66 Sunnyside Ave Winthrop — Photo 1 of 42
Recent Drop: $199,112
$999,888
Investment Analysis — 66 Sunnyside Ave
Winthrop, MA 02152 — Cottage Park
Based on rent reported on the MLS listing, a 2-unit multi-family in 02152 carries $7,100/mo in gross rent — about a 5.48% cap rate and $54,824/yr in estimated NOI at the $999,888 list price. Adjust every assumption in the calculator below.
Beds
5
Baths
2
SqFt
2,635
Style
Multi Family
Built
1920
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!
Estimates — not financial advice
These figures are illustrative estimates for informational purposes only — not an appraisal, valuation, or guarantee of rent, income, or returns, and not financial, tax, or investment advice. Rent is either the figure reported on the MLS listing — in-place rent that may differ from market and is not verified against the actual leases — or, where the listing reports none, an estimate from HUD Small Area Fair Market Rents, a government benchmark that may differ from actual market rent. Each figure is labelled with its source. Cap rate, NOI, and returns depend on the assumptions shown, which you can change. MLS and other third-party data may be inaccurate or out of date. Verify all figures independently and consult your own financial, tax, and legal advisors before making any investment decision.
Property Details
Financials
Parking
Interior Specifications
Climate & Utilities
Building & Exterior
Property & Lot
Geography
Property History
$999,888
Was $1,199,000
Jul 10, 2026
MLS® 73529063
$1,199,000
Jun 3, 2026
MLS® 73529063
Listing Agent: Mirna Orellana
Listing Office: COM-PRO Real Estate Services, Inc
MLS® Number: 73529063