540 Pennsylvania Avenue, FL540 Pennsylvania Avenue, FL540 Pennsylvania Avenue, FL
Stellar MLS
1 / 5

$3,950,000

540 Pennsylvania Avenue

Winter Park, FL 32789

Listing updated: September 15, 2026 at 6:51 AM ET

Active
Stellar MLSListing courtesy of Coldwell Banker Realty · Mary Heidrich · MLS #O6436046 · Active · 407-647-1211
4
Beds
2
Baths
1,652
Sq Ft
0.45
Acres
1938
Built
$2,391/sqft360° tour
Single Family Residence

Property type

1938

Year built

19,542 sqft

Lot size

$2,391

Price / sq ft

No HOA

HOA dues

1

Day on market

X

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

Principal & interest$19,973
Property taxes$821
Home insurance (est.)$1,810

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

  1. Status: Active
    Sep 15, 2026
  2. Listed$3,950,000
    Sep 14, 2026
  3. 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

RoomLevelDimensions
Primary BedroomFirst
Bedroom 2First
Bathroom 1First
KitchenFirst
Living RoomFirst

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 riskFEMA Zone XPanel 12095C0255F

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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MLS GRID

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.

Ryan Solberg, Broker · MaxLife Realty LLC · FL License #BK3354351 · Equal Housing Opportunity · Full disclaimer · DMCA