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

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 Details tap to expand

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: 10/17/25

Property History tap to expand

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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Seller's Representative: Mission Realty Advisors, Compass
Sub Agent Compensation: n/a
Buyer Agent Compensation: n/a
Facilitator Compensation: n/a
Compensation Based On: n/a
Sub-Agency Relationship Offered: No

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MLS PIN data last updated at 2025-10-17 15:39:00