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Beds/Baths

Bedrooms

Bathrooms

For Sale

Status

Property Type (6)

Property Type

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Square Feet

Lot Size

Year Built

Projected Rent

Cash on Cash Return

Monthly Cash Flow

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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.

248 out of 282 properties for sale in Winter Haven, FL

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Property photo
Active
StellarMLS

$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
Property photo
Active
StellarMLS

$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
Property photo
Active
StellarMLS

$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
Property photo
Active
StellarMLS

$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
Property photo
Active
StellarMLS

$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
Property photo
Active
StellarMLS

$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
Property photo
Active
StellarMLS

$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
Property photo
Active
StellarMLS

$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
Property photo
Active
StellarMLS

$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
Property photo
Active
StellarMLS

$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
Property photo
Active
StellarMLS

$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
Property photo
Active
StellarMLS

$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
Property photo
Active
StellarMLS

$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
Property photo
Active
StellarMLS

$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
Property photo
Active
StellarMLS

$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
Property photo
Active
StellarMLS

$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
Property photo
Active
StellarMLS

$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
Property photo
Active
StellarMLS

$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
Property photo
Active
StellarMLS

$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
Property photo
Active
StellarMLS

$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
Property photo
Active
StellarMLS

$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
Property photo
Active
StellarMLS

$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
Property photo
Active
StellarMLS

$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
Property photo
Active
StellarMLS

$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
Property photo
Active
StellarMLS

$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
Property photo
Active
StellarMLS

$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
Property photo
Active
StellarMLS

$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
Property photo
Active
StellarMLS

$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
Property photo
Active
StellarMLS

$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
Property photo
Active
StellarMLS

$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
Property photo
Active
StellarMLS

$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
Property photo
Active
StellarMLS

$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
Property photo
Active
StellarMLS

$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
Property photo
Active
StellarMLS

$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
Property photo
Active
StellarMLS

$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
Property photo
Active
StellarMLS

$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
Property photo
Active
StellarMLS

$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
Property photo
Active
StellarMLS

$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