Real Estate Investment Properties for Sale in Winter Garden, FL

Looking for investment property in Winter Garden, FL with high ROI ?

Explore a variety of short-term homes & houses in Winter Garden, FL. Invest wisely with VRBO & Winter Garden, 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 Winter Garden, FL

Search for Single Family Residential for Sale in Winter Garden, 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 622 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
607 E Oakland Ave Winter Garden, FL Welcome to this exceptional Winter Garden home with 4 bedrooms, 3.5-bathrooms, PLUS home o...	4 beds \| 3 baths \| 3,406 sq.ft.	$875,000	Airbnb cash on cash: 2.86% Traditional cash on cash: 2.99% Airbnb Rental Income: $5064 Traditional Rental Income: $4139 Airbnb ROI: 2.86% Traditional ROI: 2.99%
330 E Story Rd Winter Garden, FL One or more photo(s) has been virtually staged. Welcome to an incredible opportunity to ow...	2 beds \| 1 baths \| 760 sq.ft.	$285,000	Airbnb cash on cash: 3.39% Traditional cash on cash: 3.94% Airbnb Rental Income: $2340 Traditional Rental Income: $1929 Airbnb ROI: 3.39% Traditional ROI: 3.94%
12456 Westfield Lakes Cir Winter Garden, FL Welcome home to this stunning residence in the highly desirable Westfield Lakes community,...	4 beds \| 3 baths \| 2,180 sq.ft.	$549,000	Airbnb cash on cash: 5.52% Traditional cash on cash: 3.13% Airbnb Rental Income: $5064 Traditional Rental Income: $2747 Airbnb ROI: 5.52% Traditional ROI: 3.13%
7189 Summerlake Groves St Winter Garden, FL COME set your eyes on this Gorgeous 2-Story Winter Garden home located in Highlands at Sum...	3 beds \| 2 baths \| 2,138 sq.ft.	$619,999	Airbnb cash on cash: -0.51% Traditional cash on cash: 2.51% Airbnb Rental Income: $1636 Traditional Rental Income: $2922 Airbnb ROI: -0.51% Traditional ROI: 2.51%
14372 Sunbridge Cir Winter Garden, FL This is a unique opportunity to live in the highly sought-after gated community of Bradfor...	4 beds \| 4 baths \| 3,468 sq.ft.	$799,000	Airbnb cash on cash: 3.33% Traditional cash on cash: 5.68% Airbnb Rental Income: $5064 Traditional Rental Income: $5780 Airbnb ROI: 3.33% Traditional ROI: 5.68%
14046 Fox Glove St Winter Garden, FL Stunning golf course frontage home in the highly desirable Stoneybrook West gated communit...	4 beds \| 3 baths \| 2,970 sq.ft.	$765,000	Airbnb cash on cash: N/A Traditional cash on cash: 2.61% Airbnb Rental Income: $null Traditional Rental Income: $3329 Airbnb ROI: N/A Traditional ROI: 2.61%
714 Parkmont Pl Winter Garden, FL Welcome to the GOLF CART district of WINTER GARDEN! This STUNNING home was the former Ryan...	3 beds \| 2 baths \| 2,190 sq.ft.	$549,900	Airbnb cash on cash: -0.31% Traditional cash on cash: 2.35% Airbnb Rental Income: $1636 Traditional Rental Income: $2588 Airbnb ROI: -0.31% Traditional ROI: 2.35%
14282 Creekbed Cir Winter Garden, FL Price improvement and quick close available. WELCOME HOME: YOUR WINTER GARDEN ESCAPE AWAI...	4 beds \| 4 baths \| 3,479 sq.ft.	$937,500	Airbnb cash on cash: 2.52% Traditional cash on cash: 3.44% Airbnb Rental Income: $5064 Traditional Rental Income: $4828 Airbnb ROI: 2.52% Traditional ROI: 3.44%
14645 Scott Key Dr Winter Garden, FL Beautifully updated single-family home featuring NEW EXTERIOR PAINT AND NEW FLOORING THROU...	4 beds \| 3 baths \| 3,427 sq.ft.	$935,000	Airbnb cash on cash: 2.07% Traditional cash on cash: 1.81% Airbnb Rental Income: $5064 Traditional Rental Income: $3797 Airbnb ROI: 2.07% Traditional ROI: 1.81%
15852 Shorebird Ln Winter Garden, FL Stunning 2-Story Home in Winter Garden â 4 Bedrooms, Solar Panels, and Exceptional Featu...	4 beds \| 4 baths \| 2,766 sq.ft.	$859,000	Airbnb cash on cash: 1.99% Traditional cash on cash: 1.78% Airbnb Rental Income: $5064 Traditional Rental Income: $3857 Airbnb ROI: 1.99% Traditional ROI: 1.78%
15372 Gilligan Ct Winter Garden, FL Stunning One-Story Home in the Heart of Horizon West â Beautifully Renovated and Move-In...	4 beds \| 3 baths \| 2,781 sq.ft.	$884,500	Airbnb cash on cash: 2.75% Traditional cash on cash: 2.34% Airbnb Rental Income: $5064 Traditional Rental Income: $3697 Airbnb ROI: 2.75% Traditional ROI: 2.34%
5531 Cypress Hill Rd Winter Garden, FL Exquisitely upgraded 4-bedroom, 3-bath smart home in the highly sought-after Orchard Hills...	4 beds \| 3 baths \| 2,204 sq.ft.	$625,000	Airbnb cash on cash: 4.02% Traditional cash on cash: 1.96% Airbnb Rental Income: $5064 Traditional Rental Income: $2827 Airbnb ROI: 4.02% Traditional ROI: 1.96%
8256 Bayview Crossing Dr Winter Garden, FL PRICE IMPROVEMENT....UPGRADED POOL HOME in Horizon West! Welcome to this 4-bed, 3.5-bath,...	4 beds \| 3 baths \| 2,557 sq.ft.	$675,000	Airbnb cash on cash: 3.27% Traditional cash on cash: 2.5% Airbnb Rental Income: $5064 Traditional Rental Income: $3546 Airbnb ROI: 3.27% Traditional ROI: 2.5%
634 Foster Ave Winter Garden, FL Charming bungalow that's been completely renovated and is now move-in ready! Rebuilt down ...	2 beds \| 1 baths \| 696 sq.ft.	$285,000	Airbnb cash on cash: 3.9% Traditional cash on cash: 2.86% Airbnb Rental Income: $2340 Traditional Rental Income: $1483 Airbnb ROI: 3.9% Traditional ROI: 2.86%
14602 Winter Stay Dr Winter Garden, FL Fantastic opportunity to own this exceptional home in the highly sought-after WATERMARK co...	4 beds \| 3 baths \| 3,433 sq.ft.	$780,000	Airbnb cash on cash: 3.25% Traditional cash on cash: 3.24% Airbnb Rental Income: $5064 Traditional Rental Income: $4026 Airbnb ROI: 3.25% Traditional ROI: 3.24%
16253 Pebble Bluff Loop Winter Garden, FL Currently house has a tenant - opportunity for investors Waterleigh is a resort-s...	3 beds \| 2 baths \| 1,700 sq.ft.	$476,900	Airbnb cash on cash: -0.54% Traditional cash on cash: 2.06% Airbnb Rental Income: $1636 Traditional Rental Income: $2332 Airbnb ROI: -0.54% Traditional ROI: 2.06%
17661 Davenport Rd Winter Garden, FL Located in the Rare Lake Avalon Rural Settlement where oversized lots and protected rural ...	3 beds \| 3 baths \| 2,400 sq.ft.	$1,150,000	Airbnb cash on cash: -0.79% Traditional cash on cash: 3.03% Airbnb Rental Income: $1636 Traditional Rental Income: $5347 Airbnb ROI: -0.79% Traditional ROI: 3.03%
15058 Sawgrass Bluff Dr Winter Garden, FL Location! Location! Located just 10 minutes from historic downtown Winter Garden and adjac...	4 beds \| 2 baths \| 2,626 sq.ft.	$600,000	Airbnb cash on cash: 4.72% Traditional cash on cash: 2.93% Airbnb Rental Income: $5064 Traditional Rental Income: $3031 Airbnb ROI: 4.72% Traditional ROI: 2.93%
16125 Azure Key St Winter Garden, FL Welcome home to the highly sought-after Waterleigh community in Horizon West. This bright ...	3 beds \| 2 baths \| 1,685 sq.ft.	$490,000	Airbnb cash on cash: -0.53% Traditional cash on cash: 4.27% Airbnb Rental Income: $1636 Traditional Rental Income: $3377 Airbnb ROI: -0.53% Traditional ROI: 4.27%
1534 E Spring Ridge Cir Winter Garden, FL Welcome to this stunning updated 3-bedroom, 2-bath home located in one of Winter Gardenâ...	3 beds \| 2 baths \| 1,688 sq.ft.	$554,000	Airbnb cash on cash: 0.14% Traditional cash on cash: 3.1% Airbnb Rental Income: $1636 Traditional Rental Income: $2709 Airbnb ROI: 0.14% Traditional ROI: 3.1%
500 Teacup Springs Ct Winter Garden, FL Short Sale. An exceptional opportunity for investors, builders, and developersâthis prop...	4 beds \| 3 baths \| 2,397 sq.ft.	$530,000	Airbnb cash on cash: 5.79% Traditional cash on cash: 3.83% Airbnb Rental Income: $5064 Traditional Rental Income: $3060 Airbnb ROI: 5.79% Traditional ROI: 3.83%
17117 HEARTWOOD LOOP Winter Garden, FL Welcome to your very own slice of Winter Garden paradise! This impressive 5.3-acre, high-a...	5 beds \| 4 baths \| 3,265 sq.ft.	$1,249,900	Airbnb cash on cash: N/A Traditional cash on cash: 1.23% Airbnb Rental Income: $null Traditional Rental Income: $3785 Airbnb ROI: N/A Traditional ROI: 1.23%
14200 AVALON ROAD #406 Winter Garden, FL Discover a Hidden Gem in the Heart of Winter Garden! This rarely available, fully furni...	3 beds \| 2 baths \| 1,288 sq.ft.	$225,000	Airbnb cash on cash: -1.07% Traditional cash on cash: 3.33% Airbnb Rental Income: $1636 Traditional Rental Income: $2112 Airbnb ROI: -1.07% Traditional ROI: 3.33%
634 Burch Ave Winter Garden, FL One or more photo(s) has been virtually staged. Seller offering $7,500 towards buyerâs c...	4 beds \| 3 baths \| 2,351 sq.ft.	$625,000	Airbnb cash on cash: 4.67% Traditional cash on cash: 4.18% Airbnb Rental Income: $5064 Traditional Rental Income: $3731 Airbnb ROI: 4.67% Traditional ROI: 4.18%
15452 Firelight Dr Winter Garden, FL Welcome to this stunning 4 bedroom, 3 bathroom home nestled in the highly sought-after gat...	4 beds \| 3 baths \| 2,648 sq.ft.	$639,900	Airbnb cash on cash: 4.67% Traditional cash on cash: 3.51% Airbnb Rental Income: $5064 Traditional Rental Income: $3338 Airbnb ROI: 4.67% Traditional ROI: 3.51%
14212 Murcott Blossom Blvd Winter Garden, FL Welcome to your new home in Lakeview Pointe â Horizon West! Built in 2016, this beautif...	3 beds \| 2 baths \| 1,954 sq.ft.	$499,990	Airbnb cash on cash: -0.56% Traditional cash on cash: 3.24% Airbnb Rental Income: $1636 Traditional Rental Income: $2951 Airbnb ROI: -0.56% Traditional ROI: 3.24%
15309 Honeybell Dr Winter Garden, FL One or more photo(s) has been virtually staged. Welcome to 3,094 sq ft of contemporary liv...	4 beds \| 3 baths \| 3,094 sq.ft.	$779,900	Airbnb cash on cash: 3.41% Traditional cash on cash: 3.09% Airbnb Rental Income: $5064 Traditional Rental Income: $3792 Airbnb ROI: 3.41% Traditional ROI: 3.09%
16394 Taliesin St Winter Garden, FL Stunning two-story house with a permanent lake view. Be enchanted by this magnificent l...	5 beds \| 4 baths \| 3,093 sq.ft.	$899,000	Airbnb cash on cash: N/A Traditional cash on cash: 2.43% Airbnb Rental Income: $null Traditional Rental Income: $4313 Airbnb ROI: N/A Traditional ROI: 2.43%
308 Florida Ave Winter Garden, FL Welcome to a quaint, quiet and cozy home in Winter Gardens. This recently renovated 1050 s...	3 beds \| 2 baths \| 1,050 sq.ft.	$320,000	Airbnb cash on cash: 1.18% Traditional cash on cash: 4.71% Airbnb Rental Income: $1636 Traditional Rental Income: $2237 Airbnb ROI: 1.18% Traditional ROI: 4.71%
13978 LANYARD WAY Winter Garden, FL One or more photo(s) has been virtually staged. Step into your dream residence! Perfect fo...	5 beds \| 4 baths \| 3,610 sq.ft.	$819,990	Airbnb cash on cash: N/A Traditional cash on cash: 3.03% Airbnb Rental Income: $null Traditional Rental Income: $4370 Airbnb ROI: N/A Traditional ROI: 3.03%
14571 Bahama Swallow Blvd Winter Garden, FL Welcome to this charming single-story home located in the highly desirable Summerlake comm...	4 beds \| 2 baths \| 2,063 sq.ft.	$534,900	Airbnb cash on cash: 4.88% Traditional cash on cash: 2.74% Airbnb Rental Income: $5064 Traditional Rental Income: $2953 Airbnb ROI: 4.88% Traditional ROI: 2.74%
13151 Calming Breeze Way Winter Garden, FL Built in the Fall of 2024, this meticulously crafted 3-bedroom, 2.5-bathroom home in the h...	3 beds \| 2 baths \| 2,096 sq.ft.	$551,990	Airbnb cash on cash: -0.56% Traditional cash on cash: 2.3% Airbnb Rental Income: $1636 Traditional Rental Income: $2656 Airbnb ROI: -0.56% Traditional ROI: 2.3%
8060 Bowery Dr Winter Garden, FL Priced to Sell! Elegant Home! 5 bedrooms, 3 bathroom, 2 car garage. Home features all the ...	5 beds \| 3 baths \| 3,013 sq.ft.	$680,000	Airbnb cash on cash: N/A Traditional cash on cash: 2.37% Airbnb Rental Income: $null Traditional Rental Income: $3138 Airbnb ROI: N/A Traditional ROI: 2.37%
8906 Doddington Way Winter Garden, FL Discover the ideal blend of modern comfort and family-friendly living in this beautifully ...	4 beds \| 3 baths \| 2,352 sq.ft.	$550,000	Airbnb cash on cash: 4.59% Traditional cash on cash: 2.04% Airbnb Rental Income: $5064 Traditional Rental Income: $2673 Airbnb ROI: 4.59% Traditional ROI: 2.04%
17850 Hither Hills Cir Winter Garden, FL Exquisite Lakefront Residence: 5 Beds, 5 Baths! This striking home, constructed by DR Hort...	5 beds \| 5 baths \| 3,416 sq.ft.	$1,199,000	Airbnb cash on cash: N/A Traditional cash on cash: 2.99% Airbnb Rental Income: $null Traditional Rental Income: $5748 Airbnb ROI: N/A Traditional ROI: 2.99%
11400 LOVERS LANE Winter Garden, FL If you've ever dreamed of country living, but don't want to give up your conveniences, the...	4 beds \| 3 baths \| 2,517 sq.ft.	$1,270,000	Airbnb cash on cash: 1.81% Traditional cash on cash: 0.99% Airbnb Rental Income: $5064 Traditional Rental Income: $3063 Airbnb ROI: 1.81% Traditional ROI: 0.99%
1674 Victoria Way Winter Garden, FL Under contract-accepting backup offers. Beautifully updated POOL home in the desirable Tus...	4 beds \| 2 baths \| 2,239 sq.ft.	$679,990	Airbnb cash on cash: 4.27% Traditional cash on cash: 3.82% Airbnb Rental Income: $5064 Traditional Rental Income: $3747 Airbnb ROI: 4.27% Traditional ROI: 3.82%
15680 Panther Lake Dr Winter Garden, FL Prepare to be awed by this stunning estate from the Toll Brothers executive collection in ...	5 beds \| 4 baths \| 4,329 sq.ft.	$2,000,000	Airbnb cash on cash: N/A Traditional cash on cash: 1.57% Airbnb Rental Income: $null Traditional Rental Income: $7205 Airbnb ROI: N/A Traditional ROI: 1.57%
14710 Scott Key Dr Winter Garden, FL PRICE REDUCTION!!!! Welcome to your dream home in the highly desirable Watermark communit...	5 beds \| 3 baths \| 2,935 sq.ft.	$749,000	Airbnb cash on cash: N/A Traditional cash on cash: 2.99% Airbnb Rental Income: $null Traditional Rental Income: $3910 Airbnb ROI: N/A Traditional ROI: 2.99%
13861 Lanyard Way Winter Garden, FL Over $60,000 in builder upgrades enhance this modern 2023-built home featuring 3 bedrooms,...	3 beds \| 2 baths \| 2,341 sq.ft.	$579,990	Airbnb cash on cash: -0.57% Traditional cash on cash: 2.49% Airbnb Rental Income: $1636 Traditional Rental Income: $2845 Airbnb ROI: -0.57% Traditional ROI: 2.49%

Your search for investment property begins and ends here

Single Family Homes for Sale in Winter Garden, FL

607 E Oakland Ave

Winter Garden, FL

4 beds | 3 baths | 3,406 sq.ft.

$875,000

Airbnb cash on cash: 2.86%

Traditional cash on cash: 2.99%

Airbnb Rental Income: $5064

Traditional Rental Income: $4139

Airbnb ROI: 2.86%

Traditional ROI: 2.99%

330 E Story Rd

Winter Garden, FL

2 beds | 1 baths | 760 sq.ft.

$285,000

Airbnb cash on cash: 3.39%

Traditional cash on cash: 3.94%

Airbnb Rental Income: $2340

Traditional Rental Income: $1929

Airbnb ROI: 3.39%

Traditional ROI: 3.94%

12456 Westfield Lakes Cir

Winter Garden, FL

4 beds | 3 baths | 2,180 sq.ft.

$549,000

Airbnb cash on cash: 5.52%

Traditional cash on cash: 3.13%

Airbnb Rental Income: $5064

Traditional Rental Income: $2747

Airbnb ROI: 5.52%

Traditional ROI: 3.13%

7189 Summerlake Groves St

Winter Garden, FL

3 beds | 2 baths | 2,138 sq.ft.

$619,999

Airbnb cash on cash: -0.51%

Traditional cash on cash: 2.51%

Airbnb Rental Income: $1636

Traditional Rental Income: $2922

Airbnb ROI: -0.51%

Traditional ROI: 2.51%

14372 Sunbridge Cir

Winter Garden, FL

4 beds | 4 baths | 3,468 sq.ft.

$799,000

Airbnb cash on cash: 3.33%

Traditional cash on cash: 5.68%

Airbnb Rental Income: $5064

Traditional Rental Income: $5780

Airbnb ROI: 3.33%

Traditional ROI: 5.68%

14046 Fox Glove St

Winter Garden, FL

4 beds | 3 baths | 2,970 sq.ft.

$765,000

Airbnb cash on cash: N/A

Traditional cash on cash: 2.61%

Airbnb Rental Income: $null

Traditional Rental Income: $3329

Airbnb ROI: N/A

Traditional ROI: 2.61%

714 Parkmont Pl

Winter Garden, FL

3 beds | 2 baths | 2,190 sq.ft.

$549,900

Airbnb cash on cash: -0.31%

Traditional cash on cash: 2.35%

Airbnb Rental Income: $1636

Traditional Rental Income: $2588

Airbnb ROI: -0.31%

Traditional ROI: 2.35%

14282 Creekbed Cir

Winter Garden, FL

4 beds | 4 baths | 3,479 sq.ft.

$937,500

Airbnb cash on cash: 2.52%

Traditional cash on cash: 3.44%

Airbnb Rental Income: $5064

Traditional Rental Income: $4828

Airbnb ROI: 2.52%