66 Sunnyside Ave Winthrop, MA ^$ 999,888

66 Sunnyside Ave

^$ 999,888

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66 Sunnyside Ave

Winthrop, MA, 02152

^$ 999,888

Bedrooms5 Baths2.0 Sq 2,635

Monthly Estimate*

^$ 6,313

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Multi-Family Home for sale in Winthrop, MA

for $999,888 with 5 bedrooms and 2 full baths. This 2,635 square foot home was built in 1920 on a lot size of 0.12.

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!

Multi-Family Active

Price

^$ 999,888

Bedrooms

Full Bath

Property Type

Multi-Family

Taxes

^$ 9,928

Style

Multi Family

Lot Size

0.12

Year Built

1920

Town/City

Winthrop

County/Region

Suffolk

MLS | Web ID

73529063

List By

Mirna Monterrosa Orellana

Listing Agent

Com-Pro Real Estate Services, Inc

Broker

Affordability Calculator

$7,141

Per Month

Monthly Principal & Interest: $6,313
Monthly Property Taxes: $827
Monthly Home Insurance: --

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Default based on a 30-year fixed rate of 6.49% with 20% down. The estimated payment is offered for convenience and is not an offer of credit. Due to market fluctuations, interest rates are subject to change at any time and without notice. Your individual rate may vary. Rates may differ for FHA, VA or jumbo loans.

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Nearby

Trends

Multi-family listings in Winthrop, MA

Average List Price ^$1,489,879

Percent of Sale Price 49%

About Winthrop, MA

17,967 Population

-2% Since 2002

^$65,929 Median Income

46.08 Median Age

21% Households with Children

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Trends Information provided by ATTOM Data Solutions.

Neighborhood & Schools

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Pricing History

Date	Price	Price Change	Description
7/10/2026	$999,888	-16.61%	Price Down
6/3/2026	$1,199,000		Listed Price

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66 Sunnyside Ave, Winthrop, MA, 02152 is a Multi-Family Home for sale at $999,888 with 2,635 sqft and a lot size of 0.12. 66 Sunnyside Ave has 5 bedrooms, 2.0 baths, and was built in 1920. The property's zip code is 02152 which is in Winthrop, MA

*Information deemed reliable but not guaranteed.

Financial calculator disclaimer: Default based on a 30-year fixed rate of 6.49% with 20% down. The estimated payment is offered for convenience and is not an offer of credit. Due to market fluctuations, interest rates are subject to change at any time and without notice. Your individual rate may vary. Rates may differ for FHA, VA or jumbo loans.

Data is updated as of 7/22/2026.

The real estate information and related content displayed on this site is provided for consumers' personal, non-commercial use and may not be used for any purpose other than to identify prospective properties consumers may be interested in purchasing.

The property listing data and information, or the Images, set forth herein were provided to MLS Property Information Network, Inc. from third party sources, including sellers, lessors and public records, and were compiled by MLS Property Information Network, Inc. The property listing data and information, and the Images, are for the personal, non-commercial use of consumers having a good faith interest in purchasing or leasing listed properties of the type displayed to them and may not be used for any purpose other than to identify prospective properties which such consumers may have a good faith interest in purchasing or leasing. MLS Property Information Network, Inc. and its subscribers disclaim any and all representations and warranties as to the accuracy of the property listing data and information, or as to the accuracy of any of the Images, set forth herein.

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66 Sunnyside Ave

Multi-Family Home for sale in Winthrop, MA

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