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.

Condos for Sale in Winter Garden, FL

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

Showing 474 Condos 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

Condos 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%