5+ Family - 5+ Units Side by Side at 299 Dudley Street, Boston MA 02119
5+ Family - 5+ Units Side by Side at 299 Dudley Street, Boston MA 02119, photo 2 of 18
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18 photos

$3,800,000

299 Dudley Street, Boston MA 02119
Boston, MA 02119
Listed by Kevin Benzinger
Bedrooms
24
Bathrooms
16
Living area
7,200 sqft
Year built
2015

About this home

299 Dudley Street, Roxbury presents an exceptional opportunity to acquire a boutique multifamily building constructed in 2015, comprising 8 thoughtfully designed three-bedroom, two-bathroom units with modern finishes throughout. Each residence features large, open floor plans bathed in natural light, offering stunning city and skyline views that elevate the everyday living experience. The property is fully equipped with all separate utilities, on-site parking, common laundry, and dedicated storage and bike storage, delivering a comprehensive amenity package that commands strong tenant demand. Situated in a vibrant, transit-oriented neighborhood, 299 Dudley Street offers residents seamless connectivity to Boston's core while benefiting from the continued growth and investment in the surrounding area. With its modern construction, desirable unit mix of spacious three-bedroom homes, and turnkey operational profile, this asset represents a compelling addition to any investor.

Property details

MLS
MLS Property Information Network
MLS #
73487339
Property type
5+ Family - 5+ Units Side by Side
Subdivision
N/A
Status
Active
Days on market
222
On market date
March 16, 2026
Stories
4
Total bathrooms
16
Garage spaces
N/A
Parking spaces
8
Lot size
0.08 acres
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Nearby schools

Within 10 miles. School directory data from the National Center for Education Statistics (NCES), accessed via the Urban Institute Education Data API. Local Score is calculated by INNOVATE Real Estate; where a state rating is shown, it comes from that state's own official school report card.

Elementary
Orchard Gardens
0.19 mi away · Grades -1-8
Nearest school -- attendance-zone data not available here
5.0
Local Score (student-teacher ratio only (preliminary -- will incorporate state test-score data once available)) -- not an official state rating
Enrollment
733
Student:teacher ratio
11.8:1
District
Boston
Middle
Higginson/Lewis K-8
0.67 mi away · Grades 3-8
Nearest school -- attendance-zone data not available here
5.0
Local Score (student-teacher ratio only (preliminary -- will incorporate state test-score data once available)) -- not an official state rating
Enrollment
188
Student:teacher ratio
7.5:1
District
Boston
High
Dearborn
0.18 mi away · Grades 6-12
Nearest school -- attendance-zone data not available here
5.0
Local Score (student-teacher ratio only (preliminary -- will incorporate state test-score data once available)) -- not an official state rating
Enrollment
578
Student:teacher ratio
11.3:1
District
Boston

Walkability

Blended score for Boston's center, calculated by INNOVATE Real Estate from two sources: the EPA's National Walkability Index (street network, transit, land-use mix) and Google Places amenity data (what's actually reachable on foot from this point). 60% EPA National Walkability Index + 40% nearby-amenity density (Google Places).

91
Highly walkable
out of 100
EPA National Walkability Index
16.8 / 20 -- Most walkable
Google Places amenity density
100 / 100
Restaurants & cafes20
Grocery stores20
Parks20
Schools20
Transit stops20
Pharmacies20

Market position

How this listing compares to current activity in Boston, from live MLS data.

On the market 222 days -- 97 more days than Boston's current average of 125 days.
For reference, the median list price across 8,983 active listings in Boston right now is $80,000.

Mortgage calculator

Estimate only - actual rate and payment depend on your lender, credit, and loan program.

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Est. monthly payment
$23,034/mo
$760,000 down
$3,040,000 loan
Principal & interest$19,717
Property tax (est.)$3,167
Home insurance (est.)$150

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Data source: Listing information provided by MLS Property Information Network via Trestle/CoreLogic. Last updated July 18, 2026.

Information herein deemed reliable but not guaranteed; all measurements, school assignments, HOA fees, taxes, and feature lists are approximate and should be independently verified. Equal Housing Opportunity.