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 $22,925/month with a 6.3% cap rate and a projected 7.2% 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 December 10, 2025
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Source: MLSPin #73435766
Listing Facts
TypeMulti-family
NeighborhoodHighland Park
Bedrooms14
Bathrooms11
Days on Prevu77
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 Spaces: 8
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
Frequently Asked Questions
How many bedrooms and bathrooms does this multi-family home have?
There are 14 bedrooms and 11 bathrooms in this multi-family home at 27 Dudley St.
Does this multi-family home have parking?
Yes, there are 8 parking spaces available for 27 Dudley St.
What are the annual taxes for 27 Dudley St?
Annual taxes for this multi-family home are estimated at $23,245.
How does 27 Dudley St compare to other multi-family homes in Highland Park?
This multi-family home is listed 3% below the average price for multi-family homes in Highland Park and has been on the market for 56 more days than the typical home in this area.
What is the square footage on this multi-family home?
According to the MLS, this listing is 6,509 sqft.
27 Dudley St is a 14-bedroom, 11-bath multi-family home for sale in Boston MA 02119. Listed on Prevu for 77 days at $3,700,000. This residence features 6,509 square feet of living space, located in Boston. The median listing price for multi-family homes in this area is $849,900. Additional amenities include dishwasher, air conditioning, parking, swimming pool, and washer/dryer. Browse more multi-family home listings in Boston.
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