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 53 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
78746 US Highway 40 unit: 221 #221 Winter Park, CO $40k incentive to use as Buyer wishes (2/1 Buy Down, hot tub, blinds, etc.) Enjoy listenin...	3 beds \| 2 baths \| 1,769 sq.ft.	$1,399,000	Airbnb cash on cash: N/A Traditional cash on cash: 0.05% Airbnb Rental Income: $null Traditional Rental Income: $2614 Airbnb ROI: N/A Traditional ROI: 0.05%
78746 US HWY 40 unit: 222 #222 Winter Park, CO $30k incentive to use as Buyer wishes (2/1 Buy Down, hot tub, blinds, etc.) This is is our...	2 beds \| 2 baths \| 1,227 sq.ft.	$999,000	Airbnb cash on cash: -0.84% Traditional cash on cash: 0.61% Airbnb Rental Income: $1480 Traditional Rental Income: $2389 Airbnb ROI: -0.84% Traditional ROI: 0.61%
432 Hi Country Drive unit: 15 #15 Winter Park, CO TOP FLOOR condo in the heart of downtown Winter Park. Unique gem beautifully renovated rig...	1 beds \| 1 baths \| 465 sq.ft.	$415,000	Airbnb cash on cash: N/A Traditional cash on cash: 0.23% Airbnb Rental Income: $null Traditional Rental Income: $1238 Airbnb ROI: N/A Traditional ROI: 0.23%
246 Hi Country Drive #3 Winter Park, CO Hi Country Condosâa modern retreat in the heart of Winter Park, CO. Completely remodeled...	2 beds \| 2 baths \| 935 sq.ft.	$674,750	Airbnb cash on cash: -0.88% Traditional cash on cash: 0.48% Airbnb Rental Income: $1480 Traditional Rental Income: $1898 Airbnb ROI: -0.88% Traditional ROI: 0.48%
78746 US HWY 40 unit: 212 #212 Winter Park, CO Only 2 of this floorplan remain. This mountain modern residence is being sold furnished. F...	2 beds \| 2 baths \| 848 sq.ft.	$795,000	Airbnb cash on cash: -0.49% Traditional cash on cash: 0.67% Airbnb Rental Income: $1480 Traditional Rental Income: $1905 Airbnb ROI: -0.49% Traditional ROI: 0.67%
273 Hi Country Drive unit: 15 #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.	$405,000	Airbnb cash on cash: N/A Traditional cash on cash: 0.05% Airbnb Rental Income: $null Traditional Rental Income: $1138 Airbnb ROI: N/A Traditional ROI: 0.05%
78746 US HWY 40 unit: 218 #218 Winter Park, CO $40k Buyer Incentive - use as you wish (2/1 buy down, hot tub, blinds, etc.) MOVE-IN READY...	3 beds \| 3 baths \| 1,506 sq.ft.	$1,230,000	Airbnb cash on cash: N/A Traditional cash on cash: 0.34% Airbnb Rental Income: $null Traditional Rental Income: $2609 Airbnb ROI: N/A Traditional ROI: 0.34%
720 BAKER Drive unit: 409 #409 Winter Park, CO Introducing the highly anticipated Headwaters Condos, a premier new construction project i...	2 beds \| 2 baths \| 958 sq.ft.	$895,000	Airbnb cash on cash: -1.08% Traditional cash on cash: 0.07% Airbnb Rental Income: $1480 Traditional Rental Income: $2002 Airbnb ROI: -1.08% Traditional ROI: 0.07%
720 BAKER Drive unit: 306 #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: -1.08% Traditional cash on cash: 0.07% Airbnb Rental Income: $1480 Traditional Rental Income: $2002 Airbnb ROI: -1.08% Traditional ROI: 0.07%
720 BAKER Drive unit: 406 #406 Winter Park, CO Introducing the highly anticipated Headwaters Condos, a premier new construction project i...	2 beds \| 2 baths \| 958 sq.ft.	$895,000	Airbnb cash on cash: -1.08% Traditional cash on cash: 0.15% Airbnb Rental Income: $1480 Traditional Rental Income: $2073 Airbnb ROI: -1.08% Traditional ROI: 0.15%
720 BAKER Drive unit: 304 #304 Winter Park, CO Introducing the highly anticipated Headwaters Condos, a premier new construction project i...	2 beds \| 1 baths \| 874 sq.ft.	$795,000	Airbnb cash on cash: -1% Traditional cash on cash: 0.06% Airbnb Rental Income: $1480 Traditional Rental Income: $1831 Airbnb ROI: -1% Traditional ROI: 0.06%
720 BAKER Drive unit: 308 #308 Winter Park, CO Introducing the highly anticipated Headwaters Condos, a premier new construction project i...	2 beds \| 2 baths \| 955 sq.ft.	$845,000	Airbnb cash on cash: -1.06% Traditional cash on cash: 0.25% Airbnb Rental Income: $1480 Traditional Rental Income: $2073 Airbnb ROI: -1.06% Traditional ROI: 0.25%
720 Baker Drive unit: 410 #410 Winter Park, CO An opportunity to own the brand new 4th floor penthouse with floor to ceiling windows to e...	3 beds \| 3 baths \| 1,482 sq.ft.	$1,480,000	Airbnb cash on cash: N/A Traditional cash on cash: -0.12% Airbnb Rental Income: $null Traditional Rental Income: $2505 Airbnb ROI: N/A Traditional ROI: -0.12%
78491 US HWY 40 unit: #5 #5 Winter Park, CO This beautifully updated 2-bedroom, 1-bath condo offers an unbeatable downtown Winter Park...	2 beds \| 1 baths \| 1,125 sq.ft.	$529,000	Airbnb cash on cash: -0.92% Traditional cash on cash: -0.01% Airbnb Rental Income: $1480 Traditional Rental Income: $1495 Airbnb ROI: -0.92% Traditional ROI: -0.01%
78746 US HWY 40 unit: 209 #209 Winter Park, CO Only 7 residences remaining. This mountain modern residence features soaring ceilings & fl...	2 beds \| 2 baths \| 852 sq.ft.	$779,000	Airbnb cash on cash: -0.48% Traditional cash on cash: 0.71% Airbnb Rental Income: $1480 Traditional Rental Income: $1903 Airbnb ROI: -0.48% Traditional ROI: 0.71%
580 Winter Park Drive unit: #4571-4573 #4571-4573 Winter Park, CO This SKI-IN/SKI-OUT 2-Bedroom Condo in Founders Pointe has Views of the Winter Park Ski Re...	2 beds \| 2 baths \| 1,025 sq.ft.	$989,000	Airbnb cash on cash: -2.3% Traditional cash on cash: -1.43% Airbnb Rental Income: $1480 Traditional Rental Income: $1842 Airbnb ROI: -2.3% Traditional ROI: -1.43%
400 Baker Drive unit: 209 #209 Winter Park, CO 2 beds with the primary King bedroom having an attached bath and designated area with buil...	1 beds \| 2 baths \| 1,011 sq.ft.	$695,000	Airbnb cash on cash: N/A Traditional cash on cash: 0.66% Airbnb Rental Income: $null Traditional Rental Income: $2044 Airbnb ROI: N/A Traditional ROI: 0.66%
247 Hi Country Drive unit: Bld 11 #16 #Bld 11 #16 Winter Park, CO This bright and well-maintained 1-bedroom, 1-bathroom condo in Hi Country Haus is perched ...	1 beds \| 1 baths \| 492 sq.ft.	$413,000	Airbnb cash on cash: N/A Traditional cash on cash: -0.37% Airbnb Rental Income: $null Traditional Rental Income: $1118 Airbnb ROI: N/A Traditional ROI: -0.37%
357 Hi Country Drive #5 Winter Park, CO Welcome to your mountain retreat in the heart of Winter Park! This 2-bedroom, 2-bath condo...	2 beds \| 2 baths \| 1,051 sq.ft.	$619,999	Airbnb cash on cash: -0.71% Traditional cash on cash: 0.23% Airbnb Rental Income: $1480 Traditional Rental Income: $1587 Airbnb ROI: -0.71% Traditional ROI: 0.23%
79050 US HWY 40 unit: A-314 #A-314 Winter Park, CO Live in the heart of it all with this beautifully located 2-bedroom, 3 bathroom condo just...	2 beds \| 3 baths \| 1,124 sq.ft.	$660,000	Airbnb cash on cash: -1.74% Traditional cash on cash: -0.54% Airbnb Rental Income: $1480 Traditional Rental Income: $1783 Airbnb ROI: -1.74% Traditional ROI: -0.54%
128 GCR 702 unit: 4-202 #4-202 Winter Park, CO Don't miss this 2-bedroom, 2-bathroom condo in Winter Park, that offers the perfect blend ...	2 beds \| 2 baths \| 850 sq.ft.	$609,000	Airbnb cash on cash: -0.76% Traditional cash on cash: 0.1% Airbnb Rental Income: $1480 Traditional Rental Income: $1535 Airbnb ROI: -0.76% Traditional ROI: 0.1%
195 HIGH SEASONS unit: 1 #1 Winter Park, CO Unique and rare condo offering at High Seasons in Winter Park. This small, quaint oasis ne...	2 beds \| 1 baths \| 576 sq.ft.	$469,000	Airbnb cash on cash: -0.59% Traditional cash on cash: -0.05% Airbnb Rental Income: $1480 Traditional Rental Income: $1280 Airbnb ROI: -0.59% Traditional ROI: -0.05%
124 GCR 702 unit: 204 #204 Winter Park, CO Come check out this bright and inviting, nicely updated 2-bedroom 2-bath end unit. The upd...	2 beds \| 2 baths \| 850 sq.ft.	$599,000	Airbnb cash on cash: -0.7% Traditional cash on cash: 0.16% Airbnb Rental Income: $1480 Traditional Rental Income: $1527 Airbnb ROI: -0.7% Traditional ROI: 0.16%
51 River Drive unit: 10 #10 Winter Park, CO Riverside Retreat in the Heart of Winter Park. This updated 2-bedroom, 2-bath condo offers...	2 beds \| 2 baths \| 899 sq.ft.	$637,000	Airbnb cash on cash: -0.88% Traditional cash on cash: 0.34% Airbnb Rental Income: $1480 Traditional Rental Income: $1773 Airbnb ROI: -0.88% Traditional ROI: 0.34%
580 WINTER PARK Drive unit: 4475 #4475 Winter Park, CO Premium location at the end of the hall with beautiful views of the Winter Park Resort and...	2 beds \| 2 baths \| 991 sq.ft.	$949,900	Airbnb cash on cash: -3.6% Traditional cash on cash: -2.76% Airbnb Rental Income: $1480 Traditional Rental Income: $1785 Airbnb ROI: -3.6% Traditional ROI: -2.76%
501 TRAILHEAD unit: 533 #533 Winter Park, CO This Trailhead Lodge top floor unit is located in the heart of downtown Winter Park but yo...	2 beds \| 2 baths \| 1,193 sq.ft.	$975,000	Airbnb cash on cash: -1.01% Traditional cash on cash: -0.01% Airbnb Rental Income: $1480 Traditional Rental Income: $1946 Airbnb ROI: -1.01% Traditional ROI: -0.01%
510 KINGS CROSSING unit: C 202 #C 202 Winter Park, CO Discover mountain living at its best in this updated 2-bedroom, 2-bath condo, ideally loca...	2 beds \| 2 baths \| 813 sq.ft.	$549,000	Airbnb cash on cash: -0.95% Traditional cash on cash: 0.08% Airbnb Rental Income: $1480 Traditional Rental Income: $1573 Airbnb ROI: -0.95% Traditional ROI: 0.08%
580 Winter Park Drive unit: 4566 #4566 Winter Park, CO LOWEST PRICED one-bedroom in the complex! This fully furnished ski-in/ski-out condo is loc...	1 beds \| 1 baths \| 533 sq.ft.	$555,000	Airbnb cash on cash: N/A Traditional cash on cash: -1.62% Airbnb Rental Income: $null Traditional Rental Income: $1491 Airbnb ROI: N/A Traditional ROI: -1.62%
357 HI COUNTRY Drive unit: 23-12 #23-12 Winter Park, CO An exceptional top floor Winter Park location at Hi Country Haus where you can walk in all...	2 beds \| 2 baths \| 1,051 sq.ft.	$609,900	Airbnb cash on cash: -0.83% Traditional cash on cash: 0.18% Airbnb Rental Income: $1480 Traditional Rental Income: $1618 Airbnb ROI: -0.83% Traditional ROI: 0.18%
128 GCR 702 unit: 4-201 #4-201 Winter Park, CO Tucked into the trees in Beaver Village, this private second-floor end unit offers a rare ...	2 beds \| 2 baths \| 850 sq.ft.	$619,000	Airbnb cash on cash: -0.71% Traditional cash on cash: 0.18% Airbnb Rental Income: $1480 Traditional Rental Income: $1557 Airbnb ROI: -0.71% Traditional ROI: 0.18%
128 GCR 702 unit: 4-104 #4-104 Winter Park, CO Nestled in the aspens and pines, this ground floor, corner unit in Beaver Village is not o...	2 beds \| 2 baths \| 850 sq.ft.	$622,500	Airbnb cash on cash: 0.28% Traditional cash on cash: 0.99% Airbnb Rental Income: $1480 Traditional Rental Income: $1458 Airbnb ROI: 0.28% Traditional ROI: 0.99%
217 Van Anderson Dr unit: 6 #6 Winter Park, CO Escape to this quintessential ski cabin in the heart of Winter Park! This inviting 2-bedro...	2 beds \| 2 baths \| 847 sq.ft.	$475,000	Airbnb cash on cash: 0.78% Traditional cash on cash: 1.97% Airbnb Rental Income: $1480 Traditional Rental Income: $1573 Airbnb ROI: 0.78% Traditional ROI: 1.97%
189 GCR 702 unit: 5-204 #5-204 Winter Park, CO Prime Location Just Minutes from Winter Park Resort and steps to the proposed Gondola and ...	2 beds \| 2 baths \| 940 sq.ft.	$589,000	Airbnb cash on cash: 0.3% Traditional cash on cash: 1.26% Airbnb Rental Income: $1480 Traditional Rental Income: $1571 Airbnb ROI: 0.3% Traditional ROI: 1.26%
670 WINTER PARK Drive unit: 3129 #3129 Winter Park, CO This ground floor 2 bedroom, 2 bath unit is easily accessible from Winter Park Drive and t...	2 beds \| 2 baths \| 1,006 sq.ft.	$949,000	Airbnb cash on cash: -0.53% Traditional cash on cash: 0.37% Airbnb Rental Income: $1480 Traditional Rental Income: $1837 Airbnb ROI: -0.53% Traditional ROI: 0.37%
670 Winter Park Drive unit: 3307 #3307 Winter Park, CO This larger one-bedroom condo at Fraser Crossing offers extra space and is in a prime loca...	1 beds \| 1 baths \| 620 sq.ft.	$585,000	Airbnb cash on cash: N/A Traditional cash on cash: 0.93% Airbnb Rental Income: $null Traditional Rental Income: $1509 Airbnb ROI: N/A Traditional ROI: 0.93%
580 Winter Park Drive unit: 4370 #4370 Winter Park, CO This turnkey and low maintenance condo will become your favorite oasis at the Winter Park ...	1 beds \| 1 baths \| 533 sq.ft.	$555,000	Airbnb cash on cash: N/A Traditional cash on cash: 0.99% Airbnb Rental Income: $null Traditional Rental Income: $1434 Airbnb ROI: N/A Traditional ROI: 0.99%
40 GCR 702 / Village Drive unit: 1-101 #1-101 Winter Park, CO Beautiful 2BD/2BA condo in Beaver Village, just minutes from downtown Winter Park and reso...	2 beds \| 2 baths \| 850 sq.ft.	$595,000	Airbnb cash on cash: 0.31% Traditional cash on cash: 1.24% Airbnb Rental Income: $1480 Traditional Rental Income: $1559 Airbnb ROI: 0.31% Traditional ROI: 1.24%
216 GCR 702 #18-101 Winter Park, CO Beautifully updated ground-floor end unit condo in the heart of Winter Park with an open f...	2 beds \| 2 baths \| 940 sq.ft.	$589,900	Airbnb cash on cash: 0.29% Traditional cash on cash: 1.26% Airbnb Rental Income: $1480 Traditional Rental Income: $1578 Airbnb ROI: 0.29% Traditional ROI: 1.26%
30 E Viking Drive unit: A201 #A201 Winter Park, CO Three-bedroom condo borders Arapahoe National Forest with a generous open living area that...	3 beds \| 3 baths \| 1,266 sq.ft.	$869,000	Airbnb cash on cash: N/A Traditional cash on cash: 1.13% Airbnb Rental Income: $null Traditional Rental Income: $2133 Airbnb ROI: N/A Traditional ROI: 1.13%

Your search for investment property begins and ends here

Condos for Sale in Winter Park, CO

78746 US Highway 40 unit: 221 #221

Winter Park, CO

3 beds | 2 baths | 1,769 sq.ft.

$1,399,000

Airbnb cash on cash: N/A

Traditional cash on cash: 0.05%

Airbnb Rental Income: $null

Traditional Rental Income: $2614

Airbnb ROI: N/A

Traditional ROI: 0.05%

78746 US HWY 40 unit: 222 #222

Winter Park, CO

2 beds | 2 baths | 1,227 sq.ft.

$999,000

Airbnb cash on cash: -0.84%

Traditional cash on cash: 0.61%

Airbnb Rental Income: $1480

Traditional Rental Income: $2389

Airbnb ROI: -0.84%

Traditional ROI: 0.61%

432 Hi Country Drive unit: 15 #15

Winter Park, CO

1 beds | 1 baths | 465 sq.ft.

$415,000

Airbnb cash on cash: N/A

Traditional cash on cash: 0.23%

Airbnb Rental Income: $null

Traditional Rental Income: $1238

Airbnb ROI: N/A

Traditional ROI: 0.23%

246 Hi Country Drive #3

Winter Park, CO

2 beds | 2 baths | 935 sq.ft.

$674,750

Airbnb cash on cash: -0.88%

Traditional cash on cash: 0.48%

Airbnb Rental Income: $1480

Traditional Rental Income: $1898

Airbnb ROI: -0.88%

Traditional ROI: 0.48%

78746 US HWY 40 unit: 212 #212

Winter Park, CO

2 beds | 2 baths | 848 sq.ft.

$795,000

Airbnb cash on cash: -0.49%

Traditional cash on cash: 0.67%

Airbnb Rental Income: $1480

Traditional Rental Income: $1905

Airbnb ROI: -0.49%

Traditional ROI: 0.67%

273 Hi Country Drive unit: 15 #15

Winter Park, CO

1 beds | 1 baths | 459 sq.ft.

$405,000

Airbnb cash on cash: N/A

Traditional cash on cash: 0.05%

Airbnb Rental Income: $null

Traditional Rental Income: $1138

Airbnb ROI: N/A

Traditional ROI: 0.05%

78746 US HWY 40 unit: 218 #218

Winter Park, CO

3 beds | 3 baths | 1,506 sq.ft.

$1,230,000

Airbnb cash on cash: N/A

Traditional cash on cash: 0.34%

Airbnb Rental Income: $null

Traditional Rental Income: $2609

Airbnb ROI: N/A

Traditional ROI: 0.34%

720 BAKER Drive unit: 409 #409

Winter Park, CO

2 beds | 2 baths | 958 sq.ft.

$895,000

Airbnb cash on cash: -1.08%

Traditional cash on cash: 0.07%

Airbnb Rental Income: $1480

Traditional Rental Income: $2002

Airbnb ROI: -1.08%