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 174 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
11035 Schooner Way Windermere, FL Nestled among the Butler Chain of Lakes in the charming Town of Windermere, this 4-bedroom...	4 beds \| 3 baths \| 3,517 sq.ft.	$1,500,000	Airbnb cash on cash: -0.37% Traditional cash on cash: 1.08% Airbnb Rental Income: $2485 Traditional Rental Income: $3908 Airbnb ROI: -0.37% Traditional ROI: 1.08%
11938 Silverlake Park Dr Windermere, FL Move-In Ready! Beautifully Updated Home in the Highly Desirable Windermere Area! Welcome t...	4 beds \| 2 baths \| 2,074 sq.ft.	$519,900	Airbnb cash on cash: 1.2% Traditional cash on cash: 2.88% Airbnb Rental Income: $2485 Traditional Rental Income: $2732 Airbnb ROI: 1.2% Traditional ROI: 2.88%
13228 ROSKIN Lane Windermere, FL Virtually Staged. 13228 Roskin Ln is a two-story Windermere home with a two-story foyer an...	4 beds \| 2 baths \| 2,745 sq.ft.	$645,000	Airbnb cash on cash: 0.96% Traditional cash on cash: 2.19% Airbnb Rental Income: $2485 Traditional Rental Income: $2618 Airbnb ROI: 0.96% Traditional ROI: 2.19%
910 Lascala Dr Windermere, FL PRICE REDUCTION and SIGNIFICANT recent upgrades include the installation of a NEW WATER HE...	4 beds \| 3 baths \| 2,742 sq.ft.	$725,000	Airbnb cash on cash: 0.56% Traditional cash on cash: 3.65% Airbnb Rental Income: $2485 Traditional Rental Income: $3965 Airbnb ROI: 0.56% Traditional ROI: 3.65%
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: -2.27% Traditional cash on cash: -1.09% Airbnb Rental Income: $3361 Traditional Rental Income: $6658 Airbnb ROI: -2.27% Traditional ROI: -1.09%
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.	$1,572,000	Airbnb cash on cash: -0.37% Traditional cash on cash: 0.44% Airbnb Rental Income: $2485 Traditional Rental Income: $3068 Airbnb ROI: -0.37% Traditional ROI: 0.44%
212 W 1st Ave Windermere, FL Virtually Staged. Positioned along the coveted Butler Chain of Lakes, this waterfront resi...	4 beds \| 2 baths \| 2,627 sq.ft.	$1,599,000	Airbnb cash on cash: -0.58% Traditional cash on cash: -0.59% Airbnb Rental Income: $2485 Traditional Rental Income: $1866 Airbnb ROI: -0.58% Traditional ROI: -0.59%
7033 BRAMLEA Lane Windermere, FL Modern elegance meets resort-style living in the Lakes of Windermere. Welcome to a beautif...	3 beds \| 3 baths \| 2,229 sq.ft.	$647,000	Airbnb cash on cash: 1.71% Traditional cash on cash: 2.96% Airbnb Rental Income: $3361 Traditional Rental Income: $3362 Airbnb ROI: 1.71% Traditional ROI: 2.96%
12718 Windermere Isles Pl Windermere, FL Spectacular residence tucked away on a quiet cul-de-sac in the heart of Windermere. Situat...	5 beds \| 4 baths \| 3,487 sq.ft.	$1,365,000	Airbnb cash on cash: 9.28% Traditional cash on cash: 2.37% Airbnb Rental Income: $17742 Traditional Rental Income: $5349 Airbnb ROI: 9.28% Traditional ROI: 2.37%
12001 Lake Butler Blvd Windermere, FL Exceptional Contemporary Estate in the Heart of Windermere! Discover the perfect blend of ...	3 beds \| 3 baths \| 3,135 sq.ft.	$1,775,000	Airbnb cash on cash: -0.28% Traditional cash on cash: 1.17% Airbnb Rental Income: $3361 Traditional Rental Income: $4998 Airbnb ROI: -0.28% Traditional ROI: 1.17%
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: 1.69% Traditional cash on cash: 4.33% Airbnb Rental Income: $2485 Traditional Rental Income: $3265 Airbnb ROI: 1.69% Traditional ROI: 4.33%
4948 WISE BIRD Drive Windermere, FL One or more photo(s) has been virtually staged. Don't miss the opportunity to live in the ...	3 beds \| 2 baths \| 1,979 sq.ft.	$679,000	Airbnb cash on cash: 1.49% Traditional cash on cash: 1.71% Airbnb Rental Income: $3361 Traditional Rental Income: $2752 Airbnb ROI: 1.49% Traditional ROI: 1.71%
12102 Montalcino Cir Windermere, FL Virtually Staged. Welcome to 12102 Montalcino Circle, an exceptional custom built waterfro...	4 beds \| 4 baths \| 4,296 sq.ft.	$3,100,000	Airbnb cash on cash: -1.54% Traditional cash on cash: 0.28% Airbnb Rental Income: $2485 Traditional Rental Income: $7101 Airbnb ROI: -1.54% Traditional ROI: 0.28%
11021 Hawkshead Ct Windermere, FL Under contract-accepting backup offers. Welcome to this exquisite 5-bedroom, 4-bathroom re...	5 beds \| 4 baths \| 3,557 sq.ft.	$1,100,000	Airbnb cash on cash: 6.3% Traditional cash on cash: 1.83% Airbnb Rental Income: $11724 Traditional Rental Income: $5010 Airbnb ROI: 6.3% Traditional ROI: 1.83%
12264 Montalcino Cir Windermere, FL Lakefront, Luxurious, home with Private Pool in Windermere. A True Paradise! Discover this...	4 beds \| 4 baths \| 7,872 sq.ft.	$5,390,000	Airbnb cash on cash: -2.33% Traditional cash on cash: -1.48% Airbnb Rental Income: $2485 Traditional Rental Income: $6123 Airbnb ROI: -2.33% Traditional ROI: -1.48%
5138 Fairway Oaks Dr Windermere, FL Set along Isleworth's signature 12th fairway, this fully reimagined estate captures the es...	4 beds \| 5 baths \| 4,330 sq.ft.	$4,999,500	Airbnb cash on cash: -1.29% Traditional cash on cash: -0.36% Airbnb Rental Income: $2485 Traditional Rental Income: $6220 Airbnb ROI: -1.29% Traditional ROI: -0.36%
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: 3.39% Traditional cash on cash: 1.52% Airbnb Rental Income: $17742 Traditional Rental Income: $9064 Airbnb ROI: 3.39% Traditional ROI: 1.52%
11923 Lake Butler Blvd Windermere, FL Nestled on one of Windermere's most desirable streets, this charming home offers a rare op...	3 beds \| 2 baths \| 2,238 sq.ft.	$1,630,000	Airbnb cash on cash: -0.12% Traditional cash on cash: 0.35% Airbnb Rental Income: $3361 Traditional Rental Income: $3332 Airbnb ROI: -0.12% Traditional ROI: 0.35%
13226 Zori Ln Windermere, FL WELCOME to this STUNNING, BEAUTIFULLY UPDATED, MOVE-IN READY home in one of Windermere's m...	4 beds \| 2 baths \| 2,521 sq.ft.	$645,000	Airbnb cash on cash: 1.18% Traditional cash on cash: 2.32% Airbnb Rental Income: $2485 Traditional Rental Income: $2572 Airbnb ROI: 1.18% Traditional ROI: 2.32%
14371 Crest Palm Ave Windermere, FL One or more photo(s) has been virtually staged. Arlington Floorplan - 3153 Sq. Ft. \| 4 Bed...	4 beds \| 4 baths \| 3,153 sq.ft.	$989,990	Airbnb cash on cash: 0.46% Traditional cash on cash: 1.84% Airbnb Rental Income: $2485 Traditional Rental Income: $3202 Airbnb ROI: 0.46% Traditional ROI: 1.84%
8724 Peachtree Park Ct Windermere, FL Recent pricing adjustment creates an exceptional opportunity to own a thoughtfully designe...	4 beds \| 3 baths \| 3,315 sq.ft.	$809,500	Airbnb cash on cash: -0.18% Traditional cash on cash: 3.03% Airbnb Rental Income: $2485 Traditional Rental Income: $4361 Airbnb ROI: -0.18% Traditional ROI: 3.03%
9319 Woodbreeze Blvd Windermere, FL WONDERFUL WINDERMERE 4 BED/ 2 BATH HOME LOCATED IN THE CHARMING COMMUNITY OF SILVER WOODS....	4 beds \| 2 baths \| 1,798 sq.ft.	$554,555	Airbnb cash on cash: 1.78% Traditional cash on cash: 3.7% Airbnb Rental Income: $2485 Traditional Rental Income: $2877 Airbnb ROI: 1.78% Traditional ROI: 3.7%
13542 Gorgona Isle Dr Windermere, FL Virtually Staged. Lake View Home with Private Pool & Fireworks Views - Minutes from Walt D...	4 beds \| 3 baths \| 2,224 sq.ft.	$850,000	Airbnb cash on cash: -0.28% Traditional cash on cash: 2.16% Airbnb Rental Income: $2485 Traditional Rental Income: $3879 Airbnb ROI: -0.28% Traditional ROI: 2.16%
3629 Lake Buynak Rd Windermere, FL Now offered at an exceptional value, this 1.3-acre property in Lake Buynak Estates present...	4 beds \| 3 baths \| 2,618 sq.ft.	$975,000	Airbnb cash on cash: 0.1% Traditional cash on cash: 3.18% Airbnb Rental Income: $2485 Traditional Rental Income: $4677 Airbnb ROI: 0.1% Traditional ROI: 3.18%
4819 Alexandra Garden Ct Windermere, FL Discover the effortless blend of luxury, privacy, and modern design in this lovely Gardens...	4 beds \| 4 baths \| 3,745 sq.ft.	$3,200,000	Airbnb cash on cash: -2.33% Traditional cash on cash: -0.95% Airbnb Rental Income: $2485 Traditional Rental Income: $5979 Airbnb ROI: -2.33% Traditional ROI: -0.95%
13420 BONICA Way Windermere, FL Experience the Florida lifestyle in this stunning fully furnished 5-Bed/4-Bath pool home o...	5 beds \| 4 baths \| 4,489 sq.ft.	$1,875,000	Airbnb cash on cash: 6.12% Traditional cash on cash: 1.72% Airbnb Rental Income: $17742 Traditional Rental Income: $6932 Airbnb ROI: 6.12% Traditional ROI: 1.72%
8225 Bryce Canyon Ave Windermere, FL Beautiful 4-Bedroom Home in Windermere, FL - Prime Location and Comfort for the Whole Fami...	4 beds \| 2 baths \| 1,840 sq.ft.	$560,000	Airbnb cash on cash: 1.08% Traditional cash on cash: 3.45% Airbnb Rental Income: $2485 Traditional Rental Income: $3120 Airbnb ROI: 1.08% Traditional ROI: 3.45%
4301 Down Point Ln Windermere, FL Lakefront estate on Lake Down in the Butler Chain of Lakes with over 150 feet of frontage ...	5 beds \| 4 baths \| 7,153 sq.ft.	$2,950,000	Airbnb cash on cash: 3.66% Traditional cash on cash: 0.83% Airbnb Rental Income: $17742 Traditional Rental Income: $6855 Airbnb ROI: 3.66% Traditional ROI: 0.83%

Your search for investment property begins and ends here

Single Family Homes for Sale in Windermere, FL

11035 Schooner Way

Windermere, FL

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

$1,500,000

Airbnb cash on cash: -0.37%

Traditional cash on cash: 1.08%

Airbnb Rental Income: $2485

Traditional Rental Income: $3908

Airbnb ROI: -0.37%

Traditional ROI: 1.08%

11938 Silverlake Park Dr

Windermere, FL

4 beds | 2 baths | 2,074 sq.ft.

$519,900

Airbnb cash on cash: 1.2%

Traditional cash on cash: 2.88%

Airbnb Rental Income: $2485

Traditional Rental Income: $2732

Airbnb ROI: 1.2%

Traditional ROI: 2.88%

13228 ROSKIN Lane

Windermere, FL

4 beds | 2 baths | 2,745 sq.ft.

$645,000

Airbnb cash on cash: 0.96%

Traditional cash on cash: 2.19%

Airbnb Rental Income: $2485

Traditional Rental Income: $2618

Airbnb ROI: 0.96%

Traditional ROI: 2.19%

910 Lascala Dr

Windermere, FL

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

$725,000

Airbnb cash on cash: 0.56%

Traditional cash on cash: 3.65%

Airbnb Rental Income: $2485

Traditional Rental Income: $3965

Airbnb ROI: 0.56%

Traditional ROI: 3.65%

4812 Alexandra Garden Ct

Windermere, FL

3 beds | 3 baths | 4,262 sq.ft.

$3,699,000

Airbnb cash on cash: -2.27%

Traditional cash on cash: -1.09%

Airbnb Rental Income: $3361

Traditional Rental Income: $6658

Airbnb ROI: -2.27%

Traditional ROI: -1.09%

33 Main St

Windermere, FL

4 beds | 2 baths | 2,130 sq.ft.

$1,572,000

Airbnb cash on cash: -0.37%

Traditional cash on cash: 0.44%

Airbnb Rental Income: $2485

Traditional Rental Income: $3068

Airbnb ROI: -0.37%

Traditional ROI: 0.44%

212 W 1st Ave

Windermere, FL

4 beds | 2 baths | 2,627 sq.ft.

$1,599,000

Airbnb cash on cash: -0.58%

Traditional cash on cash: -0.59%

Airbnb Rental Income: $2485

Traditional Rental Income: $1866

Airbnb ROI: -0.58%

Traditional ROI: -0.59%

7033 BRAMLEA Lane

Windermere, FL

3 beds | 3 baths | 2,229 sq.ft.

$647,000

Airbnb cash on cash: 1.71%

Traditional cash on cash: 2.96%

Airbnb Rental Income: $3361

Traditional Rental Income: $3362

Airbnb ROI: 1.71%