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Real Estate Market Trends and Analytics in Winter Park, FL

In January 2026, Winter Park, FL homes were selling for an average price of $885,926, Winter Park, FL homes on average sell after 62 days on the market compared to 53 days last year. There were 1099 homes sold in Winter Park, FL for January 2026, compared to 1074 last year.
View all properties for sale in Winter Park, FL

Winter Park, FL Market Trend

Average List Price
The average list price of Winter Park, FL, was $1,148,462 in January 2026, compared to $956,000 in January 2025.

Winter Park, FL Market Trend for Houses

Average List Price
The average list price of houses in Winter Park, FL, was $1,664,357 in January 2026, compared to $1,357,134 in January 2025.

Winter Park, FL Market Trend for Condos / Townhouses / Penthouses

Average List Price
The average list price of condos/co-ops in Winter Park, FL, was $401,811 in January 2026, compared to $374,188 in January 2025.

Winter Park, FL Market Trend for Lots/Land

Average List Price
The average list price of lots/land in Winter Park, FL, was $1,284,077 in January 2026, compared to $876,125 in January 2025.

Winter Park, FL Market Trend for Commercial

Average List Price
The average list price of commercial in Winter Park, FL, was $345,452 in January 2026, compared to $716,274 in January 2025.

Winter Park, FL Housing Market Analysis

The average list price in Winter Park, FL is $1,148,462. The average list price in Winter Park, FL went up 33.32% from 2025 to 2026. Winter Park, FL home resale inventories is 282, which increased 2.17% since 2025. The average list price per square foot in Winter Park, FL is $414. 2025 it was $366.
282
for sale
103
for rent
8,211
sold
Price Range
$12 - $8.9M
Avg. SQFT Price
$414
SF Range
482 - 17,600 SF
Beds
1 - 7
Avg. Dom
133 days
Year Built
1920 - 2026

Properties in Winter Park, FL

311 E MORSE BOULEVARD UNIT 5 placeholder 311 E MORSE BOULEVARD UNIT 5
New
For Sale
$2,100,000
2 bds 2 ba 1,900 sqft
311 E MORSE BOULEVARD UNIT 5
860 N DENNING DRIVE placeholder 860 N DENNING DRIVE
+$100K (2026/01/04)
For Sale
House
$749,900
3 bds 2 ba 1,290 sqft
860 N DENNING DRIVE
2232 SHADOWLAND LOOP placeholder 2232 SHADOWLAND LOOP
2 days
For Sale
Townhouse
$429,000
3 bds 2 ba 1,755 sqft
2232 SHADOWLAND LOOP
731 BONGART ROAD placeholder 731 BONGART ROAD
3 days
For Sale
House
$570,000
4 bds 3 ba 1,526 sqft
731 BONGART ROAD
2002 INDIANA AVENUE placeholder 2002 INDIANA AVENUE
4 days
For Sale
Lots/Land
$358,000
0 room(s)
2002 INDIANA AVENUE
1280 GLADIOLAS DR placeholder 1280 GLADIOLAS DR
4 days
For Sale
House
$499,500
3 bds 2 ba 1,624 sqft
1280 GLADIOLAS DR
636 DUNBLANE DRIVE placeholder 636 DUNBLANE DRIVE
4 days
For Sale
House
$725,000
3 bds 2 ba 1,803 sqft
636 DUNBLANE DRIVE
637 N PARK AVENUE placeholder 637 N PARK AVENUE
5 days
For Sale
Townhouse
$3,895,000
3 bds 3 ba 4,237 sqft
637 N PARK AVENUE

Market Trends nearby