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
607 E Oakland Ave Winter Garden, FL Welcome to this exceptional Winter Garden home with 4 bedrooms, 3.5-bathrooms, PLUS home o...	4 beds \| 3 baths \| 3,406 sq.ft.	$865,000	Airbnb cash on cash: 2.86% Traditional cash on cash: 2.99% Airbnb Rental Income: $5064 Traditional Rental Income: $4139 Airbnb ROI: 2.86% Traditional ROI: 2.99%
7189 Summerlake Groves St Winter Garden, FL COME set your eyes on this Gorgeous 2-Story Winter Garden home located in Highlands at Sum...	3 beds \| 2 baths \| 2,138 sq.ft.	$609,999	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%
14372 Sunbridge Cir Winter Garden, FL This is a unique opportunity to live in the highly sought-after gated community of Bradfor...	4 beds \| 4 baths \| 3,468 sq.ft.	$775,000	Airbnb cash on cash: 3.33% Traditional cash on cash: 5.68% Airbnb Rental Income: $5064 Traditional Rental Income: $5780 Airbnb ROI: 3.33% Traditional ROI: 5.68%
14046 Fox Glove St Winter Garden, FL Stunning golf course frontage home in the highly desirable Stoneybrook West gated communit...	4 beds \| 3 baths \| 2,970 sq.ft.	$755,000	Airbnb cash on cash: N/A Traditional cash on cash: 2.61% Airbnb Rental Income: $null Traditional Rental Income: $3329 Airbnb ROI: N/A Traditional ROI: 2.61%
373 Eron Way #47 Winter Garden, FL Short Sale. MOVE-IN READY and quietly positioned within a well-established Winter Garden c...	2 beds \| 2 baths \| 840 sq.ft.	$163,999	Airbnb cash on cash: 5.22% Traditional cash on cash: 4.64% Airbnb Rental Income: $2340 Traditional Rental Income: $1667 Airbnb ROI: 5.22% Traditional ROI: 4.64%
14501 Grove Resort Ave #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: -0.54% Traditional cash on cash: 1.18% Airbnb Rental Income: $2340 Traditional Rental Income: $2110 Airbnb ROI: -0.54% Traditional ROI: 1.18%
714 Parkmont Pl 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.	$549,900	Airbnb cash on cash: -0.31% Traditional cash on cash: 2.35% Airbnb Rental Income: $1636 Traditional Rental Income: $2588 Airbnb ROI: -0.31% Traditional ROI: 2.35%
14282 Creekbed Cir Winter Garden, FL Price improvement and quick close available. WELCOME HOME: YOUR WINTER GARDEN ESCAPE AWAI...	4 beds \| 4 baths \| 3,479 sq.ft.	$929,500	Airbnb cash on cash: 2.52% Traditional cash on cash: 3.44% Airbnb Rental Income: $5064 Traditional Rental Income: $4828 Airbnb ROI: 2.52% Traditional ROI: 3.44%
14645 Scott Key Dr Winter Garden, FL Beautifully updated single-family home featuring NEW EXTERIOR PAINT AND NEW FLOORING THROU...	4 beds \| 3 baths \| 3,427 sq.ft.	$890,000	Airbnb cash on cash: 2.07% Traditional cash on cash: 1.81% Airbnb Rental Income: $5064 Traditional Rental Income: $3797 Airbnb ROI: 2.07% Traditional ROI: 1.81%
14801 Evergreen Oak Loop Winter Garden, FL Welcome to Your Dream Townhome! Perfectly situated on a desirable corner lot, this charmi...	3 beds \| 2 baths \| 1,741 sq.ft.	$399,000	Airbnb cash on cash: -0.72% Traditional cash on cash: 2.72% Airbnb Rental Income: $1636 Traditional Rental Income: $2512 Airbnb ROI: -0.72% Traditional ROI: 2.72%
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.	$490,000	Airbnb cash on cash: -0.14% Traditional cash on cash: 3.17% Airbnb Rental Income: $1636 Traditional Rental Income: $2723 Airbnb ROI: -0.14% Traditional ROI: 3.17%
14095 Title Way Winter Garden, FL Welcome to this move-in-ready townhome in the heart of Winter Gardenâs highly sought-aft...	3 beds \| 2 baths \| 1,628 sq.ft.	$440,000	Airbnb cash on cash: -0.49% Traditional cash on cash: 3% Airbnb Rental Income: $1636 Traditional Rental Income: $2648 Airbnb ROI: -0.49% Traditional ROI: 3%
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: -2.56% Traditional cash on cash: 0.48% Airbnb Rental Income: $1636 Traditional Rental Income: $2171 Airbnb ROI: -2.56% Traditional ROI: 0.48%
15852 Shorebird Ln Winter Garden, FL Stunning 2-Story Home in Winter Garden â 4 Bedrooms, Solar Panels, and Exceptional Featu...	4 beds \| 4 baths \| 2,766 sq.ft.	$829,000	Airbnb cash on cash: 1.99% Traditional cash on cash: 1.78% Airbnb Rental Income: $5064 Traditional Rental Income: $3857 Airbnb ROI: 1.99% Traditional ROI: 1.78%
15372 Gilligan Ct Winter Garden, FL Stunning One-Story Home in the Heart of Horizon West â Beautifully Renovated and Move-In...	4 beds \| 3 baths \| 2,781 sq.ft.	$870,000	Airbnb cash on cash: 2.75% Traditional cash on cash: 2.34% Airbnb Rental Income: $5064 Traditional Rental Income: $3697 Airbnb ROI: 2.75% Traditional ROI: 2.34%
5531 Cypress Hill Rd Winter Garden, FL Exquisitely upgraded 4-bedroom, 3-bath smart home in the highly sought-after Orchard Hills...	4 beds \| 3 baths \| 2,204 sq.ft.	$625,000	Airbnb cash on cash: 4.02% Traditional cash on cash: 1.96% Airbnb Rental Income: $5064 Traditional Rental Income: $2827 Airbnb ROI: 4.02% Traditional ROI: 1.96%
8256 Bayview Crossing Dr Winter Garden, FL PRICE IMPROVEMENT....UPGRADED POOL HOME in Horizon West! Welcome to this 4-bed, 3.5-bath,...	4 beds \| 3 baths \| 2,557 sq.ft.	$675,000	Airbnb cash on cash: 3.27% Traditional cash on cash: 2.5% Airbnb Rental Income: $5064 Traditional Rental Income: $3546 Airbnb ROI: 3.27% Traditional ROI: 2.5%
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: 3.9% Traditional cash on cash: 2.86% Airbnb Rental Income: $2340 Traditional Rental Income: $1483 Airbnb ROI: 3.9% Traditional ROI: 2.86%
14501 Grove Resort Ave #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: 1.66% Airbnb Rental Income: $2340 Traditional Rental Income: $2327 Airbnb ROI: -0.36% Traditional ROI: 1.66%
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.	$895,000	Airbnb cash on cash: -1.51% Traditional cash on cash: 1% Airbnb Rental Income: $1636 Traditional Rental Income: $3266 Airbnb ROI: -1.51% Traditional ROI: 1%
14501 Grove Resort Ave #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%
14501 Grove Resort Ave #3535 Winter Garden, FL GREAT OWNER FINANCING AVAILABLE: CONTACT US FOR ADDITIONAL INFORMATION. BEAUTIFUL 2 BED/2 ...	2 beds \| 2 baths \| 1,434 sq.ft.	$389,990	Airbnb cash on cash: -0.99% Traditional cash on cash: 0.19% Airbnb Rental Income: $2340 Traditional Rental Income: $2193 Airbnb ROI: -0.99% Traditional ROI: 0.19%
14602 Winter Stay Dr Winter Garden, FL Fantastic opportunity to own this exceptional home in the highly sought-after WATERMARK co...	4 beds \| 3 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.	$476,900	Airbnb cash on cash: -0.54% Traditional cash on cash: 2.06% Airbnb Rental Income: $1636 Traditional Rental Income: $2332 Airbnb ROI: -0.54% Traditional ROI: 2.06%
17661 Davenport Rd Winter Garden, FL Located in the Rare Lake Avalon Rural Settlement where oversized lots and protected rural ...	3 beds \| 3 baths \| 2,400 sq.ft.	$1,125,000	Airbnb cash on cash: -0.79% Traditional cash on cash: 3.03% Airbnb Rental Income: $1636 Traditional Rental Income: $5347 Airbnb ROI: -0.79% Traditional ROI: 3.03%
14501 Grove Resort Ave #1440 Winter Garden, FL ust minutes from Disney, this fully furnished condo at The Grove Resort and Waterpark offe...	2 beds \| 2 baths \| 1,375 sq.ft.	$245,000	Airbnb cash on cash: -0.72% Traditional cash on cash: 1.57% Airbnb Rental Income: $2340 Traditional Rental Income: $2362 Airbnb ROI: -0.72% Traditional ROI: 1.57%
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: -3.47% Traditional cash on cash: 0.08% Airbnb Rental Income: $1636 Traditional Rental Income: $2174 Airbnb ROI: -3.47% Traditional ROI: 0.08%
14501 Grove Resort Ave #2119 Winter Garden, FL Gorgeous Lakeview Condo at The Grove Resort & Water Park Orlando! Perfect for snowbirds o...	3 beds \| 2 baths \| 1,396 sq.ft.	$224,000	Airbnb cash on cash: -3.54% Traditional cash on cash: 0.5% Airbnb Rental Income: $1636 Traditional Rental Income: $2238 Airbnb ROI: -3.54% Traditional ROI: 0.5%
14501 Grove Resort Ave #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: -0.14% Traditional cash on cash: 1.26% Airbnb Rental Income: $2340 Traditional Rental Income: $2089 Airbnb ROI: -0.14% Traditional ROI: 1.26%
15508 Blackbead St Winter Garden, FL One or more photo(s) has been virtually staged. If youâre looking for low-maintenance li...	3 beds \| 2 baths \| 1,754 sq.ft.	$440,000	Airbnb cash on cash: -0.72% Traditional cash on cash: 2.5% Airbnb Rental Income: $1636 Traditional Rental Income: $2515 Airbnb ROI: -0.72% Traditional ROI: 2.5%
14501 Grove Resort Ave #3406 Winter Garden, FL Gorgeous Lakeview Condo at The Grove Resort & Water Park Orlando! Perfect for snowbirds o...	2 beds \| 2 baths \| 1,265 sq.ft.	$204,000	Airbnb cash on cash: -0.29% Traditional cash on cash: 1.38% Airbnb Rental Income: $2340 Traditional Rental Income: $2194 Airbnb ROI: -0.29% Traditional ROI: 1.38%
14501 Grove Resort Ave #1220 Winter Garden, FL Great Location â Steps from Resort Amenities at The Grove! Enjoy the ultimate Orlando v...	2 beds \| 2 baths \| 1,375 sq.ft.	$325,890	Airbnb cash on cash: -0.18% Traditional cash on cash: 1.43% Airbnb Rental Income: $2340 Traditional Rental Income: $2255 Airbnb ROI: -0.18% Traditional ROI: 1.43%
15058 Sawgrass Bluff Dr Winter Garden, FL Location! Location! Located just 10 minutes from historic downtown Winter Garden and adjac...	4 beds \| 2 baths \| 2,626 sq.ft.	$600,000	Airbnb cash on cash: 4.72% Traditional cash on cash: 2.93% Airbnb Rental Income: $5064 Traditional Rental Income: $3031 Airbnb ROI: 4.72% Traditional ROI: 2.93%
428 Sand Lime Rd Winter Garden, FL Short Sale. Short Sale. Short Sale. SHORT SALE. SHORT SALE, 3 bedroom, 1.5 bath townhome ...	3 beds \| 1 baths \| 1,234 sq.ft.	$220,000	Airbnb cash on cash: 2.79% Traditional cash on cash: 6.2% Airbnb Rental Income: $1636 Traditional Rental Income: $1901 Airbnb ROI: 2.79% Traditional ROI: 6.2%
16125 Azure Key St Winter Garden, FL Welcome home to the highly sought-after Waterleigh community in Horizon West. This bright ...	3 beds \| 2 baths \| 1,685 sq.ft.	$480,000	Airbnb cash on cash: -0.53% Traditional cash on cash: 4.27% Airbnb Rental Income: $1636 Traditional Rental Income: $3377 Airbnb ROI: -0.53% Traditional ROI: 4.27%
5637 Water Rose Rd Winter Garden, FL Welcome to this beautifully maintained townhome located in the highly desirable Independen...	3 beds \| 2 baths \| 1,617 sq.ft.	$419,990	Airbnb cash on cash: -0.73% Traditional cash on cash: 2.24% Airbnb Rental Income: $1636 Traditional Rental Income: $2397 Airbnb ROI: -0.73% Traditional ROI: 2.24%
1534 E Spring Ridge Cir Winter Garden, FL Welcome to this stunning updated 3-bedroom, 2-bath home located in one of Winter Gardenâ...	3 beds \| 2 baths \| 1,688 sq.ft.	$554,000	Airbnb cash on cash: 0.14% Traditional cash on cash: 3.1% Airbnb Rental Income: $1636 Traditional Rental Income: $2709 Airbnb ROI: 0.14% Traditional ROI: 3.1%
11032 Great Rock St Winter Garden, FL The Ibis at Waterleigh is a spacious town home with 3 bedrooms, 2.5 baths with stainless s...	3 beds \| 2 baths \| 1,567 sq.ft.	$409,900	Airbnb cash on cash: 0.33% Traditional cash on cash: 3.64% Airbnb Rental Income: $1636 Traditional Rental Income: $2447 Airbnb ROI: 0.33% Traditional ROI: 3.64%
500 Teacup Springs Ct Winter Garden, FL Short Sale. An exceptional opportunity for investors, builders, and developersâthis prop...	4 beds \| 3 baths \| 2,397 sq.ft.	$530,000	Airbnb cash on cash: 5.79% Traditional cash on cash: 3.83% Airbnb Rental Income: $5064 Traditional Rental Income: $3060 Airbnb ROI: 5.79% Traditional ROI: 3.83%
14501 Grove Resort Ave #1622 Winter Garden, FL BEST VIEW IN THE ENTIRE RESORT! This is the largest condo offered at The Grove Resort & W...	3 beds \| 3 baths \| 1,544 sq.ft.	$449,000	Airbnb cash on cash: -2.24% Traditional cash on cash: 1.31% Airbnb Rental Income: $1636 Traditional Rental Income: $2666 Airbnb ROI: -2.24% Traditional ROI: 1.31%

Real Estate investment in Winter-garden, FL

There are 898 properties for sale in the city of Winter Garden . The median list price in Winter Garden is $614,995 and the average price per square foot is $253. In March 2026, the average monthly cash on cash return in Winter Garden is 3.00%. The average monthly rental income in Winter Garden is $2,782.

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

There are 898 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 $2,782.

Your search for investment property begins and ends here

Investment Property for Sale in Winter Garden, FL

607 E Oakland Ave

Winter Garden, FL

4 beds | 3 baths | 3,406 sq.ft.

$865,000

Airbnb cash on cash: 2.86%

Traditional cash on cash: 2.99%

Airbnb Rental Income: $5064

Traditional Rental Income: $4139

Airbnb ROI: 2.86%

Traditional ROI: 2.99%

7189 Summerlake Groves St

Winter Garden, FL

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

$609,999

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%

14372 Sunbridge Cir

Winter Garden, FL

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

$775,000

Airbnb cash on cash: 3.33%

Traditional cash on cash: 5.68%

Airbnb Rental Income: $5064

Traditional Rental Income: $5780

Airbnb ROI: 3.33%

Traditional ROI: 5.68%

14046 Fox Glove St

Winter Garden, FL

4 beds | 3 baths | 2,970 sq.ft.

$755,000

Airbnb cash on cash: N/A

Traditional cash on cash: 2.61%

Airbnb Rental Income: $null

Traditional Rental Income: $3329

Airbnb ROI: N/A

Traditional ROI: 2.61%

373 Eron Way #47

Winter Garden, FL

2 beds | 2 baths | 840 sq.ft.

$163,999

Airbnb cash on cash: 5.22%

Traditional cash on cash: 4.64%

Airbnb Rental Income: $2340

Traditional Rental Income: $1667

Airbnb ROI: 5.22%

Traditional ROI: 4.64%

14501 Grove Resort Ave #1111

Winter Garden, FL

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

$205,000

Airbnb cash on cash: -0.54%

Traditional cash on cash: 1.18%

Airbnb Rental Income: $2340

Traditional Rental Income: $2110

Airbnb ROI: -0.54%

Traditional ROI: 1.18%

714 Parkmont Pl

Winter Garden, FL

3 beds | 2 baths | 2,190 sq.ft.

$549,900

Airbnb cash on cash: -0.31%

Traditional cash on cash: 2.35%

Airbnb Rental Income: $1636

Traditional Rental Income: $2588

Airbnb ROI: -0.31%

Traditional ROI: 2.35%

14282 Creekbed Cir

Winter Garden, FL

4 beds | 4 baths | 3,479 sq.ft.

$929,500

Airbnb cash on cash: 2.52%

Traditional cash on cash: 3.44%

Airbnb Rental Income: $5064

Traditional Rental Income: $4828

Airbnb ROI: 2.52%