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 July 2026, the average Airbnb occupancy rate in Winter-park is 44%.

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.	$1,380,000	Airbnb cash on cash: 1.63% Traditional cash on cash: 1.11% Airbnb Rental Income: $5539 Traditional Rental Income: $3743 Airbnb ROI: 1.63% Traditional ROI: 1.11%
2500 Lee Rd #220 Winter Park, FL **This house comes with a REDUCED RATE through the seller's preferred lender. This is a le...	2 beds \| 1 baths \| 851 sq.ft.	$199,900	Airbnb cash on cash: 6.04% Traditional cash on cash: 3.58% Airbnb Rental Income: $2559 Traditional Rental Income: $1477 Airbnb ROI: 6.04% Traditional ROI: 3.58%
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.	$699,000	Airbnb cash on cash: 4.69% Traditional cash on cash: 2.56% Airbnb Rental Income: $5539 Traditional Rental Income: $3035 Airbnb ROI: 4.69% Traditional ROI: 2.56%
363 N Phelps Ave 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: 2.03% Traditional cash on cash: 1.75% Airbnb Rental Income: $5539 Traditional Rental Income: $4109 Airbnb ROI: 2.03% Traditional ROI: 1.75%
1800 Magnolia Ave Winter Park, FL One or more photo(s) has been virtually staged. PRICE IMPROVEMENT! NO HOA! Experience refi...	4 beds \| 2 baths \| 2,431 sq.ft.	$994,000	Airbnb cash on cash: 2.51% Traditional cash on cash: 2.5% Airbnb Rental Income: $5539 Traditional Rental Income: $4421 Airbnb ROI: 2.51% Traditional ROI: 2.5%
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: 3.76% Traditional cash on cash: 3.03% Airbnb Rental Income: $2559 Traditional Rental Income: $1705 Airbnb ROI: 3.76% Traditional ROI: 3.03%
2560 Franklin Ave 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: 6.71% Traditional cash on cash: 3.26% Airbnb Rental Income: $5539 Traditional Rental Income: $2821 Airbnb ROI: 6.71% Traditional ROI: 3.26%
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: 2.08% Traditional cash on cash: 1.23% Airbnb Rental Income: $5539 Traditional Rental Income: $3522 Airbnb ROI: 2.08% 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: 2.17% Traditional cash on cash: 1.14% Airbnb Rental Income: $5539 Traditional Rental Income: $3328 Airbnb ROI: 2.17% Traditional ROI: 1.14%
1695 Lee Rd #E103 Winter Park, FL One or more photo(s) has been virtually staged. One or more photo(s) has been virtually st...	2 beds \| 1 baths \| 881 sq.ft.	$134,900	Airbnb cash on cash: 7.67% Traditional cash on cash: 7.52% Airbnb Rental Income: $2559 Traditional Rental Income: $1924 Airbnb ROI: 7.67% Traditional ROI: 7.52%
3006 Northwood Blvd Winter Park, FL Reimagined from the ground up for modern living while honoring its original mid-century mo...	4 beds \| 3 baths \| 2,075 sq.ft.	$1,199,000	Airbnb cash on cash: 2.4% Traditional cash on cash: 0.87% Airbnb Rental Income: $5539 Traditional Rental Income: $2644 Airbnb ROI: 2.4% Traditional ROI: 0.87%
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 \| 3 baths \| 2,662 sq.ft.	$944,890	Airbnb cash on cash: 3.7% Traditional cash on cash: 3.4% Airbnb Rental Income: $5539 Traditional Rental Income: $4170 Airbnb ROI: 3.7% Traditional ROI: 3.4%
1780 Bryan Ave 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: 3.62% Traditional cash on cash: 2.01% Airbnb Rental Income: $5539 Traditional Rental Income: $3153 Airbnb ROI: 3.62% Traditional ROI: 2.01%
440 Cambridge Blvd Winter Park, FL Under contract-accepting backup offers. **This house comes with a REDUCED RATE through the...	2 beds \| 1 baths \| 988 sq.ft.	$380,000	Airbnb cash on cash: 3.05% Traditional cash on cash: 2.35% Airbnb Rental Income: $2559 Traditional Rental Income: $1697 Airbnb ROI: 3.05% Traditional ROI: 2.35%
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: 3.42% Traditional cash on cash: 2.23% Airbnb Rental Income: $2559 Traditional Rental Income: $1565 Airbnb ROI: 3.42% Traditional ROI: 2.23%
2831 Mulford Ave Winter Park, FL Rare opportunity to own on one of the most desirable streets in Audubon Park with a covete...	4 beds \| 2 baths \| 1,647 sq.ft.	$715,000	Airbnb cash on cash: 4.89% Traditional cash on cash: 2.63% Airbnb Rental Income: $5539 Traditional Rental Income: $2874 Airbnb ROI: 4.89% Traditional ROI: 2.63%
1521 CAVENDISH RD Winter Park, FL Virtually Staged. Located in the heart of Orwin Manor, one of Winter Parkâs most beloved...	2 beds \| 1 baths \| 1,036 sq.ft.	$470,000	Airbnb cash on cash: 2.62% Traditional cash on cash: 2.34% Airbnb Rental Income: $2559 Traditional Rental Income: $1823 Airbnb ROI: 2.62% Traditional ROI: 2.34%
2625 Park Place Dr Winter Park, FL 2625 Park Place Dr, Winter Park, FL 32789 \| Single Family Residential	4 beds \| 4 baths \| 3,460 sq.ft.	$1,799,000	Airbnb cash on cash: 0.61% Traditional cash on cash: 0.03% Airbnb Rental Income: $5539 Traditional Rental Income: $3453 Airbnb ROI: 0.61% Traditional ROI: 0.03%
2041 Jewell Ave Winter Park, FL 2041 Jewell Ave, Winter Park, FL 32789 \| Single Family Residential	3 beds \| 1 baths \| 1,508 sq.ft.	$470,000	Airbnb cash on cash: 2.1% Traditional cash on cash: 2.06% Airbnb Rental Income: $2443 Traditional Rental Income: $1827 Airbnb ROI: 2.1% Traditional ROI: 2.06%
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: 3.52% Traditional cash on cash: 3.51% Airbnb Rental Income: $5539 Traditional Rental Income: $4423 Airbnb ROI: 3.52% Traditional ROI: 3.51%
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: 4.75% Traditional cash on cash: 1.86% Airbnb Rental Income: $5539 Traditional Rental Income: $2476 Airbnb ROI: 4.75% Traditional ROI: 1.86%
1695 LEE ROAD #E116 Winter Park, FL Under contract-accepting backup offers. Located in the heart of Winter Park, this 3-bedroo...	3 beds \| 2 baths \| 1,149 sq.ft.	$110,000	Airbnb cash on cash: 6.96% Traditional cash on cash: 6.05% Airbnb Rental Income: $2443 Traditional Rental Income: $1750 Airbnb ROI: 6.96% Traditional ROI: 6.05%
641 W LYMAN AVENUE Winter Park, FL Under contract-accepting backup offers. LOCATION. LOCATION. LOCATION. Heres the thing; in ...	3 beds \| 2 baths \| 1,120 sq.ft.	$509,000	Airbnb cash on cash: 1.45% Traditional cash on cash: 1.39% Airbnb Rental Income: $2443 Traditional Rental Income: $1821 Airbnb ROI: 1.45% Traditional ROI: 1.39%
3114 HEARTLEAF PLACE Winter Park, FL Tucked away on a rare and breathtaking .96-acre homesite, this one-of-a-kind property in L...	4 beds \| 3 baths \| 2,702 sq.ft.	$685,000	Airbnb cash on cash: 4.78% Traditional cash on cash: 3.59% Airbnb Rental Income: $5539 Traditional Rental Income: $3669 Airbnb ROI: 4.78% Traditional ROI: 3.59%
744 Cornwall Rd Winter Park, FL Welcome to your dream home! This exceptional 4-bedroom residence features a desirable spli...	4 beds \| 2 baths \| 1,968 sq.ft.	$675,000	Airbnb cash on cash: 4.92% Traditional cash on cash: 2.89% Airbnb Rental Income: $5539 Traditional Rental Income: $3114 Airbnb ROI: 4.92% Traditional ROI: 2.89%
2918 Antique Oaks Cir #25 Winter Park, FL 2 Bedroom 2 bath condo 1 block south of University Blvd great location for UCF or Full Sai...	2 beds \| 2 baths \| 1,018 sq.ft.	$189,000	Airbnb cash on cash: 5.48% Traditional cash on cash: 5.4% Airbnb Rental Income: $2559 Traditional Rental Income: $1930 Airbnb ROI: 5.48% Traditional ROI: 5.4%
2217 SUSSEX ROAD Winter Park, FL Back in market after upgrades !!! Welcome to 2217 Sussex Road â a beautifully maintained...	4 beds \| 2 baths \| 2,092 sq.ft.	$519,999	Airbnb cash on cash: 6.97% Traditional cash on cash: 4.63% Airbnb Rental Income: $5539 Traditional Rental Income: $3288 Airbnb ROI: 6.97% Traditional ROI: 4.63%
1946 Strathaven Rd Winter Park, FL ? FULLY REMODELED WINTER PARK POOL HOME NEAR BALDWIN PARK! ? Welcome to 1946 Strathaven...	4 beds \| 2 baths \| 2,102 sq.ft.	$625,000	Airbnb cash on cash: 4.84% Traditional cash on cash: 2.37% Airbnb Rental Income: $5539 Traditional Rental Income: $2931 Airbnb ROI: 4.84% Traditional ROI: 2.37%
1842 Puritan Ave Winter Park, FL Modern design , open concept layout , sleek quartz counter top , all new appliances, new l...	4 beds \| 2 baths \| N/A	$429,000	Airbnb cash on cash: 8.92% Traditional cash on cash: 4.33% Airbnb Rental Income: $5539 Traditional Rental Income: $2586 Airbnb ROI: 8.92% Traditional ROI: 4.33%
2383 SUN VALLEY CIRCLE #2383 Winter Park, FL Nestled in a peaceful setting within the serene Cedarwood Village community, this charming...	2 beds \| 2 baths \| 1,295 sq.ft.	$250,000	Airbnb cash on cash: 3.48% Traditional cash on cash: 3.07% Airbnb Rental Income: $2559 Traditional Rental Income: $1847 Airbnb ROI: 3.48% Traditional ROI: 3.07%
2222 Marsh Sedge Lane Winter Park, FL Welcome to your dream Home! This stunning and elegant single-story home, built by Meritage...	4 beds \| 3 baths \| 2,192 sq.ft.	$739,000	Airbnb cash on cash: 3.84% Traditional cash on cash: 1.91% Airbnb Rental Income: $5539 Traditional Rental Income: $3097 Airbnb ROI: 3.84% Traditional ROI: 1.91%
205 LEWFIELD CIRCLE #205 Winter Park, FL MOTIVATED SELLER! Wonderful! Exceptional Winter Park location! Amenities include 2 pools, ...	2 beds \| 2 baths \| 927 sq.ft.	$182,900	Airbnb cash on cash: 6.28% Traditional cash on cash: 5.09% Airbnb Rental Income: $2559 Traditional Rental Income: $1737 Airbnb ROI: 6.28% Traditional ROI: 5.09%
2052 LEANNE COURT Winter Park, FL Welcome to 2052 Leanne Ct, a home that exudes warmth and elegance. The living room is grac...	4 beds \| 2 baths \| 2,264 sq.ft.	$440,000	Airbnb cash on cash: 9.16% Traditional cash on cash: 5.8% Airbnb Rental Income: $5539 Traditional Rental Income: $3043 Airbnb ROI: 9.16% Traditional ROI: 5.8%
7300 Daniel Webster Dr #M7 Winter Park, FL Welcome home to this stunningly updated two-story condo that perfectly combines modern ele...	2 beds \| 2 baths \| 1,108 sq.ft.	$159,000	Airbnb cash on cash: 6.47% Traditional cash on cash: 6.28% Airbnb Rental Income: $2559 Traditional Rental Income: $1914 Airbnb ROI: 6.47% Traditional ROI: 6.28%
3027 Aaron Burr Ave #L1 Winter Park, FL Step into this beautifully renovated two-story condo offering the perfect blend of modern ...	2 beds \| 2 baths \| 1,090 sq.ft.	$159,000	Airbnb cash on cash: 6.47% Traditional cash on cash: 6.23% Airbnb Rental Income: $2559 Traditional Rental Income: $1907 Airbnb ROI: 6.47% Traditional ROI: 6.23%
1131 WILDMEADOW RUN Winter Park, FL Winter Park - Located in the gated community of Hawks Crest, this 4-bedroom, 3.5-bath home...	4 beds \| 4 baths \| 2,589 sq.ft.	$825,000	Airbnb cash on cash: 3.76% Traditional cash on cash: 2.64% Airbnb Rental Income: $5539 Traditional Rental Income: $3566 Airbnb ROI: 3.76% Traditional ROI: 2.64%
5143 LAZY OAKS DRIVE #5143 Winter Park, FL Quiet Living in the Desirable Lazy Oaks Community of Winter Park. Welcome to the ...	2 beds \| 2 baths \| 1,008 sq.ft.	$275,000	Airbnb cash on cash: 4.7% Traditional cash on cash: 3.64% Airbnb Rental Income: $2559 Traditional Rental Income: $1668 Airbnb ROI: 4.7% Traditional ROI: 3.64%
2317 SUN VALLEY CIRCLE #2317 Winter Park, FL Discover comfort and convenience in this charming, spacious 2-bedroom, 2-bath residence ne...	2 beds \| 2 baths \| 1,295 sq.ft.	$259,000	Airbnb cash on cash: 3.82% Traditional cash on cash: 3.42% Airbnb Rental Income: $2559 Traditional Rental Income: $1846 Airbnb ROI: 3.82% Traditional ROI: 3.42%
1287 VERDANT GLADE PLACE Winter Park, FL **This house comes with a REDUCED RATE through the seller's preferred lender. This is a le...	4 beds \| 4 baths \| 3,020 sq.ft.	$825,000	Airbnb cash on cash: 3.3% Traditional cash on cash: 2.1% Airbnb Rental Income: $5539 Traditional Rental Income: $3498 Airbnb ROI: 3.3% Traditional ROI: 2.1%

Vacation Rentals in Winter Park

There are 134 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 $799,522 and the average price per square foot is $397. The cash on cash return on vacation rentals in Winter Park is 3.00%. The average monthly short term rental income in Winter Park is $2,559.

Winter Park, FL Short Term Rentals FAQs for Buyers, Sellers and Investors

There are 134 Airbnb properties available for sale in Winter Park.

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

In July 2026, the average Airbnb occupancy rate in Winter Park is 44%.

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.

$1,380,000

Airbnb cash on cash: 1.63%

Traditional cash on cash: 1.11%

Airbnb Rental Income: $5539

Traditional Rental Income: $3743

Airbnb ROI: 1.63%

Traditional ROI: 1.11%

2500 Lee Rd #220

Winter Park, FL

2 beds | 1 baths | 851 sq.ft.

$199,900

Airbnb cash on cash: 6.04%

Traditional cash on cash: 3.58%

Airbnb Rental Income: $2559

Traditional Rental Income: $1477

Airbnb ROI: 6.04%

Traditional ROI: 3.58%

2333 WESTMINSTER COURT

Winter Park, FL

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

$699,000

Airbnb cash on cash: 4.69%

Traditional cash on cash: 2.56%

Airbnb Rental Income: $5539

Traditional Rental Income: $3035

Airbnb ROI: 4.69%

Traditional ROI: 2.56%

363 N Phelps Ave

Winter Park, FL

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

$1,249,000

Airbnb cash on cash: 2.03%

Traditional cash on cash: 1.75%

Airbnb Rental Income: $5539

Traditional Rental Income: $4109

Airbnb ROI: 2.03%

Traditional ROI: 1.75%

1800 Magnolia Ave

Winter Park, FL

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

$994,000

Airbnb cash on cash: 2.51%

Traditional cash on cash: 2.5%

Airbnb Rental Income: $5539

Traditional Rental Income: $4421

Airbnb ROI: 2.51%

Traditional ROI: 2.5%

811 Overspin Dr

Winter Park, FL

2 beds | 1 baths | 749 sq.ft.

$349,000

Airbnb cash on cash: 3.76%

Traditional cash on cash: 3.03%

Airbnb Rental Income: $2559

Traditional Rental Income: $1705

Airbnb ROI: 3.76%

Traditional ROI: 3.03%

2560 Franklin Ave

Winter Park, FL

4 beds | 2 baths | 1,514 sq.ft.

$499,000

Airbnb cash on cash: 6.71%

Traditional cash on cash: 3.26%

Airbnb Rental Income: $5539

Traditional Rental Income: $2821

Airbnb ROI: 6.71%

Traditional ROI: 3.26%

1981 BLUE RIDGE ROAD

Winter Park, FL

4 beds | 2 baths | 2,750 sq.ft.

$1,150,000

Airbnb cash on cash: 2.08%

Traditional cash on cash: 1.23%

Airbnb Rental Income: $5539

Traditional Rental Income: $3522

Airbnb ROI: 2.08%