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.	$1,815,000	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%
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%
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%
14815 DRIFTWATER DRIVE Winter Garden, FL One or more photo(s) has been virtually staged. New Price! Discover this beautifully updat...	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.	$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%
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.	$489,900	Airbnb cash on cash: -0.12% Traditional cash on cash: 3.26% Airbnb Rental Income: $1636 Traditional Rental Income: $2723 Airbnb ROI: -0.12% Traditional ROI: 3.26%
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.	$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 Exceptional opportunity! Seller is offering $5,000 toward buyerâs closing costs or rate ...	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%
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%
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%
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%
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 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%
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%
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 Welcome to your slice of paradise in Winter Garden, FL---where luxury, fun, and income pot...	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.	$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%

Real Estate investment in Winter-garden, FL

There are 442 properties for sale in the city of Winter Garden . The median list price in Winter Garden is $598,400 and the average price per square foot is $250. In October 2025, the average monthly cash on cash return in Winter Garden is 3.00%. The average monthly rental income in Winter Garden is $2,727.

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

There are 442 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 $2,727.

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.

$1,815,000

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%

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%

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%