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.

Single Family Homes for Sale in Winter Garden, FL

Search for Single Family Residential for Sale in Winter Garden, Florida. Browse all of Mashvisor’s Single Family Residential listings and other investment property types including Single Family Homes, Multi Family Homes, Condos, Townhouses and Other Homes.

Showing 342 Single Family Residential listings of over 500,000 total investment properties for sale. Visit Mashvisor.com to all investment properties.

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PROPERTY	DETAILS	SALE PRICE	INVESTMENT PERFORMANCE
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%
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%
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 #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%
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%
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%
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%
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%
15859 SHOREBIRD LANE Winter Garden, FL Luxury Home, Bavaro Model â Toll Brothers \| 4 Bedrooms \| Pool \| Gourmet Area \| Lakeshore...	4 beds \| 4 baths \| 2,812 sq.ft.	$880,000	Airbnb cash on cash: 1.94% Traditional cash on cash: 1.96% Airbnb Rental Income: $5064 Traditional Rental Income: $4050 Airbnb ROI: 1.94% Traditional ROI: 1.96%
500 TEACUP SPRINGS COURT 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 AVENUE #1743 Winter Garden, FL GREAT OPPORTUNITY TO PURCHASE A LUXURY BIRCH DESIGN 2 BEDROOM 2 BATHROOM FULLY FURNISHED C...	2 beds \| 2 baths \| 1,375 sq.ft.	$306,990	Airbnb cash on cash: -0.8% Traditional cash on cash: 0.31% Airbnb Rental Income: $2340 Traditional Rental Income: $2083 Airbnb ROI: -0.8% Traditional ROI: 0.31%

Your search for investment property begins and ends here

Single Family Homes for Sale in Winter Garden, FL

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%

Traditional ROI: 2.05%

15261 HONEYBELL DRIVE

Winter Garden, FL

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%