Multi Family at 66 Sunnyside Ave, Winthrop MA 02152, Winthrop
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42 photos

$999,888

66 Sunnyside Ave, Winthrop MA 02152
Winthrop, MA 02152
Listed by Mirna Monterrosa Orellana
Bedrooms
5
Bathrooms
2
Living area
2,635 sqft
Year built
1920

About this home

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!

Highlights

Waterfront

Property details

MLS #
73529063
Property type
Multi Family
Subdivision
N/A
Status
Active
Days on market
127
On market date
June 3, 2026
Stories
3
Total bathrooms
2
Garage spaces
N/A
Parking spaces
2
Lot size
0.12 acres
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Nearby schools

Within 10 miles. School directory data from the National Center for Education Statistics (NCES), accessed via the Urban Institute Education Data API. Local Score is calculated by INNOVATE Real Estate; where a state rating is shown, it comes from that state's own official school report card (e.g. NC Dept. of Public Instruction, SC Report Card).

Elementary
Arthur T. Cummings Elementary School
0.45 mi away · Grades 3-5
Nearest school -- attendance-zone data not available here
5.0
Local Score (student-teacher ratio only (preliminary -- will incorporate state test-score data once available)) -- not an official state rating
Enrollment
415
Student:teacher ratio
11.9:1
District
Winthrop
Middle
Winthrop Middle School
0.71 mi away · Grades 6-8
Nearest school -- attendance-zone data not available here
5.0
Local Score (student-teacher ratio only (preliminary -- will incorporate state test-score data once available)) -- not an official state rating
Enrollment
423
Student:teacher ratio
11.1:1
District
Winthrop
High
Winthrop High School
0.69 mi away · Grades 9-12
Nearest school -- attendance-zone data not available here
4.0
Local Score (student-teacher ratio only (preliminary -- will incorporate state test-score data once available)) -- not an official state rating
Enrollment
564
Student:teacher ratio
13.4:1
District
Winthrop

Walkability

Blended score for Winthrop's center, calculated by INNOVATE Real Estate from two sources: the EPA's National Walkability Index (street network, transit, land-use mix) and Google Places amenity data (what's actually reachable on foot from this point). 60% EPA National Walkability Index + 40% nearby-amenity density (Google Places).

69
Walkable
out of 100
EPA National Walkability Index
12.3 / 20 -- Above average walkable
Google Places amenity density
80 / 100
Restaurants & cafes20
Grocery stores1
Parks20
Schools10
Transit stops20
Pharmacies1

Market position

How this listing compares to current activity in Winthrop, from live MLS data.

On the market 127 days -- 48 more days than Winthrop's current average of 79 days.
For reference, the median list price across 229 active listings in Winthrop right now is $499,900.

Mortgage calculator

Estimate only - actual rate and payment depend on your lender, credit, and loan program.

$
%
%
Adjust tax / insurance estimates
% / yr
$
/mo
Est. monthly payment
$6,171/mo
$199,978 down
$799,910 loan
Principal & interest$5,188
Property tax (est.)$833
Home insurance (est.)$150

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Data source: Listing information provided by MLS Property Information Network via Trestle/CoreLogic. Last updated July 14, 2026.

Information herein deemed reliable but not guaranteed; all measurements, school assignments, HOA fees, taxes, and feature lists are approximate and should be independently verified. Equal Housing Opportunity.