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!
Listing last checked: Listing updated:
Listed by Mirna Monterrosa Orellana · COM-PRO Real Estate Services, Inc · MLS #73529063
Request property information
Select a document to start a request. You can add others in the form. Availability varies.
Details at a glance
Interior2 property facts
- Rooms
- 16
- Basement
- Yes · Walk-Out Access, Interior Entry, Sump Pump, Concrete
Building5 property facts
- Style
- Multi Family
- Year built
- 1920
- Parking
- 2
- Foundation
- Brick/Mortar
- Roof
- Rubber
Land & utilities6 property facts
- Lot size
- 0.12 acres
- Water
- Public
- Sewer
- Public Sewer
- Waterfront
- Y
- Pool
- Not reported
- Zoning
- Res
Financial2 property facts
- Annual taxes
- $9,928
- Assessment year
- 2026
Location
Estimated monthly cost
Explore costs at the $999,888 asking price. Adjust the assumptions to your situation.
Known monthly costs$5,883 / monthAdjust
- Principal & interest
- $5,056
- Property tax
- $827
- Insurance
- Not entered
- HOA
- Not entered
Listing annual taxes: $9,928. Initial monthly tax is one twelfth of that amount. HOA amount was not supplied.
Partial estimate: add insurance, monthly HOA to include those costs. Blank amounts are unknown.
The initial 6.5% rate is illustrative, not a current rate or lender quote. Excludes utilities, maintenance, closing costs and mortgage insurance, which may apply with a down payment below 20%. Taxes and insurance can change.
More property insights
Automated value estimate $1,252,858
Estimated range $1,125,101–$1,380,616.
Automated estimates are not appraisals or guarantees of market value.
Request a professional market analysisPhoto-based condition insights
Overall presentation: average
Explore more of Winthrop
Continue your search in Winthrop.
Need help making sense of this home?
About 66 Sunnyside Ave
Can I request a private showing?
Request a tour of 66 Sunnyside Ave and a Bean Group agent will help coordinate an available time with the listing side.
Can you help me evaluate this property?
Yes. We can discuss condition, comparable sales, offer strategy and the questions worth asking before you decide whether to proceed.
Are property documents available?
Availability varies by property and source. Request the documents you need and we will help obtain what is available.

