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Front View

1421 Chestnut AvenueWinter Park, FL, 32789

3beds
1baths
1,325sqft
Single Family Residence
Built in 1952
$675,000
Sold
Price per sqft
$509
Sold on
Oct 22, 2026
MLS #O6442587Updated Oct 22, 2026

About this property

Prime Winter Park builder and luxury custom home opportunity with rare dual access! Nestled in this Winter Park enclave just one block from the Via Streets, this location offers a massive competitive advantage and features a dedicated rear easement providing direct vehicle or construction access to the adjacent side street (Sunset). Whether you are an investor looking for a high-end project or designing your private sanctuary, this unique dual-access point is a designer’s dream—opening up incredible architectural flexibility, private rear-loading/garage options, or seamless construction staging. The property boasts an unobstructed view of the serene park setting at the intersection of Chestnut and Sunset, providing a picturesque backdrop for custom luxury home architecture. Surrounding properties are rapidly redeveloping into spectacular modern estates. Bring your custom builder and your vision to claim one of Winter Park's unique footprints. Property is being sold As-Is with value in the land. One car garage at rear of property with access thru deeded easement. Shed next to garage.

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Property details

Property type
Single Family Residence
Street address
1421 Chestnut Avenue
City
Winter Park
State
FL
ZIP code
32789
Year built
1952
New construction
No
Faces
South
Rooms
3
Building stories
1
Living area
1,325 sqft
Total building area
1,980 sqft
Architectural style
Traditional
Levels
One

Stellar MLSThe data relating to real estate displayed on this website comes in part from the Internet Data Exchange (IDX) Program of Stellar MLS. All listing information is deemed reliable but not guaranteed and should be independently verified through personal inspection by appropriate professionals. Listings displayed on this website may be subject to prior sale or removal from sale; the availability of any listing should always be independently verified. Listing information is provided for consumers' personal, non-commercial use, solely to identify potential properties for potential purchase; all other use is strictly prohibited and may violate relevant federal and state law.Stellar (MFR) data last updated at November 7, 2026 at 10:30 PM EST

Price & sale history

EventPrice
SoldMLS #O6442995$675,000
SoldMLS #O6442587$675,000
Listed for saleMLS #O6442995$750,000
Listed for saleMLS #O6442587$750,000
History may be incomplete.
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Location

Front View
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