Winter Park Homes for Sale

$11,900,000

Virtual Tour

1120 Preserve Point Dr, Winter Park, FL 32789

11,255 SqFt

7 Beds | 11 Baths

ACTIVE

$8,995,000

Virtual Tour

2001 Bett Mar Ln, Winter Park, FL 32789

8,583 SqFt

8 Beds | 9 Baths

PENDING

$8,799,000

Virtual Tour

2660 Via Tuscany, Winter Park, FL 32789

4,564 SqFt

4 Beds | 5 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

ACTIVE

$5,400,000

Virtual Tour

2228 Azalea Pl, Winter Park, FL 32789

5,072 SqFt

5 Beds | 6 Baths

ACTIVE

$5,200,000

Virtual Tour

1660 Palmer Ave, Winter Park, FL 32789

6,406 SqFt

5 Beds | 7 Baths

ACTIVE

$4,985,000

2161 Sharon Rd, Winter Park, FL 32789

6,338 SqFt

5 Beds | 7 Baths

ACTIVE

$4,799,900

Virtual Tour

1691 Chestnut Ave, Winter Park, FL 32789

4,582 SqFt

5 Beds | 5 Baths

PENDING

$4,600,000

Virtual Tour

2118 Lake Dr, Winter Park, FL 32789

6,000 SqFt

6 Beds | 6 Baths

PENDING

$4,500,000

1336 College Pt, Winter Park, FL 32789

3,181 SqFt

4 Beds | 5 Baths

PENDING

$4,500,000

Virtual Tour

702 Via Bella, Winter Park, FL 32789

3,720 SqFt

5 Beds | 6 Baths

ACTIVE

$4,500,000

Virtual Tour

421 Lakewood Dr, Winter Park, FL 32789

5,847 SqFt

5 Beds | 9 Baths

PENDING

$4,395,000

Virtual Tour

229 Alexander Pl, Winter Park, FL 32789

4,431 SqFt

4 Beds | 6 Baths

ACTIVE

$4,395,000

1840 W Fawsett Rd, Winter Park, FL 32789

4,129 SqFt

5 Beds | 5 Baths

ACTIVE

$4,200,000

Virtual Tour

571 Lake Front Blvd, Winter Park, FL 32789

5,500 SqFt

7 Beds | 5 Baths

ACTIVE

$4,100,000

Virtual Tour

1782 Pine Ave, Winter Park, FL 32789

4,782 SqFt

5 Beds | 7 Baths

ACTIVE

$3,995,000

Virtual Tour

2020 Venetian Way, Winter Park, FL 32789

4,188 SqFt

4 Beds | 4 Baths

PENDING

$3,950,000

Virtual Tour

851 Georgia Ave, Winter Park, FL 32789

4,314 SqFt

4 Beds | 4 Baths

PENDING

$3,850,000

Virtual Tour

2171 Forrest Rd, Winter Park, FL 32789

4,565 SqFt

5 Beds | 6 Baths

ACTIVE

$3,850,000

Virtual Tour

861 Bonita Dr, Winter Park, FL 32789

6,939 SqFt

6 Beds | 8 Baths

PENDING

$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

$3,400,000

Virtual Tour

1911 Stonehurst Rd, Winter Park, FL 32789

5,097 SqFt

4 Beds | 6 Baths

PENDING

$3,350,000

649 N Park Ave, Winter Park, FL 32789

3,180 SqFt

3 Beds | 5 Baths

ACTIVE

$3,295,000

Virtual Tour

1730 Winchester Dr, Winter Park, FL 32789

4,080 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

$3,250,000

Virtual Tour

1900 W Fawsett Rd, Winter Park, FL 32789

4,600 SqFt

4 Beds | 5 Baths

PENDING

$3,250,000

Virtual Tour

1833 Loch Berry Rd, Winter Park, FL 32789

4,770 SqFt

5 Beds | 5 Baths

PENDING

$3,250,000

Virtual Tour

266 Chase Ave, Winter Park, FL 32789

4,088 SqFt

5 Beds | 6 Baths

ACTIVE

$3,195,000

1020 Mayfield Ave, Winter Park, FL 32789

2,663 SqFt

4 Beds | 3 Baths

ACTIVE

$2,950,000

Virtual Tour

1860 Via Contessa, Winter Park, FL 32789

7,000 SqFt

8 Beds | 6 Baths

ACTIVE

$2,949,999

2652 Lake Howell Ln, Winter Park, FL 32792

3,898 SqFt

5 Beds | 4 Baths

ACTIVE

$2,895,000

Virtual Tour

1630 Lasbury Ave, Winter Park, FL 32789

4,912 SqFt

5 Beds | 5 Baths

ACTIVE

$2,850,000

Virtual Tour

2550 Venetian Way, Winter Park, FL 32789

4,875 SqFt

4 Beds | 5 Baths

ACTIVE

$2,850,000

Virtual Tour

1400 Place Picardy, Winter Park, FL 32789

4,411 SqFt

5 Beds | 6 Baths

ACTIVE

$2,695,000

Virtual Tour

254 Sylvan Blvd, Winter Park, FL 32789

3,653 SqFt

3 Beds | 3 Baths

PENDING

$2,650,000

1700 Palm Ave, Winter Park, FL 32789

3,770 SqFt

4 Beds | 5 Baths

ACTIVE

$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

ACTIVE

$2,400,000

Virtual Tour

673 Balmoral Rd, Winter Park, FL 32789

2,663 SqFt

4 Beds | 3 Baths

PENDING

$2,399,900

Virtual Tour

301 Rippling Ln, Winter Park, FL 32789

3,694 SqFt

4 Beds | 6 Baths

ACTIVE

$2,395,000

Virtual Tour

2814 Parkland Dr, Winter Park, FL 32789

3,089 SqFt

4 Beds | 4 Baths

PENDING

$2,395,000

Virtual Tour

2412 Chantilly Ave, Winter Park, FL 32789

4,506 SqFt

5 Beds | 7 Baths

ACTIVE

$2,350,000

Virtual Tour

2522 Lafayette Ave, Winter Park, FL 32789

3,399 SqFt

4 Beds | 4 Baths

ACTIVE

$2,254,000

Virtual Tour

141 Oakwood Way, Winter Park, FL 32789

3,909 SqFt

5 Beds | 4 Baths

ACTIVE

$2,249,000

Virtual Tour

1299 Harding Street, Winter Park, FL 32789

3,784 SqFt

6 Beds | 5 Baths

ACTIVE

$2,200,000

Virtual Tour

4469 Old Bear Run, Winter Park, FL 32792

4,288 SqFt

5 Beds | 5 Baths

ACTIVE

$2,199,000

Virtual Tour

1394 Stewart St, Winter Park, FL 32789

3,907 SqFt

5 Beds | 5 Baths

ACTIVE

$2,160,000

Virtual Tour

2234 Via Luna, Winter Park, FL 32789

3,554 SqFt

6 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

$2,000,000

2260 Mulbry Dr, Winter Park, FL 32789

3,246 SqFt

5 Beds | 4 Baths

ACTIVE

$1,999,993

Virtual Tour

1451 Lyndale Blvd, Winter Park, FL 32789

3,853 SqFt

6 Beds | 4 Baths

ACTIVE

$1,950,000

Virtual Tour

622 Penn Pl, Winter Park, FL 32789

2,767 SqFt

3 Beds | 4 Baths

ACTIVE

$1,875,000

Virtual Tour

1970 Laurel Rd, Winter Park, FL 32789

3,440 SqFt

4 Beds | 4 Baths

PENDING

$1,825,000

Virtual Tour

817 Antonette Ave, Winter Park, FL 32789

3,971 SqFt

4 Beds | 3 Baths

ACTIVE

$1,800,000

1682 Arbor Park Dr, Winter Park, FL 32789

2,950 SqFt

4 Beds | 4 Baths

PENDING

$1,795,000

Virtual Tour

2813 Northwood Blvd, Winter Park, FL 32789

3,444 SqFt

4 Beds | 4 Baths

ACTIVE

$1,775,000

1702 Arbor Park Dr, Winter Park, FL 32789

2,950 SqFt

4 Beds | 4 Baths

ACTIVE

$1,770,000

Virtual Tour

1470 Place Picardy, Winter Park, FL 32789

4,227 SqFt

5 Beds | 6 Baths

ACTIVE

$1,759,000

1660 Walnut Ave, Winter Park, FL 32789

2,172 SqFt

4 Beds | 4 Baths

ACTIVE

$1,750,000

Virtual Tour

279 Rippling Ln, Winter Park, FL 32789

3,472 SqFt

4 Beds | 3 Baths

ACTIVE

$1,690,000

Virtual Tour

8041 Lake Waunatta Dr, Winter Park, FL 32792

5,329 SqFt

5 Beds | 5 Baths

ACTIVE

$1,675,000

607 Ellen Dr, Winter Park, FL 32789

2,812 SqFt

4 Beds | 5 Baths

ACTIVE

$1,650,000

1701 Palmer Ave, Winter Park, FL 32789

2,841 SqFt

4 Beds | 3 Baths

ACTIVE

$1,625,000

Virtual Tour

1650 Lakehurst Ave, Winter Park, FL 32789

3,777 SqFt

4 Beds | 4 Baths

ACTIVE

$1,600,000

Virtual Tour

281 Brewer Ave, Winter Park, FL 32789

4,029 SqFt

5 Beds | 5 Baths

PENDING

$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

$1,595,000

335 Beloit Ave, Winter Park, FL 32789

2,420 SqFt

3 Beds | 2 Baths

PENDING

$1,575,000

Virtual Tour

627 Country Club Dr, Winter Park, FL 32789

2,858 SqFt

4 Beds | 4 Baths

PENDING

$1,575,000

Virtual Tour

690 Osceola Ave Unit 604, Winter Park, FL 32789

2,128 SqFt

3 Beds | 3 Baths

ACTIVE

$1,550,000

Virtual Tour

1661 Woodland Ave, Winter Park, FL 32789

3,215 SqFt

3 Beds | 4 Baths

ACTIVE

$1,550,000

Virtual Tour

2408 Lafayette Ave, Winter Park, FL 32789

2,838 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

747 McIntyre Ave, Winter Park, FL 32789

1,457 SqFt

3 Beds | 2 Baths

PENDING

$1,500,000

Virtual Tour

1741 Pine Ave, Winter Park, FL 32789

3,297 SqFt

4 Beds | 3 Baths

PENDING

$1,500,000

Virtual Tour

2015 Summerfield Rd, Winter Park, FL 32792

2,958 SqFt

4 Beds | 4 Baths

ACTIVE

$1,495,000

Virtual Tour

1601 Chestnut Ave, Winter Park, FL 32789

2,795 SqFt

4 Beds | 3 Baths

PENDING

$1,475,000

Virtual Tour

1750 Winchester Dr, Winter Park, FL 32789

2,637 SqFt

4 Beds | 4 Baths

ACTIVE

$1,475,000

1600 Barcelona Way, Winter Park, FL 32789

3,014 SqFt

4 Beds | 4 Baths

ACTIVE

$1,400,000

Virtual Tour

1370 Alberta Dr, Winter Park, FL 32789

3,483 SqFt

5 Beds | 6 Baths

ACTIVE

$1,397,000

Virtual Tour

1371 Lyndale Blvd, Winter Park, FL 32789

2,739 SqFt

4 Beds | 3 Baths

ACTIVE

$1,395,000

Virtual Tour

2536 Brookshire Ave, Winter Park, FL 32792

3,140 SqFt

4 Beds | 4 Baths

ACTIVE

$1,395,000

Virtual Tour

1633 Pine Ave, Winter Park, FL 32789

2,481 SqFt

4 Beds | 4 Baths

PENDING

$1,395,000

Virtual Tour

777 Halifax Ave, Winter Park, FL 32792

3,161 SqFt

5 Beds | 5 Baths

ACTIVE

$1,360,000

Virtual Tour

1269 Wading Waters Cir, Winter Park, FL 32792

4,468 SqFt

6 Beds | 4 Baths

ACTIVE

$1,350,000

Virtual Tour

181 N Phelps Ave, Winter Park, FL 32789

3,000 SqFt

4 Beds | 4 Baths

PENDING

$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

2,060 SqFt

4 Beds | 3 Baths

ACTIVE

$1,299,000

1213 Richmond Rd, Winter Park, FL 32789

3,204 SqFt

4 Beds | 3 Baths

ACTIVE

$1,299,000

Virtual Tour

7440 Aloma Ave, Winter Park, FL 32792

4,435 SqFt

5 Beds | 5 Baths

ACTIVE

$1,295,000

Virtual Tour

632 Country Club Dr, Winter Park, FL 32789

2,342 SqFt

3 Beds | 2 Baths

ACTIVE

$1,295,000

Virtual Tour

1611 Chestnut Ave, Winter Park, FL 32789

2,916 SqFt

4 Beds | 4 Baths

ACTIVE

$1,295,000

Virtual Tour

433 Carolina Ave, Winter Park, FL 32789

2,700 SqFt

5 Beds | 4 Baths

ACTIVE

$1,295,000

Virtual Tour

7706 Waunatta Ct, Winter Park, FL 32792

3,858 SqFt

5 Beds | 3 Baths

ACTIVE

$1,290,000

Virtual Tour

1201 Wading Waters Cir, Winter Park, FL 32792

4,266 SqFt

5 Beds | 5 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

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

2,284 SqFt

6 Beds | 4 Baths

ACTIVE

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