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 205 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
5825 OXFORD MOOR BOULEVARD Windermere, FL Under contract-accepting backup offers. Completely Remodeled 2022 \| Single Story \|Gated Wi...	4 beds \| 4 baths \| 4,319 sq.ft.	$1,500,000	Airbnb cash on cash: -0.46% Traditional cash on cash: 1.26% Airbnb Rental Income: $3311 Traditional Rental Income: $4973 Airbnb ROI: -0.46% Traditional ROI: 1.26%
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.	$475,000	Airbnb cash on cash: 3.23% Traditional cash on cash: 4.82% Airbnb Rental Income: $3311 Traditional Rental Income: $3275 Airbnb ROI: 3.23% Traditional ROI: 4.82%
2806 WINDSOR HILL DRIVE Windermere, FL Under contract-accepting backup offers. Step into this stunning 4-bedroom, 3-bathroom pool...	4 beds \| 3 baths \| 3,181 sq.ft.	$1,099,000	Airbnb cash on cash: 0.12% Traditional cash on cash: 0.97% Airbnb Rental Income: $3311 Traditional Rental Income: $3441 Airbnb ROI: 0.12% Traditional ROI: 0.97%
9620 Maywood Dr Windermere, FL Lake Front Living at its finest! The perfect family friendly lake house with lots of room...	4 beds \| 3 baths \| 3,004 sq.ft.	$2,400,000	Airbnb cash on cash: -0.37% Traditional cash on cash: -0.11% Airbnb Rental Income: $3311 Traditional Rental Income: $3143 Airbnb ROI: -0.37% Traditional ROI: -0.11%
1317 GLENHEATHER DRIVE Windermere, FL Under contract-accepting backup offers. Welcome to 1317 Glenheather Drive, a 2,811-square-...	4 beds \| 3 baths \| 2,811 sq.ft.	$974,900	Airbnb cash on cash: 0.77% Traditional cash on cash: 2.12% Airbnb Rental Income: $3311 Traditional Rental Income: $3803 Airbnb ROI: 0.77% Traditional ROI: 2.12%
2428 Butler Bay Dr N Windermere, FL Distinctive water view Pool home offers 4 Bedrooms, 4 Baths, Plus Office/Bonus Room and 3-...	4 beds \| 4 baths \| 3,387 sq.ft.	$1,150,000	Airbnb cash on cash: 0.44% Traditional cash on cash: 1.59% Airbnb Rental Income: $3311 Traditional Rental Income: $3791 Airbnb ROI: 0.44% Traditional ROI: 1.59%
11903 CAVE RUN AVENUE Windermere, FL Stunning move-in ready home in the highly sought-after Windermere Trails community, locate...	4 beds \| 4 baths \| 3,413 sq.ft.	$750,000	Airbnb cash on cash: 0.97% Traditional cash on cash: 3.76% Airbnb Rental Income: $3311 Traditional Rental Income: $4521 Airbnb ROI: 0.97% Traditional ROI: 3.76%
6130 Grosvenor Shore Dr Windermere, FL Remarkable Waterview Estate in Keeneâs Pointe! Heated Saltwater Pool, Main-Floor Living,...	4 beds \| 4 baths \| 4,676 sq.ft.	$3,150,000	Airbnb cash on cash: -1.04% Traditional cash on cash: 0.14% Airbnb Rental Income: $3311 Traditional Rental Income: $6032 Airbnb ROI: -1.04% Traditional ROI: 0.14%
6442 GOLDEN DEWDROP TRAIL Windermere, FL Short Sale. Come see this beautiful place. This immaculate home features include over 2,10...	3 beds \| 3 baths \| 2,139 sq.ft.	$575,000	Airbnb cash on cash: 0.93% Traditional cash on cash: 3.31% Airbnb Rental Income: $2597 Traditional Rental Income: $3256 Airbnb ROI: 0.93% Traditional ROI: 3.31%
2127 LILYPAD LANE Windermere, FL Under contract-accepting backup offers. Welcome to a rare opportunity in the highly sought...	4 beds \| 3 baths \| 3,349 sq.ft.	$1,250,000	Airbnb cash on cash: 0.15% Traditional cash on cash: 1.31% Airbnb Rental Income: $3311 Traditional Rental Income: $3918 Airbnb ROI: 0.15% Traditional ROI: 1.31%
6117 LOUISE COVE DRIVE Windermere, FL Under contract-accepting backup offers. Nestled along the shores of Lake Louise within Isl...	4 beds \| 5 baths \| 5,752 sq.ft.	$5,250,000	Airbnb cash on cash: -1.73% Traditional cash on cash: -0.55% Airbnb Rental Income: $3311 Traditional Rental Income: $8308 Airbnb ROI: -1.73% Traditional ROI: -0.55%
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: 3.12% Airbnb Rental Income: $3311 Traditional Rental Income: $3518 Airbnb ROI: 1.61% Traditional ROI: 3.12%
5199 Latrobe Dr Windermere, FL Positioned along the front nine of Isleworthâs famed championship golf course, this golf...	6 beds \| 6 baths \| 4,665 sq.ft.	$5,300,000	Airbnb cash on cash: -0.71% Traditional cash on cash: 0.12% Airbnb Rental Income: $5841 Traditional Rental Income: $8738 Airbnb ROI: -0.71% Traditional ROI: 0.12%
1136 Lake Whitney Dr Windermere, FL Resort style living. Spectacular, Unique & Richly designed, EXCLUSIVE VILLA D'ESTE. From t...	4 beds \| 5 baths \| 5,722 sq.ft.	$2,295,000	Airbnb cash on cash: -0.9% Traditional cash on cash: 1.4% Airbnb Rental Income: $3311 Traditional Rental Income: $7463 Airbnb ROI: -0.9% Traditional ROI: 1.4%
7231 SANGALLA DRIVE Windermere, FL Located in the gated community of Casa Del Lago in Windermere, featuring just 88 luxury ho...	5 beds \| 5 baths \| 3,835 sq.ft.	$1,398,000	Airbnb cash on cash: 1.53% Traditional cash on cash: 2.5% Airbnb Rental Income: $5841 Traditional Rental Income: $5936 Airbnb ROI: 1.53% Traditional ROI: 2.5%
811 Main St Windermere, FL Exclusive Rare Opportunity to own this expansivev100'x160' double lot in downtown Winderme...	2 beds \| 1 baths \| 1,398 sq.ft.	$649,999	Airbnb cash on cash: 3.83% Traditional cash on cash: 0.75% Airbnb Rental Income: $4898 Traditional Rental Income: $2026 Airbnb ROI: 3.83% Traditional ROI: 0.75%
8632 ABBOTSBURY DRIVE Windermere, FL One or more photo(s) has been virtually staged. Welcome to this beautifully updated 4-bedr...	4 beds \| 4 baths \| 2,720 sq.ft.	$625,000	Airbnb cash on cash: 1.57% Traditional cash on cash: 3.64% Airbnb Rental Income: $3311 Traditional Rental Income: $3777 Airbnb ROI: 1.57% Traditional ROI: 3.64%
11536 Claymont Cir Windermere, FL Attention to detail, craftsmanship truly describes this move-in ready home. As you enter, ...	4 beds \| 3 baths \| 2,882 sq.ft.	$1,175,000	Airbnb cash on cash: 0.36% Traditional cash on cash: 1.5% Airbnb Rental Income: $3311 Traditional Rental Income: $3815 Airbnb ROI: 0.36% Traditional ROI: 1.5%
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: -2.06% Traditional cash on cash: -0.69% Airbnb Rental Income: $2597 Traditional Rental Income: $6658 Airbnb ROI: -2.06% Traditional ROI: -0.69%
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: -1.74% Traditional cash on cash: -0.49% Airbnb Rental Income: $2597 Traditional Rental Income: $6376 Airbnb ROI: -1.74% Traditional ROI: -0.49%
81 Oakdale St Windermere, FL MASSIVE PRICE DROP! A rare find! Extremely well appointed custom home in the heart of D...	5 beds \| 4 baths \| 4,284 sq.ft.	$2,300,000	Airbnb cash on cash: 0.62% Traditional cash on cash: 0.98% Airbnb Rental Income: $5841 Traditional Rental Income: $5454 Airbnb ROI: 0.62% Traditional ROI: 0.98%
33 MAIN STREET Windermere, FL BUTLER CHAIN WATERFRONT Windermere 4/3 HOME WITH BOAT SLIP on a .37 acre Lot. Cypress tree...	4 beds \| 2 baths \| 2,130 sq.ft.	$1,575,000	Airbnb cash on cash: 0.1% Traditional cash on cash: 0.44% Airbnb Rental Income: $3311 Traditional Rental Income: $3068 Airbnb ROI: 0.1% Traditional ROI: 0.44%
325 Magnolia St Windermere, FL Best value on one of the largest lakefront properties on famed The Butler Chain of Lakes w...	4 beds \| 3 baths \| 3,975 sq.ft.	$2,450,000	Airbnb cash on cash: -0.66% Traditional cash on cash: -0.15% Airbnb Rental Income: $3311 Traditional Rental Income: $3748 Airbnb ROI: -0.66% Traditional ROI: -0.15%
5145 Latrobe Dr Windermere, FL Nestled along Isleworthâs famed championship golf course overlooking Hole 4, this beauti...	4 beds \| 4 baths \| 4,512 sq.ft.	$3,299,000	Airbnb cash on cash: -1.37% Traditional cash on cash: -0.27% Airbnb Rental Income: $3311 Traditional Rental Income: $5926 Airbnb ROI: -1.37% Traditional ROI: -0.27%
4906 Aviva Garden Ct Windermere, FL Nestled within the gates of the renowned Isleworth Golf & Country Club, this two-story est...	3 beds \| 4 baths \| 6,236 sq.ft.	$4,690,000	Airbnb cash on cash: -1.89% Traditional cash on cash: -1.33% Airbnb Rental Income: $2597 Traditional Rental Income: $4413 Airbnb ROI: -1.89% Traditional ROI: -1.33%
3013 SEIGNEURY DRIVE Windermere, FL Stylish and elegant with contemporary touches, welcome home to a magnificent and expansive...	4 beds \| 5 baths \| 5,130 sq.ft.	$1,750,000	Airbnb cash on cash: -1.03% Traditional cash on cash: 2.05% Airbnb Rental Income: $3311 Traditional Rental Income: $7579 Airbnb ROI: -1.03% Traditional ROI: 2.05%
11226 MACAW COURT Windermere, FL The Ultimate Entertainerâs Dream Home. Welcome to this exceptional custom-built courtyar...	4 beds \| 5 baths \| 4,549 sq.ft.	$1,825,000	Airbnb cash on cash: -0.78% Traditional cash on cash: 0.89% Airbnb Rental Income: $3311 Traditional Rental Income: $5391 Airbnb ROI: -0.78% Traditional ROI: 0.89%
5128 BUTLER RIDGE DRIVE Windermere, FL Calling all car enthusiasts or artisans needing a large, detached workshop on your propert...	4 beds \| 3 baths \| 2,816 sq.ft.	$1,250,000	Airbnb cash on cash: 0.34% Traditional cash on cash: 1.48% Airbnb Rental Income: $3311 Traditional Rental Income: $3894 Airbnb ROI: 0.34% Traditional ROI: 1.48%
12633 HADDON DRIVE Windermere, FL Sitting on a premium corner lot with mature landscaping, this beautiful Kensington model b...	5 beds \| 4 baths \| 3,000 sq.ft.	$650,000	Airbnb cash on cash: 5.28% Traditional cash on cash: 4.18% Airbnb Rental Income: $5841 Traditional Rental Income: $4012 Airbnb ROI: 5.28% Traditional ROI: 4.18%
109 E 12TH AVENUE Windermere, FL Modern style blends with Windermere charm. This totally renovated home is located just st...	4 beds \| 4 baths \| 2,791 sq.ft.	$1,198,000	Airbnb cash on cash: -0.46% Traditional cash on cash: 1.28% Airbnb Rental Income: $3311 Traditional Rental Income: $4506 Airbnb ROI: -0.46% Traditional ROI: 1.28%
12863 HOLDENBURY LANE Windermere, FL LOCATION! LOCATION! $5,000 CONCESSION FOR BUYER'S CLOSING COSTS. Experience refined living...	3 beds \| 2 baths \| 2,148 sq.ft.	$539,000	Airbnb cash on cash: 1.2% Traditional cash on cash: 3.36% Airbnb Rental Income: $2597 Traditional Rental Income: $3062 Airbnb ROI: 1.2% Traditional ROI: 3.36%
3328 WAX BERRY COURT Windermere, FL One or more photo(s) has been virtually staged. Located within Lake Butler Estates, one of...	4 beds \| 4 baths \| 2,636 sq.ft.	$925,000	Airbnb cash on cash: 0.68% Traditional cash on cash: 3.36% Airbnb Rental Income: $3311 Traditional Rental Income: $4878 Airbnb ROI: 0.68% Traditional ROI: 3.36%
212 W 1ST AVENUE Windermere, FL Pre-Construction. To be built. Positioned along the coveted Butler Chain of Lakes, this wa...	5 beds \| 5 baths \| 3,800 sq.ft.	$3,900,000	Airbnb cash on cash: -0.05% Traditional cash on cash: -0.82% Airbnb Rental Income: $5841 Traditional Rental Income: $1866 Airbnb ROI: -0.05% Traditional ROI: -0.82%
12533 CRAGSIDE LANE Windermere, FL **This house comes with a REDUCED RATE through the seller's preferred lender. This is a le...	4 beds \| 2 baths \| 2,151 sq.ft.	$575,000	Airbnb cash on cash: 1.98% Traditional cash on cash: 1.45% Airbnb Rental Income: $3311 Traditional Rental Income: $2287 Airbnb ROI: 1.98% Traditional ROI: 1.45%
4 CHASE ROAD Windermere, FL Under contract-accepting backup offers. FULLY RENOVATED DREAM HOME. This home is located r...	3 beds \| 2 baths \| 2,386 sq.ft.	$875,000	Airbnb cash on cash: 0.44% Traditional cash on cash: 2.03% Airbnb Rental Income: $2597 Traditional Rental Income: $3266 Airbnb ROI: 0.44% Traditional ROI: 2.03%
1028 LASCALA DRIVE Windermere, FL Under contract-accepting backup offers. Introducing an EXCEPTIONAL opportunity to own a RE...	4 beds \| 3 baths \| 2,208 sq.ft.	$749,000	Airbnb cash on cash: 1.24% Traditional cash on cash: 1.95% Airbnb Rental Income: $3311 Traditional Rental Income: $3064 Airbnb ROI: 1.24% Traditional ROI: 1.95%
6142 GROSVENOR SHORE DRIVE Windermere, FL Located in Grosvenor Village within Keeneâs Pointe, this estate overlooks a pond and the...	4 beds \| 6 baths \| 6,950 sq.ft.	$5,150,000	Airbnb cash on cash: -1.89% Traditional cash on cash: 0.04% Airbnb Rental Income: $3311 Traditional Rental Income: $11763 Airbnb ROI: -1.89% Traditional ROI: 0.04%
9119 Balmoral Mews Sq Windermere, FL MARCH MADNESS MOVING SALE - PRICE IMPROVEMENT for a home in Balmoral and your new highly s...	4 beds \| 4 baths \| 4,052 sq.ft.	$1,450,000	Airbnb cash on cash: -0.07% Traditional cash on cash: 1.02% Airbnb Rental Income: $3311 Traditional Rental Income: $4039 Airbnb ROI: -0.07% Traditional ROI: 1.02%
12718 WINDERMERE ISLES PLACE Windermere, FL Welcome to 12718 Windermere Isles Place, a spectacular residence tucked away on a quiet cu...	5 beds \| 4 baths \| 3,487 sq.ft.	$1,490,000	Airbnb cash on cash: 1.77% Traditional cash on cash: 2.25% Airbnb Rental Income: $5841 Traditional Rental Income: $5349 Airbnb ROI: 1.77% Traditional ROI: 2.25%
6897 NORTHWICH DRIVE Windermere, FL Under contract-accepting backup offers. Welcome to the highly desirable Lakes of Windermer...	4 beds \| 3 baths \| 2,229 sq.ft.	$574,900	Airbnb cash on cash: 2.08% Traditional cash on cash: 2.89% Airbnb Rental Income: $3311 Traditional Rental Income: $3007 Airbnb ROI: 2.08% Traditional ROI: 2.89%

Your search for investment property begins and ends here

Single Family Homes for Sale in Windermere, FL

5825 OXFORD MOOR BOULEVARD

Windermere, FL

4 beds | 4 baths | 4,319 sq.ft.

$1,500,000

Airbnb cash on cash: -0.46%

Traditional cash on cash: 1.26%

Airbnb Rental Income: $3311

Traditional Rental Income: $4973

Airbnb ROI: -0.46%

Traditional ROI: 1.26%

10624 REAMS ROAD

Windermere, FL

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

$475,000

Airbnb cash on cash: 3.23%

Traditional cash on cash: 4.82%

Airbnb Rental Income: $3311

Traditional Rental Income: $3275

Airbnb ROI: 3.23%

Traditional ROI: 4.82%

2806 WINDSOR HILL DRIVE

Windermere, FL

4 beds | 3 baths | 3,181 sq.ft.

$1,099,000

Airbnb cash on cash: 0.12%

Traditional cash on cash: 0.97%

Airbnb Rental Income: $3311

Traditional Rental Income: $3441

Airbnb ROI: 0.12%

Traditional ROI: 0.97%

9620 Maywood Dr

Windermere, FL

4 beds | 3 baths | 3,004 sq.ft.

$2,400,000

Airbnb cash on cash: -0.37%

Traditional cash on cash: -0.11%

Airbnb Rental Income: $3311

Traditional Rental Income: $3143

Airbnb ROI: -0.37%

Traditional ROI: -0.11%

1317 GLENHEATHER DRIVE

Windermere, FL

4 beds | 3 baths | 2,811 sq.ft.

$974,900

Airbnb cash on cash: 0.77%

Traditional cash on cash: 2.12%

Airbnb Rental Income: $3311

Traditional Rental Income: $3803

Airbnb ROI: 0.77%

Traditional ROI: 2.12%

2428 Butler Bay Dr N

Windermere, FL

4 beds | 4 baths | 3,387 sq.ft.

$1,150,000

Airbnb cash on cash: 0.44%

Traditional cash on cash: 1.59%

Airbnb Rental Income: $3311

Traditional Rental Income: $3791

Airbnb ROI: 0.44%

Traditional ROI: 1.59%

11903 CAVE RUN AVENUE

Windermere, FL

4 beds | 4 baths | 3,413 sq.ft.

$750,000

Airbnb cash on cash: 0.97%

Traditional cash on cash: 3.76%

Airbnb Rental Income: $3311

Traditional Rental Income: $4521

Airbnb ROI: 0.97%

Traditional ROI: 3.76%

6130 Grosvenor Shore Dr

Windermere, FL

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

$3,150,000

Airbnb cash on cash: -1.04%

Traditional cash on cash: 0.14%

Airbnb Rental Income: $3311

Traditional Rental Income: $6032

Airbnb ROI: -1.04%