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.

Investment Property for Sale in Winter Park, CO

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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: 0.14% Traditional cash on cash: 0.52% Airbnb Rental Income: $2486 Traditional Rental Income: $2186 Airbnb ROI: 0.14% 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: 0.16% Traditional cash on cash: 0.48% Airbnb Rental Income: $2261 Traditional Rental Income: $1898 Airbnb ROI: 0.16% 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: -0.51% Traditional cash on cash: 0.05% Airbnb Rental Income: $2486 Traditional Rental Income: $2614 Airbnb ROI: -0.51% 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: -0.14% Traditional cash on cash: 0.61% Airbnb Rental Income: $2261 Traditional Rental Income: $2389 Airbnb ROI: -0.14% Traditional ROI: 0.61%
490 Kings Crossing Road 631-633 Winter Park, CO OPEN HOUSE Saturday 10/4, 4-7PM; Sunday 10/5, 1-4PM Unique opportunity!!! This is the ONLY...	4 beds \| 4 baths \| 1,720 sq.ft.	$899,999	Airbnb cash on cash: 1.23% Traditional cash on cash: 1.83% Airbnb Rental Income: $3094 Traditional Rental Income: $2886 Airbnb ROI: 1.23% Traditional ROI: 1.83%
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.	$2,879,709	Airbnb cash on cash: -0.75% Traditional cash on cash: -0.34% Airbnb Rental Income: $3094 Traditional Rental Income: $3491 Airbnb ROI: -0.75% Traditional ROI: -0.34%
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.	$2,626,860	Airbnb cash on cash: -0.68% Traditional cash on cash: -0.35% Airbnb Rental Income: $3094 Traditional Rental Income: $3179 Airbnb ROI: -0.68% Traditional ROI: -0.35%
45 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.	$2,616,629	Airbnb cash on cash: -0.67% Traditional cash on cash: -0.35% Airbnb Rental Income: $3094 Traditional Rental Income: $3179 Airbnb ROI: -0.67% Traditional ROI: -0.35%
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: -0.3% Traditional cash on cash: 0.07% Airbnb Rental Income: $2261 Traditional Rental Income: $2002 Airbnb ROI: -0.3% 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: -0.3% Traditional cash on cash: 0.07% Airbnb Rental Income: $2261 Traditional Rental Income: $2002 Airbnb ROI: -0.3% 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: -0.3% Traditional cash on cash: 0.15% Airbnb Rental Income: $2261 Traditional Rental Income: $2073 Airbnb ROI: -0.3% 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: -0.12% Traditional cash on cash: 0.06% Airbnb Rental Income: $2261 Traditional Rental Income: $1831 Airbnb ROI: -0.12% 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: 0.17% Traditional cash on cash: 0.05% Airbnb Rental Income: $1649 Traditional Rental Income: $1138 Airbnb ROI: 0.17% Traditional ROI: 0.05%
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: -0.23% Traditional cash on cash: 0.61% Airbnb Rental Income: $3094 Traditional Rental Income: $4517 Airbnb ROI: -0.23% Traditional ROI: 0.61%
580 WINTER PARK unit: 4474 #4474 Winter Park, CO This is the one you have been waiting for! A ski in/walk out condominium that has been com...	2 beds \| 2 baths \| 991 sq.ft.	$975,000	Airbnb cash on cash: -2.12% Traditional cash on cash: -1.64% Airbnb Rental Income: $2261 Traditional Rental Income: $2126 Airbnb ROI: -2.12% Traditional ROI: -1.64%
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: -0.23% Traditional cash on cash: 0.25% Airbnb Rental Income: $2261 Traditional Rental Income: $2073 Airbnb ROI: -0.23% Traditional ROI: 0.25%
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: -1.06% Traditional cash on cash: -0.11% Airbnb Rental Income: $1649 Traditional Rental Income: $2097 Airbnb ROI: -1.06% Traditional ROI: -0.11%
442 Lions Gate Dr Winter Park, CO UNDER NEW MANAGEMENT & NEW CONTRACTOR! Things are moving along for Reunion Lofts! Stunning...	3 beds \| 3 baths \| 2,240 sq.ft.	$1,650,000	Airbnb cash on cash: -1.24% Traditional cash on cash: -0.68% Airbnb Rental Income: $2486 Traditional Rental Income: $2743 Airbnb ROI: -1.24% Traditional ROI: -0.68%
454 Lions Gate Dr Winter Park, CO UNDER NEW MANAGEMENT & NEW CONTRACTOR! Things are moving along for Reunion Lofts! Stunning...	3 beds \| 3 baths \| 2,240 sq.ft.	$1,525,000	Airbnb cash on cash: 0.17% Traditional cash on cash: 0.84% Airbnb Rental Income: $2486 Traditional Rental Income: $2830 Airbnb ROI: 0.17% Traditional ROI: 0.84%
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: 1.18% Traditional cash on cash: 1.32% Airbnb Rental Income: $1649 Traditional Rental Income: $1246 Airbnb ROI: 1.18% Traditional ROI: 1.32%
601 Trailside Lane Winter Park, CO Incredible Views from this spectacular townhome in Lakota! Welcome to 601 Trailside Lane, ...	3 beds \| 3 baths \| 1,973 sq.ft.	$1,745,000	Airbnb cash on cash: -0.27% Traditional cash on cash: 0.24% Airbnb Rental Income: $2486 Traditional Rental Income: $2713 Airbnb ROI: -0.27% Traditional ROI: 0.24%
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: 1.74% Traditional cash on cash: 1.42% Airbnb Rental Income: $2261 Traditional Rental Income: $1528 Airbnb ROI: 1.74% Traditional ROI: 1.42%
378 Lake Trail Winter Park, CO Final Opportunity! Don't miss your chance to own one of the last remaining Lake Trail view...	3 beds \| N/A baths \| 1,948 sq.ft.	$1,399,000	Airbnb cash on cash: 0.15% Traditional cash on cash: 0.38% Airbnb Rental Income: $2486 Traditional Rental Income: $2177 Airbnb ROI: 0.15% Traditional ROI: 0.38%
374 Lake Trail Winter Park, CO Experience mountain living at its finest in this stylish and serene Mountain Modern townho...	3 beds \| N/A baths \| 1,306 sq.ft.	$1,099,000	Airbnb cash on cash: 0.56% Traditional cash on cash: 0.83% Airbnb Rental Income: $2486 Traditional Rental Income: $2158 Airbnb ROI: 0.56% Traditional ROI: 0.83%
1080 WINTER PARK Drive unit: 15 #15 Winter Park, CO To-the-studs renovation! This fully-furnished and ready for immediate rental or luxury liv...	2 beds \| N/A baths \| 1,377 sq.ft.	$990,000	Airbnb cash on cash: 0.46% Traditional cash on cash: 1.33% Airbnb Rental Income: $2261 Traditional Rental Income: $2500 Airbnb ROI: 0.46% Traditional ROI: 1.33%
385 Lions Gate Drive unit: C #C Winter Park, CO Welcome to Lion's Rock Townhomes-Winter Park's most premium and sophisticated boutique dev...	4 beds \| N/A baths \| 2,807 sq.ft.	$2,150,000	Airbnb cash on cash: -0.11% Traditional cash on cash: 1.59% Airbnb Rental Income: $3094 Traditional Rental Income: $5775 Airbnb ROI: -0.11% Traditional ROI: 1.59%
385 Lions Gate Drive unit: B #B Winter Park, CO Welcome to Lion's Rock Townhomes-Winter Park's most premium and sophisticated boutique dev...	4 beds \| N/A baths \| 2,824 sq.ft.	$1,875,000	Airbnb cash on cash: 0.02% Traditional cash on cash: 1.96% Airbnb Rental Income: $3094 Traditional Rental Income: $5775 Airbnb ROI: 0.02% Traditional ROI: 1.96%
120 Whistlestop Circle unit: B1 #B1 Winter Park, CO Rare 5-Bedroom Luxury Townhome in the Heart of Downtown Winter Park! Opportunities like th...	5 beds \| 5 baths \| 3,002 sq.ft.	$2,350,000	Airbnb cash on cash: 1.36% Traditional cash on cash: 1.01% Airbnb Rental Income: $6571 Traditional Rental Income: $4524 Airbnb ROI: 1.36% Traditional ROI: 1.01%
580 WINTER PARK unit: #4549 #4549 Winter Park, CO Enjoy the ultimate mountain lifestyle with direct access to the slopes and trails right ou...	2 beds \| 2 baths \| 900 sq.ft.	$939,000	Airbnb cash on cash: 0.27% Traditional cash on cash: 0.33% Airbnb Rental Income: $2261 Traditional Rental Income: $1751 Airbnb ROI: 0.27% Traditional ROI: 0.33%
476 KINGS CROSSING RD Winter Park, CO Rare Find in the Heart of Winter Park! This 3-level townhome offers an unbeatable location...	3 beds \| N/A baths \| 1,572 sq.ft.	$925,000	Airbnb cash on cash: 0.69% Traditional cash on cash: 1.86% Airbnb Rental Income: $2486 Traditional Rental Income: $2890 Airbnb ROI: 0.69% Traditional ROI: 1.86%
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: 0.85% Traditional cash on cash: 1.19% Airbnb Rental Income: $2261 Traditional Rental Income: $1943 Airbnb ROI: 0.85% 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: 0.3% Traditional cash on cash: 0.51% Airbnb Rental Income: $1649 Traditional Rental Income: $1324 Airbnb ROI: 0.3% 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: 0.42% Traditional cash on cash: 0.32% Airbnb Rental Income: $2261 Traditional Rental Income: $1604 Airbnb ROI: 0.42% Traditional ROI: 0.32%
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: 0.49% Traditional cash on cash: 0.98% Airbnb Rental Income: $6571 Traditional Rental Income: $6623 Airbnb ROI: 0.49% Traditional ROI: 0.98%
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: 1.42% Traditional cash on cash: 1.44% Airbnb Rental Income: $1649 Traditional Rental Income: $1191 Airbnb ROI: 1.42% 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: 1.77% Traditional cash on cash: 1.44% Airbnb Rental Income: $2486 Traditional Rental Income: $1696 Airbnb ROI: 1.77% Traditional ROI: 1.44%
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: 0.26% Traditional cash on cash: 0.67% Airbnb Rental Income: $6571 Traditional Rental Income: $6606 Airbnb ROI: 0.26% Traditional ROI: 0.67%
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: 1.44% Traditional cash on cash: 1.9% Airbnb Rental Income: $2486 Traditional Rental Income: $2158 Airbnb ROI: 1.44% Traditional ROI: 1.9%
405 Bear Trail Winter Park, CO Mountain Luxury Meets Adventure: 4 Bedroom Ski Townhome in Winter Park. This spacious 4 be...	4 beds \| N/A baths \| 2,143 sq.ft.	$1,775,000	Airbnb cash on cash: 0.2% Traditional cash on cash: 0.45% Airbnb Rental Income: $3094 Traditional Rental Income: $2807 Airbnb ROI: 0.2% Traditional ROI: 0.45%
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: 0.79% Traditional cash on cash: 1.46% Airbnb Rental Income: $2261 Traditional Rental Income: $2194 Airbnb ROI: 0.79% Traditional ROI: 1.46%

Real Estate investment in Winter-park, CO

There are 95 properties for sale in the city of Winter Park . The median list price in Winter Park is $999,000 and the average price per square foot is $594. In November 2025, the average monthly cash on cash return in Winter Park is N/A%. The average monthly rental income in Winter Park is $2,334.

Winter-park, CO Real Estate Investing: FAQs for Buyers, Sellers and Investors

There are 95 investment properties available for sale in Winter-park.

In 2025, the best neighborhood to buy investment property is Winter Park.

The ROI for Short-Term is higher than the Long-Term in Winter-park with average rental income of $2,486.

Your search for investment property begins and ends here

Investment Property 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: 0.14%

Traditional cash on cash: 0.52%

Airbnb Rental Income: $2486

Traditional Rental Income: $2186

Airbnb ROI: 0.14%

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: 0.16%

Traditional cash on cash: 0.48%

Airbnb Rental Income: $2261

Traditional Rental Income: $1898

Airbnb ROI: 0.16%

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: -0.51%

Traditional cash on cash: 0.05%

Airbnb Rental Income: $2486

Traditional Rental Income: $2614

Airbnb ROI: -0.51%

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: -0.14%

Traditional cash on cash: 0.61%

Airbnb Rental Income: $2261

Traditional Rental Income: $2389

Airbnb ROI: -0.14%

Traditional ROI: 0.61%

490 Kings Crossing Road 631-633

Winter Park, CO

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

$899,999

Airbnb cash on cash: 1.23%

Traditional cash on cash: 1.83%

Airbnb Rental Income: $3094

Traditional Rental Income: $2886

Airbnb ROI: 1.23%

Traditional ROI: 1.83%

57 Scenic Trail

Winter Park, CO

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

$2,879,709

Airbnb cash on cash: -0.75%

Traditional cash on cash: -0.34%

Airbnb Rental Income: $3094

Traditional Rental Income: $3491

Airbnb ROI: -0.75%

Traditional ROI: -0.34%

19 Scenic Trail

Winter Park, CO

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

$2,626,860

Airbnb cash on cash: -0.68%

Traditional cash on cash: -0.35%

Airbnb Rental Income: $3094

Traditional Rental Income: $3179

Airbnb ROI: -0.68%

Traditional ROI: -0.35%

45 Scenic Trail

Winter Park, CO

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

$2,616,629

Airbnb cash on cash: -0.67%

Traditional cash on cash: -0.35%

Airbnb Rental Income: $3094

Traditional Rental Income: $3179

Airbnb ROI: -0.67%