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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

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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.

405 out of 455 properties for sale in Winter Haven, FL

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Property photo
Active
StellarMLS

$424,900

4 bds | 3 ba | 3,034 sqft | built 2006
5392 Chandler Dr, Winter Haven, FL 33884
$-1,005
Cash flow
-12.3%
Cash-on-Cash Return

3.3%
Cap rate
0.6%
Rent to Value Ratio
Property photo
Active
StellarMLS

$375,000

5 bds | 3 ba | 2,952 sqft | built 2007
368 Fish Hawk Dr, Winter Haven, FL 33884
$-679
Cash flow
-9.4%
Cash-on-Cash Return

4.0%
Cap rate
0.7%
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

$289,500

3 bds | 2 ba | 1,659 sqft | built 2007
1732 Torrey Pines St, Winter Haven, FL 33881
$-481
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 | 1,756 sqft | built 1999
409 Bigstaff Ct, Winter Haven, FL 33884
$-489
Cash flow
-8.5%
Cash-on-Cash Return

4.2%
Cap rate
0.7%
Rent to Value Ratio
Property photo
Active
StellarMLS

$448,000

5 bds | 4 ba | 2,805 sqft | built 2018
1676 Tressel Ct, Winter Haven, FL 33881
$-477
Cash flow
-5.6%
Cash-on-Cash Return

4.9%
Cap rate
0.7%
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

$399,000

3 bds | 2 ba | 1,758 sqft | built 1990
115 Quailwood Dr, Winter Haven, FL 33880
$-612
Cash flow
-8.0%
Cash-on-Cash Return

4.3%
Cap rate
0.6%
Rent to Value Ratio
Property photo
Active
StellarMLS

$985,000

4 bds | 4 ba | 5,762 sqft | built 1927
1332 Evalyn Dr SE, Winter Haven, FL 33880
$-3,219
Cash flow
-17.1%
Cash-on-Cash Return

2.2%
Cap rate
0.3%
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

$269,900

2 bds | 2 ba | 1,281 sqft | built 1988
3025 Silverado Ter, Winter Haven, FL 33884
$-426
Cash flow
-8.2%
Cash-on-Cash Return

4.3%
Cap rate
0.7%
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

$238,000

3 bds | 2 ba | 1,338 sqft | built 1989
667 Lake Dexter Cir, Winter Haven, FL 33884
$-295
Cash flow
-6.5%
Cash-on-Cash Return

4.7%
Cap rate
0.8%
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

$350,000

4 bds | 2 ba | 1,707 sqft | built 2023
2638 San Marco Way, Winter Haven, FL 33884
$-723
Cash flow
-10.8%
Cash-on-Cash Return

3.7%
Cap rate
0.7%
Rent to Value Ratio
Property photo
Active
StellarMLS

$438,888

2 bds | 2 ba | 1,677 sqft | built 2016
5332 Hogan Ln, Winter Haven, FL 33884
$-930
Cash flow
-11.1%
Cash-on-Cash Return

3.6%
Cap rate
0.5%
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

$400,000

3 bds | 2 ba | 1,728 sqft | built 2004
2017 Misty Morning Dr, Winter Haven, FL 33880
$-895
Cash flow
-11.7%
Cash-on-Cash Return

3.5%
Cap rate
0.5%
Rent to Value Ratio
Property photo
Active
StellarMLS

$625,000

4 bds | 4 ba | 3,655 sqft | built 2006
4318 Thomas Wood Ln E, Winter Haven, FL 33880
$-1,229
Cash flow
-10.3%
Cash-on-Cash Return

3.8%
Cap rate
0.5%
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

$260,000

3 bds | 2 ba | 1,247 sqft | built 1981
4118 Fishermans Lndg, Winter Haven, FL 33884
$-559
Cash flow
-11.2%
Cash-on-Cash Return

3.6%
Cap rate
0.6%
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

$279,000

4 bds | 2 ba | 1,867 sqft | built 2021
352 Alexzander Way, Winter Haven, FL 33881
$-269
Cash flow
-5.0%
Cash-on-Cash Return

5.0%
Cap rate
0.8%
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

$399,900

3 bds | 3 ba | 2,010 sqft | built 1986
4305 Sea Pines Run, Winter Haven, FL 33884
$-691
Cash flow
-9.0%
Cash-on-Cash Return

4.1%
Cap rate
0.6%
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