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 53 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
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%
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%
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%
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%
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%
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%
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%
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%
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%
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%
720 BAKER Drive unit: 408 #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%
1008 Winter Park Drive unit: 2 #2 Winter Park, CO The A-Frame Owners Club transports you to the golden era of ski-town culture, where fires ...	1 beds \| 1 baths \| 595 sq.ft.	$679,000	Airbnb cash on cash: -0.95% Traditional cash on cash: 0.51% Airbnb Rental Income: $908 Traditional Rental Income: $1496 Airbnb ROI: -0.95% Traditional ROI: 0.51%
1008 Winter Park Drive unit: 11 #11 Winter Park, CO The A-Frame Owners Club transports you to the golden era of ski-town culture, where fires ...	1 beds \| 1 baths \| 595 sq.ft.	$679,000	Airbnb cash on cash: -0.95% Traditional cash on cash: 0.51% Airbnb Rental Income: $908 Traditional Rental Income: $1496 Airbnb ROI: -0.95% Traditional ROI: 0.51%
1008 Winter Park Drive unit: 24 #24 Winter Park, CO The A-Frame Owners Club transports you to the golden era of ski-town culture, where fires ...	1 beds \| 1 baths \| 595 sq.ft.	$649,000	Airbnb cash on cash: -0.95% Traditional cash on cash: 0.58% Airbnb Rental Income: $908 Traditional Rental Income: $1496 Airbnb ROI: -0.95% Traditional ROI: 0.58%
1008 Winter Park Drive unit: 25 #25 Winter Park, CO The A-Frame Owners Club transports you to the golden era of ski-town culture, where fires ...	1 beds \| 1 baths \| 595 sq.ft.	$699,000	Airbnb cash on cash: -0.95% Traditional cash on cash: 0.47% Airbnb Rental Income: $908 Traditional Rental Income: $1496 Airbnb ROI: -0.95% Traditional ROI: 0.47%
79050 US HWY 40 unit: A-303 #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 #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.	$529,000	Airbnb cash on cash: -0.36% Traditional cash on cash: 0.88% Airbnb Rental Income: $908 Traditional Rental Income: $1178 Airbnb ROI: -0.36% Traditional ROI: 0.88%
357 Hi Country Drive unit: #23-1 #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.	$599,000	Airbnb cash on cash: 0.07% Traditional cash on cash: 1.3% Airbnb Rental Income: $1363 Traditional Rental Income: $1633 Airbnb ROI: 0.07% Traditional ROI: 1.3%
1080 WINTER PARK unit: 1 #1 Winter Park, CO Mountain CHIC* Fully Updated 3B Condo in Old Town Winter Park. ONE OF A KIND condo, two un...	3 beds \| 2 baths \| 1,609 sq.ft.	$1,255,555	Airbnb cash on cash: -0.32% Traditional cash on cash: 0.83% Airbnb Rental Income: $1699 Traditional Rental Income: $2568 Airbnb ROI: -0.32% Traditional ROI: 0.83%
400 Baker Drive unit: 209 #209 Winter Park, CO In the heart of downtown Winter Park, this sharp and unique condo with over 1000 sq ft con...	1 beds \| 2 baths \| 1,011 sq.ft.	$640,000	Airbnb cash on cash: -1.67% Traditional cash on cash: 0.8% Airbnb Rental Income: $908 Traditional Rental Income: $2044 Airbnb ROI: -1.67% Traditional ROI: 0.8%
701 Trailhead unit: 721 #721 Winter Park, CO Here's an amazing opportunity to own a rarely available 1-bed, 1-bath condo in one of Wint...	1 beds \| 1 baths \| 793 sq.ft.	$675,000	Airbnb cash on cash: -0.63% Traditional cash on cash: 1.29% Airbnb Rental Income: $908 Traditional Rental Income: $1774 Airbnb ROI: -0.63% Traditional ROI: 1.29%
670 Winter Park Drive unit: 3413 #3413 Winter Park, CO Seller will prepay for 3 months of HOA Dues Mountain base convenience meets year-round...	1 beds \| 1 baths \| 622 sq.ft.	$550,000	Airbnb cash on cash: -0.76% Traditional cash on cash: 1.01% Airbnb Rental Income: $908 Traditional Rental Income: $1481 Airbnb ROI: -0.76% Traditional ROI: 1.01%
128 GCR 702 unit: 4-201 #4-201 Winter Park, CO Don't miss out on this price reduction and great value for your perfect 2-bedroom ski cond...	2 beds \| 2 baths \| 850 sq.ft.	$555,000	Airbnb cash on cash: -0.84% Traditional cash on cash: 0.34% Airbnb Rental Income: $1363 Traditional Rental Income: $1557 Airbnb ROI: -0.84% Traditional ROI: 0.34%
670 Winter Park Drive unit: 3307 #3307 Winter Park, CO Unlike most one-bedroom condos at Winter Park Resort, this spacious one-bedroom condo with...	1 beds \| 1 baths \| 620 sq.ft.	$550,000	Airbnb cash on cash: -0.76% Traditional cash on cash: 1.07% Airbnb Rental Income: $908 Traditional Rental Income: $1509 Airbnb ROI: -0.76% Traditional ROI: 1.07%
580 Winter Park Drive unit: 4370 #4370 Winter Park, CO This turnkey and low maintenance condo will become your favorite oasis at the Winter Park ...	1 beds \| 1 baths \| 533 sq.ft.	$545,000	Airbnb cash on cash: -0.64% Traditional cash on cash: 1.06% Airbnb Rental Income: $908 Traditional Rental Income: $1434 Airbnb ROI: -0.64% Traditional ROI: 1.06%
216 GCR 702 #18-101 Winter Park, CO Beautifully updated ground-floor end unit condo in the heart of Winter Park with an open f...	2 beds \| 2 baths \| 940 sq.ft.	$574,900	Airbnb cash on cash: 0.16% Traditional cash on cash: 1.33% Airbnb Rental Income: $1363 Traditional Rental Income: $1578 Airbnb ROI: 0.16% Traditional ROI: 1.33%
201 Zephyr Way unit: 2008 #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.	$684,900	Airbnb cash on cash: -0.59% Traditional cash on cash: 0.6% Airbnb Rental Income: $908 Traditional Rental Income: $1330 Airbnb ROI: -0.59% Traditional ROI: 0.6%
1008 Winter Park Drive unit: 31 #31 Winter Park, CO The A-Frame Owners Club transports you to the golden era of ski-town culture, where fires ...	1 beds \| 1 baths \| 595 sq.ft.	$599,000	Airbnb cash on cash: -0.95% Traditional cash on cash: 0.71% Airbnb Rental Income: $908 Traditional Rental Income: $1496 Airbnb ROI: -0.95% Traditional ROI: 0.71%
401 Nystrom Lane unit: 1404 #1404 Winter Park, CO Exceptional ski-in/ski-out condo in Zephyr Mountain Lodge, offering a rare 1 BD / 1 BA slo...	1 beds \| 1 baths \| 517 sq.ft.	$685,000	Airbnb cash on cash: -0.59% Traditional cash on cash: 0.38% Airbnb Rental Income: $908 Traditional Rental Income: $1193 Airbnb ROI: -0.59% Traditional ROI: 0.38%
144 SKI IDLEWILD Road unit: 3304 #3304 Winter Park, CO A stunning condo on the south end of downtown Winter Park in the vibrant new Roam communit...	2 beds \| 2 baths \| 1,101 sq.ft.	$1,039,000	Airbnb cash on cash: -0.8% Traditional cash on cash: 0.28% Airbnb Rental Income: $1363 Traditional Rental Income: $1986 Airbnb ROI: -0.8% Traditional ROI: 0.28%
21 Telemark Drive unit: 303 #303 Winter Park, CO Modern mountain convenience! Welcome to this stylish and updated 2-bed, 2-bath condo in th...	2 beds \| 2 baths \| 1,158 sq.ft.	$680,000	Airbnb cash on cash: -0.08% Traditional cash on cash: 1.59% Airbnb Rental Income: $1363 Traditional Rental Income: $2007 Airbnb ROI: -0.08% Traditional ROI: 1.59%
78683 US HWY 40 unit: 13-151 #13-151 Winter Park, CO You can't beat the location of this 3-bedroom, 2-bath top-floor end unit in the heart of d...	3 beds \| 2 baths \| 1,152 sq.ft.	$650,000	Airbnb cash on cash: 0.37% Traditional cash on cash: 1.9% Airbnb Rental Income: $1699 Traditional Rental Income: $2158 Airbnb ROI: 0.37% Traditional ROI: 1.9%

Your search for investment property begins and ends here

Condos 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%

720 BAKER Drive unit: 404 #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 #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%

580 Winter Park Drive unit: 4362 #4362

Winter Park, CO

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%

477 Iron Horse Way unit: H3308 #H3308

Winter Park, CO

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%

121 ELK Trail unit: 6 #6

Winter Park, CO

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%