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

$6,950,000

Virtual Tour

1400 Alabama Dr, Winter Park, FL 32789

7,916 SqFt

5 Beds | 9 Baths

ACTIVE

$6,100,000

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

PENDING

$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

$4,200,000

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

$3,295,000

Virtual Tour

100 E Rockwood Way, Winter Park, FL 32789

4,304 SqFt

4 Beds | 6 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

$3,130,000

Virtual Tour

210 E Lake Sue Ave, Winter Park, FL 32789

4,188 SqFt

5 Beds | 6 Baths

PENDING

$3,000,000

425 Alberta Dr, Winter Park, FL 32789

2,310 SqFt

3 Beds | 2 Baths

PENDING

$2,999,999

2652 Lake Howell Ln, Winter Park, FL 32792

3,898 SqFt

5 Beds | 4 Baths

ACTIVE

$2,999,900

Virtual Tour

2550 Venetian Way, Winter Park, FL 32789

4,875 SqFt

4 Beds | 5 Baths

ACTIVE

$2,995,000

Virtual Tour

884 Audubon Ln, Winter Park, FL 32789

2,995 SqFt

4 Beds | 4 Baths

PENDING

$2,995,000

Virtual Tour

1400 Place Picardy, Winter Park, FL 32789

4,411 SqFt

5 Beds | 6 Baths

ACTIVE

$2,890,000

Virtual Tour

140 E Morse Blvd J, Winter Park, FL 32789

2,143 SqFt

3 Beds | 3 Baths

ACTIVE

$2,650,000

Virtual Tour

1010 N Pennsylvania Ave, Winter Park, FL 32789

4,074 SqFt

4 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

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

$2,395,000

Virtual Tour

2412 Chantilly Ave, Winter Park, FL 32789

4,506 SqFt

5 Beds | 7 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

PENDING

$2,279,000

Virtual Tour

141 Oakwood Way, Winter Park, FL 32789

3,909 SqFt

5 Beds | 4 Baths

ACTIVE

$2,200,000

Virtual Tour

1446 Berkshire Ave, Winter Park, FL 32789

4,612 SqFt

5 Beds | 6 Baths

PENDING

$2,190,000

Virtual Tour

2234 Via Luna, Winter Park, FL 32789

3,554 SqFt

6 Beds | 4 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

140 Dana Way, Winter Park, FL 32789

3,441 SqFt

3 Beds | 3 Baths

ACTIVE

$2,000,000

2260 Mulbry Dr, Winter Park, FL 32789

3,246 SqFt

5 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

Virtual Tour

817 Antonette Ave, Winter Park, FL 32789

3,971 SqFt

4 Beds | 3 Baths

ACTIVE

$1,977,000

Virtual Tour

1340 Chestnut Ave, Winter Park, FL 32789

4,182 SqFt

6 Beds | 6 Baths

ACTIVE

$1,950,000

Virtual Tour

622 Penn Pl, Winter Park, FL 32789

2,767 SqFt

3 Beds | 4 Baths

ACTIVE

$1,950,000

Virtual Tour

1470 Place Picardy, Winter Park, FL 32789

4,227 SqFt

5 Beds | 6 Baths

ACTIVE

$1,899,900

Virtual Tour

1764 Elizabeths Walk, Winter Park, FL 32789

3,989 SqFt

4 Beds | 4 Baths

PENDING

$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

PENDING

$1,775,000

Virtual Tour

1781 Goodrich Ave, Winter Park, FL 32789

2,701 SqFt

4 Beds | 4 Baths

PENDING

$1,759,000

1660 Walnut Ave, Winter Park, FL 32789

2,172 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

$1,750,000

Virtual Tour

2185 Talman Ct, Winter Park, FL 32792

4,760 SqFt

5 Beds | 6 Baths

PENDING

$1,695,000

Virtual Tour

101 S New York Ave Unit 302, Winter Park, FL 32789

3,174 SqFt

3 Beds | 4 Baths

ACTIVE

$1,675,000

607 Ellen Dr, Winter Park, FL 32789

2,812 SqFt

4 Beds | 5 Baths

ACTIVE

$1,674,999

Virtual Tour

1429 Chapman Cir, Winter Park, FL 32789

3,116 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

1716 Palmer Ave, Winter Park, FL 32789

3,270 SqFt

4 Beds | 3 Baths

PENDING

$1,599,900

1417 Miller Ave, Winter Park, FL 32789

3,312 SqFt

5 Beds | 4 Baths

ACTIVE

$1,595,000

335 Beloit Ave, Winter Park, FL 32789

2,420 SqFt

3 Beds | 2 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

$1,500,000

747 McIntyre Ave, Winter Park, FL 32789

1,457 SqFt

3 Beds | 2 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

Virtual Tour

1101 Kenwood Ave, Winter Park, FL 32789

2,955 SqFt

3 Beds | 3 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

$1,380,000

Virtual Tour

1400 S Pennsylvania Ave, Winter Park, FL 32789

2,060 SqFt

4 Beds | 3 Baths

ACTIVE

$1,350,000

Virtual Tour

632 Country Club Dr, Winter Park, FL 32789

2,342 SqFt

3 Beds | 2 Baths

ACTIVE

$1,350,000

Virtual Tour

858 Douglas Ave, Winter Park, FL 32789

2,334 SqFt

4 Beds | 4 Baths

ACTIVE

$1,299,990

Virtual Tour

2258 E Howard Dr, Winter Park, FL 32789

2,747 SqFt

4 Beds | 3 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

1932 Temple Dr, Winter Park, FL 32789

2,432 SqFt

3 Beds | 3 Baths

ACTIVE

$1,295,000

Virtual Tour

1611 Walnut Ave, Winter Park, FL 32789

2,635 SqFt

4 Beds | 3 Baths

ACTIVE

$1,295,000

1611 Chestnut Ave, Winter Park, FL 32789

2,916 SqFt

4 Beds | 4 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

1585 Chestnut Ave, Winter Park, FL 32789

2,220 SqFt

4 Beds | 3 Baths

PENDING

$1,250,000

Virtual Tour

567 Osceola Ave, Winter Park, FL 32789

2,651 SqFt

4 Beds | 4 Baths

ACTIVE

$1,250,000

Virtual Tour

1778 Mondrian Cir, Winter Park, FL 32789

2,377 SqFt

3 Beds | 4 Baths

ACTIVE

$1,200,000

Virtual Tour

193 Overlook Rd, Winter Park, FL 32789

2,201 SqFt

3 Beds | 2 Baths

PENDING

$1,200,000

Virtual Tour

5049 Lake Howell Rd, Winter Park, FL 32792

4,462 SqFt

4 Beds | 5 Baths

PENDING

$1,195,000

Virtual Tour

1690 Oneco Ave, Winter Park, FL 32789

2,703 SqFt

4 Beds | 3 Baths

ACTIVE

$1,190,000

Virtual Tour

1885 Temple Dr, Winter Park, FL 32789

3,691 SqFt

4 Beds | 4 Baths

PENDING

$1,175,000

Virtual Tour

3818 Kinsley Place, Winter Park, FL 32792

3,613 SqFt

4 Beds | 4 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

$1,125,000

Virtual Tour

1975 Biscayne Dr, Winter Park, FL 32789

3,270 SqFt

5 Beds | 4 Baths

ACTIVE

$1,100,000

2330 Westminster Ct, Winter Park, FL 32789

3,296 SqFt

5 Beds | 3 Baths

ACTIVE

$1,095,000

100 S Virginia Ave Unit 401, Winter Park, FL 32789

2,615 SqFt

3 Beds | 3 Baths

PENDING

$1,069,000

Virtual Tour

1001 Tuscany Pl, Winter Park, FL 32789

2,458 SqFt

3 Beds | 2 Baths

ACTIVE

$995,000

870 Carver St, Winter Park, FL 32789

1,844 SqFt

3 Beds | 4 Baths

ACTIVE

$990,000

Virtual Tour

1484 Via Sangro Pl, Winter Park, FL 32792

3,063 SqFt

4 Beds | 3 Baths

PENDING

$975,000

Virtual Tour

1760 Mondrian Cir, Winter Park, FL 32789

2,245 SqFt

3 Beds | 4 Baths

ACTIVE

$950,000

Virtual Tour

830 W Canton Ave, Winter Park, FL 32789

1,965 SqFt

3 Beds | 3 Baths

PENDING

$949,900

Virtual Tour

533 Balmoral Rd, Winter Park, FL 32789

1,900 SqFt

3 Beds | 3 Baths

ACTIVE

$940,000

Virtual Tour

2050 Temple Dr W, Winter Park, FL 32789

1,449 SqFt

3 Beds | 1 Bath

PENDING

$930,000

Virtual Tour

675 Overspin Dr, Winter Park, FL 32789

2,962 SqFt

4 Beds | 4 Baths

ACTIVE

$925,000

Virtual Tour

1762 Mondrian Cir, Winter Park, FL 32789

2,265 SqFt

3 Beds | 4 Baths

ACTIVE

$899,500

Virtual Tour

1907 S Lakemont Ave, Winter Park, FL 32792

2,063 SqFt

3 Beds | 4 Baths

ACTIVE

$899,000

Virtual Tour

1919 S Lakemont Ave, Winter Park, FL 32792

2,085 SqFt

3 Beds | 4 Baths

ACTIVE

$899,000

Virtual Tour

1917 S Lakemont Ave, Winter Park, FL 32792

2,051 SqFt

3 Beds | 4 Baths

ACTIVE

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