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 For Sale in Winter Park, FL

Q: How to get Winter-park, FL Airbnb data?

Airbnb data on vacation rentals in Winter-park, FL is available at Mashvisor. You can access data such as listings, real-time pricing trends, Winter-park, FL market insights, guest information and booking details, seasonality trends and historical Winter-park, FL Airbnb performance data .

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PROPERTY	DETAILS	SALE PRICE	INVESTMENT PERFORMANCE
500 N PENNSYLVANIA Avenue #G Winter Park, FL Virtually Staged. LOCATION, LOCATION, LOCATION in Winter Park!!! **Rare opportunity to own...	2 beds \| 1 baths \| 709 sq.ft.	$349,500	Airbnb cash on cash: 3.53% Traditional cash on cash: 1.13% Airbnb Rental Income: $3120 Traditional Rental Income: $1624 Airbnb ROI: 3.53% Traditional ROI: 1.13%
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.	$1,380,000	Airbnb cash on cash: 1.29% Traditional cash on cash: 1.18% Airbnb Rental Income: $4888 Traditional Rental Income: $3743 Airbnb ROI: 1.29% Traditional ROI: 1.18%
437 N CAPEN Avenue Winter Park, FL Virtually Staged. Nestled in the heart of Winter Park, just blocks from Park Avenue and Wi...	3 beds \| 3 baths \| 1,904 sq.ft.	$849,000	Airbnb cash on cash: 1.16% Traditional cash on cash: 0.2% Airbnb Rental Income: $4249 Traditional Rental Income: $2595 Airbnb ROI: 1.16% Traditional ROI: 0.2%
1840 BRYAN Avenue Winter Park, FL Welcome to modern luxury in the heart of Winter Park! This custom 2014-built estate rests ...	4 beds \| 4 baths \| 3,727 sq.ft.	$1,725,000	Airbnb cash on cash: 0.24% Traditional cash on cash: -0.32% Airbnb Rental Income: $4888 Traditional Rental Income: $2986 Airbnb ROI: 0.24% Traditional ROI: -0.32%
1611 CHESTNUT Avenue Winter Park, FL Located on one of Winter Park's beautiful oak-lined brick streets, 1611 Chestnut Avenue is...	4 beds \| 4 baths \| 2,916 sq.ft.	$985,000	Airbnb cash on cash: 2.76% Traditional cash on cash: 2.17% Airbnb Rental Income: $4888 Traditional Rental Income: $3341 Airbnb ROI: 2.76% Traditional ROI: 2.17%
7498 ALOMA PINES Court Winter Park, FL Welcome to beautiful Winter Park. This Townhome in Gated Aloma Trails has been meticulosly...	3 beds \| 3 baths \| 1,872 sq.ft.	$355,000	Airbnb cash on cash: 6.22% Traditional cash on cash: 3.61% Airbnb Rental Income: $4249 Traditional Rental Income: $2484 Airbnb ROI: 6.22% Traditional ROI: 3.61%
2500 LEE Road #220 Winter Park, FL **This house comes with a REDUCED RATE through the seller's preferred lender. This is a le...	2 beds \| 1 baths \| 851 sq.ft.	$199,900	Airbnb cash on cash: 8.51% Traditional cash on cash: 3.59% Airbnb Rental Income: $3120 Traditional Rental Income: $1477 Airbnb ROI: 8.51% Traditional ROI: 3.59%
3020 NICHOLSON Drive Winter Park, FL UPDATED 4-BEDROOM POOL HOME IN WINTER PARK WITH NO HOA! Welcome to 3020 Nicholson Drive, a...	4 beds \| 2 baths \| 1,756 sq.ft.	$470,000	Airbnb cash on cash: 6.52% Traditional cash on cash: 3.83% Airbnb Rental Income: $4888 Traditional Rental Income: $2702 Airbnb ROI: 6.52% Traditional ROI: 3.83%
2322 Woodcrest Dr Winter Park, FL Set on a quiet, landscaped, quarter-acre lot, this 4-bedroom, 2-bath POOL HOME offers a ra...	4 beds \| 2 baths \| 1,650 sq.ft.	$650,000	Airbnb cash on cash: 4.36% Traditional cash on cash: 2.54% Airbnb Rental Income: $4888 Traditional Rental Income: $2780 Airbnb ROI: 4.36% Traditional ROI: 2.54%
7463 CANFORD Court #15 Winter Park, FL Welcome to this beautifully updated corner home in the Whisperwood community of Winter Par...	3 beds \| 3 baths \| 1,580 sq.ft.	$270,000	Airbnb cash on cash: 7.96% Traditional cash on cash: 4.26% Airbnb Rental Income: $4249 Traditional Rental Income: $2408 Airbnb ROI: 7.96% Traditional ROI: 4.26%
2918 ANTIQUE OAKS Circle #25 Winter Park, FL 2 Bedroom 2 bath condo 1 block south of University Blvd great location for UCF or Full Sai...	2 beds \| 2 baths \| 1,018 sq.ft.	$189,000	Airbnb cash on cash: 8.09% Traditional cash on cash: 5.41% Airbnb Rental Income: $3120 Traditional Rental Income: $1930 Airbnb ROI: 8.09% Traditional ROI: 5.41%
1407 BROAD WING Lane Winter Park, FL Welcome to The Enclave at Hawks Crest! This 2019-built townhome offers 3 bedrooms, 2.5 bat...	3 beds \| 3 baths \| 2,308 sq.ft.	$482,000	Airbnb cash on cash: 4.26% Traditional cash on cash: 2.88% Airbnb Rental Income: $4249 Traditional Rental Income: $2731 Airbnb ROI: 4.26% Traditional ROI: 2.88%
1652 Berkshire Ave Winter Park, FL Rare opportunity in Winter Park in the highly coveted Orwin Manor! Location, location, loc...	3 beds \| 2 baths \| 1,498 sq.ft.	$429,000	Airbnb cash on cash: 6.87% Traditional cash on cash: 4.52% Airbnb Rental Income: $4249 Traditional Rental Income: $2407 Airbnb ROI: 6.87% Traditional ROI: 4.52%
900 CARVER Street Winter Park, FL Completely Renovated \| Move-In Ready \| Single-Story Living. A comprehensive renovation bri...	3 beds \| 3 baths \| 1,794 sq.ft.	$659,000	Airbnb cash on cash: 4.16% Traditional cash on cash: 3.5% Airbnb Rental Income: $4249 Traditional Rental Income: $2945 Airbnb ROI: 4.16% Traditional ROI: 3.5%
1931 ASTER Drive Winter Park, FL MOVE-IN READY, BEAUTIFULLY UPDATED, AND DESIGNED FOR FLORIDA LIVING! Welcome to 1931 Aster...	3 beds \| 3 baths \| 2,031 sq.ft.	$575,000	Airbnb cash on cash: 4.32% Traditional cash on cash: 3.28% Airbnb Rental Income: $4249 Traditional Rental Income: $2797 Airbnb ROI: 4.32% Traditional ROI: 3.28%
2217 SUSSEX Road Winter Park, FL NEW FLOORS, POOL, NO HOA, 4-YEAR-OLD ROOF & NEWER A/C!** Move-in ready 4-bedroom + office ...	4 beds \| 2 baths \| 2,092 sq.ft.	$479,999	Airbnb cash on cash: 6.43% Traditional cash on cash: 5.1% Airbnb Rental Income: $4888 Traditional Rental Income: $3288 Airbnb ROI: 6.43% Traditional ROI: 5.1%
5405 JUSTINE Way Winter Park, FL Welcome to 5405 Justine Way, a charming 3-bedroom, 2-bathroom single-family home in the de...	3 beds \| 2 baths \| 1,247 sq.ft.	$399,900	Airbnb cash on cash: 6.61% Traditional cash on cash: 3.91% Airbnb Rental Income: $4249 Traditional Rental Income: $2340 Airbnb ROI: 6.61% Traditional ROI: 3.91%
1946 STRATHAVEN Road Winter Park, FL *FULLY REMODELED WINTER PARK HOME NEAR BALDWIN PARK! * 1 YR HOME WARRANTY INCLUDED - a...	4 beds \| 3 baths \| 2,102 sq.ft.	$599,000	Airbnb cash on cash: 4.36% Traditional cash on cash: 2.66% Airbnb Rental Income: $4888 Traditional Rental Income: $2931 Airbnb ROI: 4.36% Traditional ROI: 2.66%
2430 CHANTILLY Avenue Winter Park, FL Architecture, design, and function come together with remarkable intention in this custom ...	4 beds \| 4 baths \| 2,916 sq.ft.	$1,550,000	Airbnb cash on cash: 1.32% Traditional cash on cash: -0.15% Airbnb Rental Income: $4888 Traditional Rental Income: $1768 Airbnb ROI: 1.32% Traditional ROI: -0.15%
2286 MARSH SEDGE Lane Winter Park, FL Virtually Staged. Welcome to one of the most uniquely positioned homes in the highly sough...	4 beds \| 3 baths \| 2,192 sq.ft.	$770,000	Airbnb cash on cash: 2.82% Traditional cash on cash: 2.22% Airbnb Rental Income: $4888 Traditional Rental Income: $3457 Airbnb ROI: 2.82% Traditional ROI: 2.22%
5080 SEMINOLE Avenue Winter Park, FL FULLY FURNISHED and ready for its next owner! This 3-bedroom, 2-bath Winter Park home offe...	3 beds \| 2 baths \| 1,078 sq.ft.	$299,900	Airbnb cash on cash: 9.38% Traditional cash on cash: 5.47% Airbnb Rental Income: $4249 Traditional Rental Income: $2249 Airbnb ROI: 9.38% Traditional ROI: 5.47%
811 Overspin Dr Winter Park, FL 811 Overspin Dr, Orlando, FL 32789 \| Single Family Residential	2 beds \| 1 baths \| 749 sq.ft.	$395,000	Airbnb cash on cash: 4.38% Traditional cash on cash: 2.47% Airbnb Rental Income: $3120 Traditional Rental Income: $1705 Airbnb ROI: 4.38% Traditional ROI: 2.47%
7641 VILLAGE GREEN Drive Winter Park, FL This three-bedroom, three-bath home in Village Green, Winter Park, offers 1,602 square fee...	3 beds \| 3 baths \| 1,602 sq.ft.	$515,000	Airbnb cash on cash: 4.67% Traditional cash on cash: 2.73% Airbnb Rental Income: $4249 Traditional Rental Income: $2417 Airbnb ROI: 4.67% Traditional ROI: 2.73%
1250 Formosa Ave Winter Park, FL Modern living meets unbeatable location in this stunning 3 bedroom, 3.5 bathroom home nest...	3 beds \| 3 baths \| 1,937 sq.ft.	$535,000	Airbnb cash on cash: 3.41% Traditional cash on cash: 3.21% Airbnb Rental Income: $4249 Traditional Rental Income: $3249 Airbnb ROI: 3.41% Traditional ROI: 3.21%
3601 Midiron Dr Winter Park, FL BUILD YOUR DREAM HOME IN WINTER PARK! Nestled directly across from the historic Dubsdread...	2 beds \| N/A baths \| 954 sq.ft.	$459,900	Airbnb cash on cash: 3.08% Traditional cash on cash: 1.68% Airbnb Rental Income: $3120 Traditional Rental Income: $1811 Airbnb ROI: 3.08% Traditional ROI: 1.68%
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.	$419,000	Airbnb cash on cash: 7.77% Traditional cash on cash: 4.46% Airbnb Rental Income: $4888 Traditional Rental Income: $2586 Airbnb ROI: 7.77% Traditional ROI: 4.46%
151 N ORLANDO AVENUE #142 Winter Park, FL Lakeside Living Meets Urban Convenience in the Heart of Winter Park! Welcome home to t...	1 beds \| 1 baths \| 582 sq.ft.	$199,900	Airbnb cash on cash: 4.28% Traditional cash on cash: 2.45% Airbnb Rental Income: $2297 Traditional Rental Income: $1378 Airbnb ROI: 4.28% Traditional ROI: 2.45%
4786 TANGERINE Avenue #4786 Winter Park, FL Discover comfort, style, and convenience in the heart of Winter Park! This beautifully upd...	2 beds \| 2 baths \| 1,281 sq.ft.	$220,000	Airbnb cash on cash: 6.29% Traditional cash on cash: 3.34% Airbnb Rental Income: $3120 Traditional Rental Income: $1797 Airbnb ROI: 6.29% Traditional ROI: 3.34%
2383 SUN VALLEY Circle #2383 Winter Park, FL Don't miss your opportunity on this super clean 2 bed 2 bath Winter Park condo! Updated ki...	2 beds \| 2 baths \| 1,295 sq.ft.	$234,900	Airbnb cash on cash: 5.92% Traditional cash on cash: 3.38% Airbnb Rental Income: $3120 Traditional Rental Income: $1847 Airbnb ROI: 5.92% Traditional ROI: 3.38%

Vacation Rentals in Winter Park

There are 137 vacation rental properties available for sale in the city of Winter Park . The median list price of Airbnb properties available for sale in Winter Park is $839,600 and the average price per square foot is $408. The cash on cash return on vacation rentals in Winter Park is 4.00%. The average monthly short term rental income in Winter Park is $4,249.

Winter Park, FL Short Term Rentals FAQs for Buyers, Sellers and Investors

There are 137 Airbnb properties available for sale in Winter Park.

In November 2026, the average Airbnb occupancy rate in Winter Park is 40%.

Airbnb data on vacation rentals in Winter Park, FL is available at Mashvisor. You can access data such as listings, real-time pricing trends, Winter Park, FL market insights, guest information and booking details, seasonality trends and historical Winter Park, FL Airbnb performance data.

Your search for investment property begins and ends here

Airbnb For Sale in Winter Park, FL

500 N PENNSYLVANIA Avenue #G

Winter Park, FL

2 beds | 1 baths | 709 sq.ft.

$349,500

Airbnb cash on cash: 3.53%

Traditional cash on cash: 1.13%

Airbnb Rental Income: $3120

Traditional Rental Income: $1624

Airbnb ROI: 3.53%

Traditional ROI: 1.13%

1751 GOODRICH Avenue

Winter Park, FL

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

$1,380,000

Airbnb cash on cash: 1.29%

Traditional cash on cash: 1.18%

Airbnb Rental Income: $4888

Traditional Rental Income: $3743

Airbnb ROI: 1.29%

Traditional ROI: 1.18%

437 N CAPEN Avenue

Winter Park, FL

3 beds | 3 baths | 1,904 sq.ft.

$849,000

Airbnb cash on cash: 1.16%

Traditional cash on cash: 0.2%

Airbnb Rental Income: $4249

Traditional Rental Income: $2595

Airbnb ROI: 1.16%

Traditional ROI: 0.2%

1840 BRYAN Avenue

Winter Park, FL

4 beds | 4 baths | 3,727 sq.ft.

$1,725,000

Airbnb cash on cash: 0.24%

Traditional cash on cash: -0.32%

Airbnb Rental Income: $4888

Traditional Rental Income: $2986

Airbnb ROI: 0.24%

Traditional ROI: -0.32%

1611 CHESTNUT Avenue

Winter Park, FL

4 beds | 4 baths | 2,916 sq.ft.

$985,000

Airbnb cash on cash: 2.76%

Traditional cash on cash: 2.17%

Airbnb Rental Income: $4888

Traditional Rental Income: $3341

Airbnb ROI: 2.76%

Traditional ROI: 2.17%

7498 ALOMA PINES Court

Winter Park, FL

3 beds | 3 baths | 1,872 sq.ft.

$355,000

Airbnb cash on cash: 6.22%

Traditional cash on cash: 3.61%

Airbnb Rental Income: $4249

Traditional Rental Income: $2484

Airbnb ROI: 6.22%

Traditional ROI: 3.61%

2500 LEE Road #220

Winter Park, FL

2 beds | 1 baths | 851 sq.ft.

$199,900

Airbnb cash on cash: 8.51%

Traditional cash on cash: 3.59%

Airbnb Rental Income: $3120

Traditional Rental Income: $1477

Airbnb ROI: 8.51%

Traditional ROI: 3.59%

3020 NICHOLSON Drive

Winter Park, FL

4 beds | 2 baths | 1,756 sq.ft.

$470,000

Airbnb cash on cash: 6.52%

Traditional cash on cash: 3.83%

Airbnb Rental Income: $4888

Traditional Rental Income: $2702

Airbnb ROI: 6.52%