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.

Townhouses for Sale in Winter Park, CO

Search for Townhouse for Sale in Winter Park, Colorado. Browse all of Mashvisor’s Townhouse listings and other investment property types including Single Family Homes, Multi Family Homes, Condos, Townhouses and Other Homes.

Showing 38 Townhouse listings of over 500,000 total investment properties for sale. Visit Mashvisor.com to all investment properties.

separator

PROPERTY	DETAILS	SALE PRICE	INVESTMENT PERFORMANCE
454 Lions Gate Dr Winter Park, CO Certificate of occupancy expected this Spring 2026! Things are moving along for Reunion Lo...	3 beds \| 3 baths \| 2,240 sq.ft.	$1,525,000	Airbnb cash on cash: -0.43% Traditional cash on cash: 0.7% Airbnb Rental Income: $1699 Traditional Rental Income: $2830 Airbnb ROI: -0.43% Traditional ROI: 0.7%
442 Lions Gate Dr Winter Park, CO Things are moving along for Reunion Lofts! We are expecting to get the certificate of occu...	3 beds \| 3 baths \| 2,240 sq.ft.	$1,650,000	Airbnb cash on cash: -0.47% Traditional cash on cash: 0.52% Airbnb Rental Income: $1699 Traditional Rental Income: $2743 Airbnb ROI: -0.47% Traditional ROI: 0.52%
120 Whistlestop Circle unit: B1 Winter Park, CO Rare 5-Bedroom Luxury Townhome in the Heart of Downtown Winter Park! Opportunities like th...	5 beds \| 5 baths \| 3,002 sq.ft.	$2,350,000	Airbnb cash on cash: 0.35% Traditional cash on cash: 1.02% Airbnb Rental Income: $3915 Traditional Rental Income: $4524 Airbnb ROI: 0.35% Traditional ROI: 1.02%
185 Vasquez Road unit: B3 Winter Park, CO	4 beds \| 3 baths \| 2,312 sq.ft.	$1,975,000	Airbnb cash on cash: -0.28% Traditional cash on cash: 0.31% Airbnb Rental Income: $2565 Traditional Rental Income: $3026 Airbnb ROI: -0.28% Traditional ROI: 0.31%
88 Wheeler Road Winter Park, CO Welcome to Sojourn at Idlewild, showcasing our beautifully finished Graysill townhomes! En...	3 beds \| 4 baths \| 1,716 sq.ft.	$1,219,000	Airbnb cash on cash: -0.06% Traditional cash on cash: 1.25% Airbnb Rental Income: $1699 Traditional Rental Income: $2702 Airbnb ROI: -0.06% Traditional ROI: 1.25%
78 Wheeler Road Winter Park, CO Welcome to Sojourn at Idlewild, showcasing our beautifully finished Graysill model townhom...	3 beds \| 4 baths \| 1,716 sq.ft.	$1,350,000	Airbnb cash on cash: -0.6% Traditional cash on cash: 0.28% Airbnb Rental Income: $1699 Traditional Rental Income: $2332 Airbnb ROI: -0.6% Traditional ROI: 0.28%
105 Wheeler Road Winter Park, CO Welcome to Sojourn at Idlewild, now showcasing our beautifully finished Coalmont floor pla...	3 beds \| 3 baths \| 1,870 sq.ft.	$1,450,000	Airbnb cash on cash: -0.22% Traditional cash on cash: 1.01% Airbnb Rental Income: $1699 Traditional Rental Income: $2888 Airbnb ROI: -0.22% Traditional ROI: 1.01%
250 LIONS GATE Drive Winter Park, CO Step into elevated mountain living where refined design meets an exceptional Winter Park l...	3 beds \| 3 baths \| 1,436 sq.ft.	$1,199,000	Airbnb cash on cash: -0.34% Traditional cash on cash: 0.42% Airbnb Rental Income: $1699 Traditional Rental Income: $2077 Airbnb ROI: -0.34% Traditional ROI: 0.42%
380 Lake Trail Winter Park, CO Close-Out Opportunity - Final Lake Trail Townhome Available! This is your last chance to o...	3 beds \| 3 baths \| 1,306 sq.ft.	$1,050,000	Airbnb cash on cash: 0.06% Traditional cash on cash: 1.02% Airbnb Rental Income: $1699 Traditional Rental Income: $2165 Airbnb ROI: 0.06% Traditional ROI: 1.02%
62 Wheeler Road Winter Park, CO Welcome to Sojourn at Idlewild, showcasing our beautifully finished Graysill townhomes! En...	3 beds \| 4 baths \| 1,716 sq.ft.	$1,199,000	Airbnb cash on cash: -0.06% Traditional cash on cash: 0.78% Airbnb Rental Income: $1699 Traditional Rental Income: $2165 Airbnb ROI: -0.06% Traditional ROI: 0.78%
119 Wheeler Road Winter Park, CO Center of Winter Park with 1 bed apartment in Sojourn, designed for true mountain-town liv...	4 beds \| 3 baths \| 2,223 sq.ft.	$1,675,000	Airbnb cash on cash: 0.13% Traditional cash on cash: 0.84% Airbnb Rental Income: $2565 Traditional Rental Income: $3064 Airbnb ROI: 0.13% Traditional ROI: 0.84%
509 Red Quill Way Winter Park, CO Spacious 4BR townhome conveniently located in Downtown Winter Park within walking distance...	4 beds \| 5 baths \| 2,360 sq.ft.	$1,395,000	Airbnb cash on cash: -0.3% Traditional cash on cash: 0.85% Airbnb Rental Income: $2565 Traditional Rental Income: $3437 Airbnb ROI: -0.3% Traditional ROI: 0.85%
190 Dreamcatcher S Winter Park, CO Welcome to 190 Dreamcatcher S, a classic mountain home in the prestigious Lakota neighborh...	5 beds \| 5 baths \| 3,567 sq.ft.	$2,799,000	Airbnb cash on cash: -0.15% Traditional cash on cash: 0.55% Airbnb Rental Income: $3915 Traditional Rental Income: $4887 Airbnb ROI: -0.15% Traditional ROI: 0.55%
30 Wheeler Road Winter Park, CO Welcome to Sojourn at Idlewild, showcasing our beautifully furnished Graysill townhome! Bu...	3 beds \| 4 baths \| 1,716 sq.ft.	$1,235,000	Airbnb cash on cash: -0.09% Traditional cash on cash: 1.19% Airbnb Rental Income: $1699 Traditional Rental Income: $2702 Airbnb ROI: -0.09% Traditional ROI: 1.19%
151 TELEMARK #15 Winter Park, CO Prime Downtown Winter Park Location! Just a few blocks from Main Street, this beautifully ...	2 beds \| 3 baths \| 1,338 sq.ft.	$810,000	Airbnb cash on cash: -0.16% Traditional cash on cash: 1.16% Airbnb Rental Income: $1363 Traditional Rental Income: $1941 Airbnb ROI: -0.16% Traditional ROI: 1.16%
185 Vasquez unit: B3 Winter Park, CO FINAL UNIT IS ON THE MARKET! The Landing: Luxury Townhomes across the street from Winter P...	4 beds \| 3 baths \| 2,329 sq.ft.	$1,975,000	Airbnb cash on cash: -0.49% Traditional cash on cash: 0.1% Airbnb Rental Income: $2565 Traditional Rental Income: $3031 Airbnb ROI: -0.49% Traditional ROI: 0.1%
374 Lake Trail Winter Park, CO Experience mountain living at its finest in this stylish and serene Mountain Modern townho...	3 beds \| 3 baths \| 1,306 sq.ft.	$1,099,000	Airbnb cash on cash: 0.01% Traditional cash on cash: 0.92% Airbnb Rental Income: $1699 Traditional Rental Income: $2158 Airbnb ROI: 0.01% Traditional ROI: 0.92%
185 Vasquez Road unit: C2 Winter Park, CO	4 beds \| 3 baths \| 2,272 sq.ft.	$1,875,000	Airbnb cash on cash: -0.02% Traditional cash on cash: 0.6% Airbnb Rental Income: $2565 Traditional Rental Income: $3026 Airbnb ROI: -0.02% Traditional ROI: 0.6%
185 Vasquez Road unit: C3 Winter Park, CO	4 beds \| 3 baths \| 2,272 sq.ft.	$1,875,000	Airbnb cash on cash: -0.24% Traditional cash on cash: 0.38% Airbnb Rental Income: $2565 Traditional Rental Income: $3026 Airbnb ROI: -0.24% Traditional ROI: 0.38%
185 Vasquez Lane unit: D4 Winter Park, CO	5 beds \| 4 baths \| 2,459 sq.ft.	$2,220,000	Airbnb cash on cash: 0.19% Traditional cash on cash: 0.19% Airbnb Rental Income: $3915 Traditional Rental Income: $3075 Airbnb ROI: 0.19% Traditional ROI: 0.19%
185 Vasquez Lane unit: D3 Winter Park, CO	5 beds \| 4 baths \| 2,422 sq.ft.	$2,150,000	Airbnb cash on cash: 0.23% Traditional cash on cash: 0.23% Airbnb Rental Income: $3915 Traditional Rental Income: $3072 Airbnb ROI: 0.23% Traditional ROI: 0.23%
101 Wheeler Road Winter Park, CO Nestled in the beauty of Winter Park, Sojourn at Idlewild is the area's newest neighborhoo...	4 beds \| 3 baths \| 2,223 sq.ft.	$1,675,000	Airbnb cash on cash: -0.31% Traditional cash on cash: 0.43% Airbnb Rental Income: $2565 Traditional Rental Income: $3112 Airbnb ROI: -0.31% Traditional ROI: 0.43%
160 Dreamcatcher S Winter Park, CO Situated in the Lakota neighborhood, directly across from Winter Park Ski Resort, this stu...	5 beds \| 5 baths \| 3,778 sq.ft.	$2,890,000	Airbnb cash on cash: -0.17% Traditional cash on cash: -0.03% Airbnb Rental Income: $3915 Traditional Rental Income: $3471 Airbnb ROI: -0.17% Traditional ROI: -0.03%
185 Vasquez Lane unit: D1 Winter Park, CO The Landing: Luxury Townhomes near Winter Park's planned gondola. Steps across the street ...	5 beds \| 4 baths \| 2,460 sq.ft.	$2,220,000	Airbnb cash on cash: 0.25% Traditional cash on cash: 0.25% Airbnb Rental Income: $3915 Traditional Rental Income: $3075 Airbnb ROI: 0.25% Traditional ROI: 0.25%
185 Vasquez Lane unit: D2 Winter Park, CO ONLY ONE LEFT! The Landing: Luxury Townhomes across the street from Winter Park's planned ...	5 beds \| 4 baths \| 2,423 sq.ft.	$2,250,000	Airbnb cash on cash: 0.23% Traditional cash on cash: 0.23% Airbnb Rental Income: $3915 Traditional Rental Income: $3072 Airbnb ROI: 0.23% Traditional ROI: 0.23%
470 Kings Crossing Rd Winter Park, CO This end-unit townhome in Kings Crossing Place offers an exceptional opportunity to own a ...	3 beds \| 3 baths \| 1,572 sq.ft.	$893,500	Airbnb cash on cash: 0% Traditional cash on cash: 1.34% Airbnb Rental Income: $1699 Traditional Rental Income: $2341 Airbnb ROI: 0% Traditional ROI: 1.34%
406 ANTLER Way Winter Park, CO Coming Soon in Lakota, pictures will be taken on 3/31! This highly sought-after quarter sh...	3 beds \| 3 baths \| 1,774 sq.ft.	$340,000	Airbnb cash on cash: -1.02% Traditional cash on cash: 3.7% Airbnb Rental Income: $1699 Traditional Rental Income: $2737 Airbnb ROI: -1.02% Traditional ROI: 3.7%
203 Sawyer Circle Winter Park, CO Located just moments from Hideaway Park in downtown Winter Park, this 3-bedroom, 3.5-bath ...	3 beds \| 4 baths \| 1,488 sq.ft.	$1,035,000	Airbnb cash on cash: -0.21% Traditional cash on cash: 1.03% Airbnb Rental Income: $1699 Traditional Rental Income: $2424 Airbnb ROI: -0.21% Traditional ROI: 1.03%

Your search for investment property begins and ends here

Townhouses 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: -0.43%

Traditional cash on cash: 0.7%

Airbnb Rental Income: $1699

Traditional Rental Income: $2830

Airbnb ROI: -0.43%

Traditional ROI: 0.7%

442 Lions Gate Dr

Winter Park, CO

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

$1,650,000

Airbnb cash on cash: -0.47%

Traditional cash on cash: 0.52%

Airbnb Rental Income: $1699

Traditional Rental Income: $2743

Airbnb ROI: -0.47%

Traditional ROI: 0.52%

120 Whistlestop Circle unit: B1

Winter Park, CO

5 beds | 5 baths | 3,002 sq.ft.

$2,350,000

Airbnb cash on cash: 0.35%

Traditional cash on cash: 1.02%

Airbnb Rental Income: $3915

Traditional Rental Income: $4524

Airbnb ROI: 0.35%

Traditional ROI: 1.02%

185 Vasquez Road unit: B3

Winter Park, CO

4 beds | 3 baths | 2,312 sq.ft.

$1,975,000

Airbnb cash on cash: -0.28%

Traditional cash on cash: 0.31%

Airbnb Rental Income: $2565

Traditional Rental Income: $3026

Airbnb ROI: -0.28%

Traditional ROI: 0.31%

88 Wheeler Road

Winter Park, CO

3 beds | 4 baths | 1,716 sq.ft.

$1,219,000

Airbnb cash on cash: -0.06%

Traditional cash on cash: 1.25%

Airbnb Rental Income: $1699

Traditional Rental Income: $2702

Airbnb ROI: -0.06%

Traditional ROI: 1.25%

78 Wheeler Road

Winter Park, CO

3 beds | 4 baths | 1,716 sq.ft.

$1,350,000

Airbnb cash on cash: -0.6%

Traditional cash on cash: 0.28%

Airbnb Rental Income: $1699

Traditional Rental Income: $2332

Airbnb ROI: -0.6%

Traditional ROI: 0.28%

105 Wheeler Road

Winter Park, CO

3 beds | 3 baths | 1,870 sq.ft.

$1,450,000

Airbnb cash on cash: -0.22%

Traditional cash on cash: 1.01%

Airbnb Rental Income: $1699

Traditional Rental Income: $2888

Airbnb ROI: -0.22%

Traditional ROI: 1.01%

250 LIONS GATE Drive

Winter Park, CO

3 beds | 3 baths | 1,436 sq.ft.

$1,199,000

Airbnb cash on cash: -0.34%

Traditional cash on cash: 0.42%

Airbnb Rental Income: $1699

Traditional Rental Income: $2077

Airbnb ROI: -0.34%