295 Listings
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$11,900,000
Virtual Tour
1120 Preserve Point Dr, Winter Park, FL 32789
11,255 SqFt
7 Beds | 11 Baths

ACTIVE

$10,999,999
Virtual Tour
2660 Via Tuscany, Winter Park, FL 32789
4,564 SqFt
4 Beds | 5 Baths

ACTIVE

$6,950,000
Virtual Tour
1400 Alabama Dr, Winter Park, FL 32789
7,916 SqFt
5 Beds | 9 Baths

ACTIVE

$6,100,000
Virtual Tour
541 Virginia Dr, Winter Park, FL 32789
4,725 SqFt
4 Beds | 4 Baths

ACTIVE

$5,400,000
Virtual Tour
2228 Azalea Pl, Winter Park, FL 32789
5,072 SqFt
5 Beds | 6 Baths

ACTIVE

$4,985,000
2161 Sharon Rd, Winter Park, FL 32789
6,338 SqFt
5 Beds | 7 Baths

ACTIVE

$4,500,000
Virtual Tour
702 Via Bella, Winter Park, FL 32789
3,720 SqFt
5 Beds | 6 Baths

ACTIVE

$4,200,000
Virtual Tour
571 Lake Front Blvd, Winter Park, FL 32789
5,500 SqFt
7 Beds | 5 Baths

ACTIVE

$4,100,000
Virtual Tour
1751 Glencoe Rd, Winter Park, FL 32789
4,520 SqFt
5 Beds | 6 Baths

ACTIVE

$3,892,000
Virtual Tour
1391 Richmond Rd, Winter Park, FL 32789
4,635 SqFt
4 Beds | 6 Baths

ACTIVE

$3,295,000
Virtual Tour
1730 Winchester Dr, Winter Park, FL 32789
4,080 SqFt
5 Beds | 6 Baths

ACTIVE

$3,250,000
Virtual Tour
1900 W Fawsett Rd, Winter Park, FL 32789
4,600 SqFt
4 Beds | 5 Baths

ACTIVE

$2,999,999
2652 Lake Howell Ln, Winter Park, FL 32792
3,898 SqFt
5 Beds | 4 Baths

ACTIVE

$2,999,900
Virtual Tour
2550 Venetian Way, Winter Park, FL 32789
4,875 SqFt
4 Beds | 5 Baths

ACTIVE

$2,995,000
Virtual Tour
1400 Place Picardy, Winter Park, FL 32789
4,411 SqFt
5 Beds | 6 Baths

ACTIVE

$2,890,000
Virtual Tour
140 E Morse Blvd J, Winter Park, FL 32789
2,143 SqFt
3 Beds | 3 Baths

ACTIVE

$2,495,000
Virtual Tour
147 S Interlachen Ave Unit 400, Winter Park, FL 32789
5,159 SqFt
4 Beds | 5 Baths

ACTIVE

$2,399,000
Virtual Tour
2522 Lafayette Ave, Winter Park, FL 32789
3,399 SqFt
4 Beds | 4 Baths

ACTIVE

$2,395,000
Virtual Tour
2412 Chantilly Ave, Winter Park, FL 32789
4,506 SqFt
5 Beds | 7 Baths

ACTIVE

$2,279,000
Virtual Tour
141 Oakwood Way, Winter Park, FL 32789
3,909 SqFt
5 Beds | 4 Baths

ACTIVE

$2,190,000
Virtual Tour
2234 Via Luna, Winter Park, FL 32789
3,554 SqFt
6 Beds | 4 Baths

ACTIVE

$2,119,000
Virtual Tour
785 N Phelps Ave, Winter Park, FL 32789
2,964 SqFt
5 Beds | 5 Baths

ACTIVE

$2,100,000
140 Dana Way, Winter Park, FL 32789
3,441 SqFt
3 Beds | 3 Baths

ACTIVE

$2,000,000
2260 Mulbry Dr, Winter Park, FL 32789
3,246 SqFt
5 Beds | 4 Baths

ACTIVE

$1,999,993
Virtual Tour
1451 Lyndale Blvd, Winter Park, FL 32789
3,853 SqFt
6 Beds | 4 Baths

ACTIVE

$1,995,000
Virtual Tour
817 Antonette Ave, Winter Park, FL 32789
3,971 SqFt
4 Beds | 3 Baths

ACTIVE

$1,977,000
Virtual Tour
1340 Chestnut Ave, Winter Park, FL 32789
4,182 SqFt
6 Beds | 6 Baths

ACTIVE

$1,950,000
Virtual Tour
622 Penn Pl, Winter Park, FL 32789
2,767 SqFt
3 Beds | 4 Baths

ACTIVE

$1,950,000
Virtual Tour
1470 Place Picardy, Winter Park, FL 32789
4,227 SqFt
5 Beds | 6 Baths

ACTIVE

$1,795,000
Virtual Tour
279 Rippling Ln, Winter Park, FL 32789
3,472 SqFt
4 Beds | 3 Baths

ACTIVE

$1,759,000
1660 Walnut Ave, Winter Park, FL 32789
2,172 SqFt
4 Beds | 4 Baths

ACTIVE

$1,750,000
Virtual Tour
1350 Lyndale Blvd, Winter Park, FL 32789
3,478 SqFt
4 Beds | 5 Baths

ACTIVE

$1,695,000
Virtual Tour
101 S New York Ave Unit 302, Winter Park, FL 32789
3,174 SqFt
3 Beds | 4 Baths

ACTIVE

$1,675,000
607 Ellen Dr, Winter Park, FL 32789
2,812 SqFt
4 Beds | 5 Baths

ACTIVE

$1,674,999
Virtual Tour
1429 Chapman Cir, Winter Park, FL 32789
3,116 SqFt
4 Beds | 4 Baths

ACTIVE

$1,625,000
Virtual Tour
1650 Lakehurst Ave, Winter Park, FL 32789
3,777 SqFt
4 Beds | 4 Baths

ACTIVE

$1,599,900
1417 Miller Ave, Winter Park, FL 32789
3,312 SqFt
5 Beds | 4 Baths

ACTIVE

$1,595,000
335 Beloit Ave, Winter Park, FL 32789
2,420 SqFt
3 Beds | 2 Baths

ACTIVE

$1,500,000
Virtual Tour
2015 Summerfield Rd, Winter Park, FL 32792
2,958 SqFt
4 Beds | 4 Baths

ACTIVE

$1,495,000
Virtual Tour
1371 Lyndale Blvd, Winter Park, FL 32789
2,739 SqFt
4 Beds | 3 Baths

ACTIVE

$1,470,000
Virtual Tour
840 W Comstock Ave, Winter Park, FL 32789
2,350 SqFt
4 Beds | 4 Baths

ACTIVE

$1,450,000
Virtual Tour
777 Halifax Ave, Winter Park, FL 32792
3,161 SqFt
5 Beds | 5 Baths

ACTIVE

$1,395,000
Virtual Tour
433 Carolina Ave, Winter Park, FL 32789
2,700 SqFt
5 Beds | 4 Baths

ACTIVE

$1,380,000
Virtual Tour
1400 S Pennsylvania Ave, Winter Park, FL 32789
2,060 SqFt
4 Beds | 3 Baths

ACTIVE

$1,350,000
Virtual Tour
632 Country Club Dr, Winter Park, FL 32789
2,342 SqFt
3 Beds | 2 Baths

ACTIVE

$1,350,000
Virtual Tour
858 Douglas Ave, Winter Park, FL 32789
2,334 SqFt
4 Beds | 4 Baths

ACTIVE

$1,299,990
Virtual Tour
2258 E Howard Dr, Winter Park, FL 32789
2,747 SqFt
4 Beds | 3 Baths

ACTIVE

$1,299,000
Virtual Tour
7440 Aloma Ave, Winter Park, FL 32792
4,435 SqFt
5 Beds | 5 Baths

ACTIVE

$1,295,000
Virtual Tour
1932 Temple Dr, Winter Park, FL 32789
2,432 SqFt
3 Beds | 3 Baths

ACTIVE

$1,295,000
Virtual Tour
1611 Walnut Ave, Winter Park, FL 32789
2,635 SqFt
4 Beds | 3 Baths

ACTIVE

$1,295,000
1611 Chestnut Ave, Winter Park, FL 32789
2,916 SqFt
4 Beds | 4 Baths

ACTIVE

$1,250,000
Virtual Tour
567 Osceola Ave, Winter Park, FL 32789
2,651 SqFt
4 Beds | 4 Baths

ACTIVE

$1,250,000
Virtual Tour
1778 Mondrian Cir, Winter Park, FL 32789
2,377 SqFt
3 Beds | 4 Baths

ACTIVE

$1,195,000
Virtual Tour
1690 Oneco Ave, Winter Park, FL 32789
2,703 SqFt
4 Beds | 3 Baths

ACTIVE

$1,150,000
Virtual Tour
708 Balmoral Rd, Winter Park, FL 32789
2,786 SqFt
4 Beds | 3 Baths

ACTIVE

$1,149,000
Virtual Tour
1840 Biscayne Dr, Winter Park, FL 32789
2,641 SqFt
5 Beds | 3 Baths

ACTIVE

$1,125,000
Virtual Tour
1975 Biscayne Dr, Winter Park, FL 32789
3,270 SqFt
5 Beds | 4 Baths

ACTIVE

$1,100,000
2330 Westminster Ct, Winter Park, FL 32789
3,296 SqFt
5 Beds | 3 Baths

ACTIVE

$1,069,000
Virtual Tour
1001 Tuscany Pl, Winter Park, FL 32789
2,458 SqFt
3 Beds | 2 Baths

ACTIVE

$995,000
Virtual Tour
2260 Hawick Ln, Winter Park, FL 32792
1,374 SqFt
2 Beds | 2 Baths

ACTIVE

$995,000
870 Carver St, Winter Park, FL 32789
1,844 SqFt
3 Beds | 4 Baths

ACTIVE

$975,000
Virtual Tour
1760 Mondrian Cir, Winter Park, FL 32789
2,245 SqFt
3 Beds | 4 Baths

ACTIVE

$949,900
Virtual Tour
533 Balmoral Rd, Winter Park, FL 32789
1,900 SqFt
3 Beds | 3 Baths

ACTIVE

$930,000
Virtual Tour
675 Overspin Dr, Winter Park, FL 32789
2,962 SqFt
4 Beds | 4 Baths

ACTIVE

$925,000
Virtual Tour
1762 Mondrian Cir, Winter Park, FL 32789
2,265 SqFt
3 Beds | 4 Baths

ACTIVE

$899,500
Virtual Tour
1907 S Lakemont Ave, Winter Park, FL 32792
2,063 SqFt
3 Beds | 4 Baths

ACTIVE

$899,000
Virtual Tour
1919 S Lakemont Ave, Winter Park, FL 32792
2,085 SqFt
3 Beds | 4 Baths

ACTIVE

$899,000
Virtual Tour
1917 S Lakemont Ave, Winter Park, FL 32792
2,051 SqFt
3 Beds | 4 Baths

ACTIVE

$899,000
Virtual Tour
1811 Oneco Ave, Winter Park, FL 32789
1,348 SqFt
3 Beds | 2 Baths

ACTIVE

$895,000
Virtual Tour
1655 N Park Ave, Winter Park, FL 32789
1,134 SqFt
2 Beds | 1 Bath

ACTIVE

$895,000
Virtual Tour
1263 Verdant Glade Pl, Winter Park, FL 32792
2,589 SqFt
4 Beds | 4 Baths

ACTIVE

$888,999
Virtual Tour
2128 Sycamore Dr, Winter Park, FL 32789
1,760 SqFt
3 Beds | 2 Baths

ACTIVE

$878,500
Virtual Tour
1915 S Lakemont Ave, Winter Park, FL 32792
2,104 SqFt
3 Beds | 4 Baths

ACTIVE

$875,000
Virtual Tour
1223 Formosa Ave, Winter Park, FL 32789
3,834 SqFt
4 Beds | 3 Baths

ACTIVE

$869,000
1795 Walker Ave, Winter Park, FL 32789
1,813 SqFt
5 Beds | 3 Baths

ACTIVE

$849,900
Virtual Tour
1905 S Lakemont Ave, Winter Park, FL 32792
2,066 SqFt
3 Beds | 4 Baths

ACTIVE

$849,000
Virtual Tour
411 Sylvan Dr, Winter Park, FL 32789
2,270 SqFt
3 Beds | 2 Baths

ACTIVE

$849,000
Virtual Tour
2955 Lolissa Ln, Winter Park, FL 32789
3,902 SqFt
4 Beds | 3 Baths

ACTIVE

$825,000
Virtual Tour
1316 Fountain Hills Ct, Winter Park, FL 32792
2,823 SqFt
4 Beds | 4 Baths

ACTIVE

$819,900
Virtual Tour
648 Brechin Dr, Winter Park, FL 32792
1,820 SqFt
3 Beds | 3 Baths

ACTIVE

$819,000
Virtual Tour
625 Brechin Dr, Winter Park, FL 32792
1,827 SqFt
3 Beds | 2 Baths

ACTIVE

$811,500
Virtual Tour
1250 S Pennsylvania Ave Unit 8, Winter Park, FL 32789
1,957 SqFt
3 Beds | 3 Baths

ACTIVE

$799,900
Virtual Tour
731 Midget Dr, Winter Park, FL 32789
960 SqFt
2 Beds | 1 Bath

ACTIVE

$799,900
Virtual Tour
2804 Dike Rd, Winter Park, FL 32792
2,503 SqFt
4 Beds | 3 Baths

ACTIVE

$799,000
Virtual Tour
786 Antonette Ave, Winter Park, FL 32789
1,146 SqFt
2 Beds | 1 Bath

ACTIVE

$799,000
Virtual Tour
744 London Rd, Winter Park, FL 32792
2,804 SqFt
5 Beds | 3 Baths

ACTIVE

$795,000
1037 N Virginia Ave, Winter Park, FL 32789
1,101 SqFt
3 Beds | 1 Bath

ACTIVE

$795,000
Virtual Tour
607 Dunblane Dr, Winter Park, FL 32792
2,046 SqFt
4 Beds | 3 Baths

ACTIVE

$769,000
Virtual Tour
1375 Suffolk Rd, Winter Park, FL 32789
2,548 SqFt
4 Beds | 3 Baths

ACTIVE

$750,000
2009 Oglesby Ave, Winter Park, FL 32789
1,318 SqFt
3 Beds | 1 Bath

ACTIVE

$750,000
Virtual Tour
1818 Mondrian Cir, Winter Park, FL 32789
2,265 SqFt
3 Beds | 4 Baths

ACTIVE

$749,900
Virtual Tour
2612 Lafayette Ave, Winter Park, FL 32789
2,447 SqFt
3 Beds | 3 Baths

ACTIVE

$749,900
Virtual Tour
1521 Harmon Ave, Winter Park, FL 32789
2,302 SqFt
3 Beds | 3 Baths

ACTIVE

$725,000
Virtual Tour
432 W Swoope Ave, Winter Park, FL 32789
2,317 SqFt
4 Beds | 4 Baths

ACTIVE

$725,000
Virtual Tour
350 Carolina Ave Unit 301, Winter Park, FL 32789
1,544 SqFt
2 Beds | 2 Baths

ACTIVE

$725,000
Virtual Tour
100 S Interlachen Ave Unit 111, Winter Park, FL 32789
901 SqFt
2 Beds | 2 Baths

ACTIVE

$715,000
Virtual Tour
958 Dunraven Dr, Winter Park, FL 32792
1,835 SqFt
4 Beds | 3 Baths

ACTIVE

$699,900
Virtual Tour
1806 Mondrian Cir, Winter Park, FL 32789
2,016 SqFt
3 Beds | 4 Baths

ACTIVE