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.

Fort Worth Investment Property for Sale in Winter Garden, FL

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

Showing 432 Fort Worth 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.	$1,850,000	Airbnb cash on cash: N/A Traditional cash on cash: 3% Airbnb Rental Income: $null Traditional Rental Income: $9335 Airbnb ROI: N/A Traditional ROI: 3%
660 EGRET PLACE DRIVE Winter Garden, FL "What if your next home wasnât just a house â but a complete lifestyle upgrade?" Welc...	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%
15318 SANDFIELD LOOP Winter Garden, FL Under contract-accepting backup offers. PRICED REDUCED. Step into this stunning residence ...	5 beds \| 4 baths \| 4,288 sq.ft.	$800,000	Airbnb cash on cash: N/A Traditional cash on cash: 3.35% Airbnb Rental Income: $null Traditional Rental Income: $4503 Airbnb ROI: N/A Traditional ROI: 3.35%
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.	$590,000	Airbnb cash on cash: 5.25% Traditional cash on cash: 2.67% Airbnb Rental Income: $5064 Traditional Rental Income: $2610 Airbnb ROI: 5.25% Traditional ROI: 2.67%
706 GRANDHAVEN WAY Winter Garden, FL Welcome to 706 Grandhaven Way, a beautifully updated home in the heart of Winter Gardenâ...	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%
13609 GLYNSHEL DRIVE Winter Garden, FL Stunning Executive Home in Gated Glynwood â One-of-a-Kind Custom Renovation! This modern...	4 beds \| 3 baths \| 2,923 sq.ft.	$879,000	Airbnb cash on cash: 2.88% Traditional cash on cash: 2.58% Airbnb Rental Income: $5064 Traditional Rental Income: $3783 Airbnb ROI: 2.88% Traditional ROI: 2.58%
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.	$950,000	Airbnb cash on cash: 2.48% Traditional cash on cash: 3.2% Airbnb Rental Income: $5064 Traditional Rental Income: $4669 Airbnb ROI: 2.48% Traditional ROI: 3.2%
14815 DRIFTWATER DRIVE Winter Garden, FL One or more photo(s) has been virtually staged. Welcome to 14815 Driftwater Driveâan upd...	4 beds \| 3 baths \| 1,997 sq.ft.	$450,000	Airbnb cash on cash: 5.76% Traditional cash on cash: 2.57% Airbnb Rental Income: $5064 Traditional Rental Income: $2686 Airbnb ROI: 5.76% Traditional ROI: 2.57%
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%
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 Welcome to 9404 Woodcrane Drive in Winter Gardenâs highly sought-after Horizon West area...	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%
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.	$500,000	Airbnb cash on cash: -0.14% Traditional cash on cash: 3.17% Airbnb Rental Income: $1636 Traditional Rental Income: $2723 Airbnb ROI: -0.14% Traditional ROI: 3.17%
1551 SCARLET OAK LOOP #B Winter Garden, FL Under contract-accepting backup offers. LOCATION, LOCATION, LOCATION! Welcome to Tucker Oa...	3 beds \| 3 baths \| 1,422 sq.ft.	$329,000	Airbnb cash on cash: 1.32% Traditional cash on cash: 4.77% Airbnb Rental Income: $1636 Traditional Rental Income: $2239 Airbnb ROI: 1.32% Traditional ROI: 4.77%
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%
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.	$795,000	Airbnb cash on cash: 3.3% Traditional cash on cash: 1.54% Airbnb Rental Income: $5064 Traditional Rental Income: $2722 Airbnb ROI: 3.3% Traditional ROI: 1.54%
14815 TULLAMORE LOOP Winter Garden, FL BACK ON MARKET, BUYER'S FINANCING FELL THROUGH. Don't miss the chance to own this 4 Bedroo...	4 beds \| 2 baths \| 2,314 sq.ft.	$595,000	Airbnb cash on cash: 4.91% Traditional cash on cash: 2.27% Airbnb Rental Income: $5064 Traditional Rental Income: $2563 Airbnb ROI: 4.91% Traditional ROI: 2.27%
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%
5755 NEW INDEPENDENCE PARKWAY Winter Garden, FL Under contract-accepting backup offers. Rare 4-bedroom, 2.5-bathroom townhome offering ove...	4 beds \| 3 baths \| 2,061 sq.ft.	$418,000	Airbnb cash on cash: 7.25% Traditional cash on cash: 3.98% Airbnb Rental Income: $5064 Traditional Rental Income: $2752 Airbnb ROI: 7.25% Traditional ROI: 3.98%
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%
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: 0.64% Traditional cash on cash: 3.37% Airbnb Rental Income: $1636 Traditional Rental Income: $2604 Airbnb ROI: 0.64% Traditional ROI: 3.37%
1312 AZALEA WAY Winter Garden, FL Under contract-accepting backup offers. Located in the heart of Winter Garden, this 3 bedr...	3 beds \| 2 baths \| 1,216 sq.ft.	$265,000	Airbnb cash on cash: 1.97% Traditional cash on cash: 4.88% Airbnb Rental Income: $1636 Traditional Rental Income: $1902 Airbnb ROI: 1.97% Traditional ROI: 4.88%
6578 CALAMONDIN DRIVE Winter Garden, FL This luxury 4bd/3ba townhouse is located in the highly sought-after Hamlin Reserve at Wint...	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%
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%
15206 SUNRISE GROVE COURT Winter Garden, FL Under contract-accepting backup offers. For the first time on the market, this impeccably ...	3 beds \| 3 baths \| 1,874 sq.ft.	$398,800	Airbnb cash on cash: 0.32% Traditional cash on cash: 4.49% Airbnb Rental Income: $1636 Traditional Rental Income: $2733 Airbnb ROI: 0.32% Traditional ROI: 4.49%
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%
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.	$299,000	Airbnb cash on cash: -3.37% Traditional cash on cash: 0.4% Airbnb Rental Income: $1636 Traditional Rental Income: $2238 Airbnb ROI: -3.37% Traditional ROI: 0.4%
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.	$1,099,000	Airbnb cash on cash: -1.67% Traditional cash on cash: 0.97% Airbnb Rental Income: $1636 Traditional Rental Income: $3876 Airbnb ROI: -1.67% Traditional ROI: 0.97%
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.	$259,900	Airbnb cash on cash: -1.04% Traditional cash on cash: 0.37% Airbnb Rental Income: $2340 Traditional Rental Income: $2109 Airbnb ROI: -1.04% Traditional ROI: 0.37%
15508 BLACKBEAD STREET Winter Garden, FL New PRICE!!!! This charming home features a long driveway, providing ample parking and a w...	3 beds \| 3 baths \| 1,754 sq.ft.	$449,000	Airbnb cash on cash: -0.37% Traditional cash on cash: 2.82% Airbnb Rental Income: $1636 Traditional Rental Income: $2515 Airbnb ROI: -0.37% Traditional ROI: 2.82%
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.	$289,000	Airbnb cash on cash: -0.33% Traditional cash on cash: 1.26% Airbnb Rental Income: $2340 Traditional Rental Income: $2194 Airbnb ROI: -0.33% Traditional ROI: 1.26%
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%
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%

Your search for investment property begins and ends here

Fort Worth Investment Property for Sale in Winter Garden, FL

1224 UNION CLUB DRIVE

Winter Garden, FL

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

$1,850,000

Airbnb cash on cash: N/A

Traditional cash on cash: 3%

Airbnb Rental Income: $null

Traditional Rental Income: $9335

Airbnb ROI: N/A

Traditional ROI: 3%

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%

15318 SANDFIELD LOOP

Winter Garden, FL

5 beds | 4 baths | 4,288 sq.ft.

$800,000

Airbnb cash on cash: N/A

Traditional cash on cash: 3.35%

Airbnb Rental Income: $null

Traditional Rental Income: $4503

Airbnb ROI: N/A

Traditional ROI: 3.35%

2018 BAY CLOVER DRIVE

Winter Garden, FL

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

$590,000

Airbnb cash on cash: 5.25%

Traditional cash on cash: 2.67%

Airbnb Rental Income: $5064

Traditional Rental Income: $2610

Airbnb ROI: 5.25%

Traditional ROI: 2.67%

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%

13609 GLYNSHEL DRIVE

Winter Garden, FL

4 beds | 3 baths | 2,923 sq.ft.

$879,000

Airbnb cash on cash: 2.88%

Traditional cash on cash: 2.58%

Airbnb Rental Income: $5064

Traditional Rental Income: $3783

Airbnb ROI: 2.88%

Traditional ROI: 2.58%

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%