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
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: -0.87% Traditional cash on cash: -0.38% Airbnb Rental Income: $2565 Traditional Rental Income: $3179 Airbnb ROI: -0.87% Traditional ROI: -0.38%
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: -0.87% Traditional cash on cash: -0.38% Airbnb Rental Income: $2565 Traditional Rental Income: $3179 Airbnb ROI: -0.87% Traditional ROI: -0.38%
40 Cub Creek Way Winter Park, CO Welcome to Lakota Pointe, where luxury living meets the majestic Rocky Mountains. Meticulo...	4 beds \| 4 baths \| 3,629 sq.ft.	$3,465,000	Airbnb cash on cash: -0.96% Traditional cash on cash: -0.11% Airbnb Rental Income: $2565 Traditional Rental Income: $4673 Airbnb ROI: -0.96% Traditional ROI: -0.11%
54 Cub Creek Way Winter Park, CO Welcome to Lakota Pointe, where luxury living meets the majestic Rocky Mountains. Meticulo...	4 beds \| 4 baths \| 3,629 sq.ft.	$3,470,000	Airbnb cash on cash: -0.93% Traditional cash on cash: -0.45% Airbnb Rental Income: $2565 Traditional Rental Income: $3479 Airbnb ROI: -0.93% Traditional ROI: -0.45%
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: -0.89% Traditional cash on cash: 0.12% Airbnb Rental Income: $2565 Traditional Rental Income: $4517 Airbnb ROI: -0.89% Traditional ROI: 0.12%
720 BAKER Drive unit: 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: -1.64% Traditional cash on cash: -0.03% Airbnb Rental Income: $908 Traditional Rental Income: $2097 Airbnb ROI: -1.64% Traditional ROI: -0.03%
720 BAKER Drive unit: 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: -0.97% Traditional cash on cash: 0.22% Airbnb Rental Income: $1363 Traditional Rental Income: $1831 Airbnb ROI: -0.97% Traditional ROI: 0.22%
454 Lions Gate Dr Winter Park, CO Certificate of occupancy expected this Spring 2026! Things are moving along for Reunion Lo...	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 Things are moving along for Reunion Lofts! We are expecting to get the certificate of occu...	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%
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: -0.63% Traditional cash on cash: 0.24% Airbnb Rental Income: $1699 Traditional Rental Income: $2973 Airbnb ROI: -0.63% Traditional ROI: 0.24%
385 Lions Gate Drive unit: I Winter Park, CO COMING SUMMER 2026! Welcome to Lion's Rock Townhomes-Winter Park's most premium and sophis...	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%
113 Apres Way Winter Park, CO Discover an alpine sanctuary of uncompromising luxury built with a legacy mindset. Located...	5 beds \| 6 baths \| 3,664 sq.ft.	$3,950,000	Airbnb cash on cash: -0.69% Traditional cash on cash: 0.35% Airbnb Rental Income: $3915 Traditional Rental Income: $6897 Airbnb ROI: -0.69% Traditional ROI: 0.35%
385 Lions Gate Drive unit: C Winter Park, CO ESTIMATED COMPLETION SUMMER 2026! Welcome to Lion's Rock Townhomes-Winter Park's most prem...	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 Winter Park, CO ESTIMATED COMPLETION SUMMER 2026! Welcome to Lion's Rock Townhomes-Winter Park's most prem...	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 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%
490 KINGS CROSSING unit: 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: 0.38% Traditional cash on cash: 1.48% Airbnb Rental Income: $1363 Traditional Rental Income: $1473 Airbnb ROI: 0.38% 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 \| 4 baths \| 3,629 sq.ft.	$3,455,000	Airbnb cash on cash: -0.93% Traditional cash on cash: -0.45% Airbnb Rental Income: $2565 Traditional Rental Income: $3479 Airbnb ROI: -0.93% Traditional ROI: -0.45%
301 RESERVE Way Winter Park, CO Lovely home in Lakota, offering breathtaking, serene views of the Continental Divide, Wint...	5 beds \| 4 baths \| 3,172 sq.ft.	$2,850,000	Airbnb cash on cash: -0.16% Traditional cash on cash: -0.07% Airbnb Rental Income: $3915 Traditional Rental Income: $3312 Airbnb ROI: -0.16% Traditional ROI: -0.07%
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%
78746 US HWY 40 unit: 211 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: -0.36% Traditional cash on cash: 0.64% Airbnb Rental Income: $1699 Traditional Rental Income: $2345 Airbnb ROI: -0.36% Traditional ROI: 0.64%
580 Winter Park Drive unit: 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: -0.69% Traditional cash on cash: 0.72% Airbnb Rental Income: $908 Traditional Rental Income: $1358 Airbnb ROI: -0.69% Traditional ROI: 0.72%
160 Exploration Trail Winter Park, CO SOLD FULLY FURNISHED & TURNKEY Tucked away on a private double lot along the Fraser Ri...	4 beds \| 5 baths \| 3,174 sq.ft.	$3,435,000	Airbnb cash on cash: -0.92% Traditional cash on cash: -0.33% Airbnb Rental Income: $2565 Traditional Rental Income: $3845 Airbnb ROI: -0.92% Traditional ROI: -0.33%
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.	$2,075,000	Airbnb cash on cash: -0.05% Traditional cash on cash: 1.69% Airbnb Rental Income: $2565 Traditional Rental Income: $5303 Airbnb ROI: -0.05% Traditional ROI: 1.69%
207 LAKOTA PARK Drive Winter Park, CO Stunning views in this beautiful 5 Bedroom 4 Bath home in sought after Lakota. Mountain co...	5 beds \| 4 baths \| 2,998 sq.ft.	$2,850,000	Airbnb cash on cash: -0.09% Traditional cash on cash: 0.01% Airbnb Rental Income: $3915 Traditional Rental Income: $3337 Airbnb ROI: -0.09% Traditional ROI: 0.01%
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: -0.65% Traditional cash on cash: 0.21% Airbnb Rental Income: $1699 Traditional Rental Income: $3011 Airbnb ROI: -0.65% Traditional ROI: 0.21%
670 WINTER PARK unit: 3129 Winter Park, CO INVESTORS / ROI* This condo has proven track record for desirability** GUEST FEEDBACK: C...	2 beds \| 2 baths \| 1,006 sq.ft.	$899,000	Airbnb cash on cash: -0.62% Traditional cash on cash: 0.37% Airbnb Rental Income: $1363 Traditional Rental Income: $1771 Airbnb ROI: -0.62% Traditional ROI: 0.37%
78746 US HWY 40 unit: 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: -0.36% Traditional cash on cash: 0.52% Airbnb Rental Income: $1699 Traditional Rental Income: $2206 Airbnb ROI: -0.36% Traditional ROI: 0.52%
185 Vasquez Road unit: B3 Winter Park, CO	4 beds \| 3 baths \| 2,312 sq.ft.	$1,975,000	Airbnb cash on cash: -0.28% Traditional cash on cash: 0.31% Airbnb Rental Income: $2565 Traditional Rental Income: $3026 Airbnb ROI: -0.28% Traditional ROI: 0.31%
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: -0.5% Traditional cash on cash: 0.5% Airbnb Rental Income: $2565 Traditional Rental Income: $3107 Airbnb ROI: -0.5% Traditional ROI: 0.5%
720 BAKER Drive unit: 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: -0.28% Traditional cash on cash: 0.91% Airbnb Rental Income: $1363 Traditional Rental Income: $1889 Airbnb ROI: -0.28% Traditional ROI: 0.91%
720 BAKER Drive unit: 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: -0.32% Traditional cash on cash: 0.81% Airbnb Rental Income: $1363 Traditional Rental Income: $1889 Airbnb ROI: -0.32% Traditional ROI: 0.81%
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.	$1,492,512	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%
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: -0.64% Traditional cash on cash: 0.45% Airbnb Rental Income: $1699 Traditional Rental Income: $2651 Airbnb ROI: -0.64% Traditional ROI: 0.45%
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: -0.06% Traditional cash on cash: 1.25% Airbnb Rental Income: $1699 Traditional Rental Income: $2702 Airbnb ROI: -0.06% Traditional ROI: 1.25%
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.	$1,362,059	Airbnb cash on cash: -0.61% Traditional cash on cash: 0.49% Airbnb Rental Income: $1699 Traditional Rental Income: $2616 Airbnb ROI: -0.61% Traditional ROI: 0.49%
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: -0.6% Traditional cash on cash: 0.28% Airbnb Rental Income: $1699 Traditional Rental Income: $2332 Airbnb ROI: -0.6% Traditional ROI: 0.28%
79050 US HWY 40 unit: 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: -0.15% Traditional cash on cash: 1.02% Airbnb Rental Income: $1363 Traditional Rental Income: $1783 Airbnb ROI: -0.15% Traditional ROI: 1.02%
313 IRON HORSE unit: 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.	$515,000	Airbnb cash on cash: -0.34% Traditional cash on cash: 0.93% Airbnb Rental Income: $908 Traditional Rental Income: $1178 Airbnb ROI: -0.34% Traditional ROI: 0.93%
357 Hi Country Drive unit: #23-1 Winter Park, CO Discover this exceptional updated 2-bedroom, 2-bath condo boasting an open floor plan and ...	2 beds \| 2 baths \| 1,051 sq.ft.	$589,000	Airbnb cash on cash: 0.09% Traditional cash on cash: 1.34% Airbnb Rental Income: $1363 Traditional Rental Income: $1633 Airbnb ROI: 0.09% Traditional ROI: 1.34%
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: -0.22% Traditional cash on cash: 1.01% Airbnb Rental Income: $1699 Traditional Rental Income: $2888 Airbnb ROI: -0.22% Traditional ROI: 1.01%

Real Estate investment in Winter-park, CO

There are 127 properties for sale in the city of Winter Park . The median list price in Winter Park is $1,584,970 and the average price per square foot is $772. In March 2026, the average monthly cash on cash return in Winter Park is N/A%. The average monthly rental income in Winter Park is $2,368.

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

There are 127 investment properties available for sale in Winter-park.

In 2026, 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 $1,699.

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: -0.87%

Traditional cash on cash: -0.38%

Airbnb Rental Income: $2565

Traditional Rental Income: $3179

Airbnb ROI: -0.87%

Traditional ROI: -0.38%

45 Scenic Trail

Winter Park, CO

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

$2,684,411

Airbnb cash on cash: -0.87%

Traditional cash on cash: -0.38%

Airbnb Rental Income: $2565

Traditional Rental Income: $3179

Airbnb ROI: -0.87%

Traditional ROI: -0.38%

40 Cub Creek Way

Winter Park, CO

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

$3,465,000

Airbnb cash on cash: -0.96%

Traditional cash on cash: -0.11%

Airbnb Rental Income: $2565

Traditional Rental Income: $4673

Airbnb ROI: -0.96%

Traditional ROI: -0.11%

54 Cub Creek Way

Winter Park, CO

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

$3,470,000

Airbnb cash on cash: -0.93%

Traditional cash on cash: -0.45%

Airbnb Rental Income: $2565

Traditional Rental Income: $3479

Airbnb ROI: -0.93%

Traditional ROI: -0.45%

64 Overlook Place

Winter Park, CO

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

$2,744,642

Airbnb cash on cash: -0.89%

Traditional cash on cash: 0.12%

Airbnb Rental Income: $2565

Traditional Rental Income: $4517

Airbnb ROI: -0.89%

Traditional ROI: 0.12%

720 BAKER Drive unit: 404

Winter Park, CO

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

$1,025,000

Airbnb cash on cash: -1.64%

Traditional cash on cash: -0.03%

Airbnb Rental Income: $908

Traditional Rental Income: $2097

Airbnb ROI: -1.64%

Traditional ROI: -0.03%

720 BAKER Drive unit: 304

Winter Park, CO

2 beds | 1 baths | 874 sq.ft.

$795,000

Airbnb cash on cash: -0.97%

Traditional cash on cash: 0.22%

Airbnb Rental Income: $1363

Traditional Rental Income: $1831

Airbnb ROI: -0.97%

Traditional ROI: 0.22%

454 Lions Gate Dr

Winter Park, CO

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%