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 34 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: -0.59% Airbnb Rental Income: $2565 Traditional Rental Income: $3031 Airbnb ROI: -0.93% Traditional ROI: -0.59%
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: -0.16% Airbnb Rental Income: $1699 Traditional Rental Income: $2165 Airbnb ROI: -0.63% Traditional ROI: -0.16%
113 Apres Way Winter Park, CO Discover 113 Apres Way, an alpine sanctuary of uncompromising luxury. Located within River...	5 beds \| 6 baths \| 3,664 sq.ft.	$3,950,000	Airbnb cash on cash: -0.69% Traditional cash on cash: N/A Airbnb Rental Income: $3915 Traditional Rental Income: $0 Airbnb ROI: -0.69% Traditional ROI: N/A
118 Apres Way Winter Park, CO Welcome to 118 Apres Way - a brand new mountain modern retreat in the heart of Winter Park...	4 beds \| 5 baths \| 3,360 sq.ft.	$3,450,000	Airbnb cash on cash: -0.93% Traditional cash on cash: -0.59% Airbnb Rental Income: $2565 Traditional Rental Income: $3031 Airbnb ROI: -0.93% Traditional ROI: -0.59%
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: -0.59% Airbnb Rental Income: $2565 Traditional Rental Income: $3031 Airbnb ROI: -0.93% Traditional ROI: -0.59%
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: -0.58% Airbnb Rental Income: $2565 Traditional Rental Income: $3031 Airbnb ROI: -0.92% Traditional ROI: -0.58%
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: -0.2% Airbnb Rental Income: $1699 Traditional Rental Income: $2165 Airbnb ROI: -0.65% Traditional ROI: -0.2%
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: -0.23% Airbnb Rental Income: $1699 Traditional Rental Income: $2165 Airbnb ROI: -0.66% Traditional ROI: -0.23%
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: -0.26% Airbnb Rental Income: $1699 Traditional Rental Income: $2165 Airbnb ROI: -0.68% Traditional ROI: -0.26%
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.	$4,275,000	Airbnb cash on cash: -0.54% Traditional cash on cash: -0.07% Airbnb Rental Income: $3915 Traditional Rental Income: $4957 Airbnb ROI: -0.54% Traditional ROI: -0.07%
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: 0.15% Airbnb Rental Income: $2565 Traditional Rental Income: $3031 Airbnb ROI: -0.34% Traditional ROI: 0.15%
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: -0.13% Airbnb Rental Income: $1699 Traditional Rental Income: $2165 Airbnb ROI: -0.62% Traditional ROI: -0.13%
185 Vasquez Rd #B1 Winter Park, CO The Landing: Luxury Townhomes near Winter Park's planned gondola: 6 of 10 have been sold i...	4 beds \| 3 baths \| 2,476 sq.ft.	$1,995,000	Airbnb cash on cash: -0.55% Traditional cash on cash: 0.14% Airbnb Rental Income: $2565 Traditional Rental Income: $3229 Airbnb ROI: -0.55% Traditional ROI: 0.14%
185 Vasquez Rd #B5 Winter Park, CO The Landing: Luxury Townhomes near Winter Park's planned gondola. Steps across the street ...	4 beds \| 3 baths \| 2,476 sq.ft.	$1,995,000	Airbnb cash on cash: -0.52% Traditional cash on cash: 0.18% Airbnb Rental Income: $2565 Traditional Rental Income: $3229 Airbnb ROI: -0.52% Traditional ROI: 0.18%
185 Vasquez Rd #B2 Winter Park, CO ONLY FOUR LEFT! The Landing: Luxury Townhomes across the street from Winter Park's planned...	4 beds \| 3 baths \| 2,314 sq.ft.	$1,950,000	Airbnb cash on cash: -0.54% Traditional cash on cash: 0.14% Airbnb Rental Income: $2565 Traditional Rental Income: $3165 Airbnb ROI: -0.54% Traditional ROI: 0.14%
701 Red Quill Way Winter Park, CO This stunning end-unit 4 bed, 5 bath townhome in the heart of downtown Winter Park offers ...	4 beds \| 5 baths \| 2,360 sq.ft.	$1,495,000	Airbnb cash on cash: -0.78% Traditional cash on cash: 0.46% Airbnb Rental Income: $2565 Traditional Rental Income: $3673 Airbnb ROI: -0.78% Traditional ROI: 0.46%
185 Vasquez Rd Winter Park, CO ONLY ONE LEFT! The Landing: Luxury Townhomes across the street from Winter Park's planned ...	5 beds \| 4 baths \| 2,423 sq.ft.	$2,250,000	Airbnb cash on cash: -0.06% Traditional cash on cash: 0.16% Airbnb Rental Income: $3915 Traditional Rental Income: $3532 Airbnb ROI: -0.06% Traditional ROI: 0.16%
185 Vasquez Rd #C1 Winter Park, CO The Landing: Luxury Townhomes near Winter Park's planned gondola: 6 of 10 have been sold i...	4 beds \| 3 baths \| 2,476 sq.ft.	$1,995,000	Airbnb cash on cash: -0.55% Traditional cash on cash: 0.16% Airbnb Rental Income: $2565 Traditional Rental Income: $3269 Airbnb ROI: -0.55% Traditional ROI: 0.16%
185 Vasquez Rd #D1 Winter Park, CO Final Phase - PRIME end unit. Steps across the street from Winter Park's planned gondola, ...	5 beds \| 3 baths \| 2,476 sq.ft.	$2,220,000	Airbnb cash on cash: -0.05% Traditional cash on cash: 0.06% Airbnb Rental Income: $3915 Traditional Rental Income: $3283 Airbnb ROI: -0.05% Traditional ROI: 0.06%
185 Vasquez Rd #C4 Winter Park, CO The Landing: Luxury Townhomes near Winter Park's planned gondola: now HALF sold out and th...	4 beds \| 3 baths \| 2,383 sq.ft.	$1,995,000	Airbnb cash on cash: -0.58% Traditional cash on cash: 0.1% Airbnb Rental Income: $2565 Traditional Rental Income: $3222 Airbnb ROI: -0.58% Traditional ROI: 0.1%
185 Vasquez Rd #D3 Winter Park, CO ONLY FOUR LEFT! The Landing: Luxury Townhomes across the street from Winter Park's planned...	5 beds \| 4 baths \| 2,423 sq.ft.	$2,150,000	Airbnb cash on cash: -0.05% Traditional cash on cash: -0.02% Airbnb Rental Income: $3915 Traditional Rental Income: $3122 Airbnb ROI: -0.05% Traditional ROI: -0.02%
185 Vasquez Rd #B4 Winter Park, CO ONLY FOUR LEFT! The Landing: Luxury Townhomes across the street from Winter Park's planned...	4 beds \| 3 baths \| 2,329 sq.ft.	$1,950,000	Airbnb cash on cash: -0.57% Traditional cash on cash: 0.12% Airbnb Rental Income: $2565 Traditional Rental Income: $3200 Airbnb ROI: -0.57% Traditional ROI: 0.12%
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: N/A Airbnb Rental Income: $3915 Traditional Rental Income: $0 Airbnb ROI: -0.69% Traditional ROI: N/A
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%

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: -0.59%

Airbnb Rental Income: $2565

Traditional Rental Income: $3031

Airbnb ROI: -0.93%

Traditional ROI: -0.59%

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: -0.16%

Airbnb Rental Income: $1699

Traditional Rental Income: $2165

Airbnb ROI: -0.63%

Traditional ROI: -0.16%

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: N/A

Airbnb Rental Income: $3915

Traditional Rental Income: $0

Airbnb ROI: -0.69%

Traditional ROI: N/A

118 Apres Way

Winter Park, CO

4 beds | 5 baths | 3,360 sq.ft.

$3,450,000

Airbnb cash on cash: -0.93%

Traditional cash on cash: -0.59%

Airbnb Rental Income: $2565

Traditional Rental Income: $3031

Airbnb ROI: -0.93%