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.

Investment Property for Sale in Winter Garden, FL

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PROPERTY	DETAILS	SALE PRICE	INVESTMENT PERFORMANCE
1073 VINSETTA CIRCLE Winter Garden, FL Dare to dream of this 4/3.5 Winter Garden turn-key single family home in the exclusive com...	4 beds \| 4 baths \| 3,568 sq.ft.	$815,000	Airbnb cash on cash: 3.38% Traditional cash on cash: 3.82% Airbnb Rental Income: $5064 Traditional Rental Income: $4365 Airbnb ROI: 3.38% Traditional ROI: 3.82%
1226 SCARLET OAK LOOP Winter Garden, FL Under contract-accepting backup offers. Discover your new retreat in this delightful 3-bed...	3 beds \| 3 baths \| 1,592 sq.ft.	$355,000	Airbnb cash on cash: 0.32% Traditional cash on cash: 3.9% Airbnb Rental Income: $1636 Traditional Rental Income: $2366 Airbnb ROI: 0.32% Traditional ROI: 3.9%
7224 DESERT MANDARIN STREET Winter Garden, FL Welcome to the crown jewel of the neighborhood! This stunning 3-bedroom, 2.5-bathroom home...	3 beds \| 3 baths \| 1,657 sq.ft.	$549,000	Airbnb cash on cash: 0.21% Traditional cash on cash: 2.57% Airbnb Rental Income: $1636 Traditional Rental Income: $2384 Airbnb ROI: 0.21% Traditional ROI: 2.57%
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.	$835,000	Airbnb cash on cash: 3.14% Traditional cash on cash: 5.39% Airbnb Rental Income: $5064 Traditional Rental Income: $5780 Airbnb ROI: 3.14% Traditional ROI: 5.39%
1569 VICTORIA WAY Winter Garden, FL Located in the desirable community of Tuscany, this four-bedroom two bath custom-built hom...	4 beds \| 2 baths \| 2,258 sq.ft.	$590,000	Airbnb cash on cash: 5.04% Traditional cash on cash: 3.45% Airbnb Rental Income: $5064 Traditional Rental Income: $3157 Airbnb ROI: 5.04% Traditional ROI: 3.45%
1060 VINSETTA CIRCLE Winter Garden, FL Immaculate single-story pool home sitting on a corner lot in the secluded enclave of Avalo...	4 beds \| 3 baths \| 2,704 sq.ft.	$750,000	Airbnb cash on cash: 3.77% Traditional cash on cash: 2.4% Airbnb Rental Income: $5064 Traditional Rental Income: $3073 Airbnb ROI: 3.77% Traditional ROI: 2.4%
14132 MURCOTT BLOSSOM BOULEVARD Winter Garden, FL Step into a lifestyle of luxury and convenience in this stunning former model home, where ...	4 beds \| 3 baths \| 2,726 sq.ft.	$715,000	Airbnb cash on cash: 3.67% Traditional cash on cash: 2.15% Airbnb Rental Income: $5064 Traditional Rental Income: $3015 Airbnb ROI: 3.67% Traditional ROI: 2.15%
14177 AVENUE OF THE GRVS Winter Garden, FL Nestled in the picturesque community of Signature Lakes in Independence, this beautifully ...	2 beds \| 3 baths \| 1,249 sq.ft.	$374,000	Airbnb cash on cash: 1.38% Traditional cash on cash: 2.63% Airbnb Rental Income: $2340 Traditional Rental Income: $2199 Airbnb ROI: 1.38% Traditional ROI: 2.63%
15691 ORANGE HARVEST LOOP Winter Garden, FL IMMACULATE TOWNHOME WITH ALL THE EXTRAS IN HIGHLY DESIRED WINTER GARDEN GATED COMMUNITY. T...	3 beds \| 3 baths \| 2,444 sq.ft.	$547,000	Airbnb cash on cash: -0.74% Traditional cash on cash: 2.57% Airbnb Rental Income: $1636 Traditional Rental Income: $2866 Airbnb ROI: -0.74% Traditional ROI: 2.57%
7612 LOON AVENUE Winter Garden, FL Under contract-accepting backup offers. Welcome to this exceptional 4-bedroom, 3-bathroom ...	4 beds \| 3 baths \| 2,133 sq.ft.	$599,900	Airbnb cash on cash: 4.75% Traditional cash on cash: 3.35% Airbnb Rental Income: $5064 Traditional Rental Income: $3242 Airbnb ROI: 4.75% Traditional ROI: 3.35%
13923 DANIELS LANDING CIRCLE Winter Garden, FL Under contract-accepting backup offers. Expect to be impressed with this updated townhome ...	2 beds \| 3 baths \| 1,233 sq.ft.	$319,900	Airbnb cash on cash: 2.37% Traditional cash on cash: 3.7% Airbnb Rental Income: $2340 Traditional Rental Income: $2160 Airbnb ROI: 2.37% Traditional ROI: 3.7%
16736 RUSTY ANCHOR ROAD Winter Garden, FL Introducing the exquisite Carlisle Plan, a beautiful single-story home featuring four bedr...	4 beds \| 3 baths \| 2,696 sq.ft.	$975,000	Airbnb cash on cash: 2.19% Traditional cash on cash: 1.47% Airbnb Rental Income: $5064 Traditional Rental Income: $3374 Airbnb ROI: 2.19% Traditional ROI: 1.47%
14494 WHITTRIDGE DRIVE Winter Garden, FL Experience luxury living in this beautifully remodeled 3-bedroom + office, 2.5-bath townho...	3 beds \| 3 baths \| 2,067 sq.ft.	$475,000	Airbnb cash on cash: 0.17% Traditional cash on cash: 3.35% Airbnb Rental Income: $1636 Traditional Rental Income: $2592 Airbnb ROI: 0.17% Traditional ROI: 3.35%
8024 JEREMY JOSEPH ALLEY Winter Garden, FL Exceedingly Captivating Energy-Efficient Townhome with Private Covered Courtyard! Situated...	3 beds \| 3 baths \| 1,644 sq.ft.	$449,000	Airbnb cash on cash: 0.07% Traditional cash on cash: 3.14% Airbnb Rental Income: $1636 Traditional Rental Income: $2466 Airbnb ROI: 0.07% Traditional ROI: 3.14%
2414 BALFORN TOWER WAY Winter Garden, FL This move-in-ready gem, with a new roof (02/24), new AC (2024), and a washer (2023) & drye...	4 beds \| 3 baths \| 2,428 sq.ft.	$619,900	Airbnb cash on cash: 4.41% Traditional cash on cash: 2.32% Airbnb Rental Income: $5064 Traditional Rental Income: $2820 Airbnb ROI: 4.41% Traditional ROI: 2.32%
14791 CRIMSON BLUFF ALLEY Winter Garden, FL Watermark a resort-style new community in Winter Garden, incredibly energy-efficient home...	3 beds \| 3 baths \| 2,094 sq.ft.	$559,900	Airbnb cash on cash: -0.42% Traditional cash on cash: 2.57% Airbnb Rental Income: $1636 Traditional Rental Income: $2740 Airbnb ROI: -0.42% Traditional ROI: 2.57%
14501 GROVE RESORT AVENUE #3338 Winter Garden, FL *MOTIVATED SELLERMOTIVATED SELLERMOTIVATED SELLER* Welcome to this NICE "THE GRO...	3 beds \| 2 baths \| 1,396 sq.ft.	$340,000	Airbnb cash on cash: -2.04% Traditional cash on cash: 0.79% Airbnb Rental Income: $1636 Traditional Rental Income: $2079 Airbnb ROI: -2.04% Traditional ROI: 0.79%
14815 TULLAMORE LOOP Winter Garden, FL Don't miss the chance to own this 4 Bedrooms 2 Bath Modern Fully REMODELED house. Once ent...	4 beds \| 2 baths \| 2,314 sq.ft.	$630,000	Airbnb cash on cash: 4.59% Traditional cash on cash: 2.09% Airbnb Rental Income: $5064 Traditional Rental Income: $2563 Airbnb ROI: 4.59% Traditional ROI: 2.09%
17000 RED BIRD ROAD Winter Garden, FL Gorgeous 2.25 acres of mature landscaping just 15 minutes from Disney and 5 minutes from H...	5 beds \| 4 baths \| 3,370 sq.ft.	$1,250,000	Airbnb cash on cash: N/A Traditional cash on cash: 2% Airbnb Rental Income: $null Traditional Rental Income: $4816 Airbnb ROI: N/A Traditional ROI: 2%
14501 GROVE RESORT AVENUE #2201 Winter Garden, FL Great New Price: $357,500. MOTIVATED SELLER OF THIS GREAT SABLE DESIGN CONDO FOR SALE AT...	3 beds \| 3 baths \| 1,544 sq.ft.	$357,500	Airbnb cash on cash: -3.03% Traditional cash on cash: 0.42% Airbnb Rental Income: $1636 Traditional Rental Income: $2334 Airbnb ROI: -3.03% Traditional ROI: 0.42%
336 ERON WAY #10 Winter Garden, FL Under contract-accepting backup offers. SUPERB LOCATION! IMMACCULATE quaint home made of S...	2 beds \| 2 baths \| 930 sq.ft.	$229,900	Airbnb cash on cash: 5.17% Traditional cash on cash: 5.62% Airbnb Rental Income: $2340 Traditional Rental Income: $1859 Airbnb ROI: 5.17% Traditional ROI: 5.62%
15116 DRAGON FLY COURT Winter Garden, FL One or more photo(s) has been virtually staged. Welcome to your future home, where eleganc...	4 beds \| 3 baths \| 2,449 sq.ft.	$642,000	Airbnb cash on cash: 4.34% Traditional cash on cash: 2.39% Airbnb Rental Income: $5064 Traditional Rental Income: $2862 Airbnb ROI: 4.34% Traditional ROI: 2.39%
4984 WILDWOOD POINTE ROAD Winter Garden, FL Charming 3-bedroom, 2.5-bathroom home in the desirable Orchard Hills community of Winter G...	3 beds \| 3 baths \| 1,997 sq.ft.	$560,000	Airbnb cash on cash: -0.63% Traditional cash on cash: 3.13% Airbnb Rental Income: $1636 Traditional Rental Income: $3142 Airbnb ROI: -0.63% Traditional ROI: 3.13%
14501 Grove Resort Avenue #1617 Winter Garden, FL Complete turnkey unit with prime views to the lake, pool and Disney parks area. One of the...	2 beds \| 2 baths \| 1,375 sq.ft.	$499,000	Airbnb cash on cash: -0.83% Traditional cash on cash: 0.85% Airbnb Rental Income: $2340 Traditional Rental Income: $2545 Airbnb ROI: -0.83% Traditional ROI: 0.85%
8943 LAKESHORE POINTE DRIVE Winter Garden, FL ONE OF THE PRETTIEST LOCATIONS AND VIEWS IN LAKESHORE!! SHOWS BETTER THAN A MODEL WITH TO...	3 beds \| 3 baths \| 2,052 sq.ft.	$639,900	Airbnb cash on cash: -0.78% Traditional cash on cash: 2.27% Airbnb Rental Income: $1636 Traditional Rental Income: $2996 Airbnb ROI: -0.78% Traditional ROI: 2.27%
15326 BEAMLEIGH ROAD Winter Garden, FL Under contract-accepting backup offers. Welcome to charming Winter Garden, FL! This deligh...	3 beds \| 3 baths \| 1,828 sq.ft.	$465,000	Airbnb cash on cash: -0.05% Traditional cash on cash: 3.1% Airbnb Rental Income: $1636 Traditional Rental Income: $2548 Airbnb ROI: -0.05% Traditional ROI: 3.1%
14501 GROVE RESORT AVENUE #3535 Winter Garden, FL MOTIVATED SELLER; OWNER FINANCING AVAILABLE. BEAUTIFUL 2 BED/2 BATH LUXURY FULLY FURNISHED...	2 beds \| 2 baths \| 1,434 sq.ft.	$364,000	Airbnb cash on cash: -0.84% Traditional cash on cash: 0.42% Airbnb Rental Income: $2340 Traditional Rental Income: $2193 Airbnb ROI: -0.84% Traditional ROI: 0.42%
16253 PEBBLE BLUFF LOOP Winter Garden, FL Waterleigh is a resort-style living community. Situated on a picturesque setting of over 1...	3 beds \| 2 baths \| 1,700 sq.ft.	$505,000	Airbnb cash on cash: -0.56% Traditional cash on cash: 1.89% Airbnb Rental Income: $1636 Traditional Rental Income: $2332 Airbnb ROI: -0.56% Traditional ROI: 1.89%
7570 BISHOP SQUARE DRIVE Winter Garden, FL Welcome to Your New Beginning! This charming 4-bedroom, 2-bath home in the highly sought-a...	4 beds \| 2 baths \| 1,952 sq.ft.	$565,000	Airbnb cash on cash: 4.71% Traditional cash on cash: 1.72% Airbnb Rental Income: $5064 Traditional Rental Income: $2449 Airbnb ROI: 4.71% Traditional ROI: 1.72%
14501 GROVE RESORT AVENUE #1440 Winter Garden, FL NEW PRICE!!! OVERSIZED 2 BEDROOM WITH ROTUNDA VIEW WITH ALL OF THE CONVENIENCE OF TOWER 1....	2 beds \| 2 baths \| 1,375 sq.ft.	$298,000	Airbnb cash on cash: 3.3% Traditional cash on cash: 5.44% Airbnb Rental Income: $2340 Traditional Rental Income: $2362 Airbnb ROI: 3.3% Traditional ROI: 5.44%
208 SURPRISE DRIVE Winter Garden, FL Under contract-accepting backup offers. Location, Location, Location! This spectacular 2,5...	3 beds \| 3 baths \| 2,577 sq.ft.	$818,900	Airbnb cash on cash: -0.85% Traditional cash on cash: 2.01% Airbnb Rental Income: $1636 Traditional Rental Income: $3354 Airbnb ROI: -0.85% Traditional ROI: 2.01%
14501 GROVE RESORT AVENUE #1535 Winter Garden, FL MOTIVATED SELLER. BEAUTIFUL FULLY FURNISHED LUXURY 3 BED 2 BATH CONDO WITH GREAT VIEWS. T...	3 beds \| 2 baths \| 1,396 sq.ft.	$428,990	Airbnb cash on cash: -2.02% Traditional cash on cash: 0.28% Airbnb Rental Income: $1636 Traditional Rental Income: $2098 Airbnb ROI: -2.02% Traditional ROI: 0.28%
1755 DELAFIELD DRIVE Winter Garden, FL This beautifully updated 4-bedroom home is located in the tranquil, gated community of Eme...	4 beds \| 3 baths \| 2,934 sq.ft.	$628,000	Airbnb cash on cash: 4.63% Traditional cash on cash: 2.81% Airbnb Rental Income: $5064 Traditional Rental Income: $2965 Airbnb ROI: 4.63% Traditional ROI: 2.81%
14501 GROVE RESORT AVENUE #1443 Winter Garden, FL MOTIVATED SELLER AT THE GROVE RESORT & WATER PARK. CONDO-HOTEL, LOCATED MINUTES FROM WALT ...	2 beds \| 2 baths \| 1,375 sq.ft.	$352,500	Airbnb cash on cash: -0.39% Traditional cash on cash: 0.79% Airbnb Rental Income: $2340 Traditional Rental Income: $2152 Airbnb ROI: -0.39% Traditional ROI: 0.79%
470 REGAL DOWNS CIRCLE Winter Garden, FL PRICE REDUCTION!!! First Time Homebuyers - Special Financing available with potentially Z...	4 beds \| 3 baths \| 2,316 sq.ft.	$585,000	Airbnb cash on cash: 5.8% Traditional cash on cash: 4.48% Airbnb Rental Income: $5064 Traditional Rental Income: $3311 Airbnb ROI: 5.8% Traditional ROI: 4.48%
4251 WILLOW BAY DR Winter Garden, FL RARE OPPORTUNITY âthis home has GOLF and WATER views, in a charming CUL-DE-SAC with larg...	3 beds \| 3 baths \| 2,612 sq.ft.	$822,599	Airbnb cash on cash: -0.86% Traditional cash on cash: 2.03% Airbnb Rental Income: $1636 Traditional Rental Income: $3393 Airbnb ROI: -0.86% Traditional ROI: 2.03%
15060 STUTTGART ALLEY Winter Garden, FL Beautiful 2 story house in desirable Watermark in Winter Garden. This house includes stain...	4 beds \| 3 baths \| 1,696 sq.ft.	$520,000	Airbnb cash on cash: 5.56% Traditional cash on cash: 2.19% Airbnb Rental Income: $5064 Traditional Rental Income: $2395 Airbnb ROI: 5.56% Traditional ROI: 2.19%
16269 ADMIRALS COVE LANE Winter Garden, FL Welcome to this pristine, modern townhouse in the highly desirable Waterleigh community in...	3 beds \| 3 baths \| 1,568 sq.ft.	$412,500	Airbnb cash on cash: -0.12% Traditional cash on cash: 3.13% Airbnb Rental Income: $1636 Traditional Rental Income: $2433 Airbnb ROI: -0.12% Traditional ROI: 3.13%
2640 BALFORN TOWER WAY Winter Garden, FL One or more photo(s) has been virtually staged. Welcome to the perfect location for your d...	4 beds \| 2 baths \| 1,980 sq.ft.	$479,000	Airbnb cash on cash: 6.59% Traditional cash on cash: 3.05% Airbnb Rental Income: $5064 Traditional Rental Income: $2444 Airbnb ROI: 6.59% Traditional ROI: 3.05%
13633 DANIELS LANDING CIRCLE Winter Garden, FL Do not miss out on this unique opportunity to see this property within the gated community...	3 beds \| 3 baths \| 1,455 sq.ft.	$355,000	Airbnb cash on cash: 0.22% Traditional cash on cash: 3.24% Airbnb Rental Income: $1636 Traditional Rental Income: $2184 Airbnb ROI: 0.22% Traditional ROI: 3.24%

Real Estate investment in Winter-garden, FL

There are 418 properties for sale in the city of Winter Garden . The median list price in Winter Garden is $568,857 and the average price per square foot is $243. In November 2024, the average monthly cash on cash return in Winter Garden is 3.00%. The average monthly rental income in Winter Garden is $2,750.

Winter-garden, FL Real Estate Investing: FAQs for Buyers, Sellers and Investors

There are 418 investment properties available for sale in Winter-garden.

In 2024, the best neighborhood to buy investment property is Winter Garden.

The ROI for Long-Term is higher than the Short-Term in Winter-garden with average rental income of $2,750.

Your search for investment property begins and ends here

Investment Property for Sale in Winter Garden, FL

1073 VINSETTA CIRCLE

Winter Garden, FL

4 beds | 4 baths | 3,568 sq.ft.

$815,000

Airbnb cash on cash: 3.38%

Traditional cash on cash: 3.82%

Airbnb Rental Income: $5064

Traditional Rental Income: $4365

Airbnb ROI: 3.38%

Traditional ROI: 3.82%

1226 SCARLET OAK LOOP

Winter Garden, FL

3 beds | 3 baths | 1,592 sq.ft.

$355,000

Airbnb cash on cash: 0.32%

Traditional cash on cash: 3.9%

Airbnb Rental Income: $1636

Traditional Rental Income: $2366

Airbnb ROI: 0.32%

Traditional ROI: 3.9%

7224 DESERT MANDARIN STREET

Winter Garden, FL

3 beds | 3 baths | 1,657 sq.ft.

$549,000

Airbnb cash on cash: 0.21%

Traditional cash on cash: 2.57%

Airbnb Rental Income: $1636

Traditional Rental Income: $2384

Airbnb ROI: 0.21%

Traditional ROI: 2.57%

14372 SUNBRIDGE CIRCLE

Winter Garden, FL

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

$835,000

Airbnb cash on cash: 3.14%

Traditional cash on cash: 5.39%

Airbnb Rental Income: $5064

Traditional Rental Income: $5780

Airbnb ROI: 3.14%

Traditional ROI: 5.39%

1569 VICTORIA WAY

Winter Garden, FL

4 beds | 2 baths | 2,258 sq.ft.

$590,000

Airbnb cash on cash: 5.04%

Traditional cash on cash: 3.45%

Airbnb Rental Income: $5064

Traditional Rental Income: $3157

Airbnb ROI: 5.04%

Traditional ROI: 3.45%

1060 VINSETTA CIRCLE

Winter Garden, FL

4 beds | 3 baths | 2,704 sq.ft.

$750,000

Airbnb cash on cash: 3.77%

Traditional cash on cash: 2.4%

Airbnb Rental Income: $5064

Traditional Rental Income: $3073

Airbnb ROI: 3.77%

Traditional ROI: 2.4%

14132 MURCOTT BLOSSOM BOULEVARD

Winter Garden, FL

4 beds | 3 baths | 2,726 sq.ft.

$715,000

Airbnb cash on cash: 3.67%

Traditional cash on cash: 2.15%

Airbnb Rental Income: $5064

Traditional Rental Income: $3015

Airbnb ROI: 3.67%

Traditional ROI: 2.15%

14177 AVENUE OF THE GRVS

Winter Garden, FL

2 beds | 3 baths | 1,249 sq.ft.

$374,000

Airbnb cash on cash: 1.38%

Traditional cash on cash: 2.63%

Airbnb Rental Income: $2340

Traditional Rental Income: $2199

Airbnb ROI: 1.38%