Winter Park Homes for Sale

$13,500,000

Virtual Tour

1461 Via Tuscany, Winter Park, FL 32789

8,353 SqFt

5 Beds | 6 Baths

ACTIVE

$10,950,000

4 Isle Of Sicily, Winter Park, FL 32789

9,522 SqFt

5 Beds | 8 Baths

ACTIVE

$7,250,000

Virtual Tour

1001 Anchorage Ct, Winter Park, FL 32789

8,883 SqFt

5 Beds | 7 Baths

ACTIVE

$6,750,000

Virtual Tour

654 W Morse Blvd, Winter Park, FL 32789

8,752 SqFt

5 Beds | 8 Baths

ACTIVE

$6,475,000

901 Golfview Terrace, Winter Park, FL 32789

5,406 SqFt

5 Beds | 6 Baths

PENDING

$5,995,000

300 S Interlachen Ave Unit 601, Winter Park, FL 32789

5,430 SqFt

4 Beds | 5 Baths

PENDING

$5,400,000

Virtual Tour

2228 Azalea Pl, Winter Park, FL 32789

5,072 SqFt

5 Beds | 6 Baths

ACTIVE

$4,900,000

Virtual Tour

550 Palmer Ave, Winter Park, FL 32789

5,952 SqFt

5 Beds | 8 Baths

ACTIVE

$4,400,000

Virtual Tour

1391 Richmond Rd, Winter Park, FL 32789

4,635 SqFt

4 Beds | 6 Baths

ACTIVE

$4,299,000

Virtual Tour

664 W Morse Blvd, Winter Park, FL 32789

5,819 SqFt

4 Beds | 6 Baths

PENDING

$4,250,000

Virtual Tour

120 Trismen Ter, Winter Park, FL 32789

4,072 SqFt

4 Beds | 5 Baths

PENDING

$3,999,999

Virtual Tour

2056 Lake Dr, Winter Park, FL 32789

5,907 SqFt

5 Beds | 6 Baths

ACTIVE

$3,995,000

Virtual Tour

2379 Forrest Rd, Winter Park, FL 32789

4,483 SqFt

5 Beds | 7 Baths

ACTIVE

$3,990,000

Virtual Tour

140 E Morse Blvd J, Winter Park, FL 32789

2,143 SqFt

3 Beds | 3 Baths

ACTIVE

$3,800,000

Virtual Tour

674 W Morse Blvd, Winter Park, FL 32789

4,390 SqFt

4 Beds | 5 Baths

ACTIVE

$3,500,000

Virtual Tour

1727 Lake Berry Dr, Winter Park, FL 32789

4,961 SqFt

5 Beds | 6 Baths

ACTIVE

$3,500,000

Virtual Tour

1635 Highland Rd, Winter Park, FL 32789

4,325 SqFt

5 Beds | 6 Baths

ACTIVE

$3,495,000

Virtual Tour

1150 Via Salerno, Winter Park, FL 32789

3,826 SqFt

4 Beds | 5 Baths

ACTIVE

$3,385,000

1824 Harland Park Dr, Winter Park, FL 32789

4,522 SqFt

6 Beds | 5 Baths

ACTIVE

$3,350,000

2080 Sharon Rd, Winter Park, FL 32789

4,080 SqFt

4 Beds | 6 Baths

ACTIVE

$3,095,000

633 S Phelps Ave, Winter Park, FL 32789

4,950 SqFt

5 Beds | 5 Baths

ACTIVE

$3,050,000

Virtual Tour

2138 Lake Dr, Winter Park, FL 32789

5,100 SqFt

4 Beds | 4 Baths

ACTIVE

$2,850,000

235 W Fawsett Rd, Winter Park, FL 32789

3,481 SqFt

4 Beds | 5 Baths

PENDING

$2,750,000

2726 Lake Howell Ln, Winter Park, FL 32792

4,413 SqFt

4 Beds | 4 Baths

ACTIVE

$2,749,000

Virtual Tour

1741 Glencoe Rd, Winter Park, FL 32789

4,692 SqFt

4 Beds | 5 Baths

ACTIVE

$2,649,000

Virtual Tour

520 Shepherd Ave, Winter Park, FL 32789

4,587 SqFt

4 Beds | 4 Baths

PENDING

$2,499,000

Virtual Tour

200 S Interlachen Ave Unit 450, Winter Park, FL 32789

3,110 SqFt

3 Beds | 4 Baths

ACTIVE

$2,399,000

Virtual Tour

140 E Morse Blvd I, Winter Park, FL 32789

2,291 SqFt

3 Beds | 2 Baths

PENDING

$2,350,000

1640 Oneco Ave, Winter Park, FL 32789

4,000 SqFt

5 Beds | 6 Baths

ACTIVE

$2,275,000

Virtual Tour

2100 Lake Dr, Winter Park, FL 32789

3,555 SqFt

4 Beds | 4 Baths

ACTIVE

$2,249,900

1022 McKean Cir, Winter Park, FL 32789

4,610 SqFt

4 Beds | 4 Baths

PENDING

$2,200,000

Virtual Tour

465 N Phelps Ave, Winter Park, FL 32789

4,517 SqFt

7 Beds | 6 Baths

ACTIVE

$2,195,000

2701 Norris Ave, Winter Park, FL 32789

3,259 SqFt

4 Beds | 4 Baths

ACTIVE

$2,175,000

2723 Norris Ave, Winter Park, FL 32789

4,000 SqFt

4 Beds | 4 Baths

ACTIVE

$1,995,000

Virtual Tour

1731 Windsor Dr, Winter Park, FL 32789

3,669 SqFt

4 Beds | 4 Baths

ACTIVE

$1,995,000

Virtual Tour

1800 Bryan Ave, Winter Park, FL 32789

2,951 SqFt

4 Beds | 5 Baths

ACTIVE

$1,995,000

Virtual Tour

106 S Interlachen Ave 219a, Winter Park, FL 32789

1,952 SqFt

3 Beds | 2 Baths

ACTIVE

$1,950,000

Virtual Tour

513 Worthington Dr, Winter Park, FL 32789

3,112 SqFt

3 Beds | 4 Baths

ACTIVE

$1,950,000

Virtual Tour

1814 Barker Dr, Winter Park, FL 32789

4,100 SqFt

5 Beds | 4 Baths

ACTIVE

$1,899,000

Virtual Tour

130 Burks Cir, Winter Park, FL 32789

3,733 SqFt

4 Beds | 5 Baths

PENDING

$1,895,000

Virtual Tour

151 N Virginia Ave, Winter Park, FL 32789

2,778 SqFt

2 Beds | 3 Baths

ACTIVE

$1,895,000

Virtual Tour

1020 N Pennsylvania, Winter Park, FL 32789

2,609 SqFt

4 Beds | 3 Baths

ACTIVE

$1,895,000

Virtual Tour

1530 Via Tuscany, Winter Park, FL 32789

3,341 SqFt

4 Beds | 4 Baths

ACTIVE

$1,850,000

Virtual Tour

431 Fletcher Pl, Winter Park, FL 32789

4,257 SqFt

4 Beds | 4 Baths

ACTIVE

$1,799,900

Virtual Tour

2016 Lake Dr, Winter Park, FL 32789

2,560 SqFt

3 Beds | 2 Baths

ACTIVE

$1,799,000

Virtual Tour

1400 Lyndale Blvd, Winter Park, FL 32789

2,829 SqFt

4 Beds | 4 Baths

ACTIVE

$1,795,000

Virtual Tour

2435 Lafayette Ave, Winter Park, FL 32789

2,785 SqFt

4 Beds | 4 Baths

ACTIVE

$1,795,000

Virtual Tour

600 Maiden Ln, Winter Park, FL 32789

3,781 SqFt

4 Beds | 5 Baths

ACTIVE

$1,750,000

Virtual Tour

1800 Temple Dr, Winter Park, FL 32789

3,298 SqFt

4 Beds | 4 Baths

ACTIVE

$1,700,000

Virtual Tour

4091 Scarlet Iris Pl, Winter Park, FL 32792

6,252 SqFt

6 Beds | 6 Baths

PENDING

$1,699,000

Virtual Tour

341 E Reading Way, Winter Park, FL 32789

3,723 SqFt

4 Beds | 4 Baths

ACTIVE

$1,649,000

Virtual Tour

1871 Taylor Ave, Winter Park, FL 32789

3,401 SqFt

4 Beds | 5 Baths

ACTIVE

$1,600,000

Virtual Tour

504 N Wymore Rd, Winter Park, FL 32789

924 SqFt

2 Beds | 1 Bath

ACTIVE

$1,600,000

571 Lake Front Blvd, Winter Park, FL 32789

1,620 SqFt

2 Beds | 2 Baths

ACTIVE

$1,600,000

Virtual Tour

281 Brewer Ave, Winter Park, FL 32789

4,029 SqFt

5 Beds | 5 Baths

ACTIVE

$1,598,880

Virtual Tour

1331 Hibiscus Ave, Winter Park, FL 32789

4,137 SqFt

5 Beds | 5 Baths

ACTIVE

$1,595,000

Virtual Tour

40 Palmer Ave, Winter Park, FL 32789

4,166 SqFt

5 Beds | 5 Baths

ACTIVE

$1,590,000

Virtual Tour

311 E Morse Blvd 1-1, Winter Park, FL 32789

2,066 SqFt

3 Beds | 2 Baths

PENDING

$1,550,000

Virtual Tour

1600 Barcelona Way, Winter Park, FL 32789

3,014 SqFt

4 Beds | 4 Baths

ACTIVE

$1,550,000

1805 Harland Park Dr, Winter Park, FL 32789

3,052 SqFt

4 Beds | 4 Baths

ACTIVE

$1,545,000

Virtual Tour

518 W Swoope Ave, Winter Park, FL 32789

2,734 SqFt

3 Beds | 3 Baths

ACTIVE

$1,499,990

Virtual Tour

413 Balmoral Rd, Winter Park, FL 32789

3,845 SqFt

3 Beds | 3 Baths

ACTIVE

$1,495,000

Virtual Tour

621 Huntington Ave, Winter Park, FL 32789

2,399 SqFt

3 Beds | 4 Baths

ACTIVE

$1,495,000

Virtual Tour

1701 Summerland, Winter Park, FL 32789

3,148 SqFt

4 Beds | 3 Baths

ACTIVE

$1,450,000

Virtual Tour

1270 Arlington Pl, Winter Park, FL 32789

2,964 SqFt

3 Beds | 4 Baths

ACTIVE

$1,450,000

Virtual Tour

601 Ellen Dr, Winter Park, FL 32789

2,841 SqFt

4 Beds | 5 Baths

PENDING

$1,445,000

Virtual Tour

1420 Magnolia Ave, Winter Park, FL 32789

3,174 SqFt

4 Beds | 4 Baths

PENDING

$1,400,000

Virtual Tour

504 W Swoope Ave, Winter Park, FL 32789

2,796 SqFt

3 Beds | 3 Baths

ACTIVE

$1,399,000

Virtual Tour

1717 Hollywood Ave, Winter Park, FL 32789

3,353 SqFt

4 Beds | 3 Baths

ACTIVE

$1,399,000

Virtual Tour

1511 Palm Ave, Winter Park, FL 32789

2,460 SqFt

4 Beds | 4 Baths

PENDING

$1,399,000

Virtual Tour

2531 Lafayette Ave, Winter Park, FL 32789

2,742 SqFt

4 Beds | 4 Baths

ACTIVE

$1,395,000

Virtual Tour

1049 Tuscany Pl, Winter Park, FL 32789

2,471 SqFt

4 Beds | 2 Baths

ACTIVE

$1,395,000

Virtual Tour

2019 Natalen Rd, Winter Park, FL 32792

3,093 SqFt

4 Beds | 4 Baths

ACTIVE

$1,375,000

Virtual Tour

1405 Chapman Cir Or, Winter Park, FL 32789

2,950 SqFt

3 Beds | 4 Baths

ACTIVE

$1,350,000

Virtual Tour

800 Hamilton Place Ct, Winter Park, FL 32789

3,363 SqFt

3 Beds | 4 Baths

ACTIVE

$1,350,000

Virtual Tour

311 E Morse Blvd 6-18, Winter Park, FL 32789

2,096 SqFt

2 Beds | 2 Baths

ACTIVE

$1,349,000

Virtual Tour

132 Burks Cir, Winter Park, FL 32789

3,022 SqFt

4 Beds | 5 Baths

PENDING

$1,325,000

Virtual Tour

1525 Wilbar Cir, Winter Park, FL 32789

2,842 SqFt

4 Beds | 5 Baths

ACTIVE

$1,295,000

2131 Loch Lomond Dr, Winter Park, FL 32792

2,855 SqFt

4 Beds | 5 Baths

PENDING

$1,279,000

Virtual Tour

1921 Englewood Rd, Winter Park, FL 32789

2,922 SqFt

3 Beds | 3 Baths

PENDING

$1,275,000

Virtual Tour

690 Osceola Ave Unit 504, Winter Park, FL 32789

2,079 SqFt

3 Beds | 3 Baths

ACTIVE

$1,249,900

Virtual Tour

1737 Indiana Ave, Winter Park, FL 32789

2,984 SqFt

4 Beds | 4 Baths

ACTIVE

$1,200,000

Virtual Tour

2600 Venetian Way, Winter Park, FL 32789

1,368 SqFt

3 Beds | 3 Baths

ACTIVE

$1,199,000

Virtual Tour

2417 Lafayette Ave, Winter Park, FL 32789

2,080 SqFt

4 Beds | 3 Baths

ACTIVE

$1,199,000

Virtual Tour

1700 Diana Dr, Winter Park, FL 32789

2,935 SqFt

5 Beds | 4 Baths

PENDING

$1,179,000

Virtual Tour

1913 S Lakemont Ave, Winter Park, FL 32792

2,085 SqFt

3 Beds | 4 Baths

ACTIVE

$1,150,000

Virtual Tour

1772 Mondrian Cir, Winter Park, FL 32789

2,193 SqFt

3 Beds | 4 Baths

ACTIVE

$1,111,000

Virtual Tour

1305 Heavenly Cove, Winter Park, FL 32792

2,654 SqFt

4 Beds | 3 Baths

ACTIVE

$1,099,000

1887 Lake Spier Dr, Winter Park, FL 32789

1,852 SqFt

4 Beds | 2 Baths

PENDING

$1,075,000

Virtual Tour

2521 Minnesota Ave, Winter Park, FL 32789

3,658 SqFt

5 Beds | 4 Baths

PENDING

$1,050,000

1911 S Lakemont Ave, Winter Park, FL 32792

2,085 SqFt

3 Beds | 4 Baths

PENDING

$1,049,000

Virtual Tour

1602 Alabama Dr Unit 107, Winter Park, FL 32789

993 SqFt

2 Beds | 2 Baths

PENDING

$1,020,000

Virtual Tour

210 Laurel Park Ct, Winter Park, FL 32792

2,867 SqFt

4 Beds | 3 Baths

ACTIVE

$1,000,000

1927 S Lakemont Ave, Winter Park, FL 32792

2,104 SqFt

3 Beds | 4 Baths

PENDING

$1,000,000

1929 S Lakemont Ave, Winter Park, FL 32792

2,085 SqFt

3 Beds | 4 Baths

PENDING

$999,000

Virtual Tour

1716 Palmer Ave, Winter Park, FL 32789

3,243 SqFt

3 Beds | 3 Baths

ACTIVE

$997,500

Virtual Tour

2400 Roxbury Rd, Winter Park, FL 32789

3,110 SqFt

4 Beds | 4 Baths

ACTIVE

$995,000

Virtual Tour

911 Osceola Ave, Winter Park, FL 32789

2,342 SqFt

3 Beds | 4 Baths

ACTIVE

$995,000

Virtual Tour

1320 Orchid Ave, Winter Park, FL 32789

2,998 SqFt

4 Beds | 4 Baths

ACTIVE

$991,500

Virtual Tour

2430 Roxbury Rd, Winter Park, FL 32789

2,811 SqFt

4 Beds | 4 Baths

ACTIVE

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