247 Homes
Winter Park, FL homes on Orchard for more than 30 days
In the last 30 days, Winter Park home prices were up 12.1% compared to last year. The median price of a home was $510,000. View Winter Park Market Insights
1 / 18
$3,950,000
PHIL KEAN REAL ESTATE LLC • MLS O6337162 • Status: Active
1 / 60
Price Drop
$2,299,000
$2,329,000
COMPASS FLORIDA LLC • MLS O6338650 • Status: Active
1 / 52
$1,200,000
PREMIER SOTHEBY'S INTL. REALTY • MLS O6330566 • Status: Active
1 / 15
Price Drop
$165,000
$175,000
COLDWELL BANKER REALTY • MLS O6337083 • Status: Active
1 / 15
$329,999
FLAT FEE MLS REALTY • MLS TB8387465 • Status: Active
1 / 51
$1,285,000
KELLER WILLIAMS REALTY AT THE PARKS • MLS O6337890 • Status: Active
1 / 55
Price Drop
$1,695,000
$1,700,000
RE/MAX 200 REALTY • MLS O6324320 • Status: Active
1 / 56
Price Drop
$2,049,400
$2,090,000
JW GASTON LLC • MLS O6301489 • Status: Active
1 / 58
Price Drop
$3,650,000
$3,799,000
PREMIER SOTHEBY'S INTL. REALTY • MLS O6320054 • Status: Active
1 / 53
Price Drop
$460,000
$469,000
FOWLKES REALTY CO • MLS O6336213 • Status: Active
1 / 27
$158,500
CHARLES RUTENBERG REALTY ORLANDO • MLS O6336219 • Status: Active
1 / 72
Price Drop
$942,500
$945,000
KELLER WILLIAMS CLASSIC • MLS O6336887 • Status: Active
1 / 20
Price Drop
$375,000
$400,000
THE AGENCY ORLANDO • MLS O6336526 • Status: Active
1 / 32
Price Drop
$469,900
$475,000
THE WILKINS WAY LLC • MLS O6337220 • Status: Active
1 / 88
$8,500,000
KELLY PRICE & COMPANY LLC • MLS O6312768 • Status: Active
1 / 64
Price Drop
$2,099,000
$2,199,999
KELLER WILLIAMS WINTER PARK • MLS O6331369 • Status: Active
1 / 53
$1,349,000
CHARLES RUTENBERG REALTY ORLANDO • MLS O6316445 • Status: Active
1 / 66
$4,650,000
THE REAL ESTATE COLLECTION LLC • MLS O6330736 • Status: Active
1 / 19
$5,950,000
PHIL KEAN REAL ESTATE LLC • MLS O6332790 • Status: Active
1 / 99
Price Drop
$2,300,000
$2,497,000
FLORIDA CONNEXION PROPERTIES • MLS O6314404 • Status: Active
1 / 34
Price Drop
$725,000
$795,000
KELLER WILLIAMS WINTER PARK • MLS O6323574 • Status: Active
1 / 57
Price Drop
$999,950
$1,070,000
TRANSCEND REALTY • MLS S5122502 • Status: Active
1 / 35
$4,250,000
PHIL KEAN REAL ESTATE LLC • MLS O6332795 • Status: Active
1 / 41
$599,000
EXP REALTY LLC • MLS O6183345 • Status: Active
1 / 50
$1,050,000
SAND DOLLAR REALTY GROUP INC • MLS O6334421 • Status: Active
1 / 49
Price Drop
$210,000
$215,000
KELLER WILLIAMS REALTY AT THE PARKS • MLS O6297570 • Status: Active
1 / 72
$1,095,000
FORTUNE INTERNATIONAL REALTY • MLS O6314734 • Status: Active
1 / 42
$765,000
KELLY PRICE & COMPANY LLC • MLS O6280564 • Status: Active
1 / 48
$1,275,000
BHHS FLORIDA REALTY • MLS O6330075 • Status: Active
1 / 45
Price Drop
$798,000
$815,000
RE/MAX PRIME PROPERTIES • MLS O6329169 • Status: Active
1 / 37
$489,500
CENTURY 21 CARIOTI • MLS O6308136 • Status: Active
1 / 12
$3,490,000
COMPASS FLORIDA LLC • MLS O6294091 • Status: Active
1 / 38
Price Drop
$965,000
$995,000
PR REAL ESTATE SERVICES • MLS O6279127 • Status: Active
1 / 11
$1,759,000
COMPASS FLORIDA LLC • MLS O6275164 • Status: Active
1 / 36
$386,500
ABSOLUTE REALTY GROUP, LLC • MLS O6285965 • Status: Active
1 / 39
Price Drop
$509,000
$519,000
KELLER WILLIAMS WINTER PARK • MLS O6323244 • Status: Active
Viewing 1-36 of 247 homes
Winter Park Market Trends
All Home Types
In the last 30 days, homes for sale in Winter Park, FL sold for a median price of $510,000, up 12.1% compared to the same period last year. The median price per square foot was $298.60, up 8.1% year-over-year. There were 65 homes sold, down from 79 last year.
Median Sale Price
$510,000
+12.1% year-over-year
Median Price per Sq. Ft.
$298.60
+8.1% year-over-year
Number of Homes Sold
65
-17.7% year-over-year
Frequently Asked Questions
What is the median home sale price in Winter Park, FL?
In the last 30 days, the median home sale price in Winter Park was $510,000, up 12.1% compared to the same period last year. The "median" price is the middle price - half of the homes here were sold for less, the other half for more.
How many homes are for sale in Winter Park, FL?
There were 332 homes for sale in Winter Park as of September 24, 2025. There were 101 new listings within the last 30 days as well. The more homes on the market, the more choices buyers have.
How up-to-date are Orchard's new listings in Winter Park, FL?
The new homes and houses for sale on Orchard's listings pages are updated hundreds of times each day, with listings in Winter Park last seen updated at . New listings can appear every day, but many listings first appear on the market mid-week.
How much competition is there to buy a home in Winter Park, FL?
In the last 30 days, the median number of days a home in Winter Park remained on the market (DOM) was 26. In areas with a low DOM, homes are sold quickly and the competition is fierce; in areas with higher DOMs, you may have more options and more time to make an offer.
Home Buying Resources
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Based on information submitted to the MLS GRID as of 9/26/2025, 12:39AM. 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.