27 Dudley St, Roxbury, MA 02119
Property image
Property image
SOLD
JUL 9, 2026

$3,450,000

Last sold price
  • 14 Beds
  • 11 Baths
  • 6,509 sqft

27 Dudley St, Roxbury, MA 02119

Roxbury
Est. Refi. Payment $20,343/mo*
Refinance Your Home
Currently Off Market - Sold Jul 9, 2026 for $3,450,000 (5% below list price)

Home Value

Learn more about this home's value by checking out the value of nearby homes and how much similar homes have sold for.

Comparable sales

These are recently sold homes that have a similar location or other similar features to this home, like bedrooms, bathrooms, and square footage. Get a sense of the expected prices in the area by viewing these homes.
Address
Distance
Property Type
Sold Price
Sold Date
Bed
Bath
Sqft
23 Hillside St, Roxbury, MA
0.55
Multi-Family Home
$3,255,000
07/15/26
13
7
5,457
34-36 Alleghany St, Roxbury Crossing, MA
0.51
Multi-Family Home
$2,300,000
08/03/26
16
5
4,902
94 Walnut Ave, Roxbury, MA
0.56
Multi-Family Home
$2,300,000
07/08/26
26
9
7,812
22 Fisher Ave, Roxbury, MA
0.62
Multi-Family Home
$2,790,000
12/23/25
14
4
5,155
10-12 Rockledge St, Roxbury, MA
0.19
Multi-Family Home
$1,318,500
07/31/26
10
5
3,381
70 Rockland St, Roxbury, MA
0.47
Multi-Family Home
$1,625,000
03/06/26
11
4.5
4,734
409 Dudley St, Boston, MA
0.74
Multi-Family Home
$3,625,000
08/03/26
22
16
13,440
97 Hillside St, Roxbury, MA
0.78
Multi-Family Home
$3,250,000
01/12/26
14
7
4,546
51 Saint James St, Roxbury, MA
0.22
Multi-Family Home
$700,000
04/07/26
6
3
3,104

Nearby home prices

Get a sense of expected prices in the area by checking the value of nearby homes.
Address
Distance
Price
Bed
Bath
Sqft
Status
64 Bartlett St #4, Roxbury, MA 02119
0.05
$615,000
3
1.5
1,267
For Sale
27 Kenilworth St #2, Roxbury, MA 02119
0.05
$584,000
1
1
730
For Sale
53 Dudley St, Roxbury, MA 02119
0.06
$957,100
4
3
2,967
Off Market
14 John Eliot Sq #3A, Roxbury, MA 02119
0.07
-
2
1
774
Off Market
51-53 Norfolk St, Roxbury, MA 02119
0.09
$699,900
3
1
1,712
For Sale
10-18 John Eliot Sq #3D, Roxbury, MA 02119
0.07
$429,000
1
1
579
Recently Sold
22 Kenilworth St, Roxbury, MA 02119
0.10
$1,250,000
3
2.5
2,100
Recently Sold
10-18 John Eliot Sq #3D, Roxbury, MA 02119
0.10
-
1
1
579
Off Market
19-21 Norfolk St #1, Roxbury, MA 02119
0.11
$625,000
3
2
1,338
Recently Sold
19-21 Norfolk St #1, Roxbury, MA 02119
0.12
-
3
2
1,338
Off Market
30 Millmont St #2, Roxbury, MA 02119
0.13
$469,000
2
1
1,032
Recently Sold

Local Information

  • Map ViewExplore the area around 27 Dudley St.
  • Schools30 Preschool Schools31 Elementary Schools20 Middle Schools19 High Schools
  • Shop & Eat
-- mins to
Commute Destination

Home Highlights

Multi-Family
Built in 1900
6,509 sqft
$530/sqft
8 Open Spaces

About this House

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.
27 Dudley St, Roxbury, MA 02119 is a 14 bedroom, 11 bathroom, 6,509 sqft multi-family in Roxbury, built in 1900. It last sold for $3,450,000 on Jul 9, 2026 (5% below the $3,625,000 asking price). More recently, it was listed as a rental in April 2020 with an asking price of $3,330 per month. That rental listing was removed on May 1, 2020. This property is not currently displayed as for sale or rent on Trulia. The Trulia Estimate rent is $2,165/month.
Last check for updates: about 20 hours ago
Listed by Mission Realty Advisors, (617) 942-1609
Compass, (617) 752-6845
Bought with: The Zur Attias Team, (978) 621-0734, The Attias Group, LLC, (978) 371-1234
Source: MLS PIN, MLS#73478206

Home Details for 27 Dudley St

Interior Features

Interior Details
Number of Rooms: 28
Beds & Baths
Number of Bedrooms: 14Number of Bathrooms: 11Number of Bathrooms (full): 11
Dimensions and Layout
Living Area: 6509 Square Feet
Appliances & Utilities
Utilities: for Gas Range, for Gas Oven, for Electric Dryer, Washer HookupAppliances: Range, Dishwasher, Disposal, Microwave, Refrigerator, Washer, DryerDishwasherDisposalDryerLaundry: Electric Dryer Hookup,Washer HookupMicrowaveRefrigeratorWasher
Heating & Cooling
Heating: CentralHas CoolingAir Conditioning: Central AirHas HeatingHeating Fuel: Central
Fireplace & Spa
No FireplaceNo Spa
Windows, Doors, Floors & Walls
Window: Insulated WindowsFlooring: Wood, Tile
Levels, Entrance, & Accessibility
Number of Stories: 8Floors: Wood, Tile

Exterior Features

Exterior Home Features
Roof: Shingle RubberFencing: FencedFoundation: Brick/Mortar
Parking & Garage
Open Parking Spaces: 8No GarageHas Open ParkingParking Spaces: 8Parking: Paved Drive,Off Street
Frontage
Road Frontage: PublicNot on Waterfront
Water & Sewer
Sewer: Public Sewer
Finished Area
Finished Area (above surface): 5291Finished Area (below surface): 1218

Property Information

Year Built
Year Built: 1900
Property Type / Style
Property Type: Residential IncomeProperty Subtype: 5-9 Family
Building
Construction Materials: BrickDoes Not Include Home Warranty
Property Information
Parcel Number: W:09 P:03293 S:000, 3397293

Price & Status

Price
List Price: $3,625,000Price Per Sqft: $530/sqft
Status Change & Dates
Off Market Date: Thu May 21 2026

Active Status

MLS Status: Sold

Location

Direction & Address
City: Boston

Building

Building Area
Building Area: 6509 Square Feet

Community

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, OtherNot Senior Community

Lot Information

Lot Area: 8241 sqft

Miscellaneous

Mls Number: 73478206Above Grade Unfinished Area: 5291

Additional Information

Public TransportationShoppingPoolTennis Court(s)ParkWalk/Jog TrailsMedical FacilityLaundromatBike PathConservation AreaHighway AccessHouse of WorshipMarinaPrivate SchoolPublic SchoolT-StationUniversityOther

Price and Tax history

DateEventPrice
Jul 9, 2026
Source: MLS PIN #73478206
Sold
$3,450,000
May 21, 2026
Source: MLS PIN #73478206
Pending
$3,625,000
Feb 18, 2026
Source: MLS PIN #73478206
Listed For Sale
$3,625,000
Dec 21, 2025
Source: MLS PIN #73435766
ListingRemoved
$3,700,000
Sep 25, 2025
Source: MLS PIN #73435766
Listed For Sale
$3,700,000

Market trends in Boston

Last updated August 2026
Buyer'sMarketSeller'sMarket
Avg. sale price
$830K
$6.67KMoM
Sale-to-List Price
99.3%
0.3%MoM
Price per sq ft
$759
$20MoM
Available listings
1905
310MoM

Around this home

View nearby schools on GreatSchools
The GreatSchools Rating compares schools on a variety of school quality indicators including test scores, college readiness, equity and more. Learn more.

Neighborhood Overview

Roxbury
See Local Highlights
Neighborhood stats provided by third party data sources.

What Locals Say about Roxbury

At least 326 Trulia users voted on each feature.

  • 87 % Say there are sidewalks

  • 77 % Say it's walkable to grocery stores

  • 71 % Say streets are well-lit

  • 68 % Say it's dog friendly

  • 66 % Say it's walkable to restaurants

  • 60 % Say there's holiday spirit

  • 57 % Say yards are well-kept

  • 55 % Say kids play outside

  • 54 % Say parking is easy

  • 50 % Say car is needed

  • 47 % Say people would walk alone at night

  • 47 % Say neighbors are friendly

  • 43 % Say they plan to stay for at least 5 years

  • 39 % Say there are community events

  • 35 % Say it's quiet

  • 33 % Say there's wildlife

Sourced by Trulia users. Learn more about our methodology.
  • Khai
    "Public transit is very accessible with two entirely free of charge buses in the neighborhood and a transit hub within a half mile walk"
    0
    Flag
  • Ju N.
    "You see lots of people walking dogs but most people as myself are refused rentals in these same neighborhoods because of a few incidents from others who care not to pick cleanup of lease their dogs. Otherwise great place"
    1
    Flag
  • Trulia User
    "Roxbury has come a long way. It’s a good place.im happy with the way it looks and the way it fits in my route."
    0
    Flag
  • Trulia User
    "I've only lived in boston for a year but from what I've noticed dog owners have very friendly dogs but I haven't seen any dog parks in or around Roxbury "
    1
    Flag
  • Trulia User
    "The public transportation is good. The bus station is six short blocks away from my home. There are several bus routes to take you all over the city."
    0
    Flag
  • Trulia User
    "it is a family safe zone and plenty schools for kids available in the area ..it is a good neighborhood "
    1
    Flag
  • Trulia User
    "friendly neighbors that look out for each other a lot of holiday spirit quiet street well maintained in winter as far as snow removal and shoveling very respectful of each other's property very family oriented everyone looks after each other's property "
    0
    Flag
  • Trulia User
    "Dogs are very welcome as long as the owners pick up after them so the dog owners will be happy there is a park nearby"
    0
    Flag
  • Rcorreabwh
    "It’s close to hospitals, schools and restaurants, supermarket, laundromat, post office, train station, parks, library."
    10
    Flag
  • T02119
    "Certain areas are becoming crowded with all of the new builds. Street parking can be challenging at times. Most neighbors are great but some are not very considerate when it comes to noise levels and parking. "
    6
    Flag
  • Daniel B.
    "It is fair, no complaints. I can get train and buses though I have to walk everyday to either train or bus stations."
    2
    Flag
  • Djackson3710
    "There’s not a lot of areas that are dog friendly or allows dog in also it’s literally one dogs parks in the neighborhood "
    2
    Flag
  • Nicole F.
    "SOWA is great. Sidewalk shopping days at local businesses. But it’s less about events, more about living in the perfect place for a summer evening stroll, glasses clinking at small restaurants, music on the breeze. "
    0
    Flag
  • Michael M.
    "old architecture. diverse culture. close to the city center. near highway and public transportation. "
    6
    Flag
  • Louis-gregory F. M.
    "The people who care for it. It also has two neighborhood parks that are fairly close. It’s also very accessible to the new library being built and accessibility to public transportation."
    4
    Flag
  • Tashima H.
    "I drive myself to work in Revere and it is not bad at all a bad commute from how to work. The MBTA is accessible however, it would take about an hour and forty five minutes to two hours just to get to work. "
    3
    Flag
  • Arallansys L.
    "Commute is easy in the Roxbury area. There’s easy access to Dudley station and bussies that can take you to the orange line, green line, red line and silver line "
    1
    Flag
  • Sarahabbott824
    "I bike 2 miles down Dudley to Tremont. Not the safest way to go. Lots of buses, street parking, weird intersections... but there is a path on a different road, just takes a bit longer. "
    1
    Flag
  • Andreaplara07
    "This is not the greatest area but is not the worst I have lived there 30 years and just moved to Worcester and is not much of a difference "
    1
    Flag
  • Matthew R.
    "Fort Hill is a hidden gem. It’s great for families and kids. It’s a really quiet, tight knit community. "
    1
    Flag
  • Buiznessmailonly
    "the neighborhood is not too bad. I can walk to resteraunts and I can walk to convenient stores and I can also take the bus and train to places. drivers do be driving crazy around my area and some streets need to be fixed"
    5
    Flag
  • Mary N.
    "Dog owners would love the fact that there is a pretty dog park , and dog friendly parks all around. People normally love dogs so 10 times out of 10 you’ll get someone who wants to pet your dog , wether it be a small child or adult."
    0
    Flag
  • Matthew R.
    "Highland Park/Fort Hill is an amazing place to raise kids. There a ton of young families in this diverse community. Our kids love the parks. It’s also really quiet for a city neighborhood. "
    1
    Flag
  • Yajaira P.
    "Good schools and programs for children. Nice and quiet neighborhood. Everything is close by supermarkets, stores, church, shopping center and much more! "
    2
    Flag
  • Trulia User
    "My commute is easy going there is a bus stop on every corner and it’s easy to get to the train stations"
    1
    Flag
  • Patricia R.
    "I have lived here for 10 yrs, I have a community of neighbors who care. when we see something we say something. we make a difference in our community"
    6
    Flag
  • AnonymousD
    " Close to everything but not worth it. It’s nice that you are close to a lot of the city and a lot of other surrounding cities but it is way too unfriendly to live here. I hate living here."
    0
    Flag
  • Valerie G.
    "That is a great neighborhood and that there are a lot of things around there that you can get to easily and transportation is very good I’m looking to move into soon as possible me and my two kids Sometimes it gets very busy There is plenty of grocery stores around the area"
    0
    Flag
  • Yajaira P.
    "You see people walking their dogs all the time. Quiet neighborhood and public transportation everywhere. "
    2
    Flag
  • Chastity R.
    "It has a lot of history around the neighborhood one of the oldest churches in Boston is across the street. Schools are in the area and nice schools. Friendly corner stores and the owners remember faces."
    0
    Flag
  • Antonio Crespo
    "They would like the parks but they would like living in apartments because there are no pet friendly apartments "
    1
    Flag
  • Shea G.
    "I see people walking their dogs on the regular and dogs always seem loved by the niebors and children in the area."
    1
    Flag
  • Loanny M.
    "Well is close to the city any where you go is about 15 to 20 minutes. But beside that nothing else it’s a crazy neighborhood can be very quite but at the same time dangerous "
    0
    Flag
  • Todd
    "Parks and history, beautiful homes. Good mix of community, families with children and young professionals, older longtime residents balance it out."
    2
    Flag
  • Jaysonnicholson17
    "Very good people here. So much history here in the southend. When you come to the south end there is a whole lot of "
    0
    Flag
  • Todd
    "the culture and the history. The character of the buildings and the spirit of the people that live there that make it a community."
    0
    Flag
  • Jamie M.
    "It is a minority neighborhood."
    0
    Flag
  • Melzina H.
    "Roxbury is unique to me for the food. I feel as though there are many options. Spanish food, Jamician, Chinese food, or Indian. I always have an option."
    1
    Flag
  • Kisha H.
    "The diversity makes it unique -- the many faces of Roxbury. And the history within my city make it unique too."
    1
    Flag
  • Vanessa M.
    "Roxbury has so many activities! Everyone is eventually brought together, whether it's a block party, or just a regualr cookout!"
    1
    Flag

LGBTQ Local Legal Protections

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.
The MLS listing information displayed is deemed reliable, but is not guaranteed accurate by the MLS.

Frequently asked questions about 27 Dudley St

  • What is the price history for 27 Dudley St?
    27 Dudley St in Roxbury, MA last sold for $3,450,000 in July 2026.
  • Is Roxbury a buyer's or seller's market?
    Roxbury is currently a balanced market, based on recent for-sale activity.
  • What's the median sale price in Roxbury?
    The median sale price in Roxbury is $830K. That is down $6.67K from the prior month.
  • What do residents say about Roxbury?
    Residents describe Roxbury, MA as pedestrian-friendly, walkable to grocery stores, and dog-friendly. See recently sold homes in Roxbury, MA.
  • Does 27 Dudley St have air conditioning?
    Yes, 27 Dudley St in Roxbury, MA has air conditioning.
  • Does 27 Dudley St have a pool?
    Yes, 27 Dudley St in Roxbury, MA has a pool.

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