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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.

More Info

Basic Information

  • Gross Income $291,000
  • Lot Features Corner Lot
  • Mls StatusUnder Agreement
  • Parcel Number W:09 P:03293 S:000,3397293

Tax Information

  • Tax Assessed Value $2,056,900
  • Tax Year 2026
  • Taxes$25,748

Parking

  • Open Parking YN Yes
  • Parking Features Paved Drive, Off Street
  • Parking Spaces8

Rooms

  • Bathroom11
  • Bathrooms Total Decimal 11
  • Bedrooms14
  • Full Bath11

Basic Information

  • List Price$3,625,000
  • MLS Number73478206
  • Modification Date05/21/2026
  • Property SubType5-9 Family
  • Purchase Contract Date05/21/2026
  • Virtual TourView Tour

Location

  • Address27 Dudley Street
  • Building Number27
  • CountySuffolk
  • NeighborhoodRoxbury's Fort Hill
  • StateMA
  • StreetDudley Street
  • SubdivisionRoxbury's Fort Hill
  • TownBoston
  • Zip02119

Building

  • Building Area Units Square Feet
  • Construction Materials Brick
  • FoundationBrick/Mortar
  • Levels 8
  • Rooms28
  • Stories8
  • Units7
  • Utilities For Gas Range, For Gas Oven, For Electric Dryer, Washer Hookup
  • Window Features Insulated Windows
  • Year Built1900
  • Year Built Details Approximate
  • Year Built Source Public Records

Property

  • Acreage0.19

Interior

  • Flooring Wood, Tile
  • Interior Features Living Room, Dining Room, Kitchen, Laundry Room

Exterior

  • Fencing Fenced
  • RoofShingle, Rubber

Utilities

  • Cooling Central Air
  • Cooling YN Yes
  • Heat SystemYes
  • Heating Central
  • Sewer Public Sewer
  • Water Source Public

Property Information

  • Building Area Source Measured
  • Living Area 6,509
  • Lot Size Square Feet 8,241
  • Lot Size Units Acres
  • Square Feet6,509

Amenities

  • Amenities
    • Bike Path
    • Conservation Area
    • Highway Access
    • House of Worship
    • Laundromat
    • Marina
    • Medical Facility
    • Other
    • Park
    • Pool
    • Private School
    • Public School
    • Public Transportation
    • Shopping
    • T-Station
    • Tennis Court(s)
    • University
    • Walk/Jog Trails
  • Appliances IncludedRange, Dishwasher, Disposal, Microwave, Refrigerator, Washer, Dryer
  • Other AmenitiesTennis

Legal

  • ZoningR4

Other

  • Date Listed02/18/2026
  • Farm Land Area Units Square Feet
  • View Count5

Map Location

Driving Directions

Listed by Mission Realty Advisors of Compass

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