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 April 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 AVENUE Winter Park, FL Welcome to 1751 Goodrich Ave, a beautifully designed residence in the heart of Winter Park...	4 beds \| 4 baths \| 2,170 sq.ft.	$1,475,000	Airbnb cash on cash: 1.66% Traditional cash on cash: 1.04% Airbnb Rental Income: $5745 Traditional Rental Income: $3743 Airbnb ROI: 1.66% Traditional ROI: 1.04%
668 OVERSPIN DRIVE Winter Park, FL One or more photo(s) has been virtually staged. A contemporary, beautifully finished home ...	4 beds \| 3 baths \| 2,509 sq.ft.	$875,000	Airbnb cash on cash: 3.21% Traditional cash on cash: 2.32% Airbnb Rental Income: $5745 Traditional Rental Income: $3878 Airbnb ROI: 3.21% Traditional ROI: 2.32%
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.	$335,000	Airbnb cash on cash: 4.49% Traditional cash on cash: 3.55% Airbnb Rental Income: $3260 Traditional Rental Income: $2233 Airbnb ROI: 4.49% Traditional ROI: 3.55%
720 W WEBSTER AVENUE Winter Park, FL One or more photo(s) has been virtually staged. This home can be purchased with NO INCOME ...	3 beds \| 2 baths \| 1,356 sq.ft.	$525,000	Airbnb cash on cash: 4.82% Traditional cash on cash: 3.39% Airbnb Rental Income: $4337 Traditional Rental Income: $2724 Airbnb ROI: 4.82% Traditional ROI: 3.39%
1800 MAGNOLIA AVENUE Winter Park, FL One or more photo(s) has been virtually staged. Experience refined living in this exquisit...	4 beds \| 3 baths \| 2,431 sq.ft.	$1,148,000	Airbnb cash on cash: 2.2% Traditional cash on cash: 2.04% Airbnb Rental Income: $5745 Traditional Rental Income: $4421 Airbnb ROI: 2.2% Traditional ROI: 2.04%
2036 VIA TUSCANY Winter Park, FL WINTER PARK VIAâS!!! Incredible Oversized Lot is located in the âHeartâ of Winter Pa...	3 beds \| 2 baths \| 2,148 sq.ft.	$2,000,000	Airbnb cash on cash: 0.04% Traditional cash on cash: -0.02% Airbnb Rental Income: $4337 Traditional Rental Income: $3307 Airbnb ROI: 0.04% Traditional ROI: -0.02%
811 Overspin Dr Winter Park, FL 811 Overspin Dr, Orlando, FL 32789 \| Single Family Residential	2 beds \| 1 baths \| 749 sq.ft.	$349,000	Airbnb cash on cash: 5.54% Traditional cash on cash: 3.03% Airbnb Rental Income: $3260 Traditional Rental Income: $1705 Airbnb ROI: 5.54% Traditional ROI: 3.03%
1250 FORMOSA AVENUE Winter Park, FL Modern living meets unbeatable location in this stunning 3 bedroom, 3.5 bathroom home nest...	3 beds \| 4 baths \| 1,937 sq.ft.	$560,000	Airbnb cash on cash: 3.36% Traditional cash on cash: 3.02% Airbnb Rental Income: $4337 Traditional Rental Income: $3249 Airbnb ROI: 3.36% Traditional ROI: 3.02%
2560 Franklin Avenue Winter Park, FL Come see this charming 4 bed, 2 bath, 2 story home in Winter Park/ Lake Killarney location...	4 beds \| 2 baths \| 1,514 sq.ft.	$499,000	Airbnb cash on cash: 7.07% Traditional cash on cash: 3.26% Airbnb Rental Income: $5745 Traditional Rental Income: $2821 Airbnb ROI: 7.07% Traditional ROI: 3.26%
1010 Garden Dr Winter Park, FL 1010 Garden Dr, Orlando, FL 32789 \| Other	N/A beds \| N/A baths \| N/A	$485,000	Airbnb cash on cash: 1.55% Traditional cash on cash: 1.33% Airbnb Rental Income: $2207 Traditional Rental Income: $1553 Airbnb ROI: 1.55% Traditional ROI: 1.33%
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: -0.05% Airbnb Rental Income: $2207 Traditional Rental Income: $1290 Airbnb ROI: 0.51% Traditional ROI: -0.05%
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.	$180,000	Airbnb cash on cash: 9.58% Traditional cash on cash: 7.87% Airbnb Rental Income: $3260 Traditional Rental Income: $2235 Airbnb ROI: 9.58% Traditional ROI: 7.87%
1399 ALOMA AVENUE Winter Park, FL *Price Adjustment * Motivated Seller! Charming 1948 Winter Park Home! This 3-bedroom, ...	3 beds \| 2 baths \| 1,804 sq.ft.	$600,000	Airbnb cash on cash: 4.6% Traditional cash on cash: 4.09% Airbnb Rental Income: $4337 Traditional Rental Income: $3142 Airbnb ROI: 4.6% Traditional ROI: 4.09%
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: 0.54% Traditional cash on cash: 0.12% Airbnb Rental Income: $2412 Traditional Rental Income: $1680 Airbnb ROI: 0.54% Traditional ROI: 0.12%
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.	$944,890	Airbnb cash on cash: 3.89% Traditional cash on cash: 3.4% Airbnb Rental Income: $5745 Traditional Rental Income: $4170 Airbnb ROI: 3.89% Traditional ROI: 3.4%
3018 NORTHWOOD BOULEVARD Winter Park, FL "MOTIVATED SELLER" - NEED SOME CLOSING COST? RATE BUY DOWN? WE CAN HELP GET YOU INTO THIS ...	3 beds \| 2 baths \| 1,761 sq.ft.	$679,000	Airbnb cash on cash: 3.29% Traditional cash on cash: 3.11% Airbnb Rental Income: $4337 Traditional Rental Income: $3308 Airbnb ROI: 3.29% Traditional ROI: 3.11%
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: 3.16% Airbnb Rental Income: $3260 Traditional Rental Income: $2075 Airbnb ROI: 4.78% Traditional ROI: 3.16%
1780 BRYAN AVENUE 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.	$849,000	Airbnb cash on cash: 3.84% Traditional cash on cash: 2.01% Airbnb Rental Income: $5745 Traditional Rental Income: $3153 Airbnb ROI: 3.84% Traditional ROI: 2.01%
851 MILES AVENUE #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: 7.99% Traditional cash on cash: 5.31% Airbnb Rental Income: $3260 Traditional Rental Income: $1995 Airbnb ROI: 7.99% Traditional ROI: 5.31%
2500 LEE RD. #222 Winter Park, FL Lakefront access in Winter Park under $200K! One of the few condos at this price point off...	1 beds \| 1 baths \| 645 sq.ft.	$189,500	Airbnb cash on cash: 6.59% Traditional cash on cash: 6.4% Airbnb Rental Income: $2412 Traditional Rental Income: $1787 Airbnb ROI: 6.59% Traditional ROI: 6.4%
423 OLOLU DRIVE Winter Park, FL Welcome to this beautifully remodeled two story home in one of Winter Parkâs most desira...	3 beds \| 3 baths \| 1,920 sq.ft.	$589,000	Airbnb cash on cash: 4.38% Traditional cash on cash: 3.57% Airbnb Rental Income: $4337 Traditional Rental Income: $2979 Airbnb ROI: 4.38% Traditional ROI: 3.57%
1809 Hammerlin Ave Winter Park, FL 1809 Hammerlin Ave, Winter Park, FL 32789 \| Condo/Coop	3 beds \| 2 baths \| 1,818 sq.ft.	$585,000	Airbnb cash on cash: 3.4% Traditional cash on cash: 1.92% Airbnb Rental Income: $4337 Traditional Rental Income: $2615 Airbnb ROI: 3.4% Traditional ROI: 1.92%
841 W SWOOPE AVENUE Winter Park, FL This Winter Park property offers exceptional potential in one of the most desirable and ra...	2 beds \| 1 baths \| 1,396 sq.ft.	$499,000	Airbnb cash on cash: 3.46% Traditional cash on cash: 3.03% Airbnb Rental Income: $3260 Traditional Rental Income: $2330 Airbnb ROI: 3.46% Traditional ROI: 3.03%
630 KILLARNEY BAY COURT #3 Winter Park, FL Lakefront townhome in desirable Killarney Bay directly on Lake Killarney, offering 2 bedro...	2 beds \| 3 baths \| 1,428 sq.ft.	$495,000	Airbnb cash on cash: 1.87% Traditional cash on cash: 1.84% Airbnb Rental Income: $3260 Traditional Rental Income: $2514 Airbnb ROI: 1.87% Traditional ROI: 1.84%
1951 STAUNTON AVENUE Winter Park, FL TRANSFERABLE TERMITE BOND INCLUDED. Welcome home to the charm and character of the bygone ...	3 beds \| 2 baths \| 2,556 sq.ft.	$599,000	Airbnb cash on cash: 4.54% Traditional cash on cash: 2.25% Airbnb Rental Income: $4337 Traditional Rental Income: $2142 Airbnb ROI: 4.54% Traditional ROI: 2.25%
1781 Indiana Ave #A Winter Park, FL 1781 Indiana Ave #A, Winter Park, FL 32789 \| Townhouse	3 beds \| 2 baths \| 1,616 sq.ft.	$545,000	Airbnb cash on cash: 3.65% Traditional cash on cash: 1.82% Airbnb Rental Income: $4337 Traditional Rental Income: $2492 Airbnb ROI: 3.65% Traditional ROI: 1.82%
1354 INDIANA AVENUE Winter Park, FL One or more photo(s) has been virtually staged. Fabulous location in Winter Park! Complete...	3 beds \| 2 baths \| 1,269 sq.ft.	$599,900	Airbnb cash on cash: 4.06% Traditional cash on cash: 2.86% Airbnb Rental Income: $4337 Traditional Rental Income: $2752 Airbnb ROI: 4.06% Traditional ROI: 2.86%
2779 SANBINA STREET Winter Park, FL Rare opportunity in the heart of 32789 â priced under $500K, this 3-bedroom, 2-bathroom ...	3 beds \| 2 baths \| 1,405 sq.ft.	$460,000	Airbnb cash on cash: 5.53% Traditional cash on cash: 3.89% Airbnb Rental Income: $4337 Traditional Rental Income: $2723 Airbnb ROI: 5.53% Traditional ROI: 3.89%
1807 HAMMERLIN AVENUE #G Winter Park, FL Welcome home to this beautifully updated two-story end-unit, ideally located just steps fr...	3 beds \| 3 baths \| 1,818 sq.ft.	$580,000	Airbnb cash on cash: 3.27% Traditional cash on cash: 2.4% Airbnb Rental Income: $4337 Traditional Rental Income: $2954 Airbnb ROI: 3.27% Traditional ROI: 2.4%
405 LAKE FAIR LANE Winter Park, FL One or more photo(s) has been virtually staged. Fully rebuilt, not just renovated. This Wi...	3 beds \| 2 baths \| 1,491 sq.ft.	$459,999	Airbnb cash on cash: 6.44% Traditional cash on cash: 4.75% Airbnb Rental Income: $4337 Traditional Rental Income: $2697 Airbnb ROI: 6.44% Traditional ROI: 4.75%
2713 EASTERN PARKWAY Winter Park, FL Welcome to this charming, meticulously maintained 3-bedroom, 2-bath residence in the heart...	3 beds \| 2 baths \| 1,304 sq.ft.	$670,000	Airbnb cash on cash: 3.93% Traditional cash on cash: 1.9% Airbnb Rental Income: $4337 Traditional Rental Income: $2154 Airbnb ROI: 3.93% Traditional ROI: 1.9%
950 HANOVER AVENUE Winter Park, FL Preferred lender credit available. Welcome home to your peaceful retreat tucked away near ...	3 beds \| 2 baths \| 1,606 sq.ft.	$470,000	Airbnb cash on cash: 5.83% Traditional cash on cash: 3.4% Airbnb Rental Income: $4337 Traditional Rental Income: $2358 Airbnb ROI: 5.83% Traditional ROI: 3.4%
1618 INDIANA AVENUE Winter Park, FL Beautiful income-producing duplex located in the highly desirable Winter Park area! This w...	4 beds \| N/A baths \| 1,604 sq.ft.	$685,000	Airbnb cash on cash: 3.42% Traditional cash on cash: 1.12% Airbnb Rental Income: $4337 Traditional Rental Income: $1957 Airbnb ROI: 3.42% Traditional ROI: 1.12%
1905 BONANZA CT Winter Park, FL This beautifully updated 4-bedroom, 2-bath bungalow with a 2-car garage sits on a quiet cu...	4 beds \| 2 baths \| 1,774 sq.ft.	$490,000	Airbnb cash on cash: 7.81% Traditional cash on cash: 3.89% Airbnb Rental Income: $5745 Traditional Rental Income: $2802 Airbnb ROI: 7.81% Traditional ROI: 3.89%
1830 EDWIN BOULEVARD Winter Park, FL Welcome to this beautifully designed and thoughtfully upgraded home that perfectly blends ...	3 beds \| 2 baths \| 1,287 sq.ft.	$679,800	Airbnb cash on cash: 3.68% Traditional cash on cash: 1.53% Airbnb Rental Income: $4337 Traditional Rental Income: $2064 Airbnb ROI: 3.68% Traditional ROI: 1.53%
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.	$775,000	Airbnb cash on cash: 3.75% Traditional cash on cash: 3.51% Airbnb Rental Income: $5745 Traditional Rental Income: $4423 Airbnb ROI: 3.75% Traditional ROI: 3.51%
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: 5.94% Airbnb Rental Income: $2412 Traditional Rental Income: $1512 Airbnb ROI: 8.17% Traditional ROI: 5.94%
446 ALBERTA DRIVE Winter Park, FL Under contract-accepting backup offers. Charming Opportunity in Prime Winter Park â 446 ...	4 beds \| 3 baths \| 3,263 sq.ft.	$1,675,000	Airbnb cash on cash: 1.49% Traditional cash on cash: 0.64% Airbnb Rental Income: $5745 Traditional Rental Income: $3271 Airbnb ROI: 1.49% Traditional ROI: 0.64%
770 W WEBSTER AVENUE Winter Park, FL Under contract-accepting backup offers. Stop the car! Develop your dream project on this ...	4 beds \| 2 baths \| 1,008 sq.ft.	$725,000	Airbnb cash on cash: 5% Traditional cash on cash: 1.86% Airbnb Rental Income: $5745 Traditional Rental Income: $2476 Airbnb ROI: 5% Traditional ROI: 1.86%
311 E MORSE BOULEVARD #6-3 Winter Park, FL Under contract-accepting backup offers. Discover your new downtown Winter Park ground-floo...	1 beds \| 1 baths \| 570 sq.ft.	$315,000	Airbnb cash on cash: 0.39% Traditional cash on cash: -0.01% Airbnb Rental Income: $2412 Traditional Rental Income: $1704 Airbnb ROI: 0.39% Traditional ROI: -0.01%

Vacation Rentals in Winter Park

There are 131 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 $524,900 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 131 Airbnb properties available for sale in Winter Park.

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

In April 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 AVENUE

Winter Park, FL

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

$1,475,000

Airbnb cash on cash: 1.66%

Traditional cash on cash: 1.04%

Airbnb Rental Income: $5745

Traditional Rental Income: $3743

Airbnb ROI: 1.66%

Traditional ROI: 1.04%

668 OVERSPIN DRIVE

Winter Park, FL

4 beds | 3 baths | 2,509 sq.ft.

$875,000

Airbnb cash on cash: 3.21%

Traditional cash on cash: 2.32%

Airbnb Rental Income: $5745

Traditional Rental Income: $3878

Airbnb ROI: 3.21%

Traditional ROI: 2.32%

150 KILLARNEY BAY COURT #5

Winter Park, FL

2 beds | 2 baths | 1,140 sq.ft.

$335,000

Airbnb cash on cash: 4.49%

Traditional cash on cash: 3.55%

Airbnb Rental Income: $3260

Traditional Rental Income: $2233

Airbnb ROI: 4.49%

Traditional ROI: 3.55%

720 W WEBSTER AVENUE

Winter Park, FL

3 beds | 2 baths | 1,356 sq.ft.

$525,000

Airbnb cash on cash: 4.82%

Traditional cash on cash: 3.39%

Airbnb Rental Income: $4337

Traditional Rental Income: $2724

Airbnb ROI: 4.82%

Traditional ROI: 3.39%

1800 MAGNOLIA AVENUE

Winter Park, FL

4 beds | 3 baths | 2,431 sq.ft.

$1,148,000

Airbnb cash on cash: 2.2%

Traditional cash on cash: 2.04%

Airbnb Rental Income: $5745

Traditional Rental Income: $4421

Airbnb ROI: 2.2%

Traditional ROI: 2.04%

2036 VIA TUSCANY

Winter Park, FL

3 beds | 2 baths | 2,148 sq.ft.

$2,000,000

Airbnb cash on cash: 0.04%

Traditional cash on cash: -0.02%

Airbnb Rental Income: $4337

Traditional Rental Income: $3307

Airbnb ROI: 0.04%

Traditional ROI: -0.02%

811 Overspin Dr

Winter Park, FL

2 beds | 1 baths | 749 sq.ft.

$349,000

Airbnb cash on cash: 5.54%

Traditional cash on cash: 3.03%

Airbnb Rental Income: $3260

Traditional Rental Income: $1705

Airbnb ROI: 5.54%

Traditional ROI: 3.03%

1250 FORMOSA AVENUE

Winter Park, FL

3 beds | 4 baths | 1,937 sq.ft.

$560,000

Airbnb cash on cash: 3.36%

Traditional cash on cash: 3.02%

Airbnb Rental Income: $4337

Traditional Rental Income: $3249

Airbnb ROI: 3.36%