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
14025 OASIS SPRINGS LANE #901 Windermere, FL *3D Tour on Virtual Tour Link 1* This immaculately kept, gated end unit townhome boast...	3 beds \| 3 baths \| 1,786 sq.ft.	$385,999	Airbnb cash on cash: 1.33% Traditional cash on cash: 4.68% Airbnb Rental Income: $2597 Traditional Rental Income: $3189 Airbnb ROI: 1.33% Traditional ROI: 4.68%
14242 DESERT HAVEN STREET #GE Windermere, FL Located in the gated community of Oasis Cove, this 3-bedroom, 2.5-bathroom condo offers a ...	3 beds \| 3 baths \| 1,534 sq.ft.	$330,000	Airbnb cash on cash: 2.29% Traditional cash on cash: 4.13% Airbnb Rental Income: $2597 Traditional Rental Income: $2548 Airbnb ROI: 2.29% Traditional ROI: 4.13%
14234 DESERT HAVEN STREET #14234 Windermere, FL Under contract-accepting backup offers. PRICED TO SELL. Spacious and well-appointed, this ...	4 beds \| 3 baths \| 2,067 sq.ft.	$370,000	Airbnb cash on cash: 3.55% Traditional cash on cash: 4.44% Airbnb Rental Income: $3311 Traditional Rental Income: $2878 Airbnb ROI: 3.55% Traditional ROI: 4.44%
8168 BOAT HOOK LOOP #107 Windermere, FL Stunning Oasis in the Heart of Windermere! This is a must-see jewel with nice appointments...	3 beds \| 2 baths \| 1,455 sq.ft.	$339,000	Airbnb cash on cash: 3.43% Traditional cash on cash: 4.12% Airbnb Rental Income: $2597 Traditional Rental Income: $2194 Airbnb ROI: 3.43% Traditional ROI: 4.12%
Other Investment Properties for Sale in Windermere
5141 AUTUMN RIDGE LANE Windermere , FL Under contract-accepting backup offers. Welcome home to this beautifully renovated one-sto...	4 beds \| 3 baths \| 2,390 sq.ft.	$949,000	Airbnb cash on cash: 0.96% Traditional cash on cash: 2.17% Airbnb Rental Income: $3311 Traditional Rental Income: $3633 Airbnb ROI: 0.96% Traditional ROI: 2.17%
12654 CRAGSIDE LANE Windermere , FL Welcome to a truly rare opportunity in Windermere with full GARAGE APARTMENT, FULLY PAID ...	5 beds \| 4 baths \| 3,072 sq.ft.	$679,900	Airbnb cash on cash: 4.68% Traditional cash on cash: 3.32% Airbnb Rental Income: $5841 Traditional Rental Income: $3812 Airbnb ROI: 4.68% Traditional ROI: 3.32%
11325 FENIMORE COURT Windermere , FL Come home to a golf enthusiastâs dream set along the 6th Hole of the renowned Jack Nickl...	4 beds \| 4 baths \| 2,658 sq.ft.	$1,300,000	Airbnb cash on cash: -0.19% Traditional cash on cash: 1.23% Airbnb Rental Income: $3311 Traditional Rental Income: $4288 Airbnb ROI: -0.19% Traditional ROI: 1.23%
7462 BENTONSHIRE AVE Windermere , FL BIG price reduction for this move in ready 3/2.5 Townhome in Windermere! New roof 2024. AC...	3 beds \| 3 baths \| 1,480 sq.ft.	$369,800	Airbnb cash on cash: 2.43% Traditional cash on cash: 3.32% Airbnb Rental Income: $2597 Traditional Rental Income: $2285 Airbnb ROI: 2.43% Traditional ROI: 3.32%
13808 ANCILLA BOULEVARD Windermere , FL One or more photo(s) has been virtually staged. One or more photo(s) has been virtually st...	3 beds \| 3 baths \| 1,461 sq.ft.	$414,999	Airbnb cash on cash: 2.45% Traditional cash on cash: 3.13% Airbnb Rental Income: $2597 Traditional Rental Income: $2239 Airbnb ROI: 2.45% Traditional ROI: 3.13%
8752 LOOKOUT POINTE DRIVE Windermere , FL Experience the enchantment of a luxurious lifestyle with a home that offers elegance, comf...	4 beds \| 4 baths \| 3,270 sq.ft.	$899,000	Airbnb cash on cash: 0.72% Traditional cash on cash: 3.77% Airbnb Rental Income: $3311 Traditional Rental Income: $5123 Airbnb ROI: 0.72% Traditional ROI: 3.77%
9485 WOODBREEZE BOULEVARD Windermere , FL Located in the highly sought-after Silver Woods community in Windermere, this beautifully ...	3 beds \| 2 baths \| 1,723 sq.ft.	$554,900	Airbnb cash on cash: 1.29% Traditional cash on cash: 2.57% Airbnb Rental Income: $2597 Traditional Rental Income: $2639 Airbnb ROI: 1.29% Traditional ROI: 2.57%
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.	$680,000	Airbnb cash on cash: 1.57% Traditional cash on cash: 2.36% Airbnb Rental Income: $3311 Traditional Rental Income: $3071 Airbnb ROI: 1.57% Traditional ROI: 2.36%
7545 LAKE ALBERT DRIVE Windermere , FL Welcome to 7545 Lake Albert Drive. Where timeless architecture meets modern luxury. Nestl...	4 beds \| 5 baths \| 3,425 sq.ft.	$1,100,000	Airbnb cash on cash: 0.59% Traditional cash on cash: 4.9% Airbnb Rental Income: $3311 Traditional Rental Income: $6985 Airbnb ROI: 0.59% Traditional ROI: 4.9%
6864 HELMSLEY CIRCLE Windermere , FL Under contract-accepting backup offers. One or more photo(s) has been virtually staged. **...	3 beds \| 2 baths \| 1,609 sq.ft.	$485,000	Airbnb cash on cash: 1.95% Traditional cash on cash: 2.79% Airbnb Rental Income: $2597 Traditional Rental Income: $2355 Airbnb ROI: 1.95% Traditional ROI: 2.79%
6734 BRIDGEWATER VILLAGE ROAD Windermere , FL Welcome to 6734 Bridgewater Village Road, a true gem nestled in the highly sought-after Vi...	3 beds \| 3 baths \| 3,094 sq.ft.	$699,000	Airbnb cash on cash: 0.24% Traditional cash on cash: 1.65% Airbnb Rental Income: $2597 Traditional Rental Income: $2894 Airbnb ROI: 0.24% Traditional ROI: 1.65%
11660 DELWICK DRIVE Windermere , FL Golden season, golden opportunity in The Reserve at Belmere. Seller contribution to the bu...	4 beds \| 5 baths \| 3,051 sq.ft.	$850,000	Airbnb cash on cash: 0.46% Traditional cash on cash: 5.06% Airbnb Rental Income: $3311 Traditional Rental Income: $6215 Airbnb ROI: 0.46% Traditional ROI: 5.06%
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: -2.04% Traditional cash on cash: -1.39% Airbnb Rental Income: $2597 Traditional Rental Income: $4218 Airbnb ROI: -2.04% Traditional ROI: -1.39%
7673 RIPPLEPOINTE WAY Windermere , FL Welcome to Lake Burden, one of Windermereâs most desirable and well-established communit...	4 beds \| 3 baths \| 2,212 sq.ft.	$469,500	Airbnb cash on cash: 2.56% Traditional cash on cash: 3.13% Airbnb Rental Income: $3311 Traditional Rental Income: $2822 Airbnb ROI: 2.56% Traditional ROI: 3.13%
13225 CHARFIELD STREET Windermere , FL Welcome Home to your Spacious ENCLOSED and Private POOL HOME located in the sought-after c...	4 beds \| 4 baths \| 2,628 sq.ft.	$649,000	Airbnb cash on cash: 2.03% Traditional cash on cash: 4.24% Airbnb Rental Income: $3311 Traditional Rental Income: $3913 Airbnb ROI: 2.03% Traditional ROI: 4.24%

Your search for investment property begins and ends here

Condos for Sale in Windermere, FL

14025 OASIS SPRINGS LANE #901

Windermere, FL

3 beds | 3 baths | 1,786 sq.ft.

$385,999

Airbnb cash on cash: 1.33%

Traditional cash on cash: 4.68%

Airbnb Rental Income: $2597

Traditional Rental Income: $3189

Airbnb ROI: 1.33%

Traditional ROI: 4.68%

14242 DESERT HAVEN STREET #GE

Windermere, FL

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

$330,000

Airbnb cash on cash: 2.29%

Traditional cash on cash: 4.13%

Airbnb Rental Income: $2597

Traditional Rental Income: $2548

Airbnb ROI: 2.29%

Traditional ROI: 4.13%

14234 DESERT HAVEN STREET #14234

Windermere, FL

4 beds | 3 baths | 2,067 sq.ft.

$370,000

Airbnb cash on cash: 3.55%

Traditional cash on cash: 4.44%

Airbnb Rental Income: $3311

Traditional Rental Income: $2878

Airbnb ROI: 3.55%

Traditional ROI: 4.44%

8168 BOAT HOOK LOOP #107

Windermere, FL

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

$339,000

Airbnb cash on cash: 3.43%

Traditional cash on cash: 4.12%

Airbnb Rental Income: $2597

Traditional Rental Income: $2194

Airbnb ROI: 3.43%

Traditional ROI: 4.12%

Other Investment Properties for Sale in Windermere

Windermere , FL

4 beds | 3 baths | 2,390 sq.ft.

$949,000

Airbnb cash on cash: 0.96%

Traditional cash on cash: 2.17%

Airbnb Rental Income: $3311

Traditional Rental Income: $3633

Airbnb ROI: 0.96%

Traditional ROI: 2.17%

Windermere , FL

5 beds | 4 baths | 3,072 sq.ft.

$679,900

Airbnb cash on cash: 4.68%

Traditional cash on cash: 3.32%

Airbnb Rental Income: $5841

Traditional Rental Income: $3812

Airbnb ROI: 4.68%

Traditional ROI: 3.32%

Windermere , FL

4 beds | 4 baths | 2,658 sq.ft.

$1,300,000

Airbnb cash on cash: -0.19%

Traditional cash on cash: 1.23%

Airbnb Rental Income: $3311

Traditional Rental Income: $4288

Airbnb ROI: -0.19%

Traditional ROI: 1.23%

Windermere , FL

3 beds | 3 baths | 1,480 sq.ft.

$369,800

Airbnb cash on cash: 2.43%

Traditional cash on cash: 3.32%

Airbnb Rental Income: $2597

Traditional Rental Income: $2285

Airbnb ROI: 2.43%

Traditional ROI: 3.32%

Windermere , FL

3 beds | 3 baths | 1,461 sq.ft.