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%
1481 HARMON AVENUE Winter Park, FL Owner Financing Available! Welcome to this charming four-bedroom, three-bath home nestled ...	4 beds \| 3 baths \| 1,705 sq.ft.	$545,000	Airbnb cash on cash: 6.76% Traditional cash on cash: 2.56% Airbnb Rental Income: $5745 Traditional Rental Income: $2462 Airbnb ROI: 6.76% Traditional ROI: 2.56%
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.	$949,000	Airbnb cash on cash: 2.36% Traditional cash on cash: 2.05% Airbnb Rental Income: $4337 Traditional Rental Income: $3147 Airbnb ROI: 2.36% Traditional ROI: 2.05%
5318 POINSETTA AVENUE Winter Park, FL Welcome to your beautifully updated Winter Park home! This inviting property features an e...	3 beds \| 2 baths \| 1,467 sq.ft.	$420,000	Airbnb cash on cash: 6.87% Traditional cash on cash: 3.48% Airbnb Rental Income: $4337 Traditional Rental Income: $2093 Airbnb ROI: 6.87% Traditional ROI: 3.48%
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.	$469,000	Airbnb cash on cash: 8.56% Traditional cash on cash: 4.97% Airbnb Rental Income: $5745 Traditional Rental Income: $3019 Airbnb ROI: 8.56% Traditional ROI: 4.97%
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%
5211 WOODCREST COURT Winter Park, FL Under contract-accepting backup offers. Stylish fully renovated 3 bedroom 2 bath home, wit...	3 beds \| 2 baths \| 1,578 sq.ft.	$484,000	Airbnb cash on cash: 5.78% Traditional cash on cash: 2.92% Airbnb Rental Income: $4337 Traditional Rental Income: $2132 Airbnb ROI: 5.78% Traditional ROI: 2.92%
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.	$824,000	Airbnb cash on cash: 4.04% Traditional cash on cash: 2.11% Airbnb Rental Income: $5745 Traditional Rental Income: $3113 Airbnb ROI: 4.04% Traditional ROI: 2.11%
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%
432 WORTHINGTON DRIVE Winter Park, FL Under contract-accepting backup offers. Discover a charming, single story home in the hear...	3 beds \| 1 baths \| 1,243 sq.ft.	$749,000	Airbnb cash on cash: 2.87% Traditional cash on cash: 0.76% Airbnb Rental Income: $4337 Traditional Rental Income: $1950 Airbnb ROI: 2.87% Traditional ROI: 0.76%
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 Welcome to 5240 North Lake Burkett Lane, a classic 4 bedroom, 2.5 bathroom home, located i...	4 beds \| 3 baths \| 2,290 sq.ft.	$575,000	Airbnb cash on cash: 6.63% Traditional cash on cash: 3.74% Airbnb Rental Income: $5745 Traditional Rental Income: $3049 Airbnb ROI: 6.63% Traditional ROI: 3.74%
1190 VILLAGE FOREST PLACE Winter Park, FL NO HOA. HURRICANE PROOF WINDOWS! No preparation required, owner has updated all windows in...	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%
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%
2434 BARBADOS DRIVE Winter Park, FL Great Schools, Great Location! Great investment property. Low HOA's. This unit offers 3 ...	3 beds \| 2 baths \| 1,284 sq.ft.	$299,000	Airbnb cash on cash: 9.48% Traditional cash on cash: 3.7% Airbnb Rental Income: $4337 Traditional Rental Income: $1797 Airbnb ROI: 9.48% Traditional ROI: 3.7%
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.	$340,000	Airbnb cash on cash: 5.77% Traditional cash on cash: 3.66% Airbnb Rental Income: $3260 Traditional Rental Income: $1856 Airbnb ROI: 5.77% Traditional ROI: 3.66%
2720 AMBERGATE ROAD Winter Park, FL Under contract-accepting backup offers. Price ImprovementCharming Remodeled Winter Par...	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 Beautiful Winter Park Home Looking for New Owner! Seller Financing is Available Conv...	4 beds \| 4 baths \| 3,215 sq.ft.	$699,900	Airbnb cash on cash: 4.51% Traditional cash on cash: 3.44% Airbnb Rental Income: $5745 Traditional Rental Income: $3899 Airbnb ROI: 4.51% Traditional ROI: 3.44%
1571 ONECO AVENUE Winter Park, FL Stunning, custom-built home in the Winter Park Tree Streets. This beautifully designed, Me...	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 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.	$1,170,000	Airbnb cash on cash: 2.44% Traditional cash on cash: 1.99% Airbnb Rental Income: $5745 Traditional Rental Income: $4109 Airbnb ROI: 2.44% Traditional ROI: 1.99%
1616 HIBISCUS AVENUE Winter Park, FL Under contract-accepting backup offers. Stunning transitional modern home located in the h...	4 beds \| 5 baths \| 3,897 sq.ft.	$2,150,000	Airbnb cash on cash: 0.23% Traditional cash on cash: -0.04% Airbnb Rental Income: $5745 Traditional Rental Income: $4062 Airbnb ROI: 0.23% Traditional ROI: -0.04%
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%
2427 GALLERY VIEW DRIVE #7 Winter Park, FL Remarkable Winter Park condo looking for new owner. Great opportunity 1st floor, overlook...	2 beds \| 2 baths \| 1,004 sq.ft.	$295,000	Airbnb cash on cash: 5.31% Traditional cash on cash: 4.13% Airbnb Rental Income: $3260 Traditional Rental Income: $2201 Airbnb ROI: 5.31% Traditional ROI: 4.13%
3463 ARNEL DRIVE Winter Park, FL **This property qualifies for a closing cost credit up to $3,100 through the Sellerâs pr...	3 beds \| 2 baths \| 1,750 sq.ft.	$398,900	Airbnb cash on cash: 6.79% Traditional cash on cash: 4.9% Airbnb Rental Income: $4337 Traditional Rental Income: $2718 Airbnb ROI: 6.79% Traditional ROI: 4.9%
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.	$450,000	Airbnb cash on cash: 3.9% Traditional cash on cash: 2.79% Airbnb Rental Income: $3260 Traditional Rental Income: $2061 Airbnb ROI: 3.9% Traditional ROI: 2.79%
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%
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.	$819,999	Airbnb cash on cash: 0.75% Traditional cash on cash: -0.31% Airbnb Rental Income: $4337 Traditional Rental Income: $2610 Airbnb ROI: 0.75% Traditional ROI: -0.31%
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%
3031 NORTHWOOD BOULEVARD Winter Park, FL Under Construction. Welcome to this stunning 4-bedroom, 4-bathroom home nestled in the hea...	4 beds \| 4 baths \| 2,978 sq.ft.	$1,699,995	Airbnb cash on cash: 1.56% Traditional cash on cash: 1.25% Airbnb Rental Income: $5745 Traditional Rental Income: $4118 Airbnb ROI: 1.56% Traditional ROI: 1.25%
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.	$799,000	Airbnb cash on cash: 2.64% Traditional cash on cash: 2.63% Airbnb Rental Income: $4337 Traditional Rental Income: $3412 Airbnb ROI: 2.64% Traditional ROI: 2.63%

Vacation Rentals in Winter Park

There are 149 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 $492,450 and the average price per square foot is $249. 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 149 Airbnb properties available for sale in Winter Park.

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

In November 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%

1481 HARMON AVENUE

Winter Park, FL

4 beds | 3 baths | 1,705 sq.ft.

$545,000

Airbnb cash on cash: 6.76%

Traditional cash on cash: 2.56%

Airbnb Rental Income: $5745

Traditional Rental Income: $2462

Airbnb ROI: 6.76%

Traditional ROI: 2.56%

648 CALLAHAN STREET

Winter Park, FL

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

$949,000

Airbnb cash on cash: 2.36%

Traditional cash on cash: 2.05%

Airbnb Rental Income: $4337

Traditional Rental Income: $3147

Airbnb ROI: 2.36%

Traditional ROI: 2.05%

5318 POINSETTA AVENUE

Winter Park, FL

3 beds | 2 baths | 1,467 sq.ft.

$420,000

Airbnb cash on cash: 6.87%

Traditional cash on cash: 3.48%

Airbnb Rental Income: $4337

Traditional Rental Income: $2093

Airbnb ROI: 6.87%

Traditional ROI: 3.48%

3455 ATHENA DRIVE

Winter Park, FL

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

$469,000

Airbnb cash on cash: 8.56%

Traditional cash on cash: 4.97%

Airbnb Rental Income: $5745

Traditional Rental Income: $3019

Airbnb ROI: 8.56%

Traditional ROI: 4.97%

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%

5211 WOODCREST COURT

Winter Park, FL

3 beds | 2 baths | 1,578 sq.ft.

$484,000

Airbnb cash on cash: 5.78%

Traditional cash on cash: 2.92%

Airbnb Rental Income: $4337

Traditional Rental Income: $2132

Airbnb ROI: 5.78%