Skip to content
×
Pro Members Get
Full Access!
Get off the sidelines and take action in real estate investing with BiggerPockets Pro. Our comprehensive suite of tools and resources minimize mistakes, support informed decisions, and propel you to success.
Advanced networking features
Market and Deal Finder tools
Property analysis calculators
Landlord Command Center
ANNUAL Save 16%
$32.50 /mo
$390 billed annualy
MONTHLY
$39 /mo
billed monthly
7 day free trial. Cancel anytime

Let's keep in touch

Subscribe to our newsletter for timely insights and actionable tips on your real estate journey.

By signing up, you indicate that you agree to the BiggerPockets Terms & Conditions

Filters

Price

Price Range

$
  • $0
  • $50,000
  • $100,000
  • $150,000
  • $200,000
  • $250,000
  • $300,000
  • $350,000
  • $400,000
  • $450,000
  • $500,000
  • $550,000
  • $600,000
  • $650,000
  • $700,000
  • $750,000
  • $800,000
  • $850,000
  • $900,000
  • $950,000
  • $1M
  • $1.25M
  • $1.5M
  • $1.75M
  • $2M
  • $2.25M
  • $2.5M
  • $2.75M
  • $3M
  • $4M
  • $5M+
$
  • $0
  • $50,000
  • $100,000
  • $150,000
  • $200,000
  • $250,000
  • $300,000
  • $350,000
  • $400,000
  • $450,000
  • $500,000
  • $550,000
  • $600,000
  • $650,000
  • $700,000
  • $750,000
  • $800,000
  • $850,000
  • $900,000
  • $950,000
  • $1M
  • $1.25M
  • $1.5M
  • $1.75M
  • $2M
  • $2.25M
  • $2.5M
  • $2.75M
  • $3M
  • $4M
  • $5M+
Beds/Baths

Bedrooms

Bathrooms

For Sale

Status

Property Type (6)

Property Type

More

Square Feet

Lot Size

Year Built

Projected Rent

Cash on Cash Return

Monthly Cash Flow

Cap Rate

Copied

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.

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.

Property photo
Active
StellarMLS

$1,448,000

5 bds | 4 ba | 3,358 sqft | built 2003
11524 Claymont Cir, Windermere, FL 34786
$-3,491
Cash flow
-12.6%
Cash-on-Cash Return

3.3%
Cap rate
0.4%
Rent to Value Ratio
Property photo
Active
StellarMLS

$649,000

4 bds | 4 ba | 2,628 sqft | built 2008
13225 Charfield St, Windermere, FL 34786
$-1,766
Cash flow
-14.2%
Cash-on-Cash Return

2.9%
Cap rate
0.5%
Rent to Value Ratio
Property photo
Active
StellarMLS

$1,150,000

5 bds | 5 ba | 4,061 sqft | built 2018
8420 Vivaro Isle Way, Windermere, FL 34786
$-3,714
Cash flow
-16.8%
Cash-on-Cash Return

2.3%
Cap rate
0.4%
Rent to Value Ratio
Property photo
Active
StellarMLS

$1,890,000

6 bds | 4 ba | 3,894 sqft | built 2000
9922 Brentford Ct, Windermere, FL 34786
$-5,832
Cash flow
-16.1%
Cash-on-Cash Return

2.4%
Cap rate
0.5%
Rent to Value Ratio
Property photo
Active
StellarMLS

$3,400,000

4 bds | 4 ba | 4,877 sqft | built 1986
9731 Chestnut Ridge Dr, Windermere, FL 34786
$-16,182
Cash flow
-24.8%
Cash-on-Cash Return

0.4%
Cap rate
0.2%
Rent to Value Ratio
Property photo
Active
StellarMLS

$990,000

4 bds | 4 ba | 3,938 sqft | built 2003
1451 Whitney Isles Dr, Windermere, FL 34786
$-2,923
Cash flow
-15.4%
Cash-on-Cash Return

2.6%
Cap rate
0.5%
Rent to Value Ratio
Property photo
Active
StellarMLS

$625,000

4 bds | 3 ba | 2,981 sqft | built 2013
12925 Holdenbury Ln, Windermere, FL 34786
$-1,343
Cash flow
-11.2%
Cash-on-Cash Return

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

$378,800

3 bds | 3 ba | 1,461 sqft | built 2005
5318 Kumquat Loop, Windermere, FL 34786
$-1,032
Cash flow
-14.2%
Cash-on-Cash Return

2.9%
Cap rate
0.7%
Rent to Value Ratio
Property photo
Active
StellarMLS

$1,170,000

4 bds | 4 ba | 4,676 sqft | built 1999
2107 Westover Reserve Blvd, Windermere, FL 34786
$-1,955
Cash flow
-8.7%
Cash-on-Cash Return

4.1%
Cap rate
0.6%
Rent to Value Ratio
Property photo
Active
StellarMLS

$3,450,000

6 bds | 8 ba | 7,559 sqft | built 2016
4077 Isabella Cir, Windermere, FL 34786
$-15,371
Cash flow
-23.2%
Cash-on-Cash Return

0.8%
Cap rate
0.3%
Rent to Value Ratio
Property photo
Active
StellarMLS

$1,750,000

5 bds | 4 ba | 3,805 sqft | built 1913
311 E 8th Ave, Windermere, FL 34786
$-5,855
Cash flow
-17.5%
Cash-on-Cash Return

2.1%
Cap rate
0.4%
Rent to Value Ratio
Property photo
Active
StellarMLS

$679,000

3 bds | 3 ba | 2,463 sqft | built 2018
12815 Westside Village Loop, Windermere, FL 34786
$-2,035
Cash flow
-15.6%
Cash-on-Cash Return

2.6%
Cap rate
0.5%
Rent to Value Ratio
Property photo
Active
StellarMLS

$570,000

3 bds | 3 ba | 1,984 sqft | built 2012
6266 Golden Dewdrop Trl, Windermere, FL 34786
$-1,519
Cash flow
-13.9%
Cash-on-Cash Return

2.9%
Cap rate
0.6%
Rent to Value Ratio
Property photo
Active
StellarMLS

$3,200,000

4 bds | 5 ba | 3,745 sqft | built 2006
4819 Alexandra Garden Ct, Windermere, FL 34786
$-17,540
Cash flow
-28.6%
Cash-on-Cash Return

-0.4%
Cap rate
0.2%
Rent to Value Ratio
Property photo
Active
StellarMLS

$1,596,027

7 bds | 5 ba | 4,940 sqft | built 2004
1524 Lake Rhea Dr, Windermere, FL 34786
$-3,071
Cash flow
-10.0%
Cash-on-Cash Return

3.8%
Cap rate
0.6%
Rent to Value Ratio
Property photo
Active
StellarMLS

$974,900

5 bds | 5 ba | 3,285 sqft | built 2003
11096 Ledgement Ln, Windermere, FL 34786
$-2,961
Cash flow
-15.8%
Cash-on-Cash Return

2.5%
Cap rate
0.5%
Rent to Value Ratio
Property photo
Active
StellarMLS

$630,000

4 bds | 2 ba | 2,505 sqft | built 2005
11520 Via Lucerna Cir, Windermere, FL 34786
$-1,665
Cash flow
-13.8%
Cash-on-Cash Return

3.0%
Cap rate
0.6%
Rent to Value Ratio
Property photo
Active
StellarMLS

$539,900

3 bds | 3 ba | 2,154 sqft | built 2015
8575 Lookout Pointe Dr, Windermere, FL 34786
$-1,440
Cash flow
-13.9%
Cash-on-Cash Return

2.9%
Cap rate
0.5%
Rent to Value Ratio
Property photo
Active
StellarMLS

$895,000

4 bds | 5 ba | 3,051 sqft | built 2004
11660 Delwick Dr, Windermere, FL 34786
$-1,981
Cash flow
-11.5%
Cash-on-Cash Return

3.5%
Cap rate
0.6%
Rent to Value Ratio
Property photo
Active
StellarMLS

$2,895,000

5 bds | 7 ba | 6,105 sqft | built 2003
11209 Macaw Ct, Windermere, FL 34786
$-11,128
Cash flow
-20.1%
Cash-on-Cash Return

1.5%
Cap rate
0.3%
Rent to Value Ratio
Property photo
Active
StellarMLS

$1,200,000

7 bds | 4 ba | 3,928 sqft | built 2012
12023 Gold Creek Trl, Windermere, FL 34786
$-2,239
Cash flow
-9.7%
Cash-on-Cash Return

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

$530,000

3 bds | 3 ba | 1,826 sqft | built 2015
10750 Reams Rd, Windermere, FL 34786
$-867
Cash flow
-8.5%
Cash-on-Cash Return

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

$1,050,000

4 bds | 3 ba | 2,224 sqft | built 2018
13542 Gorgona Isle Dr, Windermere, FL 34786
$-3,977
Cash flow
-19.8%
Cash-on-Cash Return

1.6%
Cap rate
0.3%
Rent to Value Ratio
Property photo
Active
StellarMLS

$3,799,000

4 bds | 5 ba | 6,054 sqft | built 2007
12812 Jacob Grace Ct, Windermere, FL 34786
$-15,887
Cash flow
-21.8%
Cash-on-Cash Return

1.1%
Cap rate
0.2%
Rent to Value Ratio
Property photo
Active
StellarMLS

$585,000

4 bds | 2 ba | 2,159 sqft | built 2002
11322 Rapallo Ln, Windermere, FL 34786
$-1,834
Cash flow
-16.4%
Cash-on-Cash Return

2.4%
Cap rate
0.5%
Rent to Value Ratio
Property photo
Active
StellarMLS

$3,795,000

5 bds | 7 ba | 7,263 sqft | built 1987
10545 Down Lakeview Cir, Windermere, FL 34786
$-19,548
Cash flow
-26.9%
Cash-on-Cash Return

0.0%
Cap rate
0.1%
Rent to Value Ratio
Property photo
Active
StellarMLS

$5,890,000

4 bds | 7 ba | 7,872 sqft | built 2017
12264 Montalcino Cir, Windermere, FL 34786
$-31,638
Cash flow
-28.0%
Cash-on-Cash Return

-0.3%
Cap rate
0.2%
Rent to Value Ratio
Property photo
Active
StellarMLS

$401,990

3 bds | 3 ba | 1,554 sqft | built 2016
8625 Coventry Park Way, Windermere, FL 34786
$-1,035
Cash flow
-13.4%
Cash-on-Cash Return

3.1%
Cap rate
0.7%
Rent to Value Ratio
Property photo
Active
StellarMLS

$2,195,000

5 bds | 5 ba | 5,052 sqft | built 2006
9210 Tibet Pointe Cir, Windermere, FL 34786
$-8,259
Cash flow
-19.6%
Cash-on-Cash Return

1.6%
Cap rate
0.3%
Rent to Value Ratio
Property photo
Active
StellarMLS

$659,900

3 bds | 3 ba | 2,433 sqft | built 2005
1656 Whitney Isles Dr, Windermere, FL 34786
$-1,481
Cash flow
-11.7%
Cash-on-Cash Return

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

$1,350,000

4 bds | 3 ba | 3,888 sqft | built 1985
10506 Down Lakeview Cir, Windermere, FL 34786
$-4,419
Cash flow
-17.1%
Cash-on-Cash Return

2.2%
Cap rate
0.4%
Rent to Value Ratio
Property photo
Active
StellarMLS

$3,250,000

4 bds | 6 ba | 4,849 sqft | built 2002
6186 Louise Cove Dr, Windermere, FL 34786
$-13,560
Cash flow
-21.8%
Cash-on-Cash Return

1.1%
Cap rate
0.3%
Rent to Value Ratio
Property photo
Active
StellarMLS

$389,990

3 bds | 3 ba | 1,520 sqft | built 2012
7621 Sutherton Ln, Windermere, FL 34786
$-869
Cash flow
-11.6%
Cash-on-Cash Return

3.5%
Cap rate
0.6%
Rent to Value Ratio
Property photo
Active
StellarMLS

$389,000

3 bds | 3 ba | 1,369 sqft | built 2004
12744 Langstaff Dr, Windermere, FL 34786
$-902
Cash flow
-12.1%
Cash-on-Cash Return

3.4%
Cap rate
0.6%
Rent to Value Ratio
Property photo
Active
StellarMLS

$1,399,000

4 bds | 4 ba | 2,681 sqft | built 1987
3417 Bay Meadow Ct, Windermere, FL 34786
$-5,392
Cash flow
-20.1%
Cash-on-Cash Return

1.5%
Cap rate
0.3%
Rent to Value Ratio
Property photo
Active
StellarMLS

$409,000

3 bds | 3 ba | 1,584 sqft | built 2017
11686 Water Run Aly, Windermere, FL 34786
$-936
Cash flow
-11.9%
Cash-on-Cash Return

3.4%
Cap rate
0.6%
Rent to Value Ratio
Property photo
Active
StellarMLS

$399,990

3 bds | 3 ba | 1,462 sqft | built 2004
5235 Keenes Pheasant Dr, Windermere, FL 34786
$-1,162
Cash flow
-15.2%
Cash-on-Cash Return

2.7%
Cap rate
0.6%
Rent to Value Ratio
Property photo
Active
StellarMLS

$1,499,900

5 bds | 5 ba | 4,477 sqft | built 2007
1450 Belfiore Way, Windermere, FL 34786
$-4,190
Cash flow
-14.6%
Cash-on-Cash Return

2.8%
Cap rate
0.5%
Rent to Value Ratio