Winchester, VA Homes for Sale

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  /73

  $615,000

  Open Sat 12PM - 2PM

  • 5 Beds
  • 3.5 Baths
  • 3,626 Sq Ft

  922 Wayne Dr, Winchester, VA 22601

  Welcome home to this beautifully updated brick-front residence in the City of Winchester, where a thoughtful floor plan, generous living spaces with 9' ceilings on the main and upper levels, and meaningful improvements come together across three finished levels.The main level is designed for connection and comfort, beginning with a two-story foyer that opens into an airy, open-concept layout.

  Katrina Smith Samson Properties

  922 Wayne Dr, Winchester, VA 22601
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  /85

  $690,000

  $10K PRICE DROP

  • 4 Beds
  • 4.5 Baths
  • 4,918 Sq Ft

  108 Norfolk Ct, Winchester, VA 22602

  Welcome home to Norfolk Ct!!! Oh my, where to begin? If you're looking for a turnkey home with ample space and lots of room for your dreams, then this is the home for you! Located on a quiet Cul-de-Sac, this beautiful brick home welcomes you with an impressive foyer and high ceilings. The first floor of this home houses a lovely kitchen with an ample great room, combination formal living/dining

  Nicole Lewis Coldwell Banker Premier

  108 Norfolk Ct, Winchester, VA 22602
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  /9

  $17,000

  • Land
  • 18,295 Sq Ft
  • $40,476 per Acre

  Lot 76 Bear Trail, Winchester, VA 22602

  Looking for a lot in a quiet, rural development where you can enjoy the beauty of nature, listen to the birds, and view an occasional wild turkey or deer? This undeveloped lot in Shawneeland may be just the place for you. With its spring-fed lake, great for fishing or swimming, and mountain trails, Shawneeland is the perfect place to build a getaway retreat or a full-time residence. Located

  Rebecca McTavish Long & Foster Real Estate, Inc.

  Lot 76 Bear Trail, Winchester, VA 22602
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  /8

  $1,400,000

  • Land
  • 5.73 Acres
  • $244,328 per Acre

  1667 N Frederick Pike, Winchester, VA 22603

  Great highway exposure exposure to state route 37 the bypass around the West side of Winchester and and 5222 north or North Frederick Pike entrance at a signalized intersection

  John Scully Colony Realty

  1667 N Frederick Pike, Winchester, VA 22603
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  /25

  $559,990

  New Construction $16K PRICE DROP

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

  133 Wappinger Terrace, Winchester, VA 22602

  The Hayden is a spacious two-story home offering 6 bedrooms, 4 bathrooms, and over 3,100 square feet of thoughtfully designed living space, perfect for both everyday living and entertaining. The main level features a versatile flex room off the foyer, ideal for a formal dining room, home office, or additional living space. The gourmet kitchen includes an oversized island with seating, a large

  D.R. Horton Builder

  133 Wappinger Terrace, Winchester, VA 22602
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  /2

  $2,525,100

  • Land
  • 8.86 Acres
  • $285,000 per Acre

  0 Kavanaugh Dr Unit VAFV2017570, Winchester, VA 22602

  8.86 Acres of undeveloped commercial land zoned B-2 with excellent US 37 future signage visibility, exposure, and location. All utilities available for connection. Approved uses include self-storage warehouses, distribution warehouses, car washes, new car dealerships, hotels and restaurants.

  Marie DiLorenzo Oakcrest Commercial LLC.

  0 Kavanaugh Dr Unit VAFV2017570, Winchester, VA 22602
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  /40

  $289,000

  $11K PRICE DROP

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

  110 Brookland Ct Unit 10, Winchester, VA 22602

  Welcome home to this one-of-a-kind, fully renovated penthouse condo that has been transformed right down to the studs! Offering luxury finishes rarely found at this price point, this stunning residence is unlike anything else available in Frederick County under $300,000.Every detail has been thoughtfully updated, including a new gas furnace, new HVAC system, new flooring throughout,

  Traci Shoberg Samson Properties

  110 Brookland Ct Unit 10, Winchester, VA 22602
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  /40

  $359,990

  New Construction

  • 3 Beds
  • 3.5 Baths
  • 1,756 Sq Ft

  237 Monteith Dr, Winchester, VA 22601

  The most affordable townhomes in Winchester City! Luxury 3-level, 3-bedroom townhome with 1-car garage located in the heart of Winchester! Home backing to trees for added privacy and peaceful views. Possibility of 4th bedroom or flex space in the finished lower level with private full bath and walk-in shower; ideal for guests, home office, or recreation room***OFFERING UP TO $5K IN CLOSING

  Brittany Newman DRB Group Realty, LLC

  237 Monteith Dr, Winchester, VA 22601
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  /20

  $154,650

  • Land
  • 12.9 Acres
  • $11,988 per Acre

  0 Hodges Lot 11 Ln, Winchester, VA 22603

  Own a piece of the beautiful Back Creek Heights community in Cross Junction. Located just minutes north of Winchester in the Dehaven part of the county. Access is secured via road frontage on Hodges Lane. Experience exciting hunting as many types of wildlife call this property home including deer, turkey, and many small game species. This tract is currently being used for recreation and hunting.

  Chad Pangle Whitetail Properties Real Estate, LLC

  0 Hodges Lot 11 Ln, Winchester, VA 22603
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  /31

  $608,745

  New Construction

  • 2 Beds
  • 2 Baths
  • 1,748 Sq Ft

  227 Hydrangea 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

  227 Hydrangea Way, Winchester, VA 22602
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  /65

  $389,999

  Open Sun 12PM - 2PM

  • 3 Beds
  • 3.5 Baths
  • 2,232 Sq Ft

  114 Comanche Trail, Winchester, VA 22602

  Mountain living meets modern convenience! This immaculate Shawneeland home offers the ultimate retreat while keeping you perfectly close to both the community entrance and the beach. Meticulously maintained and completely move-in ready, this property truly has it all. Step inside to find freshly painted walls throughout, highlighted by gleaming hardwood floors on the main level and cozy, plush

  Hailey Mooney Real Broker, LLC

  114 Comanche Trail, Winchester, VA 22602
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  /46

  $372,990

  New Construction

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

  ADAMS Plan at Retreat at Winding Creek - Townhomes, Winchester, VA 22602

  The 1,889 sq. ft. Adams townhome design comes complete with 4 bedrooms, 3.5 bathrooms, and a 1-car garage. You will love the granite counter tops, stainless steel appliances, and recessed lighting in the kitchen. Create the rec room, home office or 4th bedroom of your dreams in the lower level bonus space! The Adams comes with a 12'x10' deck off the rear of the home, perfect for outdoor

  D.R. Horton Builder

  137 Seminole Dr Unit 36203787, Winchester, VA 22602
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  /13

  $299,000

  • 3 Beds
  • 1.5 Baths
  • 1,161 Sq Ft

  519 Virginia Ave, Winchester, VA 22601

  This charming house has great potential. It is located directly across from the Virginia Avenue School campus, close to downtown Winchester. The exterior was recently painted and a new roof installed in 2025. This home would be great "Handyman's Delight" as the interior needs quite a bit of attention as the bath and kitchen are outdated. The 100 amp electric service was updated in 1993, water

  Katherine Solenberger Colony Realty

  519 Virginia Ave, Winchester, VA 22601
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  /22

  $574,990

  New Construction

  • 3 - 5 Beds
  • 2 - 4 Baths
  • 2,137+ Sq Ft

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

  The Rembrandt is thoughtfully designed to offer a seamless balance of private and communal spaces, all while prioritizing main-level living. A covered entryway gracefully welcomes you home, leading to a central gathering area encompassing the family room, kitchen, and dining area. The kitchen is a culinary enthusiast's haven, featuring a substantial center island, ample cabinetry, and a

  Brookfield Residential Builder

  105 Wagtail Ln Unit 36578844, Winchester, VA 22603
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  /2

  $1,170,000

  Coming Soon Sep 3

  • 5 Beds
  • 5.5 Baths
  • 3,846 Sq Ft

  854 Valley Mill Rd, Winchester, VA 22602

  Unique 5+ acre property in Winchester. Beautiful home with plenty of space for everyone's interests. 5 bedrooms- all with en suite bathrooms. High end kitchen designed by a chef. Plenty of outdoor entertaining areas. 2400 sq ft garage/workshop, green house, extensive gardens including koi pond. Abrams Creek runs along the back of property. Wildlife including Bald eagles, Blue heron, and deer

  Linden McLean Samson Properties

  854 Valley Mill Rd, Winchester, VA 22602
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  /11

  $624,880

  New Construction

  • 2 Beds
  • 2 Baths
  • 2,658 Sq Ft

  159 Williamson Rd, Winchester, VA 22602

  159 Williamson Rd, Winchester, VA 22602
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  /27

  $609,990

  New Construction

  • 4 Beds
  • 3 Baths
  • 3,000 Sq Ft

  601 Granite Ridge Dr, Winchester, VA 22603

  Brand New Main Level home is under construction and with special financing and closing cost assistance available, there is no reason to wait to make this the next place you call home! Located within Hiatt Pointe at Snowden Bridge, an active adult community for those 55 or better!This Rembrandt, located on a corner lot, a stunning home offering a harmonious blend of private sanctuaries and

  Elizabeth Ellis Brookfield Mid-Atlantic Brokerage, LLC

  601 Granite Ridge Dr, Winchester, VA 22603
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  /23

  $424,990

  New Construction $5K PRICE INCREASE

  • 4 Beds
  • 3.5 Baths
  • 2,094 Sq Ft

  126 Swansong Place, Winchester, VA 22603

  BUILDER OFFERING BELOW MARKET RATE FINANCING ON THIS MOVE IN READY HOME!!Exceptional value for a 4‑bedroom END‑UNIT townhome is ready for move‑in! Brand‑new construction offers modern style and comfort with oak stairs with upgraded railings and durable LVP flooring throughout the main level. Backing to open space in the newest section of Snowden Bridge, this spacious home includes a flexible

  Elizabeth Ellis Brookfield Mid-Atlantic Brokerage, LLC

  126 Swansong Place, Winchester, VA 22603
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  /15

  $299,999

  $30K PRICE DROP

  • 3 Beds
  • 1 Bath
  • 1,056 Sq Ft

  211 Fair Ln, Winchester, VA 22603

  Beautifully newly remodeled ranch-style home set on a spacious 0.62-acre flat lot. This move-in ready residence features a fully updated interior with a modern kitchen complete with granite countertops, brand-new stainless steel appliances, and all-new cabinetry. The home showcases rich hardwood flooring throughout and has been thoughtfully upgraded with new windows and a newer metal roof for

  Kenny Ritenour Samson Properties

  211 Fair Ln, Winchester, VA 22603
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  /30

  $379,900

  • 2 Beds
  • 1.5 Baths
  • 1,186 Sq Ft

  711 E Cork St, Winchester, VA 22601

  This stunning property boasts a brand-new kitchen with quartz countertops, new appliances (refrigerator, microwave, stove) and a fresh new look. The laundry room got an upgrade too, with brand-new appliances. Newly installed waterproof vinyl flooring that's been laid down throughout, perfect for any occasion. Also, with a fresh coat of paint on the walls including the garage along with the door.

  Marco Novillo Spring Hill Real Estate, LLC.

  711 E Cork St, Winchester, VA 22601
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  /2

  $3,200,000

  • Land
  • 451 Acres
  • $7,095 per Acre

  472 Mccubbin, Winchester, VA 22601

  Adrian Small TTR Sotheby's International Realty

  472 Mccubbin, Winchester, VA 22601
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  /61

  $649,900

  $25K PRICE DROP

  • 3 Beds
  • 2 Baths
  • 2,242 Sq Ft

  132 Triangle Ct, Winchester, VA 22602

  **HUGE PRICE REDUCTION** Nearly new and designed for easy main-level living, this beautifully maintained Winchester ranch offers 2,242 finished square feet on the main level plus a full 2,242-square-foot walkout lower level—more than 4,400 total square feet of space and opportunity.Built in 2024, the warm, open floor plan features 9-foot ceilings, abundant natural light, durable LVP

  Kelly Davis RE/MAX Gateway, LLC

  132 Triangle Ct, Winchester, VA 22602
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  /7

  $1,150,000

  New Construction

  • 3 Beds
  • 3 Baths
  • 2,947 Sq Ft

  60 Gravenstein Ct, Winchester, VA 22602

  MAIN LEVEL LIVING in an Idyllic Setting - Welcome to Stonymeade ! -2 acre Home Site in Winchester VirginiaBase price shown is for the Dogwood MAIN LEVEL LIVING FLOORPLAN and we have many other plans including those with first floor primary suites, farmhouse kitchens, and multi-generational options.All homes include exceptional standard features including 10' main level ceilings,

  Daniel Boris Pearson Smith Realty, LLC

  60 Gravenstein Ct, Winchester, VA 22602
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  /22

  $599,950

  $25K PRICE DROP

  • 5 Beds
  • 2 Baths
  • 1,948 Sq Ft

  446 N Loudoun St, Winchester, VA 22601

  Fully renovated in 2022, this upgraded duplex near Winchester's historic Walking Mall features all new electrical, HVAC, plumbing, windows, insulation, and appliances. The downstairs is a 3-bed/1-bath unit, and the upstairs is a 2-bed/1-bath unit. Separate utilities, with landlord covering water/sewer. Gross income: $44,640 annually, including shed rental. Quality tenants and off-street parking

  Lawrence Lessin Homes By Owner, Inc.

  446 N Loudoun St, Winchester, VA 22601
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  /31

  $824,900

  $75K PRICE DROP

  • 4 Beds
  • 3 Baths
  • 3,943 Sq Ft

  230 Conifer Ln, Winchester, VA 22602

  WOW - what a price improvement - schedule your viewing now!! Perched on a picturesque knoll with sweeping mountain views, this thoughtfully designed modern farmhouse colonial offers the perfect balance of luxury, comfort, and peaceful country living—without sacrificing modern convenience. Built in 2018, this 4-bedroom, 3-bath home offers over 3,100 square feet of beautifully designed living space

  Traci Shoberg Samson Properties

  230 Conifer Ln, Winchester, VA 22602
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  /3

  $3,200,000

  • Land
  • 13.05 Acres
  • $245,211 per Acre

  0 0 Northwestern Pike, Winchester, VA 22602

  Prime opportunity on 13.05 acres in an unbeatable high-visibility location along Route 50 in Winchester, VA. Positioned directly across from major retailers and conveniences—including Walmart, Sheetz, Tractor Supply, Applebee’s, Dunkin’, Bojangles, and the Winchester Medical Center campus—this property offers exceptional exposure and accessibility. Zoned for multiple development possibilities,

  Sarah Reynolds Keller Williams Realty

  0 0 Northwestern Pike, Winchester, VA 22602
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  /50

  $849,900

  New Construction

  • 5 Beds
  • 3 Baths
  • 3,057 Sq Ft

  Lot 10 Desant Cir, Winchester, VA 22603

  Four month build time from contract. Seize a rare opportunity to own one of just fifteen premier lots within the prestigious, upper-scale Keplinger Estates near the Apple Pie Ridge area. This is not just a house; it is a bespoke sanctuary offering a sophisticated lifestyle with the ultimate convenience of being close to town, yet free from the constraints of an HOA. Experience the pinnacle of a

  Jim Thomson Realty ONE Group Old Towne

  Lot 10 Desant Cir, Winchester, VA 22603
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  /83

  $825,000

  $64K PRICE DROP

  • 5 Beds
  • 3.5 Baths
  • 3,800 Sq Ft

  107 Launchris Dr, Winchester, VA 22602

  Looking for a home that gives you space, style, privacy, and the freedom to make it your own? Welcome to this stately Colonial set on nearly an acre of beautiful, private land—where timeless architecture meets the upgrades today's buyers want.The seller has invested more than $150,000 in improvements, including a fully renovated HVAC system with all-new ductwork and high-end components.

  Laura White ERA Oakcrest Realty, Inc.

  107 Launchris Dr, Winchester, VA 22602
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  /47

  $419,924

  $20K PRICE DROP

  • 4 Beds
  • 2 Baths
  • 1,868 Sq Ft

  187 Village Ct, Winchester, VA 22602

  **New Price!!** Move-In Ready • No HOA • Great location across from Winchester Country Club! * Oversized 2-Car Garage! * Beautifully updated split foyer tucked away on a quiet cul-de-sac in the desirable Rolling Fields community. Freshly painted throughout with brand-new carpet, gleaming hardwood floors, updated luxury vinyl plank flooring, granite countertops, and stainless steel appliances,

  Bob Caines RE/MAX Distinctive Real Estate, Inc.

  187 Village Ct, Winchester, VA 22602
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  /31

  $649,500

  • 3 Beds
  • 2 Baths
  • 2,450 Sq Ft

  1400 Gordon Place, Winchester, VA 22601

  One level living in The Downs at Meadow Branch, a sought after community convenient to shopping, medical center, and Old Town Winchester. Expansive all-brick home offers 3 bedrooms, 2 bathrooms, attached 2-car garage and 2450 square feet of living space! What's better than an idyllic 1/5 acre corner lot... how about an idyllic 1/5 acre corner lot you don't have to mow? HOA fees include lawn

  Stacy Rodgers Berkshire Hathaway HomeServices PenFed Realty

  1400 Gordon Place, Winchester, VA 22601
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  /38

  $369,900

  • 3 Beds
  • 1 Bath
  • 1,256 Sq Ft

  201 Marple Rd, Winchester, VA 22603

  2.44 Acres with 1-Car Attached + 3-Bay Detached Workshop Garage — Close to WinchesterSolid 1953 stucco home on 2.44 acres with a small wet weather pond and livestock fencing—ready for animals, a hobby farm, or just keeping the property secure. 1,256 square feet, 3 bedrooms, 1 full bath, and an unfinished basement. 2 Bedrooms are on the main level.Check out the shop space! The

  Scott Wachtel Century 21 Redwood Realty

  201 Marple Rd, Winchester, VA 22603
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  /9

  $9,500

  • Land
  • 23,958 Sq Ft
  • $17,273 per Acre

  LOTS 8 & 9 Elk Trail, Winchester, VA 22602

  Great opportunity to own two beautiful wooded lots full of mature trees and plenty of privacy! These adjoining parcels offer a wonderful chance to connect with nature and enjoy peaceful surroundings. Located just about 30 minutes from downtown Winchester, you get the perfect mix of country calm and town convenience. Whether you’re thinking about outdoor fun, future plans, or simply an investment,

  Kristin Crosby Samson Properties

  LOTS 8 & 9 Elk Trail, Winchester, VA 22602
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  /101

  $849,900

  $40K PRICE DROP

  • 5 Beds
  • 5 Baths
  • 5,226 Sq Ft

  102 Julie Ct, Winchester, VA 22602

  Opportunities of this caliber in the highly coveted Stonebrook Farms community are exceptionally rare. Positioned on a premium cul-de-sac lot backing directly to mature, private woods, this property is a true unicorn in today’s market: a sprawling, intelligently designed estate paired with a resort-style backyard and an exhaustive list of major capital improvements.The main level makes an

  Charles Witt Nova Home Hunters Realty

  102 Julie Ct, Winchester, VA 22602
• 

  

  /31

  $524,990

  New Construction

  • 3 - 5 Beds
  • 2 - 4.5 Baths
  • 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, abundant

  Brookfield Residential Builder

  105 Wagtail Ln Unit 36578843, Winchester, VA 22603
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  /33

  $340,000

  $20K PRICE DROP

  • 3 Beds
  • 2 Baths
  • 1,218 Sq Ft

  544 Bluebird Trail, Winchester, VA 22602

  Opportunity is knocking! The Sellers are Motivated and open to reasonable offers. If your considering making a move, now is the time to take a closer look!Escape to the peaceful mountain community of Wilde Acres and discover this charming 3-bedroom, 2-bath home situated on a spacious ½-acre lot. This well-maintained property offers privacy, tranquility, and numerous recent upgrades

  Dona Shiley ERA Oakcrest Realty, Inc.

  544 Bluebird Trail, Winchester, VA 22602
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  /38

  $350,000

  New Construction $10K PRICE DROP

  • 3 Beds
  • 2 Baths
  • 2,072 Sq Ft

  604 Gatling Dr, Winchester, VA 22602

  Welcome to this beautiful 3-bedroom, 2-bathroom split-level home, a brand-new build nestled on a spacious 0.26-acre lot in the Mountain Falls Park community. Enjoy a warm welcome with a cozy covered porch. Inside, the home features luxury vinyl plank flooring throughout, providing a modern, durable finish. The kitchen is a chef's delight, with stainless steel appliances, premium shaker-style

  Sheila Pack RE/MAX Roots

  604 Gatling Dr, Winchester, VA 22602
• 

  /2

  $299,000

  $66K PRICE DROP

  • 4 Beds
  • 2.5 Baths
  • 2,678 Sq Ft

  719 National Ave, Winchester, VA 22601

  Priced to sell! A true Federal‑style gem, this solid brick home offers the chance to restore a piece of architectural history. Rich with original craftsmanship, it features high ceilings, original hardwood floors, solid wood doors and trim, and a beautiful covered front porch—timeless details that showcase the home’s enduring character. Designed with good bones and a layout that adapts to many

  Windy Harris Hunt Country Sotheby's International Realty

  719 National Ave, Winchester, VA 22601
• 

  

  /39

  $749,900

  • 3 Beds
  • 3 Baths
  • 2,112 Sq Ft

  1049 Laurel Grove Rd, Winchester, VA 22602

  This is the one that offers the perfect blend of privacy, comfort, and natural beauty. This custom-built 3-bedroom, 3-bath retreat sits on a private, wooded lot with expansive mountain views, creating a peaceful setting that still keeps you close to everyday conveniences.The main-level primary suite provides a relaxing escape with its elegant walk-in shower and soaking tub. Two additional

  LESLIE WEBB Long & Foster Real Estate, Inc.

  1049 Laurel Grove Rd, Winchester, VA 22602
• 

  

  /50

  $1,179,000

  • 4 Beds
  • 5 Baths
  • 4,970 Sq Ft

  1004 Heth Place, Winchester, VA 22601

  Stepping onto the Southern style covered front porc.h you enter the large foyer with a Schoenbek chandelier. There is a living room to the left which opens to a separate dining room with a hand painted blue and gold ceiling. The kitchen is eating size with granite counter and large island. Double doors lead to a small back porch and stairs to the patio. The first floor family room has a gas

  Kathryn Hallett Long & Foster Real Estate, Inc.

  1004 Heth Place, Winchester, VA 22601
• 

  

  /137

  $819,900

  • 3 Beds
  • 3.5 Baths
  • 2,484 Sq Ft

  250 Creola Dr, Winchester, VA 22603

  Contract fell thru at no fault of the seller or the home. Contract was contingent on Home Sale. Tucked away on 3.54 private wooded acres, this beautifully designed custom home offers the perfect balance of luxury, privacy, and convenience—just 15 minutes from Winchester, VA and Winchester Medical Center. With almost 2,500 square feet of thoughtfully designed living space, a full unfinished

  Curtis Siever NextHome Realty Select

  250 Creola Dr, Winchester, VA 22603

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