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%
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%
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%
14282 CREEKBED CIRCLE Winter Garden, FL WELCOME HOME: YOUR WINTER GARDEN ESCAPE AWAITS Imagine stepping into a life of effortless...	4 beds \| 4 baths \| 3,479 sq.ft.	$949,900	Airbnb cash on cash: 2.48% Traditional cash on cash: 3.38% Airbnb Rental Income: $5064 Traditional Rental Income: $4828 Airbnb ROI: 2.48% Traditional ROI: 3.38%
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%
5685 NEW INDEPENDENCE PARKWAY Winter Garden, FL Welcome to this newly UPDATED and uniquely UPGRADED 3-bedroom, 2.5-bath END-UNIT townhome ...	3 beds \| 3 baths \| 1,751 sq.ft.	$475,000	Airbnb cash on cash: -0.11% Traditional cash on cash: 2.71% Airbnb Rental Income: $1636 Traditional Rental Income: $2430 Airbnb ROI: -0.11% Traditional ROI: 2.71%
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%
10061 BEDTIME STORY DRIVE Winter Garden, FL Under contract-accepting backup offers. !!!WELCOME TO THE BEAUTIFUL UPSCALE HORIZON WEST I...	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%
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%
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.	$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%
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.	$283,000	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 Under contract-accepting backup offers. Welcome to the largest 2 bedroom/2 bath Cypress Mo...	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 NEW PRICE! Welcome to your move-in ready haven in Winter Garden's highly desirable Johns...	4 beds \| 3 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%
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%
15060 STUTTGART ALLEY Winter Garden, FL Beautiful 2 story house in desirable Watermark in Winter Garden. This house includes stain...	4 beds \| 3 baths \| 1,696 sq.ft.	$490,000	Airbnb cash on cash: 5.96% Traditional cash on cash: 2.39% Airbnb Rental Income: $5064 Traditional Rental Income: $2395 Airbnb ROI: 5.96% Traditional ROI: 2.39%
1534 E SPRING RIDGE CIRCLE 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.	$569,000	Airbnb cash on cash: 0.11% Traditional cash on cash: 3% Airbnb Rental Income: $1636 Traditional Rental Income: $2709 Airbnb ROI: 0.11% Traditional ROI: 3%
1350 WINTER GREEN WAY Winter Garden, FL Simply Perfect Home or Investment Opportunity in Winter Garden! Welcome to 1350 Winter Gr...	2 beds \| 2 baths \| 1,190 sq.ft.	$264,000	Airbnb cash on cash: 4.54% Traditional cash on cash: 4.67% Airbnb Rental Income: $2340 Traditional Rental Income: $1795 Airbnb ROI: 4.54% Traditional ROI: 4.67%
15522 MURCOTT BLOSSOM BOULEVARD Winter Garden, FL LUXURY END-UNIT TOWNHOME IN HORIZON WEST! Move right in to this beautiful former model-ho...	3 beds \| 3 baths \| 2,207 sq.ft.	$485,000	Airbnb cash on cash: -0.68% Traditional cash on cash: 4.5% Airbnb Rental Income: $1636 Traditional Rental Income: $3526 Airbnb ROI: -0.68% Traditional ROI: 4.5%
15412 AMBERBEAM BOULEVARD Winter Garden, FL Welcome to your future beautifully updated home in Stoneybrook Westâone of the most soug...	3 beds \| 2 baths \| 1,484 sq.ft.	$485,000	Airbnb cash on cash: -0.59% Traditional cash on cash: 3.56% Airbnb Rental Income: $1636 Traditional Rental Income: $3059 Airbnb ROI: -0.59% Traditional ROI: 3.56%
1065 LINCOLN TERRACE Winter Garden, FL Under contract-accepting backup offers. This beautifully updated 3 bedroom, 2 bathroom hom...	3 beds \| 2 baths \| 910 sq.ft.	$289,000	Airbnb cash on cash: 2.63% Traditional cash on cash: 5.04% Airbnb Rental Income: $1636 Traditional Rental Income: $1829 Airbnb ROI: 2.63% Traditional ROI: 5.04%

Real Estate investment in Winter-garden, FL

There are 399 properties for sale in the city of Winter Garden . The median list price in Winter Garden is $599,999 and the average price per square foot is $251. 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 $2,696.

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

There are 399 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 $2,696.

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%

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%

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%

Traditional ROI: 2.05%

14282 CREEKBED CIRCLE

Winter Garden, FL

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

$949,900

Airbnb cash on cash: 2.48%

Traditional cash on cash: 3.38%

Airbnb Rental Income: $5064

Traditional Rental Income: $4828

Airbnb ROI: 2.48%

Traditional ROI: 3.38%

14801 EVERGREEN OAK LOOP

Winter Garden, FL

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%