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

separator

PROPERTY	DETAILS	SALE PRICE	INVESTMENT PERFORMANCE
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.	$2,683,729	Airbnb cash on cash: -1.04% Traditional cash on cash: 0.04% Airbnb Rental Income: $826 Traditional Rental Income: $3179 Airbnb ROI: -1.04% Traditional ROI: 0.04%
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.	$2,684,411	Airbnb cash on cash: -1.04% Traditional cash on cash: 0.04% Airbnb Rental Income: $826 Traditional Rental Income: $3179 Airbnb ROI: -1.04% Traditional ROI: 0.04%
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.	$869,000	Airbnb cash on cash: -1% Traditional cash on cash: 1.95% Airbnb Rental Income: $826 Traditional Rental Income: $2886 Airbnb ROI: -1% Traditional ROI: 1.95%
64 Overlook Place Winter Park, CO Perched in Winter Park, this uphill 4-bedroom, 4.5-bath mountain home defines modern luxur...	4 beds \| 5 baths \| 3,057 sq.ft.	$2,744,642	Airbnb cash on cash: -1.18% Traditional cash on cash: 0.4% Airbnb Rental Income: $826 Traditional Rental Income: $4517 Airbnb ROI: -1.18% Traditional ROI: 0.4%
720 BAKER Drive #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: -1.93% Traditional cash on cash: 0.16% Airbnb Rental Income: $351 Traditional Rental Income: $2097 Airbnb ROI: -1.93% Traditional ROI: 0.16%
40 Cub Creek Way Winter Park, CO Welcome to Lakota Pointe, where luxury living meets the majestic Rocky Mountains. Meticulo...	4 beds \| 5 baths \| 3,629 sq.ft.	$3,465,000	Airbnb cash on cash: -1.16% Traditional cash on cash: 0.14% Airbnb Rental Income: $826 Traditional Rental Income: $4673 Airbnb ROI: -1.16% Traditional ROI: 0.14%
54 Cub Creek Way Winter Park, CO Welcome to Lakota Pointe, where luxury living meets the majestic Rocky Mountains. Meticulo...	4 beds \| 5 baths \| 3,629 sq.ft.	$3,470,000	Airbnb cash on cash: -1.12% Traditional cash on cash: -0.19% Airbnb Rental Income: $826 Traditional Rental Income: $3479 Airbnb ROI: -1.12% Traditional ROI: -0.19%
454 Lions Gate Dr Winter Park, CO Estimated completion is Summer 2026! Things are moving along for Reunion Lofts! Stunning t...	3 beds \| 3 baths \| 2,240 sq.ft.	$1,525,000	Airbnb cash on cash: -0.74% Traditional cash on cash: 0.76% Airbnb Rental Income: $1081 Traditional Rental Income: $2830 Airbnb ROI: -0.74% Traditional ROI: 0.76%
442 Lions Gate Dr Winter Park, CO Stunning townhomes located in Downtown Winter Park. New Construction homes - the floor pla...	3 beds \| 3 baths \| 2,240 sq.ft.	$1,650,000	Airbnb cash on cash: -0.76% Traditional cash on cash: 0.57% Airbnb Rental Income: $1081 Traditional Rental Income: $2743 Airbnb ROI: -0.76% Traditional ROI: 0.57%
18 Exploration Trail Winter Park, CO Within ROAM, you'll find Wilds 360, a collection of single family residences designed spec...	3 beds \| 4 baths \| 2,597 sq.ft.	$2,150,000	Airbnb cash on cash: -0.83% Traditional cash on cash: 0.3% Airbnb Rental Income: $1081 Traditional Rental Income: $2973 Airbnb ROI: -0.83% Traditional ROI: 0.3%
385 Lions Gate Drive #I Winter Park, CO COMING SUMMER 2026! Welcome to Lion's Rock Townhomes-Winter Park's most premium and sophis...	3 beds \| 5 baths \| 2,843 sq.ft.	$1,875,000	Airbnb cash on cash: -1.22% Traditional cash on cash: 1.3% Airbnb Rental Income: $1081 Traditional Rental Income: $5112 Airbnb ROI: -1.22% Traditional ROI: 1.3%
385 Lions Gate Drive #C Winter Park, CO ESTIMATED COMPLETION SUMMER 2026! Welcome to Lion's Rock Townhomes-Winter Park's most prem...	4 beds \| 5 baths \| 2,807 sq.ft.	$2,150,000	Airbnb cash on cash: -1.3% Traditional cash on cash: 1.34% Airbnb Rental Income: $826 Traditional Rental Income: $5775 Airbnb ROI: -1.3% Traditional ROI: 1.34%
385 Lions Gate Drive #B Winter Park, CO ESTIMATED COMPLETION SUMMER 2026! Welcome to Lion's Rock Townhomes-Winter Park's most prem...	4 beds \| 5 baths \| 2,824 sq.ft.	$1,875,000	Airbnb cash on cash: -1.35% Traditional cash on cash: 1.68% Airbnb Rental Income: $826 Traditional Rental Income: $5775 Airbnb ROI: -1.35% Traditional ROI: 1.68%
120 Whistlestop Circle #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: -0.33% Traditional cash on cash: 0.97% Airbnb Rental Income: $2237 Traditional Rental Income: $4524 Airbnb ROI: -0.33% Traditional ROI: 0.97%
580 Winter Park Drive #4564 Winter Park, CO Get ready for ski season! Enjoy Winter Park's year-round magic with this updated 1-bed / 1...	1 beds \| 1 baths \| 533 sq.ft.	$599,000	Airbnb cash on cash: -1.51% Traditional cash on cash: 0.76% Airbnb Rental Income: $351 Traditional Rental Income: $1373 Airbnb ROI: -1.51% Traditional ROI: 0.76%
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: -0.8% Traditional cash on cash: 0.74% Airbnb Rental Income: $2237 Traditional Rental Income: $6606 Airbnb ROI: -0.8% Traditional ROI: 0.74%
490 KINGS CROSSING #331 Winter Park, CO This top floor unit boasts Divide views & a fantastic location for all of your mountain en...	2 beds \| 2 baths \| 860 sq.ft.	$515,000	Airbnb cash on cash: -0.99% Traditional cash on cash: 1.48% Airbnb Rental Income: $566 Traditional Rental Income: $1473 Airbnb ROI: -0.99% Traditional ROI: 1.48%
24 Cub Creek Way Winter Park, CO Welcome to Lakota Pointe, where luxury living meets the majestic Rocky Mountains. Meticulo...	4 beds \| 5 baths \| 3,629 sq.ft.	$3,455,000	Airbnb cash on cash: -1.12% Traditional cash on cash: -0.19% Airbnb Rental Income: $826 Traditional Rental Income: $3479 Airbnb ROI: -1.12% Traditional ROI: -0.19%
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.	$1,249,000	Airbnb cash on cash: -1.73% Traditional cash on cash: 0.51% Airbnb Rental Income: $826 Traditional Rental Income: $3107 Airbnb ROI: -1.73% Traditional ROI: 0.51%
78746 US HWY 40 #210 Winter Park, CO FURNISHED & MOVE-IN READY. Only 5 residences remaing. Quite possibly the best downtown loc...	3 beds \| 3 baths \| 1,506 sq.ft.	$1,199,000	Airbnb cash on cash: -0.81% Traditional cash on cash: 0.53% Airbnb Rental Income: $1081 Traditional Rental Income: $2206 Airbnb ROI: -0.81% Traditional ROI: 0.53%
60 Ski Idlewild Road Winter Park, CO Within ROAM, you'll find Wilds 360, a collection of single family residences designed spec...	3 beds \| 4 baths \| 2,649 sq.ft.	$2,250,000	Airbnb cash on cash: -0.84% Traditional cash on cash: 0.26% Airbnb Rental Income: $1081 Traditional Rental Income: $3011 Airbnb ROI: -0.84% Traditional ROI: 0.26%
185 Vasquez Road #B3 Winter Park, CO	4 beds \| 3 baths \| 2,312 sq.ft.	$1,975,000	Airbnb cash on cash: -0.91% Traditional cash on cash: 0.47% Airbnb Rental Income: $826 Traditional Rental Income: $3026 Airbnb ROI: -0.91% Traditional ROI: 0.47%
720 BAKER Drive #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: -1.11% Traditional cash on cash: 0.93% Airbnb Rental Income: $566 Traditional Rental Income: $1889 Airbnb ROI: -1.11% Traditional ROI: 0.93%
720 BAKER Drive #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: -1.01% Traditional cash on cash: 0.92% Airbnb Rental Income: $566 Traditional Rental Income: $1889 Airbnb ROI: -1.01% Traditional ROI: 0.92%
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 \| 1,935 sq.ft.	$1,500,634	Airbnb cash on cash: -0.72% Traditional cash on cash: 0.68% Airbnb Rental Income: $1081 Traditional Rental Income: $2671 Airbnb ROI: -0.72% Traditional ROI: 0.68%
94 High Grove Loop Winter Park, CO Experience elevated mountain living in this brand-new end-unit townhome in Rendezvous. Cur...	3 beds \| 3 baths \| 1,842 sq.ft.	$1,409,533	Airbnb cash on cash: -0.71% Traditional cash on cash: 0.77% Airbnb Rental Income: $1081 Traditional Rental Income: $2651 Airbnb ROI: -0.71% Traditional ROI: 0.77%
88 Wheeler Road Winter Park, CO Welcome to Sojourn at Idlewild, showcasing our beautifully finished Graysill townhomes! En...	3 beds \| 4 baths \| 1,716 sq.ft.	$1,219,000	Airbnb cash on cash: -0.62% Traditional cash on cash: 1.13% Airbnb Rental Income: $1081 Traditional Rental Income: $2702 Airbnb ROI: -0.62% Traditional ROI: 1.13%
86 High Grove Loop Winter Park, CO Experience elevated mountain living in this brand-new interior-unit townhome in Rendezvous...	3 beds \| 3 baths \| 1,805 sq.ft.	$1,363,484	Airbnb cash on cash: -0.7% Traditional cash on cash: 0.81% Airbnb Rental Income: $1081 Traditional Rental Income: $2616 Airbnb ROI: -0.7% Traditional ROI: 0.81%
78 Wheeler Road Winter Park, CO Welcome to Sojourn at Idlewild, showcasing our beautifully finished Graysill model townhom...	3 beds \| 4 baths \| 1,716 sq.ft.	$1,350,000	Airbnb cash on cash: -0.94% Traditional cash on cash: 0.35% Airbnb Rental Income: $1081 Traditional Rental Income: $2332 Airbnb ROI: -0.94% Traditional ROI: 0.35%
79050 US HWY 40 #A-303 Winter Park, CO Turn-key condo in the heart of downtown Winter Park! Sleeps 10 total, including a private ...	2 beds \| 3 baths \| 1,124 sq.ft.	$765,000	Airbnb cash on cash: -1.07% Traditional cash on cash: 1.04% Airbnb Rental Income: $566 Traditional Rental Income: $1783 Airbnb ROI: -1.07% Traditional ROI: 1.04%
313 IRON HORSE #C2023 Winter Park, CO This impeccably maintained 1-bedroom residence at Iron Horse offers true ski-in/ski-out li...	1 beds \| 1 baths \| 562 sq.ft.	$500,000	Airbnb cash on cash: -1.37% Traditional cash on cash: 0.92% Airbnb Rental Income: $351 Traditional Rental Income: $1178 Airbnb ROI: -1.37% Traditional ROI: 0.92%
105 Wheeler Road Winter Park, CO Welcome to Sojourn at Idlewild, now showcasing our beautifully finished Coalmont floor pla...	3 beds \| 3 baths \| 1,870 sq.ft.	$1,450,000	Airbnb cash on cash: -0.62% Traditional cash on cash: 1% Airbnb Rental Income: $1081 Traditional Rental Income: $2888 Airbnb ROI: -0.62% Traditional ROI: 1%
1080 WINTER PARK Drive #1 Winter Park, CO Mountain CHIC* Fully Updated 3B Condo in Old Town Winter Park. WALK TO GONDOLA ONE OF A ...	3 beds \| 3 baths \| 1,609 sq.ft.	$1,255,555	Airbnb cash on cash: -0.74% Traditional cash on cash: 0.85% Airbnb Rental Income: $1081 Traditional Rental Income: $2568 Airbnb ROI: -0.74% Traditional ROI: 0.85%
54 Ski Idlewild Road Winter Park, CO Within ROAM, you'll find Wilds 360, a collection of single-family residences designed spec...	3 beds \| 5 baths \| 2,742 sq.ft.	$2,350,000	Airbnb cash on cash: -0.85% Traditional cash on cash: 0.21% Airbnb Rental Income: $1081 Traditional Rental Income: $3011 Airbnb ROI: -0.85% Traditional ROI: 0.21%
40 Ski Idlewild Road Winter Park, CO Within ROAM, you'll find Wilds 360, a collection of single family residences designed spec...	3 beds \| 4 baths \| 3,112 sq.ft.	$2,450,000	Airbnb cash on cash: -0.85% Traditional cash on cash: 0.22% Airbnb Rental Income: $1081 Traditional Rental Income: $3136 Airbnb ROI: -0.85% Traditional ROI: 0.22%
250 LIONS GATE Drive Winter Park, CO Step into elevated mountain living where refined design meets an exceptional Winter Park l...	3 beds \| 3 baths \| 1,436 sq.ft.	$1,199,000	Airbnb cash on cash: -0.82% Traditional cash on cash: 0.4% Airbnb Rental Income: $1081 Traditional Rental Income: $2077 Airbnb ROI: -0.82% Traditional ROI: 0.4%
670 Winter Park Drive #3413 Winter Park, CO Mountain base convenience meets year-round comfort! This 1-bedroom, 1-bath condo in Fraser...	1 beds \| 1 baths \| 622 sq.ft.	$529,000	Airbnb cash on cash: -1.67% Traditional cash on cash: 1.11% Airbnb Rental Income: $351 Traditional Rental Income: $1481 Airbnb ROI: -1.67% Traditional ROI: 1.11%
12 Exploration Trail Winter Park, CO Within ROAM, you'll find Wilds 360, a collection of single family residences designed spec...	3 beds \| 4 baths \| 2,597 sq.ft.	$2,075,000	Airbnb cash on cash: -0.83% Traditional cash on cash: 0.35% Airbnb Rental Income: $1081 Traditional Rental Income: $2973 Airbnb ROI: -0.83% Traditional ROI: 0.35%
158 SCENIC Trail Winter Park, CO Situated in Winter Park, this uphill 4-bedroom, 4.5-bath residence showcases modern mounta...	4 beds \| 6 baths \| 3,057 sq.ft.	$2,722,291	Airbnb cash on cash: -0.93% Traditional cash on cash: 0.6% Airbnb Rental Income: $826 Traditional Rental Income: $4351 Airbnb ROI: -0.93% Traditional ROI: 0.6%
170 Scenic Trail Winter Park, CO Ideally situated in Winter Park, this uphill 4-bedroom, 4.5-bath residence showcases moder...	4 beds \| 5 baths \| 3,057 sq.ft.	$2,768,308	Airbnb cash on cash: -0.93% Traditional cash on cash: 0.16% Airbnb Rental Income: $826 Traditional Rental Income: $3295 Airbnb ROI: -0.93% Traditional ROI: 0.16%

Real Estate investment in Winter-park, CO

There are 120 properties for sale in the city of Winter Park . The median list price in Winter Park is $1,509,320 and the average price per square foot is $783. In May 2026, the average monthly cash on cash return in Winter Park is N/A%. The average monthly rental income in Winter Park is $2,401.

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

There are 120 investment properties available for sale in Winter-park.

In 2026, 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 $2,401.

Your search for investment property begins and ends here

Investment Property for Sale in Winter Park, CO

19 Scenic Trail

Winter Park, CO

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

$2,683,729

Airbnb cash on cash: -1.04%

Traditional cash on cash: 0.04%

Airbnb Rental Income: $826

Traditional Rental Income: $3179

Airbnb ROI: -1.04%

Traditional ROI: 0.04%

45 Scenic Trail

Winter Park, CO

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

$2,684,411

Airbnb cash on cash: -1.04%

Traditional cash on cash: 0.04%

Airbnb Rental Income: $826

Traditional Rental Income: $3179

Airbnb ROI: -1.04%

Traditional ROI: 0.04%

490 Kings Crossing Road 631-633

Winter Park, CO

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

$869,000

Airbnb cash on cash: -1%

Traditional cash on cash: 1.95%

Airbnb Rental Income: $826

Traditional Rental Income: $2886

Airbnb ROI: -1%

Traditional ROI: 1.95%

64 Overlook Place

Winter Park, CO

4 beds | 5 baths | 3,057 sq.ft.

$2,744,642

Airbnb cash on cash: -1.18%

Traditional cash on cash: 0.4%

Airbnb Rental Income: $826

Traditional Rental Income: $4517

Airbnb ROI: -1.18%

Traditional ROI: 0.4%

720 BAKER Drive #404

Winter Park, CO

1 beds | 2 baths | 1,154 sq.ft.

$1,025,000

Airbnb cash on cash: -1.93%

Traditional cash on cash: 0.16%

Airbnb Rental Income: $351

Traditional Rental Income: $2097

Airbnb ROI: -1.93%

Traditional ROI: 0.16%

40 Cub Creek Way

Winter Park, CO

4 beds | 5 baths | 3,629 sq.ft.

$3,465,000

Airbnb cash on cash: -1.16%

Traditional cash on cash: 0.14%

Airbnb Rental Income: $826

Traditional Rental Income: $4673

Airbnb ROI: -1.16%

Traditional ROI: 0.14%

54 Cub Creek Way

Winter Park, CO

4 beds | 5 baths | 3,629 sq.ft.

$3,470,000

Airbnb cash on cash: -1.12%

Traditional cash on cash: -0.19%

Airbnb Rental Income: $826

Traditional Rental Income: $3479

Airbnb ROI: -1.12%

Traditional ROI: -0.19%

454 Lions Gate Dr

Winter Park, CO

3 beds | 3 baths | 2,240 sq.ft.

$1,525,000

Airbnb cash on cash: -0.74%

Traditional cash on cash: 0.76%

Airbnb Rental Income: $1081

Traditional Rental Income: $2830

Airbnb ROI: -0.74%