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66 Sunnyside Ave, Winthrop MA 02152

$999,888

Estimated $2,449/month Calculator

Multi Family

Total Units: 2

Price Per Unit: $499,944

Total Rent: 85200/year

Estimated CAP Rate:

5 Bedrooms

Baths

2635

Total Parking: 2

5,336 (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!

This home has been viewed 16 times

Last Checked: July 15th, 2026 at 5:58am (Source: MLS PIN #73529063)

Gross Income: $85,200

Gross Expenses: $18,228

Net Income Calc: $66,972

Waterfront

Water Views

Annual Expenses for 66 Sunnyside Ave, Winthrop MA 02152

Total Gross Expenses (Calculated)$18,228/year

APOD AvailableNo

Heating

Electricity

Water

Gas

Insurance

Sewer

Trash Removal

Repair & Maintenance

Management

Miscellaneous

Real Estate Tax9928

Annual Income & Unit Breakdown for 66 Sunnyside Ave, Winthrop MA 02152

Total Gross Income (Calculated)$85,200

Unit 1

Rental Income$0

LeaseY

Bedrooms2

Bathrooms1 Full

Floor1

Levels in Unit1

Rent Includes

Unit 2

Rental Income$0

LeaseY

Bedrooms3

Bathrooms1 Full

Floor2

Levels in Unit2

Rent Includes

General Information for 66 Sunnyside Ave, Winthrop MA 02152

Listing ID73529063

Property TypeMulti Family

Price999888 ($379.46/SqFt)

StyleMulti Family

CityWinthrop

CountySuffolk

MLS AreaCottage Park

Neighborhood(s)

Approximate Living Area Total2635

Approximate Lot Size (Acres)0.12

Total Parking2

Garage Parking0

Year Built1920

Year Built SourcePublic Records

Year Built DetailsActual

WaterPublic

SewerPublic Sewer

Electric220 Volts

Hot Water

Roof MaterialAsphalt/fiberglass Shingles

BasementFull

Construction Materials

Lot FeaturesGentle Sloping

Foundation Description

Accessible Features

Outdoor SpaceCovered

ZoningRes

Water ViewsYes

Water Views FeaturesBay

Waterfront1

Waterfront FeaturesRiver

Terms

Disclosures for 66 Sunnyside Ave, Winthrop MA 02152

Lead PaintNone

UFFI

Living Area Includes BasementNo

Living Area Disclosure

Building Area SourcePublic Records

ExclusionsAll Basement Shelves & Tv. Kitch Mirror & Musical Clock.1st Fl Lr Tv. Dartboard. Shelves In Dr.

Financial Data SourceEstimated

Total Gross Expenses By Broker

Total Gross Income By Broker

Total Net Income By Broker

Short Sale / Forclosure (Bank Owned)

Compensation Based On

Financial Information for 66 Sunnyside Ave, Winthrop MA 02152

Real Estate Taxes9928

Tax Year2026

Assessed Value$891,200

Financial Data SourceEstimated

Total Gross Expenses By Broker

BostonRealEstate.com Gross Expenses

Total Gross Income By Broker

BostonRealEstate.com Gross Income

Total Net Income By Broker

BostonRealEstate.com Gross NOI

CAP Rate (based on Broker info)

Location Information for 66 Sunnyside Ave, Winthrop MA 02152

Neighborhood(s)

MLS AreaCottage Park

Area Amenities

Contact Information for 66 Sunnyside Ave, Winthrop MA 02152

Agent

Name: Mirna Monterrosa Orellana

Office

Name: COM-PRO Real Estate Services, Inc

Phone: 617-381-9010

Team Members

Payment Calculator

, Interest

Property Taxes 827.33

Principal & Interest 6160.99

HOA Dues

Term

Interest

Home Price

Down Payment

Exclusive Listing Agent

COM-PRO Real Estate Services, Inc

Mirna Monterrosa Orellana

Agent Phone

Office Phone

(617) 381-9010

Text Agent Call Agent Call Office

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    [unparsed] => 66 Sunnyside Ave, Winthrop MA 02152
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EXIT

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