Winchester, VA Houses for Sale

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  /46

  $995,000

  • 4 Beds
  • 2.5 Baths
  • 2,859 Sq Ft

  247 Mcguire Rd, Winchester, VA 22603

  Tucked away on a private 2.7-acre wooded lot, this stunning all-brick colonial has been fully renovated from top to bottom. Inside, 3/4" solid ash, 5"wide herringbone flooring flows throughout, accented by designer lighting, crown molding, and elegant chair rail trim. The chef’s kitchen is a true showstopper—featuring a massive island, striking white and gold appliances, and custom finishes. The

  

  Lori Bales

  Keller Williams Realty

  (540) 701-5541

  247 Mcguire Rd, Winchester, VA 22603
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  /46

  $415,000

  • 3 Beds
  • 3 Baths
  • 1,806 Sq Ft

  133 Woodrow Rd, Winchester, VA 22602

  Welcome home to this charming split foyer in Carlisle Heights, ideally located on the east side of Winchester—just off Route 7 for an easy commute!Step inside to a light-filled interior featuring low-maintenance flooring throughout the main living areas and bedrooms, offering both comfort and practicality. The spacious, updated kitchen showcases white cabinetry, stainless steel

  

  Angie Ordonez

  NextHome Realty Select

  (540) 384-4063

  133 Woodrow Rd, Winchester, VA 22602
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  /42

  $344,900

  • 3 Beds
  • 1.5 Baths
  • 1,178 Sq Ft

  107 E Monmouth St, Winchester, VA 22601

  Price Reduction!! Charming Historic Home in Downtown Winchester – Move-In Ready!If you love timeless craftsmanship—think original wood floors, custom built-ins, and vintage doors—but still want the ease of modern living, this beautifully updated downtown Winchester home is calling your name!From the moment you step onto the inviting covered porch and through the front door, you’ll

  

  Jeanne Mezzatesta

  Colony Realty

  (540) 619-5037

  107 E Monmouth St, Winchester, VA 22601
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  /56

  $517,000

  • 3 Beds
  • 2 Baths
  • 2,302 Sq Ft

  101 Delaware Trail, Winchester, VA 22602

  Outdoor activities are everywhere you turn at this completely renovated home in Winchester. Hiking, swimming, biking, and kayaking are all close by. As you sit on the beautiful deck, you can listen to the birds while you have your coffee. There are stunning views out of every window of this open concept home. Come see this home for yourself and fall in love.

  

  Kimberly Pace

  EXP Realty, LLC

  (540) 240-9877

  101 Delaware Trail, Winchester, VA 22602
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  /99

  $869,500

  • 4 Beds
  • 4.5 Baths
  • 6,368 Sq Ft

  1517 Brookdale Ct, Winchester, VA 22601

  A rare opportunity to own the largest model in the Morlyn Hills neighborhood--more than 6500 square feet when including the fully finished basement. Situated on a premier lot and in immaculate, move-in-ready condition, this home is competitively priced and an exceptional value. This home features 4 bedrooms, 4.5 baths, and an impressive array of upgrades throughout.From the moment you enter

  

  Brock Harris

  Samson Properties

  (540) 596-5570

  1517 Brookdale Ct, Winchester, VA 22601
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  /8

  $690,000

  • 4 Beds
  • 2.5 Baths
  • 3,108 Sq Ft

  1950 Melvor Ln, Winchester, VA 22601

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  Kim Kroner

  Washington Dulles Real Estate Group

  (540) 453-8579

  1950 Melvor Ln, Winchester, VA 22601
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  /41

  $549,000

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

  1420 Fishel Rd, Winchester, VA 22602

  Nestled away in the trees, this updated retreat on 2.67 acres offers the perfect blend of peace, privacy, and one-level living. Inside, you’ll find 3 bedrooms, 2 renovated baths, brand-new flooring, and fresh paint throughout. The bright eat-in kitchen with island and stainless appliances flows into a spacious sitting room, enclosed rear porch with A/C, and a covered front porch for year-round

  

  Katherine (Kat) Wetzel

  Century 21 Redwood Realty

  (540) 779-1383

  1420 Fishel Rd, Winchester, VA 22602
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  /53

  $633,000

  • 4 Beds
  • 3 Baths
  • 3,959 Sq Ft

  320 Linden Dr, Winchester, VA 22601

  *2-1 Buydown being offered. Contact Agent for Details!* Experience generational refined living in this stunning luxury home just minutes from Winchester Medical Center. Designed for both elegance and comfort, this residence boasts exquisite crown moldings, rich wood floors, wainscoting, and cathedral ceilings throughout. The main level offers one-level living with an entry-level bedroom, a

  

  Kimberly Schroeder

  Long & Foster Real Estate, Inc.

  (540) 274-0212

  320 Linden Dr, Winchester, VA 22601
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  /25

  $279,999

  • 2 Beds
  • 1 Bath
  • 856 Sq Ft

  621 Panther Dr, Winchester, VA 22602

  Wilde Acres offers peaceful country living just 15–20 minutes from Winchester City. The property spans three lots, for a total of approximately .75 acres, and features multiple outbuildings with power and heat. It's ideal for outdoor enthusiasts, nature lovers, and gardeners. The various outdoor spaces provide perfect areas for a workshop, recreation room, or extensive storage. This

  

  Lori Bales

  Keller Williams Realty

  (540) 779-1824

  621 Panther Dr, Winchester, VA 22602
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  /83

  $649,900

  • 4 Beds
  • 3.5 Baths
  • 2,923 Sq Ft

  114 Nassau Dr, Winchester, VA 22602

  Discover Your Dream Home on Nassau Drive! Welcome to this stunning Colonial home, nestled on a beautifully landscaped, lot within the highly sought-after Fieldstone community. Conveniently located just off Route 7, this spacious property offers the perfect blend of commuter-friendly access and the privacy and tranquility of a large, fully fenced backyard. This impressive home features four

  

  Brock Harris

  Samson Properties

  (540) 781-1173

  114 Nassau Dr, Winchester, VA 22602
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  /34

  $870,000

  • 3 Beds
  • 2 Baths
  • 2,175 Sq Ft

  601 Fall Run Ln, Winchester, VA 22602

  Prepare to be captivated by the beauty and tranquility of this exceptional custom-built home, nestled on 20.10 acres with breathtaking mountain views. Offering desirable one-level living, this nearly new (under 3 years old) home boasts a gorgeous covered porch and an expansive deck perfect for savoring the stunning surroundings.Step inside to discover a meticulously designed open-plan

  Theo Theologis Slones Real Estate

  601 Fall Run Ln, Winchester, VA 22602
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  /44

  $850,000

  • 5 Beds
  • 4.5 Baths
  • 6,122 Sq Ft

  939 Buckner Dr, Winchester, VA 22601

  Listed well below market value, this stunning all-brick home in the sought-after Meadow Branch community was built in 2000 and has undergone extensive renovations in 2023 and 2024. The main-level bedroom includes a spacious, newly updated ensuite featuring an oversized marble-tiled shower, dual vanities, and a custom walk-in closet designed by ClosetsByDesign. The beautifully reimagined kitchen

  Kiran K. Morzaria Parekh Redfin Corporation

  939 Buckner Dr, Winchester, VA 22601
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  /53

  $774,900

  • 5 Beds
  • 3.5 Baths
  • 3,928 Sq Ft

  977 W Parkins Mill Rd, Winchester, VA 22602

  Welcome to your dream retreat—set on 5 private acres just outside Winchester, this fully renovated home offers the perfect blend of luxury and land. With 5 spacious bedrooms and 3.5 beautifully updated bathrooms, this property is designed for comfort, functionality, and style.From the chef’s kitchen to the expansive living areas, every detail has been thoughtfully upgraded. Whether you're

  Nicole Renzetti EXP Realty, LLC

  977 W Parkins Mill Rd, Winchester, VA 22602
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  /56

  $619,900 Open Sun 2PM - 4:30PM

  • 3 Beds
  • 2.5 Baths
  • 2,618 Sq Ft

  281 Light Rd, Winchester, VA 22603

  Century 21 Redwood Realty makes no representation as to the accuracy or reliability of information provided in the listing. Buyer should verify information provided, that is material to the Buyer’s decisions, as they relate to this property. Any provided documents should be researched and verified. ** Price Improvement!! Property previously appraised for just under $647,000! Now

  Jennifer Watt Century 21 Redwood Realty

  281 Light Rd, Winchester, VA 22603
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  /19

  $464,990 New Construction

  • 3 Beds
  • 2.5 Baths
  • 1,637 Sq Ft

  226 Munsee Cir, Winchester, VA 22602

  Step into 1,657 square feet of well-designed living space in the Cabral, featuring 3 spacious bedrooms, 2.5 bathrooms, and a flexible loft upstairs—perfect for a home office, playroom, or additional lounge area. This home showcases a charming Linen siding exterior with brick accents, while the interior boasts sleek gray kitchen and bathroom cabinets paired with modern finishes throughout. Enjoy

  Brooks Sears D R Horton Realty of Virginia LLC

  226 Munsee Cir, Winchester, VA 22602
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  /19

  $459,990 New Construction

  • 3 Beds
  • 2.5 Baths
  • 1,637 Sq Ft

  216 Munsee Cir, Winchester, VA 22602

  The Cabral offers 1,657 square feet of thoughtfully designed living space, featuring 3 spacious bedrooms, 2.5 bathrooms, and a versatile loft on the bedroom level—perfect for a home office, playroom, or additional lounge area. This home features a beautiful cypress green exterior with stone accents, and inside, you’ll find stylish white kitchen and bathroom cabinets paired with modern finishes

  Brooks Sears D R Horton Realty of Virginia LLC

  216 Munsee Cir, Winchester, VA 22602
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  /39

  $734,610 New Construction

  • 4 Beds
  • 3 Baths
  • 3,567 Sq Ft

  103 Wagtail Ln, Winchester, VA 22603

  Step into the Sierra 39-F2 – Homesite 1025 at Hiatt Pointe (55+)—a two-car, front-load garage SINGLE FAMILY home with four bedrooms and three full bathrooms will be ready IMMEDIATELY.. Designed for ease and everyday function, this factory-framed floorplan is as innovative as it stylish! Enter through the inviting front porch and be immediately welcomed by 9’ ceilings on both levels, oak main

  Shannon L Bray Pearson Smith Realty, LLC

  103 Wagtail Ln, Winchester, VA 22603
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  /31

  $524,990 New Construction

  • 3 Beds
  • 1 Bath
  • 1,841 Sq Ft

  Matisse Plan at Hiatt Pointe at Snowden Bridge - 55+ Single Family Homes Collection, Winchester, VA 22603

  Experience the epitome of modern living in the Matisse. This thoughtfully designed home offers main-level living at its finest, providing unparalleled comfort and flexibility to suit your unique lifestyle. 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,

  

  Brookfield Residential

  Builder

  105 Wagtail Ln Unit 36578843, Winchester, VA 22603
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  $579,990 New Construction

  • 3 - 4 Beds
  • 2 - 3 Baths
  • 1,498+ Sq Ft

  Avalon Plan at Abrams Pointe - Heritage, Winchester, VA 22602

  The Avalon home design by Maronda Homes blends elegant design with everyday functionality to create a home that's both stylish and smart. With 3 bedrooms, 2 bathrooms, and up to 2,538 square feet of living space, the Avalon is ideal for those looking for main-level living. As soon as you walk in, you will be greeted by a spacious, open-concept layout. The main level includes the option to convert

  

  Maronda Homes

  Builder

  161 Williamson Rd Unit 37110562, Winchester, VA 22602
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  $632,990 New Construction

  • 3 Beds
  • 2 - 3 Baths
  • 1,956+ Sq Ft

  Drexel Plan at Abrams Pointe - Heritage, Winchester, VA 22602

  The Drexel home design is a spacious and versatile single-family home designed to suit a variety of lifestyles. With up to 3,213 finished square feet, the Drexel offers generous living space that can be customized to meet your needs. It features main-level living with three bedrooms, including a private master suite with a walk-in closet and en-suite bathroom, along with two full bathrooms and a

  

  Maronda Homes

  Builder

  161 Williamson Rd Unit 37110564, Winchester, VA 22602
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  $611,990 New Construction

  • 4 Beds
  • 2.5 - 3.5 Baths
  • 2,382+ Sq Ft

  Somerset Plan at Abrams Pointe - Americana, Winchester, VA 22602

  The Somerset home design by Maronda Homes is designed with today’s lifestyle in mind—blending open-concept living, functional spaces, and refined details into one beautifully crafted home. With 4 bedrooms, 2 to 4 bathrooms, and up to 3,514 square feet of living space, the Somerset offers flexibility for families at every stage of life.The heart of the home is the expansive great room, which opens

  

  Maronda Homes

  Builder

  161 Williamson Rd Unit 37110563, Winchester, VA 22602
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  $591,990 New Construction

  • 4 Beds
  • 2.5 - 3.5 Baths
  • 2,035+ Sq Ft

  Rockford Plan at Abrams Pointe - Americana, Winchester, VA 22602

  The Rockford home design offers a thoughtful blend of modern functionality and classic comfort, perfect for homeowners who value both style and efficiency. With 4 bedrooms, 2 to 3 bathrooms, and up to 2,833 square feet of living space, the Rockford is an ideal choice for first-time buyers, growing families, or anyone looking to right-size their lifestyle.Step inside to find an inviting

  

  Maronda Homes

  Builder

  161 Williamson Rd Unit 37110038, Winchester, VA 22602
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  $619,990 New Construction

  • 4 Beds
  • 2.5 - 3.5 Baths
  • 2,687+ Sq Ft

  Birmingham Plan at Abrams Pointe - Americana, Winchester, VA 22602

  The Birmingham home design offers a harmonious blend of space, comfort, and elegance, perfect for families who value both form and function. With 4 bedrooms, 2.5 to 3.5 bathrooms, and up to 3,717 square feet of thoughtfully designed living space, the Birmingham is a home that adapts to your lifestyle.Step through the welcoming foyer into a bright, open-concept layout that includes a flex space

  

  Maronda Homes

  Builder

  161 Williamson Rd Unit 37110033, Winchester, VA 22602
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  $632,990 New Construction

  • 4 - 6 Beds
  • 2.5 - 5.5 Baths
  • 2,817+ Sq Ft

  Carlisle Plan at Abrams Pointe - Americana, Winchester, VA 22602

  The Carlisle home design by Maronda Homes offers the perfect balance of style, space, and flexibility—designed to meet the needs of modern families and active lifestyles. Featuring 4 to 6 bedrooms, 2.5 to 5 bathrooms, and up to 3,789 square feet of living space, the Carlisle provides room to grow without sacrificing comfort or function.From the welcoming front entry to the spacious open-concept

  

  Maronda Homes

  Builder

  161 Williamson Rd Unit 37110558, Winchester, VA 22602
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  /68

  $794,950

  • 5 Beds
  • 4.5 Baths
  • 4,434 Sq Ft

  111 Abrams Pointe Blvd, Winchester, VA 22602

  Gracious living abounds in this 3 years young Preston model in the prestigious community of Abrams Pointe. Designed for daily living and entertaining with several upgrades and custom features, this home offers it all on a .49AC lot backing to trees for privacy. The first floor offers 10' high ceilings and 9' doors for added ambiance. A custom double sliding glass door in the great room provides

  Becky Hanrahan Coldwell Banker Realty

  111 Abrams Pointe Blvd, Winchester, VA 22602
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  /96

  $858,375

  • 3 Beds
  • 3.5 Baths
  • 4,469 Sq Ft

  650 Gough Rd, Winchester, VA 22602

  A "MacKenzie-Childs" inspired home awaits you and is better than new. Much detail put into this home where French country meets whimsical! Some highlights are as follows: Almost 2.75 acres of peaceful views/setting. Professional hardscaping and landscaping to include paver patio and walkways, BBQ station and fire pit area, new shed with herb garden station behind it and covered rear deck has

  Jim Thomson Realty ONE Group Old Towne

  650 Gough Rd, Winchester, VA 22602
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  /48

  $534,900

  • 3 Beds
  • 3 Baths
  • 2,285 Sq Ft

  257 Jefferson St, Winchester, VA 22601

  Charming Craftsman in West Whitlock Avenue – Walk to John Handley!Welcome to 257 Jefferson Street, a beautifully maintained 3-bedroom, 1 full and 2 half bath Craftsman-style home located in the highly desirable West Whitlock Avenue subdivision. This 2,285 sq ft gem offers timeless charm, modern updates, and a prime location within walking distance to the prestigious John Handley High

  Kathrin Donovan Keller Williams Realty

  257 Jefferson St, Winchester, VA 22601
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  /80

  $679,900

  • 3 Beds
  • 2.5 Baths
  • 2,333 Sq Ft

  1153 Merrimans Ln, Winchester, VA 22602

  Welcome to this one-owner Cape Cod on sought-after Merrimans Lane, just steps from Roscommons. Thoughtfully designed and custom built, this home offers timeless style and comfortable living.Step inside to find gleaming hardwood floors, a well-appointed kitchen with a sunny breakfast area, and a lovely sunroom with direct access to the Trex deck—perfect for enjoying the peaceful views of

  Traci Shoberg RE/MAX Roots

  1153 Merrimans Ln, Winchester, VA 22602
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  /65

  $537,900

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

  341 Warm Springs Rd, Winchester, VA 22603

  What a find! Gorgeous views with this 4BR 2.5BA Colonial situated on 1.22 acre lot. Features main level family room, living room, dining room and kitchen. Enjoy the screened in porch with hot tub; refreshing in ground pool with privacy fence. 2 car garage, basement for added comfort. Must see to appreciate!

  Toni Carone Long & Foster Real Estate, Inc.

  341 Warm Springs Rd, Winchester, VA 22603
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  /50

  $629,900

  • 4 Beds
  • 3.5 Baths
  • 3,829 Sq Ft

  114 Nassau Dr, Winchester, VA 22602

  Beautifully updated 4 bed, 3.5 bath colonial in a prime commuter location just minutes from I-81 and Route 7. Enjoy outdoor living with a fenced backyard, low-maintenance composite decking, brick patio, outdoor fireplace, and a storage shed. The spacious primary suite includes a large walk-in closet. The finished basement is ideal for entertaining, featuring a full bath and wet bar. Recent

  Sheila Pack RE/MAX Roots

  114 Nassau Dr, Winchester, VA 22602
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  /50

  $685,000

  • 4 Beds
  • 2.5 Baths
  • 2,998 Sq Ft

  441 Fair Ln, Winchester, VA 22603

  Discover your perfect retreat at 441 Fair Ln, Winchester, VA 22603, in the peaceful Fairway Estates neighborhood! This stunning 4-bedroom, 2.5-bathroom single-family home spans 2,998 square feet on a sprawling 5.54-acre lot, offering a blend of modern luxury and serene country living. Built in 2000, this meticulously updated residence is just minutes from Historic Downtown Winchester and major

  Caleb Fowler Samson Properties

  441 Fair Ln, Winchester, VA 22603
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  /90

  $515,000

  • 3 Beds
  • 2.5 Baths
  • 1,984 Sq Ft

  2623 Middle Rd, Winchester, VA 22601

  Welcome home to 2623 Middle Rd! Located near all that Winchester has to offer, Middle Rd is a lovely private oasis to come home to. With a myriad of upgrades including a gorgeous screened in back porch, this home offers many conveniences, a spacious layout and bedrooms, and plenty of room for entertainment, hobbies, and whatever you can dream of. Outfitted with a new greenhouse and shed, both

  Nicole Lewis Coldwell Banker Premier

  2623 Middle Rd, Winchester, VA 22601
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  /36

  $565,000 Open Sat 10AM - 1PM

  • 3 Beds
  • 2 Baths
  • 2,517 Sq Ft

  101 Dutton Place, Winchester, VA 22601

  Welcome to 101 Dutton Place— Location, Location, Location! + One Level living! Nestled just inside the Frederick County line in the highly sought-after Merrimans Estates community. This beautifully maintained ranch-style home is ideally situated on a peaceful and meticulously landscaped 1.26-acre lot, minutes from WMC Hospital, downtown Winchester & major commuter routes! Step through

  Lisa Behr Coldwell Banker Premier

  101 Dutton Place, Winchester, VA 22601
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  /35

  $575,000

  • 3 Beds
  • 2 Baths
  • 2,233 Sq Ft

  143 Harvest Ridge Dr, Winchester, VA 22601

  Welcome to 143 Harvest Ridge Drive located in the highly desirable VILLAGE AT HARVEST RIDGE, a 55+ community in Winchester, Virginia. The address says Winchester, but the home is located in Frederick County, just outside of the Winchester City limits making it convenient for shopping, dining out, and medical appointments. This home is elegant, well designed, and meticulously maintained. The

  Elizabeth Page Boxwell MarketPlace REALTY

  143 Harvest Ridge Dr, Winchester, VA 22601
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  /70

  $599,000

  • 3 Beds
  • 2 Baths
  • 1,456 Sq Ft

  251 Heather Hill Ln, Winchester, VA 22603

  Priced below appraised value! Have you been looking for peace and serenity, then you've found it. This gorgeous property offers 10 acres (there are two different parcels included in this sale. Parcels that are included are: 19-3-7 (house parcel, 5 acres), and 19-3-10 (garage, pole barn parcel, 5 acres) The lovely Chalet offers 3 bedrooms and 2 full bathrooms. The main level of the home

  Amber Jenkins Century 21 Redwood Realty

  251 Heather Hill Ln, Winchester, VA 22603
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  /53

  $585,000

  • 3 Beds
  • 2.5 Baths
  • 2,527 Sq Ft

  125 Dewberry Dr, Winchester, VA 22602

  Discover the perfect blend of comfort and convenience in this 3 bedroom, 2 and a half bath single-story rambler nestled in the sought after neighborhood of Ravenwing. This home delivers spacious single level living with outdoor entertaining space and is move in ready. With sidewalks throughout the neighborhood, you can enjoy walking, running, or biking. This home is conveniently located close to

  Brittany Sims Keller Williams Capital Properties

  125 Dewberry Dr, Winchester, VA 22602
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  /114

  $550,000

  • 4 Beds
  • 2.5 Baths
  • 1,798 Sq Ft

  720 S Kent St, Winchester, VA 22601

  Welcome to the beautifully preserved American Foursquare where music legend Patsy Cline once lived with her mother—and later, with her husband, Charlie Dick. Built in 1931, this four-bedroom, one-and-a-half-bath home blends timeless character with thoughtful updates, all wrapped in the charm of one of Winchester’s most historic neighborhoods.Inside, you’ll find nearly 1,800 square feet of

  Krissy Cruse Pearson Smith Realty, LLC

  720 S Kent St, Winchester, VA 22601
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  /48

  $574,900

  • 4 Beds
  • 3.5 Baths
  • 2,602 Sq Ft

  1629 Pondview Dr, Winchester, VA 22601

  Discover tranquility and spacious living in this exceptional 4-bedroom, 3.5-bath home, with a main-level primary suite, ideally situated on one half of an acre backing to picturesque trees and wide-open fields. From the moment you step inside, you'll appreciate the meticulously maintained interior and inviting open floor plan. The living room features a cathedral ceiling and a cozy gas fireplace,

  Kerry & Ed Stinson Berkshire Hathaway HomeServices PenFed Realty

  1629 Pondview Dr, Winchester, VA 22601
• 

  

  /49

  $599,000

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

  1019 Berryville Ave, Winchester, VA 22601

  1019 Berryville Avenue, Winchester, VA 22601 is a Fully-rented triplex located just minutes from Old Town Winchester and Shenandoah University. This approximately 3,000 sq. ft. property is configured as three fully independent residential and commercial units. All units have private entrances, full kitchens, and separate electric. Middle unit may be used for commercial space. Units have been

  Pamela Debnam Houwzer, LLC

  1019 Berryville Ave, Winchester, VA 22601
• 

  

  /47

  $575,000

  • 4 Beds
  • 3 Baths
  • 2,203 Sq Ft

  167 Morning Glory Dr, Winchester, VA 22602

  Welcome to the beautiful Twin Lakes Community! This charming ranch-style residence offers the ease of one-level living with a spacious and thoughtfully designed floor plan. The main level features a welcoming front den—perfect for a home office or reading nook—an updated kitchen with a large pantry area, a dining room filled with natural light, and a cozy family room complete with a gas

  Lisa Behr Coldwell Banker Premier

  167 Morning Glory Dr, Winchester, VA 22602

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