Winter Haven, FL Investment Properties for Sale
Browse homes for sale and investment properties in Winter Haven, FL. Refine your search by price, property type, or more.
Best cash flowing properties in Winter Haven, FL

Active

$219,900
2
bds
|
2
ba
|
1,419
sqft
|
built
2006
2642 Rutledge Ct, Winter Haven, FL 33884
$-34
Cash flow
-0.8%
Cash-on-Cash Return
6.0%
Cap rate
0.8%
Rent to Value Ratio

Active

$257,000
3
bds
|
2
ba
|
1,511
sqft
|
built
1958
121 Coleman Rd, Winter Haven, FL 33880
$-174
Cash flow
-3.5%
Cash-on-Cash Return
5.3%
Cap rate
0.8%
Rent to Value Ratio
248 out of 282 properties for sale in Winter Haven, FL
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Active

$399,900
4
bds
|
3
ba
|
3,034
sqft
|
built
2006
5392 Chandler Dr, Winter Haven, FL 33884
$-876
Cash flow
-11.4%
Cash-on-Cash Return
3.5%
Cap rate
0.6%
Rent to Value Ratio

Active

$849,000
4
bds
|
4
ba
|
3,480
sqft
|
built
1996
3211 Heron Cv, Winter Haven, FL 33884
$-1,513
Cash flow
-9.3%
Cash-on-Cash Return
4.0%
Cap rate
0.5%
Rent to Value Ratio

Active

$299,000
3
bds
|
2
ba
|
1,914
sqft
|
built
2000
131 Ruby Lake Dr, Winter Haven, FL 33884
$-454
Cash flow
-7.9%
Cash-on-Cash Return
4.3%
Cap rate
0.7%
Rent to Value Ratio

Active

$462,000
3
bds
|
3
ba
|
2,149
sqft
|
built
1981
35 S Lake Fox Rd, Winter Haven, FL 33884
$-1,273
Cash flow
-14.4%
Cash-on-Cash Return
2.8%
Cap rate
0.4%
Rent to Value Ratio

Active

$305,000
4
bds
|
2
ba
|
1,863
sqft
|
built
2012
249 Majestic Gardens Ln, Winter Haven, FL 33880
$-290
Cash flow
-5.0%
Cash-on-Cash Return
5.0%
Cap rate
0.7%
Rent to Value Ratio

Active

$299,500
3
bds
|
2
ba
|
1,424
sqft
|
built
1961
1505 Avenue F NE, Winter Haven, FL 33881
$-527
Cash flow
-9.2%
Cash-on-Cash Return
4.0%
Cap rate
0.6%
Rent to Value Ratio

Active

$245,000
3
bds
|
2
ba
|
950
sqft
|
built
1986
605 Kings Ln SW, Winter Haven, FL 33880
$-247
Cash flow
-5.3%
Cash-on-Cash Return
4.9%
Cap rate
0.7%
Rent to Value Ratio

Active

$325,000
4
bds
|
2
ba
|
1,822
sqft
|
built
2020
2363 Twin Lake View Rd, Winter Haven, FL 33881
$-378
Cash flow
-6.1%
Cash-on-Cash Return
4.8%
Cap rate
0.8%
Rent to Value Ratio

Active

$375,000
4
bds
|
2
ba
|
2,639
sqft
|
built
2006
258 Terranova Blvd, Winter Haven, FL 33884
$-860
Cash flow
-12.0%
Cash-on-Cash Return
3.4%
Cap rate
0.6%
Rent to Value Ratio

Active

$439,000
3
bds
|
2
ba
|
2,603
sqft
|
built
1986
2997 Plantation Rd, Winter Haven, FL 33884
$-686
Cash flow
-8.2%
Cash-on-Cash Return
4.3%
Cap rate
0.6%
Rent to Value Ratio

Active

$279,900
2
bds
|
2
ba
|
1,681
sqft
|
built
1977
263 Mariposa, Winter Haven, FL 33884
$-668
Cash flow
-12.5%
Cash-on-Cash Return
3.3%
Cap rate
0.6%
Rent to Value Ratio

Active

$1,100,000
4
bds
|
4
ba
|
3,197
sqft
|
built
2020
4741 Emerald Palms Ct, Winter Haven, FL 33884
$-2,958
Cash flow
-14.0%
Cash-on-Cash Return
2.9%
Cap rate
0.5%
Rent to Value Ratio

Active

$349,000
3
bds
|
2
ba
|
1,858
sqft
|
built
1973
417 Alachua Dr, Winter Haven, FL 33884
$-634
Cash flow
-9.5%
Cash-on-Cash Return
4.0%
Cap rate
0.5%
Rent to Value Ratio

Active

$379,900
4
bds
|
3
ba
|
3,075
sqft
|
built
2019
411 Sunfish Dr, Winter Haven, FL 33881
$-415
Cash flow
-5.7%
Cash-on-Cash Return
4.8%
Cap rate
0.8%
Rent to Value Ratio

Active

$466,500
4
bds
|
4
ba
|
2,723
sqft
|
built
1998
14 Pilot Pl, Winter Haven, FL 33881
$-217
Cash flow
-2.4%
Cash-on-Cash Return
5.6%
Cap rate
0.8%
Rent to Value Ratio

Active

$419,000
4
bds
|
2
ba
|
2,113
sqft
|
built
1994
115 Lake Mariam Way, Winter Haven, FL 33884
$-794
Cash flow
-9.9%
Cash-on-Cash Return
3.9%
Cap rate
0.5%
Rent to Value Ratio

Active

$315,000
4
bds
|
2
ba
|
1,488
sqft
|
built
1980
3356 Avenue Q NW, Winter Haven, FL 33881
$-1,013
Cash flow
-16.8%
Cash-on-Cash Return
2.3%
Cap rate
0.4%
Rent to Value Ratio

Active

$180,000
2
bds
|
2
ba
|
826
sqft
|
built
1984
2037 San Marcos Dr SE, Winter Haven, FL 33880
$-177
Cash flow
-5.1%
Cash-on-Cash Return
5.0%
Cap rate
0.8%
Rent to Value Ratio

Active

$369,990
4
bds
|
2
ba
|
2,280
sqft
|
built
2006
820 Sun Ridge Village Dr, Winter Haven, FL 33880
$-532
Cash flow
-7.5%
Cash-on-Cash Return
4.4%
Cap rate
0.6%
Rent to Value Ratio

Active

$334,999
5
bds
|
2
ba
|
1,904
sqft
|
built
2009
4515 Magnolia Preserve Ct, Winter Haven, FL 33880
$-472
Cash flow
-7.4%
Cash-on-Cash Return
4.5%
Cap rate
0.7%
Rent to Value Ratio

Active

$320,000
4
bds
|
2
ba
|
2,004
sqft
|
built
2023
983 Gotthard Pass Dr, Winter Haven, FL 33881
$-558
Cash flow
-9.1%
Cash-on-Cash Return
4.1%
Cap rate
0.7%
Rent to Value Ratio

Active

$365,000
4
bds
|
2
ba
|
1,717
sqft
|
built
2018
308 Lake Lucerne Way, Winter Haven, FL 33881
$-940
Cash flow
-13.4%
Cash-on-Cash Return
3.1%
Cap rate
0.5%
Rent to Value Ratio

Active

$279,900
3
bds
|
2
ba
|
1,479
sqft
|
built
1961
3409 Sherry Ave, Winter Haven, FL 33881
$-265
Cash flow
-4.9%
Cash-on-Cash Return
5.0%
Cap rate
0.7%
Rent to Value Ratio

Active

$319,900
3
bds
|
2
ba
|
1,585
sqft
|
built
2013
1152 Bowline St, Winter Haven, FL 33880
$-649
Cash flow
-10.6%
Cash-on-Cash Return
3.7%
Cap rate
0.6%
Rent to Value Ratio

Active

$369,000
4
bds
|
3
ba
|
2,798
sqft
|
built
2006
600 Sunway Ln, Winter Haven, FL 33880
$-301
Cash flow
-4.3%
Cash-on-Cash Return
5.2%
Cap rate
0.7%
Rent to Value Ratio

Active

$419,000
3
bds
|
2
ba
|
2,107
sqft
|
built
1998
357 Ruby Lake Loop, Winter Haven, FL 33884
$-637
Cash flow
-7.9%
Cash-on-Cash Return
4.3%
Cap rate
0.6%
Rent to Value Ratio

Active

$380,000
4
bds
|
3
ba
|
2,215
sqft
|
built
2003
714 Sunset Cove Dr, Winter Haven, FL 33880
$-805
Cash flow
-11.1%
Cash-on-Cash Return
3.6%
Cap rate
0.6%
Rent to Value Ratio

Active

$589,000
3
bds
|
3
ba
|
1,900
sqft
|
built
1950
125 Lake Roy Dr, Winter Haven, FL 33884
$-1,333
Cash flow
-11.8%
Cash-on-Cash Return
3.4%
Cap rate
0.5%
Rent to Value Ratio

Active

$330,000
3
bds
|
2
ba
|
1,734
sqft
|
built
2023
2748 San Marco Way, Winter Haven, FL 33884
$-696
Cash flow
-11.0%
Cash-on-Cash Return
3.6%
Cap rate
0.7%
Rent to Value Ratio

Active

$285,000
3
bds
|
2
ba
|
1,317
sqft
|
built
2023
726 Eagle Landing Blvd, Winter Haven, FL 33880
$-474
Cash flow
-8.7%
Cash-on-Cash Return
4.2%
Cap rate
0.7%
Rent to Value Ratio

Active

$299,000
3
bds
|
2
ba
|
1,700
sqft
|
built
1985
676 Augusta Rd, Winter Haven, FL 33884
$-516
Cash flow
-9.0%
Cash-on-Cash Return
4.1%
Cap rate
0.7%
Rent to Value Ratio

Active

$280,000
3
bds
|
2
ba
|
1,666
sqft
|
built
1990
2817 Wingfoot Ct, Winter Haven, FL 33884
$-598
Cash flow
-11.1%
Cash-on-Cash Return
3.6%
Cap rate
0.6%
Rent to Value Ratio

Active

$265,000
3
bds
|
2
ba
|
1,445
sqft
|
built
1990
132 Saint Kitts Cir, Winter Haven, FL 33884
$-230
Cash flow
-4.5%
Cash-on-Cash Return
5.1%
Cap rate
0.7%
Rent to Value Ratio

Active

$325,000
4
bds
|
2
ba
|
1,847
sqft
|
built
2006
1070 Summer Glen Dr, Winter Haven, FL 33880
$-389
Cash flow
-6.2%
Cash-on-Cash Return
4.7%
Cap rate
0.7%
Rent to Value Ratio

Active

$345,000
3
bds
|
2
ba
|
1,645
sqft
|
built
1999
221 Golf Aire Blvd, Winter Haven, FL 33884
$-1,034
Cash flow
-15.6%
Cash-on-Cash Return
2.5%
Cap rate
0.6%
Rent to Value Ratio

Active

$279,900
2
bds
|
2
ba
|
1,368
sqft
|
built
1995
14 Enclave Dr, Winter Haven, FL 33884
$-874
Cash flow
-16.3%
Cash-on-Cash Return
2.4%
Cap rate
0.6%
Rent to Value Ratio

Active

$490,000
4
bds
|
3
ba
|
2,733
sqft
|
built
1991
4338 Thomas Wood Ln E, Winter Haven, FL 33880
$-514
Cash flow
-5.5%
Cash-on-Cash Return
4.9%
Cap rate
0.7%
Rent to Value Ratio

Active

$289,999
3
bds
|
2
ba
|
1,432
sqft
|
built
1995
153 Rebecca Dr NE, Winter Haven, FL 33881
$-458
Cash flow
-8.2%
Cash-on-Cash Return
4.3%
Cap rate
0.7%
Rent to Value Ratio