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 695 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
849 Shadowmoss Dr Winter Garden, FL One or more photo(s) has been virtually staged. Prime Winter Garden Location \| Westfield L...	5 beds \| 3 baths \| 2,620 sq.ft.	$750,000	Airbnb cash on cash: N/A Traditional cash on cash: 2.48% Airbnb Rental Income: $null Traditional Rental Income: $3077 Airbnb ROI: N/A Traditional ROI: 2.48%
13728 Fox Glove St Winter Garden, FL Short Sale. Short Sale--AS IS4 bedroom, 2 1/2 baths pool home in Stoneybrook West Comm...	5 beds \| 3 baths \| 3,391 sq.ft.	$739,900	Airbnb cash on cash: N/A Traditional cash on cash: 3.04% Airbnb Rental Income: $null Traditional Rental Income: $3736 Airbnb ROI: N/A Traditional ROI: 3.04%
7189 Summerlake Groves St Winter Garden, FL COME set your eyes on your Gorgeous 2-Story Winter Garden DREAM HOME located in the Highla...	3 beds \| 2 baths \| 2,138 sq.ft.	$609,999	Airbnb cash on cash: -0.5% Traditional cash on cash: 3.22% Airbnb Rental Income: $1636 Traditional Rental Income: $3295 Airbnb ROI: -0.5% Traditional ROI: 3.22%
14372 Sunbridge Cir Winter Garden, FL This is a unique opportunity to live in the highly sought-after gated community of Bradfor...	4 beds \| 4 baths \| 3,468 sq.ft.	$745,000	Airbnb cash on cash: 3.64% Traditional cash on cash: 6.44% Airbnb Rental Income: $5064 Traditional Rental Income: $5980 Airbnb ROI: 3.64% Traditional ROI: 6.44%
16197 Wind View Ln Winter Garden, FL Welcome to Waterleigh-Marina Bay! This quiet & lovely neighborhood is beautifully maintain...	3 beds \| 2 baths \| 2,027 sq.ft.	$527,000	Airbnb cash on cash: -0.44% Traditional cash on cash: 3.19% Airbnb Rental Income: $1636 Traditional Rental Income: $2962 Airbnb ROI: -0.44% Traditional ROI: 3.19%
264 BLUE STONE CIRCLE Winter Garden, FL LOCATION, LOCATION, LOCATION! Welcome to 264 Blue Stone Cir in the highly desirable Winter...	4 beds \| 3 baths \| 2,538 sq.ft.	$725,000	Airbnb cash on cash: 4.02% Traditional cash on cash: 3.53% Airbnb Rental Income: $5064 Traditional Rental Income: $3698 Airbnb ROI: 4.02% Traditional ROI: 3.53%
2202 Romanum Dr Winter Garden, FL Welcome to your next home in the heart of Winter Gardenâwhere location, lifestyle, and u...	3 beds \| 2 baths \| 1,889 sq.ft.	$585,000	Airbnb cash on cash: -0.1% Traditional cash on cash: 2.21% Airbnb Rental Income: $1636 Traditional Rental Income: $2435 Airbnb ROI: -0.1% Traditional ROI: 2.21%
16232 ROCK COAST DRIVE Winter Garden, FL Under contract-accepting backup offers. Welcome to your dream home and backyard oasis! Thi...	4 beds \| 5 baths \| 3,491 sq.ft.	$925,000	Airbnb cash on cash: 2.41% Traditional cash on cash: 6.22% Airbnb Rental Income: $5064 Traditional Rental Income: $7312 Airbnb ROI: 2.41% Traditional ROI: 6.22%
15558 Sandfield Loop Winter Garden, FL NEW PRICE MAKES THIS THE BEST DEAL ON THE BLOCK! This one will check ALL your boxes...Tayl...	4 beds \| 3 baths \| 4,307 sq.ft.	$765,000	Airbnb cash on cash: 3.49% Traditional cash on cash: 2.23% Airbnb Rental Income: $5064 Traditional Rental Income: $3134 Airbnb ROI: 3.49% Traditional ROI: 2.23%
2154 Oakington St Winter Garden, FL Welcome to this beautifully maintained, single-story home that perfectly blends comfort, s...	3 beds \| 2 baths \| 1,585 sq.ft.	$469,900	Airbnb cash on cash: -0.25% Traditional cash on cash: 2.23% Airbnb Rental Income: $1636 Traditional Rental Income: $2263 Airbnb ROI: -0.25% Traditional ROI: 2.23%
897 Landrum Dr Winter Garden, FL Welcome to one of Winter Garden's most coveted addresses â nestled in the heart of the G...	4 beds \| 3 baths \| 3,012 sq.ft.	$899,900	Airbnb cash on cash: 2.73% Traditional cash on cash: 1.96% Airbnb Rental Income: $5064 Traditional Rental Income: $3383 Airbnb ROI: 2.73% Traditional ROI: 1.96%
9338 Tyrella Pine Trl Winter Garden, FL You will love this beautiful 4 bedrooms, 2.5 bathrooms, 2 car garage home located in the d...	4 beds \| 2 baths \| 1,696 sq.ft.	$449,000	Airbnb cash on cash: 7.75% Traditional cash on cash: 4.89% Airbnb Rental Income: $5064 Traditional Rental Income: $2829 Airbnb ROI: 7.75% Traditional ROI: 4.89%
14282 Creekbed Cir Winter Garden, FL *Seller is willing to contribute up to $5,000 towards interest rate buy down or closing co...	4 beds \| 4 baths \| 3,479 sq.ft.	$924,500	Airbnb cash on cash: 2.57% Traditional cash on cash: 4.61% Airbnb Rental Income: $5064 Traditional Rental Income: $5782 Airbnb ROI: 2.57% Traditional ROI: 4.61%
5401 BOWMAN DRIVE Winter Garden, FL Welcome to Horizon West living at its finest in the highly sought-after Overlook at Hamlin...	4 beds \| 4 baths \| 4,044 sq.ft.	$1,250,000	Airbnb cash on cash: 1.46% Traditional cash on cash: 1.96% Airbnb Rental Income: $5064 Traditional Rental Income: $4606 Airbnb ROI: 1.46% Traditional ROI: 1.96%
604 FOSTER AVENUE Winter Garden, FL Under contract-accepting backup offers. Situated just two blocks outside the Golf Cart Dis...	3 beds \| 2 baths \| 1,275 sq.ft.	$400,000	Airbnb cash on cash: 1.48% Traditional cash on cash: 3.92% Airbnb Rental Income: $1636 Traditional Rental Income: $2092 Airbnb ROI: 1.48% Traditional ROI: 3.92%
1672 Malcolm Pointe Dr Winter Garden, FL Charming 3BD/2BA HOME sits on 1/4 ACRE LOT in a quiet CUL-DE-SAC with a NEW ROOF (2021), N...	3 beds \| 2 baths \| 2,035 sq.ft.	$509,900	Airbnb cash on cash: 0.56% Traditional cash on cash: 2.94% Airbnb Rental Income: $1636 Traditional Rental Income: $2311 Airbnb ROI: 0.56% Traditional ROI: 2.94%
7832 Freestyle Ln Winter Garden, FL BETTER THAN NEW and less than 1 year old. Ideal MODERN one story floor plan with all the r...	4 beds \| 3 baths \| 2,650 sq.ft.	$1,075,000	Airbnb cash on cash: 2.44% Traditional cash on cash: 1.44% Airbnb Rental Income: $5064 Traditional Rental Income: $3030 Airbnb ROI: 2.44% Traditional ROI: 1.44%
261 Zachary Wade St Winter Garden, FL *** Multiple offers received, deadline for highest and best is Wednesday 06/01/2022 @ 10am...	4 beds \| 3 baths \| 3,728 sq.ft.	$1,699,000	Airbnb cash on cash: 0.96% Traditional cash on cash: 0.65% Airbnb Rental Income: $5064 Traditional Rental Income: $3554 Airbnb ROI: 0.96% Traditional ROI: 0.65%
13536 Sunset Lakes Cir Winter Garden, FL Experience luxury living in this gorgeous home in the highly sought after Sunset Lakes com...	5 beds \| 4 baths \| 3,389 sq.ft.	$1,150,000	Airbnb cash on cash: N/A Traditional cash on cash: 3.72% Airbnb Rental Income: $null Traditional Rental Income: $6227 Airbnb ROI: N/A Traditional ROI: 3.72%
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: 0.02% Airbnb Rental Income: $null Traditional Rental Income: $7090 Airbnb ROI: N/A Traditional ROI: 0.02%
10007 Little Alcove Loop Winter Garden, FL Don't wait to build new- enjoy the upgraded finishes in this Emerald Home now! Beautifully...	4 beds \| 3 baths \| 2,921 sq.ft.	$999,990	Airbnb cash on cash: 2.84% Traditional cash on cash: 2.49% Airbnb Rental Income: $5064 Traditional Rental Income: $3702 Airbnb ROI: 2.84% Traditional ROI: 2.49%
7266 Desert Mandarin St Winter Garden, FL Great investment opportunity! Welcome to this beautifully maintained home built in 2018, f...	4 beds \| 3 baths \| 2,365 sq.ft.	$595,000	Airbnb cash on cash: 4.34% Traditional cash on cash: 2.29% Airbnb Rental Income: $5064 Traditional Rental Income: $2890 Airbnb ROI: 4.34% Traditional ROI: 2.29%
9355 Tyrella Pine Trl Winter Garden, FL This Winter Garden two-story home offers a den, kitchen quartz countertops, stainless stee...	3 beds \| 2 baths \| 1,670 sq.ft.	$475,000	Airbnb cash on cash: 0.34% Traditional cash on cash: 2.76% Airbnb Rental Income: $1636 Traditional Rental Income: $2250 Airbnb ROI: 0.34% Traditional ROI: 2.76%
15508 PEBBLE RIDGE STREET Winter Garden, FL This is the one youâve been waiting for. A beautifully maintained four bedroom pool home...	4 beds \| 3 baths \| 2,763 sq.ft.	$695,000	Airbnb cash on cash: 3.79% Traditional cash on cash: 3.14% Airbnb Rental Income: $5064 Traditional Rental Income: $3612 Airbnb ROI: 3.79% Traditional ROI: 3.14%
705 Garden West Ter Winter Garden, FL New Construction by custom builder. Enjoy TRAILSIDE living at it's finest! Garden West is ...	4 beds \| 3 baths \| 2,698 sq.ft.	$1,350,000	Airbnb cash on cash: 1.05% Traditional cash on cash: 0.2% Airbnb Rental Income: $5064 Traditional Rental Income: $2963 Airbnb ROI: 1.05% Traditional ROI: 0.2%
1646 Holcomb Creek St Winter Garden, FL LOOK NO MORE! This is one of the most spectacular and energy efficient Meritage Home's fl...	4 beds \| 4 baths \| 3,841 sq.ft.	$929,000	Airbnb cash on cash: 2.65% Traditional cash on cash: 3.32% Airbnb Rental Income: $5064 Traditional Rental Income: $4609 Airbnb ROI: 2.65% Traditional ROI: 3.32%
16137 Wind View Ln Winter Garden, FL DON'T WAIT FOR A NEW BUILT, WHEN YOU CAN PURCHASE THIS AMAZING HOME THAT JUST HIT THE MARK...	4 beds \| 3 baths \| 2,477 sq.ft.	$565,000	Airbnb cash on cash: 5.05% Traditional cash on cash: 4.44% Airbnb Rental Income: $5064 Traditional Rental Income: $3707 Airbnb ROI: 5.05% Traditional ROI: 4.44%
16029 Tollington Aly Winter Garden, FL This beautiful MODEL HOME WITH LEASEBACK delivers 3 beds, 2.5 bath, and a 2-car alley-load...	3 beds \| 2 baths \| 2,341 sq.ft.	$619,500	Airbnb cash on cash: 0.38% Traditional cash on cash: 2.85% Airbnb Rental Income: $1636 Traditional Rental Income: $2597 Airbnb ROI: 0.38% Traditional ROI: 2.85%
5460 Bowman Dr Winter Garden, FL Video Tour Available Welcome to Overlook at Hamlin, where an active, vibrant lifestyle...	3 beds \| 3 baths \| 2,474 sq.ft.	$625,000	Airbnb cash on cash: -1.19% Traditional cash on cash: 1.91% Airbnb Rental Income: $1636 Traditional Rental Income: $2981 Airbnb ROI: -1.19% Traditional ROI: 1.91%
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%
8721 Bayview Crossing Dr Winter Garden, FL Amazing opportunity for a corner lot pool home, within the highly demanded Waterleigh - Ma...	4 beds \| 3 baths \| 2,842 sq.ft.	$695,000	Airbnb cash on cash: 3.34% Traditional cash on cash: 3.46% Airbnb Rental Income: $5064 Traditional Rental Income: $4111 Airbnb ROI: 3.34% Traditional ROI: 3.46%
15852 Shorebird Ln Winter Garden, FL Stunning 2-Story Home in Winter Garden â 4 Bedrooms, Solar Panels, and Exceptional Featu...	4 beds \| 4 baths \| 2,766 sq.ft.	$799,000	Airbnb cash on cash: 2.36% Traditional cash on cash: 2.67% Airbnb Rental Income: $5064 Traditional Rental Income: $4262 Airbnb ROI: 2.36% Traditional ROI: 2.67%
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: 4.09% Airbnb Rental Income: $5064 Traditional Rental Income: $5070 Airbnb ROI: 2.81% Traditional ROI: 4.09%
5531 CYPRESS HILL ROAD Winter Garden, FL Under contract-accepting backup offers. Exquisitely upgraded 4-bedroom, 3-bath smart home ...	4 beds \| 3 baths \| 2,204 sq.ft.	$610,000	Airbnb cash on cash: 4.14% Traditional cash on cash: 3.02% Airbnb Rental Income: $5064 Traditional Rental Income: $3393 Airbnb ROI: 4.14% Traditional ROI: 3.02%
1112 Juniper Hammock Ct 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.	$520,000	Airbnb cash on cash: 5.77% Traditional cash on cash: 3.96% Airbnb Rental Income: $5064 Traditional Rental Income: $3154 Airbnb ROI: 5.77% Traditional ROI: 3.96%
10224 Atwater Bay Dr Winter Garden, FL GLAMOROUS MODEL HOME SITUATED IN THE UP AND COMING HORIZON WEST AREA! THIS MOVE-IN READY M...	5 beds \| 3 baths \| 3,227 sq.ft.	$759,000	Airbnb cash on cash: N/A Traditional cash on cash: 2.46% Airbnb Rental Income: $null Traditional Rental Income: $3304 Airbnb ROI: N/A Traditional ROI: 2.46%
8256 BAYVIEW CROSSING DRIVE Winter Garden, FL Under contract-accepting backup offers. PRICE IMPROVEMENT....UPGRADED POOL HOME in Horizon...	4 beds \| 4 baths \| 2,557 sq.ft.	$675,000	Airbnb cash on cash: 3.27% Traditional cash on cash: 4.32% Airbnb Rental Income: $5064 Traditional Rental Income: $4693 Airbnb ROI: 3.27% Traditional ROI: 4.32%
634 Foster Ave 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: 4.48% Airbnb Rental Income: $2340 Traditional Rental Income: $1916 Airbnb ROI: 3.9% Traditional ROI: 4.48%
14254 Sunridge Blvd Winter Garden, FL Stunning 4BD/3.5BA Winter Garden POOL HOME in the Cypress Reserve community has everything...	5 beds \| 3 baths \| 4,004 sq.ft.	$1,150,000	Airbnb cash on cash: N/A Traditional cash on cash: 1.96% Airbnb Rental Income: $null Traditional Rental Income: $3885 Airbnb ROI: N/A Traditional ROI: 1.96%
217 W Bay St Winter Garden, FL STEPS from HISTORIC Winter Garden, Shopping, Dining and Small Town Charm just out your FRO...	5 beds \| 4 baths \| 2,800 sq.ft.	$1,495,000	Airbnb cash on cash: N/A Traditional cash on cash: -0.13% Airbnb Rental Income: $null Traditional Rental Income: $1326 Airbnb ROI: N/A Traditional ROI: -0.13%

Your search for investment property begins and ends here

Single Family Homes for Sale in Winter Garden, FL

849 Shadowmoss Dr

Winter Garden, FL

5 beds | 3 baths | 2,620 sq.ft.

$750,000

Airbnb cash on cash: N/A

Traditional cash on cash: 2.48%

Airbnb Rental Income: $null

Traditional Rental Income: $3077

Airbnb ROI: N/A

Traditional ROI: 2.48%

13728 Fox Glove St

Winter Garden, FL

5 beds | 3 baths | 3,391 sq.ft.

$739,900

Airbnb cash on cash: N/A

Traditional cash on cash: 3.04%

Airbnb Rental Income: $null

Traditional Rental Income: $3736

Airbnb ROI: N/A

Traditional ROI: 3.04%

7189 Summerlake Groves St

Winter Garden, FL

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

$609,999

Airbnb cash on cash: -0.5%

Traditional cash on cash: 3.22%

Airbnb Rental Income: $1636

Traditional Rental Income: $3295

Airbnb ROI: -0.5%

Traditional ROI: 3.22%

14372 Sunbridge Cir

Winter Garden, FL

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

$745,000

Airbnb cash on cash: 3.64%

Traditional cash on cash: 6.44%

Airbnb Rental Income: $5064

Traditional Rental Income: $5980

Airbnb ROI: 3.64%

Traditional ROI: 6.44%

16197 Wind View Ln

Winter Garden, FL

3 beds | 2 baths | 2,027 sq.ft.

$527,000

Airbnb cash on cash: -0.44%

Traditional cash on cash: 3.19%

Airbnb Rental Income: $1636

Traditional Rental Income: $2962

Airbnb ROI: -0.44%

Traditional ROI: 3.19%

264 BLUE STONE CIRCLE

Winter Garden, FL

4 beds | 3 baths | 2,538 sq.ft.

$725,000

Airbnb cash on cash: 4.02%

Traditional cash on cash: 3.53%

Airbnb Rental Income: $5064

Traditional Rental Income: $3698

Airbnb ROI: 4.02%

Traditional ROI: 3.53%

2202 Romanum Dr

Winter Garden, FL

3 beds | 2 baths | 1,889 sq.ft.

$585,000

Airbnb cash on cash: -0.1%

Traditional cash on cash: 2.21%

Airbnb Rental Income: $1636

Traditional Rental Income: $2435

Airbnb ROI: -0.1%

Traditional ROI: 2.21%

16232 ROCK COAST DRIVE

Winter Garden, FL

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

$925,000

Airbnb cash on cash: 2.41%

Traditional cash on cash: 6.22%

Airbnb Rental Income: $5064

Traditional Rental Income: $7312

Airbnb ROI: 2.41%