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
$119,900
2
bds
|
3
ba
|
1,085
sqft
|
built
1974
7449 Daniel Webster Dr, Winter Park, FL 32792
$404
Cash flow
17.6%
Cash-on-Cash Return
10.2%
Cap rate
1.4%
Rent to Value Ratio
Active
$159,900
2
bds
|
2
ba
|
1,049
sqft
|
built
1969
1000 S Semoran Blvd, Winter Park, FL 32792
$140
Cash flow
4.6%
Cash-on-Cash Return
7.2%
Cap rate
1.0%
Rent to Value Ratio
106 out of 119 properties for sale in Winter Park, FL
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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
Active
$127,000
2
bds
|
2
ba
|
1,066
sqft
|
built
1974
3057 Aaron Burr Ave, Winter Park, FL 32792
$-122
Cash flow
-5.0%
Cash-on-Cash Return
5.0%
Cap rate
1.3%
Rent to Value Ratio
Active
$2,299,000
3
bds
|
4
ba
|
3,440
sqft
|
built
2001
922 N Pennsylvania Ave, Winter Park, FL 32789
$-9,190
Cash flow
-20.9%
Cash-on-Cash Return
1.4%
Cap rate
0.2%
Rent to Value Ratio
Active
$599,000
3
bds
|
2
ba
|
1,875
sqft
|
built
1960
151 N Orlando Ave, Winter Park, FL 32789
$-1,629
Cash flow
-14.2%
Cash-on-Cash Return
2.9%
Cap rate
0.7%
Rent to Value Ratio
Active
$1,100,000
5
bds
|
5
ba
|
3,839
sqft
|
built
1993
2880 Old Castle Dr, Winter Park, FL 32792
$-3,462
Cash flow
-16.4%
Cash-on-Cash Return
2.4%
Cap rate
0.4%
Rent to Value Ratio
Active
$8,500,000
5
bds
|
6
ba
|
6,502
sqft
|
built
2013
1112 Preserve Point Dr, Winter Park, FL 32789
$-44,967
Cash flow
-27.6%
Cash-on-Cash Return
-0.2%
Cap rate
0.1%
Rent to Value Ratio
Active
$299,999
2
bds
|
1
ba
|
710
sqft
|
built
1960
151 N Orlando Ave, Winter Park, FL 32789
$-550
Cash flow
-9.6%
Cash-on-Cash Return
3.9%
Cap rate
0.6%
Rent to Value Ratio
Active
$197,990
2
bds
|
2
ba
|
1,393
sqft
|
built
1974
7466 Canford Ct, Winter Park, FL 32792
$-556
Cash flow
-14.7%
Cash-on-Cash Return
2.8%
Cap rate
0.9%
Rent to Value Ratio
Active
$2,455,000
4
bds
|
5
ba
|
3,883
sqft
|
built
2015
521 S Phelps Ave, Winter Park, FL 32789
$-10,666
Cash flow
-22.7%
Cash-on-Cash Return
0.9%
Cap rate
0.3%
Rent to Value Ratio
Active
$1,445,000
3
bds
|
3
ba
|
2,351
sqft
|
built
2013
1741 Palmer Ave, Winter Park, FL 32789
$-4,416
Cash flow
-15.9%
Cash-on-Cash Return
2.5%
Cap rate
0.4%
Rent to Value Ratio
Active
$480,000
4
bds
|
2
ba
|
2,313
sqft
|
built
1987
1742 Willa Cir, Winter Park, FL 32792
$-940
Cash flow
-10.2%
Cash-on-Cash Return
3.8%
Cap rate
0.6%
Rent to Value Ratio
Active
$250,000
2
bds
|
1
ba
|
818
sqft
|
built
1938
1996 Indiana Ave, Winter Park, FL 32789
$-18
Cash flow
-0.4%
Cash-on-Cash Return
6.1%
Cap rate
0.8%
Rent to Value Ratio
Active
$409,988
3
bds
|
2
ba
|
1,540
sqft
|
built
1956
920 Gloriosa Ave, Winter Park, FL 32789
$-645
Cash flow
-8.2%
Cash-on-Cash Return
4.3%
Cap rate
0.6%
Rent to Value Ratio
Active
$479,900
3
bds
|
2
ba
|
1,939
sqft
|
built
1973
3054 Bluebrook Dr, Winter Park, FL 32792
$-966
Cash flow
-10.5%
Cash-on-Cash Return
3.7%
Cap rate
0.6%
Rent to Value Ratio
Active
$1,899,900
4
bds
|
3
ba
|
2,843
sqft
|
built
2022
1521 Chestnut Ave, Winter Park, FL 32789
$-8,272
Cash flow
-22.7%
Cash-on-Cash Return
0.9%
Cap rate
0.2%
Rent to Value Ratio
Active
$950,000
4
bds
|
4
ba
|
3,074
sqft
|
built
1998
4107 Gabriella Ln, Winter Park, FL 32792
$-2,562
Cash flow
-14.1%
Cash-on-Cash Return
2.9%
Cap rate
0.5%
Rent to Value Ratio
Active
$1,888,000
5
bds
|
5
ba
|
3,133
sqft
|
built
2018
2407 Lafayette Ave, Winter Park, FL 32789
$-4,948
Cash flow
-13.7%
Cash-on-Cash Return
3.0%
Cap rate
0.5%
Rent to Value Ratio
Active
$600,000
2
bds
|
0
ba
|
1,452
sqft
|
built
1947
1550 Michigan Ave, Winter Park, FL 32789
$-1,952
Cash flow
-17.0%
Cash-on-Cash Return
2.2%
Cap rate
0.4%
Rent to Value Ratio
Active
$160,000
1
bds
|
1
ba
|
678
sqft
|
built
1973
296 Lewfield Cir, Winter Park, FL 32792
$-284
Cash flow
-9.3%
Cash-on-Cash Return
4.0%
Cap rate
0.9%
Rent to Value Ratio
Active
$1,595,000
4
bds
|
4
ba
|
3,204
sqft
|
built
2016
1831 Mizell Ave, Winter Park, FL 32789
$-3,470
Cash flow
-11.4%
Cash-on-Cash Return
3.5%
Cap rate
0.6%
Rent to Value Ratio
Active
$564,900
2
bds
|
1
ba
|
901
sqft
|
built
1971
100 S Interlachen Ave, Winter Park, FL 32789
$-2,731
Cash flow
-25.2%
Cash-on-Cash Return
0.3%
Cap rate
0.4%
Rent to Value Ratio
Active
$1,999,500
4
bds
|
4
ba
|
3,727
sqft
|
built
2014
1840 Bryan Ave, Winter Park, FL 32789
$-5,587
Cash flow
-14.6%
Cash-on-Cash Return
2.8%
Cap rate
0.4%
Rent to Value Ratio
Active
$319,900
3
bds
|
3
ba
|
1,803
sqft
|
built
1978
2487 Harbour Way, Winter Park, FL 32792
$-646
Cash flow
-10.5%
Cash-on-Cash Return
3.7%
Cap rate
0.7%
Rent to Value Ratio
Active
$1,999,999
6
bds
|
0
ba
|
4,056
sqft
|
built
1964
1903 S Lakemont Ave, Winter Park, FL 32792
$-8,598
Cash flow
-22.4%
Cash-on-Cash Return
1.0%
Cap rate
0.2%
Rent to Value Ratio
Active
$479,000
2
bds
|
1
ba
|
954
sqft
|
built
1945
3601 Midiron Dr, Winter Park, FL 32789
$-1,373
Cash flow
-15.0%
Cash-on-Cash Return
2.7%
Cap rate
0.5%
Rent to Value Ratio
Active
$149,000
1
bds
|
1
ba
|
776
sqft
|
built
1969
1000 S Semoran Blvd, Winter Park, FL 32792
$-38
Cash flow
-1.3%
Cash-on-Cash Return
5.8%
Cap rate
0.9%
Rent to Value Ratio
Active
$149,000
1
bds
|
1
ba
|
796
sqft
|
built
1969
1000 S Semoran Blvd, Winter Park, FL 32792
$-42
Cash flow
-1.5%
Cash-on-Cash Return
5.8%
Cap rate
0.9%
Rent to Value Ratio
Active
$149,000
1
bds
|
1
ba
|
776
sqft
|
built
1969
1000 S Semoran Blvd, Winter Park, FL 32792
$-38
Cash flow
-1.3%
Cash-on-Cash Return
5.8%
Cap rate
0.9%
Rent to Value Ratio
Active
$185,000
3
bds
|
2
ba
|
1,149
sqft
|
built
1966
1695 Lee Rd, Winter Park, FL 32789
$-484
Cash flow
-13.6%
Cash-on-Cash Return
3.0%
Cap rate
1.0%
Rent to Value Ratio
Active
$2,950,000
4
bds
|
3
ba
|
2,663
sqft
|
built
1989
1020 Mayfield Ave, Winter Park, FL 32789
$-12,680
Cash flow
-22.4%
Cash-on-Cash Return
1.0%
Cap rate
0.2%
Rent to Value Ratio
Active
$3,595,000
5
bds
|
6
ba
|
4,565
sqft
|
built
2016
2171 Forrest Rd, Winter Park, FL 32789
$-13,349
Cash flow
-19.4%
Cash-on-Cash Return
1.7%
Cap rate
0.3%
Rent to Value Ratio
Active
$480,000
4
bds
|
2
ba
|
2,171
sqft
|
built
1995
1157 Valley Creek Run, Winter Park, FL 32792
$-753
Cash flow
-8.2%
Cash-on-Cash Return
4.3%
Cap rate
0.6%
Rent to Value Ratio
Active
$244,900
2
bds
|
3
ba
|
1,031
sqft
|
built
1984
3254 Oak Lake Pl, Winter Park, FL 32792
$-162
Cash flow
-3.5%
Cash-on-Cash Return
5.4%
Cap rate
1.0%
Rent to Value Ratio
Active
$215,000
2
bds
|
2
ba
|
956
sqft
|
built
1969
2500 Lee Rd, Winter Park, FL 32789
$-371
Cash flow
-9.0%
Cash-on-Cash Return
4.1%
Cap rate
0.8%
Rent to Value Ratio
Active
$380,000
4
bds
|
2
ba
|
1,678
sqft
|
built
1977
1041 Manchester Cir, Winter Park, FL 32792
$-337
Cash flow
-4.6%
Cash-on-Cash Return
5.1%
Cap rate
0.7%
Rent to Value Ratio
Active
$575,000
3
bds
|
2
ba
|
2,268
sqft
|
built
1961
701 Denton Rd, Winter Park, FL 32792
$-1,256
Cash flow
-11.4%
Cash-on-Cash Return
3.5%
Cap rate
0.6%
Rent to Value Ratio
Active
$250,000
3
bds
|
2
ba
|
1,322
sqft
|
built
1970
200 Saint Andrews Blvd, Winter Park, FL 32792
$-34
Cash flow
-0.7%
Cash-on-Cash Return
6.0%
Cap rate
0.8%
Rent to Value Ratio
Active
$2,150,000
5
bds
|
5
ba
|
3,851
sqft
|
built
1990
1560 Woodland Ave, Winter Park, FL 32789
$-8,127
Cash flow
-19.7%
Cash-on-Cash Return
1.6%
Cap rate
0.3%
Rent to Value Ratio