566 Shirley St contains six (6) units, consisting of two (2), 2-Bedroom/1-Bathroom units and four (4), 3-Bedroom/1-Bathroom units with 5,553 square feet of living area in 7,968 square feet of total gross area on a 0.09-acre corner parcel. The Property is across the street from the Crystal Cove Marina and is 1,000 feet from Winthrop Beach and the shores of the Atlantic Ocean. The Property has been well maintained and features all new common area lighting and carpeting, the foundation (interior and exterior) has been repointed. The Property has new blown-in insulation, and the rear deck system has been updated with refinished decks and new railings. The Property also has a new 11-camera security system and credit card operated washers and dryers. Two of the units have been fully renovated and two units have renovated bathrooms. The Property is separately metered for a mix of gas & electric powered heat & hot water, as well as electrictity. The Landlord provides town water & sewer.
| Units | 6 |
| Living area | 5,553 sqft |
| Lot size | 3,920 sqft |
| Year built | 1900 |
| Price / sqft | $405 |
| County | Suffolk |
| MLS # | 73554183 |
| Days on market | 4 days |
| Listed on | July 23, 2026 |
| Annual property tax | $16,964 |
| Tax year | 2026 |
| Assessed value | $1,522,800 |
| Zoning | N/A |
| Gross income (actual) | $204,900/yr |
| Net operating income (actual) | $146,029/yr |
| Total actual rent | $16,825/mo |
| Stories | 5 |
| Total rooms | 28 |
| Lot size | 0.09 acres |
| Garage spaces | 0 |
| Parking spaces | 0 |
| Parking | On Street |
| Foundation | Other |
| Roof | Rubber |
| Sewer | Public Sewer |
| Water | Public |
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Listing courtesy of a MLS PIN member office. Listing data © MLS PIN.
Auto-generated from the listing data — richer AI answers coming with the live site.
It is a 6-unit multi-family property with 5,553 sqft of living area, built in 1900.
566 Shirley St, Winthrop MA 02152 has been listed for 4 days (since July 23, 2026).
At a list price of $2,250,000 across 6 units, that works out to roughly $375,000 per unit.
Annual property taxes are $16,964 (2026), on an assessed value of $1,522,800.
At $2,250,000 for 5,553 sqft, that's about $405 per square foot.
566 Shirley St, Winthrop MA 02152 is in Winthrop, Suffolk County, MA 02152.

Justin Rollo is a Broker Associate with Signal Real Estate (MA Lic. #9534264) and a lifelong Massachusetts resident. Over 14 years and hundreds of transactions, he has worked investment properties — multi-families and house-hacking — across Greater Boston full-time. Away from real estate, Justin is a proud dad, youth coach and local school-committee member — and a former professional poker player who still loves golf and following local sports.