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
10624 REAMS ROAD Windermere, FL Welcome to this beautiful 4-bedroom, 2.5-bath home in the highly desirable Windermere Trai...	4 beds \| 3 baths \| 2,092 sq.ft.	$505,000	Airbnb cash on cash: 2.98% Traditional cash on cash: 3.4% Airbnb Rental Income: $3311 Traditional Rental Income: $2769 Airbnb ROI: 2.98% Traditional ROI: 3.4%
12307 LANGSTAFF DRIVE Windermere, FL One or more photo(s) has been virtually staged. Live Where the Magic Happens! This beautif...	3 beds \| 3 baths \| 1,520 sq.ft.	$369,999	Airbnb cash on cash: 2.36% Traditional cash on cash: 3.4% Airbnb Rental Income: $2597 Traditional Rental Income: $2338 Airbnb ROI: 2.36% Traditional ROI: 3.4%
11325 Fenimore Ct Windermere, FL One or more photo(s) has been virtually staged. Newly added virtually staged images to hel...	4 beds \| 3 baths \| 2,658 sq.ft.	$1,200,000	Airbnb cash on cash: -0.12% Traditional cash on cash: 1.42% Airbnb Rental Income: $3311 Traditional Rental Income: $4288 Airbnb ROI: -0.12% Traditional ROI: 1.42%
7462 BENTONSHIRE AVE Windermere, FL BIG price reduction for this move in ready 3/2.5 Townhome in Windermere! New roof 2024. AC...	3 beds \| 3 baths \| 1,480 sq.ft.	$359,000	Airbnb cash on cash: 2.53% Traditional cash on cash: 3.45% Airbnb Rental Income: $2597 Traditional Rental Income: $2285 Airbnb ROI: 2.53% Traditional ROI: 3.45%
6130 Grosvenor Shore Dr Windermere, FL Remarkable Waterview Estate in Keeneâs Pointe! Heated Saltwater Pool, Main-Floor Living,...	4 beds \| 4 baths \| 4,676 sq.ft.	$3,500,000	Airbnb cash on cash: -1.04% Traditional cash on cash: 0.49% Airbnb Rental Income: $3311 Traditional Rental Income: $7548 Airbnb ROI: -1.04% Traditional ROI: 0.49%
6442 Golden Dewdrop Trl Windermere, FL Come see this beautiful place. This immaculate home features include over 2,100 square fee...	3 beds \| 2 baths \| 2,139 sq.ft.	$585,000	Airbnb cash on cash: 0.89% Traditional cash on cash: 2.87% Airbnb Rental Income: $2597 Traditional Rental Income: $3055 Airbnb ROI: 0.89% Traditional ROI: 2.87%
6117 Louise Cove Dr Windermere, FL Nestled along the shores of Lake Louise within Isleworth West, this exceptional two-story ...	4 beds \| 4 baths \| 5,752 sq.ft.	$5,400,000	Airbnb cash on cash: -1.71% Traditional cash on cash: -0.8% Airbnb Rental Income: $3311 Traditional Rental Income: $7149 Airbnb ROI: -1.71% Traditional ROI: -0.8%
6615 Helmsley Cir Windermere, FL Beautifully remodeled and impeccably maintained, this spacious 3,390 sq. ft. two-story hom...	5 beds \| 3 baths \| 3,390 sq.ft.	$799,900	Airbnb cash on cash: 4.9% Traditional cash on cash: 4.43% Airbnb Rental Income: $5841 Traditional Rental Income: $4329 Airbnb ROI: 4.9% Traditional ROI: 4.43%
8582 POWDER RIDGE TRAIL Windermere, FL AN IRRESISTIBLE INVESTMENT OPPORTUNITY â OR YOUR FIRST HOME! Welcome to this stunning K...	4 beds \| 4 baths \| 2,297 sq.ft.	$670,000	Airbnb cash on cash: 1.61% Traditional cash on cash: 2.41% Airbnb Rental Income: $3311 Traditional Rental Income: $3071 Airbnb ROI: 1.61% Traditional ROI: 2.41%
7545 Lake Albert Dr Windermere, FL Welcome to 7545 Lake Albert Drive. Where timeless architecture meets modern luxury. Nestl...	4 beds \| 3 baths \| 3,425 sq.ft.	$1,100,000	Airbnb cash on cash: 0.59% Traditional cash on cash: 4.9% Airbnb Rental Income: $3311 Traditional Rental Income: $6985 Airbnb ROI: 0.59% Traditional ROI: 4.9%
7482 BENTONSHIRE AVENUE Windermere, FL Under contract-accepting backup offers. Discover this beautiful corner-unit townhome locat...	3 beds \| 3 baths \| 1,428 sq.ft.	$399,900	Airbnb cash on cash: 2.61% Traditional cash on cash: 3.54% Airbnb Rental Income: $2597 Traditional Rental Income: $2324 Airbnb ROI: 2.61% Traditional ROI: 3.54%
7777 MOSER AVENUE Windermere, FL BACK ON MARKET DUE TO BUYER DEFAULT - This upscale, meticulously maintained end-unit townh...	3 beds \| 3 baths \| 1,670 sq.ft.	$399,000	Airbnb cash on cash: 1.52% Traditional cash on cash: 2.74% Airbnb Rental Income: $2597 Traditional Rental Income: $2434 Airbnb ROI: 1.52% Traditional ROI: 2.74%
6734 BRIDGEWATER VILLAGE ROAD Windermere, FL LUXURY WINDERMERE HOME ON OVERSIZED CONSERVATION LOT - Welcome to Windermere living at its...	3 beds \| 3 baths \| 3,094 sq.ft.	$649,000	Airbnb cash on cash: 0.33% Traditional cash on cash: 1.85% Airbnb Rental Income: $2597 Traditional Rental Income: $2894 Airbnb ROI: 0.33% Traditional ROI: 1.85%
106 Butler St Windermere, FL Located within the coveted town limits of Windermere, this completely updated four-bedroom...	4 beds \| 2 baths \| 2,058 sq.ft.	$1,199,999	Airbnb cash on cash: 0.46% Traditional cash on cash: 0.84% Airbnb Rental Income: $3311 Traditional Rental Income: $3002 Airbnb ROI: 0.46% Traditional ROI: 0.84%
11660 DELWICK DRIVE Windermere, FL Under contract-accepting backup offers. This season, discover a home where gratitude meets...	4 beds \| 5 baths \| 3,051 sq.ft.	$795,000	Airbnb cash on cash: 0.56% Traditional cash on cash: 5.48% Airbnb Rental Income: $3311 Traditional Rental Income: $6215 Airbnb ROI: 0.56% Traditional ROI: 5.48%
4812 Alexandra Garden Ct Windermere, FL Luxury villa living within the exclusive Gardens of Isleworth, part of the Isleworth Golf ...	3 beds \| 3 baths \| 4,262 sq.ft.	$3,699,000	Airbnb cash on cash: -2.04% Traditional cash on cash: -1.39% Airbnb Rental Income: $2597 Traditional Rental Income: $4218 Airbnb ROI: -2.04% Traditional ROI: -1.39%
9648 Mccormick Pl Windermere, FL Stunning golf and lake views and beautifully updated grounds are hallmarks of this elegant...	3 beds \| 3 baths \| 4,751 sq.ft.	$3,800,000	Airbnb cash on cash: -1.68% Traditional cash on cash: -1.01% Airbnb Rental Income: $2597 Traditional Rental Income: $4324 Airbnb ROI: -1.68% Traditional ROI: -1.01%
13833 ANCILLA BOULEVARD Windermere, FL Under contract-accepting backup offers. Welcome to this ONE STORY TOWNHOME on a CORNER LOT...	2 beds \| 2 baths \| 1,155 sq.ft.	$355,000	Airbnb cash on cash: 8.78% Traditional cash on cash: 2.84% Airbnb Rental Income: $4898 Traditional Rental Income: $1913 Airbnb ROI: 8.78% Traditional ROI: 2.84%
81 Oakdale St Windermere, FL MASSIVE PRICE DROP! A rare find! Extremely well appointed custom home in the heart of D...	5 beds \| 4 baths \| 4,284 sq.ft.	$2,500,000	Airbnb cash on cash: 0.49% Traditional cash on cash: 0.75% Airbnb Rental Income: $5841 Traditional Rental Income: $5272 Airbnb ROI: 0.49% Traditional ROI: 0.75%
6533 Cartmel Ln Windermere, FL Tucked away in the prestigious guard-gated community of The Reserve at Lake Butler Sound, ...	4 beds \| 3 baths \| 3,751 sq.ft.	$1,298,000	Airbnb cash on cash: -0.7% Traditional cash on cash: 1.31% Airbnb Rental Income: $3311 Traditional Rental Income: $4987 Airbnb ROI: -0.7% Traditional ROI: 1.31%
2844 Marquesas Ct Windermere, FL Welcome to your private sanctuary, where every sunrise and sunset dances over the shimmeri...	4 beds \| 3 baths \| 5,365 sq.ft.	$3,700,000	Airbnb cash on cash: -0.81% Traditional cash on cash: -0.33% Airbnb Rental Income: $3311 Traditional Rental Income: $4224 Airbnb ROI: -0.81% Traditional ROI: -0.33%
11922 ANGLE POND AVENUE Windermere, FL One or more photo(s) has been virtually staged. Disney at your doorstep and vibes for days...	4 beds \| 4 baths \| 3,382 sq.ft.	$775,000	Airbnb cash on cash: 1.26% Traditional cash on cash: 3.5% Airbnb Rental Income: $3311 Traditional Rental Income: $4187 Airbnb ROI: 1.26% Traditional ROI: 3.5%
109 E 12th Ave Windermere, FL Modern sophistication and timeless Windermere charm come together in this fully reimagined...	4 beds \| 3 baths \| 2,791 sq.ft.	$1,224,000	Airbnb cash on cash: -0.42% Traditional cash on cash: 1.56% Airbnb Rental Income: $3311 Traditional Rental Income: $4825 Airbnb ROI: -0.42% Traditional ROI: 1.56%
3328 WAX BERRY COURT Windermere, FL One or more photo(s) has been virtually staged. Price improvement of $25,000! A rare...	4 beds \| 4 baths \| 2,636 sq.ft.	$950,000	Airbnb cash on cash: 0.64% Traditional cash on cash: 3.13% Airbnb Rental Income: $3311 Traditional Rental Income: $4777 Airbnb ROI: 0.64% Traditional ROI: 3.13%
7418 BENTONSHIRE AVENUE Windermere, FL Experience the ideal blend of comfort, style, and convenience in the highly sought-after W...	2 beds \| 3 baths \| 1,228 sq.ft.	$330,000	Airbnb cash on cash: 9.2% Traditional cash on cash: 3.68% Airbnb Rental Income: $4898 Traditional Rental Income: $2183 Airbnb ROI: 9.2% Traditional ROI: 3.68%
11520 Via Lucerna Cir Windermere, FL Beautifully Freshly painted Home in Windermereâs Belmere Village Welcome to this ligh...	4 beds \| 2 baths \| 2,505 sq.ft.	$599,000	Airbnb cash on cash: 1.6% Traditional cash on cash: 3.05% Airbnb Rental Income: $3311 Traditional Rental Income: $3381 Airbnb ROI: 1.6% Traditional ROI: 3.05%
12001 Lake Butler Blvd Windermere, FL Exceptional Contemporary Estate in the Heart of Windermere! Discover the perfect blend ...	3 beds \| 3 baths \| 3,135 sq.ft.	$1,775,000	Airbnb cash on cash: -0.66% Traditional cash on cash: 0.2% Airbnb Rental Income: $2597 Traditional Rental Income: $3399 Airbnb ROI: -0.66% Traditional ROI: 0.2%
13285 GORGONA ISLE DRIVE Windermere, FL One or more photo(s) has been virtually staged. Welcome to this meticulously maintained 2 ...	3 beds \| 3 baths \| 1,547 sq.ft.	$418,000	Airbnb cash on cash: 1.68% Traditional cash on cash: 2.55% Airbnb Rental Income: $2597 Traditional Rental Income: $2315 Airbnb ROI: 1.68% Traditional ROI: 2.55%
11818 WATER RUN ALLEY Windermere, FL Under contract-accepting backup offers. SELLER OFFERS up to $3,000 toward buyer's closing ...	3 beds \| 3 baths \| 1,588 sq.ft.	$410,000	Airbnb cash on cash: 1.53% Traditional cash on cash: 3.16% Airbnb Rental Income: $2597 Traditional Rental Income: $2601 Airbnb ROI: 1.53% Traditional ROI: 3.16%
3443 WILD MYRTLE COURT Windermere, FL Welcome to 3443 Wild Myrtle Court, a beautifully renovated executive home nestled on a ser...	5 beds \| 3 baths \| 2,918 sq.ft.	$1,200,000	Airbnb cash on cash: 2.99% Traditional cash on cash: 2.11% Airbnb Rental Income: $5841 Traditional Rental Income: $3693 Airbnb ROI: 2.99% Traditional ROI: 2.11%
1077 Lascala Dr Windermere, FL Under contract-accepting backup offers. Welcome to this inviting 3 bed, 2 bath home in the...	3 beds \| 2 baths \| 2,514 sq.ft.	$674,995	Airbnb cash on cash: 0.8% Traditional cash on cash: 2.26% Airbnb Rental Income: $2597 Traditional Rental Income: $2896 Airbnb ROI: 0.8% Traditional ROI: 2.26%
7011 NOBLETON DRIVE Windermere, FL Under contract-accepting backup offers. Don't miss an Opportunity to own this Great Crafts...	4 beds \| 3 baths \| 2,460 sq.ft.	$560,000	Airbnb cash on cash: 3.02% Traditional cash on cash: 4.35% Airbnb Rental Income: $3311 Traditional Rental Income: $3265 Airbnb ROI: 3.02% Traditional ROI: 4.35%
12540 Park Ave Windermere, FL Offering a prime lakefront location along the shores of Lake Butler in the esteemed gated ...	5 beds \| 5 baths \| 7,183 sq.ft.	$4,650,000	Airbnb cash on cash: -1.02% Traditional cash on cash: -0.33% Airbnb Rental Income: $5841 Traditional Rental Income: $7657 Airbnb ROI: -1.02% Traditional ROI: -0.33%
1803 Glenbay Ct Windermere, FL Welcome to The Reserve at Belmere. Experience refined living in this exclusive guard-gated...	4 beds \| 3 baths \| 3,040 sq.ft.	$825,000	Airbnb cash on cash: 0.63% Traditional cash on cash: 2.36% Airbnb Rental Income: $3311 Traditional Rental Income: $3900 Airbnb ROI: 0.63% Traditional ROI: 2.36%
13106 ORANGE ISLE DRIVE Windermere, FL Explore the WINTERSET model from Ryan Homes of the Sanctuary at Lakes of Windermere, a cor...	5 beds \| 5 baths \| 3,312 sq.ft.	$870,000	Airbnb cash on cash: 3.17% Traditional cash on cash: 4.6% Airbnb Rental Income: $5841 Traditional Rental Income: $5839 Airbnb ROI: 3.17% Traditional ROI: 4.6%
6443 Cartmel Ln Windermere, FL Exquisitely appointed home being sold fully furnished. Nestled within the highly coveted R...	5 beds \| 4 baths \| 4,257 sq.ft.	$1,475,000	Airbnb cash on cash: 0.94% Traditional cash on cash: 1.99% Airbnb Rental Income: $5841 Traditional Rental Income: $6118 Airbnb ROI: 0.94% Traditional ROI: 1.99%
409 W 2ND AVENUE Windermere, FL Under contract-accepting backup offers. Step inside this beautifully updated home where cl...	5 beds \| 5 baths \| 4,688 sq.ft.	$2,375,000	Airbnb cash on cash: 0.51% Traditional cash on cash: 1.33% Airbnb Rental Income: $5841 Traditional Rental Income: $6481 Airbnb ROI: 0.51% Traditional ROI: 1.33%
14025 OASIS SPRINGS LANE #901 Windermere, FL *3D Tour on Virtual Tour Link 1* This immaculately kept, gated end unit townhome boast...	3 beds \| 3 baths \| 1,786 sq.ft.	$365,000	Airbnb cash on cash: 1.46% Traditional cash on cash: 5.01% Airbnb Rental Income: $2597 Traditional Rental Income: $3189 Airbnb ROI: 1.46% Traditional ROI: 5.01%
11618 Vinci Dr Windermere, FL Behind the gates of Keene's Pointe, on the pristine shores of Lake Burden, an extraordinar...	5 beds \| 5 baths \| 6,188 sq.ft.	$4,950,000	Airbnb cash on cash: -0.88% Traditional cash on cash: -0.3% Airbnb Rental Income: $5841 Traditional Rental Income: $7351 Airbnb ROI: -0.88% Traditional ROI: -0.3%
2107 Westover Reserve Blvd Windermere, FL Discover this beautifully updated 4-bedroom, 4-bathroom home tucked inside the exclusive g...	4 beds \| 4 baths \| 4,676 sq.ft.	$1,060,000	Airbnb cash on cash: 0.47% Traditional cash on cash: 3.32% Airbnb Rental Income: $3311 Traditional Rental Income: $5387 Airbnb ROI: 0.47% Traditional ROI: 3.32%

Real Estate investment in Windermere, FL

There are 199 properties for sale in the city of Windermere . The median list price in Windermere is $1,125,970 and the average price per square foot is $290. In January 2026, the average monthly cash on cash return in Windermere is 1.00%. The average monthly rental income in Windermere is $3,055.

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

There are 199 investment properties available for sale in Windermere.

In 2026, 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

10624 REAMS ROAD

Windermere, FL

4 beds | 3 baths | 2,092 sq.ft.

$505,000

Airbnb cash on cash: 2.98%

Traditional cash on cash: 3.4%

Airbnb Rental Income: $3311

Traditional Rental Income: $2769

Airbnb ROI: 2.98%

Traditional ROI: 3.4%

12307 LANGSTAFF DRIVE

Windermere, FL

3 beds | 3 baths | 1,520 sq.ft.

$369,999

Airbnb cash on cash: 2.36%

Traditional cash on cash: 3.4%

Airbnb Rental Income: $2597

Traditional Rental Income: $2338

Airbnb ROI: 2.36%

Traditional ROI: 3.4%

11325 Fenimore Ct

Windermere, FL

4 beds | 3 baths | 2,658 sq.ft.

$1,200,000

Airbnb cash on cash: -0.12%

Traditional cash on cash: 1.42%

Airbnb Rental Income: $3311

Traditional Rental Income: $4288

Airbnb ROI: -0.12%

Traditional ROI: 1.42%

7462 BENTONSHIRE AVE

Windermere, FL

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

$359,000

Airbnb cash on cash: 2.53%

Traditional cash on cash: 3.45%

Airbnb Rental Income: $2597

Traditional Rental Income: $2285

Airbnb ROI: 2.53%

Traditional ROI: 3.45%

6130 Grosvenor Shore Dr

Windermere, FL

4 beds | 4 baths | 4,676 sq.ft.

$3,500,000

Airbnb cash on cash: -1.04%

Traditional cash on cash: 0.49%

Airbnb Rental Income: $3311

Traditional Rental Income: $7548

Airbnb ROI: -1.04%

Traditional ROI: 0.49%

6442 Golden Dewdrop Trl

Windermere, FL

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

$585,000

Airbnb cash on cash: 0.89%

Traditional cash on cash: 2.87%

Airbnb Rental Income: $2597

Traditional Rental Income: $3055

Airbnb ROI: 0.89%

Traditional ROI: 2.87%

6117 Louise Cove Dr

Windermere, FL

4 beds | 4 baths | 5,752 sq.ft.

$5,400,000

Airbnb cash on cash: -1.71%

Traditional cash on cash: -0.8%

Airbnb Rental Income: $3311

Traditional Rental Income: $7149

Airbnb ROI: -1.71%

Traditional ROI: -0.8%

6615 Helmsley Cir

Windermere, FL

5 beds | 3 baths | 3,390 sq.ft.

$799,900

Airbnb cash on cash: 4.9%

Traditional cash on cash: 4.43%

Airbnb Rental Income: $5841

Traditional Rental Income: $4329

Airbnb ROI: 4.9%