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 $23,125/month with a 6.3% cap rate and a projected 7.3% 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.
Listed by Eric W. Johnson
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Compass
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203-893-8316
Listed by William MacDonald
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Compass
Listed by Mission Realty Advisors
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Compass
Last updated October 17, 2025
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Source: MLSPin #73435766
Listing Facts
TypeMulti-family
NeighborhoodHighland Park
Bedrooms14
Bathrooms11
Days on Prevu27
Taxes$23,245.5/year
Size6,509 sqft
Price per sqft$568
Amenities
Dishwasher
Washer/Dryer
Air Conditioning
Parking
Swimming Pool
Location
Mortgage Calculator
Listing History
09/25/2025
Listed by Compass
$3,700,000
Property Details for 27 Dudley St
Association
Amenities
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
Interior Features: Living Room, Dining Room, Kitchen, Laundry Room
Measurements
Living Area: 6,509
Living Area Source: Measured
Rooms
Bathrooms Full: 11
Bathrooms Total Integer: 11
Bedrooms Total: 14
Rooms Total: 28
Parking
Parking
Open Parking: Yes
Parking Features: Paved Drive, Off Street
Parking Total: 8
Utilities
Equipment
Cooling: Central Air
Has Cooling: Yes
Heating: Central
Has Heating: Yes
Laundry Features: Electric Dryer Hookup, Washer Hookup
Sewer: Public Sewer
Utilities: For Gas Range, For Gas Oven, For Electric Dryer, Washer Hookup
Water Source: Public
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