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
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.	$819,000	Airbnb cash on cash: -0.01% Traditional cash on cash: 2.15% Airbnb Rental Income: $1704 Traditional Rental Income: $2886 Airbnb ROI: -0.01% Traditional ROI: 2.15%
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: -0.96% Traditional cash on cash: -0.18% Airbnb Rental Income: $1704 Traditional Rental Income: $3179 Airbnb ROI: -0.96% Traditional ROI: -0.18%
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.	$2,685,643	Airbnb cash on cash: -0.92% Traditional cash on cash: -0.13% Airbnb Rental Income: $1704 Traditional Rental Income: $3179 Airbnb ROI: -0.92% Traditional ROI: -0.13%
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: -0.93% Traditional cash on cash: 0.14% Airbnb Rental Income: $1704 Traditional Rental Income: $4673 Airbnb ROI: -0.93% 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: -0.89% Traditional cash on cash: -0.19% Airbnb Rental Income: $1704 Traditional Rental Income: $3479 Airbnb ROI: -0.89% Traditional ROI: -0.19%
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: -1.53% Traditional cash on cash: 0.16% Airbnb Rental Income: $813 Traditional Rental Income: $2097 Airbnb ROI: -1.53% Traditional ROI: 0.16%
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: -0.51% Traditional cash on cash: 0.57% Airbnb Rental Income: $1538 Traditional Rental Income: $2743 Airbnb ROI: -0.51% 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: -0.64% Traditional cash on cash: 0.3% Airbnb Rental Income: $1538 Traditional Rental Income: $2973 Airbnb ROI: -0.64% Traditional ROI: 0.3%
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: -0.47% Traditional cash on cash: 0.76% Airbnb Rental Income: $1538 Traditional Rental Income: $2830 Airbnb ROI: -0.47% Traditional ROI: 0.76%
385 Lions Gate Drive #I Winter Park, CO COMING SUMMER 2026! Welcome to Lion's Rock Townhomes--Winter Park's most premium and sophi...	3 beds \| 5 baths \| 2,843 sq.ft.	$1,875,000	Airbnb cash on cash: -1.01% Traditional cash on cash: 1.3% Airbnb Rental Income: $1538 Traditional Rental Income: $5112 Airbnb ROI: -1.01% 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: -0.94% Traditional cash on cash: 1.34% Airbnb Rental Income: $1704 Traditional Rental Income: $5775 Airbnb ROI: -0.94% Traditional ROI: 1.34%
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.	$560,000	Airbnb cash on cash: -0.81% Traditional cash on cash: 0.88% Airbnb Rental Income: $813 Traditional Rental Income: $1373 Airbnb ROI: -0.81% Traditional ROI: 0.88%
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: -0.93% Traditional cash on cash: 1.68% Airbnb Rental Income: $1704 Traditional Rental Income: $5775 Airbnb ROI: -0.93% 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: 0.09% Traditional cash on cash: 0.97% Airbnb Rental Income: $3337 Traditional Rental Income: $4524 Airbnb ROI: 0.09% Traditional ROI: 0.97%
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: -0.51% Traditional cash on cash: 0.74% Airbnb Rental Income: $3337 Traditional Rental Income: $6606 Airbnb ROI: -0.51% 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.	$500,000	Airbnb cash on cash: -1.01% Traditional cash on cash: 1.55% Airbnb Rental Income: $554 Traditional Rental Income: $1473 Airbnb ROI: -1.01% Traditional ROI: 1.55%
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: -0.47% Traditional cash on cash: 0.53% Airbnb Rental Income: $1538 Traditional Rental Income: $2206 Airbnb ROI: -0.47% 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: -0.66% Traditional cash on cash: 0.26% Airbnb Rental Income: $1538 Traditional Rental Income: $3011 Airbnb ROI: -0.66% 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: -0.51% Traditional cash on cash: 0.47% Airbnb Rental Income: $1704 Traditional Rental Income: $3026 Airbnb ROI: -0.51% 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: -1.13% Traditional cash on cash: 0.93% Airbnb Rental Income: $554 Traditional Rental Income: $1889 Airbnb ROI: -1.13% 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: -1.02% Traditional cash on cash: 0.92% Airbnb Rental Income: $554 Traditional Rental Income: $1889 Airbnb ROI: -1.02% 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.	$1,553,831	Airbnb cash on cash: -0.47% Traditional cash on cash: 0.63% Airbnb Rental Income: $1538 Traditional Rental Income: $2671 Airbnb ROI: -0.47% Traditional ROI: 0.63%
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: -0.29% Traditional cash on cash: 1.13% Airbnb Rental Income: $1538 Traditional Rental Income: $2702 Airbnb ROI: -0.29% Traditional ROI: 1.13%
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.	$1,412,709	Airbnb cash on cash: -0.42% Traditional cash on cash: 0.77% Airbnb Rental Income: $1538 Traditional Rental Income: $2651 Airbnb ROI: -0.42% Traditional ROI: 0.77%
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.	$1,369,865	Airbnb cash on cash: -0.4% Traditional cash on cash: 0.8% Airbnb Rental Income: $1538 Traditional Rental Income: $2616 Airbnb ROI: -0.4% Traditional ROI: 0.8%
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: -0.64% Traditional cash on cash: 0.35% Airbnb Rental Income: $1538 Traditional Rental Income: $2332 Airbnb ROI: -0.64% Traditional ROI: 0.35%
101 Wheeler Road Winter Park, CO Nestled in the beauty of Winter Park, Sojourn at Idlewild is the area's newest neighborhoo...	4 beds \| 3 baths \| 2,223 sq.ft.	$1,675,000	Airbnb cash on cash: -0.33% Traditional cash on cash: 0.87% Airbnb Rental Income: $1704 Traditional Rental Income: $3112 Airbnb ROI: -0.33% Traditional ROI: 0.87%
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: -0.55% Traditional cash on cash: 0.92% Airbnb Rental Income: $813 Traditional Rental Income: $1178 Airbnb ROI: -0.55% 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: -0.33% Traditional cash on cash: 1% Airbnb Rental Income: $1538 Traditional Rental Income: $2888 Airbnb ROI: -0.33% 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: -0.42% Traditional cash on cash: 0.85% Airbnb Rental Income: $1538 Traditional Rental Income: $2568 Airbnb ROI: -0.42% 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: -0.67% Traditional cash on cash: 0.21% Airbnb Rental Income: $1538 Traditional Rental Income: $3011 Airbnb ROI: -0.67% 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: -0.68% Traditional cash on cash: 0.22% Airbnb Rental Income: $1538 Traditional Rental Income: $3136 Airbnb ROI: -0.68% Traditional ROI: 0.22%
250 LIONS GATE Drive Winter Park, CO Welcome to 250 Lions Gate Drive. If you're seeking a luxury mountain residence that offers...	3 beds \| 3 baths \| 1,436 sq.ft.	$1,169,000	Airbnb cash on cash: -0.47% Traditional cash on cash: 0.44% Airbnb Rental Income: $1538 Traditional Rental Income: $2077 Airbnb ROI: -0.47% Traditional ROI: 0.44%
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: -0.63% Traditional cash on cash: 0.35% Airbnb Rental Income: $1538 Traditional Rental Income: $2973 Airbnb ROI: -0.63% 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: -0.8% Traditional cash on cash: 0.44% Airbnb Rental Income: $1704 Traditional Rental Income: $4351 Airbnb ROI: -0.8% Traditional ROI: 0.44%
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: -0.8% Traditional cash on cash: 0% Airbnb Rental Income: $1704 Traditional Rental Income: $3295 Airbnb ROI: -0.8% Traditional ROI: 0%
490 KINGS CROSSING #423 Winter Park, CO Get ready for your new beautifully remodeled 2-bedroom condo with new wood-look tile floor...	2 beds \| 2 baths \| 860 sq.ft.	$535,000	Airbnb cash on cash: -0.97% Traditional cash on cash: 1.53% Airbnb Rental Income: $554 Traditional Rental Income: $1523 Airbnb ROI: -0.97% Traditional ROI: 1.53%
97 KINNEY Way #A Winter Park, CO Welcome to the Slopeside Village Luxury Chalet 97 A, a stunning retreat nestled in the pea...	2 beds \| 2 baths \| 1,376 sq.ft.	$1,169,000	Airbnb cash on cash: -1.16% Traditional cash on cash: 0.61% Airbnb Rental Income: $554 Traditional Rental Income: $2188 Airbnb ROI: -1.16% Traditional ROI: 0.61%
385 Lions Gate Drive #G Winter Park, CO ESTIMATED COMPLETION SUMMER 2026! Welcome to Lion's Rock Townhomes-Winter Park's most refi...	4 beds \| 5 baths \| 2,807 sq.ft.	$2,350,000	Airbnb cash on cash: -0.94% Traditional cash on cash: 0.15% Airbnb Rental Income: $1704 Traditional Rental Income: $3610 Airbnb ROI: -0.94% Traditional ROI: 0.15%
151 TELEMARK #15 Winter Park, CO Prime Downtown Winter Park Location! Just a few blocks from Main Street, this beautifully ...	2 beds \| 3 baths \| 1,338 sq.ft.	$810,000	Airbnb cash on cash: -1.06% Traditional cash on cash: 1.15% Airbnb Rental Income: $554 Traditional Rental Income: $1941 Airbnb ROI: -1.06% Traditional ROI: 1.15%

Real Estate investment in Winter-park, CO

There are 138 properties for sale in the city of Winter Park . The median list price in Winter Park is $838,998 and the average price per square foot is $445. In July 2026, the average monthly cash on cash return in Winter Park is N/A%. The average monthly rental income in Winter Park is $2,422.

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

There are 138 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 $2,422.

Your search for investment property begins and ends here

Investment Property for Sale in Winter Park, CO

490 Kings Crossing Road 631-633

Winter Park, CO

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

$819,000

Airbnb cash on cash: -0.01%

Traditional cash on cash: 2.15%

Airbnb Rental Income: $1704

Traditional Rental Income: $2886

Airbnb ROI: -0.01%

Traditional ROI: 2.15%

19 Scenic Trail

Winter Park, CO

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

$2,683,729

Airbnb cash on cash: -0.96%

Traditional cash on cash: -0.18%

Airbnb Rental Income: $1704

Traditional Rental Income: $3179

Airbnb ROI: -0.96%

Traditional ROI: -0.18%

45 Scenic Trail

Winter Park, CO

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

$2,685,643

Airbnb cash on cash: -0.92%

Traditional cash on cash: -0.13%

Airbnb Rental Income: $1704

Traditional Rental Income: $3179

Airbnb ROI: -0.92%

Traditional ROI: -0.13%

40 Cub Creek Way

Winter Park, CO

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

$3,465,000

Airbnb cash on cash: -0.93%

Traditional cash on cash: 0.14%

Airbnb Rental Income: $1704

Traditional Rental Income: $4673

Airbnb ROI: -0.93%

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: -0.89%

Traditional cash on cash: -0.19%

Airbnb Rental Income: $1704

Traditional Rental Income: $3479

Airbnb ROI: -0.89%

Traditional ROI: -0.19%

720 BAKER Drive #404

Winter Park, CO

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

$1,025,000

Airbnb cash on cash: -1.53%

Traditional cash on cash: 0.16%

Airbnb Rental Income: $813

Traditional Rental Income: $2097

Airbnb ROI: -1.53%

Traditional ROI: 0.16%

442 Lions Gate Dr

Winter Park, CO

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

$1,650,000

Airbnb cash on cash: -0.51%

Traditional cash on cash: 0.57%

Airbnb Rental Income: $1538

Traditional Rental Income: $2743

Airbnb ROI: -0.51%

Traditional ROI: 0.57%

18 Exploration Trail

Winter Park, CO

3 beds | 4 baths | 2,597 sq.ft.

$2,150,000

Airbnb cash on cash: -0.64%

Traditional cash on cash: 0.3%

Airbnb Rental Income: $1538

Traditional Rental Income: $2973

Airbnb ROI: -0.64%