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 .

separator

PROPERTY	DETAILS	SALE PRICE	INVESTMENT PERFORMANCE
2844 SCARLET ROAD Winter Park, FL Under contract-accepting backup offers. Welcome to this stunning mid-century modern beauty...	4 beds \| 2 baths \| 1,508 sq.ft.	$499,000	Airbnb cash on cash: 7.56% Traditional cash on cash: 3.52% Airbnb Rental Income: $5745 Traditional Rental Income: $2713 Airbnb ROI: 7.56% Traditional ROI: 3.52%
1308 S PENNSYLVANIA AVENUE #3 Winter Park, FL This beautifully updated 1-bedroom, 1-bath condo offers 823 sq. ft. of stylish living spac...	1 beds \| 1 baths \| 823 sq.ft.	$325,000	Airbnb cash on cash: 3.63% Traditional cash on cash: 2.2% Airbnb Rental Income: $2412 Traditional Rental Income: $1384 Airbnb ROI: 3.63% Traditional ROI: 2.2%
690 S LAKEMONT AVENUE Winter Park, FL Under contract-accepting backup offers. Short Sale. Beautifully updated 4BR/3BA pool home ...	4 beds \| 3 baths \| 1,897 sq.ft.	$550,000	Airbnb cash on cash: 6.35% Traditional cash on cash: 3.9% Airbnb Rental Income: $5745 Traditional Rental Income: $3342 Airbnb ROI: 6.35% Traditional ROI: 3.9%
8065 PLEASANT PINE CIRCLE Winter Park, FL **This property qualifies for a closing cost credit up to $8,800 through the Sellerâs pr...	4 beds \| 2 baths \| 1,843 sq.ft.	$560,000	Airbnb cash on cash: 6.66% Traditional cash on cash: 2.39% Airbnb Rental Income: $5745 Traditional Rental Income: $2364 Airbnb ROI: 6.66% Traditional ROI: 2.39%
744 CORNWALL ROAD Winter Park, FL Charming 4-Bedroom Home in Desirable Winter Park Pines Welcome to your new home in the he...	4 beds \| 2 baths \| 1,968 sq.ft.	$750,000	Airbnb cash on cash: 4.73% Traditional cash on cash: 2.13% Airbnb Rental Income: $5745 Traditional Rental Income: $2775 Airbnb ROI: 4.73% Traditional ROI: 2.13%
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: 1.34% Airbnb Rental Income: $5745 Traditional Rental Income: $3752 Airbnb ROI: 2.17% Traditional ROI: 1.34%
1516 PINEWOOD DRIVE Winter Park, FL PINEWOOD SUB N/9 LOT 12 BLK A Well-maintained, modest 2-1 home in College Park with c...	2 beds \| 1 baths \| 1,028 sq.ft.	$349,000	Airbnb cash on cash: 5.04% Traditional cash on cash: 2.51% Airbnb Rental Income: $3260 Traditional Rental Income: $1698 Airbnb ROI: 5.04% Traditional ROI: 2.51%
2812 WOODSIDE AVENUE Winter Park, FL Under contract-accepting backup offers. In the heart of the Audubon Park Garden District y...	3 beds \| 2 baths \| 1,842 sq.ft.	$625,000	Airbnb cash on cash: 3.49% Traditional cash on cash: 2.72% Airbnb Rental Income: $4337 Traditional Rental Income: $2979 Airbnb ROI: 3.49% Traditional ROI: 2.72%
720 N PENNSYLVANIA AVENUE Winter Park, FL Nestled in one of Winter Parkâs most sought-after locations, this 3-bedroom, 2-bathroom ...	3 beds \| 2 baths \| 1,115 sq.ft.	$550,000	Airbnb cash on cash: 4.56% Traditional cash on cash: 1.6% Airbnb Rental Income: $4337 Traditional Rental Income: $1903 Airbnb ROI: 4.56% Traditional ROI: 1.6%
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.	$1,290,000	Airbnb cash on cash: 1.7% Traditional cash on cash: 0.56% Airbnb Rental Income: $5745 Traditional Rental Income: $3232 Airbnb ROI: 1.7% Traditional ROI: 0.56%
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.	$362,500	Airbnb cash on cash: 4.55% Traditional cash on cash: 2.26% Airbnb Rental Income: $3260 Traditional Rental Income: $1751 Airbnb ROI: 4.55% Traditional ROI: 2.26%
1420 PALMER AVENUE Winter Park, FL DON'T LET THIS OPPORTUNITY PASS YOU BY, BACK ON MARKET DUE TO BUYERS FINANCING. Luxuri...	4 beds \| 4 baths \| 2,953 sq.ft.	$1,325,000	Airbnb cash on cash: 1.88% Traditional cash on cash: 1.47% Airbnb Rental Income: $5745 Traditional Rental Income: $4099 Airbnb ROI: 1.88% Traditional ROI: 1.47%
1521 CHESTNUT AVENUE Winter Park, FL Modern Luxury in the Heart of Winter Park! Welcome to this stunning modern residence, buil...	4 beds \| 3 baths \| 2,843 sq.ft.	$1,899,900	Airbnb cash on cash: 0.48% Traditional cash on cash: -0.08% Airbnb Rental Income: $5745 Traditional Rental Income: $3620 Airbnb ROI: 0.48% Traditional ROI: -0.08%
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%
700 MELROSE AVENUE #D21 Winter Park, FL Located in the historic Winter Park Gardens community, this condo has been meticulously ma...	1 beds \| 1 baths \| 871 sq.ft.	$198,800	Airbnb cash on cash: 6.51% Traditional cash on cash: 4.32% Airbnb Rental Income: $2412 Traditional Rental Income: $1409 Airbnb ROI: 6.51% Traditional ROI: 4.32%
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.	$540,000	Airbnb cash on cash: 4.62% Traditional cash on cash: 2.37% Airbnb Rental Income: $4337 Traditional Rental Income: $2291 Airbnb ROI: 4.62% Traditional ROI: 2.37%
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%
3490 BOUGAINVILLEA DRIVE Winter Park, FL Under contract-accepting backup offers. Step into the charm and comfort of this inviting 3...	3 beds \| 2 baths \| 1,461 sq.ft.	$348,000	Airbnb cash on cash: 8.38% Traditional cash on cash: 5.26% Airbnb Rental Income: $4337 Traditional Rental Income: $2405 Airbnb ROI: 8.38% Traditional ROI: 5.26%
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: 3.98% Airbnb Rental Income: $5745 Traditional Rental Income: $2479 Airbnb ROI: 9.18% Traditional ROI: 3.98%
1849 VIBURNUM LANE Winter Park, FL Nestled near the highly sought-after Winter Park area, this beautifully updated 4-bedroom,...	4 beds \| 2 baths \| 1,627 sq.ft.	$444,900	Airbnb cash on cash: 9% Traditional cash on cash: 3.54% Airbnb Rental Income: $5745 Traditional Rental Income: $2323 Airbnb ROI: 9% Traditional ROI: 3.54%
720 W WEBSTER AVENUE Winter Park, FL Discover the charm of Winter Park living in this beautifully maintained 1950s home, where ...	3 beds \| 2 baths \| 1,356 sq.ft.	$625,000	Airbnb cash on cash: 3.9% Traditional cash on cash: 1.8% Airbnb Rental Income: $4337 Traditional Rental Income: $2200 Airbnb ROI: 3.9% Traditional ROI: 1.8%
200 SAINT ANDREWS BOULEVARD #601 Winter Park, FL Under contract-accepting backup offers. Welcome to this spacious and beautifully updated f...	1 beds \| 1 baths \| 727 sq.ft.	$169,900	Airbnb cash on cash: 8.19% Traditional cash on cash: 5.74% Airbnb Rental Income: $2412 Traditional Rental Income: $1424 Airbnb ROI: 8.19% Traditional ROI: 5.74%
541 W CANTON AVENUE Winter Park, FL Timeless elegance meets boutique craftsmanship at 541 W Canton Avenueâan exceptional new...	4 beds \| 4 baths \| 3,553 sq.ft.	$3,150,000	Airbnb cash on cash: 0.4% Traditional cash on cash: 0.36% Airbnb Rental Income: $5745 Traditional Rental Income: $4490 Airbnb ROI: 0.4% Traditional ROI: 0.36%
151 N ORLANDO AVENUE #212 Winter Park, FL Experience luxury lakefront living in this stunning and truly unique 3-bedroom, 2-bathroom...	3 beds \| 2 baths \| 1,875 sq.ft.	$575,000	Airbnb cash on cash: 2.47% Traditional cash on cash: 1.39% Airbnb Rental Income: $4337 Traditional Rental Income: $2846 Airbnb ROI: 2.47% Traditional ROI: 1.39%
2405 FIRSTLIGHT WAY Winter Park, FL Experience refined living in the sought-after gated community of Hawks Crest. This elegant...	3 beds \| 3 baths \| 1,964 sq.ft.	$460,000	Airbnb cash on cash: 4.99% Traditional cash on cash: 3.65% Airbnb Rental Income: $4337 Traditional Rental Income: $2850 Airbnb ROI: 4.99% Traditional ROI: 3.65%
2238 HAWICK LANE #2238 Winter Park, FL Welcome to 2238 Hawick Lane, where modern living meets timeless charm in Winter Park, FL! ...	3 beds \| 3 baths \| 1,775 sq.ft.	$519,000	Airbnb cash on cash: 4.12% Traditional cash on cash: 2.24% Airbnb Rental Income: $4337 Traditional Rental Income: $2514 Airbnb ROI: 4.12% Traditional ROI: 2.24%
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.	$829,000	Airbnb cash on cash: 3.5% Traditional cash on cash: 2.7% Airbnb Rental Income: $5745 Traditional Rental Income: $3980 Airbnb ROI: 3.5% Traditional ROI: 2.7%
2774 BANCHORY ROAD Winter Park, FL Under contract-accepting backup offers. Welcome to this beautifully maintained 3-bedroom, ...	3 beds \| 2 baths \| 1,560 sq.ft.	$490,000	Airbnb cash on cash: 4.95% Traditional cash on cash: 2.42% Airbnb Rental Income: $4337 Traditional Rental Income: $2268 Airbnb ROI: 4.95% Traditional ROI: 2.42%
1816 AZALEA AVENUE Winter Park, FL Under contract-accepting backup offers. Short Sale. Short Sale. Subject to seller's lender...	3 beds \| 2 baths \| 1,584 sq.ft.	$500,000	Airbnb cash on cash: 5.72% Traditional cash on cash: 3.98% Airbnb Rental Income: $4337 Traditional Rental Income: $2609 Airbnb ROI: 5.72% Traditional ROI: 3.98%
1561 NOTTINGHAM DRIVE Winter Park, FL Under contract-accepting backup offers. Welcome to your dream home in the heart of Winter ...	4 beds \| 2 baths \| 1,889 sq.ft.	$569,990	Airbnb cash on cash: 6.61% Traditional cash on cash: 3.29% Airbnb Rental Income: $5745 Traditional Rental Income: $2833 Airbnb ROI: 6.61% Traditional ROI: 3.29%
5122 N WOODCREST DRIVE Winter Park, FL Under contract-accepting backup offers. This is your chance to own a rare updated 3-bedroo...	3 beds \| 2 baths \| 1,499 sq.ft.	$430,000	Airbnb cash on cash: 6.22% Traditional cash on cash: 3.98% Airbnb Rental Income: $4337 Traditional Rental Income: $2521 Airbnb ROI: 6.22% Traditional ROI: 3.98%
1621 PURITAN, Winter Park, FL Down Payment Assistance Available! Welcome to 1621 Puritan Ave, a beautifully renovated po...	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%
250 Cortland Avenue 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.	$955,000	Airbnb cash on cash: 2.29% Traditional cash on cash: 1.79% Airbnb Rental Income: $4337 Traditional Rental Income: $2974 Airbnb ROI: 2.29% Traditional ROI: 1.79%
3019 ANTIQUE OAKS CIRCLE #124 Winter Park, FL PRICE IMPROVEMENT!! Prime Location and Zip Code are key! Low HOA! Welcome home to 3019 Ant...	1 beds \| 1 baths \| 749 sq.ft.	$163,500	Airbnb cash on cash: 6.71% Traditional cash on cash: 5.71% Airbnb Rental Income: $2412 Traditional Rental Income: $1666 Airbnb ROI: 6.71% Traditional ROI: 5.71%
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.	$689,000	Airbnb cash on cash: 2.88% Traditional cash on cash: 1.76% Airbnb Rental Income: $4337 Traditional Rental Income: $2702 Airbnb ROI: 2.88% Traditional ROI: 1.76%
3128 PATEL DRIVE Winter Park, FL Don't miss this income producing duplex just minutes from University Ave and the UCF area!...	4 beds \| N/A baths \| 1,934 sq.ft.	$409,900	Airbnb cash on cash: 9.9% Traditional cash on cash: 2.04% Airbnb Rental Income: $5745 Traditional Rental Income: $1578 Airbnb ROI: 9.9% Traditional ROI: 2.04%
1907 S LAKEMONT AVENUE Winter Park, FL Special financing or closing cost credits available for qualified buyers! Introducing t...	3 beds \| 4 baths \| 2,063 sq.ft.	$824,900	Airbnb cash on cash: 2.65% Traditional cash on cash: 2.27% Airbnb Rental Income: $4337 Traditional Rental Income: $3129 Airbnb ROI: 2.65% Traditional ROI: 2.27%
535 N INTERLACHEN AVENUE #106 Winter Park, FL Combining luxury living with exceptional value, this immaculate, move-in-ready condo is ju...	2 beds \| 2 baths \| 1,000 sq.ft.	$599,900	Airbnb cash on cash: 2.97% Traditional cash on cash: 2.08% Airbnb Rental Income: $3260 Traditional Rental Income: $2028 Airbnb ROI: 2.97% Traditional ROI: 2.08%
3601 MIDIRON DRIVE Winter Park, FL BUILD YOUR DREAM HOME IN WINTER PARK! Nestled directly across from the historic Dubsdread...	2 beds \| 1 baths \| 954 sq.ft.	$459,000	Airbnb cash on cash: 3.36% Traditional cash on cash: 1.18% Airbnb Rental Income: $3260 Traditional Rental Income: $1593 Airbnb ROI: 3.36% Traditional ROI: 1.18%

Vacation Rentals in Winter Park

There are 147 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 $549,900 and the average price per square foot is $262. 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 147 Airbnb properties available for sale in Winter Park.

In 2025, the best neighborhood to buy short term rental property is Winter Park.

In October 2025, 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

2844 SCARLET ROAD

Winter Park, FL

4 beds | 2 baths | 1,508 sq.ft.

$499,000

Airbnb cash on cash: 7.56%

Traditional cash on cash: 3.52%

Airbnb Rental Income: $5745

Traditional Rental Income: $2713

Airbnb ROI: 7.56%

Traditional ROI: 3.52%

1308 S PENNSYLVANIA AVENUE #3

Winter Park, FL

1 beds | 1 baths | 823 sq.ft.

$325,000

Airbnb cash on cash: 3.63%

Traditional cash on cash: 2.2%

Airbnb Rental Income: $2412

Traditional Rental Income: $1384

Airbnb ROI: 3.63%

Traditional ROI: 2.2%

690 S LAKEMONT AVENUE

Winter Park, FL

4 beds | 3 baths | 1,897 sq.ft.

$550,000

Airbnb cash on cash: 6.35%

Traditional cash on cash: 3.9%

Airbnb Rental Income: $5745

Traditional Rental Income: $3342

Airbnb ROI: 6.35%

Traditional ROI: 3.9%

8065 PLEASANT PINE CIRCLE

Winter Park, FL

4 beds | 2 baths | 1,843 sq.ft.

$560,000

Airbnb cash on cash: 6.66%

Traditional cash on cash: 2.39%

Airbnb Rental Income: $5745

Traditional Rental Income: $2364

Airbnb ROI: 6.66%

Traditional ROI: 2.39%

744 CORNWALL ROAD

Winter Park, FL

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

$750,000

Airbnb cash on cash: 4.73%

Traditional cash on cash: 2.13%

Airbnb Rental Income: $5745

Traditional Rental Income: $2775

Airbnb ROI: 4.73%

Traditional ROI: 2.13%

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: 1.34%

Airbnb Rental Income: $5745

Traditional Rental Income: $3752

Airbnb ROI: 2.17%

Traditional ROI: 1.34%

1516 PINEWOOD DRIVE

Winter Park, FL

2 beds | 1 baths | 1,028 sq.ft.

$349,000

Airbnb cash on cash: 5.04%

Traditional cash on cash: 2.51%

Airbnb Rental Income: $3260

Traditional Rental Income: $1698

Airbnb ROI: 5.04%

Traditional ROI: 2.51%

2812 WOODSIDE AVENUE

Winter Park, FL

3 beds | 2 baths | 1,842 sq.ft.

$625,000

Airbnb cash on cash: 3.49%

Traditional cash on cash: 2.72%

Airbnb Rental Income: $4337

Traditional Rental Income: $2979

Airbnb ROI: 3.49%