Winter Park Homes for Sale

$10,900,000

Virtual Tour

1120 Preserve Point Dr, Winter Park, FL 32789

11,255 SqFt

7 Beds | 11 Baths

ACTIVE

$8,799,000

Virtual Tour

2660 Via Tuscany, Winter Park, FL 32789

4,564 SqFt

4 Beds | 5 Baths

ACTIVE

$8,500,000

1112 Preserve Point Dr, Winter Park, FL 32789

6,502 SqFt

5 Beds | 6 Baths

ACTIVE

$6,500,000

Virtual Tour

1400 Alabama Dr, Winter Park, FL 32789

7,916 SqFt

5 Beds | 9 Baths

ACTIVE

$5,800,000

Virtual Tour

541 Virginia Dr, Winter Park, FL 32789

4,725 SqFt

4 Beds | 4 Baths

PENDING

$5,200,000

Virtual Tour

1660 Palmer Ave, Winter Park, FL 32789

6,406 SqFt

5 Beds | 7 Baths

ACTIVE

$5,000,000

Virtual Tour

2228 Azalea Pl, Winter Park, FL 32789

5,072 SqFt

5 Beds | 6 Baths

ACTIVE

$4,750,000

2161 Sharon Rd, Winter Park, FL 32789

6,338 SqFt

5 Beds | 7 Baths

ACTIVE

$4,500,000

Virtual Tour

421 Lakewood Dr, Winter Park, FL 32789

5,847 SqFt

5 Beds | 9 Baths

ACTIVE

$4,395,000

1840 W Fawsett Rd, Winter Park, FL 32789

4,129 SqFt

5 Beds | 5 Baths

ACTIVE

$4,175,000

Virtual Tour

1581 Forest Ave, Winter Park, FL 32789

4,683 SqFt

4 Beds | 6 Baths

ACTIVE

$4,100,000

Virtual Tour

1782 Pine Ave, Winter Park, FL 32789

4,782 SqFt

5 Beds | 7 Baths

ACTIVE

$3,750,000

Virtual Tour

2171 Forrest Rd, Winter Park, FL 32789

4,565 SqFt

5 Beds | 6 Baths

ACTIVE

$3,600,000

182 N Phelps Ave, Winter Park, FL 32789

4,812 SqFt

4 Beds | 5 Baths

ACTIVE

$3,599,999

Virtual Tour

1761 Legion Dr, Winter Park, FL 32789

4,955 SqFt

5 Beds | 6 Baths

ACTIVE

$3,595,000

Virtual Tour

141 S Phelps Ave, Winter Park, FL 32789

5,878 SqFt

6 Beds | 6 Baths

ACTIVE

$3,499,500

Virtual Tour

1391 Richmond Rd, Winter Park, FL 32789

4,635 SqFt

4 Beds | 6 Baths

ACTIVE

$3,490,000

1910 Glencoe Rd, Winter Park, FL 32789

4,205 SqFt

4 Beds | 6 Baths

ACTIVE

$3,300,000

Virtual Tour

1820 Englewood Rd, Winter Park, FL 32789

4,263 SqFt

5 Beds | 6 Baths

ACTIVE

$3,295,000

Virtual Tour

532 Worthington Dr, Winter Park, FL 32789

3,974 SqFt

5 Beds | 6 Baths

ACTIVE

$3,195,000

Virtual Tour

1911 Stonehurst Rd, Winter Park, FL 32789

5,097 SqFt

4 Beds | 6 Baths

PENDING

$3,180,000

Virtual Tour

731 Williams Dr, Winter Park, FL 32789

4,260 SqFt

5 Beds | 6 Baths

PENDING

$3,150,000

Virtual Tour

541 W Canton Ave, Winter Park, FL 32789

3,553 SqFt

4 Beds | 4 Baths

ACTIVE

$3,150,000

Virtual Tour

1730 Winchester Dr, Winter Park, FL 32789

4,080 SqFt

5 Beds | 6 Baths

ACTIVE

$2,999,000

Virtual Tour

1891 Lake Spier Dr, Winter Park, FL 32789

3,932 SqFt

5 Beds | 4 Baths

ACTIVE

$2,950,000

Virtual Tour

1020 Mayfield Ave, Winter Park, FL 32789

2,663 SqFt

4 Beds | 3 Baths

ACTIVE

$2,900,000

Virtual Tour

1401 Green Cove Rd, Winter Park, FL 32789

5,416 SqFt

4 Beds | 7 Baths

ACTIVE

$2,895,000

Virtual Tour

940 Lincoln Cir, Winter Park, FL 32789

3,551 SqFt

4 Beds | 5 Baths

ACTIVE

$2,875,000

Virtual Tour

1860 Via Contessa, Winter Park, FL 32789

7,000 SqFt

8 Beds | 6 Baths

ACTIVE

$2,849,000

Virtual Tour

2652 Lake Howell Ln, Winter Park, FL 32792

3,298 SqFt

5 Beds | 4 Baths

ACTIVE

$2,799,000

Virtual Tour

2550 Venetian Way, Winter Park, FL 32789

4,875 SqFt

4 Beds | 5 Baths

ACTIVE

$2,795,000

Virtual Tour

1630 Lasbury Ave, Winter Park, FL 32789

4,912 SqFt

5 Beds | 5 Baths

ACTIVE

$2,749,000

1690 Palm Ave, Winter Park, FL 32789

3,967 SqFt

5 Beds | 6 Baths

ACTIVE

$2,725,000

Virtual Tour

1400 Place Picardy, Winter Park, FL 32789

4,338 SqFt

5 Beds | 6 Baths

ACTIVE

$2,700,000

Virtual Tour

1781 Pine Ave, Winter Park, FL 32789

3,882 SqFt

5 Beds | 5 Baths

ACTIVE

$2,590,000

Virtual Tour

185 Sylvan Blvd, Winter Park, FL 32789

3,138 SqFt

4 Beds | 5 Baths

ACTIVE

$2,550,000

1700 Palm Ave, Winter Park, FL 32789

3,770 SqFt

4 Beds | 5 Baths

PENDING

$2,500,000

Virtual Tour

450 Lakewood Dr, Winter Park, FL 32789

4,676 SqFt

5 Beds | 6 Baths

ACTIVE

$2,499,900

Virtual Tour

7849 Georgeann St, Winter Park, FL 32792

4,860 SqFt

6 Beds | 8 Baths

PENDING

$2,490,000

Virtual Tour

1795 Greenwich Ave, Winter Park, FL 32789

3,852 SqFt

5 Beds | 6 Baths

PENDING

$2,455,000

521 S Phelps Ave, Winter Park, FL 32789

3,883 SqFt

4 Beds | 5 Baths

ACTIVE

$2,389,000

Virtual Tour

2412 Chantilly Ave, Winter Park, FL 32789

4,506 SqFt

5 Beds | 7 Baths

ACTIVE

$2,375,000

104 Cortland Ave, Winter Park, FL 32789

3,182 SqFt

4 Beds | 3 Baths

ACTIVE

$2,349,900

Virtual Tour

301 Rippling Ln, Winter Park, FL 32789

3,694 SqFt

4 Beds | 6 Baths

PENDING

$2,349,000

Virtual Tour

1361 Palmer Ave, Winter Park, FL 32789

3,558 SqFt

5 Beds | 4 Baths

ACTIVE

$2,295,000

1760 Bryan Ave, Winter Park, FL 32789

3,005 SqFt

4 Beds | 4 Baths

ACTIVE

$2,270,000

Virtual Tour

2522 Lafayette Ave, Winter Park, FL 32789

3,399 SqFt

4 Beds | 4 Baths

ACTIVE

$2,199,000

Virtual Tour

1394 Stewart St, Winter Park, FL 32789

3,907 SqFt

5 Beds | 5 Baths

PENDING

$2,175,000

Virtual Tour

2614 Parkland Dr, Winter Park, FL 32789

3,307 SqFt

4 Beds | 4 Baths

ACTIVE

$2,150,000

Virtual Tour

1560 Woodland Ave, Winter Park, FL 32789

3,851 SqFt

5 Beds | 5 Baths

ACTIVE

$2,119,000

Virtual Tour

785 N Phelps Ave, Winter Park, FL 32789

2,964 SqFt

5 Beds | 5 Baths

ACTIVE

$2,070,000

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

$1,999,900

Virtual Tour

1521 Chestnut Ave, Winter Park, FL 32789

3,117 SqFt

4 Beds | 3 Baths

ACTIVE

$1,999,500

Virtual Tour

1840 Bryan Ave, Winter Park, FL 32789

3,727 SqFt

4 Beds | 4 Baths

ACTIVE

$1,999,000

Virtual Tour

633 Balmoral Rd, Winter Park, FL 32789

2,674 SqFt

4 Beds | 3 Baths

ACTIVE

$1,899,999

Virtual Tour

1299 Harding Street, Winter Park, FL 32789

3,784 SqFt

6 Beds | 5 Baths

ACTIVE

$1,899,000

Virtual Tour

1665 Temple Dr, Winter Park, FL 32789

3,830 SqFt

4 Beds | 4 Baths

PENDING

$1,899,000

Virtual Tour

4469 Old Bear Run, Winter Park, FL 32792

4,288 SqFt

5 Beds | 5 Baths

ACTIVE

$1,897,000

Virtual Tour

2260 Mulbry Dr, Winter Park, FL 32789

3,246 SqFt

5 Beds | 4 Baths

ACTIVE

$1,888,000

Virtual Tour

2407 Lafayette Ave, Winter Park, FL 32789

3,133 SqFt

5 Beds | 5 Baths

ACTIVE

$1,800,000

1682 Arbor Park Dr, Winter Park, FL 32789

2,950 SqFt

4 Beds | 4 Baths

PENDING

$1,799,000

Virtual Tour

2402.5 Temple Dr, Winter Park, FL 32789

3,248 SqFt

4 Beds | 5 Baths

ACTIVE

$1,795,000

Virtual Tour

817 Antonette Ave, Winter Park, FL 32789

3,971 SqFt

4 Beds | 3 Baths

ACTIVE

$1,775,000

1702 Arbor Park Dr, Winter Park, FL 32789

2,950 SqFt

4 Beds | 4 Baths

ACTIVE

$1,759,000

1660 Walnut Ave, Winter Park, FL 32789

2,172 SqFt

4 Beds | 4 Baths

PENDING

$1,699,000

Virtual Tour

2339 Lafayette Ave, Winter Park, FL 32789

3,379 SqFt

4 Beds | 6 Baths

PENDING

$1,699,000

Virtual Tour

1742 Barcelona Way, Winter Park, FL 32789

3,626 SqFt

5 Beds | 8 Baths

ACTIVE

$1,695,000

Virtual Tour

279 Rippling Ln, Winter Park, FL 32789

3,472 SqFt

4 Beds | 3 Baths

ACTIVE

$1,695,000

1831 Mizell Ave, Winter Park, FL 32789

3,204 SqFt

4 Beds | 4 Baths

ACTIVE

$1,675,000

607 Ellen Dr, Winter Park, FL 32789

2,812 SqFt

4 Beds | 5 Baths

ACTIVE

$1,645,000

Virtual Tour

7841 Georgeann St, Winter Park, FL 32792

4,000 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

$1,599,999

Virtual Tour

1429 Chapman Cir, Winter Park, FL 32789

3,116 SqFt

4 Beds | 4 Baths

ACTIVE

$1,599,900

1417 Miller Ave, Winter Park, FL 32789

3,312 SqFt

5 Beds | 4 Baths

ACTIVE

$1,599,000

Virtual Tour

1327 Bridgeport Dr, Winter Park, FL 32789

4,181 SqFt

5 Beds | 4 Baths

ACTIVE

$1,595,000

Virtual Tour

1733 Harmon Ave, Winter Park, FL 32789

3,267 SqFt

5 Beds | 5 Baths

ACTIVE

$1,590,000

Virtual Tour

8041 Lake Waunatta Dr, Winter Park, FL 32792

5,329 SqFt

5 Beds | 5 Baths

ACTIVE

$1,575,000

Virtual Tour

627 Country Club Dr, Winter Park, FL 32789

2,858 SqFt

4 Beds | 4 Baths

PENDING

$1,554,950

Virtual Tour

952 Moss Ln, Winter Park, FL 32789

3,474 SqFt

4 Beds | 4 Baths

ACTIVE

$1,550,000

Virtual Tour

1871 Taylor Ave, Winter Park, FL 32789

3,401 SqFt

4 Beds | 5 Baths

PENDING

$1,500,000

Virtual Tour

2401 Lafayette Ave, Winter Park, FL 32789

3,349 SqFt

4 Beds | 4 Baths

ACTIVE

$1,495,000

Virtual Tour

1420 Palmer Ave, Winter Park, FL 32789

2,953 SqFt

4 Beds | 4 Baths

ACTIVE

$1,490,000

Virtual Tour

2408 Lafayette Ave, Winter Park, FL 32789

2,838 SqFt

4 Beds | 4 Baths

ACTIVE

$1,485,000

Virtual Tour

2015 Summerfield Rd, Winter Park, FL 32792

2,958 SqFt

4 Beds | 4 Baths

ACTIVE

$1,475,000

1600 Barcelona Way, Winter Park, FL 32789

3,014 SqFt

4 Beds | 4 Baths

ACTIVE

$1,425,000

Virtual Tour

1750 Winchester Dr, Winter Park, FL 32789

2,637 SqFt

4 Beds | 4 Baths

PENDING

$1,425,000

Virtual Tour

2922 Reef Knot Pl, Winter Park, FL 32792

3,153 SqFt

4 Beds | 4 Baths

ACTIVE

$1,395,000

1701 Palmer Ave, Winter Park, FL 32789

2,841 SqFt

4 Beds | 3 Baths

ACTIVE

$1,385,000

Virtual Tour

2105 Fosgate Dr, Winter Park, FL 32789

3,068 SqFt

5 Beds | 4 Baths

ACTIVE

$1,349,000

Virtual Tour

1077 Minnesota Ave, Winter Park, FL 32789

3,046 SqFt

4 Beds | 4 Baths

ACTIVE

$1,300,000

Virtual Tour

1400 S Pennsylvania Ave, Winter Park, FL 32789

2,310 SqFt

4 Beds | 3 Baths

ACTIVE

$1,299,000

Virtual Tour

1341 Lyndale Blvd, Winter Park, FL 32789

2,388 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

1611 Chestnut Ave, Winter Park, FL 32789

2,916 SqFt

4 Beds | 4 Baths

ACTIVE

$1,275,000

Virtual Tour

2536 Brookshire Ave, Winter Park, FL 32792

3,140 SqFt

4 Beds | 4 Baths

PENDING

$1,275,000

Virtual Tour

N 726/720 Pennsylvania Ave, Winter Park, FL 32789

2,284 SqFt

6 Beds | 4 Baths

ACTIVE

$1,275,000

Virtual Tour

N 726 And 720 Pennsylvania Ave, Winter Park, FL 32789

2,284 SqFt

6 Beds | 4 Baths

ACTIVE

$1,265,000

Virtual Tour

1611 Walnut Ave, Winter Park, FL 32789

2,635 SqFt

4 Beds | 3 Baths

ACTIVE

$1,210,000

Virtual Tour

4048 Gilder Rose Pl, Winter Park, FL 32792

3,321 SqFt

4 Beds | 4 Baths

ACTIVE

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