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
849 SHADOWMOSS DRIVE Winter Garden, FL Prime Winter Garden Location \| Westfield Lakes Welcome to this lovely 5-bedroom, 3-bath...	5 beds \| 3 baths \| 2,620 sq.ft.	$745,000	Airbnb cash on cash: N/A Traditional cash on cash: 2.51% Airbnb Rental Income: $null Traditional Rental Income: $3077 Airbnb ROI: N/A Traditional ROI: 2.51%
2200 ROMANUM DRIVE Winter Garden, FL Come see 2200 Romanum Dr, recently updated with fresh interior paint and partial flooring ...	4 beds \| 4 baths \| 2,561 sq.ft.	$560,000	Airbnb cash on cash: 4.51% Traditional cash on cash: 3.4% Airbnb Rental Income: $5064 Traditional Rental Income: $3451 Airbnb ROI: 4.51% Traditional ROI: 3.4%
7189 SUMMERLAKE GROVES STREET Winter Garden, FL COME set your eyes on your Gorgeous 2-Story Winter Garden DREAM HOME located in the Highla...	3 beds \| 3 baths \| 2,138 sq.ft.	$609,999	Airbnb cash on cash: -0.5% Traditional cash on cash: 3.22% Airbnb Rental Income: $1636 Traditional Rental Income: $3295 Airbnb ROI: -0.5% Traditional ROI: 3.22%
15140 SUNRISE GROVE COURT Winter Garden, FL Under contract-accepting backup offers. Imagine a life where lakeside serenity meets moder...	3 beds \| 3 baths \| 2,012 sq.ft.	$390,987	Airbnb cash on cash: -0.74% Traditional cash on cash: 5.07% Airbnb Rental Income: $1636 Traditional Rental Income: $3302 Airbnb ROI: -0.74% Traditional ROI: 5.07%
14372 SUNBRIDGE CIRCLE Winter Garden, FL This is a unique opportunity to live in the highly sought-after gated community of Bradfor...	4 beds \| 5 baths \| 3,468 sq.ft.	$745,000	Airbnb cash on cash: 3.64% Traditional cash on cash: 6.44% Airbnb Rental Income: $5064 Traditional Rental Income: $5980 Airbnb ROI: 3.64% Traditional ROI: 6.44%
264 BLUE STONE CIRCLE Winter Garden, FL LOCATION, LOCATION, LOCATION! Welcome to 264 Blue Stone Cir in the highly desirable Winter...	4 beds \| 3 baths \| 2,538 sq.ft.	$725,000	Airbnb cash on cash: 4.02% Traditional cash on cash: 3.53% Airbnb Rental Income: $5064 Traditional Rental Income: $3698 Airbnb ROI: 4.02% Traditional ROI: 3.53%
2202 ROMANUM DRIVE Winter Garden, FL Welcome to your next home in the heart of Winter Gardenâwhere location, lifestyle, and u...	3 beds \| 2 baths \| 1,889 sq.ft.	$579,900	Airbnb cash on cash: -0.09% Traditional cash on cash: 2.23% Airbnb Rental Income: $1636 Traditional Rental Income: $2435 Airbnb ROI: -0.09% Traditional ROI: 2.23%
16232 ROCK COAST DRIVE Winter Garden, FL Under contract-accepting backup offers. Welcome to your dream home and backyard oasis! Thi...	4 beds \| 5 baths \| 3,491 sq.ft.	$925,000	Airbnb cash on cash: 2.41% Traditional cash on cash: 6.22% Airbnb Rental Income: $5064 Traditional Rental Income: $7312 Airbnb ROI: 2.41% Traditional ROI: 6.22%
373 ERON WAY #47 Winter Garden, FL Short Sale. SHORT SALE APPROVED READY TO CLOSE AND MOVE-IN READY and quietly positioned wi...	2 beds \| 2 baths \| 840 sq.ft.	$182,000	Airbnb cash on cash: 4.82% Traditional cash on cash: 5.54% Airbnb Rental Income: $2340 Traditional Rental Income: $1885 Airbnb ROI: 4.82% Traditional ROI: 5.54%
2154 OAKINGTON STREET Winter Garden, FL Welcome to this beautifully maintained, single-story home that perfectly blends comfort, s...	3 beds \| 2 baths \| 1,585 sq.ft.	$469,900	Airbnb cash on cash: -0.25% Traditional cash on cash: 2.23% Airbnb Rental Income: $1636 Traditional Rental Income: $2263 Airbnb ROI: -0.25% Traditional ROI: 2.23%
14501 GROVE RESORT AVENUE #1111 Winter Garden, FL Ground Floor Unit \| Pond and Fountain Views \| Aggressively Priced Ground floor residence f...	2 beds \| 2 baths \| 1,265 sq.ft.	$205,000	Airbnb cash on cash: -0.51% Traditional cash on cash: 3.98% Airbnb Rental Income: $2340 Traditional Rental Income: $2636 Airbnb ROI: -0.51% Traditional ROI: 3.98%
897 LANDRUM DRIVE Winter Garden, FL Welcome to one of Winter Garden's most coveted addresses â nestled in the heart of the G...	4 beds \| 4 baths \| 3,012 sq.ft.	$899,900	Airbnb cash on cash: 2.73% Traditional cash on cash: 1.96% Airbnb Rental Income: $5064 Traditional Rental Income: $3383 Airbnb ROI: 2.73% Traditional ROI: 1.96%
14282 CREEKBED CIRCLE Winter Garden, FL *Seller is willing to contribute up to $5,000 towards interest rate buy down or closing co...	4 beds \| 4 baths \| 3,479 sq.ft.	$924,500	Airbnb cash on cash: 2.57% Traditional cash on cash: 4.61% Airbnb Rental Income: $5064 Traditional Rental Income: $5782 Airbnb ROI: 2.57% Traditional ROI: 4.61%
604 FOSTER AVENUE Winter Garden, FL Under contract-accepting backup offers. Situated just two blocks outside the Golf Cart Dis...	3 beds \| 2 baths \| 1,275 sq.ft.	$400,000	Airbnb cash on cash: 1.48% Traditional cash on cash: 3.92% Airbnb Rental Income: $1636 Traditional Rental Income: $2092 Airbnb ROI: 1.48% Traditional ROI: 3.92%
13536 SUNSET LAKES CIRCLE Winter Garden, FL Experience luxury living in this gorgeous home in the highly sought after Sunset Lakes com...	5 beds \| 4 baths \| 3,389 sq.ft.	$1,150,000	Airbnb cash on cash: N/A Traditional cash on cash: 3.72% Airbnb Rental Income: $null Traditional Rental Income: $6227 Airbnb ROI: N/A Traditional ROI: 3.72%
7266 DESERT MANDARIN STREET Winter Garden, FL Great investment opportunity! Welcome to this beautifully maintained home built in 2018, f...	4 beds \| 3 baths \| 2,365 sq.ft.	$595,000	Airbnb cash on cash: 4.34% Traditional cash on cash: 2.29% Airbnb Rental Income: $5064 Traditional Rental Income: $2890 Airbnb ROI: 4.34% Traditional ROI: 2.29%
14447 PRUNNINGWOOD PLACE Winter Garden, FL One or more photo(s) has been virtually staged. This stylish townhome in the highly sought...	2 beds \| 3 baths \| 1,250 sq.ft.	$340,000	Airbnb cash on cash: 1.81% Traditional cash on cash: 4.01% Airbnb Rental Income: $2340 Traditional Rental Income: $2464 Airbnb ROI: 1.81% Traditional ROI: 4.01%
15508 PEBBLE RIDGE STREET Winter Garden, FL This is the one youâve been waiting for. A beautifully maintained four bedroom pool home...	4 beds \| 3 baths \| 2,763 sq.ft.	$695,000	Airbnb cash on cash: 3.79% Traditional cash on cash: 3.14% Airbnb Rental Income: $5064 Traditional Rental Income: $3612 Airbnb ROI: 3.79% Traditional ROI: 3.14%
900 WALKERS GROVE LANE Winter Garden, FL Downtown Winter Garden â Golf Cart District! Donât miss this amazing opportunity to...	3 beds \| 3 baths \| 1,905 sq.ft.	$475,000	Airbnb cash on cash: -0.09% Traditional cash on cash: 4.21% Airbnb Rental Income: $1636 Traditional Rental Income: $3086 Airbnb ROI: -0.09% Traditional ROI: 4.21%
15518 FOUNTAIN COVE COURT Winter Garden, FL Nestled within the exclusive Marina Bay enclave of Waterleigh, one of Horizon Westâs mos...	3 beds \| 3 baths \| 2,040 sq.ft.	$574,990	Airbnb cash on cash: -1.15% Traditional cash on cash: 1.49% Airbnb Rental Income: $1636 Traditional Rental Income: $2590 Airbnb ROI: -1.15% Traditional ROI: 1.49%
5755 CYPRESS HILL ROAD Winter Garden, FL Welcome to this beautifully maintained corner townhouse in the sought-after Orchard Hills ...	3 beds \| 3 baths \| 1,797 sq.ft.	$455,000	Airbnb cash on cash: -0.33% Traditional cash on cash: 3.31% Airbnb Rental Income: $1636 Traditional Rental Income: $2722 Airbnb ROI: -0.33% Traditional ROI: 3.31%
8170 BLUEJACK OAK DRIVE Winter Garden, FL Welcome to 8170 Bluejack Oak Drive, a beautifully situated corner unit in the heart of the...	3 beds \| 3 baths \| 1,853 sq.ft.	$465,000	Airbnb cash on cash: -0.33% Traditional cash on cash: 2.68% Airbnb Rental Income: $1636 Traditional Rental Income: $2487 Airbnb ROI: -0.33% Traditional ROI: 2.68%
5460 BOWMAN DRIVE Winter Garden, FL Video Tour Available Welcome to Overlook at Hamlin, where an active, vibrant lifestyle...	3 beds \| 4 baths \| 2,474 sq.ft.	$625,000	Airbnb cash on cash: -1.19% Traditional cash on cash: 1.91% Airbnb Rental Income: $1636 Traditional Rental Income: $2981 Airbnb ROI: -1.19% 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: 2.02% Airbnb Rental Income: $1636 Traditional Rental Income: $2677 Airbnb ROI: -2.56% Traditional ROI: 2.02%
213 W TILDEN STREET Winter Garden, FL Located in DOWNTOWN WINTER GARDEN!! This beautifully renovated single story home combi...	4 beds \| 2 baths \| 2,151 sq.ft.	$765,000	Airbnb cash on cash: 3.47% Traditional cash on cash: 2.24% Airbnb Rental Income: $5064 Traditional Rental Income: $3152 Airbnb ROI: 3.47% Traditional ROI: 2.24%
14755 MASTHEAD LANDING CIRCLE Winter Garden, FL Located in the highly desirable Stoneybrook West community, this beautifully maintained 4-...	4 beds \| 2 baths \| 2,258 sq.ft.	$580,000	Airbnb cash on cash: 4.31% Traditional cash on cash: 1.47% Airbnb Rental Income: $5064 Traditional Rental Income: $2492 Airbnb ROI: 4.31% Traditional ROI: 1.47%
8721 BAYVIEW CROSSING DRIVE Winter Garden, FL Amazing opportunity for a corner lot pool home, within the highly demanded Waterleigh - Ma...	4 beds \| 4 baths \| 2,842 sq.ft.	$695,000	Airbnb cash on cash: 3.34% Traditional cash on cash: 3.46% Airbnb Rental Income: $5064 Traditional Rental Income: $4111 Airbnb ROI: 3.34% Traditional ROI: 3.46%
15852 SHOREBIRD LANE Winter Garden, FL Stunning 2-Story Home in Winter Garden â 4 Bedrooms, Solar Panels, and Exceptional Featu...	4 beds \| 5 baths \| 2,766 sq.ft.	$785,000	Airbnb cash on cash: 2.42% Traditional cash on cash: 2.73% Airbnb Rental Income: $5064 Traditional Rental Income: $4262 Airbnb ROI: 2.42% Traditional ROI: 2.73%
15372 GILLIGAN COURT Winter Garden, FL Stunning One-Story Home in the Heart of Horizon West â Beautifully Renovated and Move-In...	4 beds \| 4 baths \| 2,781 sq.ft.	$870,000	Airbnb cash on cash: 2.81% Traditional cash on cash: 4.09% Airbnb Rental Income: $5064 Traditional Rental Income: $5070 Airbnb ROI: 2.81% Traditional ROI: 4.09%
5531 CYPRESS HILL ROAD Winter Garden, FL Under contract-accepting backup offers. Exquisitely upgraded 4-bedroom, 3-bath smart home ...	4 beds \| 3 baths \| 2,204 sq.ft.	$610,000	Airbnb cash on cash: 4.14% Traditional cash on cash: 3.02% Airbnb Rental Income: $5064 Traditional Rental Income: $3393 Airbnb ROI: 4.14% Traditional ROI: 3.02%
1112 JUNIPER HAMMOCK COURT Winter Garden, FL One or more photo(s) has been virtually staged. Welcome to this beautiful and spacious 4-b...	4 beds \| 2 baths \| 2,545 sq.ft.	$520,000	Airbnb cash on cash: 5.77% Traditional cash on cash: 3.96% Airbnb Rental Income: $5064 Traditional Rental Income: $3154 Airbnb ROI: 5.77% Traditional ROI: 3.96%
648 ORANGE BELT LOOP Winter Garden, FL Welcome to your opportunity to own in one of the most desirable locations near downtown Wi...	3 beds \| 3 baths \| 1,688 sq.ft.	$499,990	Airbnb cash on cash: -0.32% Traditional cash on cash: 3.37% Airbnb Rental Income: $1636 Traditional Rental Income: $2902 Airbnb ROI: -0.32% Traditional ROI: 3.37%
634 FOSTER AVENUE Winter Garden, FL Charming bungalow that's been completely renovated and is now move-in ready! Rebuilt down ...	2 beds \| 1 baths \| 696 sq.ft.	$285,000	Airbnb cash on cash: 3.9% Traditional cash on cash: 4.48% Airbnb Rental Income: $2340 Traditional Rental Income: $1916 Airbnb ROI: 3.9% Traditional ROI: 4.48%
14501 GROVE RESORT AVENUE #1727 Winter Garden, FL This luxurious 2-bedroom, 2-bath vacation condo is the ultimate retreat for those seeking ...	2 beds \| 2 baths \| 1,265 sq.ft.	$298,500	Airbnb cash on cash: -0.36% Traditional cash on cash: 2.56% Airbnb Rental Income: $2340 Traditional Rental Income: $2582 Airbnb ROI: -0.36% Traditional ROI: 2.56%
131 OAK LAUREL DRIVE Winter Garden, FL 131 Oak Laurel Drive is a stunning, modern townhome built in 2019 in the highly desirable ...	3 beds \| 4 baths \| 1,906 sq.ft.	$834,000	Airbnb cash on cash: -1.55% Traditional cash on cash: 1.83% Airbnb Rental Income: $1636 Traditional Rental Income: $3797 Airbnb ROI: -1.55% Traditional ROI: 1.83%
15334 MURCOTT BLOSSOM BOULEVARD Winter Garden, FL Beautiful 3-bedroom, 2.5-bathroom townhouse available in the great Summerlake community of...	3 beds \| 3 baths \| 1,868 sq.ft.	$430,000	Airbnb cash on cash: -0.85% Traditional cash on cash: 4.09% Airbnb Rental Income: $1636 Traditional Rental Income: $3164 Airbnb ROI: -0.85% Traditional ROI: 4.09%
14501 GROVE RESORT AVENUE #3535 Winter Garden, FL New reduced Price: $369,990. GREAT NEW OWNER FINANCING AVAILABLE: CONTACT US FOR ADDITIONA...	2 beds \| 2 baths \| 1,434 sq.ft.	$369,990	Airbnb cash on cash: -1.35% Traditional cash on cash: 1.66% Airbnb Rental Income: $2340 Traditional Rental Income: $2808 Airbnb ROI: -1.35% Traditional ROI: 1.66%
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: 3.79% Airbnb Rental Income: $5064 Traditional Rental Income: $4427 Airbnb ROI: 3.25% Traditional ROI: 3.79%
14501 GROVE RESORT AVENUE #1440 Winter Garden, FL Seller is offering $5,000 toward the buyerâs closing costs, making this fully furnished ...	2 beds \| 2 baths \| 1,375 sq.ft.	$245,000	Airbnb cash on cash: -0.68% Traditional cash on cash: 3.26% Airbnb Rental Income: $2340 Traditional Rental Income: $2672 Airbnb ROI: -0.68% Traditional ROI: 3.26%
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.	$299,000	Airbnb cash on cash: -3.47% Traditional cash on cash: 1.87% Airbnb Rental Income: $1636 Traditional Rental Income: $2678 Airbnb ROI: -3.47% Traditional ROI: 1.87%

Real Estate investment in Winter-garden, FL

There are 494 properties for sale in the city of Winter Garden . The median list price in Winter Garden is $617,995 and the average price per square foot is $260. In May 2026, the average monthly cash on cash return in Winter Garden is 3.00%. The average monthly rental income in Winter Garden is $2,999.

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

There are 494 investment properties available for sale in Winter-garden.

In 2026, 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 $2,999.

Your search for investment property begins and ends here

Investment Property for Sale in Winter Garden, FL

849 SHADOWMOSS DRIVE

Winter Garden, FL

5 beds | 3 baths | 2,620 sq.ft.

$745,000

Airbnb cash on cash: N/A

Traditional cash on cash: 2.51%

Airbnb Rental Income: $null

Traditional Rental Income: $3077

Airbnb ROI: N/A

Traditional ROI: 2.51%

2200 ROMANUM DRIVE

Winter Garden, FL

4 beds | 4 baths | 2,561 sq.ft.

$560,000

Airbnb cash on cash: 4.51%

Traditional cash on cash: 3.4%

Airbnb Rental Income: $5064

Traditional Rental Income: $3451

Airbnb ROI: 4.51%

Traditional ROI: 3.4%

7189 SUMMERLAKE GROVES STREET

Winter Garden, FL

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

$609,999

Airbnb cash on cash: -0.5%

Traditional cash on cash: 3.22%

Airbnb Rental Income: $1636

Traditional Rental Income: $3295

Airbnb ROI: -0.5%

Traditional ROI: 3.22%

15140 SUNRISE GROVE COURT

Winter Garden, FL

3 beds | 3 baths | 2,012 sq.ft.

$390,987

Airbnb cash on cash: -0.74%

Traditional cash on cash: 5.07%

Airbnb Rental Income: $1636

Traditional Rental Income: $3302

Airbnb ROI: -0.74%

Traditional ROI: 5.07%

14372 SUNBRIDGE CIRCLE

Winter Garden, FL

4 beds | 5 baths | 3,468 sq.ft.

$745,000

Airbnb cash on cash: 3.64%

Traditional cash on cash: 6.44%

Airbnb Rental Income: $5064

Traditional Rental Income: $5980

Airbnb ROI: 3.64%

Traditional ROI: 6.44%

264 BLUE STONE CIRCLE

Winter Garden, FL

4 beds | 3 baths | 2,538 sq.ft.

$725,000

Airbnb cash on cash: 4.02%

Traditional cash on cash: 3.53%

Airbnb Rental Income: $5064

Traditional Rental Income: $3698

Airbnb ROI: 4.02%

Traditional ROI: 3.53%

2202 ROMANUM DRIVE

Winter Garden, FL

3 beds | 2 baths | 1,889 sq.ft.

$579,900

Airbnb cash on cash: -0.09%

Traditional cash on cash: 2.23%

Airbnb Rental Income: $1636

Traditional Rental Income: $2435

Airbnb ROI: -0.09%

Traditional ROI: 2.23%

16232 ROCK COAST DRIVE

Winter Garden, FL

4 beds | 5 baths | 3,491 sq.ft.

$925,000

Airbnb cash on cash: 2.41%

Traditional cash on cash: 6.22%

Airbnb Rental Income: $5064

Traditional Rental Income: $7312

Airbnb ROI: 2.41%