Listings in 32789 - Other County, Florida
Displaying 1 – 200 of 389 Real estate listings
1591 Cardinal Court, Winter Park, FL 32789
Winter Park, FL | Active
Listed: Jun, 01, 2026
Price: $2,995,000
Living Area: 3,523 Sq. Ft.
Winter Park, FL | Active
Listed: Jun, 01, 2026
Price: $2,995,000
Living Area: 3,523 Sq. Ft.
2661 Via Tuscany
Winter Park, FL | Withdrawn
Listed: May, 15, 2026
Price: $6,888,888
Living Area: 4,636 Sq. Ft.
Winter Park, FL | Withdrawn
Listed: May, 15, 2026
Price: $6,888,888
Living Area: 4,636 Sq. Ft.
1451 Cavendish Road
Winter Park, FL | Closed
Listed: Oct, 30, 2025
Price: $619,500
Living Area: 1,437 Sq. Ft.
Winter Park, FL | Closed
Listed: Oct, 30, 2025
Price: $619,500
Living Area: 1,437 Sq. Ft.
405 Lake Fair Lane
Winter Park, FL | Closed
Listed: Jul, 29, 2026
Price: $434,990
Living Area: 0 Sq. Ft.
Winter Park, FL | Closed
Listed: Jul, 29, 2026
Price: $434,990
Living Area: 0 Sq. Ft.
443 Broadview Ave
Winter Park, FL | Active
Listed: Aug, 31, 2026
Price: $1,095,000
Living Area: 2,803 Sq. Ft.
Winter Park, FL | Active
Listed: Aug, 31, 2026
Price: $1,095,000
Living Area: 2,803 Sq. Ft.
2500 Lee Rd #232
Winter Park, FL | Closed
Listed: May, 06, 2026
Price: $149,000
Living Area: 645 Sq. Ft.
Winter Park, FL | Closed
Listed: May, 06, 2026
Price: $149,000
Living Area: 645 Sq. Ft.
1409 Michigan Ave
Winter Park, FL | Active
Listed: Aug, 01, 2026
Price: $3,100
Living Area: 1,803 Sq. Ft.
Winter Park, FL | Active
Listed: Aug, 01, 2026
Price: $3,100
Living Area: 1,803 Sq. Ft.
1821 Englewood Rd
Winter Park, FL | Active
Listed: Sep, 19, 2025
Price: $3,075,000
Living Area: 3,863 Sq. Ft.
Winter Park, FL | Active
Listed: Sep, 19, 2025
Price: $3,075,000
Living Area: 3,863 Sq. Ft.
870 N Phelps Ave
Winter Park, FL | Active
Listed: Sep, 28, 2026
Price: $850,000
Living Area: 2,301 Sq. Ft.
Winter Park, FL | Active
Listed: Sep, 28, 2026
Price: $850,000
Living Area: 2,301 Sq. Ft.
870 N Phelps Ave
Winter Park, FL | Active
Listed: Sep, 28, 2026
Price: $850,000
Living Area: 0 Sq. Ft.
Winter Park, FL | Active
Listed: Sep, 28, 2026
Price: $850,000
Living Area: 0 Sq. Ft.
1271 Palmer Ave
Winter Park, FL | Active
Listed: Sep, 16, 2026
Price: $2,195,000
Living Area: 2,850 Sq. Ft.
Winter Park, FL | Active
Listed: Sep, 16, 2026
Price: $2,195,000
Living Area: 2,850 Sq. Ft.
1951 Winter Park Rd
Winter Park, FL | Active
Listed: Sep, 23, 2026
Price: $2,089,000
Living Area: 3,479 Sq. Ft.
Winter Park, FL | Active
Listed: Sep, 23, 2026
Price: $2,089,000
Living Area: 3,479 Sq. Ft.
2831 Mulford Ave
Winter Park, FL | Active
Listed: Jun, 05, 2026
Price: $655,000
Living Area: 1,647 Sq. Ft.
Winter Park, FL | Active
Listed: Jun, 05, 2026
Price: $655,000
Living Area: 1,647 Sq. Ft.
1421 Chapman Cir
Winter Park, FL | Active Under Contract
Listed: Jun, 12, 2026
Price: $1,377,500
Living Area: 3,578 Sq. Ft.
Winter Park, FL | Active Under Contract
Listed: Jun, 12, 2026
Price: $1,377,500
Living Area: 3,578 Sq. Ft.
1800 Magnolia Ave
Winter Park, FL | Closed
Listed: Mar, 14, 2026
Price: $950,000
Living Area: 2,431 Sq. Ft.
Winter Park, FL | Closed
Listed: Mar, 14, 2026
Price: $950,000
Living Area: 2,431 Sq. Ft.
1695 Lee Road D213
Winter Park, FL | Closed
Listed: Apr, 10, 2026
Price: $1,300
Living Area: 881 Sq. Ft.
Winter Park, FL | Closed
Listed: Apr, 10, 2026
Price: $1,300
Living Area: 881 Sq. Ft.
635 Huntington Avenue 2
Winter Park, FL | Closed
Listed: Aug, 27, 2022
Price: $399,000
Living Area: 1,204 Sq. Ft.
Winter Park, FL | Closed
Listed: Aug, 27, 2022
Price: $399,000
Living Area: 1,204 Sq. Ft.
2560 Franklin Avenue
Winter Park, FL | Withdrawn
Listed: Mar, 22, 2024
Price: $479,000
Living Area: 1,514 Sq. Ft.
Winter Park, FL | Withdrawn
Listed: Mar, 22, 2024
Price: $479,000
Living Area: 1,514 Sq. Ft.
500 N Pennsylvania Ave #g
Winter Park, FL | Active Under Contract
Listed: Aug, 28, 2026
Price: $349,500
Living Area: 709 Sq. Ft.
Winter Park, FL | Active Under Contract
Listed: Aug, 28, 2026
Price: $349,500
Living Area: 709 Sq. Ft.
1500 Gay Rd #4d
Winter Park, FL | Active
Listed: Jul, 15, 2026
Price: $164,500
Living Area: 732 Sq. Ft.
Winter Park, FL | Active
Listed: Jul, 15, 2026
Price: $164,500
Living Area: 732 Sq. Ft.
950 Hanover Ave
Winter Park, FL | Active
Listed: Apr, 10, 2026
Price: $439,000
Living Area: 1,606 Sq. Ft.
Winter Park, FL | Active
Listed: Apr, 10, 2026
Price: $439,000
Living Area: 1,606 Sq. Ft.
1760 Oakhurst Ave
Winter Park, FL | Coming Soon
Listed: Sep, 27, 2026
Price: $2,500,000
Living Area: 3,700 Sq. Ft.
Winter Park, FL | Coming Soon
Listed: Sep, 27, 2026
Price: $2,500,000
Living Area: 3,700 Sq. Ft.
2207 Kindel Ave
Winter Park, FL | Active
Listed: Aug, 16, 2026
Price: $1,600,000
Living Area: 2,733 Sq. Ft.
Winter Park, FL | Active
Listed: Aug, 16, 2026
Price: $1,600,000
Living Area: 2,733 Sq. Ft.
1754 Taylor Ave
Winter Park, FL | Active Under Contract
Listed: Jul, 08, 2026
Price: $2,569,999
Living Area: 3,670 Sq. Ft.
Winter Park, FL | Active Under Contract
Listed: Jul, 08, 2026
Price: $2,569,999
Living Area: 3,670 Sq. Ft.
1702 Arbor Park Dr
Winter Park, FL | Active Under Contract
Listed: Sep, 01, 2026
Price: $1,900,000
Living Area: 2,950 Sq. Ft.
Winter Park, FL | Active Under Contract
Listed: Sep, 01, 2026
Price: $1,900,000
Living Area: 2,950 Sq. Ft.
698 N New York Ave
Winter Park, FL | Active
Listed: Sep, 09, 2026
Price: $6,195,000
Living Area: 5,096 Sq. Ft.
Winter Park, FL | Active
Listed: Sep, 09, 2026
Price: $6,195,000
Living Area: 5,096 Sq. Ft.
440 Clarendon Ave
Winter Park, FL | Active
Listed: Sep, 23, 2026
Price: $8,500
Living Area: 3,184 Sq. Ft.
Winter Park, FL | Active
Listed: Sep, 23, 2026
Price: $8,500
Living Area: 3,184 Sq. Ft.
1417 Williams Dr
Winter Park, FL | Closed
Listed: Aug, 18, 2026
Price: $3,999,000
Living Area: 4,891 Sq. Ft.
Winter Park, FL | Closed
Listed: Aug, 18, 2026
Price: $3,999,000
Living Area: 4,891 Sq. Ft.
231 Chelton Cir
Winter Park, FL | Active
Listed: Jun, 09, 2026
Price: $4,700,000
Living Area: 5,550 Sq. Ft.
Winter Park, FL | Active
Listed: Jun, 09, 2026
Price: $4,700,000
Living Area: 5,550 Sq. Ft.
1627 Orange Ave
Winter Park, FL | Active
Listed: Jul, 17, 2026
Price: $2,500
Living Area: 1,302 Sq. Ft.
Winter Park, FL | Active
Listed: Jul, 17, 2026
Price: $2,500
Living Area: 1,302 Sq. Ft.
2500 Lee Rd #104
Winter Park, FL | Active
Listed: Jun, 09, 2026
Price: $242,400
Living Area: 956 Sq. Ft.
Winter Park, FL | Active
Listed: Jun, 09, 2026
Price: $242,400
Living Area: 956 Sq. Ft.
100 S Interlachen Ave #101
Winter Park, FL | Active Under Contract
Listed: Sep, 24, 2026
Price: $1,299,000
Living Area: 1,734 Sq. Ft.
Winter Park, FL | Active Under Contract
Listed: Sep, 24, 2026
Price: $1,299,000
Living Area: 1,734 Sq. Ft.
1885 Temple Dr
Winter Park, FL | Active Under Contract
Listed: Nov, 10, 2025
Price: $2,195,000
Living Area: 3,691 Sq. Ft.
Winter Park, FL | Active Under Contract
Listed: Nov, 10, 2025
Price: $2,195,000
Living Area: 3,691 Sq. Ft.
948 Poinciana Ln
Winter Park, FL | Closed
Listed: Aug, 14, 2026
Price: $2,750,000
Living Area: 3,676 Sq. Ft.
Winter Park, FL | Closed
Listed: Aug, 14, 2026
Price: $2,750,000
Living Area: 3,676 Sq. Ft.
1884 Biscayne Dr
Winter Park, FL | Closed
Listed: Sep, 27, 2026
Price: $315,000
Living Area: 678 Sq. Ft.
Winter Park, FL | Closed
Listed: Sep, 27, 2026
Price: $315,000
Living Area: 678 Sq. Ft.
1523 Miller Ave
Winter Park, FL | Closed
Listed: Jan, 07, 2026
Price: $1,399,000
Living Area: 3,164 Sq. Ft.
Winter Park, FL | Closed
Listed: Jan, 07, 2026
Price: $1,399,000
Living Area: 3,164 Sq. Ft.
1009 Lake Bell Dr
Winter Park, FL | Canceled
Listed: May, 22, 2026
Price: $650,000
Living Area: 0 Sq. Ft.
Winter Park, FL | Canceled
Listed: May, 22, 2026
Price: $650,000
Living Area: 0 Sq. Ft.
2234 Howard Dr
Winter Park, FL | Active
Listed: Jul, 23, 2026
Price: $7,995
Living Area: 3,295 Sq. Ft.
Winter Park, FL | Active
Listed: Jul, 23, 2026
Price: $7,995
Living Area: 3,295 Sq. Ft.
525 Ololu Dr
Winter Park, FL | Active
Listed: Apr, 28, 2026
Price: $490,900
Living Area: 1,786 Sq. Ft.
Winter Park, FL | Active
Listed: Apr, 28, 2026
Price: $490,900
Living Area: 1,786 Sq. Ft.
1250 Formosa Ave
Winter Park, FL | Active
Listed: Jun, 03, 2026
Price: $535,000
Living Area: 1,937 Sq. Ft.
Winter Park, FL | Active
Listed: Jun, 03, 2026
Price: $535,000
Living Area: 1,937 Sq. Ft.
860 N Denning Dr
Winter Park, FL | Active
Listed: Jun, 01, 2026
Price: $649,900
Living Area: 1,411 Sq. Ft.
Winter Park, FL | Active
Listed: Jun, 01, 2026
Price: $649,900
Living Area: 1,411 Sq. Ft.
1421 Michigan Ave
Winter Park, FL | Pending
Listed: Sep, 10, 2026
Price: $586,567
Living Area: 2,031 Sq. Ft.
Winter Park, FL | Pending
Listed: Sep, 10, 2026
Price: $586,567
Living Area: 2,031 Sq. Ft.
310 Granada Dr
Winter Park, FL | Expired
Listed: Aug, 05, 2026
Price: $315,000
Living Area: 1,344 Sq. Ft.
Winter Park, FL | Expired
Listed: Aug, 05, 2026
Price: $315,000
Living Area: 1,344 Sq. Ft.
1695 Lee Rd #b210
Winter Park, FL | Active Under Contract
Listed: Jan, 20, 2026
Price: $89,000
Living Area: 638 Sq. Ft.
Winter Park, FL | Active Under Contract
Listed: Jan, 20, 2026
Price: $89,000
Living Area: 638 Sq. Ft.
1416 Border Dr
Winter Park, FL | Active
Listed: Aug, 21, 2026
Price: $620,000
Living Area: 0 Sq. Ft.
Winter Park, FL | Active
Listed: Aug, 21, 2026
Price: $620,000
Living Area: 0 Sq. Ft.
1416 Border Dr
Winter Park, FL | Active
Listed: Aug, 21, 2026
Price: $620,000
Living Area: 1,243 Sq. Ft.
Winter Park, FL | Active
Listed: Aug, 21, 2026
Price: $620,000
Living Area: 1,243 Sq. Ft.
188 Sandlewood #1
Winter Park, FL | Active
Listed: Sep, 24, 2026
Price: $290,000
Living Area: 1,133 Sq. Ft.
Winter Park, FL | Active
Listed: Sep, 24, 2026
Price: $290,000
Living Area: 1,133 Sq. Ft.
307 Sandlewood Trl
Winter Park, FL | Active
Listed: Oct, 01, 2026
Price: $1,895
Living Area: 960 Sq. Ft.
Winter Park, FL | Active
Listed: Oct, 01, 2026
Price: $1,895
Living Area: 960 Sq. Ft.
1225 Sharon Pl
Winter Park, FL | Pending
Listed: Sep, 25, 2026
Price: $1,749,000
Living Area: 3,097 Sq. Ft.
Winter Park, FL | Pending
Listed: Sep, 25, 2026
Price: $1,749,000
Living Area: 3,097 Sq. Ft.
1016 Aragon Ave
Winter Park, FL | Active
Listed: Aug, 23, 2026
Price: $660,000
Living Area: 1,840 Sq. Ft.
Winter Park, FL | Active
Listed: Aug, 23, 2026
Price: $660,000
Living Area: 1,840 Sq. Ft.
1016 Aragon Ave
Winter Park, FL | Active
Listed: Aug, 23, 2026
Price: $660,000
Living Area: 1,840 Sq. Ft.
Winter Park, FL | Active
Listed: Aug, 23, 2026
Price: $660,000
Living Area: 1,840 Sq. Ft.
1354 Indiana Ave
Winter Park, FL | Expired
Listed: Mar, 05, 2026
Price: $574,900
Living Area: 1,269 Sq. Ft.
Winter Park, FL | Expired
Listed: Mar, 05, 2026
Price: $574,900
Living Area: 1,269 Sq. Ft.
471 Holt Ave
Winter Park, FL | Active
Listed: Aug, 29, 2026
Price: $950,000
Living Area: 2,528 Sq. Ft.
Winter Park, FL | Active
Listed: Aug, 29, 2026
Price: $950,000
Living Area: 2,528 Sq. Ft.
1871 Bryan Ave
Winter Park, FL | Active
Listed: Oct, 01, 2026
Price: $599,000
Living Area: 0 Sq. Ft.
Winter Park, FL | Active
Listed: Oct, 01, 2026
Price: $599,000
Living Area: 0 Sq. Ft.
1741 Mizell Ave
Winter Park, FL | Pending
Listed: Aug, 22, 2026
Price: $4,200
Living Area: 2,015 Sq. Ft.
Winter Park, FL | Pending
Listed: Aug, 22, 2026
Price: $4,200
Living Area: 2,015 Sq. Ft.
313 Sylvan Dr
Winter Park, FL | Pending
Listed: Jul, 10, 2026
Price: $1,750,000
Living Area: 0 Sq. Ft.
Winter Park, FL | Pending
Listed: Jul, 10, 2026
Price: $1,750,000
Living Area: 0 Sq. Ft.
2119 Howard Dr
Winter Park, FL | Active
Listed: Sep, 16, 2026
Price: $3,195,000
Living Area: 4,139 Sq. Ft.
Winter Park, FL | Active
Listed: Sep, 16, 2026
Price: $3,195,000
Living Area: 4,139 Sq. Ft.
720 Killarney Bay Ct #7-6
Winter Park, FL | Canceled
Listed: Sep, 17, 2026
Price: $389,000
Living Area: 1,140 Sq. Ft.
Winter Park, FL | Canceled
Listed: Sep, 17, 2026
Price: $389,000
Living Area: 1,140 Sq. Ft.
641 Northwood Circle
Winter Park, FL | Active
Listed: Jun, 01, 2026
Price: $1,499,000
Living Area: 2,756 Sq. Ft.
Winter Park, FL | Active
Listed: Jun, 01, 2026
Price: $1,499,000
Living Area: 2,756 Sq. Ft.
311 E Morse Blvd #1-3
Winter Park, FL | Closed
Listed: May, 08, 2026
Price: $1,825,000
Living Area: 2,304 Sq. Ft.
Winter Park, FL | Closed
Listed: May, 08, 2026
Price: $1,825,000
Living Area: 2,304 Sq. Ft.
660 W Morse Blvd
Winter Park, FL | Active
Listed: May, 21, 2026
Price: $2,695,000
Living Area: 3,286 Sq. Ft.
Winter Park, FL | Active
Listed: May, 21, 2026
Price: $2,695,000
Living Area: 3,286 Sq. Ft.
3006 Northwood Blvd
Winter Park, FL | Active
Listed: Jun, 22, 2026
Price: $925,000
Living Area: 2,075 Sq. Ft.
Winter Park, FL | Active
Listed: Jun, 22, 2026
Price: $925,000
Living Area: 2,075 Sq. Ft.
723 Symonds Ave
Winter Park, FL | Active
Listed: May, 28, 2026
Price: $1,600,000
Living Area: 3,065 Sq. Ft.
Winter Park, FL | Active
Listed: May, 28, 2026
Price: $1,600,000
Living Area: 3,065 Sq. Ft.
341 E Reading Way
Winter Park, FL | Active
Listed: Jun, 30, 2026
Price: $1,525,000
Living Area: 3,723 Sq. Ft.
Winter Park, FL | Active
Listed: Jun, 30, 2026
Price: $1,525,000
Living Area: 3,723 Sq. Ft.
128 Oak Grove Rd
Winter Park, FL | Closed
Listed: Sep, 10, 2026
Price: $2,200
Living Area: 1,156 Sq. Ft.
Winter Park, FL | Closed
Listed: Sep, 10, 2026
Price: $2,200
Living Area: 1,156 Sq. Ft.
1695 Lee Rd #c210
Winter Park, FL | Closed
Listed: Sep, 28, 2026
Price: $80,000
Living Area: 638 Sq. Ft.
Winter Park, FL | Closed
Listed: Sep, 28, 2026
Price: $80,000
Living Area: 638 Sq. Ft.
2401 Albert Lee Pkwy
Winter Park, FL | Active
Listed: Jul, 27, 2026
Price: $2,600
Living Area: 1,450 Sq. Ft.
Winter Park, FL | Active
Listed: Jul, 27, 2026
Price: $2,600
Living Area: 1,450 Sq. Ft.
1546 Miller Ave
Winter Park, FL | Hold
Listed: Jul, 24, 2026
Price: $1,419,900
Living Area: 2,984 Sq. Ft.
Winter Park, FL | Hold
Listed: Jul, 24, 2026
Price: $1,419,900
Living Area: 2,984 Sq. Ft.
660 Osceola Ave #101
Winter Park, FL | Active
Listed: Sep, 07, 2026
Price: $8,900
Living Area: 2,714 Sq. Ft.
Winter Park, FL | Active
Listed: Sep, 07, 2026
Price: $8,900
Living Area: 2,714 Sq. Ft.
1500 Gay Rd #20d
Winter Park, FL | Active Under Contract
Listed: Feb, 25, 2026
Price: $245,000
Living Area: 1,026 Sq. Ft.
Winter Park, FL | Active Under Contract
Listed: Feb, 25, 2026
Price: $245,000
Living Area: 1,026 Sq. Ft.
857 Brock St
Winter Park, FL | Active
Listed: Aug, 10, 2026
Price: $4,350,000
Living Area: 4,827 Sq. Ft.
Winter Park, FL | Active
Listed: Aug, 10, 2026
Price: $4,350,000
Living Area: 4,827 Sq. Ft.
408 Holt Ave
Winter Park, FL | Active
Listed: May, 08, 2026
Price: $745,000
Living Area: 1,440 Sq. Ft.
Winter Park, FL | Active
Listed: May, 08, 2026
Price: $745,000
Living Area: 1,440 Sq. Ft.
2500 Lee Rd #123
Winter Park, FL | Active
Listed: Oct, 01, 2026
Price: $169,900
Living Area: 645 Sq. Ft.
Winter Park, FL | Active
Listed: Oct, 01, 2026
Price: $169,900
Living Area: 645 Sq. Ft.
1061 Aragon Ave #1061
Winter Park, FL | Active
Listed: Jul, 30, 2026
Price: $510,000
Living Area: 1,669 Sq. Ft.
Winter Park, FL | Active
Listed: Jul, 30, 2026
Price: $510,000
Living Area: 1,669 Sq. Ft.
250 W Reading Way
Winter Park, FL | Active
Listed: Sep, 13, 2026
Price: $4,325,000
Living Area: 4,853 Sq. Ft.
Winter Park, FL | Active
Listed: Sep, 13, 2026
Price: $4,325,000
Living Area: 4,853 Sq. Ft.
1256 Melissa Ct
Winter Park, FL | Active
Listed: Aug, 17, 2026
Price: $660,000
Living Area: 1,690 Sq. Ft.
Winter Park, FL | Active
Listed: Aug, 17, 2026
Price: $660,000
Living Area: 1,690 Sq. Ft.
913 Moss Ln
Winter Park, FL | Active
Listed: Sep, 15, 2026
Price: $950,000
Living Area: 1,887 Sq. Ft.
Winter Park, FL | Active
Listed: Sep, 15, 2026
Price: $950,000
Living Area: 1,887 Sq. Ft.
1695 Lee Rd #a101
Winter Park, FL | Active
Listed: Jun, 24, 2026
Price: $1,575
Living Area: 1,149 Sq. Ft.
Winter Park, FL | Active
Listed: Jun, 24, 2026
Price: $1,575
Living Area: 1,149 Sq. Ft.
1742 Temple Dr
Winter Park, FL | Active
Listed: Sep, 20, 2026
Price: $3,695,999
Living Area: 3,658 Sq. Ft.
Winter Park, FL | Active
Listed: Sep, 20, 2026
Price: $3,695,999
Living Area: 3,658 Sq. Ft.
1220 Howell Branch Rd
Winter Park, FL | Active
Listed: Aug, 26, 2026
Price: $999,500
Living Area: 1,487 Sq. Ft.
Winter Park, FL | Active
Listed: Aug, 26, 2026
Price: $999,500
Living Area: 1,487 Sq. Ft.
2702 Parkland Dr
Winter Park, FL | Active
Listed: Apr, 10, 2026
Price: $1,049,000
Living Area: 2,656 Sq. Ft.
Winter Park, FL | Active
Listed: Apr, 10, 2026
Price: $1,049,000
Living Area: 2,656 Sq. Ft.
2260 Mulbry Dr
Winter Park, FL | Active
Listed: Sep, 11, 2026
Price: $1,925,000
Living Area: 3,246 Sq. Ft.
Winter Park, FL | Active
Listed: Sep, 11, 2026
Price: $1,925,000
Living Area: 3,246 Sq. Ft.
786 W Canton Ave
Winter Park, FL | Active
Listed: Sep, 15, 2026
Price: $450,000
Living Area: 0 Sq. Ft.
Winter Park, FL | Active
Listed: Sep, 15, 2026
Price: $450,000
Living Area: 0 Sq. Ft.
662 Granville Drive
Winter Park, FL | Active
Listed: Sep, 18, 2026
Price: $3,495,000
Living Area: 4,478 Sq. Ft.
Winter Park, FL | Active
Listed: Sep, 18, 2026
Price: $3,495,000
Living Area: 4,478 Sq. Ft.
2417 Chantilly Ave
Winter Park, FL | Active
Listed: Sep, 16, 2026
Price: $1,579,000
Living Area: 2,718 Sq. Ft.
Winter Park, FL | Active
Listed: Sep, 16, 2026
Price: $1,579,000
Living Area: 2,718 Sq. Ft.
447 N Phelps Ave
Winter Park, FL | Active
Listed: Sep, 13, 2026
Price: $960,000
Living Area: 0 Sq. Ft.
Winter Park, FL | Active
Listed: Sep, 13, 2026
Price: $960,000
Living Area: 0 Sq. Ft.
2183 Crandon Ave
Winter Park, FL | Active
Listed: Aug, 14, 2026
Price: $489,000
Living Area: 1,200 Sq. Ft.
Winter Park, FL | Active
Listed: Aug, 14, 2026
Price: $489,000
Living Area: 1,200 Sq. Ft.
2228 Azalea Pl
Winter Park, FL | Active
Listed: Jun, 12, 2026
Price: $5,600,000
Living Area: 5,152 Sq. Ft.
Winter Park, FL | Active
Listed: Jun, 12, 2026
Price: $5,600,000
Living Area: 5,152 Sq. Ft.
800 W Canton Ave
Winter Park, FL | Active
Listed: Sep, 23, 2026
Price: $2,500
Living Area: 924 Sq. Ft.
Winter Park, FL | Active
Listed: Sep, 23, 2026
Price: $2,500
Living Area: 924 Sq. Ft.
432 W Swoope Ave
Winter Park, FL | Active
Listed: Jan, 16, 2026
Price: $680,000
Living Area: 2,664 Sq. Ft.
Winter Park, FL | Active
Listed: Jan, 16, 2026
Price: $680,000
Living Area: 2,664 Sq. Ft.
157 E New England Ave #302
Winter Park, FL | Active
Listed: May, 08, 2026
Price: $425,000
Living Area: 940 Sq. Ft.
Winter Park, FL | Active
Listed: May, 08, 2026
Price: $425,000
Living Area: 940 Sq. Ft.
1113 Via Del Mar
Winter Park, FL | Active
Listed: Feb, 04, 2026
Price: $1,595,000
Living Area: 2,012 Sq. Ft.
Winter Park, FL | Active
Listed: Feb, 04, 2026
Price: $1,595,000
Living Area: 2,012 Sq. Ft.
250 Killarney
Winter Park, FL | Active
Listed: Jul, 07, 2026
Price: $1,600,000
Living Area: 2,568 Sq. Ft.
Winter Park, FL | Active
Listed: Jul, 07, 2026
Price: $1,600,000
Living Area: 2,568 Sq. Ft.
901 Harmon Ave
Winter Park, FL | Active
Listed: Jul, 15, 2026
Price: $650,000
Living Area: 1,277 Sq. Ft.
Winter Park, FL | Active
Listed: Jul, 15, 2026
Price: $650,000
Living Area: 1,277 Sq. Ft.
1368 Hibiscus Ave
Winter Park, FL | Active
Listed: Jul, 29, 2026
Price: $7,250
Living Area: 2,394 Sq. Ft.
Winter Park, FL | Active
Listed: Jul, 29, 2026
Price: $7,250
Living Area: 2,394 Sq. Ft.
1881 Lake Spier Dr
Winter Park, FL | Active
Listed: Apr, 06, 2026
Price: $1,350,000
Living Area: 1,750 Sq. Ft.
Winter Park, FL | Active
Listed: Apr, 06, 2026
Price: $1,350,000
Living Area: 1,750 Sq. Ft.
1881 Lake Spier Dr
Winter Park, FL | Active
Listed: Apr, 07, 2026
Price: $1,350,000
Living Area: 0 Sq. Ft.
Winter Park, FL | Active
Listed: Apr, 07, 2026
Price: $1,350,000
Living Area: 0 Sq. Ft.
437 N Capen Ave
Winter Park, FL | Active
Listed: Jun, 11, 2026
Price: $849,000
Living Area: 1,904 Sq. Ft.
Winter Park, FL | Active
Listed: Jun, 11, 2026
Price: $849,000
Living Area: 1,904 Sq. Ft.
1278 S Pennsylvania Ave #13
Winter Park, FL | Active
Listed: Jun, 17, 2026
Price: $799,000
Living Area: 1,957 Sq. Ft.
Winter Park, FL | Active
Listed: Jun, 17, 2026
Price: $799,000
Living Area: 1,957 Sq. Ft.
1107 S Pennsylvania Ave
Winter Park, FL | Active
Listed: Sep, 09, 2026
Price: $1,800
Living Area: 737 Sq. Ft.
Winter Park, FL | Active
Listed: Sep, 09, 2026
Price: $1,800
Living Area: 737 Sq. Ft.
350 N Phelps Ave
Winter Park, FL | Active
Listed: Sep, 08, 2026
Price: $4,677
Living Area: 2,267 Sq. Ft.
Winter Park, FL | Active
Listed: Sep, 08, 2026
Price: $4,677
Living Area: 2,267 Sq. Ft.
2661 Via Tuscany
Winter Park, FL | Active
Listed: Sep, 09, 2026
Price: $5,999,990
Living Area: 3,880 Sq. Ft.
Winter Park, FL | Active
Listed: Sep, 09, 2026
Price: $5,999,990
Living Area: 3,880 Sq. Ft.
1442 Palm Ave
Winter Park, FL | Active
Listed: Jul, 27, 2026
Price: $9,900
Living Area: 2,735 Sq. Ft.
Winter Park, FL | Active
Listed: Jul, 27, 2026
Price: $9,900
Living Area: 2,735 Sq. Ft.
2612 Roxbury Rd
Winter Park, FL | Active
Listed: Dec, 08, 2025
Price: $629,900
Living Area: 2,472 Sq. Ft.
Winter Park, FL | Active
Listed: Dec, 08, 2025
Price: $629,900
Living Area: 2,472 Sq. Ft.
1562 Arbor Park Dr
Winter Park, FL | Active
Listed: Jul, 16, 2026
Price: $775,000
Living Area: 1,899 Sq. Ft.
Winter Park, FL | Active
Listed: Jul, 16, 2026
Price: $775,000
Living Area: 1,899 Sq. Ft.
1695 Lee Rd #c103
Winter Park, FL | Active
Listed: Jul, 13, 2026
Price: $1,600
Living Area: 881 Sq. Ft.
Winter Park, FL | Active
Listed: Jul, 13, 2026
Price: $1,600
Living Area: 881 Sq. Ft.
276 Detmar Dr
Winter Park, FL | Active
Listed: Aug, 24, 2026
Price: $3,600,000
Living Area: 4,202 Sq. Ft.
Winter Park, FL | Active
Listed: Aug, 24, 2026
Price: $3,600,000
Living Area: 4,202 Sq. Ft.
1751 Goodrich Ave
Winter Park, FL | Active
Listed: Jan, 29, 2026
Price: $1,380,000
Living Area: 2,170 Sq. Ft.
Winter Park, FL | Active
Listed: Jan, 29, 2026
Price: $1,380,000
Living Area: 2,170 Sq. Ft.
2041 Jewell Ave
Winter Park, FL | Active
Listed: Jun, 28, 2026
Price: $439,900
Living Area: 1,508 Sq. Ft.
Winter Park, FL | Active
Listed: Jun, 28, 2026
Price: $439,900
Living Area: 1,508 Sq. Ft.
301 W Comstock Ave
Winter Park, FL | Active
Listed: Feb, 25, 2026
Price: $6,000
Living Area: 1,500 Sq. Ft.
Winter Park, FL | Active
Listed: Feb, 25, 2026
Price: $6,000
Living Area: 1,500 Sq. Ft.
540 N Pennsylvania Ave
Winter Park, FL | Active
Listed: Aug, 06, 2026
Price: $3,950,000
Living Area: 0 Sq. Ft.
Winter Park, FL | Active
Listed: Aug, 06, 2026
Price: $3,950,000
Living Area: 0 Sq. Ft.
151 N Orlando Ave #207
Winter Park, FL | Active
Listed: Jul, 14, 2026
Price: $2,150
Living Area: 710 Sq. Ft.
Winter Park, FL | Active
Listed: Jul, 14, 2026
Price: $2,150
Living Area: 710 Sq. Ft.
301 S Capen Ave
Winter Park, FL | Active
Listed: Jun, 26, 2026
Price: $2,200
Living Area: 1,158 Sq. Ft.
Winter Park, FL | Active
Listed: Jun, 26, 2026
Price: $2,200
Living Area: 1,158 Sq. Ft.
1136 S Pennsylvania Ave
Winter Park, FL | Active
Listed: Aug, 02, 2026
Price: $5,600
Living Area: 2,434 Sq. Ft.
Winter Park, FL | Active
Listed: Aug, 02, 2026
Price: $5,600
Living Area: 2,434 Sq. Ft.
150 E Reading Way
Winter Park, FL | Active
Listed: Aug, 12, 2026
Price: $1,449,000
Living Area: 0 Sq. Ft.
Winter Park, FL | Active
Listed: Aug, 12, 2026
Price: $1,449,000
Living Area: 0 Sq. Ft.
2667 Cochise Trl
Winter Park, FL | Active
Listed: Aug, 03, 2026
Price: $985,000
Living Area: 2,868 Sq. Ft.
Winter Park, FL | Active
Listed: Aug, 03, 2026
Price: $985,000
Living Area: 2,868 Sq. Ft.
150 E Reading Way
Winter Park, FL | Active
Listed: Aug, 23, 2026
Price: $1,449,000
Living Area: 2,080 Sq. Ft.
Winter Park, FL | Active
Listed: Aug, 23, 2026
Price: $1,449,000
Living Area: 2,080 Sq. Ft.
1261 Indiana Ave
Winter Park, FL | Pending
Listed: Apr, 20, 2026
Price: $540,000
Living Area: 1,660 Sq. Ft.
Winter Park, FL | Pending
Listed: Apr, 20, 2026
Price: $540,000
Living Area: 1,660 Sq. Ft.
2803 Riddle Dr
Winter Park, FL | Active Under Contract
Listed: Jul, 09, 2026
Price: $525,000
Living Area: 1,709 Sq. Ft.
Winter Park, FL | Active Under Contract
Listed: Jul, 09, 2026
Price: $525,000
Living Area: 1,709 Sq. Ft.
1530 Alabama Dr
Winter Park, FL | Active Under Contract
Listed: Sep, 20, 2026
Price: $5,900,000
Living Area: 3,680 Sq. Ft.
Winter Park, FL | Active Under Contract
Listed: Sep, 20, 2026
Price: $5,900,000
Living Area: 3,680 Sq. Ft.
2157 Lake Dr
Winter Park, FL | Active Under Contract
Listed: May, 30, 2026
Price: $689,000
Living Area: 2,124 Sq. Ft.
Winter Park, FL | Active Under Contract
Listed: May, 30, 2026
Price: $689,000
Living Area: 2,124 Sq. Ft.
2418 Euston Rd
Winter Park, FL | Active
Listed: May, 21, 2026
Price: $624,444
Living Area: 2,228 Sq. Ft.
Winter Park, FL | Active
Listed: May, 21, 2026
Price: $624,444
Living Area: 2,228 Sq. Ft.
2403 Euston Rd
Winter Park, FL | Active
Listed: Aug, 24, 2026
Price: $4,299,000
Living Area: 0 Sq. Ft.
Winter Park, FL | Active
Listed: Aug, 24, 2026
Price: $4,299,000
Living Area: 0 Sq. Ft.
1500 Gay Rd #3c
Winter Park, FL | Active
Listed: Jun, 18, 2026
Price: $235,000
Living Area: 1,026 Sq. Ft.
Winter Park, FL | Active
Listed: Jun, 18, 2026
Price: $235,000
Living Area: 1,026 Sq. Ft.
300 Carolina Ave #402c
Winter Park, FL | Active
Listed: May, 22, 2026
Price: $710,000
Living Area: 1,350 Sq. Ft.
Winter Park, FL | Active
Listed: May, 22, 2026
Price: $710,000
Living Area: 1,350 Sq. Ft.
759 Antonette Ave
Winter Park, FL | Active
Listed: Sep, 07, 2026
Price: $1,800
Living Area: 705 Sq. Ft.
Winter Park, FL | Active
Listed: Sep, 07, 2026
Price: $1,800
Living Area: 705 Sq. Ft.
1618 Indiana Ave
Winter Park, FL | Active
Listed: Aug, 17, 2026
Price: $1,800
Living Area: 1,604 Sq. Ft.
Winter Park, FL | Active
Listed: Aug, 17, 2026
Price: $1,800
Living Area: 1,604 Sq. Ft.
1477 W Fairbanks Ave
Winter Park, FL | Active
Listed: Jul, 09, 2026
Price: $2,500,000
Living Area: 6,049 Sq. Ft.
Winter Park, FL | Active
Listed: Jul, 09, 2026
Price: $2,500,000
Living Area: 6,049 Sq. Ft.
687 Harold Ave
Winter Park, FL | Active
Listed: Mar, 04, 2026
Price: $84,000
Living Area: 4,500 Sq. Ft.
Winter Park, FL | Active
Listed: Mar, 04, 2026
Price: $84,000
Living Area: 4,500 Sq. Ft.
250 Carolina Ave #205
Winter Park, FL | Active
Listed: Aug, 15, 2026
Price: $739,000
Living Area: 1,311 Sq. Ft.
Winter Park, FL | Active
Listed: Aug, 15, 2026
Price: $739,000
Living Area: 1,311 Sq. Ft.
2525 Temple Dr
Winter Park, FL | Active Under Contract
Listed: Jul, 27, 2026
Price: $4,750,000
Living Area: 4,542 Sq. Ft.
Winter Park, FL | Active Under Contract
Listed: Jul, 27, 2026
Price: $4,750,000
Living Area: 4,542 Sq. Ft.
770 W Webster Ave
Winter Park, FL | Active Under Contract
Listed: Jul, 03, 2025
Price: $725,000
Living Area: 1,008 Sq. Ft.
Winter Park, FL | Active Under Contract
Listed: Jul, 03, 2025
Price: $725,000
Living Area: 1,008 Sq. Ft.
632 Country Club Dr
Winter Park, FL | Pending
Listed: Oct, 19, 2024
Price: $1,050,000
Living Area: 2,342 Sq. Ft.
Winter Park, FL | Pending
Listed: Oct, 19, 2024
Price: $1,050,000
Living Area: 2,342 Sq. Ft.
1049 N Kentucky Ave
Winter Park, FL | Pending
Listed: Jan, 12, 2026
Price: $6,000
Living Area: 2,112 Sq. Ft.
Winter Park, FL | Pending
Listed: Jan, 12, 2026
Price: $6,000
Living Area: 2,112 Sq. Ft.
1409 Sunset Dr
Winter Park, FL | Active Under Contract
Listed: Aug, 14, 2026
Price: $649,000
Living Area: 1,107 Sq. Ft.
Winter Park, FL | Active Under Contract
Listed: Aug, 14, 2026
Price: $649,000
Living Area: 1,107 Sq. Ft.
1230 Sunset Dr
Winter Park, FL | Active Under Contract
Listed: Aug, 07, 2026
Price: $1,795,000
Living Area: 3,250 Sq. Ft.
Winter Park, FL | Active Under Contract
Listed: Aug, 07, 2026
Price: $1,795,000
Living Area: 3,250 Sq. Ft.
393 Holt Ave
Winter Park, FL | Active Under Contract
Listed: Aug, 31, 2026
Price: $1,050,000
Living Area: 1,469 Sq. Ft.
Winter Park, FL | Active Under Contract
Listed: Aug, 31, 2026
Price: $1,050,000
Living Area: 1,469 Sq. Ft.
1200 Woodmere Dr
Winter Park, FL | Active Under Contract
Listed: Sep, 03, 2026
Price: $1,649,000
Living Area: 2,857 Sq. Ft.
Winter Park, FL | Active Under Contract
Listed: Sep, 03, 2026
Price: $1,649,000
Living Area: 2,857 Sq. Ft.
1150 Via Salerno
Winter Park, FL | Active Under Contract
Listed: Jun, 28, 2025
Price: $3,750,000
Living Area: 3,826 Sq. Ft.
Winter Park, FL | Active Under Contract
Listed: Jun, 28, 2025
Price: $3,750,000
Living Area: 3,826 Sq. Ft.
2500 Lee Rd #220
Winter Park, FL | Active
Listed: May, 27, 2026
Price: $199,900
Living Area: 851 Sq. Ft.
Winter Park, FL | Active
Listed: May, 27, 2026
Price: $199,900
Living Area: 851 Sq. Ft.
281 Brewer Ave
Winter Park, FL | Active
Listed: Jul, 13, 2026
Price: $1,800,000
Living Area: 4,029 Sq. Ft.
Winter Park, FL | Active
Listed: Jul, 13, 2026
Price: $1,800,000
Living Area: 4,029 Sq. Ft.
1695 Lee Rd #c202
Winter Park, FL | Active
Listed: Feb, 26, 2025
Price: $205,000
Living Area: 1,149 Sq. Ft.
Winter Park, FL | Active
Listed: Feb, 26, 2025
Price: $205,000
Living Area: 1,149 Sq. Ft.
690 Osceola Ave #407
Winter Park, FL | Active
Listed: Oct, 02, 2026
Price: $2,200
Living Area: 915 Sq. Ft.
Winter Park, FL | Active
Listed: Oct, 02, 2026
Price: $2,200
Living Area: 915 Sq. Ft.
1602 Alabama Dr #107
Winter Park, FL | Coming Soon
Listed: Sep, 22, 2026
Price: $1,150,000
Living Area: 993 Sq. Ft.
Winter Park, FL | Coming Soon
Listed: Sep, 22, 2026
Price: $1,150,000
Living Area: 993 Sq. Ft.
1695 Lee Rd #e215
Winter Park, FL | Active
Listed: Aug, 18, 2026
Price: $1,850
Living Area: 1,149 Sq. Ft.
Winter Park, FL | Active
Listed: Aug, 18, 2026
Price: $1,850
Living Area: 1,149 Sq. Ft.
1016 tuscany place
Winter Park, FL | Closed
Listed: Feb, 12, 2024
Price: $1,595,000
Living Area: 3,300 Sq. Ft.
Winter Park, FL | Closed
Listed: Feb, 12, 2024
Price: $1,595,000
Living Area: 3,300 Sq. Ft.
413 W Morse Blvd
Winter Park, FL | Active
Listed: Jun, 06, 2026
Price: $2,625,000
Living Area: 3,048 Sq. Ft.
Winter Park, FL | Active
Listed: Jun, 06, 2026
Price: $2,625,000
Living Area: 3,048 Sq. Ft.
532 Langholm Dr
Winter Park, FL | Active
Listed: Sep, 23, 2026
Price: $2,990,000
Living Area: 4,050 Sq. Ft.
Winter Park, FL | Active
Listed: Sep, 23, 2026
Price: $2,990,000
Living Area: 4,050 Sq. Ft.
338 Blue Heron Dr
Winter Park, FL | Active
Listed: May, 23, 2026
Price: $836,000
Living Area: 2,017 Sq. Ft.
Winter Park, FL | Active
Listed: May, 23, 2026
Price: $836,000
Living Area: 2,017 Sq. Ft.
1660 Orange Ave
Winter Park, FL | Active
Listed: Sep, 24, 2026
Price: $479,900
Living Area: 1,614 Sq. Ft.
Winter Park, FL | Active
Listed: Sep, 24, 2026
Price: $479,900
Living Area: 1,614 Sq. Ft.
120 Broadview Ave
Winter Park, FL | Active
Listed: Sep, 22, 2026
Price: $1,250,000
Living Area: 1,747 Sq. Ft.
Winter Park, FL | Active
Listed: Sep, 22, 2026
Price: $1,250,000
Living Area: 1,747 Sq. Ft.
1138 S Pennsylvania Ave
Winter Park, FL | Active
Listed: Jun, 25, 2026
Price: $925,000
Living Area: 2,434 Sq. Ft.
Winter Park, FL | Active
Listed: Jun, 25, 2026
Price: $925,000
Living Area: 2,434 Sq. Ft.
712 Baffie Ave
Winter Park, FL | Active
Listed: Sep, 29, 2026
Price: $448,000
Living Area: 1,304 Sq. Ft.
Winter Park, FL | Active
Listed: Sep, 29, 2026
Price: $448,000
Living Area: 1,304 Sq. Ft.
7 Carver Ct
Winter Park, FL | Closed
Listed: Sep, 08, 2026
Price: $589,000
Living Area: 1,384 Sq. Ft.
Winter Park, FL | Closed
Listed: Sep, 08, 2026
Price: $589,000
Living Area: 1,384 Sq. Ft.
1741 Westchester Ave
Winter Park, FL | Active Under Contract
Listed: Apr, 16, 2026
Price: $529,000
Living Area: 1,434 Sq. Ft.
Winter Park, FL | Active Under Contract
Listed: Apr, 16, 2026
Price: $529,000
Living Area: 1,434 Sq. Ft.
1795 Killarney Drive
Winter Park, FL | Closed
Listed: Jan, 10, 2023
Price: $3,700,000
Living Area: 4,363 Sq. Ft.
Winter Park, FL | Closed
Listed: Jan, 10, 2023
Price: $3,700,000
Living Area: 4,363 Sq. Ft.
2607 Lafayette Avenue
Winter Park, FL | Closed
Listed: Jun, 26, 2025
Price: $1,095,000
Living Area: 2,770 Sq. Ft.
Winter Park, FL | Closed
Listed: Jun, 26, 2025
Price: $1,095,000
Living Area: 2,770 Sq. Ft.
240 E Lake Sue Avenue
Winter Park, FL | Closed
Listed: Nov, 20, 2025
Price: $1,107,750
Living Area: 1,329 Sq. Ft.
Winter Park, FL | Closed
Listed: Nov, 20, 2025
Price: $1,107,750
Living Area: 1,329 Sq. Ft.
1451 Cavendish Road
Winter Park, FL | Closed
Listed: Oct, 30, 2025
Price: $619,500
Living Area: 1,437 Sq. Ft.
Winter Park, FL | Closed
Listed: Oct, 30, 2025
Price: $619,500
Living Area: 1,437 Sq. Ft.
405 Lake Fair Lane
Winter Park, FL | Withdrawn
Listed: Jul, 29, 2026
Price: $434,990
Living Area: 0 Sq. Ft.
Winter Park, FL | Withdrawn
Listed: Jul, 29, 2026
Price: $434,990
Living Area: 0 Sq. Ft.
2211 Azalea Pl
Winter Park, FL | Withdrawn
Listed: Jun, 26, 2025
Price: $5,250,000
Living Area: 7,278 Sq. Ft.
Winter Park, FL | Withdrawn
Listed: Jun, 26, 2025
Price: $5,250,000
Living Area: 7,278 Sq. Ft.
1707 Harmon Ave
Winter Park, FL | Canceled
Listed: May, 19, 2026
Price: $599,000
Living Area: 1,669 Sq. Ft.
Winter Park, FL | Canceled
Listed: May, 19, 2026
Price: $599,000
Living Area: 1,669 Sq. Ft.
311 E Morse Blvd #6-12
Winter Park, FL | Active Under Contract
Listed: Jun, 03, 2026
Price: $275,000
Living Area: 570 Sq. Ft.
Winter Park, FL | Active Under Contract
Listed: Jun, 03, 2026
Price: $275,000
Living Area: 570 Sq. Ft.
700 Melrose Ave #j24
Winter Park, FL | Active
Listed: May, 22, 2026
Price: $350,000
Living Area: 987 Sq. Ft.
Winter Park, FL | Active
Listed: May, 22, 2026
Price: $350,000
Living Area: 987 Sq. Ft.
1751 Westchester Ave
Winter Park, FL | Active
Listed: Aug, 12, 2026
Price: $2,200
Living Area: 1,068 Sq. Ft.
Winter Park, FL | Active
Listed: Aug, 12, 2026
Price: $2,200
Living Area: 1,068 Sq. Ft.
1319 Bessmor Rd
Winter Park, FL | Hold
Listed: Apr, 17, 2026
Price: $589,000
Living Area: 1,126 Sq. Ft.
Winter Park, FL | Hold
Listed: Apr, 17, 2026
Price: $589,000
Living Area: 1,126 Sq. Ft.
151 N Orlando Ave #242
Winter Park, FL | Active
Listed: Aug, 28, 2026
Price: $269,000
Living Area: 710 Sq. Ft.
Winter Park, FL | Active
Listed: Aug, 28, 2026
Price: $269,000
Living Area: 710 Sq. Ft.
1250 S Denning Dr #119
Winter Park, FL | Active
Listed: Sep, 25, 2026
Price: $265,000
Living Area: 908 Sq. Ft.
Winter Park, FL | Active
Listed: Sep, 25, 2026
Price: $265,000
Living Area: 908 Sq. Ft.
555 E Lake Sue Ave
Winter Park, FL | Active
Listed: Sep, 17, 2026
Price: $2,095,000
Living Area: 3,776 Sq. Ft.
Winter Park, FL | Active
Listed: Sep, 17, 2026
Price: $2,095,000
Living Area: 3,776 Sq. Ft.
720 Pansy Ave
Winter Park, FL | Active
Listed: Aug, 19, 2026
Price: $1,295,000
Living Area: 2,191 Sq. Ft.
Winter Park, FL | Active
Listed: Aug, 19, 2026
Price: $1,295,000
Living Area: 2,191 Sq. Ft.
106 S Interlachen Ave #518
Winter Park, FL | Active Under Contract
Listed: Apr, 21, 2026
Price: $1,795,000
Living Area: 1,807 Sq. Ft.
Winter Park, FL | Active Under Contract
Listed: Apr, 21, 2026
Price: $1,795,000
Living Area: 1,807 Sq. Ft.
1415 Harmon Ave
Winter Park, FL | Canceled
Listed: May, 27, 2026
Price: $3,200
Living Area: 1,700 Sq. Ft.
Winter Park, FL | Canceled
Listed: May, 27, 2026
Price: $3,200
Living Area: 1,700 Sq. Ft.
1009 Lake Bell Dr
Winter Park, FL | Closed
Listed: May, 22, 2026
Price: $650,000
Living Area: 1,467 Sq. Ft.
Winter Park, FL | Closed
Listed: May, 22, 2026
Price: $650,000
Living Area: 1,467 Sq. Ft.
259 Orange Terrace Drive
Winter Park, FL | Active
Listed: Jun, 25, 2026
Price: $449,900
Living Area: 1,248 Sq. Ft.
Winter Park, FL | Active
Listed: Jun, 25, 2026
Price: $449,900
Living Area: 1,248 Sq. Ft.
2333 Westminster Ct
Winter Park, FL | Active Under Contract
Listed: Aug, 20, 2026
Price: $649,900
Living Area: 1,877 Sq. Ft.
Winter Park, FL | Active Under Contract
Listed: Aug, 20, 2026
Price: $649,900
Living Area: 1,877 Sq. Ft.
1773 Walnut Ave
Winter Park, FL | Active
Listed: Sep, 11, 2026
Price: $2,725,000
Living Area: 3,784 Sq. Ft.
Winter Park, FL | Active
Listed: Sep, 11, 2026
Price: $2,725,000
Living Area: 3,784 Sq. Ft.
1517 Harmon Ave
Winter Park, FL | Active
Listed: Sep, 18, 2026
Price: $1,095,000
Living Area: 2,135 Sq. Ft.
Winter Park, FL | Active
Listed: Sep, 18, 2026
Price: $1,095,000
Living Area: 2,135 Sq. Ft.
2227 Howard Dr
Winter Park, FL | Active Under Contract
Listed: Sep, 01, 2026
Price: $1,100,000
Living Area: 2,196 Sq. Ft.
Winter Park, FL | Active Under Contract
Listed: Sep, 01, 2026
Price: $1,100,000
Living Area: 2,196 Sq. Ft.
1695 Lee Rd #d211
Winter Park, FL | Active
Listed: Apr, 08, 2026
Price: $102,500
Living Area: 881 Sq. Ft.
Winter Park, FL | Active
Listed: Apr, 08, 2026
Price: $102,500
Living Area: 881 Sq. Ft.
1256 S Pennsylvania Ave #9
Winter Park, FL | Active
Listed: Sep, 06, 2026
Price: $950,000
Living Area: 1,957 Sq. Ft.
Winter Park, FL | Active
Listed: Sep, 06, 2026
Price: $950,000
Living Area: 1,957 Sq. Ft.
952 Moss Ln
Winter Park, FL | Active Under Contract
Listed: Sep, 10, 2026
Price: $1,319,950
Living Area: 3,474 Sq. Ft.
Winter Park, FL | Active Under Contract
Listed: Sep, 10, 2026
Price: $1,319,950
Living Area: 3,474 Sq. Ft.
1974 Staunton Ave
Winter Park, FL | Closed
Listed: Oct, 01, 2026
Price: $240,000
Living Area: 962 Sq. Ft.
Winter Park, FL | Closed
Listed: Oct, 01, 2026
Price: $240,000
Living Area: 962 Sq. Ft.
1220 Sharon Pl
Winter Park, FL | Closed
Listed: Aug, 24, 2026
Price: $1,800,000
Living Area: 0 Sq. Ft.
Winter Park, FL | Closed
Listed: Aug, 24, 2026
Price: $1,800,000
Living Area: 0 Sq. Ft.
2361 Roxbury Rd
Winter Park, FL | Closed
Listed: Jun, 18, 2026
Price: $599,000
Living Area: 1,723 Sq. Ft.
Winter Park, FL | Closed
Listed: Jun, 18, 2026
Price: $599,000
Living Area: 1,723 Sq. Ft.
1652 Berkshire Ave
Winter Park, FL | Active
Listed: Aug, 13, 2026
Price: $479,000
Living Area: 1,498 Sq. Ft.
Winter Park, FL | Active
Listed: Aug, 13, 2026
Price: $479,000
Living Area: 1,498 Sq. Ft.
1620 Palm Ave
Winter Park, FL | Active
Listed: Sep, 01, 2026
Price: $10,000
Living Area: 3,806 Sq. Ft.
Winter Park, FL | Active
Listed: Sep, 01, 2026
Price: $10,000
Living Area: 3,806 Sq. Ft.
1526 Miller Ave
Winter Park, FL | Active Under Contract
Listed: Aug, 20, 2026
Price: $1,574,900
Living Area: 3,252 Sq. Ft.
Winter Park, FL | Active Under Contract
Listed: Aug, 20, 2026
Price: $1,574,900
Living Area: 3,252 Sq. Ft.
151 N Orlando Ave ##115
Winter Park, FL | Active
Listed: Dec, 01, 2025
Price: $285,000
Living Area: 710 Sq. Ft.
Winter Park, FL | Active
Listed: Dec, 01, 2025
Price: $285,000
Living Area: 710 Sq. Ft.
541 W Canton Ave
Winter Park, FL | Active
Listed: Mar, 14, 2026
Price: $2,495,000
Living Area: 3,553 Sq. Ft.
Winter Park, FL | Active
Listed: Mar, 14, 2026
Price: $2,495,000
Living Area: 3,553 Sq. Ft.
1260 Alabama Dr
Winter Park, FL | Active
Listed: Mar, 03, 2026
Price: $6,900,000
Living Area: 6,396 Sq. Ft.
Winter Park, FL | Active
Listed: Mar, 03, 2026
Price: $6,900,000
Living Area: 6,396 Sq. Ft.
2407 Lafayette Ave
Winter Park, FL | Active
Listed: Aug, 11, 2026
Price: $1,625,000
Living Area: 3,133 Sq. Ft.
Winter Park, FL | Active
Listed: Aug, 11, 2026
Price: $1,625,000
Living Area: 3,133 Sq. Ft.
2614 Parkland Dr
Winter Park, FL | Active
Listed: Sep, 23, 2026
Price: $1,890,000
Living Area: 3,307 Sq. Ft.
Winter Park, FL | Active
Listed: Sep, 23, 2026
Price: $1,890,000
Living Area: 3,307 Sq. Ft.
462 W Lyman Ave
Winter Park, FL | Active
Listed: Jul, 13, 2026
Price: $1,495,000
Living Area: 1,944 Sq. Ft.
Winter Park, FL | Active
Listed: Jul, 13, 2026
Price: $1,495,000
Living Area: 1,944 Sq. Ft.
922 N Pennsylvania Ave
Winter Park, FL | Active
Listed: Jul, 14, 2026
Price: $1,875,000
Living Area: 3,440 Sq. Ft.
Winter Park, FL | Active
Listed: Jul, 14, 2026
Price: $1,875,000
Living Area: 3,440 Sq. Ft.
620 Virginia Dr
Winter Park, FL | Active
Listed: Aug, 13, 2026
Price: $3,890,000
Living Area: 4,677 Sq. Ft.
Winter Park, FL | Active
Listed: Aug, 13, 2026
Price: $3,890,000
Living Area: 4,677 Sq. Ft.
1621 Chestnut Ave
Winter Park, FL | Active
Listed: Aug, 20, 2026
Price: $899,000
Living Area: 2,022 Sq. Ft.
Winter Park, FL | Active
Listed: Aug, 20, 2026
Price: $899,000
Living Area: 2,022 Sq. Ft.
1807 Hammerlin Ave #g
Winter Park, FL | Closed
Listed: Mar, 17, 2026
Price: $499,000
Living Area: 1,818 Sq. Ft.
Winter Park, FL | Closed
Listed: Mar, 17, 2026
Price: $499,000
Living Area: 1,818 Sq. Ft.
1421 Chestnut Ave
Winter Park, FL | Active Under Contract
Listed: Sep, 18, 2026
Price: $750,000
Living Area: 0 Sq. Ft.
Winter Park, FL | Active Under Contract
Listed: Sep, 18, 2026
Price: $750,000
Living Area: 0 Sq. Ft.
