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 Completely Remodeled 2022 \| Single Story \|Gated Windermere Community \| Set on nearly three...	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.	$499,000	Airbnb cash on cash: 3.03% Traditional cash on cash: 4.54% Airbnb Rental Income: $3311 Traditional Rental Income: $3275 Airbnb ROI: 3.03% Traditional ROI: 4.54%
2806 WINDSOR HILL DRIVE Windermere, FL Step into this stunning 4-bedroom, 3-bathroom pool home nestled on nearly half an acre in ...	4 beds \| 3 baths \| 3,181 sq.ft.	$1,150,000	Airbnb cash on cash: 0.07% Traditional cash on cash: 0.89% Airbnb Rental Income: $3311 Traditional Rental Income: $3441 Airbnb ROI: 0.07% Traditional ROI: 0.89%
13240 ROSKIN LANE Windermere, FL Under contract-accepting backup offers. Tucked within a beautiful Windermere community sur...	4 beds \| 4 baths \| 3,108 sq.ft.	$724,000	Airbnb cash on cash: 1.37% Traditional cash on cash: 2.91% Airbnb Rental Income: $3311 Traditional Rental Income: $3614 Airbnb ROI: 1.37% Traditional ROI: 2.91%
8520 GREENBANK BOULEVARD Windermere, FL Beautiful and inviting home located in the heart of Windermere, nestled within a charming ...	3 beds \| 2 baths \| 1,726 sq.ft.	$549,900	Airbnb cash on cash: 1.04% Traditional cash on cash: 2.65% Airbnb Rental Income: $2597 Traditional Rental Income: $2801 Airbnb ROI: 1.04% Traditional ROI: 2.65%
8447 WOBURN COURT Windermere, FL Under contract-accepting backup offers. PREMIUM PRESERVE HOMESITE backing directly to Tibe...	4 beds \| 3 baths \| 2,945 sq.ft.	$1,325,000	Airbnb cash on cash: -0.24% Traditional cash on cash: 1.38% Airbnb Rental Income: $3311 Traditional Rental Income: $4560 Airbnb ROI: -0.24% Traditional ROI: 1.38%
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.	$445,000	Airbnb cash on cash: 1.35% Traditional cash on cash: 3.99% Airbnb Rental Income: $2597 Traditional Rental Income: $3074 Airbnb ROI: 1.35% Traditional ROI: 3.99%
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%
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: 0.03% Airbnb Rental Income: $3311 Traditional Rental Income: $6032 Airbnb ROI: -1.04% Traditional ROI: 0.03%
6442 GOLDEN DEWDROP TRAIL Windermere, FL Come see this beautiful place. This immaculate home features include over 2,100 square fee...	3 beds \| 3 baths \| 2,139 sq.ft.	$585,000	Airbnb cash on cash: 0.89% Traditional cash on cash: 3.24% Airbnb Rental Income: $2597 Traditional Rental Income: $3256 Airbnb ROI: 0.89% Traditional ROI: 3.24%
910 LASCALA DRIVE Windermere, FL Unique opportunity to own a stunning Mediterranean-style home with WATER VIEWS and a PRIVA...	4 beds \| 4 baths \| 2,742 sq.ft.	$770,000	Airbnb cash on cash: 1.46% Traditional cash on cash: 3.4% Airbnb Rental Income: $3311 Traditional Rental Income: $3965 Airbnb ROI: 1.46% Traditional ROI: 3.4%
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%
6615 HELMSLEY CIRCLE Windermere, FL Beautifully remodeled and impeccably maintained, this spacious 3,390 sq. ft. two-story hom...	5 beds \| 4 baths \| 3,390 sq.ft.	$769,900	Airbnb cash on cash: 5.13% Traditional cash on cash: 4.56% Airbnb Rental Income: $5841 Traditional Rental Income: $4270 Airbnb ROI: 5.13% Traditional ROI: 4.56%
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%
1420 DINGENS AVENUE Windermere, FL One or more photo(s) has been virtually staged. No HOA custom pool home on over half an ac...	4 beds \| 4 baths \| 4,072 sq.ft.	$1,600,000	Airbnb cash on cash: -0.16% Traditional cash on cash: 1.3% Airbnb Rental Income: $3311 Traditional Rental Income: $4752 Airbnb ROI: -0.16% Traditional ROI: 1.3%
13263 STRODE LANE Windermere, FL This beautifully maintained residence showcases rich engineered oak wood flooring througho...	4 beds \| 4 baths \| 2,559 sq.ft.	$798,900	Airbnb cash on cash: 1.16% Traditional cash on cash: 3.05% Airbnb Rental Income: $3311 Traditional Rental Income: $3976 Airbnb ROI: 1.16% Traditional ROI: 3.05%
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.	$1,498,000	Airbnb cash on cash: 1.36% Traditional cash on cash: 2.26% Airbnb Rental Income: $5841 Traditional Rental Income: $5936 Airbnb ROI: 1.36% Traditional ROI: 2.26%
8632 ABBOTSBURY DRIVE Windermere, FL **This house comes with a REDUCED RATE through the seller's preferred lender. This is a le...	4 beds \| 4 baths \| 2,720 sq.ft.	$609,999	Airbnb cash on cash: 1.63% Traditional cash on cash: 3.75% Airbnb Rental Income: $3311 Traditional Rental Income: $3777 Airbnb ROI: 1.63% Traditional ROI: 3.75%
11536 Claymont Cir Windermere, FL Attention to detail, craftsmanship truly describes this move-in ready home. As you enter, ...	4 beds \| 3 baths \| 2,882 sq.ft.	$1,250,000	Airbnb cash on cash: 0.28% Traditional cash on cash: 1.35% Airbnb Rental Income: $3311 Traditional Rental Income: $3815 Airbnb ROI: 0.28% Traditional ROI: 1.35%
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%
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.	$2,300,000	Airbnb cash on cash: 0.62% Traditional cash on cash: 0.98% Airbnb Rental Income: $5841 Traditional Rental Income: $5454 Airbnb ROI: 0.62% Traditional ROI: 0.98%
11816 ANGLE POND AVENUE Windermere, FL Under contract-accepting backup offers. Under 15 minutes to Magic Kingdom. Fireworks on yo...	4 beds \| 4 baths \| 3,391 sq.ft.	$835,000	Airbnb cash on cash: 0.88% Traditional cash on cash: 4.09% Airbnb Rental Income: $3311 Traditional Rental Income: $5068 Airbnb ROI: 0.88% Traditional ROI: 4.09%
2722 PARK ROYAL DRIVE Windermere, FL Under contract-accepting backup offers. One or more photo(s) has been virtually staged. Un...	4 beds \| 3 baths \| 2,967 sq.ft.	$950,000	Airbnb cash on cash: 0.68% Traditional cash on cash: 2.23% Airbnb Rental Income: $3311 Traditional Rental Income: $3946 Airbnb ROI: 0.68% Traditional ROI: 2.23%
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.	$489,999	Airbnb cash on cash: 1.35% Traditional cash on cash: 4.11% Airbnb Rental Income: $2597 Traditional Rental Income: $3242 Airbnb ROI: 1.35% Traditional ROI: 4.11%
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: -0.17% Airbnb Rental Income: $3311 Traditional Rental Income: $4759 Airbnb ROI: -0.81% Traditional ROI: -0.17%
5145 Latrobe Dr Windermere, FL Nestled along Isleworthâs famed championship golf course overlooking Hole 4, this beauti...	4 beds \| 4 baths \| 4,512 sq.ft.	$3,449,000	Airbnb cash on cash: -1.35% Traditional cash on cash: -0.31% Airbnb Rental Income: $3311 Traditional Rental Income: $5926 Airbnb ROI: -1.35% Traditional ROI: -0.31%
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.	$1,890,000	Airbnb cash on cash: -1.03% Traditional cash on cash: 1.83% Airbnb Rental Income: $3311 Traditional Rental Income: $7579 Airbnb ROI: -1.03% Traditional ROI: 1.83%
11922 ANGLE POND AVENUE Windermere, FL One or more photo(s) has been virtually staged. Welcome to this beautifully maintained fou...	4 beds \| 4 baths \| 3,382 sq.ft.	$760,000	Airbnb cash on cash: 1.3% Traditional cash on cash: 4.13% Airbnb Rental Income: $3311 Traditional Rental Income: $4576 Airbnb ROI: 1.3% Traditional ROI: 4.13%
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%
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.	$1,225,000	Airbnb cash on cash: -0.47% Traditional cash on cash: 1.23% Airbnb Rental Income: $3311 Traditional Rental Income: $4506 Airbnb ROI: -0.47% Traditional ROI: 1.23%
12863 HOLDENBURY LANE Windermere, FL Experience refined living in this impeccably upgraded residence located in Lakes of Winder...	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 in Lake Butler Estates, one of Win...	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 Ave Windermere, FL Exceptional opportunity to own a waterfront home with dock on famed Lake Butler in the Old...	N/A beds \| N/A baths \| 2,627 sq.ft.	$1,600,000	Airbnb cash on cash: -1.4% Traditional cash on cash: -0.25% Airbnb Rental Income: $413 Traditional Rental Income: $1866 Airbnb ROI: -1.4% Traditional ROI: -0.25%
606 E 6th Ave Windermere, FL Home Ownership dreams come true with this beautiful custom home with breathtaking views of...	4 beds \| 4 baths \| 4,471 sq.ft.	$2,350,000	Airbnb cash on cash: -0.4% Traditional cash on cash: 0.27% Airbnb Rental Income: $3311 Traditional Rental Income: $4037 Airbnb ROI: -0.4% Traditional ROI: 0.27%
4 CHASE ROAD Windermere, FL FULLY RENOVATED DREAM HOME. This home is located right in the heart of the Town of Winderm...	3 beds \| 2 baths \| 2,386 sq.ft.	$900,000	Airbnb cash on cash: 0.4% Traditional cash on cash: 1.94% Airbnb Rental Income: $2597 Traditional Rental Income: $3266 Airbnb ROI: 0.4% Traditional ROI: 1.94%
6638 BRIDGEWATER VILLAGE ROAD Windermere, FL Under contract-accepting backup offers. Welcome to Vineyards Horizon West, this stunning 4...	4 beds \| 3 baths \| 2,908 sq.ft.	$664,900	Airbnb cash on cash: 1.33% Traditional cash on cash: 2.21% Airbnb Rental Income: $3311 Traditional Rental Income: $3114 Airbnb ROI: 1.33% Traditional ROI: 2.21%
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...	4 beds \| 4 baths \| 3,487 sq.ft.	$1,490,000	Airbnb cash on cash: 0.24% Traditional cash on cash: 2.25% Airbnb Rental Income: $3311 Traditional Rental Income: $5349 Airbnb ROI: 0.24% Traditional ROI: 2.25%
11 Main St Windermere, FL Heart of Downtown Windermere! Walking distance to downtown events, farmers market, food tr...	5 beds \| 5 baths \| 4,723 sq.ft.	$6,700,000	Airbnb cash on cash: -0.35% Traditional cash on cash: -0.15% Airbnb Rental Income: $5841 Traditional Rental Income: $5959 Airbnb ROI: -0.35% Traditional ROI: -0.15%

Real Estate investment in Windermere, FL

There are 228 properties for sale in the city of Windermere . The median list price in Windermere is $1,255,000 and the average price per square foot is $310. In April 2026, the average monthly cash on cash return in Windermere is 2.00%. The average monthly rental income in Windermere is $3,868.

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

There are 228 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

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.

$499,000

Airbnb cash on cash: 3.03%

Traditional cash on cash: 4.54%

Airbnb Rental Income: $3311

Traditional Rental Income: $3275

Airbnb ROI: 3.03%

Traditional ROI: 4.54%

2806 WINDSOR HILL DRIVE

Windermere, FL

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

$1,150,000

Airbnb cash on cash: 0.07%

Traditional cash on cash: 0.89%

Airbnb Rental Income: $3311

Traditional Rental Income: $3441

Airbnb ROI: 0.07%

Traditional ROI: 0.89%

13240 ROSKIN LANE

Windermere, FL

4 beds | 4 baths | 3,108 sq.ft.

$724,000

Airbnb cash on cash: 1.37%

Traditional cash on cash: 2.91%

Airbnb Rental Income: $3311

Traditional Rental Income: $3614

Airbnb ROI: 1.37%

Traditional ROI: 2.91%

8520 GREENBANK BOULEVARD

Windermere, FL

3 beds | 2 baths | 1,726 sq.ft.

$549,900

Airbnb cash on cash: 1.04%

Traditional cash on cash: 2.65%

Airbnb Rental Income: $2597

Traditional Rental Income: $2801

Airbnb ROI: 1.04%

Traditional ROI: 2.65%

8447 WOBURN COURT

Windermere, FL

4 beds | 3 baths | 2,945 sq.ft.

$1,325,000

Airbnb cash on cash: -0.24%

Traditional cash on cash: 1.38%

Airbnb Rental Income: $3311

Traditional Rental Income: $4560

Airbnb ROI: -0.24%

Traditional ROI: 1.38%

7644 RIPPLEPOINTE WAY

Windermere, FL

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

$445,000

Airbnb cash on cash: 1.35%

Traditional cash on cash: 3.99%

Airbnb Rental Income: $2597

Traditional Rental Income: $3074

Airbnb ROI: 1.35%

Traditional ROI: 3.99%

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%