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 93 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
5978 FLOWERING CHERRY Bend Winter Garden, FL Virtually Staged. Pre-Construction. To be built. The Davis Plan by Dream Finders Homes is ...	4 beds \| 3 baths \| 2,802 sq.ft.	$714,990	Airbnb cash on cash: 2.78% Traditional cash on cash: 2.39% Airbnb Rental Income: $4271 Traditional Rental Income: $3111 Airbnb ROI: 2.78% Traditional ROI: 2.39%
13184 DENDY Way Winter Garden, FL $5,000 Buyer Credit toward Closing Costs or an Interest Rate Buy-Down! Experience exceptio...	4 beds \| 3 baths \| 2,211 sq.ft.	$664,000	Airbnb cash on cash: 3.64% Traditional cash on cash: 3.59% Airbnb Rental Income: $4271 Traditional Rental Income: $3336 Airbnb ROI: 3.64% Traditional ROI: 3.59%
1061 PORTMOOR Way Winter Garden, FL Welcome to 1061 Portmoor Way, a single-story 4-bedroom, 2-bathroom home located in the hig...	4 beds \| 2 baths \| 1,804 sq.ft.	$515,000	Airbnb cash on cash: 3.94% Traditional cash on cash: 1.87% Airbnb Rental Income: $4271 Traditional Rental Income: $2376 Airbnb ROI: 3.94% Traditional ROI: 1.87%
13043 SERENE GLADE Road Winter Garden, FL Virtually Staged. Welcome to your Newbury model home! This Dream Finders Home is a 4-bedro...	4 beds \| 3 baths \| 2,083 sq.ft.	$574,000	Airbnb cash on cash: 4.41% Traditional cash on cash: 3.35% Airbnb Rental Income: $4271 Traditional Rental Income: $2800 Airbnb ROI: 4.41% Traditional ROI: 3.35%
301 VALENCIA Court Winter Garden, FL Welcome to 301 Valencia Ct., a well maintained 4bedroom 2.5 bath home situated on a large,...	4 beds \| 3 baths \| 2,029 sq.ft.	$750,000	Airbnb cash on cash: 3.43% Traditional cash on cash: 2.91% Airbnb Rental Income: $4271 Traditional Rental Income: $3008 Airbnb ROI: 3.43% Traditional ROI: 2.91%
1075 CHASE Drive Winter Garden, FL Zoned for the Golf Cart District! Welcome to 1075 Chase Drive-located in downtown Winter G...	4 beds \| 2 baths \| 2,125 sq.ft.	$625,000	Airbnb cash on cash: 4.1% Traditional cash on cash: 3.87% Airbnb Rental Income: $4271 Traditional Rental Income: $3231 Airbnb ROI: 4.1% Traditional ROI: 3.87%
16153 WATER SPRING Boulevard Winter Garden, FL Single Family bungalow, 4 bedrooms and 3 full bathrooms, with backyard is rare. Designed f...	4 beds \| 3 baths \| 2,042 sq.ft.	$549,990	Airbnb cash on cash: 3.91% Traditional cash on cash: 3.61% Airbnb Rental Income: $4271 Traditional Rental Income: $3221 Airbnb ROI: 3.91% Traditional ROI: 3.61%
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.	$505,000	Airbnb cash on cash: 4.57% Traditional cash on cash: 4.11% Airbnb Rental Income: $4271 Traditional Rental Income: $3154 Airbnb ROI: 4.57% Traditional ROI: 4.11%
5679 ORANGE ORCHARD Drive Winter Garden, FL Move-In Ready Home Near Hamlin Town Center with Open Layout and Private Backyard. Built in...	4 beds \| 3 baths \| 2,235 sq.ft.	$649,900	Airbnb cash on cash: 3.09% Traditional cash on cash: 3.07% Airbnb Rental Income: $4271 Traditional Rental Income: $3357 Airbnb ROI: 3.09% Traditional ROI: 3.07%
884 KLONDIKE Street Winter Garden, FL Welcome to Historic Winter Garden, Florida. NO HOA! Where small-town charm, community, and...	4 beds \| 2 baths \| 1,485 sq.ft.	$372,500	Airbnb cash on cash: 7.09% Traditional cash on cash: 5.51% Airbnb Rental Income: $4271 Traditional Rental Income: $2819 Airbnb ROI: 7.09% Traditional ROI: 5.51%
14006 FRASIER STREET Winter Garden, FL Stunning Corner Lot Home Welcome to this beautifully designed, home situated on a desirabl...	4 beds \| 3 baths \| 2,098 sq.ft.	$655,500	Airbnb cash on cash: 2.92% Traditional cash on cash: 1.99% Airbnb Rental Income: $4271 Traditional Rental Income: $2797 Airbnb ROI: 2.92% Traditional ROI: 1.99%
11243 PIXIE MANDARIN Court Winter Garden, FL Stunning Home in Winter Garden - Prime Location! Welcome to this beautiful and meticulousl...	4 beds \| 3 baths \| 2,122 sq.ft.	$849,000	Airbnb cash on cash: 1.97% Traditional cash on cash: 1.46% Airbnb Rental Income: $4271 Traditional Rental Income: $2966 Airbnb ROI: 1.97% Traditional ROI: 1.46%
7190 ENCHANTED LAKE Drive Winter Garden, FL BACK ON MARKET: BRAND-NEW HVAC & INCREDIBLE VALUE! Welcome to 7190 Enchanted Lake Drive-yo...	4 beds \| 3 baths \| 2,113 sq.ft.	$535,000	Airbnb cash on cash: 4.04% Traditional cash on cash: 2.92% Airbnb Rental Income: $4271 Traditional Rental Income: $2813 Airbnb ROI: 4.04% Traditional ROI: 2.92%
16185 TALIESIN Street Winter Garden, FL Virtually Staged. Beautifully maintained 4-bedroom, 3-bathroom two-story home located in t...	4 beds \| 3 baths \| 2,372 sq.ft.	$649,990	Airbnb cash on cash: 3.25% Traditional cash on cash: 2.6% Airbnb Rental Income: $4271 Traditional Rental Income: $2975 Airbnb ROI: 3.25% Traditional ROI: 2.6%
6316 MANUSCRIPT Street Winter Garden, FL Such a Charming, Family-Friendly 4 Bedroom 2.5 Bath Home in Beautiful Winter Garden. The b...	4 beds \| 3 baths \| 2,608 sq.ft.	$599,000	Airbnb cash on cash: 3.04% Traditional cash on cash: 2.34% Airbnb Rental Income: $4271 Traditional Rental Income: $2978 Airbnb ROI: 3.04% Traditional ROI: 2.34%
11036 ROBERT FROST Drive Winter Garden, FL Amazing Single Family, 4 bedrooms and 3 full bathrooms with fenced backyard for privacy an...	4 beds \| 3 baths \| 2,136 sq.ft.	$614,990	Airbnb cash on cash: 2.93% Traditional cash on cash: 1.95% Airbnb Rental Income: $4271 Traditional Rental Income: $2809 Airbnb ROI: 2.93% Traditional ROI: 1.95%
11165 GREEN CITRON Alley Winter Garden, FL Welcome to this stunning, nearly new home, just two years old and thoughtfully designed fo...	4 beds \| 3 baths \| 2,043 sq.ft.	$646,000	Airbnb cash on cash: 2.94% Traditional cash on cash: 2.01% Airbnb Rental Income: $4271 Traditional Rental Income: $2810 Airbnb ROI: 2.94% Traditional ROI: 2.01%
20 E DIVISION Street Winter Garden, FL Appraisal in hand! Welcome to one of Winter Garden's most remarkable custom transformation...	4 beds \| 3 baths \| 2,729 sq.ft.	$1,080,000	Airbnb cash on cash: 1.6% Traditional cash on cash: 1.49% Airbnb Rental Income: $4271 Traditional Rental Income: $3262 Airbnb ROI: 1.6% Traditional ROI: 1.49%
13361 SUNNY RETREAT Lane Winter Garden, FL Better Than New in Del Webb Oasis at Horizon West! Located within this sought after gated,...	4 beds \| 3 baths \| 3,172 sq.ft.	$859,900	Airbnb cash on cash: 1.2% Traditional cash on cash: 1.01% Airbnb Rental Income: $4271 Traditional Rental Income: $3221 Airbnb ROI: 1.2% Traditional ROI: 1.01%
11043 JACKSON Cove Winter Garden, FL Located in the sought-after community of Waterleigh, Welcome Home to this freshly upgraded...	4 beds \| 3 baths \| 2,095 sq.ft.	$639,999	Airbnb cash on cash: 2.57% Traditional cash on cash: 1.52% Airbnb Rental Income: $4271 Traditional Rental Income: $2740 Airbnb ROI: 2.57% Traditional ROI: 1.52%
16082 HAMPTON CROSSING Drive Winter Garden, FL ONE-OF-A-KIND IN MARINA BAY AT WATERLEIGH! Custom craftsmanship, incredible energy upgrade...	4 beds \| 3 baths \| 2,240 sq.ft.	$729,900	Airbnb cash on cash: 2.58% Traditional cash on cash: 1.8% Airbnb Rental Income: $4271 Traditional Rental Income: $2839 Airbnb ROI: 2.58% Traditional ROI: 1.8%
932 LOST GROVE Circle Winter Garden, FL A home that's finally been paid attention to. Four bedrooms, two-and-a-half baths, 2,891 s...	4 beds \| 3 baths \| 2,891 sq.ft.	$619,000	Airbnb cash on cash: 2.99% Traditional cash on cash: 2.46% Airbnb Rental Income: $4271 Traditional Rental Income: $3064 Airbnb ROI: 2.99% Traditional ROI: 2.46%
11031 JACKSON Cove Winter Garden, FL Virtually Staged. 2023 CONSTRUCTION - PRIVATE CUL-DE-SAC - FIRST-FLOOR BEDROOM & FULL BATH...	4 beds \| 3 baths \| 2,931 sq.ft.	$700,000	Airbnb cash on cash: 1.96% Traditional cash on cash: 1.61% Airbnb Rental Income: $4271 Traditional Rental Income: $3141 Airbnb ROI: 1.96% Traditional ROI: 1.61%
231 E LAFAYETTE Street Winter Garden, FL Brand-New Construction in Winter Garden! Welcome to 231 E Lafayette Street, a beautifully ...	4 beds \| 3 baths \| 1,608 sq.ft.	$479,900	Airbnb cash on cash: 6.04% Traditional cash on cash: 3.85% Airbnb Rental Income: $4271 Traditional Rental Income: $2386 Airbnb ROI: 6.04% Traditional ROI: 3.85%
16968 HAMLIN OASIS Loop Winter Garden, FL Welcome to this beautiful like-new residence in the highly desirable Hamlin Pointe communi...	4 beds \| 3 baths \| 2,088 sq.ft.	$570,000	Airbnb cash on cash: 4.28% Traditional cash on cash: 3.82% Airbnb Rental Income: $4271 Traditional Rental Income: $3128 Airbnb ROI: 4.28% Traditional ROI: 3.82%
2031 WINTERMERE POINTE Drive Winter Garden, FL Virtually Staged. $10,000 TOWARD BUYER'S CLOSING COSTS! SELLER MOTIVATED TO SELL!!! NEWLY ...	4 beds \| 2 baths \| 2,048 sq.ft.	$550,000	Airbnb cash on cash: 4.33% Traditional cash on cash: 3.39% Airbnb Rental Income: $4271 Traditional Rental Income: $2890 Airbnb ROI: 4.33% Traditional ROI: 3.39%
17854 HITHER HILLS Circle Winter Garden, FL Move in ready home with remarkable sunsets, breathtaking panoramic views of Lake Apopka, a...	4 beds \| 3 baths \| 2,929 sq.ft.	$1,100,000	Airbnb cash on cash: 1.15% Traditional cash on cash: 0.58% Airbnb Rental Income: $4271 Traditional Rental Income: $2788 Airbnb ROI: 1.15% Traditional ROI: 0.58%
17802 JEFFERSON Street Winter Garden, FL Virtually Staged. Step into 17802 Jefferson St, a residence presenting a refreshed exterio...	4 beds \| 2 baths \| 1,778 sq.ft.	$433,000	Airbnb cash on cash: 6.08% Traditional cash on cash: 3.84% Airbnb Rental Income: $4271 Traditional Rental Income: $2461 Airbnb ROI: 6.08% Traditional ROI: 3.84%
4981 CORAL BEAN Alley Winter Garden, FL BETTER THAN NEW - NO CDD FEE! Welcome to this like-new, move-in-ready home in Silverleaf R...	4 beds \| 3 baths \| 2,114 sq.ft.	$574,900	Airbnb cash on cash: 3.95% Traditional cash on cash: 2.92% Airbnb Rental Income: $4271 Traditional Rental Income: $2814 Airbnb ROI: 3.95% Traditional ROI: 2.92%
14704 SETON CREEK Boulevard Winter Garden, FL Welcome to resort-style living in the highly sought-after Watermark community of Winter Ga...	4 beds \| 3 baths \| 1,877 sq.ft.	$525,000	Airbnb cash on cash: 3.86% Traditional cash on cash: 2.34% Airbnb Rental Income: $4271 Traditional Rental Income: $2625 Airbnb ROI: 3.86% Traditional ROI: 2.34%
13527 FOX GLOVE Street Winter Garden, FL Some photos are virtually staged. Video tour available. This home has a full-home SOLAR ...	4 beds \| 3 baths \| 3,255 sq.ft.	$710,000	Airbnb cash on cash: 2.16% Traditional cash on cash: 1.8% Airbnb Rental Income: $4271 Traditional Rental Income: $3132 Airbnb ROI: 2.16% Traditional ROI: 1.8%
15081 MASTHEAD LANDING Circle Winter Garden, FL Virtually Staged. Welcome to this beautifully renovated golf-front home in the gated commu...	4 beds \| 3 baths \| 2,842 sq.ft.	$635,000	Airbnb cash on cash: 3.66% Traditional cash on cash: 3.16% Airbnb Rental Income: $4271 Traditional Rental Income: $3076 Airbnb ROI: 3.66% Traditional ROI: 3.16%
531 HEARTHGLEN Boulevard Winter Garden, FL Located in the Oakglen Estates community of Winter Garden, this spacious 4-bedroom, 3-bath...	4 beds \| 3 baths \| 3,029 sq.ft.	$660,000	Airbnb cash on cash: 3.55% Traditional cash on cash: 3.04% Airbnb Rental Income: $4271 Traditional Rental Income: $3057 Airbnb ROI: 3.55% Traditional ROI: 3.04%
2549 BALFORN TOWER Way Winter Garden, FL Welcome to Stoneybrook West-a one-of-a-kind community in Winter Garden! This premier neigh...	4 beds \| 3 baths \| 3,279 sq.ft.	$689,000	Airbnb cash on cash: 3% Traditional cash on cash: 2.63% Airbnb Rental Income: $4271 Traditional Rental Income: $3131 Airbnb ROI: 3% Traditional ROI: 2.63%
8016 SWEET ORANGE Avenue Winter Garden, FL Virtually Staged. ~Seller may consider buyer concessions if made in an offer~Perfectly sit...	4 beds \| 3 baths \| 2,084 sq.ft.	$514,900	Airbnb cash on cash: 4.15% Traditional cash on cash: 2.93% Airbnb Rental Income: $4271 Traditional Rental Income: $2785 Airbnb ROI: 4.15% Traditional ROI: 2.93%
12523 GOLD HONEYSUCKLE Street Winter Garden, FL Under Construction. .	4 beds \| 3 baths \| 2,552 sq.ft.	$834,990	Airbnb cash on cash: 1.96% Traditional cash on cash: 1.4% Airbnb Rental Income: $4271 Traditional Rental Income: $2928 Airbnb ROI: 1.96% Traditional ROI: 1.4%
427 TIERRA VERDE Lane Winter Garden, FL Virtually Staged. Welcome to this beautifully maintained custom home located in the gated ...	4 beds \| 3 baths \| 2,368 sq.ft.	$849,988	Airbnb cash on cash: 1.89% Traditional cash on cash: 1.31% Airbnb Rental Income: $4271 Traditional Rental Income: $2908 Airbnb ROI: 1.89% Traditional ROI: 1.31%
7179 SPRING PARK Drive Winter Garden, FL Located in the vibrant Lakeview Pointe community within Horizon West, this model-like 4-be...	4 beds \| 3 baths \| 2,272 sq.ft.	$535,000	Airbnb cash on cash: 3.96% Traditional cash on cash: 2.15% Airbnb Rental Income: $4271 Traditional Rental Income: $2467 Airbnb ROI: 3.96% Traditional ROI: 2.15%
17418 HONEYBELL TANGELO Court Winter Garden, FL Under Construction. Near Walt Disney World Theme Parks! Welcome to the Eliot plan, a luxur...	4 beds \| 4 baths \| 3,041 sq.ft.	$829,000	Airbnb cash on cash: 2.82% Traditional cash on cash: 2.1% Airbnb Rental Income: $4271 Traditional Rental Income: $2814 Airbnb ROI: 2.82% Traditional ROI: 2.1%
1906 SHERBOURNE Street Winter Garden, FL Experience luxury living in one of Winter Garden's most desirable areas. This beautifully ...	4 beds \| 3 baths \| 2,029 sq.ft.	$477,000	Airbnb cash on cash: 5.64% Traditional cash on cash: 4.53% Airbnb Rental Income: $4271 Traditional Rental Income: $2873 Airbnb ROI: 5.64% Traditional ROI: 4.53%

Your search for investment property begins and ends here

Airbnb Single Family Residential For Sale in Winter Garden, FL

5978 FLOWERING CHERRY Bend

Winter Garden, FL

4 beds | 3 baths | 2,802 sq.ft.

$714,990

Airbnb cash on cash: 2.78%

Traditional cash on cash: 2.39%

Airbnb Rental Income: $4271

Traditional Rental Income: $3111

Airbnb ROI: 2.78%

Traditional ROI: 2.39%

13184 DENDY Way

Winter Garden, FL

4 beds | 3 baths | 2,211 sq.ft.

$664,000

Airbnb cash on cash: 3.64%

Traditional cash on cash: 3.59%

Airbnb Rental Income: $4271

Traditional Rental Income: $3336

Airbnb ROI: 3.64%

Traditional ROI: 3.59%

1061 PORTMOOR Way

Winter Garden, FL

4 beds | 2 baths | 1,804 sq.ft.

$515,000

Airbnb cash on cash: 3.94%

Traditional cash on cash: 1.87%

Airbnb Rental Income: $4271

Traditional Rental Income: $2376

Airbnb ROI: 3.94%

Traditional ROI: 1.87%

13043 SERENE GLADE Road

Winter Garden, FL

4 beds | 3 baths | 2,083 sq.ft.

$574,000

Airbnb cash on cash: 4.41%

Traditional cash on cash: 3.35%

Airbnb Rental Income: $4271

Traditional Rental Income: $2800

Airbnb ROI: 4.41%

Traditional ROI: 3.35%

301 VALENCIA Court

Winter Garden, FL

4 beds | 3 baths | 2,029 sq.ft.

$750,000

Airbnb cash on cash: 3.43%

Traditional cash on cash: 2.91%

Airbnb Rental Income: $4271

Traditional Rental Income: $3008

Airbnb ROI: 3.43%

Traditional ROI: 2.91%

1075 CHASE Drive

Winter Garden, FL

4 beds | 2 baths | 2,125 sq.ft.

$625,000

Airbnb cash on cash: 4.1%

Traditional cash on cash: 3.87%

Airbnb Rental Income: $4271

Traditional Rental Income: $3231

Airbnb ROI: 4.1%

Traditional ROI: 3.87%

16153 WATER SPRING Boulevard

Winter Garden, FL

4 beds | 3 baths | 2,042 sq.ft.

$549,990

Airbnb cash on cash: 3.91%

Traditional cash on cash: 3.61%

Airbnb Rental Income: $4271

Traditional Rental Income: $3221

Airbnb ROI: 3.91%

Traditional ROI: 3.61%

1112 JUNIPER HAMMOCK Court

Winter Garden, FL

4 beds | 2 baths | 2,545 sq.ft.

$505,000

Airbnb cash on cash: 4.57%

Traditional cash on cash: 4.11%

Airbnb Rental Income: $4271

Traditional Rental Income: $3154

Airbnb ROI: 4.57%