$999,888
66 Sunnyside Ave
Winthrop, MA, 02152
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!
Property Details
Price:
$999,888
MLS #:
73529063
Status:
Active
Beds:
5
Baths:
2
Type:
Multi Family
Neighborhood:
cottagepark
Listed Date:
Jun 3, 2026
Finished Sq Ft:
2,635
Total Sq Ft:
2,635
Lot Size:
5,336 sqft / 0.12 acres (approx)
Year Built:
1920
Units:
2
Schools
Interior
Above Grade Finished Area
2635
Bathrooms
2 Full Bathrooms
Levels
3
Exterior
Exterior Features
Professional Landscaping
Fencing
Fenced
Lot Features
Other
Open Parking Spaces
2
Open Parking YN
1
Parking Features
Off Street, Paved
Parking Spots
2
Parking Total
2
Patio And Porch Features
Enclosed, Deck
Roof
Rubber
Stories
3
Waterfront Features
Waterfront, Bay, Ocean, 1/10 to 3/10 To Beach, Beach Ownership(Public)
Financial
Tax Year
2026
Taxes
$9,928
Marie Andrews is an award-winning, licensed real estate broker with licenses in Massachusetts and Florida. She has been selling real estate in the greater Boston area for over 20 years. Over the past two decades, Marie has worked for Century 21 Advanced Realty, building a reputation as a multi-million dollar producer. She has developed an extensive network of investors, lenders, and attorneys. Marie has a wide knowledge base on property management, Massachusetts real estate law, and building…
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Map
Current real estate data for Multi Family in Winthrop as of Jul 17, 2026
19
Multi Family Listed
154
Avg DOM
378
Avg $ / SqFt
$1,298,235
Avg List Price
Community
- Address66 Sunnyside Ave Winthrop MA
- CityWinthrop
- CountySuffolk
- Zip Code02152
Subdivisions in Winthrop
Similar Listings Nearby
Property Summary
- 66 Sunnyside Ave Winthrop MA is a Multi Family for sale in Winthrop, MA, 02152. It is listed for $999,888 To schedule a showing of MLS#73529063 at 66 Sunnyside Ave in Winthrop, MA, contact your Pegasus Realty LLC agent at 781-858-3505.
Courtesy of COM-PRO Real Estate Services, Inc. The property listing data and information 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 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 set forth herein.
66 Sunnyside Ave
Winthrop, MA