Real Estate Investment Properties for Sale in Wintergreen Resort, VA

Looking for investment property in Wintergreen Resort, VA with high ROI ?

Explore a variety of short-term homes & houses in Wintergreen Resort, VA. Invest wisely with VRBO & Wintergreen Resort, VA 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 Wintergreen Resort, VA

separator

PROPERTY	DETAILS	SALE PRICE	INVESTMENT PERFORMANCE
24 TRILLIUM CLOSE WINTERGREEN RESORT, VA This beautifully updated and spacious 4BR, triâlevel, Townhome is just steps from the Wi...	4 beds \| 4 baths \| 2,263 sq.ft.	$375,000	Airbnb cash on cash: -1.65% Traditional cash on cash: 5.15% Airbnb Rental Income: $923 Traditional Rental Income: $2973 Airbnb ROI: -1.65% Traditional ROI: 5.15%
1717 HIGH RIDGE CONDOS WINTERGREEN RESORT, VA Enjoy yourself at this 2 bed, 2 bath condo with gorgeous views in Wintergreen! This home p...	2 beds \| 2 baths \| 1,237 sq.ft.	$430,000	Airbnb cash on cash: -2.7% Traditional cash on cash: 1.16% Airbnb Rental Income: $438 Traditional Rental Income: $1730 Airbnb ROI: -2.7% Traditional ROI: 1.16%
12 POWDERHORN LN WINTERGREEN RESORT, VA OPEN HOUSE Saturday 5/9 2:00-4:00 Best Value at Wintergreen! This Lovely corner lot home w...	4 beds \| 3 baths \| 2,200 sq.ft.	$569,500	Airbnb cash on cash: -0.96% Traditional cash on cash: 3.37% Airbnb Rental Income: $923 Traditional Rental Income: $2883 Airbnb ROI: -0.96% Traditional ROI: 3.37%
490 THREE RIDGES CONDOS WINTERGREEN RESORT, VA Nestled in the picturesque Wintergreen Ski Resort, this charming one-bedroom condo offers ...	1 beds \| 1 baths \| 648 sq.ft.	$170,000	Airbnb cash on cash: -3.09% Traditional cash on cash: 3.25% Airbnb Rental Income: $431 Traditional Rental Income: $1197 Airbnb ROI: -3.09% Traditional ROI: 3.25%
216 TIMBERS CONDOS WINTERGREEN RESORT, VA Located just steps away to the slopes and the cozy Mountain Inn, 216 Timbers is an attract...	1 beds \| 1 baths \| 405 sq.ft.	$139,900	Airbnb cash on cash: -3.29% Traditional cash on cash: 4.27% Airbnb Rental Income: $431 Traditional Rental Income: $1184 Airbnb ROI: -3.29% Traditional ROI: 4.27%
2209 TANNERS RIDGE CONDOS WINTERGREEN RESORT, VA If you're looking for a sweet spot overlooking the golf course, this top floor Tanners Rid...	2 beds \| 2 baths \| 852 sq.ft.	$235,000	Airbnb cash on cash: -3.03% Traditional cash on cash: 3.21% Airbnb Rental Income: $438 Traditional Rental Income: $1563 Airbnb ROI: -3.03% Traditional ROI: 3.21%
67 S FOREST DR WINTERGREEN RESORT, VA Nestled high near the top of Wintergreen Resort, this unique Wintergreen property that off...	4 beds \| 4 baths \| 2,336 sq.ft.	$639,000	Airbnb cash on cash: -0.62% Traditional cash on cash: 3.23% Airbnb Rental Income: $923 Traditional Rental Income: $2878 Airbnb ROI: -0.62% Traditional ROI: 3.23%
27 VEERY LN WINTERGREEN RESORT, VA OPEN HOUSE Saturday 3/28 12-2:00 Located on the golf course at Wintergreen Resort, this...	4 beds \| 3 baths \| 2,098 sq.ft.	$599,000	Airbnb cash on cash: -0.98% Traditional cash on cash: 2.77% Airbnb Rental Income: $923 Traditional Rental Income: $2677 Airbnb ROI: -0.98% Traditional ROI: 2.77%
775 LAURELWOOD CONDOS #775 WINTERGREEN RESORT, VA Back on market due to buyers failing to gain financing. This updated condo is located in t...	2 beds \| 2 baths \| 972 sq.ft.	$252,000	Airbnb cash on cash: -3.61% Traditional cash on cash: 2.52% Airbnb Rental Income: $438 Traditional Rental Income: $1635 Airbnb ROI: -3.61% Traditional ROI: 2.52%
2247 TANNERS RIDGE WINTERGREEN RESORT, VA You will not be disappointed with this Stunning, Updated Condo! Easy access via long fla...	2 beds \| 2 baths \| N/A	$228,000	Airbnb cash on cash: -3.06% Traditional cash on cash: 3.15% Airbnb Rental Income: $438 Traditional Rental Income: $1515 Airbnb ROI: -3.06% Traditional ROI: 3.15%
44 EAST CATOCTIN DR WINTERGREEN RESORT, VA Located on the 13th hole of Devils Knob Golf Course, 44 E Catoctin Drive is a standout amo...	4 beds \| 4 baths \| 2,045 sq.ft.	$685,000	Airbnb cash on cash: -0.74% Traditional cash on cash: 2.82% Airbnb Rental Income: $923 Traditional Rental Income: $2856 Airbnb ROI: -0.74% Traditional ROI: 2.82%
952 BLUE RIDGE DR WINTERGREEN RESORT, VA This charming mountain house has been a successful rental and family vacation spot for the...	5 beds \| 4 baths \| 2,537 sq.ft.	$649,000	Airbnb cash on cash: -0.04% Traditional cash on cash: 3.05% Airbnb Rental Income: $1677 Traditional Rental Income: $3085 Airbnb ROI: -0.04% Traditional ROI: 3.05%
247 TIMBERS CONDOS WINTERGREEN RESORT, VA Experience the ultimate mountain lifestyle in this premier ski-front studio at Wintergreen...	1 beds \| 1 baths \| 405 sq.ft.	$159,000	Airbnb cash on cash: -3.21% Traditional cash on cash: 3.02% Airbnb Rental Income: $431 Traditional Rental Income: $1116 Airbnb ROI: -3.21% Traditional ROI: 3.02%
30 GUMTREE DR WINTERGREEN RESORT, VA Original owners, never a rental, has been a primary residence for 40 years. Beautiful, ove...	4 beds \| 4 baths \| 3,632 sq.ft.	$649,000	Airbnb cash on cash: -1.17% Traditional cash on cash: 4.09% Airbnb Rental Income: $923 Traditional Rental Income: $3766 Airbnb ROI: -1.17% Traditional ROI: 4.09%

Real Estate investment in Wintergreen-resort, VA

There are 14 properties for sale in the city of Wintergreen Resort . The median list price in Wintergreen Resort is $402,500 and the average price per square foot is $242. In May 2026, the average monthly cash on cash return in Wintergreen Resort is 3.00%. The average monthly rental income in Wintergreen Resort is $1,730.

Wintergreen-resort, VA Real Estate Investing: FAQs for Buyers, Sellers and Investors

There are 14 investment properties available for sale in Wintergreen-resort.

In 2026, the best neighborhood to buy investment property is WINTERGREEN RESORT.

The ROI for Long-Term is higher than the Short-Term in Wintergreen-resort with average rental income of $1,730.

Your search for investment property begins and ends here

Investment Property for Sale in Wintergreen Resort, VA

24 TRILLIUM CLOSE

WINTERGREEN RESORT, VA

4 beds | 4 baths | 2,263 sq.ft.

$375,000

Airbnb cash on cash: -1.65%

Traditional cash on cash: 5.15%

Airbnb Rental Income: $923

Traditional Rental Income: $2973

Airbnb ROI: -1.65%

Traditional ROI: 5.15%

1717 HIGH RIDGE CONDOS

WINTERGREEN RESORT, VA

2 beds | 2 baths | 1,237 sq.ft.

$430,000

Airbnb cash on cash: -2.7%

Traditional cash on cash: 1.16%

Airbnb Rental Income: $438

Traditional Rental Income: $1730

Airbnb ROI: -2.7%

Traditional ROI: 1.16%

12 POWDERHORN LN

WINTERGREEN RESORT, VA

4 beds | 3 baths | 2,200 sq.ft.

$569,500

Airbnb cash on cash: -0.96%

Traditional cash on cash: 3.37%

Airbnb Rental Income: $923

Traditional Rental Income: $2883

Airbnb ROI: -0.96%

Traditional ROI: 3.37%

490 THREE RIDGES CONDOS

WINTERGREEN RESORT, VA

1 beds | 1 baths | 648 sq.ft.

$170,000

Airbnb cash on cash: -3.09%

Traditional cash on cash: 3.25%

Airbnb Rental Income: $431

Traditional Rental Income: $1197

Airbnb ROI: -3.09%

Traditional ROI: 3.25%

216 TIMBERS CONDOS

WINTERGREEN RESORT, VA

1 beds | 1 baths | 405 sq.ft.

$139,900

Airbnb cash on cash: -3.29%

Traditional cash on cash: 4.27%

Airbnb Rental Income: $431

Traditional Rental Income: $1184

Airbnb ROI: -3.29%

Traditional ROI: 4.27%

2209 TANNERS RIDGE CONDOS

WINTERGREEN RESORT, VA

2 beds | 2 baths | 852 sq.ft.

$235,000

Airbnb cash on cash: -3.03%

Traditional cash on cash: 3.21%

Airbnb Rental Income: $438

Traditional Rental Income: $1563

Airbnb ROI: -3.03%

Traditional ROI: 3.21%

67 S FOREST DR

WINTERGREEN RESORT, VA

4 beds | 4 baths | 2,336 sq.ft.

$639,000

Airbnb cash on cash: -0.62%

Traditional cash on cash: 3.23%

Airbnb Rental Income: $923

Traditional Rental Income: $2878

Airbnb ROI: -0.62%

Traditional ROI: 3.23%

27 VEERY LN

WINTERGREEN RESORT, VA

4 beds | 3 baths | 2,098 sq.ft.

$599,000

Airbnb cash on cash: -0.98%

Traditional cash on cash: 2.77%

Airbnb Rental Income: $923

Traditional Rental Income: $2677

Airbnb ROI: -0.98%