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 416 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
330 E STORY ROAD Winter Garden, FL Under contract-accepting backup offers. One or more photo(s) has been virtually staged. We...	2 beds \| 1 baths \| 760 sq.ft.	$285,000	Airbnb cash on cash: 4% Traditional cash on cash: 4.63% Airbnb Rental Income: $2340 Traditional Rental Income: $1929 Airbnb ROI: 4% Traditional ROI: 4.63%
12456 WESTFIELD LAKES CIRCLE 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: 5.83% Traditional cash on cash: 3.32% Airbnb Rental Income: $5064 Traditional Rental Income: $2747 Airbnb ROI: 5.83% Traditional ROI: 3.32%
7189 SUMMERLAKE GROVES STREET Winter Garden, FL COME set your eyes on your Gorgeous 2-Story Winter Garden DREAM HOME located in the Highla...	3 beds \| 3 baths \| 2,138 sq.ft.	$609,999	Airbnb cash on cash: -0.5% Traditional cash on cash: 3.22% Airbnb Rental Income: $1636 Traditional Rental Income: $3295 Airbnb ROI: -0.5% Traditional ROI: 3.22%
337 SUNSET OAKS RD Winter Garden, FL This exceptional home is ideally located in the desirable Golf Cart District, offering par...	4 beds \| 3 baths \| 2,186 sq.ft.	$599,900	Airbnb cash on cash: 4.61% Traditional cash on cash: 4.05% Airbnb Rental Income: $5064 Traditional Rental Income: $3717 Airbnb ROI: 4.61% Traditional ROI: 4.05%
14372 SUNBRIDGE CIRCLE Winter Garden, FL This is a unique opportunity to live in the highly sought-after gated community of Bradfor...	4 beds \| 5 baths \| 3,468 sq.ft.	$775,000	Airbnb cash on cash: 3.46% Traditional cash on cash: 6.16% Airbnb Rental Income: $5064 Traditional Rental Income: $5980 Airbnb ROI: 3.46% Traditional ROI: 6.16%
2202 ROMANUM DRIVE Winter Garden, FL Welcome to your next home in the heart of Winter Gardenâwhere location, lifestyle, and u...	3 beds \| 2 baths \| 1,889 sq.ft.	$585,000	Airbnb cash on cash: -0.1% Traditional cash on cash: 2.21% Airbnb Rental Income: $1636 Traditional Rental Income: $2435 Airbnb ROI: -0.1% Traditional ROI: 2.21%
16232 ROCK COAST DRIVE Winter Garden, FL Welcome to your dream home and backyard oasis! This beautiful GAS HEATED SALTWATER POOL ho...	4 beds \| 5 baths \| 3,491 sq.ft.	$925,000	Airbnb cash on cash: 2.41% Traditional cash on cash: 6.22% Airbnb Rental Income: $5064 Traditional Rental Income: $7312 Airbnb ROI: 2.41% Traditional ROI: 6.22%
714 PARKMONT PLACE 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: -0.29% Traditional cash on cash: 3.31% Airbnb Rental Income: $1636 Traditional Rental Income: $3022 Airbnb ROI: -0.29% Traditional ROI: 3.31%
14282 CREEKBED CIRCLE Winter Garden, FL *Seller is willing to contribute up to $5,000 towards interest rate buy down or closing co...	4 beds \| 4 baths \| 3,479 sq.ft.	$924,500	Airbnb cash on cash: 2.57% Traditional cash on cash: 4.61% Airbnb Rental Income: $5064 Traditional Rental Income: $5782 Airbnb ROI: 2.57% Traditional ROI: 4.61%
5401 BOWMAN DRIVE Winter Garden, FL Welcome to Horizon West living at its finest in the highly sought-after Overlook at Hamlin...	4 beds \| 4 baths \| 4,044 sq.ft.	$1,250,000	Airbnb cash on cash: 1.46% Traditional cash on cash: 1.96% Airbnb Rental Income: $5064 Traditional Rental Income: $4606 Airbnb ROI: 1.46% Traditional ROI: 1.96%
604 FOSTER AVENUE Winter Garden, FL Situated just two blocks outside the Golf Cart District and directly across from Veterans ...	3 beds \| 2 baths \| 1,275 sq.ft.	$400,000	Airbnb cash on cash: 1.48% Traditional cash on cash: 3.92% Airbnb Rental Income: $1636 Traditional Rental Income: $2092 Airbnb ROI: 1.48% Traditional ROI: 3.92%
374 MILLWOOD PLACE Winter Garden, FL Under contract-accepting backup offers. READY TO DISCOVER A HOME THAT TRULY STANDS OUT? S...	3 beds \| 2 baths \| 2,200 sq.ft.	$575,000	Airbnb cash on cash: 0.03% Traditional cash on cash: 3.57% Airbnb Rental Income: $1636 Traditional Rental Income: $3076 Airbnb ROI: 0.03% Traditional ROI: 3.57%
13536 SUNSET LAKES CIRCLE Winter Garden, FL Experience luxury living in this gorgeous home in the highly sought after Sunset Lakes com...	5 beds \| 4 baths \| 3,389 sq.ft.	$1,200,000	Airbnb cash on cash: N/A Traditional cash on cash: 3.52% Airbnb Rental Income: $null Traditional Rental Income: $6227 Airbnb ROI: N/A Traditional ROI: 3.52%
7266 DESERT MANDARIN STREET Winter Garden, FL Great investment opportunity! Welcome to this beautifully maintained home built in 2018, f...	4 beds \| 3 baths \| 2,365 sq.ft.	$595,000	Airbnb cash on cash: 4.34% Traditional cash on cash: 2.29% Airbnb Rental Income: $5064 Traditional Rental Income: $2890 Airbnb ROI: 4.34% Traditional ROI: 2.29%
16554 RAVEN ROCK PLACE Winter Garden, FL Twinwaters Former MODEL home built with BEAUTIFUL UPGRADES 3 car garage ** Heated PO...	4 beds \| 3 baths \| 3,032 sq.ft.	$875,000	Airbnb cash on cash: 2.82% Traditional cash on cash: 3.35% Airbnb Rental Income: $5064 Traditional Rental Income: $4466 Airbnb ROI: 2.82% Traditional ROI: 3.35%
14501 GROVE RESORT AVENUE #3202 Winter Garden, FL Welcome to Your Perfect Orlando Investment & Vacation Escape! This beautifully appointed c...	3 beds \| 2 baths \| 1,396 sq.ft.	$350,000	Airbnb cash on cash: -2.56% Traditional cash on cash: 2.02% Airbnb Rental Income: $1636 Traditional Rental Income: $2677 Airbnb ROI: -2.56% Traditional ROI: 2.02%
213 W TILDEN STREET Winter Garden, FL Located in DOWNTOWN WINTER GARDEN!! This beautifully renovated single story home combi...	4 beds \| 2 baths \| 2,151 sq.ft.	$765,000	Airbnb cash on cash: 3.47% Traditional cash on cash: 2.24% Airbnb Rental Income: $5064 Traditional Rental Income: $3152 Airbnb ROI: 3.47% Traditional ROI: 2.24%
15852 SHOREBIRD LANE Winter Garden, FL Stunning 2-Story Home in Winter Garden â 4 Bedrooms, Solar Panels, and Exceptional Featu...	4 beds \| 5 baths \| 2,766 sq.ft.	$779,000	Airbnb cash on cash: 2.44% Traditional cash on cash: 2.76% Airbnb Rental Income: $5064 Traditional Rental Income: $4262 Airbnb ROI: 2.44% Traditional ROI: 2.76%
15372 GILLIGAN COURT Winter Garden, FL Stunning One-Story Home in the Heart of Horizon West â Beautifully Renovated and Move-In...	4 beds \| 4 baths \| 2,781 sq.ft.	$870,000	Airbnb cash on cash: 2.81% Traditional cash on cash: 4.09% Airbnb Rental Income: $5064 Traditional Rental Income: $5070 Airbnb ROI: 2.81% Traditional ROI: 4.09%
5531 CYPRESS HILL ROAD 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.	$610,000	Airbnb cash on cash: 4.14% Traditional cash on cash: 3.02% Airbnb Rental Income: $5064 Traditional Rental Income: $3393 Airbnb ROI: 4.14% Traditional ROI: 3.02%
1112 JUNIPER HAMMOCK COURT Winter Garden, FL One or more photo(s) has been virtually staged. Welcome to this beautiful and spacious 4-b...	4 beds \| 2 baths \| 2,545 sq.ft.	$520,000	Airbnb cash on cash: 5.77% Traditional cash on cash: 3.96% Airbnb Rental Income: $5064 Traditional Rental Income: $3154 Airbnb ROI: 5.77% Traditional ROI: 3.96%
8256 BAYVIEW CROSSING DRIVE Winter Garden, FL Under contract-accepting backup offers. PRICE IMPROVEMENT....UPGRADED POOL HOME in Horizon...	4 beds \| 4 baths \| 2,557 sq.ft.	$675,000	Airbnb cash on cash: 3.27% Traditional cash on cash: 4.32% Airbnb Rental Income: $5064 Traditional Rental Income: $4693 Airbnb ROI: 3.27% Traditional ROI: 4.32%
634 FOSTER AVENUE 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: 4.48% Airbnb Rental Income: $2340 Traditional Rental Income: $1916 Airbnb ROI: 3.9% Traditional ROI: 4.48%
14501 GROVE RESORT AVENUE #1727 Winter Garden, FL This luxurious 2-bedroom, 2-bath vacation condo is the ultimate retreat for those seeking ...	2 beds \| 2 baths \| 1,265 sq.ft.	$298,500	Airbnb cash on cash: -0.36% Traditional cash on cash: 2.56% Airbnb Rental Income: $2340 Traditional Rental Income: $2582 Airbnb ROI: -0.36% Traditional ROI: 2.56%
14501 GROVE RESORT AVENUE #3535 Winter Garden, FL GREAT OWNER FINANCING AVAILABLE: CONTACT US FOR ADDITIONAL INFORMATION. BEAUTIFUL 2 BED/2 ...	2 beds \| 2 baths \| 1,434 sq.ft.	$389,990	Airbnb cash on cash: -0.99% Traditional cash on cash: 1.87% Airbnb Rental Income: $2340 Traditional Rental Income: $2808 Airbnb ROI: -0.99% Traditional ROI: 1.87%
14602 WINTER STAY DRIVE Winter Garden, FL Fantastic opportunity to own this exceptional home in the highly sought-after WATERMARK co...	4 beds \| 4 baths \| 3,433 sq.ft.	$780,000	Airbnb cash on cash: 3.25% Traditional cash on cash: 3.79% Airbnb Rental Income: $5064 Traditional Rental Income: $4427 Airbnb ROI: 3.25% Traditional ROI: 3.79%
17661 DAVENPORT ROAD Winter Garden, FL Under contract-accepting backup offers. Located in the Rare Lake Avalon Rural Settlement w...	3 beds \| 3 baths \| 2,400 sq.ft.	$1,125,000	Airbnb cash on cash: -0.78% Traditional cash on cash: 2.89% Airbnb Rental Income: $1636 Traditional Rental Income: $5018 Airbnb ROI: -0.78% Traditional ROI: 2.89%
14501 GROVE RESORT AVENUE #1440 Winter Garden, FL ust minutes from Disney, this fully furnished condo at The Grove Resort and Waterpark offe...	2 beds \| 2 baths \| 1,375 sq.ft.	$245,000	Airbnb cash on cash: -0.68% Traditional cash on cash: 3.26% Airbnb Rental Income: $2340 Traditional Rental Income: $2672 Airbnb ROI: -0.68% Traditional ROI: 3.26%
14501 GROVE RESORT AVENUE #2602 Winter Garden, FL Experience the best of both worlds with this incredible fully furnished 3-bedroom, 2-bath ...	3 beds \| 2 baths \| 1,396 sq.ft.	$299,000	Airbnb cash on cash: -3.47% Traditional cash on cash: 1.87% Airbnb Rental Income: $1636 Traditional Rental Income: $2678 Airbnb ROI: -3.47% Traditional ROI: 1.87%
14501 GROVE RESORT AVENUE #2119 Winter Garden, FL Attention SNOWBIRDS! Great resorts for snowbirds! Gorgeous Lakeview Condo at The Grove R...	3 beds \| 2 baths \| 1,396 sq.ft.	$224,000	Airbnb cash on cash: -4.15% Traditional cash on cash: 2.9% Airbnb Rental Income: $1636 Traditional Rental Income: $2671 Airbnb ROI: -4.15% Traditional ROI: 2.9%
14501 GROVE RESORT AVENUE #3215 Winter Garden, FL Welcome to Grove Resort! Located on the second floor of Building 3, this unit is your laun...	2 beds \| 2 baths \| 1,265 sq.ft.	$239,000	Airbnb cash on cash: -0.1% Traditional cash on cash: 3.69% Airbnb Rental Income: $2340 Traditional Rental Income: $2617 Airbnb ROI: -0.1% Traditional ROI: 3.69%
14501 GROVE RESORT AVENUE #3406 Winter Garden, FL Attention SNOWBIRDS! Great resorts for snowbirds! Gorgeous Lakeview Condo at The Grove R...	2 beds \| 2 baths \| 1,265 sq.ft.	$204,000	Airbnb cash on cash: -0.05% Traditional cash on cash: 4.08% Airbnb Rental Income: $2340 Traditional Rental Income: $2562 Airbnb ROI: -0.05% Traditional ROI: 4.08%
14501 GROVE RESORT AVENUE #1443 Winter Garden, FL GREAT NEW LISTING & PRICE: $300,000.00 MOTIVATED SELLER. WELCOME TO THE GROVE RESORT & WAT...	2 beds \| 2 baths \| 1,375 sq.ft.	$300,000	Airbnb cash on cash: -0.65% Traditional cash on cash: 2.76% Airbnb Rental Income: $2340 Traditional Rental Income: $2726 Airbnb ROI: -0.65% Traditional ROI: 2.76%
14501 GROVE RESORT AVENUE #1220 Winter Garden, FL The Birch â 2 Bed / 2 Bath Condo-Hotel The only floorplan at The Grove with two true pr...	2 beds \| 2 baths \| 1,375 sq.ft.	$325,890	Airbnb cash on cash: -0.18% Traditional cash on cash: 3.18% Airbnb Rental Income: $2340 Traditional Rental Income: $2792 Airbnb ROI: -0.18% Traditional ROI: 3.18%
15058 SAWGRASS BLUFF DRIVE Winter Garden, FL Location! Location! Located just 10 minutes from historic downtown Winter Garden and adjac...	4 beds \| 3 baths \| 2,626 sq.ft.	$579,900	Airbnb cash on cash: 4.85% Traditional cash on cash: 3.43% Airbnb Rental Income: $5064 Traditional Rental Income: $3262 Airbnb ROI: 4.85% Traditional ROI: 3.43%
16125 AZURE KEY STREET Winter Garden, FL Under contract-accepting backup offers. *Incentives available through seller's preferred l...	3 beds \| 2 baths \| 1,685 sq.ft.	$480,000	Airbnb cash on cash: -0.52% Traditional cash on cash: 3.37% Airbnb Rental Income: $1636 Traditional Rental Income: $2925 Airbnb ROI: -0.52% Traditional ROI: 3.37%
14255 HAMPSHIRE BAY CIRCLE Winter Garden, FL One or more photo(s) has been virtually staged. NEW ROOF (2025) ~ TWO NEW A/C UNITS (2024)...	4 beds \| 5 baths \| 4,625 sq.ft.	$1,300,000	Airbnb cash on cash: 1.18% Traditional cash on cash: 4.03% Airbnb Rental Income: $5064 Traditional Rental Income: $7475 Airbnb ROI: 1.18% Traditional ROI: 4.03%
15594 SHOREBIRD LANE Winter Garden, FL One or more photo(s) has been virtually staged. PANORAMIC LAKE VIEWS â¢ DISNEY FIREWORKS ...	4 beds \| 4 baths \| 3,022 sq.ft.	$1,258,000	Airbnb cash on cash: 0.61% Traditional cash on cash: 0.7% Airbnb Rental Income: $5064 Traditional Rental Income: $4140 Airbnb ROI: 0.61% Traditional ROI: 0.7%
15187 HARROWGATE WAY Winter Garden, FL Location! Location! Welcome to this wel maintained 3 beds 2 bath single family home locate...	3 beds \| 2 baths \| 1,296 sq.ft.	$450,000	Airbnb cash on cash: 0.17% Traditional cash on cash: 3.14% Airbnb Rental Income: $1636 Traditional Rental Income: $2425 Airbnb ROI: 0.17% Traditional ROI: 3.14%
10043 SEQUEL ALLEY Winter Garden, FL About 10 minutes to Disney. Corner lot facing open green space. Main floor primary suite w...	4 beds \| 4 baths \| 2,502 sq.ft.	$569,000	Airbnb cash on cash: 4.76% Traditional cash on cash: 4.09% Airbnb Rental Income: $5064 Traditional Rental Income: $3675 Airbnb ROI: 4.76% Traditional ROI: 4.09%

Your search for investment property begins and ends here

Single Family Homes for Sale in Winter Garden, FL

330 E STORY ROAD

Winter Garden, FL

2 beds | 1 baths | 760 sq.ft.

$285,000

Airbnb cash on cash: 4%

Traditional cash on cash: 4.63%

Airbnb Rental Income: $2340

Traditional Rental Income: $1929

Airbnb ROI: 4%

Traditional ROI: 4.63%

12456 WESTFIELD LAKES CIRCLE

Winter Garden, FL

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

$549,000

Airbnb cash on cash: 5.83%

Traditional cash on cash: 3.32%

Airbnb Rental Income: $5064

Traditional Rental Income: $2747

Airbnb ROI: 5.83%

Traditional ROI: 3.32%

7189 SUMMERLAKE GROVES STREET

Winter Garden, FL

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

$609,999

Airbnb cash on cash: -0.5%

Traditional cash on cash: 3.22%

Airbnb Rental Income: $1636

Traditional Rental Income: $3295

Airbnb ROI: -0.5%

Traditional ROI: 3.22%

337 SUNSET OAKS RD

Winter Garden, FL

4 beds | 3 baths | 2,186 sq.ft.

$599,900

Airbnb cash on cash: 4.61%

Traditional cash on cash: 4.05%

Airbnb Rental Income: $5064

Traditional Rental Income: $3717

Airbnb ROI: 4.61%

Traditional ROI: 4.05%

14372 SUNBRIDGE CIRCLE

Winter Garden, FL

4 beds | 5 baths | 3,468 sq.ft.

$775,000

Airbnb cash on cash: 3.46%

Traditional cash on cash: 6.16%

Airbnb Rental Income: $5064

Traditional Rental Income: $5980

Airbnb ROI: 3.46%

Traditional ROI: 6.16%

2202 ROMANUM DRIVE

Winter Garden, FL

3 beds | 2 baths | 1,889 sq.ft.

$585,000

Airbnb cash on cash: -0.1%

Traditional cash on cash: 2.21%

Airbnb Rental Income: $1636

Traditional Rental Income: $2435

Airbnb ROI: -0.1%

Traditional ROI: 2.21%

16232 ROCK COAST DRIVE

Winter Garden, FL

4 beds | 5 baths | 3,491 sq.ft.

$925,000

Airbnb cash on cash: 2.41%

Traditional cash on cash: 6.22%

Airbnb Rental Income: $5064

Traditional Rental Income: $7312

Airbnb ROI: 2.41%

Traditional ROI: 6.22%

714 PARKMONT PLACE

Winter Garden, FL

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

$549,900

Airbnb cash on cash: -0.29%

Traditional cash on cash: 3.31%

Airbnb Rental Income: $1636

Traditional Rental Income: $3022

Airbnb ROI: -0.29%