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
5825 OXFORD MOOR BOULEVARD Windermere, FL Under contract-accepting backup offers. Completely Remodeled 2022 \| Single Story \|Gated Wi...	4 beds \| 4 baths \| 4,319 sq.ft.	$1,500,000	Airbnb cash on cash: -0.46% Traditional cash on cash: 1.26% Airbnb Rental Income: $3311 Traditional Rental Income: $4973 Airbnb ROI: -0.46% Traditional ROI: 1.26%
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.	$475,000	Airbnb cash on cash: 3.23% Traditional cash on cash: 4.82% Airbnb Rental Income: $3311 Traditional Rental Income: $3275 Airbnb ROI: 3.23% Traditional ROI: 4.82%
2806 WINDSOR HILL DRIVE Windermere, FL Under contract-accepting backup offers. Step into this stunning 4-bedroom, 3-bathroom pool...	4 beds \| 3 baths \| 3,181 sq.ft.	$1,099,000	Airbnb cash on cash: 0.12% Traditional cash on cash: 0.97% Airbnb Rental Income: $3311 Traditional Rental Income: $3441 Airbnb ROI: 0.12% Traditional ROI: 0.97%
1317 GLENHEATHER DRIVE Windermere, FL Under contract-accepting backup offers. Welcome to 1317 Glenheather Drive, a 2,811-square-...	4 beds \| 3 baths \| 2,811 sq.ft.	$974,900	Airbnb cash on cash: 0.77% Traditional cash on cash: 2.12% Airbnb Rental Income: $3311 Traditional Rental Income: $3803 Airbnb ROI: 0.77% Traditional ROI: 2.12%
7644 RIPPLEPOINTE WAY Windermere, FL Welcome to Lake Burden, one of Windermereâs most desirable and well-established communit...	3 beds \| 3 baths \| 1,881 sq.ft.	$435,000	Airbnb cash on cash: 1.4% Traditional cash on cash: 4.1% Airbnb Rental Income: $2597 Traditional Rental Income: $3074 Airbnb ROI: 1.4% Traditional ROI: 4.1%
11903 CAVE RUN AVENUE Windermere, FL Stunning move-in ready home in the highly sought-after Windermere Trails community, locate...	4 beds \| 4 baths \| 3,413 sq.ft.	$750,000	Airbnb cash on cash: 0.97% Traditional cash on cash: 3.76% Airbnb Rental Income: $3311 Traditional Rental Income: $4521 Airbnb ROI: 0.97% Traditional ROI: 3.76%
13019 LANGSTAFF DRIVE Windermere, FL Under contract-accepting backup offers. Tucked away in the peaceful Lake Reams Townhome co...	2 beds \| 3 baths \| 1,375 sq.ft.	$360,000	Airbnb cash on cash: 8.13% Traditional cash on cash: 3.02% Airbnb Rental Income: $4898 Traditional Rental Income: $2167 Airbnb ROI: 8.13% Traditional ROI: 3.02%
6442 GOLDEN DEWDROP TRAIL Windermere, FL Short Sale. Come see this beautiful place. This immaculate home features include over 2,10...	3 beds \| 3 baths \| 2,139 sq.ft.	$575,000	Airbnb cash on cash: 0.93% Traditional cash on cash: 3.31% Airbnb Rental Income: $2597 Traditional Rental Income: $3256 Airbnb ROI: 0.93% Traditional ROI: 3.31%
2127 LILYPAD LANE Windermere, FL Under contract-accepting backup offers. Welcome to a rare opportunity in the highly sought...	4 beds \| 3 baths \| 3,349 sq.ft.	$1,250,000	Airbnb cash on cash: 0.15% Traditional cash on cash: 1.31% Airbnb Rental Income: $3311 Traditional Rental Income: $3918 Airbnb ROI: 0.15% Traditional ROI: 1.31%
6117 LOUISE COVE DRIVE Windermere, FL Under contract-accepting backup offers. Nestled along the shores of Lake Louise within Isl...	4 beds \| 5 baths \| 5,752 sq.ft.	$5,250,000	Airbnb cash on cash: -1.73% Traditional cash on cash: -0.55% Airbnb Rental Income: $3311 Traditional Rental Income: $8308 Airbnb ROI: -1.73% Traditional ROI: -0.55%
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: 3.12% Airbnb Rental Income: $3311 Traditional Rental Income: $3518 Airbnb ROI: 1.61% Traditional ROI: 3.12%
7231 SANGALLA DRIVE Windermere, FL Located in the gated community of Casa Del Lago in Windermere, featuring just 88 luxury ho...	5 beds \| 5 baths \| 3,835 sq.ft.	$1,398,000	Airbnb cash on cash: 1.53% Traditional cash on cash: 2.5% Airbnb Rental Income: $5841 Traditional Rental Income: $5936 Airbnb ROI: 1.53% Traditional ROI: 2.5%
8632 ABBOTSBURY DRIVE Windermere, FL One or more photo(s) has been virtually staged. Welcome to this beautifully updated 4-bedr...	4 beds \| 4 baths \| 2,720 sq.ft.	$625,000	Airbnb cash on cash: 1.57% Traditional cash on cash: 3.64% Airbnb Rental Income: $3311 Traditional Rental Income: $3777 Airbnb ROI: 1.57% Traditional ROI: 3.64%
4812 ALEXANDRA GARDEN COURT Windermere, FL Luxury villa living within the exclusive Gardens of Isleworth, part of the Isleworth Golf ...	3 beds \| 5 baths \| 4,262 sq.ft.	$3,699,000	Airbnb cash on cash: -2.06% Traditional cash on cash: -0.69% Airbnb Rental Income: $2597 Traditional Rental Income: $6658 Airbnb ROI: -2.06% Traditional ROI: -0.69%
9648 MCCORMICK PLACE Windermere, FL Stunning golf and lake views and beautifully updated grounds are hallmarks of this elegant...	3 beds \| 4 baths \| 4,751 sq.ft.	$3,800,000	Airbnb cash on cash: -1.74% Traditional cash on cash: -0.49% Airbnb Rental Income: $2597 Traditional Rental Income: $6376 Airbnb ROI: -1.74% Traditional ROI: -0.49%
33 MAIN STREET Windermere, FL BUTLER CHAIN WATERFRONT Windermere 4/3 HOME WITH BOAT SLIP on a .37 acre Lot. Cypress tree...	4 beds \| 2 baths \| 2,130 sq.ft.	$1,575,000	Airbnb cash on cash: 0.1% Traditional cash on cash: 0.44% Airbnb Rental Income: $3311 Traditional Rental Income: $3068 Airbnb ROI: 0.1% Traditional ROI: 0.44%
6390 SOUTHBRIDGE STREET Windermere, FL One or more photo(s) has been virtually staged. Seller may consider buyer concessions if m...	4 beds \| 3 baths \| 1,632 sq.ft.	$395,000	Airbnb cash on cash: 3.42% Traditional cash on cash: 2.61% Airbnb Rental Income: $3311 Traditional Rental Income: $2269 Airbnb ROI: 3.42% Traditional ROI: 2.61%
13755 BRAVANTE ALLEY Windermere, FL **This house comes with a REDUCED RATE through the seller's preferred lender. This is a le...	3 beds \| 3 baths \| 1,996 sq.ft.	$480,000	Airbnb cash on cash: 1.39% Traditional cash on cash: 4.22% Airbnb Rental Income: $2597 Traditional Rental Income: $3242 Airbnb ROI: 1.39% Traditional ROI: 4.22%
3013 SEIGNEURY DRIVE Windermere, FL Stylish and elegant with contemporary touches, welcome home to a magnificent and expansive...	4 beds \| 5 baths \| 5,130 sq.ft.	$1,750,000	Airbnb cash on cash: -1.03% Traditional cash on cash: 2.05% Airbnb Rental Income: $3311 Traditional Rental Income: $7579 Airbnb ROI: -1.03% Traditional ROI: 2.05%
11226 MACAW COURT Windermere, FL The Ultimate Entertainerâs Dream Home. Welcome to this exceptional custom-built courtyar...	4 beds \| 5 baths \| 4,549 sq.ft.	$1,825,000	Airbnb cash on cash: -0.78% Traditional cash on cash: 0.89% Airbnb Rental Income: $3311 Traditional Rental Income: $5391 Airbnb ROI: -0.78% Traditional ROI: 0.89%
5128 BUTLER RIDGE DRIVE Windermere, FL Calling all car enthusiasts or artisans needing a large, detached workshop on your propert...	4 beds \| 3 baths \| 2,816 sq.ft.	$1,250,000	Airbnb cash on cash: 0.34% Traditional cash on cash: 1.48% Airbnb Rental Income: $3311 Traditional Rental Income: $3894 Airbnb ROI: 0.34% Traditional ROI: 1.48%
12633 HADDON DRIVE Windermere, FL Sitting on a premium corner lot with mature landscaping, this beautiful Kensington model b...	5 beds \| 4 baths \| 3,000 sq.ft.	$650,000	Airbnb cash on cash: 5.28% Traditional cash on cash: 4.18% Airbnb Rental Income: $5841 Traditional Rental Income: $4012 Airbnb ROI: 5.28% Traditional ROI: 4.18%
9055 LEGADO DRIVE Windermere, FL Under contract-accepting backup offers. Welcome to this beautiful former model townhome in...	3 beds \| 3 baths \| 1,584 sq.ft.	$425,000	Airbnb cash on cash: 1.56% Traditional cash on cash: 2.67% Airbnb Rental Income: $2597 Traditional Rental Income: $2417 Airbnb ROI: 1.56% Traditional ROI: 2.67%
109 E 12TH AVENUE Windermere, FL Modern style blends with Windermere charm. This totally renovated home is located just st...	4 beds \| 4 baths \| 2,791 sq.ft.	$1,198,000	Airbnb cash on cash: -0.46% Traditional cash on cash: 1.28% Airbnb Rental Income: $3311 Traditional Rental Income: $4506 Airbnb ROI: -0.46% Traditional ROI: 1.28%
12863 HOLDENBURY LANE Windermere, FL LOCATION! LOCATION! $5,000 CONCESSION FOR BUYER'S CLOSING COSTS. Experience refined living...	3 beds \| 2 baths \| 2,148 sq.ft.	$539,000	Airbnb cash on cash: 1.2% Traditional cash on cash: 3.36% Airbnb Rental Income: $2597 Traditional Rental Income: $3062 Airbnb ROI: 1.2% Traditional ROI: 3.36%
3328 WAX BERRY COURT Windermere, FL One or more photo(s) has been virtually staged. Located within Lake Butler Estates, one of...	4 beds \| 4 baths \| 2,636 sq.ft.	$925,000	Airbnb cash on cash: 0.68% Traditional cash on cash: 3.36% Airbnb Rental Income: $3311 Traditional Rental Income: $4878 Airbnb ROI: 0.68% Traditional ROI: 3.36%
212 W 1ST AVENUE Windermere, FL Pre-Construction. To be built. Positioned along the coveted Butler Chain of Lakes, this wa...	5 beds \| 5 baths \| 3,800 sq.ft.	$3,900,000	Airbnb cash on cash: -0.05% Traditional cash on cash: -0.82% Airbnb Rental Income: $5841 Traditional Rental Income: $1866 Airbnb ROI: -0.05% Traditional ROI: -0.82%
12533 CRAGSIDE LANE Windermere, FL **This house comes with a REDUCED RATE through the seller's preferred lender. This is a le...	4 beds \| 2 baths \| 2,151 sq.ft.	$575,000	Airbnb cash on cash: 1.98% Traditional cash on cash: 1.45% Airbnb Rental Income: $3311 Traditional Rental Income: $2287 Airbnb ROI: 1.98% Traditional ROI: 1.45%
4 CHASE ROAD Windermere, FL Under contract-accepting backup offers. FULLY RENOVATED DREAM HOME. This home is located r...	3 beds \| 2 baths \| 2,386 sq.ft.	$875,000	Airbnb cash on cash: 0.44% Traditional cash on cash: 2.03% Airbnb Rental Income: $2597 Traditional Rental Income: $3266 Airbnb ROI: 0.44% Traditional ROI: 2.03%
11951 VERMILLION AVENUE Windermere, FL LOCATION! LOCATION! BRAND NEW roof and gutters were installed in late 2023. Discover this ...	3 beds \| 3 baths \| 1,539 sq.ft.	$459,000	Airbnb cash on cash: 1.65% Traditional cash on cash: 4.71% Airbnb Rental Income: $2597 Traditional Rental Income: $3287 Airbnb ROI: 1.65% Traditional ROI: 4.71%
1028 LASCALA DRIVE Windermere, FL Under contract-accepting backup offers. Introducing an EXCEPTIONAL opportunity to own a RE...	4 beds \| 3 baths \| 2,208 sq.ft.	$749,000	Airbnb cash on cash: 1.24% Traditional cash on cash: 1.95% Airbnb Rental Income: $3311 Traditional Rental Income: $3064 Airbnb ROI: 1.24% Traditional ROI: 1.95%
6142 GROSVENOR SHORE DRIVE Windermere, FL Located in Grosvenor Village within Keeneâs Pointe, this estate overlooks a pond and the...	4 beds \| 6 baths \| 6,950 sq.ft.	$5,150,000	Airbnb cash on cash: -1.89% Traditional cash on cash: 0.04% Airbnb Rental Income: $3311 Traditional Rental Income: $11763 Airbnb ROI: -1.89% Traditional ROI: 0.04%
12718 WINDERMERE ISLES PLACE Windermere, FL Welcome to 12718 Windermere Isles Place, a spectacular residence tucked away on a quiet cu...	5 beds \| 4 baths \| 3,487 sq.ft.	$1,490,000	Airbnb cash on cash: 1.77% Traditional cash on cash: 2.25% Airbnb Rental Income: $5841 Traditional Rental Income: $5349 Airbnb ROI: 1.77% Traditional ROI: 2.25%
6897 NORTHWICH DRIVE Windermere, FL Under contract-accepting backup offers. Welcome to the highly desirable Lakes of Windermer...	4 beds \| 3 baths \| 2,229 sq.ft.	$574,900	Airbnb cash on cash: 2.08% Traditional cash on cash: 2.89% Airbnb Rental Income: $3311 Traditional Rental Income: $3007 Airbnb ROI: 2.08% Traditional ROI: 2.89%
12001 LAKE BUTLER BOULEVARD 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: 1.17% Airbnb Rental Income: $2597 Traditional Rental Income: $4998 Airbnb ROI: -0.66% Traditional ROI: 1.17%
7327 MILLSTONE STREET Windermere, FL A rare find in townhome living in the exclusive Lake Burden community of Windermere â th...	3 beds \| 3 baths \| 1,531 sq.ft.	$459,000	Airbnb cash on cash: 1.64% Traditional cash on cash: 2.58% Airbnb Rental Income: $2597 Traditional Rental Income: $2377 Airbnb ROI: 1.64% Traditional ROI: 2.58%
14255 SONCO AVENUE Windermere, FL Super Rare Opportunity! Tucked away in one of Windermereâs most desirable areas is the b...	4 beds \| 3 baths \| 2,698 sq.ft.	$849,900	Airbnb cash on cash: 0.64% Traditional cash on cash: 3.53% Airbnb Rental Income: $3311 Traditional Rental Income: $4861 Airbnb ROI: 0.64% Traditional ROI: 3.53%
4071 Isabella Cir Windermere, FL Embraced on nearly an acre within the prestigious gated community of Casabella, The Renais...	5 beds \| 9 baths \| 7,058 sq.ft.	$3,290,000	Airbnb cash on cash: -0.59% Traditional cash on cash: 0.26% Airbnb Rental Income: $5841 Traditional Rental Income: $7260 Airbnb ROI: -0.59% Traditional ROI: 0.26%
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 AVENUE Windermere, FL Under contract-accepting backup offers. Extraordinary Lake Butler views abound from this c...	5 beds \| 6 baths \| 7,740 sq.ft.	$4,599,000	Airbnb cash on cash: -0.98% Traditional cash on cash: 0.96% Airbnb Rental Income: $5841 Traditional Rental Income: $12983 Airbnb ROI: -0.98% Traditional ROI: 0.96%

Real Estate investment in Windermere, FL

There are 154 properties for sale in the city of Windermere . The median list price in Windermere is $962,450 and the average price per square foot is $287. In June 2026, the average monthly cash on cash return in Windermere is 2.00%. The average monthly rental income in Windermere is $3,299.

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

There are 154 investment properties available for sale in Windermere.

In 2026, the best neighborhood to buy investment property is Windermere.

The ROI for Long-Term is higher than the Short-Term in Windermere with average rental income of $3,299.

Your search for investment property begins and ends here

Investment Property for Sale in Windermere, FL

5825 OXFORD MOOR BOULEVARD

Windermere, FL

4 beds | 4 baths | 4,319 sq.ft.

$1,500,000

Airbnb cash on cash: -0.46%

Traditional cash on cash: 1.26%

Airbnb Rental Income: $3311

Traditional Rental Income: $4973

Airbnb ROI: -0.46%

Traditional ROI: 1.26%

10624 REAMS ROAD

Windermere, FL

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

$475,000

Airbnb cash on cash: 3.23%

Traditional cash on cash: 4.82%

Airbnb Rental Income: $3311

Traditional Rental Income: $3275

Airbnb ROI: 3.23%

Traditional ROI: 4.82%

2806 WINDSOR HILL DRIVE

Windermere, FL

4 beds | 3 baths | 3,181 sq.ft.

$1,099,000

Airbnb cash on cash: 0.12%

Traditional cash on cash: 0.97%

Airbnb Rental Income: $3311

Traditional Rental Income: $3441

Airbnb ROI: 0.12%

Traditional ROI: 0.97%

1317 GLENHEATHER DRIVE

Windermere, FL

4 beds | 3 baths | 2,811 sq.ft.

$974,900

Airbnb cash on cash: 0.77%

Traditional cash on cash: 2.12%

Airbnb Rental Income: $3311

Traditional Rental Income: $3803

Airbnb ROI: 0.77%

Traditional ROI: 2.12%

7644 RIPPLEPOINTE WAY

Windermere, FL

3 beds | 3 baths | 1,881 sq.ft.

$435,000

Airbnb cash on cash: 1.4%

Traditional cash on cash: 4.1%

Airbnb Rental Income: $2597

Traditional Rental Income: $3074

Airbnb ROI: 1.4%

Traditional ROI: 4.1%

11903 CAVE RUN AVENUE

Windermere, FL

4 beds | 4 baths | 3,413 sq.ft.

$750,000

Airbnb cash on cash: 0.97%

Traditional cash on cash: 3.76%

Airbnb Rental Income: $3311

Traditional Rental Income: $4521

Airbnb ROI: 0.97%

Traditional ROI: 3.76%

13019 LANGSTAFF DRIVE

Windermere, FL

2 beds | 3 baths | 1,375 sq.ft.

$360,000

Airbnb cash on cash: 8.13%

Traditional cash on cash: 3.02%

Airbnb Rental Income: $4898

Traditional Rental Income: $2167

Airbnb ROI: 8.13%

Traditional ROI: 3.02%

6442 GOLDEN DEWDROP TRAIL

Windermere, FL

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

$575,000

Airbnb cash on cash: 0.93%

Traditional cash on cash: 3.31%

Airbnb Rental Income: $2597

Traditional Rental Income: $3256

Airbnb ROI: 0.93%