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 113 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
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%
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%
9485 WOODBREEZE BOULEVARD Windermere, FL Under contract-accepting backup offers. Located in the highly sought-after Silver Woods co...	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.	$675,000	Airbnb cash on cash: 0.28% Traditional cash on cash: 1.74% Airbnb Rental Income: $2597 Traditional Rental Income: $2894 Airbnb ROI: 0.28% Traditional ROI: 1.74%
11660 DELWICK DRIVE Windermere, FL Golden Season, Spelltacular Living in The Reserve at Belmere! A rare treat awaits behin...	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%
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%
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.	$3,900,000	Airbnb cash on cash: -0.82% Traditional cash on cash: -0.36% Airbnb Rental Income: $3311 Traditional Rental Income: $4224 Airbnb ROI: -0.82% Traditional ROI: -0.36%
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.	$1,750,000	Airbnb cash on cash: -0.51% Traditional cash on cash: 2.37% Airbnb Rental Income: $3311 Traditional Rental Income: $7244 Airbnb ROI: -0.51% Traditional ROI: 2.37%
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.	$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%
9631 HOLLYGLEN PLACE Windermere, FL Under contract-accepting backup offers. Nestled in the sought-after community of Windermer...	4 beds \| 3 baths \| 2,854 sq.ft.	$765,000	Airbnb cash on cash: 0.92% Traditional cash on cash: 2.34% Airbnb Rental Income: $3311 Traditional Rental Income: $3586 Airbnb ROI: 0.92% Traditional ROI: 2.34%
2540 HEMPEL COVE CT Windermere, FL Under contract-accepting backup offers. Stunning Renovation on 1 Acre in Lake Down Cove. L...	5 beds \| 3 baths \| 3,356 sq.ft.	$1,275,000	Airbnb cash on cash: 1.47% Traditional cash on cash: 0.94% Airbnb Rental Income: $5841 Traditional Rental Income: $4045 Airbnb ROI: 1.47% Traditional ROI: 0.94%
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 An exceptional estate, masterfully renovated and transformed into a reimagined showplace: ...	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%
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%
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%
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%
1927 WATERMERE LANE Windermere, FL Under contract-accepting backup offers. Luxury living in one of Central Florida's most sou...	4 beds \| 4 baths \| 3,053 sq.ft.	$1,146,000	Airbnb cash on cash: 0.04% Traditional cash on cash: 1.68% Airbnb Rental Income: $3311 Traditional Rental Income: $4315 Airbnb ROI: 0.04% Traditional ROI: 1.68%
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 Under contract-accepting backup offers. One or more photo(s) has been virtually staged. Th...	5 beds \| 4 baths \| 3,720 sq.ft.	$769,000	Airbnb cash on cash: 4.01% Traditional cash on cash: 5.31% Airbnb Rental Income: $5841 Traditional Rental Income: $5610 Airbnb ROI: 4.01% Traditional ROI: 5.31%
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.	$2,399,000	Airbnb cash on cash: 0.49% Traditional cash on cash: 1.3% Airbnb Rental Income: $5841 Traditional Rental Income: $6481 Airbnb ROI: 0.49% Traditional ROI: 1.3%
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%
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%
11923 LAKE BUTLER BOULEVARD Windermere, FL Nestled on one of Windermereâs most desirable streets, this charming home offers a rare ...	3 beds \| 2 baths \| 2,238 sq.ft.	$1,630,000	Airbnb cash on cash: -0.54% Traditional cash on cash: -0.03% Airbnb Rental Income: $2597 Traditional Rental Income: $2746 Airbnb ROI: -0.54% Traditional ROI: -0.03%
9106 PANZANI PLACE Windermere, FL Discover this beautiful 5-bedroom, 4-bathroom residence nestled inside the exclusive gated...	5 beds \| 4 baths \| 3,610 sq.ft.	$950,000	Airbnb cash on cash: 2.68% Traditional cash on cash: 1.5% Airbnb Rental Income: $5841 Traditional Rental Income: $3632 Airbnb ROI: 2.68% Traditional ROI: 1.5%
4926 INDIAN DEER ROAD Windermere, FL WOW! Check out this stunningly renovated Summerport multi-generational home! This expansiv...	5 beds \| 5 baths \| 3,849 sq.ft.	$930,000	Airbnb cash on cash: 3.08% Traditional cash on cash: 4.59% Airbnb Rental Income: $5841 Traditional Rental Income: $5991 Airbnb ROI: 3.08% Traditional ROI: 4.59%
11025 LEDGEMENT LANE Windermere, FL The seller is offering $10,000 in seller concessions. Welcome to 11025 Ledgement Lane, a...	4 beds \| 4 baths \| 3,024 sq.ft.	$949,000	Airbnb cash on cash: 1.06% Traditional cash on cash: 2.65% Airbnb Rental Income: $3311 Traditional Rental Income: $3981 Airbnb ROI: 1.06% Traditional ROI: 2.65%

Your search for investment property begins and ends here

Single Family Homes 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%

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.

$1,300,000

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%

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%

9485 WOODBREEZE BOULEVARD

Windermere, FL

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

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

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

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%