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
$299,900
3
bds
|
1
ba
|
1,114
sqft
|
built
1956
7102 Easter St, Winter Park, FL 32792
$-114
Cash flow
-2.0%
Cash-on-Cash Return
5.7%
Cap rate
0.8%
Rent to Value Ratio
Pending
$269,000
1
bds
|
1
ba
|
736
sqft
|
built
1948
1979 Staunton Ave, Winter Park, FL 32789
$-281
Cash flow
-5.5%
Cash-on-Cash Return
4.9%
Cap rate
0.6%
Rent to Value Ratio
171 out of 175 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
$-1,309
Cash flow
-11.9%
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
$-990
Cash flow
-12.0%
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
$-16,284
Cash flow
-23.6%
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
$-515
Cash flow
-5.1%
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
$-957
Cash flow
-10.2%
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
$-114
Cash flow
-2.0%
Cash-on-Cash Return
5.7%
Cap rate
0.8%
Rent to Value Ratio
Active
$575,000
3
bds
|
2
ba
|
1,867
sqft
|
built
1979
1387 Sawgrass Ct, Winter Park, FL 32792
$-1,227
Cash flow
-11.1%
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
$-4,952
Cash flow
-17.2%
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
$-4,127
Cash flow
-17.8%
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
$-1,965
Cash flow
-16.1%
Cash-on-Cash Return
2.4%
Cap rate
0.3%
Rent to Value Ratio
Pending
$949,900
3
bds
|
3
ba
|
1,981
sqft
|
built
1960
609 Langholm Dr, Winter Park, FL 32789
$-2,916
Cash flow
-16.0%
Cash-on-Cash Return
2.5%
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
$-2,753
Cash flow
-18.5%
Cash-on-Cash Return
1.9%
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
$-4,568
Cash flow
-16.7%
Cash-on-Cash Return
2.3%
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
$-1,571
Cash flow
-14.5%
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
$-9,702
Cash flow
-21.1%
Cash-on-Cash Return
1.3%
Cap rate
0.2%
Rent to Value Ratio
Active
$379,500
3
bds
|
2
ba
|
1,637
sqft
|
built
1983
1050 Reading Ct, Winter Park, FL 32792
$-637
Cash flow
-8.8%
Cash-on-Cash Return
4.1%
Cap rate
0.6%
Rent to Value Ratio
Active
$420,000
3
bds
|
2
ba
|
1,613
sqft
|
built
2003
5559 Pats Pt, Winter Park, FL 32792
$-1,050
Cash flow
-13.0%
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
$-12,116
Cash flow
-19.2%
Cash-on-Cash Return
1.7%
Cap rate
0.3%
Rent to Value Ratio
Active
$425,000
3
bds
|
2
ba
|
1,675
sqft
|
built
1981
2003 Bentwood Dr, Winter Park, FL 32792
$-354
Cash flow
-4.3%
Cash-on-Cash Return
5.1%
Cap rate
0.7%
Rent to Value Ratio
Active
$650,000
4
bds
|
2
ba
|
2,003
sqft
|
built
1981
1507 Golfside Dr, Winter Park, FL 32792
$-1,343
Cash flow
-10.8%
Cash-on-Cash Return
3.7%
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
$-2,358
Cash flow
-16.6%
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
$-4,094
Cash flow
-18.1%
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
$-1,470
Cash flow
-13.5%
Cash-on-Cash Return
3.1%
Cap rate
0.4%
Rent to Value Ratio
Pending
$269,000
1
bds
|
1
ba
|
736
sqft
|
built
1948
1979 Staunton Ave, Winter Park, FL 32789
$-281
Cash flow
-5.5%
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
$-1,743
Cash flow
-11.7%
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
$-3,590
Cash flow
-16.6%
Cash-on-Cash Return
2.3%
Cap rate
0.4%
Rent to Value Ratio
Active
$439,999
4
bds
|
2
ba
|
2,027
sqft
|
built
1986
2209 Fairglenn Way, Winter Park, FL 32792
$-548
Cash flow
-6.5%
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
$-650
Cash flow
-8.1%
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
$-604
Cash flow
-7.7%
Cash-on-Cash Return
4.4%
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
$-2,211
Cash flow
-14.6%
Cash-on-Cash Return
2.8%
Cap rate
0.5%
Rent to Value Ratio
Active
$559,000
3
bds
|
2
ba
|
1,630
sqft
|
built
1950
240 Cambridge Blvd, Winter Park, FL 32789
$-1,060
Cash flow
-9.9%
Cash-on-Cash Return
3.9%
Cap rate
0.6%
Rent to Value Ratio
Active
$1,495,000
4
bds
|
4
ba
|
2,953
sqft
|
built
2004
1420 Palmer Ave, Winter Park, FL 32789
$-4,593
Cash flow
-16.0%
Cash-on-Cash Return
2.5%
Cap rate
0.4%
Rent to Value Ratio
Active
$499,000
3
bds
|
3
ba
|
1,880
sqft
|
built
1961
2835 Bongart Rd, Winter Park, FL 32792
$-1,023
Cash flow
-10.7%
Cash-on-Cash Return
3.7%
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
$-5,209
Cash flow
-17.0%
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
$-743
Cash flow
-9.4%
Cash-on-Cash Return
4.0%
Cap rate
0.6%
Rent to Value Ratio
Active
$399,990
4
bds
|
2
ba
|
1,704
sqft
|
built
1974
1017 Manchester Cir, Winter Park, FL 32792
$-571
Cash flow
-7.4%
Cash-on-Cash Return
4.4%
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
$-19,537
Cash flow
-24.4%
Cash-on-Cash Return
0.5%
Cap rate
0.1%
Rent to Value Ratio
Active
$924,900
3
bds
|
3
ba
|
1,314
sqft
|
built
1949
251 Glenridge Way, Winter Park, FL 32789
$-3,399
Cash flow
-19.2%
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
$-44,967
Cash flow
-27.6%
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
$-699
Cash flow
-8.4%
Cash-on-Cash Return
4.2%
Cap rate
0.6%
Rent to Value Ratio