Winchester, VA Homes for Sale

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  /44

  $374,900

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

  166 Graywolf Trail, Winchester, VA 22602

  Welcome to 166 Graywolf Trail, a stunningly renovated 4-bedroom, 3-bath home nestled on nearly a half acre of peaceful woodland in beautiful Winchester, VA. This move-in ready retreat blends modern comfort with a cozy family feel — the kind of home where memories are made. Step inside and discover an entirely new interior from top to bottom. Every inch has been thoughtfully updated: brand-new

  Mike Webber EXP Realty, LLC

  166 Graywolf Trail, Winchester, VA 22602
• Explore Winchester

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  /19

  $325,000

  • 4 Beds
  • 1.5 Baths
  • 1,659 Sq Ft

  728 Green St, Winchester, VA 22601

  This spacious rancher is ideal for someone looking to add their personal touch on a home! With some updates needed, the canvas is ready for you to add some fresh paint and new flooring to bring new life into this home! It does feature a charming brick fireplace, oversized living room, formal dining area, and spacious bedrooms. You'll also notice upgrades to the kitchen along with a newer roof.

  Gavin Washington Weichert Realtors - Blue Ribbon

  728 Green St, Winchester, VA 22601
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  /95

  $660,000

  • 4 Beds
  • 3.5 Baths
  • 4,101 Sq Ft

  608 Kernstown Ct, Winchester, VA 22601

  Discover the charm and serenity of suburban living at 608 Kernstown Court, nestled in the storied landscape of Winchester, Virginia. This picturesque address offers an ideal blend of history, convenience, and modern comfort, an inviting sanctuary for families, professionals, or anyone seeking a peaceful yet well connected lifestyle.This desirable property features a beautifully appointed

  Aaron Richert Realty FC, LLC

  608 Kernstown Ct, Winchester, VA 22601
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  /50

  $350,000

  • 3 Beds
  • 2 Baths
  • 1,152 Sq Ft

  163 Denny Ln, Winchester, VA 22603

  Excellent outdoor workspace and storage on the east side of Winchester. NO HOA - This property offers a detached two-car carport, a wired shed/workshop, and a wrap-around paved driveway, providing ideal space for vehicles, tools, hobbies, and additional parking. Inside, this one-level ranch home features several recent updates, including new carpet, new paint in the living room, primary bedroom,

  Robin Gebhardt EXP Realty, LLC

  163 Denny Ln, Winchester, VA 22603
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  /116

  $599,900

  • 3 Beds
  • 1.5 Baths
  • 2,874 Sq Ft

  510 S Washington St, Winchester, VA 22601

  Welcome to a piece of Winchester History. This historic Colonial Revival residence, built of enduring brick construction, offers an opportunity of owning a significant piece of the city's heritage. Situated on a .20 city acre lot, this property is ideally positioned directly on the route of the Shenandoah Apple Blossom Festival Parade, offering unparalleled viewing opportunities.With winter

  Laurie Webber Century 21 Modern Realty Results

  510 S Washington St, Winchester, VA 22601
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  /37

  $639,990 New Construction

  • 4 Beds
  • 3 Baths
  • 1,865 Sq Ft

  111 Scented Rose Way, Winchester, VA 22602

  Experience effortless living in our Willow Run Active Adult community! Our Clifton floorplan is a thoughtfully designed 1,865 sq.ft. ranch home, blending style and functionality in a single-level open layout. The moment you step inside the home; you will be greeted by an inviting foyer leading you into the heart of the home. The kitchen opens to a large great room with two windows that let in

  D.R. Horton Builder

  111 Scented Rose Way, Winchester, VA 22602
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  /46

  $629,990 New Construction

  • 4 Beds
  • 3 Baths
  • 1,888 Sq Ft

  113 Scented Rose Way, Winchester, VA 22602

  Experience effortless living in our Willow Run Active Adult community! Our Azalea floorplan is a thoughtfully designed 1,888 sq. ft. ranch home blending style and functionality in a single-level open layout. The moment you step inside the home; you will be greeted by an inviting foyer leading you into the heart of the home. The dining room seamlessly connects with the living room and kitchen,

  D.R. Horton Builder

  113 Scented Rose Way, Winchester, VA 22602
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  /27

  $509,990 New Construction

  • 4 Beds
  • 3 Baths
  • 2,168 Sq Ft

  113 Trellis View Ln, Winchester, VA 22602

  Experience effortless living in our Willow Run Active Adult community! Our Freeport floorplan is a thoughtfully designed villa blending style and functionality in a single-level open layout and finished loft. The moment you step inside the home; you will be greeted by an inviting foyer leading you into the heart of the home. The dining room seamlessly connects with the living room and kitchen,

  D.R. Horton Builder

  113 Trellis View Ln, Winchester, VA 22602
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  /24

  $499,990 New Construction

  • 4 Beds
  • 2.5 Baths
  • 1,964 Sq Ft

  128 Mascouten St, Winchester, VA 22602

  Offering 1,964 square feet of modern living space, the Pine floor plan is perfect for growing families or those who love to entertain. This thoughtfully designed single-family home features four spacious bedrooms, two and a half bathrooms, and a two-car garage on a slab foundation for added convenience. The open-concept layout highlights a stylish kitchen with stainless steel appliances, quartz

  D.R. Horton Builder

  128 Mascouten St, Winchester, VA 22602
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  /35

  $599,990 New Construction

  • 5 Beds
  • 3 Baths
  • 2,511 Sq Ft

  121 Mascouten St, Winchester, VA 22602

  The Hayden is a spacious two-story home featuring 6 bedrooms and 4 bathrooms across more than 3,100 square feet. The main level includes a versatile flex room off the foyer—perfect for a formal dining area or home office. The gourmet kitchen boasts an oversized island with seating, a large pantry, and opens to the dining area and expansive living room. A main-level bedroom with a full bathroom

  D.R. Horton Builder

  121 Mascouten St, Winchester, VA 22602
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  /27

  $509,990 New Construction

  • 4 Beds
  • 3 Baths
  • 2,168 Sq Ft

  111 Trellis View Ln, Winchester, VA 22601

  Experience effortless living in our Willow Run Active Adult community! Our Freeport floorplan is a thoughtfully designed villa blending style and functionality in a single-level open layout and finished loft. The moment you step inside the home; you will be greeted by an inviting foyer leading you into the heart of the home. The dining room seamlessly connects with the living room and kitchen,

  D.R. Horton Builder

  111 Trellis View Ln, Winchester, VA 22601
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  /36

  $449,990 New Construction

  • 4 Beds
  • 3.5 Baths
  • 1,889 Sq Ft

  1802 Blythe Way, Winchester, VA 22601

  1802 Blythe Way is an attractive new 3 level end townhome with full brick front in Winchester, VA scheduled for a November move-in. Our modern Adams floorplan features a 1-car garage, and along with a bedroom and full bathroom on the first floor. Stained oak stairs lead you to the main level with LVP floors. The kitchen is equipped with beautiful quartz countertops, white cabinets, and

  D.R. Horton Builder

  1802 Blythe Way, Winchester, VA 22601
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  /35

  $449,990 New Construction

  • 4 Beds
  • 3.5 Baths
  • 1,889 Sq Ft

  1822 Blythe Way, Winchester, VA 22601

  1822 Blythe Way is an attractive new 3 level end townhome with full brick front in Winchester, VA for November move-in. Our modern Adams floorplan features a 1-car garage, and along with a bedroom and full bathroom on the first floor. Stained Oak stairs lead you to the main level with LVP Floors. The kitchen is equipped with beautiful quartz countertops, white cabinets, and stainless-steel

  D.R. Horton Builder

  1822 Blythe Way, Winchester, VA 22601
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  /38

  $629,990 New Construction

  • 4 Beds
  • 3 Baths
  • 1,748 Sq Ft

  115 Scented Rose Way, Winchester, VA 22602

  Experience effortless living in our Willow Run Active Adult community! Our Bristol floorplan is a thoughtfully designed 1,748 sq. ft. ranch home, blending style and functionality in a single-level open layout. The moment you step inside the home; you will be greeted by an inviting foyer leading you into the heart of the home. The dining room seamlessly connects with the living room and kitchen,

  D.R. Horton Builder

  115 Scented Rose Way, Winchester, VA 22602
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  /35

  $434,990 New Construction

  • 4 Beds
  • 3.5 Baths
  • 1,923 Sq Ft

  1818 Blythe Way, Winchester, VA 22601

  1818 Blythe Way is an attractive new 3-level townhome with full brick front in Winchester, VA scheduled for a November move-in. Our modern Adams floorplan features a 1-car garage, and along with a bedroom and full bathroom on the first floor. Stained Oak stairs lead you to the main level with LVP Floors. The kitchen is equipped with beautiful quartz countertops, sarsaparilla cabinets, and

  D.R. Horton Builder

  1818 Blythe Way, Winchester, VA 22601
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  /27

  $362,990 New Construction

  • 3 Beds
  • 2.5 Baths
  • 1,500 Sq Ft

  102 Pomo Ln, Winchester, VA 22602

  Introducing the Delmar by D.R. Horton—a spacious and stylish interior townhome designed for easy, low-maintenance living. This two-story home offers 1,500 square feet of well-planned space with 3 bedrooms, 2.5 bathrooms, and a 1-car garage. The open-concept main level features a modern kitchen with a large island, plenty of cabinet space, and an oversized pantry—all flowing seamlessly into the

  D.R. Horton Builder

  102 Pomo Ln, Winchester, VA 22602
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  $619,990 New Construction

  • 4 Beds
  • 3 Baths
  • 1,888 Sq Ft

  121 Hydrangea Way, Winchester, VA 22602

  Experience effortless living in our Willow Run Active Adult community! Our Azalea floorplan is a thoughtfully designed 1,888 sq. ft. ranch home blending style and functionality in a single-level open layout. The moment you step inside the home; you will be greeted by an inviting foyer leading you into the heart of the home. The dining room seamlessly connects with the living room and kitchen,

  D.R. Horton Builder

  121 Hydrangea Way, Winchester, VA 22602
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  $599,990 New Construction

  • 4 Beds
  • 3 Baths
  • 1,958 Sq Ft

  114 Scented Rose Way, Winchester, VA 22602

  The Dover by D.R. Horton is a stunning new construction, ranch home plan featuring 1,958 square feet of living space on the main-level with 3 bedrooms, 2 bathrooms and a 2-car garage. A generous loft offers the perfect space for overnight guests, with an additional 754 square feet with a bedroom and full bathroom. The foyer welcomes you in with two versatile bedrooms, sharing a well-appointed

  D.R. Horton Builder

  114 Scented Rose Way, Winchester, VA 22602
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  /10

  $650,000 Open House 11/29

  • 5 Beds
  • 3.5 Baths
  • 3,552 Sq Ft

  2708 Cassidy Ct, Winchester, VA 22601

  Coming Soon in Rolling Hills Estates! Located in the Winchester City area, this beautifully maintained 5-bedroom, 3.5-bath home offers 3,552 sq ft of finished living space on a .35-acre cul-de-sac lot. Featuring a 3-car garage, fully fenced backyard, covered front porch, and a rear Trex deck with lighting and stairs to the yard, this home is built for comfortable living and entertaining. Inside,

  Geri Deane Hunt Country Sotheby's International Realty

  2708 Cassidy Ct, Winchester, VA 22601
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  /6

  $225,000 Coming Soon

  • Land
  • 15 Acres
  • $15,000 per Acre

  0 N Frederick Pike Unit VAFV2038096, Winchester, VA 22603

  Just 7 miles/minutes from Winchester Medical Center and 10 miles from downtown Winchester, this 15-acre parcel offers privacy and convenience in one. The land features rolling hills, unlogged mature hardwood forest, and mountain views, with a gravel driveway crossing a private bridge into a secluded, untouched setting. Zoned residential, it’s ideal for building a custom home, a weekend retreat,

  Kristina Towns Weichert Realtors - Blue Ribbon

  0 N Frederick Pike Unit VAFV2038096, Winchester, VA 22603
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  $1,485,000 Coming Soon

  • 4 Beds
  • 4.5 Baths
  • 3,484 Sq Ft

  Lot 18 Honeycrisp Way, Winchester, VA 22603

  Remarkable and new to the market Anderson subdivision lots. Located 5 minutes from downtown Winchester and Valley Health Medical Center (2 minutes from James Wood High School) off Apple Pie Ridge. These lots feature panoramic views of the entire Shenandoah Valley from Harper's Ferry to Strasburg to the Western Mountains, providing stunning views from an elevated, very private environment. These 5

  JP Carr Merrifield Realty, LLC

  Lot 18 Honeycrisp Way, Winchester, VA 22603
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  /13

  $200,000

  • 3 Beds
  • 2 Baths
  • 2,430 Sq Ft

  163 Cabin Ln, Winchester, VA 22603

  Discover the potential in this 3 bedroom, 2 bath home on 6.10 unrestricted acres, the perfect opportunity for buyers looking to create their own country retreat. The home is in need of significant work and is being sold AS IS. Outside, you’ll find a detached garage with an apartment above, ideal for guests, rental income, or multi-generational living. Multiple sheds provide ample storage for

  

  Kerry Wysong

  Long & Foster Real Estate, Inc.

  (540) 709-8545

  163 Cabin Ln, Winchester, VA 22603
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  /16

  $279,900

  • 3 Beds
  • 1.5 Baths
  • 1,332 Sq Ft

  2901 Sorrell Ct, Winchester, VA 22601

  *Investor Opportunity, current tenants have a lease until May of 2027* Welcome to your new home! This beautifully maintained 3 -bedroom, 1.5 bath townhome offers comfort, convenience, and style in a great location. On the main level you will find a spacious kitchen with ample cabinetry and a breakfast area, the living room offers plenty of natural light, off the living room is a convenient half

  Amber Jenkins Century 21 Redwood Realty

  2901 Sorrell Ct, Winchester, VA 22601
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  /4

  $265,000

  • Land
  • 5.18 Acres
  • $51,158 per Acre

  Lot 4 Handley Dr, Winchester, VA 22603

  Spring Valley Estates. A rare opportunity to find a 5-Acre lots within 5 minutes of downtown Winchester and the Valley Health Medical Center. James Wood High School and Apple Pie Elementary within a mile of this lot. Fully built lot with approved perc on file. Buyer can buy the lot and build their dream house or for future investment purposes. This corner lot is cleared with existing road

  JP Carr Merrifield Realty, LLC

  Lot 4 Handley Dr, Winchester, VA 22603
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  /30

  $340,000

  • 3 Beds
  • 2.5 Baths
  • 1,488 Sq Ft

  138 Windstone Dr, Winchester, VA 22602

  HAVE IT ALL! BEAUTIFUL 3-LEVEL TOWNHOUSE WITH A GAS LOG FIREPLACE, GARAGE AND A COMMUNITY SWIMMING POOL! Just east of Winchester and commuter convenient to I-81 and Rt. 7, shopping and services. An easy drive to Dulles Airport and Northern Virginia. Welcome to Windstone, a community with a fenced outdoor pool and plenty of places to walk. 3 bedrooms, 2 1/2 baths., including a primary suite with

  Teresa Strohmeyer ERA Oakcrest Realty, Inc.

  138 Windstone Dr, Winchester, VA 22602
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  /6

  $55,000

  • Land
  • 5.23 Acres
  • $10,516 per Acre

  0 0 Shockeysville Rd, Winchester, VA 22603

  Embrace the serenity of nature on this 5.23-acre wooded lot, offering the perfect blend of privacy, beauty, and possibility. Tucked away in a peaceful setting, this property features a picturesque pond, creating an ideal backdrop for your future home, weekend getaway, or recreational escape. Whether you're dreaming of building a custom home, setting up a private retreat, or simply investing in

  

  Kerry Wysong

  Long & Foster Real Estate, Inc.

  (540) 329-2751

  0 0 Shockeysville Rd, Winchester, VA 22603
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  /2

  $310,000

  • 3 Beds
  • 2 Baths
  • 954 Sq Ft

  614 Battle Ave, Winchester, VA 22601

  Photo's will be published soon! This charming ranch-style home, built in 1961, offers a perfect blend of comfort and modern convenience. Nestled in the thriving town of Winchester, the property features three bedrooms and two full bathrooms, providing ample space for relaxation and privacy. Enjoy a 15 minute walk to downtown Winchester (or a 5 min bike ride) and also the ability to easily access

  MARYELLEN CURRAN Burch Real Estate Group, LLC

  614 Battle Ave, Winchester, VA 22601
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  /45

  $541,724 New Construction

  • 3 Beds
  • 2.5 Baths
  • 2,263 Sq Ft

  108 Webster Ct, Winchester, VA 22603

  Welcome to the Vale 34-F2 – Homesite 1048 at Hiatt Pointe—a two-car, front-load garage villa with three bedrooms, two full bathrooms, and one half bathroom is ready to move in IMMEDIATELY. Visit our website for more information on our Black Friday Sale, between 11/19/2025- 11/25/25. Open and adaptable, this floorplan blends functionality with comfort. Enter through the welcoming front porch and

  Shannon L Bray Pearson Smith Realty, LLC

  108 Webster Ct, Winchester, VA 22603
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  /35

  $419,990 New Construction

  • 4 Beds
  • 3.5 Baths
  • 1,889 Sq Ft

  1814 Blythe Way, Winchester, VA 22601

  1814 Blythe Way is an attractive new 3 level townhome with full brick front in Winchester, VA for November move-in. Our modern Adams floorplan features a 1-car garage, and along with a bedroom and full bathroom on the first floor. Stained Oak stairs lead you to the main level with LVP Floors. The kitchen is equipped with beautiful Quartz countertops, Stone Grey cabinets, and stainless-steel

  D.R. Horton Builder

  1814 Blythe Way, Winchester, VA 22601
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  /27

  $499,990 New Construction

  • 4 Beds
  • 3 Baths
  • 2,168 Sq Ft

  109 Trellis View Ln, Winchester, VA 22602

  Experience effortless living in our Willow Run Active Adult community! Our Freeport floorplan is a thoughtfully designed villa blending style and functionality in a single-level open layout and finished loft. The moment you step inside the home; you will be greeted by an inviting foyer leading you into the heart of the home. The dining room seamlessly connects with the living room and kitchen,

  D.R. Horton Builder

  109 Trellis View Ln, Winchester, VA 22602
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  /41

  $650,259 New Construction

  • 3 Beds
  • 3 Baths
  • 3,200 Sq Ft

  108 Magpie Ln, Winchester, VA 22603

  Step into the Sierra 39-F2 – Homesite 1035 at Hiatt Pointe—a two-car, front-load garage single family home with three bedrooms and three full bathrooms is move in ready IMMEDIATELY. Visit our website for more information on our Black Friday Sale, between 11/19/2025- 11/25/25. Designed for ease and everyday function, this floorplan is as innovative as it stylish! Enter through the inviting front

  Shannon L Bray Pearson Smith Realty, LLC

  108 Magpie Ln, Winchester, VA 22603
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  /28

  $250,000

  • 2 Beds
  • 2 Baths
  • 1,173 Sq Ft

  115 12 Brookland Terrace Unit 12, Winchester, VA 22602

  Penthouse condo in excellent condition and move in ready. The cathedral ceilings and skylights in the living room provide for a bright, cheerful space, while the gas fireplace provides a cozy feel. . Sliding glass doors to a charming balcony with some mountain views provide additional enjoyable space. The interior of the unit includes a dining area, kitchen with electric range, dishwasher,

  Darcy Amburn Colony Realty

  115 12 Brookland Terrace Unit 12, Winchester, VA 22602
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  /42

  $399,000

  • 2 Beds
  • 2 Baths
  • 2,516 Sq Ft

  2913 Wardensville Grade, Winchester, VA 22602

  This fully remodeled stone ranch offers many recent upgrades, including a brand-new kitchen with granite countertops, new HVAC system, new hot water heater, new water softener, all-new kitchen appliances, and a new washer and dryer. Bring your barbecue and patio furniture to enjoy the spacious back deck overlooking a peaceful wooded area—perfect for outdoor entertaining or relaxing in

  Amanda Magana RE/MAX Roots

  2913 Wardensville Grade, Winchester, VA 22602
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  /16

  $349,999

  • 5 Beds
  • 2 Baths
  • 3,378 Sq Ft

  3339 N Frederick Pike, Winchester, VA 22603

  5 Wooded Acres with a pond – 7 miles/minutes from Winchester Medical CenterLarge 5-bedroom, 2-bath brick home on 5 wooded acres features its own pond, and a creek with bridge and asphalt driveway. Property offers fishing, wildlife, and privacy just minutes from Winchester Medical Center and downtown.Home requires major renovation and is being sold strictly as-is. Cash or renovation

  Kristina Towns Weichert Realtors - Blue Ribbon

  3339 N Frederick Pike, Winchester, VA 22603
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  /21

  $360,000 New Construction

  • 3 Beds
  • 2 Baths
  • 1,276 Sq Ft

  425 Bluebird Trail, Winchester, VA 22602

  Welcome to your brand-new retreat in Mountain Falls! This thoughtfully designed split foyer home offers the perfect balance of modern comfort and functional living. The upper level features an open layout with a bright living room, dining area, and kitchen—ideal for gatherings or everyday living. Down the hall, you’ll find a comfortable private suite with its own full bath, plus two additional

  Abby Walters Preslee Real Estate

  425 Bluebird Trail, Winchester, VA 22602
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  /38

  $369,000 Open Sat 11:30AM - 4PM

  • 4 Beds
  • 3 Baths
  • 2,378 Sq Ft

  218 Gazelle Trail, Winchester, VA 22602

  This stunning 4-bedroom, 3 bathroom home offers the perfect blend of tranquility and convenience. With brand new luxury vinyl plank on all levels and fresh paint throughout, this home is light-filled and sparkles with charm. The main level features a spacious living room with vaulted ceilings, perfect for entertaining guests, and a beautifully updated kitchen with large cabinets and island, new

  Gavin Kersellius Coldwell Banker Realty - Washington

  218 Gazelle Trail, Winchester, VA 22602
• 

  

  /23

  $279,000

  • 3 Beds
  • 1 Bath
  • 907 Sq Ft

  208 Shenandoah Ave, Winchester, VA 22601

  Welcome home to 208 Shenandoah Ave in Winchester, VA! This updated ranch home offers the coveted simplicity of easy, one-level living and is perfectly situated in a prime, convenient Winchester location. Featuring 3 bedrooms and 1 full bath, the interior is turn-key with newer flooring and fresh paint throughout. The living spaces are bright and inviting with lots of natural light, creating a

  Dan Whitacre Colony Realty

  208 Shenandoah Ave, Winchester, VA 22601
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  /17

  $330,000

  • 3 Beds
  • 1 Bath
  • 1,237 Sq Ft

  117 W Oates Ave, Winchester, VA 22601

  This charming bungalow, nestled in the heart of the Arthur C Oates Estate, offers a delightful blend of comfort and community. Built in 1953, this home features 3 cozy bedrooms, 1 full bathrooms, and an upstairs loft perfect for relaxation. The inviting kitchen is equipped with essential appliances, including a single oven and refrigerator, making meal preparation a breeze. The unfinished

  Jeffrey Konrady Realty ONE Group Old Towne

  117 W Oates Ave, Winchester, VA 22601
• 

  /2

  $425,000

  • 10 Beds
  • 6 Baths
  • 12,128 Sq Ft

  910 Franklin St, Winchester, VA 22601

  What a remarkable and unique opportunity!Assessed for $571630.00 Brand new roof on entire building, newly demolished warehouse has made way to enormous area for expansion and or parking. SOOO MUCH potential - Upper level has two apartments -However only one is approved for rental unitLower level is ready for its new transformation as residential or allowed commercial use - Conditional use

  Pakeeza Akhtar The KOR Group, Inc.

  910 Franklin St, Winchester, VA 22601
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  /18

  $539,990 New Construction

  • 3 Beds
  • 3 Baths
  • 2,050 Sq Ft

  113 Sunflower Way, Winchester, VA 22603

  Brand new main level living Hemingway is almost finished construction and nearly ready for you to call home! At the heart of the home, the gourmet kitchen shines with stainless steel appliances, quartz countertops, and upgraded cabinetry. The kitchen flows seamlessly into the dining and family rooms, where additional windows create a bright, inviting atmosphere—perfect for entertaining. Just

  Elizabeth Ellis Brookfield Mid-Atlantic Brokerage, LLC

  113 Sunflower Way, Winchester, VA 22603

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