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 43 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
300 Kings Crossing Road #B3 Winter Park, CO Welcome to your ideal mountain retreat! This inviting 3-bedroom, 3-bath townhome is perfec...	3 beds \| 3 baths \| 1,378 sq.ft.	$850,000	Airbnb cash on cash: -0.69% Traditional cash on cash: 0.52% Airbnb Rental Income: $1699 Traditional Rental Income: $2186 Airbnb ROI: -0.69% Traditional ROI: 0.52%
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.	$672,500	Airbnb cash on cash: -1.03% Traditional cash on cash: 0.48% Airbnb Rental Income: $1363 Traditional Rental Income: $1898 Airbnb ROI: -1.03% Traditional ROI: 0.48%
78746 US Highway 40 unit: 221 #221 Winter Park, CO 30-year fixed financing as low as 5.625% for qualified buyers. MOVE-IN READY. Enjoy listen...	3 beds \| N/A baths \| 1,769 sq.ft.	$1,399,000	Airbnb cash on cash: -1.01% Traditional cash on cash: 0.05% Airbnb Rental Income: $1699 Traditional Rental Income: $2614 Airbnb ROI: -1.01% Traditional ROI: 0.05%
78746 US HWY 40 unit: 222 #222 Winter Park, CO 30-year fixed financing as low as 5.625% for qualified buyers. MOVE-IN READY. This is is o...	2 beds \| N/A baths \| 1,227 sq.ft.	$999,000	Airbnb cash on cash: -0.95% Traditional cash on cash: 0.61% Airbnb Rental Income: $1363 Traditional Rental Income: $2389 Airbnb ROI: -0.95% Traditional ROI: 0.61%
490 Kings Crossing Road 631-633 Winter Park, CO PRICE IMPROVEMENT! Motivated Seller, bring offer!! Unique opportunity!!! This is the ONLY ...	4 beds \| 4 baths \| 1,720 sq.ft.	$875,000	Airbnb cash on cash: 0.77% Traditional cash on cash: 1.92% Airbnb Rental Income: $2565 Traditional Rental Income: $2886 Airbnb ROI: 0.77% Traditional ROI: 1.92%
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: -1.2% Traditional cash on cash: 0.07% Airbnb Rental Income: $1363 Traditional Rental Income: $2002 Airbnb ROI: -1.2% 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.	$845,000	Airbnb cash on cash: -1.18% Traditional cash on cash: 0.16% Airbnb Rental Income: $1363 Traditional Rental Income: $2002 Airbnb ROI: -1.18% Traditional ROI: 0.16%
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: -1.13% Traditional cash on cash: 0.06% Airbnb Rental Income: $1363 Traditional Rental Income: $1831 Airbnb ROI: -1.13% Traditional ROI: 0.06%
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: -1.45% Traditional cash on cash: 0.05% Airbnb Rental Income: $908 Traditional Rental Income: $1138 Airbnb ROI: -1.45% Traditional ROI: 0.05%
720 BAKER Drive unit: 404 #404 Winter Park, CO Introducing the highly anticipated Headwaters Condos, a premier new construction project i...	1 beds \| 2 baths \| 1,154 sq.ft.	$1,025,000	Airbnb cash on cash: -1.71% Traditional cash on cash: -0.11% Airbnb Rental Income: $908 Traditional Rental Income: $2097 Airbnb ROI: -1.71% Traditional ROI: -0.11%
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: -1.18% Traditional cash on cash: 0.25% Airbnb Rental Income: $1363 Traditional Rental Income: $2073 Airbnb ROI: -1.18% Traditional ROI: 0.25%
400 Baker Drive unit: Te103 #Te103 Winter Park, CO Priced to Move! This fully furnished 2BR/2BA condo is ready to make your summer sing! Brig...	2 beds \| 2 baths \| 1,307 sq.ft.	$914,000	Airbnb cash on cash: -0.42% Traditional cash on cash: 1.07% Airbnb Rental Income: $1363 Traditional Rental Income: $2221 Airbnb ROI: -0.42% Traditional ROI: 1.07%
1128 Winter Park Drive unit: #7 #7 Winter Park, CO Welcome to your perfect mountain retreat! This light and bright one-bedroom condo offers a...	1 beds \| 1 baths \| 595 sq.ft.	$475,000	Airbnb cash on cash: -0.21% Traditional cash on cash: 1.32% Airbnb Rental Income: $908 Traditional Rental Income: $1246 Airbnb ROI: -0.21% Traditional ROI: 1.32%
121 ELK Trail unit: 6 #6 Winter Park, CO Welcome to your alpine getaway at 121 Elk Trail. A beautifully situated condo in the heart...	3 beds \| N/A baths \| 2,217 sq.ft.	$875,000	Airbnb cash on cash: -0.01% Traditional cash on cash: 1.26% Airbnb Rental Income: $1699 Traditional Rental Income: $2264 Airbnb ROI: -0.01% Traditional ROI: 1.26%
169 VAN ANDERSON unit: #3 #3 Winter Park, CO Thoughtfully updated 2-bed, 2-bath condo nestled in the pines just 1 mile from downtown Wi...	2 beds \| 2 baths \| 895 sq.ft.	$555,000	Airbnb cash on cash: 0.3% Traditional cash on cash: 1.42% Airbnb Rental Income: $1363 Traditional Rental Income: $1528 Airbnb ROI: 0.3% Traditional ROI: 1.42%
1080 WINTER PARK unit: #18 #18 Winter Park, CO Your Perfect Mountain Retreat - Remodeled 2-Bedroom Condo on the River, Steps from Winter ...	2 beds \| 2 baths \| 1,377 sq.ft.	$779,000	Airbnb cash on cash: -0.18% Traditional cash on cash: 1.19% Airbnb Rental Income: $1363 Traditional Rental Income: $1943 Airbnb ROI: -0.18% Traditional ROI: 1.19%
401 NYSTROM unit: #1307 #1307 Winter Park, CO This beautifully remodeled platinum rated one bedroom unit offers the ultimate ski in/ski ...	1 beds \| 1 baths \| 521 sq.ft.	$698,000	Airbnb cash on cash: -0.65% Traditional cash on cash: 0.51% Airbnb Rental Income: $908 Traditional Rental Income: $1324 Airbnb ROI: -0.65% Traditional ROI: 0.51%
201 ZEPHYR Way unit: 2700 #2700 Winter Park, CO Top floor condo with vaulted ceilings in the Riverside Building at Zephyr Mountain Lodge. ...	2 beds \| 2 baths \| 777 sq.ft.	$974,900	Airbnb cash on cash: -0.41% Traditional cash on cash: 0.32% Airbnb Rental Income: $1363 Traditional Rental Income: $1604 Airbnb ROI: -0.41% Traditional ROI: 0.32%
273 Hi Country Drive unit: #9 #9 Winter Park, CO Quietly tucked along the Fraser River in downtown Winter Park sits this beautifully and co...	1 beds \| 1 baths \| 460 sq.ft.	$415,000	Airbnb cash on cash: -0.17% Traditional cash on cash: 1.44% Airbnb Rental Income: $908 Traditional Rental Income: $1191 Airbnb ROI: -0.17% Traditional ROI: 1.44%
432 Hi Country Drive unit: 10-13 #10-13 Winter Park, CO Welcome to your perfect mountain getaway! This beautifully furnished 3-bedroom ski condo o...	3 beds \| N/A baths \| 804 sq.ft.	$600,000	Airbnb cash on cash: 0.6% Traditional cash on cash: 1.44% Airbnb Rental Income: $1699 Traditional Rental Income: $1696 Airbnb ROI: 0.6% Traditional ROI: 1.44%
78683 US HWY 40 unit: 13-151 #13-151 Winter Park, CO You can't beat the location of this 3-bedroom, 2-bath top-floor end unit in the heart of d...	3 beds \| N/A baths \| 1,152 sq.ft.	$650,000	Airbnb cash on cash: 0.36% Traditional cash on cash: 1.9% Airbnb Rental Income: $1699 Traditional Rental Income: $2158 Airbnb ROI: 0.36% Traditional ROI: 1.9%
225 Hi Country Drive unit: 11-1213 #11-1213 Winter Park, CO Listen to the river from this beautifully remodeled 2-bedroom, 2-bathroom end-unit condo a...	2 beds \| N/A baths \| 798 sq.ft.	$649,000	Airbnb cash on cash: 0.01% Traditional cash on cash: 0.92% Airbnb Rental Income: $1363 Traditional Rental Income: $1495 Airbnb ROI: 0.01% Traditional ROI: 0.92%
78746 US HWY 40 unit: 211 #211 Winter Park, CO 30-year fixed financing as low as 5.625% for qualified buyers. FURNISHED & MOVE-IN READY. ...	3 beds \| N/A baths \| 1,506 sq.ft.	$1,199,000	Airbnb cash on cash: -0.37% Traditional cash on cash: 0.63% Airbnb Rental Income: $1699 Traditional Rental Income: $2345 Airbnb ROI: -0.37% Traditional ROI: 0.63%
435 Iron Horse Way unit: J4209 #J4209 Winter Park, CO Discover your perfect mountain retreat in this top-floor, ski-in/ski-out condo at Iron Hor...	2 beds \| 3 baths \| 1,453 sq.ft.	$799,000	Airbnb cash on cash: -0.21% Traditional cash on cash: 1.46% Airbnb Rental Income: $1363 Traditional Rental Income: $2194 Airbnb ROI: -0.21% Traditional ROI: 1.46%
580 Winter Park Drive unit: 4571-4573 #4571-4573 Winter Park, CO SKI-IN/SKI-OUT at Founders Pointe! This 2-bed condo boasts panoramic views of Winter Park ...	2 beds \| 2 baths \| 1,025 sq.ft.	$949,000	Airbnb cash on cash: -2.44% Traditional cash on cash: -1.42% Airbnb Rental Income: $1363 Traditional Rental Income: $1842 Airbnb ROI: -2.44% Traditional ROI: -1.42%
78321 US Hwy 40 unit: 23 #23 Winter Park, CO See Virtual Tour for more photos! Step into mountain modern comfort with this bright, two-...	2 beds \| N/A baths \| 1,130 sq.ft.	$799,500	Airbnb cash on cash: -0.27% Traditional cash on cash: 1.3% Airbnb Rental Income: $1363 Traditional Rental Income: $2116 Airbnb ROI: -0.27% Traditional ROI: 1.3%
78746 US HWY 40 unit: 210 #210 Winter Park, CO 0-year fixed financing as low as 5.625% for qualified buyers. FURNISHED & MOVE-IN READY. O...	3 beds \| N/A baths \| 1,506 sq.ft.	$1,199,000	Airbnb cash on cash: -0.37% Traditional cash on cash: 0.5% Airbnb Rental Income: $1699 Traditional Rental Income: $2206 Airbnb ROI: -0.37% Traditional ROI: 0.5%
400 Baker Drive unit: 209 #209 Winter Park, CO In the heart of downtown Winter Park, this sharp and unique condo with over 1000 sq ft con...	1 beds \| 2 baths \| 1,011 sq.ft.	$650,000	Airbnb cash on cash: -1.66% Traditional cash on cash: 0.77% Airbnb Rental Income: $908 Traditional Rental Income: $2044 Airbnb ROI: -1.66% Traditional ROI: 0.77%
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.	$579,000	Airbnb cash on cash: -0.93% Traditional cash on cash: 0.15% Airbnb Rental Income: $1363 Traditional Rental Income: $1535 Airbnb ROI: -0.93% Traditional ROI: 0.15%
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: -3.4% Traditional cash on cash: -1.62% Airbnb Rental Income: $908 Traditional Rental Income: $1491 Airbnb ROI: -3.4% Traditional ROI: -1.62%
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.	$570,000	Airbnb cash on cash: -0.87% Traditional cash on cash: 0.27% Airbnb Rental Income: $1363 Traditional Rental Income: $1557 Airbnb ROI: -0.87% Traditional ROI: 0.27%
670 Winter Park Drive unit: 3307 #3307 Winter Park, CO Unlike most one-bedroom condos at Winter Park Resort, this spacious one-bedroom condo with...	1 beds \| 1 baths \| 620 sq.ft.	$575,000	Airbnb cash on cash: -0.79% Traditional cash on cash: 0.97% Airbnb Rental Income: $908 Traditional Rental Income: $1509 Airbnb ROI: -0.79% Traditional ROI: 0.97%
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.	$545,000	Airbnb cash on cash: -0.68% Traditional cash on cash: 1.02% Airbnb Rental Income: $908 Traditional Rental Income: $1434 Airbnb ROI: -0.68% Traditional ROI: 1.02%
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 \| N/A baths \| 850 sq.ft.	$574,000	Airbnb cash on cash: 0.18% Traditional cash on cash: 1.32% Airbnb Rental Income: $1363 Traditional Rental Income: $1559 Airbnb ROI: 0.18% Traditional ROI: 1.32%
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: 0.11% Traditional cash on cash: 1.26% Airbnb Rental Income: $1363 Traditional Rental Income: $1578 Airbnb ROI: 0.11% Traditional ROI: 1.26%
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: -1.2% Traditional cash on cash: 0.15% Airbnb Rental Income: $1363 Traditional Rental Income: $2073 Airbnb ROI: -1.2% Traditional ROI: 0.15%
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.	$599,900	Airbnb cash on cash: 0.15% Traditional cash on cash: 1.07% Airbnb Rental Income: $1363 Traditional Rental Income: $1458 Airbnb ROI: 0.15% Traditional ROI: 1.07%
1080 WINTER PARK Drive unit: 17 #17 Winter Park, CO In the heart of Old Town Winter Park, this beautifully updated 2-bedroom condo offers the ...	2 beds \| 2 baths \| 1,377 sq.ft.	$799,000	Airbnb cash on cash: -0.2% Traditional cash on cash: 1.14% Airbnb Rental Income: $1363 Traditional Rental Income: $1943 Airbnb ROI: -0.2% Traditional ROI: 1.14%
193 GCR 702 unit: 3-203 #3-203 Winter Park, CO Where adventure meets resort convenience, this Winter Park property is an invitation to em...	2 beds \| N/A baths \| 940 sq.ft.	$588,000	Airbnb cash on cash: 0.13% Traditional cash on cash: 1.33% Airbnb Rental Income: $1363 Traditional Rental Income: $1604 Airbnb ROI: 0.13% Traditional ROI: 1.33%
79114 Hwy 40 unit: C-11 #C-11 Winter Park, CO Don't miss this well-maintained 2 bd/2 bath end-unit condo in the heart of downtown Winter...	2 beds \| 2 baths \| 1,044 sq.ft.	$690,000	Airbnb cash on cash: -0.04% Traditional cash on cash: 1.08% Airbnb Rental Income: $1363 Traditional Rental Income: $1666 Airbnb ROI: -0.04% Traditional ROI: 1.08%

Your search for investment property begins and ends here

Condos for Sale in Winter Park, CO

300 Kings Crossing Road #B3

Winter Park, CO

3 beds | 3 baths | 1,378 sq.ft.

$850,000

Airbnb cash on cash: -0.69%

Traditional cash on cash: 0.52%

Airbnb Rental Income: $1699

Traditional Rental Income: $2186

Airbnb ROI: -0.69%

Traditional ROI: 0.52%

246 Hi Country Drive #3

Winter Park, CO

2 beds | 2 baths | 935 sq.ft.

$672,500

Airbnb cash on cash: -1.03%

Traditional cash on cash: 0.48%

Airbnb Rental Income: $1363

Traditional Rental Income: $1898

Airbnb ROI: -1.03%

Traditional ROI: 0.48%

78746 US Highway 40 unit: 221 #221

Winter Park, CO

3 beds | N/A baths | 1,769 sq.ft.

$1,399,000

Airbnb cash on cash: -1.01%

Traditional cash on cash: 0.05%

Airbnb Rental Income: $1699

Traditional Rental Income: $2614

Airbnb ROI: -1.01%

Traditional ROI: 0.05%

78746 US HWY 40 unit: 222 #222

Winter Park, CO

2 beds | N/A baths | 1,227 sq.ft.

$999,000

Airbnb cash on cash: -0.95%

Traditional cash on cash: 0.61%

Airbnb Rental Income: $1363

Traditional Rental Income: $2389

Airbnb ROI: -0.95%

Traditional ROI: 0.61%

490 Kings Crossing Road 631-633

Winter Park, CO

4 beds | 4 baths | 1,720 sq.ft.

$875,000

Airbnb cash on cash: 0.77%

Traditional cash on cash: 1.92%

Airbnb Rental Income: $2565

Traditional Rental Income: $2886

Airbnb ROI: 0.77%

Traditional ROI: 1.92%

720 BAKER Drive unit: 409 #409

Winter Park, CO

2 beds | 2 baths | 958 sq.ft.

$895,000

Airbnb cash on cash: -1.2%

Traditional cash on cash: 0.07%

Airbnb Rental Income: $1363

Traditional Rental Income: $2002

Airbnb ROI: -1.2%

Traditional ROI: 0.07%

720 BAKER Drive unit: 306 #306

Winter Park, CO

2 beds | 2 baths | 956 sq.ft.

$845,000

Airbnb cash on cash: -1.18%

Traditional cash on cash: 0.16%

Airbnb Rental Income: $1363

Traditional Rental Income: $2002

Airbnb ROI: -1.18%

Traditional ROI: 0.16%

720 BAKER Drive unit: 304 #304

Winter Park, CO

2 beds | 1 baths | 874 sq.ft.

$795,000

Airbnb cash on cash: -1.13%

Traditional cash on cash: 0.06%

Airbnb Rental Income: $1363

Traditional Rental Income: $1831

Airbnb ROI: -1.13%