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.

Woodlawn Investment Property for Sale in Windermere, FL

Search for Woodlawn Investment Property for Sale in Windermere, Florida. Browse all of Mashvisor’s Woodlawn Investment Property listings and other investment property types including Single Family Homes, Multi Family Homes, Condos, Townhouses and Other Homes.

Showing 274 Woodlawn Investment Property 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
10624 Reams Rd Windermere, FL Welcome to this beautiful 4-bedroom, 2.5-bath home in the highly desirable Windermere Trai...	4 beds \| 2 baths \| 2,092 sq.ft.	$499,000	Airbnb cash on cash: 2.98% Traditional cash on cash: 3.4% Airbnb Rental Income: $3311 Traditional Rental Income: $2769 Airbnb ROI: 2.98% Traditional ROI: 3.4%
11325 Fenimore Ct Windermere, FL One or more photo(s) has been virtually staged. Newly added virtually staged images to hel...	4 beds \| 3 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%
5463 GEMGOLD COURT Windermere, FL Under contract-accepting backup offers. Welcome home to this beautiful residence situated ...	4 beds \| 3 baths \| 2,246 sq.ft.	$599,000	Airbnb cash on cash: 2.61% Traditional cash on cash: 3.41% Airbnb Rental Income: $3311 Traditional Rental Income: $3018 Airbnb ROI: 2.61% Traditional ROI: 3.41%
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%
6442 Golden Dewdrop Trl Windermere, FL Come see this beautiful place. This immaculate home features include over 2,100 square fee...	3 beds \| 2 baths \| 2,139 sq.ft.	$585,000	Airbnb cash on cash: 0.89% Traditional cash on cash: 2.87% Airbnb Rental Income: $2597 Traditional Rental Income: $3055 Airbnb ROI: 0.89% Traditional ROI: 2.87%
6117 Louise Cove Dr Windermere, FL Nestled along the shores of Lake Louise within Isleworth West, this exceptional two-story ...	4 beds \| 4 baths \| 5,752 sq.ft.	$5,250,000	Airbnb cash on cash: -1.71% Traditional cash on cash: -0.8% Airbnb Rental Income: $3311 Traditional Rental Income: $7149 Airbnb ROI: -1.71% Traditional ROI: -0.8%
6615 Helmsley Cir Windermere, FL Beautifully remodeled and impeccably maintained, this spacious 3,390 sq. ft. two-story hom...	5 beds \| 3 baths \| 3,390 sq.ft.	$769,900	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 Trl Windermere, FL AN IRRESISTIBLE INVESTMENT OPPORTUNITY â OR YOUR FIRST HOME! Welcome to this stunning K...	4 beds \| 3 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%
7545 Lake Albert Dr Windermere, FL Welcome to 7545 Lake Albert Drive. Where timeless architecture meets modern luxury. Nestl...	4 beds \| 3 baths \| 3,425 sq.ft.	$1,075,000	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%
7482 BENTONSHIRE AVENUE Windermere, FL Under contract-accepting backup offers. Discover this beautiful corner-unit townhome locat...	3 beds \| 3 baths \| 1,428 sq.ft.	$399,900	Airbnb cash on cash: 2.61% Traditional cash on cash: 3.54% Airbnb Rental Income: $2597 Traditional Rental Income: $2324 Airbnb ROI: 2.61% Traditional ROI: 3.54%
7777 Moser Ave Windermere, FL BACK ON MARKET DUE TO BUYER DEFAULT - This upscale, meticulously maintained end-unit townh...	3 beds \| 2 baths \| 1,670 sq.ft.	$399,000	Airbnb cash on cash: 1.52% Traditional cash on cash: 2.74% Airbnb Rental Income: $2597 Traditional Rental Income: $2434 Airbnb ROI: 1.52% Traditional ROI: 2.74%
6734 Bridgewater Village Rd Windermere, FL LUXURY WINDERMERE HOME ON OVERSIZED CONSERVATION LOT - Welcome to Windermere living at its...	3 beds \| 2 baths \| 3,094 sq.ft.	$645,000	Airbnb cash on cash: 0.34% Traditional cash on cash: 1.87% Airbnb Rental Income: $2597 Traditional Rental Income: $2894 Airbnb ROI: 0.34% Traditional ROI: 1.87%
106 Butler St Windermere, FL Located within the coveted town limits of Windermere, this completely updated four-bedroom...	4 beds \| 2 baths \| 2,058 sq.ft.	$1,100,000	Airbnb cash on cash: 0.59% Traditional cash on cash: 1.01% Airbnb Rental Income: $3311 Traditional Rental Income: $3002 Airbnb ROI: 0.59% Traditional ROI: 1.01%
8632 Abbotsbury Dr Windermere, FL **This house comes with a REDUCED RATE through the seller's preferred lender. This is a le...	4 beds \| 3 baths \| 2,720 sq.ft.	$609,999	Airbnb cash on cash: 1.59% Traditional cash on cash: 3.16% Airbnb Rental Income: $3311 Traditional Rental Income: $3479 Airbnb ROI: 1.59% Traditional ROI: 3.16%
4812 Alexandra Garden Ct Windermere, FL Luxury villa living within the exclusive Gardens of Isleworth, part of the Isleworth Golf ...	3 beds \| 3 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 Pl Windermere, FL Stunning golf and lake views and beautifully updated grounds are hallmarks of this elegant...	3 beds \| 3 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%
11922 Angle Pond Ave Windermere, FL One or more photo(s) has been virtually staged. Welcome to this beautifully maintained fou...	4 beds \| 3 baths \| 3,382 sq.ft.	$760,000	Airbnb cash on cash: 1.27% Traditional cash on cash: 3.53% Airbnb Rental Income: $3311 Traditional Rental Income: $4187 Airbnb ROI: 1.27% Traditional ROI: 3.53%
3328 Wax Berry Ct Windermere, FL One or more photo(s) has been virtually staged. Price improvement of $25,000! A rare...	4 beds \| 4 baths \| 2,636 sq.ft.	$925,000	Airbnb cash on cash: 0.64% Traditional cash on cash: 3.13% Airbnb Rental Income: $3311 Traditional Rental Income: $4777 Airbnb ROI: 0.64% Traditional ROI: 3.13%
6638 Bridgewater Village Rd Windermere, FL Welcome to Vineyards Horizon West, this stunning 4-bedroom, 2.5-bath home offers about 3,0...	4 beds \| 2 baths \| 2,908 sq.ft.	$664,900	Airbnb cash on cash: 1.29% Traditional cash on cash: 2.16% Airbnb Rental Income: $3311 Traditional Rental Income: $3114 Airbnb ROI: 1.29% Traditional ROI: 2.16%
11520 Via Lucerna Cir Windermere, FL Beautifully Freshly Painted Home in Windermereâs Belmere Village Welcome to this ligh...	4 beds \| 2 baths \| 2,505 sq.ft.	$590,000	Airbnb cash on cash: 1.64% Traditional cash on cash: 3.11% Airbnb Rental Income: $3311 Traditional Rental Income: $3381 Airbnb ROI: 1.64% Traditional ROI: 3.11%
12001 Lake Butler Blvd 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%
13048 Lake Roper Ct Windermere, FL Auction Property. Waterfront home featuring 4 bedrooms, 3.5 baths, and a gracious amount ...	5 beds \| 3 baths \| 4,130 sq.ft.	$1,950,000	Airbnb cash on cash: 0.67% Traditional cash on cash: 0.45% Airbnb Rental Income: $5841 Traditional Rental Income: $4282 Airbnb ROI: 0.67% Traditional ROI: 0.45%
13285 Gorgona Isle Dr Windermere, FL One or more photo(s) has been virtually staged. Welcome to this meticulously maintained 2 ...	3 beds \| 2 baths \| 1,547 sq.ft.	$410,000	Airbnb cash on cash: 1.7% Traditional cash on cash: 2.57% Airbnb Rental Income: $2597 Traditional Rental Income: $2315 Airbnb ROI: 1.7% Traditional ROI: 2.57%
11818 WATER RUN ALLEY Windermere, FL Under contract-accepting backup offers. SELLER OFFERS up to $3,000 toward buyer's closing ...	3 beds \| 3 baths \| 1,588 sq.ft.	$410,000	Airbnb cash on cash: 1.53% Traditional cash on cash: 3.16% Airbnb Rental Income: $2597 Traditional Rental Income: $2601 Airbnb ROI: 1.53% Traditional ROI: 3.16%
3443 Wild Myrtle Ct 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%
14261 CREST PALM AVENUE Windermere, FL Under contract-accepting backup offers. One or more photo(s) has been virtually staged. Th...	4 beds \| 4 baths \| 3,199 sq.ft.	$1,130,735	Airbnb cash on cash: 0.95% Traditional cash on cash: 2.45% Airbnb Rental Income: $3311 Traditional Rental Income: $4148 Airbnb ROI: 0.95% Traditional ROI: 2.45%
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 Ave Windermere, FL Offering a prime lakefront location along the shores of Lake Butler in the esteemed gated ...	5 beds \| 5 baths \| 7,740 sq.ft.	$4,599,000	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 Under contract-accepting backup offers. Welcome to The Reserve at Belmere. Experience refi...	4 beds \| 3 baths \| 3,040 sq.ft.	$825,000	Airbnb cash on cash: 0.63% Traditional cash on cash: 2.36% Airbnb Rental Income: $3311 Traditional Rental Income: $3900 Airbnb ROI: 0.63% Traditional ROI: 2.36%
12936 Droxford Rd Windermere, FL Lakes of Windermere STUNNER! This Ashton Woods Kensington model comes with an amazing bonu...	5 beds \| 3 baths \| 2,960 sq.ft.	$649,000	Airbnb cash on cash: 4.49% Traditional cash on cash: 3.2% Airbnb Rental Income: $5841 Traditional Rental Income: $3839 Airbnb ROI: 4.49% Traditional ROI: 3.2%
6109 Orta Ct Windermere, FL Within the gates of the Waterstone community, this exceptional lakefront estate offers app...	5 beds \| 5 baths \| 5,895 sq.ft.	$4,495,000	Airbnb cash on cash: -1.47% Traditional cash on cash: -0.81% Airbnb Rental Income: $5841 Traditional Rental Income: $7407 Airbnb ROI: -1.47% Traditional ROI: -0.81%
13106 Orange Isle Dr Windermere, FL Explore the WINTERSET model from Ryan Homes of the Sanctuary at Lakes of Windermere, a cor...	5 beds \| 4 baths \| 3,312 sq.ft.	$830,000	Airbnb cash on cash: 3.17% Traditional cash on cash: 4.6% Airbnb Rental Income: $5841 Traditional Rental Income: $5839 Airbnb ROI: 3.17% Traditional ROI: 4.6%
6443 Cartmel Ln Windermere, FL Exquisitely appointed home being sold fully furnished. Nestled within the highly coveted R...	4 beds \| 4 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 Ave Windermere, FL Under contract-accepting backup offers. Step inside this beautifully updated home where cl...	5 beds \| 4 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 Under contract-accepting backup offers. *3D Tour on Virtual Tour Link 1* This immacula...	3 beds \| 3 baths \| 1,786 sq.ft.	$365,000	Airbnb cash on cash: 1.46% Traditional cash on cash: 5.01% Airbnb Rental Income: $2597 Traditional Rental Income: $3189 Airbnb ROI: 1.46% Traditional ROI: 5.01%
11618 Vinci Dr Windermere, FL Behind the gates of Keene's Pointe, on the pristine shores of Lake Burden, an extraordinar...	5 beds \| 5 baths \| 6,188 sq.ft.	$4,950,000	Airbnb cash on cash: -0.88% Traditional cash on cash: -0.3% Airbnb Rental Income: $5841 Traditional Rental Income: $7351 Airbnb ROI: -0.88% Traditional ROI: -0.3%
2107 Westover Reserve Blvd Windermere, FL Discover this beautifully updated 4-bedroom, 4-bathroom home tucked inside the exclusive g...	4 beds \| 4 baths \| 4,676 sq.ft.	$1,060,000	Airbnb cash on cash: 0.47% Traditional cash on cash: 3.32% Airbnb Rental Income: $3311 Traditional Rental Income: $5387 Airbnb ROI: 0.47% Traditional ROI: 3.32%
11021 Hawkshead Ct 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 Cir Windermere, FL Lakefront, Luxurious, Fully Furnished Home with Private Pool in Windermere. A True Para...	4 beds \| 4 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 Blvd Windermere, FL Extraordinary lake front opportunity in Windermere on 1.75 acres! PRIVATE GATES! NO HOA! S...	5 beds \| 3 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%

Your search for investment property begins and ends here

Woodlawn Investment Property for Sale in Windermere, FL

10624 Reams Rd

Windermere, FL

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

$499,000

Airbnb cash on cash: 2.98%

Traditional cash on cash: 3.4%

Airbnb Rental Income: $3311

Traditional Rental Income: $2769

Airbnb ROI: 2.98%

Traditional ROI: 3.4%

11325 Fenimore Ct

Windermere, FL

4 beds | 3 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%

5463 GEMGOLD COURT

Windermere, FL

4 beds | 3 baths | 2,246 sq.ft.

$599,000

Airbnb cash on cash: 2.61%

Traditional cash on cash: 3.41%

Airbnb Rental Income: $3311

Traditional Rental Income: $3018

Airbnb ROI: 2.61%

Traditional ROI: 3.41%

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%

6442 Golden Dewdrop Trl

Windermere, FL

3 beds | 2 baths | 2,139 sq.ft.

$585,000

Airbnb cash on cash: 0.89%

Traditional cash on cash: 2.87%

Airbnb Rental Income: $2597

Traditional Rental Income: $3055

Airbnb ROI: 0.89%

Traditional ROI: 2.87%

6117 Louise Cove Dr

Windermere, FL

4 beds | 4 baths | 5,752 sq.ft.

$5,250,000

Airbnb cash on cash: -1.71%

Traditional cash on cash: -0.8%

Airbnb Rental Income: $3311

Traditional Rental Income: $7149

Airbnb ROI: -1.71%

Traditional ROI: -0.8%

6615 Helmsley Cir

Windermere, FL

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

$769,900

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 Trl

Windermere, FL

4 beds | 3 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%