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.

Single Family Homes for Sale in Winter Park, CO

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

Showing 21 Single Family Residential 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
19 Scenic Trail Winter Park, CO Nestled in the heart of Winter Park, this downhill single-family mountain home embodies th...	4 beds \| 4 baths \| 2,775 sq.ft.	$2,683,729	Airbnb cash on cash: -0.98% Traditional cash on cash: -0.18% Airbnb Rental Income: $1646 Traditional Rental Income: $3179 Airbnb ROI: -0.98% Traditional ROI: -0.18%
45 Scenic Trail Winter Park, CO Nestled in the heart of Winter Park, this downhill single-family mountain home embodies th...	4 beds \| 4 baths \| 2,775 sq.ft.	$2,685,643	Airbnb cash on cash: -0.93% Traditional cash on cash: -0.13% Airbnb Rental Income: $1646 Traditional Rental Income: $3179 Airbnb ROI: -0.93% Traditional ROI: -0.13%
54 Cub Creek Way Winter Park, CO Welcome to Lakota Pointe, where luxury living meets the majestic Rocky Mountains. Meticulo...	4 beds \| 5 baths \| 3,629 sq.ft.	$3,470,000	Airbnb cash on cash: -0.91% Traditional cash on cash: -0.19% Airbnb Rental Income: $1646 Traditional Rental Income: $3479 Airbnb ROI: -0.91% Traditional ROI: -0.19%
18 Exploration Trail Winter Park, CO Within ROAM, you'll find Wilds 360, a collection of single family residences designed spec...	3 beds \| 4 baths \| 2,597 sq.ft.	$2,150,000	Airbnb cash on cash: -0.66% Traditional cash on cash: 0.3% Airbnb Rental Income: $1500 Traditional Rental Income: $2973 Airbnb ROI: -0.66% Traditional ROI: 0.3%
100 PRESERVE Way Winter Park, CO Experience luxury mountain living in Winter Park Preserve, an exclusive community of only ...	5 beds \| 6 baths \| 3,249 sq.ft.	$3,449,000	Airbnb cash on cash: -0.58% Traditional cash on cash: 0.74% Airbnb Rental Income: $3085 Traditional Rental Income: $6606 Airbnb ROI: -0.58% Traditional ROI: 0.74%
60 Ski Idlewild Road Winter Park, CO Within ROAM, you'll find Wilds 360, a collection of single family residences designed spec...	3 beds \| 4 baths \| 2,649 sq.ft.	$2,250,000	Airbnb cash on cash: -0.67% Traditional cash on cash: 0.26% Airbnb Rental Income: $1500 Traditional Rental Income: $3011 Airbnb ROI: -0.67% Traditional ROI: 0.26%
54 Ski Idlewild Road Winter Park, CO Within ROAM, you'll find Wilds 360, a collection of single-family residences designed spec...	3 beds \| 5 baths \| 2,742 sq.ft.	$2,350,000	Airbnb cash on cash: -0.69% Traditional cash on cash: 0.21% Airbnb Rental Income: $1500 Traditional Rental Income: $3011 Airbnb ROI: -0.69% Traditional ROI: 0.21%
40 Ski Idlewild Road Winter Park, CO Within ROAM, you'll find Wilds 360, a collection of single family residences designed spec...	3 beds \| 4 baths \| 3,112 sq.ft.	$2,450,000	Airbnb cash on cash: -0.7% Traditional cash on cash: 0.22% Airbnb Rental Income: $1500 Traditional Rental Income: $3136 Airbnb ROI: -0.7% Traditional ROI: 0.22%
12 Exploration Trail Winter Park, CO Within ROAM, you'll find Wilds 360, a collection of single family residences designed spec...	3 beds \| 4 baths \| 2,597 sq.ft.	$2,075,000	Airbnb cash on cash: -0.64% Traditional cash on cash: 0.35% Airbnb Rental Income: $1500 Traditional Rental Income: $2973 Airbnb ROI: -0.64% Traditional ROI: 0.35%
113 Apres Way Winter Park, CO Experience luxury mountain living at 113 Apres Way in Riverwalk, Winter Park's premier riv...	5 beds \| 6 baths \| 3,664 sq.ft.	$3,950,000	Airbnb cash on cash: -0.76% Traditional cash on cash: 0.47% Airbnb Rental Income: $3085 Traditional Rental Income: $6897 Airbnb ROI: -0.76% Traditional ROI: 0.47%
158 SCENIC Trail Winter Park, CO Situated in Winter Park, this uphill 4-bedroom, 4.5-bath residence showcases modern mounta...	4 beds \| 6 baths \| 3,057 sq.ft.	$2,722,291	Airbnb cash on cash: -0.82% Traditional cash on cash: 0.44% Airbnb Rental Income: $1646 Traditional Rental Income: $4351 Airbnb ROI: -0.82% Traditional ROI: 0.44%
170 Scenic Trail Winter Park, CO Ideally situated in Winter Park, this uphill 4-bedroom, 4.5-bath residence showcases moder...	4 beds \| 5 baths \| 3,057 sq.ft.	$2,768,308	Airbnb cash on cash: -0.82% Traditional cash on cash: 0% Airbnb Rental Income: $1646 Traditional Rental Income: $3295 Airbnb ROI: -0.82% Traditional ROI: 0%
265 LAKOTA PARK Drive Winter Park, CO Experience breathtaking, unobstructed views of the Continental Divide and the renowned Win...	4 beds \| 5 baths \| 2,616 sq.ft.	$2,495,000	Airbnb cash on cash: -0.86% Traditional cash on cash: 0.32% Airbnb Rental Income: $1646 Traditional Rental Income: $3926 Airbnb ROI: -0.86% Traditional ROI: 0.32%
115 Lions Gate Drive Winter Park, CO An exceptional opportunity in the heart of Winter Park. This commercially zoned property b...	4 beds \| 3 baths \| 2,352 sq.ft.	$2,449,000	Airbnb cash on cash: -0.72% Traditional cash on cash: 0.24% Airbnb Rental Income: $1646 Traditional Rental Income: $3359 Airbnb ROI: -0.72% Traditional ROI: 0.24%
674 Leland Creek Circle Winter Park, CO Mountain Modern home located in Leland Creek, this 2023-built, 5-bed, 5-bath offers unpara...	5 beds \| 5 baths \| 4,574 sq.ft.	$4,250,000	Airbnb cash on cash: -0.79% Traditional cash on cash: -0.13% Airbnb Rental Income: $3085 Traditional Rental Income: $4957 Airbnb ROI: -0.79% Traditional ROI: -0.13%
118 Apres Way Winter Park, CO The rarest offering in Grand County: a turnkey luxury home with a perpetual short-term ren...	4 beds \| 5 baths \| 3,360 sq.ft.	$3,750,000	Airbnb cash on cash: -0.78% Traditional cash on cash: 0.2% Airbnb Rental Income: $1646 Traditional Rental Income: $4596 Airbnb ROI: -0.78% Traditional ROI: 0.2%
364 Timber Drive Winter Park, CO Luxury mountain chalet with exceptional vacation rental potential fully furnished just 3 m...	5 beds \| 5 baths \| 4,033 sq.ft.	$2,995,000	Airbnb cash on cash: -0.51% Traditional cash on cash: -0.18% Airbnb Rental Income: $3085 Traditional Rental Income: $3301 Airbnb ROI: -0.51% Traditional ROI: -0.18%
57 Scenic Trail Winter Park, CO Discover mountain tranquility in this brand new walkout style Rendezvous home. Dual owner'...	4 beds \| 4 baths \| 3,361 sq.ft.	$2,884,860	Airbnb cash on cash: -0.93% Traditional cash on cash: -0.06% Airbnb Rental Income: $1646 Traditional Rental Income: $3491 Airbnb ROI: -0.93% Traditional ROI: -0.06%
31 Scenic Trail Winter Park, CO Newly released! Discover mountain tranquility in this brand new walkout style Rendezvous h...	4 beds \| 4 baths \| 3,361 sq.ft.	$2,969,388	Airbnb cash on cash: -1.01% Traditional cash on cash: -0.18% Airbnb Rental Income: $1646 Traditional Rental Income: $3478 Airbnb ROI: -1.01% Traditional ROI: -0.18%
4 Ramble Lane Winter Park, CO This highly sought after James Peak floor plan boast spectacular view of the James Peak, P...	4 beds \| 4 baths \| 2,890 sq.ft.	$2,600,000	Airbnb cash on cash: -0.66% Traditional cash on cash: 0.16% Airbnb Rental Income: $1646 Traditional Rental Income: $3172 Airbnb ROI: -0.66% Traditional ROI: 0.16%
64 Overlook Place Winter Park, CO Perched in Winter Park, this uphill 4-bedroom, 4.5-bath mountain home defines modern luxur...	4 beds \| 5 baths \| 3,057 sq.ft.	$2,774,642	Airbnb cash on cash: -1.25% Traditional cash on cash: 0.05% Airbnb Rental Income: $1646 Traditional Rental Income: $4517 Airbnb ROI: -1.25% Traditional ROI: 0.05%

Your search for investment property begins and ends here

Single Family Homes for Sale in Winter Park, CO

19 Scenic Trail

Winter Park, CO

4 beds | 4 baths | 2,775 sq.ft.

$2,683,729

Airbnb cash on cash: -0.98%

Traditional cash on cash: -0.18%

Airbnb Rental Income: $1646

Traditional Rental Income: $3179

Airbnb ROI: -0.98%

Traditional ROI: -0.18%

45 Scenic Trail

Winter Park, CO

4 beds | 4 baths | 2,775 sq.ft.

$2,685,643

Airbnb cash on cash: -0.93%

Traditional cash on cash: -0.13%

Airbnb Rental Income: $1646

Traditional Rental Income: $3179

Airbnb ROI: -0.93%

Traditional ROI: -0.13%

54 Cub Creek Way

Winter Park, CO

4 beds | 5 baths | 3,629 sq.ft.

$3,470,000

Airbnb cash on cash: -0.91%

Traditional cash on cash: -0.19%

Airbnb Rental Income: $1646

Traditional Rental Income: $3479

Airbnb ROI: -0.91%

Traditional ROI: -0.19%

18 Exploration Trail

Winter Park, CO

3 beds | 4 baths | 2,597 sq.ft.

$2,150,000

Airbnb cash on cash: -0.66%

Traditional cash on cash: 0.3%

Airbnb Rental Income: $1500

Traditional Rental Income: $2973

Airbnb ROI: -0.66%

Traditional ROI: 0.3%

100 PRESERVE Way

Winter Park, CO

5 beds | 6 baths | 3,249 sq.ft.

$3,449,000

Airbnb cash on cash: -0.58%

Traditional cash on cash: 0.74%

Airbnb Rental Income: $3085

Traditional Rental Income: $6606

Airbnb ROI: -0.58%

Traditional ROI: 0.74%

60 Ski Idlewild Road

Winter Park, CO

3 beds | 4 baths | 2,649 sq.ft.

$2,250,000

Airbnb cash on cash: -0.67%

Traditional cash on cash: 0.26%

Airbnb Rental Income: $1500

Traditional Rental Income: $3011

Airbnb ROI: -0.67%

Traditional ROI: 0.26%

54 Ski Idlewild Road

Winter Park, CO

3 beds | 5 baths | 2,742 sq.ft.

$2,350,000

Airbnb cash on cash: -0.69%

Traditional cash on cash: 0.21%

Airbnb Rental Income: $1500

Traditional Rental Income: $3011

Airbnb ROI: -0.69%

Traditional ROI: 0.21%

40 Ski Idlewild Road

Winter Park, CO

3 beds | 4 baths | 3,112 sq.ft.

$2,450,000

Airbnb cash on cash: -0.7%

Traditional cash on cash: 0.22%

Airbnb Rental Income: $1500

Traditional Rental Income: $3136

Airbnb ROI: -0.7%