Active Under Contract
191 Days on market
299 Dudley Street Boston — Photo 1 of 18

299 Dudley Street Boston — Photo 1 of 18

Recent Drop: $775,000

$4,575,000
$3,800,000

$3,800,000

299 Dudley Street, Boston, MA 02119

Boston, MA 02119 — Roxbury

Investor Analysis

Beds

24

Baths

16

SqFt

7,200

Style

5+ Family - 5+ Units Side by Side

Built

2015

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.

Market Value Analysis

This Property
Size (SqFt) →Price →
This Property$528/sqft
Local Avg (Boston)$623/sqft
15% BelowMarket Average

* Analysis is based on 24 actively listed and recently sold comparable properties strictly within Boston, MA.

Property Details

Financials

Original Price$4,575,000
Annual Taxes$99

Parking

Garage0
Off-Street8

Interior Specifications

Total Rooms56
FireplacesNone
Flooring--
BasementFull

Climate & Utilities

Heating--
Cooling--
WaterPublic
SewerPublic Sewer

Building & Exterior

Construction--
Roof--
FoundationOther
Zoning99

Property & Lot

Acres0.08
SqFt Lot3,698
Lot FeaturesOther

Neighborhood

Other

Geography

Property History

Price Drop
$3,800,000

Was $4,375,000

Jul 14, 2026

MLS® 73487339

Price Drop
$4,375,000

Was $4,575,000

May 11, 2026

MLS® 73487339

Listed
$4,575,000

Mar 16, 2026

MLS® 73487339

Population

27,377

U.S. Census Bureau, ACS 2024 5-Year Estimates (B01003)

Median Household Income

$48K

U.S. Census Bureau, ACS 2024 5-Year Estimates (B19013)

Renter-Occupied Homes

73.5%

U.S. Census Bureau, ACS 2024 5-Year Estimates (B25003)

New Construction Permits — Suffolk County

2,337 housing units permitted in the last 12 months (+13% vs the prior 12 months) — 2,062 in 5+ unit buildings

U.S. Census Bureau, Building Permits Survey (through Jul '26)

Listing Provided By

Listing Agent: Kevin Benzinger

Listing Office: Boston Realty Advisors

MLS® Number: 73487339

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