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
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.	$474,000	Airbnb cash on cash: 6.2% Traditional cash on cash: 3.66% Airbnb Rental Income: $5064 Traditional Rental Income: $2907 Airbnb ROI: 6.2% Traditional ROI: 3.66%
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.	$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%
111 LAKEVIEW RESERVE BOULEVARD Winter Garden, FL Move-in ready! From the extra wide paver driveway, Bahama shutters, modern sculptures, th...	4 beds \| 3 baths \| 2,882 sq.ft.	$634,900	Airbnb cash on cash: 4.97% Traditional cash on cash: 3.64% Airbnb Rental Income: $5064 Traditional Rental Income: $3244 Airbnb ROI: 4.97% Traditional ROI: 3.64%
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.	$1,225,000	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%
15504 SANDFIELD LOOP Winter Garden, FL BRAND NEW ROOF!!! Welcome to the gated community of Reserve at Carriage Pointe, where luxu...	4 beds \| 4 baths \| 4,126 sq.ft.	$875,000	Airbnb cash on cash: 2.78% Traditional cash on cash: 3.56% Airbnb Rental Income: $5064 Traditional Rental Income: $4669 Airbnb ROI: 2.78% Traditional ROI: 3.56%
849 MEADOW GLADE DRIVE Winter Garden, FL Prepare to be impressed by this beautifully maintained 4-bedroom, 2-bath home located in t...	4 beds \| 2 baths \| 1,844 sq.ft.	$625,000	Airbnb cash on cash: 5.05% Traditional cash on cash: 2.94% Airbnb Rental Income: $5064 Traditional Rental Income: $2805 Airbnb ROI: 5.05% Traditional ROI: 2.94%
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.	$569,000	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%
417 S MAIN STREET Winter Garden, FL Experience the perfect blend of historic charm and modern comfort in this home nestled in ...	3 beds \| 3 baths \| 2,172 sq.ft.	$775,000	Airbnb cash on cash: -0.4% Traditional cash on cash: 2.05% Airbnb Rental Income: $1636 Traditional Rental Income: $2941 Airbnb ROI: -0.4% Traditional ROI: 2.05%
14801 EVERGREEN OAK LOOP Winter Garden, FL Welcome to Your Dream Townhome! Perfectly situated on a desirable corner lot, this charmi...	3 beds \| 3 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%
15261 HONEYBELL DRIVE Winter Garden, FL Under contract-accepting backup offers. Welcome to this professionally designed and fully ...	4 beds \| 4 baths \| 3,084 sq.ft.	$829,000	Airbnb cash on cash: 2.81% Traditional cash on cash: 2.56% Airbnb Rental Income: $5064 Traditional Rental Income: $3838 Airbnb ROI: 2.81% Traditional ROI: 2.56%
1166 WESTSIDE DRIVE 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%
7448 POMELO GROVE DRIVE Winter Garden, FL Welcome to 7448 Pomelo Grove Drive â a beautifully curated 4-bedroom, 3-bath pool home i...	4 beds \| 3 baths \| 2,683 sq.ft.	$809,000	Airbnb cash on cash: 2.79% Traditional cash on cash: 2.21% Airbnb Rental Income: $5064 Traditional Rental Income: $3588 Airbnb ROI: 2.79% Traditional ROI: 2.21%
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%
10061 BEDTIME STORY DRIVE Winter Garden, FL !!!WELCOME TO THE BEAUTIFUL UPSCALE HORIZON WEST IN THE WINTER GARDEN AREA!!! This beauti...	3 beds \| 3 baths \| 1,770 sq.ft.	$450,000	Airbnb cash on cash: 0.35% Traditional cash on cash: 3.64% Airbnb Rental Income: $1636 Traditional Rental Income: $2564 Airbnb ROI: 0.35% Traditional ROI: 3.64%
10131 AUDUBON TRACE ALLEY Winter Garden, FL JUST REDUCED $10,000! BEST PRICE with MOST UPGRADES! SINGLE STORY Laurel on a PREMIUM LO...	3 beds \| 2 baths \| 1,685 sq.ft.	$489,000	Airbnb cash on cash: -0.67% Traditional cash on cash: 2.1% Airbnb Rental Income: $1636 Traditional Rental Income: $2440 Airbnb ROI: -0.67% Traditional ROI: 2.1%
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 Located in the heart of DOWNTOWN WINTER GARDEN!! This beautifully renova...	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%
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.	$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%
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%
16190 Harbor Mist Alley Winter Garden, FL This amazing all concrete block construction single-family home features 3 bedrooms and 2....	3 beds \| 3 baths \| 2,014 sq.ft.	$529,900	Airbnb cash on cash: -0.3% Traditional cash on cash: 3.71% Airbnb Rental Income: $1636 Traditional Rental Income: $3164 Airbnb ROI: -0.3% Traditional ROI: 3.71%
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%
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.	$315,000	Airbnb cash on cash: 3.44% Traditional cash on cash: 2.5% Airbnb Rental Income: $2340 Traditional Rental Income: $1483 Airbnb ROI: 3.44% Traditional ROI: 2.5%
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%
14501 GROVE RESORT AVENUE #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 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.	$355,000	Airbnb cash on cash: 2.29% Traditional cash on cash: 3.06% Airbnb Rental Income: $2340 Traditional Rental Income: $2020 Airbnb ROI: 2.29% Traditional ROI: 3.06%
17661 DAVENPORT ROAD 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 AVENUE #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.	$284,000	Airbnb cash on cash: -0.72% Traditional cash on cash: 1.53% Airbnb Rental Income: $2340 Traditional Rental Income: $2362 Airbnb ROI: -0.72% Traditional ROI: 1.53%
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%
14501 GROVE RESORT AVENUE #2119 Winter Garden, FL This absolute Gorgeous Lakeview property presents a unique opportunity for real estate inv...	3 beds \| 2 baths \| 1,396 sq.ft.	$289,000	Airbnb cash on cash: -3.45% Traditional cash on cash: 0.45% Airbnb Rental Income: $1636 Traditional Rental Income: $2238 Airbnb ROI: -3.45% Traditional ROI: 0.45%
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.	$259,000	Airbnb cash on cash: -0.17% Traditional cash on cash: 1.17% Airbnb Rental Income: $2340 Traditional Rental Income: $2089 Airbnb ROI: -0.17% Traditional ROI: 1.17%
149 S PARK AVENUE Winter Garden, FL Gorgeous former model in this beautiful masonry wrapped complex in the heart of Winter Gar...	3 beds \| 4 baths \| 2,938 sq.ft.	$1,044,000	Airbnb cash on cash: -1.71% Traditional cash on cash: 1.07% Airbnb Rental Income: $1636 Traditional Rental Income: $3876 Airbnb ROI: -1.71% Traditional ROI: 1.07%
14501 GROVE RESORT AVENUE #3636 Winter Garden, FL Just Reduced - LOWEST PRICE condo at The Grove Resort. Welcome to the largest 2 bedroom/2 ...	2 beds \| 2 baths \| 1,434 sq.ft.	$199,900	Airbnb cash on cash: -0.79% Traditional cash on cash: 1.05% Airbnb Rental Income: $2340 Traditional Rental Income: $2109 Airbnb ROI: -0.79% Traditional ROI: 1.05%
14501 GROVE RESORT AVENUE #3406 Winter Garden, FL This property presents a unique opportunity for real estate investors seeking a proven, in...	2 beds \| 2 baths \| 1,265 sq.ft.	$279,000	Airbnb cash on cash: -0.3% Traditional cash on cash: 1.34% Airbnb Rental Income: $2340 Traditional Rental Income: $2194 Airbnb ROI: -0.3% Traditional ROI: 1.34%
14501 GROVE RESORT AVENUE #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 DRIVE Winter Garden, FL Welcome to your move-in ready haven in Winter Garden's highly desirable Johns Lake Pointe ...	4 beds \| 3 baths \| 2,626 sq.ft.	$620,000	Airbnb cash on cash: 4.53% Traditional cash on cash: 2.8% Airbnb Rental Income: $5064 Traditional Rental Income: $3031 Airbnb ROI: 4.53% Traditional ROI: 2.8%
13748 WERRINGTON DRIVE Winter Garden, FL Seller offering concessions to compete with new construction in the area! 13748 Werringto...	3 beds \| 3 baths \| 1,796 sq.ft.	$515,000	Airbnb cash on cash: -0.54% Traditional cash on cash: 2.47% Airbnb Rental Income: $1636 Traditional Rental Income: $2624 Airbnb ROI: -0.54% Traditional ROI: 2.47%
428 SAND LIME ROAD Winter Garden, FL Short Sale. Short Sale. Short Sale. SHORT SALE. SHORT SALE, 3 bedroom, 1.5 bath townhome ...	3 beds \| 2 baths \| 1,234 sq.ft.	$225,000	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 STREET Winter Garden, FL Welcome to your new home in the highly sought-after Waterleigh community of Horizon West! ...	3 beds \| 2 baths \| 1,685 sq.ft.	$500,000	Airbnb cash on cash: -0.54% Traditional cash on cash: 4.17% Airbnb Rental Income: $1636 Traditional Rental Income: $3377 Airbnb ROI: -0.54% Traditional ROI: 4.17%

Real Estate investment in Winter-garden, FL

There are 426 properties for sale in the city of Winter Garden . The median list price in Winter Garden is $600,000 and the average price per square foot is $250. In December 2025, the average monthly cash on cash return in Winter Garden is 3.00%. The average monthly rental income in Winter Garden is $2,731.

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

There are 426 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 $2,731.

Your search for investment property begins and ends here

Investment Property for Sale in Winter Garden, FL

14488 WHITTRIDGE DRIVE

Winter Garden, FL

4 beds | 3 baths | 2,159 sq.ft.

$474,000

Airbnb cash on cash: 6.2%

Traditional cash on cash: 3.66%

Airbnb Rental Income: $5064

Traditional Rental Income: $2907

Airbnb ROI: 6.2%

Traditional ROI: 3.66%

14372 SUNBRIDGE CIRCLE

Winter Garden, FL

4 beds | 5 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%

111 LAKEVIEW RESERVE BOULEVARD

Winter Garden, FL

4 beds | 3 baths | 2,882 sq.ft.

$634,900

Airbnb cash on cash: 4.97%

Traditional cash on cash: 3.64%

Airbnb Rental Income: $5064

Traditional Rental Income: $3244

Airbnb ROI: 4.97%

Traditional ROI: 3.64%

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%

15504 SANDFIELD LOOP

Winter Garden, FL

4 beds | 4 baths | 4,126 sq.ft.

$875,000

Airbnb cash on cash: 2.78%

Traditional cash on cash: 3.56%

Airbnb Rental Income: $5064

Traditional Rental Income: $4669

Airbnb ROI: 2.78%

Traditional ROI: 3.56%

849 MEADOW GLADE DRIVE

Winter Garden, FL

4 beds | 2 baths | 1,844 sq.ft.

$625,000

Airbnb cash on cash: 5.05%

Traditional cash on cash: 2.94%

Airbnb Rental Income: $5064

Traditional Rental Income: $2805

Airbnb ROI: 5.05%

Traditional ROI: 2.94%

714 PARKMONT PLACE

Winter Garden, FL

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

$569,000

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%

417 S MAIN STREET

Winter Garden, FL

3 beds | 3 baths | 2,172 sq.ft.

$775,000

Airbnb cash on cash: -0.4%

Traditional cash on cash: 2.05%

Airbnb Rental Income: $1636

Traditional Rental Income: $2941

Airbnb ROI: -0.4%