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 Homes for Sale in Windermere, FL

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

Showing 235 Single Family 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.	$475,000	Airbnb cash on cash: 1.6% Traditional cash on cash: 4.82% Airbnb Rental Income: $2441 Traditional Rental Income: $3275 Airbnb ROI: 1.6% Traditional ROI: 4.82%
9620 Maywood Dr Windermere, FL Lake Front Living at its finest! The perfect family friendly lake house with lots of room...	4 beds \| 3 baths \| 3,004 sq.ft.	$2,349,000	Airbnb cash on cash: -0.69% Traditional cash on cash: -0.09% Airbnb Rental Income: $2441 Traditional Rental Income: $3143 Airbnb ROI: -0.69% Traditional ROI: -0.09%
11035 Schooner Way Windermere, FL Nestled among the Butler Chain of Lakes in the charming Town of Windermere, this 4-bedroo...	4 beds \| 3 baths \| 3,517 sq.ft.	$1,500,000	Airbnb cash on cash: -0.4% Traditional cash on cash: 1.08% Airbnb Rental Income: $2441 Traditional Rental Income: $3908 Airbnb ROI: -0.4% Traditional ROI: 1.08%
11903 CAVE RUN AVENUE Windermere, FL Under contract-accepting backup offers. Stunning move-in ready home in the highly sought-a...	4 beds \| 4 baths \| 3,413 sq.ft.	$750,000	Airbnb cash on cash: -0.06% Traditional cash on cash: 3.76% Airbnb Rental Income: $2441 Traditional Rental Income: $4521 Airbnb ROI: -0.06% 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.	$2,950,000	Airbnb cash on cash: -1.29% Traditional cash on cash: 0.14% Airbnb Rental Income: $2441 Traditional Rental Income: $6032 Airbnb ROI: -1.29% Traditional ROI: 0.14%
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: -0.06% Traditional cash on cash: 3.31% Airbnb Rental Income: $1961 Traditional Rental Income: $3256 Airbnb ROI: -0.06% Traditional ROI: 3.31%
910 Lascala Dr Windermere, FL Unique opportunity to own a stunning Mediterranean-style home with WATER VIEWS and a PRIVA...	4 beds \| 3 baths \| 2,742 sq.ft.	$750,000	Airbnb cash on cash: 0.43% Traditional cash on cash: 3.41% Airbnb Rental Income: $2441 Traditional Rental Income: $3965 Airbnb ROI: 0.43% Traditional ROI: 3.41%
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: -0.47% Traditional cash on cash: 1.31% Airbnb Rental Income: $2441 Traditional Rental Income: $3918 Airbnb ROI: -0.47% 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: -1.88% Traditional cash on cash: -0.55% Airbnb Rental Income: $2441 Traditional Rental Income: $8308 Airbnb ROI: -1.88% Traditional ROI: -0.55%
6558 Helmsley Cir Windermere, FL This gorgeous Windermere 4-bedroom, 3-bath home features a charming front porch to welcome...	4 beds \| 3 baths \| 2,575 sq.ft.	$630,000	Airbnb cash on cash: 1.16% Traditional cash on cash: 2.74% Airbnb Rental Income: $2441 Traditional Rental Income: $2773 Airbnb ROI: 1.16% Traditional ROI: 2.74%
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: 0.45% Traditional cash on cash: 3.12% Airbnb Rental Income: $2441 Traditional Rental Income: $3518 Airbnb ROI: 0.45% Traditional ROI: 3.12%
5199 Latrobe Dr Windermere, FL Positioned along the front nine of Isleworthâs famed championship golf course, this golf...	6 beds \| 6 baths \| 4,665 sq.ft.	$5,300,000	Airbnb cash on cash: 1.49% Traditional cash on cash: 0.12% Airbnb Rental Income: $18773 Traditional Rental Income: $8738 Airbnb ROI: 1.49% Traditional ROI: 0.12%
1136 Lake Whitney Dr Windermere, FL Resort style living. Spectacular, Unique & Richly designed, EXCLUSIVE VILLA D'ESTE. From t...	4 beds \| 5 baths \| 5,722 sq.ft.	$2,225,000	Airbnb cash on cash: -1.24% Traditional cash on cash: 1.48% Airbnb Rental Income: $2441 Traditional Rental Income: $7463 Airbnb ROI: -1.24% Traditional ROI: 1.48%
811 Main St Windermere, FL Exclusive Rare Opportunity to own this expansivev100'x160' double lot in downtown Winderme...	2 beds \| 1 baths \| 1,398 sq.ft.	$649,999	Airbnb cash on cash: -1.23% Traditional cash on cash: 0.75% Airbnb Rental Income: $1221 Traditional Rental Income: $2026 Airbnb ROI: -1.23% Traditional ROI: 0.75%
8632 ABBOTSBURY DRIVE Windermere, FL Under contract-accepting backup offers. Virtually Staged. Seller credit of $5,000 availabl...	4 beds \| 4 baths \| 2,720 sq.ft.	$625,000	Airbnb cash on cash: 0.32% Traditional cash on cash: 3.64% Airbnb Rental Income: $2441 Traditional Rental Income: $3777 Airbnb ROI: 0.32% Traditional ROI: 3.64%
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.	$1,175,000	Airbnb cash on cash: -0.3% Traditional cash on cash: 1.5% Airbnb Rental Income: $2441 Traditional Rental Income: $3815 Airbnb ROI: -0.3% Traditional ROI: 1.5%
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: -2.21% Traditional cash on cash: -0.69% Airbnb Rental Income: $1961 Traditional Rental Income: $6658 Airbnb ROI: -2.21% 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: -1.89% Traditional cash on cash: -0.49% Airbnb Rental Income: $1961 Traditional Rental Income: $6376 Airbnb ROI: -1.89% Traditional ROI: -0.49%
33 Main St 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: -0.4% Traditional cash on cash: 0.44% Airbnb Rental Income: $2441 Traditional Rental Income: $3068 Airbnb ROI: -0.4% Traditional ROI: 0.44%
9110 Palm Tree Dr Windermere, FL Located in the sought after neighborhood of Silver Woods sits this wonderful 3 bedroom 2 b...	3 beds \| 2 baths \| 1,819 sq.ft.	$650,000	Airbnb cash on cash: 0.31% Traditional cash on cash: 2.45% Airbnb Rental Income: $1961 Traditional Rental Income: $2744 Airbnb ROI: 0.31% Traditional ROI: 2.45%
20 Oakdale St Windermere, FL One or more photo(s) has been virtually staged. Nestled in the picturesque town of Winderm...	3 beds \| 2 baths \| 2,188 sq.ft.	$1,499,000	Airbnb cash on cash: -1.11% Traditional cash on cash: 1.58% Airbnb Rental Income: $1961 Traditional Rental Income: $5196 Airbnb ROI: -1.11% Traditional ROI: 1.58%
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.	$2,999,999	Airbnb cash on cash: -1.61% Traditional cash on cash: -0.27% Airbnb Rental Income: $2441 Traditional Rental Income: $5926 Airbnb ROI: -1.61% Traditional ROI: -0.27%
4906 Aviva Garden Ct Windermere, FL Nestled within the gates of the renowned Isleworth Golf & Country Club, this two-story est...	3 beds \| 4 baths \| 6,236 sq.ft.	$4,390,000	Airbnb cash on cash: -2.08% Traditional cash on cash: -1.35% Airbnb Rental Income: $1961 Traditional Rental Income: $4413 Airbnb ROI: -2.08% Traditional ROI: -1.35%
3013 Seigneury Dr Windermere, FL Stylish and elegant with contemporary touches, welcome home to a magnificent and expansive...	4 beds \| 3 baths \| 5,130 sq.ft.	$1,750,000	Airbnb cash on cash: -1.48% Traditional cash on cash: 2.05% Airbnb Rental Income: $2441 Traditional Rental Income: $7579 Airbnb ROI: -1.48% Traditional ROI: 2.05%
11226 Macaw Ct Windermere, FL The Ultimate Entertainerâs Dream Home. Welcome to this exceptional custom-built courtyar...	4 beds \| 4 baths \| 4,549 sq.ft.	$1,825,000	Airbnb cash on cash: -1.2% Traditional cash on cash: 0.89% Airbnb Rental Income: $2441 Traditional Rental Income: $5391 Airbnb ROI: -1.2% Traditional ROI: 0.89%
5128 BUTLER RIDGE DRIVE Windermere, FL Under contract-accepting backup offers. Calling all car enthusiasts or artisans needing a ...	4 beds \| 3 baths \| 2,816 sq.ft.	$1,175,000	Airbnb cash on cash: -0.24% Traditional cash on cash: 1.64% Airbnb Rental Income: $2441 Traditional Rental Income: $3894 Airbnb ROI: -0.24% Traditional ROI: 1.64%
2128 Lake Crescent Ct Windermere, FL Short Sale. Come see it today! Finally Bank above price to close. This property sounds li...	4 beds \| 2 baths \| 2,987 sq.ft.	$790,900	Airbnb cash on cash: -0.22% Traditional cash on cash: 1.52% Airbnb Rental Income: $2441 Traditional Rental Income: $3132 Airbnb ROI: -0.22% Traditional ROI: 1.52%
109 E 12th Ave Windermere, FL Modern style blends with Windermere charm. This totally renovated home is located just st...	4 beds \| 3 baths \| 2,791 sq.ft.	$1,195,000	Airbnb cash on cash: -0.99% Traditional cash on cash: 1.4% Airbnb Rental Income: $2441 Traditional Rental Income: $4506 Airbnb ROI: -0.99% Traditional ROI: 1.4%
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: -0.16% Traditional cash on cash: 3.36% Airbnb Rental Income: $2441 Traditional Rental Income: $4878 Airbnb ROI: -0.16% Traditional ROI: 3.36%
212 W 1st Ave 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: 2.93% Traditional cash on cash: -0.82% Airbnb Rental Income: $18773 Traditional Rental Income: $1866 Airbnb ROI: 2.93% 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: 0.63% Traditional cash on cash: 1.45% Airbnb Rental Income: $2441 Traditional Rental Income: $2287 Airbnb ROI: 0.63% Traditional ROI: 1.45%
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: 0.2% Traditional cash on cash: 1.95% Airbnb Rental Income: $2441 Traditional Rental Income: $3064 Airbnb ROI: 0.2% 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: -2.04% Traditional cash on cash: 0.04% Airbnb Rental Income: $2441 Traditional Rental Income: $11763 Airbnb ROI: -2.04% Traditional ROI: 0.04%
9119 Balmoral Mews Sq Windermere, FL MARCH MADNESS MOVING SALE - PRICE IMPROVEMENT for a home in Balmoral and your new highly s...	4 beds \| 4 baths \| 4,052 sq.ft.	$1,399,000	Airbnb cash on cash: -0.61% Traditional cash on cash: 1.02% Airbnb Rental Income: $2441 Traditional Rental Income: $4039 Airbnb ROI: -0.61% Traditional ROI: 1.02%
12718 Windermere Isles Pl 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.	$1,480,000	Airbnb cash on cash: 9.55% Traditional cash on cash: 2.25% Airbnb Rental Income: $18773 Traditional Rental Income: $5349 Airbnb ROI: 9.55% 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: 0.73% Traditional cash on cash: 2.89% Airbnb Rental Income: $2441 Traditional Rental Income: $3007 Airbnb ROI: 0.73% Traditional ROI: 2.89%
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: -0.99% Traditional cash on cash: 1.17% Airbnb Rental Income: $1961 Traditional Rental Income: $4998 Airbnb ROI: -0.99% Traditional ROI: 1.17%
14255 Sonco Ave Windermere, FL Super Rare Opportunity! Tucked away in one of Windermereâs most desirable areas is the b...	4 beds \| 2 baths \| 2,698 sq.ft.	$749,900	Airbnb cash on cash: -0.28% Traditional cash on cash: 3.53% Airbnb Rental Income: $2441 Traditional Rental Income: $4861 Airbnb ROI: -0.28% Traditional ROI: 3.53%
7011 Nobleton Dr Windermere, FL Under contract-accepting backup offers. Don't miss an Opportunity to own this Great Crafts...	4 beds \| 2 baths \| 2,460 sq.ft.	$580,000	Airbnb cash on cash: 1.64% Traditional cash on cash: 4.35% Airbnb Rental Income: $2441 Traditional Rental Income: $3265 Airbnb ROI: 1.64% Traditional ROI: 4.35%
4948 WISE BIRD DRIVE Windermere, FL One or more photo(s) has been virtually staged. Donât miss the opportunity to live in th...	3 beds \| 2 baths \| 1,979 sq.ft.	$679,000	Airbnb cash on cash: -0.35% Traditional cash on cash: 1.71% Airbnb Rental Income: $1961 Traditional Rental Income: $2752 Airbnb ROI: -0.35% Traditional ROI: 1.71%

Your search for investment property begins and ends here

Single Family Homes for Sale in Windermere, FL

10624 REAMS ROAD

Windermere, FL

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

$475,000

Airbnb cash on cash: 1.6%

Traditional cash on cash: 4.82%

Airbnb Rental Income: $2441

Traditional Rental Income: $3275

Airbnb ROI: 1.6%

Traditional ROI: 4.82%

9620 Maywood Dr

Windermere, FL

4 beds | 3 baths | 3,004 sq.ft.

$2,349,000

Airbnb cash on cash: -0.69%

Traditional cash on cash: -0.09%

Airbnb Rental Income: $2441

Traditional Rental Income: $3143

Airbnb ROI: -0.69%

Traditional ROI: -0.09%

11035 Schooner Way

Windermere, FL

4 beds | 3 baths | 3,517 sq.ft.

$1,500,000

Airbnb cash on cash: -0.4%

Traditional cash on cash: 1.08%

Airbnb Rental Income: $2441

Traditional Rental Income: $3908

Airbnb ROI: -0.4%

Traditional ROI: 1.08%

11903 CAVE RUN AVENUE

Windermere, FL

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

$750,000

Airbnb cash on cash: -0.06%

Traditional cash on cash: 3.76%

Airbnb Rental Income: $2441

Traditional Rental Income: $4521

Airbnb ROI: -0.06%

Traditional ROI: 3.76%

6130 Grosvenor Shore Dr

Windermere, FL

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

$2,950,000

Airbnb cash on cash: -1.29%

Traditional cash on cash: 0.14%

Airbnb Rental Income: $2441

Traditional Rental Income: $6032

Airbnb ROI: -1.29%

Traditional ROI: 0.14%

6442 GOLDEN DEWDROP TRAIL

Windermere, FL

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

$575,000

Airbnb cash on cash: -0.06%

Traditional cash on cash: 3.31%

Airbnb Rental Income: $1961

Traditional Rental Income: $3256

Airbnb ROI: -0.06%

Traditional ROI: 3.31%

910 Lascala Dr

Windermere, FL

4 beds | 3 baths | 2,742 sq.ft.

$750,000

Airbnb cash on cash: 0.43%

Traditional cash on cash: 3.41%

Airbnb Rental Income: $2441

Traditional Rental Income: $3965

Airbnb ROI: 0.43%

Traditional ROI: 3.41%

2127 LILYPAD LANE

Windermere, FL

4 beds | 3 baths | 3,349 sq.ft.

$1,250,000

Airbnb cash on cash: -0.47%

Traditional cash on cash: 1.31%

Airbnb Rental Income: $2441

Traditional Rental Income: $3918

Airbnb ROI: -0.47%