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
$134,900
2
bds
|
2
ba
|
1,267
sqft
|
built
1974
7340 Daniel Webster Dr, Winter Park, FL 32792
$404
Cash flow
15.6%
Cash-on-Cash Return
9.7%
Cap rate
1.3%
Rent to Value Ratio
Active
$144,900
1
bds
|
1
ba
|
638
sqft
|
built
1966
1695 Lee Rd, Winter Park, FL 32789
$106
Cash flow
3.8%
Cash-on-Cash Return
7.0%
Cap rate
1.0%
Rent to Value Ratio
250 out of 288 properties for sale in Winter Park, FL
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Active
$218,000
2
bds
|
2
ba
|
1,018
sqft
|
built
1984
2935 Antique Oaks Cir, Winter Park, FL 32792
$-514
Cash flow
-12.3%
Cash-on-Cash Return
3.3%
Cap rate
0.8%
Rent to Value Ratio
Active
$1,300,000
4
bds
|
3
ba
|
2,310
sqft
|
built
1962
1400 S Pennsylvania Ave, Winter Park, FL 32789
$-3,523
Cash flow
-14.1%
Cash-on-Cash Return
2.9%
Cap rate
0.5%
Rent to Value Ratio
Active
$599,000
4
bds
|
2
ba
|
2,036
sqft
|
built
1954
1875 Staunton Ave, Winter Park, FL 32789
$-1,052
Cash flow
-9.2%
Cash-on-Cash Return
4.0%
Cap rate
0.7%
Rent to Value Ratio
Active
$398,000
3
bds
|
2
ba
|
1,606
sqft
|
built
1984
1309 Paradise Ln, Winter Park, FL 32792
$-452
Cash flow
-5.9%
Cash-on-Cash Return
4.8%
Cap rate
0.6%
Rent to Value Ratio
Active
$144,900
1
bds
|
1
ba
|
638
sqft
|
built
1966
1695 Lee Rd, Winter Park, FL 32789
$106
Cash flow
3.8%
Cash-on-Cash Return
7.0%
Cap rate
1.0%
Rent to Value Ratio
Active
$665,000
4
bds
|
3
ba
|
2,082
sqft
|
built
1958
1792 Killarney Dr, Winter Park, FL 32789
$-1,146
Cash flow
-9.0%
Cash-on-Cash Return
4.1%
Cap rate
0.6%
Rent to Value Ratio
Active
$210,000
2
bds
|
2
ba
|
1,105
sqft
|
built
1984
2924 Antique Oaks Cir, Winter Park, FL 32792
$-528
Cash flow
-13.1%
Cash-on-Cash Return
3.1%
Cap rate
0.9%
Rent to Value Ratio
Active
$449,900
4
bds
|
2
ba
|
1,827
sqft
|
built
1969
1354 Tierra Cir, Winter Park, FL 32792
$-693
Cash flow
-8.0%
Cash-on-Cash Return
4.3%
Cap rate
0.6%
Rent to Value Ratio
Active
$549,900
3
bds
|
2
ba
|
1,738
sqft
|
built
1978
1116 Fairway Dr, Winter Park, FL 32792
$-1,126
Cash flow
-10.7%
Cash-on-Cash Return
3.7%
Cap rate
0.6%
Rent to Value Ratio
Active
$220,000
3
bds
|
3
ba
|
1,161
sqft
|
built
1983
7403 Glen Oaks Way, Winter Park, FL 32792
$96
Cash flow
2.3%
Cash-on-Cash Return
6.7%
Cap rate
0.8%
Rent to Value Ratio
Active
$10,900,000
7
bds
|
11
ba
|
11,255
sqft
|
built
2009
1120 Preserve Point Dr, Winter Park, FL 32789
$-55,692
Cash flow
-26.7%
Cash-on-Cash Return
0.0%
Cap rate
0.1%
Rent to Value Ratio
Active
$190,000
2
bds
|
2
ba
|
1,049
sqft
|
built
1969
1000 S Semoran Blvd, Winter Park, FL 32792
$55
Cash flow
1.5%
Cash-on-Cash Return
6.5%
Cap rate
0.9%
Rent to Value Ratio
Active
$999,000
5
bds
|
3
ba
|
3,296
sqft
|
built
1928
2330 Westminster Ct, Winter Park, FL 32789
$-1,386
Cash flow
-7.2%
Cash-on-Cash Return
4.5%
Cap rate
0.6%
Rent to Value Ratio
Active
$499,900
4
bds
|
2
ba
|
1,827
sqft
|
built
1968
1422 Tierra Cir, Winter Park, FL 32792
$-737
Cash flow
-7.7%
Cash-on-Cash Return
4.4%
Cap rate
0.6%
Rent to Value Ratio
Active
$235,000
2
bds
|
2
ba
|
1,026
sqft
|
built
1972
1500 Gay Rd, Winter Park, FL 32789
$-94
Cash flow
-2.1%
Cash-on-Cash Return
5.7%
Cap rate
0.9%
Rent to Value Ratio
Active
$475,000
3
bds
|
2
ba
|
1,807
sqft
|
built
1983
1608 Bomi Cir, Winter Park, FL 32792
$-651
Cash flow
-7.2%
Cash-on-Cash Return
4.5%
Cap rate
0.6%
Rent to Value Ratio
Active
$196,400
2
bds
|
2
ba
|
1,105
sqft
|
built
1984
2923 Antique Oaks Cir, Winter Park, FL 32792
$-427
Cash flow
-11.3%
Cash-on-Cash Return
3.5%
Cap rate
0.9%
Rent to Value Ratio
Active
$134,900
2
bds
|
2
ba
|
1,267
sqft
|
built
1974
7340 Daniel Webster Dr, Winter Park, FL 32792
$404
Cash flow
15.6%
Cash-on-Cash Return
9.7%
Cap rate
1.3%
Rent to Value Ratio
Active
$4,750,000
5
bds
|
7
ba
|
6,338
sqft
|
built
2023
2161 Sharon Rd, Winter Park, FL 32789
$-25,605
Cash flow
-28.1%
Cash-on-Cash Return
-0.3%
Cap rate
0.1%
Rent to Value Ratio
Active
$510,000
4
bds
|
2
ba
|
2,122
sqft
|
built
1979
4026 Tenita Dr, Winter Park, FL 32792
$-620
Cash flow
-6.3%
Cash-on-Cash Return
4.7%
Cap rate
0.6%
Rent to Value Ratio
Pending
$695,000
2
bds
|
1
ba
|
1,146
sqft
|
built
1925
786 Antonette Ave, Winter Park, FL 32789
$-2,053
Cash flow
-15.4%
Cash-on-Cash Return
2.6%
Cap rate
0.4%
Rent to Value Ratio
Active
$460,000
4
bds
|
2
ba
|
1,765
sqft
|
built
1963
1621 Puritan Ave, Winter Park, FL 32792
$-504
Cash flow
-5.7%
Cash-on-Cash Return
4.8%
Cap rate
0.7%
Rent to Value Ratio
Active
$189,900
1
bds
|
1
ba
|
653
sqft
|
built
1967
1250 S Denning Dr, Winter Park, FL 32789
$-296
Cash flow
-8.1%
Cash-on-Cash Return
4.3%
Cap rate
0.8%
Rent to Value Ratio
Active
$189,900
3
bds
|
2
ba
|
1,149
sqft
|
built
1966
1695 Lee Rd, Winter Park, FL 32789
$102
Cash flow
2.8%
Cash-on-Cash Return
6.8%
Cap rate
0.9%
Rent to Value Ratio
Active
$256,900
2
bds
|
2
ba
|
1,068
sqft
|
built
1984
7707 Country Pl, Winter Park, FL 32792
$-512
Cash flow
-10.4%
Cash-on-Cash Return
3.8%
Cap rate
0.7%
Rent to Value Ratio
Active
$1,599,999
4
bds
|
4
ba
|
3,116
sqft
|
built
2014
1429 Chapman Cir, Winter Park, FL 32789
$-3,954
Cash flow
-12.9%
Cash-on-Cash Return
3.2%
Cap rate
0.5%
Rent to Value Ratio
Active
$149,900
2
bds
|
2
ba
|
1,030
sqft
|
built
1974
3053 George Mason Ave, Winter Park, FL 32792
$-176
Cash flow
-6.1%
Cash-on-Cash Return
4.7%
Cap rate
1.1%
Rent to Value Ratio
Active
$295,000
3
bds
|
2
ba
|
1,356
sqft
|
built
1956
4908 Seminole Ave, Winter Park, FL 32792
$-209
Cash flow
-3.7%
Cash-on-Cash Return
5.3%
Cap rate
0.7%
Rent to Value Ratio
Active
$425,000
3
bds
|
3
ba
|
1,725
sqft
|
built
1990
1820 Blaine Ter, Winter Park, FL 32792
$-767
Cash flow
-9.4%
Cash-on-Cash Return
4.0%
Cap rate
0.6%
Rent to Value Ratio
Active
$799,999
3
bds
|
2
ba
|
1,760
sqft
|
built
1953
2128 Sycamore Dr, Winter Park, FL 32789
$-2,110
Cash flow
-13.8%
Cash-on-Cash Return
3.0%
Cap rate
0.4%
Rent to Value Ratio
Active
$675,000
4
bds
|
4
ba
|
2,717
sqft
|
built
1995
3136 Heartleaf Pl, Winter Park, FL 32792
$-1,311
Cash flow
-10.1%
Cash-on-Cash Return
3.8%
Cap rate
0.6%
Rent to Value Ratio
Active
$1,295,000
3
bds
|
2
ba
|
2,342
sqft
|
built
1952
632 Country Club Dr, Winter Park, FL 32789
$-2,674
Cash flow
-10.8%
Cash-on-Cash Return
3.7%
Cap rate
0.5%
Rent to Value Ratio
Active
$129,000
1
bds
|
1
ba
|
803
sqft
|
built
1974
3045 Aaron Burr Ave, Winter Park, FL 32792
$-195
Cash flow
-7.9%
Cash-on-Cash Return
4.3%
Cap rate
1.1%
Rent to Value Ratio
Active
$2,270,000
4
bds
|
4
ba
|
3,399
sqft
|
built
2022
2522 Lafayette Ave, Winter Park, FL 32789
$-5,643
Cash flow
-13.0%
Cash-on-Cash Return
3.2%
Cap rate
0.5%
Rent to Value Ratio
Active
$5,000,000
5
bds
|
6
ba
|
5,072
sqft
|
built
2008
2228 Azalea Pl, Winter Park, FL 32789
$-21,762
Cash flow
-22.7%
Cash-on-Cash Return
0.9%
Cap rate
0.2%
Rent to Value Ratio
Active
$599,900
4
bds
|
2
ba
|
1,843
sqft
|
built
2013
8162 Lazy Bear Ln, Winter Park, FL 32792
$-1,738
Cash flow
-15.1%
Cash-on-Cash Return
2.7%
Cap rate
0.5%
Rent to Value Ratio
Active
$195,000
2
bds
|
2
ba
|
1,018
sqft
|
built
1984
3043 Antique Oaks Cir, Winter Park, FL 32792
$-436
Cash flow
-11.7%
Cash-on-Cash Return
3.5%
Cap rate
0.9%
Rent to Value Ratio
Active
$565,000
3
bds
|
2
ba
|
1,420
sqft
|
built
1963
274 N Ranger Blvd, Winter Park, FL 32792
$-832
Cash flow
-7.7%
Cash-on-Cash Return
4.4%
Cap rate
0.6%
Rent to Value Ratio
Active
$1,695,000
4
bds
|
3
ba
|
3,472
sqft
|
built
1961
279 Rippling Ln, Winter Park, FL 32789
$-3,947
Cash flow
-12.1%
Cash-on-Cash Return
3.4%
Cap rate
0.5%
Rent to Value Ratio
Active
$179,900
3
bds
|
2
ba
|
0
sqft
|
built
1974
7340 Daniel Webster Dr, Winter Park, FL 32792
$-661
Cash flow
-19.2%
Cash-on-Cash Return
1.7%
Cap rate
0.9%
Rent to Value Ratio