Real Estate Investment Properties for Sale in Windermere, FL

Looking for investment property in Windermere, FL with high ROI ?

Explore a variety of short-term homes & houses in Windermere, FL. Invest wisely with VRBO & Windermere, FL Airbnb properties available for purchase. Find your ideal investment property among our curated listings for a rewarding real estate venture.

Investment Property for Sale in Windermere, FL

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PROPERTY	DETAILS	SALE PRICE	INVESTMENT PERFORMANCE
6018 Tarawood Dr Windermere, FL 6018 Tarawood Dr, Windermere, FL 32819 \| Single Family Residential	6 beds \| 6 baths \| 5,825 sq.ft.	$2,850,000	Airbnb cash on cash: -0.19% Traditional cash on cash: 0.55% Airbnb Rental Income: $5841 Traditional Rental Income: $6622 Airbnb ROI: -0.19% Traditional ROI: 0.55%
8734 Crestgate Cir Windermere, FL 8734 Crestgate Cir, Windermere, FL 32819 \| Single Family Residential	4 beds \| 4 baths \| 3,998 sq.ft.	$1,725,000	Airbnb cash on cash: -0.45% Traditional cash on cash: 0.17% Airbnb Rental Income: $3311 Traditional Rental Income: $3568 Airbnb ROI: -0.45% Traditional ROI: 0.17%
8719 S Bay Dr Windermere, FL 8719 S Bay Dr, Windermere, FL 32819 \| Single Family Residential	3 beds \| 2 baths \| 2,518 sq.ft.	$1,150,000	Airbnb cash on cash: -0.26% Traditional cash on cash: 0.54% Airbnb Rental Income: $2597 Traditional Rental Income: $2832 Airbnb ROI: -0.26% Traditional ROI: 0.54%
9130 Bayway Dr Windermere, FL 9130 Bayway Dr, Windermere, FL 32819 \| Other	N/A beds \| N/A baths \| N/A	$849,000	Airbnb cash on cash: -2.33% Traditional cash on cash: -1.5% Airbnb Rental Income: $413 Traditional Rental Income: $811 Airbnb ROI: -2.33% Traditional ROI: -1.5%
8968 Bay Cove Ct Windermere, FL 8968 Bay Cove Ct, Windermere, FL 32819 \| Single Family Residential	6 beds \| 6 baths \| 5,428 sq.ft.	$4,499,995	Airbnb cash on cash: -0.81% Traditional cash on cash: -0.28% Airbnb Rental Income: $5841 Traditional Rental Income: $6877 Airbnb ROI: -0.81% Traditional ROI: -0.28%
6025 Lady Bet Dr Windermere, FL 6025 Lady Bet Dr, Windermere, FL 32819 \| Single Family Residential	4 beds \| 4 baths \| 4,500 sq.ft.	$2,995,000	Airbnb cash on cash: -1.11% Traditional cash on cash: -0.76% Airbnb Rental Income: $3311 Traditional Rental Income: $3534 Airbnb ROI: -1.11% Traditional ROI: -0.76%
8661 Crestgate Cir Windermere, FL 8661 Crestgate Cir, Windermere, FL 32819 \| Single Family Residential	5 beds \| 5 baths \| 4,167 sq.ft.	$995,000	Airbnb cash on cash: 2.84% Traditional cash on cash: 3.25% Airbnb Rental Income: $5841 Traditional Rental Income: $5058 Airbnb ROI: 2.84% Traditional ROI: 3.25%
8117 Whitford Court Windermere, FL ''Under contract accepting back up offers'' Stunning Custom Golf Course Estate in Keene's ...	4 beds \| 3 baths \| N/A	$1,599,000	Airbnb cash on cash: -0.43% Traditional cash on cash: 0.06% Airbnb Rental Income: $3311 Traditional Rental Income: $3301 Airbnb ROI: -0.43% Traditional ROI: 0.06%
5852 Medinah Way Windermere, FL 5852 Medinah Way, Windermere, FL 32819 \| Single Family Residential	8 beds \| 6 baths \| 6,380 sq.ft.	$2,000,000	Airbnb cash on cash: 0.53% Traditional cash on cash: 1.47% Airbnb Rental Income: $5841 Traditional Rental Income: $6429 Airbnb ROI: 0.53% Traditional ROI: 1.47%
7011 Via Carmel Way Windermere, FL 7011 Via Carmel Way, Windermere, FL 32819 \| Single Family Residential	5 beds \| 7 baths \| 10,519 sq.ft.	$12,000,000	Airbnb cash on cash: -1.6% Traditional cash on cash: -1.4% Airbnb Rental Income: $5841 Traditional Rental Income: $6931 Airbnb ROI: -1.6% Traditional ROI: -1.4%
5410 Bay Side Dr Windermere, FL 5410 Bay Side Dr, Windermere, FL 32819 \| Single Family Residential	4 beds \| 4 baths \| 3,479 sq.ft.	$3,150,000	Airbnb cash on cash: -1.06% Traditional cash on cash: -0.71% Airbnb Rental Income: $3311 Traditional Rental Income: $3589 Airbnb ROI: -1.06% Traditional ROI: -0.71%
9107 Dollanger Ct Windermere, FL 9107 Dollanger Ct, Windermere, FL 32819 \| Single Family Residential	4 beds \| 2 baths \| 2,872 sq.ft.	$785,000	Airbnb cash on cash: 1.43% Traditional cash on cash: 1.38% Airbnb Rental Income: $3311 Traditional Rental Income: $2539 Airbnb ROI: 1.43% Traditional ROI: 1.38%
5329 Foxshire Ct Windermere, FL 5329 Foxshire Ct, Windermere, FL 32819 \| Single Family Residential	4 beds \| 3 baths \| 3,189 sq.ft.	$865,000	Airbnb cash on cash: 1.1% Traditional cash on cash: 1.38% Airbnb Rental Income: $3311 Traditional Rental Income: $2797 Airbnb ROI: 1.1% Traditional ROI: 1.38%
15115 Pigeon Plum Ln Windermere, FL Single family home in sought-after Winter Garden with NO HOA-bring your boat, RV or toys w...	3 beds \| 2 baths \| 1,728 sq.ft.	$505,000	Airbnb cash on cash: 1.66% Traditional cash on cash: 2.56% Airbnb Rental Income: $2597 Traditional Rental Income: $2401 Airbnb ROI: 1.66% Traditional ROI: 2.56%
8029 Gillette Ct Windermere, FL 8029 Gillette Ct, Windermere, FL 32836 \| Single Family Residential	3 beds \| 2 baths \| 1,638 sq.ft.	$514,997	Airbnb cash on cash: 1.97% Traditional cash on cash: 2.3% Airbnb Rental Income: $2597 Traditional Rental Income: $2131 Airbnb ROI: 1.97% Traditional ROI: 2.3%
6064 Masters Blvd Windermere, FL 6064 Masters Blvd, Windermere, FL 32819 \| Single Family Residential	4 beds \| 3 baths \| 3,766 sq.ft.	$1,575,000	Airbnb cash on cash: -0.26% Traditional cash on cash: -0.1% Airbnb Rental Income: $3311 Traditional Rental Income: $2804 Airbnb ROI: -0.26% Traditional ROI: -0.1%
8521 Sandberry Blvd Windermere, FL 8521 Sandberry Blvd, Windermere, FL 32819 \| Single Family Residential	4 beds \| 2 baths \| 2,440 sq.ft.	$635,000	Airbnb cash on cash: 2.28% Traditional cash on cash: 2.02% Airbnb Rental Income: $3311 Traditional Rental Income: $2415 Airbnb ROI: 2.28% Traditional ROI: 2.02%
10915 Ledgement Lane Windermere, FL Luxury Living Awaits at Glenmuir! Welcome home to 10915 Ledgement Lane, an absolutely stun...	4 beds \| 4 baths \| 2,818 sq.ft.	$1,037,000	Airbnb cash on cash: 0.73% Traditional cash on cash: 2.48% Airbnb Rental Income: $3311 Traditional Rental Income: $4254 Airbnb ROI: 0.73% Traditional ROI: 2.48%
6208 Donegal Dr Windermere, FL 6208 Donegal Dr, Windermere, FL 32819 \| Single Family Residential	5 beds \| N/A baths \| 6,445 sq.ft.	$5,920,000	Airbnb cash on cash: -1.05% Traditional cash on cash: -1.51% Airbnb Rental Income: $5841 Traditional Rental Income: $2126 Airbnb ROI: -1.05% Traditional ROI: -1.51%
6204 Donegal Dr Windermere, FL 6204 Donegal Dr, Windermere, FL 32819 \| Single Family Residential	4 beds \| N/A baths \| 3,088 sq.ft.	$1,975,000	Airbnb cash on cash: -0.53% Traditional cash on cash: -0.83% Airbnb Rental Income: $3311 Traditional Rental Income: $2030 Airbnb ROI: -0.53% Traditional ROI: -0.83%
8632 Spindletop Dr Windermere, FL 8632 Spindletop Dr, Windermere, FL 32819 \| Single Family Residential	6 beds \| 4 baths \| 3,645 sq.ft.	$980,000	Airbnb cash on cash: 2.96% Traditional cash on cash: 1.84% Airbnb Rental Income: $5841 Traditional Rental Income: $3660 Airbnb ROI: 2.96% Traditional ROI: 1.84%

Real Estate investment in Windermere, FL

There are 21 properties for sale in the city of Windermere . The median list price in Windermere is $1,575,000 and the average price per square foot is $381. In December 2025, the average monthly cash on cash return in Windermere is N/A%. The average monthly rental income in Windermere is $2,173.

Windermere, FL Real Estate Investing: FAQs for Buyers, Sellers and Investors

There are 21 investment properties available for sale in Windermere.

In 2025, the best neighborhood to buy investment property is Windermere.

The ROI for Short-Term is higher than the Long-Term in Windermere with average rental income of $3,311.

Your search for investment property begins and ends here

Investment Property for Sale in Windermere, FL

6018 Tarawood Dr

Windermere, FL

6 beds | 6 baths | 5,825 sq.ft.

$2,850,000

Airbnb cash on cash: -0.19%

Traditional cash on cash: 0.55%

Airbnb Rental Income: $5841

Traditional Rental Income: $6622

Airbnb ROI: -0.19%

Traditional ROI: 0.55%

8734 Crestgate Cir

Windermere, FL

4 beds | 4 baths | 3,998 sq.ft.

$1,725,000

Airbnb cash on cash: -0.45%

Traditional cash on cash: 0.17%

Airbnb Rental Income: $3311

Traditional Rental Income: $3568

Airbnb ROI: -0.45%

Traditional ROI: 0.17%

8719 S Bay Dr

Windermere, FL

3 beds | 2 baths | 2,518 sq.ft.

$1,150,000

Airbnb cash on cash: -0.26%

Traditional cash on cash: 0.54%

Airbnb Rental Income: $2597

Traditional Rental Income: $2832

Airbnb ROI: -0.26%

Traditional ROI: 0.54%

9130 Bayway Dr

Windermere, FL

N/A beds | N/A baths | N/A

$849,000

Airbnb cash on cash: -2.33%

Traditional cash on cash: -1.5%

Airbnb Rental Income: $413

Traditional Rental Income: $811

Airbnb ROI: -2.33%

Traditional ROI: -1.5%

8968 Bay Cove Ct

Windermere, FL

6 beds | 6 baths | 5,428 sq.ft.

$4,499,995

Airbnb cash on cash: -0.81%

Traditional cash on cash: -0.28%

Airbnb Rental Income: $5841

Traditional Rental Income: $6877

Airbnb ROI: -0.81%

Traditional ROI: -0.28%

6025 Lady Bet Dr

Windermere, FL

4 beds | 4 baths | 4,500 sq.ft.

$2,995,000

Airbnb cash on cash: -1.11%

Traditional cash on cash: -0.76%

Airbnb Rental Income: $3311

Traditional Rental Income: $3534

Airbnb ROI: -1.11%

Traditional ROI: -0.76%

8661 Crestgate Cir

Windermere, FL

5 beds | 5 baths | 4,167 sq.ft.

$995,000

Airbnb cash on cash: 2.84%

Traditional cash on cash: 3.25%

Airbnb Rental Income: $5841

Traditional Rental Income: $5058

Airbnb ROI: 2.84%

Traditional ROI: 3.25%

8117 Whitford Court

Windermere, FL

4 beds | 3 baths | N/A

$1,599,000

Airbnb cash on cash: -0.43%

Traditional cash on cash: 0.06%

Airbnb Rental Income: $3311

Traditional Rental Income: $3301

Airbnb ROI: -0.43%