BMN Boston

Get our mobile app!

Download on the App Store

66 Sunnyside Ave, Winthrop MA 02152

Winthrop, MA 02152 • Cottage Park
$1,199,000
$999,888
Est. $6,083/month
5
Beds
2
Baths
2,635
Sq Ft
$379
Price/Sq Ft
0.12
Acres
1920
Year Built
2
Parking
45
Days on Market
Active Price Drop -$199,112 Listed Jun 3, 2026 • MLS# 73529063 Copied! • Updated Jul 14, 2026

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!

View in the App

Save this property, schedule tours instantly, and get alerts when the price drops

Scan to download BMN Boston app Scan with phone
Get the full experience in the BMN Boston app

BMN Estimate

Get the number an algorithm can't give you

A free agent CMA factors in condition, upgrades, and the street — the things comps alone can't see.

Recently Sold Nearby

Property History

Market Insights

1
Price Changes
23.7%
Price Range
1
Previous Sales

Property Timeline

Price Reduced
Jul 10, 2026
$999,888 $199,112 (-16.61%)
From $1,199,000 to $999,888 (-16.6%)
🏠
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

Tax History

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

Financial Details

Annual Property Tax
$9,928
Tax Year 2026
Assessed Value
$891,200

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 5
Full Baths 2
Total Rooms 16

Investment Metrics

Units 2
Unit 1 Rent $3,100/mo · Y
Unit 2 Rent $4,000/mo · Y
Total Monthly Rent $7,100/mo
Gross Income $85,200
Net Operating Income $76,900
Operating Expenses $8,300
Water/Sewer Expense $3,000
Insurance Expense $3,200
Cap Rate 7.69%
Heating None
Cooling None
Flooring None
Appliances None
Fireplace None
Basement Walk-out Access, Interior Entry, Sump Pump, Concrete
Laundry None
Features None
Construction None
Architecture None
Roof Rubber
Features Professional Landscaping
Pool None
Spa None
Fencing Fenced
Patio/Porch Enclosed, Deck
Features Off Street, Paved
Total Spaces 2
Electric Circuit Breakers, Individually Metered
Water Public
Sewer Public Sewer
Gas None
Other None

Financial

Annual Tax $9,928
Assessed Value $891,200
Fee Includes None
Amenities None
Optional Fee Includes None
Seller Disclosures Property Is Located In A Flood Zone. Basement Is Equipped With A Sump Pump System. The Seller Reserves The Right To Accept An Offer At Any Time
Possession None
Accepted Financing None
Structure Type []
Sq Ft Source Public Record
Documents None
County Suffolk
Total market time (incl. prior listings) 41 days

Property Overview

Property Type
Multi Family
Listing Type
For Sale
Year Built
1920
Bedrooms
5
Full Bathrooms
2
Living Area
2,635 sq ft
Total Rooms
16
Stories
3
Levels
3

Room Details

Other Floor

Bathroom1
Bedroom5
Bedroom4
Bedroom3
Dining Room
Kitchen
Bathroom2
Bedroom2
Living Room
Bathroom3
Master Bedroom
Office
Family Room
Master Bathroom

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:
School District
Winthrop School District local
C
School Safety 2024-25
0.3% Low
0.3% Suspensions
5.2% below state avg
E

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
M

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
H

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
Learn about these ratings

Monthly Payment Calculator

Monthly Payment
$0
Principal, interest, taxes & insurance
Loan Amount
$0
After down payment
Total Interest
$0
Over life of loan
Total Cost
$0
Including down payment
%
Down: $0
%

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

Rate Impact

-0.5% Rate
$0/mo
Save $0/mo
Current Rate
$0/mo
+0.5% Rate
$0/mo
Cost $0/mo

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.

Location

Loading map...

Neighborhood

Cottage Park

66 Sunnyside Ave, Winthrop MA 02152

Winthrop, MA 02152

Listing Information

Listing Agent Mirna Monterrosa Orellana
Listing Office COM-PRO Real Estate Services, Inc
Office Phone 617-381-9010
Agent MLS ID CN229530
Office MLS ID B95159
Listing Data Updated Jul 14, 2026 3:05 AM EDT
Listing information is deemed reliable but not guaranteed. Data provided by MLS Property Information Network, Inc. All information should be independently verified.

Contact Us

Steven Novak
Steven Novak
BMN Boston Real Estate
Ask about this property — free, no obligation.

Similar Homes for Sale

Comparable Properties

Customize Comparable Search

Finding comparable properties...

Market Analytics for Winthrop, MA

Real-time market trends and pricing data for this area

66 Sunnyside Ave, Winthrop MA 02152 - Photo 1 66 Sunnyside Ave, Winthrop MA 02152 - Photo 2 66 Sunnyside Ave, Winthrop MA 02152 - Photo 3 66 Sunnyside Ave, Winthrop MA 02152 - Photo 4 66 Sunnyside Ave, Winthrop MA 02152 - Photo 5 66 Sunnyside Ave, Winthrop MA 02152 - Photo 6 66 Sunnyside Ave, Winthrop MA 02152 - Photo 7 66 Sunnyside Ave, Winthrop MA 02152 - Photo 8 66 Sunnyside Ave, Winthrop MA 02152 - Photo 9 66 Sunnyside Ave, Winthrop MA 02152 - Photo 10 66 Sunnyside Ave, Winthrop MA 02152 - Photo 11 66 Sunnyside Ave, Winthrop MA 02152 - Photo 12 66 Sunnyside Ave, Winthrop MA 02152 - Photo 13 66 Sunnyside Ave, Winthrop MA 02152 - Photo 14 66 Sunnyside Ave, Winthrop MA 02152 - Photo 15 66 Sunnyside Ave, Winthrop MA 02152 - Photo 16 66 Sunnyside Ave, Winthrop MA 02152 - Photo 17 66 Sunnyside Ave, Winthrop MA 02152 - Photo 18 66 Sunnyside Ave, Winthrop MA 02152 - Photo 19 66 Sunnyside Ave, Winthrop MA 02152 - Photo 20 66 Sunnyside Ave, Winthrop MA 02152 - Photo 21 66 Sunnyside Ave, Winthrop MA 02152 - Photo 22 66 Sunnyside Ave, Winthrop MA 02152 - Photo 23 66 Sunnyside Ave, Winthrop MA 02152 - Photo 24 66 Sunnyside Ave, Winthrop MA 02152 - Photo 25 66 Sunnyside Ave, Winthrop MA 02152 - Photo 26 66 Sunnyside Ave, Winthrop MA 02152 - Photo 27 66 Sunnyside Ave, Winthrop MA 02152 - Photo 28 66 Sunnyside Ave, Winthrop MA 02152 - Photo 29 66 Sunnyside Ave, Winthrop MA 02152 - Photo 30 66 Sunnyside Ave, Winthrop MA 02152 - Photo 31 66 Sunnyside Ave, Winthrop MA 02152 - Photo 32 66 Sunnyside Ave, Winthrop MA 02152 - Photo 33 66 Sunnyside Ave, Winthrop MA 02152 - Photo 34 66 Sunnyside Ave, Winthrop MA 02152 - Photo 35 66 Sunnyside Ave, Winthrop MA 02152 - Photo 36 66 Sunnyside Ave, Winthrop MA 02152 - Photo 37 66 Sunnyside Ave, Winthrop MA 02152 - Photo 38 66 Sunnyside Ave, Winthrop MA 02152 - Photo 39 66 Sunnyside Ave, Winthrop MA 02152 - Photo 40 66 Sunnyside Ave, Winthrop MA 02152 - Photo 41 66 Sunnyside Ave, Winthrop MA 02152 - Photo 42
Steven Novak

Steven Novak

BMN Boston Real Estate

Your message will be sent to Steven Novak.

Schedule a Tour