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
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: -0.93% Traditional cash on cash: -0.13% Airbnb Rental Income: $1646 Traditional Rental Income: $3179 Airbnb ROI: -0.93% Traditional ROI: -0.13%
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: -1.57% Traditional cash on cash: 0.16% Airbnb Rental Income: $760 Traditional Rental Income: $2097 Airbnb ROI: -1.57% Traditional ROI: 0.16%
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: -0.98% Traditional cash on cash: -0.18% Airbnb Rental Income: $1646 Traditional Rental Income: $3179 Airbnb ROI: -0.98% Traditional ROI: -0.18%
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: -0.91% Traditional cash on cash: -0.19% Airbnb Rental Income: $1646 Traditional Rental Income: $3479 Airbnb ROI: -0.91% Traditional ROI: -0.19%
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: -0.53% Traditional cash on cash: 0.57% Airbnb Rental Income: $1500 Traditional Rental Income: $2743 Airbnb ROI: -0.53% 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: -0.66% Traditional cash on cash: 0.3% Airbnb Rental Income: $1500 Traditional Rental Income: $2973 Airbnb ROI: -0.66% 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: -0.49% Traditional cash on cash: 0.76% Airbnb Rental Income: $1500 Traditional Rental Income: $2830 Airbnb ROI: -0.49% Traditional ROI: 0.76%
385 Lions Gate Drive #I Winter Park, CO Welcome to Lion's Rock Townhomes--Winter Park's most premium and sophisticated boutique de...	3 beds \| 5 baths \| 2,843 sq.ft.	$1,875,000	Airbnb cash on cash: -1.02% Traditional cash on cash: 1.3% Airbnb Rental Income: $1500 Traditional Rental Income: $5112 Airbnb ROI: -1.02% Traditional ROI: 1.3%
385 Lions Gate Drive #C Winter Park, CO Welcome to Lion's Rock Townhomes--Winter Park's most premium and sophisticated boutique de...	4 beds \| 5 baths \| 2,807 sq.ft.	$2,150,000	Airbnb cash on cash: -0.96% Traditional cash on cash: 1.34% Airbnb Rental Income: $1646 Traditional Rental Income: $5775 Airbnb ROI: -0.96% Traditional ROI: 1.34%
385 Lions Gate Drive #B Winter Park, CO Welcome to Lion's Rock Townhomes--Winter Park's most premium and sophisticated boutique de...	4 beds \| 5 baths \| 2,824 sq.ft.	$1,875,000	Airbnb cash on cash: -0.95% Traditional cash on cash: 1.68% Airbnb Rental Income: $1646 Traditional Rental Income: $5775 Airbnb ROI: -0.95% 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: -0.01% Traditional cash on cash: 0.97% Airbnb Rental Income: $3085 Traditional Rental Income: $4524 Airbnb ROI: -0.01% Traditional ROI: 0.97%
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: -0.39% Traditional cash on cash: 1.55% Airbnb Rental Income: $903 Traditional Rental Income: $1473 Airbnb ROI: -0.39% Traditional ROI: 1.55%
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: -0.89% Traditional cash on cash: 0.88% Airbnb Rental Income: $760 Traditional Rental Income: $1373 Airbnb ROI: -0.89% Traditional ROI: 0.88%
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: -0.58% Traditional cash on cash: 0.74% Airbnb Rental Income: $3085 Traditional Rental Income: $6606 Airbnb ROI: -0.58% Traditional ROI: 0.74%
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: -0.67% Traditional cash on cash: 0.26% Airbnb Rental Income: $1500 Traditional Rental Income: $3011 Airbnb ROI: -0.67% Traditional ROI: 0.26%
78746 US HWY 40 #210 Winter Park, CO Quite possibly the best downtown location in Winter Park. Located across from Hideaway Par...	3 beds \| 3 baths \| 1,506 sq.ft.	$1,199,000	Airbnb cash on cash: -0.5% Traditional cash on cash: 0.53% Airbnb Rental Income: $1500 Traditional Rental Income: $2206 Airbnb ROI: -0.5% Traditional ROI: 0.53%
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: -0.76% Traditional cash on cash: 0.93% Airbnb Rental Income: $903 Traditional Rental Income: $1889 Airbnb ROI: -0.76% 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: -0.67% Traditional cash on cash: 0.92% Airbnb Rental Income: $903 Traditional Rental Income: $1889 Airbnb ROI: -0.67% Traditional ROI: 0.92%
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: -0.32% Traditional cash on cash: 1.13% Airbnb Rental Income: $1500 Traditional Rental Income: $2702 Airbnb ROI: -0.32% Traditional ROI: 1.13%
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 \| 1,935 sq.ft.	$1,555,593	Airbnb cash on cash: -0.49% Traditional cash on cash: 0.62% Airbnb Rental Income: $1500 Traditional Rental Income: $2671 Airbnb ROI: -0.49% Traditional ROI: 0.62%
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: -0.44% Traditional cash on cash: 0.77% Airbnb Rental Income: $1500 Traditional Rental Income: $2651 Airbnb ROI: -0.44% 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: -0.42% Traditional cash on cash: 0.8% Airbnb Rental Income: $1500 Traditional Rental Income: $2616 Airbnb ROI: -0.42% Traditional ROI: 0.8%
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: -0.37% Traditional cash on cash: 0.87% Airbnb Rental Income: $1646 Traditional Rental Income: $3112 Airbnb ROI: -0.37% Traditional ROI: 0.87%
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: -0.67% Traditional cash on cash: 0.35% Airbnb Rental Income: $1500 Traditional Rental Income: $2332 Airbnb ROI: -0.67% Traditional ROI: 0.35%
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: -0.65% Traditional cash on cash: 0.92% Airbnb Rental Income: $760 Traditional Rental Income: $1178 Airbnb ROI: -0.65% 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: -0.36% Traditional cash on cash: 1% Airbnb Rental Income: $1500 Traditional Rental Income: $2888 Airbnb ROI: -0.36% 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: -0.44% Traditional cash on cash: 0.85% Airbnb Rental Income: $1500 Traditional Rental Income: $2568 Airbnb ROI: -0.44% 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: -0.69% Traditional cash on cash: 0.21% Airbnb Rental Income: $1500 Traditional Rental Income: $3011 Airbnb ROI: -0.69% 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: -0.7% Traditional cash on cash: 0.22% Airbnb Rental Income: $1500 Traditional Rental Income: $3136 Airbnb ROI: -0.7% Traditional ROI: 0.22%
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: -0.64% Traditional cash on cash: 0.35% Airbnb Rental Income: $1500 Traditional Rental Income: $2973 Airbnb ROI: -0.64% Traditional ROI: 0.35%
135 Spruce Tree Way Winter Park, CO This brand-new 3-bedroom, 3.5-bath home is ideal to entertain or unwind after you enjoy al...	3 beds \| 3 baths \| 1,761 sq.ft.	$1,677,000	Airbnb cash on cash: -0.53% Traditional cash on cash: 0.42% Airbnb Rental Income: $1500 Traditional Rental Income: $2540 Airbnb ROI: -0.53% Traditional ROI: 0.42%
400 Baker Drive #Te-204 Winter Park, CO Located right in the heart of downtown Winter Park, this modern 2-bedroom, 2-bath condo bu...	2 beds \| 2 baths \| 1,289 sq.ft.	$995,000	Airbnb cash on cash: -0.93% Traditional cash on cash: 1.46% Airbnb Rental Income: $903 Traditional Rental Income: $2775 Airbnb ROI: -0.93% Traditional ROI: 1.46%
405 Bear Trail Winter Park, CO This is the very best of Winter Park living, with views you truly have to see to believe. ...	4 beds \| 4 baths \| 2,143 sq.ft.	$1,650,000	Airbnb cash on cash: -0.69% Traditional cash on cash: 0.37% Airbnb Rental Income: $1646 Traditional Rental Income: $2807 Airbnb ROI: -0.69% Traditional ROI: 0.37%
250 LIONS GATE Drive Winter Park, CO Hot tub. Rooftop deck. Continental Divide views. Premier four-season destination. Welcome ...	3 beds \| 3 baths \| 1,436 sq.ft.	$1,169,000	Airbnb cash on cash: -0.5% Traditional cash on cash: 0.44% Airbnb Rental Income: $1500 Traditional Rental Income: $2077 Airbnb ROI: -0.5% Traditional ROI: 0.44%
113 Apres Way Winter Park, CO Experience luxury mountain living at 113 Apres Way in Riverwalk, Winter Park's premier riv...	5 beds \| 6 baths \| 3,664 sq.ft.	$3,950,000	Airbnb cash on cash: -0.76% Traditional cash on cash: 0.47% Airbnb Rental Income: $3085 Traditional Rental Income: $6897 Airbnb ROI: -0.76% Traditional ROI: 0.47%
78679 US Hwy 40 #Building 2 7 Winter Park, CO Quietly tucked along the Fraser River in central downtown Winter Park sits a bright end un...	3 beds \| 1 baths \| 784 sq.ft.	$480,000	Airbnb cash on cash: 0.65% Traditional cash on cash: 1.81% Airbnb Rental Income: $1500 Traditional Rental Income: $1585 Airbnb ROI: 0.65% Traditional ROI: 1.81%
432 Hi Country Drive #10-13 Winter Park, CO Don't miss this opportunity to own an affordable 3-bedroom condo in the heart of downtown ...	3 beds \| 2 baths \| 804 sq.ft.	$560,000	Airbnb cash on cash: 0.4% Traditional cash on cash: 2.26% Airbnb Rental Income: $1500 Traditional Rental Income: $2036 Airbnb ROI: 0.4% Traditional ROI: 2.26%
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: -0.82% Traditional cash on cash: 0.44% Airbnb Rental Income: $1646 Traditional Rental Income: $4351 Airbnb ROI: -0.82% 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: -0.82% Traditional cash on cash: 0% Airbnb Rental Income: $1646 Traditional Rental Income: $3295 Airbnb ROI: -0.82% 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: -0.39% Traditional cash on cash: 1.53% Airbnb Rental Income: $903 Traditional Rental Income: $1523 Airbnb ROI: -0.39% Traditional ROI: 1.53%

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 $465. In August 2026, the average monthly cash on cash return in Winter Park is N/A%. The average monthly rental income in Winter Park is $2,388.

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 $2,388.

Your search for investment property begins and ends here

Investment Property for Sale in Winter Park, CO

45 Scenic Trail

Winter Park, CO

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

$2,685,643

Airbnb cash on cash: -0.93%

Traditional cash on cash: -0.13%

Airbnb Rental Income: $1646

Traditional Rental Income: $3179

Airbnb ROI: -0.93%

Traditional ROI: -0.13%

720 BAKER Drive #404

Winter Park, CO

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

$1,025,000

Airbnb cash on cash: -1.57%

Traditional cash on cash: 0.16%

Airbnb Rental Income: $760

Traditional Rental Income: $2097

Airbnb ROI: -1.57%

Traditional ROI: 0.16%

19 Scenic Trail

Winter Park, CO

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

$2,683,729

Airbnb cash on cash: -0.98%

Traditional cash on cash: -0.18%

Airbnb Rental Income: $1646

Traditional Rental Income: $3179

Airbnb ROI: -0.98%

Traditional ROI: -0.18%

54 Cub Creek Way

Winter Park, CO

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

$3,470,000

Airbnb cash on cash: -0.91%

Traditional cash on cash: -0.19%

Airbnb Rental Income: $1646

Traditional Rental Income: $3479

Airbnb ROI: -0.91%

Traditional ROI: -0.19%

442 Lions Gate Dr

Winter Park, CO

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

$1,650,000

Airbnb cash on cash: -0.53%

Traditional cash on cash: 0.57%

Airbnb Rental Income: $1500

Traditional Rental Income: $2743

Airbnb ROI: -0.53%

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: -0.66%

Traditional cash on cash: 0.3%

Airbnb Rental Income: $1500

Traditional Rental Income: $2973

Airbnb ROI: -0.66%

Traditional ROI: 0.3%

454 Lions Gate Dr

Winter Park, CO

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

$1,525,000

Airbnb cash on cash: -0.49%

Traditional cash on cash: 0.76%

Airbnb Rental Income: $1500

Traditional Rental Income: $2830

Airbnb ROI: -0.49%

Traditional ROI: 0.76%

385 Lions Gate Drive #I

Winter Park, CO

3 beds | 5 baths | 2,843 sq.ft.

$1,875,000

Airbnb cash on cash: -1.02%

Traditional cash on cash: 1.3%

Airbnb Rental Income: $1500

Traditional Rental Income: $5112

Airbnb ROI: -1.02%