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66 Sunnyside Ave, 
Winthrop, MA 02152

$999,888

5

Beds

2

Baths

2,635

Sq Ft

Multi-Family

Active

Listed by

Mirna Orellana

, 

Mirna Orellana

Com-Pro Real Estate Services, Inc

617-381-9010

Last updated:

July 16, 2026, 11:11 AM

MLS#

73529063

Source:

MLSPIN

About This Home

66 Sunnyside Ave

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!

Home Facts

Multi-Family

2 Baths

5 Bedrooms

Built in 1920

Price Summary

999,888

$379 per Sq. Ft.

MLS #:

73529063

Last Updated:

July 16, 2026, 11:11 AM

Rooms & Interior

Bedrooms

Total Bedrooms:

5

Bathrooms

Total Bathrooms:

2

Full Bathrooms:

2

Interior

Living Area:

2,635 Sq. Ft.

Structure

Structure

Building Area:

2,635 Sq. Ft.

Year Built:

1920

Lot

Lot Size (Sq. Ft):

5,336

Finances & Disclosures

Finances

Price:

$999,888

Price per Sq. Ft:

$379 per Sq. Ft.

Source:MLSPIN
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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Contact an Agent

Yes, I would like more information. Please use and/or share my information with a Coldwell Banker ® affiliated agent to contact me about my real estate needs. By clicking Contact, I request to be contacted by phone or text message and consent to being contacted by automated means. I understand that my consent to receive calls or texts is not a condition of purchasing any property, goods, or services. Alternatively, I understand that I can access real estate services by email or I can contact the agent myself.

If a Coldwell Banker affiliated agent is not available in the area where I need assistance, I agree to be contacted by a real estate agent affiliated with another brand owned or licensed by Anywhere Real Estate (BHGRE®, CENTURY 21®, Corcoran®, ERA®, or Sotheby's International Realty®). I acknowledge that I have read and agree to the terms of use and privacy notice.