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
$139,900
2
bds
|
3
ba
|
1,085
sqft
|
built
1974
7449 Daniel Webster Dr, Winter Park, FL 32792
$285
Cash flow
10.6%
Cash-on-Cash Return
8.7%
Cap rate
1.2%
Rent to Value Ratio
Active
$137,500
2
bds
|
1
ba
|
881
sqft
|
built
1966
1695 Lee Rd, Winter Park, FL 32789
$212
Cash flow
8.0%
Cash-on-Cash Return
8.1%
Cap rate
1.2%
Rent to Value Ratio
59 out of 91 properties for sale in Winter Park, FL
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Active
$195,000
2
bds
|
2
ba
|
1,049
sqft
|
built
1969
1000 S Semoran Blvd, Winter Park, FL 32792
$-321
Cash flow
-8.6%
Cash-on-Cash Return
4.3%
Cap rate
0.8%
Rent to Value Ratio
Active
$127,000
2
bds
|
2
ba
|
1,066
sqft
|
built
1974
3057 Aaron Burr Ave, Winter Park, FL 32792
$-136
Cash flow
-5.6%
Cash-on-Cash Return
5.0%
Cap rate
1.3%
Rent to Value Ratio
Active
$225,000
2
bds
|
1
ba
|
808
sqft
|
built
1984
851 Miles Ave, Winter Park, FL 32789
$-18
Cash flow
-0.4%
Cash-on-Cash Return
6.2%
Cap rate
0.8%
Rent to Value Ratio
Active
$610,000
3
bds
|
2
ba
|
1,875
sqft
|
built
1960
151 N Orlando Ave, Winter Park, FL 32789
$-1,755
Cash flow
-15.0%
Cash-on-Cash Return
2.8%
Cap rate
0.7%
Rent to Value Ratio
Active
$192,000
2
bds
|
2
ba
|
840
sqft
|
built
1990
3651 N Goldenrod Rd, Winter Park, FL 32792
$-69
Cash flow
-1.9%
Cash-on-Cash Return
5.9%
Cap rate
0.8%
Rent to Value Ratio
Active
$139,900
2
bds
|
3
ba
|
1,085
sqft
|
built
1974
7449 Daniel Webster Dr, Winter Park, FL 32792
$285
Cash flow
10.6%
Cash-on-Cash Return
8.7%
Cap rate
1.2%
Rent to Value Ratio
Active
$188,500
1
bds
|
1
ba
|
658
sqft
|
built
1967
1250 S Denning Dr, Winter Park, FL 32789
$-351
Cash flow
-9.7%
Cash-on-Cash Return
4.0%
Cap rate
0.8%
Rent to Value Ratio
Active
$350,000
2
bds
|
3
ba
|
1,133
sqft
|
built
1985
184 Sandlewood Trl, Winter Park, FL 32789
$-489
Cash flow
-7.3%
Cash-on-Cash Return
4.6%
Cap rate
0.7%
Rent to Value Ratio
Active
$219,000
2
bds
|
2
ba
|
1,393
sqft
|
built
1974
7466 Canford Ct, Winter Park, FL 32792
$-689
Cash flow
-16.4%
Cash-on-Cash Return
2.5%
Cap rate
0.8%
Rent to Value Ratio
Active
$299,999
2
bds
|
1
ba
|
710
sqft
|
built
1960
151 N Orlando Ave, Winter Park, FL 32789
$-584
Cash flow
-10.2%
Cash-on-Cash Return
3.9%
Cap rate
0.6%
Rent to Value Ratio
Active
$267,000
2
bds
|
2
ba
|
1,219
sqft
|
built
1970
200 Saint Andrews Blvd, Winter Park, FL 32792
$-297
Cash flow
-5.8%
Cash-on-Cash Return
4.9%
Cap rate
0.7%
Rent to Value Ratio
Active
$349,900
1
bds
|
1
ba
|
823
sqft
|
built
1983
1308 S Pennsylvania Ave, Winter Park, FL 32789
$-731
Cash flow
-10.9%
Cash-on-Cash Return
3.8%
Cap rate
0.6%
Rent to Value Ratio
Active
$207,900
1
bds
|
1
ba
|
645
sqft
|
built
1969
2500 Lee Rd, Winter Park, FL 32789
$-32
Cash flow
-0.8%
Cash-on-Cash Return
6.1%
Cap rate
0.8%
Rent to Value Ratio
Active
$160,000
1
bds
|
1
ba
|
678
sqft
|
built
1973
296 Lewfield Cir, Winter Park, FL 32792
$-302
Cash flow
-9.8%
Cash-on-Cash Return
4.0%
Cap rate
0.9%
Rent to Value Ratio
Active
$245,000
2
bds
|
1
ba
|
710
sqft
|
built
1960
151 N Orlando Ave, Winter Park, FL 32789
$-706
Cash flow
-15.0%
Cash-on-Cash Return
2.8%
Cap rate
0.7%
Rent to Value Ratio
Active
$564,900
2
bds
|
1
ba
|
901
sqft
|
built
1971
100 S Interlachen Ave, Winter Park, FL 32789
$-2,795
Cash flow
-25.8%
Cash-on-Cash Return
0.3%
Cap rate
0.4%
Rent to Value Ratio
Active
$1,749,000
3
bds
|
4
ba
|
3,112
sqft
|
built
2008
101 S New York Ave, Winter Park, FL 32789
$-8,311
Cash flow
-24.8%
Cash-on-Cash Return
0.6%
Cap rate
0.3%
Rent to Value Ratio
Active
$274,900
3
bds
|
3
ba
|
1,578
sqft
|
built
1974
7484 Canford Ct, Winter Park, FL 32792
$-593
Cash flow
-11.3%
Cash-on-Cash Return
3.7%
Cap rate
0.8%
Rent to Value Ratio
Active
$149,000
1
bds
|
1
ba
|
796
sqft
|
built
1969
1000 S Semoran Blvd, Winter Park, FL 32792
$-59
Cash flow
-2.1%
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
$-55
Cash flow
-1.9%
Cash-on-Cash Return
5.8%
Cap rate
0.9%
Rent to Value Ratio
Active
$205,990
3
bds
|
2
ba
|
1,149
sqft
|
built
1966
1695 Lee Rd, Winter Park, FL 32789
$-615
Cash flow
-15.6%
Cash-on-Cash Return
2.7%
Cap rate
0.9%
Rent to Value Ratio
Active
$137,500
2
bds
|
1
ba
|
881
sqft
|
built
1966
1695 Lee Rd, Winter Park, FL 32789
$212
Cash flow
8.0%
Cash-on-Cash Return
8.1%
Cap rate
1.2%
Rent to Value Ratio
Pending
$1,080,000
4
bds
|
4
ba
|
2,286
sqft
|
built
1971
100 S Interlachen Ave, Winter Park, FL 32789
$-3,913
Cash flow
-18.9%
Cash-on-Cash Return
1.9%
Cap rate
0.4%
Rent to Value Ratio
Active
$829,000
3
bds
|
3
ba
|
1,957
sqft
|
built
2007
1276 S Pennsylvania Ave, Winter Park, FL 32789
$-2,159
Cash flow
-13.6%
Cash-on-Cash Return
3.2%
Cap rate
0.5%
Rent to Value Ratio
Active
$915,000
2
bds
|
2
ba
|
1,143
sqft
|
built
1971
100 S Interlachen Ave, Winter Park, FL 32789
$-3,721
Cash flow
-21.2%
Cash-on-Cash Return
1.4%
Cap rate
0.3%
Rent to Value Ratio
Active
$259,000
2
bds
|
2
ba
|
908
sqft
|
built
1967
1250 S Denning Dr, Winter Park, FL 32789
$-275
Cash flow
-5.5%
Cash-on-Cash Return
5.0%
Cap rate
0.7%
Rent to Value Ratio
Active
$549,000
2
bds
|
2
ba
|
1,400
sqft
|
built
1969
690 Osceola Ave, Winter Park, FL 32789
$-1,866
Cash flow
-17.7%
Cash-on-Cash Return
2.2%
Cap rate
0.7%
Rent to Value Ratio
Active
$214,900
3
bds
|
3
ba
|
1,151
sqft
|
built
1984
3251 Oak Lake Pl, Winter Park, FL 32792
$-120
Cash flow
-2.9%
Cash-on-Cash Return
5.6%
Cap rate
0.8%
Rent to Value Ratio
Active
$239,900
2
bds
|
3
ba
|
1,578
sqft
|
built
1974
7461 Swallow Run, Winter Park, FL 32792
$-141
Cash flow
-3.1%
Cash-on-Cash Return
5.6%
Cap rate
0.8%
Rent to Value Ratio
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
$177,000
1
bds
|
1
ba
|
835
sqft
|
built
1970
200 Saint Andrews Blvd, Winter Park, FL 32792
$-492
Cash flow
-14.5%
Cash-on-Cash Return
2.9%
Cap rate
0.8%
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
$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
$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
$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
$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