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 16 Townhouse listings of over 500,000 total investment properties for sale. Visit Mashvisor.com to all investment properties.

separator

PROPERTY	DETAILS	SALE PRICE	INVESTMENT PERFORMANCE
1375 MERRYDALE WAY Winter Park, FL Under contract-accepting backup offers. Wake up to tranquil lake views and effortless luxu...	3 beds \| 3 baths \| 1,756 sq.ft.	$439,000	Airbnb cash on cash: 5.09% Traditional cash on cash: 3% Airbnb Rental Income: $4337 Traditional Rental Income: $2566 Airbnb ROI: 5.09% Traditional ROI: 3%
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: 3.78% Airbnb Rental Income: $4337 Traditional Rental Income: $2683 Airbnb ROI: 5.48% Traditional ROI: 3.78%
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: 5.43% Airbnb Rental Income: $4337 Traditional Rental Income: $2538 Airbnb ROI: 8.38% Traditional ROI: 5.43%
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: 1.35% Airbnb Rental Income: $4337 Traditional Rental Income: $3895 Airbnb ROI: 0.89% Traditional ROI: 1.35%
7444 WOODBURN COURT #29 Winter Park, FL Sought after Winter Park Location! 2-bedroom, 2.5-bath townhome located in the desirable ...	2 beds \| 3 baths \| 1,031 sq.ft.	$165,000	Airbnb cash on cash: 9.99% Traditional cash on cash: 5.94% Airbnb Rental Income: $3260 Traditional Rental Income: $1891 Airbnb ROI: 9.99% Traditional ROI: 5.94%
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.	$320,000	Airbnb cash on cash: 8.84% Traditional cash on cash: 5.93% Airbnb Rental Income: $4337 Traditional Rental Income: $2549 Airbnb ROI: 8.84% Traditional ROI: 5.93%
2224 SHADOWLAND LOOP Winter Park, FL **This house comes with a REDUCED RATE through the seller's preferred lender. This is a le...	3 beds \| 3 baths \| 2,346 sq.ft.	$435,000	Airbnb cash on cash: 4.95% Traditional cash on cash: 3.96% Airbnb Rental Income: $4337 Traditional Rental Income: $3019 Airbnb ROI: 4.95% Traditional ROI: 3.96%
1951 CANNY COVE Winter Park, FL Price improvement! Discover comfortable Winter Park living in this bright 3-bedroom, 2.5-b...	3 beds \| 3 baths \| 1,782 sq.ft.	$444,900	Airbnb cash on cash: 4.46% Traditional cash on cash: 2.51% Airbnb Rental Income: $4337 Traditional Rental Income: $2611 Airbnb ROI: 4.46% Traditional ROI: 2.51%
5473 BRACKEN COURT Winter Park, FL One or more photo(s) has been virtually staged. Move-in ready 3-bedroom, 2-bath townhome i...	3 beds \| 2 baths \| 1,178 sq.ft.	$295,000	Airbnb cash on cash: 9.85% Traditional cash on cash: 5.52% Airbnb Rental Income: $4337 Traditional Rental Income: $2223 Airbnb ROI: 9.85% Traditional ROI: 5.52%
1781 Indiana Ave #A Winter Park, FL 1781 Indiana Ave #A, Winter Park, FL 32789 \| Townhouse	3 beds \| 2 baths \| 1,616 sq.ft.	$565,000	Airbnb cash on cash: 3.45% Traditional cash on cash: 1.54% Airbnb Rental Income: $4337 Traditional Rental Income: $2417 Airbnb ROI: 3.45% Traditional ROI: 1.54%
2530 LEEWARD WAY Winter Park, FL Well-maintained 2-bedroom, 2-bath home with 1,199 sq ft in a desirable Winter Park 32792 l...	2 beds \| 2 baths \| 1,199 sq.ft.	$265,000	Airbnb cash on cash: 8% Traditional cash on cash: 4.69% Airbnb Rental Income: $3260 Traditional Rental Income: $1701 Airbnb ROI: 8% Traditional ROI: 4.69%
1289 HARMON AVENUE Winter Park, FL Under contract-accepting backup offers. Multiple Offers! Highest and Best due by 12:00pm o...	2 beds \| 2 baths \| 1,683 sq.ft.	$500,000	Airbnb cash on cash: 3.79% Traditional cash on cash: 3.22% Airbnb Rental Income: $3260 Traditional Rental Income: $2264 Airbnb ROI: 3.79% Traditional ROI: 3.22%
1780 MONDRIAN CIRCLE Winter Park, FL Luxury Lakeview Townhome in Winter Park! Experience elevated living in this newly built 3-...	3 beds \| 4 baths \| 2,310 sq.ft.	$1,395,000	Airbnb cash on cash: 0.49% Traditional cash on cash: 0.92% Airbnb Rental Income: $4337 Traditional Rental Income: $3985 Airbnb ROI: 0.49% Traditional ROI: 0.92%
1515 WINTER GREEN BOULEVARD Winter Park, FL Offering the comfort and feel of a single-family home with the convenience of townhome liv...	3 beds \| 4 baths \| 1,652 sq.ft.	$315,000	Airbnb cash on cash: 8.29% Traditional cash on cash: 5.97% Airbnb Rental Income: $4337 Traditional Rental Income: $2740 Airbnb ROI: 8.29% Traditional ROI: 5.97%
2612 EXUMA WAY Winter Park, FL Hidden gem in the heart of Winter Park! This beautifully updated 2-bedroom, 2-bath single-...	2 beds \| 2 baths \| 1,020 sq.ft.	$275,000	Airbnb cash on cash: 6.88% Traditional cash on cash: 3.33% Airbnb Rental Income: $3260 Traditional Rental Income: $1606 Airbnb ROI: 6.88% Traditional ROI: 3.33%
2400 DOMINICA RUN Winter Park, FL CHARMING 2/1 MOVE IN READY TOWNHOME in highly sought-after Windward Square community of Wi...	2 beds \| 1 baths \| 854 sq.ft.	$225,000	Airbnb cash on cash: 9.75% Traditional cash on cash: 5.76% Airbnb Rental Income: $3260 Traditional Rental Income: $1677 Airbnb ROI: 9.75% Traditional ROI: 5.76%

Your search for investment property begins and ends here

Townhouses for Sale in Winter Park, FL

1375 MERRYDALE WAY

Winter Park, FL

3 beds | 3 baths | 1,756 sq.ft.

$439,000

Airbnb cash on cash: 5.09%

Traditional cash on cash: 3%

Airbnb Rental Income: $4337

Traditional Rental Income: $2566

Airbnb ROI: 5.09%

Traditional ROI: 3%

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: 3.78%

Airbnb Rental Income: $4337

Traditional Rental Income: $2683

Airbnb ROI: 5.48%

Traditional ROI: 3.78%

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: 5.43%

Airbnb Rental Income: $4337

Traditional Rental Income: $2538

Airbnb ROI: 8.38%

Traditional ROI: 5.43%

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: 1.35%

Airbnb Rental Income: $4337

Traditional Rental Income: $3895

Airbnb ROI: 0.89%

Traditional ROI: 1.35%

7444 WOODBURN COURT #29

Winter Park, FL

2 beds | 3 baths | 1,031 sq.ft.

$165,000

Airbnb cash on cash: 9.99%

Traditional cash on cash: 5.94%

Airbnb Rental Income: $3260

Traditional Rental Income: $1891

Airbnb ROI: 9.99%

Traditional ROI: 5.94%

2401 ANTILLES DRIVE

Winter Park, FL

3 beds | 2 baths | 1,719 sq.ft.

$320,000

Airbnb cash on cash: 8.84%

Traditional cash on cash: 5.93%

Airbnb Rental Income: $4337

Traditional Rental Income: $2549

Airbnb ROI: 8.84%

Traditional ROI: 5.93%

2224 SHADOWLAND LOOP

Winter Park, FL

3 beds | 3 baths | 2,346 sq.ft.

$435,000

Airbnb cash on cash: 4.95%

Traditional cash on cash: 3.96%

Airbnb Rental Income: $4337

Traditional Rental Income: $3019

Airbnb ROI: 4.95%

Traditional ROI: 3.96%

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: 2.51%

Airbnb Rental Income: $4337

Traditional Rental Income: $2611

Airbnb ROI: 4.46%