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 333 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
607 E OAKLAND AVENUE Winter Garden, FL Welcome to this exceptional Winter Garden home with 4 bedrooms, 3.5-bathrooms, PLUS home o...	4 beds \| 4 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%
15445 PEBBLE RIDGE STREET Winter Garden, FL Under contract-accepting backup offers. Video Tour Available Welcome to Stoneybrook We...	4 beds \| 2 baths \| 2,375 sq.ft.	$575,000	Airbnb cash on cash: 4.79% Traditional cash on cash: 3.32% Airbnb Rental Income: $5064 Traditional Rental Income: $3245 Airbnb ROI: 4.79% Traditional ROI: 3.32%
7189 SUMMERLAKE GROVES STREET Winter Garden, FL COME set your eyes on this Gorgeous 2-Story Winter Garden home located in Highlands at Sum...	3 beds \| 3 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 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 Under contract-accepting backup offers. Multiple offers! We listened to feed back. We hav...	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 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%
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 Price improvement and quick close available. WELCOME HOME: YOUR WINTER GARDEN ESCAPE AWAI...	4 beds \| 4 baths \| 3,479 sq.ft.	$939,900	Airbnb cash on cash: 2.52% Traditional cash on cash: 3.43% Airbnb Rental Income: $5064 Traditional Rental Income: $4828 Airbnb ROI: 2.52% Traditional ROI: 3.43%
14645 SCOTT KEY DRIVE Winter Garden, FL Beautifully updated single-family home featuring NEW EXTERIOR PAINT AND NEW FLOORING THROU...	4 beds \| 4 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%
13377 Lake Butler Blvd Winter Garden, FL One or more photo(s) has been virtually staged. BACK ON MARKET: Buyer's inability to obtai...	5 beds \| 4 baths \| 6,000 sq.ft.	$5,995,000	Airbnb cash on cash: N/A Traditional cash on cash: -0.16% Airbnb Rental Income: $null Traditional Rental Income: $6091 Airbnb ROI: N/A Traditional ROI: -0.16%
15210 E OAKLAND AVENUE Winter Garden, FL Discover the pinnacle of custom-built luxury in Winter Garden with this spectacular 5-bedr...	5 beds \| 3 baths \| 3,789 sq.ft.	$1,775,000	Airbnb cash on cash: N/A Traditional cash on cash: -0.31% Airbnb Rental Income: $null Traditional Rental Income: $3612 Airbnb ROI: N/A Traditional ROI: -0.31%
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.	$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 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.	$299,000	Airbnb cash on cash: -0.36% Traditional cash on cash: 1.65% Airbnb Rental Income: $2340 Traditional Rental Income: $2327 Airbnb ROI: -0.36% Traditional ROI: 1.65%
16162 JOHNS LAKE OVERLOOK DRIVE Winter Garden, FL Set on an oversized corner lot spanning over a quarter acre, this exceptional home offers ...	5 beds \| 4 baths \| 3,528 sq.ft.	$799,000	Airbnb cash on cash: N/A Traditional cash on cash: 3.33% Airbnb Rental Income: $null Traditional Rental Income: $4474 Airbnb ROI: N/A Traditional ROI: 3.33%
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.	$281,000	Airbnb cash on cash: -0.72% Traditional cash on cash: 1.55% Airbnb Rental Income: $2340 Traditional Rental Income: $2362 Airbnb ROI: -0.72% Traditional ROI: 1.55%
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 Gorgeous Lakeview Condo at The Grove Resort & Water Park Orlando! Perfect for snowbirds o...	3 beds \| 2 baths \| 1,396 sq.ft.	$284,000	Airbnb cash on cash: -3.5% Traditional cash on cash: 0.48% Airbnb Rental Income: $1636 Traditional Rental Income: $2238 Airbnb ROI: -3.5% Traditional ROI: 0.48%
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.	$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%
14501 GROVE RESORT AVENUE #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.	$274,000	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 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%
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%
15594 SHOREBIRD LANE Winter Garden, FL Wake up to serene lake views and enjoy a private Disney fireworks show every night! Locate...	4 beds \| 4 baths \| 3,022 sq.ft.	$1,275,000	Airbnb cash on cash: 0.57% Traditional cash on cash: 0.48% Airbnb Rental Income: $5064 Traditional Rental Income: $3926 Airbnb ROI: 0.57% Traditional ROI: 0.48%
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.	$554,000	Airbnb cash on cash: 0.14% Traditional cash on cash: 3.1% Airbnb Rental Income: $1636 Traditional Rental Income: $2709 Airbnb ROI: 0.14% Traditional ROI: 3.1%
15859 SHOREBIRD LANE Winter Garden, FL Under contract-accepting backup offers. UNDER CONTRACT IN ONLY 2 WEEKS ACCEPTING BACKUP OF...	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%
17117 HEARTWOOD LOOP Winter Garden, FL Welcome to your very own slice of Winter Garden paradise! This impressive 5.3-acre, high-a...	5 beds \| 4 baths \| 3,265 sq.ft.	$1,249,900	Airbnb cash on cash: N/A Traditional cash on cash: 1.23% Airbnb Rental Income: $null Traditional Rental Income: $3785 Airbnb ROI: N/A Traditional ROI: 1.23%
14200 AVALON ROAD #406 Winter Garden, FL Discover a Hidden Gem in the Heart of Winter Garden! This rarely available, fully furni...	3 beds \| 2 baths \| 1,288 sq.ft.	$225,000	Airbnb cash on cash: -1.07% Traditional cash on cash: 3.33% Airbnb Rental Income: $1636 Traditional Rental Income: $2112 Airbnb ROI: -1.07% Traditional ROI: 3.33%
10386 ATWATER BAY DRIVE Winter Garden, FL Experience the best of resort-style living in the desirable Waterleigh community of Winter...	4 beds \| 3 baths \| 2,117 sq.ft.	$699,900	Airbnb cash on cash: 3.37% Traditional cash on cash: 1.49% Airbnb Rental Income: $5064 Traditional Rental Income: $2805 Airbnb ROI: 3.37% Traditional ROI: 1.49%
634 BURCH AVENUE Winter Garden, FL One or more photo(s) has been virtually staged. Seller offering $7,500 towards buyerâs c...	4 beds \| 4 baths \| 2,351 sq.ft.	$650,000	Airbnb cash on cash: 4.67% Traditional cash on cash: 4.18% Airbnb Rental Income: $5064 Traditional Rental Income: $3731 Airbnb ROI: 4.67% Traditional ROI: 4.18%

Your search for investment property begins and ends here

Single Family Homes for Sale in Winter Garden, FL

607 E OAKLAND AVENUE

Winter Garden, FL

4 beds | 4 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%

15445 PEBBLE RIDGE STREET

Winter Garden, FL

4 beds | 2 baths | 2,375 sq.ft.

$575,000

Airbnb cash on cash: 4.79%

Traditional cash on cash: 3.32%

Airbnb Rental Income: $5064

Traditional Rental Income: $3245

Airbnb ROI: 4.79%

Traditional ROI: 3.32%

7189 SUMMERLAKE GROVES STREET

Winter Garden, FL

3 beds | 3 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 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%

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%