
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!
Key facts
It was listed on June 3, 2026. The price has come down from an original $1,199,000 to $999,888, most recently on July 10, 2026. The annual property taxes are $9,928 (2026 tax year). It sits on a 0.12-acre (5,336 sq ft) lot.
Market Value Analysis
* Analysis is based on 22 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
Questions about this home
When was 66 Sunnyside Ave, Winthrop listed?
66 Sunnyside Ave, Winthrop was listed on June 3, 2026.
Has the price of 66 Sunnyside Ave, Winthrop changed?
The price has come down from an original $1,199,000 to $999,888, most recently on July 10, 2026.
What are the property taxes for 66 Sunnyside Ave, Winthrop?
The annual property taxes for 66 Sunnyside Ave, Winthrop are $9,928 (2026 tax year).
How big is the lot at 66 Sunnyside Ave, Winthrop?
66 Sunnyside Ave, Winthrop sits on a 0.12-acre (5,336 sq ft) lot.
What is the status of 66 Sunnyside Ave, Winthrop?
66 Sunnyside Ave, Winthrop is actively listed for sale.
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
2,337 housing units permitted in the last 12 months (+13% vs the prior 12 months) — 2,062 in 5+ unit buildings
U.S. Census Bureau, Building Permits Survey (through Jul '26)
Listing Agent: Mirna Monterrosa Orellana
Listing Office: COM-PRO Real Estate Services, Inc
MLS® Number: 73529063









