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
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: 2.12% Traditional cash on cash: 1.18% Airbnb Rental Income: $6159 Traditional Rental Income: $3743 Airbnb ROI: 2.12% Traditional ROI: 1.18%
1840 Bryan Ave Winter Park, FL Welcome to modern luxury in the heart of Winter Park! This custom 2014-built estate rests ...	4 beds \| 3 baths \| 3,727 sq.ft.	$1,725,000	Airbnb cash on cash: 0.9% Traditional cash on cash: -0.32% Airbnb Rental Income: $6159 Traditional Rental Income: $2986 Airbnb ROI: 0.9% Traditional ROI: -0.32%
1941 Oglesby Ave Winter Park, FL Welcome home to this charming 2-bedroom, 1-bathroom gem nestled in the heart of Winter Par...	2 beds \| 1 baths \| 780 sq.ft.	$340,000	Airbnb cash on cash: 3.35% Traditional cash on cash: 3.11% Airbnb Rental Income: $2157 Traditional Rental Income: $1531 Airbnb ROI: 3.35% Traditional ROI: 3.11%
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: 4.28% Traditional cash on cash: 3.59% Airbnb Rental Income: $2157 Traditional Rental Income: $1477 Airbnb ROI: 4.28% Traditional ROI: 3.59%
2430 Chantilly Ave Winter Park, FL Architecture, design, and function come together with remarkable intention in this custom ...	4 beds \| 4 baths \| 2,916 sq.ft.	$1,598,000	Airbnb cash on cash: 1.96% Traditional cash on cash: -0.18% Airbnb Rental Income: $6159 Traditional Rental Income: $1768 Airbnb ROI: 1.96% Traditional ROI: -0.18%
708 BALMORAL Road Winter Park, FL A rare elevated corner lot in the heart of Winter Park - walkable to Park Avenue's boutiqu...	4 beds \| 3 baths \| 2,786 sq.ft.	$1,590,000	Airbnb cash on cash: 1.88% Traditional cash on cash: -0.02% Airbnb Rental Income: $6159 Traditional Rental Income: $2127 Airbnb ROI: 1.88% Traditional ROI: -0.02%
3006 Northwood Blvd Winter Park, FL Reinvented from the ground up for modern living while honoring its 1953 mid-century modern...	4 beds \| 3 baths \| 2,075 sq.ft.	$950,000	Airbnb cash on cash: 3.8% Traditional cash on cash: 1.33% Airbnb Rental Income: $6159 Traditional Rental Income: $2644 Airbnb ROI: 3.8% Traditional ROI: 1.33%
1695 Lee Rd #D211 Winter Park, FL Welcome to this lovely open-concept 2 bedroom, 1 bathroom condo, perfectly situated in a f...	2 beds \| 1 baths \| 881 sq.ft.	$107,000	Airbnb cash on cash: 6.52% Traditional cash on cash: 5% Airbnb Rental Income: $2157 Traditional Rental Income: $1449 Airbnb ROI: 6.52% Traditional ROI: 5%
1550 Palm Ave Winter Park, FL Under Construction. LUXURY NEW CONSTRUCTION IN WINTER PARK'S HIGHLY SOUGHT-AFTER TREE STRE...	4 beds \| 3 baths \| 2,706 sq.ft.	$1,829,000	Airbnb cash on cash: 1.43% Traditional cash on cash: 0.3% Airbnb Rental Income: $6159 Traditional Rental Income: $3021 Airbnb ROI: 1.43% Traditional ROI: 0.3%
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 \| 2 baths \| 2,662 sq.ft.	$918,000	Airbnb cash on cash: 4.44% Traditional cash on cash: 3.53% Airbnb Rental Income: $6159 Traditional Rental Income: $4170 Airbnb ROI: 4.44% Traditional ROI: 3.53%
2308 Mulbry Dr Winter Park, FL Under Construction. In a coveted Winter Park enclave, this masterful LUIH residence balanc...	4 beds \| 3 baths \| 2,530 sq.ft.	$1,699,000	Airbnb cash on cash: 1.86% Traditional cash on cash: 0.24% Airbnb Rental Income: $6159 Traditional Rental Income: $2401 Airbnb ROI: 1.86% Traditional ROI: 0.24%
2007 Cornell Ave Winter Park, FL Tucked away on a quiet street just minutes from the heart of Winter Park, this beautifully...	3 beds \| 2 baths \| 1,154 sq.ft.	$449,000	Airbnb cash on cash: 1.24% Traditional cash on cash: 0.93% Airbnb Rental Income: $2174 Traditional Rental Income: $1494 Airbnb ROI: 1.24% Traditional ROI: 0.93%
723 Symonds Ave 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.	$1,700,000	Airbnb cash on cash: 1.14% Traditional cash on cash: 0.38% Airbnb Rental Income: $6159 Traditional Rental Income: $3746 Airbnb ROI: 1.14% Traditional ROI: 0.38%
1421 Chapman Cir Winter Park, FL Welcome to 1421 Chapman Circle, an elegant Spanish-Mediterranean home nestled within the h...	4 beds \| 3 baths \| 3,578 sq.ft.	$1,377,500	Airbnb cash on cash: 1.65% Traditional cash on cash: 1.35% Airbnb Rental Income: $6159 Traditional Rental Income: $4534 Airbnb ROI: 1.65% Traditional ROI: 1.35%
1562 Arbor Park Dr Winter Park, FL Welcome to 1562 Arbor Park Drive, a beautifully maintained four-bedroom, two-and-a-half-ba...	4 beds \| 2 baths \| 1,899 sq.ft.	$775,000	Airbnb cash on cash: 4.47% Traditional cash on cash: 2.54% Airbnb Rental Income: $6159 Traditional Rental Income: $3552 Airbnb ROI: 4.47% Traditional ROI: 2.54%
2667 Cochise Trl Winter Park, FL A MUST SEE BEAUTIFUL WELL MAINTAINED POOL HOME by ORIGINAL OWNERS in SOUGHT AFTER WINTER P...	4 beds \| 3 baths \| 2,868 sq.ft.	$985,000	Airbnb cash on cash: 3.76% Traditional cash on cash: 2.52% Airbnb Rental Income: $6159 Traditional Rental Income: $3793 Airbnb ROI: 3.76% Traditional ROI: 2.52%
471 Holt Ave Winter Park, FL Exceptional Winter Park Opportunity with In-Law Suite & Income Potential Discover the oppo...	4 beds \| 3 baths \| 2,528 sq.ft.	$975,000	Airbnb cash on cash: 3.38% Traditional cash on cash: 2.07% Airbnb Rental Income: $6159 Traditional Rental Income: $3733 Airbnb ROI: 3.38% Traditional ROI: 2.07%
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.	$479,000	Airbnb cash on cash: 8.18% Traditional cash on cash: 3.44% Airbnb Rental Income: $6159 Traditional Rental Income: $2821 Airbnb ROI: 8.18% Traditional ROI: 3.44%
1695 LEE Road #B108 Winter Park, FL This charming 1bedroom, 1bathroom condo is a fantastic opportunity for both homeowners and...	1 beds \| 1 baths \| 638 sq.ft.	$88,999	Airbnb cash on cash: 6.59% Traditional cash on cash: 5.91% Airbnb Rental Income: $1793 Traditional Rental Income: $1246 Airbnb ROI: 6.59% Traditional ROI: 5.91%
943 Fairway Dr Winter Park, FL Welcome to this beautifully maintained four-bedroom, three-bathroom home offering over 2,0...	4 beds \| 3 baths \| 2,067 sq.ft.	$689,900	Airbnb cash on cash: 5.9% Traditional cash on cash: 2.84% Airbnb Rental Income: $6159 Traditional Rental Income: $2978 Airbnb ROI: 5.9% Traditional ROI: 2.84%
1946 Strathaven Rd Winter Park, FL Under contract-accepting backup offers. ***FULLY REMODELED WINTER PARK HOME NEAR BALDWIN P...	4 beds \| 3 baths \| 2,102 sq.ft.	$599,000	Airbnb cash on cash: 6.26% Traditional cash on cash: 2.66% Airbnb Rental Income: $6159 Traditional Rental Income: $2931 Airbnb ROI: 6.26% Traditional ROI: 2.66%
4353 Steed Ter Winter Park, FL MOTIVATED SELLER - QUICK CLOSE AVAILABLE! Welcome to this beautifully maintained 4-bedroom...	4 beds \| 2 baths \| 2,275 sq.ft.	$599,900	Airbnb cash on cash: 6.44% Traditional cash on cash: 3.23% Airbnb Rental Income: $6159 Traditional Rental Income: $3145 Airbnb ROI: 6.44% Traditional ROI: 3.23%
2286 Marsh Sedge Ln Winter Park, FL Virtually Staged. Welcome to one of the most uniquely positioned homes in the highly sough...	4 beds \| 3 baths \| 2,192 sq.ft.	$770,000	Airbnb cash on cash: 3.96% Traditional cash on cash: 1.89% Airbnb Rental Income: $6159 Traditional Rental Income: $3457 Airbnb ROI: 3.96% Traditional ROI: 1.89%
2627 Ambergate Rd Winter Park, FL Welcome home to this beautifully presented 4-bedroom, 3-bath home located in Winter Park E...	4 beds \| 3 baths \| 1,745 sq.ft.	$575,000	Airbnb cash on cash: 7.01% Traditional cash on cash: 3.55% Airbnb Rental Income: $6159 Traditional Rental Income: $3085 Airbnb ROI: 7.01% Traditional ROI: 3.55%
102 Bell Pl Winter Park, FL Step into elevated Florida living with this stunning brand-new residence, where modern des...	4 beds \| 3 baths \| 2,459 sq.ft.	$1,299,000	Airbnb cash on cash: 2.7% Traditional cash on cash: 2.64% Airbnb Rental Income: $6159 Traditional Rental Income: $4876 Airbnb ROI: 2.7% Traditional ROI: 2.64%
501 Heritage Blvd Winter Park, FL Welcome to this beautifully remodeled, move-in-ready home in the highly sought-after Winte...	4 beds \| 2 baths \| 1,376 sq.ft.	$426,000	Airbnb cash on cash: 8.73% Traditional cash on cash: 3.94% Airbnb Rental Income: $6159 Traditional Rental Income: $3032 Airbnb ROI: 8.73% Traditional ROI: 3.94%
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 \| 3 baths \| 2,589 sq.ft.	$825,000	Airbnb cash on cash: 4.08% Traditional cash on cash: 2.29% Airbnb Rental Income: $6159 Traditional Rental Income: $3566 Airbnb ROI: 4.08% Traditional ROI: 2.29%
1090 Wildmeadow Run Winter Park, FL One or more photo(s) has been virtually staged. **This house comes with a REDUCED RATE thr...	4 beds \| 3 baths \| 2,589 sq.ft.	$835,000	Airbnb cash on cash: 3.9% Traditional cash on cash: 1% Airbnb Rental Income: $6159 Traditional Rental Income: $2687 Airbnb ROI: 3.9% Traditional ROI: 1%
333 CORNWALL Road Winter Park, FL Located in the heart of Winter Park, Winter Park Pines is a well-established neighborhood ...	4 beds \| 2 baths \| 1,660 sq.ft.	$549,900	Airbnb cash on cash: 7.95% Traditional cash on cash: 3.23% Airbnb Rental Income: $6159 Traditional Rental Income: $2516 Airbnb ROI: 7.95% Traditional ROI: 3.23%
1320 Gladiolas Dr Winter Park, FL Been looking for a 4 bedroom home? Well, you have found it!!! This one owner home definite...	4 beds \| 2 baths \| 1,624 sq.ft.	$469,900	Airbnb cash on cash: 9.74% Traditional cash on cash: 3.89% Airbnb Rental Income: $6159 Traditional Rental Income: $2371 Airbnb ROI: 9.74% Traditional ROI: 3.89%
2054 Eastbrook Blvd Winter Park, FL Check out this private pool home in lovely Winter Park. Offers 4 bedrooms, 3 baths and a 2...	4 beds \| 3 baths \| 2,031 sq.ft.	$500,000	Airbnb cash on cash: 8.37% Traditional cash on cash: 5.12% Airbnb Rental Income: $6159 Traditional Rental Income: $3423 Airbnb ROI: 8.37% Traditional ROI: 5.12%
2008 Houndslake Dr Winter Park, FL Virtually staged. Discover space, comfort, and flexibility in this beautifully updated 4-b...	4 beds \| 2 baths \| 2,250 sq.ft.	$475,000	Airbnb cash on cash: 8.4% Traditional cash on cash: 3.54% Airbnb Rental Income: $6159 Traditional Rental Income: $2713 Airbnb ROI: 8.4% Traditional ROI: 3.54%
2712 Tortoise Cv Winter Park, FL Why Rent WHEN you can own this 2 bedroom 1 bath single car garage on this 1/2 duplex with ...	2 beds \| 1 baths \| 924 sq.ft.	$235,000	Airbnb cash on cash: 4.85% Traditional cash on cash: 4.36% Airbnb Rental Income: $2174 Traditional Rental Income: $1513 Airbnb ROI: 4.85% Traditional ROI: 4.36%
722 S Ranger Blvd Winter Park, FL REDUCED PRICE TO SELL! Impeccably Renovated Turn-Key Oasis with a Resort-Style Backyard! N...	4 beds \| 3 baths \| 2,164 sq.ft.	$775,000	Airbnb cash on cash: 5.62% Traditional cash on cash: 3.7% Airbnb Rental Income: $6159 Traditional Rental Income: $3548 Airbnb ROI: 5.62% Traditional ROI: 3.7%

Vacation Rentals in Winter Park

There are 129 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 $410. The cash on cash return on vacation rentals in Winter Park is 2.00%. The average monthly short term rental income in Winter Park is $2,174.

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

There are 129 Airbnb properties available for sale in Winter Park.

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

In September 2026, the average Airbnb occupancy rate in Winter Park is 39%.

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: 2.12%

Traditional cash on cash: 1.18%

Airbnb Rental Income: $6159

Traditional Rental Income: $3743

Airbnb ROI: 2.12%

Traditional ROI: 1.18%

1840 Bryan Ave

Winter Park, FL

4 beds | 3 baths | 3,727 sq.ft.

$1,725,000

Airbnb cash on cash: 0.9%

Traditional cash on cash: -0.32%

Airbnb Rental Income: $6159

Traditional Rental Income: $2986

Airbnb ROI: 0.9%

Traditional ROI: -0.32%

1941 Oglesby Ave

Winter Park, FL

2 beds | 1 baths | 780 sq.ft.

$340,000

Airbnb cash on cash: 3.35%

Traditional cash on cash: 3.11%

Airbnb Rental Income: $2157

Traditional Rental Income: $1531

Airbnb ROI: 3.35%

Traditional ROI: 3.11%

2500 Lee Rd #220

Winter Park, FL

2 beds | 1 baths | 851 sq.ft.

$199,900

Airbnb cash on cash: 4.28%

Traditional cash on cash: 3.59%

Airbnb Rental Income: $2157

Traditional Rental Income: $1477

Airbnb ROI: 4.28%

Traditional ROI: 3.59%

2430 Chantilly Ave

Winter Park, FL

4 beds | 4 baths | 2,916 sq.ft.

$1,598,000

Airbnb cash on cash: 1.96%

Traditional cash on cash: -0.18%

Airbnb Rental Income: $6159

Traditional Rental Income: $1768

Airbnb ROI: 1.96%

Traditional ROI: -0.18%

708 BALMORAL Road

Winter Park, FL

4 beds | 3 baths | 2,786 sq.ft.

$1,590,000

Airbnb cash on cash: 1.88%

Traditional cash on cash: -0.02%

Airbnb Rental Income: $6159

Traditional Rental Income: $2127

Airbnb ROI: 1.88%

Traditional ROI: -0.02%

3006 Northwood Blvd

Winter Park, FL

4 beds | 3 baths | 2,075 sq.ft.

$950,000

Airbnb cash on cash: 3.8%

Traditional cash on cash: 1.33%

Airbnb Rental Income: $6159

Traditional Rental Income: $2644

Airbnb ROI: 3.8%

Traditional ROI: 1.33%

1695 Lee Rd #D211

Winter Park, FL

2 beds | 1 baths | 881 sq.ft.

$107,000

Airbnb cash on cash: 6.52%

Traditional cash on cash: 5%

Airbnb Rental Income: $2157

Traditional Rental Income: $1449

Airbnb ROI: 6.52%