278 Listings
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$17,486,000
1220 N Park Ave, Winter Park, FL 32789
12,475 SqFt
7 Beds | 7 Baths
Listing Provided By Premier Sotheby's Intl. Realty ACTIVE
$10,950,000
4 Isle Of Sicily, Winter Park, FL 32789
9,522 SqFt
5 Beds | 8 Baths
Listing Provided By Premier Sotheby's Intl. Realty ACTIVE
$8,500,000
Virtual Tour
1190 N Park Ave, Winter Park, FL 32789
19,619 SqFt
8 Beds | 10 Baths
Listing Provided By RE/MAX 200 Realty ACTIVE
$7,900,000
Virtual Tour
1311 Via Tuscany, Winter Park, FL 32789
10,997 SqFt
7 Beds | 8 Baths
Listing Provided By Premier Sotheby's Intl. Realty ACTIVE
$5,650,000
Virtual Tour
785 Via Lombardy, Winter Park, FL 32789
6,736 SqFt
5 Beds | 7 Baths
Listing Provided By Premier Sotheby's Intl. Realty PENDING
$4,999,000
Virtual Tour
466 Henkel Cir, Winter Park, FL 32789
4,416 SqFt
4 Beds | 5 Baths
Listing Provided By Coldwell Banker Realty ACTIVE
$4,950,000
Virtual Tour
227 Genius Dr, Winter Park, FL 32789
7,568 SqFt
5 Beds | 7 Baths
Listing Provided By Miller Grant And Company PENDING
$4,900,000
Virtual Tour
550 Palmer Ave, Winter Park, FL 32789
5,952 SqFt
5 Beds | 8 Baths
Listing Provided By Fannie Hillman & Associates ACTIVE
$4,600,000
Virtual Tour
690 N New York Ave, Winter Park, FL 32789
4,901 SqFt
4 Beds | 5 Baths
Listing Provided By 407 Properties PENDING
$4,325,000
Virtual Tour
1106 Palmer Ave, Winter Park, FL 32789
6,256 SqFt
4 Beds | 6 Baths
Listing Provided By Fannie Hillman & Associates ACTIVE
$4,299,000
Virtual Tour
664 W Morse Blvd, Winter Park, FL 32789
5,819 SqFt
4 Beds | 6 Baths
Listing Provided By Corcoran Premier Realty ACTIVE
$4,150,000
Virtual Tour
526 Genius Dr, Winter Park, FL 32789
6,390 SqFt
4 Beds | 5 Baths
Listing Provided By Kelly Price & Company LLC ACTIVE
$3,999,777
Virtual Tour
4400 Tuscany Island Ct, Winter Park, FL 32792
7,226 SqFt
4 Beds | 7 Baths
Listing Provided By Royalty R E Boutique Inc ACTIVE
$3,995,000
Virtual Tour
1290 Park Ave, Winter Park, FL 32789
3,823 SqFt
4 Beds | 5 Baths
Listing Provided By Premier Sotheby's Intl. Realty ACTIVE
$3,895,000
Virtual Tour
637 N Park Ave Unit 5, Winter Park, FL 32789
4,237 SqFt
3 Beds | 5 Baths
Listing Provided By Maroon Realty Group LLC ACTIVE
$3,700,000
Virtual Tour
1795 Killarney Dr, Winter Park, FL 32789
4,363 SqFt
4 Beds | 5 Baths
Listing Provided By Douglas Elliman PENDING
$3,550,000
Virtual Tour
1252 Via Del Mar, Winter Park, FL 32789
4,131 SqFt
5 Beds | 6 Baths
Listing Provided By Kelly Price & Company LLC ACTIVE
$3,495,000
Virtual Tour
1150 Via Salerno, Winter Park, FL 32789
3,826 SqFt
4 Beds | 5 Baths
Listing Provided By Kelly Price & Company LLC ACTIVE
$3,395,000
Virtual Tour
1441 Cardinal Ct, Winter Park, FL 32789
4,060 SqFt
4 Beds | 6 Baths
Listing Provided By Maroon Realty Group LLC PENDING
$3,295,000
Virtual Tour
2138 Lake Dr, Winter Park, FL 32789
5,100 SqFt
4 Beds | 4 Baths
Listing Provided By Wemert Group Realty LLC ACTIVE
$3,295,000
Virtual Tour
1180 N New York Ave, Winter Park, FL 32789
3,734 SqFt
4 Beds | 5 Baths
Listing Provided By Maroon Realty Group LLC PENDING
$3,295,000
Virtual Tour
147 S Interlachen Ave Unit 250, Winter Park, FL 32789
3,272 SqFt
3 Beds | 5 Baths
Listing Provided By Keys Realty Redefined LLC ACTIVE
$3,290,000
Virtual Tour
610 Genius Dr, Winter Park, FL 32789
5,196 SqFt
5 Beds | 6 Baths
Listing Provided By Kelly Price & Company LLC ACTIVE
$3,250,000
Virtual Tour
2413 Winter Park Rd, Winter Park, FL 32789
4,905 SqFt
5 Beds | 7 Baths
Listing Provided By The Hope Group ACTIVE
$3,250,000
Virtual Tour
1824 Harland Park Dr, Winter Park, FL 32789
4,522 SqFt
6 Beds | 5 Baths
Listing Provided By Top Florida Homes ACTIVE
$3,175,000
Virtual Tour
1745 Lake Berry Dr, Winter Park, FL 32789
3,680 SqFt
4 Beds | 4 Baths
Listing Provided By Kelly Price & Company LLC ACTIVE
$2,999,990
Virtual Tour
1420 Holts Grove Cir, Winter Park, FL 32789
4,014 SqFt
4 Beds | 7 Baths
Listing Provided By Kelly Price & Company LLC ACTIVE
$2,999,500
Virtual Tour
1229 Via Del Mar, Winter Park, FL 32789
4,737 SqFt
5 Beds | 6 Baths
Listing Provided By Charles Rutenberg Realty Orlando PENDING
$2,999,000
Virtual Tour
1949 Killarney Dr, Winter Park, FL 32789
4,817 SqFt
4 Beds | 5 Baths
Listing Provided By Keller Williams Winter Park PENDING
$2,950,000
Virtual Tour
125 S Interlachen Ave Unit 2, Winter Park, FL 32789
3,244 SqFt
3 Beds | 5 Baths
Listing Provided By Keller Williams Winter Park ACTIVE
$2,900,000
Virtual Tour
1064 Howell Branch Rd, Winter Park, FL 32789
6,452 SqFt
5 Beds | 5 Baths
Listing Provided By Corcoran Premier Realty PENDING
$2,800,000
Virtual Tour
170 S Phelps Ave, Winter Park, FL 32789
4,288 SqFt
4 Beds | 5 Baths
Listing Provided By The Hope Group ACTIVE
$2,650,000
2172 Temple Dr, Winter Park, FL 32789
3,507 SqFt
5 Beds | 4 Baths
Listing Provided By Coldwell Banker Realty ACTIVE
$2,500,000
Virtual Tour
1428 Holts Grove Cir, Winter Park, FL 32789
4,191 SqFt
5 Beds | 5 Baths
Listing Provided By Bhhs Results Realty ACTIVE
$2,450,000
Virtual Tour
1771 Taylor Ave, Winter Park, FL 32789
4,010 SqFt
5 Beds | 6 Baths
Listing Provided By Premier Sotheby's Intl. Realty ACTIVE
$2,350,000
Virtual Tour
660 W Morse Blvd, Winter Park, FL 32789
3,286 SqFt
3 Beds | 4 Baths
Listing Provided By Hyser LLC ACTIVE
$2,250,000
Virtual Tour
2522 Lafayette Ave, Winter Park, FL 32789
3,500 SqFt
4 Beds | 4 Baths
Listing Provided By Roman's Pro Realty LLC ACTIVE
$2,200,000
Virtual Tour
532 Worthington Dr, Winter Park, FL 32789
4,214 SqFt
5 Beds | 6 Baths
Listing Provided By Keller Williams Winter Park PENDING
$2,200,000
Virtual Tour
255 Stirling Ave, Winter Park, FL 32789
3,635 SqFt
4 Beds | 4 Baths
Listing Provided By Corcoran Premier Realty PENDING
$2,199,999
2723 Norris Ave, Winter Park, FL 32789
4,000 SqFt
4 Beds | 4 Baths
Listing Provided By Nest Fl LLC ACTIVE
$2,175,000
870 Georgia Ave, Winter Park, FL 32789
2,709 SqFt
3 Beds | 3 Baths
Listing Provided By Kelly Price & Company LLC ACTIVE
$1,995,000
Virtual Tour
1017 Via Tuscany Oaks Way, Winter Park, FL 32789
4,230 SqFt
5 Beds | 6 Baths
Listing Provided By Premier Sotheby's Intl. Realty PENDING
$1,990,000
Virtual Tour
2015 N Park Ave, Winter Park, FL 32789
3,617 SqFt
4 Beds | 5 Baths
Listing Provided By Baldwin Park Realty LLC ACTIVE
$1,980,000
Virtual Tour
2011 N Park Ave, Winter Park, FL 32789
3,502 SqFt
4 Beds | 4 Baths
Listing Provided By Baldwin Park Realty LLC ACTIVE
$1,899,000
Virtual Tour
130 Burks Cir, Winter Park, FL 32789
3,733 SqFt
4 Beds | 5 Baths
Listing Provided By Keller Williams Winter Park PENDING
$1,895,000
Virtual Tour
1531 Place Picardy, Winter Park, FL 32789
3,964 SqFt
4 Beds | 4 Baths
Listing Provided By Premier Sotheby's Intl. Realty ACTIVE
$1,850,000
Virtual Tour
1318 Morton Rd, Winter Park, FL 32789
2,579 SqFt
4 Beds | 4 Baths
Listing Provided By Roman's Pro Realty LLC ACTIVE
$1,825,000
Virtual Tour
266 Detmar Dr, Winter Park, FL 32789
3,805 SqFt
4 Beds | 5 Baths
Listing Provided By Sotera Living ACTIVE
$1,800,000
Virtual Tour
2726 Lake Howell Ln, Winter Park, FL 32792
1,552 SqFt
3 Beds | 2 Baths
Listing Provided By Coldwell Banker Realty ACTIVE
$1,750,000
Virtual Tour
1166 Oaks Blvd, Winter Park, FL 32789
2,812 SqFt
4 Beds | 4 Baths
Listing Provided By Premier Sotheby's Intl. Realty ACTIVE
$1,750,000
Virtual Tour
1742 Temple Dr, Winter Park, FL 32789
3,418 SqFt
4 Beds | 5 Baths
Listing Provided By Kelly Price & Company LLC PENDING
$1,750,000
Virtual Tour
2343 Versailles Ave, Winter Park, FL 32789
3,227 SqFt
4 Beds | 4 Baths
Listing Provided By Core Group Real Estate LLC PENDING
$1,700,000
Virtual Tour
281 Brewer Ave, Winter Park, FL 32789
4,029 SqFt
5 Beds | 5 Baths
Listing Provided By Keller Williams Realty At The Parks ACTIVE
$1,699,000
Virtual Tour
2325 Chantilly Ave, Winter Park, FL 32789
4,014 SqFt
5 Beds | 6 Baths
Listing Provided By Premier Sothebys Int'l Realty ACTIVE
$1,699,000
Virtual Tour
450 Ololu Dr, Winter Park, FL 32789
4,518 SqFt
5 Beds | 6 Baths
Listing Provided By Primestate Realty ACTIVE
$1,695,000
Virtual Tour
1120 Palmer Ave, Winter Park, FL 32789
3,341 SqFt
3 Beds | 4 Baths
Listing Provided By Premier Sotheby's Intl. Realty PENDING
$1,650,000
Virtual Tour
2234 Via Luna, Winter Park, FL 32789
3,222 SqFt
4 Beds | 4 Baths
Listing Provided By Lokation ACTIVE
$1,625,000
Virtual Tour
234 Detmar Dr, Winter Park, FL 32789
3,609 SqFt
4 Beds | 5 Baths
Listing Provided By Kelly Price & Company LLC ACTIVE
$1,599,000
Virtual Tour
1809 Harland Park Dr, Winter Park, FL 32789
3,660 SqFt
4 Beds | 4 Baths
Listing Provided By Beycome Of Florida LLC PENDING
$1,595,000
Virtual Tour
690 Osceola Ave Unit 504, Winter Park, FL 32789
1,998 SqFt
3 Beds | 3 Baths
Listing Provided By Keller Williams Winter Park ACTIVE
$1,580,000
Virtual Tour
1580 Grove Terrace, Winter Park, FL 32789
4,264 SqFt
5 Beds | 5 Baths
Listing Provided By Fannie Hillman & Associates ACTIVE
$1,500,000
Virtual Tour
3520 Wilde Ave, Winter Park, FL 32792
4,367 SqFt
6 Beds | 6 Baths
Listing Provided By Coldwell Banker Realty ACTIVE
$1,500,000
Virtual Tour
3580 Wilde Ave, Winter Park, FL 32792
4,367 SqFt
6 Beds | 6 Baths
Listing Provided By Coldwell Banker Realty ACTIVE
$1,500,000
Virtual Tour
4464 Tuscany Island Ct, Winter Park, FL 32792
4,625 SqFt
4 Beds | 5 Baths
Listing Provided By The Property Pros Real Estate Inc ACTIVE
$1,495,000
Virtual Tour
580 Ololu Dr, Winter Park, FL 32789
2,812 SqFt
3 Beds | 3 Baths
Listing Provided By Sotera Living ACTIVE
$1,479,000
Virtual Tour
1016 Tuscany Pl, Winter Park, FL 32789
3,151 SqFt
5 Beds | 4 Baths
Listing Provided By Fannie Hillman & Associates PENDING
$1,475,000
1913 Sycamore Dr, Winter Park, FL 32789
3,130 SqFt
4 Beds | 5 Baths
Listing Provided By Keller Williams Winter Park ACTIVE
$1,475,000
361 Beloit Ave, Winter Park, FL 32789
2,793 SqFt
3 Beds | 3 Baths
Listing Provided By Fannie Hillman & Associates PENDING
$1,475,000
Virtual Tour
195 Cortland Ave, Winter Park, FL 32789
3,018 SqFt
3 Beds | 4 Baths
Listing Provided By Fannie Hillman & Associates ACTIVE
$1,399,000
Virtual Tour
601 Ellen Dr, Winter Park, FL 32789
2,783 SqFt
4 Beds | 5 Baths
Listing Provided By Colony Realty Group ACTIVE
$1,399,000
Virtual Tour
1511 Palm Ave, Winter Park, FL 32789
2,460 SqFt
4 Beds | 4 Baths
Listing Provided By Coldwell Banker Realty PENDING
$1,397,000
Virtual Tour
1209 Sharon Pl, Winter Park, FL 32789
2,079 SqFt
4 Beds | 3 Baths
Listing Provided By Kelly Price & Company LLC ACTIVE
$1,300,000
840 W Comstock Ave, Winter Park, FL 32789
2,700 SqFt
4 Beds | 4 Baths
Listing Provided By Corcoran Premier Realty ACTIVE
$1,295,000
2131 Loch Lomond Dr, Winter Park, FL 32792
2,855 SqFt
4 Beds | 5 Baths
Listing Provided By Keller Williams Winter Park ACTIVE
$1,275,000
Virtual Tour
3708 Vinsetta Ct, Winter Park, FL 32792
5,021 SqFt
6 Beds | 5 Baths
Listing Provided By Coldwell Banker Realty PENDING
$1,250,000
1050 Via Merano Ct, Winter Park, FL 32789
2,617 SqFt
4 Beds | 3 Baths
Listing Provided By Fannie Hillman & Associates PENDING
$1,200,000
Virtual Tour
3540 Wilde Ave, Winter Park, FL 32792
4,325 SqFt
5 Beds | 6 Baths
Listing Provided By Coldwell Banker Realty ACTIVE
$1,200,000
Virtual Tour
1368 Hibiscus Ave, Winter Park, FL 32789
2,394 SqFt
4 Beds | 3 Baths
Listing Provided By Exp Realty LLC PENDING
$1,195,000
1832 Pineview Cir, Winter Park, FL 32792
2,843 SqFt
3 Beds | 4 Baths
Listing Provided By Keller Williams Winter Park ACTIVE
$1,195,000
1551 Dale Ave, Winter Park, FL 32789
2,451 SqFt
4 Beds | 3 Baths
Listing Provided By Fannie Hillman & Associates PENDING
$1,179,000
Virtual Tour
1404 Border Dr, Winter Park, FL 32789
2,505 SqFt
4 Beds | 4 Baths
Listing Provided By Hyser LLC ACTIVE
$1,153,050
516 W Swoope Ave, Winter Park, FL 32789
2,666 SqFt
3 Beds | 3 Baths
Listing Provided By Kelly Price & Company LLC PENDING
$1,150,000
Virtual Tour
1572 Sunset Dr, Winter Park, FL 32789
2,626 SqFt
4 Beds | 4 Baths
Listing Provided By Outlet Realty PENDING
$1,125,000
1400 Lyndale Blvd, Winter Park, FL 32789
2,829 SqFt
4 Beds | 3 Baths
Listing Provided By Premier Sotheby's Intl. Realty PENDING
$1,125,000
Virtual Tour
911 Osceola Ave, Winter Park, FL 32789
2,342 SqFt
3 Beds | 4 Baths
Listing Provided By Coldwell Banker Realty ACTIVE
$1,100,000
3720 Vinsetta Ct, Winter Park, FL 32792
5,021 SqFt
6 Beds | 5 Baths
Listing Provided By Keller Williams Advantage Real PENDING
$1,100,000
Virtual Tour
210 Laurel Park Ct, Winter Park, FL 32792
2,867 SqFt
4 Beds | 3 Baths
Listing Provided By Pr Real Estate Services ACTIVE
$1,098,625
514 W Swoope Ave, Winter Park, FL 32789
2,585 SqFt
3 Beds | 3 Baths
Listing Provided By Kelly Price & Company LLC PENDING
$1,095,000
Virtual Tour
266 W Lyman Ave, Winter Park, FL 32789
2,000 SqFt
3 Beds | 3 Baths
Listing Provided By Coldwell Banker Realty ACTIVE
$1,079,730
500 W Swoope Ave, Winter Park, FL 32789
2,666 SqFt
3 Beds | 3 Baths
Listing Provided By Kelly Price & Company LLC PENDING
$1,050,000
502 W Swoope Ave, Winter Park, FL 32789
2,585 SqFt
3 Beds | 3 Baths
Listing Provided By Kelly Price & Company LLC PENDING
$1,046,925
512 W Swoope Ave, Winter Park, FL 32789
2,585 SqFt
3 Beds | 3 Baths
Listing Provided By Kelly Price & Company LLC PENDING
$1,046,925
518 W Swoope Ave, Winter Park, FL 32789
2,585 SqFt
3 Beds | 3 Baths
Listing Provided By Kelly Price & Company LLC PENDING
$995,000
Virtual Tour
942 Poinciana Ln, Winter Park, FL 32789
2,350 SqFt
3 Beds | 3 Baths
Listing Provided By Fannie Hillman & Associates PENDING
$990,000
Virtual Tour
100 S Virginia Ave Unit 316, Winter Park, FL 32789
2,599 SqFt
3 Beds | 3 Baths
Listing Provided By Fannie Hillman & Associates ACTIVE
$980,000
Virtual Tour
244 W Kings Way, Winter Park, FL 32789
2,290 SqFt
3 Beds | 2 Baths
Listing Provided By Fannie Hillman & Associates ACTIVE
$979,999
507 Langholm Dr, Winter Park, FL 32789
2,174 SqFt
4 Beds | 3 Baths
Listing Provided By Listwithfreedom.Com ACTIVE
$976,000
Virtual Tour
2232 Banchory Rd, Winter Park, FL 32792
2,597 SqFt
4 Beds | 3 Baths
Listing Provided By Olde Town Brokers Inc PENDING
