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Winter Park Real Estate & Winter Park, FL Homes For Sale | Page 8

484 Homes
 
1540 Miller Ave, Winter Park, FL 32789
  • $1,399,900
  • 4Bd
  • 4Ba
  • 2,984 Sq Ft
100 S Interlachen Ave #101, Winter Park, FL 32789
  • $1,299,000
  • 3Bd
  • 2Ba
  • 1,734 Sq Ft
8113 Lazy Bear Ln, Winter Park, FL 32792
  • $585,000
  • 4Bd
  • 3Ba
  • 2,267 Sq Ft
1530 Alabama Dr, Winter Park, FL 32789
  • $5,900,000
  • 5Bd
  • 4Ba
  • 3,680 Sq Ft
624 Fitzwalter Dr, Winter Park, FL 32792
  • $549,000
  • 3Bd
  • 2Ba
  • 1,335 Sq Ft
3484 Seagrape Dr, Winter Park, FL 32792
  • $299,900
  • 4Bd
  • 2Ba
  • 1,227 Sq Ft
1421 Chestnut Ave, Winter Park, FL 32789
  • $750,000
  • 0.17 Acre
1818 Dover Rd, Winter Park, FL 32792
  • $439,900
  • 3Bd
  • 2Ba
  • 1,873 Sq Ft
720 Killarney Bay Ct #7-6, Winter Park, FL 32789
  • $389,000
  • 2Bd
  • 2Ba
  • 1,140 Sq Ft
4599 Whimbrel Pl, Winter Park, FL 32792
  • $675,000
  • 4Bd
  • 3Ba
  • 2,366 Sq Ft
5218 Lake Howell Rd, Winter Park, FL 32792
  • $355,000
  • 4Bd
  • 2Ba
  • 1,582 Sq Ft
657 Minnesota Ave, Winter Park, FL 32789
  • $550,000
  • 4Bd
  • 2Ba
  • 1,548 Sq Ft
952 Moss Ln, Winter Park, FL 32789
  • $1,319,950
  • 4Bd
  • 5Ba
  • 3,474 Sq Ft
1421 Michigan Ave, Winter Park, FL 32789
  • $586,567
  • 5Bd
  • 3Ba
  • 2,031 Sq Ft
2825 Mulford Ave, Winter Park, FL 32789
  • $629,000
  • 2Bd
  • 2Ba
  • 1,249 Sq Ft
1521 Bantam Way, Winter Park, FL 32792
  • $424,900
  • 3Bd
  • 3Ba
  • 1,755 Sq Ft
2873 Old Castle Dr, Winter Park, FL 32792
  • $1,395,000
  • 4Bd
  • 4Ba
  • 4,247 Sq Ft
500 N Pennsylvania Ave #G, Winter Park, FL 32789
  • $349,500
  • 2Bd
  • 1Ba
  • 709 Sq Ft
3020 Antique Oaks Cir #129, Winter Park, FL 32792
  • $135,000
  • 2Bd
  • 2Ba
  • 1,018 Sq Ft
330 Elkhorn Ct, Winter Park, FL 32792
  • $539,900
  • 3Bd
  • 2Ba
  • 1,570 Sq Ft
$5K
432 W Swoope Ave, Winter Park, FL 32789
  • $680,000
  • 4Bd
  • 4Ba
  • 2,664 Sq Ft
$15K
1840 Anzle Ave, Winter Park, FL 32789
  • $1,750,000
  • 4Bd
  • 3Ba
  • 2,350 Sq Ft
3220 Netherwood Dr, Winter Park, FL 32792
  • $268,950
  • 2Bd
  • 2Ba
  • 1,036 Sq Ft
$50
205 Lewfield Cir #205, Winter Park, FL 32792
  • $182,900
  • 2Bd
  • 2Ba
  • 927 Sq Ft
$37.1K
2231 Nairn Dr, Winter Park, FL 32792
  • $499,000
  • 3Bd
  • 2Ba
  • 1,088 Sq Ft
230 Strathy Ln, Winter Park, FL 32792
  • $499,000
  • 2Bd
  • 1Ba
  • 920 Sq Ft
2500 Lee Rd #222, Winter Park, FL 32789
  • $184,400
  • 1Bd
  • 1Ba
  • 645 Sq Ft
$500
3601 Midiron Dr, Winter Park, FL 32789
  • $459,900
  • 0.21 Acre
$15K
731 Midget Dr, Winter Park, FL 32789
  • $899,000
  • 0.19 Acre
$41K
2217 Sussex Rd, Winter Park, FL 32792
  • $485,000
  • 4Bd
  • 2Ba
  • 2,092 Sq Ft
$14K
2612 Roxbury Rd, Winter Park, FL 32789
  • $629,900
  • 5Bd
  • 3Ba
  • 2,472 Sq Ft
$100
560 Ololu Dr, Winter Park, FL 32789
  • $899,000
  • 2Bd
  • 2Ba
  • 1,086 Sq Ft
$26K
151 N Orlando Ave # 115, Winter Park, FL 32789
  • $285,000
  • 2Bd
  • 1Ba
  • 710 Sq Ft
$5K
311 Scottsdale Sq #311, Winter Park, FL 32792
  • $109,400
  • 1Bd
  • 1Ba
  • 785 Sq Ft
$100
7340 Daniel Webster Dr, Winter Park, FL 32792
  • $179,900
  • 3Bd
  • 2Ba
7471 Canford Ct #19, Winter Park, FL 32792
  • $199,000
  • 2Bd
  • 2Ba
  • 1,393 Sq Ft
$6K
2336 Sun Valley Cir #BLDG 20, Winter Park, FL 32792
  • $285,000
  • 2Bd
  • 2Ba
  • 1,669 Sq Ft
$10K
207 E Kings Way, Winter Park, FL 32789
  • $3,600,000
  • 5Bd
  • 5Ba
  • 3,719 Sq Ft
$50K
1821 Englewood Rd, Winter Park, FL 32789
  • $3,075,000
  • 5Bd
  • 6Ba
  • 3,863 Sq Ft
Open SAT 12-2
2948 Antique Oaks Cir #94, Winter Park, FL 32792
  • $150,000
  • 1Bd
  • 1Ba
  • 749 Sq Ft
311 E Morse Blvd #7-11, Winter Park, FL 32789
  • $279,000
  • 1Bd
  • 1Ba
  • 570 Sq Ft
$20K
1849 Viburnum Ln, Winter Park, FL 32792
  • $389,900
  • 4Bd
  • 2Ba
  • 1,627 Sq Ft
$10K
503 N Interlachen Ave, Winter Park, FL 32789
  • $4,500,000
  • 0.48 Acre
$499K
2758 Banchory Rd, Winter Park, FL 32792
  • $619,500
  • 3Bd
  • 3Ba
  • 1,539 Sq Ft
$19.5K
5331 Oak Ct, Winter Park, FL 32792
  • $460,000
  • 3Bd
  • 2Ba
  • 1,263 Sq Ft
3370 Cedar Springs Pl #156, Winter Park, FL 32792
  • $179,990
  • 2Bd
  • 3Ba
  • 1,031 Sq Ft
$2.51K
151 N Orlando Ave #118, Winter Park, FL 32789
  • $299,999
  • 2Bd
  • 1Ba
  • 710 Sq Ft
$297K
3718 N Goldenrod Rd, Winter Park, FL 32792
  • $499,000
  • 0.62 Acre
3071 George Mason Ave #5, Winter Park, FL 32792
  • $89,900
  • —Bd
  • 1Ba
  • 549 Sq Ft
$7.1K
1695 Lee Rd #C202, Winter Park, FL 32789
  • $205,000
  • 3Bd
  • 2Ba
  • 1,149 Sq Ft
$5K
351 - 400 of 484 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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