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
12307 LANGSTAFF DRIVE Windermere, FL One or more photo(s) has been virtually staged. Live Where the Magic Happens! This beautif...	3 beds \| 3 baths \| 1,520 sq.ft.	$369,999	Airbnb cash on cash: 2.36% Traditional cash on cash: 3.4% Airbnb Rental Income: $2597 Traditional Rental Income: $2338 Airbnb ROI: 2.36% Traditional ROI: 3.4%
12654 CRAGSIDE LANE Windermere, FL Under contract-accepting backup offers. Welcome to a truly rare opportunity in Windermere ...	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 One or more photo(s) has been virtually staged. Newly added virtually staged images to hel...	4 beds \| 4 baths \| 2,658 sq.ft.	$1,200,000	Airbnb cash on cash: -0.12% Traditional cash on cash: 1.42% Airbnb Rental Income: $3311 Traditional Rental Income: $4288 Airbnb ROI: -0.12% Traditional ROI: 1.42%
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.	$359,000	Airbnb cash on cash: 2.53% Traditional cash on cash: 3.45% Airbnb Rental Income: $2597 Traditional Rental Income: $2285 Airbnb ROI: 2.53% Traditional ROI: 3.45%
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.	$879,000	Airbnb cash on cash: 0.76% Traditional cash on cash: 3.87% Airbnb Rental Income: $3311 Traditional Rental Income: $5123 Airbnb ROI: 0.76% Traditional ROI: 3.87%
6130 GROSVENOR SHORE DRIVE Windermere, FL Remarkable Waterview Estate in Keeneâs Pointe! Heated Saltwater Pool, Main-Floor Living,...	4 beds \| 5 baths \| 4,676 sq.ft.	$3,500,000	Airbnb cash on cash: -1.04% Traditional cash on cash: 0.49% Airbnb Rental Income: $3311 Traditional Rental Income: $7548 Airbnb ROI: -1.04% Traditional ROI: 0.49%
6615 HELMSLEY CIRCLE Windermere, FL Beautifully remodeled and impeccably maintained, this spacious 3,390 sq. ft. two-story hom...	5 beds \| 4 baths \| 3,390 sq.ft.	$799,900	Airbnb cash on cash: 4.9% Traditional cash on cash: 4.43% Airbnb Rental Income: $5841 Traditional Rental Income: $4329 Airbnb ROI: 4.9% Traditional ROI: 4.43%
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: 1.61% Traditional cash on cash: 2.41% Airbnb Rental Income: $3311 Traditional Rental Income: $3071 Airbnb ROI: 1.61% Traditional ROI: 2.41%
299 W 4TH AVENUE Windermere, FL This traditional farmhouse blends Old Florida charm with everyday comfort â a rare oppor...	4 beds \| 3 baths \| 2,410 sq.ft.	$895,000	Airbnb cash on cash: 0.8% Traditional cash on cash: 1.67% Airbnb Rental Income: $3311 Traditional Rental Income: $3292 Airbnb ROI: 0.8% Traditional ROI: 1.67%
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%
6734 BRIDGEWATER VILLAGE ROAD Windermere, FL LUXURY WINDERMERE HOME ON OVERSIZED CONSERVATION LOT - Welcome to Windermere living at its...	3 beds \| 3 baths \| 3,094 sq.ft.	$649,000	Airbnb cash on cash: 0.33% Traditional cash on cash: 1.85% Airbnb Rental Income: $2597 Traditional Rental Income: $2894 Airbnb ROI: 0.33% Traditional ROI: 1.85%
11660 DELWICK DRIVE Windermere, FL Under contract-accepting backup offers. This season, discover a home where gratitude meets...	4 beds \| 5 baths \| 3,051 sq.ft.	$795,000	Airbnb cash on cash: 0.56% Traditional cash on cash: 5.48% Airbnb Rental Income: $3311 Traditional Rental Income: $6215 Airbnb ROI: 0.56% Traditional ROI: 5.48%
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%
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: -1.68% Traditional cash on cash: -1.01% Airbnb Rental Income: $2597 Traditional Rental Income: $4324 Airbnb ROI: -1.68% Traditional ROI: -1.01%
13833 ANCILLA BOULEVARD Windermere, FL Under contract-accepting backup offers. Welcome to this ONE STORY TOWNHOME on a CORNER LOT...	2 beds \| 2 baths \| 1,155 sq.ft.	$355,000	Airbnb cash on cash: 8.78% Traditional cash on cash: 2.84% Airbnb Rental Income: $4898 Traditional Rental Income: $1913 Airbnb ROI: 8.78% Traditional ROI: 2.84%
7628 BILLINGHAM STREET Windermere, FL Under contract-accepting backup offers. SUPER DEAL. Discover this beautiful townhome locat...	3 beds \| 3 baths \| 1,480 sq.ft.	$398,000	Airbnb cash on cash: 2.8% Traditional cash on cash: 3.68% Airbnb Rental Income: $2597 Traditional Rental Income: $2302 Airbnb ROI: 2.8% Traditional ROI: 3.68%
6533 CARTMEL LANE Windermere, FL Tucked away in the prestigious guard-gated community of The Reserve at Lake Butler Sound, ...	4 beds \| 4 baths \| 3,751 sq.ft.	$1,398,888	Airbnb cash on cash: -0.72% Traditional cash on cash: 1.14% Airbnb Rental Income: $3311 Traditional Rental Income: $4987 Airbnb ROI: -0.72% Traditional ROI: 1.14%
2844 MARQUESAS COURT Windermere, FL Welcome to your private sanctuary, where every sunrise and sunset dances over the shimmeri...	4 beds \| 3 baths \| 5,365 sq.ft.	$3,700,000	Airbnb cash on cash: -0.81% Traditional cash on cash: -0.33% Airbnb Rental Income: $3311 Traditional Rental Income: $4224 Airbnb ROI: -0.81% Traditional ROI: -0.33%
11922 ANGLE POND AVENUE Windermere, FL One or more photo(s) has been virtually staged. Disney at your doorstep and vibes for days...	4 beds \| 4 baths \| 3,382 sq.ft.	$775,000	Airbnb cash on cash: 1.26% Traditional cash on cash: 3.5% Airbnb Rental Income: $3311 Traditional Rental Income: $4187 Airbnb ROI: 1.26% Traditional ROI: 3.5%
3328 WAX BERRY COURT Windermere, FL One or more photo(s) has been virtually staged. A rare find in the heart of Downtown Winde...	4 beds \| 4 baths \| 2,636 sq.ft.	$975,000	Airbnb cash on cash: 0.6% Traditional cash on cash: 3.03% Airbnb Rental Income: $3311 Traditional Rental Income: $4777 Airbnb ROI: 0.6% Traditional ROI: 3.03%
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.	$765,000	Airbnb cash on cash: 1.09% Traditional cash on cash: 3.78% Airbnb Rental Income: $3311 Traditional Rental Income: $4489 Airbnb ROI: 1.09% Traditional ROI: 3.78%
3426 COCARD COURT Windermere, FL Under contract-accepting backup offers. An exceptional estate, masterfully renovated and t...	4 beds \| 5 baths \| 7,222 sq.ft.	$3,450,000	Airbnb cash on cash: -1.1% Traditional cash on cash: -0.15% Airbnb Rental Income: $3311 Traditional Rental Income: $5600 Airbnb ROI: -1.1% Traditional ROI: -0.15%
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.	$599,000	Airbnb cash on cash: 1.6% Traditional cash on cash: 3.05% Airbnb Rental Income: $3311 Traditional Rental Income: $3381 Airbnb ROI: 1.6% Traditional ROI: 3.05%
6018 Tarawood Dr Windermere, FL 6018 Tarawood Dr, Windermere, FL 32819 \| Single Family Residential	6 beds \| 6 baths \| 5,825 sq.ft.	$2,850,000	Airbnb cash on cash: -0.19% Traditional cash on cash: 0.55% Airbnb Rental Income: $5841 Traditional Rental Income: $6622 Airbnb ROI: -0.19% Traditional ROI: 0.55%
8734 Crestgate Cir Windermere, FL 8734 Crestgate Cir, Windermere, FL 32819 \| Single Family Residential	4 beds \| 4 baths \| 3,998 sq.ft.	$1,720,000	Airbnb cash on cash: -0.45% Traditional cash on cash: 0.18% Airbnb Rental Income: $3311 Traditional Rental Income: $3568 Airbnb ROI: -0.45% Traditional ROI: 0.18%
12001 LAKE BUTLER BOULEVARD 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: -0.66% Traditional cash on cash: 0.2% Airbnb Rental Income: $2597 Traditional Rental Income: $3399 Airbnb ROI: -0.66% Traditional ROI: 0.2%
11818 Water Run Alley Windermere, FL SELLER OFFERS up to $3,000 toward buyer's closing costs. NEW exterior paint completed by H...	3 beds \| 3 baths \| 1,588 sq.ft.	$410,000	Airbnb cash on cash: 2.42% Traditional cash on cash: 4.05% Airbnb Rental Income: $2597 Traditional Rental Income: $2601 Airbnb ROI: 2.42% Traditional ROI: 4.05%
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%
12540 PARK AVENUE Windermere, FL Offering a prime lakefront location along the shores of Lake Butler in the esteemed gated ...	5 beds \| 6 baths \| 7,183 sq.ft.	$4,650,000	Airbnb cash on cash: -1.02% Traditional cash on cash: -0.33% Airbnb Rental Income: $5841 Traditional Rental Income: $7657 Airbnb ROI: -1.02% Traditional ROI: -0.33%
1803 GLENBAY COURT Windermere, FL Welcome to The Reserve at Belmere. Experience refined living in this exclusive guard-gated...	4 beds \| 3 baths \| 3,040 sq.ft.	$875,000	Airbnb cash on cash: 0.53% Traditional cash on cash: 2.17% Airbnb Rental Income: $3311 Traditional Rental Income: $3900 Airbnb ROI: 0.53% Traditional ROI: 2.17%
13106 ORANGE ISLE DRIVE Windermere, FL Explore the WINTERSET model from Ryan Homes of the Sanctuary at Lakes of Windermere, a cor...	5 beds \| 5 baths \| 3,312 sq.ft.	$899,000	Airbnb cash on cash: 3.04% Traditional cash on cash: 4.42% Airbnb Rental Income: $5841 Traditional Rental Income: $5839 Airbnb ROI: 3.04% Traditional ROI: 4.42%
11019 KENTMERE COURT Windermere, FL Under contract-accepting backup offers. Meticulously upgraded and thoughtfully designed, t...	4 beds \| 4 baths \| 3,813 sq.ft.	$1,500,000	Airbnb cash on cash: -0.26% Traditional cash on cash: 0.86% Airbnb Rental Income: $3311 Traditional Rental Income: $4124 Airbnb ROI: -0.26% Traditional ROI: 0.86%
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%
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.	$2,375,000	Airbnb cash on cash: 0.51% Traditional cash on cash: 1.33% Airbnb Rental Income: $5841 Traditional Rental Income: $6481 Airbnb ROI: 0.51% Traditional ROI: 1.33%
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.	$375,000	Airbnb cash on cash: 1.4% Traditional cash on cash: 4.85% Airbnb Rental Income: $2597 Traditional Rental Income: $3189 Airbnb ROI: 1.4% Traditional ROI: 4.85%
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.	$1,080,000	Airbnb cash on cash: 0.44% Traditional cash on cash: 3.24% Airbnb Rental Income: $3311 Traditional Rental Income: $5387 Airbnb ROI: 0.44% Traditional ROI: 3.24%
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.	$1,299,000	Airbnb cash on cash: 1.22% Traditional cash on cash: 1.37% Airbnb Rental Income: $5841 Traditional Rental Income: $4855 Airbnb ROI: 1.22% Traditional ROI: 1.37%
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.	$5,860,000	Airbnb cash on cash: -2.1% Traditional cash on cash: -1.06% Airbnb Rental Income: $3311 Traditional Rental Income: $8215 Airbnb ROI: -2.1% Traditional ROI: -1.06%
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 162 properties for sale in the city of Windermere . The median list price in Windermere is $949,500 and the average price per square foot is $277. In December 2025, the average monthly cash on cash return in Windermere is 2.00%. The average monthly rental income in Windermere is $3,279.

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

There are 162 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 $3,279.

Your search for investment property begins and ends here

Investment Property for Sale in Windermere, FL

12307 LANGSTAFF DRIVE

Windermere, FL

3 beds | 3 baths | 1,520 sq.ft.

$369,999

Airbnb cash on cash: 2.36%

Traditional cash on cash: 3.4%

Airbnb Rental Income: $2597

Traditional Rental Income: $2338

Airbnb ROI: 2.36%

Traditional ROI: 3.4%

12654 CRAGSIDE LANE

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%

11325 FENIMORE COURT

Windermere, FL

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

$1,200,000

Airbnb cash on cash: -0.12%

Traditional cash on cash: 1.42%

Airbnb Rental Income: $3311

Traditional Rental Income: $4288

Airbnb ROI: -0.12%

Traditional ROI: 1.42%

7462 BENTONSHIRE AVE

Windermere, FL

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

$359,000

Airbnb cash on cash: 2.53%

Traditional cash on cash: 3.45%

Airbnb Rental Income: $2597

Traditional Rental Income: $2285

Airbnb ROI: 2.53%

Traditional ROI: 3.45%

8752 LOOKOUT POINTE DRIVE

Windermere, FL

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

$879,000

Airbnb cash on cash: 0.76%

Traditional cash on cash: 3.87%

Airbnb Rental Income: $3311

Traditional Rental Income: $5123

Airbnb ROI: 0.76%

Traditional ROI: 3.87%

6130 GROSVENOR SHORE DRIVE

Windermere, FL

4 beds | 5 baths | 4,676 sq.ft.

$3,500,000

Airbnb cash on cash: -1.04%

Traditional cash on cash: 0.49%

Airbnb Rental Income: $3311

Traditional Rental Income: $7548

Airbnb ROI: -1.04%

Traditional ROI: 0.49%

6615 HELMSLEY CIRCLE

Windermere, FL

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

$799,900

Airbnb cash on cash: 4.9%

Traditional cash on cash: 4.43%

Airbnb Rental Income: $5841

Traditional Rental Income: $4329

Airbnb ROI: 4.9%

Traditional ROI: 4.43%

8582 POWDER RIDGE TRAIL

Windermere, FL

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

$670,000

Airbnb cash on cash: 1.61%

Traditional cash on cash: 2.41%

Airbnb Rental Income: $3311

Traditional Rental Income: $3071

Airbnb ROI: 1.61%