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

Showing 4 Condo 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
8168 BOAT HOOK Loop #724 Windermere, FL Virtually Staged. Imagine coming home to a resort-style community just minutes from Walt D...	3 beds \| 2 baths \| 1,455 sq.ft.	$325,000	Airbnb cash on cash: 4.08% Traditional cash on cash: 1.41% Airbnb Rental Income: $3361 Traditional Rental Income: $1797 Airbnb ROI: 4.08% Traditional ROI: 1.41%
14442 DESERT HAVEN Street #4305 Windermere, FL Beautiful Two-Story Condo in Gated Windermere Community - Minutes from Disney World Welcom...	3 beds \| 3 baths \| 1,534 sq.ft.	$359,900	Airbnb cash on cash: 3.54% Traditional cash on cash: 3.38% Airbnb Rental Income: $3361 Traditional Rental Income: $2558 Airbnb ROI: 3.54% Traditional ROI: 3.38%
8218 MYSTIC VIEW Way #2801 Windermere, FL NEW PRICE ADJUSTMENT! Welcome home to GATED OASIS COVE COMMUNITY offering resort style liv...	3 beds \| 3 baths \| 1,840 sq.ft.	$399,999	Airbnb cash on cash: 3.05% Traditional cash on cash: 3.64% Airbnb Rental Income: $3361 Traditional Rental Income: $2835 Airbnb ROI: 3.05% Traditional ROI: 3.64%
8001 Enchantment Drive #1001 Windermere, FL Welcome to this rare 4-bedroom, 3.5-bath corner-unit condo in the gated community of Oasis...	4 beds \| 4 baths \| 1,792 sq.ft.	$399,900	Airbnb cash on cash: 3.23% Traditional cash on cash: 7.17% Airbnb Rental Income: $2485 Traditional Rental Income: $3362 Airbnb ROI: 3.23% Traditional ROI: 7.17%
Other Investment Properties for Sale in Windermere
6363 SEDONA LEAF Court Windermere , FL Virtually Staged. Welcome to this beautifully maintained 4-bedroom, 3-bathroom home tucked...	4 beds \| 3 baths \| 2,665 sq.ft.	$724,900	Airbnb cash on cash: -0.02% Traditional cash on cash: 2.03% Airbnb Rental Income: $2485 Traditional Rental Income: $3262 Airbnb ROI: -0.02% Traditional ROI: 2.03%
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 Drive Windermere , FL Move-In Ready! Beautifully Updated Home in the Highly Desirable Windermere Area! Welcome t...	4 beds \| 3 baths \| 2,074 sq.ft.	$539,900	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 Drive Windermere , FL PRICE REDUCTION and SIGNIFICANT recent upgrades include the installation of a NEW WATER HE...	4 beds \| 4 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%
7712 FORDSON Lane Windermere , FL This Berkshire Place townhome offers a thoughtfully arranged two-story layout with three b...	3 beds \| 3 baths \| 1,644 sq.ft.	$350,000	Airbnb cash on cash: 3.61% Traditional cash on cash: 2.92% Airbnb Rental Income: $3361 Traditional Rental Income: $2384 Airbnb ROI: 3.61% Traditional ROI: 2.92%
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: -2.27% Traditional cash on cash: -1.09% Airbnb Rental Income: $3361 Traditional Rental Income: $6658 Airbnb ROI: -2.27% Traditional ROI: -1.09%
33 MAIN Street 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%
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 \| 2,091 sq.ft.	$465,000	Airbnb cash on cash: 2.46% Traditional cash on cash: 3.91% Airbnb Rental Income: $3361 Traditional Rental Income: $3242 Airbnb ROI: 2.46% Traditional ROI: 3.91%
12303 LANGSTAFF Drive Windermere , FL ABSOLUTELY STUNNING WINDERMERE END-UNIT TOWNHOME! Welcome home to this exceptional end-uni...	3 beds \| 3 baths \| 1,545 sq.ft.	$420,000	Airbnb cash on cash: 3.66% Traditional cash on cash: 3.1% Airbnb Rental Income: $3361 Traditional Rental Income: $2392 Airbnb ROI: 3.66% Traditional ROI: 3.1%

Your search for investment property begins and ends here

Condos for Sale in Windermere, FL

8168 BOAT HOOK Loop #724

Windermere, FL

3 beds | 2 baths | 1,455 sq.ft.

$325,000

Airbnb cash on cash: 4.08%

Traditional cash on cash: 1.41%

Airbnb Rental Income: $3361

Traditional Rental Income: $1797

Airbnb ROI: 4.08%

Traditional ROI: 1.41%

14442 DESERT HAVEN Street #4305

Windermere, FL

3 beds | 3 baths | 1,534 sq.ft.

$359,900

Airbnb cash on cash: 3.54%

Traditional cash on cash: 3.38%

Airbnb Rental Income: $3361

Traditional Rental Income: $2558

Airbnb ROI: 3.54%

Traditional ROI: 3.38%

8218 MYSTIC VIEW Way #2801

Windermere, FL

3 beds | 3 baths | 1,840 sq.ft.

$399,999

Airbnb cash on cash: 3.05%

Traditional cash on cash: 3.64%

Airbnb Rental Income: $3361

Traditional Rental Income: $2835

Airbnb ROI: 3.05%

Traditional ROI: 3.64%

8001 Enchantment Drive #1001

Windermere, FL

4 beds | 4 baths | 1,792 sq.ft.

$399,900

Airbnb cash on cash: 3.23%

Traditional cash on cash: 7.17%

Airbnb Rental Income: $2485

Traditional Rental Income: $3362

Airbnb ROI: 3.23%

Traditional ROI: 7.17%

Other Investment Properties for Sale in Windermere

Windermere , FL

4 beds | 3 baths | 2,665 sq.ft.

$724,900

Airbnb cash on cash: -0.02%

Traditional cash on cash: 2.03%

Airbnb Rental Income: $2485

Traditional Rental Income: $3262

Airbnb ROI: -0.02%

Traditional ROI: 2.03%

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%

Windermere , FL

4 beds | 3 baths | 2,074 sq.ft.

$539,900

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%

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%

Windermere , FL

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