27 Dudley St Boston, MA $ 3,700,000
27 Dudley St
$ 3,700,000
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27 Dudley St

Boston, MA, 02119
$ 3,700,000
Bedrooms14 Baths11.0 Sq 6,509

Monthly Estimate*

$ 23,083

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Multi-Family Home for sale in Boston, MA

for $3,700,000 with 14 bedrooms and 11 full baths. This 6,509 square foot home was built in 1900 on a lot size of 0.19.

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.

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Multi-Family Active

Price

$ 3,700,000

Bedrooms

14

Full Bath

11

Property Type

Multi-Family

Taxes

$ 23,245

Style

5-9 Family

Lot Size

0.19

Year Built

1900

Town/City

Boston

County/Region

Suffolk

MLS | Web ID

73435766

List By
Mission Realty Advisors

Listing Agent

Compass

Broker

Affordability Calculator

$25,020
Per Month
92%
8%
0%
Monthly Principal & Interest
$23,083
Monthly Property Taxes
$1,937
Monthly Home Insurance
--
Default based on a 30-year fixed rate of 6.375% with 20% down. The estimated payment is offered for convenience and is not an offer of credit. Due to market fluctuations, interest rates are subject to change at any time and without notice. Your individual rate may vary. Rates may differ for FHA, VA or jumbo loans.
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Pricing History
DatePricePrice ChangeDescription
9/25/2025$3,700,000 Listed Price

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27 Dudley St, Boston, MA, 02119 is a Multi-Family Home for sale at $3,700,000 with 6,509 sqft and a lot size of 0.19. 27 Dudley St has 14 bedrooms, 11.0 baths, and was built in 1900. The property's zip code is 02119 which is in Boston, MA