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.

Townhouses for Sale in Windermere, FL

Search for Townhouse for Sale in Windermere, Florida. Browse all of Mashvisor’s Townhouse listings and other investment property types including Single Family Homes, Multi Family Homes, Condos, Townhouses and Other Homes.

Showing 19 Townhouse listings of over 500,000 total investment properties for sale. Visit Mashvisor.com to all investment properties.

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PROPERTY	DETAILS	SALE PRICE	INVESTMENT PERFORMANCE
7462 BENTONSHIRE AVE Windermere, FL Move in ready 3/2.5 Townhome in Windermere! New roof 2024. AC compressor new June 2025. Re...	3 beds \| 3 baths \| 1,480 sq.ft.	$378,000	Airbnb cash on cash: 2.36% Traditional cash on cash: 3.23% Airbnb Rental Income: $2597 Traditional Rental Income: $2285 Airbnb ROI: 2.36% Traditional ROI: 3.23%
7673 RIPPLEPOINTE WAY Windermere, FL Move in ready! Rarely available, 4 bedroom/3 bathroom townhouse located in the sought afte...	4 beds \| 3 baths \| 2,212 sq.ft.	$475,000	Airbnb cash on cash: 2.53% Traditional cash on cash: 3.09% Airbnb Rental Income: $3311 Traditional Rental Income: $2822 Airbnb ROI: 2.53% Traditional ROI: 3.09%
14466 BRIDGEWATER CROSSINGS BOULEVARD Windermere, FL Video Tour Available Welcome to Summerport where location is everything as great schoo...	4 beds \| 3 baths \| 1,642 sq.ft.	$418,000	Airbnb cash on cash: 3.88% Traditional cash on cash: 2.77% Airbnb Rental Income: $3311 Traditional Rental Income: $2136 Airbnb ROI: 3.88% Traditional ROI: 2.77%
5318 KUMQUAT LOOP Windermere, FL This beautifully updated three-bedroom townhome in Windermere offers the perfect blend of ...	3 beds \| 3 baths \| 1,461 sq.ft.	$378,800	Airbnb cash on cash: 2.15% Traditional cash on cash: 2.9% Airbnb Rental Income: $2597 Traditional Rental Income: $2242 Airbnb ROI: 2.15% Traditional ROI: 2.9%
13715 BRESSLER ALLEY Windermere, FL Under contract-accepting backup offers. Price Just Got Better! Don't miss this incredible ...	3 beds \| 3 baths \| 2,139 sq.ft.	$489,000	Airbnb cash on cash: 1.57% Traditional cash on cash: 3.71% Airbnb Rental Income: $2597 Traditional Rental Income: $2955 Airbnb ROI: 1.57% Traditional ROI: 3.71%
13730 LENSDALE LANE Windermere, FL Under contract-accepting backup offers. One or more photo(s) has been virtually staged. Th...	4 beds \| 3 baths \| 1,640 sq.ft.	$375,000	Airbnb cash on cash: 5.23% Traditional cash on cash: 4.4% Airbnb Rental Income: $3311 Traditional Rental Income: $2278 Airbnb ROI: 5.23% Traditional ROI: 4.4%
12930 VENNETTA WAY Windermere, FL Welcome to this beautifully renovated 3-bedroom, 2.5-bathroom townhouse in Berkshire Park,...	3 beds \| 3 baths \| 1,644 sq.ft.	$439,900	Airbnb cash on cash: 2.16% Traditional cash on cash: 3.04% Airbnb Rental Income: $2597 Traditional Rental Income: $2336 Airbnb ROI: 2.16% Traditional ROI: 3.04%
7348 YODER STREET Windermere, FL Welcome to this beautifully maintained 3-bedroom, 2.5-bathroom townhome with a private cou...	3 beds \| 3 baths \| 1,479 sq.ft.	$389,900	Airbnb cash on cash: 2.68% Traditional cash on cash: 3.42% Airbnb Rental Income: $2597 Traditional Rental Income: $2247 Airbnb ROI: 2.68% Traditional ROI: 3.42%
8500 IRON MOUNTAIN TRAIL Windermere, FL Step into this beautifully updated 3-bedroom, 2.5-bath townhome with a dedicated home offi...	3 beds \| 3 baths \| 1,818 sq.ft.	$468,900	Airbnb cash on cash: 1.09% Traditional cash on cash: 2.55% Airbnb Rental Income: $2597 Traditional Rental Income: $2616 Airbnb ROI: 1.09% Traditional ROI: 2.55%
7715 ANSELMO LANE Windermere, FL Under contract-accepting backup offers. $5000 CREDIT at closing towards whatever you want-...	3 beds \| 3 baths \| 1,644 sq.ft.	$385,000	Airbnb cash on cash: 1.93% Traditional cash on cash: 3% Airbnb Rental Income: $2597 Traditional Rental Income: $2361 Airbnb ROI: 1.93% Traditional ROI: 3%
12335 CRUXBURY DRIVE Windermere, FL Discover this spacious 2-bedroom, 2.5-bath end-unit townhome nestled in a charming Winderm...	2 beds \| 3 baths \| 1,510 sq.ft.	$399,999	Airbnb cash on cash: 7.77% Traditional cash on cash: 3.33% Airbnb Rental Income: $4898 Traditional Rental Income: $2227 Airbnb ROI: 7.77% Traditional ROI: 3.33%
5235 KEENES PHEASANT DRIVE Windermere, FL Charming 3-Bedroom Townhome in a Prime Location! Welcome home to this beautifully maintai...	3 beds \| 3 baths \| 1,462 sq.ft.	$399,990	Airbnb cash on cash: 1.92% Traditional cash on cash: 2.55% Airbnb Rental Income: $2597 Traditional Rental Income: $2211 Airbnb ROI: 1.92% Traditional ROI: 2.55%
11686 WATER RUN ALLEY Windermere, FL Located in the heart of Windermere, this 3-bedroom, 2.5-bath townhome blends modern comfor...	3 beds \| 3 baths \| 1,584 sq.ft.	$409,000	Airbnb cash on cash: 2.07% Traditional cash on cash: 3.17% Airbnb Rental Income: $2597 Traditional Rental Income: $2396 Airbnb ROI: 2.07% Traditional ROI: 3.17%
12449 CRUXBURY DRIVE Windermere, FL Seller will pay $5,000 towards buyer's closing costs or a interest rate buy down. Welcome ...	3 beds \| 3 baths \| 1,429 sq.ft.	$379,000	Airbnb cash on cash: 2.92% Traditional cash on cash: 3.51% Airbnb Rental Income: $2597 Traditional Rental Income: $2184 Airbnb ROI: 2.92% Traditional ROI: 3.51%
12975 CALDERDALE AVENUE Windermere, FL Welcome to this beautifully maintained 3-bedroom, 2.5-bath end-unit townhouse nestled in t...	3 beds \| 3 baths \| 1,645 sq.ft.	$399,990	Airbnb cash on cash: 2.14% Traditional cash on cash: 3.12% Airbnb Rental Income: $2597 Traditional Rental Income: $2343 Airbnb ROI: 2.14% Traditional ROI: 3.12%
12744 LANGSTAFF DRIVE Windermere, FL Beautiful townhouse located in Windermere, 3 br, 2.5 baths, full of natural lighting an...	3 beds \| 3 baths \| 1,369 sq.ft.	$389,000	Airbnb cash on cash: 2.22% Traditional cash on cash: 2.76% Airbnb Rental Income: $2597 Traditional Rental Income: $2171 Airbnb ROI: 2.22% Traditional ROI: 2.76%
14155 ANCILLA BOULEVARD Windermere, FL Welcome to 14155 Ancilla Blvd, a charming three-bedroom, two-and-a-half-bathroom townhouse...	3 beds \| 3 baths \| 1,629 sq.ft.	$415,000	Airbnb cash on cash: 1.5% Traditional cash on cash: 2.45% Airbnb Rental Income: $2597 Traditional Rental Income: $2343 Airbnb ROI: 1.5% Traditional ROI: 2.45%
8259 MARITIME FLAG STREET #4 Windermere, FL One or more photo(s) has been virtually staged. Experience the best of Windermere living! ...	3 beds \| 3 baths \| 1,460 sq.ft.	$345,000	Airbnb cash on cash: 2.07% Traditional cash on cash: 2.87% Airbnb Rental Income: $2597 Traditional Rental Income: $2234 Airbnb ROI: 2.07% Traditional ROI: 2.87%
13333 GORGONA ISLE DRIVE Windermere, FL Welcome to this spacious 3-bedroom, 2.5-bath townhome located in one of Windermereâs mos...	3 beds \| 3 baths \| 1,779 sq.ft.	$480,000	Airbnb cash on cash: 1.86% Traditional cash on cash: 3.19% Airbnb Rental Income: $2597 Traditional Rental Income: $2575 Airbnb ROI: 1.86% Traditional ROI: 3.19%

Your search for investment property begins and ends here

Townhouses for Sale in Windermere, FL

7462 BENTONSHIRE AVE

Windermere, FL

3 beds | 3 baths | 1,480 sq.ft.

$378,000

Airbnb cash on cash: 2.36%

Traditional cash on cash: 3.23%

Airbnb Rental Income: $2597

Traditional Rental Income: $2285

Airbnb ROI: 2.36%

Traditional ROI: 3.23%

7673 RIPPLEPOINTE WAY

Windermere, FL

4 beds | 3 baths | 2,212 sq.ft.

$475,000

Airbnb cash on cash: 2.53%

Traditional cash on cash: 3.09%

Airbnb Rental Income: $3311

Traditional Rental Income: $2822

Airbnb ROI: 2.53%

Traditional ROI: 3.09%

14466 BRIDGEWATER CROSSINGS BOULEVARD

Windermere, FL

4 beds | 3 baths | 1,642 sq.ft.

$418,000

Airbnb cash on cash: 3.88%

Traditional cash on cash: 2.77%

Airbnb Rental Income: $3311

Traditional Rental Income: $2136

Airbnb ROI: 3.88%

Traditional ROI: 2.77%

5318 KUMQUAT LOOP

Windermere, FL

3 beds | 3 baths | 1,461 sq.ft.

$378,800

Airbnb cash on cash: 2.15%

Traditional cash on cash: 2.9%

Airbnb Rental Income: $2597

Traditional Rental Income: $2242

Airbnb ROI: 2.15%

Traditional ROI: 2.9%

13715 BRESSLER ALLEY

Windermere, FL

3 beds | 3 baths | 2,139 sq.ft.

$489,000

Airbnb cash on cash: 1.57%

Traditional cash on cash: 3.71%

Airbnb Rental Income: $2597

Traditional Rental Income: $2955

Airbnb ROI: 1.57%

Traditional ROI: 3.71%

13730 LENSDALE LANE

Windermere, FL

4 beds | 3 baths | 1,640 sq.ft.

$375,000

Airbnb cash on cash: 5.23%

Traditional cash on cash: 4.4%

Airbnb Rental Income: $3311

Traditional Rental Income: $2278

Airbnb ROI: 5.23%

Traditional ROI: 4.4%

12930 VENNETTA WAY

Windermere, FL

3 beds | 3 baths | 1,644 sq.ft.

$439,900

Airbnb cash on cash: 2.16%

Traditional cash on cash: 3.04%

Airbnb Rental Income: $2597

Traditional Rental Income: $2336

Airbnb ROI: 2.16%

Traditional ROI: 3.04%

7348 YODER STREET

Windermere, FL

3 beds | 3 baths | 1,479 sq.ft.

$389,900

Airbnb cash on cash: 2.68%

Traditional cash on cash: 3.42%

Airbnb Rental Income: $2597

Traditional Rental Income: $2247

Airbnb ROI: 2.68%