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301-305 Dudley Street, Boston MA 02119 - Preview 1 301-305 Dudley Street, Boston MA 02119 - Preview 2 301-305 Dudley Street, Boston MA 02119 - Preview 3 301-305 Dudley Street, Boston MA 02119 - Preview 4 301-305 Dudley Street, Boston MA 02119 - Preview 5 301-305 Dudley Street, Boston MA 02119 - Preview 6 301-305 Dudley Street, Boston MA 02119 - Preview 7 301-305 Dudley Street, Boston MA 02119 - Preview 8 301-305 Dudley Street, Boston MA 02119 - Preview 9 301-305 Dudley Street, Boston MA 02119 - Preview 10 301-305 Dudley Street, Boston MA 02119 - Preview 11 301-305 Dudley Street, Boston MA 02119 - Preview 12 301-305 Dudley Street, Boston MA 02119 - Preview 13 301-305 Dudley Street, Boston MA 02119 - Preview 14
301-305 Dudley Street, Boston MA 02119 - Preview 1 301-305 Dudley Street, Boston MA 02119 - Preview 2 301-305 Dudley Street, Boston MA 02119 - Preview 3 301-305 Dudley Street, Boston MA 02119 - Preview 4 301-305 Dudley Street, Boston MA 02119 - Preview 5 301-305 Dudley Street, Boston MA 02119 - Preview 6 301-305 Dudley Street, Boston MA 02119 - Preview 7 301-305 Dudley Street, Boston MA 02119 - Preview 8 301-305 Dudley Street, Boston MA 02119 - Preview 9 301-305 Dudley Street, Boston MA 02119 - Preview 10 301-305 Dudley Street, Boston MA 02119 - Preview 11 301-305 Dudley Street, Boston MA 02119 - Preview 12 301-305 Dudley Street, Boston MA 02119 - Preview 13 301-305 Dudley Street, Boston MA 02119 - Preview 14

301-305 Dudley Street, Boston MA 02119

Boston, MA 02119 • Roxbury
$4,950,000
Est. $25,238/month
31
Beds
15
Baths
18,990
Sq Ft
$261
Price/Sq Ft
0.09
Acres
1900
Year Built
5+ Family - 5+ Units Side by Side
Type
81
Days on Market
Active Price Drop -$300,000 Listed Mar 16, 2026 • MLS# 73487348 Copied!

About this home

301-305 Dudley Street, Roxbury presents a unique mixed-use investment opportunity featuring eight residential units and two street-level commercial spaces, in one of Boston's most rapidly evolving corridors. The handsome brick facade building boasts generously sized residential units, with seven of eight having undergone recent renovations, delivering modern living spaces while preserving the classic character of the property. Each residence offers excellent natural light and air, creating bright and comfortable homes that appeal to today's discerning renter. The property includes coveted off-street parking, a highly sought-after amenity in this transit-oriented neighborhood that further enhances tenant retention. With its rare combination of renovated residential units, active commercial income, and brick construction, 301-305 Dudley Street represents a truly compelling value-add and stabilized investment opportunity.

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Public Records

Current Owner

Owner BOSTON MULTI FAMILY PROPERTY
Mailing Address 305 DUDLEY ST, ROXBURY, MA, 02119

Land Use

Use Code 013
Description N/A
Style APT 7-30 UNITS

Tax Information

Assessed Value $1,961,600

Assessment History

Year Land Building Total Change
FY2023 $500,700 $1,460,900 $1,961,600 —

Sale History

Date Price Book/Page
Nov 30, 2012 $1,855,000 50570/187

Building Permit History

Issued Type / Work Status Value
Jul 7, 2023 Short Form Bldg Permit
INTEXT
Interior/Exterior Work
Permit #SF1491914 		Open $6,000
Apr 14, 2022 Short Form Bldg Permit
INTEXT
Interior/Exterior Work
Permit #SF1318717 		Open $11,000
Nov 28, 2021 Gas Permit
GAS
Gas
Permit #G1272323 		Closed $1,200
Nov 28, 2021 Plumbing Permit
PLUMBING
Plumbing
Permit #PL1272322 		Closed $13,000
Nov 8, 2021 Electrical Permit
ELECTRICAL
Electrical
Permit #E1266285 		Closed $13,000
Nov 1, 2021 Short Form Bldg Permit
INTEXT
Interior/Exterior Work
Permit #SF1262900 		Open $106,750
Oct 17, 2021 Gas Permit
GAS
Gas
Permit #G1257910 		Open $1,500
Oct 14, 2021 Electrical Permit
ELECTRICAL
Electrical
Permit #E1258397 		Closed $13,000
Oct 12, 2021 Plumbing Permit
PLUMBING
Plumbing
Permit #PL1256892 		Closed $13,000
Oct 12, 2021 Gas Permit
GAS
Gas
Permit #G1257327 		Open $500
Sep 3, 2021 Short Form Bldg Permit
INTREN
Renovations - Interior NSC
Permit #SF1246237 		Closed $95,000
Data: City of Boston Open Data (Analyze Boston)

Municipal Context: BOSTON

Property Data Comparison

Field Assessor MLS Match
Sqft 18,990 18,990 ✓
Year built 1,900 1,900 ✓
Match: geocode_proximity (89.6% confidence) · Data as of Jun 1, 2026

Property Overview

Property Type
5+ Family - 5+ Units Side by Side
Listing Type
For Sale
Year Built
1900
Bedrooms
31
Full Bathrooms
15
Living Area
18,990 sq ft
Total Rooms
60
Stories
5
Levels
5

Facts & Features

Home Facts

Type Residential Income
Style 5+ Family - 5+ Units Side by Side
Year Built 1900
Living Area 18,990 sq ft
Lot Size 0.09 acres
Bedrooms 31
Full Baths 15
Total Rooms 60

Interior

Heating None
Cooling None
Flooring None
Appliances None
Fireplace None
Basement None
Laundry None
Features None

Exterior

Construction None
Architecture None
Roof None
Features None
Pool None
Spa None
Fencing None
Patio/Porch None

Parking

Features None
Total Spaces 2

Utilities

Electric None
Water Public
Sewer Public Sewer
Gas None
Other None

Financial

Annual Tax $99
Assessed Value $99

Interior Features

Flooring:
Appliances:
Interior Features:
Windows:
Basement:
Laundry:
Security:

Construction & Materials

Year Built: 1900
Structure Type:
Exterior Materials:
Roof:
Foundation: Other
Stories: 5

Heating, Cooling & Utilities

Heating:
Cooling:
Hot Water:
Water Source: Public
Sewer: Public Sewer
Energy Features:

Exterior & Lot

Exterior Features:
Patio & Porch:
Fencing:
Other Structures:
Lot Features: Other
Road Surface:

Parking & Garage

Total Parking Spaces: 2
Parking Features:

Location

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Neighborhood

Roxbury

301-305 Dudley Street, Boston MA 02119

Boston, MA 02119

Walkability

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Nearby Schools

School District
Boston School District local
C-
🎓 Where Graduates Go Class of 2021
52% attend college
38% 4-Year 14% 2-Year 7% Out of State 7% Working
⚠ School Safety 2024-25
3.7% Above Average
3.2% Suspensions 0.3% In-School 0.5% Emergency
↓ 1.8% below state avg
E

Elementary Schools

10 schools
D
Orchard Gardens K-8 School
0.2 mi | #326 of 352 | Score: 28.7
Improved 13 spots from last year
-29.5 below state avg
689 students Diverse
Grades PK-08
B
Excel Academy Charter School
0.7 mi | #155 of 346 | Score: 54.9
Improved 160 spots from last year
-3.3 below state avg
1,379 students Moderate
High Graduation Rate Rising School
Grades 05-12
C
Hale Elementary School
0.7 mi | #582 of 824 | Score: 41.7
Dropped 281 spots from last year
-16.5 below state avg
162 students Diverse
Diverse Student Body
Grades PK-06
C-
Winthrop Elementary School
0.7 mi | #665 of 824 | Score: 37.6
Dropped 171 spots from last year
-20.6 below state avg
226 students Diverse
Grades PK-06
D
Perkins Elementary School
0.8 mi | #772 of 824 | Score: 30.9
Improved 29 spots from last year
-27.3 below state avg
167 students Diverse
Rising School Diverse Student Body
Grades PK-06
C
Hurley K-8 School
0.8 mi | #258 of 352 | Score: 35.8
Dropped 23 spots from last year
-22.4 below state avg
335 students Moderate
Grades PK-08
C+
Bridge Boston Charter School
0.8 mi | #241 of 352 | Score: 37.2
Dropped 80 spots from last year
-21 below state avg
329 students Diverse
Grades PK-08
B
Boston Collegiate Charter School
1.0 mi | #167 of 346 | Score: 53.7
Improved 31 spots from last year
-4.5 below state avg
708 students Diverse
Rising School College Ready Curriculum Diverse Student Body
Grades 05-12
F
Blackstone Elementary School
1.0 mi | #809 of 824 | Score: 26.3
Improved 12 spots from last year
-31.9 below state avg
582 students Moderate
Grades PK-06
F
Trotter Elementary School
1.0 mi | #794 of 824 | Score: 29.2
Dropped 6 spots from last year
-29 below state avg
352 students Diverse
Grades PK-06
M

Middle Schools

10 schools
F
Higginson/Lewis K-8 School
0.7 mi | #349 of 352 | Score: 23.6
Improved 3 spots from last year
-34.6 below state avg
213 students Diverse
Grades 03-08
A
Uncommon Schools - Roxbury Preparatory Dorchester Campus Middle School
1.2 mi | #4 of 16 | Score: 41.9
Improved 187 spots from last year
-16.3 below state avg
1,126 students Diverse
Rising School College Ready Curriculum
Grades 05-08
Nativity Prep School
1.3 mi
Grades 05-08
Dearborn Middle School
1.4 mi
Mother Caroline Academy
1.4 mi
Grades 05-08
Middle School Academy
1.5 mi
Epiphany School
2.5 mi
Grades 05-08
C
Ohrenberger School
5.9 mi | #265 of 352 | Score: 34.9
Improved 20 spots from last year
-23.3 below state avg
477 students Diverse
Rising School Diverse Student Body
Grades 03-08
Timilty Middle
0.7 mi
Frederick Pilot Middle
1.3 mi
H

High Schools

10 schools
B
Dearborn STEM Academy
0.2 mi | #13 of 25 | Score: 31.7
Improved 356 spots from last year
-26.6 below state avg
565 students Diverse
10 sports • 242 athletes
Early College Program Rising School
Grades 07-12
A-
O'Bryant School of Math & Science
0.7 mi | #90 of 346 | Score: 61.1
Improved 94 spots from last year
+2.9 above state avg
1,509 students Very Diverse
High Graduation Rate Rising School College Ready Curriculum Diverse Student Body
Grades 07-12
A+
Boston Latin Academy
0.9 mi | #2 of 25 | Score: 63.9
Improved 214 spots from last year
+5.7 above state avg
1,693 students Very Diverse
17 sports • 1,298 athletes
High Graduation Rate Rising School Strong Athletics Diverse Student Body
Grades 07-12
Cathedral High School
1.0 mi
9 sports • 430 athletes
Grades 07-12
A+
Boston Latin School
1.4 mi | #19 of 346 | Score: 73.3
Improved 61 spots from last year
+15.1 above state avg
2,424 students Very Diverse
18 sports • 2,006 athletes
Strong AP Program High Graduation Rate Rising School Strong Athletics
Grades 07-12
C
Quincy Upper School
1.5 mi | #268 of 346 | Score: 44.6
Improved 4 spots from last year
-13.6 below state avg
557 students Very Diverse
12 sports • 208 athletes
High Graduation Rate Diverse Student Body
Grades 06-12
Meridian Academy
1.7 mi
Grades 06-09
Newman School
1.7 mi
Grades 07-12
C
Ruth Batson Academy
1.9 mi | #19 of 25 | Score: 27.6
Improved 346 spots from last year
-30.6 below state avg
604 students Diverse
8 sports • 128 athletes
Early College Program Rising School
Grades 07-12
D
English High School
2.2 mi | #324 of 346 | Score: 29.7
Improved 34 spots from last year
-28.5 below state avg
720 students Moderate
8 sports • 332 athletes
Rising School Career Tech Programs
Grades 07-12
Learn about these ratings
School data provided by BMN Schools

Monthly Payment Calculator

Monthly Payment
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Principal, interest, taxes & insurance
Loan Amount
$0
After down payment
Total Interest
$0
Over life of loan
Total Cost
$0
Including down payment
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Down: $0
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Monthly Payment Breakdown

Principal & Interest $0
Property Tax $8
Homeowners Insurance $200
PMI (if <20% down) $0

Loan Summary

Total of 360 payments $0
Total principal paid $0
Total interest paid $0

Rate Impact

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Current Rate
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Payment Over Time

Interest
Principal
Year 1
95% Interest
Year 15
50/50
Year 30
95% Principal
* Estimates only. Actual payments may vary. Consult with a lender for accurate figures.

Property History

Market Insights

1
Price Changes
5.7%
Price Range

Property Timeline

↓
Price Reduced
May 11, 2026
$4,950,000 $300,000 (-5.71%)
From $5,250,000 to $4,950,000 (-5.7%)
🏠
Listed for Sale
Mar 16, 2026
$5,250,000
Original listing
Agent: Kevin Benzinger Office: Boston Realty Advisors

Price & Status History

Date Event Price Change
May 11, 2026 Price Changed $4,950,000 -$300,000
Mar 16, 2026 New Listing Added $5,250,000 —

Market Statistics

Days on Market
81 days
Price per Sq Ft
$261
Total Price Drop
-$300,000

Tax History

Year Taxes Assessment
99 $99 $99

Financial Details

Annual Property Tax
$99
Tax Year 99
Assessed Value
$99

Listing Information

Listing Agent Kevin Benzinger
Listing Office Boston Realty Advisors
Agent MLS ID CN216101
Office MLS ID AN8461
Listing Data Updated May 15, 2026 3:05 AM EDT
Listing information is deemed reliable but not guaranteed. Data provided by MLS Property Information Network, Inc. All information should be independently verified.

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301-305 Dudley Street, Boston MA 02119 - Photo 1 301-305 Dudley Street, Boston MA 02119 - Photo 2 301-305 Dudley Street, Boston MA 02119 - Photo 3 301-305 Dudley Street, Boston MA 02119 - Photo 4 301-305 Dudley Street, Boston MA 02119 - Photo 5 301-305 Dudley Street, Boston MA 02119 - Photo 6 301-305 Dudley Street, Boston MA 02119 - Photo 7 301-305 Dudley Street, Boston MA 02119 - Photo 8 301-305 Dudley Street, Boston MA 02119 - Photo 9 301-305 Dudley Street, Boston MA 02119 - Photo 10 301-305 Dudley Street, Boston MA 02119 - Photo 11 301-305 Dudley Street, Boston MA 02119 - Photo 12 301-305 Dudley Street, Boston MA 02119 - Photo 13 301-305 Dudley Street, Boston MA 02119 - Photo 14
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