Windermere, FL Investment Properties for Sale
Browse homes for sale and investment properties in Windermere, FL. Refine your search by price, property type, or more.
Best cash flowing properties in Windermere, FL
Active
$335,000
3
bds
|
2
ba
|
1,455
sqft
|
built
2007
11446 Jasper Kay Ter, Windermere, FL 34786
$-239
Cash flow
-3.7%
Cash-on-Cash Return
5.3%
Cap rate
0.7%
Rent to Value Ratio
Active
$389,999
3
bds
|
3
ba
|
1,500
sqft
|
built
2012
7819 Hardenton St, Windermere, FL 34786
$-710
Cash flow
-9.5%
Cash-on-Cash Return
4.0%
Cap rate
0.6%
Rent to Value Ratio
89 out of 99 properties for sale in Windermere, FL
Limited Results Shown
Create a free account, or log in to reveal all property listings and enjoy the complete experience.
Active
$2,650,000
5
bds
|
8
ba
|
7,621
sqft
|
built
2011
9905 Lanai View Ct, Windermere, FL 34786
$-9,467
Cash flow
-18.6%
Cash-on-Cash Return
1.9%
Cap rate
0.3%
Rent to Value Ratio
Active
$759,500
4
bds
|
4
ba
|
2,820
sqft
|
built
2008
6832 Thornhill Cir, Windermere, FL 34786
$-1,899
Cash flow
-13.0%
Cash-on-Cash Return
3.1%
Cap rate
0.5%
Rent to Value Ratio
Active
$399,999
2
bds
|
3
ba
|
1,510
sqft
|
built
2006
12335 Cruxbury Dr, Windermere, FL 34786
$-781
Cash flow
-10.2%
Cash-on-Cash Return
3.8%
Cap rate
0.6%
Rent to Value Ratio
Active
$8,325,000
5
bds
|
7
ba
|
6,937
sqft
|
built
1988
5074 Isleworth Country Club Dr, Windermere, FL 34786
$-39,872
Cash flow
-25.0%
Cash-on-Cash Return
0.4%
Cap rate
0.1%
Rent to Value Ratio
Active
$2,595,000
5
bds
|
7
ba
|
5,934
sqft
|
built
2008
11106 Coniston Way, Windermere, FL 34786
$-9,396
Cash flow
-18.9%
Cash-on-Cash Return
1.8%
Cap rate
0.3%
Rent to Value Ratio
Active
$1,700,000
5
bds
|
5
ba
|
3,868
sqft
|
built
2004
11015 Hawkshead Ct, Windermere, FL 34786
$-5,169
Cash flow
-15.9%
Cash-on-Cash Return
2.5%
Cap rate
0.5%
Rent to Value Ratio
Active
$829,900
4
bds
|
3
ba
|
2,867
sqft
|
built
2002
1932 Reed Hill Dr, Windermere, FL 34786
$-1,666
Cash flow
-10.5%
Cash-on-Cash Return
3.7%
Cap rate
0.6%
Rent to Value Ratio
Active
$1,425,000
5
bds
|
4
ba
|
3,684
sqft
|
built
1999
11425 Claymont Cir, Windermere, FL 34786
$-4,373
Cash flow
-16.0%
Cash-on-Cash Return
2.5%
Cap rate
0.5%
Rent to Value Ratio
Active
$535,000
3
bds
|
2
ba
|
1,492
sqft
|
built
1986
9375 Woodbreeze Blvd, Windermere, FL 34786
$-1,379
Cash flow
-13.4%
Cash-on-Cash Return
3.1%
Cap rate
0.5%
Rent to Value Ratio
Active
$5,494,000
5
bds
|
7
ba
|
4,665
sqft
|
built
1993
5199 Latrobe Dr, Windermere, FL 34786
$-25,291
Cash flow
-24.0%
Cash-on-Cash Return
0.6%
Cap rate
0.2%
Rent to Value Ratio
Active
$940,000
5
bds
|
5
ba
|
3,615
sqft
|
built
2017
9257 Outlook Rock Trl, Windermere, FL 34786
$-2,183
Cash flow
-12.1%
Cash-on-Cash Return
3.4%
Cap rate
0.4%
Rent to Value Ratio
Active
$4,150,000
4
bds
|
7
ba
|
6,265
sqft
|
built
2008
9253 Tibet Pointe Cir, Windermere, FL 34786
$-20,713
Cash flow
-26.0%
Cash-on-Cash Return
0.2%
Cap rate
0.1%
Rent to Value Ratio
Active
$1,630,000
3
bds
|
2
ba
|
2,238
sqft
|
built
1985
11923 Lake Butler Blvd, Windermere, FL 34786
$-6,390
Cash flow
-20.5%
Cash-on-Cash Return
1.4%
Cap rate
0.3%
Rent to Value Ratio
Active
$895,000
5
bds
|
4
ba
|
3,151
sqft
|
built
2004
1638 Whitney Isles Dr, Windermere, FL 34786
$-2,546
Cash flow
-14.8%
Cash-on-Cash Return
2.7%
Cap rate
0.5%
Rent to Value Ratio
Active
$3,200,000
5
bds
|
8
ba
|
6,753
sqft
|
built
2017
4071 Isabella Cir, Windermere, FL 34786
$-13,572
Cash flow
-22.1%
Cash-on-Cash Return
1.1%
Cap rate
0.3%
Rent to Value Ratio
Active
$1,200,000
5
bds
|
3
ba
|
2,918
sqft
|
built
1985
3443 Wild Myrtle Ct, Windermere, FL 34786
$-2,405
Cash flow
-10.5%
Cash-on-Cash Return
3.7%
Cap rate
0.5%
Rent to Value Ratio
Active
$14,250,000
5
bds
|
6
ba
|
9,511
sqft
|
built
1999
5525 Isleworth Country Club Dr, Windermere, FL 34786
$-71,632
Cash flow
-26.2%
Cash-on-Cash Return
0.1%
Cap rate
0.1%
Rent to Value Ratio
Active
$3,750,000
6
bds
|
6
ba
|
6,819
sqft
|
built
1989
2828 Marquesas Ct, Windermere, FL 34786
$-17,928
Cash flow
-24.9%
Cash-on-Cash Return
0.4%
Cap rate
0.1%
Rent to Value Ratio
Active
$1,850,000
5
bds
|
6
ba
|
6,375
sqft
|
built
1986
11056 Clipper Ct, Windermere, FL 34786
$-7,300
Cash flow
-20.6%
Cash-on-Cash Return
1.4%
Cap rate
0.3%
Rent to Value Ratio
Active
$549,900
4
bds
|
4
ba
|
2,461
sqft
|
built
2015
7349 Ella Ln, Windermere, FL 34786
$-1,477
Cash flow
-14.0%
Cash-on-Cash Return
2.9%
Cap rate
0.6%
Rent to Value Ratio
Active
$1,459,900
4
bds
|
4
ba
|
3,586
sqft
|
built
2014
11706 Waterstone Loop Dr, Windermere, FL 34786
$-5,206
Cash flow
-18.6%
Cash-on-Cash Return
1.9%
Cap rate
0.4%
Rent to Value Ratio
Active
$874,900
4
bds
|
5
ba
|
2,450
sqft
|
built
2004
11994 Mc Kinnon Rd, Windermere, FL 34786
$-2,396
Cash flow
-14.3%
Cash-on-Cash Return
2.9%
Cap rate
0.4%
Rent to Value Ratio
Active
$2,299,995
4
bds
|
6
ba
|
5,457
sqft
|
built
2011
5909 Oxford Moor Blvd, Windermere, FL 34786
$-9,257
Cash flow
-21.0%
Cash-on-Cash Return
1.3%
Cap rate
0.2%
Rent to Value Ratio
Active
$2,995,000
6
bds
|
8
ba
|
8,372
sqft
|
built
2019
4047 Isabella Cir, Windermere, FL 34786
$-13,070
Cash flow
-22.8%
Cash-on-Cash Return
0.9%
Cap rate
0.3%
Rent to Value Ratio
Active
$2,600,000
5
bds
|
6
ba
|
5,853
sqft
|
built
2013
12030 Waterstone Loop Dr, Windermere, FL 34786
$-12,055
Cash flow
-24.2%
Cash-on-Cash Return
0.6%
Cap rate
0.2%
Rent to Value Ratio
Active
$1,649,000
5
bds
|
3
ba
|
3,300
sqft
|
built
1989
13124 Filly Ct, Windermere, FL 34786
$-5,434
Cash flow
-17.2%
Cash-on-Cash Return
2.2%
Cap rate
0.4%
Rent to Value Ratio
Active
$999,990
4
bds
|
3
ba
|
3,206
sqft
|
built
2003
11508 Delwick Dr, Windermere, FL 34786
$-3,059
Cash flow
-16.0%
Cash-on-Cash Return
2.5%
Cap rate
0.4%
Rent to Value Ratio
Active
$439,900
3
bds
|
3
ba
|
1,644
sqft
|
built
2008
12930 Vennetta Way, Windermere, FL 34786
$-1,048
Cash flow
-12.4%
Cash-on-Cash Return
3.3%
Cap rate
0.6%
Rent to Value Ratio
Active
$1,994,999
3
bds
|
4
ba
|
3,240
sqft
|
built
1999
13137 Lake Butler Blvd, Windermere, FL 34786
$-7,472
Cash flow
-19.5%
Cash-on-Cash Return
1.7%
Cap rate
0.2%
Rent to Value Ratio
Active
$749,000
4
bds
|
4
ba
|
3,064
sqft
|
built
2018
12755 Westside Village Loop, Windermere, FL 34786
$-1,769
Cash flow
-12.3%
Cash-on-Cash Return
3.3%
Cap rate
0.6%
Rent to Value Ratio
Active
$9,500,000
6
bds
|
9
ba
|
9,571
sqft
|
built
2010
6137 Grosvenor Shore Dr, Windermere, FL 34786
$-50,075
Cash flow
-27.5%
Cash-on-Cash Return
-0.2%
Cap rate
0.1%
Rent to Value Ratio
Active
$2,050,000
6
bds
|
6
ba
|
6,601
sqft
|
built
2014
1984 Windermere Rd, Windermere, FL 34786
$-8,163
Cash flow
-20.8%
Cash-on-Cash Return
1.4%
Cap rate
0.3%
Rent to Value Ratio
Active
$20,000,000
7
bds
|
9
ba
|
10,649
sqft
|
built
2014
11900 Lake Butler Blvd, Windermere, FL 34786
$-105,366
Cash flow
-27.5%
Cash-on-Cash Return
-0.2%
Cap rate
0.0%
Rent to Value Ratio
Active
$2,799,000
4
bds
|
5
ba
|
3,636
sqft
|
built
1987
6120 Payne Stewart Dr, Windermere, FL 34786
$-12,415
Cash flow
-23.1%
Cash-on-Cash Return
0.8%
Cap rate
0.2%
Rent to Value Ratio
Active
$3,490,000
6
bds
|
8
ba
|
6,930
sqft
|
built
2014
13305 Bellaria Cir, Windermere, FL 34786
$-15,025
Cash flow
-22.5%
Cash-on-Cash Return
1.0%
Cap rate
0.3%
Rent to Value Ratio
Active
$3,590,000
8
bds
|
8
ba
|
8,203
sqft
|
built
2017
13643 Lake Cawood Dr, Windermere, FL 34786
$-15,516
Cash flow
-22.5%
Cash-on-Cash Return
1.0%
Cap rate
0.2%
Rent to Value Ratio
Active
$5,000,000
6
bds
|
8
ba
|
6,855
sqft
|
built
2017
4089 Isabella Cir, Windermere, FL 34786
$-23,721
Cash flow
-24.8%
Cash-on-Cash Return
0.5%
Cap rate
0.2%
Rent to Value Ratio
Active
$1,699,000
5
bds
|
5
ba
|
3,520
sqft
|
built
2005
6001 Caymus Loop, Windermere, FL 34786
$-4,275
Cash flow
-13.1%
Cash-on-Cash Return
3.1%
Cap rate
0.5%
Rent to Value Ratio