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 167 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 Ave Winter Park, FL Welcome to 1751 Goodrich Ave, a beautifully designed residence in the heart of Winter Park...	4 beds \| 3 baths \| 2,170 sq.ft.	$1,475,000	Airbnb cash on cash: 1.66% Traditional cash on cash: 0.78% Airbnb Rental Income: $5745 Traditional Rental Income: $3386 Airbnb ROI: 1.66% Traditional ROI: 0.78%
1324 INDIANA AVENUE Winter Park, FL Charming two story bungalow built in 1935. Timeless character meets modern comfort in this...	4 beds \| 3 baths \| 1,692 sq.ft.	$745,000	Airbnb cash on cash: 4.32% Traditional cash on cash: 1.95% Airbnb Rental Income: $5745 Traditional Rental Income: $2954 Airbnb ROI: 4.32% Traditional ROI: 1.95%
726 N PENNSYLVANIA AVENUE Winter Park, FL Welcome to this beautifully designed 3-bedroom, 2-bathroom home, offering a blend of moder...	3 beds \| 2 baths \| 1,167 sq.ft.	$695,000	Airbnb cash on cash: 3.43% Traditional cash on cash: 1.13% Airbnb Rental Income: $4337 Traditional Rental Income: $1931 Airbnb ROI: 3.43% Traditional ROI: 1.13%
250 Cortland Ave Winter Park, FL Welcome to the epitome of the Winter Park lifestyle at 250 Cortland Ave, nestled among mil...	3 beds \| 2 baths \| 2,114 sq.ft.	$950,000	Airbnb cash on cash: 2.31% Traditional cash on cash: 1.8% Airbnb Rental Income: $4337 Traditional Rental Income: $2974 Airbnb ROI: 2.31% Traditional ROI: 1.8%
1981 BLUE RIDGE ROAD Winter Park, FL One or more photo(s) has been virtually staged. **This house comes with a REDUCED RATE thr...	4 beds \| 2 baths \| 2,750 sq.ft.	$1,180,000	Airbnb cash on cash: 2.8% Traditional cash on cash: 1.1% Airbnb Rental Income: $5745 Traditional Rental Income: $2726 Airbnb ROI: 2.8% Traditional ROI: 1.1%
1564 CAVENDISH ROAD Winter Park, FL Charming 3BR bungalow in sought-after Orwin Manor with timeless appeal and tons of potenti...	3 beds \| 1 baths \| 1,140 sq.ft.	$450,000	Airbnb cash on cash: 5.72% Traditional cash on cash: 1.95% Airbnb Rental Income: $4337 Traditional Rental Income: $1838 Airbnb ROI: 5.72% Traditional ROI: 1.95%
1996 Indiana Ave Winter Park, FL Investor Special â Fixer Upper Opportunity in Winter Park / College Park Area. Rare o...	2 beds \| 1 baths \| 818 sq.ft.	$249,900	Airbnb cash on cash: 8.76% Traditional cash on cash: 4.26% Airbnb Rental Income: $3260 Traditional Rental Income: $1467 Airbnb ROI: 8.76% Traditional ROI: 4.26%
446 Alberta Dr Winter Park, FL Charming Opportunity in Prime Winter Park â 446 Alberta Drive, Winter Park, FL! First t...	4 beds \| 2 baths \| 3,263 sq.ft.	$1,675,000	Airbnb cash on cash: 1.39% Traditional cash on cash: 0.84% Airbnb Rental Income: $5745 Traditional Rental Income: $3714 Airbnb ROI: 1.39% Traditional ROI: 0.84%
2580 Euston Rd #0 Winter Park, FL just over .25 acre in winter park with block construction 3 bedroom 2 bath. Opportunity to...	3 beds \| 2 baths \| 1,158 sq.ft.	$415,000	Airbnb cash on cash: 6.37% Traditional cash on cash: 2.9% Airbnb Rental Income: $4337 Traditional Rental Income: $2043 Airbnb ROI: 6.37% Traditional ROI: 2.9%
2009 Cornell Ave Winter Park, FL 2009 Cornell Ave, Orlando, FL 32789 \| Single Family Residential	2 beds \| 1 baths \| 762 sq.ft.	$259,000	Airbnb cash on cash: 8.08% Traditional cash on cash: 3.68% Airbnb Rental Income: $3260 Traditional Rental Income: $1453 Airbnb ROI: 8.08% Traditional ROI: 3.68%
1451 Cavendish Rd Winter Park, FL Welcome to 1451 Cavendish Road, a beautifully renovated home in the heart of Orwin Manor, ...	3 beds \| 2 baths \| 1,437 sq.ft.	$619,500	Airbnb cash on cash: 3.7% Traditional cash on cash: 1.63% Airbnb Rental Income: $4337 Traditional Rental Income: $2225 Airbnb ROI: 3.7% Traditional ROI: 1.63%
560 Ololu Dr Winter Park, FL Nestled on the shores of private, skiable Lake Killarney, this beautifully updated and abs...	2 beds \| 2 baths \| 1,086 sq.ft.	$949,000	Airbnb cash on cash: 0.85% Traditional cash on cash: 0.36% Airbnb Rental Income: $3260 Traditional Rental Income: $2093 Airbnb ROI: 0.85% Traditional ROI: 0.36%
1780 Bryan Ave 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.	$800,000	Airbnb cash on cash: 4.13% Traditional cash on cash: 1.32% Airbnb Rental Income: $5745 Traditional Rental Income: $2505 Airbnb ROI: 4.13% Traditional ROI: 1.32%
2361 Mulbry Dr Winter Park, FL Under Construction. Signature new construction currently under way, thoughtfully designed ...	4 beds \| 4 baths \| 3,111 sq.ft.	$2,395,000	Airbnb cash on cash: 0.78% Traditional cash on cash: 0.53% Airbnb Rental Income: $5745 Traditional Rental Income: $4042 Airbnb ROI: 0.78% Traditional ROI: 0.53%
1500 Berkshire Ave Winter Park, FL Welcome to this beautifully renovated historic home in the heart of Orwin Manor, one of Wi...	3 beds \| 1 baths \| 1,485 sq.ft.	$625,000	Airbnb cash on cash: 3.64% Traditional cash on cash: 2.6% Airbnb Rental Income: $4337 Traditional Rental Income: $2816 Airbnb ROI: 3.64% Traditional ROI: 2.6%
681 Overspin Dr Winter Park, FL Well-maintained and beautifully upgraded, this exceptional home is located in the highly d...	4 beds \| 2 baths \| 2,220 sq.ft.	$669,000	Airbnb cash on cash: 5.29% Traditional cash on cash: 1.33% Airbnb Rental Income: $5745 Traditional Rental Income: $2085 Airbnb ROI: 5.29% Traditional ROI: 1.33%
841 W Swoope Ave Winter Park, FL Prime Winter Park Redevelopment Opportunity â R-2 Zoned Rare opportunity to acquire a...	2 beds \| 1 baths \| 1,396 sq.ft.	$740,000	Airbnb cash on cash: 2.02% Traditional cash on cash: 0.64% Airbnb Rental Income: $3260 Traditional Rental Income: $1579 Airbnb ROI: 2.02% Traditional ROI: 0.64%
740 BAFFIE AVENUE Winter Park, FL Under contract-accepting backup offers. Welcome to this fully remodeled, move in ready hom...	3 beds \| 2 baths \| 1,456 sq.ft.	$420,000	Airbnb cash on cash: 6.22% Traditional cash on cash: 3.18% Airbnb Rental Income: $4337 Traditional Rental Income: $2229 Airbnb ROI: 6.22% Traditional ROI: 3.18%
1400 S PENNSYLVANIA AVENUE Winter Park, FL Look at this rare opportunity to own a chic and trendy residence in winter park in an incr...	4 beds \| 3 baths \| 2,310 sq.ft.	$1,250,000	Airbnb cash on cash: 1.79% Traditional cash on cash: 0.61% Airbnb Rental Income: $5745 Traditional Rental Income: $3232 Airbnb ROI: 1.79% Traditional ROI: 0.61%
2811 EASTERN PARKWAY Winter Park, FL Under contract-accepting backup offers. Mid-Century Modern architecture meets modern comfo...	3 beds \| 2 baths \| 1,433 sq.ft.	$625,000	Airbnb cash on cash: 3.82% Traditional cash on cash: 3% Airbnb Rental Income: $4337 Traditional Rental Income: $2945 Airbnb ROI: 3.82% Traditional ROI: 3%
1600 Palmer Ave Winter Park, FL Discover refined elegance in this meticulously updated 3-bedroom, 2.5-bath two-story resid...	3 beds \| 3 baths \| 2,550 sq.ft.	$1,200,000	Airbnb cash on cash: 1.24% Traditional cash on cash: 0.68% Airbnb Rental Income: $4337 Traditional Rental Income: $2805 Airbnb ROI: 1.24% Traditional ROI: 0.68%
875 W LYMAN AVENUE Winter Park, FL Don't miss this rare opportunity to own a slice of historic Hannibal Square! This 2 bed 2 ...	2 beds \| 2 baths \| 760 sq.ft.	$425,000	Airbnb cash on cash: 4.28% Traditional cash on cash: 2.7% Airbnb Rental Income: $3260 Traditional Rental Income: $1899 Airbnb ROI: 4.28% Traditional ROI: 2.7%
1875 STAUNTON AVENUE Winter Park, FL Under contract-accepting backup offers. Welcome to this newer single-family home tucked aw...	4 beds \| 2 baths \| 2,036 sq.ft.	$560,000	Airbnb cash on cash: 6.18% Traditional cash on cash: 0.81% Airbnb Rental Income: $5745 Traditional Rental Income: $1793 Airbnb ROI: 6.18% Traditional ROI: 0.81%
770 W WEBSTER AVENUE Winter Park, FL Under contract-accepting backup offers. Stop the car! Check out this classic 4/2 Florida ...	4 beds \| 2 baths \| 1,008 sq.ft.	$725,000	Airbnb cash on cash: 5% Traditional cash on cash: 1.09% Airbnb Rental Income: $5745 Traditional Rental Income: $1955 Airbnb ROI: 5% Traditional ROI: 1.09%
1007 EARLY AVENUE Winter Park, FL Under contract-accepting backup offers. Welcome to your next chapter at 1007 Early Ave in ...	3 beds \| 2 baths \| 1,721 sq.ft.	$379,900	Airbnb cash on cash: 8.04% Traditional cash on cash: 5.45% Airbnb Rental Income: $4337 Traditional Rental Income: $2502 Airbnb ROI: 8.04% Traditional ROI: 5.45%
701 DENTON ROAD Winter Park, FL Motivated Seller! Contact us today. Welcome to this beautifully upgraded home in Winter Pa...	3 beds \| 2 baths \| 2,268 sq.ft.	$565,000	Airbnb cash on cash: 4.22% Traditional cash on cash: 3.44% Airbnb Rental Income: $4337 Traditional Rental Income: $3016 Airbnb ROI: 4.22% Traditional ROI: 3.44%
1213 Lindenwood Ln Winter Park, FL Discover the perfect blend of mid-century modern architecture and contemporary living in t...	4 beds \| 2 baths \| 2,505 sq.ft.	$739,900	Airbnb cash on cash: 4.66% Traditional cash on cash: 2.7% Airbnb Rental Income: $5745 Traditional Rental Income: $3233 Airbnb ROI: 4.66% Traditional ROI: 2.7%
346 S Ranger Blvd 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.	$495,000	Airbnb cash on cash: 5.01% Traditional cash on cash: 2.61% Airbnb Rental Income: $4337 Traditional Rental Income: $2291 Airbnb ROI: 5.01% Traditional ROI: 2.61%
1849 Viburnum Ln 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: 3.75% Airbnb Rental Income: $5745 Traditional Rental Income: $2323 Airbnb ROI: 9.46% Traditional ROI: 3.75%

Your search for investment property begins and ends here

Airbnb Single Family Residential For Sale in Winter Park, FL

1751 Goodrich Ave

Winter Park, FL

4 beds | 3 baths | 2,170 sq.ft.

$1,475,000

Airbnb cash on cash: 1.66%

Traditional cash on cash: 0.78%

Airbnb Rental Income: $5745

Traditional Rental Income: $3386

Airbnb ROI: 1.66%

Traditional ROI: 0.78%

1324 INDIANA AVENUE

Winter Park, FL

4 beds | 3 baths | 1,692 sq.ft.

$745,000

Airbnb cash on cash: 4.32%

Traditional cash on cash: 1.95%

Airbnb Rental Income: $5745

Traditional Rental Income: $2954

Airbnb ROI: 4.32%

Traditional ROI: 1.95%

726 N PENNSYLVANIA AVENUE

Winter Park, FL

3 beds | 2 baths | 1,167 sq.ft.

$695,000

Airbnb cash on cash: 3.43%

Traditional cash on cash: 1.13%

Airbnb Rental Income: $4337

Traditional Rental Income: $1931

Airbnb ROI: 3.43%

Traditional ROI: 1.13%

250 Cortland Ave

Winter Park, FL

3 beds | 2 baths | 2,114 sq.ft.

$950,000

Airbnb cash on cash: 2.31%

Traditional cash on cash: 1.8%

Airbnb Rental Income: $4337

Traditional Rental Income: $2974

Airbnb ROI: 2.31%

Traditional ROI: 1.8%

1981 BLUE RIDGE ROAD

Winter Park, FL

4 beds | 2 baths | 2,750 sq.ft.

$1,180,000

Airbnb cash on cash: 2.8%

Traditional cash on cash: 1.1%

Airbnb Rental Income: $5745

Traditional Rental Income: $2726

Airbnb ROI: 2.8%

Traditional ROI: 1.1%

1564 CAVENDISH ROAD

Winter Park, FL

3 beds | 1 baths | 1,140 sq.ft.

$450,000

Airbnb cash on cash: 5.72%

Traditional cash on cash: 1.95%

Airbnb Rental Income: $4337

Traditional Rental Income: $1838

Airbnb ROI: 5.72%

Traditional ROI: 1.95%

1996 Indiana Ave

Winter Park, FL

2 beds | 1 baths | 818 sq.ft.

$249,900

Airbnb cash on cash: 8.76%

Traditional cash on cash: 4.26%

Airbnb Rental Income: $3260

Traditional Rental Income: $1467

Airbnb ROI: 8.76%

Traditional ROI: 4.26%

446 Alberta Dr

Winter Park, FL

4 beds | 2 baths | 3,263 sq.ft.

$1,675,000

Airbnb cash on cash: 1.39%

Traditional cash on cash: 0.84%

Airbnb Rental Income: $5745

Traditional Rental Income: $3714

Airbnb ROI: 1.39%