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

$8,995,000

Virtual Tour

2001 Bett Mar Ln, Winter Park, FL 32789

8,583 SqFt

8 Beds | 9 Baths

PENDING

$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

$5,400,000

Virtual Tour

2228 Azalea Pl, Winter Park, FL 32789

5,072 SqFt

5 Beds | 6 Baths

ACTIVE

$5,200,000

Virtual Tour

1660 Palmer Ave, Winter Park, FL 32789

6,406 SqFt

5 Beds | 7 Baths

ACTIVE

$4,985,000

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

$4,500,000

1336 College Pt, Winter Park, FL 32789

3,181 SqFt

4 Beds | 5 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

PENDING

$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

$4,100,000

Virtual Tour

1782 Pine Ave, Winter Park, FL 32789

4,782 SqFt

5 Beds | 7 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

2171 Forrest Rd, Winter Park, FL 32789

4,565 SqFt

5 Beds | 6 Baths

ACTIVE

$3,490,000

1910 Glencoe Rd, Winter Park, FL 32789

4,205 SqFt

4 Beds | 6 Baths

ACTIVE

$3,400,000

Virtual Tour

1911 Stonehurst Rd, Winter Park, FL 32789

5,097 SqFt

4 Beds | 6 Baths

ACTIVE

$3,295,000

Virtual Tour

1730 Winchester Dr, Winter Park, FL 32789

4,080 SqFt

5 Beds | 6 Baths

ACTIVE

$3,295,000

Virtual Tour

532 Worthington Dr, Winter Park, FL 32789

3,974 SqFt

5 Beds | 6 Baths

ACTIVE

$3,250,000

Virtual Tour

1833 Loch Berry Rd, Winter Park, FL 32789

4,770 SqFt

5 Beds | 5 Baths

PENDING

$3,195,000

1020 Mayfield Ave, Winter Park, FL 32789

2,663 SqFt

4 Beds | 3 Baths

ACTIVE

$2,950,000

Virtual Tour

1860 Via Contessa, Winter Park, FL 32789

7,000 SqFt

8 Beds | 6 Baths

ACTIVE

$2,895,000

Virtual Tour

1630 Lasbury Ave, Winter Park, FL 32789

4,912 SqFt

5 Beds | 5 Baths

ACTIVE

$2,850,000

Virtual Tour

1400 Place Picardy, Winter Park, FL 32789

4,411 SqFt

5 Beds | 6 Baths

ACTIVE

$2,695,000

Virtual Tour

254 Sylvan Blvd, Winter Park, FL 32789

3,653 SqFt

3 Beds | 3 Baths

PENDING

$2,650,000

1700 Palm Ave, Winter Park, FL 32789

3,770 SqFt

4 Beds | 5 Baths

ACTIVE

$2,575,000

Virtual Tour

1795 Greenwich Ave, Winter Park, FL 32789

3,852 SqFt

5 Beds | 6 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

$2,400,000

Virtual Tour

673 Balmoral Rd, Winter Park, FL 32789

2,663 SqFt

4 Beds | 3 Baths

PENDING

$2,395,000

Virtual Tour

2814 Parkland Dr, Winter Park, FL 32789

3,089 SqFt

4 Beds | 4 Baths

PENDING

$2,395,000

Virtual Tour

2412 Chantilly Ave, Winter Park, FL 32789

4,506 SqFt

5 Beds | 7 Baths

ACTIVE

$2,379,900

Virtual Tour

301 Rippling Ln, Winter Park, FL 32789

3,694 SqFt

4 Beds | 6 Baths

ACTIVE

$2,350,000

Virtual Tour

2522 Lafayette Ave, Winter Park, FL 32789

3,399 SqFt

4 Beds | 4 Baths

ACTIVE

$2,295,000

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

$2,100,000

Virtual Tour

4469 Old Bear Run, Winter Park, FL 32792

4,288 SqFt

5 Beds | 5 Baths

ACTIVE

$1,999,993

Virtual Tour

1451 Lyndale Blvd, Winter Park, FL 32789

3,853 SqFt

6 Beds | 4 Baths

ACTIVE

$1,875,000

Virtual Tour

1970 Laurel Rd, Winter Park, FL 32789

3,440 SqFt

4 Beds | 4 Baths

PENDING

$1,800,000

1682 Arbor Park Dr, Winter Park, FL 32789

2,950 SqFt

4 Beds | 4 Baths

PENDING

$1,795,000

Virtual Tour

2813 Northwood Blvd, Winter Park, FL 32789

3,444 SqFt

4 Beds | 4 Baths

PENDING

$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

ACTIVE

$1,759,000

1660 Walnut Ave, Winter Park, FL 32789

2,172 SqFt

4 Beds | 4 Baths

ACTIVE

$1,690,000

Virtual Tour

8041 Lake Waunatta Dr, Winter Park, FL 32792

5,329 SqFt

5 Beds | 5 Baths

ACTIVE

$1,675,000

607 Ellen Dr, Winter Park, FL 32789

2,812 SqFt

4 Beds | 5 Baths

ACTIVE

$1,600,000

Virtual Tour

281 Brewer Ave, Winter Park, FL 32789

4,029 SqFt

5 Beds | 5 Baths

PENDING

$1,599,900

1417 Miller Ave, Winter Park, FL 32789

3,312 SqFt

5 Beds | 4 Baths

ACTIVE

$1,575,000

Virtual Tour

627 Country Club Dr, Winter Park, FL 32789

2,858 SqFt

4 Beds | 4 Baths

PENDING

$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

Virtual Tour

1741 Pine Ave, Winter Park, FL 32789

3,297 SqFt

4 Beds | 3 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

1644 Hibiscus Ave, Winter Park, FL 32789

2,145 SqFt

3 Beds | 3 Baths

ACTIVE

$1,495,000

1701 Palmer Ave, Winter Park, FL 32789

2,841 SqFt

4 Beds | 3 Baths

ACTIVE

$1,475,000

1600 Barcelona Way, Winter Park, FL 32789

3,014 SqFt

4 Beds | 4 Baths

ACTIVE

$1,400,000

Virtual Tour

1370 Alberta Dr, Winter Park, FL 32789

3,483 SqFt

5 Beds | 6 Baths

ACTIVE

$1,395,000

Virtual Tour

1633 Pine Ave, Winter Park, FL 32789

2,481 SqFt

4 Beds | 4 Baths

PENDING

$1,360,000

Virtual Tour

1269 Wading Waters Cir, Winter Park, FL 32792

4,468 SqFt

6 Beds | 4 Baths

ACTIVE

$1,350,000

Virtual Tour

181 N Phelps Ave, Winter Park, FL 32789

3,000 SqFt

4 Beds | 4 Baths

PENDING

$1,299,000

Virtual Tour

7440 Aloma Ave, Winter Park, FL 32792

4,435 SqFt

5 Beds | 5 Baths

ACTIVE

$1,295,000

Virtual Tour

632 Country Club Dr, Winter Park, FL 32789

2,342 SqFt

3 Beds | 2 Baths

ACTIVE

$1,290,000

Virtual Tour

1201 Wading Waters Cir, Winter Park, FL 32792

4,266 SqFt

5 Beds | 5 Baths

PENDING

$1,165,000

Virtual Tour

2832 Bear Island Pointe, Winter Park, FL 32792

3,983 SqFt

5 Beds | 5 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

$1,070,000

Virtual Tour

250 Cortland Ave, Winter Park, FL 32789

2,114 SqFt

3 Beds | 2 Baths

ACTIVE

$1,025,000

Virtual Tour

2923 Cove Trl, Winter Park, FL 32789

3,377 SqFt

4 Beds | 4 Baths

ACTIVE

$995,000

Virtual Tour

210 Laurel Park Ct, Winter Park, FL 32792

2,838 SqFt

4 Beds | 3 Baths

ACTIVE

$975,000

Virtual Tour

1265 Park Pointe Ln, Winter Park, FL 32789

2,295 SqFt

4 Beds | 3 Baths

ACTIVE

$950,000

Virtual Tour

5325 Cypress Reserve Pl, Winter Park, FL 32792

3,598 SqFt

5 Beds | 4 Baths

ACTIVE

$950,000

Virtual Tour

901 Golfside Dr, Winter Park, FL 32792

2,392 SqFt

5 Beds | 3 Baths

PENDING

$875,000

1832 Magnolia Ave, Winter Park, FL 32789

2,910 SqFt

5 Beds | 4 Baths

PENDING

$849,000

Virtual Tour

2955 Lolissa Ln, Winter Park, FL 32789

3,902 SqFt

4 Beds | 3 Baths

ACTIVE

$839,900

2168 Marsh Sedge Ln, Winter Park, FL 32792

2,192 SqFt

4 Beds | 4 Baths

ACTIVE

$815,000

Virtual Tour

1316 Fountain Hills Ct, Winter Park, FL 32792

2,823 SqFt

4 Beds | 4 Baths

PENDING

$800,000

Virtual Tour

600 Brechin Dr, Winter Park, FL 32792

2,360 SqFt

4 Beds | 3 Baths

ACTIVE

$799,900

Virtual Tour

2804 Dike Rd, Winter Park, FL 32792

2,503 SqFt

4 Beds | 3 Baths

PENDING

$780,000

Virtual Tour

5275 Pine Lily Cir, Winter Park, FL 32792

3,152 SqFt

5 Beds | 4 Baths

ACTIVE

$760,000

Virtual Tour

1312 Golfside Dr, Winter Park, FL 32792

1,867 SqFt

3 Beds | 2 Baths

ACTIVE

$749,900

Virtual Tour

2925 Banchory Rd, Winter Park, FL 32792

2,419 SqFt

5 Beds | 3 Baths

PENDING

$749,000

Virtual Tour

2907 Summerfield Rd, Winter Park, FL 32792

2,532 SqFt

5 Beds | 2 Baths

PENDING

$735,000

Virtual Tour

7945 Pleasant Pine Cir, Winter Park, FL 32792

3,496 SqFt

5 Beds | 4 Baths

PENDING

$699,000

Virtual Tour

2368 Summerfield Rd, Winter Park, FL 32792

1,904 SqFt

3 Beds | 2 Baths

PENDING

$699,000

Virtual Tour

3136 Heartleaf Pl, Winter Park, FL 32792

2,717 SqFt

4 Beds | 4 Baths

ACTIVE

$699,000

690 S Lakemont Ave, Winter Park, FL 32792

1,897 SqFt

4 Beds | 3 Baths

ACTIVE

$685,000

Virtual Tour

1726 Sarong Pl, Winter Park, FL 32792

2,636 SqFt

4 Beds | 3 Baths

PENDING

$650,000

Virtual Tour

2855 Lion Heart Rd, Winter Park, FL 32792

1,727 SqFt

3 Beds | 2 Baths

ACTIVE

$625,000

Virtual Tour

2707 Prince John Rd, Winter Park, FL 32792

1,670 SqFt

3 Beds | 2 Baths

PENDING

$599,900

Virtual Tour

2100 Suffield Dr, Winter Park, FL 32792

1,807 SqFt

3 Beds | 3 Baths

PENDING

$599,000

Virtual Tour

701 Denton Rd, Winter Park, FL 32792

2,268 SqFt

3 Beds | 2 Baths

ACTIVE

$589,000

Virtual Tour

274 N Ranger Blvd, Winter Park, FL 32792

1,420 SqFt

3 Beds | 2 Baths

ACTIVE

$569,999

Virtual Tour

7730 Broken Arrow Trl, Winter Park, FL 32792

2,706 SqFt

3 Beds | 2 Baths

ACTIVE

$569,900

Virtual Tour

7584 Lodge Pole Trl, Winter Park, FL 32792

1,906 SqFt

3 Beds | 2 Baths

ACTIVE

$569,000

Virtual Tour

426 S Lakemont Ave, Winter Park, FL 32792

1,656 SqFt

3 Beds | 2 Baths

ACTIVE

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