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.
For sale
$3,625,000
27 Dudley St, Roxbury, MA 02119
14beds
6,509sqft
Est.:
5-9 Family
Built in 1900
-- sqft lot
$-- Zestimate®
$557/sqft
$-- HOA
What's special
Modern finishesCentral hvacIn-unit laundryHardwood floorsWaterfall quartz countertops
- 5 days |
- 285 |
- 17 |
Zillow last checked: 8 hours ago
Listing updated: February 22, 2026 at 12:07am
Listed by:
Mission Realty Advisors 617-942-1609,
Compass 617-752-6845
Source: MLS PIN,MLS#: 73478206
Tour with a local agent
Facts & features
Interior
Bedrooms & bathrooms
- Bedrooms: 14
- Bathrooms: 11
- Full bathrooms: 11
Heating
- Central
Cooling
- Central Air
Appliances
- Included: Range, Dishwasher, Disposal, Microwave, Refrigerator, Washer, Dryer
- Laundry: Electric Dryer Hookup, Washer Hookup
Features
- Living Room, Dining Room, Kitchen, Laundry Room
- Flooring: Wood, Tile
- Windows: Insulated Windows
- Has basement: No
- Has fireplace: No
Interior area
- Total structure area: 6,509
- Total interior livable area: 6,509 sqft
- Finished area above ground: 5,291
- Finished area below ground: 1,218
Property
Parking
- Total spaces: 8
- Parking features: Paved Drive, Off Street
- Uncovered spaces: 8
Features
- Fencing: Fenced
Lot
- Size: 8,241 Square Feet
- Features: Corner Lot
Details
- Parcel number: W:09 P:03293 S:000,3397293
- Zoning: R4
Construction
Type & style
- Home type: MultiFamily
- Property subtype: 5-9 Family
Materials
- Brick
- Foundation: Brick/Mortar
- Roof: Shingle,Rubber
Condition
- Year built: 1900
Utilities & green energy
- Sewer: Public Sewer
- Water: Public
- Utilities for property: for Gas Range, for Gas Oven, for Electric Dryer, Washer Hookup
Community & HOA
Community
- Features: Public Transportation, Shopping, Pool, Tennis Court(s), 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
Location
- Region: Roxbury
Financial & listing details
- Price per square foot: $557/sqft
- Tax assessed value: $2,056,900
- Annual tax amount: $25,748
- Date on market: 2/18/2026
- Total actual rent: 22925
Estimated market value
Not available
Estimated sales range
Not available
$3,677/mo
Price history
Price history
| Date | Event | Price |
|---|---|---|
| 2/18/2026 | Listed for sale | $3,625,000-2%$557/sqft |
Source: MLS PIN #73478206 Report a problem | ||
| 12/21/2025 | Listing removed | $3,700,000$568/sqft |
Source: MLS PIN #73435766 Report a problem | ||
| 9/25/2025 | Listed for sale | $3,700,000$568/sqft |
Source: MLS PIN #73435766 Report a problem | ||
| 8/11/2025 | Listing removed | $3,700,000$568/sqft |
Source: MLS PIN #73343819 Report a problem | ||
| 4/15/2025 | Price change | $3,700,000-2.6%$568/sqft |
Source: MLS PIN #73343819 Report a problem | ||
| 3/11/2025 | Listed for sale | $3,800,000-5%$584/sqft |
Source: MLS PIN #73343819 Report a problem | ||
| 6/3/2022 | Listing removed | -- |
Source: MLS PIN #72865029 Report a problem | ||
| 1/1/2022 | Listing removed | $4,000,000$615/sqft |
Source: MLS PIN #72865029 Report a problem | ||
| 9/21/2021 | Listed for sale | $4,000,000+201.9%$615/sqft |
Source: MLS PIN #72865029 Report a problem | ||
| 5/1/2020 | Listing removed | $3,330$1/sqft |
Source: Kirby Taylor Properties Report a problem | ||
| 4/10/2020 | Listed for rent | $3,330+51.4%$1/sqft |
Source: Kirby Taylor Properties Report a problem | ||
| 2/1/2018 | Listing removed | $2,200 |
Source: Weichert Realtors Hudson Morgan Group Report a problem | ||
| 1/2/2018 | Listed for rent | $2,200 |
Source: Weichert Realtors Hudson Morgan Group Report a problem | ||
| 9/14/2017 | Sold | $1,325,000+1.9%$204/sqft |
Source: Public Record Report a problem | ||
| 6/22/2017 | Pending sale | $1,300,000$200/sqft |
Source: Preferred Real Estate Group #72181478 Report a problem | ||
| 6/14/2017 | Listed for sale | $1,300,000+203.7%$200/sqft |
Source: Preferred Real Estate Group #72181478 Report a problem | ||
| 1/31/2003 | Sold | $428,000$66/sqft |
Source: Public Record Report a problem | ||
Public tax history
Public tax history
| Year | Property taxes | Tax assessment |
|---|---|---|
| 2025 | $23,027 +2.3% | $1,988,500 -3.7% |
| 2024 | $22,516 0% | $2,065,700 -1.5% |
| 2023 | $22,522 +1.9% | $2,097,000 +3.3% |
| 2022 | $22,092 +3.4% | $2,030,500 +1.4% |
| 2021 | $21,363 +54.5% | $2,002,200 +52.9% |
| 2020 | $13,826 +47.5% | $1,309,300 +47.3% |
| 2019 | $9,371 +24.7% | $889,105 +24% |
| 2018 | $7,516 +499.7% | $717,155 +1% |
| 2017 | $1,253 -82% | $710,125 +12% |
| 2016 | $6,974 +34% | $634,030 +47.5% |
| 2015 | $5,205 | $429,780 +58.6% |
| 2011 | -- | $271,000 -0.9% |
| 2010 | -- | $273,500 -4.4% |
| 2009 | -- | $286,000 |
| 2008 | -- | $286,000 +1.4% |
| 2007 | -- | $282,000 |
Find assessor info on the county website
BuyAbility℠ payment
Est. payment
$19,986/mo
Principal & interest
$18022
Property taxes
$1964
Climate risks
Neighborhood: Roxbury
Nearby schools
GreatSchools rating
- 6/10Hale Elementary SchoolGrades: PK-6Distance: 0.3 mi
- 8/10O'Bryant School Math/ScienceGrades: 7-12Distance: 0.1 mi
- 1/10Madison Park HighGrades: 9-12Distance: 0.2 mi
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