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 72 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.	$445,000	Airbnb cash on cash: 5.82% Traditional cash on cash: 2.95% Airbnb Rental Income: $4337 Traditional Rental Income: $2229 Airbnb ROI: 5.82% Traditional ROI: 2.95%
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%
1324 INDIANA AVENUE Winter Park, FL Charming two story bungalow built in 1935. Timeless character meets modern comfort in this...	4 beds \| 3 baths \| 1,692 sq.ft.	$745,000	Airbnb cash on cash: 4.32% Traditional cash on cash: 1.95% Airbnb Rental Income: $5745 Traditional Rental Income: $2954 Airbnb ROI: 4.32% Traditional ROI: 1.95%
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.	$1,250,000	Airbnb cash on cash: 1.79% Traditional cash on cash: 0.61% Airbnb Rental Income: $5745 Traditional Rental Income: $3232 Airbnb ROI: 1.79% Traditional ROI: 0.61%
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.	$575,000	Airbnb cash on cash: 4.32% Traditional cash on cash: 2.04% Airbnb Rental Income: $4337 Traditional Rental Income: $2200 Airbnb ROI: 4.32% Traditional ROI: 2.04%
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.	$815,000	Airbnb cash on cash: 3.57% Traditional cash on cash: 2.76% Airbnb Rental Income: $5745 Traditional Rental Income: $3980 Airbnb ROI: 3.57% Traditional ROI: 2.76%
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.	$1,199,900	Airbnb cash on cash: 2.74% Traditional cash on cash: 1.06% Airbnb Rental Income: $5745 Traditional Rental Income: $2726 Airbnb ROI: 2.74% Traditional ROI: 1.06%
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%
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%
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 #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.	$916,050	Airbnb cash on cash: 4.04% Traditional cash on cash: 2.83% Airbnb Rental Income: $5745 Traditional Rental Income: $3560 Airbnb ROI: 4.04% Traditional ROI: 2.83%
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%
3018 NORTHWOOD BOULEVARD Winter Park, FL One or more photo(s) has been virtually staged. "MOVE-IN READY", 3-BED, 2-FULL BATHS, SING...	3 beds \| 2 baths \| 1,761 sq.ft.	$734,000	Airbnb cash on cash: 2.97% Traditional cash on cash: 2.29% Airbnb Rental Income: $4337 Traditional Rental Income: $2958 Airbnb ROI: 2.97% Traditional ROI: 2.29%
1451 Cavendish Road Winter Park, FL Welcome to 1451 Cavendish Road, a beautifully renovated home in the heart of Orwin Manor, ...	3 beds \| 2 baths \| 1,437 sq.ft.	$619,500	Airbnb cash on cash: 3.7% Traditional cash on cash: 1.63% Airbnb Rental Income: $4337 Traditional Rental Income: $2225 Airbnb ROI: 3.7% Traditional ROI: 1.63%
240 E Lake Sue Ave Winter Park, FL Discover the perfect blend of convenience and tranquility with this delightful single-fami...	2 beds \| 2 baths \| 1,329 sq.ft.	$1,107,750	Airbnb cash on cash: 0.55% Traditional cash on cash: 0.33% Airbnb Rental Income: $3260 Traditional Rental Income: $2304 Airbnb ROI: 0.55% Traditional ROI: 0.33%
224 OVERLOOK ROAD Winter Park, FL Discover the timeless allure of this enchanting 2 bedroom, 1.5 bath home, built in 1936 an...	2 beds \| 2 baths \| 1,399 sq.ft.	$665,000	Airbnb cash on cash: 2.08% Traditional cash on cash: 1.94% Airbnb Rental Income: $3260 Traditional Rental Income: $2441 Airbnb ROI: 2.08% Traditional ROI: 1.94%
1341 LYNDALE BOULEVARD Winter Park, FL Under contract-accepting backup offers. Ideally located in the heart of Winter Park, just ...	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%
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%
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%
Lot #20 KAROLINA AVE Winter Park, FL Under contract-accepting backup offers. Pre-Construction. To be built. Experience a life w...	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%
1450 CHESTNUT AVENUE Winter Park, FL Under contract-accepting backup offers. Located in the coveted Tree Streets just a block a...	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%
2580 EUSTON ROAD Winter Park, FL just over .25 acre in winter park with block construction 3 bedroom 2 bath. Opportunity to...	3 beds \| 2 baths \| 1,158 sq.ft.	$425,000	Airbnb cash on cash: 6.37% Traditional cash on cash: 2.9% Airbnb Rental Income: $4337 Traditional Rental Income: $2043 Airbnb ROI: 6.37% Traditional ROI: 2.9%
701 DENTON ROAD Winter Park, FL Motivated Seller! Contact us today. Welcome to this beautifully upgraded home in Winter Pa...	3 beds \| 2 baths \| 2,268 sq.ft.	$565,000	Airbnb cash on cash: 4.22% Traditional cash on cash: 3.44% Airbnb Rental Income: $4337 Traditional Rental Income: $3016 Airbnb ROI: 4.22% Traditional ROI: 3.44%
346 S RANGER BOULEVARD Winter Park, FL PRIME LOCATION! Beautiful 3 Bedroom 2 Bathroom home is located in sought after Winter Park...	3 beds \| 2 baths \| 1,592 sq.ft.	$530,000	Airbnb cash on cash: 4.73% Traditional cash on cash: 2.44% Airbnb Rental Income: $4337 Traditional Rental Income: $2291 Airbnb ROI: 4.73% Traditional ROI: 2.44%
1849 VIBURNUM LANE Winter Park, FL Nestled near the highly sought-after Winter Park area, this beautifully updated 4-bedroom,...	4 beds \| 2 baths \| 1,627 sq.ft.	$425,000	Airbnb cash on cash: 9.46% Traditional cash on cash: 3.75% Airbnb Rental Income: $5745 Traditional Rental Income: $2323 Airbnb ROI: 9.46% Traditional ROI: 3.75%
2218 KING RICHARDS COURT Winter Park, FL One or more photo(s) has been virtually staged. Welcome home to 2218 King Richards Court â...	3 beds \| 2 baths \| 1,562 sq.ft.	$460,000	Airbnb cash on cash: 5.68% Traditional cash on cash: 3.28% Airbnb Rental Income: $4337 Traditional Rental Income: $2391 Airbnb ROI: 5.68% Traditional ROI: 3.28%
2189 SUSSEX ROAD Winter Park, FL One or more photo(s) has been virtually staged. -----MOTIVATED SELLER----- Welcome to 2...	4 beds \| 3 baths \| 1,776 sq.ft.	$535,000	Airbnb cash on cash: 7.11% Traditional cash on cash: 3.38% Airbnb Rental Income: $5745 Traditional Rental Income: $2731 Airbnb ROI: 7.11% Traditional ROI: 3.38%
525 S LAKEMONT AVENUE Winter Park, FL Under Construction. Winter Park Luxury Awaits You! Welcome to your dream homeâa stunn...	4 beds \| 4 baths \| 3,330 sq.ft.	$2,350,000	Airbnb cash on cash: 0.77% Traditional cash on cash: -0.07% Airbnb Rental Income: $5745 Traditional Rental Income: $2773 Airbnb ROI: 0.77% Traditional ROI: -0.07%
1174 WILDMEADOW RUN Winter Park, FL Welcome to Hawks Crest â Winter Parkâs premier gated, resort-style community! This bea...	3 beds \| 3 baths \| 1,770 sq.ft.	$689,000	Airbnb cash on cash: 2.88% Traditional cash on cash: 1.76% Airbnb Rental Income: $4337 Traditional Rental Income: $2702 Airbnb ROI: 2.88% Traditional ROI: 1.76%
3425 FERNDELL DRIVE Winter Park, FL Fully Renovated Gem in Winter Park! Welcome to your dream home in one of Central Floridaâ...	3 beds \| 2 baths \| 1,516 sq.ft.	$409,000	Airbnb cash on cash: 6.77% Traditional cash on cash: 3.46% Airbnb Rental Income: $4337 Traditional Rental Income: $2155 Airbnb ROI: 6.77% Traditional ROI: 3.46%
1608 BOMI CIRCLE Winter Park, FL Your beautifully upgraded home in Winter Park with NO HOA is waiting for you! Centrally lo...	3 beds \| 2 baths \| 1,807 sq.ft.	$475,000	Airbnb cash on cash: 6.12% Traditional cash on cash: 4.18% Airbnb Rental Income: $4337 Traditional Rental Income: $2563 Airbnb ROI: 6.12% Traditional ROI: 4.18%
1422 TIERRA CIRCLE Winter Park, FL PRICE IMPROVEMENT! INCREDIBLE OPPORTUNITY! 5.75% ASSUMABLE MORTGAGE Interest Rate Availa...	4 beds \| 2 baths \| 1,827 sq.ft.	$499,000	Airbnb cash on cash: 7.69% Traditional cash on cash: 3.78% Airbnb Rental Income: $5745 Traditional Rental Income: $2773 Airbnb ROI: 7.69% Traditional ROI: 3.78%

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.

$445,000

Airbnb cash on cash: 5.82%

Traditional cash on cash: 2.95%

Airbnb Rental Income: $4337

Traditional Rental Income: $2229

Airbnb ROI: 5.82%

Traditional ROI: 2.95%

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%

1324 INDIANA AVENUE

Winter Park, FL

4 beds | 3 baths | 1,692 sq.ft.

$745,000

Airbnb cash on cash: 4.32%

Traditional cash on cash: 1.95%

Airbnb Rental Income: $5745

Traditional Rental Income: $2954

Airbnb ROI: 4.32%

Traditional ROI: 1.95%

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.

$1,250,000

Airbnb cash on cash: 1.79%

Traditional cash on cash: 0.61%

Airbnb Rental Income: $5745

Traditional Rental Income: $3232

Airbnb ROI: 1.79%

Traditional ROI: 0.61%

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.

$575,000

Airbnb cash on cash: 4.32%

Traditional cash on cash: 2.04%

Airbnb Rental Income: $4337

Traditional Rental Income: $2200

Airbnb ROI: 4.32%

Traditional ROI: 2.04%

541 W CANTON AVENUE

Winter Park, FL

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%