Winter Park Homes for Sale

$17,486,000

1220 N Park Ave, Winter Park, FL 32789

12,475 SqFt

7 Beds | 7 Baths

ACTIVE

$16,000,000

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

$7,600,000

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

$5,400,000

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

$4,200,000

Virtual Tour

2403 Euston Rd, Winter Park, FL 32789

-- SqFt

-- Beds | -- Baths

ACTIVE

$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

1580 Harris Cir, Winter Park, FL 32789

6,292 SqFt

6 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

$3,950,000

1106 Palmer Ave, Winter Park, FL 32789

6,256 SqFt

4 Beds | 6 Baths

ACTIVE

$3,950,000

Virtual Tour

674 W Morse Blvd, Winter Park, FL 32789

4,390 SqFt

4 Beds | 5 Baths

ACTIVE

$3,790,000

Virtual Tour

637 N Park Ave, Winter Park, FL 32789

4,237 SqFt

3 Beds | 5 Baths

PENDING

$3,595,000

Virtual Tour

1290 Park Ave, Winter Park, FL 32789

3,823 SqFt

4 Beds | 5 Baths

PENDING

$3,595,000

1611 Summerland Ave, Winter Park, FL 32789

4,287 SqFt

5 Beds | 7 Baths

PENDING

$3,500,000

Virtual Tour

1727 Lake Berry Dr, Winter Park, FL 32789

4,961 SqFt

5 Beds | 6 Baths

ACTIVE

$3,499,900

Virtual Tour

200 E Rockwood Way, Winter Park, FL 32789

4,178 SqFt

5 Beds | 5 Baths

PENDING

$3,495,000

Virtual Tour

1150 Via Salerno, Winter Park, FL 32789

3,826 SqFt

4 Beds | 5 Baths

ACTIVE

$3,250,000

Virtual Tour

1476 Grove Ter, Winter Park, FL 32789

5,792 SqFt

5 Beds | 7 Baths

ACTIVE

$3,100,000

4572 Palmetto Ave A, Winter Park, FL 32792

8,843 SqFt

-- Beds | -- Baths

ACTIVE

$3,050,000

Virtual Tour

2138 Lake Dr, Winter Park, FL 32789

5,100 SqFt

4 Beds | 4 Baths

ACTIVE

$2,995,000

1150 Louisiana Ave Bldg 1, Winter Park, FL 32789

2,685 SqFt

-- Beds | -- Baths

ACTIVE

$2,995,000

Virtual Tour

1405 Green Cove Rd, Winter Park, FL 32789

3,772 SqFt

4 Beds | 4 Baths

PENDING

$2,950,000

235 W Fawsett Rd, Winter Park, FL 32789

3,481 SqFt

4 Beds | 5 Baths

ACTIVE

$2,899,000

Virtual Tour

5510 Howell Branch Rd, Winter Park, FL 32792

8,055 SqFt

-- Beds | -- Baths

ACTIVE

$2,695,000

Virtual Tour

617 Penn Pl, Winter Park, FL 32789

4,888 SqFt

4 Beds | 5 Baths

ACTIVE

$2,600,000

Virtual Tour

2412 Chantilly Ave, Winter Park, FL 32789

4,500 SqFt

5 Beds | 7 Baths

ACTIVE

$2,399,000

Virtual Tour

140 E Morse Blvd I, Winter Park, FL 32789

2,291 SqFt

3 Beds | 2 Baths

ACTIVE

$2,395,000

2819 Parkland Dr, Winter Park, FL 32789

3,995 SqFt

4 Beds | 5 Baths

PENDING

$2,340,000

1400 Elizabeth Dr, Winter Park, FL 32789

-- SqFt

-- Beds | -- Baths

PENDING

$2,299,000

Virtual Tour

1460 Sunset Dr, Winter Park, FL 32789

3,155 SqFt

5 Beds | 3 Baths

ACTIVE

$2,275,000

Virtual Tour

2100 Lake Dr, Winter Park, FL 32789

3,555 SqFt

4 Beds | 4 Baths

ACTIVE

$2,250,000

Virtual Tour

1740 Summerland Ave, Winter Park, FL 32789

4,201 SqFt

5 Beds | 6 Baths

PENDING

$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

$2,175,000

2723 Norris Ave, Winter Park, FL 32789

4,000 SqFt

4 Beds | 4 Baths

ACTIVE

$2,100,000

1461 Palm Ave, Winter Park, FL 32789

3,436 SqFt

4 Beds | 5 Baths

PENDING

$2,100,000

Virtual Tour

2156 Talman Ct, Winter Park, FL 32792

7,762 SqFt

5 Beds | 8 Baths

PENDING

$2,094,000

870 Georgia Ave, Winter Park, FL 32789

2,709 SqFt

3 Beds | 3 Baths

PENDING

$2,070,000

Virtual Tour

1251 Woodmere Dr, Winter Park, FL 32789

4,738 SqFt

4 Beds | 4 Baths

ACTIVE

$2,025,000

Virtual Tour

Grove Ave, Winter Park, FL 32792

-- SqFt

-- Beds | -- Baths

ACTIVE

$1,995,000

Virtual Tour

1731 Windsor Dr, Winter Park, FL 32789

3,669 SqFt

4 Beds | 4 Baths

ACTIVE

$1,950,000

Virtual Tour

180 Whipple Ave, Winter Park, FL 32789

-- SqFt

-- Beds | -- Baths

ACTIVE

$1,950,000

Virtual Tour

431 Fletcher Pl, Winter Park, FL 32789

4,257 SqFt

4 Beds | 4 Baths

ACTIVE

$1,900,000

Virtual Tour

559 Genius Dr, Winter Park, FL 32789

3,879 SqFt

3 Beds | 4 Baths

PENDING

$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

2379 Forrest Rd, Winter Park, FL 32789

-- SqFt

-- Beds | -- Baths

ACTIVE

$1,890,000

Virtual Tour

101 S New York Ave Unit 309, Winter Park, FL 32789

2,903 SqFt

3 Beds | 4 Baths

ACTIVE

$1,845,000

Virtual Tour

600 Maiden Ln, Winter Park, FL 32789

3,781 SqFt

4 Beds | 5 Baths

ACTIVE

$1,800,000

698 N New York Ave, Winter Park, FL 32789

-- SqFt

-- Beds | -- Baths

ACTIVE

$1,799,164

Virtual Tour

1331 Hibiscus Ave, Winter Park, FL 32789

4,137 SqFt

5 Beds | 5 Baths

ACTIVE

$1,799,000

Virtual Tour

1871 Taylor Ave, Winter Park, FL 32789

3,401 SqFt

4 Beds | 5 Baths

ACTIVE

$1,795,000

Virtual Tour

1531 Place Picardy, Winter Park, FL 32789

3,964 SqFt

4 Beds | 4 Baths

ACTIVE

$1,775,000

Virtual Tour

1841 W Fairbanks Ave, Winter Park, FL 32789

4,198 SqFt

-- Beds | -- Baths

ACTIVE

$1,750,000

Virtual Tour

40 Palmer Ave, Winter Park, FL 32789

4,166 SqFt

5 Beds | 5 Baths

ACTIVE

$1,700,000

Virtual Tour

4091 Scarlet Iris Pl, Winter Park, FL 32792

6,252 SqFt

6 Beds | 6 Baths

ACTIVE

$1,699,900

270 E Lake Sue Ave, Winter Park, FL 32789

3,151 SqFt

5 Beds | 5 Baths

ACTIVE

$1,699,000

Virtual Tour

450 Ololu Dr, Winter Park, FL 32789

4,518 SqFt

5 Beds | 6 Baths

PENDING

$1,699,000

Virtual Tour

1451 Lyndale Blvd, Winter Park, FL 32789

3,853 SqFt

5 Beds | 4 Baths

ACTIVE

$1,699,000

Virtual Tour

341 E Reading Way, Winter Park, FL 32789

3,723 SqFt

4 Beds | 4 Baths

ACTIVE

$1,695,000

Virtual Tour

621 Huntington Ave, Winter Park, FL 32789

2,399 SqFt

3 Beds | 4 Baths

ACTIVE

$1,650,000

580 Palmer Ave, Winter Park, FL 32789

3,055 SqFt

3 Beds | 3 Baths

PENDING

$1,649,000

Virtual Tour

2435 Chantilly Ave, Winter Park, FL 32789

3,055 SqFt

4 Beds | 5 Baths

PENDING

$1,625,000

Virtual Tour

518 W Swoope Ave, Winter Park, FL 32789

2,585 SqFt

3 Beds | 3 Baths

ACTIVE

$1,600,000

Virtual Tour

281 Brewer Ave, Winter Park, FL 32789

4,029 SqFt

5 Beds | 5 Baths

ACTIVE

$1,600,000

Virtual Tour

2121 Loch Lomond Dr, Winter Park, FL 32792

3,167 SqFt

4 Beds | 5 Baths

PENDING

$1,600,000

Virtual Tour

1600 Barcelona Way, Winter Park, FL 32789

3,014 SqFt

4 Beds | 4 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

Virtual Tour

506 N Wymore Rd, Winter Park, FL 32789

2,754 SqFt

-- Beds | -- Baths

ACTIVE

$1,600,000

Virtual Tour

512 N Wymore Rd, Winter Park, FL 32789

-- SqFt

-- Beds | -- Baths

ACTIVE

$1,499,000

Virtual Tour

2531 Lafayette Ave, Winter Park, FL 32789

2,742 SqFt

4 Beds | 4 Baths

ACTIVE

$1,485,000

Virtual Tour

511 Fairfax Ave, Winter Park, FL 32789

3,463 SqFt

4 Beds | 3 Baths

PENDING

$1,450,000

Virtual Tour

601 Ellen Dr, Winter Park, FL 32789

2,841 SqFt

4 Beds | 5 Baths

ACTIVE

$1,450,000

Virtual Tour

1700 Diana Dr, Winter Park, FL 32789

2,935 SqFt

4 Beds | 4 Baths

ACTIVE

$1,399,000

Virtual Tour

1511 Palm Ave, Winter Park, FL 32789

2,460 SqFt

4 Beds | 4 Baths

PENDING

$1,395,000

Virtual Tour

2019 Natalen Rd, Winter Park, FL 32792

3,093 SqFt

4 Beds | 4 Baths

ACTIVE

$1,395,000

Virtual Tour

1621 Lakehurst Ave, Winter Park, FL 32789

-- SqFt

-- Beds | -- Baths

PENDING

$1,350,000

Virtual Tour

2417 Lafayette Ave, Winter Park, FL 32789

2,080 SqFt

4 Beds | 3 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

ACTIVE

$1,275,000

1000 Howell Branch Rd, Winter Park, FL 32789

-- SqFt

-- Beds | -- Baths

ACTIVE

$1,250,000

Virtual Tour

1455 W Fairbanks Ave, Winter Park, FL 32789

1,672 SqFt

-- Beds | -- Baths

PENDING

$1,250,000

Virtual Tour

1503 Palmer Ave, Winter Park, FL 32789

2,688 SqFt

4 Beds | 3 Baths

ACTIVE

$1,250,000

Virtual Tour

1320 Orchid Ave, Winter Park, FL 32789

2,998 SqFt

4 Beds | 4 Baths

ACTIVE

$1,250,000

Virtual Tour

2600 Venetian Way, Winter Park, FL 32789

1,368 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

$1,240,000

1611 Chestnut Ave, Winter Park, FL 32789

3,000 SqFt

4 Beds | 4 Baths

ACTIVE

$1,225,000

Virtual Tour

106 S Interlachen Ave 518b, Winter Park, FL 32789

1,834 SqFt

3 Beds | 2 Baths

PENDING

$1,200,000

Virtual Tour

4765 Seminole Ave, Winter Park, FL 32792

1,684 SqFt

-- Beds | -- Baths

ACTIVE

$1,195,000

Virtual Tour

1879 Lake Spier Dr, Winter Park, FL 32789

2,350 SqFt

3 Beds | 2 Baths

PENDING

$1,195,000

Virtual Tour

1531 Sunset Dr, Winter Park, FL 32789

2,619 SqFt

4 Beds | 3 Baths

PENDING

$1,150,000

Virtual Tour

1554 Harris Cir, Winter Park, FL 32789

2,801 SqFt

3 Beds | 3 Baths

ACTIVE

$1,140,000

Virtual Tour

1226 Germaine Dr, Winter Park, FL 32789

3,177 SqFt

4 Beds | 3 Baths

PENDING

$1,100,000

Virtual Tour

1716 Palmer Ave, Winter Park, FL 32789

3,243 SqFt

3 Beds | 3 Baths

ACTIVE

$1,100,000

Virtual Tour

100 S Virginia Ave Unit 201, Winter Park, FL 32789

2,756 SqFt

3 Beds | 3 Baths

PENDING

$1,099,000

Virtual Tour

2315 Janice Ave, Winter Park, FL 32789

3,249 SqFt

5 Beds | 3 Baths

PENDING

$1,075,000

Virtual Tour

2521 Minnesota Ave, Winter Park, FL 32789

3,658 SqFt

5 Beds | 4 Baths

ACTIVE

$1,055,000

Virtual Tour

911 Osceola Ave, Winter Park, FL 32789

2,342 SqFt

3 Beds | 4 Baths

ACTIVE

$1,050,000

1911 S Lakemont Ave, Winter Park, FL 32792

2,085 SqFt

3 Beds | 4 Baths

PENDING

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