Welcome home to 5156 S. Massasoit Avenue! Situated on a beautifully landscaped corner lot, this spacious and impressively well-maintained 3-bedroom, 2-bath home offers the perfect blend of character, functionality, and thoughtful updates throughout. From the moment you arrive, you’ll be welcomed by the charming wraparound porch. Once inside, you’ll love the open floor plan that offers so much room for everyday living and entertaining. The large kitchen provides an abundance of cabinet space for storage and meal preparation as well as a spacious walk-in pantry. In addition to the main living areas, the home also features a spacious den with a gas-start fireplace. Clean, dry, and well-maintained – the basement provides valuable storage space and includes a dedicated laundry area. Step outside and discover a backyard designed for enjoying every season. Whether you’re hosting summer barbecues or cooling off in the above-ground pool (new liner 2023) this outdoor space was made to be enjoyed. One of the property’s standout features is the oversized 2.5-car detached pull-through garage with attic storage above, the attached, rear pavilion creates valuable additional outdoor living space, perfect for outdoor dining, entertaining, or simply enjoying a beautiful summer evening. The list of updates offers true peace of mind, including a new roof in 2019, a new front porch roof in 2024, both central air conditioning units replaced in 2019, two furnaces (one serving the main level and one serving the upper level) installed in 2017, and a water heater replaced in 2017. Conveniently located near parks, schools, shopping, dining, and transportation. 5156 S. Massasoit Avenue offers the space, charm, outdoor living, and major updates today’s buyers are looking for. Simply move in, settle in, and start making memories.
Property Details
Price:
$475,000
MLS #:
MRD12630988
Status:
Active
Beds:
3
Baths:
2
Type:
Single Family
Neighborhood:
chigarfieldridge
Listed Date:
Jun 11, 2026
Finished Sq Ft:
2,283
Year Built:
1913
See this Listing
Schools
School District:
299
Interior
Bathrooms
2 Full Bathrooms
Cooling
Central Air
Fireplaces Total
1
Heating
Natural Gas
Laundry Features
Sink
Exterior
Construction Materials
Vinyl Siding
Fencing
Fenced
Garage Spaces
2
Lot Features
Corner Lot
Parking Features
Concrete, Garage Door Opener, Garage, Yes, Garage Owned, Detached
Parking Spots
2
Parking Total
2
Patio And Porch Features
Deck, Porch
Roof
Asphalt
Financial
HOA Fee Frequency
Not Applicable
HOA Includes
None
Tax Year
2023
Taxes
$6,334
Map
Community
- Address5156 S Massasoit Avenue Chicago IL
- CityChicago
- CountyCook
- Zip Code60638
Market Summary
Current real estate data for Single Family in Chicago as of Jun 16, 2026
2,728
Single Family Listed
67
Avg DOM
238
Avg $ / SqFt
$591,961
Avg List Price
Property Summary
- 5156 S Massasoit Avenue Chicago IL is a Single Family for sale in Chicago, IL, 60638. It is listed for $475,000 and features 3 beds, 2 baths, and has approximately 2,283 square feet of living space, and was originally constructed in 1913. The current price per square foot is $208. The average price per square foot for Single Family listings in Chicago is $238. The average listing price for Single Family in Chicago is $591,961.
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5156 S Massasoit Avenue
Chicago, IL


