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: What is the average Airbnb occupancy rate in Winter-park, FL?

In April 2026, the average Airbnb occupancy rate in Winter-park is 86%.

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
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: 0.84% Airbnb Rental Income: $5745 Traditional Rental Income: $3463 Airbnb ROI: 1.66% Traditional ROI: 0.84%
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: 3.32% Airbnb Rental Income: $5745 Traditional Rental Income: $3558 Airbnb ROI: 4.92% Traditional ROI: 3.32%
1649 Harmon Ave Winter Park, FL Priced to Close before the end of the year!!! New Construction Orwin Manor Area home tha...	4 beds \| 3 baths \| 3,223 sq.ft.	$1,450,000	Airbnb cash on cash: 2.18% Traditional cash on cash: 2.11% Airbnb Rental Income: $5745 Traditional Rental Income: $4499 Airbnb ROI: 2.18% Traditional ROI: 2.11%
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.	$715,000	Airbnb cash on cash: 5.01% Traditional cash on cash: 2.51% Airbnb Rental Income: $5745 Traditional Rental Income: $2932 Airbnb ROI: 5.01% Traditional ROI: 2.51%
2607 Lafayette Ave Winter Park, FL Welcome to 2607 Lafayette Avenueâa stunning custom home in one of Winter Parkâs most d...	4 beds \| 4 baths \| 2,770 sq.ft.	$1,095,000	Airbnb cash on cash: 2.17% Traditional cash on cash: 1.79% Airbnb Rental Income: $5745 Traditional Rental Income: $4214 Airbnb ROI: 2.17% Traditional ROI: 1.79%
1000 S SEMORAN BOULEVARD #715 Winter Park, FL Prime location meets exceptional value in the highly sought-after Winter Park area! This f...	1 beds \| 1 baths \| 735 sq.ft.	$122,990	Airbnb cash on cash: 8.99% Traditional cash on cash: 5.99% Airbnb Rental Income: $2412 Traditional Rental Income: $1465 Airbnb ROI: 8.99% Traditional ROI: 5.99%
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: 1.86% Airbnb Rental Income: $5745 Traditional Rental Income: $3501 Airbnb ROI: 3.21% Traditional ROI: 1.86%
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: 1.2% Airbnb Rental Income: $4337 Traditional Rental Income: $2452 Airbnb ROI: 2.61% Traditional ROI: 1.2%
150 KILLARNEY BAY COURT #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.	$335,000	Airbnb cash on cash: 4.49% Traditional cash on cash: 3.58% Airbnb Rental Income: $3260 Traditional Rental Income: $2243 Airbnb ROI: 4.49% Traditional ROI: 3.58%
1518 PINEWOOD DRIVE Winter Park, FL Income-producing home with a detached in-law apartment in a prime central Orlando location...	3 beds \| N/A baths \| 1,197 sq.ft.	$415,000	Airbnb cash on cash: 8.94% Traditional cash on cash: 3.96% Airbnb Rental Income: $5745 Traditional Rental Income: $2662 Airbnb ROI: 8.94% Traditional ROI: 3.96%
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: 8.73% Traditional cash on cash: 5.4% Airbnb Rental Income: $3260 Traditional Rental Income: $1930 Airbnb ROI: 8.73% Traditional ROI: 5.4%
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: 3.79% Airbnb Rental Income: $4337 Traditional Rental Income: $2760 Airbnb ROI: 5.25% Traditional ROI: 3.79%
7336 FOREST HILL COURT #240 Winter Park, FL Updated Winter Park Townhome!! If you are looking for LOCATION this is the property for yo...	2 beds \| 2 baths \| 990 sq.ft.	$179,900	Airbnb cash on cash: 8.72% Traditional cash on cash: 4.32% Airbnb Rental Income: $3260 Traditional Rental Income: $1775 Airbnb ROI: 8.72% Traditional ROI: 4.32%
144 LEWFIELD CIRCLE #144 Winter Park, FL LOCATION! LOCATION! LOCATION! Beautiful 2nd floor corner condo in desirable Winter Park, f...	1 beds \| 1 baths \| 678 sq.ft.	$144,000	Airbnb cash on cash: 8.2% Traditional cash on cash: 5.34% Airbnb Rental Income: $2412 Traditional Rental Income: $1426 Airbnb ROI: 8.2% Traditional ROI: 5.34%
764 W COMSTOCK AVENUE Winter Park, FL Under contract-accepting backup offers. Welcome to this charming 1935 Winter Park bungalow...	2 beds \| 1 baths \| 925 sq.ft.	$474,000	Airbnb cash on cash: 3.41% Traditional cash on cash: 2.3% Airbnb Rental Income: $3260 Traditional Rental Income: $2035 Airbnb ROI: 3.41% Traditional ROI: 2.3%
5418 ARDMORE DRIVE Winter Park, FL One or more photo(s) has been virtually staged. WELCOME HOME A generous .23 ACRE LOT, ...	3 beds \| 2 baths \| 1,560 sq.ft.	$450,000	Airbnb cash on cash: 5.98% Traditional cash on cash: 3.6% Airbnb Rental Income: $4337 Traditional Rental Income: $2424 Airbnb ROI: 5.98% Traditional ROI: 3.6%
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: 4.7% Airbnb Rental Income: $5745 Traditional Rental Income: $2773 Airbnb ROI: 9.18% Traditional ROI: 4.7%
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: 3.92% Airbnb Rental Income: $5745 Traditional Rental Income: $2390 Airbnb ROI: 9.46% Traditional ROI: 3.92%
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.	$550,000	Airbnb cash on cash: 4.56% Traditional cash on cash: 3.17% Airbnb Rental Income: $4337 Traditional Rental Income: $2709 Airbnb ROI: 4.56% Traditional ROI: 3.17%
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: 4.31% Airbnb Rental Income: $5745 Traditional Rental Income: $3132 Airbnb ROI: 7.32% Traditional ROI: 4.31%
503 W CANTON AVENUE Winter Park, FL Walk to Park Avenue! Model Home, tons of upgrades. Enjoy luxury living and premium sought ...	3 beds \| 3 baths \| 2,342 sq.ft.	$1,146,000	Airbnb cash on cash: 0.1% Traditional cash on cash: -0.13% Airbnb Rental Income: $4337 Traditional Rental Income: $3177 Airbnb ROI: 0.1% Traditional ROI: -0.13%
3463 ARNEL DRIVE Winter Park, FL Your pool home in Winter Park. This home offers three bedrooms plus a versatile bonus r...	3 beds \| 2 baths \| 1,770 sq.ft.	$479,900	Airbnb cash on cash: 5.45% Traditional cash on cash: 4.27% Airbnb Rental Income: $4337 Traditional Rental Income: $2895 Airbnb ROI: 5.45% Traditional ROI: 4.27%
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.	$1,150,000	Airbnb cash on cash: 2.2% Traditional cash on cash: 0.59% Airbnb Rental Income: $5745 Traditional Rental Income: $2877 Airbnb ROI: 2.2% Traditional ROI: 0.59%
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: 2.58% Airbnb Rental Income: $5745 Traditional Rental Income: $3752 Airbnb ROI: 3.75% Traditional ROI: 2.58%
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: -0.18% Airbnb Rental Income: $4337 Traditional Rental Income: $3015 Airbnb ROI: 0.04% Traditional ROI: -0.18%
189 LEWFIELD CIRCLE #189 Winter Park, FL Experience the best of the Winter Park lifestyle in this beautifully updated first-floor c...	1 beds \| 1 baths \| 678 sq.ft.	$155,000	Airbnb cash on cash: 6.87% Traditional cash on cash: 4.2% Airbnb Rental Income: $2412 Traditional Rental Income: $1426 Airbnb ROI: 6.87% Traditional ROI: 4.2%
2126 N HAMPTON CIRCLE Winter Park, FL Under contract-accepting backup offers. Step into your own private retreat in the sought-a...	3 beds \| 2 baths \| 1,745 sq.ft.	$500,000	Airbnb cash on cash: 5.18% Traditional cash on cash: 3.23% Airbnb Rental Income: $4337 Traditional Rental Income: $2513 Airbnb ROI: 5.18% Traditional ROI: 3.23%
1028 LAKE BELL DRIVE Winter Park, FL Under contract-accepting backup offers. WELCOME HOME to this rare Winter Park opportunity!...	2 beds \| 2 baths \| 1,418 sq.ft.	$400,000	Airbnb cash on cash: 4.2% Traditional cash on cash: 4.16% Airbnb Rental Income: $3260 Traditional Rental Income: $2513 Airbnb ROI: 4.2% Traditional ROI: 4.16%
3019 ANTIQUE OAKS CIRCLE #124 Winter Park, FL The Ultimate Winter Park is your every desire. Investment Potential, Student Sanctuary or ...	1 beds \| 1 baths \| 749 sq.ft.	$154,000	Airbnb cash on cash: 7.17% Traditional cash on cash: 6.11% Airbnb Rental Income: $2412 Traditional Rental Income: $1665 Airbnb ROI: 7.17% Traditional ROI: 6.11%
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: 1.81% Airbnb Rental Income: $4337 Traditional Rental Income: $2635 Airbnb ROI: 3.08% Traditional ROI: 1.81%
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.	$915,000	Airbnb cash on cash: 1.3% Traditional cash on cash: 0.74% Airbnb Rental Income: $4337 Traditional Rental Income: $2953 Airbnb ROI: 1.3% Traditional ROI: 0.74%
1985 Japonica Road Winter Park, FL One or more photo(s) has been virtually staged. New Price Adjusted, Welcome to 1985 Japoni...	4 beds \| 2 baths \| 2,096 sq.ft.	$599,997	Airbnb cash on cash: 6.18% Traditional cash on cash: 2.77% Airbnb Rental Income: $5745 Traditional Rental Income: $2688 Airbnb ROI: 6.18% Traditional ROI: 2.77%
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: 2.94% Airbnb Rental Income: $5745 Traditional Rental Income: $2669 Airbnb ROI: 7.07% Traditional ROI: 2.94%
1360 WESTDALE AVENUE Winter Park, FL Under contract-accepting backup offers. Welcome to 1360 Westdale Ave, a well-maintained Wi...	3 beds \| 2 baths \| 1,318 sq.ft.	$410,000	Airbnb cash on cash: 6.72% Traditional cash on cash: 4.57% Airbnb Rental Income: $4337 Traditional Rental Income: $2600 Airbnb ROI: 6.72% Traditional ROI: 4.57%
1810 HOLLYWOOD AVENUE Winter Park, FL Under Construction. Estimated completion August!! Experience modern luxury living in the h...	4 beds \| 4 baths \| 2,604 sq.ft.	$1,689,000	Airbnb cash on cash: 1.47% Traditional cash on cash: 1.31% Airbnb Rental Income: $5745 Traditional Rental Income: $4352 Airbnb ROI: 1.47% Traditional ROI: 1.31%
1375 MERRYDALE WAY Winter Park, FL Under contract-accepting backup offers. Wake up to tranquil lake views and effortless luxu...	3 beds \| 3 baths \| 1,756 sq.ft.	$439,000	Airbnb cash on cash: 5.09% Traditional cash on cash: 3% Airbnb Rental Income: $4337 Traditional Rental Income: $2566 Airbnb ROI: 5.09% Traditional ROI: 3%
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: -0.14% Airbnb Rental Income: $2207 Traditional Rental Income: $1231 Airbnb ROI: 0.51% Traditional ROI: -0.14%
2500 LEE ROAD #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: 5.94% Airbnb Rental Income: $2412 Traditional Rental Income: $1512 Airbnb ROI: 8.17% Traditional ROI: 5.94%
126 SCOTTSDALE SQUARE #126 Winter Park, FL Excellent opportunity to own this second-floor, 2-bedroom, 1/1-bath condo in a Convenientl...	2 beds \| 2 baths \| 1,085 sq.ft.	$150,000	Airbnb cash on cash: 7.52% Traditional cash on cash: 3.07% Airbnb Rental Income: $3260 Traditional Rental Income: $1889 Airbnb ROI: 7.52% Traditional ROI: 3.07%
2774 BRIGHT BIRD LANE Winter Park, FL Motivated seller! Brand new townhouse professionally decorated, and available today! Built...	3 beds \| 3 baths \| 1,907 sq.ft.	$465,000	Airbnb cash on cash: 5.48% Traditional cash on cash: 3.8% Airbnb Rental Income: $4337 Traditional Rental Income: $2694 Airbnb ROI: 5.48% Traditional ROI: 3.8%

Vacation Rentals in Winter Park

There are 129 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 $499,990 and the average price per square foot is $255. 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 129 Airbnb properties available for sale in Winter Park.

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

In April 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

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: 0.84%

Airbnb Rental Income: $5745

Traditional Rental Income: $3463

Airbnb ROI: 1.66%

Traditional ROI: 0.84%

3114 HEARTLEAF PLACE

Winter Park, FL

4 beds | 3 baths | 2,702 sq.ft.

$699,900

Airbnb cash on cash: 4.92%

Traditional cash on cash: 3.32%

Airbnb Rental Income: $5745

Traditional Rental Income: $3558

Airbnb ROI: 4.92%

Traditional ROI: 3.32%

1649 Harmon Ave

Winter Park, FL

4 beds | 3 baths | 3,223 sq.ft.

$1,450,000

Airbnb cash on cash: 2.18%

Traditional cash on cash: 2.11%

Airbnb Rental Income: $5745

Traditional Rental Income: $4499

Airbnb ROI: 2.18%

Traditional ROI: 2.11%

744 CORNWALL ROAD

Winter Park, FL

4 beds | 2 baths | 1,968 sq.ft.

$715,000

Airbnb cash on cash: 5.01%

Traditional cash on cash: 2.51%

Airbnb Rental Income: $5745

Traditional Rental Income: $2932

Airbnb ROI: 5.01%

Traditional ROI: 2.51%

2607 Lafayette Ave

Winter Park, FL

4 beds | 4 baths | 2,770 sq.ft.

$1,095,000

Airbnb cash on cash: 2.17%

Traditional cash on cash: 1.79%

Airbnb Rental Income: $5745

Traditional Rental Income: $4214

Airbnb ROI: 2.17%

Traditional ROI: 1.79%

1000 S SEMORAN BOULEVARD #715

Winter Park, FL

1 beds | 1 baths | 735 sq.ft.

$122,990

Airbnb cash on cash: 8.99%

Traditional cash on cash: 5.99%

Airbnb Rental Income: $2412

Traditional Rental Income: $1465

Airbnb ROI: 8.99%

Traditional ROI: 5.99%

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: 1.86%

Airbnb Rental Income: $5745

Traditional Rental Income: $3501

Airbnb ROI: 3.21%

Traditional ROI: 1.86%

418 GILBERT ROAD

Winter Park, FL

3 beds | 3 baths | 1,680 sq.ft.

$740,000

Airbnb cash on cash: 2.61%

Traditional cash on cash: 1.2%

Airbnb Rental Income: $4337

Traditional Rental Income: $2452

Airbnb ROI: 2.61%