650 Properties Available
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- Price-High To Low
- Price-Low To High
- Newest Listings
- Beds (Most)
- Baths (Most)
- Year Built (Newest)
- Square Feet (Biggest)
- 1/8 8
New$ 3,499,900
6 Beds8 Baths4,858 SqFt2905 PARKLAND DR, Winter Park, FL 32789
Single Family Home
Listed by

- 1/33 33
Active$ 3,495,000
5 Beds6 Baths3,863 SqFt1821 ENGLEWOOD RD, Winter Park, FL 32789
Single Family Home
Listed by

- 1/12 12
Active$ 3,490,000
4 Beds6 Baths4,205 SqFt1910 GLENCOE RD, Winter Park, FL 32789
Single Family Home
Listed by

- 1/44 44
Active$ 3,399,999
5 Beds6 Baths4,955 SqFt1761 LEGION DR, Winter Park, FL 32789
Single Family Home
Listed by

- 1/61 61
Pending$ 3,350,000
4 Beds5 Baths4,600 SqFt1900 W FAWSETT RD, Winter Park, FL 32789
Single Family Home
Listed by

- 1/66 66
Pending$ 3,325,000
4 Beds6 Baths4,635 SqFt1391 RICHMOND RD, Winter Park, FL 32789
Single Family Home
Listed by

- 1/53 53
Pending$ 3,100,000
4 Beds4 Baths3,635 SqFt255 STIRLING AVE, Winter Park, FL 32789
Single Family Home
Listed by

- 1/30 30
Pending$ 3,100,000
5 Beds5 Baths3,847 SqFt457 E NEW ENGLAND AVE, Winter Park, FL 32789
Single Family Home
Listed by

- 1/49 49
Active$ 2,935,000
4 Beds4 Baths3,553 SqFt541 W CANTON AVE, Winter Park, FL 32789
Single Family Home
Listed by

- 1/90 90
Active$ 2,875,000
8 Beds6 Baths7,000 SqFt1860 VIA CONTESSA, Winter Park, FL 32789
Single Family Home
Listed by

- 1/70 70
Pending$ 2,849,000
5 Beds4 Baths3,898 SqFt2652 LAKE HOWELL LN, Winter Park, FL 32792
Single Family Home
Listed by

- 1/49 49
Pending$ 2,775,000
4 Beds3 Baths2,663 SqFt1020 MAYFIELD AVE, Winter Park, FL 32789
Single Family Home
Listed by

- 1/64 64
Active$ 2,650,000
5 Beds5 Baths3,963 SqFt2015 N PARK AVE, Winter Park, FL 32789
Single Family Home
Listed by

- 1/49 49
Active$ 2,600,000
4 Beds5 Baths5,178 SqFt950 N LAKE OTIS DR SE, Winter Haven, FL 33880
Single Family Home
Listed by

- 1/34 34
Active$ 2,599,000
4 Beds5 Baths4,875 SqFt2550 VENETIAN WAY, Winter Park, FL 32789
Single Family Home
Listed by

- 1/10 10
Pending$ 2,590,000
4 Beds5 Baths3,138 SqFt185 SYLVAN BLVD, Winter Park, FL 32789
Single Family Home
Listed by

- 1/87 87
Active$ 2,500,000
5 Beds6 Baths4,676 SqFt450 LAKEWOOD DR, Winter Park, FL 32789
Single Family Home
Listed by

- 1/32 32
Active$ 2,495,000
3 Beds3 Baths2,143 SqFt140 E MORSE BLVD #J, Winter Park, FL 32789
Condo
Listed by

- 1/70 70
Pending$ 2,490,000
3 Beds4 Baths2,709 SqFt1602 ALABAMA DR #PH404, Winter Park, FL 32789
Condo
Listed by

- 1/34 34
Pending$ 2,455,000
4 Beds5 Baths3,883 SqFt521 S PHELPS AVE, Winter Park, FL 32789
Single Family Home
Listed by

- 1/36 36
Pending$ 2,350,000
4 Beds4 Baths4,315 SqFt1268 PRESERVE POINT DR, Winter Park, FL 32789
Single Family Home
Listed by

- 1/72 72
Active$ 2,350,000
5 Beds4 Baths3,691 SqFt1885 TEMPLE DR, Winter Park, FL 32789
Single Family Home
Listed by

- 1/35 35
Pending$ 2,295,000
4 Beds4 Baths3,749 SqFt600 OLOLU DR, Winter Park, FL 32789
Single Family Home
Listed by

- 1/99 99
Active$ 2,279,000
5 Beds5 Baths3,882 SqFt1781 PINE AVE, Winter Park, FL 32789
Single Family Home
Listed by

