299 Dudley Street, Roxbury presents an exceptional opportunity to acquire a boutique multifamily building constructed in 2015, comprising 8 thoughtfully designed three-bedroom, two-bathroom units with modern finishes throughout. Each residence features large, open floor plans bathed in natural light, offering stunning city and skyline views that elevate the everyday living experience. The property is fully equipped with all separate utilities, on-site parking, common laundry, and dedicated storage and bike storage, delivering a comprehensive amenity package that commands strong tenant demand. Situated in a vibrant, transit-oriented neighborhood, 299 Dudley Street offers residents seamless connectivity to Boston's core while benefiting from the continued growth and investment in the surrounding area. With its modern construction, desirable unit mix of spacious three-bedroom homes, and turnkey operational profile, this asset represents a compelling addition to any investor.
For sale
Price cut: $200K (5/11)
$4,375,000
299 Dudley St, Roxbury, MA 02119
24beds
7,200sqft
5+ Family - 5+ Units Side by Side
Built in 2015
-- sqft lot
$-- Zestimate®
$608/sqft
$-- HOA
What's special
Modern finishes throughoutOn-site parking
- 86 days |
- 107 |
- 2 |
Zillow last checked:
Listing updated:
Listed by:
Kevin Benzinger 860-424-7613,
Boston Realty Advisors 617-375-7900
Source: MLS PIN,MLS#: 73487339
Tour with a local agent
Facts & features
Interior
Bedrooms & bathrooms
- Bedrooms: 24
- Bathrooms: 16
- Full bathrooms: 16
Features
- Basement: Full
- Has fireplace: No
Interior area
- Total structure area: 7,200
- Total interior livable area: 7,200 sqft
- Finished area above ground: 7,200
Property
Parking
- Total spaces: 8
- Uncovered spaces: 8
Lot
- Size: 3,698 Square Feet
- Features: Other
Details
- Parcel number: 3399182
- Zoning: 99
Construction
Type & style
- Home type: MultiFamily
- Property subtype: 5+ Family - 5+ Units Side by Side
Materials
- Foundation: Other
Condition
- Year built: 2015
Utilities & green energy
- Sewer: Public Sewer
- Water: Public
Community & HOA
Community
- Features: Other
Location
- Region: Roxbury
Financial & listing details
- Price per square foot: $608/sqft
- Tax assessed value: $99
- Annual tax amount: $99
- Date on market: 3/16/2026
- Listing terms: Other (See Remarks)
- Total actual rent: 0
Estimated market value
Not available
Estimated sales range
Not available
$3,583/mo
Price history
| Date | Event | Price |
|---|---|---|
| 6/3/2026 | Listing removed | $3,800$1/sqft |
Source: Zillow Rentals Report a problem | ||
| 5/13/2026 | Listed for rent | $3,800$1/sqft |
Source: Zillow Rentals Report a problem | ||
| 5/11/2026 | Price change | $4,375,000-4.4%$608/sqft |
Source: MLS PIN #73487339 Report a problem | ||
| 3/16/2026 | Listed for sale | $4,575,000$635/sqft |
Source: MLS PIN #73487339 Report a problem | ||
| 6/27/2025 | Listing removed | $3,800$1/sqft |
Source: Zillow Rentals Report a problem | ||
| 5/27/2025 | Listed for rent | $3,800+11.8%$1/sqft |
Source: Zillow Rentals Report a problem | ||
| 5/23/2023 | Listing removed | -- |
Source: Zillow Rentals Report a problem | ||
| 3/9/2023 | Price change | $3,400-5.6% |
Source: Zillow Rentals Report a problem | ||
| 1/30/2023 | Listed for rent | $3,600+5.9%$1/sqft |
Source: Zillow Rentals Report a problem | ||
| 6/13/2022 | Listing removed | -- |
Source: Zillow Rental Manager Report a problem | ||
| 6/1/2022 | Listed for rent | $3,400+25.9% |
Source: Zillow Rental Manager Report a problem | ||
| 8/31/2021 | Listing removed | -- |
Source: Zillow Rental Manager Report a problem | ||
| 8/17/2021 | Listed for rent | $2,700-6.9% |
Source: Zillow Rental Manager Report a problem | ||
| 6/25/2021 | Listing removed | -- |
Source: Zillow Rental Manager Report a problem | ||
| 5/27/2021 | Listed for rent | $2,900 |
Source: Zillow Rental Manager Report a problem | ||
| 7/3/2019 | Listing removed | $2,900 |
Source: Carl Stephens Red Tree Real Estate Report a problem | ||
| 6/17/2019 | Listed for rent | $2,900-1.7% |
Source: Carl Stephens Red Tree Real Estate Report a problem | ||
| 2/19/2019 | Listing removed | $2,950 |
Source: Zillow Rental Network Report a problem | ||
| 2/16/2019 | Listed for rent | $2,950 |
Source: Zillow Rental Network Report a problem | ||
Public tax history
| Year | Property taxes | Tax assessment |
|---|---|---|
| 2025 | $16,390 +2.3% | $1,415,398 -3.7% |
| 2024 | $16,019 0% | $1,469,651 -1.5% |
| 2023 | $16,024 +1.9% | $1,491,950 +3.2% |
| 2022 | $15,721 +2.8% | $1,444,990 +0.8% |
| 2021 | $15,293 +2.5% | $1,433,290 +1.5% |
| 2020 | $14,913 +3.8% | $1,412,198 +3.6% |
| 2019 | $14,373 +14.4% | $1,363,696 +13.8% |
| 2018 | $12,562 +20948.9% | $1,198,677 +75.7% |
| 2017 | $60 -75% | $682,372 +3044.6% |
| 2016 | $239 -9.1% | $21,700 |
| 2015 | $263 | $21,700 |
Find assessor info on the county website
Monthly payment
Est. payment$--/mo
Payment breakdown
Explore the cost of this home by adjusting the details. Changes won't be saved.
All calculations are estimates and provided by Zillow, Inc. for informational purposes only. Actual amounts may vary.
HOA fees may include property taxes on listings classified as Co-Ops. Contact the listing agent and/or owner for fee details.
Mortgage interest rates are dependent on a number of factors, including credit score, down payment, and repayment length. Interest rate data provided by Zillow Group Marketplace, Inc. as of 1/1/1970 from various mortgage lenders with which we have lead or other similar arrangements; the Estimated Payment is an average of those rates.
See how much you could borrow to make a competitive offer.
Climate risks
Neighborhood: Roxbury
Nearby schools
GreatSchools rating
- 3/10Orchard Gardens K-8 SchoolGrades: PK-8Distance: 0.2 mi
- 4/10Dearborn Middle SchoolGrades: 6-12Distance: 0.2 mi
- 4/10Samuel W. Mason Pilot ElementaryGrades: PK-5Distance: 0.4 mi
A local agent can set up tours, give advice and negotiate with sellers.
A local lender can help you make sure your offer is ready when you are.
- Massachusetts
- Suffolk County
- Boston
- 02119
- Roxbury
- 299 Dudley St



