27 Dudley St, Boston, MA 02119 - Photo 1

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$3,625,000 Just Listed

For Sale
Active
Multi-Family
7 Units
14 Total Beds
0.19 Acres
Updated 11 hours ago

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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 $22,925/month with a 6.3% cap rate and a projected 7.4% 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.

Full Property Details

Full Property Details for 27 Dudley St

General

Price: $3,625,000
Taxes: $25,748 (2026)
Status: Active
Type: Multi-Family
MLS ID: 73478206
Updated: 2/19/2026
Added to Site: 2 day(s) ago

Rooms

Bathrooms

Total Bathrooms: 11
Full Bathrooms: 11

Bedrooms

Total Bedrooms: 14

Parking

Parking Features: Paved Drive, Off Street

Location

County: Suffolk

Structural Information

Stories/Levels: 8
Square Feet: 6,509
Year Built: 1900

Lot Features

Lot Size (Acres): 0.19

Financial Considerations

Tax Amount: $25,748
Tax Year: 2026

Disclosures and Reports

Property ID: W:09 P:03293 S:000, 3397293

Listed by Compass, Mission Realty Advisors and Eric W. Johnson

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Listing agents

— 27 Dudley St —

Mission Realty Advisors

Compass
Eric W. Johnson

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Schools

Schools serving 27 Dudley St

School District:Boston School District

Name	Grades	Distance
Hale Elementary School 51 Cedar Street, Boston, MA 02119	PK-5	0.3 mi
Tobin K-8 School 40 Smith St, Boston, MA 02120	PK-8	0.5 mi
Higginson/Lewis K-8 131 Walnut Avenue, Boston, MA 02119	PK-8	0.6 mi
O'Bryant School Math/Science 55 Malcolm X Boulevard, Boston, MA 02120	7-12	0.1 mi
James P Timilty Middle School 205 Roxbury Street, Boston, MA 02119	6-8	0.2 mi
Dearborn Middle School 36 Winthrop St, Boston, MA 02119	6-12	0.5 mi
Madison Park High 75 Malcolm X Blvd, Boston, MA 02120	9-12	0.2 mi
Fenway High School 67 Alleghany St, Boston, MA 02120	9-12	0.5 mi
Egleston Community High School 3134 Washington Street, Boston, MA 02130	9-12	1.2 mi

Disclaimer: School attendance boundaries provided by Pitney Bowes and are for reference only. Contact the school directly to verify enrollment eligibility.

Price & Sales History for 27 Dudley St Get Price Alerts and Save Property

Date

Details

Price

Change

Source

2/18/2026

Listed

$3,625,000

173.58%

MLS

9/13/2017

Sold

$1,325,000

—

Public Record

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Disclaimer: Historical sales information is derived from public records provided by the county offices. Information is not guaranteed and should be independently verified.

Tax History

Tax History for 27 Dudley St

Year

Property Taxes

Change

Tax Assessment

Change

2025

$23,027

$1,988,500

-4%

2024

$22,516

—

$2,065,700

-1%

2023

$22,522

$2,097,000

2022

$22,092

$2,030,500

2021

$21,363

55%

$2,002,200

53%

2020

$13,826

48%

$1,309,300

47%

2019

$9,371

25%

$889,105

24%

2018

$7,516

—

$717,155

2017

$7,520

$710,125

12%

2016

$6,974

34%

$634,030

48%

2015

$5,205

100%

$429,780

25%

2014

—

$344,500

—

View All

Disclaimer: Historical tax information is derived from public records provided by the county offices. Information is not guaranteed and should be independently verified.

Estimate the Cost

Estimate the Cost for 27 Dudley St

27 Dudley St, Boston, MA 02119 (MLS# 73478206) is a Multi-Family property with 7 units containing 14 bedrooms and 11 full bathrooms. 27 Dudley St is currently listed for $3,625,000 and was received on February 18, 2026. Want to learn more about 27 Dudley St? Do you have questions about finding other Multi-Family real estate for sale in Boston? You can browse all Boston real estate or contact a Coldwell Banker agent to request more information.

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27 Dudley St Boston, MA 02119