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.

Condos for Sale in Windermere, FL

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

Showing 130 Condos 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
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: 4.04% Airbnb Rental Income: $3311 Traditional Rental Income: $3041 Airbnb ROI: 3.03% Traditional ROI: 4.04%
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%
11325 FENIMORE COURT Windermere, FL Under contract-accepting backup offers. One or more photo(s) has been virtually staged. Ne...	4 beds \| 4 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%
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%
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: 3.14% Airbnb Rental Income: $3311 Traditional Rental Income: $4085 Airbnb ROI: 0.97% Traditional ROI: 3.14%
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: 3.06% Airbnb Rental Income: $2597 Traditional Rental Income: $3159 Airbnb ROI: 0.89% Traditional ROI: 3.06%
6117 LOUISE COVE DRIVE Windermere, FL Nestled along the shores of Lake Louise within Isleworth West, this exceptional two-story ...	4 beds \| 5 baths \| 5,752 sq.ft.	$5,250,000	Airbnb cash on cash: -1.73% Traditional cash on cash: -0.97% Airbnb Rental Income: $3311 Traditional Rental Income: $6272 Airbnb ROI: -1.73% Traditional ROI: -0.97%
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: 3.92% Airbnb Rental Income: $5841 Traditional Rental Income: $3813 Airbnb ROI: 5.13% Traditional ROI: 3.92%
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: 2.81% Airbnb Rental Income: $3311 Traditional Rental Income: $3321 Airbnb ROI: 1.61% Traditional ROI: 2.81%
7545 LAKE ALBERT DRIVE Windermere, FL Under contract-accepting backup offers. Welcome to 7545 Lake Albert Drive. Where timeless...	4 beds \| 5 baths \| 3,425 sq.ft.	$1,075,000	Airbnb cash on cash: 0.62% Traditional cash on cash: 5.04% Airbnb Rental Income: $3311 Traditional Rental Income: $6985 Airbnb ROI: 0.62% Traditional ROI: 5.04%
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: 2.07% Airbnb Rental Income: $5841 Traditional Rental Income: $5665 Airbnb ROI: 1.36% Traditional ROI: 2.07%
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: 3.07% Airbnb Rental Income: $3311 Traditional Rental Income: $3392 Airbnb ROI: 1.63% Traditional ROI: 3.07%
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: -1.47% Airbnb Rental Income: $2597 Traditional Rental Income: $3991 Airbnb ROI: -2.06% Traditional ROI: -1.47%
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: -1.12% Airbnb Rental Income: $2597 Traditional Rental Income: $4142 Airbnb ROI: -1.74% Traditional ROI: -1.12%
11816 ANGLE POND AVENUE Windermere, FL Under 15 minutes to Magic Kingdom. Fireworks on your drive home. Dinner at EPCOT on a Tues...	4 beds \| 4 baths \| 3,391 sq.ft.	$835,000	Airbnb cash on cash: 0.88% Traditional cash on cash: 2.89% Airbnb Rental Income: $3311 Traditional Rental Income: $4138 Airbnb ROI: 0.88% Traditional ROI: 2.89%
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: 1.79% Airbnb Rental Income: $3311 Traditional Rental Income: $3557 Airbnb ROI: 0.68% Traditional ROI: 1.79%
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: 3.3% Airbnb Rental Income: $2597 Traditional Rental Income: $2870 Airbnb ROI: 1.35% Traditional ROI: 3.3%
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: 0.07% Airbnb Rental Income: $3311 Traditional Rental Income: $4500 Airbnb ROI: -1.03% Traditional ROI: 0.07%
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: 2.87% Airbnb Rental Income: $3311 Traditional Rental Income: $3679 Airbnb ROI: 1.3% Traditional ROI: 2.87%
7422 BENTONSHIRE AVENUE Windermere, FL Under contract-accepting backup offers. WELCOME HOME NEW ROOF (2024), NEW A/C (2024), ...	2 beds \| 3 baths \| 1,360 sq.ft.	$349,000	Airbnb cash on cash: 8.59% Traditional cash on cash: 4.05% Airbnb Rental Income: $4898 Traditional Rental Income: $2403 Airbnb ROI: 8.59% Traditional ROI: 4.05%
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: 2.18% Airbnb Rental Income: $2597 Traditional Rental Income: $2466 Airbnb ROI: 1.2% Traditional ROI: 2.18%
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: 3.56% Airbnb Rental Income: $3311 Traditional Rental Income: $5052 Airbnb ROI: 0.68% Traditional ROI: 3.56%
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: 2.33% Airbnb Rental Income: $2597 Traditional Rental Income: $3591 Airbnb ROI: 0.4% Traditional ROI: 2.33%
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: -0.88% Airbnb Rental Income: $3311 Traditional Rental Income: $7404 Airbnb ROI: -1.89% Traditional ROI: -0.88%
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: 1.12% Airbnb Rental Income: $2597 Traditional Rental Income: $4910 Airbnb ROI: -0.66% Traditional ROI: 1.12%
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.	$874,900	Airbnb cash on cash: 0.59% Traditional cash on cash: 1.86% Airbnb Rental Income: $3311 Traditional Rental Income: $3604 Airbnb ROI: 0.59% Traditional ROI: 1.86%
9155 PANZANI PLACE Windermere, FL Under contract-accepting backup offers. Perfectly situated behind the gates of the beautif...	4 beds \| 4 baths \| 3,088 sq.ft.	$975,000	Airbnb cash on cash: 0.22% Traditional cash on cash: 1.98% Airbnb Rental Income: $3311 Traditional Rental Income: $4173 Airbnb ROI: 0.22% Traditional ROI: 1.98%
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 Extraordinary Lake Butler views abound from this classically elegant yet recently updated ...	5 beds \| 6 baths \| 7,740 sq.ft.	$4,599,000	Airbnb cash on cash: -0.98% Traditional cash on cash: -0.06% Airbnb Rental Income: $5841 Traditional Rental Income: $8642 Airbnb ROI: -0.98% Traditional ROI: -0.06%
5186 VARDON DRIVE Windermere, FL One or more photo(s) has been virtually staged. Presenting a newly remodeled luxury estate...	4 beds \| 5 baths \| 4,739 sq.ft.	$4,960,000	Airbnb cash on cash: -1.34% Traditional cash on cash: 0.04% Airbnb Rental Income: $3311 Traditional Rental Income: $8924 Airbnb ROI: -1.34% Traditional ROI: 0.04%
12936 DROXFORD ROAD Windermere, FL Seller offering up to $10,000 towards Buyer's closing cost with acceptable offer Lakes of...	5 beds \| 4 baths \| 2,960 sq.ft.	$649,000	Airbnb cash on cash: 4.9% Traditional cash on cash: 2.84% Airbnb Rental Income: $5841 Traditional Rental Income: $3429 Airbnb ROI: 4.9% Traditional ROI: 2.84%
6109 ORTA COURT Windermere, FL Under contract-accepting backup offers. Within the gates of the Waterstone community, this...	5 beds \| 7 baths \| 5,895 sq.ft.	$4,495,000	Airbnb cash on cash: -1.47% Traditional cash on cash: -0.62% Airbnb Rental Income: $5841 Traditional Rental Income: $8195 Airbnb ROI: -1.47% Traditional ROI: -0.62%
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.	$815,000	Airbnb cash on cash: 3.45% Traditional cash on cash: 3.08% Airbnb Rental Income: $5841 Traditional Rental Income: $4396 Airbnb ROI: 3.45% Traditional ROI: 3.08%
6443 CARTMEL LANE Windermere, FL Exquisitely appointed home being sold fully furnished. Nestled within the highly coveted R...	4 beds \| 5 baths \| 4,257 sq.ft.	$1,475,000	Airbnb cash on cash: -0.6% Traditional cash on cash: 1.3% Airbnb Rental Income: $3311 Traditional Rental Income: $5179 Airbnb ROI: -0.6% Traditional ROI: 1.3%
13734 LAKE CAWOOD DRIVE Windermere, FL NEW PRICE - SELLER MOTIVATED! Welcome to this stunning single-story luxury estate located...	4 beds \| 4 baths \| 4,437 sq.ft.	$1,500,000	Airbnb cash on cash: -0.12% Traditional cash on cash: 0.98% Airbnb Rental Income: $3311 Traditional Rental Income: $4091 Airbnb ROI: -0.12% Traditional ROI: 0.98%
11618 VINCI DRIVE Windermere, FL Behind the gates of Keene's Pointe, on the pristine shores of Lake Burden, an extraordinar...	5 beds \| 7 baths \| 6,188 sq.ft.	$4,950,000	Airbnb cash on cash: -0.88% Traditional cash on cash: -0.15% Airbnb Rental Income: $5841 Traditional Rental Income: $8052 Airbnb ROI: -0.88% Traditional ROI: -0.15%
11021 HAWKSHEAD COURT Windermere, FL Under contract-accepting backup offers. Welcome to this exquisite 5-bedroom, 4-bathroom re...	5 beds \| 4 baths \| 3,557 sq.ft.	$1,299,000	Airbnb cash on cash: 1.22% Traditional cash on cash: 1.49% Airbnb Rental Income: $5841 Traditional Rental Income: $5010 Airbnb ROI: 1.22% Traditional ROI: 1.49%
13161 LAKE BUTLER BOULEVARD Windermere, FL Extraordinary lake front opportunity in Windermere on 1.75 acres! PRIVATE GATES! NO HOA! S...	5 beds \| 5 baths \| 4,500 sq.ft.	$3,200,000	Airbnb cash on cash: 0.04% Traditional cash on cash: 0.1% Airbnb Rental Income: $5841 Traditional Rental Income: $4839 Airbnb ROI: 0.04% Traditional ROI: 0.1%

Your search for investment property begins and ends here

Condos for Sale in Windermere, FL

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: 4.04%

Airbnb Rental Income: $3311

Traditional Rental Income: $3041

Airbnb ROI: 3.03%

Traditional ROI: 4.04%

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%

11325 FENIMORE COURT

Windermere, FL

4 beds | 4 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%

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%

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: 3.14%

Airbnb Rental Income: $3311

Traditional Rental Income: $4085

Airbnb ROI: 0.97%

Traditional ROI: 3.14%

6442 GOLDEN DEWDROP TRAIL

Windermere, FL

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

$585,000

Airbnb cash on cash: 0.89%

Traditional cash on cash: 3.06%

Airbnb Rental Income: $2597

Traditional Rental Income: $3159

Airbnb ROI: 0.89%

Traditional ROI: 3.06%

6117 LOUISE COVE DRIVE

Windermere, FL

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

$5,250,000

Airbnb cash on cash: -1.73%

Traditional cash on cash: -0.97%

Airbnb Rental Income: $3311

Traditional Rental Income: $6272

Airbnb ROI: -1.73%

Traditional ROI: -0.97%

6615 HELMSLEY CIRCLE

Windermere, FL

5 beds | 4 baths | 3,390 sq.ft.

$769,900

Airbnb cash on cash: 5.13%

Traditional cash on cash: 3.92%

Airbnb Rental Income: $5841

Traditional Rental Income: $3813

Airbnb ROI: 5.13%