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

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PROPERTY	DETAILS	SALE PRICE	INVESTMENT PERFORMANCE
24 TRILLIUM CLOSE WINTERGREEN RESORT, VA This beautifully updated and spacious 4BR, tri-level, Townhome is just steps from the Wint...	4 beds \| 4 baths \| 2,263 sq.ft.	$349,000	Airbnb cash on cash: 0.65% Traditional cash on cash: 5.61% Airbnb Rental Income: $1846 Traditional Rental Income: $2973 Airbnb ROI: 0.65% Traditional ROI: 5.61%
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: -2.22% Traditional cash on cash: 1.16% Airbnb Rental Income: $669 Traditional Rental Income: $1730 Airbnb ROI: -2.22% Traditional ROI: 1.16%
93 VALLEY VIEW LN WINTERGREEN RESORT, VA Renovated mountain retreat with seasonal mountain views located minutes from the slopes & ...	4 beds \| 3 baths \| 1,694 sq.ft.	$597,000	Airbnb cash on cash: 0.5% Traditional cash on cash: 2.34% Airbnb Rental Income: $1846 Traditional Rental Income: $2374 Airbnb ROI: 0.5% Traditional ROI: 2.34%
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: 0.49% Traditional cash on cash: 3.37% Airbnb Rental Income: $1846 Traditional Rental Income: $2883 Airbnb ROI: 0.49% Traditional ROI: 3.37%
1460 LEDGES CONDOS WINTERGREEN RESORT, VA This one is an absolute stunner! Escape to this beautifully maintained and renovated 3br/3...	3 beds \| 3 baths \| 1,430 sq.ft.	$585,000	Airbnb cash on cash: -0.14% Traditional cash on cash: 0.71% Airbnb Rental Income: $2036 Traditional Rental Income: $1974 Airbnb ROI: -0.14% Traditional ROI: 0.71%
1501 CLIFFS CONDOS WINTERGREEN RESORT, VA Perched atop The Ridge with sweeping panoramic views of the Rockfish Valley and Blue Ridge...	1 beds \| 1 baths \| 763 sq.ft.	$325,000	Airbnb cash on cash: -3.07% Traditional cash on cash: 0.61% Airbnb Rental Income: $454 Traditional Rental Income: $1314 Airbnb ROI: -3.07% Traditional ROI: 0.61%
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: -3.14% Traditional cash on cash: 4.27% Airbnb Rental Income: $454 Traditional Rental Income: $1184 Airbnb ROI: -3.14% Traditional ROI: 4.27%
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.	$579,000	Airbnb cash on cash: 0.84% Traditional cash on cash: 3.67% Airbnb Rental Income: $1846 Traditional Rental Income: $2878 Airbnb ROI: 0.84% Traditional ROI: 3.67%
27 VEERY LN WINTERGREEN RESORT, VA Located on the golf course at Wintergreen Resort, this stunning 4-bedroom home offers hard...	4 beds \| 3 baths \| 2,098 sq.ft.	$599,000	Airbnb cash on cash: 0.4% Traditional cash on cash: 2.77% Airbnb Rental Income: $1846 Traditional Rental Income: $2677 Airbnb ROI: 0.4% Traditional ROI: 2.77%
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: -2.16% Traditional cash on cash: 3.15% Airbnb Rental Income: $669 Traditional Rental Income: $1515 Airbnb ROI: -2.16% Traditional ROI: 3.15%
44 E 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.	$499,000	Airbnb cash on cash: 0.99% Traditional cash on cash: 4.22% Airbnb Rental Income: $1846 Traditional Rental Income: $2856 Airbnb ROI: 0.99% Traditional ROI: 4.22%
952 BLUE RIDGE DR WINTERGREEN RESORT, VA This charming mountain house is back on market due to buyers remorse. It has been a succes...	5 beds \| 4 baths \| 2,537 sq.ft.	$599,000	Airbnb cash on cash: 2.06% Traditional cash on cash: 3.39% Airbnb Rental Income: $3038 Traditional Rental Income: $3085 Airbnb ROI: 2.06% Traditional ROI: 3.39%
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: -3.08% Traditional cash on cash: 3.02% Airbnb Rental Income: $454 Traditional Rental Income: $1116 Airbnb ROI: -3.08% Traditional ROI: 3.02%
4 TRILLIUM PL WINTERGREEN RESORT, VA 4 Trillium Lane sits at one of the highest vantage points in the Trillium development, off...	4 beds \| 4 baths \| 2,263 sq.ft.	$395,000	Airbnb cash on cash: 1.29% Traditional cash on cash: 4.74% Airbnb Rental Income: $1846 Traditional Rental Income: $2629 Airbnb ROI: 1.29% Traditional ROI: 4.74%
25 HICKORYNUT RD WINTERGREEN RESORT, VA The ultimate little Wintergreen cottage located in Black Rock Village, just a short walk t...	2 beds \| 2 baths \| 923 sq.ft.	$375,000	Airbnb cash on cash: -0.7% Traditional cash on cash: 2.78% Airbnb Rental Income: $669 Traditional Rental Income: $1592 Airbnb ROI: -0.7% Traditional ROI: 2.78%
2246 TANNERS RIDGE CONDOS WINTERGREEN RESORT, VA Tucked into the trees at Wintergreen, this 1BR/1BA ground-level condo offers a wooded, pri...	1 beds \| 1 baths \| 615 sq.ft.	$149,000	Airbnb cash on cash: -0.9% Traditional cash on cash: 6.1% Airbnb Rental Income: $454 Traditional Rental Income: $1187 Airbnb ROI: -0.9% Traditional ROI: 6.1%
730 LAURELWOOD CONDOS WINTERGREEN RESORT, VA Tucked into the trees at Wintergreen, this 2BR/2BA ground-floor, walk-out end unit offers ...	2 beds \| 2 baths \| 936 sq.ft.	$244,000	Airbnb cash on cash: -0.21% Traditional cash on cash: 5.11% Airbnb Rental Income: $669 Traditional Rental Income: $1595 Airbnb ROI: -0.21% Traditional ROI: 5.11%
1505 CLIFFS CONDOS WINTERGREEN RESORT, VA Enjoy sweeping mountain views right out your private patio in this ground-level, walk-out ...	1 beds \| 1 baths \| 763 sq.ft.	$249,900	Airbnb cash on cash: -0.89% Traditional cash on cash: 3.73% Airbnb Rental Income: $454 Traditional Rental Income: $1281 Airbnb ROI: -0.89% Traditional ROI: 3.73%

Real Estate investment in Wintergreen-resort, VA

There are 18 properties for sale in the city of Wintergreen Resort . The median list price in Wintergreen Resort is $385,000 and the average price per square foot is $263. In July 2026, the average monthly cash on cash return in Wintergreen Resort is 3.00%. The average monthly rental income in Wintergreen Resort is $1,595.

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

There are 18 investment properties available for sale in Wintergreen-resort.

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

The ROI for Short-Term is higher than the Long-Term in Wintergreen-resort with average rental income of $669.

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.

$349,000

Airbnb cash on cash: 0.65%

Traditional cash on cash: 5.61%

Airbnb Rental Income: $1846

Traditional Rental Income: $2973

Airbnb ROI: 0.65%

Traditional ROI: 5.61%

1717 HIGH RIDGE CONDOS

WINTERGREEN RESORT, VA

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

$430,000

Airbnb cash on cash: -2.22%

Traditional cash on cash: 1.16%

Airbnb Rental Income: $669

Traditional Rental Income: $1730

Airbnb ROI: -2.22%

Traditional ROI: 1.16%

93 VALLEY VIEW LN

WINTERGREEN RESORT, VA

4 beds | 3 baths | 1,694 sq.ft.

$597,000

Airbnb cash on cash: 0.5%

Traditional cash on cash: 2.34%

Airbnb Rental Income: $1846

Traditional Rental Income: $2374

Airbnb ROI: 0.5%

Traditional ROI: 2.34%

12 POWDERHORN LN

WINTERGREEN RESORT, VA

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

$569,500

Airbnb cash on cash: 0.49%

Traditional cash on cash: 3.37%

Airbnb Rental Income: $1846

Traditional Rental Income: $2883

Airbnb ROI: 0.49%

Traditional ROI: 3.37%

1460 LEDGES CONDOS

WINTERGREEN RESORT, VA

3 beds | 3 baths | 1,430 sq.ft.

$585,000

Airbnb cash on cash: -0.14%

Traditional cash on cash: 0.71%

Airbnb Rental Income: $2036

Traditional Rental Income: $1974

Airbnb ROI: -0.14%

Traditional ROI: 0.71%

1501 CLIFFS CONDOS

WINTERGREEN RESORT, VA

1 beds | 1 baths | 763 sq.ft.

$325,000

Airbnb cash on cash: -3.07%

Traditional cash on cash: 0.61%

Airbnb Rental Income: $454

Traditional Rental Income: $1314

Airbnb ROI: -3.07%

Traditional ROI: 0.61%

216 TIMBERS CONDOS

WINTERGREEN RESORT, VA

1 beds | 1 baths | 405 sq.ft.

$139,900

Airbnb cash on cash: -3.14%

Traditional cash on cash: 4.27%

Airbnb Rental Income: $454

Traditional Rental Income: $1184

Airbnb ROI: -3.14%

Traditional ROI: 4.27%

67 S FOREST DR

WINTERGREEN RESORT, VA

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

$579,000

Airbnb cash on cash: 0.84%

Traditional cash on cash: 3.67%

Airbnb Rental Income: $1846

Traditional Rental Income: $2878

Airbnb ROI: 0.84%