Winter Park Homes for Sale

$17,486,000

1220 N Park Ave, Winter Park, FL 32789

12,475 SqFt

7 Beds | 7 Baths

ACTIVE

$3,999,999

Virtual Tour

2056 Lake Dr, Winter Park, FL 32789

5,907 SqFt

5 Beds | 6 Baths

ACTIVE

$3,950,000

1106 Palmer Ave, Winter Park, FL 32789

6,256 SqFt

4 Beds | 6 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

$3,050,000

Virtual Tour

2138 Lake Dr, Winter Park, FL 32789

5,100 SqFt

4 Beds | 4 Baths

ACTIVE

$2,950,000

235 W Fawsett Rd, Winter Park, FL 32789

3,481 SqFt

4 Beds | 5 Baths

ACTIVE

$2,695,000

Virtual Tour

617 Penn Pl, Winter Park, FL 32789

4,888 SqFt

4 Beds | 5 Baths

ACTIVE

$2,340,000

1400 Elizabeth Dr, Winter Park, FL 32789

-- SqFt

-- Beds | -- Baths

PENDING

$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

$2,175,000

2723 Norris Ave, Winter Park, FL 32789

4,000 SqFt

4 Beds | 4 Baths

ACTIVE

$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

$1,950,000

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

$1,895,000

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

$1,799,164

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

$1,700,000

Virtual Tour

4091 Scarlet Iris Pl, Winter Park, FL 32792

6,252 SqFt

6 Beds | 6 Baths

ACTIVE

$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

$1,600,000

Virtual Tour

281 Brewer Ave, Winter Park, FL 32789

4,029 SqFt

5 Beds | 5 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

1700 Diana Dr, Winter Park, FL 32789

2,935 SqFt

4 Beds | 4 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

$1,195,000

Virtual Tour

1879 Lake Spier Dr, Winter Park, FL 32789

2,350 SqFt

3 Beds | 2 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

$1,099,000

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

$1,015,000

513 Dunblane Dr, Winter Park, FL 32792

3,022 SqFt

3 Beds | 3 Baths

ACTIVE

$998,000

Virtual Tour

1113 Via Del Mar, Winter Park, FL 32789

2,012 SqFt

3 Beds | 2 Baths

PENDING

$984,899

Virtual Tour

1401 Michigan Ave, Winter Park, FL 32789

2,505 SqFt

4 Beds | 3 Baths

ACTIVE

$939,000

Virtual Tour

244 W Kings Way, Winter Park, FL 32789

-- SqFt

-- Beds | -- Baths

ACTIVE

$899,900

Virtual Tour

1872 Jessica Ct, Winter Park, FL 32789

2,607 SqFt

4 Beds | 3 Baths

ACTIVE

$899,000

Virtual Tour

1500 Harris Cir, Winter Park, FL 32789

1,950 SqFt

2 Beds | 3 Baths

PENDING

$899,000

Virtual Tour

412 Fletcher Pl, Winter Park, FL 32789

3,146 SqFt

3 Beds | 4 Baths

PENDING

$824,900

Virtual Tour

737 N Capen Ave, Winter Park, FL 32789

1,930 SqFt

3 Beds | 2 Baths

PENDING

$820,000

Virtual Tour

1825 Loch Berry Rd, Winter Park, FL 32789

2,308 SqFt

3 Beds | 2 Baths

PENDING

$779,990

27 Stymie Pl, Winter Park, FL 32789

2,327 SqFt

5 Beds | 3 Baths

ACTIVE

$779,000

Virtual Tour

1437 Miller Ave, Winter Park, FL 32789

-- SqFt

-- Beds | -- Baths

ACTIVE

$775,000

Virtual Tour

2286 Marsh Sedge Ln, Winter Park, FL 32792

2,192 SqFt

4 Beds | 3 Baths

ACTIVE

$767,000

1231 Kenwood Ave, Winter Park, FL 32789

1,672 SqFt

3 Beds | 2 Baths

ACTIVE

$715,000

Virtual Tour

2852 Sheriff Way, Winter Park, FL 32792

2,036 SqFt

4 Beds | 3 Baths

ACTIVE

$699,000

Virtual Tour

1871 Barker Dr, Winter Park, FL 32789

2,231 SqFt

3 Beds | 3 Baths

ACTIVE

$695,900

Virtual Tour

1131 Oxford Rd, Winter Park, FL 32789

1,608 SqFt

2 Beds | 2 Baths

PENDING

$695,000

Virtual Tour

1035 Minnesota Ave, Winter Park, FL 32789

1,638 SqFt

3 Beds | 2 Baths

ACTIVE

$674,900

1740 Anzle Ave, Winter Park, FL 32789

1,808 SqFt

3 Beds | 2 Baths

ACTIVE

$658,000

Virtual Tour

220 Blossom Ln, Winter Park, FL 32789

2,193 SqFt

3 Beds | 2 Baths

ACTIVE

$650,000

Virtual Tour

730 W Swoope Ave, Winter Park, FL 32789

2,132 SqFt

5 Beds | 3 Baths

ACTIVE

$619,000

Virtual Tour

1425 Chestnut Ave, Winter Park, FL 32789

1,090 SqFt

2 Beds | 1 Bath

ACTIVE

$610,000

1122 Wildmeadow Run, Winter Park, FL 32792

1,790 SqFt

4 Beds | 3 Baths

PENDING

$605,000

Virtual Tour

1174 Wildmeadow Run, Winter Park, FL 32792

1,770 SqFt

3 Beds | 3 Baths

PENDING

$589,500

5233 Lake Howell Rd, Winter Park, FL 32792

1,778 SqFt

4 Beds | 3 Baths

ACTIVE

$575,000

Virtual Tour

724 Monmouth Way, Winter Park, FL 32792

2,832 SqFt

4 Beds | 2 Baths

ACTIVE

$575,000

2840 Cady Way, Winter Park, FL 32792

1,407 SqFt

3 Beds | 2 Baths

ACTIVE

$569,900

Virtual Tour

527 Cornwall Rd, Winter Park, FL 32792

1,620 SqFt

4 Beds | 2 Baths

PENDING

$565,000

1148 Howell Branch Rd, Winter Park, FL 32789

1,749 SqFt

4 Beds | 2 Baths

ACTIVE

$554,900

Virtual Tour

3301 Olde Wharf Run, Winter Park, FL 32792

2,562 SqFt

4 Beds | 4 Baths

PENDING

$549,900

525 S Lakemont Ave, Winter Park, FL 32792

1,520 SqFt

3 Beds | 2 Baths

ACTIVE

$514,990

262 Balfour Dr, Winter Park, FL 32792

2,019 SqFt

3 Beds | 3 Baths

ACTIVE

$499,990

Virtual Tour

2837 Scarlet Rd, Winter Park, FL 32792

1,640 SqFt

3 Beds | 2 Baths

ACTIVE

$499,000

2020 Strathaven Rd, Winter Park, FL 32792

1,504 SqFt

4 Beds | 2 Baths

ACTIVE

$495,000

1417 Miller Ave, Winter Park, FL 32789

860 SqFt

2 Beds | 1 Bath

ACTIVE

$484,999

Virtual Tour

2337 Albert Lee Pkwy, Winter Park, FL 32789

1,809 SqFt

4 Beds | 3 Baths

ACTIVE

$479,900

Virtual Tour

2630 Amsden Rd, Winter Park, FL 32792

1,800 SqFt

4 Beds | 2 Baths

ACTIVE

$479,000

Virtual Tour

690 Osceola Ave Unit 407, Winter Park, FL 32789

915 SqFt

1 Bed | 2 Baths

ACTIVE

$475,000

Virtual Tour

2445 Firstlight Way, Winter Park, FL 32792

2,010 SqFt

3 Beds | 3 Baths

PENDING

$470,000

Virtual Tour

5324 Poinsetta Ave, Winter Park, FL 32792

2,250 SqFt

5 Beds | 3 Baths

ACTIVE

$465,300

Virtual Tour

2448 Firstlight Way, Winter Park, FL 32792

2,076 SqFt

3 Beds | 3 Baths

PENDING

$465,000

663 Callahan St, Winter Park, FL 32789

1,238 SqFt

2 Beds | 1 Bath

ACTIVE

$465,000

Virtual Tour

808 Densmore Dr, Winter Park, FL 32792

1,460 SqFt

3 Beds | 2 Baths

ACTIVE

$450,000

Virtual Tour

3437 Bowman Dr, Winter Park, FL 32792

1,336 SqFt

3 Beds | 2 Baths

ACTIVE

$449,000

Virtual Tour

973 Wilma Ave, Winter Park, FL 32789

1,171 SqFt

3 Beds | 2 Baths

PENDING

$445,000

Virtual Tour

7661 Bent Bow Trl, Winter Park, FL 32792

2,223 SqFt

4 Beds | 3 Baths

ACTIVE

$435,000

Virtual Tour

5520 Albert Dr, Winter Park, FL 32792

1,680 SqFt

3 Beds | 2 Baths

PENDING

$433,333

Virtual Tour

1842 Shadyhill Ter, Winter Park, FL 32792

1,577 SqFt

3 Beds | 3 Baths

PENDING

$429,999

Virtual Tour

130 Arla Ct, Winter Park, FL 32792

1,740 SqFt

4 Beds | 2 Baths

PENDING

$420,000

Virtual Tour

690 Osceola Ave Unit 410, Winter Park, FL 32789

1,148 SqFt

2 Beds | 2 Baths

ACTIVE

$410,000

Virtual Tour

3095 Crane Strand Dr, Winter Park, FL 32792

1,524 SqFt

4 Beds | 2 Baths

PENDING

$408,700

Virtual Tour

1640 Meadowgold Ct, Winter Park, FL 32792

1,368 SqFt

3 Beds | 2 Baths

ACTIVE

$407,000

Virtual Tour

1209 Carvell Dr, Winter Park, FL 32792

2,279 SqFt

4 Beds | 2 Baths

PENDING

$399,500

Virtual Tour

782 Carnation Dr, Winter Park, FL 32792

1,264 SqFt

3 Beds | 2 Baths

ACTIVE

$391,700

Virtual Tour

3409 Ferndell Dr, Winter Park, FL 32792

1,412 SqFt

3 Beds | 2 Baths

PENDING

$385,000

Virtual Tour

780 Baffie Ave, Winter Park, FL 32789

1,283 SqFt

3 Beds | 2 Baths

ACTIVE

$385,000

1721 Brazilian Ln, Winter Park, FL 32792

1,604 SqFt

3 Beds | 2 Baths

ACTIVE

$375,000

707 Ellendale Dr, Winter Park, FL 32792

1,516 SqFt

3 Beds | 2 Baths

ACTIVE

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