Airbnb Properties for Sale in Winter Garden, FL

Looking for a vacation rental investment in Winter Garden, FL with high ROI ?

Explore a range of newly added short-term rental homes in Winter Garden, FL. Make a smart investment with newly available Airbnb properties and find the ideal high-ROI property for sale.

Airbnb Single Family Residential 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 105 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
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%
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%
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%
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%
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%
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%
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%
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%
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%
9282 WOODCRANE DRIVE Winter Garden, FL Under contract-accepting backup offers. Welcome to 9282 Woodcrane Drive, a stunning reside...	4 beds \| 4 baths \| 2,650 sq.ft.	$785,000	Airbnb cash on cash: 2.77% Traditional cash on cash: 2.03% Airbnb Rental Income: $5064 Traditional Rental Income: $3494 Airbnb ROI: 2.77% Traditional ROI: 2.03%
15452 FIRELIGHT DRIVE Winter Garden, FL Welcome to this stunning 4 bedroom, 3 bathroom home nestled in the highly sought-after gat...	4 beds \| 3 baths \| 2,648 sq.ft.	$639,900	Airbnb cash on cash: 4.67% Traditional cash on cash: 3.51% Airbnb Rental Income: $5064 Traditional Rental Income: $3338 Airbnb ROI: 4.67% Traditional ROI: 3.51%
15309 HONEYBELL DRIVE Winter Garden, FL One or more photo(s) has been virtually staged. Welcome to 3,094 sq ft of contemporary liv...	4 beds \| 4 baths \| 3,094 sq.ft.	$794,000	Airbnb cash on cash: 3.39% Traditional cash on cash: 3.06% Airbnb Rental Income: $5064 Traditional Rental Income: $3792 Airbnb ROI: 3.39% Traditional ROI: 3.06%
166 Hammock Preserve Loop Winter Garden, FL Pre-Construction. To be built. To be built. AR Homes (Arthur Rutenberg Homes) , a renowned...	4 beds \| 4 baths \| 3,186 sq.ft.	$1,575,000	Airbnb cash on cash: 1.48% Traditional cash on cash: 1.4% Airbnb Rental Income: $5064 Traditional Rental Income: $3921 Airbnb ROI: 1.48% Traditional ROI: 1.4%
14571 BAHAMA SWALLOW BOULEVARD Winter Garden, FL Welcome to this charming single-story home located in the highly desirable Summerlake comm...	4 beds \| 2 baths \| 2,063 sq.ft.	$545,000	Airbnb cash on cash: 4.82% Traditional cash on cash: 2.7% Airbnb Rental Income: $5064 Traditional Rental Income: $2953 Airbnb ROI: 4.82% Traditional ROI: 2.7%
11400 LOVERS LANE Winter Garden, FL If you've ever dreamed of country living, but don't want to give up your conveniences, the...	4 beds \| 3 baths \| 2,517 sq.ft.	$1,270,000	Airbnb cash on cash: 1.81% Traditional cash on cash: 0.99% Airbnb Rental Income: $5064 Traditional Rental Income: $3063 Airbnb ROI: 1.81% Traditional ROI: 0.99%
14902 ARRENA ROAD Winter Garden, FL WATERFRONT--2 ACRES--NO HOA 7 Miles west of Disneys' main entrance...Winter Garden addre...	4 beds \| 3 baths \| 3,392 sq.ft.	$650,000	Airbnb cash on cash: 4.31% Traditional cash on cash: 3% Airbnb Rental Income: $5064 Traditional Rental Income: $3239 Airbnb ROI: 4.31% Traditional ROI: 3%
15531 WATERLEIGH COVE DRIVE Winter Garden, FL Under contract-accepting backup offers. One or more photo(s) has been virtually staged. Gi...	4 beds \| 3 baths \| 2,295 sq.ft.	$575,000	Airbnb cash on cash: 5.03% Traditional cash on cash: 2.91% Airbnb Rental Income: $5064 Traditional Rental Income: $2892 Airbnb ROI: 5.03% Traditional ROI: 2.91%
2510 BLACK LAKE BOULEVARD Winter Garden, FL Beautifully Updated Corner-Lot Home in Guard-Gated Stoneybrook West! This stylish resid...	4 beds \| 3 baths \| 3,022 sq.ft.	$665,000	Airbnb cash on cash: 4.28% Traditional cash on cash: 2.87% Airbnb Rental Income: $5064 Traditional Rental Income: $3157 Airbnb ROI: 4.28% Traditional ROI: 2.87%
16150 PARKWYN STREET Winter Garden, FL MUST SEE THIS LUXURIOUS OPEN CONCEPT HOME SWEET HOME! * * * CLICK ON "VIRTUAL TOUR" AND SE...	4 beds \| 4 baths \| 3,093 sq.ft.	$769,990	Airbnb cash on cash: 3.38% Traditional cash on cash: 3.11% Airbnb Rental Income: $5064 Traditional Rental Income: $3839 Airbnb ROI: 3.38% Traditional ROI: 3.11%
18339 OLIVER TWIST WAY Winter Garden, FL Motivated Seller This 2023 built home has only had One-owner, highly upgraded luxury...	4 beds \| 3 baths \| 2,931 sq.ft.	$748,000	Airbnb cash on cash: 2.95% Traditional cash on cash: 1.73% Airbnb Rental Income: $5064 Traditional Rental Income: $3177 Airbnb ROI: 2.95% Traditional ROI: 1.73%
14711 WINTER STAY DRIVE Winter Garden, FL This stunning 4-bedroom, 3-bathroom home in Panther View offers the perfect blend of comfo...	4 beds \| 3 baths \| 2,662 sq.ft.	$875,000	Airbnb cash on cash: 2.48% Traditional cash on cash: 1.65% Airbnb Rental Income: $5064 Traditional Rental Income: $3356 Airbnb ROI: 2.48% Traditional ROI: 1.65%
16489 SILVER BROOK WAY Winter Garden, FL Welcome to your dream home in the heart of Winter Garden! This beautifully designed single...	4 beds \| 3 baths \| 2,080 sq.ft.	$720,000	Airbnb cash on cash: 4.32% Traditional cash on cash: 3.51% Airbnb Rental Income: $5064 Traditional Rental Income: $3482 Airbnb ROI: 4.32% Traditional ROI: 3.51%
2237 WINTERMERE POINTE DRIVE Winter Garden, FL Under contract-accepting backup offers. Welcome to this one-story 4 bed/2 Bath home, locat...	4 beds \| 2 baths \| 1,950 sq.ft.	$495,000	Airbnb cash on cash: 6.51% Traditional cash on cash: 3.37% Airbnb Rental Income: $5064 Traditional Rental Income: $2574 Airbnb ROI: 6.51% Traditional ROI: 3.37%
17359 BEACHGRASS ALLEY Winter Garden, FL Under Construction. Welcome to this beautiful new construction home located at 17359 Beach...	4 beds \| 4 baths \| 2,780 sq.ft.	$686,990	Airbnb cash on cash: 4.28% Traditional cash on cash: 3.77% Airbnb Rental Income: $5064 Traditional Rental Income: $3705 Airbnb ROI: 4.28% Traditional ROI: 3.77%
3467 BUOY CIRCLE Winter Garden, FL This move-in ready lakeview home offers 4 bedrooms, 3 full bathrooms, and a spacious bonus...	4 beds \| 3 baths \| 2,610 sq.ft.	$649,000	Airbnb cash on cash: 4.31% Traditional cash on cash: 2.37% Airbnb Rental Income: $5064 Traditional Rental Income: $2858 Airbnb ROI: 4.31% Traditional ROI: 2.37%
16632 POINT ROCK DRIVE Winter Garden, FL Short Sale. Located in the sought-after resort-style community of Waterleigh in Winter Gar...	4 beds \| 4 baths \| 2,292 sq.ft.	$550,000	Airbnb cash on cash: 4.51% Traditional cash on cash: 3.23% Airbnb Rental Income: $5064 Traditional Rental Income: $3370 Airbnb ROI: 4.51% Traditional ROI: 3.23%
1606 MALCOLM POINT DRIVE Winter Garden, FL *Golf Cart District* Nestled in a serene cul-de-sac in the heart of Winter Garden, Flo...	4 beds \| 3 baths \| 2,455 sq.ft.	$609,900	Airbnb cash on cash: 5.37% Traditional cash on cash: 3.5% Airbnb Rental Income: $5064 Traditional Rental Income: $2966 Airbnb ROI: 5.37% Traditional ROI: 3.5%
17865 ADRIFT ROAD Winter Garden, FL A home full of charm, comfort, and practicality. It features four bedrooms, including a sp...	4 beds \| 4 baths \| 2,484 sq.ft.	$629,000	Airbnb cash on cash: 3.74% Traditional cash on cash: 2.76% Airbnb Rental Income: $5064 Traditional Rental Income: $3454 Airbnb ROI: 3.74% Traditional ROI: 2.76%
10031 BEDTIME STORY DRIVE Winter Garden, FL ***ASSUMABLE VA MORTGAGE OPTION WITH 3.75 INTEREST FIXED RATE. Sellers willing to install ...	4 beds \| 4 baths \| 2,722 sq.ft.	$675,000	Airbnb cash on cash: 4.75% Traditional cash on cash: 4.06% Airbnb Rental Income: $5064 Traditional Rental Income: $3599 Airbnb ROI: 4.75% Traditional ROI: 4.06%
17993 GOURD NECK LOOP Winter Garden, FL Come see this exquisite Meritage Home in Winter Gardenâs VERDE PARK, sitting on a 1/4 ac...	4 beds \| 3 baths \| 2,736 sq.ft.	$575,000	Airbnb cash on cash: 5.45% Traditional cash on cash: 3.55% Airbnb Rental Income: $5064 Traditional Rental Income: $3011 Airbnb ROI: 5.45% Traditional ROI: 3.55%
17323 BEACHGRASS ALLEY Winter Garden, FL Under Construction. Discover this stunning new construction home, located at 17323 Beachgr...	4 beds \| 4 baths \| 2,780 sq.ft.	$659,900	Airbnb cash on cash: 3.76% Traditional cash on cash: 3.3% Airbnb Rental Income: $5064 Traditional Rental Income: $3745 Airbnb ROI: 3.76% Traditional ROI: 3.3%
17329 BEACHGRASS ALLEY Winter Garden, FL Under Construction. Discover this stunning new construction home located at 17329 Beachgra...	4 beds \| 3 baths \| 2,510 sq.ft.	$631,990	Airbnb cash on cash: 4.11% Traditional cash on cash: 2.33% Airbnb Rental Income: $5064 Traditional Rental Income: $2983 Airbnb ROI: 4.11% Traditional ROI: 2.33%
11045 BOSTWICK ALLEY Winter Garden, FL LOCATION, LOCATION, LOCATION!!!PRICE IS INCLUDING TRANSFERRABLE SOLAR PANELS PAID BY THE S...	4 beds \| 4 baths \| 2,292 sq.ft.	$649,000	Airbnb cash on cash: 3.67% Traditional cash on cash: 2.66% Airbnb Rental Income: $5064 Traditional Rental Income: $3419 Airbnb ROI: 3.67% Traditional ROI: 2.66%
16555 WINGSPREAD LOOP Winter Garden, FL This stunning 4-bedroom, 3.5-bath residence sits proudly in the highly sought-after Hawksm...	4 beds \| 4 baths \| 3,093 sq.ft.	$791,000	Airbnb cash on cash: 2.96% Traditional cash on cash: 2.72% Airbnb Rental Income: $5064 Traditional Rental Income: $3850 Airbnb ROI: 2.96% Traditional ROI: 2.72%
1085 CHASE DRIVE Winter Garden, FL Highly Motivated Seller! Enjoy the ultimate downtown lifestyleâhop on your golf cart and...	4 beds \| 3 baths \| 2,967 sq.ft.	$619,999	Airbnb cash on cash: 5.23% Traditional cash on cash: 3.95% Airbnb Rental Income: $5064 Traditional Rental Income: $3292 Airbnb ROI: 5.23% Traditional ROI: 3.95%
15075 TEA TREE DRIVE Winter Garden, FL One or more photo(s) has been virtually staged. Pre-Construction. To be built. Opportunity...	4 beds \| 3 baths \| 3,038 sq.ft.	$773,260	Airbnb cash on cash: 3.35% Traditional cash on cash: 2.19% Airbnb Rental Income: $5064 Traditional Rental Income: $3193 Airbnb ROI: 3.35% Traditional ROI: 2.19%
6517 SHORE JUNIPER STREET Winter Garden, FL One or more photo(s) has been virtually staged. Pre-Construction. To be built. Opportunity...	4 beds \| 3 baths \| 2,879 sq.ft.	$849,625	Airbnb cash on cash: 2.88% Traditional cash on cash: 1.6% Airbnb Rental Income: $5064 Traditional Rental Income: $3017 Airbnb ROI: 2.88% Traditional ROI: 1.6%

Your search for investment property begins and ends here

Airbnb Single Family Residential For Sale in Winter Garden, FL

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%

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%

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%

Traditional ROI: 2.56%

15372 GILLIGAN COURT

Winter Garden, FL

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

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

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%

14602 WINTER STAY DRIVE

Winter Garden, FL

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%

15058 SAWGRASS BLUFF DRIVE

Winter Garden, FL

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%