66 Sunnyside Ave, Winthrop MA 02152

Winthrop, MA 02152 • Cottage Park

$1,199,000

Est. $7,090/month

Beds

Baths

2,635

Sq Ft

$455

Price/Sq Ft

0.12

Acres

1920

Year Built

Multi Family

Type

1 hour 41 minutes

Time on Market

Active Open House Listed Jun 3, 2026 • MLS# 73529063 Copied!

About this home

Discover a unique opportunity at 66 Sunnyside Ave in Winthrop, MA, a 1920 multi-family property offering 2635 square feet of living space. This two-story residence, set on a generous 5227 square foot lot, presents an exceptional blend of classic charm and potential for contemporary living. The property features a total of five bedrooms, providing ample private spaces for residents. Two full bathrooms are thoughtfully integrated throughout the home, ensuring convenience and functionality for multiple occupants. This multi-family dwelling offers a versatile layout, ideal for extended family living or as an income-generating asset. Imagine the possibilities for creating distinct living areas within its expansive footprint. To truly appreciate the lifestyle and potential this property offers, schedule your private viewing today.

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Property Overview

Property Type

Multi Family

Listing Type

For Sale

Year Built

1920

Bedrooms

Full Bathrooms

Living Area

2,635 sq ft

Total Rooms

Stories

Levels

Open House Schedule

Jun

Saturday, June 6

11:00 AM - 1:00 PM EDT

Facts & Features

Home Facts

Type Residential Income

Style Multi Family

Year Built 1920

Living Area 2,635 sq ft

Lot Size 0.12 acres

Bedrooms 4

Full Baths 2

Total Rooms 12

Interior

Heating None

Cooling None

Flooring None

Appliances None

Fireplace None

Basement Walk-out Access, Interior Entry, Sump Pump, Concrete

Laundry None

Features None

Exterior

Construction None

Architecture None

Roof Rubber

Features Professional Landscaping

Pool None

Spa None

Fencing Fenced

Patio/Porch Enclosed, Deck

Parking

Features Off Street, Paved

Total Spaces 2

Utilities

Electric Circuit Breakers, Individually Metered

Water Public

Sewer Public Sewer

Gas None

Other None

Financial

Annual Tax $9,928

Assessed Value $891,200

Interior Features

Flooring:

Appliances:

Interior Features:

Windows:

Basement: Walk-Out Access, Interior Entry, Sump Pump, Concrete

Laundry:

Security:

Construction & Materials

Year Built: 1920

Structure Type:

Exterior Materials:

Roof: Rubber

Foundation: Brick/Mortar

Stories: 3

Heating, Cooling & Utilities

Heating:

Cooling:

Hot Water: Natural Gas

Water Source: Public

Sewer: Public Sewer

Energy Features:

Exterior & Lot

Exterior Features: Professional Landscaping

Patio & Porch: Enclosed, Deck

Fencing: Fenced

Other Structures:

Lot Features: Other

Road Surface:

Parking & Garage

Total Parking Spaces: 2

Parking Features: Off Street, Paved

Special Features

Waterfront: Yes

Waterfront Type: Waterfront, Bay, Ocean, 1/10 to 3/10 To Beach, Beach Ownership(Public)

Community Amenities:

Location

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Neighborhood

Cottage Park

66 Sunnyside Ave, Winthrop MA 02152

Winthrop, MA 02152

Walkability

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Nearby Schools

School District

Winthrop School District local

✓ School Safety 2024-25

0.3% Low

0.3% Suspensions

↓ 5.2% below state avg

Elementary Schools

2 schools

B-

Arthur T. Cummings Elementary School

0.5 mi | #453 of 824 | Score: 46.0

Improved 101 spots from last year

-12.2 below state avg

467 students Less Diverse

Rising School Strong Attendance

Grades 03-05

William P. Gorman/Fort Banks Elementary School

1.0 mi

487 students Less Diverse

Grades PK-02

Middle Schools

1 school

B+

Winthrop Middle School

0.8 mi | #119 of 352 | Score: 47.4

Dropped 26 spots from last year

-10.8 below state avg

439 students Less Diverse

Grades 06-08

High Schools

1 school

C+

Winthrop High School

0.7 mi | #241 of 346 | Score: 47.2

Dropped 112 spots from last year

-11 below state avg

568 students Less Diverse

18 sports • 1,118 athletes

College Ready Curriculum Strong Athletics

Grades 09-12

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Monthly Payment Calculator

Monthly Payment

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Total Interest

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Total Cost

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Home Price

Down Payment

Down: $0

Interest Rate

Loan Term

Monthly Payment Breakdown

Principal & Interest $0

Property Tax $827

Homeowners Insurance $200

PMI (if <20% down) $0

Loan Summary

Total of 360 payments $0

Total principal paid $0

Total interest paid $0

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Payment Over Time

Interest

Principal

Year 1

95% Interest

Year 15

50/50

Year 30

95% Principal

* Estimates only. Actual payments may vary. Consult with a lender for accurate figures.

Property History

Market Insights

23.7%

Price Range

Previous Sales

Property Timeline

🏠

Listed for Sale

Jun 3, 2026

$1,199,000

Original listing

Office: COM-PRO Real Estate Services, Inc

Previous Transaction - MLS #73204490

Full transaction history available when tracking began

🏷️

Previously Sold

Apr 8, 2024

$915,000

MLS #73204490

View Listing →

Date	Event	Price	Change	$/sqft	Details
06/03/2026	🏠 Listed for Sale	$1,199,000	-	-	Original listing
04/08/2024	🏷️ Previously Sold	$915,000	-	-	MLS #73204490

Price & Status History

Date	Event	Price	Change
Jun 3, 2026	New Listing Added	$1,199,000	—
Apr 8, 2024	Sold	$915,000	—

Market Statistics

Time on Market

1 hour 41 minutes

Price per Sq Ft

$455

Tax History

Year	Taxes	Assessment
2026	$9,928	$891,200

Financial Details

Annual Property Tax

$9,928

Tax Year 2026

Assessed Value

$891,200

Listing Information

Listing Agent Mirna Orellana

Listing Office COM-PRO Real Estate Services, Inc

Agent MLS ID CN229530

Office MLS ID B95159

Listing Data Updated Jun 3, 2026 10:32 AM EDT

Listing information is deemed reliable but not guaranteed. Data provided by MLS Property Information Network, Inc. All information should be independently verified.

Elementary Schools

Middle Schools

High Schools

Monthly Payment Breakdown

Loan Summary

Listed for Sale

Previous Transaction - MLS #73204490

Previously Sold

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66 Sunnyside Ave, Winthrop MA 02152

About this home

Property Overview

Open House Schedule

Facts & Features

Home Facts

Interior

Exterior

Parking

Utilities

Financial

Interior Features

Construction & Materials

Heating, Cooling & Utilities

Exterior & Lot

Parking & Garage

Special Features

Location

Neighborhood

Walkability

Nearby Schools

Elementary Schools

Middle Schools

High Schools

Monthly Payment Calculator

Monthly Payment Breakdown

Loan Summary

Rate Impact

Payment Over Time

Property History

Market Insights

Property Timeline

Listed for Sale

Previous Transaction - MLS #73204490

Previously Sold

Detailed History Table ▼

Price & Status History

Market Statistics

Tax History

Financial Details

Listing Information

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