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
$207,900
1
bds
|
1
ba
|
645
sqft
|
built
1969
2500 Lee Rd, Winter Park, FL 32789
$-8
Cash flow
-0.2%
Cash-on-Cash Return
6.1%
Cap rate
0.8%
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
250 out of 288 properties for sale in Winter Park, FL
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Active
$369,000
4
bds
|
2
ba
|
1,349
sqft
|
built
1955
657 Overspin Dr, Winter Park, FL 32789
$-288
Cash flow
-4.1%
Cash-on-Cash Return
5.2%
Cap rate
0.7%
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
$207,900
1
bds
|
1
ba
|
645
sqft
|
built
1969
2500 Lee Rd, Winter Park, FL 32789
$-8
Cash flow
-0.2%
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
$-284
Cash flow
-9.3%
Cash-on-Cash Return
4.0%
Cap rate
0.9%
Rent to Value Ratio
Active
$2,895,000
4
bds
|
5
ba
|
3,551
sqft
|
built
1995
940 Lincoln Cir, Winter Park, FL 32789
$-9,503
Cash flow
-17.1%
Cash-on-Cash Return
2.2%
Cap rate
0.3%
Rent to Value Ratio
Active
$775,000
4
bds
|
4
ba
|
2,587
sqft
|
built
2022
1340 Blue Stem Ln, Winter Park, FL 32792
$-2,691
Cash flow
-18.1%
Cash-on-Cash Return
2.0%
Cap rate
0.4%
Rent to Value Ratio
Active
$549,000
3
bds
|
3
ba
|
1,616
sqft
|
built
2008
1745 Indiana Ave, Winter Park, FL 32789
$-1,302
Cash flow
-12.4%
Cash-on-Cash Return
3.3%
Cap rate
0.5%
Rent to Value Ratio
Active
$245,000
2
bds
|
1
ba
|
710
sqft
|
built
1960
151 N Orlando Ave, Winter Park, FL 32789
$-678
Cash flow
-14.4%
Cash-on-Cash Return
2.8%
Cap rate
0.7%
Rent to Value Ratio
Active
$299,000
2
bds
|
1
ba
|
894
sqft
|
built
1957
849 Driver Ave, Winter Park, FL 32789
$-523
Cash flow
-9.1%
Cash-on-Cash Return
4.0%
Cap rate
0.7%
Rent to Value Ratio
Active
$400,000
3
bds
|
2
ba
|
1,226
sqft
|
built
1973
5234 Ohio St, Winter Park, FL 32792
$-852
Cash flow
-11.1%
Cash-on-Cash Return
3.6%
Cap rate
0.5%
Rent to Value Ratio
Active
$3,595,000
6
bds
|
6
ba
|
5,878
sqft
|
built
2006
141 S Phelps Ave, Winter Park, FL 32789
$-14,254
Cash flow
-20.7%
Cash-on-Cash Return
1.4%
Cap rate
0.3%
Rent to Value Ratio
Active
$775,000
3
bds
|
3
ba
|
1,939
sqft
|
built
2019
1429 Indiana Ave, Winter Park, FL 32789
$-1,876
Cash flow
-12.6%
Cash-on-Cash Return
3.2%
Cap rate
0.6%
Rent to Value Ratio
Pending
$777,000
4
bds
|
3
ba
|
2,192
sqft
|
built
2019
2159 Marsh Sedge Ln, Winter Park, FL 32792
$-2,141
Cash flow
-14.4%
Cash-on-Cash Return
2.8%
Cap rate
0.5%
Rent to Value Ratio
Active
$520,000
4
bds
|
2
ba
|
1,631
sqft
|
built
1956
1809 Pineview Cir, Winter Park, FL 32792
$-1,196
Cash flow
-12.0%
Cash-on-Cash Return
3.4%
Cap rate
0.5%
Rent to Value Ratio
Active
$2,725,000
5
bds
|
6
ba
|
4,338
sqft
|
built
2008
1400 Place Picardy, Winter Park, FL 32789
$-9,466
Cash flow
-18.1%
Cash-on-Cash Return
2.0%
Cap rate
0.4%
Rent to Value Ratio
Active
$950,000
5
bds
|
3
ba
|
2,406
sqft
|
built
1965
3011 Temple Trl, Winter Park, FL 32789
$-1,632
Cash flow
-9.0%
Cash-on-Cash Return
4.1%
Cap rate
0.6%
Rent to Value Ratio
Active
$525,000
3
bds
|
2
ba
|
1,752
sqft
|
built
1964
2138 Whitehall Dr, Winter Park, FL 32792
$-928
Cash flow
-9.2%
Cash-on-Cash Return
4.0%
Cap rate
0.5%
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
$475,000
4
bds
|
3
ba
|
1,766
sqft
|
built
1956
2886 Carew Ave, Winter Park, FL 32789
$-1,106
Cash flow
-12.1%
Cash-on-Cash Return
3.4%
Cap rate
0.5%
Rent to Value Ratio
Active
$2,749,000
5
bds
|
6
ba
|
3,967
sqft
|
built
2020
1690 Palm Ave, Winter Park, FL 32789
$-8,812
Cash flow
-16.7%
Cash-on-Cash Return
2.3%
Cap rate
0.4%
Rent to Value Ratio
Active
$675,000
3
bds
|
2
ba
|
1,804
sqft
|
built
1948
1399 Aloma Ave, Winter Park, FL 32789
$-1,426
Cash flow
-11.0%
Cash-on-Cash Return
3.6%
Cap rate
0.5%
Rent to Value Ratio
Active
$357,000
4
bds
|
2
ba
|
1,366
sqft
|
built
1984
3041 Dikewood Ct, Winter Park, FL 32792
$-437
Cash flow
-6.4%
Cash-on-Cash Return
4.7%
Cap rate
0.6%
Rent to Value Ratio
Active
$440,000
3
bds
|
2
ba
|
1,732
sqft
|
built
1972
5001 Tangerine Ave, Winter Park, FL 32792
$-600
Cash flow
-7.1%
Cash-on-Cash Return
4.5%
Cap rate
0.6%
Rent to Value Ratio
Active
$1,350,000
3
bds
|
3
ba
|
1,993
sqft
|
built
1953
2525 Venetian Way, Winter Park, FL 32789
$-4,917
Cash flow
-19.0%
Cash-on-Cash Return
1.8%
Cap rate
0.3%
Rent to Value Ratio
Active
$800,000
3
bds
|
3
ba
|
1,745
sqft
|
built
2017
441 N Capen Ave, Winter Park, FL 32789
$-2,153
Cash flow
-14.0%
Cash-on-Cash Return
2.9%
Cap rate
0.5%
Rent to Value Ratio
Active
$1,325,000
5
bds
|
4
ba
|
3,068
sqft
|
built
1956
2105 Fosgate Dr, Winter Park, FL 32789
$-2,131
Cash flow
-8.4%
Cash-on-Cash Return
4.2%
Cap rate
0.5%
Rent to Value Ratio
Active
$628,900
3
bds
|
2
ba
|
1,844
sqft
|
built
1963
236 N Ranger Blvd, Winter Park, FL 32792
$-1,899
Cash flow
-15.8%
Cash-on-Cash Return
2.5%
Cap rate
0.4%
Rent to Value Ratio
Active
$839,000
4
bds
|
3
ba
|
2,192
sqft
|
built
2019
2168 Marsh Sedge Ln, Winter Park, FL 32792
$-2,797
Cash flow
-17.4%
Cash-on-Cash Return
2.1%
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
$-8,111
Cash flow
-24.2%
Cash-on-Cash Return
0.6%
Cap rate
0.3%
Rent to Value Ratio
Active
$2,499,000
6
bds
|
0
ba
|
4,056
sqft
|
built
1964
1903 S Lakemont Ave, Winter Park, FL 32792
$-11,154
Cash flow
-23.3%
Cash-on-Cash Return
0.8%
Cap rate
0.1%
Rent to Value Ratio
Active
$670,000
3
bds
|
2
ba
|
1,729
sqft
|
built
1953
3006 Northwood Blvd, Winter Park, FL 32789
$-1,837
Cash flow
-14.3%
Cash-on-Cash Return
2.9%
Cap rate
0.4%
Rent to Value Ratio
Pending
$1,200,000
3
bds
|
4
ba
|
3,096
sqft
|
built
1968
309 Park North Ct, Winter Park, FL 32789
$-4,185
Cash flow
-18.2%
Cash-on-Cash Return
2.0%
Cap rate
0.4%
Rent to Value Ratio
Active
$274,900
3
bds
|
3
ba
|
1,578
sqft
|
built
1974
7484 Canford Ct, Winter Park, FL 32792
$-561
Cash flow
-10.6%
Cash-on-Cash Return
3.7%
Cap rate
0.8%
Rent to Value Ratio
Active
$1,495,000
3
bds
|
3
ba
|
2,145
sqft
|
built
1974
1644 Hibiscus Ave, Winter Park, FL 32789
$-5,574
Cash flow
-19.5%
Cash-on-Cash Return
1.7%
Cap rate
0.3%
Rent to Value Ratio
Active
$270,000
2
bds
|
2
ba
|
1,036
sqft
|
built
1982
3310 Royal St, Winter Park, FL 32792
$-245
Cash flow
-4.7%
Cash-on-Cash Return
5.1%
Cap rate
0.7%
Rent to Value Ratio
Active
$748,000
5
bds
|
4
ba
|
3,152
sqft
|
built
2014
5275 Pine Lily Cir, Winter Park, FL 32792
$-1,942
Cash flow
-13.5%
Cash-on-Cash Return
3.0%
Cap rate
0.5%
Rent to Value Ratio
Active
$499,000
2
bds
|
1
ba
|
954
sqft
|
built
1945
3601 Midiron Dr, Winter Park, FL 32789
$-1,475
Cash flow
-15.4%
Cash-on-Cash Return
2.6%
Cap rate
0.5%
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