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151 - 180 of 265 | Previous Page 6 of 9 Next

$275,000
20

1250 S Denning Drive #213, Winter Park, FL

1250 S Denning Drive #213
Winter Park, FL
2 Beds

2 Baths

908 Home (sqft)

2 Baths

13,068 Lot (sqft)
$560,000
20

1875 Staunton Avenue, Winter Park, FL

1875 Staunton Avenue
Winter Park, FL
4 Beds

2 Baths

2,036 Home (sqft)

2 Baths

6,970 Lot (sqft)
$879,000
41

100 S Interlachen Avenue #503, Winter Park, FL

100 S Interlachen Avenue #503
Winter Park, FL
2 Beds

2 Baths

1,143 Home (sqft)

2 Baths

0 Lot (sqft)
$949,000
29

560 Ololu Drive, Winter Park, FL

560 Ololu Drive
Winter Park, FL
2 Beds

2 Baths

1,086 Home (sqft)

2 Baths

5,228 Lot (sqft)
$679,000
26

1275 Michigan Avenue, Winter Park, FL

1275 Michigan Avenue
Winter Park, FL
3 Beds

3 Baths

1,866 Home (sqft)

3 Baths

2,614 Lot (sqft)
$4,750,000
12

1525 Granville Drive, Winter Park, FL

1525 Granville Drive
Winter Park, FL
5 Beds

6 Baths

5,211 Home (sqft)

6 Baths

14,811 Lot (sqft)
$1,799,000
51

825 Palmer Avenue, Winter Park, FL

825 Palmer Avenue
Winter Park, FL
3 Beds

3 Baths

3,297 Home (sqft)

3 Baths

15,246 Lot (sqft)
$158,000
36

1695 Lee Road #D113, Winter Park, FL

1695 Lee Road #D113
Winter Park, FL
2 Beds

1 Bath

881 Home (sqft)

1 Bath

17,860 Lot (sqft)
$1,649,999
43

1166 Oaks Boulevard, Winter Park, FL

1166 Oaks Boulevard
Winter Park, FL
4 Beds

4 Baths

2,860 Home (sqft)

4 Baths

7,841 Lot (sqft)
$4,250,000
46

702 Via Bella, Winter Park, FL

702 Via Bella
Winter Park, FL
4 Beds

6 Baths

3,720 Home (sqft)

6 Baths

10,019 Lot (sqft)
$1,595
33

851 Miles Avenue #21, Winter Park, FL

851 Miles Avenue #21
Winter Park, FL
2 Beds

1 Bath

808 Home (sqft)

1 Bath

5,663 Lot (sqft)
$179,000
25

2500 Lee Road #232, Winter Park, FL

2500 Lee Road #232
Winter Park, FL
1 Bed

1 Bath

645 Home (sqft)

1 Bath

1,743 Lot (sqft)
$3,300
57

2128 Sycamore Drive, Winter Park, FL

2128 Sycamore Drive
Winter Park, FL
3 Beds

2 Baths

1,760 Home (sqft)

2 Baths

10,019 Lot (sqft)
$329,900
25

311 E Morse Boulevard #7-11, Winter Park, FL

311 E Morse Boulevard #7-11
Winter Park, FL
1 Bed

1 Bath

570 Home (sqft)

1 Bath

2.77 Lot (ac)
$739,000
58

2955 Lolissa Lane, Winter Park, FL

2955 Lolissa Lane
Winter Park, FL
4 Beds

3 Baths

3,538 Home (sqft)

3 Baths

8,712 Lot (sqft)
$3,295
16

1641 Chestnut Avenue, Winter Park, FL

1641 Chestnut Avenue
Winter Park, FL
3 Beds

3 Baths

1,750 Home (sqft)

3 Baths

7,406 Lot (sqft)
$575,000
22

720 W Webster Avenue, Winter Park, FL

720 W Webster Avenue
Winter Park, FL
3 Beds

2 Baths

1,356 Home (sqft)

2 Baths

6,534 Lot (sqft)
$580,000
15

1740 Anzle Avenue, Winter Park, FL

1740 Anzle Avenue
Winter Park, FL
4 Beds

2 Baths

1,808 Home (sqft)

2 Baths

6,534 Lot (sqft)
$4,545,000
66

1161 Valencia Avenue, Winter Park, FL

1161 Valencia Avenue
Winter Park, FL
4 Beds

5 Baths

4,181 Home (sqft)

5 Baths

13,940 Lot (sqft)
$2,510
16

2843 Riddle Drive, Winter Park, FL

2843 Riddle Drive
Winter Park, FL
4 Beds

3 Baths

1,970 Home (sqft)

3 Baths

10,455 Lot (sqft)
$1,195,000
54

100 S Interlachen Avenue #404, Winter Park, FL

100 S Interlachen Avenue #404
Winter Park, FL
2 Beds

2 Baths

1,220 Home (sqft)

2 Baths

0 Lot (sqft)
$916,050
11

21 Karolina Ave, Winter Park, FL

21 Karolina Ave
Winter Park, FL
4 Beds

4 Baths

2,662 Home (sqft)

4 Baths

6,534 Lot (sqft)
$935,040
11

20 Karolina Ave, Winter Park, FL

20 Karolina Ave
Winter Park, FL
4 Beds

4 Baths

2,662 Home (sqft)

4 Baths

6,534 Lot (sqft)
$1,199,900
51

1981 Blue Ridge Road, Winter Park, FL

1981 Blue Ridge Road
Winter Park, FL
4 Beds

2 Baths

2,750 Home (sqft)

2 Baths

14,375 Lot (sqft)
$3,350
9

1288 Michigan Avenue, Winter Park, FL

1288 Michigan Avenue
Winter Park, FL
6 Beds

3 Baths

2,722 Home (sqft)

3 Baths

8,277 Lot (sqft)
$515,000
30

240 Orange Terrace Drive, Winter Park, FL

240 Orange Terrace Drive
Winter Park, FL
4 Beds

2 Baths

1,718 Home (sqft)

2 Baths

10,890 Lot (sqft)
$4,999,000
12

503 N Interlachen Avenue, Winter Park, FL

503 N Interlachen Avenue
Winter Park, FL
0 Beds

0 Baths

0 Home (sqft)

0 Baths

20,909 Lot (sqft)
$179,000
37

2500 Lee Rd #219, Winter Park, FL

2500 Lee Rd #219
Winter Park, FL
2 Beds

1 Bath

851 Home (sqft)

1 Bath

3,485 Lot (sqft)
$2,450
29

2886 Carew Avenue, Winter Park, FL

2886 Carew Avenue
Winter Park, FL
4 Beds

3 Baths

1,701 Home (sqft)

3 Baths

8,712 Lot (sqft)
$1,995,000
64

1752 Chestnut Avenue, Winter Park, FL

1752 Chestnut Avenue
Winter Park, FL
4 Beds

5 Baths

3,314 Home (sqft)

5 Baths

9,584 Lot (sqft)

Previous Page 6 of 9 Next

The information contained herein has been provided by My Florida Regional MLS DBA Stellar MLS. IDX information is provided exclusively for consumers' personal, non-commercial use, that it may not be used for any purpose other than to identify prospective properties consumers may be interested in purchasing, and that the data is deemed reliable but is not guaranteed accurate by the MLS. Listings last updated 12/14/25 11:39 PM PST.

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32789 – Winter Park community Real Estate

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