97 Listings
Sort

$17,486,000
1220 N Park Ave, Winter Park, FL 32789
12,475 SqFt
7 Beds | 7 Baths

ACTIVE

$10,950,000
4 Isle Of Sicily, Winter Park, FL 32789
9,522 SqFt
5 Beds | 8 Baths

ACTIVE

$7,900,000
Virtual Tour
1311 Via Tuscany, Winter Park, FL 32789
10,997 SqFt
7 Beds | 8 Baths

ACTIVE

$5,650,000
Virtual Tour
785 Via Lombardy, Winter Park, FL 32789
6,736 SqFt
5 Beds | 7 Baths

PENDING

$4,999,000
Virtual Tour
466 Henkel Cir, Winter Park, FL 32789
4,416 SqFt
4 Beds | 5 Baths

ACTIVE

$4,950,000
Virtual Tour
227 Genius Dr, Winter Park, FL 32789
7,568 SqFt
5 Beds | 7 Baths

PENDING

$4,900,000
Virtual Tour
550 Palmer Ave, Winter Park, FL 32789
5,952 SqFt
5 Beds | 8 Baths

ACTIVE

$4,600,000
Virtual Tour
690 N New York Ave, Winter Park, FL 32789
4,901 SqFt
4 Beds | 5 Baths

PENDING

$4,325,000
Virtual Tour
1106 Palmer Ave, Winter Park, FL 32789
6,256 SqFt
4 Beds | 6 Baths

ACTIVE

$4,299,000
Virtual Tour
664 W Morse Blvd, Winter Park, FL 32789
5,819 SqFt
4 Beds | 6 Baths

ACTIVE

$3,999,777
Virtual Tour
4400 Tuscany Island Ct, Winter Park, FL 32792
7,226 SqFt
4 Beds | 7 Baths

ACTIVE

$3,995,000
Virtual Tour
1290 Park Ave, Winter Park, FL 32789
3,823 SqFt
4 Beds | 5 Baths

ACTIVE

$3,700,000
Virtual Tour
1795 Killarney Dr, Winter Park, FL 32789
4,363 SqFt
4 Beds | 5 Baths

PENDING

$3,550,000
Virtual Tour
1252 Via Del Mar, Winter Park, FL 32789
4,131 SqFt
5 Beds | 6 Baths

ACTIVE

$3,495,000
Virtual Tour
1150 Via Salerno, Winter Park, FL 32789
3,826 SqFt
4 Beds | 5 Baths

ACTIVE

$3,395,000
Virtual Tour
1441 Cardinal Ct, Winter Park, FL 32789
4,060 SqFt
4 Beds | 6 Baths

PENDING

$3,295,000
Virtual Tour
2138 Lake Dr, Winter Park, FL 32789
5,100 SqFt
4 Beds | 4 Baths

ACTIVE

$3,295,000
Virtual Tour
1180 N New York Ave, Winter Park, FL 32789
3,734 SqFt
4 Beds | 5 Baths

PENDING

$3,295,000
Virtual Tour
147 S Interlachen Ave Unit 250, Winter Park, FL 32789
3,272 SqFt
3 Beds | 5 Baths

ACTIVE

$3,290,000
Virtual Tour
610 Genius Dr, Winter Park, FL 32789
5,196 SqFt
5 Beds | 6 Baths

ACTIVE

$3,250,000
Virtual Tour
2413 Winter Park Rd, Winter Park, FL 32789
4,905 SqFt
5 Beds | 7 Baths

ACTIVE

$3,250,000
Virtual Tour
1824 Harland Park Dr, Winter Park, FL 32789
4,522 SqFt
6 Beds | 5 Baths

ACTIVE

$3,175,000
Virtual Tour
1745 Lake Berry Dr, Winter Park, FL 32789
3,680 SqFt
4 Beds | 4 Baths

ACTIVE

$2,999,990
Virtual Tour
1420 Holts Grove Cir, Winter Park, FL 32789
4,014 SqFt
4 Beds | 7 Baths

ACTIVE

$2,999,500
Virtual Tour
1229 Via Del Mar, Winter Park, FL 32789
4,737 SqFt
5 Beds | 6 Baths

PENDING

$2,999,000
Virtual Tour
1949 Killarney Dr, Winter Park, FL 32789
4,817 SqFt
4 Beds | 5 Baths

PENDING

$2,900,000
Virtual Tour
1064 Howell Branch Rd, Winter Park, FL 32789
6,452 SqFt
5 Beds | 5 Baths

PENDING

$2,800,000
Virtual Tour
170 S Phelps Ave, Winter Park, FL 32789
4,288 SqFt
4 Beds | 5 Baths

ACTIVE

$2,650,000
2172 Temple Dr, Winter Park, FL 32789
3,507 SqFt
5 Beds | 4 Baths

ACTIVE

$2,500,000
Virtual Tour
1428 Holts Grove Cir, Winter Park, FL 32789
4,191 SqFt
5 Beds | 5 Baths

ACTIVE

$2,450,000
Virtual Tour
1771 Taylor Ave, Winter Park, FL 32789
4,010 SqFt
5 Beds | 6 Baths

ACTIVE

$2,250,000
Virtual Tour
2522 Lafayette Ave, Winter Park, FL 32789
3,500 SqFt
4 Beds | 4 Baths

ACTIVE

$2,200,000
Virtual Tour
532 Worthington Dr, Winter Park, FL 32789
4,214 SqFt
5 Beds | 6 Baths

PENDING

$2,200,000
Virtual Tour
255 Stirling Ave, Winter Park, FL 32789
3,635 SqFt
4 Beds | 4 Baths

PENDING

$2,199,999
2723 Norris Ave, Winter Park, FL 32789
4,000 SqFt
4 Beds | 4 Baths

ACTIVE

$2,175,000
870 Georgia Ave, Winter Park, FL 32789
2,709 SqFt
3 Beds | 3 Baths

ACTIVE

$1,995,000
Virtual Tour
1017 Via Tuscany Oaks Way, Winter Park, FL 32789
4,230 SqFt
5 Beds | 6 Baths

PENDING

$1,990,000
Virtual Tour
2015 N Park Ave, Winter Park, FL 32789
3,617 SqFt
4 Beds | 5 Baths

ACTIVE

$1,980,000
Virtual Tour
2011 N Park Ave, Winter Park, FL 32789
3,502 SqFt
4 Beds | 4 Baths

ACTIVE

$1,899,000
Virtual Tour
130 Burks Cir, Winter Park, FL 32789
3,733 SqFt
4 Beds | 5 Baths

PENDING

$1,850,000
Virtual Tour
1318 Morton Rd, Winter Park, FL 32789
2,579 SqFt
4 Beds | 4 Baths

ACTIVE

$1,825,000
Virtual Tour
266 Detmar Dr, Winter Park, FL 32789
3,805 SqFt
4 Beds | 5 Baths

ACTIVE

$1,750,000
Virtual Tour
1742 Temple Dr, Winter Park, FL 32789
3,418 SqFt
4 Beds | 5 Baths

PENDING

$1,750,000
Virtual Tour
2343 Versailles Ave, Winter Park, FL 32789
3,227 SqFt
4 Beds | 4 Baths

PENDING

$1,700,000
Virtual Tour
281 Brewer Ave, Winter Park, FL 32789
4,029 SqFt
5 Beds | 5 Baths

ACTIVE

$1,699,000
Virtual Tour
2325 Chantilly Ave, Winter Park, FL 32789
4,014 SqFt
5 Beds | 6 Baths

ACTIVE

$1,699,000
Virtual Tour
450 Ololu Dr, Winter Park, FL 32789
4,518 SqFt
5 Beds | 6 Baths

ACTIVE

$1,650,000
Virtual Tour
2234 Via Luna, Winter Park, FL 32789
3,222 SqFt
4 Beds | 4 Baths

ACTIVE

$1,625,000
Virtual Tour
234 Detmar Dr, Winter Park, FL 32789
3,609 SqFt
4 Beds | 5 Baths

ACTIVE

$1,580,000
Virtual Tour
1580 Grove Terrace, Winter Park, FL 32789
4,264 SqFt
5 Beds | 5 Baths

ACTIVE

$1,500,000
Virtual Tour
3520 Wilde Ave, Winter Park, FL 32792
4,367 SqFt
6 Beds | 6 Baths

ACTIVE

$1,500,000
Virtual Tour
3580 Wilde Ave, Winter Park, FL 32792
4,367 SqFt
6 Beds | 6 Baths

ACTIVE

$1,500,000
Virtual Tour
4464 Tuscany Island Ct, Winter Park, FL 32792
4,625 SqFt
4 Beds | 5 Baths

ACTIVE

$1,495,000
Virtual Tour
580 Ololu Dr, Winter Park, FL 32789
2,812 SqFt
3 Beds | 3 Baths

ACTIVE

$1,479,000
Virtual Tour
1016 Tuscany Pl, Winter Park, FL 32789
3,151 SqFt
5 Beds | 4 Baths

PENDING

$1,475,000
1913 Sycamore Dr, Winter Park, FL 32789
3,130 SqFt
4 Beds | 5 Baths

ACTIVE

$1,399,000
Virtual Tour
601 Ellen Dr, Winter Park, FL 32789
2,783 SqFt
4 Beds | 5 Baths

ACTIVE

$1,399,000
Virtual Tour
1511 Palm Ave, Winter Park, FL 32789
2,460 SqFt
4 Beds | 4 Baths

PENDING

$1,295,000
2131 Loch Lomond Dr, Winter Park, FL 32792
2,855 SqFt
4 Beds | 5 Baths

ACTIVE

$1,250,000
1050 Via Merano Ct, Winter Park, FL 32789
2,617 SqFt
4 Beds | 3 Baths

PENDING

$1,200,000
Virtual Tour
3540 Wilde Ave, Winter Park, FL 32792
4,325 SqFt
5 Beds | 6 Baths

ACTIVE

$1,200,000
Virtual Tour
1368 Hibiscus Ave, Winter Park, FL 32789
2,394 SqFt
4 Beds | 3 Baths

PENDING

$1,195,000
1832 Pineview Cir, Winter Park, FL 32792
2,843 SqFt
3 Beds | 4 Baths

ACTIVE

$1,125,000
Virtual Tour
911 Osceola Ave, Winter Park, FL 32789
2,342 SqFt
3 Beds | 4 Baths

ACTIVE

$1,100,000
3720 Vinsetta Ct, Winter Park, FL 32792
5,021 SqFt
6 Beds | 5 Baths

PENDING

$1,100,000
Virtual Tour
210 Laurel Park Ct, Winter Park, FL 32792
2,867 SqFt
4 Beds | 3 Baths

ACTIVE

$995,000
Virtual Tour
942 Poinciana Ln, Winter Park, FL 32789
2,350 SqFt
3 Beds | 3 Baths

PENDING

$979,999
507 Langholm Dr, Winter Park, FL 32789
2,174 SqFt
4 Beds | 3 Baths

ACTIVE

$976,000
Virtual Tour
2232 Banchory Rd, Winter Park, FL 32792
2,597 SqFt
4 Beds | 3 Baths

PENDING

$950,000
Virtual Tour
233 Hampden Pl, Winter Park, FL 32789
2,813 SqFt
5 Beds | 3 Baths

ACTIVE

$850,000
Virtual Tour
1762 Chestnut Ave, Winter Park, FL 32789
1,760 SqFt
3 Beds | 2 Baths

PENDING

$740,000
Virtual Tour
7909 Pleasant Pine Cir, Winter Park, FL 32792
3,496 SqFt
5 Beds | 4 Baths

ACTIVE

$725,000
Virtual Tour
659 Darcey Dr, Winter Park, FL 32792
2,251 SqFt
3 Beds | 3 Baths

PENDING

$699,900
Virtual Tour
2741 Eastham Rd, Winter Park, FL 32792
2,312 SqFt
4 Beds | 3 Baths

ACTIVE

$664,900
Virtual Tour
1530 Sugarwood Cir, Winter Park, FL 32792
3,011 SqFt
5 Beds | 3 Baths

PENDING

$649,000
2230 Howard Dr, Winter Park, FL 32789
1,574 SqFt
3 Beds | 1 Bath

PENDING

$639,000
Virtual Tour
2843 Eastern Pkwy, Winter Park, FL 32789
1,692 SqFt
3 Beds | 2 Baths

ACTIVE

$615,000
Virtual Tour
5319 Pine Lily Cir, Winter Park, FL 32792
2,265 SqFt
4 Beds | 2 Baths

PENDING

$599,900
4038 Tenita Dr, Winter Park, FL 32792
2,082 SqFt
3 Beds | 2 Baths

PENDING

$599,000
Virtual Tour
2627 Ambergate Rd, Winter Park, FL 32792
1,805 SqFt
4 Beds | 3 Baths

ACTIVE

$589,900
Virtual Tour
1331 Suffolk Rd, Winter Park, FL 32789
1,508 SqFt
3 Beds | 2 Baths

PENDING

$575,000
Virtual Tour
4353 Steed Ter, Winter Park, FL 32792
2,275 SqFt
4 Beds | 2 Baths

PENDING

$569,900
Virtual Tour
2627 Verona Trl, Winter Park, FL 32789
2,305 SqFt
4 Beds | 3 Baths

PENDING

$560,000
Virtual Tour
1164 Dodd Rd, Winter Park, FL 32792
2,840 SqFt
5 Beds | 4 Baths

PENDING

$550,000
Virtual Tour
2955 Sanbina St, Winter Park, FL 32789
1,553 SqFt
3 Beds | 2 Baths

ACTIVE

$495,000
Virtual Tour
7130 Citrus Ave, Winter Park, FL 32792
1,784 SqFt
4 Beds | 2 Baths

ACTIVE

$485,000
Virtual Tour
2810 Fitzooth Dr, Winter Park, FL 32792
1,777 SqFt
4 Beds | 2 Baths

PENDING

$460,000
Virtual Tour
4444 Steed Ter, Winter Park, FL 32792
1,928 SqFt
4 Beds | 2 Baths

PENDING

$458,000
Virtual Tour
3431 Australian Cir, Winter Park, FL 32792
2,300 SqFt
3 Beds | 2 Baths

PENDING

$425,000
Virtual Tour
1936 Summerfield Rd, Winter Park, FL 32792
1,503 SqFt
3 Beds | 2 Baths

PENDING

$425,000
Virtual Tour
3464 Athena Dr, Winter Park, FL 32792
1,674 SqFt
4 Beds | 2 Baths

PENDING

$415,000
Virtual Tour
1694 Eastbrook Blvd, Winter Park, FL 32792
1,314 SqFt
3 Beds | 2 Baths

PENDING

$394,500
Virtual Tour
1531 Gladiolas Dr, Winter Park, FL 32792
1,647 SqFt
3 Beds | 2 Baths

ACTIVE

$380,000
Virtual Tour
5405 Justine Way, Winter Park, FL 32792
1,247 SqFt
3 Beds | 2 Baths

PENDING

$335,000
Virtual Tour
2829 Salisbury Blvd, Winter Park, FL 32789
1,210 SqFt
2 Beds | 2 Baths

PENDING
1
1 - 97 of 97 Listings shown on map