Pending

$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

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.

97 days

165

9

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: 22825

Estimated market value

Not available

Estimated sales range

Not available

$3,448/mo

Price history

Date	Event	Price
5/21/2026	Pending sale	$3,625,000$557/sqft
Source: MLS PIN #73478206 Report a problem
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

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

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