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
$137,500
2
bds
|
1
ba
|
881
sqft
|
built
1966
1695 Lee Rd, Winter Park, FL 32789
$214
Cash flow
8.1%
Cash-on-Cash Return
8.1%
Cap rate
1.2%
Rent to Value Ratio
Active
$214,900
3
bds
|
3
ba
|
1,151
sqft
|
built
1984
3251 Oak Lake Pl, Winter Park, FL 32792
$-117
Cash flow
-2.8%
Cash-on-Cash Return
5.6%
Cap rate
0.8%
Rent to Value Ratio
247 out of 284 properties for sale in Winter Park, FL
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Active
$659,000
3
bds
|
2
ba
|
1,762
sqft
|
built
1963
624 Dunraven Dr, Winter Park, FL 32792
$-1,450
Cash flow
-11.5%
Cash-on-Cash Return
3.6%
Cap rate
0.5%
Rent to Value Ratio
Active
$205,990
3
bds
|
2
ba
|
1,149
sqft
|
built
1966
1695 Lee Rd, Winter Park, FL 32789
$-611
Cash flow
-15.5%
Cash-on-Cash Return
2.7%
Cap rate
0.9%
Rent to Value Ratio
Active
$1,299,000
4
bds
|
3
ba
|
2,388
sqft
|
built
2007
1341 Lyndale Blvd, Winter Park, FL 32789
$-5,008
Cash flow
-20.1%
Cash-on-Cash Return
1.6%
Cap rate
0.3%
Rent to Value Ratio
Active
$3,750,000
5
bds
|
6
ba
|
4,565
sqft
|
built
2016
2171 Forrest Rd, Winter Park, FL 32789
$-14,512
Cash flow
-20.2%
Cash-on-Cash Return
1.6%
Cap rate
0.3%
Rent to Value Ratio
Active
$2,950,000
4
bds
|
3
ba
|
2,663
sqft
|
built
1989
1020 Mayfield Ave, Winter Park, FL 32789
$-12,970
Cash flow
-22.9%
Cash-on-Cash Return
1.0%
Cap rate
0.2%
Rent to Value Ratio
Active
$950,000
3
bds
|
4
ba
|
2,116
sqft
|
built
2000
1251 Arlington Pl, Winter Park, FL 32789
$-2,706
Cash flow
-14.9%
Cash-on-Cash Return
2.8%
Cap rate
0.4%
Rent to Value Ratio
Active
$489,000
3
bds
|
2
ba
|
2,408
sqft
|
built
1985
3306 Fishermans Cv, Winter Park, FL 32792
$-636
Cash flow
-6.8%
Cash-on-Cash Return
4.7%
Cap rate
0.6%
Rent to Value Ratio
Active
$529,999
3
bds
|
2
ba
|
2,706
sqft
|
built
1971
7730 Broken Arrow Trl, Winter Park, FL 32792
$-991
Cash flow
-9.8%
Cash-on-Cash Return
4.0%
Cap rate
0.5%
Rent to Value Ratio
Active
$515,000
4
bds
|
3
ba
|
2,076
sqft
|
built
1970
2227 Coventry Dr, Winter Park, FL 32792
$-1,572
Cash flow
-15.9%
Cash-on-Cash Return
2.6%
Cap rate
0.4%
Rent to Value Ratio
Active
$137,500
2
bds
|
1
ba
|
881
sqft
|
built
1966
1695 Lee Rd, Winter Park, FL 32789
$214
Cash flow
8.1%
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
$-3,895
Cash flow
-18.8%
Cash-on-Cash Return
1.9%
Cap rate
0.4%
Rent to Value Ratio
Active
$3,295,000
5
bds
|
6
ba
|
3,974
sqft
|
built
2023
532 Worthington Dr, Winter Park, FL 32789
$-12,620
Cash flow
-20.0%
Cash-on-Cash Return
1.7%
Cap rate
0.3%
Rent to Value Ratio
Active
$1,099,000
5
bds
|
5
ba
|
4,307
sqft
|
built
2021
2011 Soaring Oak Way, Winter Park, FL 32792
$-3,261
Cash flow
-15.5%
Cash-on-Cash Return
2.7%
Cap rate
0.5%
Rent to Value Ratio
Active
$575,000
2
bds
|
1
ba
|
1,000
sqft
|
built
1955
1821 Goodrich Ave, Winter Park, FL 32789
$-2,017
Cash flow
-18.3%
Cash-on-Cash Return
2.1%
Cap rate
0.4%
Rent to Value Ratio
Pending
$640,000
3
bds
|
2
ba
|
1,727
sqft
|
built
1963
2855 Lion Heart Rd, Winter Park, FL 32792
$-1,762
Cash flow
-14.4%
Cash-on-Cash Return
3.0%
Cap rate
0.4%
Rent to Value Ratio
Active
$519,900
3
bds
|
2
ba
|
1,906
sqft
|
built
1972
7584 Lodge Pole Trl, Winter Park, FL 32792
$-1,326
Cash flow
-13.3%
Cash-on-Cash Return
3.2%
Cap rate
0.5%
Rent to Value Ratio
Active
$554,000
4
bds
|
2
ba
|
2,126
sqft
|
built
1967
3131 Lowndes Dr, Winter Park, FL 32792
$-1,435
Cash flow
-13.5%
Cash-on-Cash Return
3.2%
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
$-2,146
Cash flow
-13.5%
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
$-3,706
Cash flow
-21.1%
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
$-271
Cash flow
-5.5%
Cash-on-Cash Return
5.0%
Cap rate
0.7%
Rent to Value Ratio
Active
$349,000
3
bds
|
3
ba
|
1,456
sqft
|
built
1995
156 Oak Grove Rd, Winter Park, FL 32789
$-299
Cash flow
-4.5%
Cash-on-Cash Return
5.2%
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
$-1,857
Cash flow
-17.6%
Cash-on-Cash Return
2.2%
Cap rate
0.7%
Rent to Value Ratio
Active
$349,000
2
bds
|
2
ba
|
1,056
sqft
|
built
1983
3204 Netherwood Dr, Winter Park, FL 32792
$-935
Cash flow
-14.0%
Cash-on-Cash Return
3.0%
Cap rate
0.5%
Rent to Value Ratio
Active
$550,000
4
bds
|
2
ba
|
1,699
sqft
|
built
1957
2007 Strathaven Rd, Winter Park, FL 32792
$-1,090
Cash flow
-10.3%
Cash-on-Cash Return
3.9%
Cap rate
0.5%
Rent to Value Ratio
Active
$379,000
3
bds
|
2
ba
|
1,274
sqft
|
built
1976
5144 Orange Ave, Winter Park, FL 32792
$-463
Cash flow
-6.4%
Cash-on-Cash Return
4.8%
Cap rate
0.6%
Rent to Value Ratio
Active
$450,000
2
bds
|
2
ba
|
1,947
sqft
|
built
1987
1430 Hyde Park Dr, Winter Park, FL 32792
$-946
Cash flow
-11.0%
Cash-on-Cash Return
3.7%
Cap rate
0.6%
Rent to Value Ratio
Active
$399,900
3
bds
|
2
ba
|
1,200
sqft
|
built
1965
3214 Lowndes Dr, Winter Park, FL 32792
$-1,001
Cash flow
-13.1%
Cash-on-Cash Return
3.3%
Cap rate
0.6%
Rent to Value Ratio
Active
$525,000
4
bds
|
2
ba
|
2,053
sqft
|
built
2003
7619 Georgeann St, Winter Park, FL 32792
$-1,670
Cash flow
-16.6%
Cash-on-Cash Return
2.4%
Cap rate
0.4%
Rent to Value Ratio
Active
$214,900
3
bds
|
3
ba
|
1,151
sqft
|
built
1984
3251 Oak Lake Pl, Winter Park, FL 32792
$-117
Cash flow
-2.8%
Cash-on-Cash Return
5.6%
Cap rate
0.8%
Rent to Value Ratio
Pending
$380,000
4
bds
|
2
ba
|
1,678
sqft
|
built
1977
1041 Manchester Cir, Winter Park, FL 32792
$-374
Cash flow
-5.1%
Cash-on-Cash Return
5.1%
Cap rate
0.7%
Rent to Value Ratio
Active
$579,000
3
bds
|
2
ba
|
2,268
sqft
|
built
1961
701 Denton Rd, Winter Park, FL 32792
$-1,334
Cash flow
-12.0%
Cash-on-Cash Return
3.5%
Cap rate
0.6%
Rent to Value Ratio
Active
$1,195,000
5
bds
|
3
ba
|
3,858
sqft
|
built
1978
7706 Waunatta Ct, Winter Park, FL 32792
$-4,062
Cash flow
-17.7%
Cash-on-Cash Return
2.2%
Cap rate
0.3%
Rent to Value Ratio
Active
$239,900
2
bds
|
3
ba
|
1,578
sqft
|
built
1974
7461 Swallow Run, Winter Park, FL 32792
$-137
Cash flow
-3.0%
Cash-on-Cash Return
5.6%
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
$-8,339
Cash flow
-20.2%
Cash-on-Cash Return
1.6%
Cap rate
0.3%
Rent to Value Ratio
Active
$649,000
4
bds
|
3
ba
|
1,897
sqft
|
built
1965
690 S Lakemont Ave, Winter Park, FL 32792
$-1,560
Cash flow
-12.5%
Cash-on-Cash Return
3.4%
Cap rate
0.6%
Rent to Value Ratio
Active
$1,899,000
5
bds
|
5
ba
|
4,288
sqft
|
built
1978
4469 Old Bear Run, Winter Park, FL 32792
$-7,012
Cash flow
-19.3%
Cash-on-Cash Return
1.8%
Cap rate
0.3%
Rent to Value Ratio
Active
$549,000
3
bds
|
2
ba
|
1,656
sqft
|
built
1955
426 S Lakemont Ave, Winter Park, FL 32792
$-1,426
Cash flow
-13.6%
Cash-on-Cash Return
3.1%
Cap rate
0.5%
Rent to Value Ratio
Active
$725,000
2
bds
|
2
ba
|
949
sqft
|
built
1969
101 S Interlachen Ave, Winter Park, FL 32789
$-2,009
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
$-489
Cash flow
-14.4%
Cash-on-Cash Return
2.9%
Cap rate
0.8%
Rent to Value Ratio
Active
$625,000
3
bds
|
3
ba
|
1,890
sqft
|
built
1949
1360 Formosa Ave, Winter Park, FL 32789
$-2,441
Cash flow
-20.4%
Cash-on-Cash Return
1.6%
Cap rate
0.4%
Rent to Value Ratio