$3,950,000

139 Main St Vineyard Haven, MA 02568

Vineyard Haven Neighborhood

Estimated payment $25,829/month

Total Views 176
5 Beds
7 Baths
4,372 Sq Ft
$903 Price per Sq Ft

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 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.

Listing Agent

Leslie C. Floyd

Portfolio Real Estate, Inc. Listed on: 07/17/2025

Map

Home Details

Home Type

Single Family

Year Built

1840

Lot Details

0

Listing Details

  • Property Sub Type: Single Family Residence
  • Property Type: Residential
  • Co List Office Mls Id: 1010
  • Special Features: None
  • Year Built: 1840

Interior Features

  • Appliances: Stove: Viking, Washer: Yes
  • Has Basement: Unfinished basement with interior access and exterior walk in access ideal for outdoor furniture, bicycle and boat storage. Houses updated systems and utilities.
  • Full Bathrooms: 6
  • Half Bathrooms: 1
  • Total Bedrooms: 5
  • Fireplace Features: 2 Wood burning
  • Interior Amenities: 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.
  • Total Bedrooms: 14

Exterior Features

  • Pool Private: No
  • Foundation Details: Stone / Brick / Concrete
  • Other Structures: Detached 1-bedroom, 1-bath guest cottage offers privacy and flexibility for guests, work-from-home, or rental income.

Garage/Parking

  • Parking Features: Ample Off Street Parking

Utilities

  • Sewer: Septic Tank
  • Utilities: Cbl
  • Water Source: Town

Lot Info

  • Lot Size Sq Ft: 23565
  • Land Lease Expiration Date: 2026-06-11
  • Zoning: R25

Multi Family

  • Number Of Units Furnished: Partially

Tax Info

  • Tax Annual Amount: 21065
  • Tax Lot: 30 & 30.1
  • Tax Map Number: 6C
  • Tax Other Annual Assessment Amount: 1481100
  • Tax Year: 2025

Range of Values:

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Home Values in the Area

Source: Public Records

Average Home Value in this Area

Source: Public Records

Property History

Date Event Price Change Sq Ft Price
07/17/2025 07/17/25 For Sale $3,950,000 -- $903 / Sq Ft
Source: LINK (Vineyard)

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Source: LINK (Vineyard)

MLS Number: 43531

APN: TISB M:0006C B:00000 L:030.1

Massachusetts Dukes County Vineyard Haven 02568 Vineyard Haven

139 Main St, Vineyard Haven, MA

This home is located at 139 Main St, Vineyard Haven, MA 02568 and is currently priced at $3,950,000, approximately $903 per square foot. This property was built in 1840. 139 Main St is a home located in Dukes County with nearby schools including Tisbury Elementary School, Martha's Vineyard Regional High School, and Martha's Vineyard Charter School.

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Nearby Homes
Listing Agent
Leslie C. Floyd
Portfolio Real Estate, Inc.