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 104 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
2844 SCARLET ROAD Winter Park, FL Welcome to this stunning mid-century modern beauty where timeless design meets thoughtful,...	4 beds \| 2 baths \| 1,508 sq.ft.	$519,000	Airbnb cash on cash: 7.24% Traditional cash on cash: 3.35% Airbnb Rental Income: $5745 Traditional Rental Income: $2713 Airbnb ROI: 7.24% Traditional ROI: 3.35%
311 CORTLAND AVENUE Winter Park, FL Under contract-accepting backup offers. Location, location, location! Whether you're ready...	2 beds \| 2 baths \| 1,382 sq.ft.	$799,900	Airbnb cash on cash: 1.45% Traditional cash on cash: 0.96% Airbnb Rental Income: $3260 Traditional Rental Income: $2160 Airbnb ROI: 1.45% Traditional ROI: 0.96%
1018 TURNER ROAD Winter Park, FL Seller may consider buyer concessions if made in an offer \| Lakefront charm meets quiet lu...	4 beds \| 2 baths \| 2,237 sq.ft.	$890,000	Airbnb cash on cash: 3.49% Traditional cash on cash: 2.11% Airbnb Rental Income: $5745 Traditional Rental Income: $3458 Airbnb ROI: 3.49% Traditional ROI: 2.11%
7602 LODGE POLE TRAIL Winter Park, FL Under contract-accepting backup offers. Nestled in desirable Arrowhead Cove, this meticulo...	3 beds \| 3 baths \| 1,906 sq.ft.	$474,998	Airbnb cash on cash: 5.68% Traditional cash on cash: 3.98% Airbnb Rental Income: $4337 Traditional Rental Income: $2667 Airbnb ROI: 5.68% Traditional ROI: 3.98%
690 S LAKEMONT AVENUE Winter Park, FL Under contract-accepting backup offers. Short Sale. Beautifully updated 4BR/3BA pool home ...	4 beds \| 3 baths \| 1,897 sq.ft.	$550,000	Airbnb cash on cash: 6.35% Traditional cash on cash: 3.9% Airbnb Rental Income: $5745 Traditional Rental Income: $3342 Airbnb ROI: 6.35% Traditional ROI: 3.9%
1023 PRINCESS GATE BOULEVARD Winter Park, FL Under contract-accepting backup offers. VA AssumableA HIDDEN GEM nestled on Lake Deeks...	4 beds \| 3 baths \| 2,465 sq.ft.	$695,000	Airbnb cash on cash: 5.9% Traditional cash on cash: 4.87% Airbnb Rental Income: $5745 Traditional Rental Income: $3934 Airbnb ROI: 5.9% Traditional ROI: 4.87%
8065 PLEASANT PINE CIRCLE Winter Park, FL **This property qualifies for a closing cost credit up to $8,800 through the Sellerâs pr...	4 beds \| 2 baths \| 1,843 sq.ft.	$570,000	Airbnb cash on cash: 6.53% Traditional cash on cash: 2.33% Airbnb Rental Income: $5745 Traditional Rental Income: $2364 Airbnb ROI: 6.53% Traditional ROI: 2.33%
744 CORNWALL ROAD Winter Park, FL Charming 4-Bedroom Home in Desirable Winter Park Pines Welcome to your new home in the he...	4 beds \| 2 baths \| 1,968 sq.ft.	$750,000	Airbnb cash on cash: 4.73% Traditional cash on cash: 2.13% Airbnb Rental Income: $5745 Traditional Rental Income: $2775 Airbnb ROI: 4.73% Traditional ROI: 2.13%
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.	$369,000	Airbnb cash on cash: 4.72% Traditional cash on cash: 2.32% Airbnb Rental Income: $3260 Traditional Rental Income: $1698 Airbnb ROI: 4.72% Traditional ROI: 2.32%
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%
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%
701 DENTON ROAD Winter Park, FL Seller will consider concessions. Seller Financing available. Contact us today. Welcome to...	3 beds \| 2 baths \| 2,268 sq.ft.	$575,000	Airbnb cash on cash: 4.13% Traditional cash on cash: 3.37% Airbnb Rental Income: $4337 Traditional Rental Income: $3016 Airbnb ROI: 4.13% Traditional ROI: 3.37%
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%
1701 PALMER AVENUE Winter Park, FL One or more photo(s) has been virtually staged. Charming Winter Park Pool Home â A Rare ...	4 beds \| 3 baths \| 2,841 sq.ft.	$1,295,000	Airbnb cash on cash: 1.85% Traditional cash on cash: 1.56% Airbnb Rental Income: $5745 Traditional Rental Income: $4249 Airbnb ROI: 1.85% Traditional ROI: 1.56%
2381 ROXBURY ROAD Winter Park, FL Beautiful 3 Bedrooms 2 Baths in highly desired location. Established pet friendly neighbo...	3 beds \| 2 baths \| 1,645 sq.ft.	$525,000	Airbnb cash on cash: 5.41% Traditional cash on cash: 3.37% Airbnb Rental Income: $4337 Traditional Rental Income: $2423 Airbnb ROI: 5.41% Traditional ROI: 3.37%
1421 SUNSET DRIVE Winter Park, FL Under contract-accepting backup offers. BUYER GOT COLD FEET= YOUR OPPORTUNITY! Welcome to ...	3 beds \| 4 baths \| 1,672 sq.ft.	$835,000	Airbnb cash on cash: 2.27% Traditional cash on cash: 1.7% Airbnb Rental Income: $4337 Traditional Rental Income: $2982 Airbnb ROI: 2.27% Traditional ROI: 1.7%
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.	$750,000	Airbnb cash on cash: 3.11% Traditional cash on cash: 0.97% Airbnb Rental Income: $4337 Traditional Rental Income: $1931 Airbnb ROI: 3.11% Traditional ROI: 0.97%
3490 BOUGAINVILLEA DRIVE Winter Park, FL Step into the charm and comfort of this inviting 3-bedroom, 2-bath Winter Park home, where...	3 beds \| 2 baths \| 1,461 sq.ft.	$377,500	Airbnb cash on cash: 7.65% Traditional cash on cash: 4.77% Airbnb Rental Income: $4337 Traditional Rental Income: $2405 Airbnb ROI: 7.65% Traditional ROI: 4.77%
1354 TIERRA CIRCLE Winter Park, FL Located in the highly sought-after Casa Aloma community, this charming 1960s home offers t...	4 beds \| 2 baths \| 1,827 sq.ft.	$449,900	Airbnb cash on cash: 8.85% Traditional cash on cash: 3.82% Airbnb Rental Income: $5745 Traditional Rental Income: $2479 Airbnb ROI: 8.85% Traditional ROI: 3.82%
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.	$449,900	Airbnb cash on cash: 8.89% Traditional cash on cash: 3.49% Airbnb Rental Income: $5745 Traditional Rental Income: $2323 Airbnb ROI: 8.89% Traditional ROI: 3.49%
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.	$649,000	Airbnb cash on cash: 3.72% Traditional cash on cash: 1.7% Airbnb Rental Income: $4337 Traditional Rental Income: $2200 Airbnb ROI: 3.72% Traditional ROI: 1.7%
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.	$3,150,000	Airbnb cash on cash: 0.4% Traditional cash on cash: 0.36% Airbnb Rental Income: $5745 Traditional Rental Income: $4490 Airbnb ROI: 0.4% Traditional ROI: 0.36%
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%
2774 BANCHORY ROAD Winter Park, FL Welcome to this beautifully maintained 3-bedroom, 2-bathroom block ranch home in Winter Pa...	3 beds \| 2 baths \| 1,560 sq.ft.	$500,000	Airbnb cash on cash: 4.83% Traditional cash on cash: 2.35% Airbnb Rental Income: $4337 Traditional Rental Income: $2268 Airbnb ROI: 4.83% Traditional ROI: 2.35%
1621 PURITAN, Winter Park, FL Down Payment Assistance Available! Welcome to 1621 Puritan Ave, a beautifully renovated po...	4 beds \| 2 baths \| 1,765 sq.ft.	$440,000	Airbnb cash on cash: 8.97% Traditional cash on cash: 4.37% Airbnb Rental Income: $5745 Traditional Rental Income: $2704 Airbnb ROI: 8.97% Traditional ROI: 4.37%
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.	$960,000	Airbnb cash on cash: 2.28% Traditional cash on cash: 1.77% Airbnb Rental Income: $4337 Traditional Rental Income: $2974 Airbnb ROI: 2.28% Traditional ROI: 1.77%
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.	$479,000	Airbnb cash on cash: 3.18% Traditional cash on cash: 1.09% Airbnb Rental Income: $3260 Traditional Rental Income: $1593 Airbnb ROI: 3.18% Traditional ROI: 1.09%
5331 OAK COURT Winter Park, FL https://my.matterport.com/show/?m=o2WBZtN1TXm Welcome to Wrenwood Heights Community!! V...	3 beds \| 2 baths \| 1,263 sq.ft.	$460,000	Airbnb cash on cash: 6.24% Traditional cash on cash: 4.01% Airbnb Rental Income: $4337 Traditional Rental Income: $2464 Airbnb ROI: 6.24% Traditional ROI: 4.01%
1710 ASTER DRIVE Winter Park, FL Price improvement!!! Renovated Winter Park home offering 3 bedrooms 2 baths with 1646 sq ...	3 beds \| 2 baths \| 1,664 sq.ft.	$459,000	Airbnb cash on cash: 6.45% Traditional cash on cash: 4.38% Airbnb Rental Income: $4337 Traditional Rental Income: $2536 Airbnb ROI: 6.45% Traditional ROI: 4.38%
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.	$1,285,000	Airbnb cash on cash: 2.49% Traditional cash on cash: 0.93% Airbnb Rental Income: $5745 Traditional Rental Income: $2726 Airbnb ROI: 2.49% Traditional ROI: 0.93%
1049 TUSCANY PLACE Winter Park, FL Under contract-accepting backup offers. This is a rare opportunity to own a ONE STORY LARK...	4 beds \| 2 baths \| 2,471 sq.ft.	$1,285,000	Airbnb cash on cash: 1.55% Traditional cash on cash: 0.1% Airbnb Rental Income: $5745 Traditional Rental Income: $2871 Airbnb ROI: 1.55% Traditional ROI: 0.1%
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%
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%
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.	$420,100	Airbnb cash on cash: 6.57% Traditional cash on cash: 3.34% Airbnb Rental Income: $4337 Traditional Rental Income: $2155 Airbnb ROI: 6.57% Traditional ROI: 3.34%
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%
1309 PARADISE LANE Winter Park, FL New price. Welcome to Harbour Ridge in charming Winter Park â where thereâs no HOA and...	3 beds \| 2 baths \| 1,606 sq.ft.	$369,000	Airbnb cash on cash: 8.17% Traditional cash on cash: 4.61% Airbnb Rental Income: $4337 Traditional Rental Income: $2191 Airbnb ROI: 8.17% Traditional ROI: 4.61%
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%

Your search for investment property begins and ends here

Airbnb Single Family Residential For Sale in Winter Park, FL

2844 SCARLET ROAD

Winter Park, FL

4 beds | 2 baths | 1,508 sq.ft.

$519,000

Airbnb cash on cash: 7.24%

Traditional cash on cash: 3.35%

Airbnb Rental Income: $5745

Traditional Rental Income: $2713

Airbnb ROI: 7.24%

Traditional ROI: 3.35%

311 CORTLAND AVENUE

Winter Park, FL

2 beds | 2 baths | 1,382 sq.ft.

$799,900

Airbnb cash on cash: 1.45%

Traditional cash on cash: 0.96%

Airbnb Rental Income: $3260

Traditional Rental Income: $2160

Airbnb ROI: 1.45%

Traditional ROI: 0.96%

1018 TURNER ROAD

Winter Park, FL

4 beds | 2 baths | 2,237 sq.ft.

$890,000

Airbnb cash on cash: 3.49%

Traditional cash on cash: 2.11%

Airbnb Rental Income: $5745

Traditional Rental Income: $3458

Airbnb ROI: 3.49%

Traditional ROI: 2.11%

7602 LODGE POLE TRAIL

Winter Park, FL

3 beds | 3 baths | 1,906 sq.ft.

$474,998

Airbnb cash on cash: 5.68%

Traditional cash on cash: 3.98%

Airbnb Rental Income: $4337

Traditional Rental Income: $2667

Airbnb ROI: 5.68%

Traditional ROI: 3.98%

690 S LAKEMONT AVENUE

Winter Park, FL

4 beds | 3 baths | 1,897 sq.ft.

$550,000

Airbnb cash on cash: 6.35%

Traditional cash on cash: 3.9%

Airbnb Rental Income: $5745

Traditional Rental Income: $3342

Airbnb ROI: 6.35%

Traditional ROI: 3.9%

1023 PRINCESS GATE BOULEVARD

Winter Park, FL

4 beds | 3 baths | 2,465 sq.ft.

$695,000

Airbnb cash on cash: 5.9%

Traditional cash on cash: 4.87%

Airbnb Rental Income: $5745

Traditional Rental Income: $3934

Airbnb ROI: 5.9%

Traditional ROI: 4.87%

8065 PLEASANT PINE CIRCLE

Winter Park, FL

4 beds | 2 baths | 1,843 sq.ft.

$570,000

Airbnb cash on cash: 6.53%

Traditional cash on cash: 2.33%

Airbnb Rental Income: $5745

Traditional Rental Income: $2364

Airbnb ROI: 6.53%

Traditional ROI: 2.33%

744 CORNWALL ROAD

Winter Park, FL

4 beds | 2 baths | 1,968 sq.ft.

$750,000

Airbnb cash on cash: 4.73%

Traditional cash on cash: 2.13%

Airbnb Rental Income: $5745

Traditional Rental Income: $2775

Airbnb ROI: 4.73%