Welcome to 1621 Chestnut Avenue, ideally situated in the heart of Winter Park’s coveted “Tree Streets” neighborhood. Offered at $899,000, this single-story block home sits on a generous 50×150′ lot and offers 2,022 square feet of living space with 3 bedrooms and 2.5 baths. Whether you envision a thoughtful remodel or a ground-up new build, this property presents outstanding potential in one of Winter Park’s most desirable pockets, where similar transformations are already reshaping the streetscape.
Inside, tile flooring flows through the main living areas, complementing a versatile layout that includes a formal living room, a combined kitchen and dining area, and a separate den with pocket doors perfect for a home office or media room. The oversized bedrooms offer generous space throughout, including a primary suite with a private en suite bath. Two additional guest bedrooms share a convenient Jack-and-Jill bathroom, ideal for family or guests.
At the rear of the home, an enclosed sunroom provides a peaceful retreat overlooking the well-manicured backyard, a tranquil spot to relax and unwind. With its prime location, solid bones, and abundant possibilities, 1621 Chestnut Avenue is ready for its next owner to make it their own.
Inside, tile flooring flows through the main living areas, complementing a versatile layout that includes a formal living room, a combined kitchen and dining area, and a separate den with pocket doors perfect for a home office or media room. The oversized bedrooms offer generous space throughout, including a primary suite with a private en suite bath. Two additional guest bedrooms share a convenient Jack-and-Jill bathroom, ideal for family or guests.
At the rear of the home, an enclosed sunroom provides a peaceful retreat overlooking the well-manicured backyard, a tranquil spot to relax and unwind. With its prime location, solid bones, and abundant possibilities, 1621 Chestnut Avenue is ready for its next owner to make it their own.
Property Details
Price:
$899,000
MLS #:
O6435086
Status:
Active
Beds:
3
Baths:
2.5
Type:
Single Family
Subtype:
Single Family Residence
Subdivision:
LAKE KNOWLES TERRACE
Neighborhood:
32789winterpark
Listed Date:
Aug 20, 2026
Finished Sq Ft:
2,022
Total Sq Ft:
2,715
Lot Size:
7,512 sqft / 0.17 acres (approx)
Year Built:
1970
See this Listing
Schools
Elementary School:
Lakemont Elem
Middle School:
Maitland Middle
High School:
Winter Park High
Interior
Appliances
Built-In Oven, Cooktop, Dishwasher, Refrigerator
Bathrooms
2 Full Bathrooms, 1 Half Bathroom
Cooling
Central Air
Flooring
Carpet, Tile, Hardwood
Heating
Central, Electric
Interior Features
Ceiling Fan(s)
Laundry Features
Laundry Room
Levels
One
Exterior
Attached Garage YN
1
Construction Materials
Block
Covered Spaces
2
Direction Faces
South
Exterior Features
Sidewalk
Fencing
Fenced
Garage Spaces
2
Open Parking YN
1
Parking Features
Driveway
Roof
Shingle
Financial
Tax Year
2025
Taxes
$3,312
Map
Community
- Address1621 CHESTNUT AVENUE WINTER PARK FL
- SubdivisionLAKE KNOWLES TERRACE
- CityWINTER PARK
- CountyOrange
- Zip Code32789
Subdivisions in WINTER PARK
Market Summary
Current real estate data for Single Family in WINTER PARK as of Aug 29, 2026
301
Single Family Listed
85
Avg DOM
469
Avg $ / SqFt
$1,282,562
Avg List Price
Property Summary
- Located in the LAKE KNOWLES TERRACE subdivision, 1621 CHESTNUT AVENUE WINTER PARK FL is a Single Family for sale in WINTER PARK, FL, 32789. It is listed for $899,000 and features 3 beds, 3 baths, and has approximately 2,022 square feet of living space, and was originally constructed in 1970. The current price per square foot is $445. The average price per square foot for Single Family listings in WINTER PARK is $469. The average listing price for Single Family in WINTER PARK is $1,282,562. To schedule a showing of MLS#o6435086 at 1621 CHESTNUT AVENUE in WINTER PARK, FL, contact your InvestPro Properties, Inc. agent at 561-203-7022.
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Courtesy of KELLY PRICE & COMPANY LLC. Disclaimer: All data relating to real estate for sale on this page comes from the Broker Reciprocity (BR) of the Orlando/Tampa – FL. Detailed information about real estate listings held by brokerage firms other than InvestPro Properties, Inc. include the name of the listing broker. Neither the listing company nor InvestPro Properties, Inc. shall be responsible for any typographical errors, misinformation, misprints and shall be held totally harmless. The Broker providing this data believes it to be correct, but advises interested parties to confirm any item before relying on it in a purchase decision. Copyright 2026. Orlando/Tampa – FL. All rights reserved. 1621 CHESTNUT AVENUE
WINTER PARK, FL
