Top 10 Best Communities at Wintergreen Resort

skiier on a mountainWintergreen Resort is the mountain retreat you’ve been dreaming of.

With award-winning amenities that have launched the resort to the top of the list for “Best Ski Resorts” and “Best Golf Resorts,” the resort is a prime destination for visitors and part-time residents looking to escape to the peace and quiet of Wintergreen.

Are you considering a second home or vacation home in this excellent community? Are you trying to find the best place to call your own? Here are the 10 best condominium communities that Wintergreen has to offer.

Condo Quick Facts

Use this table to help you decide where you want your next vacation or second home to be, whether at a walk-to-ski condo or a spacious townhome in the heart of the resort.

Community NamePrice RangeSize RangeCondo FeeSpecial Features
The Cliffs$100,000 - $350,000800 - 1,750 sq.ft.$1545 QuarterlyMountain & Slopes views
Diamond Hill$100,000 - $350,000800 - 1,500 sq.ft.$1425 QuarterlyMountain & Slopes views; Ski Front
Dobie Mountain Condominiums$199,000 - $350,0001,020 - 1,428 sq.ft.$1,617 QuarterlyMountain & Slopes views; Ski Front
High Ridge$209,000 - $359,0001,248 - 1,846 sq.ft.$1250 QuarterlyMountain & Slopes views; Walk-to-Ski
High Ridge Court$159,000 - $359,0001,152 - 1,538 sq.ft.$1667 QuarterlyMountain & Slopes views; Walk-to-Ski
High Ridge Place$200,000 - $399,0001,182 - 1,541 sq.ft.$2000 QuarterlyMountain & Slopes views
Highlands$75,000 - $250,000800 - 1,500 sq.ft.$1185 QuarterlyMountain & Slopes views
The Overlook$175,000 - $370,0001,237 - 1,860 sq.ft.$1225 QuarterlyMountain & Slopes views
Trillium$160,000 - $300,0001,400 - 3,500 sq.ft.1150 QuarterlyTownhome Community
Westwood$145,000 - $300,0001,300 - 1,960 sq.ft.$825 QuarterlyTownhome Community

10 Best Wintergreen Real Estate Options

The Cliffs

Featuring million-dollar views of the mountains and valley, The Cliffs Condominiums are your ticket to paradise at Wintergreen Resort. These condos are close to the Wintergarden Spa & Fitness Center and offer 1-3 bedroom units.

Diamond Hill

If you love the ski slopes, these condos are perfect for you. Not only are they ski-front and are within easy reach of the lift, they have ski-in and ski-out accessibility. Diamond Hill offers 1-3 bedroom units.

Dobie Mountain Condominiums

Conveniently located near the resort’s ski slopes, Dobie Mountain offers condos that are 2-3 bedrooms with sunken fireplaces, ample space, vaulted ceilings, and modern upgrades that still reflect the residences’ original interiors.

High Ridge

Relax in the comforts of your very own mountain retreat with a fireplace, built-in bookcases, ceramic tile flooring, and modern upgrades in these 1-4 bedroom units. High Ridge condos are within easy reach of the best amenities Wintergreen Resort has to offer.

High Ridge Court

Low-maintenance living and endless resort amenities? High Ridge Court is perfect. This community offers 1-4 bedroom condos that have been renovated to reflect modern tastes, and include features like double vanities, a back deck, and breakfast bar.

High Ridge Place

Live a life of luxury here, where you’re just minutes from accessing Wintergreen Resort’s golf course, fitness center, The Plunge, and the ski slopes. High Ridge Place offers 1-4 bedroom condos.


Featuring 1-3 bedroom condos with upgraded kitchens, large windows, spacious bedrooms, and ski-in/ski-out accessibility, Highlands is a perfect retreat surrounded by the natural beauty of the mountains. It’s just across the street from the Wintergarden Spa & Fitness Center.

The Overlook

Panoramic views. Excellent amenities. Cozy living. The Overlook has everything you’re looking for and more, including upgrades like granite countertops and stainless steel appliances; units offer 1-4 bedrooms for you to choose from.

Trillium Place

It’s easy to get spoiled by Trillium Place. In fact, it’s designed to do just that. Built in a location that gives you ease of access to the best that the Wintergreen Resort has to offer, you’ll be within walking or shuttle distance to everything from the ski slopes to the spa.


This community offers 2-4 bedroom townhomes located along the 12th fairway of the Devils Knob golf course. Featured units even offer 2-car garages. Living in Westwood, you can enjoy the modern comforts of home within easy reach of the best amenities at the resort.

Find Your Paradise with Wintergreen Real Estate Experts

As you’re deciding which community to call your own, you don’t have to navigate the journey alone.

We are your Wintergreen real estate experts, and we’ll not only guide you through the entire condo buying process but we’ll also give you all of the information you need to know along the way — HOA dues, mortgage information, updated real estate statistics, and even a local directory.

Ready to tour the condo of your dreams? Contact us today at (877) 296-9860 or and we can schedule a showing.

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