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.

Investment Property for Sale in Winter Park, CO

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PROPERTY	DETAILS	SALE PRICE	INVESTMENT PERFORMANCE
115 LIONS GATE Winter Park, CO Own a piece of Winter Park history with this 4 bed, 4 bath home in THE PERFECT LOCATION. E...	4 beds \| 3 baths \| 4,018 sq.ft.	$2,495,000	Airbnb cash on cash: -0.91% Traditional cash on cash: 0.31% Airbnb Rental Income: $1130 Traditional Rental Income: $3561 Airbnb ROI: -0.91% Traditional ROI: 0.31%
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: -1.49% Traditional cash on cash: 0.76% Airbnb Rental Income: $790 Traditional Rental Income: $2300 Airbnb ROI: -1.49% Traditional ROI: 0.76%
155 Dreamcatcher South Winter Park, CO QUARTER OWNERSHIP opportunity in a beautiful, well-appointed home that comes fully furnish...	4 beds \| 4 baths \| 2,924 sq.ft.	$450,000	Airbnb cash on cash: -1.13% Traditional cash on cash: 5.19% Airbnb Rental Income: $1130 Traditional Rental Income: $3416 Airbnb ROI: -1.13% Traditional ROI: 5.19%
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: -1.17% Traditional cash on cash: 0.73% Airbnb Rental Income: $790 Traditional Rental Income: $1905 Airbnb ROI: -1.17% Traditional ROI: 0.73%
57 Overlook Place Winter Park, CO Nestled in the heart of Winter Park, this downhill single-family mountain home embodies th...	4 beds \| 4 baths \| 2,775 sq.ft.	$2,603,452	Airbnb cash on cash: -0.82% Traditional cash on cash: 0.31% Airbnb Rental Income: $1130 Traditional Rental Income: $3485 Airbnb ROI: -0.82% Traditional ROI: 0.31%
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: -1.17% Traditional cash on cash: 0.73% Airbnb Rental Income: $790 Traditional Rental Income: $1905 Airbnb ROI: -1.17% 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: -0.56% Traditional cash on cash: 2.04% Airbnb Rental Income: $790 Traditional Rental Income: $1632 Airbnb ROI: -0.56% 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: -0.07% Traditional cash on cash: 1.75% Airbnb Rental Income: $1057 Traditional Rental Income: $1604 Airbnb ROI: -0.07% 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: -0.56% Traditional cash on cash: 0.55% Airbnb Rental Income: $1057 Traditional Rental Income: $1391 Airbnb ROI: -0.56% 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: 0.17% Traditional cash on cash: 1.28% Airbnb Rental Income: $1057 Traditional Rental Income: $1138 Airbnb ROI: 0.17% Traditional ROI: 1.28%
107 RED QUILL Way Winter Park, CO Experience mountain luxury and convenience in this meticulously crafted townhome, cherishe...	3 beds \| 4 baths \| 2,048 sq.ft.	$1,275,000	Airbnb cash on cash: -0.38% Traditional cash on cash: 1.16% Airbnb Rental Income: $1770 Traditional Rental Income: $3108 Airbnb ROI: -0.38% Traditional ROI: 1.16%
52 Overlook Place Winter Park, CO Experience elevated mountain living in this 3-bedroom, 3.5-bath single-family home nestled...	3 beds \| 4 baths \| 2,404 sq.ft.	$2,497,970	Airbnb cash on cash: -0.52% Traditional cash on cash: 0.34% Airbnb Rental Income: $1770 Traditional Rental Income: $3273 Airbnb ROI: -0.52% Traditional ROI: 0.34%
64 Overlook Place Winter Park, CO Perched in Winter Park, this uphill 4-bedroom, 4.5-bath mountain home defines modern luxur...	4 beds \| 5 baths \| 3,057 sq.ft.	$2,626,975	Airbnb cash on cash: -0.76% Traditional cash on cash: 0.78% Airbnb Rental Income: $1130 Traditional Rental Income: $4517 Airbnb ROI: -0.76% Traditional ROI: 0.78%
71 Overlook Place Winter Park, CO Discover mountain tranquility in this brand new walkout style Rendezvous home. Dual owner'...	4 beds \| 4 baths \| 3,361 sq.ft.	$2,872,839	Airbnb cash on cash: -0.78% Traditional cash on cash: 0.36% Airbnb Rental Income: $1130 Traditional Rental Income: $3785 Airbnb ROI: -0.78% Traditional ROI: 0.36%
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: -0.88% Traditional cash on cash: 0.59% Airbnb Rental Income: $1057 Traditional Rental Income: $2097 Airbnb ROI: -0.88% 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: -0.5% Traditional cash on cash: 0.65% Airbnb Rental Income: $1770 Traditional Rental Income: $2646 Airbnb ROI: -0.5% 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: -0.41% Traditional cash on cash: 0.73% Airbnb Rental Income: $1770 Traditional Rental Income: $2609 Airbnb ROI: -0.41% 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: -0.41% Traditional cash on cash: 0.7% Airbnb Rental Income: $1770 Traditional Rental Income: $2580 Airbnb ROI: -0.41% Traditional ROI: 0.7%
215 Lakota Park Drive Winter Park, CO New Construction Now Available in Lakota!Imagine watching Alpenglow on the purple mountain...	5 beds \| 5 baths \| 3,287 sq.ft.	$2,934,947	Airbnb cash on cash: N/A Traditional cash on cash: 0.55% Airbnb Rental Income: $null Traditional Rental Income: $4689 Airbnb ROI: N/A Traditional ROI: 0.55%
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: 0.06% Traditional cash on cash: 1.61% Airbnb Rental Income: $1057 Traditional Rental Income: $1361 Airbnb ROI: 0.06% Traditional ROI: 1.61%
314 Northwoods Place Winter Park, CO New Construction in Lakota.Top of World Views with Mountain Contemporary Finishes. Locate...	4 beds \| 5 baths \| 2,983 sq.ft.	$2,859,722	Airbnb cash on cash: -0.91% Traditional cash on cash: 0.44% Airbnb Rental Income: $1130 Traditional Rental Income: $4335 Airbnb ROI: -0.91% Traditional ROI: 0.44%
312 Northwoods Place Winter Park, CO New Construction in Lakota.Top of World Views with Mountain Contemporary Finishes. Locate...	5 beds \| 6 baths \| 3,170 sq.ft.	$2,940,734	Airbnb cash on cash: N/A Traditional cash on cash: 0.89% Airbnb Rental Income: $null Traditional Rental Income: $5661 Airbnb ROI: N/A Traditional ROI: 0.89%
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: -0.28% Traditional cash on cash: 0.94% Airbnb Rental Income: $1057 Traditional Rental Income: $1381 Airbnb ROI: -0.28% Traditional ROI: 0.94%
61 Promontory Point Winter Park, CO Introducing the newest townhome design in Rendezvous! This 3-bedroom, 3.5-bath paired home...	3 beds \| 4 baths \| 1,761 sq.ft.	$1,626,492	Airbnb cash on cash: -0.72% Traditional cash on cash: 0.4% Airbnb Rental Income: $1770 Traditional Rental Income: $2966 Airbnb ROI: -0.72% Traditional ROI: 0.4%
37 Promontory Point Winter Park, CO Introducing the newest townhome design in Rendezvous! This 3-bedroom, 3.5-bath paired home...	3 beds \| 4 baths \| 1,761 sq.ft.	$1,595,720	Airbnb cash on cash: -0.7% Traditional cash on cash: 0.43% Airbnb Rental Income: $1770 Traditional Rental Income: $2966 Airbnb ROI: -0.7% Traditional ROI: 0.43%
25 Promontory Point Winter Park, CO Introducing the newest townhome design in Rendezvous! This 3-bedroom, 3.5-bath paired home...	3 beds \| 4 baths \| 1,761 sq.ft.	$1,628,632	Airbnb cash on cash: -0.72% Traditional cash on cash: 0.39% Airbnb Rental Income: $1770 Traditional Rental Income: $2966 Airbnb ROI: -0.72% Traditional ROI: 0.39%
55 Promontory Point Winter Park, CO Introducing the newest townhome design in Rendezvous! This 3-bedroom, 3.5-bath paired home...	3 beds \| 4 baths \| 1,761 sq.ft.	$1,605,915	Airbnb cash on cash: -0.71% Traditional cash on cash: 0.42% Airbnb Rental Income: $1770 Traditional Rental Income: $2966 Airbnb ROI: -0.71% Traditional ROI: 0.42%
43 Promontory Point Winter Park, CO Introducing the newest townhome design in Rendezvous! This 3-bedroom, 3.5-bath paired home...	3 beds \| 4 baths \| 1,761 sq.ft.	$1,615,035	Airbnb cash on cash: -0.71% Traditional cash on cash: 0.41% Airbnb Rental Income: $1770 Traditional Rental Income: $2966 Airbnb ROI: -0.71% Traditional ROI: 0.41%
19 Promontory Point Winter Park, CO Introducing the newest townhome design in Rendezvous! This 3-bedroom, 3.5-bath paired home...	3 beds \| 4 baths \| 1,761 sq.ft.	$1,546,855	Airbnb cash on cash: -0.68% Traditional cash on cash: 0.49% Airbnb Rental Income: $1770 Traditional Rental Income: $2966 Airbnb ROI: -0.68% Traditional ROI: 0.49%
65 LAKE TRAIL Court Winter Park, CO Exceptional duplex that lives like a ''home'' in the heart of Winter Park. This beautiful...	3 beds \| 4 baths \| 2,900 sq.ft.	$1,899,000	Airbnb cash on cash: -0.66% Traditional cash on cash: 0.42% Airbnb Rental Income: $1770 Traditional Rental Income: $3195 Airbnb ROI: -0.66% Traditional ROI: 0.42%
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: -0.75% Traditional cash on cash: 1.05% Airbnb Rental Income: $790 Traditional Rental Income: $1566 Airbnb ROI: -0.75% 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: -0.7% Traditional cash on cash: 1.91% Airbnb Rental Income: $790 Traditional Rental Income: $1896 Airbnb ROI: -0.7% 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: -0.74% Traditional cash on cash: 0.95% Airbnb Rental Income: $790 Traditional Rental Income: $1530 Airbnb ROI: -0.74% Traditional ROI: 0.95%
101 ANTLER Way Winter Park, CO Cozy up to this charming 5 bedroom, 4 bath Duplex in sought after Lakota, one of Winter Pa...	5 beds \| 4 baths \| 2,540 sq.ft.	$1,649,000	Airbnb cash on cash: N/A Traditional cash on cash: 0.73% Airbnb Rental Income: $null Traditional Rental Income: $3360 Airbnb ROI: N/A Traditional ROI: 0.73%
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: -1.07% Traditional cash on cash: 0.71% Airbnb Rental Income: $790 Traditional Rental Income: $2002 Airbnb ROI: -1.07% 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: -1.05% Traditional cash on cash: 0.78% Airbnb Rental Income: $790 Traditional Rental Income: $2002 Airbnb ROI: -1.05% 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: 0.25% Traditional cash on cash: 1.66% Airbnb Rental Income: $1057 Traditional Rental Income: $1221 Airbnb ROI: 0.25% Traditional ROI: 1.66%
185 Vasquez #3 Winter Park, CO This is the final unit still available in the "A Building"!!! The Landing: Luxury Townhome...	5 beds \| 4 baths \| 2,417 sq.ft.	$1,950,000	Airbnb cash on cash: N/A Traditional cash on cash: 0.37% Airbnb Rental Income: $null Traditional Rental Income: $3532 Airbnb ROI: N/A Traditional ROI: 0.37%
135 Whistlestop Circle Winter Park, CO Introducing Whistlestop Townhomes Phase 2!! Custom finishes throughout, exquisitely furnis...	4 beds \| 6 baths \| 2,905 sq.ft.	$2,185,000	Airbnb cash on cash: -1.18% Traditional cash on cash: 1.17% Airbnb Rental Income: $1130 Traditional Rental Income: $5519 Airbnb ROI: -1.18% Traditional ROI: 1.17%

Real Estate investment in Winter-park, CO

There are 49 properties for sale in the city of Winter Park . The median list price in Winter Park is $1,200,000 and the average price per square foot is $742. In December 2024, the average monthly cash on cash return in Winter Park is 1.00%. The average monthly rental income in Winter Park is $2,580.

Winter-park, CO Real Estate Investing: FAQs for Buyers, Sellers and Investors

There are 49 investment properties available for sale in Winter-park.

In 2024, the best neighborhood to buy investment property is Winter Park.

The ROI for Long-Term is higher than the Short-Term in Winter-park with average rental income of $2,580.

Your search for investment property begins and ends here

Investment Property for Sale in Winter Park, CO

115 LIONS GATE

Winter Park, CO

4 beds | 3 baths | 4,018 sq.ft.

$2,495,000

Airbnb cash on cash: -0.91%

Traditional cash on cash: 0.31%

Airbnb Rental Income: $1130

Traditional Rental Income: $3561

Airbnb ROI: -0.91%

Traditional ROI: 0.31%

78311 US HWY 40 #1

Winter Park, CO

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

$875,000

Airbnb cash on cash: -1.49%

Traditional cash on cash: 0.76%

Airbnb Rental Income: $790

Traditional Rental Income: $2300

Airbnb ROI: -1.49%

Traditional ROI: 0.76%

155 Dreamcatcher South

Winter Park, CO

4 beds | 4 baths | 2,924 sq.ft.

$450,000

Airbnb cash on cash: -1.13%

Traditional cash on cash: 5.19%

Airbnb Rental Income: $1130

Traditional Rental Income: $3416

Airbnb ROI: -1.13%

Traditional ROI: 5.19%

78746 US HWY 40 #213

Winter Park, CO

2 beds | 2 baths | 885 sq.ft.

$813,019

Airbnb cash on cash: -1.17%

Traditional cash on cash: 0.73%

Airbnb Rental Income: $790

Traditional Rental Income: $1905

Airbnb ROI: -1.17%

Traditional ROI: 0.73%

57 Overlook Place

Winter Park, CO

4 beds | 4 baths | 2,775 sq.ft.

$2,603,452

Airbnb cash on cash: -0.82%

Traditional cash on cash: 0.31%

Airbnb Rental Income: $1130

Traditional Rental Income: $3485

Airbnb ROI: -0.82%

Traditional ROI: 0.31%

78746 US HWY 40 #212

Winter Park, CO

2 beds | 2 baths | 885 sq.ft.

$813,687

Airbnb cash on cash: -1.17%

Traditional cash on cash: 0.73%

Airbnb Rental Income: $790

Traditional Rental Income: $1905

Airbnb ROI: -1.17%

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: -0.56%

Traditional cash on cash: 2.04%

Airbnb Rental Income: $790

Traditional Rental Income: $1632

Airbnb ROI: -0.56%

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: -0.07%

Traditional cash on cash: 1.75%

Airbnb Rental Income: $1057

Traditional Rental Income: $1604

Airbnb ROI: -0.07%