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
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: -0.92% Traditional cash on cash: 0.9% Airbnb Rental Income: $1363 Traditional Rental Income: $2389 Airbnb ROI: -0.92% Traditional ROI: 0.9%
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%
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.	$2,679,268	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.	$2,676,688	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%
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 \| 4 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 #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 #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%
580 Winter Park Drive unit: 4362 #4362 Winter Park, CO Located at the base of Winter Park Resort on the same level as the amenity deck, this spac...	1 beds \| 1 baths \| 533 sq.ft.	$549,000	Airbnb cash on cash: -0.64% Traditional cash on cash: 0.9% Airbnb Rental Income: $908 Traditional Rental Income: $1358 Airbnb ROI: -0.64% Traditional ROI: 0.9%
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%
477 Iron Horse Way unit: H3308 #H3308 Winter Park, CO SKI-IN/SKI-OUT at Iron Horse! This furnished 2-bedroom, 3-bath condo lives like a 3-bedroo...	2 beds \| 3 baths \| 1,472 sq.ft.	$749,000	Airbnb cash on cash: -0.19% Traditional cash on cash: 1.54% Airbnb Rental Income: $1363 Traditional Rental Income: $2155 Airbnb ROI: -0.19% Traditional ROI: 1.54%
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%
121 ELK Trail unit: 6 #6 Winter Park, CO NEW PRICE! Now the least expensive 3-bedroom, 3-bath Condo in Winter Park! Welcome to your...	3 beds \| 3 baths \| 2,217 sq.ft.	$850,000	Airbnb cash on cash: 0.02% Traditional cash on cash: 1.33% Airbnb Rental Income: $1699 Traditional Rental Income: $2264 Airbnb ROI: 0.02% Traditional ROI: 1.33%
66 Wheeler Road Winter Park, CO MOVE IN READY! Short term rental ''friendly'' with no HOA, the much-anticipated Sojourn at...	3 beds \| 3 baths \| 1,716 sq.ft.	$1,199,000	Airbnb cash on cash: -0.49% Traditional cash on cash: 0.64% Airbnb Rental Income: $1699 Traditional Rental Income: $2486 Airbnb ROI: -0.49% Traditional ROI: 0.64%
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: 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%
490 KINGS CROSSING unit: 331 #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%
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%
301 RESERVE Way Winter Park, CO Lovely home in Lakota, offering breathtaking, serene views of the Continental Divide, Wint...	5 beds \| 4 baths \| 2,996 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%
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: -0.36% Traditional cash on cash: 0.64% Airbnb Rental Income: $1699 Traditional Rental Income: $2345 Airbnb ROI: -0.36% Traditional ROI: 0.64%
377 Lions Gate Dr unit: 202 #202 Winter Park, CO Location alert! Don't Miss This Gorgeous 2-Bed, 2-Bath Condo in the Heart of Winter Park! ...	2 beds \| 2 baths \| 960 sq.ft.	$789,000	Airbnb cash on cash: -1.07% Traditional cash on cash: 0.32% Airbnb Rental Income: $1363 Traditional Rental Income: $1971 Airbnb ROI: -1.07% Traditional ROI: 0.32%
580 Winter Park Drive unit: 4564 #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 NOW BEING SOLD FULLY FURNISHED & TURNKEY Tucked away on a private double lot along the...	4 beds \| 4 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%
144 SKI IDLEWILD unit: 3206 #3206 Winter Park, CO Timber Fox - Experience the ultimate mountain property in this beautifully furnished 2-bed...	2 beds \| 2 baths \| 1,072 sq.ft.	$1,010,000	Airbnb cash on cash: -0.81% Traditional cash on cash: 0.61% Airbnb Rental Income: $1363 Traditional Rental Income: $2282 Airbnb ROI: -0.81% Traditional ROI: 0.61%
670 WINTER PARK unit: 3129 #3129 Winter Park, CO INVESTORS / ROI* This condo has proven track record for desirability** Carrie: Quick ,ea...	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%
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.	$1,295,000	Airbnb cash on cash: -0.52% Traditional cash on cash: 0.45% Airbnb Rental Income: $2565 Traditional Rental Income: $3107 Airbnb ROI: -0.52% Traditional ROI: 0.45%
85 RAMBLE Lane Winter Park, CO Welcome to one of Winter Park's most desirable addresses at 85 Ramble Lane at The Wilds 36...	4 beds \| 3 baths \| 2,994 sq.ft.	$2,250,000	Airbnb cash on cash: -0.67% Traditional cash on cash: -0.04% Airbnb Rental Income: $2565 Traditional Rental Income: $3275 Airbnb ROI: -0.67% Traditional ROI: -0.04%
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: -0.36% Traditional cash on cash: 0.52% Airbnb Rental Income: $1699 Traditional Rental Income: $2206 Airbnb ROI: -0.36% Traditional ROI: 0.52%
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: -0.28% Traditional cash on cash: 0.91% Airbnb Rental Income: $1363 Traditional Rental Income: $1889 Airbnb ROI: -0.28% Traditional ROI: 0.91%

Real Estate investment in Winter-park, CO

There are 130 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 $702. In February 2026, the average monthly cash on cash return in Winter Park is N/A%. The average monthly rental income in Winter Park is $2,386.

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

There are 130 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 $2,386.

Your search for investment property begins and ends here

Investment Property for Sale in Winter Park, CO

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: -0.92%

Traditional cash on cash: 0.9%

Airbnb Rental Income: $1363

Traditional Rental Income: $2389

Airbnb ROI: -0.92%

Traditional ROI: 0.9%

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%

19 Scenic Trail

Winter Park, CO

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

$2,679,268

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.

$2,676,688

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%

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 | 4 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%