53 Bailey Street, Boston MA 02124
Boston, MA 02124 • Dorchester's Ashmont
$879,000
Est. $5,138/month
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Open House Schedule
22
Aug
Saturday, August 22
11:30 AM - 1:00 PM EDT
23
Aug
Sunday, August 23
12:00 PM - 1:30 PM EDT
About this home
Welcome to 53 Bailey Street, a beautifully renovated single-family home tucked away on a quiet side street in the heart of Ashmont Village. Blending timeless character with contemporary design, this 3-bedroom + bonus space, 2.5-bath residence offers thoughtfully designed living spaces and sophisticated finishes throughout. The sun-filled main level features an open yet distinct layout, creating an ideal setting for both everyday living and entertaining. The designer kitchen features custom frameless cabinetry, quartz countertops, stainless steel appliances, and a center island, while oak hardwood floors and recessed lighting continue throughout.Upstairs, the spacious primary suite offers a walk-in closet and beautifully appointed en-suite bath. Two additional bedrooms, with large closets, and a full bath provide flexibility. Central air, efficient gas heat, smart home features, and an expansive basement with excellent storage complete the interior. Outside, enjoy a private composite deck overlooking the backyard, along with off-street parking. Ideally located just moments from Ashmont Village, neighborhood restaurants and shops like Tavolo + American Provisions, parks, the Lower Neponset River Trail, and Ashmont Station, with easy access to downtown Boston and I-93. A thoughtfully renovated home in a highly sought-after Dorchester neighborhood, 53 Bailey Street is ready to welcome its next owner.
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Recently Sold Nearby
Property History
Market Insights
14.7%
Price Range
1
Previous Sales
Property Timeline
Listed for Sale
Aug 19, 2026
$879,000
Original listing
Agent: Paul Whaley/Charlie Ring Team
Office: Coldwell Banker Realty - Boston
Previous Transaction - MLS #72509485
Full transaction history available when tracking began
Previously Sold
Aug 1, 2019
$750,000
MLS #72509485
| Date | Event | Price | Change | $/sqft | Details |
|---|---|---|---|---|---|
| 08/19/2026 | 🏠 Listed for Sale | $879,000 | - | - | Original listing |
| 08/01/2019 | 🏷️ Previously Sold | $750,000 | - | - | MLS #72509485 |
Tax History
| Year | Taxes | Assessment |
|---|---|---|
| 2027 | $5,916 | $824,500 |
Financial Details
Annual Property Tax
$5,916
Tax Year 2027
Assessed Value
$824,500
Facts & Features
Central AC
Home Facts
Type
Residential
Style
Single Family Residence
Year Built
1900
Living Area
1,588 sq ft
Lot Size
0.12 acres
Bedrooms
3
Full Baths
2
Half Baths
1
Total Rooms
9
Interior
Heating
Central
Cooling
Central Air
Flooring
Hardwood
Appliances
Gas Water Heater, Tankless Water Heater, Range, Dishwasher, Disposal, Microwave, Refrigerator, Freezer, Washer, Dryer, Wine Refrigerator, Range Hood
Fireplace
None
Basement
Full, Radon Remediation System, Concrete, Unfinished
Laundry
None
Features
None
Exterior
Construction
None
Architecture
Other (see Remarks)
Roof
None
Features
None
Pool
None
Spa
None
Fencing
None
Patio/Porch
None
Parking
Features
Shared Driveway, Off Street, Paved
Total Spaces
1
Utilities
Electric
None
Water
Public
Sewer
Public Sewer
Gas
None
Other
None
Financial
Annual Tax
$5,916
Assessed Value
$824,500
HOA & Community
Fee Includes
None
Amenities
None
Optional Fee Includes
None
MA Disclosures
Lead Paint
Unknown
Seller Disclosures
Parking/driveway Easement. In Instances Of Heavy/consistent Rain, Small Area In Front Of Basement Can Experience Moisture. Custom Basement Storage Shelves Will Stay. 53 Bailey Shares A Portion Of Snow Removal With Rear Units 1+2
Additional Details
Possession
None
Accepted Financing
None
Structure Type
[]
Sq Ft Source
Public Record
Sq Ft Disclosures
additional 920 sqft in unfinished basement
Documents
None
County
Suffolk
Property Overview
Property Type
Single Family Residence
Listing Type
For Sale
Year Built
1900
Bedrooms
3
Full Bathrooms
2
Half Bathrooms
1
Living Area
1,588 sq ft
Total Rooms
9
Floor Layout
Interactive room guide
Floor Layout
Finished Area
1,588 sq ft above grade
FeaturesYes
Display Options
Room Markers
BABathroom (4)
BRBedroom (5)
DDining (1)
KKitchen (1)
LLiving (2)
OOffice (1)
Conceptual diagram based on MLS room data. It is not to scale and is not a substitute for architectural plans or on-site measurements.
Interior Features
Flooring:
Hardwood
Appliances:
Gas Water Heater, Tankless Water Heater, Range, Dishwasher, Disposal, Microwave, Refrigerator, Freezer, Washer, Dryer, Wine Refrigerator, Range Hood
Interior Features:
Windows:
Basement:
Full, Radon Remediation System, Concrete, Unfinished
Laundry:
Security:
Construction & Materials
Style:
Other (See Remarks)
Year Built:
1900
Structure Type:
Exterior Materials:
Roof:
Foundation:
Stone
Heating, Cooling & Utilities
Heating:
Central
Heating Zones:
2
Cooling:
Central Air
Cooling Zones:
2
Hot Water:
Water Source:
Public
Sewer:
Public Sewer
Energy Features:
Exterior & Lot
Exterior Features:
Patio & Porch:
Fencing:
Other Structures:
Lot Features:
Easements
Road Surface:
Parking & Garage
Total Parking Spaces:
1
Parking Features:
Shared Driveway, Off Street, Paved
Nearby Schools
School District
Boston School District local
C-
Where Graduates Go
Class of 2021
52%
attend college
38%
4-Year
14%
2-Year
7%
Out of State
7%
Working
School Safety
2024-25
3.7%
Above Average
3.2%
Suspensions
0.3%
In-School
0.5%
Emergency
1.8% below state avg
Elementary Schools
3 schools
D
Henderson K-12 Inclusion School Upper
0.2 mi
|
#315 of 346
|
Score: 34.7
Improved 34 spots from last year
-23.5 below state avg
631 students
Diverse
Rising School
Diverse Student Body
Grades 02-12
D
Lee Academy
0.3 mi
|
#12 of 12
|
Score: 28.1
Improved 702 spots from last year
-30.1 below state avg
195 students
Diverse
Rising School
Diverse Student Body
Grades PK-03
Lee Academy
0.4 mi
Middle Schools
1 school
Epiphany School
0.6 mi
Grades 05-08
High Schools
3 schools
B+
TechBoston Academy
0.5 mi
|
#11 of 25
|
Score: 34.1
Improved 349 spots from last year
-24.1 below state avg
850 students
Diverse
Rising School
Grades 07-12
Urban Achievers School
0.6 mi
Grades 09-12
C
Boston International High School & Newcomers Academy
0.8 mi
|
#20 of 25
|
Score: 27.0
Improved 361 spots from last year
-31.2 below state avg
490 students
Diverse
12 sports
• 421 athletes
Rising School
Grades 09-12
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Monthly Payment Breakdown
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Property Tax
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Homeowners Insurance
$200
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Year 1
95% Interest
Year 15
50/50
Year 30
95% Principal
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Location
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Neighborhood
Dorchester's Ashmont
53 Bailey Street, Boston MA 02124
Boston, MA 02124
Listing Information
Listing Agent
Paul Whaley/Charlie Ring Team
Listing Office
Coldwell Banker Realty - Boston
Office Phone
617-266-4430
Agent MLS ID
TM309563
Office MLS ID
AN6192
Listing Data Updated
Aug 19, 2026 1:00 PM EDT
Listing information is deemed reliable but not guaranteed. Data provided by MLS Property Information Network, Inc. All information should be independently verified.
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