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
$137,000
1
bds
|
1
ba
|
796
sqft
|
built
1969
1000 S Semoran Blvd, Winter Park, FL 32792
$121
Cash flow
4.6%
Cash-on-Cash Return
7.2%
Cap rate
1.0%
Rent to Value Ratio
Active
$179,900
2
bds
|
2
ba
|
953
sqft
|
built
1973
224 Lewfield Cir, Winter Park, FL 32792
$38
Cash flow
1.1%
Cash-on-Cash Return
6.4%
Cap rate
0.9%
Rent to Value Ratio
208 out of 287 properties for sale in Winter Park, FL
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Active
$4,650,000
4
bds
|
5
ba
|
4,181
sqft
|
built
2021
1161 Valencia Ave, Winter Park, FL 32789
$-21,525
Cash flow
-24.2%
Cash-on-Cash Return
0.6%
Cap rate
0.2%
Rent to Value Ratio
Active
$360,000
3
bds
|
2
ba
|
1,114
sqft
|
built
1990
1827 Blaine Ter, Winter Park, FL 32792
$-740
Cash flow
-10.7%
Cash-on-Cash Return
3.7%
Cap rate
0.6%
Rent to Value Ratio
Active
$950,000
3
bds
|
3
ba
|
2,456
sqft
|
built
1955
915 Garden Dr, Winter Park, FL 32789
$-2,302
Cash flow
-12.6%
Cash-on-Cash Return
3.2%
Cap rate
0.5%
Rent to Value Ratio
Active
$1,050,000
5
bds
|
3
ba
|
3,858
sqft
|
built
1978
7706 Waunatta Ct, Winter Park, FL 32792
$-3,179
Cash flow
-15.8%
Cash-on-Cash Return
2.5%
Cap rate
0.4%
Rent to Value Ratio
Active
$829,000
4
bds
|
4
ba
|
3,062
sqft
|
built
2010
675 Overspin Dr, Winter Park, FL 32789
$-1,313
Cash flow
-8.3%
Cash-on-Cash Return
4.2%
Cap rate
0.7%
Rent to Value Ratio
Active
$475,000
4
bds
|
2
ba
|
1,778
sqft
|
built
1974
7104 Wrenwood Way, Winter Park, FL 32792
$-678
Cash flow
-7.4%
Cash-on-Cash Return
4.4%
Cap rate
0.7%
Rent to Value Ratio
Active
$135,000
2
bds
|
1
ba
|
881
sqft
|
built
1966
1695 Lee Rd, Winter Park, FL 32789
$-174
Cash flow
-6.7%
Cash-on-Cash Return
4.6%
Cap rate
1.2%
Rent to Value Ratio
Active
$377,500
3
bds
|
2
ba
|
1,461
sqft
|
built
1960
3490 Bougainvillea Dr, Winter Park, FL 32792
$-241
Cash flow
-3.3%
Cash-on-Cash Return
5.4%
Cap rate
0.7%
Rent to Value Ratio
Active
$399,900
2
bds
|
2
ba
|
1,148
sqft
|
built
1969
690 Osceola Ave, Winter Park, FL 32789
$-302
Cash flow
-3.9%
Cash-on-Cash Return
5.2%
Cap rate
0.7%
Rent to Value Ratio
Active
$195,000
2
bds
|
3
ba
|
1,031
sqft
|
built
1983
7444 Woodburn Ct, Winter Park, FL 32792
$-688
Cash flow
-18.4%
Cash-on-Cash Return
1.9%
Cap rate
0.9%
Rent to Value Ratio
Active
$199,000
2
bds
|
2
ba
|
987
sqft
|
built
1970
200 Saint Andrews Blvd, Winter Park, FL 32792
$-570
Cash flow
-14.9%
Cash-on-Cash Return
2.7%
Cap rate
0.8%
Rent to Value Ratio
Active
$625,000
3
bds
|
2
ba
|
1,842
sqft
|
built
1952
2812 Woodside Ave, Winter Park, FL 32789
$-1,430
Cash flow
-11.9%
Cash-on-Cash Return
3.4%
Cap rate
0.6%
Rent to Value Ratio
Active
$550,000
4
bds
|
2
ba
|
1,718
sqft
|
built
1955
240 Orange Terrace Dr, Winter Park, FL 32789
$-1,127
Cash flow
-10.7%
Cash-on-Cash Return
3.7%
Cap rate
0.6%
Rent to Value Ratio
Active
$455,000
4
bds
|
2
ba
|
1,627
sqft
|
built
1961
1849 Viburnum Ln, Winter Park, FL 32792
$-1,048
Cash flow
-12.0%
Cash-on-Cash Return
3.4%
Cap rate
0.5%
Rent to Value Ratio
Active
$399,900
3
bds
|
2
ba
|
1,182
sqft
|
built
1973
7553 Laurel Springs Dr, Winter Park, FL 32792
$-984
Cash flow
-12.8%
Cash-on-Cash Return
3.2%
Cap rate
0.6%
Rent to Value Ratio
Active
$775,000
4
bds
|
3
ba
|
2,637
sqft
|
built
2019
2167 Marsh Sedge Ln, Winter Park, FL 32792
$-1,588
Cash flow
-10.7%
Cash-on-Cash Return
3.7%
Cap rate
0.6%
Rent to Value Ratio
Active
$893,000
5
bds
|
3
ba
|
2,242
sqft
|
built
1957
1927 Eland Ave, Winter Park, FL 32789
$-2,908
Cash flow
-17.0%
Cash-on-Cash Return
2.2%
Cap rate
0.3%
Rent to Value Ratio
Active
$750,000
4
bds
|
2
ba
|
1,968
sqft
|
built
1968
744 Cornwall Rd, Winter Park, FL 32792
$-2,150
Cash flow
-15.0%
Cash-on-Cash Return
2.7%
Cap rate
0.4%
Rent to Value Ratio
Active
$495,000
3
bds
|
2
ba
|
1,440
sqft
|
built
1959
2821 Chantilly Ave, Winter Park, FL 32789
$-668
Cash flow
-7.0%
Cash-on-Cash Return
4.5%
Cap rate
0.6%
Rent to Value Ratio
Active
$2,199,999
4
bds
|
5
ba
|
3,314
sqft
|
built
2021
1752 Chestnut Ave, Winter Park, FL 32789
$-7,182
Cash flow
-17.0%
Cash-on-Cash Return
2.2%
Cap rate
0.4%
Rent to Value Ratio
Active
$835,000
3
bds
|
4
ba
|
1,672
sqft
|
built
1977
1421 Sunset Dr, Winter Park, FL 32789
$-2,225
Cash flow
-13.9%
Cash-on-Cash Return
2.9%
Cap rate
0.5%
Rent to Value Ratio
Active
$425,000
3
bds
|
2
ba
|
1,469
sqft
|
built
1957
524 Byron Rd, Winter Park, FL 32792
$-872
Cash flow
-10.7%
Cash-on-Cash Return
3.7%
Cap rate
0.6%
Rent to Value Ratio
Active
$450,000
4
bds
|
3
ba
|
1,804
sqft
|
built
1951
2464 Lotafun Ave, Winter Park, FL 32789
$-737
Cash flow
-8.5%
Cash-on-Cash Return
4.2%
Cap rate
0.6%
Rent to Value Ratio
Active
$649,000
3
bds
|
2
ba
|
1,539
sqft
|
built
1965
2758 Banchory Rd, Winter Park, FL 32792
$-2,072
Cash flow
-16.7%
Cash-on-Cash Return
2.3%
Cap rate
0.4%
Rent to Value Ratio
Active
$675,000
3
bds
|
3
ba
|
1,951
sqft
|
built
1987
595 Huntington Ave, Winter Park, FL 32789
$-1,744
Cash flow
-13.5%
Cash-on-Cash Return
3.0%
Cap rate
0.5%
Rent to Value Ratio
Active
$990,000
4
bds
|
4
ba
|
2,173
sqft
|
built
1925
208 Brewer Ave, Winter Park, FL 32789
$-2,283
Cash flow
-12.0%
Cash-on-Cash Return
3.4%
Cap rate
0.5%
Rent to Value Ratio
Active
$479,000
2
bds
|
3
ba
|
1,536
sqft
|
built
1986
130 Killarney Bay Ct, Winter Park, FL 32789
$-863
Cash flow
-9.4%
Cash-on-Cash Return
4.0%
Cap rate
0.6%
Rent to Value Ratio
Active
$2,149,000
5
bds
|
5
ba
|
3,174
sqft
|
built
2020
1710 Oneco Ave, Winter Park, FL 32789
$-8,777
Cash flow
-21.3%
Cash-on-Cash Return
1.2%
Cap rate
0.2%
Rent to Value Ratio
Active
$2,999,000
6
bds
|
5
ba
|
4,767
sqft
|
built
2020
575 Palmer Ave, Winter Park, FL 32789
$-13,003
Cash flow
-22.6%
Cash-on-Cash Return
0.9%
Cap rate
0.2%
Rent to Value Ratio
Active
$460,000
3
bds
|
2
ba
|
1,263
sqft
|
built
1976
5331 Oak Ct, Winter Park, FL 32792
$-617
Cash flow
-7.0%
Cash-on-Cash Return
4.5%
Cap rate
0.6%
Rent to Value Ratio
Active
$207,500
2
bds
|
3
ba
|
1,031
sqft
|
built
1984
3370 Cedar Springs Pl, Winter Park, FL 32792
$-102
Cash flow
-2.6%
Cash-on-Cash Return
5.6%
Cap rate
0.8%
Rent to Value Ratio
Active
$1,050,000
4
bds
|
4
ba
|
2,826
sqft
|
built
2001
512 Clarendon Ave, Winter Park, FL 32789
$-3,322
Cash flow
-16.5%
Cash-on-Cash Return
2.4%
Cap rate
0.4%
Rent to Value Ratio
Active
$272,000
2
bds
|
2
ba
|
1,010
sqft
|
built
1969
1920 Woodcrest Dr, Winter Park, FL 32792
$-602
Cash flow
-11.5%
Cash-on-Cash Return
3.5%
Cap rate
0.7%
Rent to Value Ratio
Active
$469,000
3
bds
|
3
ba
|
1,964
sqft
|
built
2019
2405 Firstlight Way, Winter Park, FL 32792
$-1,147
Cash flow
-12.8%
Cash-on-Cash Return
3.2%
Cap rate
0.6%
Rent to Value Ratio
Active
$369,000
2
bds
|
1
ba
|
1,028
sqft
|
built
1940
1516 Pinewood Dr, Winter Park, FL 32789
$-917
Cash flow
-13.0%
Cash-on-Cash Return
3.2%
Cap rate
0.5%
Rent to Value Ratio
Active
$425,000
3
bds
|
2
ba
|
1,516
sqft
|
built
1966
3425 Ferndell Dr, Winter Park, FL 32792
$-1,114
Cash flow
-13.7%
Cash-on-Cash Return
3.0%
Cap rate
0.5%
Rent to Value Ratio
Active
$650,000
4
bds
|
3
ba
|
2,251
sqft
|
built
1988
3759 Kinsley Pl, Winter Park, FL 32792
$-1,544
Cash flow
-12.4%
Cash-on-Cash Return
3.3%
Cap rate
0.5%
Rent to Value Ratio
Active
$1,700,000
3
bds
|
4
ba
|
2,964
sqft
|
built
2017
1270 Arlington Pl, Winter Park, FL 32789
$-4,357
Cash flow
-13.4%
Cash-on-Cash Return
3.1%
Cap rate
0.5%
Rent to Value Ratio