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 March 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 Ave Winter Park, FL Welcome to 1751 Goodrich Ave, a beautifully designed residence in the heart of Winter Park...	4 beds \| 3 baths \| 2,170 sq.ft.	$1,475,000	Airbnb cash on cash: 1.66% Traditional cash on cash: 0.78% Airbnb Rental Income: $5745 Traditional Rental Income: $3386 Airbnb ROI: 1.66% Traditional ROI: 0.78%
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%
150 Killarney Bay Ct #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%
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%
250 Cortland Ave 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.	$489,000	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 Ave #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: 5.17% Traditional cash on cash: 1.93% Airbnb Rental Income: $3260 Traditional Rental Income: $1610 Airbnb ROI: 5.17% Traditional ROI: 1.93%
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%
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 Rd #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 Ave #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: 1.55% Traditional cash on cash: -0.12% Airbnb Rental Income: $3260 Traditional Rental Income: $1543 Airbnb ROI: 1.55% Traditional ROI: -0.12%
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 Rd #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.	$190,000	Airbnb cash on cash: 9.32% Traditional cash on cash: 5.21% Airbnb Rental Income: $3260 Traditional Rental Income: $1786 Airbnb ROI: 9.32% Traditional ROI: 5.21%
1996 Indiana Ave 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 Dr Winter Park, FL Charming Opportunity in Prime Winter Park â 446 Alberta Drive, Winter Park, FL! First t...	4 beds \| 2 baths \| 3,263 sq.ft.	$1,675,000	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 Blvd #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: 0.54% Traditional cash on cash: -0.88% Airbnb Rental Income: $2412 Traditional Rental Income: $1343 Airbnb ROI: 0.54% Traditional ROI: -0.88%
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 Ave Winter Park, FL Welcome to this stunning townhome in the heart of Winter Park, built by award-winning Ospr...	3 beds \| 2 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%
151 N Orlando Ave #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: 5.42% Traditional cash on cash: 1.44% Airbnb Rental Income: $3260 Traditional Rental Income: $1551 Airbnb ROI: 5.42% Traditional ROI: 1.44%
2580 Euston Rd #0 Winter Park, FL just over .25 acre in winter park with block construction 3 bedroom 2 bath. Opportunity to...	3 beds \| 2 baths \| 1,158 sq.ft.	$415,000	Airbnb cash on cash: 6.37% Traditional cash on cash: 2.9% Airbnb Rental Income: $4337 Traditional Rental Income: $2043 Airbnb ROI: 6.37% Traditional ROI: 2.9%
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 Rd 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 Ave #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.	$215,000	Airbnb cash on cash: 5.87% Traditional cash on cash: 1.88% Airbnb Rental Income: $3260 Traditional Rental Income: $1567 Airbnb ROI: 5.87% Traditional ROI: 1.88%
311 E Morse Blvd #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.	$315,000	Airbnb cash on cash: 0.37% Traditional cash on cash: -0.36% Airbnb Rental Income: $2412 Traditional Rental Income: $1601 Airbnb ROI: 0.37% Traditional ROI: -0.36%
151 N Orlando Ave #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: 2.74% Airbnb Rental Income: $3260 Traditional Rental Income: $1958 Airbnb ROI: 4.78% Traditional ROI: 2.74%
560 Ololu Dr 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%
1780 Bryan Ave Winter Park, FL Discover a truly unique offering in the heart of Winter Park! This property, located at 17...	4 beds \| 2 baths \| 1,617 sq.ft.	$800,000	Airbnb cash on cash: 4.13% Traditional cash on cash: 1.32% Airbnb Rental Income: $5745 Traditional Rental Income: $2505 Airbnb ROI: 4.13% Traditional ROI: 1.32%
2361 Mulbry Dr Winter Park, FL Under Construction. Signature new construction currently under way, thoughtfully designed ...	4 beds \| 4 baths \| 3,111 sq.ft.	$2,395,000	Airbnb cash on cash: 0.78% Traditional cash on cash: 0.53% Airbnb Rental Income: $5745 Traditional Rental Income: $4042 Airbnb ROI: 0.78% Traditional ROI: 0.53%
851 Miles Ave #13 Winter Park, FL Welcome to 851 Miles Ave #13, a beautifully renovated 2-bedroom, 1-bathroom second-floor c...	2 beds \| 1 baths \| 808 sq.ft.	$209,999	Airbnb cash on cash: 7.78% Traditional cash on cash: 2.81% Airbnb Rental Income: $3260 Traditional Rental Income: $1515 Airbnb ROI: 7.78% Traditional ROI: 2.81%
2500 Lee Rd #222 Winter Park, FL Welcome to your next chapter of lakeside living! This charming one-bedroom, one-bathroom c...	1 beds \| 1 baths \| 645 sq.ft.	$189,500	Airbnb cash on cash: 6.24% Traditional cash on cash: 4.31% Airbnb Rental Income: $2412 Traditional Rental Income: $1457 Airbnb ROI: 6.24% Traditional ROI: 4.31%

Vacation Rentals in Winter Park

There are 252 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 $283. 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 252 Airbnb properties available for sale in Winter Park.

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

In March 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 Ave

Winter Park, FL

4 beds | 3 baths | 2,170 sq.ft.

$1,475,000

Airbnb cash on cash: 1.66%

Traditional cash on cash: 0.78%

Airbnb Rental Income: $5745

Traditional Rental Income: $3386

Airbnb ROI: 1.66%

Traditional ROI: 0.78%

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%

150 Killarney Bay Ct #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%

726 N PENNSYLVANIA AVENUE

Winter Park, FL

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%

250 Cortland Ave

Winter Park, FL

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

N/A beds | N/A baths | 954 sq.ft.

$489,000

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 Ave #118

Winter Park, FL

2 beds | 1 baths | 710 sq.ft.

$299,999

Airbnb cash on cash: 5.17%

Traditional cash on cash: 1.93%

Airbnb Rental Income: $3260

Traditional Rental Income: $1610

Airbnb ROI: 5.17%

Traditional ROI: 1.93%

1981 BLUE RIDGE ROAD

Winter Park, FL

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%