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
$174,900
1
bds
|
1
ba
|
727
sqft
|
built
1970
200 Saint Andrews Blvd, Winter Park, FL 32792
$-107
Cash flow
-3.2%
Cash-on-Cash Return
5.4%
Cap rate
0.8%
Rent to Value Ratio
102 out of 115 properties for sale in Winter Park, FL
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Active
$1,200,000
2
bds
|
2
ba
|
1,220
sqft
|
built
1971
100 S Interlachen Ave, Winter Park, FL 32789
$-5,072
Cash flow
-22.1%
Cash-on-Cash Return
1.1%
Cap rate
0.2%
Rent to Value Ratio
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
$815,000
4
bds
|
3
ba
|
2,185
sqft
|
built
2019
2074 Laurelwood Way, Winter Park, FL 32792
$-2,137
Cash flow
-13.7%
Cash-on-Cash Return
3.0%
Cap rate
0.5%
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
$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
$100,000
2
bds
|
2
ba
|
1,030
sqft
|
built
1974
3053 George Mason Ave, Winter Park, FL 32792
$-155
Cash flow
-8.1%
Cash-on-Cash Return
4.3%
Cap rate
1.6%
Rent to Value Ratio
Active
$799,000
4
bds
|
3
ba
|
2,192
sqft
|
built
2019
2222 Marsh Sedge Ln, Winter Park, FL 32792
$-2,774
Cash flow
-18.1%
Cash-on-Cash Return
2.0%
Cap rate
0.4%
Rent to Value Ratio
Active
$4,250,000
3
bds
|
4
ba
|
3,413
sqft
|
built
1951
1120 Palmer Ave, Winter Park, FL 32789
$-17,843
Cash flow
-21.9%
Cash-on-Cash Return
1.1%
Cap rate
0.2%
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
$575,000
3
bds
|
2
ba
|
1,772
sqft
|
built
1979
1123 Fairway Dr, Winter Park, FL 32792
$-1,225
Cash flow
-11.1%
Cash-on-Cash Return
3.6%
Cap rate
0.5%
Rent to Value Ratio
Active
$6,500,000
6
bds
|
6
ba
|
5,759
sqft
|
built
1924
887 Georgia Ave, Winter Park, FL 32789
$-31,558
Cash flow
-25.3%
Cash-on-Cash Return
0.3%
Cap rate
0.1%
Rent to Value Ratio
Active
$379,999
3
bds
|
2
ba
|
1,114
sqft
|
built
1994
3383 Hamlet Loop, Winter Park, FL 32792
$-687
Cash flow
-9.4%
Cash-on-Cash Return
4.0%
Cap rate
0.5%
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
$4,995,000
4
bds
|
7
ba
|
6,242
sqft
|
built
2013
1760 Via Venetia, Winter Park, FL 32789
$-21,904
Cash flow
-22.9%
Cash-on-Cash Return
0.9%
Cap rate
0.2%
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
$410,000
4
bds
|
3
ba
|
1,906
sqft
|
built
1979
3415 N Goldenrod Rd, Winter Park, FL 32792
$-615
Cash flow
-7.8%
Cash-on-Cash Return
4.3%
Cap rate
0.7%
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
$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
$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
$650,000
4
bds
|
3
ba
|
2,846
sqft
|
built
1995
3115 Heartleaf Pl, Winter Park, FL 32792
$-1,574
Cash flow
-12.6%
Cash-on-Cash Return
3.2%
Cap rate
0.5%
Rent to Value Ratio
Active
$725,000
4
bds
|
2
ba
|
1,008
sqft
|
built
1967
770 W Webster Ave, Winter Park, FL 32789
$-2,532
Cash flow
-18.2%
Cash-on-Cash Return
2.0%
Cap rate
0.3%
Rent to Value Ratio
Active
$658,900
4
bds
|
3
ba
|
2,860
sqft
|
built
1998
3110 Heartleaf Pl, Winter Park, FL 32792
$-1,558
Cash flow
-12.3%
Cash-on-Cash Return
3.3%
Cap rate
0.5%
Rent to Value Ratio
Active
$180,000
2
bds
|
2
ba
|
840
sqft
|
built
1990
3651 N Goldenrod Rd, Winter Park, FL 32792
$-347
Cash flow
-10.1%
Cash-on-Cash Return
3.8%
Cap rate
0.9%
Rent to Value Ratio
Active
$949,900
3
bds
|
2
ba
|
1,536
sqft
|
built
1958
2823 Wright Ave, Winter Park, FL 32789
$-3,440
Cash flow
-18.9%
Cash-on-Cash Return
1.8%
Cap rate
0.3%
Rent to Value Ratio
Active
$570,000
4
bds
|
2
ba
|
1,843
sqft
|
built
2013
8065 Pleasant Pine Cir, Winter Park, FL 32792
$-1,433
Cash flow
-13.1%
Cash-on-Cash Return
3.1%
Cap rate
0.5%
Rent to Value Ratio
Active
$330,000
3
bds
|
2
ba
|
987
sqft
|
built
1956
1921 Dartmouth Ave, Winter Park, FL 32789
$-126
Cash flow
-2.0%
Cash-on-Cash Return
5.7%
Cap rate
0.8%
Rent to Value Ratio
Active
$339,499
2
bds
|
2
ba
|
1,126
sqft
|
built
1984
1405 Auburn Green Loop, Winter Park, FL 32792
$-678
Cash flow
-10.4%
Cash-on-Cash Return
3.8%
Cap rate
0.6%
Rent to Value Ratio
Active
$999,500
4
bds
|
5
ba
|
3,408
sqft
|
built
1993
2890 Wild Ginger Ct, Winter Park, FL 32792
$-2,784
Cash flow
-14.5%
Cash-on-Cash Return
2.8%
Cap rate
0.4%
Rent to Value Ratio
Active
$5,495,000
5
bds
|
7
ba
|
7,278
sqft
|
built
2008
2211 Azalea Pl, Winter Park, FL 32789
$-28,060
Cash flow
-26.6%
Cash-on-Cash Return
0.0%
Cap rate
0.1%
Rent to Value Ratio
Active
$1,095,000
4
bds
|
4
ba
|
2,770
sqft
|
built
2018
2607 Lafayette Ave, Winter Park, FL 32789
$-3,658
Cash flow
-17.4%
Cash-on-Cash Return
2.1%
Cap rate
0.4%
Rent to Value Ratio
Active
$1,750,000
4
bds
|
3
ba
|
3,263
sqft
|
built
1968
446 Alberta Dr, Winter Park, FL 32789
$-5,735
Cash flow
-17.1%
Cash-on-Cash Return
2.2%
Cap rate
0.3%
Rent to Value Ratio
Active
$484,900
3
bds
|
2
ba
|
1,906
sqft
|
built
1995
1173 Valley Creek Run, Winter Park, FL 32792
$-868
Cash flow
-9.3%
Cash-on-Cash Return
4.0%
Cap rate
0.5%
Rent to Value Ratio
Active
$500,000
4
bds
|
3
ba
|
2,075
sqft
|
built
1987
1976 Shadyhill Ter, Winter Park, FL 32792
$-387
Cash flow
-4.0%
Cash-on-Cash Return
5.2%
Cap rate
0.7%
Rent to Value Ratio
Active
$1,349,000
4
bds
|
4
ba
|
3,153
sqft
|
built
2019
2922 Reef Knot Pl, Winter Park, FL 32792
$-4,178
Cash flow
-16.2%
Cash-on-Cash Return
2.4%
Cap rate
0.4%
Rent to Value Ratio