
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- Massachusetts
- Dukes County
- Tisbury
- 02568
- 139 Main St
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