Airbnb Properties for Sale in Winter Park, FL

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

Explore a range of newly added short-term rental homes in Winter Park, 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 Park, FL

Search for Single Family Residential for Sale in Winter Park, 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 71 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
1751 GOODRICH AVENUE Winter Park, FL Welcome to 1751 Goodrich Ave, a beautifully designed residence in the heart of Winter Park...	4 beds \| 4 baths \| 2,170 sq.ft.	$1,475,000	Airbnb cash on cash: 1.66% Traditional cash on cash: 1.04% Airbnb Rental Income: $5745 Traditional Rental Income: $3743 Airbnb ROI: 1.66% Traditional ROI: 1.04%
668 OVERSPIN DRIVE Winter Park, FL One or more photo(s) has been virtually staged. A contemporary, beautifully finished home ...	4 beds \| 3 baths \| 2,509 sq.ft.	$875,000	Airbnb cash on cash: 3.21% Traditional cash on cash: 2.32% Airbnb Rental Income: $5745 Traditional Rental Income: $3878 Airbnb ROI: 3.21% Traditional ROI: 2.32%
720 W WEBSTER AVENUE Winter Park, FL One or more photo(s) has been virtually staged. This home can be purchased with NO INCOME ...	3 beds \| 2 baths \| 1,356 sq.ft.	$525,000	Airbnb cash on cash: 4.82% Traditional cash on cash: 3.39% Airbnb Rental Income: $4337 Traditional Rental Income: $2724 Airbnb ROI: 4.82% Traditional ROI: 3.39%
1800 MAGNOLIA AVENUE Winter Park, FL One or more photo(s) has been virtually staged. Experience refined living in this exquisit...	4 beds \| 3 baths \| 2,431 sq.ft.	$1,148,000	Airbnb cash on cash: 2.2% Traditional cash on cash: 2.04% Airbnb Rental Income: $5745 Traditional Rental Income: $4421 Airbnb ROI: 2.2% Traditional ROI: 2.04%
2036 VIA TUSCANY Winter Park, FL WINTER PARK VIAâS!!! Incredible Oversized Lot is located in the âHeartâ of Winter Pa...	3 beds \| 2 baths \| 2,148 sq.ft.	$2,000,000	Airbnb cash on cash: 0.04% Traditional cash on cash: -0.02% Airbnb Rental Income: $4337 Traditional Rental Income: $3307 Airbnb ROI: 0.04% Traditional ROI: -0.02%
811 Overspin Dr Winter Park, FL 811 Overspin Dr, Orlando, FL 32789 \| Single Family Residential	2 beds \| 1 baths \| 749 sq.ft.	$349,000	Airbnb cash on cash: 5.54% Traditional cash on cash: 3.03% Airbnb Rental Income: $3260 Traditional Rental Income: $1705 Airbnb ROI: 5.54% Traditional ROI: 3.03%
2560 Franklin Avenue Winter Park, FL Come see this charming 4 bed, 2 bath, 2 story home in Winter Park/ Lake Killarney location...	4 beds \| 2 baths \| 1,514 sq.ft.	$499,000	Airbnb cash on cash: 7.07% Traditional cash on cash: 3.26% Airbnb Rental Income: $5745 Traditional Rental Income: $2821 Airbnb ROI: 7.07% Traditional ROI: 3.26%
1399 ALOMA AVENUE Winter Park, FL *Price Adjustment * Motivated Seller! Charming 1948 Winter Park Home! This 3-bedroom, ...	3 beds \| 2 baths \| 1,804 sq.ft.	$600,000	Airbnb cash on cash: 4.6% Traditional cash on cash: 4.09% Airbnb Rental Income: $4337 Traditional Rental Income: $3142 Airbnb ROI: 4.6% Traditional ROI: 4.09%
Lot #21 KAROLINA AVE Winter Park, FL Pre-Construction. To be built. Step into a life where charm meets convenience in the heart...	4 beds \| 4 baths \| 2,662 sq.ft.	$944,890	Airbnb cash on cash: 3.89% Traditional cash on cash: 3.4% Airbnb Rental Income: $5745 Traditional Rental Income: $4170 Airbnb ROI: 3.89% Traditional ROI: 3.4%
3018 NORTHWOOD BOULEVARD Winter Park, FL "MOTIVATED SELLER" - NEED SOME CLOSING COST? RATE BUY DOWN? WE CAN HELP GET YOU INTO THIS ...	3 beds \| 2 baths \| 1,761 sq.ft.	$679,000	Airbnb cash on cash: 3.29% Traditional cash on cash: 3.11% Airbnb Rental Income: $4337 Traditional Rental Income: $3308 Airbnb ROI: 3.29% Traditional ROI: 3.11%
1780 BRYAN AVENUE Winter Park, FL Discover a truly unique offering in the heart of Winter Park! This property, located at 17...	4 beds \| 2 baths \| 1,617 sq.ft.	$849,000	Airbnb cash on cash: 3.84% Traditional cash on cash: 2.01% Airbnb Rental Income: $5745 Traditional Rental Income: $3153 Airbnb ROI: 3.84% Traditional ROI: 2.01%
423 OLOLU DRIVE Winter Park, FL Welcome to this beautifully remodeled two story home in one of Winter Parkâs most desira...	3 beds \| 3 baths \| 1,920 sq.ft.	$589,000	Airbnb cash on cash: 4.38% Traditional cash on cash: 3.57% Airbnb Rental Income: $4337 Traditional Rental Income: $2979 Airbnb ROI: 4.38% Traditional ROI: 3.57%
841 W SWOOPE AVENUE Winter Park, FL This Winter Park property offers exceptional potential in one of the most desirable and ra...	2 beds \| 1 baths \| 1,396 sq.ft.	$499,000	Airbnb cash on cash: 3.46% Traditional cash on cash: 3.03% Airbnb Rental Income: $3260 Traditional Rental Income: $2330 Airbnb ROI: 3.46% Traditional ROI: 3.03%
1951 STAUNTON AVENUE Winter Park, FL TRANSFERABLE TERMITE BOND INCLUDED. Welcome home to the charm and character of the bygone ...	3 beds \| 2 baths \| 2,556 sq.ft.	$599,000	Airbnb cash on cash: 4.54% Traditional cash on cash: 2.25% Airbnb Rental Income: $4337 Traditional Rental Income: $2142 Airbnb ROI: 4.54% Traditional ROI: 2.25%
1354 INDIANA AVENUE Winter Park, FL One or more photo(s) has been virtually staged. Fabulous location in Winter Park! Complete...	3 beds \| 2 baths \| 1,269 sq.ft.	$599,900	Airbnb cash on cash: 4.06% Traditional cash on cash: 2.86% Airbnb Rental Income: $4337 Traditional Rental Income: $2752 Airbnb ROI: 4.06% Traditional ROI: 2.86%
2779 SANBINA STREET Winter Park, FL Rare opportunity in the heart of 32789 â priced under $500K, this 3-bedroom, 2-bathroom ...	3 beds \| 2 baths \| 1,405 sq.ft.	$460,000	Airbnb cash on cash: 5.53% Traditional cash on cash: 3.89% Airbnb Rental Income: $4337 Traditional Rental Income: $2723 Airbnb ROI: 5.53% Traditional ROI: 3.89%
405 LAKE FAIR LANE Winter Park, FL One or more photo(s) has been virtually staged. Fully rebuilt, not just renovated. This Wi...	3 beds \| 2 baths \| 1,491 sq.ft.	$459,999	Airbnb cash on cash: 6.44% Traditional cash on cash: 4.75% Airbnb Rental Income: $4337 Traditional Rental Income: $2697 Airbnb ROI: 6.44% Traditional ROI: 4.75%
2713 EASTERN PARKWAY Winter Park, FL Welcome to this charming, meticulously maintained 3-bedroom, 2-bath residence in the heart...	3 beds \| 2 baths \| 1,304 sq.ft.	$670,000	Airbnb cash on cash: 3.93% Traditional cash on cash: 1.9% Airbnb Rental Income: $4337 Traditional Rental Income: $2154 Airbnb ROI: 3.93% Traditional ROI: 1.9%
950 HANOVER AVENUE Winter Park, FL Preferred lender credit available. Welcome home to your peaceful retreat tucked away near ...	3 beds \| 2 baths \| 1,606 sq.ft.	$470,000	Airbnb cash on cash: 5.83% Traditional cash on cash: 3.4% Airbnb Rental Income: $4337 Traditional Rental Income: $2358 Airbnb ROI: 5.83% Traditional ROI: 3.4%
1905 BONANZA CT Winter Park, FL This beautifully updated 4-bedroom, 2-bath bungalow with a 2-car garage sits on a quiet cu...	4 beds \| 2 baths \| 1,774 sq.ft.	$490,000	Airbnb cash on cash: 7.81% Traditional cash on cash: 3.89% Airbnb Rental Income: $5745 Traditional Rental Income: $2802 Airbnb ROI: 7.81% Traditional ROI: 3.89%
1830 EDWIN BOULEVARD Winter Park, FL Welcome to this beautifully designed and thoughtfully upgraded home that perfectly blends ...	3 beds \| 2 baths \| 1,287 sq.ft.	$679,800	Airbnb cash on cash: 3.68% Traditional cash on cash: 1.53% Airbnb Rental Income: $4337 Traditional Rental Income: $2064 Airbnb ROI: 3.68% Traditional ROI: 1.53%
675 OVERSPIN DRIVE Winter Park, FL Seller may consider buyer concessions if made in an offer ~ Beautiful upgrades, a versatil...	4 beds \| 4 baths \| 3,062 sq.ft.	$775,000	Airbnb cash on cash: 3.75% Traditional cash on cash: 3.51% Airbnb Rental Income: $5745 Traditional Rental Income: $4423 Airbnb ROI: 3.75% Traditional ROI: 3.51%
446 ALBERTA DRIVE Winter Park, FL Under contract-accepting backup offers. Charming Opportunity in Prime Winter Park â 446 ...	4 beds \| 3 baths \| 3,263 sq.ft.	$1,675,000	Airbnb cash on cash: 1.49% Traditional cash on cash: 0.64% Airbnb Rental Income: $5745 Traditional Rental Income: $3271 Airbnb ROI: 1.49% Traditional ROI: 0.64%
770 W WEBSTER AVENUE Winter Park, FL Under contract-accepting backup offers. Stop the car! Develop your dream project on this ...	4 beds \| 2 baths \| 1,008 sq.ft.	$725,000	Airbnb cash on cash: 5% Traditional cash on cash: 1.86% Airbnb Rental Income: $5745 Traditional Rental Income: $2476 Airbnb ROI: 5% Traditional ROI: 1.86%
2119 HOWARD DRIVE Winter Park, FL Welcome to this charming residence in the heart of sought-after Winter Park. Pride of owne...	4 beds \| 2 baths \| 2,479 sq.ft.	$850,000	Airbnb cash on cash: 4.26% Traditional cash on cash: 2.24% Airbnb Rental Income: $5745 Traditional Rental Income: $3003 Airbnb ROI: 4.26% Traditional ROI: 2.24%
3114 HEARTLEAF PLACE Winter Park, FL Tucked away on a rare and breathtaking .96-acre homesite, this one-of-a-kind property in L...	4 beds \| 3 baths \| 2,702 sq.ft.	$699,900	Airbnb cash on cash: 4.92% Traditional cash on cash: 3.49% Airbnb Rental Income: $5745 Traditional Rental Income: $3669 Airbnb ROI: 4.92% Traditional ROI: 3.49%
744 CORNWALL ROAD Winter Park, FL Welcome to your dream home! This exceptional 4-bedroom residence features a desirable spli...	4 beds \| 2 baths \| 1,968 sq.ft.	$695,000	Airbnb cash on cash: 5.18% Traditional cash on cash: 2.89% Airbnb Rental Income: $5745 Traditional Rental Income: $3114 Airbnb ROI: 5.18% Traditional ROI: 2.89%
418 GILBERT ROAD Winter Park, FL Beautifully renovated solid block home on a quiet street in highly desirable Winter Park P...	3 beds \| 3 baths \| 1,680 sq.ft.	$740,000	Airbnb cash on cash: 2.61% Traditional cash on cash: 1.99% Airbnb Rental Income: $4337 Traditional Rental Income: $2995 Airbnb ROI: 2.61% Traditional ROI: 1.99%
3054 BLUEBROOK DRIVE Winter Park, FL "Open the Doors to Your Dreams" of owning an Affordable Home with a pool in Winter Park. T...	3 beds \| 2 baths \| 1,939 sq.ft.	$427,500	Airbnb cash on cash: 5.83% Traditional cash on cash: 4.14% Airbnb Rental Income: $4337 Traditional Rental Income: $2747 Airbnb ROI: 5.83% Traditional ROI: 4.14%
346 S RANGER BOULEVARD Winter Park, FL PRIME LOCATION! Beautiful 3 Bedroom 2 Bathroom home is located in sought after Winter Park...	3 beds \| 2 baths \| 1,592 sq.ft.	$485,000	Airbnb cash on cash: 5.25% Traditional cash on cash: 3.96% Airbnb Rental Income: $4337 Traditional Rental Income: $2841 Airbnb ROI: 5.25% Traditional ROI: 3.96%
2681 FITZHUGH ROAD Winter Park, FL Tucked away on a quiet street in the heart of Winter Park, this fully renovated 4-bedroom,...	4 beds \| 3 baths \| 2,375 sq.ft.	$750,000	Airbnb cash on cash: 4.66% Traditional cash on cash: 3.39% Airbnb Rental Income: $5745 Traditional Rental Income: $3713 Airbnb ROI: 4.66% Traditional ROI: 3.39%
1354 TIERRA CIRCLE Winter Park, FL Located in the highly sought-after Casa Aloma community, this charming 1960s home offers t...	4 beds \| 2 baths \| 1,827 sq.ft.	$435,000	Airbnb cash on cash: 9.18% Traditional cash on cash: 4.76% Airbnb Rental Income: $5745 Traditional Rental Income: $2797 Airbnb ROI: 9.18% Traditional ROI: 4.76%
1849 VIBURNUM LANE Winter Park, FL This beautifully renovated Winter Park home feels warm, inviting, and easy to love. Bright...	4 beds \| 2 baths \| 1,627 sq.ft.	$425,000	Airbnb cash on cash: 9.46% Traditional cash on cash: 4.47% Airbnb Rental Income: $5745 Traditional Rental Income: $2610 Airbnb ROI: 9.46% Traditional ROI: 4.47%
2217 SUSSEX ROAD Winter Park, FL PRICE REDUCED!!! 4 BEDROOMS with OFFICE POOL HOME. MOTIVATED SELLERS. MOVE IN READY! THI...	4 beds \| 2 baths \| 2,092 sq.ft.	$520,000	Airbnb cash on cash: 7.32% Traditional cash on cash: 4.63% Airbnb Rental Income: $5745 Traditional Rental Income: $3288 Airbnb ROI: 7.32% Traditional ROI: 4.63%
3463 ARNEL DRIVE Winter Park, FL PRICE IMPROVEMENT!! Your pool home in Winter Park just became an even better opportunity. ...	3 beds \| 2 baths \| 1,770 sq.ft.	$459,900	Airbnb cash on cash: 5.73% Traditional cash on cash: 5.13% Airbnb Rental Income: $4337 Traditional Rental Income: $3168 Airbnb ROI: 5.73% Traditional ROI: 5.13%
1174 WILDMEADOW RUN Winter Park, FL Welcome to 1174 Wildmeadow Run in Winter Parkâs gated Hawkâs Crest community. Located ...	3 beds \| 3 baths \| 1,770 sq.ft.	$669,900	Airbnb cash on cash: 3.08% Traditional cash on cash: 2.03% Airbnb Rental Income: $4337 Traditional Rental Income: $2773 Airbnb ROI: 3.08% Traditional ROI: 2.03%
1842 Puritan Ave Winter Park, FL Modern design , open concept layout , sleek quartz counter top , all new appliances, new l...	4 beds \| 2 baths \| 1,836 sq.ft.	$429,000	Airbnb cash on cash: 9.34% Traditional cash on cash: 4.33% Airbnb Rental Income: $5745 Traditional Rental Income: $2586 Airbnb ROI: 9.34% Traditional ROI: 4.33%
1926 NATALEN ROAD Winter Park, FL *MUST SEE WINTER PARK POOL HOME* Explore the virtual tours to fully appreciate the be...	3 beds \| 2 baths \| 1,469 sq.ft.	$649,900	Airbnb cash on cash: 3.37% Traditional cash on cash: 3.02% Airbnb Rental Income: $4337 Traditional Rental Income: $3213 Airbnb ROI: 3.37% Traditional ROI: 3.02%
2222 Marsh Sedge Lane Winter Park, FL Welcome to your dream Home! This stunning and elegant single-story home, built by Meritage...	4 beds \| 3 baths \| 2,192 sq.ft.	$764,900	Airbnb cash on cash: 4.27% Traditional cash on cash: 2.16% Airbnb Rental Income: $5745 Traditional Rental Income: $3097 Airbnb ROI: 4.27% Traditional ROI: 2.16%
2087 LAURELWOOD WAY Winter Park, FL One or more photo(s) has been virtually staged. Set within the serene gated community of H...	4 beds \| 2 baths \| 1,920 sq.ft.	$664,000	Airbnb cash on cash: 5.15% Traditional cash on cash: 2.43% Airbnb Rental Income: $5745 Traditional Rental Income: $2914 Airbnb ROI: 5.15% Traditional ROI: 2.43%

Your search for investment property begins and ends here

Airbnb Single Family Residential For Sale in Winter Park, FL

1751 GOODRICH AVENUE

Winter Park, FL

4 beds | 4 baths | 2,170 sq.ft.

$1,475,000

Airbnb cash on cash: 1.66%

Traditional cash on cash: 1.04%

Airbnb Rental Income: $5745

Traditional Rental Income: $3743

Airbnb ROI: 1.66%

Traditional ROI: 1.04%

668 OVERSPIN DRIVE

Winter Park, FL

4 beds | 3 baths | 2,509 sq.ft.

$875,000

Airbnb cash on cash: 3.21%

Traditional cash on cash: 2.32%

Airbnb Rental Income: $5745

Traditional Rental Income: $3878

Airbnb ROI: 3.21%

Traditional ROI: 2.32%

720 W WEBSTER AVENUE

Winter Park, FL

3 beds | 2 baths | 1,356 sq.ft.

$525,000

Airbnb cash on cash: 4.82%

Traditional cash on cash: 3.39%

Airbnb Rental Income: $4337

Traditional Rental Income: $2724

Airbnb ROI: 4.82%

Traditional ROI: 3.39%

1800 MAGNOLIA AVENUE

Winter Park, FL

4 beds | 3 baths | 2,431 sq.ft.

$1,148,000

Airbnb cash on cash: 2.2%

Traditional cash on cash: 2.04%

Airbnb Rental Income: $5745

Traditional Rental Income: $4421

Airbnb ROI: 2.2%

Traditional ROI: 2.04%

2036 VIA TUSCANY

Winter Park, FL

3 beds | 2 baths | 2,148 sq.ft.

$2,000,000

Airbnb cash on cash: 0.04%

Traditional cash on cash: -0.02%

Airbnb Rental Income: $4337

Traditional Rental Income: $3307

Airbnb ROI: 0.04%

Traditional ROI: -0.02%

811 Overspin Dr

Winter Park, FL

2 beds | 1 baths | 749 sq.ft.

$349,000

Airbnb cash on cash: 5.54%

Traditional cash on cash: 3.03%

Airbnb Rental Income: $3260

Traditional Rental Income: $1705

Airbnb ROI: 5.54%

Traditional ROI: 3.03%

2560 Franklin Avenue

Winter Park, FL

4 beds | 2 baths | 1,514 sq.ft.

$499,000

Airbnb cash on cash: 7.07%

Traditional cash on cash: 3.26%

Airbnb Rental Income: $5745

Traditional Rental Income: $2821

Airbnb ROI: 7.07%

Traditional ROI: 3.26%

1399 ALOMA AVENUE

Winter Park, FL

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

$600,000

Airbnb cash on cash: 4.6%

Traditional cash on cash: 4.09%

Airbnb Rental Income: $4337

Traditional Rental Income: $3142

Airbnb ROI: 4.6%