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.

Memphis Investment Property for Sale in Winter Garden, FL

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

Showing 409 Memphis 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
1224 UNION CLUB DRIVE Winter Garden, FL EXQUISITE WATERFRONT RESIDENCE blends luxury and timeless Florida charm in award-winning O...	5 beds \| 6 baths \| 5,441 sq.ft.	$1,775,000	Airbnb cash on cash: N/A Traditional cash on cash: 3.17% Airbnb Rental Income: $null Traditional Rental Income: $9335 Airbnb ROI: N/A Traditional ROI: 3.17%
2018 BAY CLOVER DRIVE Winter Garden, FL SELLER WILL REPLACE ROOF PRIOR CLOSING WITH AN ACCEPTABLE OFFER!! This beautiful 4-bedroo...	4 beds \| 2 baths \| 2,526 sq.ft.	$578,000	Airbnb cash on cash: 5.38% Traditional cash on cash: 2.75% Airbnb Rental Income: $5064 Traditional Rental Income: $2610 Airbnb ROI: 5.38% Traditional ROI: 2.75%
706 GRANDHAVEN WAY Winter Garden, FL Under contract-accepting backup offers. Welcome to 706 Grandhaven Way, a beautifully updat...	4 beds \| 3 baths \| 1,904 sq.ft.	$535,000	Airbnb cash on cash: 6.04% Traditional cash on cash: 3.29% Airbnb Rental Income: $5064 Traditional Rental Income: $2655 Airbnb ROI: 6.04% Traditional ROI: 3.29%
338 WINDFORD COURT Winter Garden, FL Discover this move-in ready 3-bedroom, 2-bathroom CBS construction home in Winter Garden, ...	3 beds \| 2 baths \| 1,050 sq.ft.	$330,000	Airbnb cash on cash: 1.75% Traditional cash on cash: 4.18% Airbnb Rental Income: $1636 Traditional Rental Income: $1930 Airbnb ROI: 1.75% Traditional ROI: 4.18%
14488 WHITTRIDGE DRIVE Winter Garden, FL Unique opportunity in highly desired Independence (Winter Garden)! This corner, end-unit t...	4 beds \| 3 baths \| 2,159 sq.ft.	$479,000	Airbnb cash on cash: 6.12% Traditional cash on cash: 3.61% Airbnb Rental Income: $5064 Traditional Rental Income: $2907 Airbnb ROI: 6.12% Traditional ROI: 3.61%
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.	$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%
17556 DEER ISLE CIRCLE Winter Garden, FL $25,000 SELLER CONCESSION TOWARDS CLOSING COSTS OR RATE BUY DOWN>> Welcome to 17556 Deer I...	4 beds \| 4 baths \| 3,214 sq.ft.	$1,299,999	Airbnb cash on cash: 1.36% Traditional cash on cash: 2.16% Airbnb Rental Income: $5064 Traditional Rental Income: $5002 Airbnb ROI: 1.36% Traditional ROI: 2.16%
15504 SANDFIELD LOOP Winter Garden, FL Welcome to the gated community of Reserve at Carriage Pointe, where sophistication meets c...	4 beds \| 4 baths \| 4,126 sq.ft.	$899,999	Airbnb cash on cash: 2.67% Traditional cash on cash: 3.43% Airbnb Rental Income: $5064 Traditional Rental Income: $4669 Airbnb ROI: 2.67% Traditional ROI: 3.43%
14815 DRIFTWATER DRIVE Winter Garden, FL Under contract-accepting backup offers. One or more photo(s) has been virtually staged. Ne...	4 beds \| 3 baths \| 1,997 sq.ft.	$439,000	Airbnb cash on cash: 5.93% Traditional cash on cash: 2.66% Airbnb Rental Income: $5064 Traditional Rental Income: $2686 Airbnb ROI: 5.93% Traditional ROI: 2.66%
8164 WOOD SAGE DRIVE Winter Garden, FL Welcome to this beautifully maintained 3-bedroom, 2.5-bath townhome in the highly desirabl...	3 beds \| 3 baths \| 1,853 sq.ft.	$449,900	Airbnb cash on cash: -0.24% Traditional cash on cash: 3.3% Airbnb Rental Income: $1636 Traditional Rental Income: $2668 Airbnb ROI: -0.24% Traditional ROI: 3.3%
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.	$579,900	Airbnb cash on cash: -0.33% Traditional cash on cash: 2.28% Airbnb Rental Income: $1636 Traditional Rental Income: $2588 Airbnb ROI: -0.33% Traditional ROI: 2.28%
1352 SCARLET OAK LOOP Winter Garden, FL Under contract-accepting backup offers. Welcome to MAINTENANCE-FREE living in the GATED co...	3 beds \| 3 baths \| 1,589 sq.ft.	$368,000	Airbnb cash on cash: 0.36% Traditional cash on cash: 3.8% Airbnb Rental Income: $1636 Traditional Rental Income: $2362 Airbnb ROI: 0.36% Traditional ROI: 3.8%
9404 WOODCRANE DRIVE Winter Garden, FL Under contract-accepting backup offers. Welcome to 9404 Woodcrane Drive in Winter Gardenâ...	3 beds \| 3 baths \| 2,058 sq.ft.	$500,000	Airbnb cash on cash: -0.02% Traditional cash on cash: 3.56% Airbnb Rental Income: $1636 Traditional Rental Income: $2850 Airbnb ROI: -0.02% Traditional ROI: 3.56%
15261 HONEYBELL DRIVE Winter Garden, FL Welcome to this professionally designed and fully remodeled two-story home in the highly s...	4 beds \| 4 baths \| 3,084 sq.ft.	$829,000	Airbnb cash on cash: 2.81% Traditional cash on cash: 2.56% Airbnb Rental Income: $5064 Traditional Rental Income: $3838 Airbnb ROI: 2.81% Traditional ROI: 2.56%
900 WALKERS GROVE LANE Winter Garden, FL Welcome to 900 Walkers Grove Lane, a stunning home located in the desirable Downtown Winte...	3 beds \| 3 baths \| 1,905 sq.ft.	$485,000	Airbnb cash on cash: -0.11% Traditional cash on cash: 3.3% Airbnb Rental Income: $1636 Traditional Rental Income: $2723 Airbnb ROI: -0.11% Traditional ROI: 3.3%
6837 PASTURELANDS PLACE Winter Garden, FL Beautifully maintained 3-bedroom, 2-bathroom home located in Signature Lakes community. Fe...	3 beds \| 2 baths \| 1,650 sq.ft.	$475,000	Airbnb cash on cash: 0.31% Traditional cash on cash: 2.68% Airbnb Rental Income: $1636 Traditional Rental Income: $2226 Airbnb ROI: 0.31% Traditional ROI: 2.68%
1873 WHITE FEATHER LOOP Winter Garden, FL Under contract-accepting backup offers. HUGE PRICE DROPPED!! Ready to move in. This well-d...	4 beds \| 3 baths \| 2,418 sq.ft.	$549,000	Airbnb cash on cash: 5.28% Traditional cash on cash: 3.07% Airbnb Rental Income: $5064 Traditional Rental Income: $2899 Airbnb ROI: 5.28% Traditional ROI: 3.07%
15506 TIDAL COVE ALLEY Winter Garden, FL PRICE IMPROVEMENT! With a $10,000 price adjustment and $5,000 toward buyerâs closing cos...	3 beds \| 2 baths \| 1,685 sq.ft.	$460,000	Airbnb cash on cash: -0.66% Traditional cash on cash: 1.97% Airbnb Rental Income: $1636 Traditional Rental Income: $2308 Airbnb ROI: -0.66% Traditional ROI: 1.97%
10131 AUDUBON TRACE ALLEY Winter Garden, FL BEST PRICE with MOST UPGRADES! SINGLE STORY Laurel on a PREMIUM LOT with a LARGE PARK for...	3 beds \| 2 baths \| 1,685 sq.ft.	$499,000	Airbnb cash on cash: -0.68% Traditional cash on cash: 2.03% Airbnb Rental Income: $1636 Traditional Rental Income: $2440 Airbnb ROI: -0.68% Traditional ROI: 2.03%
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: 0.48% Airbnb Rental Income: $1636 Traditional Rental Income: $2171 Airbnb ROI: -2.56% Traditional ROI: 0.48%
213 W TILDEN STREET Winter Garden, FL One of a kind home located in the heart of DOWNTOWN WINTER GARDEN!! This...	4 beds \| 2 baths \| 2,100 sq.ft.	$789,000	Airbnb cash on cash: 3.34% Traditional cash on cash: 1.56% Airbnb Rental Income: $5064 Traditional Rental Income: $2722 Airbnb ROI: 3.34% Traditional ROI: 1.56%
8919 Lakeshore Pointe Drive Winter Garden, FL This spacious 3-bedrooms , 3.5 bathrooms, Beautiful BONUS ROOM above the garage offers 2.5...	3 beds \| 3 baths \| 2,581 sq.ft.	$639,900	Airbnb cash on cash: -0.04% Traditional cash on cash: 3% Airbnb Rental Income: $1636 Traditional Rental Income: $2987 Airbnb ROI: -0.04% Traditional ROI: 3%
15594 HAMLIN BLOSSOM AVENUE Winter Garden, FL Immaculate 4-bedroom, 2 1/2 bathroom home available for immediate move-in in the highly so...	4 beds \| 3 baths \| 3,091 sq.ft.	$779,900	Airbnb cash on cash: 3.25% Traditional cash on cash: 2.06% Airbnb Rental Income: $5064 Traditional Rental Income: $3168 Airbnb ROI: 3.25% Traditional ROI: 2.06%
8256 BAYVIEW CROSSING DRIVE Winter Garden, FL POOL HOME â UPGRADED! Welcome to this 4-bed, 3.5-bath retreat in the highly sought-afte...	4 beds \| 4 baths \| 2,557 sq.ft.	$699,000	Airbnb cash on cash: 3.12% Traditional cash on cash: 2.38% Airbnb Rental Income: $5064 Traditional Rental Income: $3546 Airbnb ROI: 3.12% Traditional ROI: 2.38%
3255 BUOY CIRCLE Winter Garden, FL Why wait for new construction when you can move right into this like-new 2020 Pulte home? ...	3 beds \| 2 baths \| 2,190 sq.ft.	$560,000	Airbnb cash on cash: -0.61% Traditional cash on cash: 2.12% Airbnb Rental Income: $1636 Traditional Rental Income: $2604 Airbnb ROI: -0.61% Traditional ROI: 2.12%
6578 CALAMONDIN DRIVE Winter Garden, FL Under contract-accepting backup offers. This luxury 4bd/3ba townhouse is located in the hi...	4 beds \| 3 baths \| 1,853 sq.ft.	$427,000	Airbnb cash on cash: 6.16% Traditional cash on cash: 2.62% Airbnb Rental Income: $5064 Traditional Rental Income: $2616 Airbnb ROI: 6.16% Traditional ROI: 2.62%
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.	$450,000	Airbnb cash on cash: -0.9% Traditional cash on cash: 0.96% Airbnb Rental Income: $2340 Traditional Rental Income: $2545 Airbnb ROI: -0.9% Traditional ROI: 0.96%
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: 3.24% 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.	$479,900	Airbnb cash on cash: -0.54% Traditional cash on cash: 2.04% Airbnb Rental Income: $1636 Traditional Rental Income: $2332 Airbnb ROI: -0.54% Traditional ROI: 2.04%
14421 VASHONS WAY Winter Garden, FL Experience the best of Florida living just 20 minutes from Disney! This move-in ready 2 be...	2 beds \| 3 baths \| 1,088 sq.ft.	$359,900	Airbnb cash on cash: 2.27% Traditional cash on cash: 3.04% Airbnb Rental Income: $2340 Traditional Rental Income: $2020 Airbnb ROI: 2.27% Traditional ROI: 3.04%
17661 DAVENPORT ROAD Winter Garden, FL Modern Luxury Lakefront Living on Nearly 1.5 Acres in Winter Garden! Welcome to this fully...	3 beds \| 4 baths \| 2,400 sq.ft.	$1,199,000	Airbnb cash on cash: -0.8% Traditional cash on cash: 2.95% Airbnb Rental Income: $1636 Traditional Rental Income: $5347 Airbnb ROI: -0.8% Traditional ROI: 2.95%
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.	$285,000	Airbnb cash on cash: -0.72% Traditional cash on cash: 1.52% Airbnb Rental Income: $2340 Traditional Rental Income: $2362 Airbnb ROI: -0.72% Traditional ROI: 1.52%
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.	$319,000	Airbnb cash on cash: -3.32% Traditional cash on cash: 0.01% Airbnb Rental Income: $1636 Traditional Rental Income: $2174 Airbnb ROI: -3.32% Traditional ROI: 0.01%
16512 SEA GLASS STREET Winter Garden, FL Under contract-accepting backup offers. Welcome to 16512 Sea Glass Street, a beautifully u...	4 beds \| 4 baths \| 2,472 sq.ft.	$599,000	Airbnb cash on cash: 4.14% Traditional cash on cash: 3.26% Airbnb Rental Income: $5064 Traditional Rental Income: $3537 Airbnb ROI: 4.14% Traditional ROI: 3.26%
14501 GROVE RESORT AVENUE #2119 Winter Garden, FL This property presents a unique opportunity for real estate investors seeking a proven, in...	3 beds \| 2 baths \| 1,396 sq.ft.	$295,000	Airbnb cash on cash: -3.41% Traditional cash on cash: 0.42% Airbnb Rental Income: $1636 Traditional Rental Income: $2238 Airbnb ROI: -3.41% Traditional ROI: 0.42%
14501 GROVE RESORT AVENUE #3239 Winter Garden, FL The Orlando Investment Dream! This fully furnished 2-bedroom, 2-bathroom condo is located ...	2 beds \| 2 baths \| 1,375 sq.ft.	$315,000	Airbnb cash on cash: -0.67% Traditional cash on cash: 1.15% Airbnb Rental Income: $2340 Traditional Rental Income: $2300 Airbnb ROI: -0.67% Traditional ROI: 1.15%
149 S PARK AVENUE Winter Garden, FL Gorgeous former model in this beautiful masonry wrapped complex in the heart of Winter Gar...	3 beds \| 4 baths \| 2,938 sq.ft.	$1,049,000	Airbnb cash on cash: -1.71% Traditional cash on cash: 1.06% Airbnb Rental Income: $1636 Traditional Rental Income: $3876 Airbnb ROI: -1.71% Traditional ROI: 1.06%
14501 GROVE RESORT AVENUE #3636 Winter Garden, FL Just Reduced - LOWEST PRICE unit at The Grove Resort. Welcome to the largest 2 bedroom/2 b...	2 beds \| 2 baths \| 1,434 sq.ft.	$214,900	Airbnb cash on cash: -1.05% Traditional cash on cash: 0.65% Airbnb Rental Income: $2340 Traditional Rental Income: $2109 Airbnb ROI: -1.05% Traditional ROI: 0.65%
14501 GROVE RESORT AVENUE #3406 Winter Garden, FL This property presents a unique opportunity for real estate investors seeking a proven, in...	2 beds \| 2 baths \| 1,265 sq.ft.	$284,000	Airbnb cash on cash: -0.32% Traditional cash on cash: 1.3% Airbnb Rental Income: $2340 Traditional Rental Income: $2194 Airbnb ROI: -0.32% Traditional ROI: 1.3%
15113 MAYBERRY DRIVE Winter Garden, FL **This property qualifies for a closing cost credit up to $12,000 through the Sellerâs p...	5 beds \| 3 baths \| 2,927 sq.ft.	$925,000	Airbnb cash on cash: N/A Traditional cash on cash: 2.17% Airbnb Rental Income: $null Traditional Rental Income: $3908 Airbnb ROI: N/A Traditional ROI: 2.17%

Your search for investment property begins and ends here

Memphis Investment Property for Sale in Winter Garden, FL

1224 UNION CLUB DRIVE

Winter Garden, FL

5 beds | 6 baths | 5,441 sq.ft.

$1,775,000

Airbnb cash on cash: N/A

Traditional cash on cash: 3.17%

Airbnb Rental Income: $null

Traditional Rental Income: $9335

Airbnb ROI: N/A

Traditional ROI: 3.17%

2018 BAY CLOVER DRIVE

Winter Garden, FL

4 beds | 2 baths | 2,526 sq.ft.

$578,000

Airbnb cash on cash: 5.38%

Traditional cash on cash: 2.75%

Airbnb Rental Income: $5064

Traditional Rental Income: $2610

Airbnb ROI: 5.38%

Traditional ROI: 2.75%

706 GRANDHAVEN WAY

Winter Garden, FL

4 beds | 3 baths | 1,904 sq.ft.

$535,000

Airbnb cash on cash: 6.04%

Traditional cash on cash: 3.29%

Airbnb Rental Income: $5064

Traditional Rental Income: $2655

Airbnb ROI: 6.04%

Traditional ROI: 3.29%

338 WINDFORD COURT

Winter Garden, FL

3 beds | 2 baths | 1,050 sq.ft.

$330,000

Airbnb cash on cash: 1.75%

Traditional cash on cash: 4.18%

Airbnb Rental Income: $1636

Traditional Rental Income: $1930

Airbnb ROI: 1.75%

Traditional ROI: 4.18%

14488 WHITTRIDGE DRIVE

Winter Garden, FL

4 beds | 3 baths | 2,159 sq.ft.

$479,000

Airbnb cash on cash: 6.12%

Traditional cash on cash: 3.61%

Airbnb Rental Income: $5064

Traditional Rental Income: $2907

Airbnb ROI: 6.12%

Traditional ROI: 3.61%

14372 SUNBRIDGE CIRCLE

Winter Garden, FL

4 beds | 5 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%

17556 DEER ISLE CIRCLE

Winter Garden, FL

4 beds | 4 baths | 3,214 sq.ft.

$1,299,999

Airbnb cash on cash: 1.36%

Traditional cash on cash: 2.16%

Airbnb Rental Income: $5064

Traditional Rental Income: $5002

Airbnb ROI: 1.36%

Traditional ROI: 2.16%

15504 SANDFIELD LOOP

Winter Garden, FL

4 beds | 4 baths | 4,126 sq.ft.

$899,999

Airbnb cash on cash: 2.67%

Traditional cash on cash: 3.43%

Airbnb Rental Income: $5064

Traditional Rental Income: $4669

Airbnb ROI: 2.67%