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Winter Park High School Zone Homes For Sale | Page 2

467 Homes
 
1003 Golfside Dr, Winter Park, FL 32792
  • $769,900
  • 3Bd
  • 3Ba
  • 2,145 Sq Ft
173 Scottsdale Sq #173, Winter Park, FL 32792
  • $100,000
  • 1Bd
  • 1Ba
  • 785 Sq Ft
1250 S Denning Dr #119, Winter Park, FL 32789
  • $265,000
  • 2Bd
  • 2Ba
  • 908 Sq Ft
1502 Dove Dr, Orlando, FL 32803
  • $880,000
  • 4Bd
  • 3Ba
  • 2,047 Sq Ft
$39K
739 Roughbeard Rd, Winter Park, FL 32792
  • $780,000
  • 5Bd
  • 3Ba
  • 2,194 Sq Ft
5034 Old Cheney Hwy, Orlando, FL 32807
  • $450,000
  • 0.3 Acre
2818 Ambergate Rd, Winter Park, FL 32792
  • $429,900
  • 3Bd
  • 2Ba
  • 1,398 Sq Ft
2470 Ivan Ct, Orlando, FL 32807
  • $330,000
  • 3Bd
  • 2Ba
  • 1,100 Sq Ft
192 Balfour Dr #2, Winter Park, FL 32792
  • $319,000
  • 2Bd
  • 2Ba
  • 1,287 Sq Ft
3000 Chelsea St, Orlando, FL 32803
  • $676,000
  • 3Bd
  • 2Ba
  • 1,676 Sq Ft
$3K
1951 Winter Park Rd, Winter Park, FL 32789
  • $2,089,000
  • 4Bd
  • 4Ba
  • 3,479 Sq Ft
Open SUN 2-4
100 S Virginia Ave #201, Winter Park, FL 32789
  • $1,450,000
  • 3Bd
  • 3Ba
  • 2,756 Sq Ft
532 Langholm Dr, Winter Park, FL 32789
  • $2,990,000
  • 5Bd
  • 5Ba
  • 4,050 Sq Ft
2614 Parkland Dr, Winter Park, FL 32789
  • $1,890,000
  • 4Bd
  • 4Ba
  • 3,307 Sq Ft
1602 Alabama Dr #107, Winter Park, FL 32789
  • $1,150,000
  • 2Bd
  • 2Ba
  • 993 Sq Ft
2000 E Adams, Maitland, FL 32751
  • $1,700,000
  • 0.39 Acre
1418 Kingston Ave, Orlando, FL 32807
  • $179,900
  • 0.37 Acre
1742 Temple Dr, Winter Park, FL 32789
  • $3,695,999
  • 4Bd
  • 5Ba
  • 3,658 Sq Ft
1306 S Pennsylvania Ave #5, Winter Park, FL 32789
  • $359,000
  • 2Bd
  • 1Ba
  • 830 Sq Ft
7453 Daniel Webster Dr #A5, Winter Park, FL 32792
  • $150,000
  • 2Bd
  • 2Ba
  • 1,063 Sq Ft
3354 Tcu Blvd, Orlando, FL 32817
  • $484,900
  • 4Bd
  • 2Ba
  • 1,680 Sq Ft
$5K
555 E Lake Sue Ave, Winter Park, FL 32789
  • $2,095,000
  • 4Bd
  • 4Ba
  • 3,776 Sq Ft
3731 Valencia Grove Ln, Orlando, FL 32817
  • $370,000
  • 4Bd
  • 2Ba
  • 2,127 Sq Ft
$5K
250 Carolina Ave #202, Winter Park, FL 32789
  • $699,000
  • 3Bd
  • 2Ba
  • 1,450 Sq Ft
3334 Young St, Winter Park, FL 32792
  • $474,900
  • 3Bd
  • 2Ba
  • 1,706 Sq Ft
2572 Fifeshire Dr, Winter Park, FL 32792
  • $899,900
  • 4Bd
  • 3Ba
  • 2,578 Sq Ft
$25.1K
662 Granville Dr, Winter Park, FL 32789
  • $3,495,000
  • 5Bd
  • 6Ba
  • 4,478 Sq Ft
793 Eldridge St, Orlando, FL 32803
  • $390,000
  • 3Bd
  • 1Ba
  • 2,160 Sq Ft
8042 Ridge Way, Orlando, FL 32817
  • $539,000
  • 4Bd
  • 2Ba
  • 2,239 Sq Ft
Open SUN 12-3
1166 Palmer Ave, Winter Park, FL 32789
  • $5,500,000
  • 5Bd
  • 7Ba
  • 5,181 Sq Ft
2215 Woodcrest Dr, Winter Park, FL 32792
  • $675,000
  • 4Bd
  • 2Ba
  • 1,688 Sq Ft
Open SUN 11-1
2345 Brookshire Ave, Winter Park, FL 32792
  • $825,000
  • 3Bd
  • 3Ba
  • 2,488 Sq Ft
$25K
3209 Heartwood Ave, Winter Park, FL 32792
  • $439,900
  • 4Bd
  • 2Ba
  • 1,627 Sq Ft
$10K
1579 Lake Baldwin Ln, Orlando, FL 32814
  • $1,450,000
  • —Bd
  • —Ba
  • 3,150 Sq Ft
1271 Palmer Ave, Winter Park, FL 32789
  • $2,195,000
  • 4Bd
  • 5Ba
  • 2,850 Sq Ft
Open SUN 2-4
504 W Swoope Ave, Winter Park, FL 32789
  • $1,300,000
  • 3Bd
  • 3Ba
  • 2,563 Sq Ft
2119 Howard Dr, Winter Park, FL 32789
  • $3,195,000
  • 5Bd
  • 6Ba
  • 4,139 Sq Ft
618 Blairshire Cir, Winter Park, FL 32792
  • $895,000
  • 4Bd
  • 3Ba
  • 1,876 Sq Ft
Open SUN 1-3
913 Moss Ln, Winter Park, FL 32789
  • $950,000
  • 3Bd
  • 2Ba
  • 1,887 Sq Ft
1803 Barker Dr, Winter Park, FL 32789
  • $2,190,000
  • 4Bd
  • 3Ba
  • 3,463 Sq Ft
786 W Canton Ave, Winter Park, FL 32789
  • $450,000
  • 0.11 Acre
2561 Cavanaugh Dr, Orlando, FL 32817
  • $625,000
  • 5Bd
  • 3Ba
  • 3,198 Sq Ft
$10
4870 Seminole Ave, Winter Park, FL 32792
  • $380,000
  • 3Bd
  • 2Ba
  • 1,277 Sq Ft
$100
540 N Pennsylvania Ave, Winter Park, FL 32789
  • $3,950,000
  • 4Bd
  • 2Ba
  • 1,652 Sq Ft
2483 Long Meadow Way, Orlando, FL 32817
  • $315,000
  • 2Bd
  • 2Ba
  • 981 Sq Ft
2639 Cavanaugh Dr, Orlando, FL 32817
  • $600,000
  • 4Bd
  • 4Ba
  • 2,560 Sq Ft
1431 Palm Ave, Winter Park, FL 32789
  • $799,999
  • 0.16 Acre
$25K
2410 Sherbrooke Rd, Winter Park, FL 32792
  • $769,000
  • 4Bd
  • 3Ba
  • 2,141 Sq Ft
$20K
311 E Morse Blvd #1-5, Winter Park, FL 32789
  • $2,475,000
  • 3Bd
  • 3Ba
  • 2,316 Sq Ft
250 W Reading Way, Winter Park, FL 32789
  • $4,325,000
  • 5Bd
  • 5Ba
  • 4,853 Sq Ft
51 - 100 of 467 Homes for sale in Winter Park, FL
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Winter Park, FL real estate market trends

Statistics as of October 2026
$599K
Avg. list price
$346/Sqft
Avg. price/sqft
445
Homes for sale
1,786 Sqft
Avg. home size
67 Days
Avg. days on market
Movoto makes it easy to track market trends in Winter Park, FL. Whether you’re entering the market or planning your next move, understanding these key metrics can guide smart decisions. Looking for more detailed housing market stats in Winter Park, FL?
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