Wintergreen Homes

• 

  

  

  /24

  $266,500 Sold Jul 30, 2025

  • 784 Sq Ft
  • $340/SF
  • 90 Days On Market

  • 2 Beds
  • 1.5 Baths
  • Built 1976

  107 Eagles Ct Condos, Wintergreen Resort, VA 22967

  "The Highlander" on Eagles Swoop is for sale! This highly successful short-term rental ground floor ski-up & ski-out condo is priced to move and has all the big-ticket improvements (Brand new TRANE HVAC, April 2025; Highest quality luxury vinyl tile (LVT) throughout, 2023; and newer washer/dryer, high-quality extra-large sliding rear door, and a large slope-view window changeout (all in 2021).

  Michael Woolard RE/MAX REALTY SPECIALISTS-CHARLOTTESVILLE

  107 Eagles Ct Condos, Wintergreen Resort, VA 22967
• 

  

  

  /30

  Not Listed For Sale

  • 2 Beds
  • 2 Baths
  • 1,130 Sq Ft

  2029 Stone Ridge Condos, Wintergreen, VA 22958

  2029 Stone Ridge Condos, Wintergreen, VA 22958
• 

  

  

  /23

  $249,500

  • 1 Bed
  • 1 Bath
  • 800 Sq Ft

  913 Diamond Hill Condos, Wintergreen Resort, VA 22967

  Stunning slopeside condo located directly on the Diamond Hill ski slope—step out from your patio and hit the slopes! This beautifully renovated unit offers an open floor plan with a wall of windows that brings the ski action and mountain views right into your living space. A cozy wood-burning fireplace serves as the centerpiece of the living area, perfect for apres-ski relaxation. Completely

  Dima Holmes WINTERGREEN REALTY, LLC

  913 Diamond Hill Condos, Wintergreen Resort, VA 22967
• 

  

  

  /55

  $450,000 Sold Jul 30, 2025

  • 1,283 Sq Ft
  • $351/SF
  • 112 Days On Market

  • 2 Beds
  • 2 Baths
  • Built 1989

  1637 Overlook Condos, Wintergreen Resort, VA 22967

  Just wow! This is the trifecta! Stunning million-dollar views, Stunning renovation and Stunning location. Only 1/2 flight of stairs up to step into one of the most spectacular condos on the Mountain. Better yet, the outdoor deck is on grade with steps to access the rear yard which is perfect for kids and pets. Soak in the morning sunrise, gaze at Lake Monocan in the Valley or catch the

  Robert Craig WINTERGREEN REALTY, LLC

  1637 Overlook Condos, Wintergreen Resort, VA 22967
• 

  

  

  /14

  Not Listed For Sale

  • 2 Beds
  • 2 Baths
  • 852 Sq Ft

  2221 Tanners Ridge Condos, Wintergreen, VA 22967

  2221 Tanners Ridge Condos, Wintergreen, VA 22967
• 

  

  /70

  $539,000

  • 3 Beds
  • 3 Baths
  • 1,433 Sq Ft

  1442 Highlands Condos, Wintergreen Resort, VA 22967

  Tastefully decorated & furnished Top-level condo with dreamy mountain & valley views set in desirable Devils Knob area of Wintergreen. As you enter, notice the wall of windows highlighting the scenery & chalet feel with soaring two-story wood-burning fireplace wrapped in natural stone, slate tile hearth & rustic wood mantle which anchors the space beneath vaulted wooden shiplap ceilings, creating

  MELISSA DUNN AVENUE REALTY, LLC

  1442 Highlands Condos, Wintergreen Resort, VA 22967
• 

  

  /59

  $579,000 Sold Jul 28, 2025

  • 2,633 Sq Ft
  • $220/SF
  • 7 Days On Market

  • 4 Beds
  • 4.5 Baths
  • Built 1988

  32 Stony Cove Ln, Roseland, VA 22967

  Discover this beautifully updated 4-bedroom, 4.5-bath home at Wintergreen Resort, offering 2,633 sq ft of comfortable, well-designed living space across 2.5 levels. Each bedroom has its own en suite bath, including two primary suites?one on the main level?perfect for hosting family and guests. The spacious great room features a dramatic floor-to-ceiling stone wood-burning fireplace and expansive

  Dima Holmes WINTERGREEN REALTY, LLC

  32 Stony Cove Ln, Roseland, VA 22967
• 

  

  /35

  Est $501,436 Not Listed For Sale

  • 3 Beds
  • 2.5 Baths
  • 2,064 Sq Ft

  106 Oak Ln, Roseland, VA 22967

  106 Oak Ln, Roseland, VA 22967
• 

  

  /45

  $449,000

  • 2 Beds
  • 2 Baths
  • 1,237 Sq Ft

  1607 Overlook Condos, Wintergreen Resort, VA 22967

  Located in the highest Overlook buildings, this gorgeous ridge condo is positioned to have amazing views with an especially private deck, and walk-out access to the lawn. With a 1/2 flight of stairs into the building and a 1/2 flight to the front door, you might not find these kinds of views, as well as ease of access elsewhere! The interior has been upgraded in an incredibly thoughtful way with

  Kate Farley WINTERGREEN REALTY, LLC

  1607 Overlook Condos, Wintergreen Resort, VA 22967
• 

  

  /61

  $649,500 Sold Jul 24, 2025

  • 2,384 Sq Ft
  • $272/SF
  • 2 Days On Market

  • 4 Beds
  • 3 Baths
  • Built 1994

  19 Pedlars Point, Wintergreen Resort, VA 22967

  Discover your dream mountain getaway in this beautifully renovated home. Imagine creating lifelong memories in a space designed for comfort and connection. This fully furnished 4-bedroom, 3-bath home offers an open and bright layout with high ceilings and plenty of natural light. Enjoy the charm of seasonal winter views, with the possibility of enhancing them for year-round enjoyment through

  Chastity Morgan MOUNTAIN AREA NEST REALTY

  19 Pedlars Point, Wintergreen Resort, VA 22967
• 

  

  /36

  Est $515,885 Not Listed For Sale

  • 4 Beds
  • 2 Baths
  • 2,106 Sq Ft

  60 W Elkwood Dr, Wintergreen Resort, VA 22967

  60 W Elkwood Dr, Wintergreen Resort, VA 22967
• 

  

  /27

  $239,900 Open Sat 12:30PM - 2:30PM

  • 2 Beds
  • 2 Baths
  • 1,002 Sq Ft

  2134 Fairway Woods Unit 2134, Roseland, VA 22967

  This is a wonderfully updated ground floor condo located on the 18th hole of Devils Knob golf course. The Fairway Woods Complex has undergone many exterior improvements in the past several years and has one of the most efficient and well run associations on the mountain. Tastefully updated in recent years, this unit has been used for family enjoyment and a successful platinum rental on the

  Michael Woolard RE/MAX REALTY SPECIALISTS-CHARLOTTESVILLE

  2134 Fairway Woods Unit 2134, Roseland, VA 22967
• 

  

  /36

  $469,000 Sold Jul 21, 2025

  • 1,448 Sq Ft
  • $324/SF
  • 123 Days On Market

  • 3 Beds
  • 2 Baths
  • Built 2006

  25 Devils Bend, Wintergreen Resort, VA 22967

  Welcome to this delightful mountain home, featuring a spacious open floor plan that invites comfort and convenience. The one-level layout features a great room with cathedral ceilings and a stone fireplace, and it is open towards the kitchen and the dining area. The primary suite down the hallway is spacious and features a good-sized walk-in closet. The rear deck offers a hot tub for relaxation

  Dima Holmes WINTERGREEN REALTY, LLC

  25 Devils Bend, 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
• 

  

  /21

  $230,000

  • 2 Beds
  • 2 Baths
  • 978 Sq Ft

  2122 Fairway Woods, Wintergreen Resort, VA 22967

  Nestled in the heart of Wintergreen Resort, this beautifully maintained 2-bedroom, 2-bathroom Fairway Woods condo offers the perfect blend of mountain charm and modern convenience. Whether you're seeking a full-time residence, weekend getaway, or income-generating rental, this property delivers comfort, style, and year-round appeal. Step inside to find an inviting open-concept living space with

  Wayne Flood WINTERGREEN REALTY, LLC

  2122 Fairway Woods, Wintergreen Resort, VA 22967
• 

  

  /52

  $579,000 Sold Jul 15, 2025

  • 1,500 Sq Ft
  • $386/SF
  • 34 Days On Market

  • 3 Beds
  • 3 Baths
  • Built 1980

  1473 Ledges, Wintergreen Resort, VA 22967

  Experience mountain living at its finest with this beautifully updated condo offering spectacular mountain and valley views and breathtaking sunrises.This two-level floor plan features a master suite on each level. The lower level master is expansive and includes a walk-in closet, a luxurious bathroom, a private walk-out deck, a sitting area, and a wood-burning fireplace for cozy mountain

  Dima Holmes WINTERGREEN REALTY, LLC

  1473 Ledges, Wintergreen Resort, VA 22967
• 

  

  /69

  Est $758,621 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
• 

  

  /41

  $479,000

  • 3 Beds
  • 2 Baths
  • 1,536 Sq Ft

  170 Deer Springs Ln, Wintergreen Resort, VA 22967

  Cozy and charming mountain retreat in a quiet, private section of Wintergreen Resort with wonderful seasonal views of the golf fairway. From the rear deck, enjoy the soothing sound of a bold creek flowing year-round just beyond the fairway. This home has been meticulously maintained and recently upgraded with an all-new luxury primary bathroom, fresh interior and exterior paint (including deck),

  Dima Holmes WINTERGREEN REALTY, LLC

  170 Deer Springs Ln, Wintergreen Resort, VA 22967
• 

  

  /27

  $242,000 Sold Jul 11, 2025

  • 972 Sq Ft
  • $249/SF
  • 17 Days On Market

  • 2 Beds
  • 2 Baths
  • Built 1978

  705 Laurelwood Condos, Wintergreen Resort, VA 22967

  Short distance to the Ski slopes! This condo sits at the center of the Resort, minutes to the Mountain inn, and Blackrock market. Sold Turnkey and it is in Move in ready condition. The only condo association with it's own pool. Recent upgrades are HVAC, tile flooring, carpet and appliances. The floor to ceiling rock fireplace is wonderful for those cozy winter days after skiing. A Must

  FRANCESCA SAN GIORGIO FOUR SEASONS REALTY 1

  705 Laurelwood Condos, Wintergreen Resort, VA 22967
• 

  

  /66

  Est $667,775 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
• 

  

  /33

  $139,000

  • 1 Bed
  • 1 Bath
  • 405 Sq Ft

  233 Timbers, Wintergreen Resort, VA 22967

  These units are rarely available. 1st Level - true ski-in, ski-out unit - on the mountain view side of the building. Ski straight from the lift to the deck of the unit or to the unit's ski locker at the building entrance. The views from this top-of-the-mountain unit are stunning. Steps away from shops and restaurants around the Mountain Inn. Enjoy sunrises, concerts, festivals and fireworks from

  David Coy Red Cedar Real Estate

  233 Timbers, Wintergreen Resort, VA 22967
• 

  

  /26

  $190,000 Sold Jul 10, 2025

  • 936 Sq Ft
  • $203/SF
  • 103 Days On Market

  • 2 Beds
  • 2 Baths
  • Built 1978

  714 Laurelwood Condos, Wintergreen Resort, VA 22967

  Great vacation or investment condo sold turn-key and fully furnished! Enjoy the privacy that an end unit offers and the extra corner windows in the primary bedroom too. The condo building is ideally situated with woods (and seasonal mountain views!) behind it and is just catty-corner from the pool reserved just for Laurelwood owners. Prime location with easy stroll to the Market, ski slopes, and

  MARLO ALLEN MOUNTAIN AREA NEST REALTY

  714 Laurelwood Condos, Wintergreen Resort, VA 22967
• 

  

  /29

  Est $592,302 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
• 

  

  /36

  $139,000

  • 1 Bed
  • 1 Bath
  • 405 Sq Ft

  233 Timbers Condos, Wintergreen Resort, VA 22967

  Best value in Wintergreen - these slope side units are rarely available. 1st Level - true ski-in, ski-out unit - on the mountain view side of the building. Ski straight from the lift to the deck of the unit or to the unit's ski locker at the building entrance. The views from this top-of-the-mountain unit are stunning. Steps away from shops and restaurants around the Mountain Inn. Enjoy

  David Coy RED CEDAR REAL ESTATE

  233 Timbers Condos, Wintergreen Resort, VA 22967
• 

  

  /36

  $237,000 Sold Jul 08, 2025

  • 936 Sq Ft
  • $253/SF
  • 48 Days On Market

  • 2 Beds
  • 2 Baths
  • Built 1978

  740 Laurelwood Condos, Wintergreen Resort, VA 22967

  This pristine condo is the perfect place to unwind and enjoy a truly remarkable mountain getaway. With an unbeatable location, it is the perfect setting for making lasting memories with family and friends. Many upgrades throughout the unit: interior paint, LVP flooring, new windows (except transoms) and exterior doors, NEW Carrier HVAC (12/2024), and refrigerator. An open great room with wood

  CHASTITY MORGAN MOUNTAIN AREA NEST REALTY

  740 Laurelwood Condos, Wintergreen Resort, 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
• 

  

  /23

  $162,500

  • 1 Bed
  • 2 Baths
  • 765 Sq Ft

  2031 Stone Ridge Condos, Wintergreen, VA 22967

  This is a ground-floor one-bedroom with two baths and a nice sleep sofa in the living room for additional family. It is located on the 18th fairway of the Devils Knob Golf Course and is a short walk to the spa, pools, exercise facilities, as well as tennis, golf, and the Devils Grill restaurant. It is a great location and is being sold furnished.,Oak Cabinets,Fireplace in Great Room

  Tim Merrick WINTERGREEN REALTY, LLC

  2031 Stone Ridge Condos, Wintergreen, VA 22967
• 

  

  /56

  $530,000 Sold Jul 03, 2025

  • 1,713 Sq Ft
  • $309/SF
  • 8 Days On Market

  • 3 Beds
  • 3 Baths
  • Built 2004

  26 Pine Siskin Ln, Roseland, VA 22967

  This is a must see. Come experience a perfectly appointed Bungalow which is nestled in the woods and backs to the acclaimed Devils Knob Golf Course. Just enough Post and Beam effects to convey that Mountain Home feeling. Versatility and convenience with true main level living including a primary suite and guest bedroom on the first floor and a second primary in the loft. Quality construction

  Robert Craig WINTERGREEN REALTY, LLC

  26 Pine Siskin Ln, Roseland, VA 22967
• 

  

  /19

  Est $547,015 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
• 

  

  /41

  $234,900

  • 2 Beds
  • 2 Baths
  • 852 Sq Ft

  2230 Tanners Ridge, Roseland, VA 22967

  This top floor condo at Tanners Ridge offers a serene mountain retreat with 2 bedrooms, 2 baths, vaulted ceilings, open concept & views of the 12th fairway at Devils Knob Golf Course. Turnkey & ready to move in, you'll love the LVP floors, updated kitchen w/ SS appliances, & the living room fireplace with all the wood you can burn (association provided) after a long day of skiing. This year-round

  William Matthew Barrett IV Elite Realty

  2230 Tanners Ridge, Roseland, VA 22967
• 

  

  /47

  $410,000 Sold Jul 02, 2025

  • 1,999 Sq Ft
  • $205/SF
  • 5 Days On Market

  • 4 Beds
  • 3 Baths
  • Built 1984

  98 Pedlars Point, Wintergreen Resort, VA 22967

  Secluded Home for Sale at Wintergreen A Private Retreat, nestled at the base of a striking rock cliff and situated on a peaceful cul-de-sac, this secluded property at Wintergreen offers both seasonal views and unparalleled privacy. The home is on a beautiful lot, designed to maximize tranquility and connection to nature. The natural flora and fauna is stunning. The home has soaring ceilings with

  Tim Merrick WINTERGREEN REALTY, LLC

  98 Pedlars Point, Wintergreen Resort, VA 22967
• 

  

  /36

  Est $441,122 Not Listed For Sale

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

  71 Devils Bend, Roseland, VA 22967

  71 Devils Bend, Roseland, VA 22967
• 

  

  /59

  $214,500

  • 2 Beds
  • 2 Baths
  • 812 Sq Ft

  2226 Tanners Ridge Condos Unit 2226, Wintergreen Resort, VA 22967

  Wonderfully located totally renovated two bedroom, two bath condo on Devils Knob Golf Course. Everything has been done for you and it is in move in condition. Condo has been extremely well maintained and never been rented by current owners. Condo is not only on the Golf Course but is conveniently located in walking distance to the pool and Spa. Unit is a must see. Renovations were well done with

  W. FRANCE BURGER, JR. RE/MAX 1ST OLYMPIC

  2226 Tanners Ridge Condos Unit 2226, Wintergreen Resort, VA 22967
• 

  

  /32

  $265,000 Sold Jul 01, 2025

  • 1,840 Sq Ft
  • $144/SF
  • 7 Days On Market

  • 4 Beds
  • 3.5 Baths
  • Built 1989

  31 Briarwood Ln, Wintergreen Resort, VA 22967

  Located on the 12th fairway of Devils Knob Golf Course, this 4-bedroom, 3.5-bath townhouse with a two-car garage offers 1,840 square feet of comfortable living space and plenty of opportunity to update and make it your own. The main level features a spacious living room, a separate dining area, and a cozy sitting space centered around a gas fireplace?ideal for relaxing or entertaining. A private

  LISA FLOOD WINTERGREEN REALTY, LLC

  31 Briarwood Ln, Wintergreen Resort, VA 22967
• 

  

  /36

  Est $562,771 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
• 

  

  /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
• 

  

  /8

  $35,000 Sold Jul 01, 2025

  • Land
  • 0.4 Acre
  • $87,500 per Acre

  • 10 Days On Market

  17 Kestrel Point, Wintergreen Resort, VA 22967

  It's not easy to find a lot that is fairly level on the top of a mountain! You'll find that here though. Located on a short, quiet cul-de-sac, the access is easy and allows for a straight-forward architectural design with plenty of space for parking. The lot has many beautiful native plants including a fern forest. This area of Wintergreen is in the heart of the Devils Knob Golf Course, close to

  Kate Farley WINTERGREEN REALTY, LLC

  17 Kestrel Point, Wintergreen Resort, VA 22967
• 

  

  /46

  Est $683,854 Not Listed For Sale

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

  52 Pedlars End, Roseland, VA 22967

  52 Pedlars End, 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 $15,000 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
• 

  

  /59

  $560,000 Sold Jun 30, 2025

  • 1,856 Sq Ft
  • $302/SF
  • 41 Days On Market

  • 3 Beds
  • 3 Baths
  • Built 1989

  1642 Overlook, Wintergreen Resort, VA 22967

  Embrace these Breathtaking Views! This TOP level Condo w/2 Floors offers 3 Bedroom/3 Full Bath (A Primary Bedroom/Bath on each Floor), boasting 2 Decks on Main Floor, 1 on the Top Floor for everyone's own space, relaxation and capturing those amazing views! As you enter the Main living area of this condo, which accommodates all your needs on the main floor, all your stress will melt away! The

  Sherry Millard LONG & FOSTER - CHARLOTTESVILLE

  1642 Overlook, Wintergreen Resort, VA 22967

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