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.
Property Details
Price:
$879,000
MLS #:
73565616
Status:
Pending
Beds:
3
Baths:
2.5
Type:
Single Family
Subtype:
Single Family Residence
Neighborhood:
dorchestersashmont
Listed Date:
Aug 19, 2026
Finished Sq Ft:
1,588
Total Sq Ft:
1,588
Lot Size:
5,250 sqft / 0.12 acres (approx)
Year Built:
1900
See this Listing
Schools
Interior
Above Grade Finished Area
1588
Appliances
Gas Water Heater, Tankless Water Heater, Range, Dishwasher, Disposal, Microwave, Refrigerator, Freezer, Washer, Dryer, Wine Refrigerator, Range Hood
Bathrooms
2 Full Bathrooms, 1 Half Bathroom
Cooling
Central Air
Flooring
Hardwood
Heating
Central
Exterior
Architectural Style
Other (See Remarks)
Community Features
Public Transportation, Shopping, Park, Walk/Jog Trails, Medical Facility, Laundromat, Bike Path, Conservation Area, Highway Access, House of Worship, Private School, Public School, T-Station
Lot Features
Easements
Open Parking Spaces
1
Open Parking YN
1
Parking Features
Shared Driveway, Off Street, Paved
Parking Spots
1
Parking Total
1
Financial
Tax Year
2027
Taxes
$5,916
Map
Community
- Address53 Bailey Street Boston MA
- CityBoston
- CountySuffolk
- Zip Code02124
Subdivisions in Boston
- Adams Village
- Ashmont Hill
- Ashmont Hill / Carruth Area
- Back Bay
- Bay Village
- Beacon Hill
- Bellevue Hill
- Boston
- Brighton-Oak Square
- Charlestown
- Chestnut Hill
- Chestnut Hill /Brookline line
- Chestnut Hill Park Condominium
- Clam Point Neighborhood
- Eight Streets Neighborhood
- Ellis South End Neighborhood
- Fairmount Hill
- Fields Corner
- Gas Light District
- Golf Course Neighborhood
- Harbor View
- Harborview
- Highland
- Hyde Park
- Jamaica Plain
- Lower Mills
- Melville Park
- Metropolitan Heights Area
- Metropolitan Hill
- Mission Hill – Longwood Medical
- Oak Square
- Parkway neighborhood
- Roslindale
- Roslindale – WC Bates
- roslindale village
- Roxbury’s Moreland Street Historic District
- Savin Hill: Minutes to Carson Beach/UMass Boston T-Stop
- South Boston
- Suffolk County
- Sumner Hill
- Thomas Park
- Woodbourne
Market Summary
Current real estate data for Single Family in Boston as of Sep 24, 2026
387
Single Family Listed
116
Avg DOM
650
Avg $ / SqFt
$1,823,014
Avg List Price
Property Summary
- 53 Bailey Street Boston MA is a Single Family for sale in Boston, MA, 02124. It is listed for $879,000 and features 3 beds, 3 baths, and has approximately 1,588 square feet of living space, and was originally constructed in 1900. The current price per square foot is $554. The average price per square foot for Single Family listings in Boston is $650. The average listing price for Single Family in Boston is $1,823,014. To schedule a showing of MLS#73565616 at 53 Bailey Street in Boston, MA, contact your Cornerstone Real Estate agent at 617-238-7400.
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Courtesy of Coldwell Banker Realty – Back Bay. 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.
53 Bailey Street
Boston, MA