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  • 27 Dudley St, Boston, Massachusetts, 14 Bedrooms Bedrooms, 28 Rooms Rooms,11 BathroomsBathrooms,Residential Income,For Sale,Dudley St,73478206
  • 27 Dudley St, Boston, Massachusetts, 14 Bedrooms Bedrooms, 28 Rooms Rooms,11 BathroomsBathrooms,Residential Income,For Sale,Dudley St,73478206
  • 27 Dudley St, Boston, Massachusetts, 14 Bedrooms Bedrooms, 28 Rooms Rooms,11 BathroomsBathrooms,Residential Income,For Sale,Dudley St,73478206
  • 27 Dudley St, Boston, Massachusetts, 14 Bedrooms Bedrooms, 28 Rooms Rooms,11 BathroomsBathrooms,Residential Income,For Sale,Dudley St,73478206
  • 27 Dudley St, Boston, Massachusetts, 14 Bedrooms Bedrooms, 28 Rooms Rooms,11 BathroomsBathrooms,Residential Income,For Sale,Dudley St,73478206
  • 27 Dudley St, Boston, Massachusetts, 14 Bedrooms Bedrooms, 28 Rooms Rooms,11 BathroomsBathrooms,Residential Income,For Sale,Dudley St,73478206
  • 27 Dudley St, Boston, Massachusetts, 14 Bedrooms Bedrooms, 28 Rooms Rooms,11 BathroomsBathrooms,Residential Income,For Sale,Dudley St,73478206
  • 27 Dudley St, Boston, Massachusetts, 14 Bedrooms Bedrooms, 28 Rooms Rooms,11 BathroomsBathrooms,Residential Income,For Sale,Dudley St,73478206
  • 27 Dudley St, Boston, Massachusetts, 14 Bedrooms Bedrooms, 28 Rooms Rooms,11 BathroomsBathrooms,Residential Income,For Sale,Dudley St,73478206
  • 27 Dudley St, Boston, Massachusetts, 14 Bedrooms Bedrooms, 28 Rooms Rooms,11 BathroomsBathrooms,Residential Income,For Sale,Dudley St,73478206
  • 27 Dudley St, Boston, Massachusetts, 14 Bedrooms Bedrooms, 28 Rooms Rooms,11 BathroomsBathrooms,Residential Income,For Sale,Dudley St,73478206
  • 27 Dudley St, Boston, Massachusetts, 14 Bedrooms Bedrooms, 28 Rooms Rooms,11 BathroomsBathrooms,Residential Income,For Sale,Dudley St,73478206
  • 27 Dudley St, Boston, Massachusetts, 14 Bedrooms Bedrooms, 28 Rooms Rooms,11 BathroomsBathrooms,Residential Income,For Sale,Dudley St,73478206
  • 27 Dudley St, Boston, Massachusetts, 14 Bedrooms Bedrooms, 28 Rooms Rooms,11 BathroomsBathrooms,Residential Income,For Sale,Dudley St,73478206
  • 27 Dudley St, Boston, Massachusetts, 14 Bedrooms Bedrooms, 28 Rooms Rooms,11 BathroomsBathrooms,Residential Income,For Sale,Dudley St,73478206
  • 27 Dudley St, Boston, Massachusetts, 14 Bedrooms Bedrooms, 28 Rooms Rooms,11 BathroomsBathrooms,Residential Income,For Sale,Dudley St,73478206
  • 27 Dudley St, Boston, Massachusetts, 14 Bedrooms Bedrooms, 28 Rooms Rooms,11 BathroomsBathrooms,Residential Income,For Sale,Dudley St,73478206
  • 27 Dudley St, Boston, Massachusetts, 14 Bedrooms Bedrooms, 28 Rooms Rooms,11 BathroomsBathrooms,Residential Income,For Sale,Dudley St,73478206
  • 27 Dudley St, Boston, Massachusetts, 14 Bedrooms Bedrooms, 28 Rooms Rooms,11 BathroomsBathrooms,Residential Income,For Sale,Dudley St,73478206
  • 27 Dudley St, Boston, Massachusetts, 14 Bedrooms Bedrooms, 28 Rooms Rooms,11 BathroomsBathrooms,Residential Income,For Sale,Dudley St,73478206
  • 27 Dudley St, Boston, Massachusetts, 14 Bedrooms Bedrooms, 28 Rooms Rooms,11 BathroomsBathrooms,Residential Income,For Sale,Dudley St,73478206
  • 27 Dudley St, Boston, Massachusetts, 14 Bedrooms Bedrooms, 28 Rooms Rooms,11 BathroomsBathrooms,Residential Income,For Sale,Dudley St,73478206
  • 27 Dudley St, Boston, Massachusetts, 14 Bedrooms Bedrooms, 28 Rooms Rooms,11 BathroomsBathrooms,Residential Income,For Sale,Dudley St,73478206
  • 27 Dudley St, Boston, Massachusetts, 14 Bedrooms Bedrooms, 28 Rooms Rooms,11 BathroomsBathrooms,Residential Income,For Sale,Dudley St,73478206
  • 27 Dudley St, Boston, Massachusetts, 14 Bedrooms Bedrooms, 28 Rooms Rooms,11 BathroomsBathrooms,Residential Income,For Sale,Dudley St,73478206
  • 27 Dudley St, Boston, Massachusetts, 14 Bedrooms Bedrooms, 28 Rooms Rooms,11 BathroomsBathrooms,Residential Income,For Sale,Dudley St,73478206
  • 27 Dudley St, Boston, Massachusetts, 14 Bedrooms Bedrooms, 28 Rooms Rooms,11 BathroomsBathrooms,Residential Income,For Sale,Dudley St,73478206
  • 27 Dudley St, Boston, Massachusetts, 14 Bedrooms Bedrooms, 28 Rooms Rooms,11 BathroomsBathrooms,Residential Income,For Sale,Dudley St,73478206
  • 27 Dudley St, Boston, Massachusetts, 14 Bedrooms Bedrooms, 28 Rooms Rooms,11 BathroomsBathrooms,Residential Income,For Sale,Dudley St,73478206
  • 27 Dudley St, Boston, Massachusetts, 14 Bedrooms Bedrooms, 28 Rooms Rooms,11 BathroomsBathrooms,Residential Income,For Sale,Dudley St,73478206
  • 27 Dudley St, Boston, Massachusetts, 14 Bedrooms Bedrooms, 28 Rooms Rooms,11 BathroomsBathrooms,Residential Income,For Sale,Dudley St,73478206
  • 27 Dudley St, Boston, Massachusetts, 14 Bedrooms Bedrooms, 28 Rooms Rooms,11 BathroomsBathrooms,Residential Income,For Sale,Dudley St,73478206
  • 27 Dudley St, Boston, Massachusetts, 14 Bedrooms Bedrooms, 28 Rooms Rooms,11 BathroomsBathrooms,Residential Income,For Sale,Dudley St,73478206
  • 27 Dudley St, Boston, Massachusetts, 14 Bedrooms Bedrooms, 28 Rooms Rooms,11 BathroomsBathrooms,Residential Income,For Sale,Dudley St,73478206
  • 27 Dudley St, Boston, Massachusetts, 14 Bedrooms Bedrooms, 28 Rooms Rooms,11 BathroomsBathrooms,Residential Income,For Sale,Dudley St,73478206
  • 27 Dudley St, Boston, Massachusetts, 14 Bedrooms Bedrooms, 28 Rooms Rooms,11 BathroomsBathrooms,Residential Income,For Sale,Dudley St,73478206
  • 27 Dudley St, Boston, Massachusetts, 14 Bedrooms Bedrooms, 28 Rooms Rooms,11 BathroomsBathrooms,Residential Income,For Sale,Dudley St,73478206
  • 27 Dudley St, Boston, Massachusetts, 14 Bedrooms Bedrooms, 28 Rooms Rooms,11 BathroomsBathrooms,Residential Income,For Sale,Dudley St,73478206
  • 27 Dudley St, Boston, Massachusetts, 14 Bedrooms Bedrooms, 28 Rooms Rooms,11 BathroomsBathrooms,Residential Income,For Sale,Dudley St,73478206
  • 27 Dudley St, Boston, Massachusetts, 14 Bedrooms Bedrooms, 28 Rooms Rooms,11 BathroomsBathrooms,Residential Income,For Sale,Dudley St,73478206
  • 27 Dudley St, Boston, Massachusetts, 14 Bedrooms Bedrooms, 28 Rooms Rooms,11 BathroomsBathrooms,Residential Income,For Sale,Dudley St,73478206
  • 27 Dudley St, Boston, Massachusetts, 14 Bedrooms Bedrooms, 28 Rooms Rooms,11 BathroomsBathrooms,Residential Income,For Sale,Dudley St,73478206
Property Description

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.

Features
Heating System:
Central
Cooling System:
Central Air
Parking:
Off Street, Paved Drive
Appliances:
Disposal, Range, Dishwasher, Microwave, Refrigerator, Washer, Dryer
Construction:
Brick
Flooring:
Tile, Wood
Sewer:
Public Sewer
Water:
Public
Garage Parking
Interior Features:
Kitchen, Dining Room, Living Room, Laundry Room
Lead Paint:
Unknown
Laundry Features:
Washer Hookup, Electric Dryer Hookup
Additional Information
Area:
Roxbury's Fort Hill
Market Time:
8
Parking Spaces:
8
Tax Year:
2026
Status:
Active
Price Per Sqft:
$557
Zoning:
R4
No Units:
7
Orig Price:
$3,625,000
LEASE:
Yes
Waterfront:
No
MlsStatus:
Active
Address Map
City:
Boston
State:
MA
County:
Suffolk
Postal Code:
02119
Longitude:
W72° 54' 39.7''
Latitude:
N42° 19' 45.3''
  • Google Map

Residential Income

27 Dudley St, Boston, Massachusetts

14 Bedrooms
11 Total Bathrooms
6,509 Sqft
$3,625,000
Listing ID #73478206
Basic Details
Property Type :
Residential Income
Listing Type :
For Sale
Price :
$3,625,000
Bedrooms :
14
Rooms :
28
Total Bathrooms :
11
Full Bathrooms :
11
Square Footage :
6,509 Sqft
Year Built :
1900
Lot Area :
0.19 Acre
Listing ID :
73478206
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Agent info
Robb Enterprises
  • Stephen E. Robb
  • View website
  • 617-212-0251
  • srobb@robbenterprises.com

Contact Agent

The property listing data and information set forth herein were provided to MLS Property Information Network, Inc. from third party sources, including sellers, lessors and public records, and were compiled by MLS Property Information Network, Inc. The property listing data and information are for the personal, non commercial use of consumers having a good faith interest in purchasing or leasing listed properties of the type displayed to them and may not be used for any purpose other than to identify prospective properties which such consumers may have a good faith interest in purchasing or leasing. MLS Property Information Network, Inc. and its subscribers disclaim any and all representations and warranties as to the accuracy of the property listing data and information set forth herein.

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