Rare opportunity to own a legal 2 family with an inlaw apartment in one of Winthrop's most desirable locations! Completely vacant and ready for its next owner, this brick-front property offers tremendous potential for investors, owner-occupants, or multigenerational living. No flood insurance required. The spacious owner's unit lives like a single-family home, featuring 7 rooms, 3 bedrooms, a sunroom, office, dining room, deck, and a dramatic sunken living room with fireplace. Additional 2-room apartment & in-law apt provide excellent income potential. Set on a beautiful, generously sized lot with a heated 2-car garage, this property is ready for your vision and updates. Enjoy all that Winthrop has to offer—beautiful beaches, scenic waterfront walks, outstanding restaurants, local shops, and a welcoming small-town atmosphere—just minutes to the MBTA, Logan Airport, Boston, and major routes north and south.
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| Year | Land | Building | Total | Change |
|---|---|---|---|---|
| FY2025 | $361,700 | $305,300 | $669,700 | — |
| Date | Price | Book/Page |
|---|---|---|
| May 4, 1984 | $147,000 | — |
No building permits on record since 2023.
Discrepancies found between MLS and assessor records.
| Field | Assessor | MLS | Match |
|---|---|---|---|
| Sqft | 4,078 | 3,035 | ✗ |
| Year built | 1,950 | 1,950 | ✓ |
18-20 Fairview Steet, Winthrop MA 02151
Winthrop, MA 02151
| Date | Event | Price | Change | $/sqft | Details |
|---|---|---|---|---|---|
| 06/17/2026 | 🏠 Listed for Sale | $850,000 | - | - | Original listing |
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