Winter Park Homes for Sale

$7,500,000

Virtual Tour

1400 Alabama Dr, Winter Park, FL 32789

7,916 SqFt

5 Beds | 9 Baths

ACTIVE

$6,995,000

1210 Via Capri, Winter Park, FL 32789

6,774 SqFt

6 Beds | 7 Baths

ACTIVE

$6,975,000

Virtual Tour

654 W Morse Blvd, Winter Park, FL 32789

8,752 SqFt

5 Beds | 8 Baths

ACTIVE

$6,800,000

Virtual Tour

500 N Interlachen Ave, Winter Park, FL 32789

4,581 SqFt

4 Beds | 5 Baths

ACTIVE

$5,950,000

Virtual Tour

1246 Alabama Dr, Winter Park, FL 32789

5,763 SqFt

7 Beds | 7 Baths

ACTIVE

$5,750,000

Virtual Tour

1761 Pinetree Rd, Winter Park, FL 32789

4,792 SqFt

5 Beds | 6 Baths

PENDING

$5,695,000

698 N New York Ave, Winter Park, FL 32789

5,096 SqFt

4 Beds | 5 Baths

ACTIVE

$5,500,000

Virtual Tour

1660 Palmer Ave, Winter Park, FL 32789

5,636 SqFt

5 Beds | 7 Baths

ACTIVE

$4,650,000

Virtual Tour

1135 Lakeview Dr, Winter Park, FL 32789

5,681 SqFt

5 Beds | 5 Baths

ACTIVE

$4,595,000

Virtual Tour

1231 Via Salerno, Winter Park, FL 32789

5,633 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

$4,350,000

Virtual Tour

1157 Tom Gurney Dr, Winter Park, FL 32789

5,527 SqFt

5 Beds | 6 Baths

PENDING

$4,250,000

Virtual Tour

985 Lincoln Cir, Winter Park, FL 32789

3,660 SqFt

5 Beds | 7 Baths

ACTIVE

$4,250,000

Virtual Tour

1229 Via Del Mar, Winter Park, FL 32789

4,596 SqFt

5 Beds | 6 Baths

ACTIVE

$4,150,000

Virtual Tour

850 Georgia Ave, Winter Park, FL 32789

4,627 SqFt

3 Beds | 6 Baths

ACTIVE

$3,890,000

Virtual Tour

1820 Glencoe Rd, Winter Park, FL 32789

4,055 SqFt

5 Beds | 7 Baths

ACTIVE

$3,500,000

Virtual Tour

681 Virginia Dr, Winter Park, FL 32789

4,338 SqFt

4 Beds | 4 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

1618 Holts Grove Cir, Winter Park, FL 32789

4,807 SqFt

4 Beds | 8 Baths

ACTIVE

$3,150,000

Virtual Tour

1833 Loch Berry Rd, Winter Park, FL 32789

4,770 SqFt

5 Beds | 5 Baths

ACTIVE

$3,150,000

Virtual Tour

1635 Highland Rd, Winter Park, FL 32789

4,325 SqFt

5 Beds | 6 Baths

PENDING

$3,100,000

Virtual Tour

1450 Mizell Ave, Winter Park, FL 32789

4,487 SqFt

5 Beds | 7 Baths

ACTIVE

$2,750,000

Virtual Tour

1108 N New York Ave, Winter Park, FL 32789

3,576 SqFt

5 Beds | 5 Baths

ACTIVE

$2,749,000

Virtual Tour

1741 Glencoe Rd, Winter Park, FL 32789

4,692 SqFt

4 Beds | 5 Baths

ACTIVE

$2,699,999

Virtual Tour

1737 Lookout Landing Cir, Winter Park, FL 32789

5,066 SqFt

5 Beds | 6 Baths

PENDING

$2,650,000

Virtual Tour

350 E Reading Way, Winter Park, FL 32789

4,693 SqFt

4 Beds | 4 Baths

PENDING

$2,495,000

2412 Chantilly Ave, Winter Park, FL 32789

4,500 SqFt

5 Beds | 7 Baths

ACTIVE

$2,250,000

Virtual Tour

1340 Chestnut Ave, Winter Park, FL 32789

4,182 SqFt

6 Beds | 6 Baths

ACTIVE

$2,200,000

Virtual Tour

1840 Bryan Ave, Winter Park, FL 32789

3,727 SqFt

4 Beds | 4 Baths

ACTIVE

$2,199,999

Virtual Tour

1451 Lyndale Blvd, Winter Park, FL 32789

3,853 SqFt

6 Beds | 4 Baths

ACTIVE

$2,195,000

Virtual Tour

451 Shepherd Ave, Winter Park, FL 32789

4,312 SqFt

5 Beds | 5 Baths

ACTIVE

$2,190,000

Virtual Tour

1941 Englewood Rd, Winter Park, FL 32789

4,112 SqFt

4 Beds | 5 Baths

PENDING

$2,190,000

Virtual Tour

2234 Via Luna, Winter Park, FL 32789

3,554 SqFt

6 Beds | 4 Baths

ACTIVE

$2,150,000

Virtual Tour

1616 Hibiscus Ave, Winter Park, FL 32789

3,897 SqFt

4 Beds | 5 Baths

ACTIVE

$2,095,000

Virtual Tour

1711 Barcelona Way, Winter Park, FL 32789

3,669 SqFt

4 Beds | 4 Baths

PENDING

$1,999,999

Virtual Tour

1764 Elizabeths Walk, Winter Park, FL 32789

3,989 SqFt

4 Beds | 4 Baths

ACTIVE

$1,990,000

Virtual Tour

2139 Blossom Ln, Winter Park, FL 32789

3,174 SqFt

5 Beds | 4 Baths

ACTIVE

$1,950,000

Virtual Tour

2415 Versailles Ave, Winter Park, FL 32789

3,954 SqFt

4 Beds | 4 Baths

ACTIVE

$1,895,000

Virtual Tour

1181 Via Capri, Winter Park, FL 32789

3,653 SqFt

3 Beds | 3 Baths

ACTIVE

$1,895,000

Virtual Tour

1350 Place Vendome, Winter Park, FL 32789

4,049 SqFt

4 Beds | 4 Baths

ACTIVE

$1,800,000

Virtual Tour

1411 Border Dr, Winter Park, FL 32789

4,638 SqFt

4 Beds | 6 Baths

PENDING

$1,798,000

Virtual Tour

501 Country Club Dr, Winter Park, FL 32789

2,857 SqFt

4 Beds | 4 Baths

ACTIVE

$1,795,000

Virtual Tour

643 Pansy Ave, Winter Park, FL 32789

3,228 SqFt

4 Beds | 4 Baths

PENDING

$1,790,000

Virtual Tour

1540 Palm Ave, Winter Park, FL 32789

3,423 SqFt

5 Beds | 4 Baths

PENDING

$1,750,000

Virtual Tour

1350 Lyndale Blvd, Winter Park, FL 32789

3,478 SqFt

4 Beds | 5 Baths

ACTIVE

$1,750,000

Virtual Tour

2025 Loch Berry Rd, Winter Park, FL 32792

3,620 SqFt

4 Beds | 4 Baths

PENDING

$1,699,995

Virtual Tour

3031 Northwood Blvd, Winter Park, FL 32789

2,978 SqFt

4 Beds | 4 Baths

ACTIVE

$1,699,000

Virtual Tour

1731 Windsor Dr, Winter Park, FL 32789

3,669 SqFt

4 Beds | 4 Baths

ACTIVE

$1,695,000

Virtual Tour

1530 Via Tuscany, Winter Park, FL 32789

3,341 SqFt

4 Beds | 4 Baths

ACTIVE

$1,650,000

Virtual Tour

1458 Aloma Ave, Winter Park, FL 32789

3,446 SqFt

5 Beds | 4 Baths

ACTIVE

$1,600,000

Virtual Tour

281 Brewer Ave, Winter Park, FL 32789

4,029 SqFt

5 Beds | 5 Baths

PENDING

$1,599,900

Virtual Tour

2914 Reef Knot Pl, Winter Park, FL 32792

4,173 SqFt

6 Beds | 7 Baths

ACTIVE

$1,595,000

Virtual Tour

1251 Palmer Ave, Winter Park, FL 32789

2,859 SqFt

4 Beds | 3 Baths

ACTIVE

$1,590,000

Virtual Tour

840 W Comstock Ave, Winter Park, FL 32789

2,350 SqFt

4 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

$1,550,000

Virtual Tour

2105 Fosgate Dr, Winter Park, FL 32789

3,068 SqFt

5 Beds | 4 Baths

ACTIVE

$1,535,000

Virtual Tour

425 Selkirk Dr, Winter Park, FL 32792

3,330 SqFt

4 Beds | 5 Baths

ACTIVE

$1,524,000

Virtual Tour

1571 Sunset Drive, Winter Park, FL 32789

2,700 SqFt

4 Beds | 4 Baths

ACTIVE

$1,500,000

Virtual Tour

2015 Summerfield Rd, Winter Park, FL 32792

2,958 SqFt

4 Beds | 4 Baths

ACTIVE

$1,499,000

Virtual Tour

513 Worthington Dr, Winter Park, FL 32789

3,112 SqFt

3 Beds | 4 Baths

ACTIVE

$1,495,000

629 Country Club Dr, Winter Park, FL 32789

2,858 SqFt

4 Beds | 4 Baths

ACTIVE

$1,449,000

Virtual Tour

2408 Lafayette Ave, Winter Park, FL 32789

2,838 SqFt

4 Beds | 4 Baths

ACTIVE

$1,395,000

Virtual Tour

1011 Palmer Ave, Winter Park, FL 32789

2,550 SqFt

3 Beds | 3 Baths

ACTIVE

$1,395,000

Virtual Tour

1601 Chestnut Ave, Winter Park, FL 32789

2,795 SqFt

4 Beds | 3 Baths

ACTIVE

$1,349,000

Virtual Tour

1269 Wading Waters Cir, Winter Park, FL 32792

4,468 SqFt

6 Beds | 4 Baths

PENDING

$1,295,000

Virtual Tour

850 Juanita Rael, Winter Park, FL 32789

2,306 SqFt

4 Beds | 3 Baths

ACTIVE

$1,249,000

Virtual Tour

7801 Georgeann St, Winter Park, FL 32792

3,158 SqFt

3 Beds | 2 Baths

ACTIVE

$1,190,000

Virtual Tour

363 N Phelps Ave, Winter Park, FL 32789

2,871 SqFt

4 Beds | 3 Baths

ACTIVE

$1,178,000

Virtual Tour

2884 Old Castle Dr, Winter Park, FL 32792

3,381 SqFt

4 Beds | 4 Baths

PENDING

$1,150,000

Virtual Tour

345 Sylvan Blvd, Winter Park, FL 32789

2,011 SqFt

4 Beds | 3 Baths

ACTIVE

$1,150,000

Virtual Tour

3720 Vinsetta Ct, Winter Park, FL 32792

5,021 SqFt

6 Beds | 5 Baths

PENDING

$1,099,000

Virtual Tour

1718 Demetree Dr, Winter Park, FL 32789

2,752 SqFt

4 Beds | 3 Baths

PENDING

$1,025,000

Virtual Tour

1771 Windsor Dr, Winter Park, FL 32789

2,059 SqFt

3 Beds | 3 Baths

ACTIVE

$980,000

Virtual Tour

210 Laurel Park Ct, Winter Park, FL 32792

2,867 SqFt

4 Beds | 3 Baths

ACTIVE

$955,000

Virtual Tour

2421 Mandan Trl, Winter Park, FL 32789

2,310 SqFt

3 Beds | 3 Baths

PENDING

$949,900

Virtual Tour

1762 Chestnut Ave, Winter Park, FL 32789

1,760 SqFt

3 Beds | 2 Baths

ACTIVE

$929,000

Virtual Tour

2955 Lolissa Ln, Winter Park, FL 32789

3,902 SqFt

4 Beds | 3 Baths

ACTIVE

$884,900

Virtual Tour

922 Garden Dr, Winter Park, FL 32789

2,131 SqFt

3 Beds | 3 Baths

ACTIVE

$849,900

Virtual Tour

2350 Sherbrooke Rd, Winter Park, FL 32792

2,200 SqFt

4 Beds | 3 Baths

ACTIVE

$824,900

Virtual Tour

2804 Dike Rd, Winter Park, FL 32792

2,503 SqFt

4 Beds | 3 Baths

ACTIVE

$799,500

Virtual Tour

2632 Mandan Trail, Winter Park, FL 32789

2,441 SqFt

5 Beds | 3 Baths

ACTIVE

$799,000

2258 Howard Dr, Winter Park, FL 32789

2,747 SqFt

5 Beds | 3 Baths

PENDING

$795,000

Virtual Tour

2616 Verona Trl, Winter Park, FL 32789

2,452 SqFt

4 Beds | 3 Baths

PENDING

$785,000

Virtual Tour

1612 Neola Trl, Winter Park, FL 32789

2,029 SqFt

3 Beds | 3 Baths

ACTIVE

$750,000

Virtual Tour

8057 Pleasant Pine Cir, Winter Park, FL 32792

3,215 SqFt

4 Beds | 4 Baths

PENDING

$725,000

Virtual Tour

417 Gilbert Rd, Winter Park, FL 32792

2,231 SqFt

4 Beds | 3 Baths

ACTIVE

$685,000

Virtual Tour

1357 Blue Stem Ln, Winter Park, FL 32792

1,770 SqFt

4 Beds | 3 Baths

PENDING

$672,400

Virtual Tour

756 Friar Rd Unit 13, Winter Park, FL 32792

2,518 SqFt

4 Beds | 2 Baths

PENDING

$650,000

Virtual Tour

274 N Ranger Blvd, Winter Park, FL 32792

1,420 SqFt

3 Beds | 2 Baths

ACTIVE

$649,900

Virtual Tour

2955 Sanbina St, Winter Park, FL 32789

1,553 SqFt

3 Beds | 2 Baths

ACTIVE

$648,900

Virtual Tour

2344 Woodcrest Dr, Winter Park, FL 32792

1,714 SqFt

4 Beds | 2 Baths

ACTIVE

$643,000

Virtual Tour

220 Blossom Ln, Winter Park, FL 32789

2,193 SqFt

3 Beds | 2 Baths

ACTIVE

$600,000

Virtual Tour

1003 Golfside Dr, Winter Park, FL 32792

2,145 SqFt

4 Beds | 2 Baths

PENDING

$579,000

Virtual Tour

5111 Lake Howell Rd, Winter Park, FL 32792

2,278 SqFt

4 Beds | 3 Baths

ACTIVE

$562,000

5233 Lake Howell Rd, Winter Park, FL 32792

1,778 SqFt

4 Beds | 3 Baths

PENDING

$560,000

Virtual Tour

2627 Ambergate Rd, Winter Park, FL 32792

1,805 SqFt

4 Beds | 3 Baths

ACTIVE

$540,000

Virtual Tour

7569 Bent Bow Trl, Winter Park, FL 32792

2,219 SqFt

4 Beds | 3 Baths

PENDING

$535,000

Virtual Tour

1976 Shadyhill Ter, Winter Park, FL 32792

2,300 SqFt

4 Beds | 3 Baths

ACTIVE

$529,900

Virtual Tour

1216 Park Green Pl, Winter Park, FL 32789

2,020 SqFt

3 Beds | 3 Baths

ACTIVE

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