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.

Single Family Residential For Salhttf L For Salhttf L For Salhttf L For Salhttf L Fory Residential for Sale in Windermere, FL

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

Showing 130 Single Family Residential For Salhttf L For Salhttf L For Salhttf L For Salhttf L Fory Residential 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

Single Family Residential For Salhttf L For Salhttf L For Salhttf L For Salhttf L Fory Residential 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%