53 Bailey Street, Boston MA 02124
Boston, MA 02124 • Dorchester's Ashmont
$879,000
Est. $5,138/month
Estimate assumptions
20% down, a 30-year loan at 6.5%, and $200/month estimated insurance.
Includes the supplied property-tax and HOA inputs; missing inputs contribute $0. HOA fees with an unspecified frequency are treated as monthly. PMI and closing costs are excluded.
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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
Property Timeline
Status: Active under contract
Aug 25, 2026
Active → Active Under Contract
Pending Sale
Aug 24, 2026
Offer accepted, sale pending
Listed for Sale
Aug 19, 2026
$879,000
Original listing
Agent: Paul Whaley/Charlie Ring Team
Office: Coldwell Banker Realty - Boston
| Date | Event | Price | Change | $/sqft | Details |
|---|---|---|---|---|---|
| 08/25/2026 | 📋 Status: Active under contract | - | - | - | Active → Active Under Contract |
| 08/24/2026 | ⏳ Pending Sale | - | - | - | Offer accepted, sale pending |
| 08/19/2026 | 🏠 Listed for Sale | $879,000 | - | - | Original listing |
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
Down Payment Resource
Eligible
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
Total market time (incl. prior listings)
20 days
Property Overview
Property Type
Single Family Residence
Listing Type
Sale Pending
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
OOffice (1)
KKitchen (1)
BRBedroom (5)
BABathroom (4)
DDining (1)
LLiving (2)
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
10 schools
D
Henderson K-12 Inclusion School Upper
0.2 mi
|
#323 of 346
|
Score: 32.2
Improved 26 spots from last year
-26 below state avg
605 students
Diverse
Rising School
Diverse Student Body
Grades 02-12
C-
Codman Academy Charter Public School
0.5 mi
|
#308 of 346
|
Score: 36.8
Dropped 24 spots from last year
-21.4 below state avg
345 students
Diverse
College Ready Curriculum
Grades PK-12
Saint John Paul II Academy - Lower Mills
0.7 mi
Grades PK-08
C-
Kenny Elementary School
0.7 mi
|
#743 of 825
|
Score: 32.9
Dropped 31 spots from last year
-25.3 below state avg
315 students
Very Diverse
Diverse Student Body
Grades PK-06
St. Brendan Elementary School
0.8 mi
Grades K-08
F
Lee K-8 School
0.9 mi
|
#339 of 352
|
Score: 26.8
Improved 4 spots from last year
-31.4 below state avg
582 students
Diverse
Grades PK-08
C
Neighborhood House Charter School
0.9 mi
|
#277 of 346
|
Score: 44.9
Improved 14 spots from last year
-13.3 below state avg
768 students
Diverse
College Ready Curriculum
Diverse Student Body
Grades PK-12
C-
Holmes Elementary School
1.0 mi
|
#717 of 825
|
Score: 34.5
Dropped 31 spots from last year
-23.7 below state avg
301 students
Diverse
Grades PK-06
New Beginnings Academy
1.0 mi
Grades PK-12
Saint John Paul II Academy - Neponset
1.0 mi
Grades PK-08
Middle Schools
10 schools
Epiphany School
0.6 mi
Grades 05-08
Dearborn Middle School
1.8 mi
Mother Caroline Academy
1.8 mi
Grades 05-08
A
Uncommon Schools - Roxbury Preparatory Dorchester Campus Middle School
1.9 mi
|
#4 of 16
|
Score: 42.5
Improved 187 spots from last year
-15.7 below state avg
1,225 students
Diverse
Rising School
College Ready Curriculum
Grades 05-08
F
Higginson/Lewis K-8 School
2.7 mi
|
#349 of 352
|
Score: 23.2
Improved 3 spots from last year
-35 below state avg
246 students
Diverse
Grades 03-08
Nativity Prep School
3.1 mi
Grades 05-08
Middle School Academy
3.5 mi
C
Ohrenberger School
4.5 mi
|
#266 of 352
|
Score: 35.0
Improved 19 spots from last year
-23.2 below state avg
458 students
Diverse
Diverse Student Body
Grades 03-08
Frederick Pilot Middle
1.8 mi
McCormack Middle
2.6 mi
High Schools
10 schools
B+
TechBoston Academy
0.5 mi
|
#10 of 25
|
Score: 34.9
Improved 350 spots from last year
-23.3 below state avg
869 students
Diverse
Rising School
Grades 07-12
A+
Boston Latin Academy
2.4 mi
|
#2 of 25
|
Score: 64.9
Improved 214 spots from last year
+6.7 above state avg
1,669 students
Very Diverse
17 sports
• 1,298 athletes
Strong AP Program
High Graduation Rate
Rising School
Strong Athletics
Grades 07-12
C
Ruth Batson Academy
2.6 mi
|
#20 of 25
|
Score: 29.1
Improved 345 spots from last year
-29.1 below state avg
584 students
Diverse
8 sports
• 128 athletes
Early College Program
Rising School
Grades 07-12
D
English High School
2.7 mi
|
#328 of 346
|
Score: 28.9
Improved 30 spots from last year
-29.3 below state avg
653 students
Diverse
8 sports
• 332 athletes
Rising School
Career Tech Programs
Grades 07-12
A-
Boston Preparatory Charter Public School
2.7 mi
|
#8 of 25
|
Score: 43.6
Improved 287 spots from last year
-14.6 below state avg
670 students
Diverse
High Graduation Rate
Rising School
College Ready Curriculum
Grades 06-12
Meridian Academy
2.7 mi
Grades 06-09
B-
Margarita Muniz Academy
2.9 mi
|
#14 of 25
|
Score: 31.6
Improved 349 spots from last year
-26.7 below state avg
480 students
Less Diverse
Rising School
Grades 07-12
C+
New Mission High School
3.0 mi
|
#230 of 346
|
Score: 49.5
Improved 98 spots from last year
-8.7 below state avg
739 students
Diverse
13 sports
• 458 athletes
Early College Program
High Graduation Rate
Rising School
Diverse Student Body
Grades 07-12
B
Dearborn STEM Academy
3.0 mi
|
#13 of 25
|
Score: 33.4
Improved 356 spots from last year
-24.8 below state avg
565 students
Moderate
10 sports
• 242 athletes
Early College Program
Rising School
Grades 07-12
A-
O'Bryant School of Math & Science
3.5 mi
|
#90 of 346
|
Score: 61.6
Improved 94 spots from last year
+3.4 above state avg
1,518 students
Very Diverse
High Graduation Rate
Rising School
College Ready Curriculum
Diverse Student Body
Grades 07-12
Learn about these ratings
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Loan Amount
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Including down payment
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Down: $0
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Monthly Payment Breakdown
Principal & Interest
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Property Tax
$493
Homeowners Insurance
$200
PMI (if <20% down)
$0
Loan Summary
Total of 360 payments
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Payment Over Time
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
Sep 9, 2026 3:30 AM 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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