27 Dudley St, Boston MA 02119

Boston, MA 02119 • Roxbury's Fort Hill
$3,700,000
Est. $20,846/month
14
Beds
11
Baths
6,509
Sq Ft
$568
Price/Sq Ft
0.19
Acres
1900
Year Built
71
Days on Market
Active Listed Sep 25, 2025 • MLS# 73435766 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 $23,125/month with a 6.3% cap rate and a projected 7.3% 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.

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
9
Levels
9

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
Features None
Pool None
Spa None
Fencing Fenced
Patio/Porch None

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 $23,246
Assessed Value $1,988,500

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: 9

Heating, Cooling & Utilities

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

Exterior & Lot

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

Parking & Garage

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

Location

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Neighborhood

Roxbury's Fort Hill

27 Dudley St, Boston MA 02119

Boston, MA 02119

Walkability

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Schools

School information not available

Monthly Payment Calculator

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

Principal & Interest $0
Property Tax $1,937
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

Property Timeline

🏠
Listed for Sale
Sep 25, 2025
$3,700,000
Original listing
Agent: Mission Realty Advisors Office: Compass

Price & Status History

Date Event Price Change
Sep 25, 2025 New Listing Added $3,700,000

Market Statistics

Days on Market
71 days
Price per Sq Ft
$568

Tax History

Year Taxes Assessment
2025 $23,246 $1,988,500

Financial Details

Annual Property Tax
$23,246
Tax Year 2025
Assessed Value
$1,988,500

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.

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Market Analytics for Boston, MA

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