Skip main navigation
For sale
    • Price cut: $199.1K (7/10)
    $999,888

    66 Sunnyside Ave, Winthrop, MA 02152

    5beds
    2,635sqft
    : 
    $6,381/mo
    Get pre-qualified
    Multi Family
    Built in 1920
    -- sqft lot
    $981,000 Zestimate®
    $379/sqft
    $-- HOA

    What's special

    Versatile layoutFive bedroomsTwo-story residenceExpansive footprint
    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!
    52 days
    |
    446
    |
    19
    |

    Zillow last checked:

    Listing updated:

    Listed by:

    Mirna Monterrosa Orellana 617-650-7187,

    COM-PRO Real Estate Services, Inc 617-381-9010,

    Mirna Monterrosa Orellana 617-650-7187

    Source: MLS PIN,MLS#: 73529063

      Facts & features

      Interior

      Bedrooms & bathrooms
      • Bedrooms: 5
      • Bathrooms: 2
      • Full bathrooms: 2
      Features
      • Basement: Walk-Out Access,Interior Entry,Sump Pump,Concrete
      • Has fireplace: No
      Interior area
      • Total structure area: 2,635
      • Total interior livable area: 2,635 sqft
      • Finished area above ground: 2,635

      Property

      Parking
      • Total spaces: 2
      • Parking features: Off Street, Paved
      • Uncovered spaces: 2
      Features
      • Patio & porch: Enclosed, Deck
      • Exterior features: Professional Landscaping
      • Fencing: Fenced
      • Has view: Yes
      • View description: Water, Bay, Harbor, Marsh, Ocean
      • Has water view: Yes
      • Water view: Bay,Harbor,Marsh,Ocean,Water
      • Waterfront features: Waterfront, Bay, Ocean, 1/10 to 3/10 To Beach, Beach Ownership(Public)
      Lot
      • Size: 5,336 Square Feet
      • Features: Other
      Details
      • Parcel number: M:0022 B:0091 L:0000,1421230
      • Zoning: Res

      Construction

      Type & style
      • Home type: MultiFamily
      • Property subtype: Multi Family
      Materials
      • Foundation: Brick/Mortar
      • Roof: Rubber
      Condition
      • Year built: 1920

      Utilities & green energy

      • Electric: Circuit Breakers, Individually Metered
      • Sewer: Public Sewer
      • Water: Public

      Community & HOA

      Location
      • Region: Winthrop

      Financial & listing details

      • Price per square foot: $379/sqft
      • Tax assessed value: $891,200
      • Annual tax amount: $9,928
      • Date on market: 6/3/2026
      • Total actual rent: 7100

        Estimated market value

        $981,000

        $932,000 - $1.03M

        $3,712/mo

        Price history

        DateEventPrice
        7/10/2026Price change$999,888-16.6%$379/sqft
        Source: MLS PIN #73529063 Report a problem
        6/3/2026Listed for sale$1,199,000+31%$455/sqft
        Source: MLS PIN #73529063 Report a problem
        4/8/2024Sold$915,000+1.7%$347/sqft
        Source: MLS PIN #73204490 Report a problem
        3/4/2024Contingent$900,000$342/sqft
        Source: MLS PIN #73204490 Report a problem
        2/22/2024Listed for sale$900,000+80%$342/sqft
        Source: MLS PIN #73204490 Report a problem
        10/27/2023Sold$500,000$190/sqft
        Source: Public Record Report a problem

        Public tax history

        YearProperty taxesTax assessment
        2025$9,535 +7.4%$923,900 +8.4%
        2024$8,879 -7.9%$852,100 -5.4%
        2023$9,643 +1.7%$901,200 +11.8%
        2022$9,480 +2.7%$806,100 +10.8%
        2021$9,227 +2%$727,700 +1.5%
        2020$9,045 +2.3%$716,700 +6.8%
        2019$8,842 +10.9%$670,900 +19.2%
        2018$7,971 +9.3%$562,900 +11.2%
        2017$7,291 +6%$506,000 +13%
        2016$6,880 +12.1%$447,600 +4.6%
        2015$6,136 +11%$427,900 +15.4%
        2013$5,529 -1.9%$370,800 -4.7%
        2012$5,635 +13.6%$388,900 +8.2%
        2011$4,961 -1%$359,500 -8.9%
        2010$5,010 +18.5%$394,500 -7%
        2009$4,228 +0.4%$424,100 -6.4%
        2008$4,212 +2.5%$452,900 -2.8%
        2007$4,109 +4.6%$465,900 +2.4%
        2006$3,929 +14.9%$454,800 +20%
        2005$3,419 +1.2%$379,000 +17.4%
        2004$3,378 +2.1%$322,900
        2003$3,310 +7.9%$322,900 +66.4%
        2002$3,067 +28.2%$194,100
        2000$2,393 $194,100
        Find assessor info on the county website

        Monthly payment

        Est. payment

        Payment breakdown

        Explore the cost of this home by adjusting the details. Changes won't be saved.
        All calculations are estimates and provided by Zillow, Inc. for informational purposes only. Actual amounts may vary.
        HOA fees may include property taxes on listings classified as Co-Ops. Contact the listing agent and/or owner for fee details.
        Mortgage interest rates are dependent on a number of factors, including credit score, down payment, and repayment length. Interest rate data provided by Zillow Group Marketplace, Inc. as of 1/1/1970 from various mortgage lenders with which we have lead or other similar arrangements; the Estimated Payment is an average of those rates.
        See how much you could borrow to make a competitive offer.
        Get pre-qualified

        Climate risks

        Neighborhood: 02152

        Getting around

        74 / 100
        Very Walkable
        41 / 100
        Somewhat Bikeable

        Nearby schools

        GreatSchools rating

        A local agent can set up tours, give advice and negotiate with sellers.

        Browse local experts

        Similar homes

              Nearby cities

              Nearby zip codes

              Other Winthrop Topics

                Search
                Updates
                Favorites
                Plan
                Inbox