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 328 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.	$1,925,000	Airbnb cash on cash: N/A Traditional cash on cash: 2.84% Airbnb Rental Income: $null Traditional Rental Income: $9335 Airbnb ROI: N/A Traditional ROI: 2.84%
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.	$555,000	Airbnb cash on cash: 5.81% Traditional cash on cash: 4.27% Airbnb Rental Income: $5064 Traditional Rental Income: $3234 Airbnb ROI: 5.81% Traditional ROI: 4.27%
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%
7189 SUMMERLAKE GROVES STREET Winter Garden, FL COME set your eyes on this gorgeous 2-Story Winter Garden Home located in Highlands at Sum...	3 beds \| 3 baths \| 2,138 sq.ft.	$619,999	Airbnb cash on cash: -0.51% Traditional cash on cash: 2.51% Airbnb Rental Income: $1636 Traditional Rental Income: $2922 Airbnb ROI: -0.51% Traditional ROI: 2.51%
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%
5911 GRASSY POINT ROAD Winter Garden, FL Under contract-accepting backup offers. *MOTIVATED SELLERS* Welcome home to this 3 bed...	3 beds \| 3 baths \| 2,046 sq.ft.	$490,000	Airbnb cash on cash: -0.5% Traditional cash on cash: 3.05% Airbnb Rental Income: $1636 Traditional Rental Income: $2801 Airbnb ROI: -0.5% Traditional ROI: 3.05%
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.	$1,400,000	Airbnb cash on cash: 1.19% Traditional cash on cash: 1.94% Airbnb Rental Income: $5064 Traditional Rental Income: $5002 Airbnb ROI: 1.19% Traditional ROI: 1.94%
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%
705 SUNBURST COVE LANE Winter Garden, FL Under contract-accepting backup offers. In the vibrant town of Winter Garden, FL, there's ...	4 beds \| 2 baths \| 1,626 sq.ft.	$440,000	Airbnb cash on cash: 7.81% Traditional cash on cash: 3.82% Airbnb Rental Income: $5064 Traditional Rental Income: $2386 Airbnb ROI: 7.81% Traditional ROI: 3.82%
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%
714 HOME GROVE DRIVE Winter Garden, FL *MAJOR PRICE IMPROVEMENT-LOCATION, LOCATION *This home offers unparalleled comfort and...	4 beds \| 2 baths \| 1,992 sq.ft.	$520,000	Airbnb cash on cash: 5.68% Traditional cash on cash: 2.95% Airbnb Rental Income: $5064 Traditional Rental Income: $2704 Airbnb ROI: 5.68% Traditional ROI: 2.95%
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.	$509,400	Airbnb cash on cash: -0.04% Traditional cash on cash: 3.48% Airbnb Rental Income: $1636 Traditional Rental Income: $2850 Airbnb ROI: -0.04% Traditional ROI: 3.48%
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%
14048 LARKSPUR LAKE DRIVE Winter Garden, FL LAKEFRONT: Welcome to 14048 Larkspur Lake Drive, where lakefront living meets modern desig...	4 beds \| 3 baths \| 2,464 sq.ft.	$850,000	Airbnb cash on cash: 2.37% Traditional cash on cash: 1.69% Airbnb Rental Income: $5064 Traditional Rental Income: $3499 Airbnb ROI: 2.37% Traditional ROI: 1.69%
653 STEVELYNN CIRCLE Winter Garden, FL Under contract-accepting backup offers. Discover this beautifully updated 3-bedroom, 2-bat...	3 beds \| 2 baths \| 1,264 sq.ft.	$475,000	Airbnb cash on cash: 0.72% Traditional cash on cash: 2.76% Airbnb Rental Income: $1636 Traditional Rental Income: $2085 Airbnb ROI: 0.72% Traditional ROI: 2.76%
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 One or more photo(s) has been virtually staged. Welcome to home to this exceptional reside...	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%
9149 GRAND ISLAND WAY Winter Garden, FL Welcome to this immaculate, fully upgraded, energy-efficient home in the highly sought-aft...	3 beds \| 3 baths \| 1,904 sq.ft.	$475,000	Airbnb cash on cash: -0.46% Traditional cash on cash: 3.12% Airbnb Rental Income: $1636 Traditional Rental Income: $2764 Airbnb ROI: -0.46% Traditional ROI: 3.12%
14501 GROVE RESORT AVENUE #1727 Winter Garden, FL TOP FLOOR - FIREWORKS VIEW - WATER VIEW!!! This luxurious 2-bedroom, 2-bath vacation condo...	2 beds \| 2 baths \| 1,265 sq.ft.	$320,000	Airbnb cash on cash: -0.4% Traditional cash on cash: 1.48% Airbnb Rental Income: $2340 Traditional Rental Income: $2327 Airbnb ROI: -0.4% Traditional ROI: 1.48%
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%
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 Welcome to 16512 Sea Glass Street, a beautifully upgraded 4 bedroom, 3.5 bath home in the ...	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%
13224 FOX GLOVE STREET Winter Garden, FL Under contract-accepting backup offers. Welcome Home to 13224 Fox Glove Street, in the gat...	4 beds \| 2 baths \| 2,535 sq.ft.	$549,000	Airbnb cash on cash: 4.59% Traditional cash on cash: 1.7% Airbnb Rental Income: $5064 Traditional Rental Income: $2548 Airbnb ROI: 4.59% Traditional ROI: 1.7%
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.	$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%
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%
10309 ATWATER BAY DRIVE Winter Garden, FL Under contract-accepting backup offers. Lakefront property, private pool/hot tub, outdoor ...	4 beds \| 4 baths \| 2,758 sq.ft.	$1,200,000	Airbnb cash on cash: 1.29% Traditional cash on cash: 1.75% Airbnb Rental Income: $5064 Traditional Rental Income: $4537 Airbnb ROI: 1.29% Traditional ROI: 1.75%
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.	$500,000	Airbnb cash on cash: 5.82% Traditional cash on cash: 2.32% Airbnb Rental Income: $5064 Traditional Rental Income: $2395 Airbnb ROI: 5.82% Traditional ROI: 2.32%
13041 INKWELL ALLEY Winter Garden, FL This extraordinary residence is located in the charming neighborhood of Storey Grove. Almo...	4 beds \| 3 baths \| 2,042 sq.ft.	$529,000	Airbnb cash on cash: 5.97% Traditional cash on cash: 3.28% Airbnb Rental Income: $5064 Traditional Rental Income: $2700 Airbnb ROI: 5.97% Traditional ROI: 3.28%
2015 SANDY GARDEN LANE Winter Garden, FL Welcome to this exquisite 3,871 sq/ft home nestled in one of Winter Gardenâs most sought...	4 beds \| 5 baths \| 3,871 sq.ft.	$825,000	Airbnb cash on cash: 2.7% Traditional cash on cash: 5.65% Airbnb Rental Income: $5064 Traditional Rental Income: $6297 Airbnb ROI: 2.7% Traditional ROI: 5.65%
14501 GROVE RESORT AVENUE #1743 Winter Garden, FL GREAT OPPORTUNITY TO PURCHASE A LUXURY BIRCH DESIGN 2 BEDROOM 2 BATHROOM FULLY FURNISHED C...	2 beds \| 2 baths \| 1,375 sq.ft.	$306,990	Airbnb cash on cash: -0.8% Traditional cash on cash: 0.31% Airbnb Rental Income: $2340 Traditional Rental Income: $2083 Airbnb ROI: -0.8% Traditional ROI: 0.31%
14200 AVALON ROAD #406 Winter Garden, FL Under contract-accepting backup offers. Discover a Hidden Gem in the Heart of Winter Garde...	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%
14501 GROVE RESORT AVE #3208 Winter Garden, FL Under contract-accepting backup offers. Experience the Ultimate In Comfort and Convenience...	3 beds \| 2 baths \| 1,396 sq.ft.	$289,900	Airbnb cash on cash: -5.33% Traditional cash on cash: -0.53% Airbnb Rental Income: $1636 Traditional Rental Income: $2486 Airbnb ROI: -5.33% Traditional ROI: -0.53%
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.	$699,000	Airbnb cash on cash: 4.82% Traditional cash on cash: 4.36% Airbnb Rental Income: $5064 Traditional Rental Income: $3731 Airbnb ROI: 4.82% Traditional ROI: 4.36%
14501 GROVE RESORT AVENUE #2103 Winter Garden, FL High-Occupancy Investment Opportunity at The Grove Resort & Water Park Orlando Welcome ...	2 beds \| 2 baths \| 1,265 sq.ft.	$295,000	Airbnb cash on cash: -0.45% Traditional cash on cash: 0.77% Airbnb Rental Income: $2340 Traditional Rental Income: $2101 Airbnb ROI: -0.45% Traditional ROI: 0.77%

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.

$1,925,000

Airbnb cash on cash: N/A

Traditional cash on cash: 2.84%

Airbnb Rental Income: $null

Traditional Rental Income: $9335

Airbnb ROI: N/A

Traditional ROI: 2.84%

660 EGRET PLACE DRIVE

Winter Garden, FL

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

$555,000

Airbnb cash on cash: 5.81%

Traditional cash on cash: 4.27%

Airbnb Rental Income: $5064

Traditional Rental Income: $3234

Airbnb ROI: 5.81%

Traditional ROI: 4.27%

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%

7189 SUMMERLAKE GROVES STREET

Winter Garden, FL

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

$619,999

Airbnb cash on cash: -0.51%

Traditional cash on cash: 2.51%

Airbnb Rental Income: $1636

Traditional Rental Income: $2922

Airbnb ROI: -0.51%

Traditional ROI: 2.51%

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%

5911 GRASSY POINT ROAD

Winter Garden, FL

3 beds | 3 baths | 2,046 sq.ft.

$490,000

Airbnb cash on cash: -0.5%

Traditional cash on cash: 3.05%

Airbnb Rental Income: $1636

Traditional Rental Income: $2801

Airbnb ROI: -0.5%