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

$8,500,000

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

$6,180,000

Virtual Tour

2211 Azalea Pl, Winter Park, FL 32789

7,278 SqFt

5 Beds | 7 Baths

ACTIVE

$5,800,000

Virtual Tour

541 Virginia Dr, Winter Park, FL 32789

4,725 SqFt

4 Beds | 4 Baths

PENDING

$5,800,000

1221 Richmond Rd, Winter Park, FL 32789

5,164 SqFt

5 Beds | 6 Baths

ACTIVE

$5,750,000

Virtual Tour

1333 Alberta Dr, Winter Park, FL 32789

3,738 SqFt

3 Beds | 4 Baths

ACTIVE

$5,200,000

Virtual Tour

1660 Palmer Ave, Winter Park, FL 32789

6,406 SqFt

5 Beds | 7 Baths

ACTIVE

$4,795,000

Virtual Tour

765 Via Lugano, Winter Park, FL 32789

4,319 SqFt

4 Beds | 5 Baths

ACTIVE

$4,750,000

Virtual Tour

1150 Via Salerno, Winter Park, FL 32789

3,850 SqFt

4 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

PENDING

$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

$3,975,000

1742 Temple Dr, Winter Park, FL 32789

3,658 SqFt

4 Beds | 5 Baths

ACTIVE

$3,895,000

Virtual Tour

1820 Glencoe Rd, Winter Park, FL 32789

4,055 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

PENDING

$3,595,000

Virtual Tour

141 S Phelps Ave, Winter Park, FL 32789

5,878 SqFt

6 Beds | 6 Baths

PENDING

$3,544,999

Virtual Tour

1761 Legion Dr, Winter Park, FL 32789

4,955 SqFt

5 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

$3,400,000

Virtual Tour

473 Fletcher Pl, Winter Park, FL 32789

4,296 SqFt

5 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

$3,250,000

Virtual Tour

641 Virginia Dr, Winter Park, FL 32789

3,223 SqFt

4 Beds | 3 Baths

PENDING

$3,195,000

Virtual Tour

1911 Stonehurst Rd, Winter Park, FL 32789

5,097 SqFt

4 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

PENDING

$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

$2,849,000

Virtual Tour

2652 Lake Howell Ln, Winter Park, FL 32792

4,200 SqFt

5 Beds | 4 Baths

ACTIVE

$2,800,000

Virtual Tour

1341 Place Picardy, Winter Park, FL 32789

4,469 SqFt

5 Beds | 6 Baths

ACTIVE

$2,799,000

Virtual Tour

2550 Venetian Way, Winter Park, FL 32789

4,875 SqFt

4 Beds | 5 Baths

ACTIVE

$2,750,000

Virtual Tour

1860 Via Contessa, Winter Park, FL 32789

7,000 SqFt

8 Beds | 6 Baths

ACTIVE

$2,749,000

1690 Palm Ave, Winter Park, FL 32789

3,967 SqFt

5 Beds | 6 Baths

PENDING

$2,749,000

Virtual Tour

140 E Morse Blvd J, Winter Park, FL 32789

2,143 SqFt

3 Beds | 3 Baths

ACTIVE

$2,725,000

Virtual Tour

1400 Place Picardy, Winter Park, FL 32789

4,338 SqFt

5 Beds | 6 Baths

ACTIVE

$2,650,000

Virtual Tour

1630 Lasbury Ave, Winter Park, FL 32789

4,912 SqFt

5 Beds | 5 Baths

ACTIVE

$2,599,000

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

$2,500,000

Virtual Tour

450 Lakewood Dr, Winter Park, FL 32789

4,676 SqFt

5 Beds | 6 Baths

ACTIVE

$2,495,000

Virtual Tour

940 Lincoln Cir, Winter Park, FL 32789

3,551 SqFt

4 Beds | 5 Baths

PENDING

$2,490,000

Virtual Tour

1795 Greenwich Ave, Winter Park, FL 32789

3,852 SqFt

5 Beds | 6 Baths

PENDING

$2,490,000

Virtual Tour

1602 Alabama Dr Ph404, Winter Park, FL 32789

2,709 SqFt

3 Beds | 4 Baths

ACTIVE

$2,455,000

521 S Phelps Ave, Winter Park, FL 32789

3,883 SqFt

4 Beds | 5 Baths

ACTIVE

$2,399,000

Virtual Tour

922 N Pennsylvania Ave, Winter Park, FL 32789

3,440 SqFt

3 Beds | 4 Baths

ACTIVE

$2,389,000

Virtual Tour

2412 Chantilly Ave, Winter Park, FL 32789

4,506 SqFt

5 Beds | 7 Baths

ACTIVE

$2,295,000

1760 Bryan Ave, Winter Park, FL 32789

3,005 SqFt

4 Beds | 4 Baths

ACTIVE

$2,277,000

140 E Morse Blvd C, Winter Park, FL 32789

2,450 SqFt

2 Beds | 3 Baths

PENDING

$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

$2,195,000

Virtual Tour

1361 Palmer Ave, Winter Park, FL 32789

3,558 SqFt

5 Beds | 4 Baths

ACTIVE

$2,150,000

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

$2,150,000

Virtual Tour

141 Oakwood Way, Winter Park, FL 32789

3,909 SqFt

5 Beds | 4 Baths

ACTIVE

$2,119,000

Virtual Tour

785 N Phelps Ave, Winter Park, FL 32789

2,964 SqFt

5 Beds | 4 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

$1,976,000

Virtual Tour

617 Worthington Dr, Winter Park, FL 32789

3,533 SqFt

5 Beds | 5 Baths

ACTIVE

$1,925,000

Virtual Tour

1355 Hibiscus Ave, Winter Park, FL 32789

4,155 SqFt

5 Beds | 6 Baths

ACTIVE

$1,899,000

Virtual Tour

4469 Old Bear Run, Winter Park, FL 32792

4,288 SqFt

5 Beds | 5 Baths

ACTIVE

$1,895,000

Virtual Tour

622 Penn Pl, Winter Park, FL 32789

2,767 SqFt

3 Beds | 4 Baths

ACTIVE

$1,888,000

Virtual Tour

2407 Lafayette Ave, Winter Park, FL 32789

3,133 SqFt

5 Beds | 5 Baths

ACTIVE

$1,869,000

Virtual Tour

1299 Harding Street, Winter Park, FL 32789

3,784 SqFt

6 Beds | 5 Baths

ACTIVE

$1,825,000

Virtual Tour

446 Alberta Dr, Winter Park, FL 32789

3,263 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

$1,800,000

Virtual Tour

2260 Mulbry Dr, Winter Park, FL 32789

3,246 SqFt

5 Beds | 4 Baths

ACTIVE

$1,799,000

Virtual Tour

1640 Mayfield Ave, Winter Park, FL 32789

2,907 SqFt

3 Beds | 3 Baths

ACTIVE

$1,795,000

Virtual Tour

817 Antonette Ave, Winter Park, FL 32789

3,971 SqFt

4 Beds | 3 Baths

PENDING

$1,795,000

Virtual Tour

1780 Mizell Ave, Winter Park, FL 32789

2,743 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

$1,759,000

1660 Walnut Ave, Winter Park, FL 32789

2,172 SqFt

4 Beds | 4 Baths

PENDING

$1,750,000

Virtual Tour

1270 Arlington Pl, Winter Park, FL 32789

2,964 SqFt

3 Beds | 4 Baths

ACTIVE

$1,749,000

101 S New York Ave Unit 311, Winter Park, FL 32789

3,112 SqFt

3 Beds | 4 Baths

ACTIVE

$1,699,000

Virtual Tour

2402.5 Temple Dr, Winter Park, FL 32789

3,248 SqFt

4 Beds | 5 Baths

ACTIVE

$1,695,000

Virtual Tour

279 Rippling Ln, Winter Park, FL 32789

3,472 SqFt

4 Beds | 3 Baths

PENDING

$1,695,000

1831 Mizell Ave, Winter Park, FL 32789

3,204 SqFt

4 Beds | 4 Baths

ACTIVE

$1,675,000

Virtual Tour

1350 Lyndale Blvd, Winter Park, FL 32789

3,478 SqFt

4 Beds | 5 Baths

ACTIVE

$1,664,900

Virtual Tour

607 Ellen Dr, Winter Park, FL 32789

2,812 SqFt

4 Beds | 5 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

$1,595,000

Virtual Tour

1741 Palmer Ave, Winter Park, FL 32789

2,351 SqFt

3 Beds | 3 Baths

ACTIVE

$1,595,000

Virtual Tour

7841 Georgeann St, Winter Park, FL 32792

4,000 SqFt

4 Beds | 4 Baths

ACTIVE

$1,595,000

Virtual Tour

1733 Harmon Ave, Winter Park, FL 32789

3,267 SqFt

5 Beds | 5 Baths

PENDING

$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

$1,575,000

Virtual Tour

1394 Grove Ter, Winter Park, FL 32789

2,958 SqFt

4 Beds | 4 Baths

PENDING

$1,575,000

Virtual Tour

1473 Berkshire Ave, Winter Park, FL 32789

2,895 SqFt

5 Beds | 4 Baths

ACTIVE

$1,575,000

Virtual Tour

1742 Barcelona Way, Winter Park, FL 32789

3,626 SqFt

5 Beds | 8 Baths

ACTIVE

$1,575,000

Virtual Tour

690 Osceola Ave Unit 604, Winter Park, FL 32789

2,128 SqFt

3 Beds | 3 Baths

ACTIVE

$1,554,950

Virtual Tour

952 Moss Ln, Winter Park, FL 32789

3,474 SqFt

4 Beds | 4 Baths

ACTIVE

$1,550,000

1541 Chestnut Ave, Winter Park, FL 32789

2,840 SqFt

4 Beds | 3 Baths

PENDING

$1,550,000

Virtual Tour

1871 Taylor Ave, Winter Park, FL 32789

3,401 SqFt

4 Beds | 5 Baths

PENDING

266 Listings

Free Access

Free Access

Free Access

Claim Your Home

Almost there!

Log In

Accept Terms

Opt-In

Looks like your phone is invalid.

Would you like to update it?