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
57 Scenic Trail Winter Park, CO Discover mountain tranquility in this brand new walkout style Rendezvous home. Dual owner'...	4 beds \| N/A baths \| 3,361 sq.ft.	$2,884,860	Airbnb cash on cash: -0.46% Traditional cash on cash: 0.12% Airbnb Rental Income: $2565 Traditional Rental Income: $3491 Airbnb ROI: -0.46% Traditional ROI: 0.12%
19 Scenic Trail Winter Park, CO Nestled in the heart of Winter Park, this downhill single-family mountain home embodies th...	4 beds \| N/A baths \| 2,775 sq.ft.	$2,633,898	Airbnb cash on cash: -0.4% Traditional cash on cash: 0.1% Airbnb Rental Income: $2565 Traditional Rental Income: $3179 Airbnb ROI: -0.4% Traditional ROI: 0.1%
64 Overlook Place Winter Park, CO Perched in Winter Park, this uphill 4-bedroom, 4.5-bath mountain home defines modern luxur...	4 beds \| N/A baths \| 3,057 sq.ft.	$2,722,215	Airbnb cash on cash: -0.51% Traditional cash on cash: 0.51% Airbnb Rental Income: $2565 Traditional Rental Income: $4517 Airbnb ROI: -0.51% Traditional ROI: 0.51%
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%
100 PRESERVE Way Winter Park, CO Experience luxury mountain living in Winter Park Preserve, an exclusive community of only ...	5 beds \| N/A baths \| 3,249 sq.ft.	$3,449,000	Airbnb cash on cash: -0.43% Traditional cash on cash: 0.67% Airbnb Rental Income: $3915 Traditional Rental Income: $6606 Airbnb ROI: -0.43% Traditional ROI: 0.67%
233 BRIDGER Trail Winter Park, CO Rare opprtunity to purchase a ski-in, ski-out single family home at Winter Park Resort. Lo...	4 beds \| 5 baths \| 4,454 sq.ft.	$4,200,000	Airbnb cash on cash: -1.08% Traditional cash on cash: -0.74% Airbnb Rental Income: $2565 Traditional Rental Income: $3271 Airbnb ROI: -1.08% Traditional ROI: -0.74%
115 LIONS GATE Winter Park, CO THE PERFECT LOCATION IN WINTER PARK! An incredible 4 bed, 4 bath home PLUS a separate cabi...	4 beds \| N/A baths \| 2,352 sq.ft.	$2,449,000	Airbnb cash on cash: -0.38% Traditional cash on cash: 0.33% Airbnb Rental Income: $2565 Traditional Rental Income: $3561 Airbnb ROI: -0.38% Traditional ROI: 0.33%
185 Vasquez Rd 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: -0.01% Traditional cash on cash: 0.22% Airbnb Rental Income: $3915 Traditional Rental Income: $3532 Airbnb ROI: -0.01% Traditional ROI: 0.22%
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%
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%
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 #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: N/A Airbnb Rental Income: $3915 Traditional Rental Income: $0 Airbnb ROI: -0.05% Traditional ROI: N/A
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%
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.	$2,616,629	Airbnb cash on cash: -0.4% Traditional cash on cash: 0.11% Airbnb Rental Income: $2565 Traditional Rental Income: $3179 Airbnb ROI: -0.4% Traditional ROI: 0.11%
31 Scenic Trail Winter Park, CO Newly released! Discover mountain tranquility in this brand new walkout style Rendezvous h...	4 beds \| N/A 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 \| N/A 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%
80 RAMBLE Lane Winter Park, CO Welcome to ''The Rock and Star Chalet,'' a stunning 4-bedroom, 3.5-bath retreat located in...	4 beds \| N/A baths \| 2,694 sq.ft.	$2,495,000	Airbnb cash on cash: -0.68% Traditional cash on cash: -0.08% Airbnb Rental Income: $2565 Traditional Rental Income: $3351 Airbnb ROI: -0.68% Traditional ROI: -0.08%

Your search for investment property begins and ends here

Single Family Homes for Sale in Winter Park, CO

57 Scenic Trail

Winter Park, CO

4 beds | N/A baths | 3,361 sq.ft.

$2,884,860

Airbnb cash on cash: -0.46%

Traditional cash on cash: 0.12%

Airbnb Rental Income: $2565

Traditional Rental Income: $3491

Airbnb ROI: -0.46%

Traditional ROI: 0.12%

19 Scenic Trail

Winter Park, CO

4 beds | N/A baths | 2,775 sq.ft.

$2,633,898

Airbnb cash on cash: -0.4%

Traditional cash on cash: 0.1%

Airbnb Rental Income: $2565

Traditional Rental Income: $3179

Airbnb ROI: -0.4%

Traditional ROI: 0.1%

64 Overlook Place

Winter Park, CO

4 beds | N/A baths | 3,057 sq.ft.

$2,722,215

Airbnb cash on cash: -0.51%

Traditional cash on cash: 0.51%

Airbnb Rental Income: $2565

Traditional Rental Income: $4517

Airbnb ROI: -0.51%

Traditional ROI: 0.51%

106 PRESERVE Way

Winter Park, CO

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%

100 PRESERVE Way

Winter Park, CO

5 beds | N/A baths | 3,249 sq.ft.

$3,449,000

Airbnb cash on cash: -0.43%

Traditional cash on cash: 0.67%

Airbnb Rental Income: $3915

Traditional Rental Income: $6606

Airbnb ROI: -0.43%

Traditional ROI: 0.67%

233 BRIDGER Trail

Winter Park, CO

4 beds | 5 baths | 4,454 sq.ft.

$4,200,000

Airbnb cash on cash: -1.08%

Traditional cash on cash: -0.74%

Airbnb Rental Income: $2565

Traditional Rental Income: $3271

Airbnb ROI: -1.08%

Traditional ROI: -0.74%

115 LIONS GATE

Winter Park, CO

4 beds | N/A baths | 2,352 sq.ft.

$2,449,000

Airbnb cash on cash: -0.38%

Traditional cash on cash: 0.33%

Airbnb Rental Income: $2565

Traditional Rental Income: $3561

Airbnb ROI: -0.38%

Traditional ROI: 0.33%

185 Vasquez Rd

Winter Park, CO

5 beds | 4 baths | 2,423 sq.ft.

$2,150,000

Airbnb cash on cash: -0.01%

Traditional cash on cash: 0.22%

Airbnb Rental Income: $3915

Traditional Rental Income: $3532

Airbnb ROI: -0.01%