
66 Sunnyside Ave Winthrop — Photo 1 of 42
Recent Drop: $199,112
$999,888
66 Sunnyside Ave, Winthrop, MA 02152
Winthrop, MA 02152 — Cottage Park
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!
Market Value Analysis
* Analysis is based on 23 actively listed and recently sold comparable properties strictly within Winthrop, MA.
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
Population
18,759
U.S. Census Bureau, ACS 2024 5-Year Estimates (B01003)
Median Household Income
$116K
U.S. Census Bureau, ACS 2024 5-Year Estimates (B19013)
Renter-Occupied Homes
43.1%
U.S. Census Bureau, ACS 2024 5-Year Estimates (B25003)
New Construction Permits — Suffolk County
2,527 housing units permitted in the last 12 months (+37% vs the prior 12 months) — 2,269 in 5+ unit buildings
U.S. Census Bureau, Building Permits Survey (through Jun '26)
Listing Agent: Mirna Orellana
Listing Office: COM-PRO Real Estate Services, Inc
MLS® Number: 73529063
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