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
163 MOUNTAIN INN CONDOS WINTERGREEN RESORT, VA ""Capture the Essence of Wintergreen by securing one of the finest condos at WTG's Mountai...	1 beds \| 1 baths \| N/A	$229,000	Airbnb cash on cash: 2.8% Traditional cash on cash: 1.89% Airbnb Rental Income: $1832 Traditional Rental Income: $1142 Airbnb ROI: 2.8% Traditional ROI: 1.89%
2028 STONE RIDGE CONDOS WINTERGREEN RESORT, VA Beautiful turn-key condo ready to rent or enjoy at Wintergreen! This 1 bedroom 2 full bath...	1 beds \| 2 baths \| 765 sq.ft.	$165,000	Airbnb cash on cash: 3.22% Traditional cash on cash: 5.52% Airbnb Rental Income: $1832 Traditional Rental Income: $1700 Airbnb ROI: 3.22% Traditional ROI: 5.52%
12 POWDERHORN LN WINTERGREEN RESORT, VA Open House Saturday 10/18 10:00-12:00 This Lovely corner lot home with great rock croppi...	4 beds \| 3 baths \| 2,200 sq.ft.	$689,000	Airbnb cash on cash: 2.38% Traditional cash on cash: 2.62% Airbnb Rental Income: $3505 Traditional Rental Income: $2883 Airbnb ROI: 2.38% Traditional ROI: 2.62%
134 SQUIRREL TREE LN WINTERGREEN RESORT, VA Location offers excellent access, ski in ski out, close to hiking trails, wonderful year-r...	3 beds \| 3 baths \| 1,421 sq.ft.	$699,000	Airbnb cash on cash: 1.6% Traditional cash on cash: 1.56% Airbnb Rental Income: $2963 Traditional Rental Income: $2257 Airbnb ROI: 1.6% Traditional ROI: 1.56%
1921 HIGH RIDGE PL CONDOS WINTERGREEN RESORT, VA This is one of those rare opportunities to have everything you have been hoping to find! W...	2 beds \| 2 baths \| 1,340 sq.ft.	$415,000	Airbnb cash on cash: 0.01% Traditional cash on cash: 0.11% Airbnb Rental Income: $2106 Traditional Rental Income: $1604 Airbnb ROI: 0.01% Traditional ROI: 0.11%
2229 TANNERS RIDGE CONDOS WINTERGREEN RESORT, VA Come enjoy the quiet and beauty of Wintergreen and the Blue Ridge Mountains while staying ...	2 beds \| 2 baths \| 812 sq.ft.	$235,000	Airbnb cash on cash: 3.26% Traditional cash on cash: 3.35% Airbnb Rental Income: $2106 Traditional Rental Income: $1587 Airbnb ROI: 3.26% Traditional ROI: 3.35%
234 TIMBERS CONDOS WINTERGREEN RESORT, VA A perfect getaway and a minute walk to the ski front and all of Wintergreens activities at...	1 beds \| 1 baths \| 405 sq.ft.	$139,000	Airbnb cash on cash: 5.44% Traditional cash on cash: 3.3% Airbnb Rental Income: $1832 Traditional Rental Income: $1052 Airbnb ROI: 5.44% Traditional ROI: 3.3%
962 DIAMOND HILL CONDOS WINTERGREEN RESORT, VA Rare two bedroom 2.5 bath, condo featuring ski-in ski-out slope access that sleeps 8. One ...	2 beds \| 3 baths \| 1,443 sq.ft.	$479,000	Airbnb cash on cash: 0.61% Traditional cash on cash: 1.78% Airbnb Rental Income: $2106 Traditional Rental Income: $2089 Airbnb ROI: 0.61% Traditional ROI: 1.78%
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.	$149,900	Airbnb cash on cash: 5% Traditional cash on cash: 3.93% Airbnb Rental Income: $1832 Traditional Rental Income: $1184 Airbnb ROI: 5% Traditional ROI: 3.93%
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.	$239,500	Airbnb cash on cash: 3.15% Traditional cash on cash: 3.14% Airbnb Rental Income: $2106 Traditional Rental Income: $1563 Airbnb ROI: 3.15% Traditional ROI: 3.14%
127 BLACKROCK CIR WINTERGREEN RESORT, VA This mid-century modern mountain cottage is one of the first Deck House homes ever built a...	3 beds \| 2 baths \| 1,464 sq.ft.	$549,000	Airbnb cash on cash: 2.5% Traditional cash on cash: 2.39% Airbnb Rental Income: $2963 Traditional Rental Income: $2224 Airbnb ROI: 2.5% Traditional ROI: 2.39%
2226 TANNERS RIDGE CONDOS #2226 WINTERGREEN RESORT, VA Wonderfully located totally renovated two bedroom, two bath condo on Devils Knob Golf Cour...	2 beds \| 2 baths \| 812 sq.ft.	$214,500	Airbnb cash on cash: 5.72% Traditional cash on cash: 5.32% Airbnb Rental Income: $2106 Traditional Rental Income: $1485 Airbnb ROI: 5.72% Traditional ROI: 5.32%
30 CEDAR DR WINTERGREEN RESORT, VA Spend an afternoon relaxing on the covered wraparound porch or an evening by the fire of t...	3 beds \| 3 baths \| 1,752 sq.ft.	$559,000	Airbnb cash on cash: 2.31% Traditional cash on cash: 2.25% Airbnb Rental Income: $2963 Traditional Rental Income: $2249 Airbnb ROI: 2.31% Traditional ROI: 2.25%
2134 FAIRWAY WOODS #2134 WINTERGREEN RESORT, VA This is a wonderfully updated ground floor condo located on the 18th hole of Devils Knob g...	2 beds \| 2 baths \| 1,002 sq.ft.	$239,900	Airbnb cash on cash: 2.33% Traditional cash on cash: 3.41% Airbnb Rental Income: $2106 Traditional Rental Income: $1812 Airbnb ROI: 2.33% Traditional ROI: 3.41%
3234 NORTH RIDGE CONDOS WINTERGREEN RESORT, VA You are going to love this well-maintained 3 br/3 ba condo with ground floor walkout in No...	3 beds \| 3 baths \| 1,432 sq.ft.	$369,000	Airbnb cash on cash: 3.14% Traditional cash on cash: 3.09% Airbnb Rental Income: $2963 Traditional Rental Income: $2263 Airbnb ROI: 3.14% Traditional ROI: 3.09%
240 TIMBERS CONDOS WINTERGREEN RESORT, VA Rare opportunity to own a ground floor, end unit, true 1 bedroom, with a fully updated kit...	1 beds \| 1 baths \| 660 sq.ft.	$169,000	Airbnb cash on cash: 4.24% Traditional cash on cash: 3.92% Airbnb Rental Income: $1832 Traditional Rental Income: $1286 Airbnb ROI: 4.24% Traditional ROI: 3.92%
27 VEERY LN WINTERGREEN RESORT, VA Open House Saturday 10/18/25 at 10:00-12:00 Located on the golf course at Wintergreen Reso...	4 beds \| 3 baths \| 2,098 sq.ft.	$625,000	Airbnb cash on cash: 2.71% Traditional cash on cash: 2.61% Airbnb Rental Income: $3505 Traditional Rental Income: $2677 Airbnb ROI: 2.71% Traditional ROI: 2.61%
84 WEST ELKWOOD DR WINTERGREEN RESORT, VA Location, price and great condition should have this cozy Wintergreen cabin at the top of ...	3 beds \| 2 baths \| 1,365 sq.ft.	$399,000	Airbnb cash on cash: 3.87% Traditional cash on cash: 3.46% Airbnb Rental Income: $2963 Traditional Rental Income: $2129 Airbnb ROI: 3.87% Traditional ROI: 3.46%

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 $304,450 and the average price per square foot is $256. In October 2025, the average monthly cash on cash return in Wintergreen Resort is 3.00%. The average monthly rental income in Wintergreen Resort is $1,652.

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

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

In 2025, 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 $2,106.

Your search for investment property begins and ends here

Investment Property for Sale in Wintergreen Resort, VA

163 MOUNTAIN INN CONDOS

WINTERGREEN RESORT, VA

1 beds | 1 baths | N/A

$229,000

Airbnb cash on cash: 2.8%

Traditional cash on cash: 1.89%

Airbnb Rental Income: $1832

Traditional Rental Income: $1142

Airbnb ROI: 2.8%

Traditional ROI: 1.89%

2028 STONE RIDGE CONDOS

WINTERGREEN RESORT, VA

1 beds | 2 baths | 765 sq.ft.

$165,000

Airbnb cash on cash: 3.22%

Traditional cash on cash: 5.52%

Airbnb Rental Income: $1832

Traditional Rental Income: $1700

Airbnb ROI: 3.22%

Traditional ROI: 5.52%

12 POWDERHORN LN

WINTERGREEN RESORT, VA

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

$689,000

Airbnb cash on cash: 2.38%

Traditional cash on cash: 2.62%

Airbnb Rental Income: $3505

Traditional Rental Income: $2883

Airbnb ROI: 2.38%

Traditional ROI: 2.62%

134 SQUIRREL TREE LN

WINTERGREEN RESORT, VA

3 beds | 3 baths | 1,421 sq.ft.

$699,000

Airbnb cash on cash: 1.6%

Traditional cash on cash: 1.56%

Airbnb Rental Income: $2963

Traditional Rental Income: $2257

Airbnb ROI: 1.6%

Traditional ROI: 1.56%

1921 HIGH RIDGE PL CONDOS

WINTERGREEN RESORT, VA

2 beds | 2 baths | 1,340 sq.ft.

$415,000

Airbnb cash on cash: 0.01%

Traditional cash on cash: 0.11%

Airbnb Rental Income: $2106

Traditional Rental Income: $1604

Airbnb ROI: 0.01%

Traditional ROI: 0.11%

2229 TANNERS RIDGE CONDOS

WINTERGREEN RESORT, VA

2 beds | 2 baths | 812 sq.ft.

$235,000

Airbnb cash on cash: 3.26%

Traditional cash on cash: 3.35%

Airbnb Rental Income: $2106

Traditional Rental Income: $1587

Airbnb ROI: 3.26%

Traditional ROI: 3.35%

234 TIMBERS CONDOS

WINTERGREEN RESORT, VA

1 beds | 1 baths | 405 sq.ft.

$139,000

Airbnb cash on cash: 5.44%

Traditional cash on cash: 3.3%

Airbnb Rental Income: $1832

Traditional Rental Income: $1052

Airbnb ROI: 5.44%

Traditional ROI: 3.3%

962 DIAMOND HILL CONDOS

WINTERGREEN RESORT, VA

2 beds | 3 baths | 1,443 sq.ft.

$479,000

Airbnb cash on cash: 0.61%

Traditional cash on cash: 1.78%

Airbnb Rental Income: $2106

Traditional Rental Income: $2089

Airbnb ROI: 0.61%