Waynesboro, VA Homes

• 

  

  

  /48

  $43,500

  • Land
  • 0.52 Acre
  • $83,654 per Acre

  688 Shamokin Springs Trail, Nellysford, VA 22958

  This lot is ready for you to build your dream vacation home. Wait until you see it. The slope of the land makes it perfect for multiple levels, each providing a view. Being able to build your own home at Wintergreen is becoming more and more attractive, just drive around and look at all the new homes being built. This can be your lot, come check us out.

  

  Lindsey McClellan

  Real Broker, LLC

  (434) 732-7118

  688 Shamokin Springs Trail, Nellysford, VA 22958
• 

  

  

  /18

  $2,200 per month

  • 1 Bed
  • 1 Bath
  • 615 Sq Ft
  • Townhouse for Rent

  2240 Tanners Ridge, Roseland, VA 22967

  Available now for short term rental! All utilities included, and ready to rent immediately. If you are looking for a short term rental that's updated, furnished and includes utilities this one is it! Located within the wintergreen resort just past the nature foundation in Tanners Ridge.

  GABRIELLE MILLER TRIUMPH REALTY

  2240 Tanners Ridge, Roseland, VA 22967
• 

  

  

  /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
• 

  

  

  /32

  Est $174,369 Not Listed For Sale

  • 1 Bed
  • 1 Bath
  • 678 Sq Ft

  202 Timbers Condos, Wintergreen, VA 22958

  202 Timbers Condos, Wintergreen, VA 22958
• 

  

  

  /48

  $160,000

  • 1 Bed
  • 1 Bath
  • 648 Sq Ft

  752 Laurelwood, Wintergreen Resort, VA 22967

  This well-maintained one-bedroom condo is located in Laurelwood. It features a full kitchen, washer and dryer, and a fireplace. Since this unit has not been rented out, it is in excellent condition. It’s just a short walk to the resort, ski slopes (no shuttle needed), the Wintergreen Market, and the pool. If you're looking for an affordable getaway, this is the perfect spot. The atmosphere is

  

  Lindsey McClellan

  Real Broker, LLC

  (434) 533-9177

  752 Laurelwood, Wintergreen Resort, VA 22967
• 

  

  /5

  $175 per month

  • 2 Beds
  • 2 Baths
  • 1,119 Sq Ft
  • Condo for Rent

  252 Timbers, Wintergreen Resort, VA 22967

  Wintergreen Resort condo for rent short term only. $175 per night. On the third floor-no elevator. Beautifully remodeled including full kitchen. Max 6 people. Bedroom 1 has King bed. Bedroom 2 has King bed. Loft has double bed. Located at Upper Dobie and Potato Patch ski runs. Only a few steps away from the Wintergreen Resort Village stores/restaurants. Golf, tennis and pool access included with

  Ann Matteson Anchor Realty Group

  252 Timbers, 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
• 

  

  /34

  Est $581,052 Not Listed For Sale

  • 4 Beds
  • 3 Baths
  • 2,347 Sq Ft

  229 Fawn Ridge Dr, Roseland, VA 22967

  229 Fawn Ridge Dr, Roseland, VA 22967
• 

  /2

  $59,000

  • Land
  • 0.50 Acre
  • $118,000 per Acre

  1761 Blue Ridge Dr, Wintergreen Resort, VA 22967

  Premier golf front parcel! Build on one of the prettiest golf front lots along the green of Devils Knob Loop Golf Course #6 with long range fairway views. Great location with easy access to Shamokin Springs Nature Preserve and hiking trails. Benefit from lower building costs with the gentle terrain of a nearly level parcel. Electric already routed and also has access to fiber optic internet and

  

  MARLO ALLEN

  MOUNTAIN AREA NEST REALTY

  (434) 201-7910

  1761 Blue Ridge Dr, 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
• 

  

  /43

  Est $512,439 Not Listed For Sale

  • 3 Beds
  • 4 Baths
  • 1,725 Sq Ft

  18 Cobble Ln, Wintergreen Resort, VA 22967

  18 Cobble Ln, Wintergreen Resort, VA 22967
• 

  

  /40

  $405,000 Pending

  • 4 Beds
  • 4.5 Baths
  • 2,412 Sq Ft

  17 Trillium Close, Wintergreen Resort, VA 22967

  The immaculate presentation and central location of this Trillium villa at Wintergreen Resort should help put this one at the top of your list! It is located across the street from the Aquatics and Fitness Center, Wintergarden Spa, and the Wintergreen Nature Foundation and within walking distance of the Highlands Ski Slope and the pizzeria at the top of the mountain, Fire and Frost. The main

  

  Gavin Sherwood

  YES REALTY PARTNERS

  (434) 404-5309

  17 Trillium Close, Wintergreen Resort, 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
• 

  

  /50

  Est $655,191 Not Listed For Sale

  • 4 Beds
  • 3.5 Baths
  • 1,930 Sq Ft

  791 Shamokin Springs Trail, Roseland, VA 22967

  791 Shamokin Springs Trail, Roseland, VA 22967
• 

  

  /10

  $59,000

  • Land
  • 0.50 Acre
  • $118,000 per Acre

  1761 Blue Ridge Dr Unit 136, Wintergreen Resort, VA 22967

  Premier golf front parcel! Build on one of the prettiest golf front lots along the green of Devils Knob Loop Golf Course #6 with long range fairway views. Great location with easy access to Shamokin Springs Nature Preserve and hiking trails. Benefit from lower building costs with the gentle terrain of a nearly level parcel. Electric already routed and also has access to fiber optic internet and

  

  MARLO ALLEN

  MOUNTAIN AREA NEST REALTY

  (434) 577-8226

  1761 Blue Ridge Dr Unit 136, Wintergreen Resort, VA 22967
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  /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
• 

  

  /59

  Est $589,391 Not Listed For Sale

  • 4 Beds
  • 3.5 Baths
  • 2,952 Sq Ft

  33 Blue Flint Ln, Wintergreen Resort, VA 22967

  33 Blue Flint Ln, Wintergreen Resort, VA 22967
• 

  

  /18

  $155,000 Pending

  • 1 Bed
  • 1 Bath
  • 648 Sq Ft

  758 Laurelwood Condos, Wintergreen Resort, VA 22967

  Cozy 1-bedroom, 1-bath condo conveniently located just a short walk from the ski slopes and the heart of Wintergreen Resort Village. Here, you'll find a variety of restaurants, shops, a caf, and a beautiful lobby with several fireplaces and comfortable seating areas. The Market and Deli is also within easy walking distance from this condo. Laurelwood is the only condo neighborhood at Wintergreen

  Dima Holmes WINTERGREEN REALTY, LLC

  758 Laurelwood Condos, 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
• 

  

  /16

  Not Listed For Sale

  88 Deerberry Ln, Roseland, VA 22967

  88 Deerberry Ln, Roseland, VA 22967
• 

  

  /39

  $399,900 Pending

  • 4 Beds
  • 2 Baths
  • 1,500 Sq Ft

  134 Gumtree Dr, Wintergreen Resort, VA 22967

  Tucked away in the woods of Wintergreen Resort, this beautiful 4-bedroom, 2-bath home offers the perfect blend of privacy, comfort, and year-round adventure. Surrounded by lush greenery, the expansive deck invites you to relax and take in the peaceful forest views. Inside, the main level features an open floorplan with a bright, airy kitchen, a dining area that looks out to the trees, and a cozy

  Matt White REDFIN CORPORATION

  134 Gumtree Dr, 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
• 

  

  /44

  Not Listed For Sale

  • 2 Beds
  • 2 Baths
  • 1,136 Sq Ft

  1923 High Ridge Pl Condos, Wintergreen, VA 22958

  1923 High Ridge Pl Condos, Wintergreen, VA 22958
• 

  

  /26

  $89,987

  • Land
  • 0.39 Acre
  • $230,736 per Acre

  0 Blackrock Cir Unit LotWP001, Wintergreen Resort, VA 22967

  Welcome to your slice of paradise nestled in the breathtaking Blue Ridge Mountains! Own one of the last remaining building lots on Wintergreen Resorts prestigious Blackrock Circle and create your dream home where every morning begins with a stunning sunrise. Imagine sipping your coffee on the back porch, soaking in the panoramic views of the mountains as the sun crests over the horizon, shining

  KYLE WATERS Whitetail Properties Real Estate

  0 Blackrock Cir Unit LotWP001, 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

  Est $259,151 Not Listed For Sale

  • 2 Beds
  • 2 Baths
  • 972 Sq Ft

  743 Laurelwood, Wintergreen Resort, VA 22967

  743 Laurelwood, Wintergreen Resort, VA 22967
• 

  

  /33

  $285,000

  • 3 Beds
  • 3 Baths
  • 1,400 Sq Ft

  2046 Stone Ridge Condos, Wintergreen Resort, VA 22967

  Lovely and spacious 3BR/3BA condo with beautiful views of the 18th fairway and green at Devils Knob Golf Course. Enjoy one-level living with a bright, open-concept layout. The living room offers access to a private patio?perfect for relaxing and taking in the fresh mountain air and golf course scenery. The living, dining, and kitchen areas have just been freshly painted. Tastefully furnished and

  Dima Holmes WINTERGREEN REALTY, LLC

  2046 Stone Ridge Condos, Wintergreen Resort, 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
• 

  

  /54

  Est $614,605 Not Listed For Sale

  • 4 Beds
  • 4 Baths
  • 2,530 Sq Ft

  36 Pinnacle Dr, Nellysford, VA 22958

  36 Pinnacle Dr, Nellysford, VA 22958
• 

  

  /75

  $825,000

  • 5 Beds
  • 3.5 Baths
  • 3,174 Sq Ft

  74 Gray Birch Ln, Roseland, VA 22967

  Beautiful craftsman-style home built by renowned local builder Duncan Macfarlane of Macfarlane Homes. Constructed with SIPs (Structural Insulated Panels), this green-build offers excellent energy efficiency, sound insulation, and durability. The spacious floor plan features a large primary suite on the main level, with four guest bedrooms and a generous family room upstairs. An attached two-car

  Dima Holmes WINTERGREEN REALTY, LLC

  74 Gray Birch Ln, 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
• 

  

  /27

  Est $390,670 Not Listed For Sale

  • 2 Beds
  • 2 Baths
  • 1,140 Sq Ft

  957 Diamond Hill Condos, Wintergreen, VA 22958

  957 Diamond Hill Condos, Wintergreen, VA 22958
• 

  

  /31

  $285,000

  • 3 Beds
  • 3 Baths
  • 1,370 Sq Ft

  2082 Stone Ridge Condos, Wintergreen Resort, VA 22967

  This three bedroom/three bath condo, in the center of three major Wintergreen amenities, is the very closest condo on the mountain to walk to the Devils Knob Clubhouse! Imagine being able to easily jaunt down to both golf and tennis, as well as up to the aquatics center/gym/spa/pool/hot tubs! The covered terrace at the Devils Grill is one of the most incredible places to dine in the area, and

  Kate Farley WINTERGREEN REALTY, LLC

  2082 Stone Ridge Condos, 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
• 

  

  /5

  Not Listed For Sale

  352 Shamokin Springs Trail, Roseland, VA 22967

  352 Shamokin Springs Trail, Roseland, VA 22967
• 

  

  /75

  $774,000

  • 4 Beds
  • 4 Baths
  • 2,598 Sq Ft

  679 Pedlars Edge Dr, Roseland, VA 22967

  This home is absolutely pristine! Walk just a few steps from your driveway to the trail leading right out to the Tyro slope. New remote controlled gas log insert, radon mitigation system, security system, new gutters & guards and PVC band board around deck. Featuring a large deck and with views across to the Ridge with swings located below in a beautifully landscaped area. Driveway is paved with

  Wayne Flood WINTERGREEN REALTY, LLC

  679 Pedlars Edge Dr, Roseland, VA 22967
• 

  

  /8

  $35,000 Sold Jul 01, 2025

  • Land
  • 0.40 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 $411,917 Not Listed For Sale

  • 3 Beds
  • 2.5 Baths
  • 1,369 Sq Ft

  28 Fern Cir, Roseland, VA 22967

  28 Fern Cir, Roseland, VA 22967
• 

  

  /39

  $399,900

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

  1643 Overlook, Wintergreen Resort, VA 22967

  There's no disputing that the Overlook condos have the best location on the mountain for views and access, and this one is the perfect example of why. Stunning mountain & valley view's year-round, only 6 steps into the unit, and tastefully updated. Recent updates include; new carpeting, new HVAC/Heat Pump, and a renovated master bath. This unit's layout is efficient and comfortable which make

  Michael Woolard RE/MAX REALTY SPECIALISTS-CHARLOTTESVILLE

  1643 Overlook, 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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