139 Main Street, Vineyard Haven, MA 02568
Local realty services provided by:Better Homes and Gardens Real Estate The Shanahan Group
139 Main Street,Vineyard Haven, MA 02568
$3,750,000
- 5 Beds
- 7 Baths
- 4,372 sq. ft.
- Single family
- Active
Listed by: leslie c floyd
Office: portfolio properties
MLS#:22602196
Source:CAPECOD
Price summary
- Price:$3,750,000
- Price per sq. ft.:$857.73
About this home
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...
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Home facts
- Year built:1840
- Listing ID #:22602196
- Added:1 day(s) ago
- Updated:May 14, 2026 at 07:36 PM
Rooms and interior
- Bedrooms:5
- Total bathrooms:7
- Rooms Total:11
- Basement Description:Interior Access, Walk-Out Access
- Living area:4,372 sq. ft.
Heating and cooling
- Cooling:Central Air
- Heating:Forced Air
Structure and exterior
- Year built:1840
- Building area:4,372 sq. ft.
- Lot area:0.54 Acres
- Lot Features:Gentle Sloping
- Construction Materials:Stucco
- Exterior Features:Garden, Outdoor Shower
Finances and disclosures
- Price:$3,750,000
- Price per sq. ft.:$857.73
- Tax amount:$20,280
Features and amenities
- Amenities:Linen Closet
Parking
- Parking description:Driveway, Off Street
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