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For sale
    • $3,625,000

    27 Dudley St, Roxbury, MA 02119

    14beds
    6,509sqft
    : 
    5-9 Family
    Built in 1900
    -- sqft lot
    $-- Zestimate®
    $557/sqft
    $-- HOA

    What's special

    Modern finishesCentral hvacIn-unit laundryHardwood floorsWaterfall quartz countertops
    A rare turnkey 7-unit investment property with cultural significance, 27 Dudley Street was once home to Maurice Starr where New Kids on the Block and New Edition rehearsed and recorded. Fully gut-renovated in 2021, it delivers modern finishes including waterfall quartz countertops, central HVAC, in-unit laundry, hardwood floors, and 8+ off-street parking spaces, ensuring strong tenant demand. Generating $22,825/month with a 6.3% cap rate and a projected 7.3% cap rate by 9/1/26, it combines reliable cash flow with potential Opportunity Zone tax advantages. Positioned near public transit, universities, and Longwood Medical Area, this asset offers cultural legacy, premium quality, and growth potential in one of Boston’s fastest-growing neighborhoods. Ideal for 1031 exchange buyers or investors seeking a stable, high-performing asset with long-term appreciation potential. Full pro forma and unit breakdown available on request.
    40 days
    |
    386
    |
    15
    |

    Zillow last checked: 7 hours ago

    Listing updated: February 27, 2026 at 01:26pm

    Listed by:

    Mission Realty Advisors 617-942-1609,

    Compass 617-752-6845

    Source: MLS PIN,MLS#: 73478206

    Tour with a local agent

      Facts & features

      Interior

      Bedrooms & bathrooms
      • Bedrooms: 14
      • Bathrooms: 11
      • Full bathrooms: 11
      Heating
      • Central
      Cooling
      • Central Air
      Appliances
      • Included: Range, Dishwasher, Disposal, Microwave, Refrigerator, Washer, Dryer
      • Laundry: Electric Dryer Hookup, Washer Hookup
      Features
      • Living Room, Dining Room, Kitchen, Laundry Room
      • Flooring: Wood, Tile
      • Windows: Insulated Windows
      • Has basement: No
      • Has fireplace: No
      Interior area
      • Total structure area: 6,509
      • Total interior livable area: 6,509 sqft
      • Finished area above ground: 5,291
      • Finished area below ground: 1,218

      Property

      Parking
      • Total spaces: 8
      • Parking features: Paved Drive, Off Street
      • Uncovered spaces: 8
      Features
      • Fencing: Fenced
      Lot
      • Size: 8,241 Square Feet
      • Features: Corner Lot
      Details
      • Parcel number: W:09 P:03293 S:000,3397293
      • Zoning: R4

      Construction

      Type & style
      • Home type: MultiFamily
      • Property subtype: 5-9 Family
      Materials
      • Brick
      • Foundation: Brick/Mortar
      • Roof: Shingle,Rubber
      Condition
      • Year built: 1900

      Utilities & green energy

      • Sewer: Public Sewer
      • Water: Public
      • Utilities for property: for Gas Range, for Gas Oven, for Electric Dryer, Washer Hookup

      Community & HOA

      Community
      • Features: Public Transportation, Shopping, Pool, Tennis Court(s), Park, Walk/Jog Trails, Medical Facility, Laundromat, Bike Path, Conservation Area, Highway Access, House of Worship, Marina, Private School, Public School, T-Station, University, Other
      Location
      • Region: Roxbury

      Financial & listing details

      • Price per square foot: $557/sqft
      • Tax assessed value: $2,056,900
      • Annual tax amount: $25,748
      • Date on market: 3/1/2026
      • Total actual rent: 22825
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        Estimated market value

        Not available

        Estimated sales range

        Not available

        $4,035/mo

        Price history

        Price history
        DateEventPrice
        2/18/2026Listed for sale$3,625,000-2%$557/sqft
        Source: MLS PIN #73478206 Report a problem
        12/21/2025Listing removed$3,700,000$568/sqft
        Source: MLS PIN #73435766 Report a problem
        9/25/2025Listed for sale$3,700,000$568/sqft
        Source: MLS PIN #73435766 Report a problem
        8/11/2025Listing removed$3,700,000$568/sqft
        Source: MLS PIN #73343819 Report a problem
        4/15/2025Price change$3,700,000-2.6%$568/sqft
        Source: MLS PIN #73343819 Report a problem
        3/11/2025Listed for sale$3,800,000-5%$584/sqft
        Source: MLS PIN #73343819 Report a problem
        6/3/2022Listing removed--
        Source: MLS PIN #72865029 Report a problem
        1/1/2022Listing removed$4,000,000$615/sqft
        Source: MLS PIN #72865029 Report a problem
        9/21/2021Listed for sale$4,000,000+201.9%$615/sqft
        Source: MLS PIN #72865029 Report a problem
        5/1/2020Listing removed$3,330$1/sqft
        Source: Kirby Taylor Properties Report a problem
        4/10/2020Listed for rent$3,330+51.4%$1/sqft
        Source: Kirby Taylor Properties Report a problem
        2/1/2018Listing removed$2,200
        Source: Weichert Realtors Hudson Morgan Group Report a problem
        1/2/2018Listed for rent$2,200
        Source: Weichert Realtors Hudson Morgan Group Report a problem
        9/14/2017Sold$1,325,000+1.9%$204/sqft
        Source: Public Record Report a problem
        6/22/2017Pending sale$1,300,000$200/sqft
        Source: Preferred Real Estate Group #72181478 Report a problem
        6/14/2017Listed for sale$1,300,000+203.7%$200/sqft
        Source: Preferred Real Estate Group #72181478 Report a problem
        1/31/2003Sold$428,000$66/sqft
        Source: Public Record Report a problem

        Public tax history

        Public tax history
        YearProperty taxesTax assessment
        2025$23,027 +2.3%$1,988,500 -3.7%
        2024$22,516 0%$2,065,700 -1.5%
        2023$22,522 +1.9%$2,097,000 +3.3%
        2022$22,092 +3.4%$2,030,500 +1.4%
        2021$21,363 +54.5%$2,002,200 +52.9%
        2020$13,826 +47.5%$1,309,300 +47.3%
        2019$9,371 +24.7%$889,105 +24%
        2018$7,516 +499.7%$717,155 +1%
        2017$1,253 -82%$710,125 +12%
        2016$6,974 +34%$634,030 +47.5%
        2015$5,205 $429,780 +58.6%
        2011-- $271,000 -0.9%
        2010-- $273,500 -4.4%
        2009-- $286,000
        2008-- $286,000 +1.4%
        2007-- $282,000

        Find assessor info on the county website

        Monthly payment

        Est. payment
        $20,462/mo
        Principal & interest
        $18498
        Property taxes
        $1964
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          Climate risks

          Neighborhood: Roxbury

          Getting around

          82 / 100
          Very Walkable
          72 / 100
          Very Bikeable

          Nearby schools

          GreatSchools rating

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