150 Baywater Avenue, Southold, NY 11971

Southold
Local realty services provided by:Better Homes and Gardens Real Estate Realty Connect
150 Baywater Avenue,Southold, NY 11971
$850,000
  • 3 Beds
  • 4 Baths
  • 2,100 sq. ft.
  • Single family
  • Active
Listed by: marco l. maida, carl m. gambino
Office: compass greater ny llc.
MLS#:985489
Source:OneKey MLS

Price summary

  • Price:$850,000
  • Price per sq. ft.:$404.76

About this home

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...

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Home facts

  • Year built:1900
  • Listing ID #:985489
  • Added:160 day(s) ago
  • Updated:September 24, 2026 at 11:07 AM

Rooms and interior

  • Bedrooms:3
  • Total bathrooms:4
  • Full bathrooms:4
  • Rooms Total:8
  • Living area:2,100 sq. ft.

Structure and exterior

  • Year built:1900
  • Building area:2,100 sq. ft.
  • Lot area:1.05 Acres
  • Architectural Style:Victorian

Schools

  • High school:Southold Junior-Senior High School
  • Middle school:Southold Junior-Senior High School
  • Elementary school:Southold Elementary School

Utilities

  • Water:Public
  • Sewer:Cesspool, Septic Tank

Finances and disclosures

  • Price:$850,000
  • Price per sq. ft.:$404.76
  • Tax amount:$7,527 (2025)

Parking

  • Parking description:Driveway
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