139 Main Street

Print
Save

Vineyard Haven - 139 Main Street$3,750,000

ID: 43531 Owner: Vineyard Haven Captain's House LLC Available

Zip Code:: 02568
Property Type:: Single Family
Total Rooms:: 14
Total Bedrooms:: 5
Total Bathrooms:: 6 full, 1 half
Water Frontage:: None
Water Views:: Distant Harbor
Second Dwelling:: Existing
Zoning:: R25

Lot Size:: 0.54 acres
Total SqFt (ELA):: 4,372 sqft
Price/sqft:: $857.73
Year Built:: 1840 (ren. 2017 )
Water / Sewer:: Town / Septic
2025 Assessment:: $2,679,100
Land Assessment:: $1,481,100
Build Assessment:: $1,198,000
Estimated Taxes:: $21,065

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.

Primary Dwelling

Total Rooms:: 11
Bedrooms:: 4
Bathrooms:: 5 full, 1 half

Square Feet (ELA):: 3,881 sqft

Secondary Dwelling

Total Rooms:: 3
Bedrooms:: 1
Bathrooms:: 1

Square Feet (ELA):: 491 sqft

Seasonal Captain's Cottage Guest House with all necessary accoutrements for an enjoyable summer retreat. Full Kitchen, a Private deck and outdoor shower round out the charm and character of this wonderful hideaway.

First Floor

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.

Second Floor

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.

Third Floor

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.

Basement

Unfinished basement with interior access and exterior walk in access ideal for outdoor furniture, bicycle and boat storage. Houses updated systems and utilities.

Other Structures

Detached 1-bedroom, 1-bath guest cottage offers privacy and flexibility for guests, work-from-home, or rental income.

Building Information

Furnished:: Partially Furnished
First Floor Beds:: 0
Fireplaces:: 2 Wood burning
Floors:: Hardwood and tile
Heat:: Heat Pump

Foundation:: Stone / Brick / Concrete
Yard:: Expansive Yard
Parking Description:: Ample Off Street Parking
Other Buildings:: None
Lead Paint:: Unknown

Appliances

Stove:: Viking
Refrigerator:: Yes
Dishwasher:: Yes

Washer:: Yes
Dryer:: Yes
TV Service Type:: Cable

Outdoor/Recreation

Water Views, Deck, Porch, Beach Access - Public, Patio

Features

Insulation, Irrigation, Mini-Split Heat/AC, Outdoor Shower

Property / Parcel Information

Map:: 6C
Lot #:: 30 & 30.1
Plan:
Parcel:
Sub Area:: Downtown

Deed Ref:: Book 1244 Page 236
Fees:
Fee Frequency:
Fees Include:
Other Views:: Town

Directions / Comments

A private in-town sanctuary just two blocks from the ferry and harbor. Set on over half an acre, this thoughtfully updated Main Street property offers timeless charm, light-filled interiors, and beautifully landscaped grounds with a separate guest cottage. Thoughtfully updated with select new windows, updated systems, solar panels that partially offset electrical expense, and refreshed interior and exterior finishes. Directions: Main Street-Property is set back on the right, between Owen Park and Crocker Ave.