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Winter Park High School Zone Homes For Sale | Page 5

468 Homes
 
1101 N Hampton Ave, Orlando, FL 32803
  • $399,900
  • 2Bd
  • 1Ba
  • 876 Sq Ft
5401 Old Cheney Hwy, Orlando, FL 32807
  • $450,000
  • 3Bd
  • 2Ba
  • 1,364 Sq Ft
$25K
1140 S Orlando Ave #E1, Maitland, FL 32751
  • $287,000
  • 2Bd
  • 1Ba
  • 816 Sq Ft
$12K
1000 S Semoran Blvd #302, Winter Park, FL 32792
  • $105,000
  • 1Bd
  • 1Ba
  • 796 Sq Ft
$5K
1061 Aragon Ave #1061, Winter Park, FL 32789
  • $510,000
  • 3Bd
  • 3Ba
  • 1,669 Sq Ft
125 S Interlachen Ave #1, Winter Park, FL 32789
  • $3,695,000
  • 3Bd
  • 5Ba
  • 3,878 Sq Ft
$200K
1840 Laurel Rd, Winter Park, FL 32789
  • $2,299,000
  • 5Bd
  • 5Ba
  • 2,868 Sq Ft
$70K
433 Gilbert Rd, Winter Park, FL 32792
  • $669,900
  • 3Bd
  • 2Ba
  • 1,800 Sq Ft
Open SUN 12-2
1000 S Semoran Blvd #305, Winter Park, FL 32792
  • $115,000
  • 1Bd
  • 1Ba
  • 735 Sq Ft
$14K
2051 Dyan Way, Maitland, FL 32751
  • $799,000
  • 5Bd
  • 4Ba
  • 3,136 Sq Ft
$31K
3627 Bobolink Ln, Orlando, FL 32803
  • $1,415,000
  • 4Bd
  • 5Ba
  • 3,565 Sq Ft
2080 Goldwater Ct, Maitland, FL 32751
  • $779,000
  • 4Bd
  • 2Ba
  • 2,280 Sq Ft
$10K
281 Brewer Ave, Winter Park, FL 32789
  • $1,800,000
  • 5Bd
  • 5Ba
  • 4,029 Sq Ft
759 Lake Baldwin Ln, Orlando, FL 32803
  • $555,000
  • 3Bd
  • 3Ba
  • 1,842 Sq Ft
1927 S Lakemont Ave, Winter Park, FL 32792
  • $915,000
  • 3Bd
  • 4Ba
  • 2,093 Sq Ft
Open SUN 11-3
9359 Toby Ln, Orlando, FL 32817
  • $400,000
  • 3Bd
  • 2Ba
  • 1,443 Sq Ft
$5K
Photos coming soon
  • $589,900
  • 4Bd
  • 2Ba
  • 2,948 Sq Ft
$5K
1562 Arbor Park Dr, Winter Park, FL 32789
  • $775,000
  • 4Bd
  • 3Ba
  • 1,899 Sq Ft
7909 Waldorf Ct, Orlando, FL 32817
  • $435,000
  • 3Bd
  • 2Ba
  • 1,628 Sq Ft
$5K
2526 Passamonte Dr #10F, Winter Park, FL 32792
  • $335,000
  • 3Bd
  • 3Ba
  • 1,790 Sq Ft
7450 Wynnewood Sq #189, Winter Park, FL 32792
  • $170,000
  • 2Bd
  • 3Ba
  • 1,031 Sq Ft
$15K
2425 Lake Sue Dr, Orlando, FL 32803
  • $950,000
  • 3Bd
  • 3Ba
  • 2,586 Sq Ft
8243 Pamlico St, Orlando, FL 32817
  • $525,000
  • 4Bd
  • 3Ba
  • 2,084 Sq Ft
1822 Jasper Dr, Orlando, FL 32807
  • $329,900
  • 3Bd
  • 2Ba
  • 1,196 Sq Ft
$5K
922 N Pennsylvania Ave, Winter Park, FL 32789
  • $1,875,000
  • 4Bd
  • 4Ba
  • 3,440 Sq Ft
$120K
462 W Lyman Ave, Winter Park, FL 32789
  • $1,495,000
  • 3Bd
  • 3Ba
  • 1,944 Sq Ft
$100K
885 Carnation Dr, Winter Park, FL 32792
  • $368,000
  • 4Bd
  • 2Ba
  • 1,240 Sq Ft
$7K
724 Monmouth Way, Winter Park, FL 32792
  • $798,000
  • 5Bd
  • 4Ba
  • 2,832 Sq Ft
$50.9K
Photos coming soon
  • $785,500
  • 3Bd
  • 2Ba
  • 1,959 Sq Ft
Open SUN 00-2
1415 Grove Ter, Winter Park, FL 32789
  • $1,995,000
  • 0.54 Acre
$205K
1361 Audubon Rd, Maitland, FL 32751
  • $850,000
  • 0.19 Acre
$45K
777 Halifax Ave, Winter Park, FL 32792
  • $1,449,000
  • 5Bd
  • 5Ba
  • 3,109 Sq Ft
$51K
1823 Sunset Dr, Winter Park, FL 32789
  • $2,549,000
  • 5Bd
  • 5Ba
  • 3,479 Sq Ft
2216 Stonington Ave #2216, Orlando, FL 32817
  • $229,900
  • 2Bd
  • 3Ba
  • 1,228 Sq Ft
2234 Stonington Ave #2234, Orlando, FL 32817
  • $189,000
  • 2Bd
  • 2Ba
  • 874 Sq Ft
$10K
2458 Long Meadow Way, Orlando, FL 32817
  • $289,900
  • 2Bd
  • 2Ba
  • 981 Sq Ft
$5K
1205 Falcon Dr, Orlando, FL 32803
  • $2,099,000
  • 5Bd
  • 6Ba
  • 4,017 Sq Ft
Open SUN 1-3
1140 S Orlando Ave #E11, Maitland, FL 32751
  • $188,900
  • 1Bd
  • 1Ba
  • 612 Sq Ft
$7K
1000 S Semoran Blvd #408, Winter Park, FL 32792
  • $138,000
  • 1Bd
  • 1Ba
  • 776 Sq Ft
$10K
1000 S Semoran Blvd #404, Winter Park, FL 32792
  • $138,000
  • 1Bd
  • 1Ba
  • 776 Sq Ft
$10K
1000 S Semoran Blvd #306, Winter Park, FL 32792
  • $138,000
  • 1Bd
  • 1Ba
  • 796 Sq Ft
$10K
1615 Cole Rd, Orlando, FL 32803
  • $1,530,000
  • 5Bd
  • 4Ba
  • 2,895 Sq Ft
$20K
2228 Azalea Pl, Winter Park, FL 32789
  • $5,600,000
  • 5Bd
  • 6Ba
  • 5,152 Sq Ft
981 Aragon Ave, Winter Park, FL 32789
  • $494,999
  • 2Bd
  • 1Ba
  • 857 Sq Ft
$4K
1138 S Pennsylvania Ave, Winter Park, FL 32789
  • $925,000
  • 3Bd
  • 3Ba
  • 2,434 Sq Ft
$74K
3006 Northwood Blvd, Winter Park, FL 32789
  • $925,000
  • 4Bd
  • 3Ba
  • 2,075 Sq Ft
$25K
660 W Morse Blvd, Winter Park, FL 32789
  • $2,695,000
  • 3Bd
  • 4Ba
  • 3,286 Sq Ft
$105K
2656 Meeting Pl, Orlando, FL 32814
  • $2,375,000
  • 5Bd
  • 5Ba
  • 3,982 Sq Ft
$20K
1659 Common Way Rd, Orlando, FL 32814
  • $595,000
  • 3Bd
  • 4Ba
  • 1,950 Sq Ft
$10K
7488 Whisperwood Dr #28, Winter Park, FL 32792
  • $199,000
  • 2Bd
  • 3Ba
  • 1,578 Sq Ft
$11K
201 - 250 of 468 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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