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 June 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.	$1,425,000	Airbnb cash on cash: 1.76% Traditional cash on cash: 1.11% Airbnb Rental Income: $5745 Traditional Rental Income: $3743 Airbnb ROI: 1.76% Traditional ROI: 1.11%
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.	$315,000	Airbnb cash on cash: 4.83% Traditional cash on cash: 3.83% Airbnb Rental Income: $3260 Traditional Rental Income: $2233 Airbnb ROI: 4.83% Traditional ROI: 3.83%
2333 WESTMINSTER COURT Winter Park, FL Settled on a rare double lot in the heart of Winter Park, this 4-bedroom, 2-bath home deli...	4 beds \| 2 baths \| 1,877 sq.ft.	$719,000	Airbnb cash on cash: 4.79% Traditional cash on cash: 2.46% Airbnb Rental Income: $5745 Traditional Rental Income: $3035 Airbnb ROI: 4.79% Traditional ROI: 2.46%
363 N PHELPS AVENUE Winter Park, FL This light and bright, single-story, almost 3,000 square foot pool home features a split p...	4 beds \| 3 baths \| 2,871 sq.ft.	$1,249,000	Airbnb cash on cash: 2.18% Traditional cash on cash: 1.75% Airbnb Rental Income: $5745 Traditional Rental Income: $4109 Airbnb ROI: 2.18% Traditional ROI: 1.75%
1800 MAGNOLIA AVENUE Winter Park, FL One or more photo(s) has been virtually staged. PRICE IMPROVEMENT! NO HOA! Experience refi...	4 beds \| 3 baths \| 2,431 sq.ft.	$1,000,000	Airbnb cash on cash: 2.68% Traditional cash on cash: 2.48% Airbnb Rental Income: $5745 Traditional Rental Income: $4421 Airbnb ROI: 2.68% Traditional ROI: 2.48%
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%
2418 EUSTON ROAD Winter Park, FL Welcome to this beautifully updated three-bedroom, two-and-a-half-bath home located in the...	3 beds \| 3 baths \| 2,228 sq.ft.	$749,000	Airbnb cash on cash: 2.72% Traditional cash on cash: 2.7% Airbnb Rental Income: $4337 Traditional Rental Income: $3412 Airbnb ROI: 2.72% Traditional ROI: 2.7%
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%
1651 Westchester Ave Winter Park, FL Under contract-accepting backup offers. Welcome to this exquisite Orwin Manor Cape Cod cla...	3 beds \| 2 baths \| 2,426 sq.ft.	$1,175,000	Airbnb cash on cash: 1.75% Traditional cash on cash: 1.73% Airbnb Rental Income: $4337 Traditional Rental Income: $3402 Airbnb ROI: 1.75% Traditional ROI: 1.73%
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%
1707 Harmon Ave Winter Park, FL 1707 Harmon Ave, Orlando, FL 32789 \| Single Family Residential	3 beds \| 2 baths \| 1,669 sq.ft.	$695,000	Airbnb cash on cash: 3.26% Traditional cash on cash: 1.04% Airbnb Rental Income: $4337 Traditional Rental Income: $1986 Airbnb ROI: 3.26% Traditional ROI: 1.04%
1981 BLUE RIDGE ROAD Winter Park, FL Welcome to 1981 Blue Ridge Rd in Winter Park, a spacious 4-bedroom, 2-bath home featuring ...	4 beds \| 2 baths \| 2,750 sq.ft.	$1,150,000	Airbnb cash on cash: 2.24% Traditional cash on cash: 1.23% Airbnb Rental Income: $5745 Traditional Rental Income: $3522 Airbnb ROI: 2.24% Traditional ROI: 1.23%
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.	$1,150,000	Airbnb cash on cash: 2.33% Traditional cash on cash: 1.14% Airbnb Rental Income: $5745 Traditional Rental Income: $3328 Airbnb ROI: 2.33% Traditional ROI: 1.14%
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.	$175,000	Airbnb cash on cash: 9.87% Traditional cash on cash: 8.11% Airbnb Rental Income: $3260 Traditional Rental Income: $2235 Airbnb ROI: 9.87% Traditional ROI: 8.11%
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. This is your final opportunity to build a custom home in on...	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%
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 Build your dream home in one of Winter Parkâs most desirable locations. This 66.6â x 1...	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%
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 PRICE IMPROVEMENT! Welcome to this beautifully remodeled two story home in one of Winter P...	3 beds \| 3 baths \| 1,920 sq.ft.	$549,000	Airbnb cash on cash: 4.77% Traditional cash on cash: 3.9% Airbnb Rental Income: $4337 Traditional Rental Income: $2979 Airbnb ROI: 4.77% Traditional ROI: 3.9%
1809 Hammerlin Ave Winter Park, FL 1809 Hammerlin Ave, Winter Park, FL 32789 \| Condo/Coop	3 beds \| 2 baths \| 1,818 sq.ft.	$549,000	Airbnb cash on cash: 3.75% Traditional cash on cash: 2.17% Airbnb Rental Income: $4337 Traditional Rental Income: $2615 Airbnb ROI: 3.75% Traditional ROI: 2.17%
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%
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.	$589,900	Airbnb cash on cash: 4.15% Traditional cash on cash: 2.93% Airbnb Rental Income: $4337 Traditional Rental Income: $2752 Airbnb ROI: 4.15% Traditional ROI: 2.93%
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.	$429,000	Airbnb cash on cash: 5.99% Traditional cash on cash: 4.24% Airbnb Rental Income: $4337 Traditional Rental Income: $2723 Airbnb ROI: 5.99% Traditional ROI: 4.24%
1807 Hammerlin Ave #G Winter Park, FL Price Improvement Welcome home to this beautifully updated two-story end-unit, ideally...	3 beds \| 2 baths \| 1,818 sq.ft.	$525,000	Airbnb cash on cash: 3.71% Traditional cash on cash: 2.75% Airbnb Rental Income: $4337 Traditional Rental Income: $2954 Airbnb ROI: 3.71% Traditional ROI: 2.75%
405 Lake Fair Ln 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.	$455,000	Airbnb cash on cash: 6.53% Traditional cash on cash: 4.82% Airbnb Rental Income: $4337 Traditional Rental Income: $2697 Airbnb ROI: 6.53% Traditional ROI: 4.82%
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.	$460,000	Airbnb cash on cash: 5.98% Traditional cash on cash: 3.5% Airbnb Rental Income: $4337 Traditional Rental Income: $2358 Airbnb ROI: 5.98% Traditional ROI: 3.5%
1830 EDWIN BOULEVARD Winter Park, FL Beautifully RENOVATED and MOVE-IN READY/TURN-KEY home in the heart of Winter Park. From th...	3 beds \| 2 baths \| 1,287 sq.ft.	$639,900	Airbnb cash on cash: 3.97% Traditional cash on cash: 1.69% Airbnb Rental Income: $4337 Traditional Rental Income: $2064 Airbnb ROI: 3.97% Traditional ROI: 1.69%
1813 Harland Park Dr Winter Park, FL 1813 Harland Park Dr, Winter Park, FL 32789 \| Single Family Residential	4 beds \| 3 baths \| 3,551 sq.ft.	$1,875,000	Airbnb cash on cash: 0.51% Traditional cash on cash: -0.62% Airbnb Rental Income: $5745 Traditional Rental Income: $2624 Airbnb ROI: 0.51% Traditional ROI: -0.62%
340 KILLARNEY BAY COURT #4-4 Winter Park, FL Welcome to 340 Killarney Bay, a beautifully maintained residence located within one of Win...	2 beds \| 3 baths \| 1,428 sq.ft.	$395,000	Airbnb cash on cash: 5.3% Traditional cash on cash: 3.95% Airbnb Rental Income: $3260 Traditional Rental Income: $2029 Airbnb ROI: 5.3% Traditional ROI: 3.95%
1009 LAKE BELL DRIVE Winter Park, FL Offered for the first time in years, this waterfront property presents a rare opportunity ...	3 beds \| 2 baths \| 1,467 sq.ft.	$699,000	Airbnb cash on cash: 3.34% Traditional cash on cash: 2.01% Airbnb Rental Income: $4337 Traditional Rental Income: $2560 Airbnb ROI: 3.34% Traditional ROI: 2.01%
1120 WISCONSIN AVENUE Winter Park, FL Curated with intention and finished without compromise, 1120 Wisconsin Avenue is a rare op...	3 beds \| 4 baths \| 2,213 sq.ft.	$1,095,000	Airbnb cash on cash: 1.32% Traditional cash on cash: 1.18% Airbnb Rental Income: $4337 Traditional Rental Income: $3283 Airbnb ROI: 1.32% Traditional ROI: 1.18%
1841 Lake Spier Dr Winter Park, FL 1841 Lake Spier Dr, Winter Park, FL 32789 \| Single Family Residential	3 beds \| 4 baths \| 2,467 sq.ft.	$1,650,000	Airbnb cash on cash: 0.29% Traditional cash on cash: 0.28% Airbnb Rental Income: $4337 Traditional Rental Income: $3403 Airbnb ROI: 0.29% Traditional ROI: 0.28%
723 SYMONDS AVENUE Winter Park, FL Built by Clarkson Concepts and ideally located in the heart of Winter Park just moments fr...	4 beds \| 4 baths \| 3,065 sq.ft.	$2,000,000	Airbnb cash on cash: 0.64% Traditional cash on cash: 0.18% Airbnb Rental Income: $5745 Traditional Rental Income: $3746 Airbnb ROI: 0.64% Traditional ROI: 0.18%
2261 Mulbry Dr Winter Park, FL 2261 Mulbry Dr, Winter Park, FL 32789 \| Single Family Residential	4 beds \| 3 baths \| 3,696 sq.ft.	$1,995,000	Airbnb cash on cash: 0.55% Traditional cash on cash: -0.5% Airbnb Rental Income: $5745 Traditional Rental Income: $2652 Airbnb ROI: 0.55% Traditional ROI: -0.5%
2157 LAKE DRIVE Winter Park, FL Welcome to this beautifully maintained Winter Park home in coveted 32789, offering over 2,...	3 beds \| 3 baths \| 2,124 sq.ft.	$689,000	Airbnb cash on cash: 3.95% Traditional cash on cash: 3.58% Airbnb Rental Income: $4337 Traditional Rental Income: $3185 Airbnb ROI: 3.95% Traditional ROI: 3.58%
2006 Cornell Ave Winter Park, FL Welcome home to this charming and fully remodeled 2-bedroom, 1-bathroom gem nestled in the...	2 beds \| 1 baths \| 797 sq.ft.	$338,000	Airbnb cash on cash: 5.26% Traditional cash on cash: 2.23% Airbnb Rental Income: $3260 Traditional Rental Income: $1565 Airbnb ROI: 5.26% Traditional ROI: 2.23%
1307 FORMOSA AVENUE Winter Park, FL Under contract-accepting backup offers. Charming 2-bed home in Winter Park located in the ...	2 beds \| 1 baths \| 1,150 sq.ft.	$373,800	Airbnb cash on cash: 4.35% Traditional cash on cash: 3.41% Airbnb Rental Income: $3260 Traditional Rental Income: $2199 Airbnb ROI: 4.35% Traditional ROI: 3.41%
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%

Vacation Rentals in Winter Park

There are 153 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 $749,613 and the average price per square foot is $377. 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 153 Airbnb properties available for sale in Winter Park.

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

In June 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.

$1,425,000

Airbnb cash on cash: 1.76%

Traditional cash on cash: 1.11%

Airbnb Rental Income: $5745

Traditional Rental Income: $3743

Airbnb ROI: 1.76%

Traditional ROI: 1.11%

150 KILLARNEY BAY COURT #5

Winter Park, FL

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

$315,000

Airbnb cash on cash: 4.83%

Traditional cash on cash: 3.83%

Airbnb Rental Income: $3260

Traditional Rental Income: $2233

Airbnb ROI: 4.83%

Traditional ROI: 3.83%

2333 WESTMINSTER COURT

Winter Park, FL

4 beds | 2 baths | 1,877 sq.ft.

$719,000

Airbnb cash on cash: 4.79%

Traditional cash on cash: 2.46%

Airbnb Rental Income: $5745

Traditional Rental Income: $3035

Airbnb ROI: 4.79%

Traditional ROI: 2.46%

363 N PHELPS AVENUE

Winter Park, FL

4 beds | 3 baths | 2,871 sq.ft.

$1,249,000

Airbnb cash on cash: 2.18%

Traditional cash on cash: 1.75%

Airbnb Rental Income: $5745

Traditional Rental Income: $4109

Airbnb ROI: 2.18%

Traditional ROI: 1.75%

1800 MAGNOLIA AVENUE

Winter Park, FL

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

$1,000,000

Airbnb cash on cash: 2.68%

Traditional cash on cash: 2.48%

Airbnb Rental Income: $5745

Traditional Rental Income: $4421

Airbnb ROI: 2.68%

Traditional ROI: 2.48%

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%

2418 EUSTON ROAD

Winter Park, FL

3 beds | 3 baths | 2,228 sq.ft.

$749,000

Airbnb cash on cash: 2.72%

Traditional cash on cash: 2.7%

Airbnb Rental Income: $4337

Traditional Rental Income: $3412

Airbnb ROI: 2.72%

Traditional ROI: 2.7%

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%