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.

Investment Property for Sale in Windermere, FL

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PROPERTY	DETAILS	SALE PRICE	INVESTMENT PERFORMANCE
5141 AUTUMN RIDGE LANE Windermere, FL Welcome home to this beautifully renovated one-story estate, set on a rare 1.15-acre corne...	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%
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.	$520,000	Airbnb cash on cash: 2.87% Traditional cash on cash: 3.28% Airbnb Rental Income: $3311 Traditional Rental Income: $2769 Airbnb ROI: 2.87% Traditional ROI: 3.28%
7462 BENTONSHIRE AVE Windermere, FL Move in ready 3/2.5 Townhome in Windermere! New roof 2024. AC compressor new June 2025. Re...	3 beds \| 3 baths \| 1,480 sq.ft.	$378,000	Airbnb cash on cash: 2.36% Traditional cash on cash: 3.23% Airbnb Rental Income: $2597 Traditional Rental Income: $2285 Airbnb ROI: 2.36% Traditional ROI: 3.23%
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.	$929,000	Airbnb cash on cash: 0.66% Traditional cash on cash: 3.61% Airbnb Rental Income: $3311 Traditional Rental Income: $5123 Airbnb ROI: 0.66% Traditional ROI: 3.61%
9447 WESTOVER CLUB CIRCLE Windermere, FL Under contract-accepting backup offers. Welcome to this stunning Windermere pool home, loc...	4 beds \| 3 baths \| 2,568 sq.ft.	$789,000	Airbnb cash on cash: 1.57% Traditional cash on cash: 2.77% Airbnb Rental Income: $3311 Traditional Rental Income: $3452 Airbnb ROI: 1.57% Traditional ROI: 2.77%
9485 WOODBREEZE BOULEVARD Windermere, FL Located in the highly sought-after Silver Woods community in Windermere, this beautiful si...	3 beds \| 2 baths \| 1,723 sq.ft.	$589,900	Airbnb cash on cash: 1.16% Traditional cash on cash: 2.36% Airbnb Rental Income: $2597 Traditional Rental Income: $2639 Airbnb ROI: 1.16% Traditional ROI: 2.36%
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.	$695,000	Airbnb cash on cash: 1.51% Traditional cash on cash: 2.29% Airbnb Rental Income: $3311 Traditional Rental Income: $3071 Airbnb ROI: 1.51% Traditional ROI: 2.29%
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 Luxury, location, and lifestyle â this is the Reserve at Belmere. Behind the gates of...	4 beds \| 5 baths \| 3,051 sq.ft.	$895,000	Airbnb cash on cash: 0.39% Traditional cash on cash: 4.76% Airbnb Rental Income: $3311 Traditional Rental Income: $6215 Airbnb ROI: 0.39% Traditional ROI: 4.76%
7673 RIPPLEPOINTE WAY Windermere, FL Move in ready! Rarely available, 4 bedroom/3 bathroom townhouse located in the sought afte...	4 beds \| 3 baths \| 2,212 sq.ft.	$475,000	Airbnb cash on cash: 2.53% Traditional cash on cash: 3.09% Airbnb Rental Income: $3311 Traditional Rental Income: $2822 Airbnb ROI: 2.53% Traditional ROI: 3.09%
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%
14466 BRIDGEWATER CROSSINGS BOULEVARD Windermere, FL Video Tour Available Welcome to Summerport where location is everything as great schoo...	4 beds \| 3 baths \| 1,642 sq.ft.	$418,000	Airbnb cash on cash: 3.88% Traditional cash on cash: 2.77% Airbnb Rental Income: $3311 Traditional Rental Income: $2136 Airbnb ROI: 3.88% Traditional ROI: 2.77%
5318 KUMQUAT LOOP Windermere, FL This beautifully updated three-bedroom townhome in Windermere offers the perfect blend of ...	3 beds \| 3 baths \| 1,461 sq.ft.	$378,800	Airbnb cash on cash: 2.15% Traditional cash on cash: 2.9% Airbnb Rental Income: $2597 Traditional Rental Income: $2242 Airbnb ROI: 2.15% Traditional ROI: 2.9%
13120 ZORI LANE Windermere, FL Imagine waking up every morning to the serene beauty of your lakefront retreat, with Littl...	4 beds \| 5 baths \| 4,329 sq.ft.	$1,790,000	Airbnb cash on cash: -0.52% Traditional cash on cash: 2.29% Airbnb Rental Income: $3311 Traditional Rental Income: $7244 Airbnb ROI: -0.52% Traditional ROI: 2.29%
11922 ANGLE POND AVENUE Windermere, FL One or more photo(s) has been virtually staged. Located just 2 minutes from Disney in the ...	4 beds \| 4 baths \| 3,382 sq.ft.	$800,000	Airbnb cash on cash: 1.19% Traditional cash on cash: 3.36% Airbnb Rental Income: $3311 Traditional Rental Income: $4187 Airbnb ROI: 1.19% Traditional ROI: 3.36%
1009 ALGARE LOOP Windermere, FL Under contract-accepting backup offers. HIGHEST AND BEST BY 8-12-25 by 12 NOON Stop the ca...	4 beds \| 3 baths \| 2,608 sq.ft.	$875,000	Airbnb cash on cash: 0.8% Traditional cash on cash: 2.09% Airbnb Rental Income: $3311 Traditional Rental Income: $3620 Airbnb ROI: 0.8% Traditional ROI: 2.09%
2128 LAKE CRESCENT COURT Windermere, FL Short Sale. Come see it today! Finally Bank above price to close. This property sounds li...	5 beds \| 3 baths \| 2,987 sq.ft.	$856,000	Airbnb cash on cash: 3.29% Traditional cash on cash: 1.35% Airbnb Rental Income: $5841 Traditional Rental Income: $3132 Airbnb ROI: 3.29% Traditional ROI: 1.35%
2540 HEMPEL COVE CT Windermere, FL Stunning Renovation on 1 Acre in Lake Down Cove. Located at the end of a quiet cul-de-sac,...	5 beds \| 3 baths \| 3,356 sq.ft.	$1,324,900	Airbnb cash on cash: 1.38% Traditional cash on cash: 0.86% Airbnb Rental Income: $5841 Traditional Rental Income: $4045 Airbnb ROI: 1.38% Traditional ROI: 0.86%
11849 CAVE RUN AVENUE Windermere, FL Immaculate and light-filled 4-bedroom, 3.5-bath home with a huge bonus room and flex space...	4 beds \| 4 baths \| 3,414 sq.ft.	$830,000	Airbnb cash on cash: 0.93% Traditional cash on cash: 3.41% Airbnb Rental Income: $3311 Traditional Rental Income: $4489 Airbnb ROI: 0.93% Traditional ROI: 3.41%
11502 WATERSTONE LOOP DRIVE Windermere, FL THIS IS IT! THE RARE GEM YOU HAVE BEEN WAITING FOR! ALL BEDROOMS ARE ON FIRST FLOOR! COME ...	4 beds \| 6 baths \| 4,447 sq.ft.	$2,399,999	Airbnb cash on cash: -0.8% Traditional cash on cash: 2.36% Airbnb Rental Income: $3311 Traditional Rental Income: $9617 Airbnb ROI: -0.8% Traditional ROI: 2.36%
11520 VIA LUCERNA CIRCLE Windermere, FL Beautifully Freshly painted Home in Windermereâs Belmere Village Welcome to this ligh...	4 beds \| 2 baths \| 2,505 sq.ft.	$630,000	Airbnb cash on cash: 1.47% Traditional cash on cash: 2.85% Airbnb Rental Income: $3311 Traditional Rental Income: $3381 Airbnb ROI: 1.47% Traditional ROI: 2.85%
4071 ISABELLA CIRCLE Windermere, FL Welcome to Casabella at Windermere, a beautiful gated community where luxury and elegance ...	5 beds \| 8 baths \| 6,753 sq.ft.	$3,200,000	Airbnb cash on cash: -0.69% Traditional cash on cash: 0.18% Airbnb Rental Income: $5841 Traditional Rental Income: $7260 Airbnb ROI: -0.69% Traditional ROI: 0.18%
13413 HOPKINTON COURT Windermere, FL Newly Renovated Home near Disney!Stunning cul-de-sac Windermere residence, just minutes aw...	4 beds \| 4 baths \| 2,642 sq.ft.	$789,000	Airbnb cash on cash: 1.07% Traditional cash on cash: 2.47% Airbnb Rental Income: $3311 Traditional Rental Income: $3600 Airbnb ROI: 1.07% Traditional ROI: 2.47%
3443 WILD MYRTLE COURT Windermere, FL Welcome to 3443 Wild Myrtle Court, a beautifully renovated executive home nestled on a ser...	5 beds \| 3 baths \| 2,918 sq.ft.	$1,200,000	Airbnb cash on cash: 2.99% Traditional cash on cash: 2.11% Airbnb Rental Income: $5841 Traditional Rental Income: $3693 Airbnb ROI: 2.99% Traditional ROI: 2.11%
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%
11019 KENTMERE COURT Windermere, FL Privately nestled at the end of a cul-de-sac in the prestigious 24-hour guard-gated commun...	4 beds \| 4 baths \| 3,813 sq.ft.	$1,595,000	Airbnb cash on cash: -0.3% Traditional cash on cash: 0.75% Airbnb Rental Income: $3311 Traditional Rental Income: $4124 Airbnb ROI: -0.3% Traditional ROI: 0.75%
6443 CARTMEL LANE Windermere, FL Exquisitely appointed home being sold fully furnished. Nestled within the highly coveted R...	5 beds \| 5 baths \| 4,257 sq.ft.	$1,475,000	Airbnb cash on cash: 0.94% Traditional cash on cash: 1.99% Airbnb Rental Income: $5841 Traditional Rental Income: $6118 Airbnb ROI: 0.94% Traditional ROI: 1.99%
13254 PENSHURST LANE Windermere, FL Privacy, space, and a little bit of magicâthatâs what youâll find in this 5-bedroom,...	5 beds \| 4 baths \| 3,720 sq.ft.	$799,000	Airbnb cash on cash: 3.83% Traditional cash on cash: 5.08% Airbnb Rental Income: $5841 Traditional Rental Income: $5610 Airbnb ROI: 3.83% Traditional ROI: 5.08%
11514 Via Lucerna Circle Windermere, FL Welcome to your new home in the highly desirable Belmere Village community in Windermere! ...	5 beds \| 5 baths \| 2,871 sq.ft.	$724,999	Airbnb cash on cash: 4.52% Traditional cash on cash: 5.78% Airbnb Rental Income: $5841 Traditional Rental Income: $5527 Airbnb ROI: 4.52% Traditional ROI: 5.78%
409 W 2ND AVENUE Windermere, FL Step inside this beautifully updated home where clean lines, soaring ceilings, and two-sto...	5 beds \| 5 baths \| 4,688 sq.ft.	$2,499,000	Airbnb cash on cash: 0.43% Traditional cash on cash: 1.21% Airbnb Rental Income: $5841 Traditional Rental Income: $6481 Airbnb ROI: 0.43% Traditional ROI: 1.21%
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.	$394,994	Airbnb cash on cash: 1.28% Traditional cash on cash: 4.56% Airbnb Rental Income: $2597 Traditional Rental Income: $3189 Airbnb ROI: 1.28% Traditional ROI: 4.56%
5130 SUN PALM DRIVE Windermere, FL Welcome to 5130 Sun Palm Drive, located in the heart of WINDERMERE! This beautifully maint...	3 beds \| 2 baths \| 1,723 sq.ft.	$562,500	Airbnb cash on cash: 1.88% Traditional cash on cash: 3.65% Airbnb Rental Income: $2597 Traditional Rental Income: $2906 Airbnb ROI: 1.88% Traditional ROI: 3.65%
2107 WESTOVER RESERVE BOULEVARD Windermere, FL Discover this beautifully updated 4-bedroom, 4-bathroom home tucked inside the exclusive g...	4 beds \| 4 baths \| 4,676 sq.ft.	$1,170,000	Airbnb cash on cash: 0.33% Traditional cash on cash: 2.92% Airbnb Rental Income: $3311 Traditional Rental Income: $5387 Airbnb ROI: 0.33% Traditional ROI: 2.92%
8713 IRON MOUNTAIN TRAIL Windermere, FL PAID OFF TESLA SOLAR PANELS! Motivated Seller. Welcome to the desirable Windermere Trails ...	5 beds \| 4 baths \| 3,718 sq.ft.	$869,000	Airbnb cash on cash: 3.32% Traditional cash on cash: 2.03% Airbnb Rental Income: $5841 Traditional Rental Income: $3632 Airbnb ROI: 3.32% Traditional ROI: 2.03%
11021 HAWKSHEAD COURT Windermere, FL Welcome to this exquisite 5-bedroom, 4-bathroom residence nestled on a premium corner lot ...	5 beds \| 4 baths \| 3,557 sq.ft.	$1,375,000	Airbnb cash on cash: 1.1% Traditional cash on cash: 1.24% Airbnb Rental Income: $5841 Traditional Rental Income: $4855 Airbnb ROI: 1.1% Traditional ROI: 1.24%
11222 RAPALLO LANE Windermere, FL 7/1 completed with 2025 aesthetics inside and outside ---- RENOVATED KITCHEN, BATHS, Li...	4 beds \| 2 baths \| 2,145 sq.ft.	$680,000	Airbnb cash on cash: 1.95% Traditional cash on cash: 2.8% Airbnb Rental Income: $3311 Traditional Rental Income: $3113 Airbnb ROI: 1.95% Traditional ROI: 2.8%
12264 MONTALCINO CIRCLE Windermere, FL Lakefront, Luxurious, Fully Furnished Home with Private Pool in Windermere. A True Para...	4 beds \| 7 baths \| 7,872 sq.ft.	$5,890,000	Airbnb cash on cash: -2.09% Traditional cash on cash: -1.06% Airbnb Rental Income: $3311 Traditional Rental Income: $8215 Airbnb ROI: -2.09% Traditional ROI: -1.06%
5138 FAIRWAY OAKS DRIVE Windermere, FL Under contract-accepting backup offers. A captivating golf course location sets the stage ...	4 beds \| 5 baths \| 4,330 sq.ft.	$2,900,000	Airbnb cash on cash: -1.15% Traditional cash on cash: 0.21% Airbnb Rental Income: $3311 Traditional Rental Income: $6220 Airbnb ROI: -1.15% Traditional ROI: 0.21%
9905 Lanai View Ct Windermere, FL Welcome to a home that isn't just designed-it's curated. Tucked behind the gates of one...	5 beds \| 8 baths \| 7,621 sq.ft.	$2,650,000	Airbnb cash on cash: 0% Traditional cash on cash: 1.08% Airbnb Rental Income: $5841 Traditional Rental Income: $7321 Airbnb ROI: 0% Traditional ROI: 1.08%
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: 0.59% Airbnb Rental Income: $5841 Traditional Rental Income: $6288 Airbnb ROI: 0.04% Traditional ROI: 0.59%

Real Estate investment in Windermere, FL

There are 146 properties for sale in the city of Windermere . The median list price in Windermere is $895,000 and the average price per square foot is $285. In September 2025, the average monthly cash on cash return in Windermere is 2.00%. The average monthly rental income in Windermere is $3,205.

Windermere, FL Real Estate Investing: FAQs for Buyers, Sellers and Investors

There are 146 investment properties available for sale in Windermere.

In 2025, the best neighborhood to buy investment property is Windermere.

The ROI for Long-Term is higher than the Short-Term in Windermere with average rental income of $3,205.

Your search for investment property begins and ends here

Investment Property for Sale in Windermere, FL

5141 AUTUMN RIDGE LANE

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%

10624 REAMS ROAD

Windermere, FL

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

$520,000

Airbnb cash on cash: 2.87%

Traditional cash on cash: 3.28%

Airbnb Rental Income: $3311

Traditional Rental Income: $2769

Airbnb ROI: 2.87%

Traditional ROI: 3.28%

7462 BENTONSHIRE AVE

Windermere, FL

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

$378,000

Airbnb cash on cash: 2.36%

Traditional cash on cash: 3.23%

Airbnb Rental Income: $2597

Traditional Rental Income: $2285

Airbnb ROI: 2.36%

Traditional ROI: 3.23%

8752 LOOKOUT POINTE DRIVE

Windermere, FL

4 beds | 4 baths | 3,270 sq.ft.

$929,000

Airbnb cash on cash: 0.66%

Traditional cash on cash: 3.61%

Airbnb Rental Income: $3311

Traditional Rental Income: $5123

Airbnb ROI: 0.66%

Traditional ROI: 3.61%

9447 WESTOVER CLUB CIRCLE

Windermere, FL

4 beds | 3 baths | 2,568 sq.ft.

$789,000

Airbnb cash on cash: 1.57%

Traditional cash on cash: 2.77%

Airbnb Rental Income: $3311

Traditional Rental Income: $3452

Airbnb ROI: 1.57%

Traditional ROI: 2.77%

9485 WOODBREEZE BOULEVARD

Windermere, FL

3 beds | 2 baths | 1,723 sq.ft.

$589,900

Airbnb cash on cash: 1.16%

Traditional cash on cash: 2.36%

Airbnb Rental Income: $2597

Traditional Rental Income: $2639

Airbnb ROI: 1.16%

Traditional ROI: 2.36%

8582 POWDER RIDGE TRAIL

Windermere, FL

4 beds | 4 baths | 2,297 sq.ft.

$695,000

Airbnb cash on cash: 1.51%

Traditional cash on cash: 2.29%

Airbnb Rental Income: $3311

Traditional Rental Income: $3071

Airbnb ROI: 1.51%

Traditional ROI: 2.29%

6734 BRIDGEWATER VILLAGE ROAD

Windermere, FL

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%