| 4301 Old Winter Garden Rd | $546K | 1959 |
| 4408 Old Winter Garden Rd | $208K | 2000 |
| 4425 Old Winter Garden Rd | $546K | 1967 |
| 4426 Old Winter Garden Rd | $4.2M | 2019 |
| 4435 Old Winter Garden Rd | $2.4M | 2000 |
| 4436 Old Winter Garden Rd | $901K | 1978 |
| 4437 Old Winter Garden Rd | $2.7M | 1985 |
| 4446 Old Winter Garden Rd | $1.8M | 1974 |
| 4502 Old Winter Garden Rd | $2.3M | 1950 |
| 4509 Old Winter Garden Rd | $187K | 1952 |
| 4515 Old Winter Garden Rd | $1.4M | 1978 |
| 4549 Old Winter Garden Rd | $311K | — |
| 4559 Old Winter Garden Rd | $1.7M | 1972 |
| 4600 Old Winter Garden Rd | $4.5M | 1990 |
| 4625 Old Winter Garden Rd | $4M | 1985 |
| 4630 Old Winter Garden Rd | $902K | 1981 |
| 4640 Old Winter Garden Rd #A | $663K | 1986 |
| 4648 Old Winter Garden Rd | $413K | 1991 |
| 4650 Old Winter Garden Rd | $2.4M | 1982 |
| 4685 Old Winter Garden Rd | $1.1M | 1973 |
| 4690 Old Winter Garden Rd | $962K | 1950 |
| 4694 Old Winter Garden Rd | $152K | 1959 |
| 4700 Old Winter Garden Rd | $108K | — |
| 4712 Old Winter Garden Rd | $447K | 1979 |
| 4720 Old Winter Garden Rd | $939K | 1980 |
| 4726 Old Winter Garden Rd | $169K | 1961 |
| 4730 Old Winter Garden Rd | $3.6M | 1972 |
| 4777 Old Winter Garden Rd | $2.8M | 2009 |
| 4785 Old Winter Garden Rd | $980K | 1997 |
| 4808 Old Winter Garden Rd | $96K | 1952 |
| 4818 Old Winter Garden Rd | $393K | 2006 |
| 4824 Old Winter Garden Rd | $280K | 2004 |
| 4825 Old Winter Garden Rd | $1.3M | 2024 |
| 4828 Old Winter Garden Rd | $324K | 1980 |
| 4831 Old Winter Garden Rd | $441K | 2019 |
| 4840 Old Winter Garden Rd | $134K | — |
| 4900 Old Winter Garden Rd | $64K | — |
| 4901 Old Winter Garden Rd | $352K | 1968 |
| 4912 Old Winter Garden Rd | $372K | 2006 |
| 4922 Old Winter Garden Rd | $65K | — |
| 4926 Old Winter Garden Rd | $1.9M | 1961 |
| 4929 Old Winter Garden Rd | $1.2M | 1954 |
| 4947 Old Winter Garden Rd | $177K | 1955 |
| 4959 Old Winter Garden Rd | $99K | — |
| 4962 Old Winter Garden Rd | $1000K | 1982 |
| 4969 Old Winter Garden Rd | $2.3M | 2019 |
| 4970 Old Winter Garden Rd | $534K | 1980 |
| 4970 Old Winter Garden Rd | $113K | — |
| 4985 Old Winter Garden Rd | $2M | 2021 |
| 5003 Old Winter Garden Rd | $873K | 2001 |
| 5004 Old Winter Garden Rd | $1.1M | 2009 |
| 5007 Old Winter Garden Rd | $272K | 1960 |
| 5100 Old Winter Garden Rd | $618K | 1972 |
| 5115 Old Winter Garden Rd | $2.1M | 2005 |
| 5116 Old Winter Garden Rd | $310K | 1936 |
| 5130 Old Winter Garden Rd | $677K | 2009 |
| 5136 Old Winter Garden Rd | $90K | — |
| 5140 Old Winter Garden Rd | $868K | 1981 |
| 5143 Old Winter Garden Rd | $352K | 1990 |
| 5200 Old Winter Garden Rd | $1.9M | 1983 |
| 5210 Old Winter Garden Rd | $513K | 1966 |
| 5216 Old Winter Garden Rd | $53K | 1972 |
| 5220 Old Winter Garden Rd | $599K | 1959 |
| 5225 Old Winter Garden Rd | $826K | 1948 |
| 5233 Old Winter Garden Rd | $1M | 2008 |
| 5244 Old Winter Garden Rd | $756K | 2007 |
| 5300 Old Winter Garden Rd | $703K | 1950 |
| 5303 Old Winter Garden Rd | $769K | 1997 |
| 5325 Old Winter Garden Rd | $2.4M | 1986 |
| 5333 Old Winter Garden Rd | $3M | 1975 |
| 5334 Old Winter Garden Rd | $2M | 1983 |
| 5340 Old Winter Garden Rd | $1M | 1984 |
| 5358 Old Winter Garden Rd | $1.5M | 1973 |
| 5459 Old Winter Garden Rd | $533K | 1979 |
| 5480 Old Winter Garden Rd | $1.8M | — |
| 5500 Old Winter Garden Rd | $952K | 1969 |
| 5520 Old Winter Garden Rd | $556K | — |
| 5525 Old Winter Garden Rd | $313K | 1978 |
| 5604 Old Winter Garden Rd | $863K | 1967 |
| 5607 Old Winter Garden Rd | $60K | — |
| 5615 Old Winter Garden Rd | $444K | 1974 |
| 5621 Old Winter Garden Rd | $574K | 1973 |
| 5622 Old Winter Garden Rd | $5.7M | 1993 |
| 5719 Old Winter Garden Rd | $2.3M | 2015 |
| Old Winter Garden Rd | $70K | — |