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 $35k price drop just in time for ski season, let's close before the end of the year! Welco...	3 beds \| 3 baths \| 1,378 sq.ft.	$815,000	Airbnb cash on cash: -0.68% Traditional cash on cash: 0.58% Airbnb Rental Income: $1699 Traditional Rental Income: $2186 Airbnb ROI: -0.68% Traditional ROI: 0.58%
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.	$649,750	Airbnb cash on cash: -1.03% Traditional cash on cash: 0.53% Airbnb Rental Income: $1363 Traditional Rental Income: $1898 Airbnb ROI: -1.03% Traditional ROI: 0.53%
78746 US HWY 40 unit: 222 #222 Winter Park, CO MOVE-IN READY. This is is our largest 1-bedroom + loft/2-bath residence. The large loft ca...	2 beds \| 2 baths \| 1,227 sq.ft.	$849,000	Airbnb cash on cash: -2.36% Traditional cash on cash: -0.54% Airbnb Rental Income: $1363 Traditional Rental Income: $2389 Airbnb ROI: -2.36% Traditional ROI: -0.54%
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%
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%
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%
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.	$2,675,394	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%
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: -0.86% Traditional cash on cash: -0.35% Airbnb Rental Income: $2565 Traditional Rental Income: $3179 Airbnb ROI: -0.86% Traditional ROI: -0.35%
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%
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: -0.43% Traditional cash on cash: 0.7% Airbnb Rental Income: $1699 Traditional Rental Income: $2830 Airbnb ROI: -0.43% Traditional ROI: 0.7%
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: -0.47% Traditional cash on cash: 0.52% Airbnb Rental Income: $1699 Traditional Rental Income: $2743 Airbnb ROI: -0.47% Traditional ROI: 0.52%
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: -0.44% Traditional cash on cash: 1.06% Airbnb Rental Income: $1363 Traditional Rental Income: $2221 Airbnb ROI: -0.44% Traditional ROI: 1.06%
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 \| 3 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%
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.	$1,725,000	Airbnb cash on cash: -0.67% Traditional cash on cash: 0.25% Airbnb Rental Income: $1699 Traditional Rental Income: $2713 Airbnb ROI: -0.67% Traditional ROI: 0.25%
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%
374 Lake Trail Winter Park, CO Experience mountain living at its finest in this stylish and serene Mountain Modern townho...	3 beds \| 2 baths \| 1,306 sq.ft.	$1,099,000	Airbnb cash on cash: 0.01% Traditional cash on cash: 0.92% Airbnb Rental Income: $1699 Traditional Rental Income: $2158 Airbnb ROI: 0.01% Traditional ROI: 0.92%
385 Lions Gate Drive unit: I #I Winter Park, CO Welcome to Lion's Rock Townhomes-Winter Park's most premium and sophisticated boutique dev...	3 beds \| 4 baths \| 2,843 sq.ft.	$1,875,000	Airbnb cash on cash: -0.91% Traditional cash on cash: 1.32% Airbnb Rental Income: $1699 Traditional Rental Income: $5112 Airbnb ROI: -0.91% Traditional ROI: 1.32%
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 \| 4 baths \| 2,807 sq.ft.	$2,150,000	Airbnb cash on cash: -0.56% Traditional cash on cash: 1.36% Airbnb Rental Income: $2565 Traditional Rental Income: $5775 Airbnb ROI: -0.56% Traditional ROI: 1.36%
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 \| 4 baths \| 2,824 sq.ft.	$1,875,000	Airbnb cash on cash: -0.49% Traditional cash on cash: 1.71% Airbnb Rental Income: $2565 Traditional Rental Income: $5775 Airbnb ROI: -0.49% Traditional ROI: 1.71%
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: 0.35% Traditional cash on cash: 1.02% Airbnb Rental Income: $3915 Traditional Rental Income: $4524 Airbnb ROI: 0.35% Traditional ROI: 1.02%
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: -0.6% Traditional cash on cash: 0.56% Airbnb Rental Income: $908 Traditional Rental Income: $1324 Airbnb ROI: -0.6% Traditional ROI: 0.56%
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%
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%
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: -0.11% Traditional cash on cash: 1.49% Airbnb Rental Income: $908 Traditional Rental Income: $1191 Airbnb ROI: -0.11% Traditional ROI: 1.49%
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 \| 2 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%
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%
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 \| 2 baths \| 1,152 sq.ft.	$650,000	Airbnb cash on cash: 0.37% Traditional cash on cash: 1.9% Airbnb Rental Income: $1699 Traditional Rental Income: $2158 Airbnb ROI: 0.37% Traditional ROI: 1.9%
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: -2.46% Traditional cash on cash: -1.45% Airbnb Rental Income: $1363 Traditional Rental Income: $1842 Airbnb ROI: -2.46% Traditional ROI: -1.45%
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 \| 2 baths \| 798 sq.ft.	$639,000	Airbnb cash on cash: 0.03% Traditional cash on cash: 0.95% Airbnb Rental Income: $1363 Traditional Rental Income: $1495 Airbnb ROI: 0.03% Traditional ROI: 0.95%
405 Bear Trail Winter Park, CO Mountain Luxury Meets Adventure: 4 Bedroom Ski Townhome in Winter Park. This spacious 4 be...	4 beds \| 4 baths \| 2,143 sq.ft.	$1,775,000	Airbnb cash on cash: 0.01% Traditional cash on cash: 0.53% Airbnb Rental Income: $2565 Traditional Rental Income: $2807 Airbnb ROI: 0.01% Traditional ROI: 0.53%
78746 US HWY 40 unit: 211 #211 Winter Park, CO FURNISHED & MOVE-IN READY. Only 5 residences remaing. Quite possibly the best downtown loc...	3 beds \| 2 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%
115 Whistlestop Circle Winter Park, CO Luxury meets convenience in this stunning Amish-built downtown Winter Park townhome! This ...	4 beds \| 6 baths \| 2,905 sq.ft.	$2,000,000	Airbnb cash on cash: -0.02% Traditional cash on cash: 1.79% Airbnb Rental Income: $2565 Traditional Rental Income: $5303 Airbnb ROI: -0.02% Traditional ROI: 1.79%
210 SAWYER Circle Winter Park, CO Introducing 210 Sawyer Circle - Your No-Compromise Winter Park Retreat Say goodbye to trad...	4 beds \| 4 baths \| 1,768 sq.ft.	$1,350,000	Airbnb cash on cash: -0.54% Traditional cash on cash: 0.39% Airbnb Rental Income: $2565 Traditional Rental Income: $3107 Airbnb ROI: -0.54% Traditional ROI: 0.39%
78746 US HWY 40 unit: 210 #210 Winter Park, CO FURNISHED & MOVE-IN READY. Only 5 residences remaing. Quite possibly the best downtown loc...	3 beds \| 2 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%
720 BAKER Drive unit: 309 #309 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: 0.04% Traditional cash on cash: 1.23% Airbnb Rental Income: $1363 Traditional Rental Income: $1889 Airbnb ROI: 0.04% Traditional ROI: 1.23%
720 BAKER Drive unit: 408 #408 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: -0.23% Traditional cash on cash: 0.9% Airbnb Rental Income: $1363 Traditional Rental Income: $1889 Airbnb ROI: -0.23% Traditional ROI: 0.9%
73 High Grove Loop Winter Park, CO Discover mountain living at its finest in the brand-new end-unit townhome in Rendezvous Wi...	3 beds \| 3 baths \| 1,711 sq.ft.	$1,565,901	Airbnb cash on cash: -0.73% Traditional cash on cash: 0.13% Airbnb Rental Income: $1699 Traditional Rental Income: $2473 Airbnb ROI: -0.73% Traditional ROI: 0.13%
69 High Grove Loop Winter Park, CO Discover mountain living at its finest in the brand-new interior-unit townhome in Rendezvo...	3 beds \| 3 baths \| 1,853 sq.ft.	$1,492,512	Airbnb cash on cash: -0.69% Traditional cash on cash: 0.35% Airbnb Rental Income: $1699 Traditional Rental Income: $2671 Airbnb ROI: -0.69% Traditional ROI: 0.35%

Real Estate investment in Winter-park, CO

There are 82 properties for sale in the city of Winter Park . The median list price in Winter Park is $1,355,410 and the average price per square foot is $761. In December 2025, the average monthly cash on cash return in Winter Park is N/A%. The average monthly rental income in Winter Park is $2,346.

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

There are 82 investment properties available for sale in Winter-park.

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

The ROI for Long-Term is higher than the Short-Term in Winter-park with average rental income of $2,346.

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.

$815,000

Airbnb cash on cash: -0.68%

Traditional cash on cash: 0.58%

Airbnb Rental Income: $1699

Traditional Rental Income: $2186

Airbnb ROI: -0.68%

Traditional ROI: 0.58%

246 Hi Country Drive #3

Winter Park, CO

2 beds | 2 baths | 935 sq.ft.

$649,750

Airbnb cash on cash: -1.03%

Traditional cash on cash: 0.53%

Airbnb Rental Income: $1363

Traditional Rental Income: $1898

Airbnb ROI: -1.03%

Traditional ROI: 0.53%

78746 US HWY 40 unit: 222 #222

Winter Park, CO

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

$849,000

Airbnb cash on cash: -2.36%

Traditional cash on cash: -0.54%

Airbnb Rental Income: $1363

Traditional Rental Income: $2389

Airbnb ROI: -2.36%

Traditional ROI: -0.54%

57 Scenic Trail

Winter Park, CO

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%

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%

273 Hi Country Drive unit: 15 #15

Winter Park, CO

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

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%

19 Scenic Trail

Winter Park, CO

4 beds | 4 baths | 2,775 sq.ft.

$2,675,394

Airbnb cash on cash: -0.87%

Traditional cash on cash: -0.37%

Airbnb Rental Income: $2565

Traditional Rental Income: $3179

Airbnb ROI: -0.87%