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You are here:
$3,700,000
7 Unit
14 Beds
11 Baths
6509 SQFT
0.19 Acre
27 Dudley St
Boston, MA 02119

Property 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 $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

Building Information

  • Total Units: 7
  • Total Floors: 9
  • Total Bedrooms: 14
  • Total Full Baths: 11
  • Amenities: Bike Path, Conservation Area, Highway Access, House of Worship, Laundromat, Marina, Medical Facility, Other (See Remarks), Park, Private School, Public School, Public Transportation, Shopping, Swimming Pool, T-Station, Tennis Court, University, Walk/Jog Trails
  • Common Rooms: Dining Room, Kitchen, Living Room
  • Common Interior Features: Tile Floor
  • Common Appliances: Dishwasher, Disposal, Dryer, Microwave, Range, Refrigerator, Washer, Washer Hookup
  • Common Heating: Central Heat, Electric
  • Common Cooling: Central Air

Financial

  • APOD Available: Yes
  • Expenses Source: Estimated, Owner Provided
  • Gross Operating Income: 291000
  • Net Operating Income: 247147

Utilities

  • Heat Zones: 7
  • Cooling Zones: 7
  • Energy Features: Insulated Windows
  • Utility Connections: Washer Hookup, for Electric Dryer, for Gas Oven, for Gas Range
  • Water: City/Town Water, Private
  • Sewer: City/Town Sewer, Private

Unit 1 Description

  • Under Lease: Yes
  • Floors: 1
  • Levels: 2

Unit 2 Description

  • Under Lease: Yes
  • Floors: 1
  • Levels: 2

Unit 3 Description

  • Under Lease: Yes
  • Floors: 1
  • Levels: 2

Unit 4 Description

  • Under Lease: Yes
  • Floors: 3
  • Levels: 2

Construction

  • Year Built: 1900
  • Type: 5-9 Family
  • Construction Type: Brick
  • Foundation Info: Brick
  • Roof Material: Aluminum, Asphalt/Fiberglass Shingles, Rubber
  • Flooring Type: Tile, Wood
  • Lead Paint: Unknown
  • Year Round: Yes
  • Warranty: No

Other Information

  • MLS ID# 73435766
  • Last Updated: 11/20/25

Date Event Price Price/Sq Ft Source
09/29/2025Active$3,700,000$568MLSPIN
09/25/2025New$3,700,000$568MLSPIN
08/11/2025Canceled$3,700,000$568MLSPIN
07/15/2025Active$3,700,000$568MLSPIN
07/11/2025Extended$3,700,000$568MLSPIN
04/19/2025Active$3,700,000$568MLSPIN
04/15/2025Price Change$3,700,000$568MLSPIN
03/15/2025Active$3,800,000$584MLSPIN
03/11/2025New$3,800,000$584MLSPIN

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Map & Resources

O'Bryant School of Math & Science

Public Secondary School, Grades: 7-12

0.13mi

John D. O'Bryant School of Mathematics and Science

School

0.13mi

James P Timilty Middle School

Public School, Grades: 6-8

0.16mi

Madison Park Technical Vocational High School

Grades: 9-12

0.2mi

Roxbury Community College

University

0.2mi

Madison Park Technical Vocational High School

Public Secondary School, Grades: 9-12

0.21mi

Paige Academy

Private School, Grades: PK-1

0.21mi

Paige Academy

Private School, Grades: PK-6

0.21mi

Dudley Cafe

Coffee Shop & Sandwich (Cafe)

0.29mi

Arizona BBQ House of Pizza

Pizzeria

0.23mi

Yummy Yummy Chinese Food

Chinese (Fast Food)

0.23mi

Regal Fried Chicken

Chicken (Fast Food)

0.23mi

Dunkin' Donuts

Donut & Coffee Shop

0.24mi

Dudley Dough

Pizzeria

0.25mi

Domino's

Pizzeria

0.35mi

Cafe Crossing

Sandwich (Fast Food)

0.4mi

B-2 Boston Police Department

Police

0.16mi

Boston Police Department Headquarters

Local Police

0.33mi

Engine 14 and Ladder 4

Fire Station

0.33mi

Hibernian Hall

Arts Centre

0.35mi

Dillaway-Thomas House

Museum

0.12mi

Reggie Lewis Athletic Center

Sports Centre. Sports: Running

0.23mi

Roxbury Heritage State Park

Park

0.08mi

John Eliot Square

Park

0.09mi

Kitteridge Park

Municipal Park

0.12mi

Jeep Jones Park

Municipal Park

0.15mi

Justice Edward O. Gourdin Veterans Memorial Park

Park

0.16mi

Saint James Street Park

Park

0.24mi

Linwood Park

Municipal Park

0.29mi

Cedar Square

Municipal Park

0.29mi

Lambert Avenue Playground

Playground

0.15mi

Roxbury Branch of the Boston Public Library

Library

0.27mi

Roxbury Community College Learning Resources Center

Library

0.34mi

Daily Table

Supermarket

0.32mi

Tropical Foods

Supermarket

0.42mi

42A John Eliot Sq

14
41
45

0.1mi

Malcolm X Blvd opp O'Bryant HS

15
19
23
28
44
45
66

0.11mi

Malcolm X Blvd @ O'Bryant HS

15
19
23
28
44
45
66

0.11mi

205 Roxbury St

14
41
45

0.13mi

Malcolm X Blvd @ Shawmut Ave

15
19
23
28
44
45
66

0.14mi

Dudley St @ Guild Row

14
41
45

0.14mi

Washington St @ Bartlett St

42

0.14mi

Malcolm X Blvd @ Shawmut Ave

14
15
19
23
28
41
44
45
66

0.15mi

Seller's Representative: Mission Realty Advisors, Compass
MLS ID#: 73435766

© 2025 MLS Property Information Network, Inc.. All rights reserved.

The property listing data and information set forth herein were provided to MLS Property Information Network, Inc. from third party sources, including sellers, lessors and public records, and were compiled by MLS Property Information Network, Inc. The property listing data and information 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. and its subscribers disclaim any and all representations and warranties as to the accuracy of the property listing data and information set forth herein.

MLS PIN data last updated at 2025-11-20 14:29:00