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
2028 STONE RIDGE CONDOS WINTERGREEN RESORT, VA Beautiful turn-key condo just in time for your mountain getaway at Wintergreen! This 1 bed...	1 beds \| 2 baths \| 765 sq.ft.	$178,000	Airbnb cash on cash: 2.92% Traditional cash on cash: 5.06% Airbnb Rental Income: $1832 Traditional Rental Income: $1700 Airbnb ROI: 2.92% Traditional ROI: 5.06%
16 CHESTNUT LN WINTERGREEN RESORT, VA Here's a classic contemporary chalet you can enjoy year round at Wintergreen! With its con...	3 beds \| 2 baths \| 1,504 sq.ft.	$385,000	Airbnb cash on cash: 4.06% Traditional cash on cash: 3.76% Airbnb Rental Income: $2963 Traditional Rental Income: $2172 Airbnb ROI: 4.06% Traditional ROI: 3.76%
589 Pedlars Edge Drive WINTERGREEN RESORT, VA Charming 4BR/2.5BA chalet in Wintergreen with a three tier sprawling deck on over a half a...	4 beds \| 3 baths \| 2,300 sq.ft.	$498,500	Airbnb cash on cash: 3.83% Traditional cash on cash: 3.6% Airbnb Rental Income: $3505 Traditional Rental Income: $2626 Airbnb ROI: 3.83% Traditional ROI: 3.6%
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.	$425,000	Airbnb cash on cash: -0.01% Traditional cash on cash: 0.08% Airbnb Rental Income: $2106 Traditional Rental Income: $1604 Airbnb ROI: -0.01% Traditional ROI: 0.08%
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%
2148 FAIRWAY WOODS WINTERGREEN RESORT, VA Enjoy modern mountain luxury living at "Chalet on the Green," an exceptionally renovated 3...	3 beds \| 2 baths \| 1,419 sq.ft.	$325,000	Airbnb cash on cash: 3.8% Traditional cash on cash: 2.53% Airbnb Rental Income: $2963 Traditional Rental Income: $1893 Airbnb ROI: 3.8% Traditional ROI: 2.53%
1622 OVERLOOK CONDOS WINTERGREEN RESORT, VA This charming 2-bedroom, 2-bathroom condo is a winter enthusiast's dream, located within a...	2 beds \| 2 baths \| 1,283 sq.ft.	$415,000	Airbnb cash on cash: 0.61% Traditional cash on cash: 1.19% Airbnb Rental Income: $2106 Traditional Rental Income: $1793 Airbnb ROI: 0.61% Traditional ROI: 1.19%
2225 TANNERS RIDGE CONDOS WINTERGREEN RESORT, VA Step into a beautifully transformed contemporary condo where heated floors throughout crea...	1 beds \| 1 baths \| 615 sq.ft.	$182,000	Airbnb cash on cash: 3.23% Traditional cash on cash: 2.59% Airbnb Rental Income: $1832 Traditional Rental Income: $1227 Airbnb ROI: 3.23% Traditional ROI: 2.59%
2061 STONE RIDGE CONDOS #2061 WINTERGREEN RESORT, VA Spacious 3 bedroom condo located in the heart of Devils Knob Village overlooking the 18th ...	3 beds \| 3 baths \| 1,400 sq.ft.	$269,500	Airbnb cash on cash: 5.2% Traditional cash on cash: 4.52% Airbnb Rental Income: $2963 Traditional Rental Income: $2107 Airbnb ROI: 5.2% Traditional ROI: 4.52%
1610 OVERLOOK CONDOS WINTERGREEN RESORT, VA Stunning Renovated 2-Bedroom Condo at Wintergreen Resort Enjoy breathtaking views from thi...	2 beds \| 2 baths \| 1,283 sq.ft.	$415,000	Airbnb cash on cash: 0.61% Traditional cash on cash: 1.32% Airbnb Rental Income: $2106 Traditional Rental Income: $1842 Airbnb ROI: 0.61% Traditional ROI: 1.32%
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 OPEN HOUSE SATURDAY, JUNE 14 2p-4p â Located just steps away to the slopes and the cozy ...	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%
67 S FOREST DR WINTERGREEN RESORT, VA More Pictures coming soon. Nestled high near the top of Wintergreen Resort, this stunning ...	4 beds \| 4 baths \| 2,336 sq.ft.	$655,000	Airbnb cash on cash: 2.89% Traditional cash on cash: 3.13% Airbnb Rental Income: $3505 Traditional Rental Income: $2878 Airbnb ROI: 2.89% Traditional ROI: 3.13%
1643 OVERLOOK CONDOS #1643 WINTERGREEN RESORT, VA There's no disputing that the Overlook condos have the best location on the mountain for v...	2 beds \| 2 baths \| 1,237 sq.ft.	$399,900	Airbnb cash on cash: 0.75% Traditional cash on cash: 1.69% Airbnb Rental Income: $2106 Traditional Rental Income: $1919 Airbnb ROI: 0.75% Traditional ROI: 1.69%
203 Timbers WINTERGREEN RESORT, VA This is a 1st level, slope-side ""ski in ski out"" condo. 203 Timbers studio is located in...	1 beds \| 1 baths \| N/A	$158,800	Airbnb cash on cash: 6.79% Traditional cash on cash: 4.73% Airbnb Rental Income: $1832 Traditional Rental Income: $1026 Airbnb ROI: 6.79% Traditional ROI: 4.73%
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%
634 WHITE OAK CONDOS WINTERGREEN RESORT, VA LOCATION, LOCATION! Renovated, End Unit White Oaks Townhome is an easy walk to the ski slo...	2 beds \| 2 baths \| 912 sq.ft.	$239,500	Airbnb cash on cash: 3.42% Traditional cash on cash: 3.49% Airbnb Rental Income: $2106 Traditional Rental Income: $1581 Airbnb ROI: 3.42% Traditional ROI: 3.49%
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.	$225,000	Airbnb cash on cash: 5.65% Traditional cash on cash: 5.27% Airbnb Rental Income: $2106 Traditional Rental Income: $1485 Airbnb ROI: 5.65% Traditional ROI: 5.27%
21 WEEPING ROCK LN WINTERGREEN RESORT, VA Amazing privacy bordering Shamokin Springs Nature Preserve with trails and bold stream tha...	4 beds \| 5 baths \| 2,886 sq.ft.	$739,000	Airbnb cash on cash: 2.07% Traditional cash on cash: 3.93% Airbnb Rental Income: $3505 Traditional Rental Income: $4014 Airbnb ROI: 2.07% Traditional ROI: 3.93%

Real Estate investment in Wintergreen-resort, VA

There are 20 properties for sale in the city of Wintergreen Resort . The median list price in Wintergreen Resort is $355,000 and the average price per square foot is $273. In September 2025, the average monthly cash on cash return in Wintergreen Resort is 3.00%. The average monthly rental income in Wintergreen Resort is $1,747.

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

There are 20 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

2028 STONE RIDGE CONDOS

WINTERGREEN RESORT, VA

1 beds | 2 baths | 765 sq.ft.

$178,000

Airbnb cash on cash: 2.92%

Traditional cash on cash: 5.06%

Airbnb Rental Income: $1832

Traditional Rental Income: $1700

Airbnb ROI: 2.92%

Traditional ROI: 5.06%

16 CHESTNUT LN

WINTERGREEN RESORT, VA

3 beds | 2 baths | 1,504 sq.ft.

$385,000

Airbnb cash on cash: 4.06%

Traditional cash on cash: 3.76%

Airbnb Rental Income: $2963

Traditional Rental Income: $2172

Airbnb ROI: 4.06%

Traditional ROI: 3.76%

589 Pedlars Edge Drive

WINTERGREEN RESORT, VA

4 beds | 3 baths | 2,300 sq.ft.

$498,500

Airbnb cash on cash: 3.83%

Traditional cash on cash: 3.6%

Airbnb Rental Income: $3505

Traditional Rental Income: $2626

Airbnb ROI: 3.83%

Traditional ROI: 3.6%

1921 HIGH RIDGE PL CONDOS

WINTERGREEN RESORT, VA

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

$425,000

Airbnb cash on cash: -0.01%

Traditional cash on cash: 0.08%

Airbnb Rental Income: $2106

Traditional Rental Income: $1604

Airbnb ROI: -0.01%

Traditional ROI: 0.08%

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%

2148 FAIRWAY WOODS

WINTERGREEN RESORT, VA

3 beds | 2 baths | 1,419 sq.ft.

$325,000

Airbnb cash on cash: 3.8%

Traditional cash on cash: 2.53%

Airbnb Rental Income: $2963

Traditional Rental Income: $1893

Airbnb ROI: 3.8%

Traditional ROI: 2.53%

1622 OVERLOOK CONDOS

WINTERGREEN RESORT, VA

2 beds | 2 baths | 1,283 sq.ft.

$415,000

Airbnb cash on cash: 0.61%

Traditional cash on cash: 1.19%

Airbnb Rental Income: $2106

Traditional Rental Income: $1793

Airbnb ROI: 0.61%

Traditional ROI: 1.19%

2225 TANNERS RIDGE CONDOS

WINTERGREEN RESORT, VA

1 beds | 1 baths | 615 sq.ft.

$182,000

Airbnb cash on cash: 3.23%

Traditional cash on cash: 2.59%

Airbnb Rental Income: $1832

Traditional Rental Income: $1227

Airbnb ROI: 3.23%