Winter Park, FL Investment Properties for Sale
Browse homes for sale and investment properties in Winter Park, FL. Refine your search by price, property type, or more.
Best cash flowing properties in Winter Park, FL
Active
$210,000
3
bds
|
2
ba
|
1,149
sqft
|
built
1966
1695 Lee Rd, Winter Park, FL 32789
$103
Cash flow
2.6%
Cash-on-Cash Return
6.9%
Cap rate
1.0%
Rent to Value Ratio
Active
$179,900
2
bds
|
2
ba
|
1,056
sqft
|
built
1974
3011 George Mason Ave, Winter Park, FL 32792
$-1
Cash flow
0.0%
Cash-on-Cash Return
6.3%
Cap rate
0.9%
Rent to Value Ratio
251 out of 289 properties for sale in Winter Park, FL
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Active
$725,000
2
bds
|
2
ba
|
949
sqft
|
built
1969
101 S Interlachen Ave, Winter Park, FL 32789
$-2,021
Cash flow
-14.5%
Cash-on-Cash Return
2.9%
Cap rate
0.4%
Rent to Value Ratio
Active
$625,000
3
bds
|
3
ba
|
1,890
sqft
|
built
1949
1360 Formosa Ave, Winter Park, FL 32789
$-2,451
Cash flow
-20.5%
Cash-on-Cash Return
1.6%
Cap rate
0.4%
Rent to Value Ratio
Active
$539,000
3
bds
|
2
ba
|
1,645
sqft
|
built
1949
2381 Roxbury Rd, Winter Park, FL 32789
$-851
Cash flow
-8.2%
Cash-on-Cash Return
4.4%
Cap rate
0.6%
Rent to Value Ratio
Active
$405,000
4
bds
|
2
ba
|
1,598
sqft
|
built
1990
5600 Revelwood Loop, Winter Park, FL 32792
$-841
Cash flow
-10.8%
Cash-on-Cash Return
3.8%
Cap rate
0.6%
Rent to Value Ratio
Active
$399,900
4
bds
|
3
ba
|
1,788
sqft
|
built
1989
4421 Steed Ter, Winter Park, FL 32792
$-763
Cash flow
-10.0%
Cash-on-Cash Return
4.0%
Cap rate
0.6%
Rent to Value Ratio
Active
$1,645,000
4
bds
|
4
ba
|
4,000
sqft
|
built
1977
7841 Georgeann St, Winter Park, FL 32792
$-6,507
Cash flow
-20.6%
Cash-on-Cash Return
1.5%
Cap rate
0.3%
Rent to Value Ratio
Active
$1,395,000
4
bds
|
3
ba
|
2,841
sqft
|
built
1953
1701 Palmer Ave, Winter Park, FL 32789
$-3,928
Cash flow
-14.7%
Cash-on-Cash Return
2.9%
Cap rate
0.5%
Rent to Value Ratio
Active
$478,700
4
bds
|
2
ba
|
2,014
sqft
|
built
1982
1776 E Cheryl Dr, Winter Park, FL 32792
$-768
Cash flow
-8.4%
Cash-on-Cash Return
4.4%
Cap rate
0.6%
Rent to Value Ratio
Active
$995,000
3
bds
|
2
ba
|
2,114
sqft
|
built
1981
250 Cortland Ave, Winter Park, FL 32789
$-2,401
Cash flow
-12.6%
Cash-on-Cash Return
3.4%
Cap rate
0.5%
Rent to Value Ratio
Active
$1,475,000
4
bds
|
4
ba
|
3,014
sqft
|
built
1972
1600 Barcelona Way, Winter Park, FL 32789
$-3,802
Cash flow
-13.4%
Cash-on-Cash Return
3.2%
Cap rate
0.5%
Rent to Value Ratio
Active
$469,900
3
bds
|
3
ba
|
1,801
sqft
|
built
2023
2037 Canny Cv, Winter Park, FL 32792
$-1,203
Cash flow
-13.4%
Cash-on-Cash Return
3.2%
Cap rate
0.7%
Rent to Value Ratio
Active
$450,000
2
bds
|
2
ba
|
1,088
sqft
|
built
1972
535 N Interlachen Ave, Winter Park, FL 32789
$-1,309
Cash flow
-15.2%
Cash-on-Cash Return
2.8%
Cap rate
0.5%
Rent to Value Ratio
Active
$2,795,000
5
bds
|
5
ba
|
4,912
sqft
|
built
2003
1630 Lasbury Ave, Winter Park, FL 32789
$-11,952
Cash flow
-22.3%
Cash-on-Cash Return
1.2%
Cap rate
0.2%
Rent to Value Ratio
Active
$394,500
3
bds
|
3
ba
|
1,730
sqft
|
built
1965
1021 Mare Bello Dr, Winter Park, FL 32792
$-505
Cash flow
-6.7%
Cash-on-Cash Return
4.7%
Cap rate
0.6%
Rent to Value Ratio
Active
$4,395,000
5
bds
|
5
ba
|
4,129
sqft
|
built
1998
1840 W Fawsett Rd, Winter Park, FL 32789
$-19,930
Cash flow
-23.7%
Cash-on-Cash Return
0.8%
Cap rate
0.2%
Rent to Value Ratio
Active
$1,070,000
4
bds
|
3
ba
|
3,121
sqft
|
built
1984
1444 Pelican Bay Trl, Winter Park, FL 32792
$-3,704
Cash flow
-18.1%
Cash-on-Cash Return
2.1%
Cap rate
0.4%
Rent to Value Ratio
Active
$557,900
5
bds
|
3
ba
|
2,733
sqft
|
built
1979
4029 Cool Water Ct, Winter Park, FL 32792
$-1,033
Cash flow
-9.7%
Cash-on-Cash Return
4.1%
Cap rate
0.6%
Rent to Value Ratio
Active
$539,500
5
bds
|
2
ba
|
2,272
sqft
|
built
1956
5073 Lake Howell Rd, Winter Park, FL 32792
$-1,286
Cash flow
-12.4%
Cash-on-Cash Return
3.4%
Cap rate
0.5%
Rent to Value Ratio
Active
$1,575,000
3
bds
|
3
ba
|
2,128
sqft
|
built
1969
690 Osceola Ave, Winter Park, FL 32789
$-8,309
Cash flow
-27.5%
Cash-on-Cash Return
0.0%
Cap rate
0.2%
Rent to Value Ratio
Active
$210,000
3
bds
|
2
ba
|
1,149
sqft
|
built
1966
1695 Lee Rd, Winter Park, FL 32789
$103
Cash flow
2.6%
Cash-on-Cash Return
6.9%
Cap rate
1.0%
Rent to Value Ratio
Active
$399,900
3
bds
|
2
ba
|
1,200
sqft
|
built
1949
1975 Staunton Ave, Winter Park, FL 32789
$-1,039
Cash flow
-13.6%
Cash-on-Cash Return
3.2%
Cap rate
0.5%
Rent to Value Ratio
Active
$465,000
3
bds
|
3
ba
|
2,076
sqft
|
built
2021
1522 Bantam Way, Winter Park, FL 32792
$-1,296
Cash flow
-14.5%
Cash-on-Cash Return
2.9%
Cap rate
0.6%
Rent to Value Ratio
Active
$784,000
5
bds
|
4
ba
|
2,866
sqft
|
built
2020
5618 Winterbrook Way, Winter Park, FL 32792
$-1,775
Cash flow
-11.8%
Cash-on-Cash Return
3.6%
Cap rate
0.6%
Rent to Value Ratio
Active
$995,000
4
bds
|
3
ba
|
2,838
sqft
|
built
2006
210 Laurel Park Ct, Winter Park, FL 32792
$-1,908
Cash flow
-10.0%
Cash-on-Cash Return
4.0%
Cap rate
0.6%
Rent to Value Ratio
Active
$179,900
2
bds
|
2
ba
|
1,056
sqft
|
built
1974
3011 George Mason Ave, Winter Park, FL 32792
$-1
Cash flow
0.0%
Cash-on-Cash Return
6.3%
Cap rate
0.9%
Rent to Value Ratio
Active
$154,900
2
bds
|
1
ba
|
881
sqft
|
built
1966
1695 Lee Rd, Winter Park, FL 32789
$-181
Cash flow
-6.1%
Cash-on-Cash Return
4.9%
Cap rate
1.2%
Rent to Value Ratio
Active
$665,000
2
bds
|
2
ba
|
1,000
sqft
|
built
1972
535 N Interlachen Ave, Winter Park, FL 32789
$-2,289
Cash flow
-18.0%
Cash-on-Cash Return
2.2%
Cap rate
0.3%
Rent to Value Ratio
Active
$975,000
3
bds
|
1
ba
|
1,045
sqft
|
built
1925
674 W Comstock Ave, Winter Park, FL 32789
$-3,531
Cash flow
-18.9%
Cash-on-Cash Return
1.9%
Cap rate
0.2%
Rent to Value Ratio
Active
$550,000
3
bds
|
2
ba
|
1,115
sqft
|
built
2015
720 N Pennsylvania Ave, Winter Park, FL 32789
$-890
Cash flow
-8.4%
Cash-on-Cash Return
4.3%
Cap rate
0.6%
Rent to Value Ratio
Active
$750,000
3
bds
|
2
ba
|
1,167
sqft
|
built
2015
726 N Pennsylvania Ave, Winter Park, FL 32789
$-2,133
Cash flow
-14.8%
Cash-on-Cash Return
2.9%
Cap rate
0.4%
Rent to Value Ratio
Active
$185,000
2
bds
|
2
ba
|
953
sqft
|
built
1973
224 Lewfield Cir, Winter Park, FL 32792
$-9
Cash flow
-0.3%
Cash-on-Cash Return
6.2%
Cap rate
0.9%
Rent to Value Ratio
Active
$1,295,000
4
bds
|
4
ba
|
2,916
sqft
|
built
1973
1611 Chestnut Ave, Winter Park, FL 32789
$-3,965
Cash flow
-16.0%
Cash-on-Cash Return
2.6%
Cap rate
0.3%
Rent to Value Ratio
Active
$1,125,000
4
bds
|
3
ba
|
2,703
sqft
|
built
1967
1690 Oneco Ave, Winter Park, FL 32789
$-2,722
Cash flow
-12.6%
Cash-on-Cash Return
3.4%
Cap rate
0.6%
Rent to Value Ratio
Active
$795,000
3
bds
|
2
ba
|
1,827
sqft
|
built
1961
625 Brechin Dr, Winter Park, FL 32792
$-1,909
Cash flow
-12.5%
Cash-on-Cash Return
3.4%
Cap rate
0.5%
Rent to Value Ratio
Active
$170,000
3
bds
|
2
ba
|
1,356
sqft
|
built
1974
7340 Daniel Webster Dr, Winter Park, FL 32792
$-302
Cash flow
-9.3%
Cash-on-Cash Return
4.2%
Cap rate
1.1%
Rent to Value Ratio
Active
$159,000
1
bds
|
1
ba
|
638
sqft
|
built
1966
1695 Lee Rd, Winter Park, FL 32789
$-328
Cash flow
-10.8%
Cash-on-Cash Return
3.8%
Cap rate
0.9%
Rent to Value Ratio
Active
$549,000
4
bds
|
3
ba
|
2,213
sqft
|
built
1984
3901 Woodglade Cv, Winter Park, FL 32792
$-913
Cash flow
-8.7%
Cash-on-Cash Return
4.3%
Cap rate
0.7%
Rent to Value Ratio
Active
$255,000
2
bds
|
2
ba
|
956
sqft
|
built
1969
2500 Lee Rd, Winter Park, FL 32789
$-624
Cash flow
-12.8%
Cash-on-Cash Return
3.3%
Cap rate
0.7%
Rent to Value Ratio
Active
$1,950,000
3
bds
|
4
ba
|
2,767
sqft
|
built
2001
622 Penn Pl, Winter Park, FL 32789
$-6,625
Cash flow
-17.7%
Cash-on-Cash Return
2.2%
Cap rate
0.4%
Rent to Value Ratio
Active
$452,000
3
bds
|
3
ba
|
1,907
sqft
|
built
2023
2033 Canny Cv, Winter Park, FL 32792
$-1,533
Cash flow
-17.7%
Cash-on-Cash Return
2.2%
Cap rate
0.6%
Rent to Value Ratio