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Bean Group
Offered at $999,888Active
beds
5
baths
2
sq ft
2,635
Built
1920

66 Sunnyside Ave

Winthrop, MA 02152

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

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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.

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Photo-based condition insights

Overall presentation: average

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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.