150 Baywater Avenue,Southold, NY 11971
Southold, NY 11971
Description
Steeped in history and set on a 1.05-acre parcel in the heart of the North Fork, this circa-1663 residence presents a rare opportunity to preserve and reimagine one of Southold’s oldest and most significant properties. Ideally positioned, it is just moments from one of the East End’s finest sandy bay beaches and Croteaux Vineyards, as well as a short drive to renowned wineries, farm stands, and the charming village of Southold, with its shops, waterfront, and access to the Long Island Sound. The land at 150 Baywater Avenue is tied to the remarkable story of Maltby Freeman, a formerly enslaved man who earned his freedom in 1807 and, through extraordinary determination, came to own this very property along Bayview near South Harbor Road. Maltby and his wife, Dorcus Benjamin, began with a single-room structure, gradually expanding it into a family homestead in the early 1800s. Their descendants continued to acquire land, eventually owning a house and 30 acres. The Freeman family’s story is one of the earliest documented examples of Black land ownership and upward mobility on Long Island, and this property stands as a tangible connection to that chapter of American history. The property is offered strictly as-is, presenting a rare opportunity for a developer, preservationist, or visionary owner-builder. Included in the sale is a complete set of fully approved architectural and construction plans, a process that required two years of review by the Historic Preservation Commission, Town Planning Department, and Building Department. This extensive approval represents significant time, cost, and expertise that the next owner will not need to replicate. With permits and plans already secured, construction can begin immediately upon closing. For those seeking a property defined by history, character, and forward potential, 150 Baywater Avenue is ready for its next chapter.
Details
| MLS # | 985489 |
|---|---|
| Listing Type | For Sale |
| Style | House |
| Sub-Type | Resale |
| Status | Active |
| Year | 1900 |
| Days On Site | 128 |
| Listing Provided By | Compass Greater NY LLC | Marco L. Maida |
Features
| Bed(s) | 3 |
|---|---|
| Bath(s) | 4 Total |
| SQ Feet | 2,100 |
| Acreage | 1.05 |
Interior
| Cooling | None |
|---|---|
| Heating | See Remarks, Other |
| Interior Features | Other |
| Appliances | Other |
Exterior
| Construction Materials | Other |
|---|---|
| Foundation Details | Other |
Parking
| Garage Yes / No | No |
|---|---|
| Parking Features | Driveway |
Utilities
| Utilities | See Remarks |
|---|---|
| Sewer | Cesspool, Septic Tank |
Taxes
| Tax Year | 2025 |
|---|---|
| Tax Assessed Value | 4900 |
| Tax Annual Amount | 7527.08 |
Area Information
| State | NY |
|---|---|
| County | Suffolk County |
| City | Southold |
| Zip Code | 11971 |
| School District | Southold Junior-Senior High Scho |
| Elementary School | Southold Elementary School |
| High School | Southold Junior-Senior High Scho |
| Listing VS Median (in 11971) | |
Price: $850,000 low | high Med: $849,999 sqft: 2,100 low | high Med: 1,588 $ / sqft: $405 low | high Med: $535 On site: 128 low | high Med: 61 | |
Market Activity 11971
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Learn More About This Property
| State | NY |
|---|---|
| County | Suffolk County |
| City | Southold |
| Zip Code | 11971 |
| School District | Southold Junior-Senior High Scho |
| Elementary School | Southold Elementary School |
| High School | Southold Junior-Senior High Scho |
| Listing VS Median (in 11971) | |
Price: $850,000 low | high Med: $849,999 sqft: 2,100 low | high Med: 1,588 $ / sqft: $405 low | high Med: $535 On site: 128 low | high Med: 61 | |
