540 N PENNSYLVANIA AVENUE, WINTER PARK, FL, 32789
Active6 days on marketListed Sep 14, 2026MLS #O6436046
About this home
540 N PENNSYLVANIA AVENUE
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.
Facts & features
The home at a glance
4
Bedrooms
2
Bathrooms
1,652
Sqft
0.45 ac
Lot size
1938
Year built
One
Levels
$2,391
Per sqft
Inside
Outside & construction
Community & fees
Utilities & systems
The numbers
What it really costs
Built from this home's actual numbers — the most recent property-tax bill on record — not generic estimates.
$23,776 /mo · 10% down Conventional, 30-yr fixed at 6%
The assumptions
Above the FHA loan limit for our service areas, so Conventional is the default. VA buyers: switch below — $0 down.
These numbers assume a generic buyer — your credit, down payment and loan program change them. Get the real quote in minutes:
Andrew Acosta
Acosta Home Loans with PRMG · NMLS #1468866
Run your own numbers
FHA isn’t available at this price — the loan would exceed the $541,287 FHA limit for our service areas.
Estimated payment
$23,776/mo
Includes estimated PMI — it drops off once you reach 20% equity. Taxes reflect the most recent bill on record; insurance is a typical-Florida estimate. Your lender’s numbers will differ. CENTURY 21 Edge partners with Florida’s best lenders.
Value check
Is the price right?
The internet’s favorite home-value number comes from a single automated model that has never seen the street, the finishes, or the view — which is why it routinely misses by tens of thousands of dollars. The edgeAI estimate combines multiple independent data sources with our team’s on-the-ground expertise in this exact market.
vs edgeAI estimate
+788.8%
$/sqft vs Winter Park actives
$2,391 vs $349
Days on market
6 vs 43 typical
Where $2,391/sqft sits among the 350 Winter Park actives
The edgeAI estimate is a starting point, not an appraisal or a broker price opinion. It is generated from public records, listing data and market modeling, and is subject to change once a licensed real estate professional personally inspects the property. Condition, floor, view and lot are not fully captured by any model — ask us for a full comparative market analysis.
Where it sits
Inside Hannibal Square
Drive times from this address
Estimated driving times, typical traffic. Data © OpenStreetMap contributors.
Get to know Winter Park. See the full Winter Park guide →
Hannibal Square — neighborhood snapshot
Population
1,798
Median age
38
Median income
$50,175
Median home value
$528,038
Avg household
2
Households w/ children
117
For the school run
Orange County School District
School assignments and ratings via edgeAI — always verify with the district.
The numbers that matter
The Winter Park market
$470K → $512K
Winter Park median sold, yr/yr
96.8%
Sale-to-list ratio (12 mo)
158 of 350
Winter Park actives have cut their price
Median sold price, Winter Park, trailing 36 months (3-month rolling) · live MLS data.
This home is listed 385% above the WINTER PARK 32789 median. See the full Winter Park market guide →
Paper trail
This home's history
Reality check
What actually sold near 540 N PENNSYLVANIA AVENUE
Asking prices are opinions — closed sales are facts. The most comparable homes that actually changed hands nearby in the last twelve months.
Sold · Mar ’26$975,000
456 CAROLINA AVENUE · same community
3 bd · 3 ba · 1,615 sqft · $604/sqft · 9 DOM
Sold · Jun ’26$735,000
738 S PENNSYLVANIA AVENUE · same community
3 bd · 2 ba · 1,739 sqft · $423/sqft · 2 DOM
Sold · Jun ’26$550,000
650 DOUGLAS AVENUE · same community
3 bd · 2 ba · 1,280 sqft · $430/sqft · 0 DOM
Closed-sale data from the MLS, last 12 months, selected for similarity in size and location. No two homes are identical — ask us for a full comparative analysis.
Your home team
The pros in your corner
Buying a home is two conversations — the home and the money. Here’s who handles each, side by side, already working together.
Your agent
Shawn Lewis
Realtor · CENTURY 21 Edge
Tours, negotiation, and every question about 540 N PENNSYLVANIA AVENUE — start here.
Your lender
Andrew Acosta
Acosta Home Loans with PRMG · NMLS #1468866
Pre-approval, rates, and the real monthly number for 540 N PENNSYLVANIA AVENUE — before you fall in love.
See it in person
Schedule a tour
Live availability from Shawn's calendar — pick a time and it's booked. Confirmation lands in your inbox immediately.
Straight answers
540 N PENNSYLVANIA AVENUE FAQs
What would the monthly payment be for 540 N PENNSYLVANIA AVENUE?+
With 10% down on a 30-year Conventional loan at 6%, the all-in payment lands around $23,776/mo — principal and interest, the actual property-tax bill and typical Florida insurance. The payment calculator on this page lets you switch loan type (FHA, Conventional, VA) and adjust the down payment, rate and term.
What are the property taxes on 540 N PENNSYLVANIA AVENUE?+
The most recent tax bill on record (2025) was $9,848. A new owner's bill can differ once the sale price resets the assessed value — we can walk you through what to expect.
How does the price compare to other homes in Winter Park?+
At $3,950,000, this home is listed about 587% above the Winter Park median of $575,000. The market section on this page shows how the area is trending.
Which schools are assigned to 540 N PENNSYLVANIA AVENUE?+
Audubon Park School (elementary), Winter Park High (high) — Orange County School District. Always verify school assignments with the district before relying on them.
The brief
Three things that matter here
01Positioned at the premium end
$3,950,000 runs 385% above the WINTER PARK 32789 median.
02Fresh on the market
Only 6 days on market in a Winter Park market that averages 43 — if it fits, move quickly.
03Strong assigned schools
Audubon Park School, Winter Park High — Audubon Park School rates 5 of 5. Always verify assignments with the district.
Keep looking
Similar homes nearby
Listing courtesy of COLDWELL BANKER REALTY · Mary Heidrich. MLS #O6436046.
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. Data is deemed reliable but is not guaranteed accurate by Stellar MLS.
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