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
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.	$869,000	Airbnb cash on cash: -1% Traditional cash on cash: 1.95% Airbnb Rental Income: $830 Traditional Rental Income: $2886 Airbnb ROI: -1% Traditional ROI: 1.95%
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: -1.92% Traditional cash on cash: 0.16% Airbnb Rental Income: $364 Traditional Rental Income: $2097 Airbnb ROI: -1.92% Traditional ROI: 0.16%
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 \| 5 baths \| 2,843 sq.ft.	$1,875,000	Airbnb cash on cash: -1.29% Traditional cash on cash: 1.3% Airbnb Rental Income: $952 Traditional Rental Income: $5112 Airbnb ROI: -1.29% Traditional ROI: 1.3%
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 \| 5 baths \| 2,807 sq.ft.	$2,150,000	Airbnb cash on cash: -1.3% Traditional cash on cash: 1.34% Airbnb Rental Income: $830 Traditional Rental Income: $5775 Airbnb ROI: -1.3% Traditional ROI: 1.34%
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 \| 5 baths \| 2,824 sq.ft.	$1,875,000	Airbnb cash on cash: -1.35% Traditional cash on cash: 1.68% Airbnb Rental Income: $830 Traditional Rental Income: $5775 Airbnb ROI: -1.35% Traditional ROI: 1.68%
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: -0.91% Traditional cash on cash: 0.66% Airbnb Rental Income: $952 Traditional Rental Income: $2345 Airbnb ROI: -0.91% Traditional ROI: 0.66%
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: -0.98% Traditional cash on cash: 1.48% Airbnb Rental Income: $572 Traditional Rental Income: $1473 Airbnb ROI: -0.98% Traditional ROI: 1.48%
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: -1.49% Traditional cash on cash: 0.73% Airbnb Rental Income: $364 Traditional Rental Income: $1358 Airbnb ROI: -1.49% Traditional ROI: 0.73%
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: -1.35% Traditional cash on cash: 0.42% Airbnb Rental Income: $572 Traditional Rental Income: $1771 Airbnb ROI: -1.35% Traditional ROI: 0.42%
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 \| 3 baths \| 1,506 sq.ft.	$1,199,000	Airbnb cash on cash: -0.91% Traditional cash on cash: 0.53% Airbnb Rental Income: $952 Traditional Rental Income: $2206 Airbnb ROI: -0.91% Traditional ROI: 0.53%
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: -1.11% Traditional cash on cash: 0.93% Airbnb Rental Income: $572 Traditional Rental Income: $1889 Airbnb ROI: -1.11% Traditional ROI: 0.93%
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: -1% Traditional cash on cash: 0.92% Airbnb Rental Income: $572 Traditional Rental Income: $1889 Airbnb ROI: -1% Traditional ROI: 0.92%
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: -1.08% Traditional cash on cash: 1.37% Airbnb Rental Income: $572 Traditional Rental Income: $1633 Airbnb ROI: -1.08% Traditional ROI: 1.37%
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: -1.06% Traditional cash on cash: 1.04% Airbnb Rental Income: $572 Traditional Rental Income: $1783 Airbnb ROI: -1.06% Traditional ROI: 1.04%
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: -1.34% Traditional cash on cash: 0.87% Airbnb Rental Income: $364 Traditional Rental Income: $1178 Airbnb ROI: -1.34% Traditional ROI: 0.87%
1080 WINTER PARK unit: 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: -0.84% Traditional cash on cash: 0.85% Airbnb Rental Income: $952 Traditional Rental Income: $2568 Airbnb ROI: -0.84% Traditional ROI: 0.85%
128 GCR 702 unit: 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: -2.11% Traditional cash on cash: 0.34% Airbnb Rental Income: $572 Traditional Rental Income: $1557 Airbnb ROI: -2.11% Traditional ROI: 0.34%
580 Winter Park Drive unit: 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.	$520,000	Airbnb cash on cash: -1.56% Traditional cash on cash: 1.15% Airbnb Rental Income: $364 Traditional Rental Income: $1434 Airbnb ROI: -1.56% Traditional ROI: 1.15%
670 Winter Park Drive unit: 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: -1.65% Traditional cash on cash: 1.11% Airbnb Rental Income: $364 Traditional Rental Income: $1481 Airbnb ROI: -1.65% Traditional ROI: 1.11%
216 Village Dr #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: -1.05% Traditional cash on cash: 1.35% Airbnb Rental Income: $572 Traditional Rental Income: $1578 Airbnb ROI: -1.05% Traditional ROI: 1.35%
490 KINGS CROSSING unit: 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: -0.94% Traditional cash on cash: 1.43% Airbnb Rental Income: $572 Traditional Rental Income: $1477 Airbnb ROI: -0.94% Traditional ROI: 1.43%
572 Telemark Court Winter Park, CO Discover a rare & private riverfront retreat in downtown Winter Park. This townhome-style ...	3 beds \| 2 baths \| 1,537 sq.ft.	$1,199,000	Airbnb cash on cash: -0.82% Traditional cash on cash: 0.9% Airbnb Rental Income: $952 Traditional Rental Income: $2524 Airbnb ROI: -0.82% Traditional ROI: 0.9%
97 KINNEY Winter Park, CO Welcome to the Slopeside Village Luxury Chalet 97 A, a stunning retreat nestled next to th...	2 beds \| 2 baths \| 1,376 sq.ft.	$1,249,900	Airbnb cash on cash: -1.13% Traditional cash on cash: 0.5% Airbnb Rental Income: $572 Traditional Rental Income: $2188 Airbnb ROI: -1.13% Traditional ROI: 0.5%
385 Lions Gate Drive unit: 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: -1.27% Traditional cash on cash: 0.15% Airbnb Rental Income: $830 Traditional Rental Income: $3610 Airbnb ROI: -1.27% Traditional ROI: 0.15%
310 Iron Horse Way unit: 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: -1.32% Traditional cash on cash: 1.14% Airbnb Rental Income: $364 Traditional Rental Income: $1439 Airbnb ROI: -1.32% Traditional ROI: 1.14%
401 Nystrom Lane #1503 Winter Park, CO Experience the ultimate mountain getaway in the only 2-bedroom residence currently availab...	2 beds \| 2 baths \| 855 sq.ft.	$1,025,000	Airbnb cash on cash: -1.16% Traditional cash on cash: 0.16% Airbnb Rental Income: $572 Traditional Rental Income: $1546 Airbnb ROI: -1.16% Traditional ROI: 0.16%
201 Zephyr Way unit: 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: -1.3% Traditional cash on cash: 0.65% Airbnb Rental Income: $364 Traditional Rental Income: $1330 Airbnb ROI: -1.3% Traditional ROI: 0.65%
580 Winter Park Drive unit: 4566 Winter Park, CO LOWEST PRICED one-bedroom in the complex! This fully furnished ski-in/ski-out condo is loc...	1 beds \| 1 baths \| 533 sq.ft.	$545,000	Airbnb cash on cash: -1.54% Traditional cash on cash: 0.93% Airbnb Rental Income: $364 Traditional Rental Income: $1370 Airbnb ROI: -1.54% Traditional ROI: 0.93%
201 Zephyr Way unit: 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: -1.32% Traditional cash on cash: 0.48% Airbnb Rental Income: $364 Traditional Rental Income: $1204 Airbnb ROI: -1.32% Traditional ROI: 0.48%
490 KINGS CROSSING Road unit: 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: -0.96% Traditional cash on cash: 1.46% Airbnb Rental Income: $572 Traditional Rental Income: $1466 Airbnb ROI: -0.96% Traditional ROI: 1.46%
144 Ski Idlewild Road unit: #2203 Winter Park, CO Easy to tour! Discover your dream 2-bed/2-bath condo in the highly sought-after Timber Fox...	2 beds \| 2 baths \| 1,030 sq.ft.	$1,037,000	Airbnb cash on cash: -1.43% Traditional cash on cash: 0.6% Airbnb Rental Income: $572 Traditional Rental Income: $2249 Airbnb ROI: -1.43% Traditional ROI: 0.6%
310 Iron Horse Way unit: 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: -1.33% Traditional cash on cash: 1.24% Airbnb Rental Income: $364 Traditional Rental Income: $1407 Airbnb ROI: -1.33% 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.	$550,000	Airbnb cash on cash: -1% Traditional cash on cash: 1.02% Airbnb Rental Income: $572 Traditional Rental Income: $1328 Airbnb ROI: -1% Traditional ROI: 1.02%
121 ELK Trail unit: 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: -0.82% Traditional cash on cash: 1.28% Airbnb Rental Income: $952 Traditional Rental Income: $2264 Airbnb ROI: -0.82% Traditional ROI: 1.28%
78491 US Hwy 40 unit: 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: -1.02% Traditional cash on cash: 1.35% Airbnb Rental Income: $572 Traditional Rental Income: $1429 Airbnb ROI: -1.02% Traditional ROI: 1.35%
580 Winter Park Drive unit: 4474 Winter Park, CO This is the mountain escape buyers hunt for--true ski-in/walk-out access in the heart of W...	2 beds \| 2 baths \| 990 sq.ft.	$949,000	Airbnb cash on cash: -1.36% Traditional cash on cash: 0.6% Airbnb Rental Income: $572 Traditional Rental Income: $2020 Airbnb ROI: -1.36% Traditional ROI: 0.6%
401 Nystrom Lane unit: 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: -1.33% Traditional cash on cash: 0.36% Airbnb Rental Income: $364 Traditional Rental Income: $1193 Airbnb ROI: -1.33% Traditional ROI: 0.36%
477 IRON HORSE unit: 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: -1.12% Traditional cash on cash: 1.45% Airbnb Rental Income: $572 Traditional Rental Income: $2057 Airbnb ROI: -1.12% Traditional ROI: 1.45%
201 ZEPHYR WAY #2404 Winter Park, CO True ski in ski out ownership in the heart of Winter Park Resortâs base village. 201 Zep...	2 beds \| 2 baths \| 953 sq.ft.	$1,099,000	Airbnb cash on cash: -1.16% Traditional cash on cash: 0.09% Airbnb Rental Income: $572 Traditional Rental Income: $1569 Airbnb ROI: -1.16% Traditional ROI: 0.09%

Your search for investment property begins and ends here

Condos for Sale in Winter Park, CO

490 Kings Crossing Road 631-633

Winter Park, CO

4 beds | 4 baths | 1,720 sq.ft.

$869,000

Airbnb cash on cash: -1%

Traditional cash on cash: 1.95%

Airbnb Rental Income: $830

Traditional Rental Income: $2886

Airbnb ROI: -1%

Traditional ROI: 1.95%

720 BAKER Drive unit: 404

Winter Park, CO

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

$1,025,000

Airbnb cash on cash: -1.92%

Traditional cash on cash: 0.16%

Airbnb Rental Income: $364

Traditional Rental Income: $2097

Airbnb ROI: -1.92%

Traditional ROI: 0.16%

385 Lions Gate Drive unit: I

Winter Park, CO

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

$1,875,000

Airbnb cash on cash: -1.29%

Traditional cash on cash: 1.3%

Airbnb Rental Income: $952

Traditional Rental Income: $5112

Airbnb ROI: -1.29%

Traditional ROI: 1.3%

385 Lions Gate Drive unit: C

Winter Park, CO

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

$2,150,000

Airbnb cash on cash: -1.3%

Traditional cash on cash: 1.34%

Airbnb Rental Income: $830

Traditional Rental Income: $5775

Airbnb ROI: -1.3%

Traditional ROI: 1.34%

385 Lions Gate Drive unit: B

Winter Park, CO

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

$1,875,000

Airbnb cash on cash: -1.35%

Traditional cash on cash: 1.68%

Airbnb Rental Income: $830

Traditional Rental Income: $5775

Airbnb ROI: -1.35%

Traditional ROI: 1.68%

78746 US HWY 40 unit: 211

Winter Park, CO

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

$1,199,000

Airbnb cash on cash: -0.91%

Traditional cash on cash: 0.66%

Airbnb Rental Income: $952

Traditional Rental Income: $2345

Airbnb ROI: -0.91%

Traditional ROI: 0.66%

490 KINGS CROSSING unit: 331

Winter Park, CO

2 beds | 2 baths | 860 sq.ft.

$515,000

Airbnb cash on cash: -0.98%

Traditional cash on cash: 1.48%

Airbnb Rental Income: $572

Traditional Rental Income: $1473

Airbnb ROI: -0.98%

Traditional ROI: 1.48%

580 Winter Park Drive unit: 4564

Winter Park, CO

1 beds | 1 baths | 533 sq.ft.

$599,000

Airbnb cash on cash: -1.49%

Traditional cash on cash: 0.73%

Airbnb Rental Income: $364

Traditional Rental Income: $1358

Airbnb ROI: -1.49%