390 Listings
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$11,795,000
Virtual Tour
181 Virginia Dr, Winter Park, FL 32789
8,188 SqFt
5 Beds | 8 Baths
Listing Provided By Premier Sotheby's Intl. Realty PENDING
$7,500,000
Virtual Tour
1400 Alabama Dr, Winter Park, FL 32789
7,916 SqFt
5 Beds | 9 Baths
Listing Provided By Iron Valley Real Estate Central Florida ACTIVE
$6,995,000
1210 Via Capri, Winter Park, FL 32789
6,774 SqFt
6 Beds | 7 Baths
Listing Provided By Premier Sotheby's Intl. Realty ACTIVE
$6,800,000
Virtual Tour
500 N Interlachen Ave, Winter Park, FL 32789
4,581 SqFt
4 Beds | 5 Baths
Listing Provided By Kelly Price & Company LLC ACTIVE
$5,950,000
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1246 Alabama Dr, Winter Park, FL 32789
5,763 SqFt
7 Beds | 7 Baths
Listing Provided By Fannie Hillman & Associates ACTIVE
$5,750,000
Virtual Tour
1761 Pinetree Rd, Winter Park, FL 32789
4,792 SqFt
5 Beds | 6 Baths
Listing Provided By Charles Rutenberg Realty Orlando PENDING
$5,695,000
698 N New York Ave, Winter Park, FL 32789
5,096 SqFt
4 Beds | 5 Baths
Listing Provided By Corcoran Premier Realty ACTIVE
$5,500,000
Virtual Tour
1660 Palmer Ave, Winter Park, FL 32789
5,636 SqFt
5 Beds | 7 Baths
Listing Provided By Premier Sotheby's Intl. Realty ACTIVE
$5,200,000
2161 Sharon Rd, Winter Park, FL 32789
6,475 SqFt
5 Beds | 7 Baths
Listing Provided By La Rosa Realty Horizons LLC ACTIVE
$4,750,000
Virtual Tour
421 Lakewood Dr, Winter Park, FL 32789
5,847 SqFt
5 Beds | 9 Baths
Listing Provided By Premier Sotheby's Intl. Realty ACTIVE
$4,650,000
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1135 Lakeview Dr, Winter Park, FL 32789
5,681 SqFt
5 Beds | 5 Baths
Listing Provided By Premier Sotheby's Intl. Realty ACTIVE
$4,595,000
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1231 Via Salerno, Winter Park, FL 32789
5,633 SqFt
5 Beds | 7 Baths
Listing Provided By Premier Sotheby's Intl. Realty ACTIVE
$4,350,000
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1157 Tom Gurney Dr, Winter Park, FL 32789
5,527 SqFt
5 Beds | 6 Baths
Listing Provided By Premier Sotheby's Intl. Realty ACTIVE
$4,250,000
Virtual Tour
985 Lincoln Cir, Winter Park, FL 32789
3,660 SqFt
5 Beds | 7 Baths
Listing Provided By United Real Estate Preferred ACTIVE
$4,200,000
Virtual Tour
571 Lake Front Blvd, Winter Park, FL 32789
5,500 SqFt
7 Beds | 5 Baths
Listing Provided By Premier Sotheby's Intl. Realty ACTIVE
$4,150,000
Virtual Tour
850 Georgia Ave, Winter Park, FL 32789
4,627 SqFt
3 Beds | 6 Baths
Listing Provided By Premier Sotheby's Intl. Realty ACTIVE
$3,890,000
Virtual Tour
1820 Glencoe Rd, Winter Park, FL 32789
4,055 SqFt
5 Beds | 7 Baths
Listing Provided By Corcoran Premier Realty ACTIVE
$3,500,000
Virtual Tour
681 Virginia Dr, Winter Park, FL 32789
4,338 SqFt
4 Beds | 4 Baths
Listing Provided By Park 26 Realty LLC ACTIVE
$3,450,000
Virtual Tour
300 S Interlachen Ave Unit 403, Winter Park, FL 32789
3,355 SqFt
3 Beds | 4 Baths
Listing Provided By Fannie Hillman & Associates ACTIVE
$3,295,000
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1730 Winchester Dr, Winter Park, FL 32789
4,080 SqFt
5 Beds | 6 Baths
Listing Provided By Keller Williams Winter Park ACTIVE
$3,250,000
Virtual Tour
1618 Holts Grove Cir, Winter Park, FL 32789
4,807 SqFt
4 Beds | 8 Baths
Listing Provided By Fannie Hillman & Associates ACTIVE
$3,195,000
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147 S Interlachen Ave Unit 400, Winter Park, FL 32789
5,159 SqFt
4 Beds | 5 Baths
Listing Provided By Premier Sotheby's Intl. Realty ACTIVE
$3,150,000
Virtual Tour
875 Miles Ave Unit 4, Winter Park, FL 32789
1,852 SqFt
18 Beds | 18 Baths
Listing Provided By Hpl Realty Investments PENDING
$3,150,000
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1833 Loch Berry Rd, Winter Park, FL 32789
4,770 SqFt
5 Beds | 5 Baths
Listing Provided By Compass Florida ACTIVE
$3,150,000
Virtual Tour
1635 Highland Rd, Winter Park, FL 32789
4,325 SqFt
5 Beds | 6 Baths
Listing Provided By Charles Rutenberg Realty Orlando PENDING
$3,100,000
Virtual Tour
1450 Mizell Ave, Winter Park, FL 32789
4,487 SqFt
5 Beds | 7 Baths
Listing Provided By Kelly Price & Company LLC ACTIVE
$2,750,000
Virtual Tour
1108 N New York Ave, Winter Park, FL 32789
3,576 SqFt
5 Beds | 5 Baths
Listing Provided By Fannie Hillman & Associates ACTIVE
$2,749,000
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1741 Glencoe Rd, Winter Park, FL 32789
4,692 SqFt
4 Beds | 5 Baths
Listing Provided By Premier Sotheby's Intl. Realty ACTIVE
$2,749,000
Virtual Tour
1331 Lakeview Dr, Winter Park, FL 32789
4,264 SqFt
5 Beds | 5 Baths
Listing Provided By Keller Williams Realty At The Parks PENDING
$2,699,999
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1737 Lookout Landing Cir, Winter Park, FL 32789
5,066 SqFt
5 Beds | 6 Baths
Listing Provided By Keller Williams Realty At The Parks PENDING
$2,650,000
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350 E Reading Way, Winter Park, FL 32789
4,693 SqFt
4 Beds | 4 Baths
Listing Provided By Fannie Hillman & Associates PENDING
$2,600,000
Virtual Tour
1724 Pine Ave, Winter Park, FL 32789
4,425 SqFt
3 Beds | 4 Baths
Listing Provided By Keller Williams Realty At The Parks PENDING
$2,495,000
2412 Chantilly Ave, Winter Park, FL 32789
4,500 SqFt
5 Beds | 7 Baths
Listing Provided By Compass Florida LLC ACTIVE
$2,250,000
Virtual Tour
1340 Chestnut Ave, Winter Park, FL 32789
4,182 SqFt
6 Beds | 6 Baths
Listing Provided By Wra Business & Real Estate ACTIVE
$2,200,000
Virtual Tour
1840 Bryan Ave, Winter Park, FL 32789
3,727 SqFt
4 Beds | 4 Baths
Listing Provided By Olde Town Brokers Inc ACTIVE
$2,199,999
Virtual Tour
1451 Lyndale Blvd, Winter Park, FL 32789
3,853 SqFt
6 Beds | 4 Baths
Listing Provided By Realty One Group Mvp ACTIVE
$2,195,000
Virtual Tour
451 Shepherd Ave, Winter Park, FL 32789
4,312 SqFt
5 Beds | 5 Baths
Listing Provided By Premier Sotheby's Intl. Realty ACTIVE
$2,190,000
Virtual Tour
1941 Englewood Rd, Winter Park, FL 32789
4,112 SqFt
4 Beds | 5 Baths
Listing Provided By Coldwell Banker Residential RE PENDING
$2,190,000
Virtual Tour
2234 Via Luna, Winter Park, FL 32789
3,554 SqFt
6 Beds | 4 Baths
Listing Provided By Lokation ACTIVE
$2,150,000
Virtual Tour
1616 Hibiscus Ave, Winter Park, FL 32789
3,897 SqFt
4 Beds | 5 Baths
Listing Provided By Compass Florida ACTIVE
$2,095,000
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1711 Barcelona Way, Winter Park, FL 32789
3,669 SqFt
4 Beds | 4 Baths
Listing Provided By Fannie Hillman & Associates PENDING
$1,999,999
Virtual Tour
1764 Elizabeths Walk, Winter Park, FL 32789
3,989 SqFt
4 Beds | 4 Baths
Listing Provided By Compass Florida ACTIVE
$1,995,000
Virtual Tour
1362 Richmond Rd, Winter Park, FL 32789
2,925 SqFt
5 Beds | 4 Baths
Listing Provided By Potomac Land Company PENDING
$1,990,000
Virtual Tour
2816 Norris Ave, Winter Park, FL 32789
3,880 SqFt
5 Beds | 5 Baths
Listing Provided By Baldwin Park Realty LLC PENDING
$1,960,000
Virtual Tour
2144 Sycamore Drive, Winter Park, FL 32789
3,499 SqFt
4 Beds | 5 Baths
Listing Provided By Premier Sotheby's Intl. Realty ACTIVE
$1,950,000
Virtual Tour
2415 Versailles Ave, Winter Park, FL 32789
3,954 SqFt
4 Beds | 4 Baths
Listing Provided By Bhhs Florida Realty ACTIVE
$1,925,000
Virtual Tour
419 W Morse Blvd, Winter Park, FL 32789
3,027 SqFt
3 Beds | 4 Baths
Listing Provided By Premier Sotheby's Intl. Realty ACTIVE
$1,895,000
Virtual Tour
1181 Via Capri, Winter Park, FL 32789
3,653 SqFt
3 Beds | 3 Baths
Listing Provided By Fannie Hillman & Associates ACTIVE
$1,895,000
Virtual Tour
1350 Place Vendome, Winter Park, FL 32789
4,049 SqFt
4 Beds | 4 Baths
Listing Provided By Premier Sotheby's Intl. Realty ACTIVE
$1,849,000
Virtual Tour
101 S New York Ave Unit 302, Winter Park, FL 32789
3,075 SqFt
3 Beds | 4 Baths
Listing Provided By Simply Real Estate ACTIVE
$1,800,000
Virtual Tour
1411 Border Dr, Winter Park, FL 32789
4,638 SqFt
4 Beds | 6 Baths
Listing Provided By Keller Williams Winter Park PENDING
$1,799,995
Virtual Tour
3031 Northwood Blvd, Winter Park, FL 32789
2,978 SqFt
4 Beds | 4 Baths
Listing Provided By Baldwin Park Realty LLC ACTIVE
$1,795,000
Virtual Tour
1250 Via Capri, Winter Park, FL 32789
3,217 SqFt
3 Beds | 3 Baths
Listing Provided By Premier Sotheby's Intl. Realty ACTIVE
$1,795,000
Virtual Tour
508 W Swoope Ave, Winter Park, FL 32789
4,133 SqFt
4 Beds | 4 Baths
Listing Provided By Coldwell Banker Residential RE ACTIVE
$1,795,000
Virtual Tour
279 Rippling Ln, Winter Park, FL 32789
3,472 SqFt
4 Beds | 3 Baths
Listing Provided By Fannie Hillman & Associates ACTIVE
$1,795,000
Virtual Tour
643 Pansy Ave, Winter Park, FL 32789
3,228 SqFt
4 Beds | 4 Baths
Listing Provided By Premier Sotheby's Intl. Realty ACTIVE
$1,795,000
Virtual Tour
2125 Sycamore Dr, Winter Park, FL 32789
3,590 SqFt
4 Beds | 5 Baths
Listing Provided By The Hope Group PENDING
$1,790,000
Virtual Tour
1540 Palm Ave, Winter Park, FL 32789
3,423 SqFt
5 Beds | 4 Baths
Listing Provided By Kelly Price & Company LLC PENDING
$1,778,000
Virtual Tour
1350 Lyndale Blvd, Winter Park, FL 32789
3,478 SqFt
4 Beds | 5 Baths
Listing Provided By Homevest Realty ACTIVE
$1,750,000
Virtual Tour
1130 Kenwood Ave, Winter Park, FL 32789
4,162 SqFt
4 Beds | 5 Baths
Listing Provided By Lpt Realty PENDING
$1,750,000
Virtual Tour
2025 Loch Berry Rd, Winter Park, FL 32792
3,620 SqFt
4 Beds | 4 Baths
Listing Provided By Beycome Of Florida LLC PENDING
$1,735,000
331 E Reading Way, Winter Park, FL 32789
3,361 SqFt
4 Beds | 5 Baths
Listing Provided By Premier Sotheby's Intl. Realty PENDING
$1,725,000
Virtual Tour
1101 Kenwood Ave, Winter Park, FL 32789
2,955 SqFt
3 Beds | 3 Baths
Listing Provided By Corcoran Premier Realty ACTIVE
$1,699,000
Virtual Tour
1731 Windsor Dr, Winter Park, FL 32789
3,669 SqFt
4 Beds | 4 Baths
Listing Provided By Charles Rutenberg Realty Orlando ACTIVE
$1,695,000
Virtual Tour
1530 Via Tuscany, Winter Park, FL 32789
3,341 SqFt
4 Beds | 4 Baths
Listing Provided By Coldwell Banker Residential RE ACTIVE
$1,695,000
Virtual Tour
1650 Lakehurst Ave, Winter Park, FL 32789
3,777 SqFt
4 Beds | 4 Baths
Listing Provided By Kelly Price & Company LLC ACTIVE
$1,675,000
Virtual Tour
101 S New York Ave Unit 303, Winter Park, FL 32789
3,174 SqFt
3 Beds | 4 Baths
Listing Provided By Fannie Hillman & Associates ACTIVE
$1,650,000
Virtual Tour
840 W Comstock Ave, Winter Park, FL 32789
2,350 SqFt
4 Beds | 4 Baths
Listing Provided By Coldwell Banker Residential RE ACTIVE
$1,600,000
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 PENDING
$1,599,900
Virtual Tour
2914 Reef Knot Pl, Winter Park, FL 32792
4,173 SqFt
6 Beds | 7 Baths
Listing Provided By Keller Williams Winter Park ACTIVE
$1,595,000
Virtual Tour
1251 Palmer Ave, Winter Park, FL 32789
2,859 SqFt
4 Beds | 3 Baths
Listing Provided By Florida Property LLC ACTIVE
$1,595,000
Virtual Tour
1009 S Pennsylvania Ave, Winter Park, FL 32789
3,023 SqFt
4 Beds | 3 Baths
Listing Provided By Premier Sotheby's Intl. Realty ACTIVE
$1,590,000
Virtual Tour
425 Selkirk Dr, Winter Park, FL 32792
3,330 SqFt
4 Beds | 5 Baths
Listing Provided By Kelly Price & Company LLC ACTIVE
$1,575,000
Virtual Tour
627 Country Club Dr, Winter Park, FL 32789
2,858 SqFt
4 Beds | 4 Baths
Listing Provided By Classic Homes PENDING
$1,575,000
Virtual Tour
1460 Via Sangro Pl, Winter Park, FL 32792
5,111 SqFt
7 Beds | 5 Baths
Listing Provided By Orlando Regional Realty ACTIVE
$1,550,000
Virtual Tour
1871 Taylor Ave, Winter Park, FL 32789
3,401 SqFt
4 Beds | 5 Baths
Listing Provided By Corcoran Premier Realty PENDING
$1,550,000
Virtual Tour
2105 Fosgate Dr, Winter Park, FL 32789
3,068 SqFt
5 Beds | 4 Baths
Listing Provided By Lpt Realty ACTIVE
$1,524,000
Virtual Tour
1571 Sunset Drive, Winter Park, FL 32789
2,700 SqFt
4 Beds | 4 Baths
Listing Provided By Premier Sotheby's Intl. Realty ACTIVE
$1,499,000
Virtual Tour
513 Worthington Dr, Winter Park, FL 32789
3,112 SqFt
3 Beds | 4 Baths
Listing Provided By Colonialtown Realty ACTIVE
$1,495,000
629 Country Club Dr, Winter Park, FL 32789
2,858 SqFt
4 Beds | 4 Baths
Listing Provided By Classic Homes ACTIVE
$1,495,000
Virtual Tour
433 Carolina Ave, Winter Park, FL 32789
2,700 SqFt
5 Beds | 4 Baths
Listing Provided By Coldwell Banker Residential RE ACTIVE
$1,449,000
Virtual Tour
2408 Lafayette Ave, Winter Park, FL 32789
2,838 SqFt
4 Beds | 4 Baths
Listing Provided By Premier Sothebys Int'l Realty ACTIVE
$1,449,000
Virtual Tour
335 W Welbourne Ave Unit 103, Winter Park, FL 32789
2,734 SqFt
3 Beds | 3 Baths
Listing Provided By Lively Real Estate ACTIVE
$1,400,000
Virtual Tour
858 Douglas Ave, Winter Park, FL 32789
2,334 SqFt
4 Beds | 4 Baths
Listing Provided By Summer Wind Realty Central Fl ACTIVE
$1,395,000
Virtual Tour
1011 Palmer Ave, Winter Park, FL 32789
2,550 SqFt
3 Beds | 3 Baths
Listing Provided By Fannie Hillman & Associates ACTIVE
$1,395,000
Virtual Tour
1601 Chestnut Ave, Winter Park, FL 32789
2,795 SqFt
4 Beds | 3 Baths
Listing Provided By Coldwell Banker Residential RE ACTIVE
$1,350,000
Virtual Tour
311 E Morse Blvd Unit 18, Winter Park, FL 32789
2,096 SqFt
2 Beds | 2 Baths
Listing Provided By Charles Rutenberg Realty Orlando ACTIVE
$1,349,000
Virtual Tour
1269 Wading Waters Cir, Winter Park, FL 32792
4,468 SqFt
6 Beds | 4 Baths
Listing Provided By Hamilton Realty ACTIVE
$1,299,900
Virtual Tour
100 S Virginia Ave Unit 201, Winter Park, FL 32789
2,756 SqFt
3 Beds | 3 Baths
Listing Provided By Listwithfreedom.Com ACTIVE
$1,295,000
Virtual Tour
1932 Temple Dr, Winter Park, FL 32789
2,432 SqFt
3 Beds | 3 Baths
Listing Provided By Premier Sotheby's Intl. Realty ACTIVE
$1,295,000
Virtual Tour
850 Juanita Rael, Winter Park, FL 32789
2,306 SqFt
4 Beds | 3 Baths
Listing Provided By Kelly Price & Company LLC ACTIVE
$1,275,000
Virtual Tour
1503 Palmer Ave, Winter Park, FL 32789
2,688 SqFt
4 Beds | 3 Baths
Listing Provided By Kelly Price & Company LLC PENDING
$1,250,000
Virtual Tour
1320 Orchid Ave, Winter Park, FL 32789
2,998 SqFt
4 Beds | 4 Baths
Listing Provided By Exp Realty LLC ACTIVE
$1,250,000
Virtual Tour
1880 Windsor Dr, Winter Park, FL 32789
3,074 SqFt
5 Beds | 4 Baths
Listing Provided By The Hope Group PENDING
$1,249,000
Virtual Tour
7801 Georgeann St, Winter Park, FL 32792
3,158 SqFt
3 Beds | 2 Baths
Listing Provided By RE/MAX Town & Country Realty ACTIVE
$1,249,000
Virtual Tour
501 W Canton Ave Unit 501, Winter Park, FL 32789
2,372 SqFt
3 Beds | 3 Baths
Listing Provided By Fannie Hillman & Associates ACTIVE
$1,224,900
Virtual Tour
625 N Interlachen Ave A, Winter Park, FL 32789
1,718 SqFt
2 Beds | 2 Baths
Listing Provided By Kelly Price & Company LLC ACTIVE
$1,199,900
Virtual Tour
1840 Biscayne Dr, Winter Park, FL 32789
2,641 SqFt
5 Beds | 3 Baths
Listing Provided By The Hope Group ACTIVE
