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
1106 Sarah Mathews Dr Winter Garden, FL 1106 Sarah Mathews Dr, Winter Garden, FL 34760 \| Single Family Residential	5 beds \| 5 baths \| 3,596 sq.ft.	$1,975,000	Airbnb cash on cash: -1.57% Traditional cash on cash: 0.69% Airbnb Rental Income: $1240 Traditional Rental Income: $4978 Airbnb ROI: -1.57% Traditional ROI: 0.69%
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.	$675,000	Airbnb cash on cash: -0.68% Traditional cash on cash: 2.87% Airbnb Rental Income: $1240 Traditional Rental Income: $3077 Airbnb ROI: -0.68% Traditional ROI: 2.87%
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.	$550,000	Airbnb cash on cash: 0.81% Traditional cash on cash: 3.48% Airbnb Rental Income: $2718 Traditional Rental Income: $3451 Airbnb ROI: 0.81% Traditional ROI: 3.48%
14411 Hampshire Bay Cir Winter Garden, FL Nestled within the prestigious gated enclave of Bay Isle, this distinguished Toll Brothers...	4 beds \| 3 baths \| 4,010 sq.ft.	$885,000	Airbnb cash on cash: -0.19% Traditional cash on cash: 5.69% Airbnb Rental Income: $2718 Traditional Rental Income: $6971 Airbnb ROI: -0.19% Traditional ROI: 5.69%
338 Windford Ct 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: 0.91% Traditional cash on cash: 4.15% Airbnb Rental Income: $1338 Traditional Rental Income: $1930 Airbnb ROI: 0.91% Traditional ROI: 4.15%
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: 0.82% Traditional cash on cash: 6.44% Airbnb Rental Income: $2718 Traditional Rental Income: $5980 Airbnb ROI: 0.82% Traditional ROI: 6.44%
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: 0.25% Traditional cash on cash: 5.54% Airbnb Rental Income: $1391 Traditional Rental Income: $1885 Airbnb ROI: 0.25% Traditional ROI: 5.54%
14501 Grove Resort Ave #1111 Winter Garden, FL 14K PRICE DROP \| Ground Floor Unit \| Pond and Fountain Views \| Aggressively Priced Ground ...	2 beds \| 2 baths \| 1,265 sq.ft.	$179,000	Airbnb cash on cash: -4.96% Traditional cash on cash: 4.51% Airbnb Rental Income: $1391 Traditional Rental Income: $2636 Airbnb ROI: -4.96% Traditional ROI: 4.51%
7279 Duxbury Ln Winter Garden, FL Welcome to this beautifully maintained END-UNIT townhome in Lakeview Pointe, one of Horizo...	3 beds \| 2 baths \| 1,895 sq.ft.	$424,900	Airbnb cash on cash: -1.51% Traditional cash on cash: 2.84% Airbnb Rental Income: $1338 Traditional Rental Income: $2710 Airbnb ROI: -1.51% Traditional ROI: 2.84%
13536 Sunset Lakes Cir 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.	$999,900	Airbnb cash on cash: -1.33% Traditional cash on cash: 3.93% Airbnb Rental Income: $1240 Traditional Rental Income: $6227 Airbnb ROI: -1.33% Traditional ROI: 3.93%
13377 Lake Butler Blvd Winter Garden, FL One or more photo(s) has been virtually staged. BACK ON MARKET: Buyer's inability to obtai...	5 beds \| 4 baths \| 6,000 sq.ft.	$5,995,000	Airbnb cash on cash: -1.11% Traditional cash on cash: 0.02% Airbnb Rental Income: $1240 Traditional Rental Income: $7090 Airbnb ROI: -1.11% Traditional ROI: 0.02%
14776 Magnolia Ridge Loop Winter Garden, FL Discover Your Dream Home in the Exclusive Orchard Hills Community! This stunning reside...	4 beds \| 3 baths \| 2,876 sq.ft.	$880,000	Airbnb cash on cash: -0.1% Traditional cash on cash: 1.79% Airbnb Rental Income: $2718 Traditional Rental Income: $3622 Airbnb ROI: -0.1% Traditional ROI: 1.79%
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: 0.82% Traditional cash on cash: 2.29% Airbnb Rental Income: $2718 Traditional Rental Income: $2890 Airbnb ROI: 0.82% Traditional ROI: 2.29%
900 Walkers Grove Ln Winter Garden, FL Downtown Winter Garden â Golf Cart District! Donât miss this amazing opportunity to...	3 beds \| 2 baths \| 1,905 sq.ft.	$459,900	Airbnb cash on cash: -0.64% Traditional cash on cash: 4.32% Airbnb Rental Income: $1338 Traditional Rental Income: $3086 Airbnb ROI: -0.64% Traditional ROI: 4.32%
15518 Fountain Cove Ct 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.	$550,000	Airbnb cash on cash: -1.61% Traditional cash on cash: 2.08% Airbnb Rental Income: $1338 Traditional Rental Income: $2911 Airbnb ROI: -1.61% Traditional ROI: 2.08%
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: -0.91% Traditional cash on cash: 3.31% Airbnb Rental Income: $1338 Traditional Rental Income: $2722 Airbnb ROI: -0.91% Traditional ROI: 3.31%
8170 Bluejack Oak Dr Winter Garden, FL Welcome to 8170 Bluejack Oak Drive, a beautifully situated corner unit in the heart of the...	3 beds \| 2 baths \| 1,853 sq.ft.	$445,000	Airbnb cash on cash: -0.9% Traditional cash on cash: 2.72% Airbnb Rental Income: $1338 Traditional Rental Income: $2487 Airbnb ROI: -0.9% Traditional ROI: 2.72%
14501 Grove Resort Ave #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: -3.31% Traditional cash on cash: 2.02% Airbnb Rental Income: $1338 Traditional Rental Income: $2677 Airbnb ROI: -3.31% Traditional ROI: 2.02%
420 E Cypress St Winter Garden, FL Welcome to this stunning, fully renovated and fully furnished home, perfectly situated on ...	3 beds \| 2 baths \| 1,616 sq.ft.	$410,000	Airbnb cash on cash: -0.19% Traditional cash on cash: 4.29% Airbnb Rental Income: $1338 Traditional Rental Income: $2686 Airbnb ROI: -0.19% Traditional ROI: 4.29%
14755 Masthead Landing Cir Winter Garden, FL Located in the highly desirable Stoneybrook West community, this beautifully maintained 4-...	4 beds \| 2 baths \| 2,258 sq.ft.	$549,900	Airbnb cash on cash: 0.72% Traditional cash on cash: 1.49% Airbnb Rental Income: $2718 Traditional Rental Income: $2492 Airbnb ROI: 0.72% Traditional ROI: 1.49%
8721 Bayview Crossing Dr Winter Garden, FL Amazing opportunity for a corner lot pool home, within the highly demanded Waterleigh - Ma...	4 beds \| 3 baths \| 2,842 sq.ft.	$679,000	Airbnb cash on cash: 0.35% Traditional cash on cash: 3.56% Airbnb Rental Income: $2718 Traditional Rental Income: $4111 Airbnb ROI: 0.35% Traditional ROI: 3.56%
1701 E Bay St Winter Garden, FL Welcome to this beautifully renovated 2-bedroom, 2-bath home in the heart of Winter Garden...	2 beds \| 2 baths \| 825 sq.ft.	$289,000	Airbnb cash on cash: 1.3% Traditional cash on cash: 3.87% Airbnb Rental Income: $1391 Traditional Rental Income: $1685 Airbnb ROI: 1.3% Traditional ROI: 3.87%
1112 Juniper Hammock Ct Winter Garden, FL Virtually Staged. Welcome to this beautiful and spacious 4-bedroom, 2-bath home located in...	4 beds \| 2 baths \| 2,545 sq.ft.	$515,000	Airbnb cash on cash: 1.77% Traditional cash on cash: 4.01% Airbnb Rental Income: $2718 Traditional Rental Income: $3154 Airbnb ROI: 1.77% Traditional ROI: 4.01%
13542 Sunset Lakes Cir Winter Garden, FL A New Standard of Luxury...Welcome to 13542 Sunset Lakes Circle, the 5,450 square foot cro...	5 beds \| 5 baths \| 5,450 sq.ft.	$3,799,000	Airbnb cash on cash: -1.48% Traditional cash on cash: 1.24% Airbnb Rental Income: $1240 Traditional Rental Income: $10412 Airbnb ROI: -1.48% Traditional ROI: 1.24%
634 Foster Ave 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: 0.96% Traditional cash on cash: 4.48% Airbnb Rental Income: $1391 Traditional Rental Income: $1916 Airbnb ROI: 0.96% Traditional ROI: 4.48%
131 Oak Laurel Dr Winter Garden, FL 131 Oak Laurel Drive is a stunning, modern townhome built in 2019 in the highly desirable ...	3 beds \| 3 baths \| 1,906 sq.ft.	$834,000	Airbnb cash on cash: -1.87% Traditional cash on cash: 1.83% Airbnb Rental Income: $1338 Traditional Rental Income: $3797 Airbnb ROI: -1.87% Traditional ROI: 1.83%
1061 Portmoor Way Winter Garden, FL Welcome to 1061 Portmoor Way, a single-story 4-bedroom, 2-bathroom home located in the hig...	4 beds \| 2 baths \| 1,804 sq.ft.	$515,000	Airbnb cash on cash: 1.16% Traditional cash on cash: 1.76% Airbnb Rental Income: $2718 Traditional Rental Income: $2376 Airbnb ROI: 1.16% Traditional ROI: 1.76%
14501 Grove Resort Ave #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: -3.63% Traditional cash on cash: 1.66% Airbnb Rental Income: $1391 Traditional Rental Income: $2808 Airbnb ROI: -3.63% Traditional ROI: 1.66%
20 E Division St Winter Garden, FL Welcome to one of Winter Garden's most remarkable custom transformations. This wasn't a fl...	4 beds \| 3 baths \| 2,729 sq.ft.	$1,080,000	Airbnb cash on cash: 0.27% Traditional cash on cash: 1.4% Airbnb Rental Income: $2718 Traditional Rental Income: $3262 Airbnb ROI: 0.27% Traditional ROI: 1.4%
14501 Grove Resort Ave #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: -4.09% Traditional cash on cash: 3.26% Airbnb Rental Income: $1391 Traditional Rental Income: $2672 Airbnb ROI: -4.09% Traditional ROI: 3.26%
14501 Grove Resort Ave #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: -4.35% Traditional cash on cash: 1.87% Airbnb Rental Income: $1338 Traditional Rental Income: $2678 Airbnb ROI: -4.35% Traditional ROI: 1.87%
14501 Grove Resort Ave #2119 Winter Garden, FL Attention SNOWBIRDS! Great resorts for snowbirds! Gorgeous Lakeview Condo at The Grove R...	3 beds \| 2 baths \| 1,396 sq.ft.	$219,000	Airbnb cash on cash: -5.32% Traditional cash on cash: 2.9% Airbnb Rental Income: $1338 Traditional Rental Income: $2671 Airbnb ROI: -5.32% Traditional ROI: 2.9%
14501 GROVE RESORT AVENUE #3215 Winter Garden, FL Welcome to Grove Resort! Located on the second floor of Building 3, this unit is your laun...	2 beds \| 2 baths \| 1,265 sq.ft.	$239,000	Airbnb cash on cash: -4.09% Traditional cash on cash: 3.2% Airbnb Rental Income: $1391 Traditional Rental Income: $2617 Airbnb ROI: -4.09% Traditional ROI: 3.2%
6323 Hamlin Reserve Blvd Winter Garden, FL Expansive private backyard. Covered brick paver patio. Carpet free interior. Wood look til...	3 beds \| 2 baths \| 2,177 sq.ft.	$560,000	Airbnb cash on cash: -1.82% Traditional cash on cash: 2.08% Airbnb Rental Income: $1338 Traditional Rental Income: $2966 Airbnb ROI: -1.82% Traditional ROI: 2.08%
14501 Grove Resort Ave #3406 Winter Garden, FL Attention SNOWBIRDS! Great resorts for snowbirds! Gorgeous Lakeview Condo at The Grove R...	2 beds \| 2 baths \| 1,265 sq.ft.	$179,000	Airbnb cash on cash: -4.14% Traditional cash on cash: 4.08% Airbnb Rental Income: $1391 Traditional Rental Income: $2562 Airbnb ROI: -4.14% Traditional ROI: 4.08%
14501 Grove Resort Ave #1443 Winter Garden, FL GREAT NEW LISTING & PRICE: $300,000.00 MOTIVATED SELLER. WELCOME TO THE GROVE RESORT & WAT...	2 beds \| 2 baths \| 1,375 sq.ft.	$290,000	Airbnb cash on cash: -3.88% Traditional cash on cash: 2.34% Airbnb Rental Income: $1391 Traditional Rental Income: $2726 Airbnb ROI: -3.88% Traditional ROI: 2.34%
14501 Grove Resort Ave #1220 Winter Garden, FL The Birch â 2 Bed / 2 Bath Condo-Hotel The only floorplan at The Grove with two true pr...	2 beds \| 2 baths \| 1,375 sq.ft.	$325,890	Airbnb cash on cash: -2.76% Traditional cash on cash: 3.18% Airbnb Rental Income: $1391 Traditional Rental Income: $2792 Airbnb ROI: -2.76% Traditional ROI: 3.18%
15594 Shorebird Ln Winter Garden, FL One or more photo(s) has been virtually staged. EXPERIENCE ELEVATED LAKEFRONT LIVING IN TH...	4 beds \| 3 baths \| 3,022 sq.ft.	$1,219,000	Airbnb cash on cash: -1.06% Traditional cash on cash: 0.76% Airbnb Rental Income: $2718 Traditional Rental Income: $4140 Airbnb ROI: -1.06% Traditional ROI: 0.76%
15187 Harrowgate Way Winter Garden, FL Location! Location! Welcome to this wel maintained 3 beds 2 bath single family home locate...	3 beds \| 2 baths \| 1,296 sq.ft.	$425,000	Airbnb cash on cash: -0.4% Traditional cash on cash: 3.28% Airbnb Rental Income: $1338 Traditional Rental Income: $2425 Airbnb ROI: -0.4% Traditional ROI: 3.28%
14501 Grove Resort Ave #3109 Winter Garden, FL PREMIUM BUILDING 3 \| RARE 14-FOOT CEILINGS \| ELEVATOR-FREE ACCESS \| ONSITE RENTAL PROGRAM ...	2 beds \| 2 baths \| 1,434 sq.ft.	$299,900	Airbnb cash on cash: -3.41% Traditional cash on cash: 3.31% Airbnb Rental Income: $1391 Traditional Rental Income: $2867 Airbnb ROI: -3.41% Traditional ROI: 3.31%

Real Estate investment in Winter-garden, FL

There are 912 properties for sale in the city of Winter Garden . The median list price in Winter Garden is $619,629 and the average price per square foot is $259. In August 2026, the average monthly cash on cash return in Winter Garden is 3.00%. The average monthly rental income in Winter Garden is $2,843.

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

There are 912 investment properties available for sale in Winter-garden.

In 2026, the best neighborhood to buy investment property is Winter Garden.

The ROI for Short-Term is higher than the Long-Term in Winter-garden with average rental income of $1,338.

Your search for investment property begins and ends here

Investment Property for Sale in Winter Garden, FL

1106 Sarah Mathews Dr

Winter Garden, FL

5 beds | 5 baths | 3,596 sq.ft.

$1,975,000

Airbnb cash on cash: -1.57%

Traditional cash on cash: 0.69%

Airbnb Rental Income: $1240

Traditional Rental Income: $4978

Airbnb ROI: -1.57%

Traditional ROI: 0.69%

849 SHADOWMOSS DRIVE

Winter Garden, FL

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

$675,000

Airbnb cash on cash: -0.68%

Traditional cash on cash: 2.87%

Airbnb Rental Income: $1240

Traditional Rental Income: $3077

Airbnb ROI: -0.68%

Traditional ROI: 2.87%

2200 ROMANUM DRIVE

Winter Garden, FL

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

$550,000

Airbnb cash on cash: 0.81%

Traditional cash on cash: 3.48%

Airbnb Rental Income: $2718

Traditional Rental Income: $3451

Airbnb ROI: 0.81%

Traditional ROI: 3.48%

14411 Hampshire Bay Cir

Winter Garden, FL

4 beds | 3 baths | 4,010 sq.ft.

$885,000

Airbnb cash on cash: -0.19%

Traditional cash on cash: 5.69%

Airbnb Rental Income: $2718

Traditional Rental Income: $6971

Airbnb ROI: -0.19%

Traditional ROI: 5.69%

338 Windford Ct

Winter Garden, FL

3 beds | 2 baths | 1,050 sq.ft.

$330,000

Airbnb cash on cash: 0.91%

Traditional cash on cash: 4.15%

Airbnb Rental Income: $1338

Traditional Rental Income: $1930

Airbnb ROI: 0.91%

Traditional ROI: 4.15%

14372 SUNBRIDGE CIRCLE

Winter Garden, FL

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

$745,000

Airbnb cash on cash: 0.82%

Traditional cash on cash: 6.44%

Airbnb Rental Income: $2718

Traditional Rental Income: $5980

Airbnb ROI: 0.82%

Traditional ROI: 6.44%

373 Eron Way #47

Winter Garden, FL

2 beds | 2 baths | 840 sq.ft.

$182,000

Airbnb cash on cash: 0.25%

Traditional cash on cash: 5.54%

Airbnb Rental Income: $1391

Traditional Rental Income: $1885

Airbnb ROI: 0.25%

Traditional ROI: 5.54%

14501 Grove Resort Ave #1111

Winter Garden, FL

2 beds | 2 baths | 1,265 sq.ft.

$179,000

Airbnb cash on cash: -4.96%

Traditional cash on cash: 4.51%

Airbnb Rental Income: $1391

Traditional Rental Income: $2636

Airbnb ROI: -4.96%