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 Residential For Salhttf L For Salhttf L For Salhttf L For Salhttf L Fory Residential for Sale in Winter Garden, FL

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

Showing 474 Single Family Residential For Salhttf L For Salhttf L For Salhttf L For Salhttf L Fory 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.	$850,000	Airbnb cash on cash: 2.97% Traditional cash on cash: 3.15% Airbnb Rental Income: $5064 Traditional Rental Income: $4174 Airbnb ROI: 2.97% Traditional ROI: 3.15%
330 E STORY ROAD Winter Garden, FL Under contract-accepting backup offers. One or more photo(s) has been virtually staged. We...	2 beds \| 1 baths \| 760 sq.ft.	$285,000	Airbnb cash on cash: 4% Traditional cash on cash: 4.63% Airbnb Rental Income: $2340 Traditional Rental Income: $1929 Airbnb ROI: 4% Traditional ROI: 4.63%
12456 WESTFIELD LAKES CIRCLE Winter Garden, FL Welcome home to this stunning residence in the highly desirable Westfield Lakes community,...	4 beds \| 3 baths \| 2,180 sq.ft.	$549,000	Airbnb cash on cash: 5.83% Traditional cash on cash: 3.32% Airbnb Rental Income: $5064 Traditional Rental Income: $2747 Airbnb ROI: 5.83% Traditional ROI: 3.32%
7189 SUMMERLAKE GROVES STREET Winter Garden, FL COME set your eyes on your Gorgeous 2-Story Winter Garden DREAM HOME located in the Highla...	3 beds \| 3 baths \| 2,138 sq.ft.	$609,999	Airbnb cash on cash: -0.5% Traditional cash on cash: 2.85% Airbnb Rental Income: $1636 Traditional Rental Income: $3086 Airbnb ROI: -0.5% Traditional ROI: 2.85%
337 SUNSET OAKS RD Winter Garden, FL This exceptional home is ideally located in the desirable Golf Cart District, offering par...	4 beds \| 3 baths \| 2,186 sq.ft.	$599,900	Airbnb cash on cash: 4.61% Traditional cash on cash: 4.05% Airbnb Rental Income: $5064 Traditional Rental Income: $3717 Airbnb ROI: 4.61% Traditional ROI: 4.05%
15140 SUNRISE GROVE COURT Winter Garden, FL Imagine a life where lakeside serenity meets modern sophistication. Tucked behind the priv...	3 beds \| 3 baths \| 2,012 sq.ft.	$399,987	Airbnb cash on cash: -0.74% Traditional cash on cash: 4.93% Airbnb Rental Income: $1636 Traditional Rental Income: $3303 Airbnb ROI: -0.74% Traditional ROI: 4.93%
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.	$775,000	Airbnb cash on cash: 3.46% Traditional cash on cash: 4.2% Airbnb Rental Income: $5064 Traditional Rental Income: $4563 Airbnb ROI: 3.46% Traditional ROI: 4.2%
16232 ROCK COAST DRIVE Winter Garden, FL Welcome to your dream home and backyard oasis! This beautiful GAS HEATED SALTWATER POOL ho...	4 beds \| 5 baths \| 3,491 sq.ft.	$949,000	Airbnb cash on cash: 2.32% Traditional cash on cash: 5.3% Airbnb Rental Income: $5064 Traditional Rental Income: $6667 Airbnb ROI: 2.32% Traditional ROI: 5.3%
373 ERON WAY #47 Winter Garden, FL Short Sale. MOVE-IN READY and quietly positioned within a well-established Winter Garden c...	2 beds \| 2 baths \| 840 sq.ft.	$163,999	Airbnb cash on cash: 5.44% Traditional cash on cash: 6.15% Airbnb Rental Income: $2340 Traditional Rental Income: $1872 Airbnb ROI: 5.44% Traditional ROI: 6.15%
14501 GROVE RESORT AVENUE #1111 Winter Garden, FL Ground Floor Unit \| Pond and Fountain Views \| Aggressively Priced Ground floor residence f...	2 beds \| 2 baths \| 1,265 sq.ft.	$205,000	Airbnb cash on cash: -0.51% Traditional cash on cash: 3.73% Airbnb Rental Income: $2340 Traditional Rental Income: $2586 Airbnb ROI: -0.51% Traditional ROI: 3.73%
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.	$549,900	Airbnb cash on cash: -0.29% Traditional cash on cash: 3.31% Airbnb Rental Income: $1636 Traditional Rental Income: $3022 Airbnb ROI: -0.29% Traditional ROI: 3.31%
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.	$929,500	Airbnb cash on cash: 2.55% Traditional cash on cash: 4.42% Airbnb Rental Income: $5064 Traditional Rental Income: $5648 Airbnb ROI: 2.55% Traditional ROI: 4.42%
374 MILLWOOD PLACE Winter Garden, FL Under contract-accepting backup offers. READY TO DISCOVER A HOME THAT TRULY STANDS OUT? S...	3 beds \| 2 baths \| 2,200 sq.ft.	$575,000	Airbnb cash on cash: 0.03% Traditional cash on cash: 3.57% Airbnb Rental Income: $1636 Traditional Rental Income: $3076 Airbnb ROI: 0.03% Traditional ROI: 3.57%
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.	$399,000	Airbnb cash on cash: -0.71% Traditional cash on cash: 3.68% Airbnb Rental Income: $1636 Traditional Rental Income: $2814 Airbnb ROI: -0.71% Traditional ROI: 3.68%
5685 NEW INDEPENDENCE PARKWAY Winter Garden, FL Under contract-accepting backup offers. Welcome to this newly UPDATED and uniquely UPGRADE...	3 beds \| 3 baths \| 1,751 sq.ft.	$452,000	Airbnb cash on cash: -0.07% Traditional cash on cash: 2.9% Airbnb Rental Income: $1636 Traditional Rental Income: $2430 Airbnb ROI: -0.07% Traditional ROI: 2.9%
14447 PRUNNINGWOOD PLACE Winter Garden, FL One or more photo(s) has been virtually staged. This stylish townhome in the highly sought...	2 beds \| 3 baths \| 1,250 sq.ft.	$340,000	Airbnb cash on cash: 1.81% Traditional cash on cash: 3.57% Airbnb Rental Income: $2340 Traditional Rental Income: $2322 Airbnb ROI: 1.81% Traditional ROI: 3.57%
1166 WESTSIDE DRIVE Winter Garden, FL Under contract-accepting backup offers. Buy this charming 3bedroom, 2bath townhome in desi...	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%
900 WALKERS GROVE LANE Winter Garden, FL Downtown Winter Garden â Golf Cart District! Donât miss this amazing opportunity to...	3 beds \| 3 baths \| 1,905 sq.ft.	$485,000	Airbnb cash on cash: -0.11% Traditional cash on cash: 3.49% Airbnb Rental Income: $1636 Traditional Rental Income: $2810 Airbnb ROI: -0.11% Traditional ROI: 3.49%
16554 RAVEN ROCK PLACE Winter Garden, FL Twinwaters Former MODEL home built with BEAUTIFUL UPGRADES 3 car garage ** Heated PO...	4 beds \| 3 baths \| 3,032 sq.ft.	$875,000	Airbnb cash on cash: 2.82% Traditional cash on cash: 3.35% Airbnb Rental Income: $5064 Traditional Rental Income: $4466 Airbnb ROI: 2.82% Traditional ROI: 3.35%
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: 1.4% Airbnb Rental Income: $1636 Traditional Rental Income: $2476 Airbnb ROI: -2.56% Traditional ROI: 1.4%
213 W TILDEN STREET Winter Garden, FL Located in DOWNTOWN WINTER GARDEN!! This beautifully renovated single story home combi...	4 beds \| 2 baths \| 2,151 sq.ft.	$765,000	Airbnb cash on cash: 3.47% Traditional cash on cash: 2.24% Airbnb Rental Income: $5064 Traditional Rental Income: $3152 Airbnb ROI: 3.47% Traditional ROI: 2.24%
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.	$829,000	Airbnb cash on cash: 2.24% Traditional cash on cash: 1.96% Airbnb Rental Income: $5064 Traditional Rental Income: $3816 Airbnb ROI: 2.24% Traditional ROI: 1.96%
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.	$870,000	Airbnb cash on cash: 2.81% Traditional cash on cash: 3.09% Airbnb Rental Income: $5064 Traditional Rental Income: $4257 Airbnb ROI: 2.81% Traditional ROI: 3.09%
5531 CYPRESS HILL ROAD Winter Garden, FL Exquisitely upgraded 4-bedroom, 3-bath smart home in the highly sought-after Orchard Hills...	4 beds \| 3 baths \| 2,204 sq.ft.	$625,000	Airbnb cash on cash: 4.02% Traditional cash on cash: 2.92% Airbnb Rental Income: $5064 Traditional Rental Income: $3389 Airbnb ROI: 4.02% Traditional ROI: 2.92%
1112 JUNIPER HAMMOCK COURT Winter Garden, FL One or more photo(s) has been virtually staged. Welcome to this beautiful and spacious 4-b...	4 beds \| 2 baths \| 2,545 sq.ft.	$525,000	Airbnb cash on cash: 5.7% Traditional cash on cash: 3.88% Airbnb Rental Income: $5064 Traditional Rental Income: $3136 Airbnb ROI: 5.7% Traditional ROI: 3.88%
8122 RED STOPPER LANE Winter Garden, FL Beautifully presented 3-bedroom, 2.5-bath townhome built in 2017, offering 1,784 SF of liv...	3 beds \| 3 baths \| 1,784 sq.ft.	$435,000	Airbnb cash on cash: -0.48% Traditional cash on cash: 3.47% Airbnb Rental Income: $1636 Traditional Rental Income: $2783 Airbnb ROI: -0.48% Traditional ROI: 3.47%
648 ORANGE BELT LOOP Winter Garden, FL Welcome to your opportunity to own in one of the most desirable locations near downtown Wi...	3 beds \| 3 baths \| 1,688 sq.ft.	$525,000	Airbnb cash on cash: -0.35% Traditional cash on cash: 2.78% Airbnb Rental Income: $1636 Traditional Rental Income: $2710 Airbnb ROI: -0.35% Traditional ROI: 2.78%
8256 BAYVIEW CROSSING DRIVE Winter Garden, FL PRICE IMPROVEMENT....UPGRADED POOL HOME in Horizon West! Welcome to this 4-bed, 3.5-bath,...	4 beds \| 4 baths \| 2,557 sq.ft.	$675,000	Airbnb cash on cash: 3.27% Traditional cash on cash: 3.5% Airbnb Rental Income: $5064 Traditional Rental Income: $4179 Airbnb ROI: 3.27% Traditional ROI: 3.5%
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: 4.74% Airbnb Rental Income: $2340 Traditional Rental Income: $1987 Airbnb ROI: 3.9% Traditional ROI: 4.74%
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.	$298,500	Airbnb cash on cash: -0.36% Traditional cash on cash: 2.22% Airbnb Rental Income: $2340 Traditional Rental Income: $2486 Airbnb ROI: -0.36% Traditional ROI: 2.22%
131 OAK LAUREL DRIVE Winter Garden, FL 131 Oak Laurel Drive is a stunning, modern townhome built in 2019 in the highly desirable ...	3 beds \| 4 baths \| 1,906 sq.ft.	$895,000	Airbnb cash on cash: -1.51% Traditional cash on cash: 0.8% Airbnb Rental Income: $1636 Traditional Rental Income: $3103 Airbnb ROI: -1.51% Traditional ROI: 0.8%
15334 MURCOTT BLOSSOM BOULEVARD Winter Garden, FL Beautiful 3-bedroom, 2.5-bathroom townhouse available in the great Summerlake community of...	3 beds \| 3 baths \| 1,868 sq.ft.	$450,000	Airbnb cash on cash: -0.86% Traditional cash on cash: 2.89% Airbnb Rental Income: $1636 Traditional Rental Income: $2754 Airbnb ROI: -0.86% Traditional ROI: 2.89%
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: 1.88% Airbnb Rental Income: $2340 Traditional Rental Income: $2936 Airbnb ROI: -0.9% Traditional ROI: 1.88%
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: 1.77% Airbnb Rental Income: $2340 Traditional Rental Income: $2774 Airbnb ROI: -0.99% Traditional ROI: 1.77%
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: 2.59% Airbnb Rental Income: $5064 Traditional Rental Income: $3554 Airbnb ROI: 3.25% Traditional ROI: 2.59%
14421 VASHONS WAY Winter Garden, FL Motivated Seller! Experience the best of Florida living just 20 minutes from Disney! This ...	2 beds \| 3 baths \| 1,088 sq.ft.	$339,900	Airbnb cash on cash: 2.43% Traditional cash on cash: 3.24% Airbnb Rental Income: $2340 Traditional Rental Income: $2020 Airbnb ROI: 2.43% Traditional ROI: 3.24%
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.	$1,125,000	Airbnb cash on cash: -0.78% Traditional cash on cash: 2.89% Airbnb Rental Income: $1636 Traditional Rental Income: $5018 Airbnb ROI: -0.78% Traditional ROI: 2.89%
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.	$245,000	Airbnb cash on cash: -0.68% Traditional cash on cash: 3.26% Airbnb Rental Income: $2340 Traditional Rental Income: $2673 Airbnb ROI: -0.68% Traditional ROI: 3.26%
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.	$299,000	Airbnb cash on cash: -3.47% Traditional cash on cash: 1.17% Airbnb Rental Income: $1636 Traditional Rental Income: $2480 Airbnb ROI: -3.47% Traditional ROI: 1.17%
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.	$224,000	Airbnb cash on cash: -4.15% Traditional cash on cash: 1.85% Airbnb Rental Income: $1636 Traditional Rental Income: $2447 Airbnb ROI: -4.15% Traditional ROI: 1.85%

Your search for investment property begins and ends here

Single Family Residential For Salhttf L For Salhttf L For Salhttf L For Salhttf L Fory Residential for Sale in Winter Garden, FL

607 E OAKLAND AVENUE

Winter Garden, FL

4 beds | 4 baths | 3,406 sq.ft.

$850,000

Airbnb cash on cash: 2.97%

Traditional cash on cash: 3.15%

Airbnb Rental Income: $5064

Traditional Rental Income: $4174

Airbnb ROI: 2.97%

Traditional ROI: 3.15%

330 E STORY ROAD

Winter Garden, FL

2 beds | 1 baths | 760 sq.ft.

$285,000

Airbnb cash on cash: 4%

Traditional cash on cash: 4.63%

Airbnb Rental Income: $2340

Traditional Rental Income: $1929

Airbnb ROI: 4%

Traditional ROI: 4.63%

12456 WESTFIELD LAKES CIRCLE

Winter Garden, FL

4 beds | 3 baths | 2,180 sq.ft.

$549,000

Airbnb cash on cash: 5.83%

Traditional cash on cash: 3.32%

Airbnb Rental Income: $5064

Traditional Rental Income: $2747

Airbnb ROI: 5.83%

Traditional ROI: 3.32%

7189 SUMMERLAKE GROVES STREET

Winter Garden, FL

3 beds | 3 baths | 2,138 sq.ft.

$609,999

Airbnb cash on cash: -0.5%

Traditional cash on cash: 2.85%

Airbnb Rental Income: $1636

Traditional Rental Income: $3086

Airbnb ROI: -0.5%

Traditional ROI: 2.85%

337 SUNSET OAKS RD

Winter Garden, FL

4 beds | 3 baths | 2,186 sq.ft.

$599,900

Airbnb cash on cash: 4.61%

Traditional cash on cash: 4.05%

Airbnb Rental Income: $5064

Traditional Rental Income: $3717

Airbnb ROI: 4.61%

Traditional ROI: 4.05%

15140 SUNRISE GROVE COURT

Winter Garden, FL

3 beds | 3 baths | 2,012 sq.ft.

$399,987

Airbnb cash on cash: -0.74%

Traditional cash on cash: 4.93%

Airbnb Rental Income: $1636

Traditional Rental Income: $3303

Airbnb ROI: -0.74%

Traditional ROI: 4.93%

14372 SUNBRIDGE CIRCLE

Winter Garden, FL

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

$775,000

Airbnb cash on cash: 3.46%

Traditional cash on cash: 4.2%

Airbnb Rental Income: $5064

Traditional Rental Income: $4563

Airbnb ROI: 3.46%

Traditional ROI: 4.2%

16232 ROCK COAST DRIVE

Winter Garden, FL

4 beds | 5 baths | 3,491 sq.ft.

$949,000

Airbnb cash on cash: 2.32%

Traditional cash on cash: 5.3%

Airbnb Rental Income: $5064

Traditional Rental Income: $6667

Airbnb ROI: 2.32%