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.	$875,000	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%
330 E Story Rd Winter Garden, FL One or more photo(s) has been virtually staged. Welcome to an incredible opportunity to ow...	2 beds \| 1 baths \| 760 sq.ft.	$299,999	Airbnb cash on cash: 3.39% Traditional cash on cash: 3.94% Airbnb Rental Income: $2340 Traditional Rental Income: $1929 Airbnb ROI: 3.39% Traditional ROI: 3.94%
12456 Westfield Lakes Cir Winter Garden, FL Welcome home to this stunning residence in the highly desirable Westfield Lakes community,...	4 beds \| 3 baths \| 2,180 sq.ft.	$575,000	Airbnb cash on cash: 5.52% Traditional cash on cash: 3.13% Airbnb Rental Income: $5064 Traditional Rental Income: $2747 Airbnb ROI: 5.52% Traditional ROI: 3.13%
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.	$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%
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.	$799,000	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.	$765,000	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%
17556 DEER ISLE CIRCLE Winter Garden, FL Charming & Spacious Lake-Community Home in Deer Island Welcome to 17556 Deer Isle Circle,...	4 beds \| 4 baths \| 3,214 sq.ft.	$1,225,000	Airbnb cash on cash: 1.5% Traditional cash on cash: 2.36% Airbnb Rental Income: $5064 Traditional Rental Income: $5002 Airbnb ROI: 1.5% Traditional ROI: 2.36%
623 E PLANT STREET Winter Garden, FL Welcome to this beautifully maintained 3-bedroom, 2.5-bath townhome in the Heritage at Pla...	3 beds \| 3 baths \| 1,688 sq.ft.	$499,000	Airbnb cash on cash: -0.31% Traditional cash on cash: 2.44% Airbnb Rental Income: $1636 Traditional Rental Income: $2455 Airbnb ROI: -0.31% Traditional ROI: 2.44%
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.	$169,999	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.	$215,000	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.	$564,900	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.	$937,500	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.	$977,000	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.	$415,000	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%
5685 New Independence Pkwy Winter Garden, FL Welcome to this newly UPDATED and uniquely UPGRADED 3-bedroom, 2.5-bath END-UNIT townhome ...	3 beds \| 2 baths \| 1,751 sq.ft.	$469,000	Airbnb cash on cash: -0.1% Traditional cash on cash: 2.76% Airbnb Rental Income: $1636 Traditional Rental Income: $2430 Airbnb ROI: -0.1% Traditional ROI: 2.76%
1166 Westside Dr Winter Garden, FL Charming 3 bedroom, 2 bath townhome with desirable Winter Garden address. Step through the...	3 beds \| 2 baths \| 846 sq.ft.	$229,000	Airbnb cash on cash: 2.65% Traditional cash on cash: 5.21% Airbnb Rental Income: $1636 Traditional Rental Income: $1728 Airbnb ROI: 2.65% Traditional ROI: 5.21%
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.	$500,000	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 \| 3 baths \| 1,636 sq.ft.	$450,000	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.	$899,000	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.	$884,500	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%
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 \| 2 baths \| 1,088 sq.ft.	$345,000	Airbnb cash on cash: 2.38% Traditional cash on cash: 3.18% Airbnb Rental Income: $2340 Traditional Rental Income: $2020 Airbnb ROI: 2.38% Traditional ROI: 3.18%
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.	$1,175,000	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.	$278,000	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.	$279,000	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.	$249,000	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%
149 S Park Ave Winter Garden, FL Huge price reduction!! Gorgeous former model in this beautiful masonry wrapped complex in ...	3 beds \| 3 baths \| 2,938 sq.ft.	$969,000	Airbnb cash on cash: -1.76% Traditional cash on cash: 1.23% Airbnb Rental Income: $1636 Traditional Rental Income: $3876 Airbnb ROI: -1.76% Traditional ROI: 1.23%
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.	$445,000	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.	$269,000	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%

Real Estate investment in Winter-garden, FL

There are 829 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 February 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 829 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.

$875,000

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%

330 E Story Rd

Winter Garden, FL

2 beds | 1 baths | 760 sq.ft.

$299,999

Airbnb cash on cash: 3.39%

Traditional cash on cash: 3.94%

Airbnb Rental Income: $2340

Traditional Rental Income: $1929

Airbnb ROI: 3.39%

Traditional ROI: 3.94%

12456 Westfield Lakes Cir

Winter Garden, FL

4 beds | 3 baths | 2,180 sq.ft.

$575,000

Airbnb cash on cash: 5.52%

Traditional cash on cash: 3.13%

Airbnb Rental Income: $5064

Traditional Rental Income: $2747

Airbnb ROI: 5.52%

Traditional ROI: 3.13%

7189 Summerlake Groves St

Winter Garden, FL

3 beds | 2 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%

14372 Sunbridge Cir

Winter Garden, FL

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

$799,000

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.

$765,000

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%

17556 DEER ISLE CIRCLE

Winter Garden, FL

4 beds | 4 baths | 3,214 sq.ft.

$1,225,000

Airbnb cash on cash: 1.5%

Traditional cash on cash: 2.36%

Airbnb Rental Income: $5064

Traditional Rental Income: $5002

Airbnb ROI: 1.5%

Traditional ROI: 2.36%

623 E PLANT STREET

Winter Garden, FL

3 beds | 3 baths | 1,688 sq.ft.

$499,000

Airbnb cash on cash: -0.31%

Traditional cash on cash: 2.44%

Airbnb Rental Income: $1636

Traditional Rental Income: $2455

Airbnb ROI: -0.31%