BMN Boston

Get our mobile app!

Download on the App Store
(617) 955-2224
Preview 1 Preview 2 Preview 3 Preview 4 Preview 5 Preview 6 Preview 7 Preview 8 Preview 9 Preview 10 Preview 11 Preview 12 Preview 13 Preview 14 Preview 15 Preview 16 Preview 17 Preview 18 Preview 19 Preview 20 Preview 21 Preview 22 Preview 23 Preview 24 Preview 25 Preview 26 Preview 27 Preview 28 Preview 29 Preview 30 Preview 31 Preview 32 Preview 33 Preview 34 Preview 35 Preview 36 Preview 37 Preview 38 Preview 39 Preview 40 Preview 41 Preview 42
Preview 1 Preview 2 Preview 3 Preview 4 Preview 5 Preview 6 Preview 7 Preview 8 Preview 9 Preview 10 Preview 11 Preview 12 Preview 13 Preview 14 Preview 15 Preview 16 Preview 17 Preview 18 Preview 19 Preview 20 Preview 21 Preview 22 Preview 23 Preview 24 Preview 25 Preview 26 Preview 27 Preview 28 Preview 29 Preview 30 Preview 31 Preview 32 Preview 33 Preview 34 Preview 35 Preview 36 Preview 37 Preview 38 Preview 39 Preview 40 Preview 41 Preview 42

27 Dudley St, Boston MA 02119

Boston, MA 02119 • Roxbury's Fort Hill
$3,625,000
Est. $20,676/month
14
Beds
11
Baths
6,509
Sq Ft
$557
Price/Sq Ft
0.19
Acres
1900
Year Built
5-9 Family
Type
3
Days on Market
Active Listed Feb 18, 2026 • MLS# 73478206 Copied!

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 $22,925/month with a 6.3% cap rate and a projected 7.4% cap rate 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.

View in the App

Save this property, schedule tours instantly, and get alerts when the price drops

Scan to download BMN Boston app Scan with phone
Get the full experience in the BMN Boston app

Property Overview

Property Type
5-9 Family
Listing Type
For Sale
Year Built
1900
Bedrooms
14
Full Bathrooms
11
Living Area
6,509 sq ft
Total Rooms
28
Stories
8
Levels
8

Facts & Features

Central AC

Home Facts

Type Residential Income
Style 5-9 Family
Year Built 1900
Living Area 6,509 sq ft
Lot Size 0.19 acres
Bedrooms 14
Full Baths 11
Total Rooms 28

Interior

Heating Central
Cooling Central Air
Flooring Wood, Tile
Appliances Range, Dishwasher, Disposal, Microwave, Refrigerator, Washer, Dryer
Fireplace None
Basement None
Laundry Electric Dryer Hookup, Washer Hookup
Features Living Room, Dining Room, Kitchen, Laundry Room

Exterior

Construction Brick
Architecture None
Roof Shingle, Rubber

Parking

Features Paved Drive, Off Street
Total Spaces 8

Utilities

Electric None
Water Public
Sewer Public Sewer
Gas None
Other For Gas Range, For Gas Oven, For Electric Dryer, Washer Hookup

Financial

Annual Tax $25,748
Assessed Value $2,056,900

Interior Features

Flooring: Wood, Tile
Appliances: Range, Dishwasher, Disposal, Microwave, Refrigerator, Washer, Dryer
Interior Features: Living Room, Dining Room, Kitchen, Laundry Room
Windows: Insulated Windows
Basement:
Laundry: Electric Dryer Hookup, Washer Hookup
Security:

Construction & Materials

Year Built: 1900
Structure Type:
Exterior Materials: Brick
Roof: Shingle, Rubber
Foundation: Brick/Mortar
Stories: 8

Heating, Cooling & Utilities

Heating: Central
Heating Zones: 7
Cooling: Central Air
Cooling Zones: 7
Hot Water: Electric
Water Source: Public
Sewer: Public Sewer

Parking & Garage

Total Parking Spaces: 8
Parking Features: Paved Drive, Off Street

Location

Loading map...

Neighborhood

Roxbury's Fort Hill

27 Dudley St, Boston MA 02119

Boston, MA 02119

Walkability

Loading Walk Score...

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
C
Hale Elementary School
0.3 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
F
Tobin K-8 School
0.6 mi | #344 of 352 | Score: 25.1
Dropped 8 spots from last year
-33.1 below state avg
364 students Diverse
Grades PK-08
D
Perkins Elementary School
0.6 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
D
Orchard Gardens K-8 School
0.6 mi | #326 of 352 | Score: 28.7
Improved 13 spots from last year
-29.5 below state avg
689 students Diverse
Grades PK-08
Our Lady of Perpetual Help Mission Grammar School
0.7 mi
Grades K-08
C
Hurley K-8 School
0.9 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
0.9 mi | #241 of 352 | Score: 37.2
Dropped 80 spots from last year
-21 below state avg
329 students Diverse
Grades PK-08
F
Ellis Elementary School
0.9 mi | #817 of 824 | Score: 24.7
Dropped 57 spots from last year
-33.5 below state avg
391 students Moderate
Grades PK-06
F
Hennigan Elementary School
0.9 mi | #811 of 824 | Score: 26.0
Improved 2 spots from last year
-32.2 below state avg
472 students Diverse
Grades PK-06
F
Trotter Elementary School
0.9 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
0.6 mi | #349 of 352 | Score: 23.6
Improved 3 spots from last year
-34.6 below state avg
213 students Diverse
Grades 03-08
Nativity Prep School
0.8 mi
Grades 05-08
A
Uncommon Schools - Roxbury Preparatory Dorchester Campus Middle School
1.5 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
Mother Caroline Academy
1.5 mi
Grades 05-08
Dearborn Middle School
1.6 mi
Middle School Academy
2.0 mi
Epiphany School
2.8 mi
Grades 05-08
C
Ohrenberger School
5.6 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
0.1 mi
Frederick Pilot Middle
1.6 mi
H

High Schools

10 schools
A-
O'Bryant School of Math & Science
0.1 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
B
Dearborn STEM Academy
0.5 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+
Boston Latin School
0.9 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
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
1.3 mi
9 sports • 430 athletes
Grades 07-12
Meridian Academy
1.3 mi
Grades 06-09
Newman School
1.6 mi
Grades 07-12
C
Quincy Upper School
1.8 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
D
English High School
1.9 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
B-
Margarita Muniz Academy
2.0 mi | #14 of 25 | Score: 31.3
Improved 349 spots from last year
-26.9 below state avg
428 students Less Diverse
Strong AP Program Rising School
Grades 07-12
Learn about these ratings
School data provided by BMN Schools

Monthly Payment Calculator

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

Monthly Payment Breakdown

Principal & Interest $0
Property Tax $2,146
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
$0/mo
Save $0/mo
Current Rate
$0/mo
+0.5% Rate
$0/mo
Cost $0/mo

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

Property Timeline

🏠
Listed for Sale
Feb 18, 2026
$3,625,000
Original listing
Agent: Mission Realty Advisors Office: Compass

Price & Status History

Date Event Price Change
Feb 18, 2026 New Listing Added $3,625,000 —

Market Statistics

Days on Market
3 days
Price per Sq Ft
$557

Tax History

Year Taxes Assessment
2026 $25,748 $2,056,900

Financial Details

Annual Property Tax
$25,748
Tax Year 2026
Assessed Value
$2,056,900

Listing Information

Listing Agent Mission Realty Advisors
Listing Office Compass
Agent MLS ID TM334200
Office MLS ID AN3337
Listing information is deemed reliable but not guaranteed. Data provided by MLS Property Information Network, Inc. All information should be independently verified.

Comparable Properties

Customize Comparable Search

Finding comparable properties...

Market Analytics for Boston, MA

Real-time market trends and pricing data for this area

27 Dudley St, Boston MA 02119 - Photo 1 27 Dudley St, Boston MA 02119 - Photo 2 27 Dudley St, Boston MA 02119 - Photo 3 27 Dudley St, Boston MA 02119 - Photo 4 27 Dudley St, Boston MA 02119 - Photo 5 27 Dudley St, Boston MA 02119 - Photo 6 27 Dudley St, Boston MA 02119 - Photo 7 27 Dudley St, Boston MA 02119 - Photo 8 27 Dudley St, Boston MA 02119 - Photo 9 27 Dudley St, Boston MA 02119 - Photo 10 27 Dudley St, Boston MA 02119 - Photo 11 27 Dudley St, Boston MA 02119 - Photo 12 27 Dudley St, Boston MA 02119 - Photo 13 27 Dudley St, Boston MA 02119 - Photo 14 27 Dudley St, Boston MA 02119 - Photo 15 27 Dudley St, Boston MA 02119 - Photo 16 27 Dudley St, Boston MA 02119 - Photo 17 27 Dudley St, Boston MA 02119 - Photo 18 27 Dudley St, Boston MA 02119 - Photo 19 27 Dudley St, Boston MA 02119 - Photo 20 27 Dudley St, Boston MA 02119 - Photo 21 27 Dudley St, Boston MA 02119 - Photo 22 27 Dudley St, Boston MA 02119 - Photo 23 27 Dudley St, Boston MA 02119 - Photo 24 27 Dudley St, Boston MA 02119 - Photo 25 27 Dudley St, Boston MA 02119 - Photo 26 27 Dudley St, Boston MA 02119 - Photo 27 27 Dudley St, Boston MA 02119 - Photo 28 27 Dudley St, Boston MA 02119 - Photo 29 27 Dudley St, Boston MA 02119 - Photo 30 27 Dudley St, Boston MA 02119 - Photo 31 27 Dudley St, Boston MA 02119 - Photo 32 27 Dudley St, Boston MA 02119 - Photo 33 27 Dudley St, Boston MA 02119 - Photo 34 27 Dudley St, Boston MA 02119 - Photo 35 27 Dudley St, Boston MA 02119 - Photo 36 27 Dudley St, Boston MA 02119 - Photo 37 27 Dudley St, Boston MA 02119 - Photo 38 27 Dudley St, Boston MA 02119 - Photo 39 27 Dudley St, Boston MA 02119 - Photo 40 27 Dudley St, Boston MA 02119 - Photo 41 27 Dudley St, Boston MA 02119 - Photo 42
Steven Novak

Steven Novak

BMN Boston Real Estate

Schedule a Tour