299 Dudley Street, Boston MA 02119
Boston, MA 02119 • Roxbury
$4,575,000
$3,800,000
Est. $19,423/month
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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.
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Recently Sold Nearby
Property History
Market Insights
2
Price Changes
16.9%
Price Range
Property Timeline
Price Reduced
Jul 14, 2026
$3,800,000
$575,000
(-13.14%)
From $4,375,000 to $3,800,000 (-13.1%)
Price Reduced
May 11, 2026
$4,375,000
$200,000
(-4.37%)
From $4,575,000 to $4,375,000 (-4.4%)
Listed for Sale
Mar 16, 2026
$4,575,000
Original listing
Agent: Kevin Benzinger
Office: Boston Realty Advisors
| Date | Event | Price | Change | $/sqft | Details |
|---|---|---|---|---|---|
| 07/14/2026 | ↓ Price Reduced | $3,800,000 | $575,000 | - | From $4,375,000 to $3,800,000 (-13.1%) |
| 05/11/2026 | ↓ Price Reduced | $4,375,000 | $200,000 | - | From $4,575,000 to $4,375,000 (-4.4%) |
| 03/16/2026 | 🏠 Listed for Sale | $4,575,000 | - | - | Original listing |
Tax History
| Year | Taxes | Assessment |
|---|---|---|
| 99 | $99 | $99 |
Financial Details
Annual Property Tax
$99
Tax Year 99
Assessed Value
$99
Facts & Features
Home Facts
Type
Residential Income
Style
5+ Family - 5+ Units Side by Side
Year Built
2015
Living Area
7,200 sq ft
Lot Size
0.08 acres
Bedrooms
24
Full Baths
16
Total Rooms
56
Investment Metrics
Units
8
Unit 1 Rent
— · Y
Unit 2 Rent
— · Y
Interior
Heating
None
Cooling
None
Flooring
None
Appliances
None
Fireplace
None
Basement
Full
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
8
Utilities
Electric
None
Water
Public
Sewer
Public Sewer
Gas
None
Other
None
Financial
Annual Tax
$99
Assessed Value
$99
HOA & Community
Fee Includes
None
Amenities
None
Optional Fee Includes
None
MA Disclosures
Seller Disclosures
None
Additional Details
Possession
None
Accepted Financing
Other (see Remarks)
Structure Type
[]
Sq Ft Source
Other
Sq Ft Disclosures
Per plans. Further information to follow by request.
Documents
None
County
Suffolk
Total market time (incl. prior listings)
124 days
Property Overview
Property Type
5+ Family - 5+ Units Side by Side
Listing Type
For Sale
Year Built
2015
Bedrooms
24
Full Bathrooms
16
Living Area
7,200 sq ft
Total Rooms
56
Stories
4
Levels
4
Floor Layout
Interactive room guide
Floor Layout
Finished Area
7,200 sq ft above grade
Display Options
Room Markers
BABathroom (4)
BRBedroom (5)
DDining (1)
KKitchen (1)
LLiving (2)
OOffice (1)
Conceptual diagram based on MLS room data. It is not to scale and is not a substitute for architectural plans or on-site measurements.
Interior Features
Flooring:
Appliances:
Interior Features:
Windows:
Basement:
Full
Laundry:
Security:
Construction & Materials
Year Built:
2015
Structure Type:
Exterior Materials:
Roof:
Foundation:
Other
Stories:
4
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:
8
Parking Features:
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
Elementary Schools
10 schools
D
Orchard Gardens K-8 School
0.2 mi
|
#325 of 352
|
Score: 28.8
Improved 14 spots from last year
-29.4 below state avg
716 students
Diverse
Grades PK-08
B
Excel Academy Charter School
0.7 mi
|
#149 of 346
|
Score: 56.4
Improved 166 spots from last year
-1.9 below state avg
1,376 students
Moderate
High Graduation Rate
Rising School
Grades 05-12
C
Hale Elementary School
0.7 mi
|
#590 of 825
|
Score: 41.3
Dropped 289 spots from last year
-16.9 below state avg
167 students
Diverse
Diverse Student Body
Grades PK-06
C-
Winthrop Elementary School
0.7 mi
|
#670 of 825
|
Score: 37.4
Dropped 176 spots from last year
-20.8 below state avg
256 students
Diverse
Grades PK-06
D
Perkins Elementary School
0.7 mi
|
#766 of 825
|
Score: 31.2
Improved 35 spots from last year
-27 below state avg
201 students
Diverse
Rising School
Diverse Student Body
Grades PK-06
C
Hurley K-8 School
0.8 mi
|
#259 of 352
|
Score: 35.7
Dropped 24 spots from last year
-22.5 below state avg
337 students
Moderate
Grades PK-08
C+
Bridge Boston Charter School
0.8 mi
|
#238 of 352
|
Score: 37.3
Dropped 77 spots from last year
-20.9 below state avg
347 students
Diverse
Grades PK-08
B
Boston Collegiate Charter School
1.0 mi
|
#154 of 346
|
Score: 55.7
Improved 44 spots from last year
-2.5 below state avg
688 students
Diverse
High Graduation Rate
Rising School
College Ready Curriculum
Diverse Student Body
Grades 05-12
F
Blackstone Elementary School
1.0 mi
|
#808 of 825
|
Score: 26.2
Improved 13 spots from last year
-32 below state avg
572 students
Moderate
Grades PK-06
D
Trotter Elementary School
1.0 mi
|
#788 of 825
|
Score: 29.5
Same rank as last year
-28.7 below state avg
360 students
Diverse
Grades PK-06
Middle Schools
10 schools
F
Higginson/Lewis K-8 School
0.7 mi
|
#349 of 352
|
Score: 23.2
Improved 3 spots from last year
-35 below state avg
246 students
Diverse
Grades 03-08
A
Uncommon Schools - Roxbury Preparatory Dorchester Campus Middle School
1.2 mi
|
#4 of 16
|
Score: 42.5
Improved 187 spots from last year
-15.7 below state avg
1,225 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
|
#266 of 352
|
Score: 35.0
Improved 19 spots from last year
-23.2 below state avg
458 students
Diverse
Diverse Student Body
Grades 03-08
Timilty Middle
0.7 mi
Frederick Pilot Middle
1.3 mi
High Schools
10 schools
B
Dearborn STEM Academy
0.2 mi
|
#13 of 25
|
Score: 33.4
Improved 356 spots from last year
-24.8 below state avg
565 students
Moderate
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: 61.6
Improved 94 spots from last year
+3.4 above state avg
1,518 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: 64.9
Improved 214 spots from last year
+6.7 above state avg
1,669 students
Very Diverse
17 sports
• 1,298 athletes
Strong AP Program
High Graduation Rate
Rising School
Strong Athletics
Grades 07-12
Cathedral High School
1.0 mi
9 sports
• 430 athletes
Grades 07-12
A+
Boston Latin School
1.4 mi
|
#20 of 346
|
Score: 73.7
Improved 60 spots from last year
+15.5 above state avg
2,382 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
|
#279 of 346
|
Score: 44.4
Dropped 7 spots from last year
-13.8 below state avg
575 students
Very Diverse
12 sports
• 208 athletes
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
|
#20 of 25
|
Score: 29.1
Improved 345 spots from last year
-29.1 below state avg
584 students
Diverse
8 sports
• 128 athletes
Early College Program
Rising School
Grades 07-12
D
English High School
2.2 mi
|
#328 of 346
|
Score: 28.9
Improved 30 spots from last year
-29.3 below state avg
653 students
Diverse
8 sports
• 332 athletes
Rising School
Career Tech Programs
Grades 07-12
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Monthly Payment Calculator
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Loan Amount
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After down payment
Total Interest
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Over life of loan
Total Cost
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Including down payment
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Down: $0
%
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
-0.5% Rate
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Current Rate
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Payment Over Time
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.
Location
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Neighborhood
Roxbury
299 Dudley Street, Boston MA 02119
Boston, MA 02119
Listing Information
Listing Agent
Kevin Benzinger
Listing Office
Boston Realty Advisors
Office Phone
617-375-7900
Agent MLS ID
CN216101
Office MLS ID
AN8461
Listing Data Updated
Jul 18, 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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