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 Single Family Residential For Sale in Winter Park, FL

Search for Single Family Residential for Sale in Winter Park, Florida. Browse all of Mashvisor’s Single Family Residential listings and other investment property types including Single Family Homes, Multi Family Homes, Condos, Townhouses and Other Homes.

Showing 97 Single Family Residential listings of over 500,000 total investment properties for sale. Visit Mashvisor.com to all investment properties.

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PROPERTY	DETAILS	SALE PRICE	INVESTMENT PERFORMANCE
740 BAFFIE AVENUE Winter Park, FL Welcome to this fully remodeled, move in ready home perfectly situated on a spacious corne...	3 beds \| 2 baths \| 1,456 sq.ft.	$470,000	Airbnb cash on cash: 5.46% Traditional cash on cash: 2.74% Airbnb Rental Income: $4337 Traditional Rental Income: $2229 Airbnb ROI: 5.46% Traditional ROI: 2.74%
2607 Lafayette Ave Winter Park, FL Welcome to 2607 Lafayette Avenueâa stunning custom home in one of Winter Parkâs most d...	4 beds \| 4 baths \| 2,770 sq.ft.	$1,095,000	Airbnb cash on cash: 2.17% Traditional cash on cash: 1.34% Airbnb Rental Income: $5745 Traditional Rental Income: $3752 Airbnb ROI: 2.17% Traditional ROI: 1.34%
1516 PINEWOOD DRIVE Winter Park, FL PINEWOOD SUB N/9 LOT 12 BLK A Well-maintained, modest 2-1 home in College Park with c...	2 beds \| 1 baths \| 1,028 sq.ft.	$335,000	Airbnb cash on cash: 5.29% Traditional cash on cash: 2.66% Airbnb Rental Income: $3260 Traditional Rental Income: $1698 Airbnb ROI: 5.29% Traditional ROI: 2.66%
720 N PENNSYLVANIA AVENUE Winter Park, FL Nestled in one of Winter Parkâs most sought-after locations, this 3-bedroom, 2-bathroom ...	3 beds \| 2 baths \| 1,115 sq.ft.	$550,000	Airbnb cash on cash: 4.56% Traditional cash on cash: 1.6% Airbnb Rental Income: $4337 Traditional Rental Income: $1903 Airbnb ROI: 4.56% Traditional ROI: 1.6%
1400 S PENNSYLVANIA AVENUE Winter Park, FL Look at this rare opportunity to own a chic and trendy residence in winter park in an incr...	4 beds \| 3 baths \| 2,310 sq.ft.	$1,290,000	Airbnb cash on cash: 1.7% Traditional cash on cash: 0.56% Airbnb Rental Income: $5745 Traditional Rental Income: $3232 Airbnb ROI: 1.7% Traditional ROI: 0.56%
1521 CHESTNUT AVENUE Winter Park, FL Modern Luxury in the Heart of Winter Park! Welcome to this stunning modern residence, buil...	4 beds \| 3 baths \| 2,843 sq.ft.	$1,899,900	Airbnb cash on cash: 0.48% Traditional cash on cash: -0.08% Airbnb Rental Income: $5745 Traditional Rental Income: $3620 Airbnb ROI: 0.48% Traditional ROI: -0.08%
726 N PENNSYLVANIA AVENUE Winter Park, FL Welcome to this beautifully designed 3-bedroom, 2-bathroom home, offering a blend of moder...	3 beds \| 2 baths \| 1,167 sq.ft.	$695,000	Airbnb cash on cash: 3.43% Traditional cash on cash: 1.13% Airbnb Rental Income: $4337 Traditional Rental Income: $1931 Airbnb ROI: 3.43% Traditional ROI: 1.13%
720 W WEBSTER AVENUE Winter Park, FL Discover the charm of Winter Park living in this beautifully maintained 1950s home, where ...	3 beds \| 2 baths \| 1,356 sq.ft.	$599,000	Airbnb cash on cash: 4.11% Traditional cash on cash: 1.92% Airbnb Rental Income: $4337 Traditional Rental Income: $2200 Airbnb ROI: 4.11% Traditional ROI: 1.92%
541 W CANTON AVENUE Winter Park, FL Timeless elegance meets boutique craftsmanship at 541 W Canton Avenueâan exceptional new...	4 beds \| 4 baths \| 3,553 sq.ft.	$2,935,000	Airbnb cash on cash: 0.5% Traditional cash on cash: 0.46% Airbnb Rental Income: $5745 Traditional Rental Income: $4490 Airbnb ROI: 0.5% Traditional ROI: 0.46%
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.	$829,000	Airbnb cash on cash: 3.5% Traditional cash on cash: 2.7% Airbnb Rental Income: $5745 Traditional Rental Income: $3980 Airbnb ROI: 3.5% Traditional ROI: 2.7%
250 Cortland Avenue Winter Park, FL Welcome to the epitome of the Winter Park lifestyle at 250 Cortland Ave, nestled among mil...	3 beds \| 2 baths \| 2,114 sq.ft.	$950,000	Airbnb cash on cash: 2.31% Traditional cash on cash: 1.8% Airbnb Rental Income: $4337 Traditional Rental Income: $2974 Airbnb ROI: 2.31% Traditional ROI: 1.8%
3601 MIDIRON DRIVE Winter Park, FL BUILD YOUR DREAM HOME IN WINTER PARK! Nestled directly across from the historic Dubsdread...	2 beds \| 1 baths \| 954 sq.ft.	$459,000	Airbnb cash on cash: 3.36% Traditional cash on cash: 1.18% Airbnb Rental Income: $3260 Traditional Rental Income: $1593 Airbnb ROI: 3.36% Traditional ROI: 1.18%
1981 BLUE RIDGE ROAD Winter Park, FL One or more photo(s) has been virtually staged. **This house comes with a REDUCED RATE thr...	4 beds \| 2 baths \| 2,750 sq.ft.	$1,260,000	Airbnb cash on cash: 2.56% Traditional cash on cash: 0.96% Airbnb Rental Income: $5745 Traditional Rental Income: $2726 Airbnb ROI: 2.56% Traditional ROI: 0.96%
920 GLORIOSA AVENUE Winter Park, FL Charming Move-In Ready Home in the Heart of Winter Park! Discover this beautifully main...	3 beds \| 2 baths \| 1,540 sq.ft.	$409,988	Airbnb cash on cash: 7.29% Traditional cash on cash: 4.5% Airbnb Rental Income: $4337 Traditional Rental Income: $2355 Airbnb ROI: 7.29% Traditional ROI: 4.5%
2128 SYCAMORE DRIVE Winter Park, FL MUST SEE! RENOVATED, MOVE-IN READY! Donât miss this fantastic opportunity to own a beau...	3 beds \| 2 baths \| 1,760 sq.ft.	$825,000	Airbnb cash on cash: 2.72% Traditional cash on cash: 1.63% Airbnb Rental Income: $4337 Traditional Rental Income: $2586 Airbnb ROI: 2.72% Traditional ROI: 1.63%
1875 STAUNTON AVENUE Winter Park, FL Welcome to this newer single-family home tucked away in the Karolina On Killarney section ...	4 beds \| 2 baths \| 2,036 sq.ft.	$560,000	Airbnb cash on cash: 6.18% Traditional cash on cash: 0.81% Airbnb Rental Income: $5745 Traditional Rental Income: $1793 Airbnb ROI: 6.18% Traditional ROI: 0.81%
1660 WALNUT AVENUE Winter Park, FL Under Construction. Elegant and modern new construction home perfectly situated in beautif...	4 beds \| 4 baths \| 2,172 sq.ft.	$1,759,000	Airbnb cash on cash: 1.35% Traditional cash on cash: 0.67% Airbnb Rental Income: $5745 Traditional Rental Income: $3477 Airbnb ROI: 1.35% Traditional ROI: 0.67%
1564 CAVENDISH ROAD Winter Park, FL Charming 3BR bungalow in sought-after Orwin Manor with timeless appeal and tons of potenti...	3 beds \| 1 baths \| 1,140 sq.ft.	$450,000	Airbnb cash on cash: 5.72% Traditional cash on cash: 1.95% Airbnb Rental Income: $4337 Traditional Rental Income: $1838 Airbnb ROI: 5.72% Traditional ROI: 1.95%
1341 LYNDALE BOULEVARD Winter Park, FL Ideally located in the heart of Winter Park, just steps from iconic Park Avenue and around...	4 beds \| 3 baths \| 2,388 sq.ft.	$1,130,000	Airbnb cash on cash: 2.17% Traditional cash on cash: 0.44% Airbnb Rental Income: $5745 Traditional Rental Income: $2775 Airbnb ROI: 2.17% Traditional ROI: 0.44%
1399 ALOMA AVENUE Winter Park, FL *Price Adjustment * Charming 1948 Winter Park Home! This 3-bedroom, 2-bathroom gem is ...	3 beds \| 2 baths \| 1,804 sq.ft.	$665,000	Airbnb cash on cash: 4.06% Traditional cash on cash: 2.68% Airbnb Rental Income: $4337 Traditional Rental Income: $2575 Airbnb ROI: 4.06% Traditional ROI: 2.68%
240 CAMBRIDGE BOULEVARD Winter Park, FL 3-Bed, 2-Bath Home in Prime Winter Park Location! Steps away from paddleboarding, kayaking...	3 beds \| 2 baths \| 1,630 sq.ft.	$525,000	Airbnb cash on cash: 4.87% Traditional cash on cash: 2.63% Airbnb Rental Income: $4337 Traditional Rental Income: $2325 Airbnb ROI: 4.87% Traditional ROI: 2.63%
446 ALBERTA DRIVE Winter Park, FL Charming Opportunity in Prime Winter Park â 446 Alberta Drive, Winter Park, FL! First t...	4 beds \| 3 baths \| 3,263 sq.ft.	$1,750,000	Airbnb cash on cash: 1.39% Traditional cash on cash: 0.84% Airbnb Rental Income: $5745 Traditional Rental Income: $3714 Airbnb ROI: 1.39% Traditional ROI: 0.84%
Lot #20 KAROLINA AVE Winter Park, FL Pre-Construction. To be built. Experience a life where timeless craftsmanship meets modern...	4 beds \| 4 baths \| 2,662 sq.ft.	$935,040	Airbnb cash on cash: 3.94% Traditional cash on cash: 2.86% Airbnb Rental Income: $5745 Traditional Rental Income: $3657 Airbnb ROI: 3.94% Traditional ROI: 2.86%
Lot #21 KAROLINA AVE Winter Park, FL Pre-Construction. To be built. Step into a life where charm meets convenience in the heart...	4 beds \| 4 baths \| 2,662 sq.ft.	$903,050	Airbnb cash on cash: 4.12% Traditional cash on cash: 2.88% Airbnb Rental Income: $5745 Traditional Rental Income: $3560 Airbnb ROI: 4.12% Traditional ROI: 2.88%
1450 CHESTNUT AVENUE Winter Park, FL Located in the coveted Tree Streets just a block and a half from Lake Knowles, this timele...	3 beds \| 4 baths \| 1,942 sq.ft.	$1,095,000	Airbnb cash on cash: 1.63% Traditional cash on cash: 1.61% Airbnb Rental Income: $4337 Traditional Rental Income: $3410 Airbnb ROI: 1.63% Traditional ROI: 1.61%
1611 TIOGA TRAIL Winter Park, FL Built by Charles Clayton a renowned builder in Winter Park, this beautifully updated 4-bed...	4 beds \| 2 baths \| 2,388 sq.ft.	$1,125,000	Airbnb cash on cash: 2.34% Traditional cash on cash: 1% Airbnb Rental Income: $5745 Traditional Rental Income: $3188 Airbnb ROI: 2.34% Traditional ROI: 1%
1872 BISCAYNE DRIVE Winter Park, FL Donât miss this rare opportunity to own a professionally landscaped, beautifully maintai...	2 beds \| 1 baths \| 969 sq.ft.	$439,000	Airbnb cash on cash: 3.85% Traditional cash on cash: 1.85% Airbnb Rental Income: $3260 Traditional Rental Income: $1706 Airbnb ROI: 3.85% Traditional ROI: 1.85%
1007 EARLY AVENUE Winter Park, FL Welcome to your next chapter at 1007 Early Ave in Winter Park, a charming 3-bedroom, 2-bat...	3 beds \| 2 baths \| 1,721 sq.ft.	$425,000	Airbnb cash on cash: 7.09% Traditional cash on cash: 4.77% Airbnb Rental Income: $4337 Traditional Rental Income: $2502 Airbnb ROI: 7.09% Traditional ROI: 4.77%
2812 WOODSIDE AVENUE Winter Park, FL Under contract-accepting backup offers. In the heart of the Audubon Park Garden District y...	3 beds \| 2 baths \| 1,842 sq.ft.	$625,000	Airbnb cash on cash: 3.49% Traditional cash on cash: 2.72% Airbnb Rental Income: $4337 Traditional Rental Income: $2979 Airbnb ROI: 3.49% Traditional ROI: 2.72%
1420 PALMER AVENUE Winter Park, FL Under contract-accepting backup offers. **DON'T LET THIS OPPORTUNITY PASS YOU BY, BACK ON ...	4 beds \| 4 baths \| 2,953 sq.ft.	$1,325,000	Airbnb cash on cash: 1.88% Traditional cash on cash: 1.47% Airbnb Rental Income: $5745 Traditional Rental Income: $4099 Airbnb ROI: 1.88% Traditional ROI: 1.47%
786 ANTONETTE AVENUE Winter Park, FL Under contract-accepting backup offers. FIRST TIME OFFERING! Charming Bungalow in the hear...	2 beds \| 1 baths \| 1,146 sq.ft.	$695,000	Airbnb cash on cash: 1.67% Traditional cash on cash: 0.41% Airbnb Rental Income: $3260 Traditional Rental Income: $1706 Airbnb ROI: 1.67% Traditional ROI: 0.41%
1975 STAUNTON AVENUE Winter Park, FL Under contract-accepting backup offers. One or more photo(s) has been virtually staged. An...	3 beds \| 2 baths \| 1,200 sq.ft.	$386,500	Airbnb cash on cash: 7.19% Traditional cash on cash: 3.25% Airbnb Rental Income: $4337 Traditional Rental Income: $1998 Airbnb ROI: 7.19% Traditional ROI: 3.25%
1682 ARBOR PARK DRIVE Winter Park, FL Under contract-accepting backup offers. Under Construction. Modern elegance and timeless s...	4 beds \| 4 baths \| 2,950 sq.ft.	$1,800,000	Airbnb cash on cash: 1.42% Traditional cash on cash: 1.1% Airbnb Rental Income: $5745 Traditional Rental Income: $4071 Airbnb ROI: 1.42% Traditional ROI: 1.1%
1020 MAYFIELD AVENUE Winter Park, FL Under contract-accepting backup offers. Exquisite, Luxury Listing in the Heart of Winter P...	4 beds \| 3 baths \| 2,663 sq.ft.	$2,775,000	Airbnb cash on cash: 0.34% Traditional cash on cash: 0.01% Airbnb Rental Income: $5745 Traditional Rental Income: $3739 Airbnb ROI: 0.34% Traditional ROI: 0.01%
2190 TEMPLE DRIVE Winter Park, FL Under contract-accepting backup offers. LOCATION! LOCATION! LOCATION! EXPECT TO BE IMPRESS...	3 beds \| 2 baths \| 1,442 sq.ft.	$695,000	Airbnb cash on cash: 3.43% Traditional cash on cash: 2.02% Airbnb Rental Income: $4337 Traditional Rental Income: $2511 Airbnb ROI: 3.43% Traditional ROI: 2.02%
770 W WEBSTER AVENUE Winter Park, FL Under contract-accepting backup offers. Stop the car! Check out this classic 4/2 Florida ...	4 beds \| 2 baths \| 1,008 sq.ft.	$725,000	Airbnb cash on cash: 5% Traditional cash on cash: 1.09% Airbnb Rental Income: $5745 Traditional Rental Income: $1955 Airbnb ROI: 5% Traditional ROI: 1.09%
1835 KAROLINA AVE Winter Park, FL Under contract-accepting backup offers. Pre-Construction. To be built. Experience the best...	4 beds \| 4 baths \| 2,662 sq.ft.	$864,020	Airbnb cash on cash: 4.35% Traditional cash on cash: 3.14% Airbnb Rental Income: $5745 Traditional Rental Income: $3630 Airbnb ROI: 4.35% Traditional ROI: 3.14%
2308 MULBRY DRIVE Winter Park, FL Under contract-accepting backup offers. CHARMING 3 BEDROOM, 2 BATH IN THE HEART OF WINTER ...	3 beds \| 2 baths \| 1,428 sq.ft.	$549,000	Airbnb cash on cash: 4.81% Traditional cash on cash: 2.82% Airbnb Rental Income: $4337 Traditional Rental Income: $2401 Airbnb ROI: 4.81% Traditional ROI: 2.82%
260 ORANGE TERRACE DRIVE Winter Park, FL Under contract-accepting backup offers. What a great location - Ready for move in before t...	3 beds \| 3 baths \| 1,330 sq.ft.	$479,000	Airbnb cash on cash: 5.94% Traditional cash on cash: 3.99% Airbnb Rental Income: $4337 Traditional Rental Income: $2553 Airbnb ROI: 5.94% Traditional ROI: 3.99%
611 OLOLU DRIVE Winter Park, FL Under contract-accepting backup offers. RARE FIND! MUST SEE! PRIME LOCATION! NO HOA! Check...	3 beds \| 2 baths \| 1,145 sq.ft.	$354,900	Airbnb cash on cash: 7.68% Traditional cash on cash: 2.99% Airbnb Rental Income: $4337 Traditional Rental Income: $1861 Airbnb ROI: 7.68% Traditional ROI: 2.99%

Your search for investment property begins and ends here

Airbnb Single Family Residential For Sale in Winter Park, FL

740 BAFFIE AVENUE

Winter Park, FL

3 beds | 2 baths | 1,456 sq.ft.

$470,000

Airbnb cash on cash: 5.46%

Traditional cash on cash: 2.74%

Airbnb Rental Income: $4337

Traditional Rental Income: $2229

Airbnb ROI: 5.46%

Traditional ROI: 2.74%

2607 Lafayette Ave

Winter Park, FL

4 beds | 4 baths | 2,770 sq.ft.

$1,095,000

Airbnb cash on cash: 2.17%

Traditional cash on cash: 1.34%

Airbnb Rental Income: $5745

Traditional Rental Income: $3752

Airbnb ROI: 2.17%

Traditional ROI: 1.34%

1516 PINEWOOD DRIVE

Winter Park, FL

2 beds | 1 baths | 1,028 sq.ft.

$335,000

Airbnb cash on cash: 5.29%

Traditional cash on cash: 2.66%

Airbnb Rental Income: $3260

Traditional Rental Income: $1698

Airbnb ROI: 5.29%

Traditional ROI: 2.66%

720 N PENNSYLVANIA AVENUE

Winter Park, FL

3 beds | 2 baths | 1,115 sq.ft.

$550,000

Airbnb cash on cash: 4.56%

Traditional cash on cash: 1.6%

Airbnb Rental Income: $4337

Traditional Rental Income: $1903

Airbnb ROI: 4.56%

Traditional ROI: 1.6%

1400 S PENNSYLVANIA AVENUE

Winter Park, FL

4 beds | 3 baths | 2,310 sq.ft.

$1,290,000

Airbnb cash on cash: 1.7%

Traditional cash on cash: 0.56%

Airbnb Rental Income: $5745

Traditional Rental Income: $3232

Airbnb ROI: 1.7%

Traditional ROI: 0.56%

1521 CHESTNUT AVENUE

Winter Park, FL

4 beds | 3 baths | 2,843 sq.ft.

$1,899,900

Airbnb cash on cash: 0.48%

Traditional cash on cash: -0.08%

Airbnb Rental Income: $5745

Traditional Rental Income: $3620

Airbnb ROI: 0.48%

Traditional ROI: -0.08%

726 N PENNSYLVANIA AVENUE

Winter Park, FL

3 beds | 2 baths | 1,167 sq.ft.

$695,000

Airbnb cash on cash: 3.43%

Traditional cash on cash: 1.13%

Airbnb Rental Income: $4337

Traditional Rental Income: $1931

Airbnb ROI: 3.43%

Traditional ROI: 1.13%

720 W WEBSTER AVENUE

Winter Park, FL

3 beds | 2 baths | 1,356 sq.ft.

$599,000

Airbnb cash on cash: 4.11%

Traditional cash on cash: 1.92%

Airbnb Rental Income: $4337

Traditional Rental Income: $2200

Airbnb ROI: 4.11%