27 Dudley St, Boston MA 02119

Boston, MA 02119 • Roxbury's Fort Hill
$3,700,000
Est. $19,693/month
14
Beds
11
Baths
6,509
Sq Ft
$568
Price/Sq Ft
0.19
Acres
1900
Year Built
5-9 Family
Type
23 hours 52 minutes
Time on Market
Active Listed Sep 26, 2025 • MLS# 73435766

About this home

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 $23,125/month with a 6.3% cap rate and a projected 7.3% 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.

Facts & Features

Property Overview

Property Type
5-9 Family
Property Category
Residential Income
Year Built
1900
Bedrooms
14
Full Bathrooms
11
Living Area
6,509 sq ft
Total Rooms
28
Stories
9
Levels
9

Interior Features

Flooring
Wood, Tile
Heating
Central
Has Heating
Yes
Cooling
Central Air
Has Cooling
Yes
Has Fireplace
No
Appliances
Range, Dishwasher, Disposal, Microwave, Refrigerator, Washer, Dryer
Interior Features
Living Room, Dining Room, Kitchen, Laundry Room
Laundry Features
Electric Dryer Hookup, Washer Hookup
Window Features
Insulated Windows

Exterior & Structure

Construction Materials
Brick
Roof
Shingle, Rubber
Foundation
Brick/Mortar
Fencing
Fenced
Has Spa
No
Waterfront Property
No

Lot & Land

Lot Size
0.19 acres
Lot Size
8,241 sq ft
Lot Size Area
0.1900
Lot Features
Corner Lot
Road Frontage Type
Public

Parking & Garage

Has Garage
No
Total Non-Garage Parking Spaces
8
Parking Features
Paved Drive, Off Street

Utilities & Systems

Utilities Available
for Gas Range, for Gas Oven, for Electric Dryer, Washer Hookup
Water Source
Public
Sewer
Public Sewer

Community & HOA

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
Senior Community
No

Financial & Tax Information

Annual Tax Amount
$23,246
Tax Year
2025
Tax Assessed Value
$1,988,500
Parcel Number
W:09 P:03293 S:000,3397293
Zoning
R4
Financial Data Source
Estimated, Owner

Additional Details

Year Built Source
Public Records
Year Built Details
Approximate
Disclosures
Please see attached proforma for current and projected rents. The seventh unit is being finished now, owners will guarantee the rent on the unit.

Location

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Neighborhood

Roxbury's Fort Hill

27 Dudley St, Boston MA 02119

Boston, MA 02119

Walkability

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Schools

School information not available

Monthly Payment Calculator

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Estimated Monthly Payment $0

Payment Breakdown

Principal & Interest $0
Property Tax $1,937
Homeowners Insurance $200
PMI $0

Property History

Property Timeline

🏠
Listed for Sale
Sep 25, 2025
$3,700,000
Original listing
Agent: Mission Realty Advisors Office: Compass

Price & Status History

Date Event Price Change
Sep 25, 2025 New Listing Added $3,700,000

Market Statistics

Time on Market
23 hours 52 minutes
Price per Sq Ft
$568

Tax History

Year Taxes Assessment
2025 $23,246 $1,988,500

Financial Details

Annual Property Tax
$23,246
Tax Year 2025
Assessed Value
$1,988,500

Listing Information

Listing Agent Mission Realty Advisors
Listing Office Compass
Agent MLS ID TM334200
Office MLS ID AN3337

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