Active
98 Days on market
66 Sunnyside Ave Winthrop — Photo 1 of 42

66 Sunnyside Ave Winthrop — Photo 1 of 42

Recent Drop: $199,112

$1,199,000
$999,888

$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

This Property
Size (SqFt) →Price →
This Property$379/sqft
Local Avg (Winthrop)$408/sqft
7% BelowMarket Average

* Analysis is based on 23 actively listed and recently sold comparable properties strictly within Winthrop, MA.

Property Details

Financials

Original Price$1,199,000
Annual Taxes$9,928

Parking

Garage0
Off-Street2

Interior Specifications

Total Rooms16
FireplacesNone
Flooring--
BasementWalk-Out Access, Interior Entry, Sump Pump, Concrete

Climate & Utilities

Heating--
Cooling--
WaterPublic
SewerPublic Sewer

Building & Exterior

Construction--
RoofRubber
FoundationBrick/Mortar
ZoningRes

Property & Lot

Acres0.12
SqFt Lot5,336
Lot FeaturesOther

Geography

Property History

Price Drop
$999,888

Was $1,199,000

Jul 10, 2026

MLS® 73529063

Listed
$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 Provided By

Listing Agent: Mirna Orellana

Listing Office: COM-PRO Real Estate Services, Inc

MLS® Number: 73529063

Browse More Homes in Winthrop

Explore other active listings in the area.