Waynesboro, VA Homes

• 

  

  

  /19

  $181,500

  • 1 Bed
  • 1 Bath
  • 708 Sq Ft

  164 Mountain Inn Condos, Roseland, VA 22967

  Enjoy Wintergreen Resort from the heart of the Mountain Village! This prime location is located withing feet of resort restaurants, shopping and slopes. Fully renovated to Platinum status ( highest rating) in the prestigious resort rental program you can enjoy this condo as an investment rental or as your very own mountain getaway. Furnished and ready to go, there are two beds, a full bath and a

  STEVE MARIANELLA WINTERGREEN REALTY, LLC

  164 Mountain Inn Condos, Roseland, VA 22967
• 

  

  

  /38

  $410,000 Sold Jun 09, 2025

  • 2,412 Sq Ft
  • $170/SF
  • 31 Days On Market

  • 4 Beds
  • 3.5 Baths
  • Built 1990

  29 Trillium Close Unit A29, Wintergreen Resort, VA 22967

  Space, affordability and a Devils Knob Village location make the Trillium townhouses a great option to experience the Wintergreen lifestyle. This 4-bedroom 3.5 bath has plenty of space plus a 2-car garage, all within walking distance to the spa, Devils Knob Golf & Tennis and more. Plus, the main level has recently undergone a major and thorough renovation, see attached doc for a complete list.

  Michael Woolard RE/MAX REALTY SPECIALISTS-CHARLOTTESVILLE

  29 Trillium Close Unit A29, Wintergreen Resort, VA 22967
• 

  

  

  /15

  Not Listed For Sale

  • 2 Beds
  • 2 Baths
  • 812 Sq Ft

  2214 Tanners Ridge Condos, Wintergreen, VA 22958

  2214 Tanners Ridge Condos, Wintergreen, VA 22958
• 

  

  

  /6

  $79,000

  • Land
  • 0.46 Acre
  • $171,739 per Acre

  91 Shamokin Springs Trail, Nellysford, VA 22958

  Winter Views, great location with a nice slope. Perfect for a home with a walk out basement or a multi- level home, an easy building lot. Seller says bring all offers!!

  FRANCESCA SAN GIORGIO FOUR SEASONS REALTY 1

  91 Shamokin Springs Trail, Nellysford, VA 22958
• 

  

  

  /72

  $1,200,000 Sold Jun 06, 2025

  • 3,330 Sq Ft
  • $360/SF
  • 5 Days On Market

  • 4 Beds
  • 4.5 Baths
  • Built 2015

  105 Tyro Ln, Roseland, VA 22967

  A snow lover's dream! This like-new mountaintop home at Wintergreen Resort with ski-out access to the slopes is a must-see! This custom-built lodge style home features a soaring great room with vaulted ceiling and floor-to-ceiling views of the slopes. Outdoor living spaces include a composite wood deck, patio with hot tub, and brick outdoor fireplace for chilly stargazing. You'll love the modern

  DENISE RAMEY TEAM LONG & FOSTER - CHARLOTTESVILLE WEST

  105 Tyro Ln, Roseland, VA 22967
• 

  

  /32

  Est $248,205 Not Listed For Sale

  • 2 Beds
  • 2 Baths
  • 978 Sq Ft

  2101 Fairway Woods, Roseland, VA 22967

  2101 Fairway Woods, Roseland, VA 22967
• 

  

  /17

  $139,000

  • 1 Bed
  • 1 Bath
  • 405 Sq Ft

  234 Timbers Condos, Wintergreen Resort, VA 22967

  A perfect getaway and a minute walk to the ski front and all of Wintergreens activities at the Mountain Inn reception. Making over $18,000 in rental income on Evolve. This studio has eveything you need: a Kichenette that is fully furnished, king bed, large smart TV and a spacious deck. Sold Turnkey.

  FRANCESCA SAN GIORGIO FOUR SEASONS REALTY 1

  234 Timbers Condos, Wintergreen Resort, VA 22967
• 

  

  /36

  $393,000 Sold May 30, 2025

  • 1,246 Sq Ft
  • $315/SF
  • 29 Days On Market

  • 2 Beds
  • 2 Baths
  • Built 1984

  1534 Cliffs, Wintergreen Resort, VA 22967

  Best value on the mountain. Wonderful 2 bedroom with stunning views, several recent updates include: new Hvac, water heater, deck slider door, appliances, kitchen counters, FP hearth stone and all new furniture. Not used as a rental, vacant and easy to show.,Fireplace in Living Room

  Michael Woolard RE/MAX REALTY SPECIALISTS-CHARLOTTESVILLE

  1534 Cliffs, Wintergreen Resort, VA 22967
• 

  

  /69

  Est $796,495 Not Listed For Sale

  • 4 Beds
  • 3.5 Baths
  • 2,539 Sq Ft

  29 Rock Dove Ln, Roseland, VA 22967

  29 Rock Dove Ln, Roseland, VA 22967
• 

  

  /32

  $189,900

  • 2 Beds
  • 2 Baths
  • 852 Sq Ft

  2212 Tanners Ridge, Wintergreen Resort, VA 22967

  Top floor 2 bed/2 bath Tanners Ridge condo! Fresh paint top to bottom. Incredible vaulted ceilings in the living room with wood trim accents and wood burning fireplace (and the association provides firewood) provide mountain chalet vibe. Efficient floor plan with balcony overlooking the golf course provides for a nice getaway on the mountain. Fantastic mountain location in close proximity to the

  Michael Gaffney COMPASS-CHARLOTTESVILLE

  2212 Tanners Ridge, Wintergreen Resort, VA 22967
• 

  

  /15

  $150,000 Sold May 30, 2025

  • 648 Sq Ft
  • $231/SF
  • 46 Days On Market

  • 1 Bed
  • 1 Bath
  • Built 1981

  798 Laurelwood, Wintergreen Resort, VA 22967

  Welcome to 798 Laurelwood in Wintergreen Resort! This rustically charming, fully furnished 1 bedroom, 1 full bath condo is conveniently located in the heart of the Four Seasons Wintergreen Resort Village and is in close proximity to ski slopes, hiking trails, the Market, and the Mountain Inn Lodge. This end unit offers private views of the beautiful landscape from the outdoor deck, where you can

  Allison Jones The Steele Group

  798 Laurelwood, Wintergreen Resort, VA 22967
• 

  

  /66

  Est $657,204 Not Listed For Sale

  • 3 Beds
  • 3.5 Baths
  • 2,428 Sq Ft

  61 Bear Run, Roseland, VA 22967

  61 Bear Run, Roseland, VA 22967
• 

  

  /59

  $549,000

  • 3 Beds
  • 2 Baths
  • 1,464 Sq Ft

  127 Blackrock Cir, Roseland, VA 22967

  This mid-century modern mountain cottage is one of the first Deck House homes ever built at Wintergreen Resort, offering a unique blend of architectural character and mountain charm. Known for their quality construction, Deck House homes feature rich natural wood finishes, abundant windows for passive solar warmth, and an airy, light-filled layout. Enjoy one-level living with heart pine ceilings,

  Michael Woolard RE/MAX REALTY SPECIALISTS-CHARLOTTESVILLE

  127 Blackrock Cir, Roseland, VA 22967
• 

  

  /22

  $250,000 Sold May 27, 2025

  • 852 Sq Ft
  • $293/SF
  • 12 Days On Market

  • 2 Beds
  • 2 Baths
  • Built 1977

  405 Three Ridges Condos, Wintergreen Resort, VA 22967

  This fully and thoughtfully renovated 2-bedroom, 2-bath condo in the desirable Three Ridges neighborhood offers exceptional upgrades and a prime location just a 2-minute walk to the ski slopes. The current owners lived here full-time for several years, carefully designing and improving the space to maximize comfort, style, and efficiency. Highlights include: A completely remodeled kitchen

  Dima Holmes WINTERGREEN REALTY, LLC

  405 Three Ridges Condos, Wintergreen Resort, VA 22967
• 

  

  /29

  Est $636,489 Not Listed For Sale

  • 3 Beds
  • 3.5 Baths
  • 2,194 Sq Ft

  122 Warrior Run, Roseland, VA 22967

  122 Warrior Run, Roseland, VA 22967
• 

  

  /64

  $2,500,000

  • 6 Beds
  • 8 Baths
  • 5,667 Sq Ft

  880 Devils Knob Loop, Wintergreen Resort, VA 22967

  880 Devils Knob Loop is a stunning mountain estate where luxury and livability converge in the heart of Wintergreen Resort. This 6-bedroom, 5 full and 3 half-bath home blends timeless architecture with thoughtful updates, including Ipe hardwood decking, sleek glass railings, and top-tier Viking and Sub-Zero appliances. The vaulted great room, anchored by a dramatic stone fireplace, flows

  Jeff Mattie CORE REAL ESTATE PARTNERS LLC

  880 Devils Knob Loop, Wintergreen Resort, VA 22967
• 

  

  /29

  $340,000 Sold May 23, 2025

  • 1,210 Sq Ft
  • $281/SF
  • 15 Days On Market

  • 3 Beds
  • 2 Baths
  • Built 1985

  57 Butternut Ln, Roseland, VA 22967

  Charming Wintergreen Cottage ? Best Value on the Market! Discover this adorable cottage nestled in the heart of Wintergreen Resort! Offering the lowest price on the market, this cozy retreat is beautifully furnished and ready for you to enjoy. The updated kitchen features sleek granite countertops, adding a touch of elegance to the warm and inviting space. Whether you're looking for a weekend

  FRANCESCA SAN GIORGIO FOUR SEASONS REALTY 1

  57 Butternut Ln, Roseland, VA 22967
• 

  

  /26

  Not Listed For Sale

  • 4 Beds
  • 3.5 Baths
  • 1,840 Sq Ft

  19 Ivy Glen Ln, Roseland, VA 22967

  19 Ivy Glen Ln, Roseland, VA 22967
• 

  

  /31

  $235,000

  • 1 Bed
  • 1 Bath
  • 840 Sq Ft

  1420 Highlands Condos, Roseland, VA 22967

  Beautiful 1BR/1BA end-unit condo in the sought-after Highlands neighborhood. Enjoy a bright, open one-level floor plan with extra windows and natural light throughout. A unique Romeo & Juliet balcony opens from the dining area, and the spacious deck offers stunning views of the Blue Ridge Mountains, ski slopes, and unforgettable sunrises. Located directly across from the Wintergarden Spa &

  Dima Holmes WINTERGREEN REALTY, LLC

  1420 Highlands Condos, Roseland, VA 22967
• 

  

  /31

  $259,000 Sold May 16, 2025

  • 1,460 Sq Ft
  • $177/SF
  • 2 Days On Market

  • 2 Beds
  • 2.5 Baths
  • Built 1989

  8 Ivy Glen Ln, Wintergreen Resort, VA 22967

  Welcome to this beautiful, completely renovated and spacious 1,460 sq. ft. townhouse located in the heart of Wintergreen Resort. Please requset the extensive list with upgrades done in the last 4.5 years. Situated near the ski shuttle bus stop and just a short, scenic walk to hiking trails, the Nature Foundation, and the Wintergarden Spa & Aquatics Center, this home offers the perfect blend of

  Dima Holmes WINTERGREEN REALTY, LLC

  8 Ivy Glen Ln, Wintergreen Resort, VA 22967
• 

  

  /19

  Est $583,567 Not Listed For Sale

  • 2 Beds
  • 3 Baths
  • 2,385 Sq Ft

  1167 Devils Knob Loop, Roseland, VA 22967

  1167 Devils Knob Loop, Roseland, VA 22967
• 

  

  /53

  $533,671

  • 3 Beds
  • 2.5 Baths
  • 1,819 Sq Ft

  67 Timber Camp Dr, Roseland, VA 22967

  Discover your mountain retreat at Wintergreen Resort, where this beautifully renovated three-bedroom, two-and-a-half-bathroom home awaits. This property has undergone over $100,000 in recent upgrades that transform it into a true gem. The heart of the home features vaulted ceilings and a stunning wood-burning stone fireplace, perfect for cozy evenings after mountain adventures. Recent

  Cameron Carroll WINTERGREEN REALTY, LLC

  67 Timber Camp Dr, Roseland, VA 22967
• 

  

  /18

  $50,000 Sold May 16, 2025

  • Land
  • 0.35 Acre
  • $142,857 per Acre

  • 29 Days On Market

  191 Devils Knob Loop, Roseland, VA 22967

  Nice generous lot along the tee on hole # 13 of Devils Knob Golf Course. The topography of this property would be perfect for a two story home where you have the main living areas on the second floor so you can maximize the exposure and views towards the golf fairway. Some seasonal mountain and Shenandoah Valley views may be possible upon construction. Very central location off of Devils Knob

  Dima Holmes WINTERGREEN REALTY, LLC

  191 Devils Knob Loop, Roseland, VA 22967
• 

  

  /36

  Est $443,250 Not Listed For Sale

  • 3 Beds
  • 2 Baths
  • 1,539 Sq Ft

  71 Devils Bend, Roseland, VA 22967

  71 Devils Bend, Roseland, VA 22967
• 

  

  /30

  $212,000

  • 2 Beds
  • 2.5 Baths
  • 1,460 Sq Ft

  18 Briarwood Ln, Roseland, VA 22967

  Charming and light-filled 2-bedroom, 2.5-bath townhouse at Wintergreen Resort, offering 1,460 sq ft of comfortable living space. The main level features an open floor plan with the kitchen flowing into the dining and living areas. A cozy sunken conversation area surrounds the wood-burning fireplace?perfect for relaxing after a day on the slopes or trails. Upstairs, the spacious primary suite

  Dima Holmes WINTERGREEN REALTY, LLC

  18 Briarwood Ln, Roseland, VA 22967
• 

  

  /43

  $605,000 Sold May 12, 2025

  • 2,964 Sq Ft
  • $204/SF
  • 17 Days On Market

  • 4 Beds
  • 3 Baths
  • Built 1998

  21 N Forest Dr, Wintergreen Resort, VA 22967

  4-Bedroom Mountain Retreat with Massive Windows Overlooking Devils Knob Golf Course Welcome to your perfect resort mountain home. This beautifully constructed 4-bedroom, 3-bathroom retreat offers 2,900 square feet of inviting living space, perfectly positioned above the 12th hole of Devil's Knob Golf Course which is accessible by a forested trail on the 0.67 acre property. Enjoy city light views

  Tim Merrick WINTERGREEN REALTY, LLC

  21 N Forest Dr, Wintergreen Resort, VA 22967
• 

  

  /36

  Est $590,205 Not Listed For Sale

  • 3 Beds
  • 2 Baths
  • 1,684 Sq Ft

  43 S Rock Tree Ln, Roseland, VA 22967

  43 S Rock Tree Ln, Roseland, VA 22967
• 

  

  /21

  $239,500

  • 2 Beds
  • 2 Baths
  • 852 Sq Ft

  2209 Tanners Ridge Condos, Wintergreen Resort, VA 22967

  If you're looking for a sweet spot overlooking the golf course, this top floor Tanners Ridge getaway is for you! Inside this tastefully renovated and decorated 2 br/2 ba condo with vaulted ceilings, enjoy attractive laminate wood flooring throughout, along with updated kitchen and laundry appliances. Granite counters in the kitchen and bathrooms; the primary bedroom has its own private bathroom.

  Yvette Stafford MOUNTAIN AREA NEST REALTY

  2209 Tanners Ridge Condos, Wintergreen Resort, VA 22967
• 

  

  /18

  $155,000 Sold May 12, 2025

  • 648 Sq Ft
  • $239/SF
  • 126 Days On Market

  • 1 Bed
  • 1 Bath
  • Built 1978

  744 Laurelwood Condos, Wintergreen Resort, VA 22967

  Step into modern comfort and sophistication with this beautifully updated 1-bedroom, 1-bathroom condo at 744 Laurelwood. Perfectly designed for cozy living or as a stylish retreat, this home offers an unbeatable combination of luxury and convenience. This condo offers easy access to the ski slopes, local shops, dining, and recreational amenities. Features all new granite countertops, Carrera

  Wayne Flood WINTERGREEN REALTY, LLC

  744 Laurelwood Condos, Wintergreen Resort, VA 22967
• 

  

  /46

  Est $703,895 Not Listed For Sale

  • 3 Beds
  • 3 Baths
  • 2,571 Sq Ft

  52 Pedlars End, Roseland, VA 22967

  52 Pedlars End, Roseland, VA 22967
• 

  

  /7

  $45,000

  • Land
  • 0.44 Acre
  • $102,273 per Acre

  62 Split Rock Trail, Rockfish, VA 22967

  Build among the evergreens! Located on a quiet cul-de-sac setting above the road, this mostly level homesite is special as it is literally covered with an impressive, natural forest of mature mountain laurel. For hiking enthusiasts, there is a green belt/open space across the road that leads to the very popular trail system along the headwaters of Stoney Creek and a series of waterfalls. Also,

  Kate Farley WINTERGREEN REALTY, LLC

  62 Split Rock Trail, Rockfish, VA 22967
• 

  

  /47

  $299,000 Sold May 09, 2025

  • 784 Sq Ft
  • $381/SF
  • 94 Days On Market

  • 2 Beds
  • 1.5 Baths
  • Built 1976

  105 Eagles Ct Condos, Wintergreen, VA 22958

  Imagine this being your Sanctuary. Stunning ski front location in the Mt. Village with the incredible year-round views of ski slopes, mountains and valleys. Walk to the Market, Mt. Inn and to all of the ski amenities. Condominium Association has gated parking with assigned spots. Park right in front of your condo and only 1/2 flight of stairs to the front door. Fully renovated with modern

  Robert Craig WINTERGREEN REALTY, LLC

  105 Eagles Ct Condos, Wintergreen, VA 22958
• 

  

  /17

  Est $231,316 Not Listed For Sale

  • 2 Beds
  • 2 Baths
  • 978 Sq Ft

  2111 Fairway Woods, Roseland, VA 22967

  2111 Fairway Woods, Roseland, VA 22967
• 

  

  /16

  $149,900

  • 1 Bed
  • 1 Bath
  • 405 Sq Ft

  216 Timbers Condos, Wintergreen Resort, VA 22967

  OPEN HOUSE SATURDAY, JUNE 14 2p-4p ? Located just steps away to the slopes and the cozy Mountain Inn, 216 Timbers is an attractive and sharply decorated studio in the heart of Wintergreen Resort. Rated "Platinum" on the Wintergreen Resort Rental program ? a designation only assigned to properties that are well-maintained and furnished to a high standard ? this condo features luxury vinyl plank

  Yvette Stafford MOUNTAIN AREA NEST REALTY

  216 Timbers Condos, Wintergreen Resort, VA 22967
• 

  

  /17

  $50,000 Sold May 08, 2025

  • Land
  • 0.46 Acre
  • $108,696 per Acre

  • 46 Days On Market

  167 Devils Knob Loop, Roseland, VA 22967

  Nice generous lot along the tee on hole # 13 of Devils Knob Golf Course. The topography of this property would be perfect for a two story home where you have the main living areas on the second floor so you can maximize the exposure and views towards the golf fairway. Very central location off of Devils Knob Loop and at a convenient walk to the Devils Knob Overlook, the ski shuttle bus stop and

  Dima Holmes WINTERGREEN REALTY, LLC

  167 Devils Knob Loop, Roseland, VA 22967
• 

  

  /28

  Est $256,111 Not Listed For Sale

  • 2 Beds
  • 2 Baths
  • 978 Sq Ft

  2129 Fairway Woods, Roseland, VA 22967

  2129 Fairway Woods, Roseland, VA 22967
• 

  

  /32

  $388,000

  • 2 Beds
  • 2 Baths
  • 1,134 Sq Ft

  1421 Highlands, Wintergreen Resort, VA 22967

  Experience the pinnacle of alpine elegance at 1421 Highlands, a top-floor sanctuary within Wintergreen Resort, VA. This 2-bedroom, 2-bathroom condo, fully furnished and turn-key ready, offers a lifestyle of luxury with stunning views of the Blue Ridge Mountains and direct ski slope access.The expansive windows of the updated living room frame the ever-changing vistas of the slopes, providing a

  Marc Neufcourt Fathom Realty

  1421 Highlands, Wintergreen Resort, VA 22967
• 

  

  /6

  $435,000 Sold Apr 30, 2025

  • 1,088 Sq Ft
  • $400/SF
  • 0 Days On Market

  • 2 Beds
  • 2 Baths
  • Built 1984

  903 Diamond Hill Condos, Wintergreen Resort, VA 22967

  Beautifully renovated slope side condo with sleek contemporary finishes. Located in the closest Diamond Hill building to the main village.

  Michael Woolard RE/MAX REALTY SPECIALISTS-CHARLOTTESVILLE

  903 Diamond Hill Condos, Wintergreen Resort, VA 22967
• 

  

  /44

  Est $742,822 Not Listed For Sale

  • 5 Beds
  • 4.5 Baths
  • 3,007 Sq Ft

  1881 Wintergreen Dr, Roseland, VA 22967

  1881 Wintergreen Dr, Roseland, VA 22967
• 

  

  /48

  $479,000

  • 2 Beds
  • 2.5 Baths
  • 1,443 Sq Ft

  962 Diamond Hill Condos, Wintergreen Resort, VA 22967

  Rare two bedroom 2.5 bath, condo featuring ski-in ski-out slope access that sleeps 8. One of only 2 units in Diamond Hill with this unique spacious 1400 sq ft 2 level layout. Current owners have had both master bathrooms upgraded with custom tile work in showers, added closet space, replaced both water heaters, and had custom built in bunk beds in each master suite. This condo is perfect for two

  Michael Woolard RE/MAX REALTY SPECIALISTS-CHARLOTTESVILLE

  962 Diamond Hill Condos, Wintergreen Resort, VA 22967

Showing Results 81 - 120, Page 3 of 18