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

$8,799,000

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

$5,200,000

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

$4,600,000

Virtual Tour

2118 Lake Dr, Winter Park, FL 32789

6,000 SqFt

6 Beds | 6 Baths

PENDING

$4,599,000

985 Lincoln Cir, Winter Park, FL 32789

3,660 SqFt

5 Beds | 7 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

ACTIVE

$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

PENDING

$4,100,000

Virtual Tour

1782 Pine Ave, Winter Park, FL 32789

4,782 SqFt

5 Beds | 7 Baths

ACTIVE

$3,980,000

Virtual Tour

141 S Phelps Ave, Winter Park, FL 32789

5,878 SqFt

6 Beds | 6 Baths

ACTIVE

$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

861 Bonita Dr, Winter Park, FL 32789

6,939 SqFt

6 Beds | 8 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

$3,499,500

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

$3,350,000

Virtual Tour

940 Lincoln Cir, Winter Park, FL 32789

3,551 SqFt

4 Beds | 5 Baths

ACTIVE

$3,295,000

Virtual Tour

532 Worthington Dr, Winter Park, FL 32789

3,974 SqFt

5 Beds | 6 Baths

ACTIVE

$3,288,000

Virtual Tour

731 Williams Dr, Winter Park, FL 32789

4,260 SqFt

5 Beds | 6 Baths

ACTIVE

$3,250,000

Virtual Tour

266 Chase Ave, Winter Park, FL 32789

4,088 SqFt

5 Beds | 6 Baths

PENDING

$3,249,000

Virtual Tour

1730 Winchester Dr, Winter Park, FL 32789

4,080 SqFt

5 Beds | 6 Baths

ACTIVE

$3,200,000

Virtual Tour

1891 Lake Spier Dr, Winter Park, FL 32789

3,932 SqFt

5 Beds | 4 Baths

ACTIVE

$3,195,000

Virtual Tour

1020 Mayfield Ave, Winter Park, FL 32789

2,663 SqFt

4 Beds | 3 Baths

ACTIVE

$3,195,000

Virtual Tour

1911 Stonehurst Rd, Winter Park, FL 32789

5,097 SqFt

4 Beds | 6 Baths

ACTIVE

$3,150,000

Virtual Tour

541 W Canton Ave, Winter Park, FL 32789

3,553 SqFt

4 Beds | 4 Baths

ACTIVE

$2,950,000

Virtual Tour

700 Jackson Ave, Winter Park, FL 32789

10,174 SqFt

-- Beds | -- Baths

ACTIVE

$2,949,999

2652 Lake Howell Ln, Winter Park, FL 32792

3,898 SqFt

5 Beds | 4 Baths

ACTIVE

$2,900,000

Virtual Tour

1401 Green Cove Rd, Winter Park, FL 32789

5,416 SqFt

4 Beds | 7 Baths

ACTIVE

$2,900,000

Virtual Tour

1860 Via Contessa, Winter Park, FL 32789

7,000 SqFt

8 Beds | 6 Baths

ACTIVE

$2,825,000

Virtual Tour

1400 Place Picardy, Winter Park, FL 32789

4,338 SqFt

5 Beds | 6 Baths

ACTIVE

$2,800,000

4572 Palmetto Ave A, Winter Park, FL 32792

8,843 SqFt

-- Beds | -- 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

$2,550,000

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

PENDING

$2,499,000

Virtual Tour

1460 Minnesota Ave, Winter Park, FL 32789

2,700 SqFt

-- Beds | -- Baths

ACTIVE

$2,490,000

Virtual Tour

1795 Greenwich Ave, Winter Park, FL 32789

3,852 SqFt

5 Beds | 6 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

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

$2,254,000

Virtual Tour

141 Oakwood Way, Winter Park, FL 32789

3,909 SqFt

5 Beds | 4 Baths

ACTIVE

$2,249,999

Virtual Tour

2614 Parkland Dr, Winter Park, FL 32789

3,307 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

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

$2,095,000

Virtual Tour

1840 Bryan Ave, Winter Park, FL 32789

3,727 SqFt

4 Beds | 4 Baths

ACTIVE

$2,000,000

2260 Mulbry Dr, Winter Park, FL 32789

3,246 SqFt

5 Beds | 4 Baths

ACTIVE

$1,999,999

Virtual Tour

1299 Harding Street, Winter Park, FL 32789

3,784 SqFt

6 Beds | 5 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

$1,996,000

Virtual Tour

4469 Old Bear Run, Winter Park, FL 32792

4,288 SqFt

5 Beds | 5 Baths

ACTIVE

$1,990,000

Virtual Tour

681 Balmoral Rd, Winter Park, FL 32789

n/a SqFt

-- Beds | -- Baths

PENDING

$1,950,000

Virtual Tour

622 Penn Pl, Winter Park, FL 32789

2,767 SqFt

3 Beds | 4 Baths

ACTIVE

$1,899,000

Virtual Tour

2402.5 Temple Dr, Winter Park, FL 32789

3,248 SqFt

4 Beds | 5 Baths

ACTIVE

$1,888,000

Virtual Tour

2407 Lafayette Ave, Winter Park, FL 32789

3,133 SqFt

5 Beds | 5 Baths

ACTIVE

$1,875,000

Virtual Tour

1970 Laurel Rd, Winter Park, FL 32789

3,440 SqFt

4 Beds | 4 Baths

PENDING

$1,850,000

Virtual Tour

313 Sylvan Dr, Winter Park, FL 32789

n/a SqFt

-- Beds | -- Baths

ACTIVE

$1,825,000

Virtual Tour

817 Antonette Ave, Winter Park, FL 32789

3,971 SqFt

4 Beds | 3 Baths

PENDING

$1,800,000

1682 Arbor Park Dr, Winter Park, FL 32789

2,950 SqFt

4 Beds | 4 Baths

PENDING

$1,799,000

Virtual Tour

1742 Barcelona Way, Winter Park, FL 32789

3,626 SqFt

5 Beds | 8 Baths

ACTIVE

$1,795,000

2379 Forrest Rd, Winter Park, FL 32789

n/a SqFt

-- Beds | -- 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

PENDING

$1,759,000

1660 Walnut Ave, Winter Park, FL 32789

2,172 SqFt

4 Beds | 4 Baths

PENDING

$1,749,000

Virtual Tour

2339 Lafayette Ave, Winter Park, FL 32789

3,379 SqFt

4 Beds | 6 Baths

ACTIVE

$1,749,000

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

3,112 SqFt

3 Beds | 4 Baths

ACTIVE

$1,739,000

Virtual Tour

279 Rippling Ln, Winter Park, FL 32789

3,472 SqFt

4 Beds | 3 Baths

ACTIVE

$1,725,000

1181 Via Capri, Winter Park, FL 32789

n/a SqFt

-- Beds | -- Baths

ACTIVE

$1,695,000

1831 Mizell Ave, Winter Park, FL 32789

3,204 SqFt

4 Beds | 4 Baths

ACTIVE

$1,679,000

Virtual Tour

7507 Aloma Ave, Winter Park, FL 32792

6,169 SqFt

-- Beds | -- 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

$1,600,000

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

$1,590,000

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

690 Osceola Ave Unit 604, Winter Park, FL 32789

2,128 SqFt

3 Beds | 3 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

2015 Summerfield Rd, Winter Park, FL 32792

2,958 SqFt

4 Beds | 4 Baths

ACTIVE

$1,495,000

Virtual Tour

1661 Woodland Ave, Winter Park, FL 32789

3,215 SqFt

3 Beds | 4 Baths

ACTIVE

$1,495,000

1644 Hibiscus Ave, Winter Park, FL 32789

2,145 SqFt

3 Beds | 3 Baths

ACTIVE

$1,475,000

1600 Barcelona Way, Winter Park, FL 32789

3,014 SqFt

4 Beds | 4 Baths

ACTIVE

$1,450,000

Virtual Tour

2105 Fosgate Dr, Winter Park, FL 32789

3,068 SqFt

5 Beds | 4 Baths

ACTIVE

$1,425,000

Virtual Tour

1750 Winchester Dr, Winter Park, FL 32789

2,637 SqFt

4 Beds | 4 Baths

ACTIVE

$1,400,000

Virtual Tour

2525 Venetian Way, Winter Park, FL 32789

1,993 SqFt

3 Beds | 3 Baths

ACTIVE

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