171 Listings
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$8,799,000
Virtual Tour
2660 Via Tuscany, Winter Park, FL 32789
4,564 SqFt
4 Beds | 5 Baths

ACTIVE

$5,999,999
Virtual Tour
541 Virginia Dr, Winter Park, FL 32789
4,725 SqFt
4 Beds | 4 Baths

ACTIVE

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

ACTIVE

$2,949,999
2652 Lake Howell Ln, Winter Park, FL 32792
3,898 SqFt
5 Beds | 4 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

$2,399,900
Virtual Tour
301 Rippling Ln, Winter Park, FL 32789
3,694 SqFt
4 Beds | 6 Baths

ACTIVE

$2,374,000
Virtual Tour
2522 Lafayette Ave, Winter Park, FL 32789
3,399 SqFt
4 Beds | 4 Baths

ACTIVE

$2,160,000
Virtual Tour
2234 Via Luna, Winter Park, FL 32789
3,554 SqFt
6 Beds | 4 Baths

ACTIVE

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

ACTIVE

$1,895,000
Virtual Tour
817 Antonette Ave, Winter Park, FL 32789
3,971 SqFt
4 Beds | 3 Baths

ACTIVE

$1,850,000
Virtual Tour
1470 Place Picardy, Winter Park, FL 32789
4,227 SqFt
5 Beds | 6 Baths

ACTIVE

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

ACTIVE

$1,650,000
Virtual Tour
101 S New York Ave Unit 302, Winter Park, FL 32789
3,174 SqFt
3 Beds | 4 Baths

ACTIVE

$1,649,000
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

$1,445,000
Virtual Tour
1371 Lyndale Blvd, Winter Park, FL 32789
2,739 SqFt
4 Beds | 3 Baths

ACTIVE

$1,395,000
Virtual Tour
777 Halifax Ave, Winter Park, FL 32792
3,161 SqFt
5 Beds | 5 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
1400 S Pennsylvania Ave, Winter Park, FL 32789
2,060 SqFt
4 Beds | 3 Baths

ACTIVE

$1,299,000
1213 Richmond Rd, Winter Park, FL 32789
3,204 SqFt
4 Beds | 3 Baths

ACTIVE

$1,295,000
Virtual Tour
433 Carolina Ave, Winter Park, FL 32789
2,700 SqFt
5 Beds | 4 Baths

ACTIVE

$1,275,000
Virtual Tour
1611 Walnut Ave, Winter Park, FL 32789
2,635 SqFt
4 Beds | 3 Baths

ACTIVE

$1,275,000
Virtual Tour
1681 Blue Ridge Rd, Winter Park, FL 32789
n/a SqFt
-- Beds | -- Baths

ACTIVE

$1,225,000
Virtual Tour
1585 Chestnut Ave, Winter Park, FL 32789
2,220 SqFt
4 Beds | 3 Baths

ACTIVE

$1,070,000
2330 Westminster Ct, Winter Park, FL 32789
3,296 SqFt
5 Beds | 3 Baths

ACTIVE

$1,049,000
Virtual Tour
1840 Biscayne Dr, Winter Park, FL 32789
2,641 SqFt
5 Beds | 3 Baths

ACTIVE

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

ACTIVE

$995,000
Virtual Tour
1975 Biscayne Dr, Winter Park, FL 32789
3,270 SqFt
5 Beds | 4 Baths

ACTIVE

$955,000
Virtual Tour
1000 Howell Branch Rd, Winter Park, FL 32789
n/a SqFt
-- Beds | -- Baths

ACTIVE

$950,000
Virtual Tour
2445 Lee Rd, Winter Park, FL 32789
2,456 SqFt
-- Beds | -- Baths

ACTIVE

$900,000
Virtual Tour
675 Overspin Dr, Winter Park, FL 32789
2,962 SqFt
4 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
625 Worthington Dr, Winter Park, FL 32789
2,133 SqFt
4 Beds | 2 Baths

ACTIVE

$895,000
Virtual Tour
1762 Mondrian Cir, Winter Park, FL 32789
2,265 SqFt
3 Beds | 4 Baths

ACTIVE

$875,555
Virtual Tour
2128 Sycamore Dr, Winter Park, FL 32789
1,760 SqFt
3 Beds | 2 Baths

ACTIVE

$875,000
Virtual Tour
2418 Whitehall Cir, Winter Park, FL 32792
2,134 SqFt
3 Beds | 2 Baths

ACTIVE

$874,990
Virtual Tour
1429 Indiana Ave, Winter Park, FL 32789
1,844 SqFt
3 Beds | 3 Baths

ACTIVE

$849,000
Virtual Tour
1917 S Lakemont Ave, Winter Park, FL 32792
2,051 SqFt
3 Beds | 4 Baths

ACTIVE

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

ACTIVE

$829,000
1795 Walker Ave, Winter Park, FL 32789
1,813 SqFt
5 Beds | 3 Baths

ACTIVE

$820,000
Virtual Tour
5618 Winterbrook Way, Winter Park, FL 32792
2,866 SqFt
5 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
1250 S Pennsylvania Ave Unit 8, Winter Park, FL 32789
1,957 SqFt
3 Beds | 3 Baths

ACTIVE

$815,000
Virtual Tour
1316 Fountain Hills Ct, Winter Park, FL 32792
2,823 SqFt
4 Beds | 4 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

$795,000
Virtual Tour
625 Brechin Dr, Winter Park, FL 32792
1,827 SqFt
3 Beds | 2 Baths

ACTIVE

$764,900
1037 N Virginia Ave, Winter Park, FL 32789
1,101 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

$749,000
Virtual Tour
786 Antonette Ave, Winter Park, FL 32789
1,146 SqFt
2 Beds | 1 Bath

ACTIVE

$739,000
Virtual Tour
1977 Dundee Dr, Winter Park, FL 32792
1,656 SqFt
-- Beds | -- Baths

ACTIVE

$729,000
Virtual Tour
2812 Mulford Ave, Winter Park, FL 32789
1,527 SqFt
3 Beds | 2 Baths

ACTIVE

$699,000
Virtual Tour
3136 Heartleaf Pl, Winter Park, FL 32792
2,717 SqFt
4 Beds | 4 Baths

ACTIVE

$698,500
Virtual Tour
100 S Interlachen Ave Unit 111, Winter Park, FL 32789
901 SqFt
2 Beds | 2 Baths

ACTIVE

$697,000
Virtual Tour
958 Dunraven Dr, Winter Park, FL 32792
1,835 SqFt
4 Beds | 3 Baths

ACTIVE

$695,000
Virtual Tour
618 N Wymore Rd, Winter Park, FL 32789
2,165 SqFt
-- Beds | -- Baths

ACTIVE

$695,000
Virtual Tour
1806 Mondrian Cir, Winter Park, FL 32789
2,016 SqFt
3 Beds | 4 Baths

ACTIVE

$680,000
Virtual Tour
1792 Killarney Dr, Winter Park, FL 32789
2,082 SqFt
4 Beds | 3 Baths

ACTIVE

$669,000
Virtual Tour
763 Overspin Dr, Winter Park, FL 32789
n/a SqFt
-- Beds | -- Baths

ACTIVE

$649,000
Virtual Tour
535 N Interlachen Ave Unit 305, Winter Park, FL 32789
1,156 SqFt
2 Beds | 2 Baths

ACTIVE

$639,999
1401 Lone Feather Trl, Winter Park, FL 32792
1,770 SqFt
3 Beds | 3 Baths

ACTIVE

$620,000
Virtual Tour
1392 Indiana Ave, Winter Park, FL 32789
1,936 SqFt
3 Beds | 3 Baths

ACTIVE

$615,000
Virtual Tour
5255 Seminole Ave, Winter Park, FL 32792
2,170 SqFt
4 Beds | 3 Baths

ACTIVE

$599,900
Virtual Tour
2100 Suffield Dr, Winter Park, FL 32792
1,807 SqFt
3 Beds | 3 Baths

ACTIVE

$599,000
Virtual Tour
274 N Ranger Blvd, Winter Park, FL 32792
1,420 SqFt
3 Beds | 2 Baths

ACTIVE

$595,000
1848 Mizell Ave, Winter Park, FL 32789
1,162 SqFt
2 Beds | 2 Baths

ACTIVE

$592,500
Virtual Tour
1116 Fairway Dr, Winter Park, FL 32792
1,738 SqFt
3 Beds | 2 Baths

ACTIVE

$579,900
2518 Sweetwater Trl, Winter Park, FL 32789
2,205 SqFt
4 Beds | 2 Baths

ACTIVE

$559,000
Virtual Tour
3901 Woodglade Cove, Winter Park, FL 32792
2,213 SqFt
4 Beds | 3 Baths

ACTIVE

$550,000
Virtual Tour
2627 Ambergate Rd, Winter Park, FL 32792
1,805 SqFt
4 Beds | 3 Baths

ACTIVE

$549,900
Virtual Tour
2855 Cady Way, Winter Park, FL 32792
1,736 SqFt
3 Beds | 2 Baths

ACTIVE

$545,000
4200 Bear Gully Rd, Winter Park, FL 32792
1,945 SqFt
4 Beds | 3 Baths

ACTIVE

$535,000
Virtual Tour
2823 Cady Way, Winter Park, FL 32792
1,688 SqFt
4 Beds | 2 Baths

ACTIVE

$530,000
Virtual Tour
4026 Tenita Dr, Winter Park, FL 32792
2,122 SqFt
4 Beds | 2 Baths

ACTIVE

$525,000
Virtual Tour
2821 Chantilly Ave, Winter Park, FL 32789
1,440 SqFt
3 Beds | 2 Baths

ACTIVE

$520,000
Virtual Tour
1422 Tierra Cir, Winter Park, FL 32792
1,827 SqFt
4 Beds | 2 Baths

ACTIVE

$500,000
Virtual Tour
5240 N Lake Burkett Ln, Winter Park, FL 32792
2,290 SqFt
4 Beds | 3 Baths

ACTIVE

$499,900
Virtual Tour
2073 Shadyhill Ter, Winter Park, FL 32792
1,647 SqFt
3 Beds | 2 Baths

ACTIVE

$499,900
Virtual Tour
1710 Aster Dr, Winter Park, FL 32792
1,664 SqFt
3 Beds | 2 Baths

ACTIVE

$495,000
Virtual Tour
2774 Bright Bird Ln, Winter Park, FL 32792
1,907 SqFt
3 Beds | 3 Baths

ACTIVE

$489,900
Virtual Tour
3128 Patel Dr, Winter Park, FL 32792
1,934 SqFt
4 Beds | 4 Baths

ACTIVE

$489,900
Virtual Tour
7448 Grand Ct, Winter Park, FL 32792
2,158 SqFt
5 Beds | 3 Baths

ACTIVE

$485,000
Virtual Tour
1608 Bomi Cir, Winter Park, FL 32792
1,807 SqFt
3 Beds | 2 Baths

ACTIVE

$485,000
Virtual Tour
1010 Garden Dr, Winter Park, FL 32789
n/a SqFt
-- Beds | -- Baths

ACTIVE

$480,000
2244 Shadowland Loop, Winter Park, FL 32792
2,076 SqFt
3 Beds | 3 Baths

ACTIVE

$475,000
Virtual Tour
1522 Bantam Way, Winter Park, FL 32792
2,076 SqFt
3 Beds | 3 Baths

ACTIVE

$475,000
Virtual Tour
311 E Morse Blvd 7-2, Winter Park, FL 32789
900 SqFt
1 Bed | 1 Bath

ACTIVE

$475,000
Virtual Tour
1354 Tierra Cir, Winter Park, FL 32792
1,827 SqFt
4 Beds | 2 Baths

ACTIVE

$469,900
Virtual Tour
5359 Lanyard Ct, Winter Park, FL 32792
1,572 SqFt
3 Beds | 2 Baths

ACTIVE

$469,000
Virtual Tour
2229 Shadowland Loop, Winter Park, FL 32792
1,964 SqFt
3 Beds | 3 Baths

ACTIVE

$460,000
Virtual Tour
7565 Dockside St, Winter Park, FL 32792
1,948 SqFt
4 Beds | 3 Baths

ACTIVE

$459,900
Virtual Tour
2207 Winter Woods Blvd, Winter Park, FL 32792
1,710 SqFt
4 Beds | 2 Baths

ACTIVE

$457,900
Virtual Tour
4442 Glenview Ln, Winter Park, FL 32792
1,387 SqFt
3 Beds | 2 Baths

ACTIVE

$450,000
Virtual Tour
2341 Devon Ct, Winter Park, FL 32789
1,773 SqFt
3 Beds | 2 Baths

ACTIVE

$449,990
Virtual Tour
1550 Indiana Ave, Winter Park, FL 32789
1,032 SqFt
2 Beds | 2 Baths

ACTIVE

$439,500
Virtual Tour
2158 Sussex Rd, Winter Park, FL 32792
1,669 SqFt
3 Beds | 2 Baths

ACTIVE