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For sale
    • $1,800,000

    86 Chestnut St, Brookline, MA 02445

    10beds
    3,681sqft
    : 
    $11,498/mo
    Get pre-qualified
    3 Family
    Built in 1900
    -- sqft lot
    $1,703,600 Zestimate®
    $489/sqft
    $-- HOA

    What's special

    Modern updatesNew roofUpdated electrical
    Investors, take note! Don't miss this exceptional opportunity to own a three-family property in one of Brookline's most sought-after locations. Situated near Brookline Village, this property is just a 12-minute walk to the Green Line, providing convenient access to Fenway, Downtown Boston, and beyond. The MBTA Route 60 bus to the Longwood Medical Area is just steps from the front door.Enjoy a highly walkable neighborhood with easy access to grocery stores, restaurants, parks, walking trails, and all the amenities that make Brookline such a desirable place to live.The rear porches offer beautiful city views, and with modern updates, this classic property has the potential to truly shine! Major capital improvements completed within the past three years include a new roof, updated electrical, and new heating and hot water systems. Large driveway accommodates multiple cars for easy off street parking. Enjoy the ample yard space for grilling, bonfires, or just taking in the fresh air! Located in a community renowned for its exceptional schools, vibrant neighborhoods, and unbeatable location, this is an investment opportunity you won't want to miss. The property is fully leased through August 31, 2027, providing immediate, stable rental income.
    5 hours
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    67
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    3
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    Zillow last checked:

    Listing updated:

    Listed by:

    Sarah McIntyre 617-794-2045,

    Red Tree Real Estate 617-487-8015

    Source: MLS PIN,MLS#: 73559809

      Facts & features

      Interior

      Bedrooms & bathrooms
      • Bedrooms: 10
      • Bathrooms: 4
      • Full bathrooms: 4
      Heating
      • Natural Gas
      Cooling
      • None
      Appliances
      • Included: Oven, Dishwasher, Refrigerator, Range
      Features
      • Ceiling Fan(s), Pantry, Bathroom With Tub, Studio, Bathroom with Shower Stall, Living Room, Dining Room, Kitchen
      • Flooring: Hardwood, Wood
      • Windows: Insulated Windows
      • Basement: Full,Finished
      • Has fireplace: No
      Interior area
      • Total structure area: 3,681
      • Total interior livable area: 3,681 sqft
      • Finished area above ground: 3,181
      • Finished area below ground: 500

      Property

      Parking
      • Total spaces: 6
      • Parking features: Off Street
      • Uncovered spaces: 6
      Features
      • Patio & porch: Deck - Wood
      Lot
      • Size: 4,500 Square Feet
      • Features: Corner Lot
      Details
      • Parcel number: M:0316 B:0020 L:0000,40929
      • Zoning: M10

      Construction

      Type & style
      • Home type: MultiFamily
      • Property subtype: 3 Family
      Materials
      • Frame
      • Foundation: Granite
      • Roof: Shingle
      Condition
      • Year built: 1900

      Utilities & green energy

      • Electric: Circuit Breakers
      • Sewer: Public Sewer
      • Water: Public

      Community & HOA

      Community
      • Features: Public Transportation, T-Station
      Location
      • Region: Brookline

      Financial & listing details

      • Price per square foot: $489/sqft
      • Tax assessed value: $1,608,900
      • Annual tax amount: $16,475
      • Date on market: 8/6/2026
      • Total actual rent: 8000

        Estimated market value

        $1,703,600

        $1.40M - $2.06M

        $2,341/mo

        Price history

        DateEventPrice
        8/5/2026Listed for sale$1,800,000+125%$489/sqft
        Source: MLS PIN #73559809 Report a problem
        7/6/2026Listing removed$2,200$1/sqft
        Source: Zillow Rentals Report a problem
        6/22/2026Listed for rent$2,200-12%$1/sqft
        Source: Zillow Rentals Report a problem
        5/22/2018Listing removed$2,500$1/sqft
        Source: Arborview Realty Report a problem
        5/12/2018Price change$2,500-6.5%$1/sqft
        Source: Arborview Realty Report a problem
        4/18/2018Listed for rent$2,675+27.4%$1/sqft
        Source: Arborview Realty Report a problem
        10/20/2017Listing removed$2,100$1/sqft
        Source: Nextgen Realty Report a problem
        9/27/2017Price change$2,100-8.7%$1/sqft
        Source: Jacob Realty Report a problem
        8/23/2017Price change$2,300-11.5%$1/sqft
        Source: Jacob Realty Report a problem
        8/15/2017Listed for rent$2,600$1/sqft
        Source: Jacob Realty Report a problem
        4/15/2009Sold$800,000-7%$217/sqft
        Source: Public Record Report a problem
        1/13/2009Listed for sale$860,000$234/sqft
        Source: MLS Property Information Network #70861287 Report a problem

        Public tax history

        YearProperty taxesTax assessment
        2025$15,633 -0.3%$1,583,900 -1.3%
        2024$15,676 +3.5%$1,604,500 +5.6%
        2023$15,147 +2.7%$1,519,300 +5%
        2022$14,744 +8.1%$1,446,900 +4%
        2021$13,635 +5.9%$1,391,300 +2.1%
        2020$12,874 +5.9%$1,362,300 +5%
        2019$12,157 +5.6%$1,297,400 +6.6%
        2018$11,512 +3.4%$1,216,900 +8%
        2017$11,131 +4.3%$1,126,600 +10%
        2016$10,672 +7.3%$1,024,200 +10%
        2015$9,944 -0.7%$931,100 +5.9%
        2014$10,012 +2.7%$879,000 +5%
        2013$9,752 +2.2%$837,100
        2012$9,543 -0.1%$837,100 -1%
        2011$9,556 +3%$845,700
        2010$9,277 +2.6%$845,700 0%
        2009$9,043 +9.4%$845,900 +4.2%
        2008$8,263 +1.9%$811,700 -2.6%
        2007$8,106 +1.8%$833,100 -0.1%
        2006$7,961 +8.8%$833,600 +16.5%
        2005$7,319 +3%$715,400 +7%
        2004$7,106 +4.3%$668,500 +10%
        2003$6,812 +17.6%$607,700 +35.4%
        2002$5,791 -3.3%$448,900 +26.7%
        1999$5,991 $354,300
        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.
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        Climate risks

        Neighborhood: 02445

        Getting around

        72 / 100
        Very Walkable
        65 / 100
        Good Transit
        89 / 100
        Very Bikeable

        Nearby schools

        GreatSchools rating

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