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
454 Lions Gate Dr Winter Park, CO UNDER NEW MANAGEMENT & NEW CONTRACTOR! Things are moving along for Reunion Lofts! Stunning...	3 beds \| 3 baths \| 2,240 sq.ft.	$1,525,000	Airbnb cash on cash: N/A Traditional cash on cash: 0.84% Airbnb Rental Income: $null Traditional Rental Income: $2830 Airbnb ROI: N/A Traditional ROI: 0.84%
115 LIONS GATE Winter Park, CO THE PERFECT LOCATION IN WINTER PARK! An incredible 4 bed, 4 bath home PLUS a separate cabi...	4 beds \| 3 baths \| 2,352 sq.ft.	$2,449,000	Airbnb cash on cash: -0.24% Traditional cash on cash: 0.33% Airbnb Rental Income: $2949 Traditional Rental Income: $3561 Airbnb ROI: -0.24% Traditional ROI: 0.33%
671 Vasquez Road Winter Park, CO Fully Remodeled Luxury Home in Downtown Winter Park - Walk to Shops, Dining & the Future G...	4 beds \| 5 baths \| 3,779 sq.ft.	$2,500,000	Airbnb cash on cash: -0.34% Traditional cash on cash: 0.82% Airbnb Rental Income: $2949 Traditional Rental Income: $4961 Airbnb ROI: -0.34% Traditional ROI: 0.82%
211 SAWYER CIR Winter Park, CO Priced low so you can make the improvements you want! Located right in downtown Winter Par...	3 beds \| 4 baths \| 1,488 sq.ft.	$900,000	Airbnb cash on cash: N/A Traditional cash on cash: 0.34% Airbnb Rental Income: $null Traditional Rental Income: $2413 Airbnb ROI: N/A Traditional ROI: 0.34%
701 Red Quill Way Winter Park, CO This stunning end-unit 4 bed, 5 bath townhome in the heart of downtown Winter Park offers ...	4 beds \| 5 baths \| 2,360 sq.ft.	$1,495,000	Airbnb cash on cash: -0.55% Traditional cash on cash: 0.46% Airbnb Rental Income: $2949 Traditional Rental Income: $3673 Airbnb ROI: -0.55% Traditional ROI: 0.46%
80 RAMBLE Lane Winter Park, CO Welcome to ''The Rock and Star Chalet,'' a stunning 4-bedroom, 3.5-bath retreat located in...	4 beds \| 3 baths \| 2,694 sq.ft.	$2,495,000	Airbnb cash on cash: -0.53% Traditional cash on cash: -0.06% Airbnb Rental Income: $2949 Traditional Rental Income: $3351 Airbnb ROI: -0.53% Traditional ROI: -0.06%
476 KINGS CROSSING RD Winter Park, CO Rare Find in the Heart of Winter Park! This 3-level townhome offers an unbeatable location...	3 beds \| 4 baths \| 1,572 sq.ft.	$970,000	Airbnb cash on cash: N/A Traditional cash on cash: 1.73% Airbnb Rental Income: $null Traditional Rental Income: $2890 Airbnb ROI: N/A Traditional ROI: 1.73%
78746 US Highway 40 unit: 221 #221 Winter Park, CO $40k incentive to use as Buyer wishes (2/1 Buy Down, hot tub, blinds, etc.) Enjoy listenin...	3 beds \| 2 baths \| 1,769 sq.ft.	$1,399,000	Airbnb cash on cash: N/A Traditional cash on cash: 0.05% Airbnb Rental Income: $null Traditional Rental Income: $2614 Airbnb ROI: N/A Traditional ROI: 0.05%
78746 US HWY 40 unit: 222 #222 Winter Park, CO $30k incentive to use as Buyer wishes (2/1 Buy Down, hot tub, blinds, etc.) This is is our...	2 beds \| 2 baths \| 1,227 sq.ft.	$999,000	Airbnb cash on cash: -0.84% Traditional cash on cash: 0.61% Airbnb Rental Income: $1480 Traditional Rental Income: $2389 Airbnb ROI: -0.84% Traditional ROI: 0.61%
432 Hi Country Drive unit: 15 #15 Winter Park, CO TOP FLOOR condo in the heart of downtown Winter Park. Unique gem beautifully renovated rig...	1 beds \| 1 baths \| 465 sq.ft.	$415,000	Airbnb cash on cash: N/A Traditional cash on cash: 0.23% Airbnb Rental Income: $null Traditional Rental Income: $1238 Airbnb ROI: N/A Traditional ROI: 0.23%
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.	$674,750	Airbnb cash on cash: -0.88% Traditional cash on cash: 0.48% Airbnb Rental Income: $1480 Traditional Rental Income: $1898 Airbnb ROI: -0.88% Traditional ROI: 0.48%
78746 US HWY 40 unit: 212 #212 Winter Park, CO Only 2 of this floorplan remain. This mountain modern residence is being sold furnished. F...	2 beds \| 2 baths \| 848 sq.ft.	$795,000	Airbnb cash on cash: -0.49% Traditional cash on cash: 0.67% Airbnb Rental Income: $1480 Traditional Rental Income: $1905 Airbnb ROI: -0.49% Traditional ROI: 0.67%
670 WINTER PARK Drive unit: 3424 #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.	$639,900	Airbnb cash on cash: N/A Traditional cash on cash: -0.82% Airbnb Rental Income: $null Traditional Rental Income: $1391 Airbnb ROI: N/A Traditional ROI: -0.82%
273 Hi Country Drive unit: 15 #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.	$405,000	Airbnb cash on cash: N/A Traditional cash on cash: 0.05% Airbnb Rental Income: $null Traditional Rental Income: $1138 Airbnb ROI: N/A Traditional ROI: 0.05%
472 KINGS CROSSING Road Winter Park, CO Welcome to Kings Crossing Place Townhome, nestled in the vibrant heart of downtown just mo...	4 beds \| 4 baths \| 1,572 sq.ft.	$889,900	Airbnb cash on cash: 0.63% Traditional cash on cash: 0.74% Airbnb Rental Income: $2949 Traditional Rental Income: $2364 Airbnb ROI: 0.63% Traditional ROI: 0.74%
83 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.	$2,528,241	Airbnb cash on cash: -0.22% Traditional cash on cash: 0.29% Airbnb Rental Income: $2949 Traditional Rental Income: $3485 Airbnb ROI: -0.22% Traditional ROI: 0.29%
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.	$2,722,215	Airbnb cash on cash: -0.28% Traditional cash on cash: 0.61% Airbnb Rental Income: $2949 Traditional Rental Income: $4517 Airbnb ROI: -0.28% Traditional ROI: 0.61%
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.	$2,893,346	Airbnb cash on cash: -0.32% Traditional cash on cash: 0.24% Airbnb Rental Income: $2949 Traditional Rental Income: $3785 Airbnb ROI: -0.32% Traditional ROI: 0.24%
95 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.	$2,705,000	Airbnb cash on cash: -0.28% Traditional cash on cash: 0.17% Airbnb Rental Income: $2949 Traditional Rental Income: $3387 Airbnb ROI: -0.28% Traditional ROI: 0.17%
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: N/A Traditional cash on cash: -0.11% Airbnb Rental Income: $null Traditional Rental Income: $2097 Airbnb ROI: N/A Traditional ROI: -0.11%
78746 US HWY 40 unit: 218 #218 Winter Park, CO $40k Buyer Incentive - use as you wish (2/1 buy down, hot tub, blinds, etc.) MOVE-IN READY...	3 beds \| 3 baths \| 1,506 sq.ft.	$1,230,000	Airbnb cash on cash: N/A Traditional cash on cash: 0.34% Airbnb Rental Income: $null Traditional Rental Income: $2609 Airbnb ROI: N/A Traditional ROI: 0.34%
243 VASQUEZ Road Winter Park, CO PRICE REDUCED!! Truly a one of kind Mountain Contemporary home in the heart of Winter Park...	4 beds \| 3 baths \| 2,810 sq.ft.	$2,699,900	Airbnb cash on cash: -0.33% Traditional cash on cash: 0% Airbnb Rental Income: $2949 Traditional Rental Income: $3102 Airbnb ROI: -0.33% Traditional ROI: 0%
57 Scenic Trail Winter Park, CO Discover mountain tranquility in this brand new walkout style Rendezvous home. Dual owner'...	4 beds \| 4 baths \| 3,361 sq.ft.	$2,871,576	Airbnb cash on cash: -0.79% Traditional cash on cash: -0.33% Airbnb Rental Income: $2949 Traditional Rental Income: $3491 Airbnb ROI: -0.79% Traditional ROI: -0.33%
19 Scenic Trail 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.	$2,603,559	Airbnb cash on cash: -0.72% Traditional cash on cash: -0.34% Airbnb Rental Income: $2949 Traditional Rental Income: $3179 Airbnb ROI: -0.72% Traditional ROI: -0.34%
31 Scenic Trail Winter Park, CO Newly released! Discover mountain tranquility in this brand new walkout style Rendezvous h...	4 beds \| 4 baths \| 3,361 sq.ft.	$2,969,388	Airbnb cash on cash: -0.82% Traditional cash on cash: -0.38% Airbnb Rental Income: $2949 Traditional Rental Income: $3478 Airbnb ROI: -0.82% Traditional ROI: -0.38%
45 Scenic Trail 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.	$2,595,518	Airbnb cash on cash: -0.72% Traditional cash on cash: -0.34% Airbnb Rental Income: $2949 Traditional Rental Income: $3179 Airbnb ROI: -0.72% Traditional ROI: -0.34%
5 Scenic Trail 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.	$2,755,421	Airbnb cash on cash: -0.76% Traditional cash on cash: -0.41% Airbnb Rental Income: $2949 Traditional Rental Income: $3179 Airbnb ROI: -0.76% Traditional ROI: -0.41%
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: N/A Traditional cash on cash: 0.21% Airbnb Rental Income: $null Traditional Rental Income: $2966 Airbnb ROI: N/A Traditional ROI: 0.21%
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.	$1,620,720	Airbnb cash on cash: N/A Traditional cash on cash: 0.22% Airbnb Rental Income: $null Traditional Rental Income: $2966 Airbnb ROI: N/A Traditional ROI: 0.22%
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.	$1,676,683	Airbnb cash on cash: N/A Traditional cash on cash: 0.16% Airbnb Rental Income: $null Traditional Rental Income: $2966 Airbnb ROI: N/A Traditional ROI: 0.16%
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: N/A Traditional cash on cash: 0.23% Airbnb Rental Income: $null Traditional Rental Income: $2966 Airbnb ROI: N/A Traditional ROI: 0.23%
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.	$1,640,035	Airbnb cash on cash: N/A Traditional cash on cash: 0.2% Airbnb Rental Income: $null Traditional Rental Income: $2966 Airbnb ROI: N/A Traditional ROI: 0.2%
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.	$1,571,855	Airbnb cash on cash: N/A Traditional cash on cash: 0.27% Airbnb Rental Income: $null Traditional Rental Income: $2966 Airbnb ROI: N/A Traditional ROI: 0.27%
159 Hi Country Drive unit: 14 #14 Winter Park, CO Don't miss out on this fabulous location and updated 2-bedroom, 2-bathroom. The open floor...	2 beds \| 2 baths \| 960 sq.ft.	$629,000	Airbnb cash on cash: -1% Traditional cash on cash: -0.11% Airbnb Rental Income: $1480 Traditional Rental Income: $1566 Airbnb ROI: -1% Traditional ROI: -0.11%
720 BAKER Drive unit: 409 #409 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: -1.08% Traditional cash on cash: 0.07% Airbnb Rental Income: $1480 Traditional Rental Income: $2002 Airbnb ROI: -1.08% Traditional ROI: 0.07%
720 BAKER Drive unit: 306 #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: -1.08% Traditional cash on cash: 0.07% Airbnb Rental Income: $1480 Traditional Rental Income: $2002 Airbnb ROI: -1.08% Traditional ROI: 0.07%
185 Vasquez Rd Winter Park, CO We are excited to release our final four 5BR units in the D Building! The Landing: Luxury ...	5 beds \| 4 baths \| 2,423 sq.ft.	$2,095,000	Airbnb cash on cash: 0.09% Traditional cash on cash: 0.25% Airbnb Rental Income: $4105 Traditional Rental Income: $3532 Airbnb ROI: 0.09% Traditional ROI: 0.25%
720 BAKER Drive unit: 210 #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: N/A Traditional cash on cash: 0.1% Airbnb Rental Income: $null Traditional Rental Income: $2620 Airbnb ROI: N/A Traditional ROI: 0.1%
720 BAKER Drive unit: 406 #406 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: -1.08% Traditional cash on cash: 0.15% Airbnb Rental Income: $1480 Traditional Rental Income: $2073 Airbnb ROI: -1.08% Traditional ROI: 0.15%
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: -1% Traditional cash on cash: 0.06% Airbnb Rental Income: $1480 Traditional Rental Income: $1831 Airbnb ROI: -1% Traditional ROI: 0.06%

Real Estate investment in Winter-park, CO

There are 107 properties for sale in the city of Winter Park . The median list price in Winter Park is $999,000 and the average price per square foot is $620. In September 2025, the average monthly cash on cash return in Winter Park is N/A%. The average monthly rental income in Winter Park is $2,164.

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

There are 107 investment properties available for sale in Winter-park.

In 2025, the best neighborhood to buy investment property is Winter Park.

The ROI for Short-Term is higher than the Long-Term in Winter-park with average rental income of $1,480.

Your search for investment property begins and ends here

Investment Property for Sale in Winter Park, CO

454 Lions Gate Dr

Winter Park, CO

3 beds | 3 baths | 2,240 sq.ft.

$1,525,000

Airbnb cash on cash: N/A

Traditional cash on cash: 0.84%

Airbnb Rental Income: $null

Traditional Rental Income: $2830

Airbnb ROI: N/A

Traditional ROI: 0.84%

115 LIONS GATE

Winter Park, CO

4 beds | 3 baths | 2,352 sq.ft.

$2,449,000

Airbnb cash on cash: -0.24%

Traditional cash on cash: 0.33%

Airbnb Rental Income: $2949

Traditional Rental Income: $3561

Airbnb ROI: -0.24%

Traditional ROI: 0.33%

671 Vasquez Road

Winter Park, CO

4 beds | 5 baths | 3,779 sq.ft.

$2,500,000

Airbnb cash on cash: -0.34%

Traditional cash on cash: 0.82%

Airbnb Rental Income: $2949

Traditional Rental Income: $4961

Airbnb ROI: -0.34%

Traditional ROI: 0.82%

211 SAWYER CIR

Winter Park, CO

3 beds | 4 baths | 1,488 sq.ft.

$900,000

Airbnb cash on cash: N/A

Traditional cash on cash: 0.34%

Airbnb Rental Income: $null

Traditional Rental Income: $2413

Airbnb ROI: N/A

Traditional ROI: 0.34%

701 Red Quill Way

Winter Park, CO

4 beds | 5 baths | 2,360 sq.ft.

$1,495,000

Airbnb cash on cash: -0.55%

Traditional cash on cash: 0.46%

Airbnb Rental Income: $2949

Traditional Rental Income: $3673

Airbnb ROI: -0.55%

Traditional ROI: 0.46%

80 RAMBLE Lane

Winter Park, CO

4 beds | 3 baths | 2,694 sq.ft.

$2,495,000

Airbnb cash on cash: -0.53%

Traditional cash on cash: -0.06%

Airbnb Rental Income: $2949

Traditional Rental Income: $3351

Airbnb ROI: -0.53%

Traditional ROI: -0.06%

476 KINGS CROSSING RD

Winter Park, CO

3 beds | 4 baths | 1,572 sq.ft.

$970,000

Airbnb cash on cash: N/A

Traditional cash on cash: 1.73%

Airbnb Rental Income: $null

Traditional Rental Income: $2890

Airbnb ROI: N/A

Traditional ROI: 1.73%

78746 US Highway 40 unit: 221 #221

Winter Park, CO

3 beds | 2 baths | 1,769 sq.ft.

$1,399,000

Airbnb cash on cash: N/A

Traditional cash on cash: 0.05%

Airbnb Rental Income: $null

Traditional Rental Income: $2614

Airbnb ROI: N/A