27 Dudley St

6,509 Sq. Ft.
$557 / Sq. Ft.
6,509
Sq. Ft.
$557
per Sq. Ft.

Description

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...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.

Listing Agents

  1. Eric Johnson

    Eric Johnson

    Alternative Listing Agent

    Compass

    ericjohnson@compass.com

    P: (203)-893-8316

  2. Bill MacDonald

    Bill MacDonald

    Alternative Listing Agent

    Compass

Property Details for 27 Dudley Street

Town
Boston
MLS Area
Roxbury's Fort Hill
Area
MA-Boston-Roxbury's Fort Hill, MA-Boston
Garage Spaces
0
Parking Spaces
8.00
Parking Spaces Total
8
LISTING UPDATED: 02/19/2026 05:05 PM

Property Details for 27 Dudley Street

StatusNew
MLS #73478206
Days on Market3
Taxes$25,748 / year
HOA Fees-
Compass TypeMulti Family
MLS TypeMulti-family / 5-9 Family
Year Built1900
CountySuffolk County
Buyer's Agent Compensation2%
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Building Information for 27 Dudley Street

Stories8Residences7Year Built1900Building Size-Lot Size0.19 AC / 8,241 SF

Payment Calculator

$19,813 per month

30 year fixed, 6.15% Interest

Principal and Interest

$17,668

Property Taxes

$2,146

HOA Dues

$0

The Payment Calculator is for illustrative purposes only.

Property Information for 27 Dudley Street

General Details
Property Details
  • Building Area Units: Square Feet
  • Community Features: Public Transportation, Shopping, Swimming Pool, Tennis Court, Park, Walk/Jog Trails, Medical Facility, Laundromat, Bike Path, Conservation Area, Highway Access, House of Worship, Marina, Private School, Public School, T-Station, University, Other (See Remarks)
  • Living Area: 6509.0
  • SqFt with Basement: Yes
  • Total Units: 7
  • Waterfront: No
  • Year Built Details: Approximate
  • Year Built Source: Public Records
Features
Interior Features
  • Appliances: Range, Dishwasher, Disposal, Microwave, Refrigerator, Washer, Dryer
  • Num of Baths: 11.0
  • Num of Full Baths: 11
  • Num of Half Baths: 0
  • Bathrooms Total Decimal: 11.00
  • Bathrooms Total Integer: 11
  • FireplaceYN: No
  • Fireplaces: 0
  • Flooring: Wood, Tile
  • Interior Features: Living Room, Dining Room, Kitchen, Laundry Room
  • Laundry Features: Electric Dryer Hookup, Washer Hookup
  • SpaYN: No
  • Window Features: Insulated Windows
Exterior Features
  • Construction: Brick
  • Exterior Features: Fenced Yard
  • Fencing: Fenced
  • Lot Description: Corner Lot
  • Roof Material: Shingle, Rubber
Parking Features
  • Covered Spaces: .00
  • Garage: No
  • Garage Parking: Paved Drive, Off-Street
  • Open Parking: Yes
  • Parking Features: Paved Drive, Off-Street
  • Parking Features: Off-Street
Utilities
  • Cooling: Central Air
  • Cooling: Yes
  • Heating: Central
  • Heating: Yes
  • Sewer: City/Town Sewer
  • Utility Connections: for Gas Range, for Gas Oven, for Electric Dryer, Washer Hookup
  • Water: Public
Property Information
Property Info
  • Year Round: Yes
  • Farm Land Area Units: Square Feet
  • WARRANTY: No
  • Lot Size Units: Acres
  • Road Frontage Type: Public
Tax Information
  • Tax ID: W:09 P:03293 S:000,3397293
  • Assessments: $2,056,900
  • Book: 58524
  • Tax Year: 2026
  • Zoning: R4
Building / Association Information
Living Characteristics
  • Beds Total: 14
  • Total Living Levels: 8
Other Building Characteristics
  • Foundation: Brick/Mortar
  • Levels: 8
  • Cooling Units: 7
  • Cooling Zones: 7
  • Heat Units: 7
  • Heat Zones: 7
Income / Expenses
  • Annual Expenses Source: Estimated, Owner
  • GOI: $291,000.00
  • NOI: $247,147.00
Complex & Association Information
  • Adult Community: No
Unit Information
Unit 1 Description
  • Floor U1: 1
  • Lease U1: Y
  • Levels U1: 2
Unit 2 Description
  • Floor U2: 1
  • Lease U2: Y
  • Levels U2: 2
Unit 3 Description
  • Floor U3: 1
  • Lease U3: Y
  • Levels U3: 1
Unit 4 Description
  • Floor U4: 3
  • Lease U4: Y
  • Levels U4: 2
Rental Info
Rental Info
  • Total Actual Rent: $22,925.00

Property History for 27 Dudley Street

DateEvent & SourcePriceAppreciation
Feb 18, 2026

Listed (Active)

MLS PIN #73478206

$3,625,000—
Dec 21, 2025

Canceled

MLS PIN #73435766

$3,700,000—
Dec 21, 2025

Temporarily Withdrawn

MLS PIN #73435766

$3,700,000—
Sep 25, 2025

Listed (Active)

MLS PIN #73435766

$3,700,000—
Aug 11, 2025

Canceled

MLS PIN #73343819

$3,700,000—
Mar 11, 2025

Listed (Active)

MLS PIN #73343819

$3,800,000—
Dec 31, 2021

Expired

MLS PIN #72865029

$4,000,000—
Jul 13, 2021

Listed (Active)

MLS PIN #72865029

$4,200,000—
Sep 14, 2017

Sold (Public Record)

Public Record #605857563

$1,325,000

+8.0% / yr

Sep 14, 2017

Sold

MLS PIN #72181478

$1,325,000—
Jun 21, 2017

Contingent

MLS PIN #72181478

—
Jun 13, 2017

Listed (Active)

MLS PIN #72181478

$1,300,000—
Jan 31, 2003

Sold (Public Record)

Public Record #126408080

$428,000—
DateEvent & SourcePrice
02/18/2026

Listed (Active)

MLS PIN #73478206

$3,625,000
12/21/2025

Canceled

MLS PIN #73435766

$3,700,000
12/21/2025

Temporarily Withdrawn

MLS PIN #73435766

$3,700,000
09/25/2025

Listed (Active)

MLS PIN #73435766

$3,700,000
08/11/2025

Canceled

MLS PIN #73343819

$3,700,000
03/11/2025

Listed (Active)

MLS PIN #73343819

$3,800,000
12/31/2021

Expired

MLS PIN #72865029

$4,000,000
07/13/2021

Listed (Active)

MLS PIN #72865029

$4,200,000
09/14/2017

Sold (Public Record)

Public Record #605857563

$1,325,000

+8.0% / yr

09/14/2017

Sold

MLS PIN #72181478

$1,325,000
06/21/2017

Contingent

MLS PIN #72181478

—
06/13/2017

Listed (Active)

MLS PIN #72181478

$1,300,000
01/31/2003

Sold (Public Record)

Public Record #126408080

$428,000

For completeness, Compass often displays two records for one sale: the MLS record and the public record.

Public Records for 27 Dudley Street

Taxable ValueLand$476,100Additions$1,512,400Total$1,988,500
Tax Record2025$23,027 ($1,919 / month)
Home Facts
Total Finished SqFt5,660 SqFtAbove Grade Finished SqFt5,660 SqFtStories3Lot Size8,241 SqFtStyleMulti-Family Res (5+ Units)Year Built1900Year Renovated2019ZoningR4CountySUFFOLKAPNROXB W:09 P:03293 S:000

Schools near 27 Dudley Street

This home is within Boston Public Schools.
Rating
School
Type
Grades
Distance
Public - PK to 6
Public - 7 to 12
Public - 9 to 12
Public - 6 to 12
Rating
School
Distance
Hale Elementary School
PublicPK to 6

O'Bryant School Math/Science
Public7 to 12

Madison Park High
Public9 to 12

Dearborn Middle School
Public6 to 12

School ratings and boundaries are provided by GreatSchools.org and Pitney Bowes. This information should only be used as a reference. Proximity or boundaries shown here are not a guarantee of enrollment. Please reach out to schools directly to verify all information and enrollment eligibility.

Similar Homes

Similar Sold Homes

27 Dudley Street is a multi-family home for sale in Boston, MA 02119. This property was listed for sale on February 18, 2026 by Compass, it's currently listed at $3,625,000. It has been on the market for a total of 3 days and was last sold on September 14, 2017. This listing's school district is Boston Public Schools. Nearby schools include Hale Elementary School, O'Bryant School Math/Science and Madison Park High. 27 Dudley Street is a 14-bed, 11-bath, 6,509 sqft multi-family home built in 1900.

No guarantee, warranty or representation of any kind is made regarding the completeness or accuracy of descriptions or measurements (including square footage measurements and property condition), such should be independently verified, and Compass, Inc., its subsidiaries, affiliates and their agents and associated third parties expressly disclaims any liability in connection therewith. Photos may be virtually staged or digitally enhanced and may not reflect actual property conditions. Offers of compensation are subject to change at the discretion of the seller. No financial or legal advice provided. Equal Housing Opportunity.

The property listing data and information, or the images, set forth herein were provided to MLS Property Information Network, Inc., Martha's Vineyard MLS, CCIMLS, Link MLS, and Berkshire County Board of REALTORS from third party sources, including sellers, lessors and public records, and were compiled by MLS Property Information Network, Inc., Martha's Vineyard MLS, CCIMLS, Link MLS, and Berkshire County Board of REALTORS. The property listing data and information, and the images, are for the personal, non-commercial use of consumers having a good faith interest in purchasing or leasing listed properties of the type displayed to them and may not be used for any purpose other than to identify prospective properties which such consumers may have a good faith interest in purchasing or leasing. MLS Property Information Network, Inc., Martha's Vineyard MLS, CCIMLS, Link MLS, and Berkshire County Board of REALTORS and its subscribers disclaim any and all representations and warranties as to the accuracy of the property listing data and information, or as to the accuracy of any of the images, set forth herein.