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 $22,825/month with a 6.3% cap rate and a projected 7.3% 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 $22,825/month with a 6.3% cap rate and a projected 7.3% 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. Mission Realty Advisors

    Mission Realty Advisors

    Listing Agent

    Compass

    P: (203)-893-8316

  2. Eric Johnson

    Eric Johnson

    Alternative Listing Agent

    Compass

    P: (203)-893-8316

  3. Bill MacDonald

    Bill MacDonald

    Alternative Listing Agent

    Compass

    P: (857)-540-1779

  4. Ozzy Moore

    Ozzy Moore

    Alternative Listing Agent

    Compass

    P: (617)-650-0840

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
Open Parking Spaces
8.00
Parking Spaces Total
8
LISTING UPDATED: 06/28/2026 10:43 AM

Property Details for 27 Dudley Street

StatusUnder Agreement
MLS #73478206
Days on Market92
Taxes$25,748 / year
HOA Fees-
Property 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

$20,209 per month

30 year fixed, 6.36% Interest

Principal and Interest

$18,064

Property Taxes

$2,146

HOA Dues

$0

The Payment Calculator is for illustrative purposes only.

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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
  • Disclosures: Unit 3 electric is on common meter
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: $22,825.00

Property History for 27 Dudley Street

DateEvent & SourcePriceAppreciation
May 21, 2026

Under Agreement

MLS PIN #73478206

—
May 21, 2026

Contingent

MLS PIN #73478206

—
Feb 18, 2026

Listed (Active)

MLS PIN #73478206

$3,625,000—
DateEvent & SourcePrice
05/21/2026

Under Agreement

MLS PIN #73478206

—
05/21/2026

Contingent

MLS PIN #73478206

—
02/18/2026

Listed (Active)

MLS PIN #73478206

$3,625,000

For completeness, we 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.

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No guarantee, warranty or representation of any kind is made regarding the completeness or accuracy of any information, descriptions or measurements (including square footage measurements and property condition), such should be independently verified through appropriate means, including, but not limited to, in person inspection and public records, and Compass International Holdings, its subsidiaries, affiliates and independently owned and operated franchisees, and their affiliated agents and associated third parties expressly disclaim 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 seller's discretion. 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.