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
100 S VIRGINIA AVENUE #319 Winter Park, FL Under contract-accepting backup offers. Experience the best of Winter Park living in this ...	3 beds \| 3 baths \| 2,649 sq.ft.	$1,079,000	Airbnb cash on cash: 0.19% Traditional cash on cash: 0.19% Airbnb Rental Income: $4337 Traditional Rental Income: $3419 Airbnb ROI: 0.19% Traditional ROI: 0.19%
2844 SCARLET ROAD Winter Park, FL Welcome to this stunning mid-century modern beauty where timeless design meets thoughtful,...	4 beds \| 2 baths \| 1,508 sq.ft.	$519,000	Airbnb cash on cash: 7.24% Traditional cash on cash: 3.35% Airbnb Rental Income: $5745 Traditional Rental Income: $2713 Airbnb ROI: 7.24% Traditional ROI: 3.35%
311 CORTLAND AVENUE Winter Park, FL Under contract-accepting backup offers. Location, location, location! Whether you're ready...	2 beds \| 2 baths \| 1,382 sq.ft.	$799,900	Airbnb cash on cash: 1.45% Traditional cash on cash: 0.96% Airbnb Rental Income: $3260 Traditional Rental Income: $2160 Airbnb ROI: 1.45% Traditional ROI: 0.96%
1308 S PENNSYLVANIA AVENUE #3 Winter Park, FL $25,000 below appraised value! Walk to Park Ave!! Sip coffee or tea overlooking lush Mead ...	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%
1018 TURNER ROAD Winter Park, FL Seller may consider buyer concessions if made in an offer \| Lakefront charm meets quiet lu...	4 beds \| 2 baths \| 2,237 sq.ft.	$890,000	Airbnb cash on cash: 3.49% Traditional cash on cash: 2.11% Airbnb Rental Income: $5745 Traditional Rental Income: $3458 Airbnb ROI: 3.49% Traditional ROI: 2.11%
7602 LODGE POLE TRAIL Winter Park, FL Under contract-accepting backup offers. Nestled in desirable Arrowhead Cove, this meticulo...	3 beds \| 3 baths \| 1,906 sq.ft.	$474,998	Airbnb cash on cash: 5.68% Traditional cash on cash: 3.98% Airbnb Rental Income: $4337 Traditional Rental Income: $2667 Airbnb ROI: 5.68% Traditional ROI: 3.98%
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%
1023 PRINCESS GATE BOULEVARD Winter Park, FL Under contract-accepting backup offers. VA AssumableA HIDDEN GEM nestled on Lake Deeks...	4 beds \| 3 baths \| 2,465 sq.ft.	$695,000	Airbnb cash on cash: 5.9% Traditional cash on cash: 4.87% Airbnb Rental Income: $5745 Traditional Rental Income: $3934 Airbnb ROI: 5.9% Traditional ROI: 4.87%
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.	$570,000	Airbnb cash on cash: 6.53% Traditional cash on cash: 2.33% Airbnb Rental Income: $5745 Traditional Rental Income: $2364 Airbnb ROI: 6.53% Traditional ROI: 2.33%
3651 N GOLDENROD ROAD #210 Winter Park, FL beautiful Condo in of Winter Park. This spacious second-floor unit is filled with natur...	2 beds \| 2 baths \| 840 sq.ft.	$191,000	Airbnb cash on cash: 9.87% Traditional cash on cash: 4.67% Airbnb Rental Income: $3260 Traditional Rental Income: $1584 Airbnb ROI: 9.87% Traditional ROI: 4.67%
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.	$369,000	Airbnb cash on cash: 4.72% Traditional cash on cash: 2.32% Airbnb Rental Income: $3260 Traditional Rental Income: $1698 Airbnb ROI: 4.72% Traditional ROI: 2.32%
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%
1000 S SEMORAN BOULEVARD #415 Winter Park, FL NEW AC INSTALLED, PRICE REDUCTION, EXCELLENT INVESTMENT OPPORTUNITY, Great Tenant in place...	1 beds \| 1 baths \| 735 sq.ft.	$115,950	Airbnb cash on cash: 9.62% Traditional cash on cash: 6.26% Airbnb Rental Income: $2412 Traditional Rental Income: $1445 Airbnb ROI: 9.62% Traditional ROI: 6.26%
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 Seller will consider concessions. Seller Financing available. Contact us today. Welcome to...	3 beds \| 2 baths \| 2,268 sq.ft.	$575,000	Airbnb cash on cash: 4.13% Traditional cash on cash: 3.37% Airbnb Rental Income: $4337 Traditional Rental Income: $3016 Airbnb ROI: 4.13% Traditional ROI: 3.37%
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%
690 OSCEOLA AVENUE #209 Winter Park, FL One or more photo(s) has been virtually staged. Seller financing and lease to own options ...	2 beds \| 2 baths \| 1,148 sq.ft.	$393,800	Airbnb cash on cash: 4.83% Traditional cash on cash: 3.56% Airbnb Rental Income: $3260 Traditional Rental Income: $2057 Airbnb ROI: 4.83% Traditional ROI: 3.56%
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%
1701 PALMER AVENUE Winter Park, FL One or more photo(s) has been virtually staged. Charming Winter Park Pool Home â A Rare ...	4 beds \| 3 baths \| 2,841 sq.ft.	$1,295,000	Airbnb cash on cash: 1.85% Traditional cash on cash: 1.56% Airbnb Rental Income: $5745 Traditional Rental Income: $4249 Airbnb ROI: 1.85% Traditional ROI: 1.56%
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%
2381 ROXBURY ROAD Winter Park, FL Beautiful 3 Bedrooms 2 Baths in highly desired location. Established pet friendly neighbo...	3 beds \| 2 baths \| 1,645 sq.ft.	$525,000	Airbnb cash on cash: 5.41% Traditional cash on cash: 3.37% Airbnb Rental Income: $4337 Traditional Rental Income: $2423 Airbnb ROI: 5.41% Traditional ROI: 3.37%
260 KILLARNEY BAY COURT #6-6 Winter Park, FL Welcome to Killarney Bay! This beautifully updated 2-bedroom, 1-bathroom Second-floor cond...	2 beds \| 1 baths \| 1,140 sq.ft.	$345,000	Airbnb cash on cash: 4.32% Traditional cash on cash: 1.61% Airbnb Rental Income: $3260 Traditional Rental Income: $1650 Airbnb ROI: 4.32% Traditional ROI: 1.61%
1421 SUNSET DRIVE Winter Park, FL Under contract-accepting backup offers. BUYER GOT COLD FEET= YOUR OPPORTUNITY! Welcome to ...	3 beds \| 4 baths \| 1,672 sq.ft.	$835,000	Airbnb cash on cash: 2.27% Traditional cash on cash: 1.7% Airbnb Rental Income: $4337 Traditional Rental Income: $2982 Airbnb ROI: 2.27% Traditional ROI: 1.7%
1250 S DENNING DRIVE #111 Winter Park, FL Under contract-accepting backup offers. LOCATION LOCATION!! Now is your chance to own this...	2 beds \| 2 baths \| 908 sq.ft.	$259,000	Airbnb cash on cash: 4.81% Traditional cash on cash: 1.6% Airbnb Rental Income: $3260 Traditional Rental Income: $1744 Airbnb ROI: 4.81% Traditional ROI: 1.6%
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.	$750,000	Airbnb cash on cash: 3.11% Traditional cash on cash: 0.97% Airbnb Rental Income: $4337 Traditional Rental Income: $1931 Airbnb ROI: 3.11% Traditional ROI: 0.97%
3490 BOUGAINVILLEA DRIVE Winter Park, FL Step into the charm and comfort of this inviting 3-bedroom, 2-bath Winter Park home, where...	3 beds \| 2 baths \| 1,461 sq.ft.	$377,500	Airbnb cash on cash: 7.65% Traditional cash on cash: 4.77% Airbnb Rental Income: $4337 Traditional Rental Income: $2405 Airbnb ROI: 7.65% Traditional ROI: 4.77%
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.	$449,900	Airbnb cash on cash: 8.85% Traditional cash on cash: 3.82% Airbnb Rental Income: $5745 Traditional Rental Income: $2479 Airbnb ROI: 8.85% Traditional ROI: 3.82%
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.	$449,900	Airbnb cash on cash: 8.89% Traditional cash on cash: 3.49% Airbnb Rental Income: $5745 Traditional Rental Income: $2323 Airbnb ROI: 8.89% Traditional ROI: 3.49%
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.	$649,000	Airbnb cash on cash: 3.72% Traditional cash on cash: 1.7% Airbnb Rental Income: $4337 Traditional Rental Income: $2200 Airbnb ROI: 3.72% Traditional ROI: 1.7%
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.	$599,000	Airbnb cash on cash: 2.33% Traditional cash on cash: 1.3% Airbnb Rental Income: $4337 Traditional Rental Income: $2846 Airbnb ROI: 2.33% Traditional ROI: 1.3%
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.	$469,000	Airbnb cash on cash: 4.87% Traditional cash on cash: 3.56% Airbnb Rental Income: $4337 Traditional Rental Income: $2850 Airbnb ROI: 4.87% Traditional ROI: 3.56%
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.	$529,000	Airbnb cash on cash: 4.03% Traditional cash on cash: 2.18% Airbnb Rental Income: $4337 Traditional Rental Income: $2514 Airbnb ROI: 4.03% Traditional ROI: 2.18%
7777 FERNBROOK WAY Winter Park, FL Under contract-accepting backup offers. Completely Renovated 2 bedroom and 2 bath Townhome...	2 beds \| 2 baths \| 1,092 sq.ft.	$275,000	Airbnb cash on cash: 6.9% Traditional cash on cash: 3.6% Airbnb Rental Income: $3260 Traditional Rental Income: $1671 Airbnb ROI: 6.9% Traditional ROI: 3.6%
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 Welcome to this beautifully maintained 3-bedroom, 2-bathroom block ranch home in Winter Pa...	3 beds \| 2 baths \| 1,560 sq.ft.	$500,000	Airbnb cash on cash: 4.83% Traditional cash on cash: 2.35% Airbnb Rental Income: $4337 Traditional Rental Income: $2268 Airbnb ROI: 4.83% Traditional ROI: 2.35%
680 GRENADINE COURT #S Winter Park, FL Under contract-accepting backup offers. Welcome to this beautifully renovated 1-bedroom, 1...	1 beds \| 1 baths \| 759 sq.ft.	$190,000	Airbnb cash on cash: 5.01% Traditional cash on cash: 4.25% Airbnb Rental Income: $2412 Traditional Rental Income: $1684 Airbnb ROI: 5.01% Traditional ROI: 4.25%

Vacation Rentals in Winter Park

There are 165 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 $587,000 and the average price per square foot is $277. 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 165 Airbnb properties available for sale in Winter Park.

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

In September 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

100 S VIRGINIA AVENUE #319

Winter Park, FL

3 beds | 3 baths | 2,649 sq.ft.

$1,079,000

Airbnb cash on cash: 0.19%

Traditional cash on cash: 0.19%

Airbnb Rental Income: $4337

Traditional Rental Income: $3419

Airbnb ROI: 0.19%

Traditional ROI: 0.19%

2844 SCARLET ROAD

Winter Park, FL

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

$519,000

Airbnb cash on cash: 7.24%

Traditional cash on cash: 3.35%

Airbnb Rental Income: $5745

Traditional Rental Income: $2713

Airbnb ROI: 7.24%

Traditional ROI: 3.35%

311 CORTLAND AVENUE

Winter Park, FL

2 beds | 2 baths | 1,382 sq.ft.

$799,900

Airbnb cash on cash: 1.45%

Traditional cash on cash: 0.96%

Airbnb Rental Income: $3260

Traditional Rental Income: $2160

Airbnb ROI: 1.45%

Traditional ROI: 0.96%

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%

1018 TURNER ROAD

Winter Park, FL

4 beds | 2 baths | 2,237 sq.ft.

$890,000

Airbnb cash on cash: 3.49%

Traditional cash on cash: 2.11%

Airbnb Rental Income: $5745

Traditional Rental Income: $3458

Airbnb ROI: 3.49%

Traditional ROI: 2.11%

7602 LODGE POLE TRAIL

Winter Park, FL

3 beds | 3 baths | 1,906 sq.ft.

$474,998

Airbnb cash on cash: 5.68%

Traditional cash on cash: 3.98%

Airbnb Rental Income: $4337

Traditional Rental Income: $2667

Airbnb ROI: 5.68%

Traditional ROI: 3.98%

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%

1023 PRINCESS GATE BOULEVARD

Winter Park, FL

4 beds | 3 baths | 2,465 sq.ft.

$695,000

Airbnb cash on cash: 5.9%

Traditional cash on cash: 4.87%

Airbnb Rental Income: $5745

Traditional Rental Income: $3934

Airbnb ROI: 5.9%