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.
Property Details
Price:
$3,625,000
MLS #:
73478206
Status:
Active
Beds:
14
Baths:
11
Type:
Multi Family
Subtype:
5-9 Family
Neighborhood:
roxburysforthill
Listed Date:
Feb 18, 2026
Finished Sq Ft:
6,509
Total Sq Ft:
6,509
Lot Size:
8,241 sqft / 0.19 acres (approx)
Year Built:
1900
Units:
7
See this Listing
Schools
Interior
Above Grade Finished Area
5291
Appliances
Range, Dishwasher, Disposal, Microwave, Refrigerator, Washer, Dryer
Bathrooms
11 Full Bathrooms
Below Grade Finished Area
1218
Cooling
Central Air
Flooring
Wood, Tile
Heating
Central
Interior Features
Living Room, Dining Room, Kitchen, Laundry Room
Laundry Features
Electric Dryer Hookup, Washer Hookup
Levels
8
Exterior
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
Construction Materials
Brick
Fencing
Fenced
Lot Features
Corner Lot
Open Parking Spaces
8
Open Parking YN
1
Parking Features
Paved Drive, Off Street
Parking Spots
8
Parking Total
8
Roof
Shingle, Rubber
Stories
8
Window Features
Insulated Windows
Financial
Tax Year
2026
Taxes
$25,748
Map
Community
- Address27 Dudley St Boston MA
- CityBoston
- CountySuffolk
- Zip Code02119
Subdivisions in Boston
- Adams Village
- Ashmont Hill
- Ashmont Hill / Carruth Area
- Back Bay
- Bay Village
- Beacon Hill
- Bellevue Hill
- Boston
- Brighton-Oak Square
- Charlestown
- Chestnut Hill
- Chestnut Hill /Brookline line
- Chestnut Hill Park Condominium
- Clam Point Neighborhood
- Eight Streets Neighborhood
- Ellis South End Neighborhood
- Fairmount Hill
- Fields Corner
- Gas Light District
- Golf Course Neighborhood
- Harbor View
- Harborview
- Highland
- Hyde Park
- Jamaica Plain
- Lower Mills
- Melville Park
- Metropolitan Heights Area
- Metropolitan Hill
- Mission Hill – Longwood Medical
- Oak Square
- Parkway neighborhood
- Roslindale
- Roslindale – WC Bates
- roslindale village
- Roxbury’s Moreland Street Historic District
- Savin Hill: Minutes to Carson Beach/UMass Boston T-Stop
- South Boston
- Suffolk County
- Sumner Hill
- Thomas Park
- Woodbourne
Market Summary
Current real estate data for Multi Family in Boston as of Apr 08, 2026
325
Multi Family Listed
153
Avg DOM
489
Avg $ / SqFt
$2,355,383
Avg List Price
Property Summary
- 27 Dudley St Boston MA is a Multi Family for sale in Boston, MA, 02119. It is listed for $3,625,000 To schedule a showing of MLS#73478206 at 27 Dudley St in Boston, MA, contact your Cornerstone Real Estate agent at 617-238-7400.
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Courtesy of Compass. 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.
27 Dudley St
Boston, MA