Real Estate Investment Properties for Sale in Winter Park, CO

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

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

Condos for Sale in Winter Park, CO

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

Showing 24 Condo 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
78311 US HWY 40 #1 Winter Park, CO Easy to Tour! This 2-Bedroom/2.5-Bath Furnished Condo has it ALL: Modern Construction with...	2 beds \| 3 baths \| 1,149 sq.ft.	$899,000	Airbnb cash on cash: 1.24% Traditional cash on cash: 0.71% Airbnb Rental Income: $3517 Traditional Rental Income: $2300 Airbnb ROI: 1.24% Traditional ROI: 0.71%
720 Baker Drive #204 Winter Park, CO Introducing the highly anticipated Headwaters Condos, a premier new construction project i...	2 beds \| 1 baths \| 874 sq.ft.	$750,000	Airbnb cash on cash: 2.28% Traditional cash on cash: 1.13% Airbnb Rental Income: $3517 Traditional Rental Income: $1938 Airbnb ROI: 2.28% Traditional ROI: 1.13%
78746 US HWY 40 #213 Winter Park, CO There is no other condo complex in Winter Park quite like this community. Mountain modern ...	2 beds \| 2 baths \| 885 sq.ft.	$813,019	Airbnb cash on cash: 1.83% Traditional cash on cash: 0.73% Airbnb Rental Income: $3517 Traditional Rental Income: $1905 Airbnb ROI: 1.83% Traditional ROI: 0.73%
78746 US HWY 40 #212 Winter Park, CO There is no other condo complex in Winter Park quite like this community. Mountain modern ...	2 beds \| 2 baths \| 885 sq.ft.	$813,687	Airbnb cash on cash: 1.83% Traditional cash on cash: 0.73% Airbnb Rental Income: $3517 Traditional Rental Income: $1905 Airbnb ROI: 1.83% Traditional ROI: 0.73%
273 Hi Country Drive #15 Winter Park, CO Riverfront retreat in the heart of downtown WP! Enjoy this TOP FLOOR, 1 bedroom condo with...	1 beds \| 1 baths \| 459 sq.ft.	$429,000	Airbnb cash on cash: 2.01% Traditional cash on cash: 1.28% Airbnb Rental Income: $1948 Traditional Rental Income: $1138 Airbnb ROI: 2.01% Traditional ROI: 1.28%
46 TELEMARK Drive #6 Winter Park, CO Experience breathtaking mountain views from both floors of this fully renovated, end-unit,...	2 beds \| 2 baths \| 1,012 sq.ft.	$694,000	Airbnb cash on cash: 2.84% Traditional cash on cash: 1.16% Airbnb Rental Income: $3517 Traditional Rental Income: $1656 Airbnb ROI: 2.84% Traditional ROI: 1.16%
720 BAKER Drive #404 Winter Park, CO Introducing the highly anticipated Headwaters Condos, a premier new construction project i...	1 beds \| 2 baths \| 1,154 sq.ft.	$1,025,000	Airbnb cash on cash: -0.1% Traditional cash on cash: 0.59% Airbnb Rental Income: $1948 Traditional Rental Income: $2097 Airbnb ROI: -0.1% Traditional ROI: 0.59%
720 BAKER Drive #305 Winter Park, CO Introducing the highly anticipated Headwaters Condos, a premier new construction project i...	3 beds \| 3 baths \| 1,485 sq.ft.	$1,275,000	Airbnb cash on cash: 0.68% Traditional cash on cash: 0.65% Airbnb Rental Income: $3446 Traditional Rental Income: $2646 Airbnb ROI: 0.68% Traditional ROI: 0.65%
78746 US HWY 40 #218 Winter Park, CO Quite possibly the best downtown location in Winter Park. Arrow at WP will be a unique thr...	3 beds \| 3 baths \| 1,513 sq.ft.	$1,252,736	Airbnb cash on cash: 0.79% Traditional cash on cash: 0.73% Airbnb Rental Income: $3446 Traditional Rental Income: $2609 Airbnb ROI: 0.79% Traditional ROI: 0.73%
78746 US HWY 40 #215 Winter Park, CO Quite possibly the best downtown location in Winter Park. Arrow at WP will be a unique thr...	3 beds \| 3 baths \| 1,479 sq.ft.	$1,251,215	Airbnb cash on cash: 0.79% Traditional cash on cash: 0.7% Airbnb Rental Income: $3446 Traditional Rental Income: $2580 Airbnb ROI: 0.79% Traditional ROI: 0.7%
145 FOREST TRAIL #16 Winter Park, CO Priced low so you have the extra cash to do the updates you want! It has been a while sin...	1 beds \| 2 baths \| 577 sq.ft.	$495,000	Airbnb cash on cash: 1.59% Traditional cash on cash: 1.43% Airbnb Rental Income: $1948 Traditional Rental Income: $1361 Airbnb ROI: 1.59% Traditional ROI: 1.43%
201 Zephyr Way #2218 Winter Park, CO Premier - Second Floor - Ski In/Out Condo. Take advantage of this limited opportunity to o...	1 beds \| 1 baths \| 557 sq.ft.	$605,000	Airbnb cash on cash: 1.04% Traditional cash on cash: 0.94% Airbnb Rental Income: $1948 Traditional Rental Income: $1381 Airbnb ROI: 1.04% Traditional ROI: 0.94%
159 Hi Country Drive #14 Winter Park, CO Don't miss out on this fabulous location and updated 2-bedroom, 2-bathroom. The open flo...	2 beds \| 2 baths \| 960 sq.ft.	$655,000	Airbnb cash on cash: 2.97% Traditional cash on cash: 1.05% Airbnb Rental Income: $3517 Traditional Rental Income: $1566 Airbnb ROI: 2.97% Traditional ROI: 1.05%
466 HI Country Drive #17-18 Winter Park, CO Top floor, end unit right in the heart of downtown Winter Park! This spacious floor plan ...	2 beds \| 2 baths \| 714 sq.ft.	$585,000	Airbnb cash on cash: 3.46% Traditional cash on cash: 1.91% Airbnb Rental Income: $3517 Traditional Rental Income: $1896 Airbnb ROI: 3.46% Traditional ROI: 1.91%
51 River Drive Winter Park, CO Heads up! Condos in this gorgeous building along the Fraser River rarely come on the mark...	2 beds \| 2 baths \| 899 sq.ft.	$675,000	Airbnb cash on cash: 2.87% Traditional cash on cash: 0.95% Airbnb Rental Income: $3517 Traditional Rental Income: $1530 Airbnb ROI: 2.87% Traditional ROI: 0.95%
720 BAKER Drive #409 Winter Park, CO Introducing the highly anticipated Headwaters Condos, a premier new construction project i...	2 beds \| 2 baths \| 958 sq.ft.	$925,000	Airbnb cash on cash: 1.57% Traditional cash on cash: 0.71% Airbnb Rental Income: $3517 Traditional Rental Income: $2002 Airbnb ROI: 1.57% Traditional ROI: 0.71%
720 BAKER Drive #306 Winter Park, CO Introducing the highly anticipated Headwaters Condos, a premier new construction project i...	2 beds \| 2 baths \| 956 sq.ft.	$895,000	Airbnb cash on cash: 1.67% Traditional cash on cash: 0.78% Airbnb Rental Income: $3517 Traditional Rental Income: $2002 Airbnb ROI: 1.67% Traditional ROI: 0.78%
720 BAKER Drive #311 Winter Park, CO Introducing the highly anticipated Headwaters Condos, a premier new construction project i...	2 beds \| 1 baths \| 874 sq.ft.	$840,000	Airbnb cash on cash: 1.88% Traditional cash on cash: 0.85% Airbnb Rental Income: $3517 Traditional Rental Income: $1938 Airbnb ROI: 1.88% Traditional ROI: 0.85%
32 TELEMARK Drive #101 Winter Park, CO Ideal location on the north end of Winter Park close to the new future medical facility. U...	1 beds \| 1 baths \| 507 sq.ft.	$399,900	Airbnb cash on cash: 2.23% Traditional cash on cash: 1.66% Airbnb Rental Income: $1948 Traditional Rental Income: $1221 Airbnb ROI: 2.23% Traditional ROI: 1.66%
720 BAKER Drive #207 Winter Park, CO * New Developer Incentive - $40,000 credit at closing * Introducing the highly anticip...	2 beds \| 2 baths \| 955 sq.ft.	$850,000	Airbnb cash on cash: 1.84% Traditional cash on cash: 0.91% Airbnb Rental Income: $3517 Traditional Rental Income: $2002 Airbnb ROI: 1.84% Traditional ROI: 0.91%
720 BAKER Drive #210 Winter Park, CO Introducing the highly anticipated Headwaters Condos, a premier new construction project i...	3 beds \| 3 baths \| 1,483 sq.ft.	$1,200,000	Airbnb cash on cash: 0.82% Traditional cash on cash: 0.76% Airbnb Rental Income: $3446 Traditional Rental Income: $2620 Airbnb ROI: 0.82% Traditional ROI: 0.76%
801 Trailhead Circle #833 Winter Park, CO Watch Video! This 3-bedroom, 3-bath TOP FLOOR condo with vaulted ceiling comes fully furni...	3 beds \| 3 baths \| 1,507 sq.ft.	$1,224,900	Airbnb cash on cash: 0.42% Traditional cash on cash: 0.2% Airbnb Rental Income: $3446 Traditional Rental Income: $2434 Airbnb ROI: 0.42% Traditional ROI: 0.2%

Your search for investment property begins and ends here

Condos for Sale in Winter Park, CO

78311 US HWY 40 #1

Winter Park, CO

2 beds | 3 baths | 1,149 sq.ft.

$899,000

Airbnb cash on cash: 1.24%

Traditional cash on cash: 0.71%

Airbnb Rental Income: $3517

Traditional Rental Income: $2300

Airbnb ROI: 1.24%

Traditional ROI: 0.71%

720 Baker Drive #204

Winter Park, CO

2 beds | 1 baths | 874 sq.ft.

$750,000

Airbnb cash on cash: 2.28%

Traditional cash on cash: 1.13%

Airbnb Rental Income: $3517

Traditional Rental Income: $1938

Airbnb ROI: 2.28%

Traditional ROI: 1.13%

78746 US HWY 40 #213

Winter Park, CO

2 beds | 2 baths | 885 sq.ft.

$813,019

Airbnb cash on cash: 1.83%

Traditional cash on cash: 0.73%

Airbnb Rental Income: $3517

Traditional Rental Income: $1905

Airbnb ROI: 1.83%

Traditional ROI: 0.73%

78746 US HWY 40 #212

Winter Park, CO

2 beds | 2 baths | 885 sq.ft.

$813,687

Airbnb cash on cash: 1.83%

Traditional cash on cash: 0.73%

Airbnb Rental Income: $3517

Traditional Rental Income: $1905

Airbnb ROI: 1.83%

Traditional ROI: 0.73%

273 Hi Country Drive #15

Winter Park, CO

1 beds | 1 baths | 459 sq.ft.

$429,000

Airbnb cash on cash: 2.01%

Traditional cash on cash: 1.28%

Airbnb Rental Income: $1948

Traditional Rental Income: $1138

Airbnb ROI: 2.01%

Traditional ROI: 1.28%

46 TELEMARK Drive #6

Winter Park, CO

2 beds | 2 baths | 1,012 sq.ft.

$694,000

Airbnb cash on cash: 2.84%

Traditional cash on cash: 1.16%

Airbnb Rental Income: $3517

Traditional Rental Income: $1656

Airbnb ROI: 2.84%

Traditional ROI: 1.16%

720 BAKER Drive #404

Winter Park, CO

1 beds | 2 baths | 1,154 sq.ft.

$1,025,000

Airbnb cash on cash: -0.1%

Traditional cash on cash: 0.59%

Airbnb Rental Income: $1948

Traditional Rental Income: $2097

Airbnb ROI: -0.1%

Traditional ROI: 0.59%

720 BAKER Drive #305

Winter Park, CO

3 beds | 3 baths | 1,485 sq.ft.

$1,275,000

Airbnb cash on cash: 0.68%

Traditional cash on cash: 0.65%

Airbnb Rental Income: $3446

Traditional Rental Income: $2646

Airbnb ROI: 0.68%