Winter Park Homes for Sale

$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

$4,500,000

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

$3,750,000

Virtual Tour

2171 Forrest Rd, Winter Park, FL 32789

4,565 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

$3,249,000

Virtual Tour

1730 Winchester Dr, Winter Park, FL 32789

4,080 SqFt

5 Beds | 6 Baths

ACTIVE

$3,195,000

Virtual Tour

1911 Stonehurst Rd, Winter Park, FL 32789

5,097 SqFt

4 Beds | 6 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

$2,799,000

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

$2,499,900

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

$2,349,900

Virtual Tour

301 Rippling Ln, Winter Park, FL 32789

3,694 SqFt

4 Beds | 6 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

$2,160,000

Virtual Tour

2234 Via Luna, Winter Park, FL 32789

3,554 SqFt

6 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

$1,996,000

Virtual Tour

4469 Old Bear Run, Winter Park, FL 32792

4,288 SqFt

5 Beds | 5 Baths

ACTIVE

$1,899,000

Virtual Tour

2402.5 Temple Dr, Winter Park, FL 32789

3,248 SqFt

4 Beds | 5 Baths

ACTIVE

$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

$1,770,000

Virtual Tour

1470 Place Picardy, Winter Park, FL 32789

4,227 SqFt

5 Beds | 6 Baths

PENDING

$1,739,000

Virtual Tour

279 Rippling Ln, Winter Park, FL 32789

3,472 SqFt

4 Beds | 3 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

$1,590,000

Virtual Tour

8041 Lake Waunatta Dr, Winter Park, FL 32792

5,329 SqFt

5 Beds | 5 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

$1,495,000

Virtual Tour

1661 Woodland Ave, Winter Park, FL 32789

3,215 SqFt

3 Beds | 4 Baths

ACTIVE

$1,425,000

Virtual Tour

1750 Winchester Dr, Winter Park, FL 32789

2,637 SqFt

4 Beds | 4 Baths

ACTIVE

$1,397,000

Virtual Tour

1371 Lyndale Blvd, Winter Park, FL 32789

2,739 SqFt

4 Beds | 3 Baths

ACTIVE

$1,395,000

1701 Palmer Ave, Winter Park, FL 32789

2,841 SqFt

4 Beds | 3 Baths

ACTIVE

$1,385,000

Virtual Tour

1370 Alberta Dr, Winter Park, FL 32789

3,483 SqFt

5 Beds | 6 Baths

PENDING

$1,300,000

Virtual Tour

1400 S Pennsylvania Ave, Winter Park, FL 32789

2,060 SqFt

4 Beds | 3 Baths

ACTIVE

$1,299,000

1213 Richmond Rd, Winter Park, FL 32789

3,204 SqFt

4 Beds | 3 Baths

ACTIVE

$1,299,000

Virtual Tour

2536 Brookshire Ave, Winter Park, FL 32792

3,140 SqFt

4 Beds | 4 Baths

ACTIVE

$1,295,000

Virtual Tour

632 Country Club Dr, Winter Park, FL 32789

2,342 SqFt

3 Beds | 2 Baths

ACTIVE

$1,295,000

Virtual Tour

433 Carolina Ave, Winter Park, FL 32789

2,700 SqFt

5 Beds | 4 Baths

ACTIVE

$1,275,000

Virtual Tour

1611 Walnut Ave, Winter Park, FL 32789

2,635 SqFt

4 Beds | 3 Baths

ACTIVE

$1,245,000

Virtual Tour

7706 Waunatta Ct, Winter Park, FL 32792

3,858 SqFt

5 Beds | 3 Baths

ACTIVE

$1,125,000

Virtual Tour

1690 Oneco Ave, Winter Park, FL 32789

2,703 SqFt

4 Beds | 3 Baths

ACTIVE

$1,100,000

Virtual Tour

1585 Chestnut Ave, Winter Park, FL 32789

2,220 SqFt

4 Beds | 3 Baths

ACTIVE

$1,100,000

Virtual Tour

708 Balmoral Rd, Winter Park, FL 32789

2,786 SqFt

4 Beds | 3 Baths

PENDING

$1,080,000

Virtual Tour

100 S Interlachen Ave Unit 304, Winter Park, FL 32789

2,286 SqFt

4 Beds | 4 Baths

ACTIVE

$999,000

2330 Westminster Ct, Winter Park, FL 32789

3,296 SqFt

5 Beds | 3 Baths

ACTIVE

$997,000

Virtual Tour

1840 Biscayne Dr, Winter Park, FL 32789

2,641 SqFt

5 Beds | 3 Baths

ACTIVE

$995,000

Virtual Tour

2260 Hawick Ln, Winter Park, FL 32792

1,374 SqFt

2 Beds | 2 Baths

ACTIVE

$950,000

Virtual Tour

3011 Temple Trl, Winter Park, FL 32789

2,406 SqFt

5 Beds | 3 Baths

ACTIVE

$895,000

Virtual Tour

1762 Mondrian Cir, Winter Park, FL 32789

2,265 SqFt

3 Beds | 4 Baths

ACTIVE

$889,500

Virtual Tour

1907 S Lakemont Ave, Winter Park, FL 32792

2,063 SqFt

3 Beds | 4 Baths

ACTIVE

$885,000

Virtual Tour

1263 Verdant Glade Pl, Winter Park, FL 32792

2,589 SqFt

4 Beds | 4 Baths

ACTIVE

$875,000

Virtual Tour

2445 Lee Rd, Winter Park, FL 32789

2,456 SqFt

-- Beds | -- Baths

ACTIVE

$865,000

Virtual Tour

1000 Howell Branch Rd, Winter Park, FL 32789

n/a SqFt

-- Beds | -- Baths

PENDING

$855,555

Virtual Tour

2128 Sycamore Dr, Winter Park, FL 32789

1,760 SqFt

3 Beds | 2 Baths

ACTIVE

$850,000

1310 Aloma Ave, Winter Park, FL 32789

2,533 SqFt

4 Beds | 3 Baths

PENDING

$849,900

Virtual Tour

675 Overspin Dr, Winter Park, FL 32789

2,962 SqFt

4 Beds | 4 Baths

ACTIVE

$849,000

Virtual Tour

625 Worthington Dr, Winter Park, FL 32789

2,133 SqFt

4 Beds | 2 Baths

PENDING

$849,000

Virtual Tour

2955 Lolissa Ln, Winter Park, FL 32789

3,902 SqFt

4 Beds | 3 Baths

ACTIVE

$849,000

Virtual Tour

1917 S Lakemont Ave, Winter Park, FL 32792

2,051 SqFt

3 Beds | 4 Baths

ACTIVE

$839,000

Virtual Tour

2168 Marsh Sedge Ln, Winter Park, FL 32792

2,192 SqFt

4 Beds | 3 Baths

ACTIVE

$834,900

705 Baffie Ave, Winter Park, FL 32789

2,563 SqFt

4 Beds | 3 Baths

PENDING

$829,000

1795 Walker Ave, Winter Park, FL 32789

1,813 SqFt

5 Beds | 3 Baths

PENDING

$825,000

Virtual Tour

2418 Whitehall Cir, Winter Park, FL 32792

2,134 SqFt

3 Beds | 2 Baths

ACTIVE

$824,900

Virtual Tour

737 N Capen Ave, Winter Park, FL 32789

1,930 SqFt

3 Beds | 2 Baths

PENDING

$809,000

Virtual Tour

1250 S Pennsylvania Ave Unit 8, Winter Park, FL 32789

1,957 SqFt

3 Beds | 3 Baths

ACTIVE

$805,000

Virtual Tour

648 Brechin Dr, Winter Park, FL 32792

1,820 SqFt

3 Beds | 3 Baths

ACTIVE

$799,900

Virtual Tour

731 Midget Dr, Winter Park, FL 32789

960 SqFt

2 Beds | 1 Bath

PENDING

$799,900

Virtual Tour

2804 Dike Rd, Winter Park, FL 32792

2,503 SqFt

4 Beds | 3 Baths

PENDING

$799,000

Virtual Tour

5618 Winterbrook Way, Winter Park, FL 32792

2,866 SqFt

5 Beds | 4 Baths

ACTIVE

$795,000

Virtual Tour

625 Brechin Dr, Winter Park, FL 32792

1,827 SqFt

3 Beds | 2 Baths

ACTIVE

$775,000

Virtual Tour

1818 Mondrian Cir, Winter Park, FL 32789

2,265 SqFt

3 Beds | 4 Baths

PENDING

$745,000

101 S Interlachen Ave Unit 104, Winter Park, FL 32789

949 SqFt

2 Beds | 2 Baths

ACTIVE

$739,000

Virtual Tour

1977 Dundee Dr, Winter Park, FL 32792

1,656 SqFt

-- Beds | -- Baths

ACTIVE

$739,000

Virtual Tour

607 Dunblane Dr, Winter Park, FL 32792

2,046 SqFt

4 Beds | 3 Baths

ACTIVE

$735,000

Virtual Tour

1312 Golfside Dr, Winter Park, FL 32792

1,867 SqFt

3 Beds | 2 Baths

PENDING

$735,000

Virtual Tour

1312 Blue Stem Ln, Winter Park, FL 32792

2,197 SqFt

4 Beds | 3 Baths

PENDING

$719,000

Virtual Tour

1139 Fairway Dr, Winter Park, FL 32792

2,385 SqFt

4 Beds | 2 Baths

ACTIVE

$699,900

Virtual Tour

2612 Lafayette Ave, Winter Park, FL 32789

2,447 SqFt

3 Beds | 3 Baths

ACTIVE

$699,000

Virtual Tour

624 Dunraven Dr, Winter Park, FL 32792

1,762 SqFt

3 Beds | 2 Baths

ACTIVE

$699,000

Virtual Tour

1321 Medinah Ct, Winter Park, FL 32792

2,446 SqFt

4 Beds | 2 Baths

PENDING

$699,000

Virtual Tour

535 N Interlachen Ave Unit 106, Winter Park, FL 32789

1,000 SqFt

2 Beds | 2 Baths

ACTIVE

$699,000

Virtual Tour

640 Killarney Bay Ct Unit 4, Winter Park, FL 32789

1,718 SqFt

2 Beds | 3 Baths

ACTIVE

$695,000

Virtual Tour

618 N Wymore Rd, Winter Park, FL 32789

2,165 SqFt

-- Beds | -- Baths

ACTIVE

$695,000

Virtual Tour

786 Antonette Ave, Winter Park, FL 32789

1,146 SqFt

2 Beds | 1 Bath

ACTIVE

$685,000

690 S Lakemont Ave, Winter Park, FL 32792

1,897 SqFt

4 Beds | 3 Baths

ACTIVE

$680,000

Virtual Tour

1792 Killarney Dr, Winter Park, FL 32789

2,082 SqFt

4 Beds | 3 Baths

ACTIVE

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