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.

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PROPERTY	DETAILS	SALE PRICE	INVESTMENT PERFORMANCE
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%
2405 FIRSTLIGHT WAY Winter Park, FL Experience refined living in the sought-after gated community of Hawks Crest. This elegant...	3 beds \| 3 baths \| 1,964 sq.ft.	$469,000	Airbnb cash on cash: 4.87% Traditional cash on cash: 3.56% Airbnb Rental Income: $4337 Traditional Rental Income: $2850 Airbnb ROI: 4.87% Traditional ROI: 3.56%
7777 FERNBROOK WAY Winter Park, FL Under contract-accepting backup offers. Completely Renovated 2 bedroom and 2 bath Townhome...	2 beds \| 2 baths \| 1,092 sq.ft.	$275,000	Airbnb cash on cash: 6.9% Traditional cash on cash: 3.6% Airbnb Rental Income: $3260 Traditional Rental Income: $1671 Airbnb ROI: 6.9% Traditional ROI: 3.6%
1250 FORMOSA AVENUE Winter Park, FL Modern living meets unbeatable location in this stunning 3 bedroom, 3.5 bathroom home nest...	3 beds \| 4 baths \| 1,937 sq.ft.	$610,000	Airbnb cash on cash: 3.01% Traditional cash on cash: 3.58% Airbnb Rental Income: $4337 Traditional Rental Income: $3751 Airbnb ROI: 3.01% Traditional ROI: 3.58%
1907 S LAKEMONT AVENUE Winter Park, FL Special financing or closing cost credits available for qualified buyers! Introducing t...	3 beds \| 4 baths \| 2,063 sq.ft.	$849,900	Airbnb cash on cash: 2.55% Traditional cash on cash: 2.17% Airbnb Rental Income: $4337 Traditional Rental Income: $3129 Airbnb ROI: 2.55% Traditional ROI: 2.17%
2426 WINDWARD WAY Winter Park, FL Under contract-accepting backup offers. Nestled in the heart of the highly desirable Windw...	2 beds \| 2 baths \| 932 sq.ft.	$275,000	Airbnb cash on cash: 7.82% Traditional cash on cash: 4.43% Airbnb Rental Income: $3260 Traditional Rental Income: $1648 Airbnb ROI: 7.82% Traditional ROI: 4.43%
1917 S LAKEMONT AVENUE Winter Park, FL Special financing or closing cost credits available for qualified buyers! Introducing t...	3 beds \| 4 baths \| 2,051 sq.ft.	$849,000	Airbnb cash on cash: 2.53% Traditional cash on cash: 2.16% Airbnb Rental Income: $4337 Traditional Rental Income: $3129 Airbnb ROI: 2.53% Traditional ROI: 2.16%
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.	$494,900	Airbnb cash on cash: 5.09% Traditional cash on cash: 3.18% Airbnb Rental Income: $4337 Traditional Rental Income: $2540 Airbnb ROI: 5.09% Traditional ROI: 3.18%
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.	$452,000	Airbnb cash on cash: 4.53% Traditional cash on cash: 2.44% Airbnb Rental Income: $4337 Traditional Rental Income: $2540 Airbnb ROI: 4.53% Traditional ROI: 2.44%
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%
2949 CLEVER LANE Winter Park, FL Under contract-accepting backup offers. Welcome to this stunning former model townhome bui...	3 beds \| 3 baths \| 1,907 sq.ft.	$429,990	Airbnb cash on cash: 4.89% Traditional cash on cash: 2.79% Airbnb Rental Income: $4337 Traditional Rental Income: $2578 Airbnb ROI: 4.89% Traditional ROI: 2.79%
1117 PARK GREEN PLACE Winter Park, FL Charming One-Story Townhome in Prime Winter Park Location! Welcome to this adorable detac...	3 beds \| 2 baths \| 1,235 sq.ft.	$365,000	Airbnb cash on cash: 6.51% Traditional cash on cash: 2.14% Airbnb Rental Income: $4337 Traditional Rental Income: $1927 Airbnb ROI: 6.51% Traditional ROI: 2.14%
512 CLARENDON AVENUE Winter Park, FL Beautifully updated 4BD/3.5BA townhome in highly sought-after Virginia Heights, just steps...	4 beds \| 4 baths \| 2,826 sq.ft.	$1,050,000	Airbnb cash on cash: 2.58% Traditional cash on cash: 1.86% Airbnb Rental Income: $5745 Traditional Rental Income: $3898 Airbnb ROI: 2.58% Traditional ROI: 1.86%
438 W SWOOPE AVENUE Winter Park, FL Located within the private enclave of 400 Westâan exclusive 9-residence community just s...	4 beds \| 4 baths \| 2,604 sq.ft.	$790,000	Airbnb cash on cash: 3.42% Traditional cash on cash: 2.04% Airbnb Rental Income: $5745 Traditional Rental Income: $3579 Airbnb ROI: 3.42% Traditional ROI: 2.04%
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%
1221 PARK GREEN PLACE Winter Park, FL This two-bedroom, two-bath home offers comfort, character, and an unbeatable location. Bot...	2 beds \| 2 baths \| 1,272 sq.ft.	$379,000	Airbnb cash on cash: 4.78% Traditional cash on cash: 3.19% Airbnb Rental Income: $3260 Traditional Rental Income: $1962 Airbnb ROI: 4.78% Traditional ROI: 3.19%

Your search for investment property begins and ends here

Townhouses for Sale in Winter Park, FL

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%

2405 FIRSTLIGHT WAY

Winter Park, FL

3 beds | 3 baths | 1,964 sq.ft.

$469,000

Airbnb cash on cash: 4.87%

Traditional cash on cash: 3.56%

Airbnb Rental Income: $4337

Traditional Rental Income: $2850

Airbnb ROI: 4.87%

Traditional ROI: 3.56%

7777 FERNBROOK WAY

Winter Park, FL

2 beds | 2 baths | 1,092 sq.ft.

$275,000

Airbnb cash on cash: 6.9%

Traditional cash on cash: 3.6%

Airbnb Rental Income: $3260

Traditional Rental Income: $1671

Airbnb ROI: 6.9%

Traditional ROI: 3.6%

1250 FORMOSA AVENUE

Winter Park, FL

3 beds | 4 baths | 1,937 sq.ft.

$610,000

Airbnb cash on cash: 3.01%

Traditional cash on cash: 3.58%

Airbnb Rental Income: $4337

Traditional Rental Income: $3751

Airbnb ROI: 3.01%

Traditional ROI: 3.58%

1907 S LAKEMONT AVENUE

Winter Park, FL

3 beds | 4 baths | 2,063 sq.ft.

$849,900

Airbnb cash on cash: 2.55%

Traditional cash on cash: 2.17%

Airbnb Rental Income: $4337

Traditional Rental Income: $3129

Airbnb ROI: 2.55%

Traditional ROI: 2.17%

2426 WINDWARD WAY

Winter Park, FL

2 beds | 2 baths | 932 sq.ft.

$275,000

Airbnb cash on cash: 7.82%

Traditional cash on cash: 4.43%

Airbnb Rental Income: $3260

Traditional Rental Income: $1648

Airbnb ROI: 7.82%

Traditional ROI: 4.43%

1917 S LAKEMONT AVENUE

Winter Park, FL

3 beds | 4 baths | 2,051 sq.ft.

$849,000

Airbnb cash on cash: 2.53%

Traditional cash on cash: 2.16%

Airbnb Rental Income: $4337

Traditional Rental Income: $3129

Airbnb ROI: 2.53%

Traditional ROI: 2.16%

2774 BRIGHT BIRD LANE

Winter Park, FL

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

$494,900

Airbnb cash on cash: 5.09%

Traditional cash on cash: 3.18%

Airbnb Rental Income: $4337

Traditional Rental Income: $2540

Airbnb ROI: 5.09%