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
345 SYLVAN BOULEVARD Winter Park, FL Welcome to this stunning 4-bedroom, 2.5-bathroom POOL home with a NEW ROOF, offering a per...	4 beds \| 3 baths \| 2,011 sq.ft.	$1,075,000	Airbnb cash on cash: 2.4% Traditional cash on cash: 1.09% Airbnb Rental Income: $5745 Traditional Rental Income: $3285 Airbnb ROI: 2.4% Traditional ROI: 1.09%
678 DEPUGH STREET Winter Park, FL This stunning property in historic Winter Park offers an excellent price point and is idea...	4 beds \| 3 baths \| 1,940 sq.ft.	$700,000	Airbnb cash on cash: 4.71% Traditional cash on cash: 2.75% Airbnb Rental Income: $5745 Traditional Rental Income: $3325 Airbnb ROI: 4.71% Traditional ROI: 2.75%
648 CALLAHAN STREET Winter Park, FL Welcome to this stunning modern, custom-built home in the heart of Winter Park, FL! This b...	3 beds \| 3 baths \| 1,898 sq.ft.	$899,000	Airbnb cash on cash: 2.55% Traditional cash on cash: 2.22% Airbnb Rental Income: $4337 Traditional Rental Income: $3147 Airbnb ROI: 2.55% Traditional ROI: 2.22%
3455 ATHENA DRIVE Winter Park, FL Welcome to one of the larger homes in the community, where comfort and versatility meet. T...	4 beds \| 2 baths \| 2,161 sq.ft.	$465,500	Airbnb cash on cash: 8.64% Traditional cash on cash: 5.01% Airbnb Rental Income: $5745 Traditional Rental Income: $3019 Airbnb ROI: 8.64% Traditional ROI: 5.01%
5466 BRACKEN COURT Winter Park, FL Great value for a three bedroom home in Winter Park! This two story town home has the prim...	3 beds \| 3 baths \| 1,332 sq.ft.	$293,500	Airbnb cash on cash: 9.78% Traditional cash on cash: 4.71% Airbnb Rental Income: $4337 Traditional Rental Income: $2024 Airbnb ROI: 9.78% Traditional ROI: 4.71%
1005 FAIRWAY DRIVE Winter Park, FL Welcome to this newly renovated gem nestled along the ninth hole of the WP18 golf course. ...	4 beds \| 3 baths \| 2,584 sq.ft.	$799,000	Airbnb cash on cash: 4.2% Traditional cash on cash: 2.2% Airbnb Rental Income: $5745 Traditional Rental Income: $3113 Airbnb ROI: 4.2% Traditional ROI: 2.2%
3651 N GOLDENROD ROAD #204 Winter Park, FL WINTER PARK CONDO! This spacious condo is located just minutes from UCF, Rollins College a...	2 beds \| 2 baths \| 840 sq.ft.	$209,000	Airbnb cash on cash: 8.38% Traditional cash on cash: 3.24% Airbnb Rental Income: $3260 Traditional Rental Income: $1509 Airbnb ROI: 8.38% Traditional ROI: 3.24%
1244 VIA SALERNO Winter Park, FL Under contract-accepting backup offers. Stunning Mid-Century Modern Home in the Prestigiou...	3 beds \| 3 baths \| 2,505 sq.ft.	$1,875,000	Airbnb cash on cash: 0.16% Traditional cash on cash: -0.12% Airbnb Rental Income: $4337 Traditional Rental Income: $2941 Airbnb ROI: 0.16% Traditional ROI: -0.12%
5240 N LAKE BURKETT LANE Winter Park, FL One or more photo(s) has been virtually staged. Welcome to 5240 North Lake Burkett Lane, a...	4 beds \| 3 baths \| 2,290 sq.ft.	$535,000	Airbnb cash on cash: 7.19% Traditional cash on cash: 4.1% Airbnb Rental Income: $5745 Traditional Rental Income: $3049 Airbnb ROI: 7.19% Traditional ROI: 4.1%
1190 VILLAGE FOREST PLACE Winter Park, FL Under contract-accepting backup offers. NO HOA. HURRICANE PROOF WINDOWS! No preparation re...	3 beds \| 3 baths \| 1,525 sq.ft.	$420,000	Airbnb cash on cash: 6.89% Traditional cash on cash: 4.43% Airbnb Rental Income: $4337 Traditional Rental Income: $2455 Airbnb ROI: 6.89% Traditional ROI: 4.43%
3607 DATURA COURT Winter Park, FL Three bedroom/2 bath pool home located in a much sought after neighborhood in Winter Park....	3 beds \| 2 baths \| 1,380 sq.ft.	$409,900	Airbnb cash on cash: 6.78% Traditional cash on cash: 3.96% Airbnb Rental Income: $4337 Traditional Rental Income: $2344 Airbnb ROI: 6.78% Traditional ROI: 3.96%
1811 WINTER GREEN BOULEVARD Winter Park, FL Welcome to this charming property with a soothing neutral color scheme that exudes eleganc...	3 beds \| 2 baths \| 1,187 sq.ft.	$297,000	Airbnb cash on cash: 9.42% Traditional cash on cash: 3.94% Airbnb Rental Income: $4337 Traditional Rental Income: $1892 Airbnb ROI: 9.42% Traditional ROI: 3.94%
1908 CARRIGAN AVENUE Winter Park, FL One or more photo(s) has been virtually staged. Welcome to this stunning property with a n...	2 beds \| 2 baths \| 1,122 sq.ft.	$339,000	Airbnb cash on cash: 5.79% Traditional cash on cash: 3.68% Airbnb Rental Income: $3260 Traditional Rental Income: $1856 Airbnb ROI: 5.79% Traditional ROI: 3.68%
2720 AMBERGATE ROAD Winter Park, FL Price ImprovementCharming Remodeled Winter Park Home! Welcome to 2720 Ambergate Road, ...	3 beds \| 1 baths \| 1,188 sq.ft.	$375,000	Airbnb cash on cash: 7.54% Traditional cash on cash: 3.3% Airbnb Rental Income: $4337 Traditional Rental Income: $1934 Airbnb ROI: 7.54% Traditional ROI: 3.3%
8077 PLEASANT PINE CIRCLE Winter Park, FL Winter Park Home â Move in Ready Seller Financing May be Available Conveniently lo...	4 beds \| 4 baths \| 3,215 sq.ft.	$694,900	Airbnb cash on cash: 4.55% Traditional cash on cash: 3.47% Airbnb Rental Income: $5745 Traditional Rental Income: $3899 Airbnb ROI: 4.55% Traditional ROI: 3.47%
1571 ONECO AVENUE Winter Park, FL Under contract-accepting backup offers. Stunning, custom-built home in the Winter Park Tre...	4 beds \| 3 baths \| 2,510 sq.ft.	$1,190,000	Airbnb cash on cash: 2.35% Traditional cash on cash: 0.77% Airbnb Rental Income: $5745 Traditional Rental Income: $2850 Airbnb ROI: 2.35% Traditional ROI: 0.77%
3318 AMBER WOOD WAY #100 Winter Park, FL Under contract-accepting backup offers. Great investment opportunity for contractors & han...	2 beds \| 3 baths \| 1,031 sq.ft.	$190,000	Airbnb cash on cash: 9.25% Traditional cash on cash: 6.1% Airbnb Rental Income: $3260 Traditional Rental Income: $1958 Airbnb ROI: 9.25% Traditional ROI: 6.1%
363 N PHELPS AVENUE Winter Park, FL Under contract-accepting backup offers. This light and bright, single-story, almost 3,000 ...	4 beds \| 3 baths \| 2,871 sq.ft.	$1,130,000	Airbnb cash on cash: 2.56% Traditional cash on cash: 2.1% Airbnb Rental Income: $5745 Traditional Rental Income: $4109 Airbnb ROI: 2.56% Traditional ROI: 2.1%
1849 VIBURNUM LANE Winter Park, FL This charming home is located near the highly desirable area of Winter Park! 4 bedroom 2 b...	3 beds \| 2 baths \| 1,627 sq.ft.	$389,900	Airbnb cash on cash: 7.17% Traditional cash on cash: 4.15% Airbnb Rental Income: $4337 Traditional Rental Income: $2323 Airbnb ROI: 7.17% Traditional ROI: 4.15%
1310 ALOMA AVENUE Winter Park, FL Under contract-accepting backup offers. Elegant Spanish 4 bedroom, 2.5 bathroom home. Bea...	4 beds \| 3 baths \| 2,533 sq.ft.	$850,000	Airbnb cash on cash: 3.6% Traditional cash on cash: 1.78% Airbnb Rental Income: $5745 Traditional Rental Income: $3156 Airbnb ROI: 3.6% Traditional ROI: 1.78%
5229 N WOODCREST DRIVE Winter Park, FL Under contract-accepting backup offers. Location!! Stylish and affordably priced, this ...	3 beds \| 2 baths \| 1,242 sq.ft.	$347,000	Airbnb cash on cash: 8.07% Traditional cash on cash: 3.52% Airbnb Rental Income: $4337 Traditional Rental Income: $1941 Airbnb ROI: 8.07% Traditional ROI: 3.52%
512 BYRON ROAD Winter Park, FL Discover this charming home located in the desirable Winter Park area. Featuring a spaciou...	2 beds \| 2 baths \| 1,353 sq.ft.	$436,000	Airbnb cash on cash: 4.05% Traditional cash on cash: 2.91% Airbnb Rental Income: $3260 Traditional Rental Income: $2061 Airbnb ROI: 4.05% Traditional ROI: 2.91%
3136 HEARTLEAF PLACE Winter Park, FL Welcome to your Winter Park dream home! This stunning 4-bedroom, 3.5-bathroom residence of...	4 beds \| 4 baths \| 2,717 sq.ft.	$749,999	Airbnb cash on cash: 4.47% Traditional cash on cash: 3.74% Airbnb Rental Income: $5745 Traditional Rental Income: $4089 Airbnb ROI: 4.47% Traditional ROI: 3.74%
675 OVERSPIN DRIVE Winter Park, FL Welcome to this beautiful, custom-built, Mediterranean-style home located in the historic ...	4 beds \| 4 baths \| 2,764 sq.ft.	$946,500	Airbnb cash on cash: 2.99% Traditional cash on cash: 2.29% Airbnb Rental Income: $5745 Traditional Rental Income: $3980 Airbnb ROI: 2.99% Traditional ROI: 2.29%
4013 QUENITA DRIVE Winter Park, FL *MOTIVATED SELLER*Come see this "diamond in the rough" located in the sought-after cit...	4 beds \| 3 baths \| 2,327 sq.ft.	$535,000	Airbnb cash on cash: 6.68% Traditional cash on cash: 4.29% Airbnb Rental Income: $5745 Traditional Rental Income: $3404 Airbnb ROI: 6.68% Traditional ROI: 4.29%
2313 LOCH LOMOND DRIVE Winter Park, FL Incredible opportunity to own a property in the sought-after Winter Park 32792 area for th...	1 beds \| 1 baths \| 1,570 sq.ft.	$539,000	Airbnb cash on cash: 1.65% Traditional cash on cash: 1.47% Airbnb Rental Income: $2412 Traditional Rental Income: $1731 Airbnb ROI: 1.65% Traditional ROI: 1.47%
618 SAINT JOHNS COURT Winter Park, FL Investment Opportunity: (TENANT IN PLACE. UNTIL MARCH 31, 2025. DO NOT DISTURBE THE TE...	2 beds \| 2 baths \| 1,037 sq.ft.	$233,000	Airbnb cash on cash: 7.06% Traditional cash on cash: 3.91% Airbnb Rental Income: $3260 Traditional Rental Income: $1834 Airbnb ROI: 7.06% Traditional ROI: 3.91%
344 STARLING ROAD Winter Park, FL MODERN CHARM IN SOUGHT-AFTER WINTER PARK. Step into this beautifully remodeled 3-bedroom, ...	3 beds \| 3 baths \| 1,345 sq.ft.	$649,000	Airbnb cash on cash: 3.57% Traditional cash on cash: 2.07% Airbnb Rental Income: $4337 Traditional Rental Income: $2513 Airbnb ROI: 3.57% Traditional ROI: 2.07%
1250 S PENNSYLVANIA AVENUE #8 Winter Park, FL Quiet Virginia Heights Neighborhood with Stunning: private lake access park, walk to town ...	3 beds \| 3 baths \| 1,957 sq.ft.	$829,000	Airbnb cash on cash: 0.74% Traditional cash on cash: -0.32% Airbnb Rental Income: $4337 Traditional Rental Income: $2610 Airbnb ROI: 0.74% Traditional ROI: -0.32%
5118 Lake Howell Road Winter Park, FL Short Sale. Discover the perfect gem in Winter Park with no HOA or CDD fees! This fully re...	3 beds \| 2 baths \| 1,160 sq.ft.	$370,000	Airbnb cash on cash: 7.57% Traditional cash on cash: 3.69% Airbnb Rental Income: $4337 Traditional Rental Income: $2075 Airbnb ROI: 7.57% Traditional ROI: 3.69%
750 KILLARNEY BAY COURT #1 Winter Park, FL Be prepared to be impressed with this stunning ground floor unit at Winter Parkâs Killar...	2 beds \| 2 baths \| 1,140 sq.ft.	$368,000	Airbnb cash on cash: 4.6% Traditional cash on cash: 3.47% Airbnb Rental Income: $3260 Traditional Rental Income: $2138 Airbnb ROI: 4.6% Traditional ROI: 3.47%
3043 ANTIQUE OAKS CIRCLE #171 Winter Park, FL Stop The Car!!! Here it is!!! A fantastic ground floor 2/2 condominium; in sought after Wi...	2 beds \| 2 baths \| 1,018 sq.ft.	$215,000	Airbnb cash on cash: 7.61% Traditional cash on cash: 3.17% Airbnb Rental Income: $3260 Traditional Rental Income: $1622 Airbnb ROI: 7.61% Traditional ROI: 3.17%
2955 SANBINA STREET Winter Park, FL Newly updated home perfect for all-year round entertaining. The home has been tastefully u...	3 beds \| 2 baths \| 1,553 sq.ft.	$649,900	Airbnb cash on cash: 4.06% Traditional cash on cash: 2.77% Airbnb Rental Income: $4337 Traditional Rental Income: $2644 Airbnb ROI: 4.06% Traditional ROI: 2.77%
2418 EUSTON ROAD Winter Park, FL Discover this beautifully updated two-story home in the desirable 32789 ZIP code! This mov...	3 beds \| 3 baths \| 2,228 sq.ft.	$724,900	Airbnb cash on cash: 3.01% Traditional cash on cash: 2.99% Airbnb Rental Income: $4337 Traditional Rental Income: $3412 Airbnb ROI: 3.01% Traditional ROI: 2.99%
1621 PURITAN AVENUE Winter Park, FL Welcome to 1621 Puritan Ave, a beautifully renovated pool home in the desirable Winter Par...	4 beds \| 2 baths \| 1,765 sq.ft.	$499,000	Airbnb cash on cash: 7.8% Traditional cash on cash: 3.74% Airbnb Rental Income: $5745 Traditional Rental Income: $2704 Airbnb ROI: 7.8% Traditional ROI: 3.74%
851 MILES AVENUE #15 Winter Park, FL Super cute, move-in-ready 2-bedroom, 1-bath condo, perfectly situated in the heart of Wint...	2 beds \| 1 baths \| 808 sq.ft.	$245,000	Airbnb cash on cash: 8.4% Traditional cash on cash: 4.69% Airbnb Rental Income: $3260 Traditional Rental Income: $1667 Airbnb ROI: 8.4% Traditional ROI: 4.69%
114 SCOTTSDALE SQUARE #114 Winter Park, FL Under contract-accepting backup offers. Excellent Location! This 2 bedroom 1.5 bath , 2-st...	2 beds \| 2 baths \| 1,085 sq.ft.	$129,000	Airbnb cash on cash: 9.65% Traditional cash on cash: 4.85% Airbnb Rental Income: $3260 Traditional Rental Income: $1932 Airbnb ROI: 9.65% Traditional ROI: 4.85%
1223 FORMOSA AVENUE Winter Park, FL MOTIVATED SELLERS! PRICE IMPROVEMENT!!!! This home won't last at this price! Walk into thi...	4 beds \| 3 baths \| 3,834 sq.ft.	$900,000	Airbnb cash on cash: 3.58% Traditional cash on cash: 2.46% Airbnb Rental Income: $5745 Traditional Rental Income: $3658 Airbnb ROI: 3.58% Traditional ROI: 2.46%
7632 ALOMA PINES COURT Winter Park, FL *Welcome to 7632 Aloma Pines Ct!*Located in the Gated Community of Aloma Pines in Wint...	3 beds \| 3 baths \| 1,872 sq.ft.	$390,000	Airbnb cash on cash: 6.15% Traditional cash on cash: 3.42% Airbnb Rental Income: $4337 Traditional Rental Income: $2428 Airbnb ROI: 6.15% Traditional ROI: 3.42%
1716 PALMER AVENUE Winter Park, FL This stunning & revived ONE-STORY Winter Park home is the perfect mix of classic charm & m...	4 beds \| 3 baths \| 3,270 sq.ft.	$1,669,000	Airbnb cash on cash: 1.38% Traditional cash on cash: 0.77% Airbnb Rental Income: $5745 Traditional Rental Income: $3660 Airbnb ROI: 1.38% Traditional ROI: 0.77%

Vacation Rentals in Winter Park

There are 148 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 $489,000 and the average price per square foot is $254. The cash on cash return on vacation rentals in Winter Park is 6.00%. 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 148 Airbnb properties available for sale in Winter Park.

In 2024, the best neighborhood to buy short term rental property is Winter Park.

In December 2024, 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

345 SYLVAN BOULEVARD

Winter Park, FL

4 beds | 3 baths | 2,011 sq.ft.

$1,075,000

Airbnb cash on cash: 2.4%

Traditional cash on cash: 1.09%

Airbnb Rental Income: $5745

Traditional Rental Income: $3285

Airbnb ROI: 2.4%

Traditional ROI: 1.09%

678 DEPUGH STREET

Winter Park, FL

4 beds | 3 baths | 1,940 sq.ft.

$700,000

Airbnb cash on cash: 4.71%

Traditional cash on cash: 2.75%

Airbnb Rental Income: $5745

Traditional Rental Income: $3325

Airbnb ROI: 4.71%

Traditional ROI: 2.75%

648 CALLAHAN STREET

Winter Park, FL

3 beds | 3 baths | 1,898 sq.ft.

$899,000

Airbnb cash on cash: 2.55%

Traditional cash on cash: 2.22%

Airbnb Rental Income: $4337

Traditional Rental Income: $3147

Airbnb ROI: 2.55%

Traditional ROI: 2.22%

3455 ATHENA DRIVE

Winter Park, FL

4 beds | 2 baths | 2,161 sq.ft.

$465,500

Airbnb cash on cash: 8.64%

Traditional cash on cash: 5.01%

Airbnb Rental Income: $5745

Traditional Rental Income: $3019

Airbnb ROI: 8.64%

Traditional ROI: 5.01%

5466 BRACKEN COURT

Winter Park, FL

3 beds | 3 baths | 1,332 sq.ft.

$293,500

Airbnb cash on cash: 9.78%

Traditional cash on cash: 4.71%

Airbnb Rental Income: $4337

Traditional Rental Income: $2024

Airbnb ROI: 9.78%

Traditional ROI: 4.71%

1005 FAIRWAY DRIVE

Winter Park, FL

4 beds | 3 baths | 2,584 sq.ft.

$799,000

Airbnb cash on cash: 4.2%

Traditional cash on cash: 2.2%

Airbnb Rental Income: $5745

Traditional Rental Income: $3113

Airbnb ROI: 4.2%

Traditional ROI: 2.2%

3651 N GOLDENROD ROAD #204

Winter Park, FL

2 beds | 2 baths | 840 sq.ft.

$209,000

Airbnb cash on cash: 8.38%

Traditional cash on cash: 3.24%

Airbnb Rental Income: $3260

Traditional Rental Income: $1509

Airbnb ROI: 8.38%

Traditional ROI: 3.24%

1244 VIA SALERNO

Winter Park, FL

3 beds | 3 baths | 2,505 sq.ft.

$1,875,000

Airbnb cash on cash: 0.16%

Traditional cash on cash: -0.12%

Airbnb Rental Income: $4337

Traditional Rental Income: $2941

Airbnb ROI: 0.16%