Active
29 Days on market
124 Main St. Tisbury — Photo 1 of 42

124 Main St. Tisbury — Photo 1 of 42

Recent Drop: $255,000

$2,950,000
$2,695,000

$2,695,000

Investment Analysis — 124 Main St.

Tisbury, MA 02568 — Vineyard Haven

Based on HUD Small Area Fair Market Rent for Taunton-Mansfield-Norton, MA HUD Metro FMR Area, a 5-bedroom in 02568 carries an estimated $2,970/mo in gross rent — about a 0.47% cap rate and $12,762/yr in estimated NOI at the $2,695,000 list price. Adjust every assumption in the calculator below.

View Standard Listing

Beds

5

Baths

4

SqFt

2,374

Style

Single Family

Built

1808

Historic Water View Elegance Meets Modern Luxury in Vineyard Haven: Step into a piece of Martha's Vineyard history with this exceptionally charming antique Cape, originally dating back to 1808. While the home proudly retains its authentic historical character, boasting exquisite period details, rich moldings, and wide-pine floorboards, it has been thoughtfully updated to offer the ultimate in contemporary living. There are 5 total bedrooms, 2 on the first floor and 3 on the second floor. There are 2 en suite bedrooms, 1 on the first floor and 1 on the second floor. In addition, there are 4 full bathrooms (3 newly renovated), and a light-filled, spacious kitchen, designed to blend old world charm with modern needs. Additional updates include central air conditioning, 3 lined chimneys, and an upgraded septic system. A bluestone patio is ideal for al fresco dining and summer barbecues. And a lovely, professionally maintained backyard and garden complete the storybook picture. Perfectly positioned right across from picturesque Owen Park, this property places you at the very heart of Vineyard Haven culture and coastal convenience. Take in water views and the boat activity of scenic Vineyard Haven Harbor. Enjoy front-row access to Owen Park with the newly built town dock and the historic bandstand where you can enjoy the Vineyard Haven Band play Sunday evenings in the summer. When you want to explore further, you are a short walk from the village where there are several exciting new restaurants, a multitude of shops, and the historic Playhouse. Whether you are looking for a gracious year-round island residence, a seasonal getaway, or a desirable vacation rental income producer, this historic gem delivers on every front. Schedule your private tour today and experience the magic of Vineyard Haven living. Offer mostly furnished and equipped with some exclusions.

ADU Potential

Massachusetts allows one accessory dwelling unit by right in single-family zoning districts statewide (M.G.L. c. 40A §3; 760 CMR 71.00, effective Feb 2025). Estimated maximum ADU size for this property: 900 sq ft (the lesser of 900 sq ft or half the 2,374 sq ft principal dwelling). Lot size: 8,533 sq ft.

Based on listing data, which indicates the property type — not the zoning district. Local dimensional, septic (Title 5), and historic-district requirements still apply. Not legal advice — verify with the municipality.

Estimates — not financial advice

These figures are illustrative estimates for informational purposes only — not an appraisal, valuation, or guarantee of rent, income, or returns, and not financial, tax, or investment advice. Rent is either the figure reported on the MLS listing — in-place rent that may differ from market and is not verified against the actual leases — or, where the listing reports none, an estimate from HUD Small Area Fair Market Rents, a government benchmark that may differ from actual market rent. Each figure is labelled with its source. Cap rate, NOI, and returns depend on the assumptions shown, which you can change. MLS and other third-party data may be inaccurate or out of date. Verify all figures independently and consult your own financial, tax, and legal advisors before making any investment decision.

Property Details

Financials

Original Price$2,950,000
Annual Taxes$14,324

Parking

Garage1
Off-Street4

Interior Specifications

Total Rooms10
Fireplaces3
FlooringWood
BasementPartial, Unfinished

Climate & Utilities

HeatingCentral, Forced Air
CoolingCentral Air
WaterPublic
SewerInspection Required for Sale, Private Sewer

Building & Exterior

ConstructionFrame
RoofShingle
FoundationIrregular
ZoningR10

Property & Lot

Acres0.2
SqFt Lot8,533
Lot FeaturesCleared

Amenities & Appliances

Electric Water Heater • Range • Dishwasher • Refrigerator • Washer • Dryer

Neighborhood

Public Transportation • Shopping • Park

Geography

Floorplan Breakdown

Structural Layout

Second
Bedroom 3Bedroom 4Bedroom 5Bathroom 3
First
Living RoomDining RoomKitchenFamily RoomMaster BedroomBedroom 2Bathroom 1Bathroom 2
Living Room
Lvl First
Dining Room
Lvl First
Kitchen
Lvl First
Family Room
Lvl First
Master Bedroom
Lvl First
Bedroom 2
Lvl First
Bedroom 3
Lvl Second
Bedroom 4
Lvl Second
Bedroom 5
Lvl Second
Bathroom 1
Lvl First
Bathroom 2
Lvl First
Bathroom 3
Lvl Second

Property History

Price Drop
$2,695,000

Was $2,950,000

Aug 14, 2026

MLS® 73560291

Listed
$2,950,000

Aug 5, 2026

MLS® 73560291

Listing Provided By

Listing Agent: Idalyn Macchia Gilstad

Listing Office: Viewpoints; Bobbi Flake Reed, Inc.

MLS® Number: 73560291