Real Estate Investment Properties for Sale in Winter Park, FL

Looking for investment property in Winter Park, FL with high ROI ?

Explore a variety of short-term homes & houses in Winter Park, FL. Invest wisely with VRBO & Winter Park, FL Airbnb properties available for purchase. Find your ideal investment property among our curated listings for a rewarding real estate venture.

Townhouses 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 14 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
1768 MONDRIAN CIRCLE Winter Park, FL One or more photo(s) has been virtually staged. Step into refined lakeside living at the e...	3 beds \| 4 baths \| 2,193 sq.ft.	$1,099,000	Airbnb cash on cash: 0.89% Traditional cash on cash: 1.61% Airbnb Rental Income: $4337 Traditional Rental Income: $4159 Airbnb ROI: 0.89% Traditional ROI: 1.61%
962 ARAGON AVENUE Winter Park, FL Welcome to this BEAUTIFULLY MAINTAINED and thoughtfully upgraded 3-bedroom, 2-bath townhom...	3 beds \| 2 baths \| 1,680 sq.ft.	$599,900	Airbnb cash on cash: 3.79% Traditional cash on cash: 1.71% Airbnb Rental Income: $4337 Traditional Rental Income: $2260 Airbnb ROI: 3.79% Traditional ROI: 1.71%
7470 CANFORD COURT #23 Winter Park, FL New updates, a new fence, and extra outdoor space on a desirable corner lot. Beautifully u...	3 beds \| 3 baths \| 1,580 sq.ft.	$248,900	Airbnb cash on cash: 9.22% Traditional cash on cash: 3.89% Airbnb Rental Income: $4337 Traditional Rental Income: $2173 Airbnb ROI: 9.22% Traditional ROI: 3.89%
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: 4.14% Airbnb Rental Income: $4337 Traditional Rental Income: $2843 Airbnb ROI: 5.48% Traditional ROI: 4.14%
2808 BRIGHT BIRD LANE Winter Park, FL Impeccable 2-story townhome, newly built in 2024 and located in Grayson Square, a Gated Lu...	3 beds \| 3 baths \| 1,907 sq.ft.	$399,000	Airbnb cash on cash: 5.27% Traditional cash on cash: 3.28% Airbnb Rental Income: $4337 Traditional Rental Income: $2681 Airbnb ROI: 5.27% Traditional ROI: 3.28%
1951 CANNY COVE Winter Park, FL Welcome to easy, light-filled living in this beautifully maintained 3-bedroom, 2.5-bath co...	3 beds \| 3 baths \| 1,782 sq.ft.	$444,900	Airbnb cash on cash: 4.46% Traditional cash on cash: 2.78% Airbnb Rental Income: $4337 Traditional Rental Income: $2724 Airbnb ROI: 4.46% Traditional ROI: 2.78%
1995 CANNY COVE Winter Park, FL Welcome to Grayson Square at Winter Park by Pulte Homes. This interior Springdale II two-s...	3 beds \| 3 baths \| 1,907 sq.ft.	$425,000	Airbnb cash on cash: 4.93% Traditional cash on cash: 2.83% Airbnb Rental Income: $4337 Traditional Rental Income: $2587 Airbnb ROI: 4.93% Traditional ROI: 2.83%
2676 BARBADOS DRIVE Winter Park, FL Welcome to this beautifully maintained 3-bedroom, 2-bathroom corner-unit townhome located ...	3 beds \| 2 baths \| 1,743 sq.ft.	$340,000	Airbnb cash on cash: 7.89% Traditional cash on cash: 4.9% Airbnb Rental Income: $4337 Traditional Rental Income: $2472 Airbnb ROI: 7.89% Traditional ROI: 4.9%
7444 WOODBURN COURT #29 Winter Park, FL Under contract-accepting backup offers. Sought after Winter Park Location! 2-bedroom, 2.5...	2 beds \| 3 baths \| 1,031 sq.ft.	$165,000	Airbnb cash on cash: 9.99% Traditional cash on cash: 7.22% Airbnb Rental Income: $3260 Traditional Rental Income: $2092 Airbnb ROI: 9.99% Traditional ROI: 7.22%
2401 ANTILLES DRIVE Winter Park, FL Under contract-accepting backup offers. Fantastic end unit with enclosed Florida Room in t...	3 beds \| 2 baths \| 1,719 sq.ft.	$320,000	Airbnb cash on cash: 8.84% Traditional cash on cash: 6.25% Airbnb Rental Income: $4337 Traditional Rental Income: $2645 Airbnb ROI: 8.84% Traditional ROI: 6.25%
1515 WINTER GREEN BOULEVARD Winter Park, FL Under contract-accepting backup offers. Offering the comfort and feel of a single-family h...	3 beds \| 3 baths \| 1,652 sq.ft.	$300,000	Airbnb cash on cash: 8.74% Traditional cash on cash: 5.53% Airbnb Rental Income: $4337 Traditional Rental Income: $2517 Airbnb ROI: 8.74% Traditional ROI: 5.53%
2400 DOMINICA RUN Winter Park, FL Under contract-accepting backup offers. CHARMING 2/1 MOVE IN READY TOWNHOME in highly soug...	2 beds \| 1 baths \| 854 sq.ft.	$220,000	Airbnb cash on cash: 9.96% Traditional cash on cash: 6.02% Airbnb Rental Income: $3260 Traditional Rental Income: $1707 Airbnb ROI: 9.96% Traditional ROI: 6.02%
7485 ALOMA PINES COURT Winter Park, FL Under contract-accepting backup offers. Experience the perfect blend of luxury and conveni...	3 beds \| 3 baths \| 1,787 sq.ft.	$375,000	Airbnb cash on cash: 5.97% Traditional cash on cash: 3.17% Airbnb Rental Income: $4337 Traditional Rental Income: $2440 Airbnb ROI: 5.97% Traditional ROI: 3.17%

Your search for investment property begins and ends here

Townhouses for Sale in Winter Park, FL

1768 MONDRIAN CIRCLE

Winter Park, FL

3 beds | 4 baths | 2,193 sq.ft.

$1,099,000

Airbnb cash on cash: 0.89%

Traditional cash on cash: 1.61%

Airbnb Rental Income: $4337

Traditional Rental Income: $4159

Airbnb ROI: 0.89%

Traditional ROI: 1.61%

962 ARAGON AVENUE

Winter Park, FL

3 beds | 2 baths | 1,680 sq.ft.

$599,900

Airbnb cash on cash: 3.79%

Traditional cash on cash: 1.71%

Airbnb Rental Income: $4337

Traditional Rental Income: $2260

Airbnb ROI: 3.79%

Traditional ROI: 1.71%

7470 CANFORD COURT #23

Winter Park, FL

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

$248,900

Airbnb cash on cash: 9.22%

Traditional cash on cash: 3.89%

Airbnb Rental Income: $4337

Traditional Rental Income: $2173

Airbnb ROI: 9.22%

Traditional ROI: 3.89%

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: 4.14%

Airbnb Rental Income: $4337

Traditional Rental Income: $2843

Airbnb ROI: 5.48%

Traditional ROI: 4.14%

2808 BRIGHT BIRD LANE

Winter Park, FL

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

$399,000

Airbnb cash on cash: 5.27%

Traditional cash on cash: 3.28%

Airbnb Rental Income: $4337

Traditional Rental Income: $2681

Airbnb ROI: 5.27%

Traditional ROI: 3.28%

1951 CANNY COVE

Winter Park, FL

3 beds | 3 baths | 1,782 sq.ft.

$444,900

Airbnb cash on cash: 4.46%

Traditional cash on cash: 2.78%

Airbnb Rental Income: $4337

Traditional Rental Income: $2724

Airbnb ROI: 4.46%

Traditional ROI: 2.78%

1995 CANNY COVE

Winter Park, FL

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

$425,000

Airbnb cash on cash: 4.93%

Traditional cash on cash: 2.83%

Airbnb Rental Income: $4337

Traditional Rental Income: $2587

Airbnb ROI: 4.93%

Traditional ROI: 2.83%

2676 BARBADOS DRIVE

Winter Park, FL

3 beds | 2 baths | 1,743 sq.ft.

$340,000

Airbnb cash on cash: 7.89%

Traditional cash on cash: 4.9%

Airbnb Rental Income: $4337

Traditional Rental Income: $2472

Airbnb ROI: 7.89%