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$4,600,000 Just Listed

  • For Sale
  • Active
  • Lots/Land
  • 0.45 Acres
  • Updated 57 minutes ago
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Rare Winter Park redevelopment opportunity on a nearly half-acre corner parcel just minutes from Park Avenue. Zoned R-3 (Medium-Density Residential), this parcel offers outstanding residential redevelopment potential, including up to seven residential units (buyer to verify all zoning, density, development standards, and intended use with the City of Winter Park). Ideally situated between Park Avenue and Winter Park Village, the property enjoys convenient access to renowned dining, 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. Opportunities of this size and zoning in such close proximity to Park Avenue are exceptionally uncommon.

Full Property Details for 540 N Pennsylvania Ave

General

  • Price: $4,600,000
  • Taxes: $9,847 (2025)
  • Status: Active
  • Type: Lots/Land
  • Source: MidFloridaRegionalMLS
  • MLS ID: O6431538
  • Updated: Today (8/7/2026)
  • Added to Site: Today

Location

  • Area: 32789 - Winter Park
  • County: Orange
  • Development Name: 32789 - Winter Park
  • Subdivision: WINTER PARK
  • Driving 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.

Community

  • Community Name: 32789 - Winter Park

Utilities

  • Sewer: Public Sewer
  • Water: Public
  • Utility Description: Cable TV Available, Cable Connected, Electricity Available, Fiber Optics, Fire Hydrant, Phone Available, Propane, Sewer Available, Sewer Connected, Street Lights, Underground Utilities, Water Available, Water Con

Structural Information

  • Current Bldg. Use: Residential

Lot Features

  • Lot Size (Acres): 0.45
  • Lot Size (Sq. Ft.): 19,542
  • Lot Size: 19542
  • Lot Dimensions: 78 x 250
  • Frontage: Street Lights, Street Paved
  • Street/Road Desc.: Paved, Asphalt
  • Fencing (Description): Stone

Financial Considerations

  • Price Per Acre: $10,222,222
  • Assoc Fee Desc.: None
  • Tax Amount: $9,847.83
  • Tax Year: 2025

Disclosures and Reports

  • Ownership: Fee Simple
  • Special Conditions: None
  • 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 Zone Info: X
  • APN: 52230940011120
  • Property ID: 52230940011120
  • Block/Lot/Section: 11
Buyer's Brokerage Compensation: Contact Listing Agent
Not binding unless confirmed by separate agreement among applicable parties.

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— 540 N Pennsylvania Ave —

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NMLS#: 1598647

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Be ready to buy your new home!

with our affiliated lender
NMLS#: 1598647

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Schools serving 540 N Pennsylvania Ave

School District:Orange County School District
NameGradesDistance
Lakemont Elementary School
901 North Lakemont Avenue, Winter Park, FL 32792
K-51.7 mi
Maitland Middle School
701 North Thistle Lane, Maitland, FL 32751
6-82.4 mi
Winter Park High School
2100 Summerfield Road, Winter Park, FL 32792
9-122.4 mi
Disclaimer: School attendance boundaries provided by ATTOM Data Solutions and are for reference only. Contact the school directly to verify enrollment eligibility.

Price & Sales History for 540 N Pennsylvania Ave Get Price Alerts and Save Property

Date
Details
Price
Change
Source
8/07/2026
Listed
$4,600,000
1781.39%
MLS
5/31/2016
Sold
$244,500
—
Public Record
Get Price Alerts and Save Property
Disclaimer: Historical sales information is derived from public records provided by the county offices. Information is not guaranteed and should be independently verified.

Tax History for 540 N Pennsylvania Ave

Year
Property Taxes
Change
Tax Assessment
Change
2025
$9,848
8%
$670,355
16%
2024
$9,084
8%
$576,409
4%
2023
$8,418
24%
$554,407
28%
2021
$6,808
-4%
$431,639
-6%
2022
$7,074
4%
$457,862
7%
2021
$6,808
-5%
$427,071
-3%
2019
$7,156
2%
$438,609
4%
2018
$6,998
6%
$422,689
7%
2017
$6,633
33%
$395,245
-10%
2016
$4,989
65%
$439,113
178%
2015
$3,022
20%
$157,686
10%
2014
$2,525
10%
$143,351
9%
2013
$2,302
—
$131,339
—
View All
Disclaimer: Historical tax information is derived from public records provided by the county offices. Information is not guaranteed and should be independently verified.

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540 N Pennsylvania Avenue, Winter Park, FL 32789 (MLS# O6431538) is a Lots/Land property with a lot size of 0.45 acres. 540 N Pennsylvania Avenue is currently listed for $4,600,000 and was received on August 07, 2026. This property is listed by Mary Heidrich from our Winter Park Office.Want to learn more about 540 N Pennsylvania Avenue? Do you have questions about finding other Lots/Land real estate for sale in Winter Park? You can browse all Winter Park real estate or contact a Coldwell Banker agent to request more information.

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