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FRONT (SOUTH, W SWOOPE AVE) AND SIDE (WEST, N PENNSYLVANIA AVE) OF PARCEL.
Property for sale at 540 N PENNSYLVANIA AVENUE, WINTER PARK, FL, 32789
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540 N Pennsylvania AvenueWinter Park, FL, 32789

19,542 sqftLot size
Land
$3,950,000
For sale
$4,600,000−$650,000 (14%)Reduced Sep 14, 2026
Days on market
62
Listed Aug 7, 2026
MLS #O6431538Updated Sep 14, 2026

About this property

MAJOR PRICE IMPROVEMENT—NOW OFFERED BELOW $4 MILLION! Rare Winter Park redevelopment opportunity on a nearly half-acre corner parcel just minutes from Park Avenue. Newly priced at $3,950,000, this R-3 (Medium-Density Residential) property offers outstanding redevelopment potential, including capacity for up to seven residential units. Ideally positioned between Park Avenue and Winter Park Village, the property offers convenient access to renowned dining and shopping, Rollins College, cultural attractions, AdventHealth Winter Park, and major transportation corridors. Three existing residences occupy the site and contribute no value to the offering. Properties of this size and zoning, so close to Park Avenue, are exceptionally rare. THIS PROPERTY IS CROSS-LISTED AS RESIDENTIAL WITH THE MLS #O6436046.

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Property details

Property type
Land
Street address
540 N Pennsylvania Avenue
City
Winter Park
State
FL
ZIP code
32789

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 October 8, 2026 at 4:01 AM EDT

Price & sale history

Asking price reduced by $650,000 (14.1%) since first listed.

EventPrice
Listed for saleMLS #O6436046$3,950,000
Price reducedMLS #O6431538$3,950,000Change: −14.1%−$650,000
Listed for saleMLS #O6431538$4,600,000
Price changedMLS #O4737248$439,999
History may be incomplete.
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Location

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FRONT (SOUTH, W SWOOPE AVE) AND SIDE (WEST, N PENNSYLVANIA AVE) OF PARCEL.
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