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 30 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
78311 US HWY 40 #1 Winter Park, CO Easy to Tour! This 2-Bedroom/2.5-Bath Furnished Condo has it ALL: Modern Construction with...	2 beds \| 3 baths \| 1,149 sq.ft.	$875,000	Airbnb cash on cash: 0.84% Traditional cash on cash: 0.76% Airbnb Rental Income: $3067 Traditional Rental Income: $2300 Airbnb ROI: 0.84% Traditional ROI: 0.76%
78746 US HWY 40 #213 Winter Park, CO This beautiful home will be furnished with the main furniture pieces and is MOVE-IN READY!...	2 beds \| 2 baths \| 885 sq.ft.	$813,019	Airbnb cash on cash: 1.34% Traditional cash on cash: 0.73% Airbnb Rental Income: $3067 Traditional Rental Income: $1905 Airbnb ROI: 1.34% Traditional ROI: 0.73%
78746 US HWY 40 #212 Winter Park, CO $10k credit to Buyers for new contracts that close before Jan. 30, 2025. MOVE-IN READY! On...	2 beds \| 2 baths \| 885 sq.ft.	$813,687	Airbnb cash on cash: 1.34% Traditional cash on cash: 0.73% Airbnb Rental Income: $3067 Traditional Rental Income: $1905 Airbnb ROI: 1.34% Traditional ROI: 0.73%
507 HI COUNTRY #11-12 Winter Park, CO End unit, on the river, in downtown Winter Park! What more could you ask for? This one che...	2 beds \| 1 baths \| 651 sq.ft.	$479,000	Airbnb cash on cash: 3.68% Traditional cash on cash: 2.04% Airbnb Rental Income: $3067 Traditional Rental Income: $1632 Airbnb ROI: 3.68% Traditional ROI: 2.04%
1080 Winter Park Drive #7 Winter Park, CO Rates as low as 5.625% (6.987% APR) with a 25% down payment and a mid-credit score of 780+...	1 beds \| 1 baths \| 688 sq.ft.	$535,000	Airbnb cash on cash: 1.39% Traditional cash on cash: 1.75% Airbnb Rental Income: $1935 Traditional Rental Income: $1604 Airbnb ROI: 1.39% Traditional ROI: 1.75%
670 WINTER PARK Drive #3424 Winter Park, CO Be prepared to be amazed from your first steps inside this condo in the heart of the Villa...	1 beds \| 1 baths \| 600 sq.ft.	$674,900	Airbnb cash on cash: 0.6% Traditional cash on cash: 0.55% Airbnb Rental Income: $1935 Traditional Rental Income: $1391 Airbnb ROI: 0.6% Traditional ROI: 0.55%
273 Hi Country Drive #15 Winter Park, CO Riverfront retreat in the heart of downtown WP! Enjoy this TOP FLOOR, 1 bedroom condo with...	1 beds \| 1 baths \| 459 sq.ft.	$429,000	Airbnb cash on cash: 1.99% Traditional cash on cash: 1.28% Airbnb Rental Income: $1935 Traditional Rental Income: $1138 Airbnb ROI: 1.99% Traditional ROI: 1.28%
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: -0.11% Traditional cash on cash: 0.59% Airbnb Rental Income: $1935 Traditional Rental Income: $2097 Airbnb ROI: -0.11% Traditional ROI: 0.59%
720 BAKER Drive #305 Winter Park, CO Introducing the highly anticipated Headwaters Condos, a premier new construction project i...	3 beds \| 3 baths \| 1,485 sq.ft.	$1,275,000	Airbnb cash on cash: 0.28% Traditional cash on cash: 0.65% Airbnb Rental Income: $2884 Traditional Rental Income: $2646 Airbnb ROI: 0.28% Traditional ROI: 0.65%
78746 US HWY 40 #218 Winter Park, CO $20k credit to Buyer for closing before Jan. 30, 2025. MOVE-IN READY. Only 7 residences re...	3 beds \| 3 baths \| 1,513 sq.ft.	$1,252,736	Airbnb cash on cash: 0.39% Traditional cash on cash: 0.73% Airbnb Rental Income: $2884 Traditional Rental Income: $2609 Airbnb ROI: 0.39% Traditional ROI: 0.73%
78746 US HWY 40 #215 Winter Park, CO This beautiful home will be furnished with the main furniture pieces and is MOVE-IN READY!...	3 beds \| 3 baths \| 1,479 sq.ft.	$1,251,215	Airbnb cash on cash: 0.39% Traditional cash on cash: 0.7% Airbnb Rental Income: $2884 Traditional Rental Income: $2580 Airbnb ROI: 0.39% Traditional ROI: 0.7%
145 FOREST TRAIL #16 Winter Park, CO Priced low so you have the extra cash to do the updates you want! It has been a while sin...	1 beds \| 2 baths \| 577 sq.ft.	$460,000	Airbnb cash on cash: 1.76% Traditional cash on cash: 1.61% Airbnb Rental Income: $1935 Traditional Rental Income: $1361 Airbnb ROI: 1.76% Traditional ROI: 1.61%
201 Zephyr Way #2218 Winter Park, CO Premier - Second Floor - Ski In/Out Condo. Take advantage of this limited opportunity to o...	1 beds \| 1 baths \| 557 sq.ft.	$605,000	Airbnb cash on cash: 1.02% Traditional cash on cash: 0.94% Airbnb Rental Income: $1935 Traditional Rental Income: $1381 Airbnb ROI: 1.02% Traditional ROI: 0.94%
159 Hi Country Drive #14 Winter Park, CO Don't miss out on this fabulous location and updated 2-bedroom, 2-bathroom. The open flo...	2 beds \| 2 baths \| 960 sq.ft.	$655,000	Airbnb cash on cash: 2.36% Traditional cash on cash: 1.05% Airbnb Rental Income: $3067 Traditional Rental Income: $1566 Airbnb ROI: 2.36% Traditional ROI: 1.05%
466 HI Country Drive #17-18 Winter Park, CO Top floor, end unit right in the heart of downtown Winter Park! This spacious floor plan ...	2 beds \| 2 baths \| 714 sq.ft.	$585,000	Airbnb cash on cash: 2.77% Traditional cash on cash: 1.91% Airbnb Rental Income: $3067 Traditional Rental Income: $1896 Airbnb ROI: 2.77% Traditional ROI: 1.91%
51 River Drive Winter Park, CO Heads up! Condos in this gorgeous building along the Fraser River rarely come on the mark...	2 beds \| 2 baths \| 899 sq.ft.	$675,000	Airbnb cash on cash: 2.28% Traditional cash on cash: 0.95% Airbnb Rental Income: $3067 Traditional Rental Income: $1530 Airbnb ROI: 2.28% Traditional ROI: 0.95%
720 BAKER Drive #409 Winter Park, CO Introducing the highly anticipated Headwaters Condos, a premier new construction project i...	2 beds \| 2 baths \| 958 sq.ft.	$925,000	Airbnb cash on cash: 1.13% Traditional cash on cash: 0.71% Airbnb Rental Income: $3067 Traditional Rental Income: $2002 Airbnb ROI: 1.13% Traditional ROI: 0.71%
720 BAKER Drive #306 Winter Park, CO Introducing the highly anticipated Headwaters Condos, a premier new construction project i...	2 beds \| 2 baths \| 956 sq.ft.	$895,000	Airbnb cash on cash: 1.22% Traditional cash on cash: 0.78% Airbnb Rental Income: $3067 Traditional Rental Income: $2002 Airbnb ROI: 1.22% Traditional ROI: 0.78%
32 TELEMARK Drive #101 Winter Park, CO Ideal location on the north end of Winter Park close to the new future medical facility. U...	1 beds \| 1 baths \| 507 sq.ft.	$399,900	Airbnb cash on cash: 2.2% Traditional cash on cash: 1.66% Airbnb Rental Income: $1935 Traditional Rental Income: $1221 Airbnb ROI: 2.2% Traditional ROI: 1.66%
720 BAKER Drive #210 Winter Park, CO Introducing the highly anticipated Headwaters Condos, a premier new construction project i...	3 beds \| 3 baths \| 1,483 sq.ft.	$1,200,000	Airbnb cash on cash: 0.4% Traditional cash on cash: 0.76% Airbnb Rental Income: $2884 Traditional Rental Income: $2620 Airbnb ROI: 0.4% Traditional ROI: 0.76%
59 RIVER Drive #3 Winter Park, CO Available to start enjoying today! You will be so impressed with this affordable option i...	N/A beds \| 1 baths \| 483 sq.ft.	$399,000	Airbnb cash on cash: 2.94% Traditional cash on cash: 1.51% Airbnb Rental Income: $2247 Traditional Rental Income: $1151 Airbnb ROI: 2.94% Traditional ROI: 1.51%
720 BAKER Drive #406 Winter Park, CO Introducing the highly anticipated Headwaters Condos, a premier new construction project i...	2 beds \| 2 baths \| 958 sq.ft.	$925,000	Airbnb cash on cash: 1.13% Traditional cash on cash: 0.79% Airbnb Rental Income: $3067 Traditional Rental Income: $2073 Airbnb ROI: 1.13% Traditional ROI: 0.79%
720 BAKER Drive #304 Winter Park, CO * Developer Incentive - Close by 12/31/24 to receive a $15,000 credit at closing! * In...	2 beds \| 1 baths \| 874 sq.ft.	$825,000	Airbnb cash on cash: 1.45% Traditional cash on cash: 0.75% Airbnb Rental Income: $3067 Traditional Rental Income: $1831 Airbnb ROI: 1.45% Traditional ROI: 0.75%
580 WINTER PARK #4474 Winter Park, CO This is the one you have been waiting for! A ski in/walk out condominium that has been com...	2 beds \| 2 baths \| 991 sq.ft.	$1,000,000	Airbnb cash on cash: 0.84% Traditional cash on cash: 0.58% Airbnb Rental Income: $3067 Traditional Rental Income: $2126 Airbnb ROI: 0.84% Traditional ROI: 0.58%
720 BAKER Drive #308 Winter Park, CO * Developer incentive - Close by 12/31/24 to receive a $15,000 credit at closing * In...	2 beds \| 2 baths \| 955 sq.ft.	$895,000	Airbnb cash on cash: 1.22% Traditional cash on cash: 0.87% Airbnb Rental Income: $3067 Traditional Rental Income: $2073 Airbnb ROI: 1.22% Traditional ROI: 0.87%
668 Telemark Court Winter Park, CO This rare 4-bedroom townhome combines modern comfort with natural beauty. Nestled on a pea...	4 beds \| 3 baths \| 2,028 sq.ft.	$1,299,000	Airbnb cash on cash: 1.61% Traditional cash on cash: 0.95% Airbnb Rental Income: $4626 Traditional Rental Income: $2862 Airbnb ROI: 1.61% Traditional ROI: 0.95%
580 Winter Park Drive #4340 Winter Park, CO Watch Video! Premium 2-bed/2-bath, ski-in/ski-out condo located on the front of Founders P...	2 beds \| 2 baths \| 990 sq.ft.	$1,014,000	Airbnb cash on cash: -1.51% Traditional cash on cash: -1.63% Airbnb Rental Income: $3067 Traditional Rental Income: $2255 Airbnb ROI: -1.51% Traditional ROI: -1.63%
40 GCR 702 / Village Drive Drive #1-101 Winter Park, CO Welcome to your mountain retreat at Beaver Village Condominiums in Winter Park, CO! This f...	2 beds \| 2 baths \| 850 sq.ft.	$679,000	Airbnb cash on cash: 2.35% Traditional cash on cash: 1.02% Airbnb Rental Income: $3067 Traditional Rental Income: $1523 Airbnb ROI: 2.35% Traditional ROI: 1.02%

Your search for investment property begins and ends here

Condos for Sale in Winter Park, CO

78311 US HWY 40 #1

Winter Park, CO

2 beds | 3 baths | 1,149 sq.ft.

$875,000

Airbnb cash on cash: 0.84%

Traditional cash on cash: 0.76%

Airbnb Rental Income: $3067

Traditional Rental Income: $2300

Airbnb ROI: 0.84%

Traditional ROI: 0.76%

78746 US HWY 40 #213

Winter Park, CO

2 beds | 2 baths | 885 sq.ft.

$813,019

Airbnb cash on cash: 1.34%

Traditional cash on cash: 0.73%

Airbnb Rental Income: $3067

Traditional Rental Income: $1905

Airbnb ROI: 1.34%

Traditional ROI: 0.73%

78746 US HWY 40 #212

Winter Park, CO

2 beds | 2 baths | 885 sq.ft.

$813,687

Airbnb cash on cash: 1.34%

Traditional cash on cash: 0.73%

Airbnb Rental Income: $3067

Traditional Rental Income: $1905

Airbnb ROI: 1.34%

Traditional ROI: 0.73%

507 HI COUNTRY #11-12

Winter Park, CO

2 beds | 1 baths | 651 sq.ft.

$479,000

Airbnb cash on cash: 3.68%

Traditional cash on cash: 2.04%

Airbnb Rental Income: $3067

Traditional Rental Income: $1632

Airbnb ROI: 3.68%

Traditional ROI: 2.04%

1080 Winter Park Drive #7

Winter Park, CO

1 beds | 1 baths | 688 sq.ft.

$535,000

Airbnb cash on cash: 1.39%

Traditional cash on cash: 1.75%

Airbnb Rental Income: $1935

Traditional Rental Income: $1604

Airbnb ROI: 1.39%

Traditional ROI: 1.75%

670 WINTER PARK Drive #3424

Winter Park, CO

1 beds | 1 baths | 600 sq.ft.

$674,900

Airbnb cash on cash: 0.6%

Traditional cash on cash: 0.55%

Airbnb Rental Income: $1935

Traditional Rental Income: $1391

Airbnb ROI: 0.6%

Traditional ROI: 0.55%

273 Hi Country Drive #15

Winter Park, CO

1 beds | 1 baths | 459 sq.ft.

$429,000

Airbnb cash on cash: 1.99%

Traditional cash on cash: 1.28%

Airbnb Rental Income: $1935

Traditional Rental Income: $1138

Airbnb ROI: 1.99%

Traditional ROI: 1.28%

720 BAKER Drive #404

Winter Park, CO

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

$1,025,000

Airbnb cash on cash: -0.11%

Traditional cash on cash: 0.59%

Airbnb Rental Income: $1935

Traditional Rental Income: $2097

Airbnb ROI: -0.11%