For sale

Price cut: $199.1K (7/10)

$999,888

66 Sunnyside Ave, Winthrop, MA 02152

5beds

2,635sqft

$6,451/mo

Get pre-qualified

Multi Family

Built in 1920

-- sqft lot

$980,200 Zestimate^®

$379/sqft

$-- HOA

What's special

Versatile layoutFive bedroomsTwo-story residenceExpansive footprint

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!

99 days
478
14

Facts & features

Interior

Bedrooms & bathrooms

Bedrooms: 5
Bathrooms: 2
Full bathrooms: 2

Features

Basement: Walk-Out Access,Interior Entry,Sump Pump,Concrete
Has fireplace: No

Interior area

Total structure area: 2,635
Total interior livable area: 2,635 sqft
Finished area above ground: 2,635

Property

Parking

Total spaces: 2
Parking features: Off Street, Paved
Uncovered spaces: 2

Features

Patio & porch: Enclosed, Deck
Exterior features: Professional Landscaping
Fencing: Fenced
Has view: Yes
View description: Water, Bay, Harbor, Marsh, Ocean
Has water view: Yes
Water view: Bay,Harbor,Marsh,Ocean,Water
Waterfront features: Waterfront, Bay, Ocean, 1/10 to 3/10 To Beach, Beach Ownership(Public)

Lot

Size: 5,336 Square Feet
Features: Other

Details

Parcel number: M:0022 B:0091 L:0000,1421230
Zoning: Res

Construction

Type & style

Home type: MultiFamily
Property subtype: Multi Family

Materials

Foundation: Brick/Mortar
Roof: Rubber

Condition

Year built: 1920

Utilities & green energy

Electric: Circuit Breakers, Individually Metered
Sewer: Public Sewer
Water: Public

Community & HOA

Location

Region: Winthrop

Financial & listing details

Price per square foot: $379/sqft
Tax assessed value: $891,200
Annual tax amount: $9,928
Date on market: 6/3/2026
Total actual rent: 7100

Estimated market value

$980,200

$931,000 - $1.03M

$3,105/mo

Price history

Date	Event	Price
7/10/2026	Price change	$999,888-16.6%$379/sqft
Source: MLS PIN #73529063 Report a problem
6/3/2026	Listed for sale	$1,199,000+31%$455/sqft
Source: MLS PIN #73529063 Report a problem
4/8/2024	Sold	$915,000+1.7%$347/sqft
Source: MLS PIN #73204490 Report a problem
3/4/2024	Contingent	$900,000$342/sqft
Source: MLS PIN #73204490 Report a problem
2/22/2024	Listed for sale	$900,000+80%$342/sqft
Source: MLS PIN #73204490 Report a problem
10/27/2023	Sold	$500,000$190/sqft
Source: Public Record Report a problem

Public tax history

Year	Property taxes	Tax assessment
2025	$9,535 +7.4%	$923,900 +8.4%
2024	$8,879 -7.9%	$852,100 -5.4%
2023	$9,643 +1.7%	$901,200 +11.8%
2022	$9,480 +2.7%	$806,100 +10.8%
2021	$9,227 +2%	$727,700 +1.5%
2020	$9,045 +2.3%	$716,700 +6.8%
2019	$8,842 +10.9%	$670,900 +19.2%
2018	$7,971 +9.3%	$562,900 +11.2%
2017	$7,291 +6%	$506,000 +13%
2016	$6,880 +12.1%	$447,600 +4.6%
2015	$6,136 +11%	$427,900 +15.4%
2013	$5,529 -1.9%	$370,800 -4.7%
2012	$5,635 +13.6%	$388,900 +8.2%
2011	$4,961 -1%	$359,500 -8.9%
2010	$5,010 +18.5%	$394,500 -7%
2009	$4,228 +0.4%	$424,100 -6.4%
2008	$4,212 +2.5%	$452,900 -2.8%
2007	$4,109 +4.6%	$465,900 +2.4%
2006	$3,929 +14.9%	$454,800 +20%
2005	$3,419 +1.2%	$379,000 +17.4%
2004	$3,378 +2.1%	$322,900
2003	$3,310 +7.9%	$322,900 +66.4%
2002	$3,067 +28.2%	$194,100
2000	$2,393	$194,100