150 Baywater Avenue
Southold, NY 11971
3
Bed
4
Bath
2,100Sqft
1.05Acres(Lot)
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 si
Property Details
Map
Map
What's Nearby
Nearby Areas
Features
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Bedroom Information
Total beds: 3Bathroom Information
Total Baths: 4 Full Baths: 4Room Information
Rooms Total: 8 -
Interior Features
Other Appliances: Other -
Heating & Cooling
Has Heating: Yes Heating: See Remarks, Other Cooling: None
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Building Information
Year Built: 1900 Construction Materials: Other Private Pool: No
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Lot Information
Lot Size Acres: 1.05 Lot Size Square Feet: 45738
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Listing Price Information
Listing Price: $850000
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Tax Information
Parcel Number: 1000-078-00-03-00-022-000 Annual Tax: $7527.08
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Parking Information
Driveway
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School Information
Elementary School: Southold Elementary SchoolJunior High School: Southold Junior-Senior High SchoolSenior High School: Southold Junior-Senior High School -
Utility Information
See Remarks -
Location Information
WaterSource: Public
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Nearby Home Value
| Address | Estimate | Bed | Bath | Sq. Ft | Lot Size |
|---|---|---|---|---|---|
| 52755 Soundview Avenue, Southold, NY, 11971 | $1,299,999 | 3 | 2 | 1,576 | 1,576 SqFt |
| 530 Sunset Way, Southold, NY, 11971 | $1,699,000 | 5 | 2 | 1,688 | 1,688 SqFt |
| 250 Paradise Point Road, Southold, NY, 11971 | $1,299,000 | 4 | 3 | 2,200 | 2,200 SqFt |
| 920 Cedar Point Drive, Southold, NY, 11971 | $6,550,000 | 5 | 5 | 3,500 | 3,500 SqFt |
| 1455 Cedar Point Drive, Southold, NY, 11971 | $2,495,000 | 3 | 2 | 1,250 | 1,250 SqFt |
| 1135 Wildberry Lane, Southold, NY, 11971 | $2,895,000 | 5 | 6 | 3,240 | 3,240 SqFt |
| 80 Deer Run, Southold, NY, 11971 | $3,295,000 | 4 | 6 | 7,341 | 7,341 SqFt |
| 150 Deer Run, Southold, NY, 11971 | $3,695,000 | 5 | 6 | 5,285 | 5,285 SqFt |
| 5845 N Bayview Road, Southold, NY, 11971 | $970,000 | 3 | 2 | 1,989 | 1,989 SqFt |
| 445 Budds Pond Road, Southold, NY, 11971 | $975,000 | 3 | 3 | 1,988 | 1,988 SqFt |
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ByOwner last updated this listing 06/15/2026 @ 22:02
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