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
$212
Cash flow
8.0%
Cash-on-Cash Return
8.1%
Cap rate
1.2%
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
251 out of 289 properties for sale in Winter Park, FL
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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
$659,000
3
bds
|
2
ba
|
1,762
sqft
|
built
1963
624 Dunraven Dr, Winter Park, FL 32792
$-1,461
Cash flow
-11.6%
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
$-615
Cash flow
-15.6%
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
$-5,029
Cash flow
-20.2%
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
$-14,572
Cash flow
-20.3%
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
$-13,017
Cash flow
-23.0%
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
$-2,721
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
$-644
Cash flow
-6.9%
Cash-on-Cash Return
4.7%
Cap rate
0.6%
Rent to Value Ratio
Active
$1,495,000
3
bds
|
4
ba
|
3,215
sqft
|
built
1948
1661 Woodland Ave, Winter Park, FL 32789
$-5,709
Cash flow
-19.9%
Cash-on-Cash Return
1.7%
Cap rate
0.3%
Rent to Value Ratio
Active
$529,999
3
bds
|
2
ba
|
2,706
sqft
|
built
1971
7730 Broken Arrow Trl, Winter Park, FL 32792
$-999
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
$-1,580
Cash flow
-16.0%
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
$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
$3,295,000
5
bds
|
6
ba
|
3,974
sqft
|
built
2023
532 Worthington Dr, Winter Park, FL 32789
$-12,673
Cash flow
-20.1%
Cash-on-Cash Return
1.7%
Cap rate
0.3%
Rent to Value Ratio
Active
$1,115,000
5
bds
|
5
ba
|
4,307
sqft
|
built
2021
2011 Soaring Oak Way, Winter Park, FL 32792
$-3,362
Cash flow
-15.7%
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
$-2,026
Cash flow
-18.4%
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
$-1,773
Cash flow
-14.5%
Cash-on-Cash Return
3.0%
Cap rate
0.4%
Rent to Value Ratio
Active
$525,000
3
bds
|
2
ba
|
1,906
sqft
|
built
1972
7584 Lodge Pole Trl, Winter Park, FL 32792
$-1,361
Cash flow
-13.5%
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
$-1,444
Cash flow
-13.6%
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
$-2,159
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
$349,000
3
bds
|
3
ba
|
1,456
sqft
|
built
1995
156 Oak Grove Rd, Winter Park, FL 32789
$-305
Cash flow
-4.6%
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
$-1,866
Cash flow
-17.7%
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
$-941
Cash flow
-14.1%
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
$-1,099
Cash flow
-10.4%
Cash-on-Cash Return
3.9%
Cap rate
0.5%
Rent to Value Ratio
Active
$385,000
3
bds
|
2
ba
|
1,274
sqft
|
built
1976
5144 Orange Ave, Winter Park, FL 32792
$-500
Cash flow
-6.8%
Cash-on-Cash Return
4.7%
Cap rate
0.6%
Rent to Value Ratio
Active
$515,000
2
bds
|
2
ba
|
1,947
sqft
|
built
1987
1430 Hyde Park Dr, Winter Park, FL 32792
$-1,294
Cash flow
-13.1%
Cash-on-Cash Return
3.3%
Cap rate
0.5%
Rent to Value Ratio
Active
$399,900
3
bds
|
2
ba
|
1,200
sqft
|
built
1965
3214 Lowndes Dr, Winter Park, FL 32792
$-1,007
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
$-1,678
Cash flow
-16.7%
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
$-120
Cash flow
-2.9%
Cash-on-Cash Return
5.6%
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
$-380
Cash flow
-5.2%
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
$-1,343
Cash flow
-12.1%
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
$-4,081
Cash flow
-17.8%
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
$-141
Cash flow
-3.1%
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
$-8,373
Cash flow
-20.3%
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
$-1,571
Cash flow
-12.6%
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
$-7,043
Cash flow
-19.4%
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
$-1,435
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
$-2,021
Cash flow
-14.5%
Cash-on-Cash Return
2.9%
Cap rate
0.4%
Rent to Value Ratio