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 65 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: -1.57% Traditional cash on cash: 0.16% Airbnb Rental Income: $760 Traditional Rental Income: $2097 Airbnb ROI: -1.57% Traditional ROI: 0.16%
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%
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%
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%
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%
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%
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%
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%
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%
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%
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: -0.89% Traditional cash on cash: 0.61% Airbnb Rental Income: $903 Traditional Rental Income: $2188 Airbnb ROI: -0.89% Traditional ROI: 0.61%
385 Lions Gate Drive #G Winter Park, CO Welcome to Lion's Rock Townhomes--Winter Park's most refined boutique development. Unit G,...	4 beds \| 5 baths \| 2,807 sq.ft.	$2,350,000	Airbnb cash on cash: -0.96% Traditional cash on cash: 0.15% Airbnb Rental Income: $1646 Traditional Rental Income: $3610 Airbnb ROI: -0.96% Traditional ROI: 0.15%
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: -0.77% Traditional cash on cash: 0.71% Airbnb Rental Income: $760 Traditional Rental Income: $1369 Airbnb ROI: -0.77% Traditional ROI: 0.71%
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: -0.86% Traditional cash on cash: 0.19% Airbnb Rental Income: $903 Traditional Rental Income: $1546 Airbnb ROI: -0.86% Traditional ROI: 0.19%
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: -0.89% Traditional cash on cash: 0.93% Airbnb Rental Income: $760 Traditional Rental Income: $1370 Airbnb ROI: -0.89% 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.	$629,000	Airbnb cash on cash: -0.77% Traditional cash on cash: 0.64% Airbnb Rental Income: $760 Traditional Rental Income: $1269 Airbnb ROI: -0.77% Traditional ROI: 0.64%
310 Iron Horse Way #D2104 Winter Park, CO Experience true ski-in/ski-out living from this Iron Horse 1-bed, 1-bath condo-right off t...	1 beds \| 1 baths \| 583 sq.ft.	$515,000	Airbnb cash on cash: -0.67% Traditional cash on cash: 0.84% Airbnb Rental Income: $760 Traditional Rental Income: $1173 Airbnb ROI: -0.67% Traditional ROI: 0.84%
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: -0.39% Traditional cash on cash: 1.46% Airbnb Rental Income: $903 Traditional Rental Income: $1466 Airbnb ROI: -0.39% Traditional ROI: 1.46%
90 HIDEAWAY #1 Winter Park, CO Don't miss this fully furnished, turnkey condo in the heart of Winter Park's Hideaway Vill...	2 beds \| 2 baths \| 892 sq.ft.	$530,000	Airbnb cash on cash: -0.44% Traditional cash on cash: 1.1% Airbnb Rental Income: $903 Traditional Rental Income: $1328 Airbnb ROI: -0.44% Traditional ROI: 1.1%
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: -0.67% Traditional cash on cash: 1.24% Airbnb Rental Income: $760 Traditional Rental Income: $1407 Airbnb ROI: -0.67% Traditional ROI: 1.24%
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: -0.24% Traditional cash on cash: 2.42% Airbnb Rental Income: $1500 Traditional Rental Income: $3170 Airbnb ROI: -0.24% Traditional ROI: 2.42%
78491 US Hwy 40 #6 Winter Park, CO This 2-bedroom condo at Village Center puts you right in the heart of downtown Winter Park...	2 beds \| 1 baths \| 1,084 sq.ft.	$515,000	Airbnb cash on cash: -0.44% Traditional cash on cash: 1.35% Airbnb Rental Income: $903 Traditional Rental Income: $1429 Airbnb ROI: -0.44% Traditional ROI: 1.35%
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: -1.14% Traditional cash on cash: 0.3% Airbnb Rental Income: $903 Traditional Rental Income: $2083 Airbnb ROI: -1.14% Traditional ROI: 0.3%
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: -0.45% Traditional cash on cash: 1.39% Airbnb Rental Income: $760 Traditional Rental Income: $1117 Airbnb ROI: -0.45% 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: -0.65% Traditional cash on cash: 1.21% Airbnb Rental Income: $903 Traditional Rental Income: $1955 Airbnb ROI: -0.65% Traditional ROI: 1.21%
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.	$410,000	Airbnb cash on cash: -0.47% Traditional cash on cash: 1.69% Airbnb Rental Income: $760 Traditional Rental Income: $1272 Airbnb ROI: -0.47% Traditional ROI: 1.69%
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.	$1,199,900	Airbnb cash on cash: -0.84% Traditional cash on cash: 0.2% Airbnb Rental Income: $1500 Traditional Rental Income: $2224 Airbnb ROI: -0.84% Traditional ROI: 0.2%
144 Ski Idlewild Road #3304 Winter Park, CO Located on the south end of downtown Winter Park in the newer ROAM community, this beautif...	2 beds \| 2 baths \| 1,101 sq.ft.	$998,000	Airbnb cash on cash: -1.26% Traditional cash on cash: 0.31% Airbnb Rental Income: $903 Traditional Rental Income: $2018 Airbnb ROI: -1.26% Traditional ROI: 0.31%
81 KINNEY Way #3 Winter Park, CO Perfectly positioned in the coveted Slopeside Village Building G, this beautifully updated...	4 beds \| 3 baths \| 2,182 sq.ft.	$1,475,000	Airbnb cash on cash: -0.59% Traditional cash on cash: 1.13% Airbnb Rental Income: $1646 Traditional Rental Income: $3532 Airbnb ROI: -0.59% Traditional ROI: 1.13%
128 GCR 702 #4-202 Winter Park, CO A stone's throw away from the proposed SKI-BACK TRAIL and TOWN GONDOLA! Tucked among the A...	2 beds \| 2 baths \| 850 sq.ft.	$565,000	Airbnb cash on cash: -0.52% Traditional cash on cash: 1.27% Airbnb Rental Income: $903 Traditional Rental Income: $1508 Airbnb ROI: -0.52% Traditional ROI: 1.27%
201 Trailhead Circle #234 Winter Park, CO Welcome to this spectacular 4-bedroom (1 non-conforming), 3-bath spacious condo in the HEA...	4 beds \| 3 baths \| 1,588 sq.ft.	$1,238,500	Airbnb cash on cash: -0.43% Traditional cash on cash: 0.79% Airbnb Rental Income: $1646 Traditional Rental Income: $2591 Airbnb ROI: -0.43% Traditional ROI: 0.79%
370 Forest Trail #D Winter Park, CO Quintessential mountain condo in the intimate four-unit California Suites. This top-floor ...	2 beds \| 2 baths \| 1,075 sq.ft.	$625,000	Airbnb cash on cash: -0.66% Traditional cash on cash: 1.24% Airbnb Rental Income: $903 Traditional Rental Income: $1669 Airbnb ROI: -0.66% Traditional ROI: 1.24%
518 Hi Country Drive #13-148 Winter Park, CO Top-floor, move-in ready, and steps from everything Winter Park has to offer. Updated 3-be...	3 beds \| 2 baths \| 804 sq.ft.	$682,000	Airbnb cash on cash: 0.19% Traditional cash on cash: 1.09% Airbnb Rental Income: $1500 Traditional Rental Income: $1632 Airbnb ROI: 0.19% Traditional ROI: 1.09%
44 GCR 702 #2-202 Winter Park, CO Tucked into a private forest setting at Beaver Village, this nicely updated 2-bedroom cond...	2 beds \| 2 baths \| 850 sq.ft.	$585,000	Airbnb cash on cash: -0.54% Traditional cash on cash: 1.18% Airbnb Rental Income: $903 Traditional Rental Income: $1501 Airbnb ROI: -0.54% Traditional ROI: 1.18%
313 Iron Horse Way #3113 Winter Park, CO This Ski-In/Out two bedroom unit has been totally remodeled with granite counters, wood ca...	2 beds \| 2 baths \| 774 sq.ft.	$650,000	Airbnb cash on cash: -0.6% Traditional cash on cash: 0.95% Airbnb Rental Income: $903 Traditional Rental Income: $1508 Airbnb ROI: -0.6% Traditional ROI: 0.95%

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: -1.57%

Traditional cash on cash: 0.16%

Airbnb Rental Income: $760

Traditional Rental Income: $2097

Airbnb ROI: -1.57%

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: -1.02%

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

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

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%

580 Winter Park Drive #4564

Winter Park, CO

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%

490 KINGS CROSSING #331

Winter Park, CO

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%

78746 US HWY 40 #210

Winter Park, CO

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

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%