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
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%
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%
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%
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%
150 Killarney Bay Ct #5 Winter Park, FL Tucked away in the hidden gem of Killarney Bay, this move-in ready condo offers the perfec...	2 beds \| 2 baths \| 1,140 sq.ft.	$345,000	Airbnb cash on cash: 4.33% Traditional cash on cash: 1.93% Airbnb Rental Income: $3260 Traditional Rental Income: $1751 Airbnb ROI: 4.33% Traditional ROI: 1.93%
2417 PASSAMONTE DRIVE #1E Winter Park, FL Location! Location! Location! Winter Park, Top Rated Florida Zone Schools, Move-In Ready, ...	3 beds \| 3 baths \| 1,837 sq.ft.	$329,999	Airbnb cash on cash: 7.38% Traditional cash on cash: 4.13% Airbnb Rental Income: $4337 Traditional Rental Income: $2416 Airbnb ROI: 7.38% Traditional ROI: 4.13%
4591 WHIMBREL PLACE Winter Park, FL Charming home nestled in a small, quaint community on spacious, custom-home lots. This wel...	3 beds \| 2 baths \| 1,942 sq.ft.	$490,000	Airbnb cash on cash: 5.77% Traditional cash on cash: 3.55% Airbnb Rental Income: $4337 Traditional Rental Income: $2410 Airbnb ROI: 5.77% Traditional ROI: 3.55%
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%
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%
2217 Sussex Rd Winter Park, FL 4 BEDROOMS with OFFICE POOL HOME. MOTIVATED SELLERS. MOVE IN READY! THIS HOME WILL NOT L...	4 beds \| 2 baths \| 2,092 sq.ft.	$530,000	Airbnb cash on cash: 7.17% Traditional cash on cash: 3.83% Airbnb Rental Income: $5745 Traditional Rental Income: $2942 Airbnb ROI: 7.17% Traditional ROI: 3.83%
1621 PURITAN, Winter Park, FL Under contract-accepting backup offers. Down Payment Assistance Available! Welcome to 1621...	4 beds \| 2 baths \| 1,765 sq.ft.	$440,000	Airbnb cash on cash: 8.97% Traditional cash on cash: 4.37% Airbnb Rental Income: $5745 Traditional Rental Income: $2704 Airbnb ROI: 8.97% Traditional ROI: 4.37%
3019 Antique Oaks Cir #124 Winter Park, FL Investors and Owner Occupied Welcome! Investors start your portfolio of properties with mo...	1 beds \| 1 baths \| 749 sq.ft.	$155,000	Airbnb cash on cash: 7.12% Traditional cash on cash: 6.07% Airbnb Rental Income: $2412 Traditional Rental Income: $1666 Airbnb ROI: 7.12% Traditional ROI: 6.07%
2189 SUSSEX ROAD Winter Park, FL One or more photo(s) has been virtually staged. One or more photos have been virtually sta...	4 beds \| 3 baths \| 1,776 sq.ft.	$535,000	Airbnb cash on cash: 7.11% Traditional cash on cash: 3.38% Airbnb Rental Income: $5745 Traditional Rental Income: $2731 Airbnb ROI: 7.11% Traditional ROI: 3.38%
525 S LAKEMONT AVENUE Winter Park, FL Under Construction. Winter Park Luxury Awaits You! Welcome to your dream homeâa stunn...	4 beds \| 4 baths \| 3,330 sq.ft.	$2,350,000	Airbnb cash on cash: 0.77% Traditional cash on cash: -0.07% Airbnb Rental Income: $5745 Traditional Rental Income: $2773 Airbnb ROI: 0.77% Traditional ROI: -0.07%
1174 WILDMEADOW RUN Winter Park, FL Welcome to Hawks Crest â Winter Parkâs premier gated, resort-style community! This bea...	3 beds \| 3 baths \| 1,770 sq.ft.	$669,000	Airbnb cash on cash: 3% Traditional cash on cash: 1.84% Airbnb Rental Income: $4337 Traditional Rental Income: $2702 Airbnb ROI: 3% Traditional ROI: 1.84%
1929 S LAKEMONT AVENUE Winter Park, FL This modern Winter Park townhome sits in a quiet pocket between Lake Spier and Lake Compto...	3 beds \| 4 baths \| 2,160 sq.ft.	$949,000	Airbnb cash on cash: 1.22% Traditional cash on cash: 0.68% Airbnb Rental Income: $4337 Traditional Rental Income: $2953 Airbnb ROI: 1.22% Traditional ROI: 0.68%
7641 Village Green Dr Winter Park, FL Welcome to this inviting single-family home at 7641 Village Green Dr in desirable Winter P...	3 beds \| 3 baths \| 1,602 sq.ft.	$550,000	Airbnb cash on cash: 4.45% Traditional cash on cash: 3.57% Airbnb Rental Income: $4337 Traditional Rental Income: $2970 Airbnb ROI: 4.45% Traditional ROI: 3.57%
3601 Midiron Dr Winter Park, FL BUILD YOUR DREAM HOME IN WINTER PARK! Nestled directly across from the historic Dubsdread...	N/A beds \| N/A baths \| 954 sq.ft.	$489,000	Airbnb cash on cash: 1.13% Traditional cash on cash: 1.01% Airbnb Rental Income: $2207 Traditional Rental Income: $1593 Airbnb ROI: 1.13% Traditional ROI: 1.01%
151 N Orlando Ave #118 Winter Park, FL Investment opportunity! Discover this hidden gemâa 2-bed, 1-bath condo nestled in the he...	2 beds \| 1 baths \| 710 sq.ft.	$299,999	Airbnb cash on cash: 5.17% Traditional cash on cash: 1.93% Airbnb Rental Income: $3260 Traditional Rental Income: $1610 Airbnb ROI: 5.17% Traditional ROI: 1.93%
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%
763 Overspin Dr Winter Park, FL 763 Overspin Dr, Orlando, FL 32789 \| Other	N/A beds \| N/A baths \| N/A	$699,000	Airbnb cash on cash: 0.51% Traditional cash on cash: -0.75% Airbnb Rental Income: $2207 Traditional Rental Income: $835 Airbnb ROI: 0.51% Traditional ROI: -0.75%
2500 Lee Rd #243 Winter Park, FL Reasons you'll love this condo: convenient, cozy and quiet, you can't beat this community ...	1 beds \| 1 baths \| 645 sq.ft.	$145,000	Airbnb cash on cash: 8.17% Traditional cash on cash: 5.62% Airbnb Rental Income: $2412 Traditional Rental Income: $1467 Airbnb ROI: 8.17% Traditional ROI: 5.62%
2774 Bright Bird Ln Winter Park, FL Motivated seller! Brand new townhouse professionally decorated, and available today! Built...	3 beds \| 2 baths \| 1,907 sq.ft.	$465,000	Airbnb cash on cash: 5.48% Traditional cash on cash: 3.45% Airbnb Rental Income: $4337 Traditional Rental Income: $2540 Airbnb ROI: 5.48% Traditional ROI: 3.45%
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%
726 And 720 N PENNSYLVANIA AVENUE Winter Park, FL Welcome to this exceptional duplex, a rare gem in Winter Park offering unmatched flexibili...	6 beds \| N/A baths \| 2,284 sq.ft.	$1,215,000	Airbnb cash on cash: 0.33% Traditional cash on cash: -0.02% Airbnb Rental Income: $3260 Traditional Rental Income: $2125 Airbnb ROI: 0.33% Traditional ROI: -0.02%

Vacation Rentals in Winter Park

There are 236 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 $550,000 and the average price per square foot is $283. The cash on cash return on vacation rentals in Winter Park is 5.00%. The average monthly short term rental income in Winter Park is $4,337.

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

There are 236 Airbnb properties available for sale in Winter Park.

In 2026, the best neighborhood to buy short term rental property is Winter Park.

In February 2026, the average Airbnb occupancy rate in Winter Park is 86%.

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

740 BAFFIE AVENUE

Winter Park, FL

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%

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%

701 DENTON ROAD

Winter Park, FL

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%

1400 S PENNSYLVANIA AVENUE

Winter Park, FL

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

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%

150 Killarney Bay Ct #5

Winter Park, FL

2 beds | 2 baths | 1,140 sq.ft.

$345,000

Airbnb cash on cash: 4.33%

Traditional cash on cash: 1.93%

Airbnb Rental Income: $3260

Traditional Rental Income: $1751

Airbnb ROI: 4.33%

Traditional ROI: 1.93%

2417 PASSAMONTE DRIVE #1E

Winter Park, FL

3 beds | 3 baths | 1,837 sq.ft.

$329,999

Airbnb cash on cash: 7.38%

Traditional cash on cash: 4.13%

Airbnb Rental Income: $4337

Traditional Rental Income: $2416

Airbnb ROI: 7.38%

Traditional ROI: 4.13%

4591 WHIMBREL PLACE

Winter Park, FL

3 beds | 2 baths | 1,942 sq.ft.

$490,000

Airbnb cash on cash: 5.77%

Traditional cash on cash: 3.55%

Airbnb Rental Income: $4337

Traditional Rental Income: $2410

Airbnb ROI: 5.77%