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 315 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
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.	$1,815,000	Airbnb cash on cash: N/A Traditional cash on cash: 3.07% Airbnb Rental Income: $null Traditional Rental Income: $9335 Airbnb ROI: N/A Traditional ROI: 3.07%
660 EGRET PLACE DRIVE Winter Garden, FL Under contract-accepting backup offers. "What if your next home wasnât just a house â ...	4 beds \| 3 baths \| 2,647 sq.ft.	$548,500	Airbnb cash on cash: 5.89% Traditional cash on cash: 4.33% Airbnb Rental Income: $5064 Traditional Rental Income: $3234 Airbnb ROI: 5.89% Traditional ROI: 4.33%
2018 BAY CLOVER DRIVE Winter Garden, FL SELLER CONTRIBUTION OF $10,000 TOWARDS NEW ROOF!! This beautiful 4-bedroom, 2-bathroom ho...	4 beds \| 2 baths \| 2,526 sq.ft.	$580,000	Airbnb cash on cash: 5.36% Traditional cash on cash: 2.73% Airbnb Rental Income: $5064 Traditional Rental Income: $2610 Airbnb ROI: 5.36% Traditional ROI: 2.73%
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%
17556 DEER ISLE CIRCLE Winter Garden, FL Welcome to 17556 Deer Isle Circle in the gated community of Deer Island. This beautifully ...	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%
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.	$589,900	Airbnb cash on cash: -0.34% Traditional cash on cash: 2.23% Airbnb Rental Income: $1636 Traditional Rental Income: $2588 Airbnb ROI: -0.34% Traditional ROI: 2.23%
14955 SPEER LAKE DRIVE Winter Garden, FL WATER VIEW - Bring your Boat!! Welcome home to this incredible home in sought after Signa...	4 beds \| 4 baths \| 2,722 sq.ft.	$650,000	Airbnb cash on cash: 4.34% Traditional cash on cash: 3.7% Airbnb Rental Income: $5064 Traditional Rental Income: $3645 Airbnb ROI: 4.34% Traditional ROI: 3.7%
14645 SCOTT KEY DRIVE Winter Garden, FL PRICE REDUCED...Welcome to Watermark built by Meritage homes, a luxury resort style commun...	4 beds \| 4 baths \| 3,427 sq.ft.	$887,000	Airbnb cash on cash: 2.21% Traditional cash on cash: 1.93% Airbnb Rental Income: $5064 Traditional Rental Income: $3797 Airbnb ROI: 2.21% Traditional ROI: 1.93%
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%
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.	$485,000	Airbnb cash on cash: 0.29% Traditional cash on cash: 2.6% Airbnb Rental Income: $1636 Traditional Rental Income: $2226 Airbnb ROI: 0.29% Traditional ROI: 2.6%
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 Beautiful Waterleigh Move-In Ready Home with Resort-Style Amenities This 3-bed, 2-bath si...	3 beds \| 2 baths \| 1,685 sq.ft.	$470,000	Airbnb cash on cash: -0.67% Traditional cash on cash: 1.91% Airbnb Rental Income: $1636 Traditional Rental Income: $2308 Airbnb ROI: -0.67% Traditional ROI: 1.91%
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%
6238 MANUSCRIPT STREET Winter Garden, FL Under contract-accepting backup offers. One or more photo(s) has been virtually staged. We...	4 beds \| 4 baths \| 2,759 sq.ft.	$599,000	Airbnb cash on cash: 4.23% Traditional cash on cash: 3.72% Airbnb Rental Income: $5064 Traditional Rental Income: $3744 Airbnb ROI: 4.23% Traditional ROI: 3.72%
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%
975 SADIE LANE Winter Garden, FL CUSTOM SALTWATER POOL HOME ON HALF-ACRE LOT WITH PRIVATE GARDEN OASIS! Set on a spaciou...	2 beds \| 2 baths \| 1,732 sq.ft.	$535,000	Airbnb cash on cash: 0.91% Traditional cash on cash: 2.47% Airbnb Rental Income: $2340 Traditional Rental Income: $2543 Airbnb ROI: 0.91% Traditional ROI: 2.47%
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%
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%
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 #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%
14501 GROVE RESORT AVENUE #3636 Winter Garden, FL Welcome to the largest 2 bedroom/2 bath Cypress Model condo at the 4-Star rated Grove Reso...	2 beds \| 2 baths \| 1,434 sq.ft.	$239,900	Airbnb cash on cash: -1.05% Traditional cash on cash: 0.49% Airbnb Rental Income: $2340 Traditional Rental Income: $2109 Airbnb ROI: -1.05% Traditional ROI: 0.49%
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%
14501 GROVE RESORT AVENUE #1220 Winter Garden, FL Great Location â Steps from Resort Amenities at The Grove! Enjoy the ultimate Orlando v...	2 beds \| 2 baths \| 1,375 sq.ft.	$325,890	Airbnb cash on cash: -0.18% Traditional cash on cash: 1.43% Airbnb Rental Income: $2340 Traditional Rental Income: $2255 Airbnb ROI: -0.18% Traditional ROI: 1.43%
15058 SAWGRASS BLUFF DRIVE Winter Garden, FL Welcome to your move-in ready haven in Winter Garden's highly desirable Johns Lake Pointe ...	4 beds \| 3 baths \| 2,626 sq.ft.	$630,000	Airbnb cash on cash: 4.45% Traditional cash on cash: 2.74% Airbnb Rental Income: $5064 Traditional Rental Income: $3031 Airbnb ROI: 4.45% Traditional ROI: 2.74%
2540 BLACK LAKE BOULEVARD Winter Garden, FL One or more photo(s) has been virtually staged. Welcome to a beautifully updated home that...	4 beds \| 3 baths \| 3,070 sq.ft.	$695,000	Airbnb cash on cash: 3.34% Traditional cash on cash: 2.41% Airbnb Rental Income: $5064 Traditional Rental Income: $3425 Airbnb ROI: 3.34% Traditional ROI: 2.41%
13748 WERRINGTON DRIVE Winter Garden, FL Seller offering concessions to compete with new construction in the area! 13748 Werringto...	3 beds \| 3 baths \| 1,796 sq.ft.	$515,000	Airbnb cash on cash: -0.54% Traditional cash on cash: 2.47% Airbnb Rental Income: $1636 Traditional Rental Income: $2624 Airbnb ROI: -0.54% Traditional ROI: 2.47%
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.	$490,000	Airbnb cash on cash: 5.96% Traditional cash on cash: 2.39% Airbnb Rental Income: $5064 Traditional Rental Income: $2395 Airbnb ROI: 5.96% Traditional ROI: 2.39%
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.	$230,000	Airbnb cash on cash: -1.07% Traditional cash on cash: 3.24% Airbnb Rental Income: $1636 Traditional Rental Income: $2112 Airbnb ROI: -1.07% Traditional ROI: 3.24%
10386 ATWATER BAY DRIVE Winter Garden, FL Experience the best of resort-style living in the desirable Waterleigh community of Winter...	4 beds \| 3 baths \| 2,117 sq.ft.	$725,000	Airbnb cash on cash: 3.22% Traditional cash on cash: 1.41% Airbnb Rental Income: $5064 Traditional Rental Income: $2805 Airbnb ROI: 3.22% Traditional ROI: 1.41%
634 BURCH AVENUE Winter Garden, FL Welcome to your dream home in the heart of Downtown Winter Gardenâs golf cart districtâ...	4 beds \| 4 baths \| 2,448 sq.ft.	$664,000	Airbnb cash on cash: 5.13% Traditional cash on cash: 4.64% Airbnb Rental Income: $5064 Traditional Rental Income: $3731 Airbnb ROI: 5.13% Traditional ROI: 4.64%
15452 FIRELIGHT DRIVE 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.	$649,900	Airbnb cash on cash: 4.58% Traditional cash on cash: 3.44% Airbnb Rental Income: $5064 Traditional Rental Income: $3338 Airbnb ROI: 4.58% Traditional ROI: 3.44%
14212 MURCOTT BLOSSOM BOULEVARD Winter Garden, FL Welcome to your new home in Lakeview Pointe â Horizon West! Built in 2016, this beautif...	3 beds \| 3 baths \| 1,954 sq.ft.	$514,990	Airbnb cash on cash: -0.57% Traditional cash on cash: 3.12% Airbnb Rental Income: $1636 Traditional Rental Income: $2951 Airbnb ROI: -0.57% Traditional ROI: 3.12%
12216 ENCORE AT OVATION WAY Winter Garden, FL Welcome to 12216 Encore at Ovation Wayâa dream home for families who want it all: luxury...	4 beds \| 3 baths \| 2,889 sq.ft.	$679,000	Airbnb cash on cash: 3.41% Traditional cash on cash: 3.05% Airbnb Rental Income: $5064 Traditional Rental Income: $3807 Airbnb ROI: 3.41% Traditional ROI: 3.05%
15349 MURCOTT HARVEST LOOP Winter Garden, FL This two story house featuring 4 bedrooms, 3 baths with Orange County National Golf court ...	4 beds \| 3 baths \| 2,469 sq.ft.	$680,000	Airbnb cash on cash: 3.97% Traditional cash on cash: 2.96% Airbnb Rental Income: $5064 Traditional Rental Income: $3392 Airbnb ROI: 3.97% Traditional ROI: 2.96%
3227 BUOY CIRCLE Winter Garden, FL Under contract-accepting backup offers. Welcome to this MOVE-IN READY one-story 4 bed/3 Ba...	4 beds \| 3 baths \| 2,070 sq.ft.	$629,000	Airbnb cash on cash: 4.14% Traditional cash on cash: 2.66% Airbnb Rental Income: $5064 Traditional Rental Income: $3164 Airbnb ROI: 4.14% Traditional ROI: 2.66%
312 ENGLISH LAKE DRIVE Winter Garden, FL Living beautifully in a Winter Garden neighborhood, just moments from the Roper YMCA and W...	4 beds \| 3 baths \| 2,833 sq.ft.	$950,000	Airbnb cash on cash: 2.26% Traditional cash on cash: 1.07% Airbnb Rental Income: $5064 Traditional Rental Income: $2986 Airbnb ROI: 2.26% Traditional ROI: 1.07%

Your search for investment property begins and ends here

Single Family Homes for Sale in Winter Garden, FL

1224 UNION CLUB DRIVE

Winter Garden, FL

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

$1,815,000

Airbnb cash on cash: N/A

Traditional cash on cash: 3.07%

Airbnb Rental Income: $null

Traditional Rental Income: $9335

Airbnb ROI: N/A

Traditional ROI: 3.07%

660 EGRET PLACE DRIVE

Winter Garden, FL

4 beds | 3 baths | 2,647 sq.ft.

$548,500

Airbnb cash on cash: 5.89%

Traditional cash on cash: 4.33%

Airbnb Rental Income: $5064

Traditional Rental Income: $3234

Airbnb ROI: 5.89%

Traditional ROI: 4.33%

2018 BAY CLOVER DRIVE

Winter Garden, FL

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

$580,000

Airbnb cash on cash: 5.36%

Traditional cash on cash: 2.73%

Airbnb Rental Income: $5064

Traditional Rental Income: $2610

Airbnb ROI: 5.36%

Traditional ROI: 2.73%

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%

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%

Traditional ROI: 3.43%

714 PARKMONT PLACE

Winter Garden, FL

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

$589,900

Airbnb cash on cash: -0.34%

Traditional cash on cash: 2.23%

Airbnb Rental Income: $1636

Traditional Rental Income: $2588

Airbnb ROI: -0.34%