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
1073 VINSETTA CIRCLE Winter Garden, FL Dare to dream of this 4/3.5 Winter Garden turn-key single family home in the exclusive com...	4 beds \| 4 baths \| 3,568 sq.ft.	$815,000	Airbnb cash on cash: 3.38% Traditional cash on cash: 3.82% Airbnb Rental Income: $5064 Traditional Rental Income: $4365 Airbnb ROI: 3.38% Traditional ROI: 3.82%
15614 ESPALIER WAY Winter Garden, FL RARE FIND- Excellent opportunity to Buy a this CUSTOM HOME BY THE AWARD WINNING BUILDER DA...	5 beds \| 7 baths \| 6,601 sq.ft.	$4,500,000	Airbnb cash on cash: N/A Traditional cash on cash: 0.27% Airbnb Rental Income: $null Traditional Rental Income: $9380 Airbnb ROI: N/A Traditional ROI: 0.27%
7224 DESERT MANDARIN STREET Winter Garden, FL Welcome to the crown jewel of the neighborhood! This stunning 3-bedroom, 2.5-bathroom home...	3 beds \| 3 baths \| 1,657 sq.ft.	$549,000	Airbnb cash on cash: 0.21% Traditional cash on cash: 2.57% Airbnb Rental Income: $1636 Traditional Rental Income: $2384 Airbnb ROI: 0.21% Traditional ROI: 2.57%
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.	$835,000	Airbnb cash on cash: 3.14% Traditional cash on cash: 5.39% Airbnb Rental Income: $5064 Traditional Rental Income: $5780 Airbnb ROI: 3.14% Traditional ROI: 5.39%
14132 MURCOTT BLOSSOM BOULEVARD Winter Garden, FL Step into a lifestyle of luxury and convenience in this stunning former model home, where ...	4 beds \| 3 baths \| 2,726 sq.ft.	$715,000	Airbnb cash on cash: 3.67% Traditional cash on cash: 2.15% Airbnb Rental Income: $5064 Traditional Rental Income: $3015 Airbnb ROI: 3.67% Traditional ROI: 2.15%
14177 AVENUE OF THE GRVS Winter Garden, FL Nestled in the picturesque community of Signature Lakes in Independence, this beautifully ...	2 beds \| 3 baths \| 1,249 sq.ft.	$365,000	Airbnb cash on cash: 1.44% Traditional cash on cash: 2.72% Airbnb Rental Income: $2340 Traditional Rental Income: $2199 Airbnb ROI: 1.44% Traditional ROI: 2.72%
15691 ORANGE HARVEST LOOP Winter Garden, FL IMMACULATE TOWNHOME WITH ALL THE EXTRAS IN HIGHLY DESIRED WINTER GARDEN GATED COMMUNITY. T...	3 beds \| 3 baths \| 2,444 sq.ft.	$547,000	Airbnb cash on cash: -0.74% Traditional cash on cash: 2.57% Airbnb Rental Income: $1636 Traditional Rental Income: $2866 Airbnb ROI: -0.74% Traditional ROI: 2.57%
16133 PEBBLE BLUFF LOOP Winter Garden, FL Motivated Seller with too many upgrades to list. Welcome home to the beautiful and highly ...	3 beds \| 3 baths \| 1,568 sq.ft.	$439,900	Airbnb cash on cash: 0.18% Traditional cash on cash: 3.25% Airbnb Rental Income: $1636 Traditional Rental Income: $2438 Airbnb ROI: 0.18% Traditional ROI: 3.25%
16736 RUSTY ANCHOR ROAD Winter Garden, FL Introducing the exquisite Carlisle Plan, a beautiful single-story home featuring four bedr...	4 beds \| 3 baths \| 2,696 sq.ft.	$949,990	Airbnb cash on cash: 2.28% Traditional cash on cash: 1.53% Airbnb Rental Income: $5064 Traditional Rental Income: $3374 Airbnb ROI: 2.28% Traditional ROI: 1.53%
14494 WHITTRIDGE DRIVE Winter Garden, FL Experience luxury living in this beautifully remodeled 3-bedroom + office, 2.5-bath townho...	3 beds \| 3 baths \| 2,067 sq.ft.	$475,000	Airbnb cash on cash: 0.17% Traditional cash on cash: 3.35% Airbnb Rental Income: $1636 Traditional Rental Income: $2592 Airbnb ROI: 0.17% Traditional ROI: 3.35%
8024 JEREMY JOSEPH ALLEY Winter Garden, FL Exceedingly Captivating Energy-Efficient Townhome with Private Covered Courtyard! Situated...	3 beds \| 3 baths \| 1,644 sq.ft.	$449,000	Airbnb cash on cash: 0.07% Traditional cash on cash: 3.14% Airbnb Rental Income: $1636 Traditional Rental Income: $2466 Airbnb ROI: 0.07% Traditional ROI: 3.14%
2414 BALFORN TOWER WAY Winter Garden, FL This move-in-ready gem, with a new roof (02/24), new AC (2024), and a washer (2023) & drye...	4 beds \| 3 baths \| 2,428 sq.ft.	$600,000	Airbnb cash on cash: 4.59% Traditional cash on cash: 2.43% Airbnb Rental Income: $5064 Traditional Rental Income: $2820 Airbnb ROI: 4.59% Traditional ROI: 2.43%
14791 CRIMSON BLUFF ALLEY Winter Garden, FL Watermark a resort-style new community in Winter Garden, incredibly energy-efficient home...	3 beds \| 3 baths \| 2,094 sq.ft.	$559,900	Airbnb cash on cash: -0.42% Traditional cash on cash: 2.57% Airbnb Rental Income: $1636 Traditional Rental Income: $2740 Airbnb ROI: -0.42% Traditional ROI: 2.57%
14501 GROVE RESORT AVENUE #3338 Winter Garden, FL *MOTIVATED SELLERMOTIVATED SELLERMOTIVATED SELLER* Welcome to this NICE "THE GRO...	3 beds \| 2 baths \| 1,396 sq.ft.	$340,000	Airbnb cash on cash: -2.04% Traditional cash on cash: 0.79% Airbnb Rental Income: $1636 Traditional Rental Income: $2079 Airbnb ROI: -2.04% Traditional ROI: 0.79%
14815 TULLAMORE LOOP Winter Garden, FL Don't miss the chance to own this 4 Bedrooms 2 Bath Modern Fully REMODELED house. Once ent...	4 beds \| 2 baths \| 2,314 sq.ft.	$630,000	Airbnb cash on cash: 4.59% Traditional cash on cash: 2.09% Airbnb Rental Income: $5064 Traditional Rental Income: $2563 Airbnb ROI: 4.59% Traditional ROI: 2.09%
17000 RED BIRD ROAD Winter Garden, FL Gorgeous 2.25 acres of mature landscaping just 15 minutes from Disney and 5 minutes from H...	5 beds \| 4 baths \| 3,370 sq.ft.	$1,175,000	Airbnb cash on cash: N/A Traditional cash on cash: 2.19% Airbnb Rental Income: $null Traditional Rental Income: $4816 Airbnb ROI: N/A Traditional ROI: 2.19%
14501 GROVE RESORT AVENUE #2201 Winter Garden, FL Great New Price: $357,500. MOTIVATED SELLER OF THIS GREAT SABLE DESIGN CONDO FOR SALE AT...	3 beds \| 3 baths \| 1,544 sq.ft.	$357,500	Airbnb cash on cash: -3.03% Traditional cash on cash: 0.42% Airbnb Rental Income: $1636 Traditional Rental Income: $2334 Airbnb ROI: -3.03% Traditional ROI: 0.42%
15554 GWINNETT DRIVE Winter Garden, FL Beautiful home for sale in the coveted community of OVERLOOK AT HAMILIN. Have you ever dre...	3 beds \| 4 baths \| 2,304 sq.ft.	$585,000	Airbnb cash on cash: -0.73% Traditional cash on cash: 3.49% Airbnb Rental Income: $1636 Traditional Rental Income: $3481 Airbnb ROI: -0.73% Traditional ROI: 3.49%
15116 DRAGON FLY COURT Winter Garden, FL One or more photo(s) has been virtually staged. Welcome to your future home, where eleganc...	4 beds \| 3 baths \| 2,449 sq.ft.	$635,000	Airbnb cash on cash: 4.4% Traditional cash on cash: 2.43% Airbnb Rental Income: $5064 Traditional Rental Income: $2862 Airbnb ROI: 4.4% Traditional ROI: 2.43%
14501 GROVE RESORT AVENUE #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.	$325,000	Airbnb cash on cash: -0.41% Traditional cash on cash: 1.44% Airbnb Rental Income: $2340 Traditional Rental Income: $2327 Airbnb ROI: -0.41% Traditional ROI: 1.44%
15523 CAMP DUBOIS CRESCENT Winter Garden, FL Independence!!!! One of a kind community!!! Enjoy the Independence lifestyle!!! THIS HOM...	3 beds \| 2 baths \| 1,720 sq.ft.	$495,000	Airbnb cash on cash: -0.11% Traditional cash on cash: 2.42% Airbnb Rental Income: $1636 Traditional Rental Income: $2346 Airbnb ROI: -0.11% Traditional ROI: 2.42%
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.	$499,000	Airbnb cash on cash: -0.83% Traditional cash on cash: 0.85% Airbnb Rental Income: $2340 Traditional Rental Income: $2545 Airbnb ROI: -0.83% Traditional ROI: 0.85%
1156 HAWKSLADE COURT Winter Garden, FL FULLY FURNISHED BEAUTIFUL HOUSE! Ideally situated in a quiet, gated, and guarded community...	3 beds \| 2 baths \| 1,538 sq.ft.	$460,000	Airbnb cash on cash: -0.45% Traditional cash on cash: 1.93% Airbnb Rental Income: $1636 Traditional Rental Income: $2199 Airbnb ROI: -0.45% Traditional ROI: 1.93%
8943 LAKESHORE POINTE DRIVE Winter Garden, FL ONE OF THE PRETTIEST LOCATIONS AND VIEWS IN LAKESHORE!! SHOWS BETTER THAN A MODEL WITH TO...	3 beds \| 3 baths \| 2,052 sq.ft.	$639,900	Airbnb cash on cash: -0.78% Traditional cash on cash: 2.27% Airbnb Rental Income: $1636 Traditional Rental Income: $2996 Airbnb ROI: -0.78% Traditional ROI: 2.27%
14501 GROVE RESORT AVENUE #3535 Winter Garden, FL GREAT NEW REDUCED PRICE: $359,000.00. MOTIVATED SELLER; OWNER FINANCING AVAILABLE. BEAUTIF...	2 beds \| 2 baths \| 1,434 sq.ft.	$359,000	Airbnb cash on cash: -0.84% Traditional cash on cash: 0.44% Airbnb Rental Income: $2340 Traditional Rental Income: $2193 Airbnb ROI: -0.84% Traditional ROI: 0.44%
16253 PEBBLE BLUFF LOOP Winter Garden, FL Waterleigh is a resort-style living community. Situated on a picturesque setting of over 1...	3 beds \| 2 baths \| 1,700 sq.ft.	$505,000	Airbnb cash on cash: -0.56% Traditional cash on cash: 1.89% Airbnb Rental Income: $1636 Traditional Rental Income: $2332 Airbnb ROI: -0.56% Traditional ROI: 1.89%
7570 BISHOP SQUARE DRIVE Winter Garden, FL Under contract-accepting backup offers. Welcome to Your New Beginning! This charming 4-bed...	4 beds \| 2 baths \| 1,952 sq.ft.	$555,000	Airbnb cash on cash: 4.81% Traditional cash on cash: 1.76% Airbnb Rental Income: $5064 Traditional Rental Income: $2449 Airbnb ROI: 4.81% Traditional ROI: 1.76%
14501 GROVE RESORT AVENUE #1535 Winter Garden, FL GREAT NEW REDUCED PRICE: $419,990.00. MOTIVATED SELLER. SELLER FINANCING AVAILABLE. BEAU...	3 beds \| 2 baths \| 1,396 sq.ft.	$419,990	Airbnb cash on cash: -2.04% Traditional cash on cash: 0.31% Airbnb Rental Income: $1636 Traditional Rental Income: $2098 Airbnb ROI: -2.04% Traditional ROI: 0.31%
1755 DELAFIELD DRIVE Winter Garden, FL Under contract-accepting backup offers. This beautifully updated 4-bedroom home is located...	4 beds \| 3 baths \| 2,934 sq.ft.	$628,000	Airbnb cash on cash: 4.63% Traditional cash on cash: 2.81% Airbnb Rental Income: $5064 Traditional Rental Income: $2965 Airbnb ROI: 4.63% Traditional ROI: 2.81%
14501 GROVE RESORT AVENUE #3636 Winter Garden, FL Short Sale. Seller is motivated to Sell Before the FORECLOSURE Deadline - January 8th 2025...	2 beds \| 2 baths \| 1,396 sq.ft.	$345,000	Airbnb cash on cash: -1.02% Traditional cash on cash: 0.05% Airbnb Rental Income: $2340 Traditional Rental Income: $2109 Airbnb ROI: -1.02% Traditional ROI: 0.05%
14501 GROVE RESORT AVENUE #1443 Winter Garden, FL MOTIVATED SELLER AT THE GROVE RESORT & WATER PARK. CONDO-HOTEL, LOCATED MINUTES FROM WALT ...	2 beds \| 2 baths \| 1,375 sq.ft.	$352,500	Airbnb cash on cash: -0.39% Traditional cash on cash: 0.79% Airbnb Rental Income: $2340 Traditional Rental Income: $2152 Airbnb ROI: -0.39% Traditional ROI: 0.79%
470 REGAL DOWNS CIRCLE Winter Garden, FL PRICE REDUCTION!!! First Time Homebuyers - Special Financing available with potentially Z...	4 beds \| 3 baths \| 2,316 sq.ft.	$585,000	Airbnb cash on cash: 5.8% Traditional cash on cash: 4.48% Airbnb Rental Income: $5064 Traditional Rental Income: $3311 Airbnb ROI: 5.8% Traditional ROI: 4.48%
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.	$520,000	Airbnb cash on cash: 5.56% Traditional cash on cash: 2.19% Airbnb Rental Income: $5064 Traditional Rental Income: $2395 Airbnb ROI: 5.56% Traditional ROI: 2.19%
16269 ADMIRALS COVE LANE Winter Garden, FL Welcome to this pristine, modern townhouse in the highly desirable Waterleigh community in...	3 beds \| 3 baths \| 1,568 sq.ft.	$405,000	Airbnb cash on cash: -0.11% Traditional cash on cash: 3.21% Airbnb Rental Income: $1636 Traditional Rental Income: $2433 Airbnb ROI: -0.11% Traditional ROI: 3.21%
2640 BALFORN TOWER WAY Winter Garden, FL One or more photo(s) has been virtually staged. Welcome to the perfect location for your d...	4 beds \| 2 baths \| 1,980 sq.ft.	$479,000	Airbnb cash on cash: 6.59% Traditional cash on cash: 3.05% Airbnb Rental Income: $5064 Traditional Rental Income: $2444 Airbnb ROI: 6.59% Traditional ROI: 3.05%
13633 DANIELS LANDING CIRCLE Winter Garden, FL Do not miss out on this unique opportunity to see this property within the gated community...	3 beds \| 3 baths \| 1,455 sq.ft.	$352,000	Airbnb cash on cash: 0.23% Traditional cash on cash: 3.28% Airbnb Rental Income: $1636 Traditional Rental Income: $2184 Airbnb ROI: 0.23% Traditional ROI: 3.28%
7227 HALF MOON LAKE DRIVE Winter Garden, FL Under contract-accepting backup offers. One of a kind in Winter Garden....you certainly be...	3 beds \| 3 baths \| 2,290 sq.ft.	$474,900	Airbnb cash on cash: -0.69% Traditional cash on cash: 3.01% Airbnb Rental Income: $1636 Traditional Rental Income: $2821 Airbnb ROI: -0.69% Traditional ROI: 3.01%
15162 BOOK CLUB ROAD Winter Garden, FL Amazing Price Improvement! Owner Motivated!! This is a beautiful Storey Grove home featuri...	3 beds \| 2 baths \| 2,089 sq.ft.	$565,000	Airbnb cash on cash: -0.53% Traditional cash on cash: 2.15% Airbnb Rental Income: $1636 Traditional Rental Income: $2587 Airbnb ROI: -0.53% Traditional ROI: 2.15%
13041 INKWELL ALLEY Winter Garden, FL This extraordinary residence is located in the charming neighborhood of Storey Grove. Almo...	4 beds \| 3 baths \| 2,042 sq.ft.	$529,000	Airbnb cash on cash: 5.97% Traditional cash on cash: 3.28% Airbnb Rental Income: $5064 Traditional Rental Income: $2700 Airbnb ROI: 5.97% Traditional ROI: 3.28%
500 TEACUP SPRINGS COURT Winter Garden, FL Rare opportunity with this remodeled 4 bed, 3 bath corner lot home located in the beautifu...	4 beds \| 3 baths \| 2,397 sq.ft.	$549,500	Airbnb cash on cash: 5.57% Traditional cash on cash: 3.68% Airbnb Rental Income: $5064 Traditional Rental Income: $3060 Airbnb ROI: 5.57% Traditional ROI: 3.68%

Real Estate investment in Winter-garden, FL

There are 380 properties for sale in the city of Winter Garden . The median list price in Winter Garden is $560,053 and the average price per square foot is $242. In December 2024, the average monthly cash on cash return in Winter Garden is 3.00%. The average monthly rental income in Winter Garden is $2,668.

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

There are 380 investment properties available for sale in Winter-garden.

In 2024, 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 $2,668.

Your search for investment property begins and ends here

Investment Property for Sale in Winter Garden, FL

1073 VINSETTA CIRCLE

Winter Garden, FL

4 beds | 4 baths | 3,568 sq.ft.

$815,000

Airbnb cash on cash: 3.38%

Traditional cash on cash: 3.82%

Airbnb Rental Income: $5064

Traditional Rental Income: $4365

Airbnb ROI: 3.38%

Traditional ROI: 3.82%

15614 ESPALIER WAY

Winter Garden, FL

5 beds | 7 baths | 6,601 sq.ft.

$4,500,000

Airbnb cash on cash: N/A

Traditional cash on cash: 0.27%

Airbnb Rental Income: $null

Traditional Rental Income: $9380

Airbnb ROI: N/A

Traditional ROI: 0.27%

7224 DESERT MANDARIN STREET

Winter Garden, FL

3 beds | 3 baths | 1,657 sq.ft.

$549,000

Airbnb cash on cash: 0.21%

Traditional cash on cash: 2.57%

Airbnb Rental Income: $1636

Traditional Rental Income: $2384

Airbnb ROI: 0.21%

Traditional ROI: 2.57%

14372 SUNBRIDGE CIRCLE

Winter Garden, FL

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

$835,000

Airbnb cash on cash: 3.14%

Traditional cash on cash: 5.39%

Airbnb Rental Income: $5064

Traditional Rental Income: $5780

Airbnb ROI: 3.14%

Traditional ROI: 5.39%

14132 MURCOTT BLOSSOM BOULEVARD

Winter Garden, FL

4 beds | 3 baths | 2,726 sq.ft.

$715,000

Airbnb cash on cash: 3.67%

Traditional cash on cash: 2.15%

Airbnb Rental Income: $5064

Traditional Rental Income: $3015

Airbnb ROI: 3.67%

Traditional ROI: 2.15%

14177 AVENUE OF THE GRVS

Winter Garden, FL

2 beds | 3 baths | 1,249 sq.ft.

$365,000

Airbnb cash on cash: 1.44%

Traditional cash on cash: 2.72%

Airbnb Rental Income: $2340

Traditional Rental Income: $2199

Airbnb ROI: 1.44%

Traditional ROI: 2.72%

15691 ORANGE HARVEST LOOP

Winter Garden, FL

3 beds | 3 baths | 2,444 sq.ft.

$547,000

Airbnb cash on cash: -0.74%

Traditional cash on cash: 2.57%

Airbnb Rental Income: $1636

Traditional Rental Income: $2866

Airbnb ROI: -0.74%

Traditional ROI: 2.57%

16133 PEBBLE BLUFF LOOP

Winter Garden, FL

3 beds | 3 baths | 1,568 sq.ft.

$439,900

Airbnb cash on cash: 0.18%

Traditional cash on cash: 3.25%

Airbnb Rental Income: $1636

Traditional Rental Income: $2438

Airbnb ROI: 0.18%