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.

Condos for Sale in Winter Park, CO

Search for Condo for Sale in Winter Park, Colorado. Browse all of Mashvisor’s Condo listings and other investment property types including Single Family Homes, Multi Family Homes, Condos, Townhouses and Other Homes.

Showing 51 Condo listings of over 500,000 total investment properties for sale. Visit Mashvisor.com to all investment properties.

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PROPERTY	DETAILS	SALE PRICE	INVESTMENT PERFORMANCE
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: -1.99% Traditional cash on cash: 0.16% Airbnb Rental Income: $280 Traditional Rental Income: $2097 Airbnb ROI: -1.99% Traditional ROI: 0.16%
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: -1.2% Traditional cash on cash: 1.3% Airbnb Rental Income: $1136 Traditional Rental Income: $5112 Airbnb ROI: -1.2% 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% Traditional cash on cash: 1.34% Airbnb Rental Income: $1545 Traditional Rental Income: $5775 Airbnb ROI: -1% 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% Traditional cash on cash: 1.68% Airbnb Rental Income: $1545 Traditional Rental Income: $5775 Airbnb ROI: -1% Traditional ROI: 1.68%
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: -0.86% Traditional cash on cash: 1.55% Airbnb Rental Income: $637 Traditional Rental Income: $1473 Airbnb ROI: -0.86% 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: -1.66% Traditional cash on cash: 0.88% Airbnb Rental Income: $280 Traditional Rental Income: $1373 Airbnb ROI: -1.66% Traditional ROI: 0.88%
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: -0.77% Traditional cash on cash: 0.53% Airbnb Rental Income: $1136 Traditional Rental Income: $2206 Airbnb ROI: -0.77% 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: -1.04% Traditional cash on cash: 0.93% Airbnb Rental Income: $637 Traditional Rental Income: $1889 Airbnb ROI: -1.04% 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: -0.94% Traditional cash on cash: 0.92% Airbnb Rental Income: $637 Traditional Rental Income: $1889 Airbnb ROI: -0.94% Traditional ROI: 0.92%
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: -1.5% Traditional cash on cash: 0.92% Airbnb Rental Income: $280 Traditional Rental Income: $1178 Airbnb ROI: -1.5% Traditional ROI: 0.92%
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: -0.7% Traditional cash on cash: 0.85% Airbnb Rental Income: $1136 Traditional Rental Income: $2568 Airbnb ROI: -0.7% Traditional ROI: 0.85%
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: -1.79% Traditional cash on cash: 1.11% Airbnb Rental Income: $280 Traditional Rental Income: $1481 Airbnb ROI: -1.79% Traditional ROI: 1.11%
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: -0.84% Traditional cash on cash: 1.53% Airbnb Rental Income: $637 Traditional Rental Income: $1523 Airbnb ROI: -0.84% 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: -1.09% Traditional cash on cash: 0.61% Airbnb Rental Income: $637 Traditional Rental Income: $2188 Airbnb ROI: -1.09% 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: -1% Traditional cash on cash: 0.15% Airbnb Rental Income: $1545 Traditional Rental Income: $3610 Airbnb ROI: -1% Traditional ROI: 0.15%
310 Iron Horse Way #D5024 Winter Park, CO Completely reimagined with a mountain-contemporary aesthetic, this rare one-bedroom reside...	1 beds \| 1 baths \| 563 sq.ft.	$575,000	Airbnb cash on cash: -1.45% Traditional cash on cash: 1.14% Airbnb Rental Income: $280 Traditional Rental Income: $1439 Airbnb ROI: -1.45% Traditional ROI: 1.14%
401 Nystrom Lane #1503 Winter Park, CO Experience Winter Park's most desirable location, Zephyr Mountain Lodge - Slopeside. Situa...	2 beds \| 2 baths \| 855 sq.ft.	$1,005,000	Airbnb cash on cash: -1.1% Traditional cash on cash: 0.19% Airbnb Rental Income: $637 Traditional Rental Income: $1546 Airbnb ROI: -1.1% Traditional ROI: 0.19%
201 Zephyr Way #2008 Winter Park, CO Rare Ski-In/Ski-Out 1-Bedroom Riverfront Gem! One of only 7 coveted units with direct outd...	1 beds \| 1 baths \| 536 sq.ft.	$669,000	Airbnb cash on cash: -1.41% Traditional cash on cash: 0.71% Airbnb Rental Income: $280 Traditional Rental Income: $1369 Airbnb ROI: -1.41% Traditional ROI: 0.71%
580 Winter Park Drive #4566 Winter Park, CO This fully furnished ski-in/ski-out condo is located at the base of Winter Park Resort, fe...	1 beds \| 1 baths \| 533 sq.ft.	$545,000	Airbnb cash on cash: -1.68% Traditional cash on cash: 0.93% Airbnb Rental Income: $280 Traditional Rental Income: $1370 Airbnb ROI: -1.68% Traditional ROI: 0.93%
201 Zephyr Way #2216 Winter Park, CO Experience the ultimate mountain lifestyle in this beautifully updated one-bedroom ski-in/...	1 beds \| 1 baths \| 526 sq.ft.	$649,000	Airbnb cash on cash: -1.43% Traditional cash on cash: 0.59% Airbnb Rental Income: $280 Traditional Rental Income: $1269 Airbnb ROI: -1.43% Traditional ROI: 0.59%
490 KINGS CROSSING Road #611 Winter Park, CO Escape to your mountain paradise in this stunning ground-floor 2-bedroom condo at Silverad...	2 beds \| 2 baths \| 813 sq.ft.	$520,000	Airbnb cash on cash: -0.85% Traditional cash on cash: 1.46% Airbnb Rental Income: $637 Traditional Rental Income: $1466 Airbnb ROI: -0.85% Traditional ROI: 1.46%
310 Iron Horse Way #D2024 Winter Park, CO Check out this gorgeous 1 bed, 1 bath unit in Iron Horse Condominiums! Discover a spacious...	1 beds \| 1 baths \| 583 sq.ft.	$539,000	Airbnb cash on cash: -1.47% Traditional cash on cash: 1.24% Airbnb Rental Income: $280 Traditional Rental Income: $1407 Airbnb ROI: -1.47% Traditional ROI: 1.24%
90 HIDEAWAY #1 Winter Park, CO Low HOA Dues + Priced to Sell in Prime Winter Park Location! Don't miss this incredible op...	2 beds \| 2 baths \| 892 sq.ft.	$540,000	Airbnb cash on cash: -0.89% Traditional cash on cash: 1.06% Airbnb Rental Income: $637 Traditional Rental Income: $1328 Airbnb ROI: -0.89% Traditional ROI: 1.06%
121 ELK Trail #6 Winter Park, CO Check out this large 3-bedroom, 3-bath Condo in Winter Park! Welcome to your alpine getawa...	3 beds \| 3 baths \| 2,217 sq.ft.	$850,000	Airbnb cash on cash: -0.63% Traditional cash on cash: 2.42% Airbnb Rental Income: $1136 Traditional Rental Income: $3170 Airbnb ROI: -0.63% Traditional ROI: 2.42%
144 SKI IDLEWILD Road #2404 Winter Park, CO A perfect blend of alpine charm and modern comfort in this stunning 2 bedroom and 2 bath c...	2 beds \| 2 baths \| 1,136 sq.ft.	$1,129,900	Airbnb cash on cash: -1.35% Traditional cash on cash: 0.3% Airbnb Rental Income: $637 Traditional Rental Income: $2083 Airbnb ROI: -1.35% Traditional ROI: 0.3%
524 Baker Drive Winter Park, CO Townhome-style living in downtown, this 2-bed, 2-bath condo offers an attached, heated gar...	2 beds \| 2 baths \| 1,064 sq.ft.	$875,000	Airbnb cash on cash: -1.07% Traditional cash on cash: 0.62% Airbnb Rental Income: $637 Traditional Rental Income: $1718 Airbnb ROI: -1.07% Traditional ROI: 0.62%
658 TELEMARK Court #A-658 Winter Park, CO Situated in an idyllic downtown Winter Park setting along a serene pond and the Fraser Riv...	3 beds \| 3 baths \| 2,047 sq.ft.	$1,279,000	Airbnb cash on cash: -0.78% Traditional cash on cash: 1.46% Airbnb Rental Income: $1136 Traditional Rental Income: $3430 Airbnb ROI: -0.78% Traditional ROI: 1.46%
477 IRON HORSE #H 5108 Winter Park, CO Experience the ultimate in mountain luxury with this top-floor, end-unit condo, offering u...	2 beds \| 3 baths \| 1,455 sq.ft.	$739,000	Airbnb cash on cash: -1.04% Traditional cash on cash: 1.45% Airbnb Rental Income: $637 Traditional Rental Income: $2057 Airbnb ROI: -1.04% Traditional ROI: 1.45%
471 Hi Country Drive #611 Winter Park, CO End-unit condo overlooking the Fraser River in the heart of Winter Park. This fully furnis...	2 beds \| 1 baths \| 651 sq.ft.	$459,000	Airbnb cash on cash: -0.85% Traditional cash on cash: 1.35% Airbnb Rental Income: $637 Traditional Rental Income: $1290 Airbnb ROI: -0.85% Traditional ROI: 1.35%
225 HI COUNTRY DR #1313 Winter Park, CO Inviting 1-bedroom condo, perfectly positioned right along the Fraser river in the heart o...	1 beds \| 1 baths \| 481 sq.ft.	$390,000	Airbnb cash on cash: -1.55% Traditional cash on cash: 1.39% Airbnb Rental Income: $280 Traditional Rental Income: $1117 Airbnb ROI: -1.55% Traditional ROI: 1.39%
377 Lions Gate Drive #102 Winter Park, CO Right in downtown Winter Park, this 2022-built mountain-modern condo puts you steps from y...	2 beds \| 2 baths \| 957 sq.ft.	$799,000	Airbnb cash on cash: -0.95% Traditional cash on cash: 1.21% Airbnb Rental Income: $637 Traditional Rental Income: $1955 Airbnb ROI: -0.95% Traditional ROI: 1.21%
501 TRAILHEAD Circle #533 Winter Park, CO This Trailhead Lodge top floor unit is located in the heart of downtown Winter Park but yo...	2 beds \| 2 baths \| 1,193 sq.ft.	$925,000	Airbnb cash on cash: -1.48% Traditional cash on cash: 0.38% Airbnb Rental Income: $637 Traditional Rental Income: $1940 Airbnb ROI: -1.48% Traditional ROI: 0.38%
422 FOREST TRL BLDG B Winter Park, CO Tall Pines, located in Winter Park, minutes to main street/downtown for restaurants, shopp...	2 beds \| 2 baths \| 776 sq.ft.	$575,000	Airbnb cash on cash: -0.93% Traditional cash on cash: 1.2% Airbnb Rental Income: $637 Traditional Rental Income: $1489 Airbnb ROI: -0.93% Traditional ROI: 1.2%
78321 US HWY 40 #22 Winter Park, CO Enjoy easy living in Winter Park in this super bright, contemporary townhome-style condo. ...	2 beds \| 3 baths \| 1,130 sq.ft.	$785,000	Airbnb cash on cash: -1.09% Traditional cash on cash: 1.44% Airbnb Rental Income: $637 Traditional Rental Income: $2196 Airbnb ROI: -1.09% Traditional ROI: 1.44%
78415 US HWY 40 #5 Winter Park, CO Rare 4-bedroom condo in the heart of downtown Winter Park with slope views, outdoor living...	4 beds \| 3 baths \| 1,763 sq.ft.	$1,355,000	Airbnb cash on cash: -0.55% Traditional cash on cash: 0.79% Airbnb Rental Income: $1545 Traditional Rental Income: $2783 Airbnb ROI: -0.55% Traditional ROI: 0.79%
41 FOREST Trail #7 Winter Park, CO Spread across three floors with breathtaking mountain views, this fully furnished 3-bedroo...	3 beds \| 3 baths \| 1,764 sq.ft.	$1,025,000	Airbnb cash on cash: -0.63% Traditional cash on cash: 1.36% Airbnb Rental Income: $1136 Traditional Rental Income: $2657 Airbnb ROI: -0.63% Traditional ROI: 1.36%
46 E VIKING #B102 Winter Park, CO FINALLY! A fully renovated condo at Vasquez Run in Winter Park! Offering 3 sleeping spaces...	2 beds \| 2 baths \| 1,110 sq.ft.	$799,000	Airbnb cash on cash: -1.07% Traditional cash on cash: 0.77% Airbnb Rental Income: $637 Traditional Rental Income: $1710 Airbnb ROI: -1.07% Traditional ROI: 0.77%
273 Hi Country Drive #9 Winter Park, CO Quietly tucked along the Fraser River in downtown Winter Park sits this beautifully update...	1 beds \| 1 baths \| 460 sq.ft.	$415,000	Airbnb cash on cash: -1.5% Traditional cash on cash: 1.66% Airbnb Rental Income: $280 Traditional Rental Income: $1272 Airbnb ROI: -1.5% Traditional ROI: 1.66%
144 Ski Idlewild Road #3102 Winter Park, CO A sunlit condo with the best location in downtown Winter Park. The beautiful tall and larg...	3 beds \| 2 baths \| 1,375 sq.ft.	$1,299,900	Airbnb cash on cash: -1.1% Traditional cash on cash: 0.11% Airbnb Rental Income: $1136 Traditional Rental Income: $2224 Airbnb ROI: -1.1% Traditional ROI: 0.11%
201 Zephyr Way #2404 Winter Park, CO True ski in ski out ownership in the heart of Winter Park Resort's base village. 201 Zephy...	2 beds \| 2 baths \| 953 sq.ft.	$1,099,000	Airbnb cash on cash: -1.11% Traditional cash on cash: 0.09% Airbnb Rental Income: $637 Traditional Rental Income: $1569 Airbnb ROI: -1.11% Traditional ROI: 0.09%

Your search for investment property begins and ends here

Condos for Sale in Winter Park, CO

720 BAKER Drive #404

Winter Park, CO

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

$1,025,000

Airbnb cash on cash: -1.99%

Traditional cash on cash: 0.16%

Airbnb Rental Income: $280

Traditional Rental Income: $2097

Airbnb ROI: -1.99%

Traditional ROI: 0.16%

385 Lions Gate Drive #I

Winter Park, CO

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

$1,875,000

Airbnb cash on cash: -1.2%

Traditional cash on cash: 1.3%

Airbnb Rental Income: $1136

Traditional Rental Income: $5112

Airbnb ROI: -1.2%

Traditional ROI: 1.3%

385 Lions Gate Drive #C

Winter Park, CO

4 beds | 5 baths | 2,807 sq.ft.

$2,150,000

Airbnb cash on cash: -1%

Traditional cash on cash: 1.34%

Airbnb Rental Income: $1545

Traditional Rental Income: $5775

Airbnb ROI: -1%

Traditional ROI: 1.34%

385 Lions Gate Drive #B

Winter Park, CO

4 beds | 5 baths | 2,824 sq.ft.

$1,875,000

Airbnb cash on cash: -1%

Traditional cash on cash: 1.68%

Airbnb Rental Income: $1545

Traditional Rental Income: $5775

Airbnb ROI: -1%

Traditional ROI: 1.68%

490 KINGS CROSSING #331

Winter Park, CO

2 beds | 2 baths | 860 sq.ft.

$500,000

Airbnb cash on cash: -0.86%

Traditional cash on cash: 1.55%

Airbnb Rental Income: $637

Traditional Rental Income: $1473

Airbnb ROI: -0.86%

Traditional ROI: 1.55%

580 Winter Park Drive #4564

Winter Park, CO

1 beds | 1 baths | 533 sq.ft.

$560,000

Airbnb cash on cash: -1.66%

Traditional cash on cash: 0.88%

Airbnb Rental Income: $280

Traditional Rental Income: $1373

Airbnb ROI: -1.66%

Traditional ROI: 0.88%

78746 US HWY 40 #210

Winter Park, CO

3 beds | 3 baths | 1,506 sq.ft.

$1,199,000

Airbnb cash on cash: -0.77%

Traditional cash on cash: 0.53%

Airbnb Rental Income: $1136

Traditional Rental Income: $2206

Airbnb ROI: -0.77%

Traditional ROI: 0.53%

720 BAKER Drive #309

Winter Park, CO

2 beds | 2 baths | 955 sq.ft.

$845,000

Airbnb cash on cash: -1.04%

Traditional cash on cash: 0.93%

Airbnb Rental Income: $637

Traditional Rental Income: $1889

Airbnb ROI: -1.04%