Commercial Real Estate Market in Winter Park, FL
Updated monthly: sale, lease, property records, location trend, and more… · Last update: August 31
177 active listings and 1,874 off-market properties in Winter Park, FL. Commercial property asks $414/SF to buy and $20.08/SF/Yr to lease.
Market Trends
Winter Park, FL spans 19.9 square miles in Orange County, Florida. Figures below refresh monthly; last updated 31 August 2026.
Office
Office space in Winter Park, FL asks $284/SF to buy. Vacancy runs 20.2% across the South region in 2025, up from 14.4% in 2019.
Average Sale Price $/SF
Listings
Vacancy Rate % in South region
Retail
Retail space in Winter Park, FL asks $422/SF to buy. Vacancy runs 5.4% across the South region in 2025, down from 7% in 2020.
Average Sale Price $/SF
Listings
Vacancy Rate % in South region
Industrial
Industrial vacancy in Winter Park, FL runs 7.9% across the South region in 2025, up from 6% in 2019. Nearly 2.3x the 2022 low of 3.5%.
Vacancy Rate % in South region
Multifamily
Multifamily vacancy in Winter Park, FL runs 11.3% across the South region in 2025, up from 8.5% in 2022.
Vacancy Rate % in South region
Market overview
Demographics & Economy
Winter Park, FL has 77,775 residents in 37,114 households. Density runs 3,905 people per square mile. Median household income here is $77,729 and median gross rent $1,631 a month.
77,775
Population
37,114
Households
2.1
Avg Household Size
38
Median Age
49%
College-Educated
93%
High-School Grad
19.9 sq mi
ZIP Area
3,905
Density / Sq Mi
$77,729
Median Household Income
$48,262
Median Earnings
$1,631
Median Rent
$462,809
Median Home Value
Tools
Lease vs Buy Breakeven
At $20.08/SF/Yr lease vs $414/SF buy → buying wins if held > 11.2 years.
At a 4.9% gross asking yield the payback reads short relative to leasing. Assumes 30% down at 6.5% fixed, 2% a year in taxes and upkeep, 3% appreciation, 5% opportunity cost, 2% closing plus 5% selling costs, and a 3% annual rent escalator.
Nearby Markets
| Market | Average Sale Price, $/SF | Average Lease Price, $/SF/Yr |
|---|---|---|
| Maitland | — | $18.20 |
| Eatonville | — | — |
| Fern Park | — | — |
| Goldenrod | — | — |
Commercial property in Winter Park, FL asks $414/SF.
Frequently Asked Questions
What is the average price per square foot for commercial property in Winter Park?
Commercial property in Winter Park, FL asks an average of $414 per square foot. The 7 most recent recorded sales traded at a median of $670/SF. Retail carries the highest asking price at $422/SF.
How much does it cost to lease commercial space in Winter Park?
Asking lease rates in Winter Park, FL average $20.08 per square foot per year.
Is it cheaper to lease or buy commercial space in Winter Park?
Buying beats leasing in Winter Park, FL if the property is held longer than 11.2 years, comparing $20.08/SF/Yr asking rent with $414/SF asking price. The model assumes 30% down at 6.5% fixed, 2% of value per year in taxes and upkeep, 3% appreciation, 5% opportunity cost on the cash and a 3% annual rent escalator.
Where does Realmo's Winter Park market data come from?
Realmo compiles Winter Park, FL figures from 7 recent recorded sales, 91 active sale listings, 86 active lease listings, 1,874 tracked off-market properties. Sale and lease figures refresh monthly; vacancy annually. Last updated 31 August 2026.
Methodology & data sources
- Asking prices and averages
- Computed from 91 active for-sale and 86 active for-lease listings in Winter Park, FL. These are ASKING figures from live listings, not closed-transaction prices, and a segment carried by a handful of listings reads as indicative rather than an average.
- Vacancy rates
- Published per-sector market series, taken at the metro level where one exists and otherwise at the Census-region level — a chart reading "in <region> region" is a regional number, not this city's.
- Refresh
- The monthly aggregates close at the end of the previous month, so 31 August 2026 — not today — is the honest last update.
- Known limitations
- office vacancy is reported at South region level, retail vacancy is reported at South region level and industrial vacancy is reported at South region level.
- Coverage
- Metrics below the 10-observation threshold fall back one geographic level. The geography used is named on each figure.
Compiled by the Realmo Data team · reviewed 31 August 2026 · report a data issue
