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
$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
$275,000
2
bds
|
2
ba
|
932
sqft
|
built
1976
2426 Windward Way, Winter Park, FL 32792
$-328
Cash flow
-6.2%
Cash-on-Cash Return
4.9%
Cap rate
0.7%
Rent to Value Ratio
250 out of 288 properties for sale in Winter Park, FL
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Active
$439,999
4
bds
|
2
ba
|
2,027
sqft
|
built
1986
2209 Fairglenn Way, Winter Park, FL 32792
$-598
Cash flow
-7.1%
Cash-on-Cash Return
4.7%
Cap rate
0.6%
Rent to Value Ratio
Active
$420,000
4
bds
|
2
ba
|
1,996
sqft
|
built
1977
5436 Tangerine Ave, Winter Park, FL 32792
$-698
Cash flow
-8.7%
Cash-on-Cash Return
4.3%
Cap rate
0.6%
Rent to Value Ratio
Pending
$410,000
3
bds
|
2
ba
|
1,414
sqft
|
built
1985
5575 Garden Grove Cir, Winter Park, FL 32792
$-651
Cash flow
-8.3%
Cash-on-Cash Return
4.4%
Cap rate
0.6%
Rent to Value Ratio
Active
$275,000
2
bds
|
2
ba
|
932
sqft
|
built
1976
2426 Windward Way, Winter Park, FL 32792
$-328
Cash flow
-6.2%
Cash-on-Cash Return
4.9%
Cap rate
0.7%
Rent to Value Ratio
Active
$549,000
3
bds
|
2
ba
|
1,630
sqft
|
built
1950
240 Cambridge Blvd, Winter Park, FL 32789
$-1,072
Cash flow
-10.2%
Cash-on-Cash Return
3.9%
Cap rate
0.6%
Rent to Value Ratio
Active
$789,000
4
bds
|
2
ba
|
2,509
sqft
|
built
1967
627 Darcey Dr, Winter Park, FL 32792
$-2,301
Cash flow
-15.2%
Cash-on-Cash Return
2.8%
Cap rate
0.5%
Rent to Value Ratio
Active
$1,495,000
4
bds
|
4
ba
|
2,953
sqft
|
built
2004
1420 Palmer Ave, Winter Park, FL 32789
$-4,764
Cash flow
-16.6%
Cash-on-Cash Return
2.5%
Cap rate
0.4%
Rent to Value Ratio
Active
$489,000
3
bds
|
3
ba
|
1,880
sqft
|
built
1961
2835 Bongart Rd, Winter Park, FL 32792
$-1,028
Cash flow
-11.0%
Cash-on-Cash Return
3.8%
Cap rate
0.5%
Rent to Value Ratio
Active
$1,599,000
5
bds
|
4
ba
|
4,181
sqft
|
built
1979
1327 Bridgeport Dr, Winter Park, FL 32789
$-5,392
Cash flow
-17.6%
Cash-on-Cash Return
2.2%
Cap rate
0.4%
Rent to Value Ratio
Pending
$412,500
3
bds
|
2
ba
|
1,503
sqft
|
built
1967
3443 Arnel Dr, Winter Park, FL 32792
$-790
Cash flow
-10.0%
Cash-on-Cash Return
4.0%
Cap rate
0.6%
Rent to Value Ratio
Active
$4,175,000
4
bds
|
6
ba
|
4,683
sqft
|
built
1954
1581 Forest Ave, Winter Park, FL 32789
$-20,014
Cash flow
-25.0%
Cash-on-Cash Return
0.5%
Cap rate
0.1%
Rent to Value Ratio
Active
$399,990
4
bds
|
2
ba
|
1,704
sqft
|
built
1974
1017 Manchester Cir, Winter Park, FL 32792
$-617
Cash flow
-8.0%
Cash-on-Cash Return
4.4%
Cap rate
0.6%
Rent to Value Ratio
Active
$924,900
3
bds
|
3
ba
|
1,314
sqft
|
built
1949
251 Glenridge Way, Winter Park, FL 32789
$-3,504
Cash flow
-19.8%
Cash-on-Cash Return
1.7%
Cap rate
0.3%
Rent to Value Ratio
Active
$8,500,000
5
bds
|
6
ba
|
6,502
sqft
|
built
2013
1112 Preserve Point Dr, Winter Park, FL 32789
$-45,938
Cash flow
-28.2%
Cash-on-Cash Return
-0.2%
Cap rate
0.1%
Rent to Value Ratio
Active
$435,000
3
bds
|
2
ba
|
1,517
sqft
|
built
1986
5547 Garden Grove Cir, Winter Park, FL 32792
$-749
Cash flow
-9.0%
Cash-on-Cash Return
4.2%
Cap rate
0.6%
Rent to Value Ratio
Pending
$334,985
2
bds
|
2
ba
|
1,320
sqft
|
built
1985
631 Warrenton Rd, Winter Park, FL 32792
$-937
Cash flow
-14.6%
Cash-on-Cash Return
2.9%
Cap rate
0.5%
Rent to Value Ratio
Active
$1,199,000
4
bds
|
5
ba
|
4,015
sqft
|
built
1995
4052 Gilder Rose Pl, Winter Park, FL 32792
$-2,718
Cash flow
-11.8%
Cash-on-Cash Return
3.6%
Cap rate
0.5%
Rent to Value Ratio
Active
$529,900
4
bds
|
3
ba
|
2,616
sqft
|
built
1971
7679 Bent Bow Trl, Winter Park, FL 32792
$-1,403
Cash flow
-13.8%
Cash-on-Cash Return
3.1%
Cap rate
0.5%
Rent to Value Ratio
Active
$439,500
4
bds
|
2
ba
|
1,836
sqft
|
built
1963
1842 Puritan Ave, Winter Park, FL 32792
$-696
Cash flow
-8.3%
Cash-on-Cash Return
4.4%
Cap rate
0.6%
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
$465,000
3
bds
|
2
ba
|
1,804
sqft
|
built
2003
3304 Bennington Ct, Winter Park, FL 32792
$-907
Cash flow
-10.2%
Cash-on-Cash Return
3.9%
Cap rate
0.5%
Rent to Value Ratio
Active
$379,900
3
bds
|
2
ba
|
1,503
sqft
|
built
1967
3121 Thistle Hill Dr, Winter Park, FL 32792
$-519
Cash flow
-7.1%
Cash-on-Cash Return
4.6%
Cap rate
0.6%
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
Pending
$369,900
3
bds
|
2
ba
|
1,368
sqft
|
built
1987
1748 Harvest Cv, Winter Park, FL 32792
$-539
Cash flow
-7.6%
Cash-on-Cash Return
4.5%
Cap rate
0.6%
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
$1,554,950
4
bds
|
4
ba
|
3,474
sqft
|
built
2008
952 Moss Ln, Winter Park, FL 32789
$-6,378
Cash flow
-21.4%
Cash-on-Cash Return
1.4%
Cap rate
0.4%
Rent to Value Ratio
Active
$450,000
3
bds
|
2
ba
|
1,349
sqft
|
built
1957
619 Byron Rd, Winter Park, FL 32792
$-776
Cash flow
-9.0%
Cash-on-Cash Return
4.2%
Cap rate
0.6%
Rent to Value Ratio
Active
$2,455,000
4
bds
|
5
ba
|
3,883
sqft
|
built
2015
521 S Phelps Ave, Winter Park, FL 32789
$-10,946
Cash flow
-23.3%
Cash-on-Cash Return
0.9%
Cap rate
0.3%
Rent to Value Ratio
Active
$1,999,000
4
bds
|
3
ba
|
2,674
sqft
|
built
1968
633 Balmoral Rd, Winter Park, FL 32789
$-6,981
Cash flow
-18.2%
Cash-on-Cash Return
2.1%
Cap rate
0.3%
Rent to Value Ratio
Active
$1,595,000
3
bds
|
3
ba
|
2,351
sqft
|
built
2013
1741 Palmer Ave, Winter Park, FL 32789
$-5,367
Cash flow
-17.6%
Cash-on-Cash Return
2.2%
Cap rate
0.4%
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
$510,000
4
bds
|
2
ba
|
2,313
sqft
|
built
1987
1742 Willa Cir, Winter Park, FL 32792
$-1,152
Cash flow
-11.8%
Cash-on-Cash Return
3.6%
Cap rate
0.6%
Rent to Value Ratio
Active
$414,999
3
bds
|
2
ba
|
1,540
sqft
|
built
1956
920 Gloriosa Ave, Winter Park, FL 32789
$-718
Cash flow
-9.0%
Cash-on-Cash Return
4.2%
Cap rate
0.6%
Rent to Value Ratio
Active
$479,900
3
bds
|
2
ba
|
1,939
sqft
|
built
1973
3054 Bluebrook Dr, Winter Park, FL 32792
$-1,021
Cash flow
-11.1%
Cash-on-Cash Return
3.7%
Cap rate
0.6%
Rent to Value Ratio
Active
$1,999,900
4
bds
|
3
ba
|
3,117
sqft
|
built
2022
1521 Chestnut Ave, Winter Park, FL 32789
$-9,013
Cash flow
-23.5%
Cash-on-Cash Return
0.9%
Cap rate
0.2%
Rent to Value Ratio
Active
$550,000
4
bds
|
0
ba
|
1,805
sqft
|
built
1959
2627 Ambergate Rd, Winter Park, FL 32792
$-1,419
Cash flow
-13.5%
Cash-on-Cash Return
3.2%
Cap rate
0.5%
Rent to Value Ratio
Active
$499,000
2
bds
|
2
ba
|
1,260
sqft
|
built
1925
674 Douglas Ave, Winter Park, FL 32789
$-1,434
Cash flow
-15.0%
Cash-on-Cash Return
2.8%
Cap rate
0.5%
Rent to Value Ratio
Active
$499,900
4
bds
|
2
ba
|
2,195
sqft
|
built
1976
5338 Tangerine Ave, Winter Park, FL 32792
$-857
Cash flow
-8.9%
Cash-on-Cash Return
4.2%
Cap rate
0.6%
Rent to Value Ratio