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

$10,999,999

Virtual Tour

2660 Via Tuscany, Winter Park, FL 32789

4,564 SqFt

4 Beds | 5 Baths

ACTIVE

$6,975,000

Virtual Tour

654 W Morse Blvd, Winter Park, FL 32789

8,752 SqFt

5 Beds | 8 Baths

PENDING

$6,950,000

Virtual Tour

1400 Alabama Dr, Winter Park, FL 32789

7,916 SqFt

5 Beds | 9 Baths

ACTIVE

$6,250,000

Virtual Tour

541 Virginia Dr, Winter Park, FL 32789

4,725 SqFt

4 Beds | 4 Baths

ACTIVE

$5,695,000

Virtual Tour

210 Chelton Cir, Winter Park, FL 32789

5,264 SqFt

5 Beds | 6 Baths

ACTIVE

$5,400,000

Virtual Tour

2228 Azalea Pl, Winter Park, FL 32789

5,072 SqFt

5 Beds | 6 Baths

ACTIVE

$4,985,000

2161 Sharon Rd, Winter Park, FL 32789

6,338 SqFt

5 Beds | 7 Baths

ACTIVE

$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

$4,275,000

Virtual Tour

1231 Via Salerno, Winter Park, FL 32789

5,633 SqFt

5 Beds | 7 Baths

PENDING

$4,200,000

Virtual Tour

571 Lake Front Blvd, Winter Park, FL 32789

5,500 SqFt

7 Beds | 5 Baths

ACTIVE

$4,100,000

Virtual Tour

1751 Glencoe Rd, Winter Park, FL 32789

4,520 SqFt

5 Beds | 6 Baths

ACTIVE

$3,995,000

Virtual Tour

1341 College Pt, Winter Park, FL 32789

4,279 SqFt

4 Beds | 4 Baths

PENDING

$3,892,000

Virtual Tour

1391 Richmond Rd, Winter Park, FL 32789

4,635 SqFt

4 Beds | 6 Baths

ACTIVE

$3,499,000

Virtual Tour

2810 Lake Howell Ln, Winter Park, FL 32792

4,900 SqFt

7 Beds | 5 Baths

PENDING

$3,490,000

1821 Summerland Ave, Winter Park, FL 32789

5,097 SqFt

5 Beds | 5 Baths

PENDING

$3,295,000

Virtual Tour

1730 Winchester Dr, Winter Park, FL 32789

4,080 SqFt

5 Beds | 6 Baths

ACTIVE

$3,250,000

Virtual Tour

1900 W Fawsett Rd, Winter Park, FL 32789

4,600 SqFt

4 Beds | 5 Baths

ACTIVE

$3,225,000

Virtual Tour

1618 Holts Grove Cir, Winter Park, FL 32789

4,807 SqFt

5 Beds | 8 Baths

PENDING

$3,149,000

Virtual Tour

2550 Venetian Way, Winter Park, FL 32789

4,875 SqFt

4 Beds | 5 Baths

ACTIVE

$2,999,999

2652 Lake Howell Ln, Winter Park, FL 32792

3,898 SqFt

5 Beds | 4 Baths

ACTIVE

$2,995,000

Virtual Tour

884 Audubon Ln, Winter Park, FL 32789

2,995 SqFt

4 Beds | 4 Baths

ACTIVE

$2,795,000

Virtual Tour

1450 Mizell Ave, Winter Park, FL 32789

4,487 SqFt

5 Beds | 7 Baths

PENDING

$2,650,000

Virtual Tour

1010 N Pennsylvania Ave, Winter Park, FL 32789

4,074 SqFt

4 Beds | 5 Baths

ACTIVE

$2,599,000

Virtual Tour

1215 Via Salerno, Winter Park, FL 32789

3,648 SqFt

4 Beds | 5 Baths

PENDING

$2,599,000

1000 Via Tuscany Oaks Way, Winter Park, FL 32789

4,002 SqFt

5 Beds | 5 Baths

PENDING

$2,495,000

Virtual Tour

1506 Chestnut Ave, Winter Park, FL 32789

3,545 SqFt

5 Beds | 6 Baths

PENDING

$2,495,000

2412 Chantilly Ave, Winter Park, FL 32789

4,500 SqFt

5 Beds | 7 Baths

ACTIVE

$2,495,000

Virtual Tour

147 S Interlachen Ave Unit 400, Winter Park, FL 32789

5,159 SqFt

4 Beds | 5 Baths

ACTIVE

$2,399,000

Virtual Tour

2522 Lafayette Ave, Winter Park, FL 32789

3,399 SqFt

4 Beds | 4 Baths

ACTIVE

$2,375,000

Virtual Tour

1522 Lake Knowles Cir, Winter Park, FL 32789

4,144 SqFt

4 Beds | 4 Baths

PENDING

$2,300,000

Virtual Tour

1032 Early Ave, Winter Park, FL 32789

2,894 SqFt

4 Beds | 3 Baths

ACTIVE

$2,225,000

2172 Temple Dr, Winter Park, FL 32789

3,467 SqFt

5 Beds | 4 Baths

PENDING

$2,190,000

Virtual Tour

2234 Via Luna, Winter Park, FL 32789

3,554 SqFt

6 Beds | 4 Baths

ACTIVE

$2,000,000

2260 Mulbry Dr, Winter Park, FL 32789

3,246 SqFt

5 Beds | 4 Baths

ACTIVE

$1,999,999

Virtual Tour

1970 Laurel Rd, Winter Park, FL 32789

3,440 SqFt

4 Beds | 4 Baths

ACTIVE

$1,999,993

Virtual Tour

1451 Lyndale Blvd, Winter Park, FL 32789

3,853 SqFt

6 Beds | 4 Baths

ACTIVE

$1,995,000

1660 Oneco Avenue, Winter Park, FL 32789

3,101 SqFt

4 Beds | 4 Baths

PENDING

$1,977,000

Virtual Tour

1340 Chestnut Ave, Winter Park, FL 32789

4,182 SqFt

6 Beds | 6 Baths

ACTIVE

$1,899,900

Virtual Tour

1764 Elizabeths Walk, Winter Park, FL 32789

3,989 SqFt

4 Beds | 4 Baths

ACTIVE

$1,800,000

Virtual Tour

1781 Goodrich Ave, Winter Park, FL 32789

2,701 SqFt

4 Beds | 4 Baths

ACTIVE

$1,795,000

Virtual Tour

279 Rippling Ln, Winter Park, FL 32789

3,472 SqFt

4 Beds | 3 Baths

ACTIVE

$1,775,000

Virtual Tour

508 W Swoope Ave, Winter Park, FL 32789

4,133 SqFt

4 Beds | 4 Baths

ACTIVE

$1,750,000

Virtual Tour

1350 Lyndale Blvd, Winter Park, FL 32789

3,478 SqFt

4 Beds | 5 Baths

ACTIVE

$1,695,000

Virtual Tour

1321 Lakeview Dr, Winter Park, FL 32789

4,287 SqFt

4 Beds | 4 Baths

PENDING

$1,695,000

Virtual Tour

1650 Lakehurst Ave, Winter Park, FL 32789

3,777 SqFt

4 Beds | 4 Baths

ACTIVE

$1,674,999

Virtual Tour

1429 Chapman Cir, Winter Park, FL 32789

3,116 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

1716 Palmer Ave, Winter Park, FL 32789

3,270 SqFt

4 Beds | 3 Baths

ACTIVE

$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

1871 Taylor Ave, Winter Park, FL 32789

3,401 SqFt

4 Beds | 5 Baths

PENDING

$1,549,000

Virtual Tour

660 Arjay Way, Winter Park, FL 32789

3,237 SqFt

4 Beds | 4 Baths

PENDING

$1,500,000

Virtual Tour

2015 Summerfield Rd, Winter Park, FL 32792

2,958 SqFt

4 Beds | 4 Baths

ACTIVE

$1,500,000

Virtual Tour

1458 Aloma Ave, Winter Park, FL 32789

3,446 SqFt

5 Beds | 4 Baths

PENDING

$1,495,000

Virtual Tour

1371 Lyndale Blvd, Winter Park, FL 32789

2,739 SqFt

4 Beds | 3 Baths

ACTIVE

$1,470,000

Virtual Tour

840 W Comstock Ave, Winter Park, FL 32789

2,350 SqFt

4 Beds | 4 Baths

ACTIVE

$1,450,000

Virtual Tour

777 Halifax Ave, Winter Park, FL 32792

3,161 SqFt

5 Beds | 5 Baths

ACTIVE

$1,395,000

Virtual Tour

433 Carolina Ave, Winter Park, FL 32789

2,700 SqFt

5 Beds | 4 Baths

ACTIVE

$1,379,900

26 Stymie Pl, Winter Park, FL 32789

3,252 SqFt

5 Beds | 5 Baths

PENDING

$1,350,000

Virtual Tour

858 Douglas Ave, Winter Park, FL 32789

2,334 SqFt

4 Beds | 4 Baths

ACTIVE

$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

1611 Walnut Ave, Winter Park, FL 32789

2,635 SqFt

4 Beds | 3 Baths

ACTIVE

$1,275,000

Virtual Tour

1681 Blue Ridge Rd, Winter Park, FL 32789

2,762 SqFt

4 Beds | 4 Baths

PENDING

$1,250,000

Virtual Tour

567 Osceola Ave, Winter Park, FL 32789

2,651 SqFt

4 Beds | 4 Baths

ACTIVE

$1,200,000

Virtual Tour

5049 Lake Howell Rd, Winter Park, FL 32792

4,462 SqFt

4 Beds | 5 Baths

ACTIVE

$1,190,000

Virtual Tour

1571 Oneco Ave, Winter Park, FL 32789

2,510 SqFt

4 Beds | 3 Baths

PENDING

$1,180,000

Virtual Tour

1975 Biscayne Dr, Winter Park, FL 32789

3,270 SqFt

5 Beds | 4 Baths

ACTIVE

$1,175,000

Virtual Tour

850 Juanita Rael, Winter Park, FL 32789

2,306 SqFt

4 Beds | 3 Baths

PENDING

$1,150,000

Virtual Tour

708 Balmoral Rd, Winter Park, FL 32789

2,786 SqFt

4 Beds | 3 Baths

ACTIVE

$1,149,000

Virtual Tour

1840 Biscayne Dr, Winter Park, FL 32789

2,641 SqFt

5 Beds | 3 Baths

ACTIVE

$1,130,000

Virtual Tour

363 N Phelps Ave, Winter Park, FL 32789

2,871 SqFt

4 Beds | 3 Baths

PENDING

$1,100,000

2330 Westminster Ct, Winter Park, FL 32789

3,296 SqFt

5 Beds | 3 Baths

ACTIVE

$990,000

Virtual Tour

1484 Via Sangro Pl, Winter Park, FL 32792

3,063 SqFt

4 Beds | 3 Baths

ACTIVE

$939,900

Virtual Tour

675 Overspin Dr, Winter Park, FL 32789

2,962 SqFt

4 Beds | 4 Baths

ACTIVE

$929,000

1795 Walker Ave, Winter Park, FL 32789

1,813 SqFt

5 Beds | 3 Baths

ACTIVE

$895,000

Virtual Tour

1263 Verdant Glade Pl, Winter Park, FL 32792

2,589 SqFt

4 Beds | 4 Baths

ACTIVE

$889,000

Virtual Tour

2955 Lolissa Ln, Winter Park, FL 32789

3,902 SqFt

4 Beds | 3 Baths

ACTIVE

$875,000

Virtual Tour

1223 Formosa Ave, Winter Park, FL 32789

3,834 SqFt

4 Beds | 3 Baths

ACTIVE

$850,000

1310 Aloma Ave, Winter Park, FL 32789

2,533 SqFt

4 Beds | 3 Baths

PENDING

$849,000

Virtual Tour

744 London Rd, Winter Park, FL 32792

2,804 SqFt

5 Beds | 3 Baths

ACTIVE

$835,000

Virtual Tour

1316 Fountain Hills Ct, Winter Park, FL 32792

2,823 SqFt

4 Beds | 4 Baths

ACTIVE

$799,900

Virtual Tour

2804 Dike Rd, Winter Park, FL 32792

2,503 SqFt

4 Beds | 3 Baths

ACTIVE

$799,000

Virtual Tour

1375 Suffolk Rd, Winter Park, FL 32789

2,548 SqFt

4 Beds | 3 Baths

ACTIVE

$750,000

Virtual Tour

2235 Coldstream Dr, Winter Park, FL 32792

2,347 SqFt

4 Beds | 3 Baths

PENDING

$730,000

Virtual Tour

3136 Heartleaf Pl, Winter Park, FL 32792

2,717 SqFt

4 Beds | 4 Baths

ACTIVE

$725,000

Virtual Tour

432 W Swoope Ave, Winter Park, FL 32789

2,317 SqFt

4 Beds | 4 Baths

ACTIVE

$715,000

Virtual Tour

958 Dunraven Dr, Winter Park, FL 32792

1,835 SqFt

4 Beds | 3 Baths

ACTIVE

$699,495

Virtual Tour

1860 Linden Rd, Winter Park, FL 32792

1,820 SqFt

4 Beds | 2 Baths

ACTIVE

$699,000

Virtual Tour

1792 Killarney Dr, Winter Park, FL 32789

2,082 SqFt

4 Beds | 3 Baths

ACTIVE

$694,900

Virtual Tour

8077 Pleasant Pine Cir, Winter Park, FL 32792

3,215 SqFt

4 Beds | 4 Baths

ACTIVE

$675,000

Virtual Tour

678 Depugh St, Winter Park, FL 32789

1,940 SqFt

4 Beds | 3 Baths

PENDING

$660,000

Virtual Tour

1333 Orchid Ave, Winter Park, FL 32789

1,631 SqFt

4 Beds | 3 Baths

ACTIVE

$640,000

Virtual Tour

8073 Pleasant Pine Cir, Winter Park, FL 32792

2,319 SqFt

4 Beds | 3 Baths

ACTIVE

$639,900

2518 Sweetwater Trl, Winter Park, FL 32789

2,205 SqFt

4 Beds | 2 Baths

ACTIVE

$639,900

Virtual Tour

326 S Ranger Blvd, Winter Park, FL 32792

2,086 SqFt

4 Beds | 2 Baths

PENDING

$630,000

Virtual Tour

5255 Seminole Ave, Winter Park, FL 32792

2,170 SqFt

4 Beds | 3 Baths

ACTIVE

$629,999

Virtual Tour

5101 Orange Ave, Winter Park, FL 32792

1,922 SqFt

6 Beds | 2 Baths

ACTIVE

$625,000

7884 Broken Arrow Trl, Winter Park, FL 32792

1,906 SqFt

4 Beds | 2 Baths

ACTIVE

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