Studio to 5 Bedroom Homes for Sale in Winchester, VA

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  /30

  $379,990 New Construction

  • 3 Beds
  • 3.5 Baths
  • 1,784 Sq Ft

  209 Monteith Dr, Winchester, VA 22601

  OPEN HOUSE: Saturday - Sunday 1pm - 3pm 3 Level Condo with Deck! Explore Winchester’s new luxury townhome community. This three level home features three bedrooms, three and a half baths, and bright box bay window in the rear. An attached one car garage provides easy parking and storage. The main level includes a private finished recreation room and possible 4th bedroom with its own full bath and

  DRB Homes Builder

  209 Monteith Dr, Winchester, VA 22601
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  /42

  $503,929 New Construction

  • 3 Beds
  • 2.5 Baths
  • 2,181 Sq Ft

  116 Keystone, Winchester, VA 22603

  Embrace the Vera 30-F2 – Homesite 1097 at Hiatt Pointe—a two-car, front-load garage END UNIT VILLA with three bedrooms, two full bathrooms, and one half bathroom will be ready IMMEDIATELY. Visit our website for more information on our End of Year Savings Event, between 12/08/2025-12/23/25. Be welcomed by 9’ ceilings on both levels, oak main stairs, and expertly selected finishes that make this

  Shannon L Bray Pearson Smith Realty, LLC

  116 Keystone, Winchester, VA 22603
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  /22

  $879,999 New Construction

  • 4 Beds
  • 3.5 Baths
  • 2,320 Sq Ft

  Melody Plan at Abrams Pointe, Winchester, VA 22602

  The open, inviting layout of the ranch-style Melody plan makes entertaining easy. Inside, you'll find an expansive great room, a generous dining room and a well-appointed kitchen featuring a center island and roomy walk-in pantry. An elegant owner's suite boasts an oversized walk-in closet and private bath, and two additional bedrooms invite rest and relaxation. A laundry, mudroom and second full

  Richmond American Homes Builder

  101 Abrams Pointe Blvd Unit 37822593, Winchester, VA 22602
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  /41

  $77,700

  • Land
  • 6.09 Acres
  • $12,759 per Acre

  440 Iris Ln, Winchester, VA 22602

  Owner Financing Available! (see details below)Enjoy breathtaking, unrivaled views of the Shenandoah Valley below from this ridgetop property on Little North Mountain.Property Overview:Address: 440 Iris Lane, Winchester, VA 22602Size: 6.09 AcresKey Features:Gorgeous Sunset Valley ViewsTwo Lots in One Build on Both or Split Off!Extensive Road

  Robert Scott AcreTown.com

  440 Iris Ln, Winchester, VA 22602
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  /66

  $1,200,000

  • Land
  • 124 Acres
  • $9,677 per Acre

  0 Frog Hollow Rd Unit LotWP001, Winchester, VA 22603

  Heres a piece of pristine land on the market for the first time since the late 70s with nearly endless possibilities for the next owner(s). This property is located north of Winchester and very near the West Virginia line. This prime piece of real estate has been family-owned and operated for decades. It is a mix of mostly flat hay ground and wooded acreage that stretches to the top of North

  Chad Pangle Whitetail Properties Real Estate

  0 Frog Hollow Rd Unit LotWP001, Winchester, VA 22603
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  /39

  $650,000

  • 4 Beds
  • 4.5 Baths
  • 4,658 Sq Ft

  104 Heath Ct, Winchester, VA 22602

  This is the home you've been looking for! A lovely Colonial with room to spread out. A beautiful open floor plan with both elegance and comfort. Gorgeous hardwood floors on most of the main floor. Formal living and dining rooms, large gourmet kitchen with granite countertops, stainless steel appliances, stunning backsplash and an eating area. Also a main level den for added space and a cozy

  Kathryn Symenow CENTURY 21 New Millennium

  104 Heath Ct, Winchester, VA 22602
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  /20

  $534,990 New Construction

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

  108 Carnation Way, Winchester, VA 22603

  Welcome to your ideal one-level villa- the Hemingway! This thoughtfully designed home centers around a spacious kitchen, perfect for both daily life and entertaining guests. The main level offers two generous bedrooms, including a primary suite featuring a large walk-in closet and a private en suite bathroom for ultimate comfort. Convenience is key with a laundry room located just off the 2-car

  Brookfield Residential Builder

  108 Carnation Way, Winchester, VA 22603
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  /29

  $659,000

  • 3 Beds
  • 4 Baths
  • 2,973 Sq Ft

  521 Hidden Valley Ln, Winchester, VA 22603

  521 Hidden Valley is truly a hidden gem and a rare find. Pride of ownership is evident throughout this thoughtfully maintained cape cod. A paved driveway leads to the attached two-car garage and welcoming wraparound porch, where breathtaking views overlook neighboring pastures and horses.Step inside to hardwood floors and a flowing floor plan that opens to a two level living room featuring a

  Kaitlyn Behr RE/MAX Roots

  521 Hidden Valley Ln, Winchester, VA 22603
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  /61

  $799,999

  • 4 Beds
  • 3.5 Baths
  • 4,461 Sq Ft

  162 Janes Way, Winchester, VA 22602

  Discover this beautifully updated home on 5 private acres in the sought-after Brookneill Subdivision—just minutes from Winchester! The home includes numerous updates, including new hardwood floors through the living room, and stairs, new kitchen cabinets, countertops, sink, and appliances. Upstairs features two huge bedrooms with new carpet, the finished basement offers new luxury vinyl plank

  Tanner Pack RE/MAX Roots

  162 Janes Way, Winchester, VA 22602
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  /47

  $435,000

  • 3 Beds
  • 1.5 Baths
  • 1,952 Sq Ft

  164 Bethel Grange Rd, Winchester, VA 22603

  Beautiful brick ranch in a lovely, country rural setting with mountain views and only minutes to schools and town amenities. Sellers just installed new heat pump air conditioning and heat. 3 bedrooms, 1 1/2 baths with a shower stall in mud room downstairs. Country kitchen with adjoining carport. Large living room front window with nice view of Round Hill. Extra closets. 4 foot hallway with

  Cathy Durbin Crum Realty, Inc.

  164 Bethel Grange Rd, Winchester, VA 22603
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  /9

  $730,000

  • 3 Beds
  • 2 Baths
  • 2,139 Sq Ft

  1491 Pitcock Ln, Winchester, VA 22602

  New house for the New Year! Welcome to 1491 Pitcock Lane, a spacious rancher set on 2 flat, partially wooded acres built by local builder Scott and Scott Construction. Walking in the front door, you are greeted by an open floor plan with luxury vinyl plank flooring throughout. Just off the entry, a dedicated office provides the perfect work-from-home or flex space. The kitchen features timeless

  Kaitlyn Behr RE/MAX Roots

  1491 Pitcock Ln, Winchester, VA 22602
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  /86

  $641,999

  • 4 Beds
  • 3 Baths
  • 3,442 Sq Ft

  121 Sweetbriar Ln, Winchester, VA 22603

  "Private haven Rancher" on 13 plus acres with 4 Bedrooms and 3 full baths. Hardwood floors throughout home. See-thru Fireplace between Dining room and Living room. Recent upgraded kitchen with new flooring ,counter tops and fresh paint. Owners' Suite has bathroom w/whirlpool tub, separate shower, double sinks and French door access to the rear deck. Finished basement with full bath, bedroom,

  Andrew Hensley Samson Properties

  121 Sweetbriar Ln, Winchester, VA 22603
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  /67

  $399,999

  • 3 Beds
  • 2.5 Baths
  • 1,680 Sq Ft

  707 E Cork St, Winchester, VA 22601

  Don't let this location fool you - Plenty of parking on the side and back of the home and a large turn around space to exit onto Cork St easily! Centrally located colonial with gorgeous hardwood flooring and trim throughout! Step back in time, but enjoy all of the modern amenities with easy access to Jim Barnett Park just down the street, downtown walking mall and commuter roads, and even views

  Misty Weaver Samson Properties

  707 E Cork St, Winchester, VA 22601
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  /35

  $430,000

  • 4 Beds
  • 2 Baths
  • 2,100 Sq Ft

  17 E Leicester St, Winchester, VA 22601

  Classic 2100 square foot brick “American Foursquare” house in Winchester’s historic district. This very well maintained 1928 home was designed and built by “ole time” craftsmen who had an appreciation for solid, quality construction. What better way to spend wonderful lazy evenings or morning coffee than on the expansive 23-foot long front porch with a ceiling fan. This 4 bedroom, 2 bath home is

  Roger Lamborne MarketPlace REALTY

  17 E Leicester St, Winchester, VA 22601
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  /50

  $339,990

  • 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. AMAZING LOCATION! Right off of Rt.7 and close proximity to 81, you can't beat this spot! Inside, this one-level ranch home features

  Robin Gebhardt EXP Realty, LLC

  163 Denny Ln, Winchester, VA 22603
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  /47

  $519,900

  • 3 Beds
  • 1.5 Baths
  • 2,177 Sq Ft

  216 Fairmont Ave, Winchester, VA 22601

  Classy colonial on the stately Fairmont Avenue with million dollar homes nearby, walking mall in close proximity with a plethora of boutique shops and eateries. The 2000 square feet is designed for comfort and coziness accented by 9ft ceilings, sunlit formal rooms, a well appointed kitchen, spacious bedrooms, adorable loft on 3rd level for a playroom/den/office, and the best part is entering your

  Dave Spence RE/MAX Roots

  216 Fairmont Ave, Winchester, VA 22601
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  /67

  $379,000

  • 3 Beds
  • 2.5 Baths
  • 1,631 Sq Ft

  313 Beaver Trail, Winchester, VA 22602

  Looking for the perfect gift? Look no further! Beautiful Craftsman-style home in great Shawneeland location. Main level Primary Bedroom with Full Bath. Engineered Hardwood flooring in Living Room, Family Room, Dining Area and Kitchen, Upgraded Cabinetry throughout home. Oak Staircase and Railing. Upper Level has 2 Bedrooms and Bath. Ceramic Tile in all Baths and Laundry. Designer Lighting, 2 car

  Dana Durr CENTURY 21 New Millennium

  313 Beaver Trail, Winchester, VA 22602
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  /63

  $365,000 New Construction

  • 3 Beds
  • 2.5 Baths
  • 2,520 Sq Ft

  508 Grouse Dr, Winchester, VA 22602

  Nestled in the charming Wilde Acres community, this stunning new construction home, completed in 2025, offers a perfect blend of modern design and traditional comfort. The Colonial architectural style, adorned with durable vinyl siding, invites you into a warm and welcoming space. Step inside to discover a thoughtfully designed interior featuring a traditional floor plan that seamlessly connects

  Steve DuBrueler Coldwell Banker Premier

  508 Grouse Dr, Winchester, VA 22602
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  /72

  $699,900

  • 4 Beds
  • 3.5 Baths
  • 3,475 Sq Ft

  132 Amherst St, Winchester, VA 22601

  Price Improvement to make this Yours! Step back in time with this Beautifully preserved VICTORIAN Brick Home Built in 1880, a true piece of Winchester's history. This is a Registered Historic Property that showcases original architectural details, high ceilings, ornate trim, and original wood floors that reflect the artistry of a bygone era. A Well Designed Addition has allowed for generous space

  Jodi Costello ERA Oakcrest Realty, Inc.

  132 Amherst St, Winchester, VA 22601
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  $529,990 New Construction

  • 3 Beds
  • 2 Baths
  • 2,264 Sq Ft

  109 Sunflower Way, Winchester, VA 22603

  Welcome to your dream one-level villa, the Fitzgerald! This beautifully designed home features a central kitchen that serves as the heart of the house, perfect for both everyday living and entertaining. The main level includes two spacious bedrooms, including a luxurious primary suite with an expansive walk-in closet and an en suite bathroom for your comfort and privacy. Additionally, you'll find

  Brookfield Residential Builder

  109 Sunflower Way, Winchester, VA 22603
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  /13

  $605,990 Open Sun 12PM - 4PM

  • 4 Beds
  • 2.5 Baths
  • 3,134 Sq Ft

  187 Malbec Ct, Winchester, VA 22602

  Welcome to Abrams Pointe, featuring new single-family homes in an established Winchester neighborhood, complete with wooded cul-de-sac homesites. The Carlisle Floorplan is a beautiful 4-bedroom, 2.5-bath home with up to 3,789 square feet of living space. This single-family home design features an open floor plan, highlighted by a spacious great room, a light-filled kitchen, and a breakfast area.

  Dorelba Estrada New Home Star Virginia, LLC

  187 Malbec Ct, Winchester, VA 22602
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  /17

  $644,990 New Construction

  • 5 Beds
  • 4 Baths
  • 3,828 Sq Ft

  128 Wagtail Ln, Winchester, VA 22603

  Brand New Matisse is Ready for Move In at Hiatt Pointe at Snowden Bridge, a community for those 55 or better! The heart of the home is an open-concept haven, seamlessly blending a gourmet kitchen, dining room, and spacious family room. The kitchen, a chef's dream, features a functional island, abundant storage, Carrrara Mist Quartz counters, burlap and flagstone stained cabinets plus a large

  Elizabeth Ellis Brookfield Mid-Atlantic Brokerage, LLC

  128 Wagtail Ln, Winchester, VA 22603
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  /80

  $634,900

  • 5 Beds
  • 4 Baths
  • 3,432 Sq Ft

  3782 Wardensville Grade, Winchester, VA 22602

  Second chance on this Spacious Ranch-Style Retreat on 5+ Acres with Mountain Views Welcome to this beautifully updated ranch-style home offering over 5 acres of privacy, modern comforts, and sweeping mountain views. From the inviting covered front porch, step inside to a bright, open living room featuring durable LVP flooring and sliding glass doors that lead to an expansive deck—the perfect spot

  Amanda Gulla Preslee Real Estate

  3782 Wardensville Grade, Winchester, VA 22602
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  /43

  $589,990 New Construction

  • 6 Beds
  • 4.5 Baths
  • 3,619 Sq Ft

  125 Mascouten St, Winchester, VA 22602

  Introducing the Salem floorplan at The Retreat at Winding Creek! The first-floor owners' bedroom house you've been waiting for! On the main floor, you will find a formal dining room, laundry room, and half bath. The open-concept kitchen and living areas are perfect for entertaining. The kitchen has stainless steel appliances by Whirlpool with granite countertops. Upstairs are four additional

  D.R. Horton Builder

  125 Mascouten St, Winchester, VA 22602
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  /43

  $399,900

  • 3 Beds
  • 2 Baths
  • 1,580 Sq Ft

  420 Russelcroft Rd, Winchester, VA 22601

  Welcome to 420 Russelcroft Road — the house that practically checks all your boxes *and* puts a smile on your face while doing it. With 1,580 square feet of comfortable living space, this 3-bedroom, 2-bath beauty has all the right vibes. The hardwood floors throughout most of the home give it a touch of class (and make cleaning a breeze), while the carpeted bedrooms give you that perfect excuse

  Brian Yoder Realty ONE Group Old Towne

  420 Russelcroft Rd, Winchester, VA 22601
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  /36

  $410,000

  • 4 Beds
  • 3.5 Baths
  • 2,261 Sq Ft

  125 Cheshire Ct, Winchester, VA 22602

  Beautiful and well-maintained 4 bedroom, 3.5 bath townhouse at the end of a quiet cul-de-sac on the east side of Winchester. Conveniently located to Rt 7 and I-81 and historic downtown Winchester. The 3-level townhouse backs to a wooded tree area and has a fenced rear yard. New luxury vinyl floor installed in majority of the home. As you enter, you will be welcomed into a large foyer with

  Eric Kronenwetter RE/MAX Roots

  125 Cheshire Ct, Winchester, VA 22602
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  /33

  $245,000

  • 2 Beds
  • 1 Bath
  • 960 Sq Ft

  815 Pheasant Dr, Winchester, VA 22602

  Affordable and move-in ready ranch-style home on a little more than a half acre. The mature trees, abundant wildlife, and quiet location make this a serene location. Featuring 2 bedrooms and 1 full bath, this home was freshly painted (Nov 2025) and underwent a major renovation in 2017 (roof, HVAC, water heater, floors, fixtures, and more). Enjoy the comfort of 1-level living with plenty of

  Eric Kronenwetter RE/MAX Roots

  815 Pheasant Dr, Winchester, VA 22602
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  /39

  $589,990 New Construction

  • 6 Beds
  • 4 Baths
  • 3,127 Sq Ft

  HAYDEN Plan at Retreat at Winding Creek - Single Family, Winchester, VA 22602

  The Hayden is a two-story plan with 6 bedrooms and 3 bathrooms in over 3,100 total square feet. The main level features a flex room adjacent to the foyer, ideal for a formal dining room or home office. The gourmet kitchen has an oversized island for extra seating and a large pantry, and it opens to the dining area and a spacious living room. A bedroom with a full bathroom completes the main

  D.R. Horton Builder

  137 Seminole Dr Unit 36203781, Winchester, VA 22602
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  /35

  $479,990 New Construction

  • 4 Beds
  • 3 Baths
  • 1,920 Sq Ft

  1829 Harvest Dr, Winchester, VA 22601

  1829 Harvest Drive is an attractive end unit new 3 level townhome with full brick front in Winchester, VA for January move-in. Our modern Adams II floorplan features a 1-car garage, and 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

  1829 Harvest Dr, 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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  /13

  $374,990 New Construction

  • 3 Beds
  • 1.5 Baths
  • 1,752 Sq Ft

  123 Castaway Place, Winchester, VA 22603

  This stunning two-level villa boasts a modern open concept design that seamlessly connects living spaces for an inviting and spacious feel. The main level features a living room that opens effortlessly to the dining area, creating a perfect space for entertaining and family gatherings. The expansive rear kitchen includes an L-shaped layout with an eating bar and an island with additional bar

  Brookfield Residential Builder

  123 Castaway Place, Winchester, VA 22603
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  /36

  $799,900 New Construction

  • 3 Beds
  • 2.5 Baths

  6 Dicks Hollow Rd, Winchester, VA 22603

  Great Opportunity on this Brand-New Ranch Home Sitting on 2.82 Acres, Convent to Shopping and Commuter Routes to Winchester, Martinsburg and Northern Virginia. Open Concept with Split Bedroom Design. Front Board and Batten siding for a unique look. Large Primary Suite with spacious walk-in closet and 6' Shower. Main Level Private Office. Chief's Kitchen with Quarts Countertops, Island,

  Brett Sowder RE/MAX Roots

  6 Dicks Hollow Rd, Winchester, VA 22603
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  /36

  $529,990 New Construction

  • 5 Beds
  • 3 Baths
  • 2,415 Sq Ft

  ELM Plan at Retreat at Winding Creek - Single Family, Winchester, VA 22602

  Introducing the Elm, a contemporary 2,415 square feet two-story home, featuring five bedrooms, three bathrooms, a loft, and a two-car garage. As you step into the distinct foyer you will appreciate the open concept floorplan. The spacious kitchen boasts an abundance of cabinetry and counter space, an ample walk-in pantry, a large island with room for seating and stainless-steel appliances. The

  D.R. Horton Builder

  137 Seminole Dr Unit 36203780, Winchester, VA 22602
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  /65

  $799,900

  • 4 Beds
  • 3.5 Baths
  • 5,040 Sq Ft

  2411 Hunting Ridge Rd, Winchester, VA 22603

  This is the one you've been waiting for! Welcome to 2411 Hunting Ridge Rd. This large and private classic colonial is ready for you. With over 5000 sq ft and more than 5 acres of property, this beautiful home has it all. The winding tree-lined (and paved!) driveway invites you in. Enter into the welcoming two story foyer, which is flanked by lovely formal dining and sitting rooms. Exploring

  Amanda White Nova Home Hunters Realty

  2411 Hunting Ridge Rd, Winchester, VA 22603
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  /35

  $290,000

  • 2 Beds
  • 1 Bath
  • 1,176 Sq Ft

  239 Chestnut St, Winchester, VA 22601

  ******Price Reduction******239 Chestnut Street is a charming rancher in the heart of Winchester. 2 bedrooms, 1 bath, a large rear deck, eat in kitchen, laundry room could be converted into a third bedroom. Building in the back yard could be used as storage or a 1 car garage. This is a solid starter or downsizing home convenient to shopping,schools and parks. A little TLC will go a long way

  William Wertz Wildhawks Realty LLC

  239 Chestnut St, Winchester, VA 22601
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  /39

  $639,990 New Construction

  • 4 Beds
  • 3 Baths
  • 2,865 Sq Ft

  CLIFTON Plan at Willow Run, Winchester, VA 22601

  The Clifton by D.R. Horton is a stunning new construction, ranch home plan featuring 1,865 square feet of living space, 3 bedrooms, 2 bathrooms, and a 2-car garage. With a roomy and flexible floor plan, the Clifton is just as inviting as it is functional! Prepare to be enchanted by the spacious kitchen, equipped with brand-new stainless-steel appliances, sleek countertops, and cabinets that offer

  D.R. Horton Builder

  105 Trellis View Ln Unit 36406655, Winchester, VA 22601
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  /40

  $255,000

  • 3 Beds
  • 2 Baths
  • 1,615 Sq Ft

  114 Woodys Place, Winchester, VA 22602

  This exceptional residential property, located in the desirable Carlisle Estates subdivision, presents a unique opportunity for discerning buyers seeking a blend of contemporary design and functional living space. Constructed in 1988, this detached home showcases a contemporary loft architectural style, offering an inviting atmosphere that is both stylish and practical. Spanning 1,616 square

  Beth Paisley Long & Foster Real Estate, Inc.

  114 Woodys Place, Winchester, VA 22602
• 

  

  /24

  $399,900

  • 3 Beds
  • 2 Baths
  • 2,400 Sq Ft

  129 Jalapa Trail, Winchester, VA 22602

  Mountain Views & Modern Perfection: Your Turnkey Retreat Awaits!Seller offering buyer credit Welcome to your completely renovated sanctuary at 129 Jalapa Trail, where breathtaking Virginia mountain vistas meet the peace of mind of brand-new everything. Nestled on a private 1.35-acre lot, this charming home is the perfect blend of rustic tranquility and modern convenience—just 7 miles from the

  Leslie Woods-Hulse Century 21 Redwood Realty

  129 Jalapa Trail, Winchester, VA 22602
• 

  

  /69

  $605,000

  • Studio
  • 4,396 Sq Ft

  540 Monticello St, Winchester, VA 22601

  Welcome to 540 Monticello Street, a turnkey Multi-Unit Investment Opportunity in Prime Downtown Winchester Location!Presenting a Triplex in the heart of Downtown Winchester—a rare opportunity for investors seeking strong cash flow in a highly desirable and commuter-friendly location. Just minutes from I-81 and I-66, and less than an hour from Northern Virginia, this property offers

  Laura King MarketPlace REALTY

  540 Monticello St, Winchester, VA 22601
• 

  

  /42

  $419,000

  • 3 Beds
  • 2 Baths
  • 2,325 Sq Ft

  1133 Tomahawk Trail, Winchester, VA 22602

  Nestled in the serene Shawneeland community, this exquisite chalet-style residence offers a perfect blend of rustic charm and modern comfort. Set against a backdrop of breathtaking mountain views and scenic vistas, this home is a sanctuary for those seeking tranquility and an exclusive lifestyle. As you approach the property, the warm cedar exterior invites you in, exuding a sense of timeless

  Sue Goodwin Long & Foster Real Estate, Inc.

  1133 Tomahawk Trail, Winchester, VA 22602

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