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  • 27 Dudley St, Boston, Massachusetts, 14 Bedrooms Bedrooms, 28 Rooms Rooms,11 BathroomsBathrooms,Residential Income,For Sale,Dudley St,73343819
  • 27 Dudley St, Boston, Massachusetts, 14 Bedrooms Bedrooms, 28 Rooms Rooms,11 BathroomsBathrooms,Residential Income,For Sale,Dudley St,73343819
  • 27 Dudley St, Boston, Massachusetts, 14 Bedrooms Bedrooms, 28 Rooms Rooms,11 BathroomsBathrooms,Residential Income,For Sale,Dudley St,73343819
  • 27 Dudley St, Boston, Massachusetts, 14 Bedrooms Bedrooms, 28 Rooms Rooms,11 BathroomsBathrooms,Residential Income,For Sale,Dudley St,73343819
  • 27 Dudley St, Boston, Massachusetts, 14 Bedrooms Bedrooms, 28 Rooms Rooms,11 BathroomsBathrooms,Residential Income,For Sale,Dudley St,73343819
  • 27 Dudley St, Boston, Massachusetts, 14 Bedrooms Bedrooms, 28 Rooms Rooms,11 BathroomsBathrooms,Residential Income,For Sale,Dudley St,73343819
  • 27 Dudley St, Boston, Massachusetts, 14 Bedrooms Bedrooms, 28 Rooms Rooms,11 BathroomsBathrooms,Residential Income,For Sale,Dudley St,73343819
  • 27 Dudley St, Boston, Massachusetts, 14 Bedrooms Bedrooms, 28 Rooms Rooms,11 BathroomsBathrooms,Residential Income,For Sale,Dudley St,73343819
  • 27 Dudley St, Boston, Massachusetts, 14 Bedrooms Bedrooms, 28 Rooms Rooms,11 BathroomsBathrooms,Residential Income,For Sale,Dudley St,73343819
  • 27 Dudley St, Boston, Massachusetts, 14 Bedrooms Bedrooms, 28 Rooms Rooms,11 BathroomsBathrooms,Residential Income,For Sale,Dudley St,73343819
  • 27 Dudley St, Boston, Massachusetts, 14 Bedrooms Bedrooms, 28 Rooms Rooms,11 BathroomsBathrooms,Residential Income,For Sale,Dudley St,73343819
  • 27 Dudley St, Boston, Massachusetts, 14 Bedrooms Bedrooms, 28 Rooms Rooms,11 BathroomsBathrooms,Residential Income,For Sale,Dudley St,73343819
  • 27 Dudley St, Boston, Massachusetts, 14 Bedrooms Bedrooms, 28 Rooms Rooms,11 BathroomsBathrooms,Residential Income,For Sale,Dudley St,73343819
  • 27 Dudley St, Boston, Massachusetts, 14 Bedrooms Bedrooms, 28 Rooms Rooms,11 BathroomsBathrooms,Residential Income,For Sale,Dudley St,73343819
  • 27 Dudley St, Boston, Massachusetts, 14 Bedrooms Bedrooms, 28 Rooms Rooms,11 BathroomsBathrooms,Residential Income,For Sale,Dudley St,73343819
  • 27 Dudley St, Boston, Massachusetts, 14 Bedrooms Bedrooms, 28 Rooms Rooms,11 BathroomsBathrooms,Residential Income,For Sale,Dudley St,73343819
  • 27 Dudley St, Boston, Massachusetts, 14 Bedrooms Bedrooms, 28 Rooms Rooms,11 BathroomsBathrooms,Residential Income,For Sale,Dudley St,73343819
  • 27 Dudley St, Boston, Massachusetts, 14 Bedrooms Bedrooms, 28 Rooms Rooms,11 BathroomsBathrooms,Residential Income,For Sale,Dudley St,73343819
  • 27 Dudley St, Boston, Massachusetts, 14 Bedrooms Bedrooms, 28 Rooms Rooms,11 BathroomsBathrooms,Residential Income,For Sale,Dudley St,73343819
  • 27 Dudley St, Boston, Massachusetts, 14 Bedrooms Bedrooms, 28 Rooms Rooms,11 BathroomsBathrooms,Residential Income,For Sale,Dudley St,73343819
  • 27 Dudley St, Boston, Massachusetts, 14 Bedrooms Bedrooms, 28 Rooms Rooms,11 BathroomsBathrooms,Residential Income,For Sale,Dudley St,73343819
  • 27 Dudley St, Boston, Massachusetts, 14 Bedrooms Bedrooms, 28 Rooms Rooms,11 BathroomsBathrooms,Residential Income,For Sale,Dudley St,73343819
  • 27 Dudley St, Boston, Massachusetts, 14 Bedrooms Bedrooms, 28 Rooms Rooms,11 BathroomsBathrooms,Residential Income,For Sale,Dudley St,73343819
  • 27 Dudley St, Boston, Massachusetts, 14 Bedrooms Bedrooms, 28 Rooms Rooms,11 BathroomsBathrooms,Residential Income,For Sale,Dudley St,73343819
  • 27 Dudley St, Boston, Massachusetts, 14 Bedrooms Bedrooms, 28 Rooms Rooms,11 BathroomsBathrooms,Residential Income,For Sale,Dudley St,73343819
  • 27 Dudley St, Boston, Massachusetts, 14 Bedrooms Bedrooms, 28 Rooms Rooms,11 BathroomsBathrooms,Residential Income,For Sale,Dudley St,73343819
  • 27 Dudley St, Boston, Massachusetts, 14 Bedrooms Bedrooms, 28 Rooms Rooms,11 BathroomsBathrooms,Residential Income,For Sale,Dudley St,73343819
  • 27 Dudley St, Boston, Massachusetts, 14 Bedrooms Bedrooms, 28 Rooms Rooms,11 BathroomsBathrooms,Residential Income,For Sale,Dudley St,73343819
  • 27 Dudley St, Boston, Massachusetts, 14 Bedrooms Bedrooms, 28 Rooms Rooms,11 BathroomsBathrooms,Residential Income,For Sale,Dudley St,73343819
  • 27 Dudley St, Boston, Massachusetts, 14 Bedrooms Bedrooms, 28 Rooms Rooms,11 BathroomsBathrooms,Residential Income,For Sale,Dudley St,73343819
  • 27 Dudley St, Boston, Massachusetts, 14 Bedrooms Bedrooms, 28 Rooms Rooms,11 BathroomsBathrooms,Residential Income,For Sale,Dudley St,73343819
  • 27 Dudley St, Boston, Massachusetts, 14 Bedrooms Bedrooms, 28 Rooms Rooms,11 BathroomsBathrooms,Residential Income,For Sale,Dudley St,73343819
  • 27 Dudley St, Boston, Massachusetts, 14 Bedrooms Bedrooms, 28 Rooms Rooms,11 BathroomsBathrooms,Residential Income,For Sale,Dudley St,73343819
  • 27 Dudley St, Boston, Massachusetts, 14 Bedrooms Bedrooms, 28 Rooms Rooms,11 BathroomsBathrooms,Residential Income,For Sale,Dudley St,73343819
  • 27 Dudley St, Boston, Massachusetts, 14 Bedrooms Bedrooms, 28 Rooms Rooms,11 BathroomsBathrooms,Residential Income,For Sale,Dudley St,73343819
  • 27 Dudley St, Boston, Massachusetts, 14 Bedrooms Bedrooms, 28 Rooms Rooms,11 BathroomsBathrooms,Residential Income,For Sale,Dudley St,73343819
  • 27 Dudley St, Boston, Massachusetts, 14 Bedrooms Bedrooms, 28 Rooms Rooms,11 BathroomsBathrooms,Residential Income,For Sale,Dudley St,73343819
  • 27 Dudley St, Boston, Massachusetts, 14 Bedrooms Bedrooms, 28 Rooms Rooms,11 BathroomsBathrooms,Residential Income,For Sale,Dudley St,73343819
  • 27 Dudley St, Boston, Massachusetts, 14 Bedrooms Bedrooms, 28 Rooms Rooms,11 BathroomsBathrooms,Residential Income,For Sale,Dudley St,73343819
  • 27 Dudley St, Boston, Massachusetts, 14 Bedrooms Bedrooms, 28 Rooms Rooms,11 BathroomsBathrooms,Residential Income,For Sale,Dudley St,73343819
  • 27 Dudley St, Boston, Massachusetts, 14 Bedrooms Bedrooms, 28 Rooms Rooms,11 BathroomsBathrooms,Residential Income,For Sale,Dudley St,73343819
Property Description

27 Dudley Street | Roxbury’s Fort Hill | 7-Unit | 14 Beds | 11 Baths | $24,250/Month Income | 7.2% Cap Rate Projected by 9/1/25. Step into a high-performing investment with historic flair. Once home to Maurice Starr—where New Kids on the Block and New Edition recorded—27 Dudley Street blends cultural legacy with cash flow in Roxbury’s Fort Hill.This fully renovated seven-unit property is located in a federally designated Opportunity Zone, offering potential tax benefits. Gut-renovated in 2021, each unit features high-end finishes: waterfall quartz countertops, central HVAC, in-unit laundry, hardwood floors, and 8+ off-street parking spaces. By September 1, 2025, the property is projected to generate $24,250/month in rental income with a 7.2% cap rate. Located near public transit, universities, and Longwood Medical, this is a rare turnkey opportunity in one of Boston’s most dynamic growth corridors. Full pro forma and unit breakdown available upon request.

Features
: Central
: Central Air
: Off Street, Paved Drive
: Disposal, Range, Dishwasher, Microwave, Refrigerator, Washer, Dryer
: Brick
: Tile, Wood
: Public Sewer
: Public
: Kitchen, Dining Room, Living Room, Laundry Room
: Unknown
: Washer Hookup, Electric Dryer Hookup
Additional Information
Roxbury's Fort Hill
39
8
2025
Active
$568
R4
7
$3,800,000
: Yes
No
Active
Address Map
Boston
Massachusetts
Suffolk
02119
W72° 54' 39.7''
N42° 19' 45.3''
  • Google Map

Residential Income

27 Dudley St, Boston, Massachusetts

14 Bedrooms
11 Bathrooms
8,241 Sqft
$3,700,000
Listing ID #73343819
Basic Details
Property Type : Residential Income
Listing Type : For Sale
Price : $3,700,000
Bedrooms : 14
Rooms : 28
Bathrooms : 11
Square Footage : 8,241 Sqft
Year Built : 1900
Lot Area : 0.19 Acre
Listing ID : 73343819
BathroomsFull : 11
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Agent info
  • 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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