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
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%
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.	$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%
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.	$660,000	Airbnb cash on cash: 0.31% Traditional cash on cash: 1.8% Airbnb Rental Income: $2597 Traditional Rental Income: $2894 Airbnb ROI: 0.31% Traditional ROI: 1.8%
11660 DELWICK DRIVE Windermere, FL This season, discover a home where gratitude meets grandeur in the heart of Windermereâs...	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%
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 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%
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%
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%
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.	$915,000	Airbnb cash on cash: 2.82% Traditional cash on cash: 1.6% Airbnb Rental Income: $5841 Traditional Rental Income: $3632 Airbnb ROI: 2.82% Traditional ROI: 1.6%
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.	$911,400	Airbnb cash on cash: 3.16% Traditional cash on cash: 4.71% Airbnb Rental Income: $5841 Traditional Rental Income: $5991 Airbnb ROI: 3.16% Traditional ROI: 4.71%
11025 LEDGEMENT LANE Windermere, FL Under contract-accepting backup offers. *The seller is offering $10,000 in seller concessi...	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%
6102 S HAMPSHIRE COURT Windermere, FL PRICE REDUCED $150K This elegant single-story Rick Watson home, located at 6102 S Hampsh...	4 beds \| 6 baths \| 4,810 sq.ft.	$2,499,000	Airbnb cash on cash: -0.75% Traditional cash on cash: 2.09% Airbnb Rental Income: $3311 Traditional Rental Income: $9137 Airbnb ROI: -0.75% Traditional ROI: 2.09%
9792 WILD OAK DRIVE Windermere, FL Seller says SELL! Listed $20,000 BELOW APPRAISED value!!! Discover this exquisite 3-bedroo...	3 beds \| 4 baths \| 3,102 sq.ft.	$900,000	Airbnb cash on cash: 0.36% Traditional cash on cash: 3.78% Airbnb Rental Income: $2597 Traditional Rental Income: $4834 Airbnb ROI: 0.36% Traditional ROI: 3.78%
3413 LILAS COURT Windermere, FL Welcome to 3413 Lilas Court, a stunning residence located in the well renowned community o...	4 beds \| 5 baths \| 5,084 sq.ft.	$2,300,000	Airbnb cash on cash: -1.42% Traditional cash on cash: 0.89% Airbnb Rental Income: $3311 Traditional Rental Income: $7512 Airbnb ROI: -1.42% Traditional ROI: 0.89%
4818 BREEZY PALMS COURT Windermere, FL MOVE IN FOR THE HOLIDAYS! Donât miss this Silver Woods jewel box in a super central loca...	3 beds \| 2 baths \| 1,492 sq.ft.	$535,000	Airbnb cash on cash: 2.11% Traditional cash on cash: 2.52% Airbnb Rental Income: $2597 Traditional Rental Income: $2181 Airbnb ROI: 2.11% Traditional ROI: 2.52%
11507 CENTER LAKE DRIVE Windermere, FL 2025 PARADE OF HOMES GRAND AWARD WINNING BUILDER \| 2017 PARADE OF HOMES WINNER \|CUSTOM CRA...	4 beds \| 4 baths \| 3,766 sq.ft.	$989,500	Airbnb cash on cash: 1.02% Traditional cash on cash: 2.84% Airbnb Rental Income: $3311 Traditional Rental Income: $4243 Airbnb ROI: 1.02% Traditional ROI: 2.84%
14347 CREST PALM AVENUE Windermere, FL One or more photo(s) has been virtually staged. Under Construction. Sample Image Experienc...	4 beds \| 3 baths \| 3,100 sq.ft.	$1,079,004	Airbnb cash on cash: 1.04% Traditional cash on cash: 1.67% Airbnb Rental Income: $3311 Traditional Rental Income: $3202 Airbnb ROI: 1.04% Traditional ROI: 1.67%

Your search for investment property begins and ends here

Single Family Homes for Sale in Windermere, FL

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%

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.

$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%

299 W 4TH AVENUE

Windermere, FL

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

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%