


$3,950,000
540 Pennsylvania Avenue
Winter Park, FL 32789
Listing updated: September 15, 2026 at 6:51 AM ET
Property type
Year built
Lot size
Price / sq ft
HOA dues
Day on market
Flood zone
About this home
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 ZONED (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 VACANT LAND WITH THE MLS #O6431538.
Estimated monthly payment
Estimate only. Taxes use the listing's reported amount where available; insurance is a Florida-average estimate. Your actual payment will vary — run a full calculation or talk to a lender.
Price & listing history1 days on market
- Status: ActiveSep 15, 2026
- Listed$3,950,000Sep 14, 2026
- Price increased$3,950,000
Facts & features
- Property type
- Residential
- Sub type
- Single Family Residence
- Status
- Active
- Days on market
- 1
- Subdivision
- Winter Park
- County
- Orange
- Year built
- 1938
- Living area
- 1,652 sq ft
- Price/sq ft
- $2,391
- Lot size
- 19,542 sq ft
- Lot category
- 1/4 to less than 1/2
- Flood zone
- X (12095C0255F)
- Annual taxes
- $9,848 (2025)
- Parcel #
- 05-22-30-9400-11-120
- Zoning
- R-3
- MLS #
- O6436046
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Interior Details
- Bedrooms
- 4
- Full bathrooms
- 2
- Flooring
- Tile, Wood
- Appliances
- None
- Interior features
- Ninguno
- Laundry
- None
- Stories / Levels
- One
- Direction faces
- West
Heating & Cooling
- Heating
- Central, Exhaust Fan
- Cooling
- Central Air
Parking
- Carport
- Yes
HOA & Financial
- Total monthly fees
- $0/mo
- Total annual fees
- $0
- CDD
- No
- Min lease term
- 1-7 Days
- Ownership
- Fee Simple
- Available for lease
- Yes
- Lease restrictions
- No
Exterior & Construction
- Exterior features
- Garden, Lighting, Sidewalk
- Construction materials
- Block, Cement Siding
- Roof
- Shingle
- Foundation
- Block
- Road surface
- Asphalt
Utilities
- Sewer
- Public Sewer
- Water source
- Public
- Utilities
- Cable Available, Cable Connected, Electricity Available, Fiber Optics, Fire Hydrant, Phone Available, Propane, Sewer Available, Sewer Connected, Underground Utilities, Water Available, Water Connected
Room Details
| Room | Level | Dimensions |
|---|---|---|
| Primary Bedroom | First | |
| Bedroom 2 | First | |
| Bathroom 1 | First | |
| Kitchen | First | |
| Living Room | First |
Listing Details
- Listing date
- 2026-09-14
- On market date
- 2026-09-14
- Original list price
- $3,950,000
- Occupant type
- Tenant
- MLS area
- 32789 - Winter Park
- Listing AOR
- Orlando Regional
- Status changed
- 2026-09-15
- Tax legal description
- TOWN OF WINTER PARK A/67 & B/86 & MISC BOOK 3/220 LOT 12 BLK 11 & N1/2 OF VAC ALLEY ON S BLK 11
Flood risk
Minimal-risk area outside the mapped floodplain. Flood insurance is optional and typically low-cost.
Source: FEMA flood zone reported on the listing. Confirm current designation at FEMA Flood Map Service Center.
Location
Directions
From I-4, take the Fairbanks Avenue exit and travel east. Cross Orlando Avenue (US-17/92), then turn left onto Denning Dr. Turn right on W Swoope Ave. Travel across Pennsylvania Ave. The property is located on the southeast corner of N. Pennsylvania Ave and W. Swoope Ave, just minutes from Park Avenue and Winter Park Village.
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Listings courtesy of Stellar MLS as distributed by MLS GRID
IDX information is provided exclusively for consumers’ personal, non-commercial use and may not be used for any purpose other than to identify prospective properties consumers may be interested in purchasing.
Based on information submitted to the MLS GRID as of September 15, 2026 at 6:51 AM ET. All data is obtained from various sources and may not have been verified by broker or MLS GRID. Supplied Open House Information is subject to change without notice. All information should be independently reviewed and verified for accuracy. Properties may or may not be listed by the office/agent presenting the information.
All or a portion of the multiple listing information is provided by Stellar MLS, from a copyrighted compilation of listings. The compilation of listings and each individual listing are © 2026 Stellar MLS. All rights reserved.
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