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
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%
14433 PLEACH ST Winter Garden, FL Under contract-accepting backup offers. END-UNIT IN HIGHLY SOUGHT-AFTER INDEPENDENCE! This...	3 beds \| 3 baths \| 1,639 sq.ft.	$419,000	Airbnb cash on cash: -0.4% Traditional cash on cash: 2.46% Airbnb Rental Income: $1636 Traditional Rental Income: $2300 Airbnb ROI: -0.4% Traditional ROI: 2.46%
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 *MOTIVATED SELLERS* Welcome home to this 3 bedroom 2 1/2 bathroom single-family home s...	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%
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%
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%
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.	$518,000	Airbnb cash on cash: -0.17% Traditional cash on cash: 3.03% Airbnb Rental Income: $1636 Traditional Rental Income: $2723 Airbnb ROI: -0.17% Traditional ROI: 3.03%
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%
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 HISTORIC DOWNTOWN WINTER GARDEN!! ...	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%
5755 NEW INDEPENDENCE PARKWAY Winter Garden, FL Rare 4-bedroom, 2.5-bathroom townhome offering over 2,000 SQFT of living space in a highly...	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%
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%
1312 AZALEA WAY Winter Garden, FL Located in the heart of Winter Garden, this 3 bedroom 2 bath townhome features a screened ...	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%
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.	$464,000	Airbnb cash on cash: -0.82% Traditional cash on cash: 0.98% Airbnb Rental Income: $2340 Traditional Rental Income: $2545 Airbnb ROI: -0.82% Traditional ROI: 0.98%
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%
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%
14501 GROVE RESORT AVENUE #2119 Winter Garden, FL Don't miss the opportunity to make this AMAZING vacation home yours! Perfect locatio...	3 beds \| 2 baths \| 1,396 sq.ft.	$320,000	Airbnb cash on cash: -3.22% Traditional cash on cash: 0.31% Airbnb Rental Income: $1636 Traditional Rental Income: $2238 Airbnb ROI: -3.22% Traditional ROI: 0.31%
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%

Real Estate investment in Winter-garden, FL

There are 427 properties for sale in the city of Winter Garden . The median list price in Winter Garden is $577,495 and the average price per square foot is $245. In September 2025, the average monthly cash on cash return in Winter Garden is 3.00%. The average monthly rental income in Winter Garden is $2,684.

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

There are 427 investment properties available for sale in Winter-garden.

In 2025, 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 $2,684.

Your search for investment property begins and ends here

Investment Property 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%

14433 PLEACH ST

Winter Garden, FL

3 beds | 3 baths | 1,639 sq.ft.

$419,000

Airbnb cash on cash: -0.4%

Traditional cash on cash: 2.46%

Airbnb Rental Income: $1636

Traditional Rental Income: $2300

Airbnb ROI: -0.4%

Traditional ROI: 2.46%

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%