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
$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
250 out of 288 properties for sale in Winter Park, FL
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Pending
$575,000
4
bds
|
3
ba
|
2,219
sqft
|
built
1972
7852 Broken Arrow Trl, Winter Park, FL 32792
$-1,375
Cash flow
-12.5%
Cash-on-Cash Return
3.4%
Cap rate
0.5%
Rent to Value Ratio
Pending
$429,000
3
bds
|
2
ba
|
1,140
sqft
|
built
1961
2809 Sanbina St, Winter Park, FL 32789
$-1,039
Cash flow
-12.6%
Cash-on-Cash Return
3.4%
Cap rate
0.6%
Rent to Value Ratio
Active
$3,599,999
5
bds
|
6
ba
|
4,955
sqft
|
built
2017
1761 Legion Dr, Winter Park, FL 32789
$-16,695
Cash flow
-24.2%
Cash-on-Cash Return
0.7%
Cap rate
0.2%
Rent to Value Ratio
Active
$525,000
4
bds
|
3
ba
|
2,075
sqft
|
built
1987
1976 Shadyhill Ter, Winter Park, FL 32792
$-575
Cash flow
-5.7%
Cash-on-Cash Return
5.0%
Cap rate
0.7%
Rent to Value Ratio
Active
$489,000
3
bds
|
2
ba
|
1,623
sqft
|
built
1959
2648 Amsden Rd, Winter Park, FL 32792
$-1,013
Cash flow
-10.8%
Cash-on-Cash Return
3.8%
Cap rate
0.5%
Rent to Value Ratio
Active
$299,900
3
bds
|
1
ba
|
1,114
sqft
|
built
1956
7102 Easter St, Winter Park, FL 32792
$-148
Cash flow
-2.6%
Cash-on-Cash Return
5.7%
Cap rate
0.8%
Rent to Value Ratio
Pending
$575,000
3
bds
|
2
ba
|
1,867
sqft
|
built
1979
1387 Sawgrass Ct, Winter Park, FL 32792
$-1,293
Cash flow
-11.7%
Cash-on-Cash Return
3.6%
Cap rate
0.5%
Rent to Value Ratio
Active
$1,500,000
4
bds
|
4
ba
|
3,349
sqft
|
built
2014
2401 Lafayette Ave, Winter Park, FL 32789
$-5,123
Cash flow
-17.8%
Cash-on-Cash Return
2.2%
Cap rate
0.4%
Rent to Value Ratio
Active
$1,210,000
4
bds
|
4
ba
|
3,321
sqft
|
built
1992
4048 Gilder Rose Pl, Winter Park, FL 32792
$-4,265
Cash flow
-18.4%
Cash-on-Cash Return
2.1%
Cap rate
0.3%
Rent to Value Ratio
Active
$635,000
2
bds
|
1
ba
|
789
sqft
|
built
1953
1339 Orchid Ave, Winter Park, FL 32789
$-2,037
Cash flow
-16.7%
Cash-on-Cash Return
2.4%
Cap rate
0.3%
Rent to Value Ratio
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
Pending
$949,900
3
bds
|
3
ba
|
1,981
sqft
|
built
1960
609 Langholm Dr, Winter Park, FL 32789
$-3,024
Cash flow
-16.6%
Cash-on-Cash Return
2.5%
Cap rate
0.4%
Rent to Value Ratio
Active
$1,425,000
4
bds
|
4
ba
|
3,153
sqft
|
built
2019
2922 Reef Knot Pl, Winter Park, FL 32792
$-4,730
Cash flow
-17.3%
Cash-on-Cash Return
2.3%
Cap rate
0.4%
Rent to Value Ratio
Active
$775,000
3
bds
|
2
ba
|
1,598
sqft
|
built
1958
1961 Winter Park Rd, Winter Park, FL 32789
$-2,841
Cash flow
-19.1%
Cash-on-Cash Return
1.9%
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
$-136
Cash flow
-5.6%
Cash-on-Cash Return
5.0%
Cap rate
1.3%
Rent to Value Ratio
Active
$474,900
3
bds
|
3
ba
|
2,308
sqft
|
built
2019
1624 Little Wren Ln, Winter Park, FL 32792
$-1,273
Cash flow
-14.0%
Cash-on-Cash Return
3.1%
Cap rate
0.6%
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
$465,000
4
bds
|
0
ba
|
2,000
sqft
|
built
1980
131 Stefanik Rd, Winter Park, FL 32792
$-1,432
Cash flow
-16.1%
Cash-on-Cash Return
2.6%
Cap rate
0.4%
Rent to Value Ratio
Pending
$567,000
3
bds
|
2
ba
|
1,420
sqft
|
built
1957
1901 Loch Berry Rd, Winter Park, FL 32792
$-1,636
Cash flow
-15.1%
Cash-on-Cash Return
2.8%
Cap rate
0.4%
Rent to Value Ratio
Active
$2,399,000
3
bds
|
4
ba
|
3,440
sqft
|
built
2001
922 N Pennsylvania Ave, Winter Park, FL 32789
$-9,976
Cash flow
-21.7%
Cash-on-Cash Return
1.3%
Cap rate
0.2%
Rent to Value Ratio
Active
$465,000
4
bds
|
0
ba
|
2,000
sqft
|
built
1981
2608 Dora Ct, Winter Park, FL 32792
$-1,365
Cash flow
-15.3%
Cash-on-Cash Return
2.8%
Cap rate
0.5%
Rent to Value Ratio
Active
$379,500
3
bds
|
2
ba
|
1,637
sqft
|
built
1983
1050 Reading Ct, Winter Park, FL 32792
$-680
Cash flow
-9.3%
Cash-on-Cash Return
4.1%
Cap rate
0.6%
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
$355,000
3
bds
|
3
ba
|
1,406
sqft
|
built
2020
3118 Crown Jewel Ct, Winter Park, FL 32792
$-756
Cash flow
-11.1%
Cash-on-Cash Return
3.7%
Cap rate
0.6%
Rent to Value Ratio
Pending
$290,000
2
bds
|
2
ba
|
1,020
sqft
|
built
1977
2541 Leeward Way, Winter Park, FL 32792
$-856
Cash flow
-15.4%
Cash-on-Cash Return
2.7%
Cap rate
0.5%
Rent to Value Ratio
Active
$420,000
3
bds
|
2
ba
|
1,613
sqft
|
built
2003
5559 Pats Pt, Winter Park, FL 32792
$-1,098
Cash flow
-13.6%
Cash-on-Cash Return
3.1%
Cap rate
0.5%
Rent to Value Ratio
Active
$3,300,000
5
bds
|
6
ba
|
4,263
sqft
|
built
2015
1820 Englewood Rd, Winter Park, FL 32789
$-12,493
Cash flow
-19.8%
Cash-on-Cash Return
1.7%
Cap rate
0.3%
Rent to Value Ratio
Active
$305,000
3
bds
|
2
ba
|
1,284
sqft
|
built
1979
2376 Dominica Run, Winter Park, FL 32792
$-524
Cash flow
-9.0%
Cash-on-Cash Return
4.2%
Cap rate
0.7%
Rent to Value Ratio
Active
$425,000
3
bds
|
2
ba
|
1,675
sqft
|
built
1981
2003 Bentwood Dr, Winter Park, FL 32792
$-403
Cash flow
-4.9%
Cash-on-Cash Return
5.1%
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
$650,000
4
bds
|
2
ba
|
2,003
sqft
|
built
1981
1507 Golfside Dr, Winter Park, FL 32792
$-1,417
Cash flow
-11.4%
Cash-on-Cash Return
3.7%
Cap rate
0.5%
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
$950,000
4
bds
|
2
ba
|
2,237
sqft
|
built
1958
1018 Turner Rd, Winter Park, FL 32789
$-2,232
Cash flow
-12.3%
Cash-on-Cash Return
3.5%
Cap rate
0.5%
Rent to Value Ratio
Pending
$740,000
3
bds
|
2
ba
|
2,245
sqft
|
built
1957
1840 Laurel Rd, Winter Park, FL 32789
$-2,442
Cash flow
-17.2%
Cash-on-Cash Return
2.3%
Cap rate
0.5%
Rent to Value Ratio
Active
$1,180,000
4
bds
|
4
ba
|
2,770
sqft
|
built
2018
2607 Lafayette Ave, Winter Park, FL 32789
$-4,228
Cash flow
-18.7%
Cash-on-Cash Return
2.0%
Cap rate
0.4%
Rent to Value Ratio
Active
$570,000
4
bds
|
2
ba
|
1,749
sqft
|
built
1965
3231 Lowndes Dr, Winter Park, FL 32792
$-1,535
Cash flow
-14.1%
Cash-on-Cash Return
3.1%
Cap rate
0.4%
Rent to Value Ratio
Active
$365,900
3
bds
|
3
ba
|
1,628
sqft
|
built
2003
2548 Galliano Cir, Winter Park, FL 32792
$-736
Cash flow
-10.5%
Cash-on-Cash Return
3.9%
Cap rate
0.6%
Rent to Value Ratio
Pending
$269,000
1
bds
|
1
ba
|
736
sqft
|
built
1948
1979 Staunton Ave, Winter Park, FL 32789
$-312
Cash flow
-6.1%
Cash-on-Cash Return
4.9%
Cap rate
0.6%
Rent to Value Ratio
Pending
$779,000
5
bds
|
3
ba
|
3,493
sqft
|
built
1969
103 Longhorn Rd, Winter Park, FL 32792
$-1,832
Cash flow
-12.3%
Cash-on-Cash Return
3.5%
Cap rate
0.5%
Rent to Value Ratio
Active
$1,125,000
5
bds
|
5
ba
|
3,839
sqft
|
built
1993
2880 Old Castle Dr, Winter Park, FL 32792
$-3,718
Cash flow
-17.2%
Cash-on-Cash Return
2.3%
Cap rate
0.4%
Rent to Value Ratio