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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.

341 out of 355 properties for sale in Winter Haven, FL

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Property photo
Active
StellarMLS

$323,900

4 bds | 2 ba | 1,814 sqft | built 2019
140 Solis Dr, Winter Haven, FL 33880
$-422
Cash flow
-6.8%
Cash-on-Cash Return

4.6%
Cap rate
0.7%
Rent to Value Ratio
Property photo
Active
StellarMLS

$249,900

3 bds | 2 ba | 1,058 sqft | built 1966
2622 Trinity Cir NW, Winter Haven, FL 33881
$-161
Cash flow
-3.4%
Cash-on-Cash Return

5.4%
Cap rate
0.7%
Rent to Value Ratio
Property photo
Active
StellarMLS

$224,990

2 bds | 2 ba | 1,350 sqft | built 1987
3545 Harbor Cir NW, Winter Haven, FL 33881
$-245
Cash flow
-5.7%
Cash-on-Cash Return

4.8%
Cap rate
1.0%
Rent to Value Ratio
Property photo
Active
StellarMLS

$415,000

3 bds | 3 ba | 1,685 sqft | built 1978
4570 Chambliss Rd, Winter Haven, FL 33884
$-591
Cash flow
-7.4%
Cash-on-Cash Return

4.4%
Cap rate
0.6%
Rent to Value Ratio
Property photo
Active
StellarMLS

$274,900

4 bds | 2 ba | 1,532 sqft | built 1963
1024 31st St NW, Winter Haven, FL 33881
$-323
Cash flow
-6.1%
Cash-on-Cash Return

4.7%
Cap rate
0.7%
Rent to Value Ratio
Property photo
Active
StellarMLS

$364,999

3 bds | 2 ba | 1,764 sqft | built 1973
202 Saint Lucie Rd, Winter Haven, FL 33884
$-385
Cash flow
-5.5%
Cash-on-Cash Return

4.9%
Cap rate
0.7%
Rent to Value Ratio
Property photo
Active
StellarMLS

$499,900

4 bds | 3 ba | 3,472 sqft | built 1989
2 Bridgewater Dr, Winter Haven, FL 33884
$-244
Cash flow
-2.5%
Cash-on-Cash Return

5.6%
Cap rate
0.7%
Rent to Value Ratio
Property photo
Active
StellarMLS

$257,000

3 bds | 2 ba | 1,592 sqft | built 1998
72 Saint Kitts Cir, Winter Haven, FL 33884
$-184
Cash flow
-3.7%
Cash-on-Cash Return

5.3%
Cap rate
0.8%
Rent to Value Ratio
Property photo
Active
SEF

$300,000

3 bds | 1 ba | 1,300 sqft | built 1954
305 20th St SW, Winter Haven, FL 33880
$-475
Cash flow
-8.3%
Cash-on-Cash Return

4.2%
Cap rate
0.5%
Rent to Value Ratio
Property photo
Active
StellarMLS

$250,000

2 bds | 2 ba | 1,012 sqft | built 1983
326 Sand Pine Trl, Winter Haven, FL 33880
$-304
Cash flow
-6.3%
Cash-on-Cash Return

4.7%
Cap rate
0.7%
Rent to Value Ratio
Property photo
Active
StellarMLS

$299,900

3 bds | 2 ba | 1,729 sqft | built 2006
3817 Osprey Pointe Cir, Winter Haven, FL 33884
$-446
Cash flow
-7.8%
Cash-on-Cash Return

4.4%
Cap rate
0.7%
Rent to Value Ratio
Property photo
Active
StellarMLS

$275,000

2 bds | 3 ba | 2,085 sqft | built 1985
14 Casarena Ct, Winter Haven, FL 33881
$-229
Cash flow
-4.3%
Cash-on-Cash Return

5.1%
Cap rate
0.8%
Rent to Value Ratio
Property photo
Active
StellarMLS

$344,997

3 bds | 3 ba | 1,673 sqft | built 1958
980 Oleander Dr SE, Winter Haven, FL 33880
$-535
Cash flow
-8.1%
Cash-on-Cash Return

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

$318,000

3 bds | 3 ba | 1,922 sqft | built 1980
2010 Overlook Dr, Winter Haven, FL 33884
$-333
Cash flow
-5.5%
Cash-on-Cash Return

4.9%
Cap rate
0.7%
Rent to Value Ratio
Property photo
Active
StellarMLS

$300,000

4 bds | 2 ba | 1,788 sqft | built 2013
238 Lake Eloise Pointe Blvd, Winter Haven, FL 33880
$-365
Cash flow
-6.3%
Cash-on-Cash Return

4.7%
Cap rate
0.7%
Rent to Value Ratio
Property photo
Active
StellarMLS

$350,000

4 bds | 3 ba | 2,200 sqft | built 2023
2107 Cartgate Ln, Winter Haven, FL 33884
$-465
Cash flow
-6.9%
Cash-on-Cash Return

4.6%
Cap rate
0.7%
Rent to Value Ratio
Property photo
Active
StellarMLS

$499,900

3 bds | 3 ba | 2,900 sqft | built 1979
121 Greenfield Rd, Winter Haven, FL 33884
$-1,448
Cash flow
-15.1%
Cash-on-Cash Return

2.7%
Cap rate
0.5%
Rent to Value Ratio
Property photo
Active
StellarMLS

$339,900

4 bds | 2 ba | 1,963 sqft | built 1972
221 Stevenson Rd, Winter Haven, FL 33884
$-443
Cash flow
-6.8%
Cash-on-Cash Return

4.6%
Cap rate
0.6%
Rent to Value Ratio
Property photo
Active
SEF

$407,000

5 bds | 3 ba | 0 sqft | built 2020
217 Grove Branch Rd, Winter Haven, FL 33880
$-658
Cash flow
-8.4%
Cash-on-Cash Return

4.2%
Cap rate
0.6%
Rent to Value Ratio
Property photo
Active
StellarMLS

$457,500

4 bds | 3 ba | 2,797 sqft | built 2023
3217 La Salle St, Winter Haven, FL 33884
$-869
Cash flow
-9.9%
Cash-on-Cash Return

3.9%
Cap rate
0.6%
Rent to Value Ratio
Property photo
Active
StellarMLS

$310,000

2 bds | 2 ba | 1,691 sqft | built 1990
1452 Grand Cayman Cir, Winter Haven, FL 33884
$-397
Cash flow
-6.7%
Cash-on-Cash Return

4.6%
Cap rate
0.6%
Rent to Value Ratio
Property photo
Active
StellarMLS

$296,000

4 bds | 2 ba | 1,817 sqft | built 2023
135 Krenson Bay Loop, Winter Haven, FL 33881
$-279
Cash flow
-4.9%
Cash-on-Cash Return

5.0%
Cap rate
0.7%
Rent to Value Ratio
Property photo
Active
StellarMLS

$549,900

3 bds | 3 ba | 2,118 sqft | built 1954
1475 S Lake Howard Dr, Winter Haven, FL 33880
$-1,165
Cash flow
-11.1%
Cash-on-Cash Return

3.6%
Cap rate
0.6%
Rent to Value Ratio
Property photo
Active
StellarMLS

$325,000

3 bds | 2 ba | 1,917 sqft | built 1960
1841 5th St SE, Winter Haven, FL 33880
$-478
Cash flow
-7.7%
Cash-on-Cash Return

4.4%
Cap rate
0.7%
Rent to Value Ratio
Property photo
Active
StellarMLS

$435,000

4 bds | 3 ba | 2,328 sqft | built 1977
141 Greenfield Rd, Winter Haven, FL 33884
$-873
Cash flow
-10.5%
Cash-on-Cash Return

3.7%
Cap rate
0.6%
Rent to Value Ratio
Property photo
Active
StellarMLS

$240,000

3 bds | 2 ba | 961 sqft | built 1986
1756 Elbert Acres Ct NE, Winter Haven, FL 33881
$-269
Cash flow
-5.8%
Cash-on-Cash Return

4.8%
Cap rate
0.7%
Rent to Value Ratio
Property photo
Active
SEF

$319,000

3 bds | 2 ba | 0 sqft | built 2023
906 Cattleman St, Winter Haven, FL 33881
$-514
Cash flow
-8.4%
Cash-on-Cash Return

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

$450,000

4 bds | 3 ba | 2,513 sqft | built 2007
1924 Eloise Cove Dr, Winter Haven, FL 33884
$-715
Cash flow
-8.3%
Cash-on-Cash Return

4.2%
Cap rate
0.6%
Rent to Value Ratio
Property photo
Active
FGCMLS

$299,999

3 bds | 2 ba | 1,608 sqft | built 2008
4975 Mandolin Ct, Winter Haven, FL 33884
$-530
Cash flow
-9.2%
Cash-on-Cash Return

4.0%
Cap rate
0.7%
Rent to Value Ratio
Property photo
Active
StellarMLS

$319,995

3 bds | 2 ba | 1,605 sqft | built 1984
692 Augusta Rd, Winter Haven, FL 33884
$-502
Cash flow
-8.2%
Cash-on-Cash Return

4.3%
Cap rate
0.7%
Rent to Value Ratio
Property photo
Active
StellarMLS

$389,000

3 bds | 2 ba | 1,726 sqft | built 1958
919 Avenue S SE, Winter Haven, FL 33880
$-594
Cash flow
-8.0%
Cash-on-Cash Return

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

$270,000

3 bds | 2 ba | 1,144 sqft | built 1957
657 Avenue C SW, Winter Haven, FL 33880
$-315
Cash flow
-6.1%
Cash-on-Cash Return

4.7%
Cap rate
0.7%
Rent to Value Ratio
Property photo
Active
StellarMLS

$299,999

4 bds | 2 ba | 1,851 sqft | built 2019
3082 Royal Tern Dr, Winter Haven, FL 33881
$-387
Cash flow
-6.7%
Cash-on-Cash Return

4.6%
Cap rate
0.7%
Rent to Value Ratio
Property photo
Active
StellarMLS

$369,900

4 bds | 3 ba | 2,635 sqft | built 2023
1143 Seedorf Dr, Winter Haven, FL 33881
$-479
Cash flow
-6.8%
Cash-on-Cash Return

4.6%
Cap rate
0.7%
Rent to Value Ratio
Property photo
Active
StellarMLS

$499,900

4 bds | 3 ba | 2,788 sqft | built 2005
7327 Bent Grass Dr, Winter Haven, FL 33884
$-1,007
Cash flow
-10.5%
Cash-on-Cash Return

3.7%
Cap rate
0.6%
Rent to Value Ratio
Property photo
Active
StellarMLS

$260,000

3 bds | 2 ba | 1,490 sqft | built 2017
579 Lucerne Blvd, Winter Haven, FL 33881
$-151
Cash flow
-3.0%
Cash-on-Cash Return

5.5%
Cap rate
0.8%
Rent to Value Ratio
Property photo
Active
StellarMLS

$339,500

4 bds | 2 ba | 1,845 sqft | built 2021
447 Lanham Dr, Winter Haven, FL 33881
$-370
Cash flow
-5.7%
Cash-on-Cash Return

4.8%
Cap rate
0.7%
Rent to Value Ratio
Property photo
Active
StellarMLS

$289,850

3 bds | 2 ba | 1,688 sqft | built 2020
440 Kensington View Dr, Winter Haven, FL 33880
$-462
Cash flow
-8.3%
Cash-on-Cash Return

4.2%
Cap rate
0.7%
Rent to Value Ratio