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INVESTMENT SNAPSHOT
About this property
NEWLY PRICED! PRICED TO SELL! Rare waterfront two-family in Winthrop's sought-after Cottage Park neighborhood, offering stunning views of the Bay, Harbor, marsh, and ocean, a lifestyle feature you simply can't replicate at this price point. Built in 1920, this classic 2,635 sq ft two-story home sits on a 5,227 sq ft lot just steps from the beach. A perfect opportunity for first-time buyers or savvy investors. Unit 1 rents for $3,100/mo and Unit 2 for $4,000/mo, generating $85,200 in gross annual income with a net of $76,900. Five bedrooms, two full baths, and a versatile layout ideal for extended families. The property features an enclosed porch, deck, fenced yard, professional landscaping, and individually metered electric. Minutes from downtown Boston via Rt. 1A. Don't miss this opportunity; schedule your private showing today!
Property details
| Units | 2 |
| Living area | 2,635 sqft |
| Lot size | 5,336 sqft |
| Year built | 1920 |
| Price / sqft | $379 |
| County | Suffolk |
| MLS # | 73529063 |
Listing status
| Days on market | 92 days |
| Listed on | June 3, 2026 |
Taxes & financials
| Annual property tax | $9,928 |
| Tax year | 2026 |
| Assessed value | $891,200 |
| Zoning | Res |
| Gross income (actual) | $85,200/yr |
| Net operating income (actual) | $76,900/yr |
| Total actual rent | $7,100/mo |
| Insurance expense | $3,200/yr |
Building & lot
| Stories | 3 |
| Total rooms | 16 |
| Lot size | 0.12 acres |
| Garage spaces | 0 |
| Parking spaces | 2 |
| Parking | Off Street, Paved |
| Basement | Walk-Out Access, Interior Entry, Sump Pump, Concrete |
| Foundation | Brick/Mortar |
| Roof | Rubber |
Utilities & systems
| Sewer | Public Sewer |
| Water | Public |
Location
More about investing in Winthrop →
Listing courtesy of a MLS PIN member office. Listing data © MLS PIN.
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Questions & answers
Auto-generated from the listing data — richer AI answers coming with the live site.
How many units does 66 Sunnyside Ave, Winthrop MA 02152 have?
It is a 2-unit multi-family property with 2,635 sqft of living area, built in 1920.
How long has 66 Sunnyside Ave, Winthrop MA 02152 been on the market?
66 Sunnyside Ave, Winthrop MA 02152 has been listed for 92 days (since June 3, 2026).
What is the price per unit?
At a list price of $999,888 across 2 units, that works out to roughly $499,944 per unit.
What are the property taxes on 66 Sunnyside Ave, Winthrop MA 02152?
Annual property taxes are $9,928 (2026), on an assessed value of $891,200.
What is the price per square foot?
At $999,888 for 2,635 sqft, that's about $379 per square foot.
Is there parking?
2 total parking spaces (off street, paved).
Where is this property located?
66 Sunnyside Ave, Winthrop MA 02152 is in Winthrop, Suffolk County, MA 02152.
