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.	$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%
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%
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%
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%
2811 EASTERN PARKWAY Winter Park, FL Mid-Century Modern architecture meets modern comfort in this beautifully updated Winter Pa...	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 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.	$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%
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.	$449,900	Airbnb cash on cash: 5.4% Traditional cash on cash: 1.72% Airbnb Rental Income: $4337 Traditional Rental Income: $1878 Airbnb ROI: 5.4% Traditional ROI: 1.72%
1600 PALMER AVENUE Winter Park, FL Discover refined elegance in this meticulously updated 3-bedroom, 2.5-bath two-story resid...	3 beds \| 3 baths \| 2,550 sq.ft.	$1,200,000	Airbnb cash on cash: 1.24% Traditional cash on cash: 0.68% Airbnb Rental Income: $4337 Traditional Rental Income: $2805 Airbnb ROI: 1.24% Traditional ROI: 0.68%
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.	$550,000	Airbnb cash on cash: 4.56% Traditional cash on cash: 2.18% Airbnb Rental Income: $4337 Traditional Rental Income: $2200 Airbnb ROI: 4.56% Traditional ROI: 2.18%
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%
503 W CANTON AVENUE Winter Park, FL MODEL HOME. Enjoy luxury living and premium sought after location at Vilasa Homes, 2022 co...	3 beds \| 3 baths \| 2,342 sq.ft.	$1,157,000	Airbnb cash on cash: 0.09% Traditional cash on cash: -0.39% Airbnb Rental Income: $4337 Traditional Rental Income: $2907 Airbnb ROI: 0.09% Traditional ROI: -0.39%
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%
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.	$499,000	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 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.	$1,180,000	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%
1981 Blue Ridge Rd Winter Park, FL 1981 Blue Ridge Rd, Orlando, FL 32789 \| Single Family Residential	4 beds \| 2 baths \| 2,750 sq.ft.	$1,180,000	Airbnb cash on cash: 2.22% Traditional cash on cash: 1.09% Airbnb Rental Income: $5745 Traditional Rental Income: $3353 Airbnb ROI: 2.22% Traditional ROI: 1.09%
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 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: 5.62% Airbnb Rental Income: $2412 Traditional Rental Income: $1467 Airbnb ROI: 8.17% Traditional ROI: 5.62%
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%
101 S INTERLACHEN AVENUE #104 Winter Park, FL FIRST TIME ON THE MARKET! ULTRA-RARE GROUND FLOOR CONDO IN DOWNTOWN WINTER PARK'S LACHEN H...	2 beds \| 2 baths \| 949 sq.ft.	$635,000	Airbnb cash on cash: 2.43% Traditional cash on cash: 0.77% Airbnb Rental Income: $3260 Traditional Rental Income: $1543 Airbnb ROI: 2.43% Traditional ROI: 0.77%
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.	$195,000	Airbnb cash on cash: 9.06% Traditional cash on cash: 5.06% Airbnb Rental Income: $3260 Traditional Rental Income: $1786 Airbnb ROI: 9.06% Traditional ROI: 5.06%
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%
1996 INDIANA AVENUE Winter Park, FL Investor Special â Fixer Upper Opportunity in Winter Park / College Park Area. Rare o...	2 beds \| 1 baths \| 818 sq.ft.	$249,900	Airbnb cash on cash: 8.76% Traditional cash on cash: 4.26% Airbnb Rental Income: $3260 Traditional Rental Income: $1467 Airbnb ROI: 8.76% Traditional ROI: 4.26%
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.	$399,000	Airbnb cash on cash: 3.86% Traditional cash on cash: 3.01% Airbnb Rental Income: $3260 Traditional Rental Income: $2209 Airbnb ROI: 3.86% Traditional ROI: 3.01%
311 E MORSE BOULEVARD #7-5 Winter Park, FL Major Price Improvement! Here is your rare opportunity to own a studio apartment in Whispe...	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 \| 2,824 sq.ft.	$985,000	Airbnb cash on cash: 2.68% Traditional cash on cash: 1.92% Airbnb Rental Income: $5745 Traditional Rental Income: $3898 Airbnb ROI: 2.68% Traditional ROI: 1.92%
1275 MICHIGAN AVENUE Winter Park, FL Welcome to this stunning townhome in the heart of Winter Park, built by award-winning Ospr...	3 beds \| 3 baths \| 1,866 sq.ft.	$679,000	Airbnb cash on cash: 2.5% Traditional cash on cash: 1.17% Airbnb Rental Income: $4337 Traditional Rental Income: $2586 Airbnb ROI: 2.5% Traditional ROI: 1.17%
1261 INDIANA AVENUE Winter Park, FL Welcome to The Townhomes at Harper Place, where elegance meets convenience in beautiful Wi...	3 beds \| 3 baths \| 1,660 sq.ft.	$544,000	Airbnb cash on cash: 4.39% Traditional cash on cash: 1.96% Airbnb Rental Income: $4337 Traditional Rental Income: $2192 Airbnb ROI: 4.39% Traditional ROI: 1.96%
151 N ORLANDO AVENUE #101 Winter Park, FL Welcome home to this beautiful 2-bedroom, 1-bath gem in the heart of Winter Park! Nestled ...	2 beds \| 1 baths \| 804 sq.ft.	$260,000	Airbnb cash on cash: 7.61% Traditional cash on cash: 3.63% Airbnb Rental Income: $3260 Traditional Rental Income: $1551 Airbnb ROI: 7.61% Traditional ROI: 3.63%
1007 EARLY AVENUE Winter Park, FL Welcome to your next chapter at 1007 Early Ave in Winter Park, a charming 3-bedroom, 2-bat...	3 beds \| 2 baths \| 1,721 sq.ft.	$399,990	Airbnb cash on cash: 7.59% Traditional cash on cash: 5.13% Airbnb Rental Income: $4337 Traditional Rental Income: $2502 Airbnb ROI: 7.59% Traditional ROI: 5.13%
3018 NORTHWOOD BOULEVARD Winter Park, FL PRICE IMPROVEMENT - "MOVE-IN READY", 3-BED, 2-FULL BATHS, SINGLE FAMILY HOME WITH A LARGE ...	3 beds \| 2 baths \| 1,761 sq.ft.	$718,000	Airbnb cash on cash: 3.06% Traditional cash on cash: 2.36% Airbnb Rental Income: $4337 Traditional Rental Income: $2958 Airbnb ROI: 3.06% Traditional ROI: 2.36%
2009 Cornell Ave Winter Park, FL 2009 Cornell Ave, Orlando, FL 32789 \| Single Family Residential	2 beds \| 1 baths \| 762 sq.ft.	$259,000	Airbnb cash on cash: 8.08% Traditional cash on cash: 3.68% Airbnb Rental Income: $3260 Traditional Rental Income: $1453 Airbnb ROI: 8.08% Traditional ROI: 3.68%
1451 Cavendish Road Winter Park, FL Welcome to 1451 Cavendish Road, a beautifully renovated home in the heart of Orwin Manor, ...	3 beds \| 2 baths \| 1,437 sq.ft.	$619,500	Airbnb cash on cash: 3.7% Traditional cash on cash: 1.63% Airbnb Rental Income: $4337 Traditional Rental Income: $2225 Airbnb ROI: 3.7% Traditional ROI: 1.63%
151 N ORLANDO AVENUE #226 Winter Park, FL Take advantage of this newly updated 2 Bedrooms and 1 Bathroom LAKE FRONT condo convenient...	2 beds \| 1 baths \| 768 sq.ft.	$235,000	Airbnb cash on cash: 8.86% Traditional cash on cash: 4.53% Airbnb Rental Income: $3260 Traditional Rental Income: $1567 Airbnb ROI: 8.86% Traditional ROI: 4.53%
311 E MORSE BOULEVARD #6-3 Winter Park, FL Discover your new downtown Winter Park ground-floor pied-Ã -terre. Two blocks from Park Av...	1 beds \| 1 baths \| 570 sq.ft.	$319,000	Airbnb cash on cash: 3.59% Traditional cash on cash: 2.86% Airbnb Rental Income: $2412 Traditional Rental Income: $1601 Airbnb ROI: 3.59% Traditional ROI: 2.86%
151 N ORLANDO AVENUE #115 Winter Park, FL Welcome to Lake Killarney Living ... Where Winter Park charm meets everyday convenience. F...	2 beds \| 1 baths \| 710 sq.ft.	$298,000	Airbnb cash on cash: 4.78% Traditional cash on cash: 2.75% Airbnb Rental Income: $3260 Traditional Rental Income: $1958 Airbnb ROI: 4.78% Traditional ROI: 2.75%
560 OLOLU DRIVE Winter Park, FL Nestled on the shores of private, skiable Lake Killarney, this beautifully updated and abs...	2 beds \| 2 baths \| 1,086 sq.ft.	$949,000	Airbnb cash on cash: 0.85% Traditional cash on cash: 0.36% Airbnb Rental Income: $3260 Traditional Rental Income: $2093 Airbnb ROI: 0.85% Traditional ROI: 0.36%

Vacation Rentals in Winter Park

There are 125 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 $279. 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 125 Airbnb properties available for sale in Winter Park.

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

In January 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%

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%

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%

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%

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 COURT #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%

1518 PINEWOOD DRIVE

Winter Park, FL

3 beds | N/A baths | 1,197 sq.ft.

$449,900

Airbnb cash on cash: 5.4%

Traditional cash on cash: 1.72%

Airbnb Rental Income: $4337

Traditional Rental Income: $1878

Airbnb ROI: 5.4%

Traditional ROI: 1.72%

1600 PALMER AVENUE

Winter Park, FL

3 beds | 3 baths | 2,550 sq.ft.

$1,200,000

Airbnb cash on cash: 1.24%

Traditional cash on cash: 0.68%

Airbnb Rental Income: $4337

Traditional Rental Income: $2805

Airbnb ROI: 1.24%