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 26 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.	$2,679,268	Airbnb cash on cash: -0.87% Traditional cash on cash: -0.38% Airbnb Rental Income: $2565 Traditional Rental Income: $3179 Airbnb ROI: -0.87% Traditional ROI: -0.38%
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.	$2,676,688	Airbnb cash on cash: -0.87% Traditional cash on cash: -0.37% Airbnb Rental Income: $2565 Traditional Rental Income: $3179 Airbnb ROI: -0.87% Traditional ROI: -0.37%
40 Cub Creek Way Winter Park, CO Welcome to Lakota Pointe, where luxury living meets the majestic Rocky Mountains. Meticulo...	4 beds \| 4 baths \| 3,629 sq.ft.	$3,465,000	Airbnb cash on cash: -0.96% Traditional cash on cash: -0.11% Airbnb Rental Income: $2565 Traditional Rental Income: $4673 Airbnb ROI: -0.96% Traditional ROI: -0.11%
54 Cub Creek Way Winter Park, CO Welcome to Lakota Pointe, where luxury living meets the majestic Rocky Mountains. Meticulo...	4 beds \| 4 baths \| 3,629 sq.ft.	$3,470,000	Airbnb cash on cash: -0.93% Traditional cash on cash: -0.45% Airbnb Rental Income: $2565 Traditional Rental Income: $3479 Airbnb ROI: -0.93% Traditional ROI: -0.45%
64 Overlook Place Winter Park, CO Perched in Winter Park, this uphill 4-bedroom, 4.5-bath mountain home defines modern luxur...	4 beds \| 4 baths \| 3,057 sq.ft.	$2,744,642	Airbnb cash on cash: -0.89% Traditional cash on cash: 0.12% Airbnb Rental Income: $2565 Traditional Rental Income: $4517 Airbnb ROI: -0.89% Traditional ROI: 0.12%
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: -0.63% Traditional cash on cash: 0.24% Airbnb Rental Income: $1699 Traditional Rental Income: $2973 Airbnb ROI: -0.63% Traditional ROI: 0.24%
113 Apres Way Winter Park, CO Discover an alpine sanctuary of uncompromising luxury built with a legacy mindset. Located...	5 beds \| 6 baths \| 3,664 sq.ft.	$3,950,000	Airbnb cash on cash: -0.69% Traditional cash on cash: 0.35% Airbnb Rental Income: $3915 Traditional Rental Income: $6897 Airbnb ROI: -0.69% Traditional ROI: 0.35%
24 Cub Creek Way Winter Park, CO Welcome to Lakota Pointe, where luxury living meets the majestic Rocky Mountains. Meticulo...	4 beds \| 4 baths \| 3,629 sq.ft.	$3,455,000	Airbnb cash on cash: -0.93% Traditional cash on cash: -0.45% Airbnb Rental Income: $2565 Traditional Rental Income: $3479 Airbnb ROI: -0.93% Traditional ROI: -0.45%
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: -0.41% Traditional cash on cash: 0.69% Airbnb Rental Income: $3915 Traditional Rental Income: $6606 Airbnb ROI: -0.41% Traditional ROI: 0.69%
160 Exploration Trail Winter Park, CO NOW BEING SOLD FULLY FURNISHED & TURNKEY Tucked away on a private double lot along the...	4 beds \| 4 baths \| 3,174 sq.ft.	$3,435,000	Airbnb cash on cash: -0.92% Traditional cash on cash: -0.33% Airbnb Rental Income: $2565 Traditional Rental Income: $3845 Airbnb ROI: -0.92% Traditional ROI: -0.33%
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: -0.65% Traditional cash on cash: 0.21% Airbnb Rental Income: $1699 Traditional Rental Income: $3011 Airbnb ROI: -0.65% Traditional ROI: 0.21%
85 RAMBLE Lane Winter Park, CO Welcome to one of Winter Park's most desirable addresses at 85 Ramble Lane at The Wilds 36...	4 beds \| 3 baths \| 2,994 sq.ft.	$2,250,000	Airbnb cash on cash: -0.67% Traditional cash on cash: -0.04% Airbnb Rental Income: $2565 Traditional Rental Income: $3275 Airbnb ROI: -0.67% Traditional ROI: -0.04%
54 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 \| 2,742 sq.ft.	$2,350,000	Airbnb cash on cash: -0.66% Traditional cash on cash: 0.16% Airbnb Rental Income: $1699 Traditional Rental Income: $3011 Airbnb ROI: -0.66% Traditional ROI: 0.16%
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: -0.68% Traditional cash on cash: 0.16% Airbnb Rental Income: $1699 Traditional Rental Income: $3136 Airbnb ROI: -0.68% Traditional ROI: 0.16%
674 Leland Creek Circle Winter Park, CO Moutain Modern home located in Leland Creek, this 2023-built, 5-bed, 5-bath offers unparal...	5 beds \| 4 baths \| 4,574 sq.ft.	$4,000,000	Airbnb cash on cash: -0.51% Traditional cash on cash: -0.01% Airbnb Rental Income: $3915 Traditional Rental Income: $4957 Airbnb ROI: -0.51% Traditional ROI: -0.01%
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: -0.62% Traditional cash on cash: 0.29% Airbnb Rental Income: $1699 Traditional Rental Income: $2973 Airbnb ROI: -0.62% Traditional ROI: 0.29%
158 SCENIC Trail Winter Park, CO Winter Park, this uphill 4-bedroom, 4.5-bath residence showcases modern mountain luxury at...	4 beds \| 5 baths \| 3,057 sq.ft.	$2,668,492	Airbnb cash on cash: -0.25% Traditional cash on cash: 0.72% Airbnb Rental Income: $2565 Traditional Rental Income: $4351 Airbnb ROI: -0.25% Traditional ROI: 0.72%
170 Scenic Trail Winter Park, CO Winter Park, this uphill 4-bedroom, 4.5-bath residence showcases modern mountain luxury at...	4 beds \| 4 baths \| 3,057 sq.ft.	$2,721,192	Airbnb cash on cash: -0.26% Traditional cash on cash: 0.27% Airbnb Rental Income: $2565 Traditional Rental Income: $3295 Airbnb ROI: -0.26% Traditional ROI: 0.27%
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: -0.39% Traditional cash on cash: 0.11% Airbnb Rental Income: $2565 Traditional Rental Income: $3172 Airbnb ROI: -0.39% Traditional ROI: 0.11%
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: -0.92% Traditional cash on cash: -0.34% Airbnb Rental Income: $2565 Traditional Rental Income: $3491 Airbnb ROI: -0.92% Traditional ROI: -0.34%
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: -0.93% Traditional cash on cash: -0.38% Airbnb Rental Income: $2565 Traditional Rental Income: $3478 Airbnb ROI: -0.93% Traditional ROI: -0.38%
5 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.	$2,755,421	Airbnb cash on cash: -0.89% Traditional cash on cash: -0.41% Airbnb Rental Income: $2565 Traditional Rental Income: $3179 Airbnb ROI: -0.89% Traditional ROI: -0.41%
21 Apres Way Winter Park, CO Discover 21 Apres Way, an alpine sanctuary of uncompromising luxury. Located within Riverw...	5 beds \| 6 baths \| 3,787 sq.ft.	$3,950,000	Airbnb cash on cash: -0.69% Traditional cash on cash: 0.35% Airbnb Rental Income: $3915 Traditional Rental Income: $6897 Airbnb ROI: -0.69% Traditional ROI: 0.35%
106 PRESERVE Way Winter Park, CO Luxury Living in Winter Park Preserve Discover refined mountain living in this stunning th...	5 beds \| 6 baths \| 3,564 sq.ft.	$2,949,000	Airbnb cash on cash: -0.32% Traditional cash on cash: 0.98% Airbnb Rental Income: $3915 Traditional Rental Income: $6623 Airbnb ROI: -0.32% Traditional ROI: 0.98%
30-A Ramble Lane Winter Park, CO $100,000 BUYER CREDIT - LUXURY UPGRADES INCLUDED! The credit covers rooftop hot tub + wet ...	4 beds \| 4 baths \| 2,554 sq.ft.	$2,373,500	Airbnb cash on cash: -0.34% Traditional cash on cash: 0.16% Airbnb Rental Income: $2565 Traditional Rental Income: $3036 Airbnb ROI: -0.34% Traditional ROI: 0.16%
294 VASQUEZ Road Winter Park, CO Location, Location, Location!!!! Come take a look at this 1960's bunkhouse cabin in such a...	3 beds \| 2 baths \| 1,280 sq.ft.	$1,015,000	Airbnb cash on cash: 0.04% Traditional cash on cash: 0.77% Airbnb Rental Income: $1699 Traditional Rental Income: $1919 Airbnb ROI: 0.04% Traditional ROI: 0.77%

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.

$2,679,268

Airbnb cash on cash: -0.87%

Traditional cash on cash: -0.38%

Airbnb Rental Income: $2565

Traditional Rental Income: $3179

Airbnb ROI: -0.87%

Traditional ROI: -0.38%

45 Scenic Trail

Winter Park, CO

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

$2,676,688

Airbnb cash on cash: -0.87%

Traditional cash on cash: -0.37%

Airbnb Rental Income: $2565

Traditional Rental Income: $3179

Airbnb ROI: -0.87%

Traditional ROI: -0.37%

40 Cub Creek Way

Winter Park, CO

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

$3,465,000

Airbnb cash on cash: -0.96%

Traditional cash on cash: -0.11%

Airbnb Rental Income: $2565

Traditional Rental Income: $4673

Airbnb ROI: -0.96%

Traditional ROI: -0.11%

54 Cub Creek Way

Winter Park, CO

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

$3,470,000

Airbnb cash on cash: -0.93%

Traditional cash on cash: -0.45%

Airbnb Rental Income: $2565

Traditional Rental Income: $3479

Airbnb ROI: -0.93%

Traditional ROI: -0.45%

64 Overlook Place

Winter Park, CO

4 beds | 4 baths | 3,057 sq.ft.

$2,744,642

Airbnb cash on cash: -0.89%

Traditional cash on cash: 0.12%

Airbnb Rental Income: $2565

Traditional Rental Income: $4517

Airbnb ROI: -0.89%

Traditional ROI: 0.12%

18 Exploration Trail

Winter Park, CO

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

$2,150,000

Airbnb cash on cash: -0.63%

Traditional cash on cash: 0.24%

Airbnb Rental Income: $1699

Traditional Rental Income: $2973

Airbnb ROI: -0.63%

Traditional ROI: 0.24%

113 Apres Way

Winter Park, CO

5 beds | 6 baths | 3,664 sq.ft.

$3,950,000

Airbnb cash on cash: -0.69%

Traditional cash on cash: 0.35%

Airbnb Rental Income: $3915

Traditional Rental Income: $6897

Airbnb ROI: -0.69%

Traditional ROI: 0.35%

24 Cub Creek Way

Winter Park, CO

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

$3,455,000

Airbnb cash on cash: -0.93%

Traditional cash on cash: -0.45%

Airbnb Rental Income: $2565

Traditional Rental Income: $3479

Airbnb ROI: -0.93%