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 Townhouse For Sale in Winter Park, FL

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

Showing 17 Townhouse 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
1229 PARK GREEN PLACE Winter Park, FL This 2 bedroom, 2 bathroom townhome offers 1,495 square feet of beautifully designed space...	2 beds \| 2 baths \| 1,495 sq.ft.	$372,500	Airbnb cash on cash: 4.02% Traditional cash on cash: 2.56% Airbnb Rental Income: $3260 Traditional Rental Income: $2016 Airbnb ROI: 4.02% Traditional ROI: 2.56%
1275 MICHIGAN AVENUE Winter Park, FL Welcome to this stunning townhome in the heart of Winter Park, built by award-winning Ospr...	3 beds \| 3 baths \| 1,866 sq.ft.	$679,000	Airbnb cash on cash: 2.5% Traditional cash on cash: 1.17% Airbnb Rental Income: $4337 Traditional Rental Income: $2586 Airbnb ROI: 2.5% Traditional ROI: 1.17%
1261 INDIANA AVENUE Winter Park, FL Welcome to The Townhomes at Harper Place, where elegance meets convenience in beautiful Wi...	3 beds \| 3 baths \| 1,660 sq.ft.	$549,900	Airbnb cash on cash: 4.33% Traditional cash on cash: 1.93% Airbnb Rental Income: $4337 Traditional Rental Income: $2192 Airbnb ROI: 4.33% Traditional ROI: 1.93%
2417 PASSAMONTE DRIVE #1E Winter Park, FL Location! Location! Location! Winter Park, Top Rated Florida Zone Schools, Move-In Ready, ...	3 beds \| 3 baths \| 1,837 sq.ft.	$329,999	Airbnb cash on cash: 7.38% Traditional cash on cash: 4.13% Airbnb Rental Income: $4337 Traditional Rental Income: $2416 Airbnb ROI: 7.38% Traditional ROI: 4.13%
7470 CANFORD COURT #23 Winter Park, FL Beautifully updated three bedroom two and a half bath townhome in the heart of Winter Park...	3 beds \| 3 baths \| 1,580 sq.ft.	$249,900	Airbnb cash on cash: 9.53% Traditional cash on cash: 4.23% Airbnb Rental Income: $4337 Traditional Rental Income: $2173 Airbnb ROI: 9.53% Traditional ROI: 4.23%
2774 BRIGHT BIRD LANE Winter Park, FL Motivated seller! Brand new townhouse professionally decorated, and available today! Built...	3 beds \| 3 baths \| 1,907 sq.ft.	$465,000	Airbnb cash on cash: 5.48% Traditional cash on cash: 3.45% Airbnb Rental Income: $4337 Traditional Rental Income: $2540 Airbnb ROI: 5.48% Traditional ROI: 3.45%
2033 CANNY COVE Winter Park, FL Step into this stunning townhome and be greeted by an open-concept kitchen, dining, and li...	3 beds \| 3 baths \| 1,907 sq.ft.	$432,000	Airbnb cash on cash: 4.79% Traditional cash on cash: 2.6% Airbnb Rental Income: $4337 Traditional Rental Income: $2540 Airbnb ROI: 4.79% Traditional ROI: 2.6%
2487 HARBOUR WAY Winter Park, FL Unmissable opportunity in Winter Park! Beautiful house for sale with 3 bedrooms and 3 ...	3 beds \| 3 baths \| 1,803 sq.ft.	$319,900	Airbnb cash on cash: 8.38% Traditional cash on cash: 4.94% Airbnb Rental Income: $4337 Traditional Rental Income: $2390 Airbnb ROI: 8.38% Traditional ROI: 4.94%
1900 ERUDITE WAY Winter Park, FL Seller offering $10,000 credit to buyer at closingâmay be applied toward buyerâs rate ...	3 beds \| 3 baths \| 1,907 sq.ft.	$439,000	Airbnb cash on cash: 5.82% Traditional cash on cash: 3.61% Airbnb Rental Income: $4337 Traditional Rental Income: $2519 Airbnb ROI: 5.82% Traditional ROI: 3.61%
7444 WOODBURN COURT #29 Winter Park, FL * SELLER WILL PAY SPECIAL ASSESSMENT AT CLOSING BRING MONTHLY ASSESSMENT TO $420** So...	2 beds \| 3 baths \| 1,031 sq.ft.	$195,000	Airbnb cash on cash: 6.96% Traditional cash on cash: 2.66% Airbnb Rental Income: $3260 Traditional Rental Income: $1731 Airbnb ROI: 6.96% Traditional ROI: 2.66%
615 WARRENTON ROAD Winter Park, FL One or more photo(s) has been virtually staged. Donât miss out on this beautifully maint...	2 beds \| 2 baths \| 1,221 sq.ft.	$320,000	Airbnb cash on cash: 6.08% Traditional cash on cash: 3.82% Airbnb Rental Income: $3260 Traditional Rental Income: $1848 Airbnb ROI: 6.08% Traditional ROI: 3.82%
2401 ANTILLES DRIVE Winter Park, FL Fantastic end unit with enclosed Florida Room in the sought after Windward Square! This 3/...	3 beds \| 2 baths \| 1,719 sq.ft.	$325,000	Airbnb cash on cash: 8.68% Traditional cash on cash: 4.83% Airbnb Rental Income: $4337 Traditional Rental Income: $2249 Airbnb ROI: 8.68% Traditional ROI: 4.83%
2808 BRIGHT BIRD LANE Winter Park, FL Gorgeous 2-Story Townhome, newly built in 2024. Located in upscale Winter Park, Florida, c...	3 beds \| 3 baths \| 1,916 sq.ft.	$436,900	Airbnb cash on cash: 4.78% Traditional cash on cash: 2.96% Airbnb Rental Income: $4337 Traditional Rental Income: $2681 Airbnb ROI: 4.78% Traditional ROI: 2.96%
1917 S LAKEMONT AVENUE Winter Park, FL Under contract-accepting backup offers. Special financing or closing cost credits availabl...	3 beds \| 4 baths \| 2,051 sq.ft.	$819,700	Airbnb cash on cash: 2.66% Traditional cash on cash: 2.27% Airbnb Rental Income: $4337 Traditional Rental Income: $3129 Airbnb ROI: 2.66% Traditional ROI: 2.27%
607 SAINT JOHNS CT #607 Winter Park, FL Under contract-accepting backup offers. This beauty just got a Great NEW PRICE!!! Check ou...	2 beds \| 2 baths \| 1,120 sq.ft.	$199,000	Airbnb cash on cash: 7.72% Traditional cash on cash: 5.56% Airbnb Rental Income: $3260 Traditional Rental Income: $2121 Airbnb ROI: 7.72% Traditional ROI: 5.56%
1624 FLORENTINO LANE Winter Park, FL Under contract-accepting backup offers. Welcome to this beautifully updated 2-bedroom, 2.5...	2 beds \| 3 baths \| 1,550 sq.ft.	$345,000	Airbnb cash on cash: 5.32% Traditional cash on cash: 3.85% Airbnb Rental Income: $3260 Traditional Rental Income: $2053 Airbnb ROI: 5.32% Traditional ROI: 3.85%
4928 TANGERINE AVE Winter Park, FL Under contract-accepting backup offers. Welcome to this beautifully updated condo (that l...	2 beds \| 2 baths \| 1,281 sq.ft.	$205,000	Airbnb cash on cash: 7.42% Traditional cash on cash: 3.69% Airbnb Rental Income: $3260 Traditional Rental Income: $1804 Airbnb ROI: 7.42% Traditional ROI: 3.69%

Your search for investment property begins and ends here

Airbnb Townhouse For Sale in Winter Park, FL

1229 PARK GREEN PLACE

Winter Park, FL

2 beds | 2 baths | 1,495 sq.ft.

$372,500

Airbnb cash on cash: 4.02%

Traditional cash on cash: 2.56%

Airbnb Rental Income: $3260

Traditional Rental Income: $2016

Airbnb ROI: 4.02%

Traditional ROI: 2.56%

1275 MICHIGAN AVENUE

Winter Park, FL

3 beds | 3 baths | 1,866 sq.ft.

$679,000

Airbnb cash on cash: 2.5%

Traditional cash on cash: 1.17%

Airbnb Rental Income: $4337

Traditional Rental Income: $2586

Airbnb ROI: 2.5%

Traditional ROI: 1.17%

1261 INDIANA AVENUE

Winter Park, FL

3 beds | 3 baths | 1,660 sq.ft.

$549,900

Airbnb cash on cash: 4.33%

Traditional cash on cash: 1.93%

Airbnb Rental Income: $4337

Traditional Rental Income: $2192

Airbnb ROI: 4.33%

Traditional ROI: 1.93%

2417 PASSAMONTE DRIVE #1E

Winter Park, FL

3 beds | 3 baths | 1,837 sq.ft.

$329,999

Airbnb cash on cash: 7.38%

Traditional cash on cash: 4.13%

Airbnb Rental Income: $4337

Traditional Rental Income: $2416

Airbnb ROI: 7.38%

Traditional ROI: 4.13%

7470 CANFORD COURT #23

Winter Park, FL

3 beds | 3 baths | 1,580 sq.ft.

$249,900

Airbnb cash on cash: 9.53%

Traditional cash on cash: 4.23%

Airbnb Rental Income: $4337

Traditional Rental Income: $2173

Airbnb ROI: 9.53%

Traditional ROI: 4.23%

2774 BRIGHT BIRD LANE

Winter Park, FL

3 beds | 3 baths | 1,907 sq.ft.

$465,000

Airbnb cash on cash: 5.48%

Traditional cash on cash: 3.45%

Airbnb Rental Income: $4337

Traditional Rental Income: $2540

Airbnb ROI: 5.48%

Traditional ROI: 3.45%

2033 CANNY COVE

Winter Park, FL

3 beds | 3 baths | 1,907 sq.ft.

$432,000

Airbnb cash on cash: 4.79%

Traditional cash on cash: 2.6%

Airbnb Rental Income: $4337

Traditional Rental Income: $2540

Airbnb ROI: 4.79%

Traditional ROI: 2.6%

2487 HARBOUR WAY

Winter Park, FL

3 beds | 3 baths | 1,803 sq.ft.

$319,900

Airbnb cash on cash: 8.38%

Traditional cash on cash: 4.94%

Airbnb Rental Income: $4337

Traditional Rental Income: $2390

Airbnb ROI: 8.38%