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 Welcome to this fully remodeled, move in ready home perfectly situated on a spacious corne...	3 beds \| 2 baths \| 1,456 sq.ft.	$470,000	Airbnb cash on cash: 5.46% Traditional cash on cash: 2.74% Airbnb Rental Income: $4337 Traditional Rental Income: $2229 Airbnb ROI: 5.46% Traditional ROI: 2.74%
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.	$335,000	Airbnb cash on cash: 5.29% Traditional cash on cash: 2.66% Airbnb Rental Income: $3260 Traditional Rental Income: $1698 Airbnb ROI: 5.29% Traditional ROI: 2.66%
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%
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%
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%
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%
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%
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.	$599,000	Airbnb cash on cash: 4.11% Traditional cash on cash: 1.92% Airbnb Rental Income: $4337 Traditional Rental Income: $2200 Airbnb ROI: 4.11% Traditional ROI: 1.92%
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.	$2,935,000	Airbnb cash on cash: 0.5% Traditional cash on cash: 0.46% Airbnb Rental Income: $5745 Traditional Rental Income: $4490 Airbnb ROI: 0.5% Traditional ROI: 0.46%
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%
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%
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.	$950,000	Airbnb cash on cash: 2.31% Traditional cash on cash: 1.8% Airbnb Rental Income: $4337 Traditional Rental Income: $2974 Airbnb ROI: 2.31% Traditional ROI: 1.8%
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%
151 N ORLANDO AVENUE #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: 6.61% Traditional cash on cash: 3.36% Airbnb Rental Income: $3260 Traditional Rental Income: $1610 Airbnb ROI: 6.61% Traditional ROI: 3.36%
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.	$1,260,000	Airbnb cash on cash: 2.56% Traditional cash on cash: 0.96% Airbnb Rental Income: $5745 Traditional Rental Income: $2726 Airbnb ROI: 2.56% Traditional ROI: 0.96%
920 GLORIOSA AVENUE Winter Park, FL Charming Move-In Ready Home in the Heart of Winter Park! Discover this beautifully main...	3 beds \| 2 baths \| 1,540 sq.ft.	$409,988	Airbnb cash on cash: 7.29% Traditional cash on cash: 4.5% Airbnb Rental Income: $4337 Traditional Rental Income: $2355 Airbnb ROI: 7.29% Traditional ROI: 4.5%
2128 SYCAMORE DRIVE Winter Park, FL MUST SEE! RENOVATED, MOVE-IN READY! Donât miss this fantastic opportunity to own a beau...	3 beds \| 2 baths \| 1,760 sq.ft.	$825,000	Airbnb cash on cash: 2.72% Traditional cash on cash: 1.63% Airbnb Rental Income: $4337 Traditional Rental Income: $2586 Airbnb ROI: 2.72% Traditional ROI: 1.63%
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.	$200,000	Airbnb cash on cash: 5.71% Traditional cash on cash: 3.84% Airbnb Rental Income: $2412 Traditional Rental Income: $1467 Airbnb ROI: 5.71% Traditional ROI: 3.84%
1875 STAUNTON AVENUE Winter Park, FL Welcome to this newer single-family home tucked away in the Karolina On Killarney section ...	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%
1660 WALNUT AVENUE Winter Park, FL Under Construction. Elegant and modern new construction home perfectly situated in beautif...	4 beds \| 4 baths \| 2,172 sq.ft.	$1,759,000	Airbnb cash on cash: 1.35% Traditional cash on cash: 0.67% Airbnb Rental Income: $5745 Traditional Rental Income: $3477 Airbnb ROI: 1.35% Traditional ROI: 0.67%
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%
1360 FORMOSA AVENUE Winter Park, FL Discover a rare and lucrative opportunity at 1360 Formosa Ave, a corner lot triplex in the...	3 beds \| N/A baths \| 1,890 sq.ft.	$625,000	Airbnb cash on cash: 3.39% Traditional cash on cash: 1.37% Airbnb Rental Income: $4337 Traditional Rental Income: $2251 Airbnb ROI: 3.39% Traditional ROI: 1.37%
101 S INTERLACHEN AVENUE #104 Winter Park, FL FIRST TIME ON THE MARKET! SUPER RARE, GROUND FLOOR, DOWNTOWN WINTER PARK CONDO AT LACHEN H...	2 beds \| 2 baths \| 949 sq.ft.	$649,000	Airbnb cash on cash: 2.35% Traditional cash on cash: 0.73% Airbnb Rental Income: $3260 Traditional Rental Income: $1543 Airbnb ROI: 2.35% Traditional ROI: 0.73%
1564 CAVENDISH ROAD Winter Park, FL Charming 3BR bungalow in sought-after Orwin Manor with timeless appeal and tons of potenti...	3 beds \| 1 baths \| 1,140 sq.ft.	$450,000	Airbnb cash on cash: 5.72% Traditional cash on cash: 1.95% Airbnb Rental Income: $4337 Traditional Rental Income: $1838 Airbnb ROI: 5.72% Traditional ROI: 1.95%
2500 LEE ROAD #208 Winter Park, FL This charming two-bedroom, two-bathroom 2nd floor condo offers the perfect blend of comfor...	2 beds \| 2 baths \| 956 sq.ft.	$200,000	Airbnb cash on cash: 8.82% Traditional cash on cash: 4.91% Airbnb Rental Income: $3260 Traditional Rental Income: $1786 Airbnb ROI: 8.82% Traditional ROI: 4.91%
1341 LYNDALE BOULEVARD Winter Park, FL Ideally located in the heart of Winter Park, just steps from iconic Park Avenue and around...	4 beds \| 3 baths \| 2,388 sq.ft.	$1,130,000	Airbnb cash on cash: 2.17% Traditional cash on cash: 0.44% Airbnb Rental Income: $5745 Traditional Rental Income: $2775 Airbnb ROI: 2.17% Traditional ROI: 0.44%
1399 ALOMA AVENUE Winter Park, FL *Price Adjustment * Charming 1948 Winter Park Home! This 3-bedroom, 2-bathroom gem is ...	3 beds \| 2 baths \| 1,804 sq.ft.	$665,000	Airbnb cash on cash: 4.06% Traditional cash on cash: 2.68% Airbnb Rental Income: $4337 Traditional Rental Income: $2575 Airbnb ROI: 4.06% Traditional ROI: 2.68%
151 N ORLANDO AVENUE #204 Winter Park, FL One or more photo(s) has been virtually staged. Investors Dream with Minimal Lease Restric...	2 beds \| 1 baths \| 710 sq.ft.	$236,000	Airbnb cash on cash: 6.59% Traditional cash on cash: 3.28% Airbnb Rental Income: $3260 Traditional Rental Income: $1790 Airbnb ROI: 6.59% Traditional ROI: 3.28%
1550 MICHIGAN AVENUE Winter Park, FL Incredible Investment Opportunity in Winter Park! Come take a look at this amazing proper...	N/A beds \| N/A baths \| 1,452 sq.ft.	$600,000	Airbnb cash on cash: 1.3% Traditional cash on cash: 0.6% Airbnb Rental Income: $2412 Traditional Rental Income: $1429 Airbnb ROI: 1.3% Traditional ROI: 0.6%
184 SANDLEWOOD TRAIL #2 Winter Park, FL FHA, VA, and DPA approved. Nestled just minutes from the charming boutiques and award-winn...	2 beds \| 3 baths \| 1,133 sq.ft.	$315,000	Airbnb cash on cash: 6.3% Traditional cash on cash: 3.78% Airbnb Rental Income: $3260 Traditional Rental Income: $1781 Airbnb ROI: 6.3% Traditional ROI: 3.78%
240 CAMBRIDGE BOULEVARD Winter Park, FL 3-Bed, 2-Bath Home in Prime Winter Park Location! Steps away from paddleboarding, kayaking...	3 beds \| 2 baths \| 1,630 sq.ft.	$525,000	Airbnb cash on cash: 4.87% Traditional cash on cash: 2.63% Airbnb Rental Income: $4337 Traditional Rental Income: $2325 Airbnb ROI: 4.87% Traditional ROI: 2.63%
446 ALBERTA DRIVE Winter Park, FL Charming Opportunity in Prime Winter Park â 446 Alberta Drive, Winter Park, FL! First t...	4 beds \| 3 baths \| 3,263 sq.ft.	$1,750,000	Airbnb cash on cash: 1.39% Traditional cash on cash: 0.84% Airbnb Rental Income: $5745 Traditional Rental Income: $3714 Airbnb ROI: 1.39% Traditional ROI: 0.84%
240 KILLARNEY BAY COURT #4 Winter Park, FL Welcome to Killarney BayâWinter Parkâs best-kept secret for tranquil lakeside living, ...	2 beds \| 3 baths \| 1,536 sq.ft.	$410,000	Airbnb cash on cash: 3.73% Traditional cash on cash: 2.9% Airbnb Rental Income: $3260 Traditional Rental Income: $2209 Airbnb ROI: 3.73% Traditional ROI: 2.9%
311 E MORSE BOULEVARD #7-5 Winter Park, FL Major Price Improvement & Motivated Seller! Here is your rare opportunity to own a studio ...	1 beds \| 1 baths \| 482 sq.ft.	$359,000	Airbnb cash on cash: 3.19% Traditional cash on cash: 1.77% Airbnb Rental Income: $2412 Traditional Rental Income: $1343 Airbnb ROI: 3.19% Traditional ROI: 1.77%
512 CLARENDON AVENUE Winter Park, FL Beautifully updated 4BD/3.5BA townhome in highly sought-after Virginia Heights, just steps...	4 beds \| 4 baths \| 2,826 sq.ft.	$995,000	Airbnb cash on cash: 2.78% Traditional cash on cash: 2.02% Airbnb Rental Income: $5745 Traditional Rental Income: $3898 Airbnb ROI: 2.78% Traditional ROI: 2.02%
Lot #20 KAROLINA AVE Winter Park, FL Pre-Construction. To be built. Experience a life where timeless craftsmanship meets modern...	4 beds \| 4 baths \| 2,662 sq.ft.	$935,040	Airbnb cash on cash: 3.94% Traditional cash on cash: 2.86% Airbnb Rental Income: $5745 Traditional Rental Income: $3657 Airbnb ROI: 3.94% Traditional ROI: 2.86%
Lot #21 KAROLINA AVE Winter Park, FL Pre-Construction. To be built. Step into a life where charm meets convenience in the heart...	4 beds \| 4 baths \| 2,662 sq.ft.	$903,050	Airbnb cash on cash: 4.12% Traditional cash on cash: 2.88% Airbnb Rental Income: $5745 Traditional Rental Income: $3560 Airbnb ROI: 4.12% Traditional ROI: 2.88%

Vacation Rentals in Winter Park

There are 150 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 $549,450 and the average price per square foot is $260. 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 150 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

740 BAFFIE AVENUE

Winter Park, FL

3 beds | 2 baths | 1,456 sq.ft.

$470,000

Airbnb cash on cash: 5.46%

Traditional cash on cash: 2.74%

Airbnb Rental Income: $4337

Traditional Rental Income: $2229

Airbnb ROI: 5.46%

Traditional ROI: 2.74%

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.

$335,000

Airbnb cash on cash: 5.29%

Traditional cash on cash: 2.66%

Airbnb Rental Income: $3260

Traditional Rental Income: $1698

Airbnb ROI: 5.29%

Traditional ROI: 2.66%

720 N PENNSYLVANIA AVENUE

Winter Park, FL

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%

1400 S PENNSYLVANIA AVENUE

Winter Park, FL

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

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%

1521 CHESTNUT AVENUE

Winter Park, FL

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%

700 MELROSE AVENUE #D21

Winter Park, FL

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%