Historic Homes & Captain's Houses for Sale on Martha's Vineyard
Federal-era captain’s houses, Greek Revival farmhouses, and pre-1900 in-town homes. A finite inventory protected by historic-district review.
Historic homes for sale (built 1950 or earlier)
Historic Homes & Captain's Houses: A Finite, Protected Inventory
Edgartown has one of the largest concentrations of pre-1840 buildings in the United States. The whaling captains who built North Water Street, the Greek Revival farmhouses inland, the Federal-era homes along Main Street: this is housing stock that cannot be added to. The historic-district commissions will not let it be replicated, and the supply only goes one direction.
What counts as historic on Martha's Vineyard
The working definition: a home built before 1900, with the original structure substantially intact, located either inside a designated historic district or with state and National Register recognition. The Edgartown Historic District is the largest and the most strictly reviewed. Vineyard Haven has the William Street Historic District. Aquinnah, Chilmark, and West Tisbury each have smaller historic clusters tied to early farms and the lighthouses.
A captain's house is the specific type most buyers ask for: a two-story, gabled, symmetrical home, often with a widow's walk or cupola, built between roughly 1800 and 1870 with whaling money. The biggest are on North Water Street in Edgartown. Smaller versions sit on Cooke, South Summer, and Pent Lane, plus the side streets in Vineyard Haven.
What it means to own one
Inside the Edgartown Historic District, any exterior change visible from a public way requires a Certificate of Appropriateness from the Historic District Commission. Window replacements, roof color, paint color, fence height, even mailbox placement get reviewed. Most owners settle into the rhythm of it within a year. The trade is a guaranteed long-term value floor: nothing across the street will be torn down for a new modern build.
Interior work is less restricted, but in practice many owners keep the period detailing. The wide-plank pine floors, the original moldings, the small-pane windows, the working fireplaces. The Vineyard's best preservation craftspeople work almost exclusively in this housing stock.
How the market values them
Historic homes on the Vineyard trade at a premium when they have been carefully restored, kept their original layout in the public rooms, and have either a notable provenance or a North Water Street, Main Street, or Water Street Vineyard Haven address. The premium narrows or disappears for homes that have been over-renovated, where original detailing has been lost. The serious buyers in this market notice every choice.
Historic Homes & Captain's Houses on Martha's Vineyard: four angles.
The category breaks down into a handful of distinct neighborhoods, each with its own pricing, considerations, and buyer in mind. Here are the four angles we see most often.
The North Water Street archetype, c. 1820 to 1870.
The two-story symmetric Federal or Greek Revival captain's house with a widow's walk, six-over-six windows, a fanlight over the front door, and a deep linear lot running back from the street. North Water Street in Edgartown has the densest inventory anywhere on the island. Most are private residences. A few have been kept as boutique inns. When one turns over it is the Vineyard headline of the season.
- What's nearby
- Edgartown North Water Street
- South Water Street
- Main Street Edgartown
The inland sister of the captain's house.
Built by the families who farmed the inland Vineyard from the 1830s through the 1880s, these homes sit on stone foundations, with the same symmetric facade and gable end facing the road. West Tisbury, Chilmark, and the inland parts of Tisbury have most of them. They typically come with two to twenty acres, original outbuildings, and a stone wall along the road.
- What's nearby
- West Tisbury Village
- North Road Chilmark
- Middle Road farmsteads
A second, quieter historic district.
The William Street Historic District in Vineyard Haven runs from the harbor uphill to Owen Park. Smaller, denser captain's houses and merchant homes from the same whaling era, with the bonus of walking to the year-round Steamship Authority ferry. Often overlooked by buyers who fixate on Edgartown, and often priced accordingly.
- What's nearby
- William Street
- Owen Park
- Vineyard Haven Harbor
The keepers' houses, the lifesaving stations, the very early stock.
A small inventory of homes tied to the Vineyard's lighthouses (East Chop, West Chop, Edgartown, Gay Head) and the U.S. Lifesaving Service stations built between 1875 and 1915. These are the most singular properties on the island when they come up. Most are in private hands and stay there for generations.
- What's nearby
- East Chop Lighthouse area
- West Chop Lighthouse
- Aquinnah Cliffs
Historic-home market at a glance.
Buildings in the Edgartown Historic District alone, with hundreds more across Vineyard Haven's William Street district, the Chilmark farms, and the early stock in West Tisbury. Historic MV homes hold value through cycles because the rental selection is fixed, the new-build alternatives are explicitly restricted, and demand from buyers seeking provenance is steady.
What the historic market is doing
What ownership looks like
Questions buyers and renters ask about Historic Homes & Captain's Houses.
Answers our team gives most often when people are evaluating this corner of the Martha's Vineyard market.
What is the oldest house on Martha's Vineyard?
The Vincent House in Edgartown, built around 1672 and now part of the Martha's Vineyard Museum, is generally cited as the oldest surviving structure on the island. Several other late-1600s and early-1700s homes survive in private hands across Edgartown and West Tisbury, but they are not typically marketed publicly.
What is the Edgartown Historic District?
The Edgartown Historic District covers most of the downtown peninsula, including North Water Street, South Water Street, Main Street, Summer Street, and the side streets between them. Any change to the exterior of a building inside the district that is visible from a public way requires a Certificate of Appropriateness from the Historic District Commission. Window styles, paint colors, fence heights, roof materials, and addition designs all get reviewed.
What is a captain's house on Martha's Vineyard?
A captain's house is the local term for the two-story symmetric Federal or Greek Revival homes built by Vineyard whaling captains between roughly 1800 and 1870. The classic version has a center entrance, six-over-six windows, a fanlight transom, and a widow's walk on the roof. North Water Street in Edgartown has the densest concentration.
Can I renovate a historic home on Martha's Vineyard?
Yes, with the right approvals. Interior renovations are generally not restricted, though most owners choose to preserve the original layout in the public rooms. Exterior work inside a designated historic district requires Historic District Commission review and approval. Outside the districts, most renovations follow standard town zoning and building-permit rules. Additions almost always require review.
Are historic homes a good investment on MV?
Historic homes have shown strong long-term appreciation, particularly inside the Edgartown Historic District where new supply is structurally blocked. The premium is highest for homes that have been carefully restored with period detailing preserved. Over-renovated homes, where the original character has been removed, see a narrower premium or trade closer to comparable non-historic inventory.
What are the historic districts on Martha's Vineyard?
The largest is the Edgartown Historic District. Vineyard Haven has the William Street Historic District. Aquinnah, Chilmark, and West Tisbury have smaller designated historic clusters tied to early farms, lighthouses, and the Gay Head Lighthouse area. Several individual properties across the island carry National Register listings without being in a designated district.
Can I get tax credits for restoring a historic MV home?
The 20 percent Federal Historic Preservation Tax Credit and the 20 percent Massachusetts Historic Rehabilitation Tax Credit are available for income-producing properties (rentals, inns, businesses) on the National Register, individually or as part of a contributing structure in a district. Owner-occupied second homes generally do not qualify. Verify with your tax advisor before relying on either credit.
What is the difference between a captain's house and a sea captain's mansion?
Sea captain's mansion is the term often used for the larger and grander captain's houses, particularly the three-story examples on upper North Water Street and the Daniel Fisher House on Main Street. The architectural lineage is the same: Federal and Greek Revival, built with whaling-era money, often by the same Edgartown craftspeople. The size and detailing are the difference.
How do you check a historic home's true age?
Town assessor records, the Martha's Vineyard Museum archives, the Massachusetts Cultural Resource Information System (MACRIS) database, and a careful in-person review of the framing, fasteners, and original fabric. Many historic Vineyard homes have additions, dormers, and ells from multiple decades. The published date is usually the oldest section. A good historic-property inspector will date each section separately.
Are window replacements allowed in the Edgartown Historic District?
Yes, but only with Historic District Commission approval and only in materials and configurations that match the original. True-divided-light wood windows in the original six-over-six or twelve-over-twelve patterns are the default. Modern aluminum-clad replacements with snap-in grids are usually not approved. Custom wood replacements from a Vineyard or off-island sash specialist are the standard solution.
Further reading.
The Mansions of Vineyard Haven on Martha's Vineyard
A field guide to the William Street historic district and the merchant and captain's homes that shaped Vineyard Haven's harbor side.
Read article4 Popular Architectural Styles on Martha's Vineyard
Captain's houses, gingerbread cottages, shingled Carpenter Gothic, and modern shingle-style: how to spot each on the Vineyard and what each commands.
Read articleKey Questions to Ask During an Open House in Edgartown, MA
Edgartown is where most historic-home tours happen. The specific questions experienced buyers ask before, during, and after a Captain's-house walkthrough.
Read articleConsidering a historic Vineyard home?
Portfolio Properties has been working the historic-district markets for more than 25 years, with deep relationships in Edgartown, Vineyard Haven's William Street, and the Chilmark farm stock. We can walk you through what is on the market, what is coming up off-market, and what each district will and will not allow on a renovation.