Winchester, VA Homes for Sale

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  /34

  $650,490

  New Construction

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

  239 Hydrangea 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

  239 Hydrangea Way, Winchester, VA 22602
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  /17

  $450,690

  New Construction $2K PRICE DROP

  • 3 Beds
  • 2.5 Baths
  • 1,657 Sq Ft

  136 Wappinger Terrace, 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 white siding exterior with stone accents, while the interior boasts sleek white kitchen and bathroom cabinets paired with modern finishes throughout. Enjoy

  D.R. Horton Builder

  136 Wappinger Terrace, Winchester, VA 22602
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  /33

  $310,000

  • 2 Beds
  • 1 Bath
  • 1,472 Sq Ft

  323 Fairview Ave, Winchester, VA 22601

  Welcome home to this beautifully updated 2-bedroom, 1-bath single-family residence offering charm, comfort, and modern upgrades throughout. From the inviting front porch to the spacious fenced backyard, this move-in ready home combines classic character with thoughtful renovations. Inside, you’ll find brand new LVP flooring on both levels and a completely renovated kitchen featuring ceramic tile

  Jeremy Browne EXP Realty, LLC

  323 Fairview Ave, Winchester, VA 22601
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  /28

  $244,900

  $14K PRICE DROP

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

  8 Brookland Ct Unit 8, Winchester, VA 22602

  2 Bed, 2 bath condominium. New appliances, including water heater and heat pump. Gas fireplace, open concept with separate dining room. Patio/ porch with french doors and skylights in living room allow tons of natural light. Primary suite includes walk-in closet. Conveniently located off rt 7 and 81.

  Vicki Broy RE/MAX Roots

  8 Brookland Ct Unit 8, Winchester, VA 22602
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  /54

  $449,990

  • 3 Beds
  • 3.5 Baths
  • 2,239 Sq Ft

  142 Sequoia Dr, Winchester, VA 22602

  Some homes check the boxes. Others quietly stand apart the moment you pull up. This one does that. Not because it tries to impress, but because the setting, the layout, and the way the house sits on the land just make sense. Start with the lot. It’s a premium double-sized end-unit lot, something you simply don’t see often in townhouse communities. The home sits at the edge of the

  Alexander Bracke Real Broker, LLC

  142 Sequoia Dr, Winchester, VA 22602
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  /19

  $141,500

  • Land
  • 11.1 Acres
  • $12,748 per Acre

  0 Hodges Lot 14 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 14 Ln, Winchester, VA 22603
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  /16

  $2,124,900

  New Construction

  • 3 Beds
  • 2 Baths
  • 1,801 Sq Ft

  152.44 Acres Lot 2 Laurel Grove Rd, Winchester, VA 22602

  This is a rare opportunity to build a fully custom home tailored to your vision, crafted by Winchester’s award-winning builder, Hepler Homes. The home shown is a representative example of what can be built on this exceptional property. List price reflects the included options outlined in the documents section and is subject to change based on custom selections.The featured model offers a

  Nadeem Helfer Samson Properties

  152.44 Acres Lot 2 Laurel Grove Rd, Winchester, VA 22602
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  /2

  $200,000

  • 1 Bed
  • 1 Bath

  5737 N Frederick Pike, Winchester, VA 22603

  4.2 Acres, Sold As-Is, Flat Usable Lot, Partially Wooded, Well and Septic Exists, Just Outside of Winchester VA, No HOA, Unrestricted. Well and septic on property . Well is located in back of old mobile home at water pump. Septic located further back behind old mobile home marked wirh red sparay paint. Health department docs are in bright. Neither house nor mobile home livable.Sold As Is With

  Tracy Link Coldwell Banker Premier

  5737 N Frederick Pike, Winchester, VA 22603
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  /42

  $315,000

  • 3 Beds
  • 1.5 Baths
  • 1,170 Sq Ft

  126 Marple Rd, Winchester, VA 22603

  Charming Cape Cod-style home located at 126 Marple Rd in the desirable north end of Winchester! This well-maintained 3-bedroom, 1.5-bath home offers timeless character, functional living space, and a convenient commuter-friendly location. The main level features a bedroom with a 1/2 bath, a living room, a dining room, and a kitchen. Upstairs, you’ll find additional bedrooms with a shared

  RoxAnn Grimes RE/MAX Roots

  126 Marple Rd, Winchester, VA 22603
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  /35

  $675,000

  • 3 Beds
  • 2.5 Baths
  • 1,650 Sq Ft

  112 W Germain St, Winchester, VA 22601

  100-Year-Old Downtown Winchester Charmer – Fully Reimagined in 2025!This stunning, fully restored century-old home seamlessly blends historic charm with high-end modern upgrades in the heart of downtown Winchester. Completely taken down to the studs and rebuilt in 2025, every detail was thoughtfully executed—nothing was overlooked. Proudly recognized with the 2025 Preservation of Historic

  Amanda Magana RE/MAX Roots

  112 W Germain St, Winchester, VA 22601
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  /2

  $429,000

  Coming Soon

  • 2 Beds
  • 2 Baths
  • 1,031 Sq Ft

  118 1/2 E Cork St, Winchester, VA 22601

  Seeking the perfect blend of historic character and modern urban living? This exceptional Urban Lofts Condominium is just one and a half blocks from Winchester’s historic downtown walking mall, offering easy access to restaurants, bars, boutiques, and entertainment. Originally built in the 1900s, this beautifully updated home showcases exposed brick walls, timeless architectural charm, and

  Janet Flaherty Keller Williams Realty

  118 1/2 E Cork St, Winchester, VA 22601
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  /48

  $489,900

  • 5 Beds
  • 4 Baths
  • 2,288 Sq Ft

  144 Morning Glory Dr, Winchester, VA 22602

  Motivated Seller! Extraordinary 5-Bedroom Home with Pool and Dual Kitchens in Winchester This exceptional 5-bedroom, 3.5-bathroom home — complete with a private office — offers comfort, functionality, and modern elegance. Thoughtfully designed for both everyday living and relaxed entertaining, this residence features two fully renovated kitchens (one on the main level and one in the walkout

  Julieta Russell Keller Williams Realty Dulles

  144 Morning Glory Dr, Winchester, VA 22602
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  /34

  $1,585,000

  New Construction

  • 4 Beds
  • 5.5 Baths
  • 4,684 Sq Ft

  Lot 4 - Honeycrisp, 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. Entrance Road Under Construction, currently. These lots feature panoramic views of the entire Shenandoah Valley from Harper's Ferry to Strasburg to the Western Mountains, providing stunning views from

  JP Carr Merrifield Realty, LLC

  Lot 4 - Honeycrisp, Winchester, VA 22603
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  /37

  $425,000

  $5K PRICE DROP

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

  133 Woodrow Rd, Winchester, VA 22602

  Set on the east side of Winchester in Carlisle Heights, this inviting 3 bedroom, 3 full bath split foyer offers style, function, and a commuter-friendly location just minutes from Route 7. Inside, you’ll find a bright, open feel with easy-care flooring flowing through the main living spaces and bedrooms. The kitchen has been tastefully refreshed with crisp white cabinets, stainless steel

  Kevin Pringle Samson Properties

  133 Woodrow Rd, Winchester, VA 22602
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  /7

  $129,000

  • Land
  • 8.3 Acres
  • $15,542 per Acre

  0 Light Rd, Winchester, VA 22603

  Large lot available! WELL ON SITE! Over 8 acres for sale in Northern Frederick County, VA at the top of The Shenandoah Valley! Perfect for building or recreation/hunting. Turkey, deer and other wildlife abound. Only 20 minutes from Winchester! 20 minutes from Berkeley Springs, WV! Looking for that perfect get-a-way spot to enjoy wildlife and nature? This may be it! Lot is fully wooded. Ideal

  Jennifer Watt Century 21 Redwood Realty

  0 Light Rd, Winchester, VA 22603
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  /5

  $10,000

  • Land
  • 0 Sq Ft

  Lot 13 Tomahawk Trai 0, Winchester, VA 22602

  Welcome to Shawneeland! This mountain community is tucked away in a rural setting and a short distance to shopping, restaurants and Winchester's Historic Downtown. Utilize this 0.48 acre lot as a potential building lot, recreational space or enjoy the amenities such as Lake Cherokee with a beach area, fishing and picnic areas. Purchaser to verify location of boundary lines.

  Kim Hurst MarketPlace REALTY

  Lot 13 Tomahawk Trai 0, Winchester, VA 22602
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  /34

  $389,900

  $10K PRICE DROP

  • 3 Beds
  • 2.5 Baths
  • 1,986 Sq Ft

  107 Tye Ct, Winchester, VA 22602

  PRICE REDUCED and OPEN HOUSES this weekend, Saturday 5/23 12pm-2pm - Sunday, May 24th 10:am-2pm. Welcome to this beautifully maintained and thoughtfully enhanced home, built in 2023 and offering the feel of nearly new construction. Since purchasing, the current owners have added valuable upgrades including a spacious deck, a water filtration and softener system, and ceiling fans in the bedrooms

  Robin Gebhardt EXP Realty, LLC

  107 Tye Ct, Winchester, VA 22602
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  /94

  $795,000

  • 5 Beds
  • 4 Baths
  • 4,075 Sq Ft

  274 Woodside Ln, Winchester, VA 22603

  Welcome to 274 Woodside - a secluded house on 5.06 acres with tons of storage! This 4,310 SF rambler style home has 2 masters (one up and one down), 4 bathrooms (2 on the main floor have heated floors), a huge kitchen with tons of cabinets, a large island with a 5 burner propane cooktop, and a pantry cabinet with pull-out shelves for storage, two fireplaces - one propane and one wood-burning

  Cindy Butler Virginia Property Group, Inc.

  274 Woodside Ln, Winchester, VA 22603
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  /13

  $598,990

  New Construction $76K PRICE DROP

  • 3 Beds
  • 3 Baths
  • 2,875 Sq Ft

  TO BE BUILT-HOMESITE Duke Ct, Winchester, VA 22602

  TO BE BUILT – This home has not been constructed yet. Photos are of a similar model and may show optional features. Appointment at model home – 154 Williamson Rd. Price reflects base price plus options. Estimated delivery timeline is approximately 6–7 months. The Drexel offers generous living space in a beautifully designed ranch home featuring 3 bedrooms and 3 bathrooms, with approximately 3,213

  Greta Fernandez New Home Star Virginia, LLC

  TO BE BUILT-HOMESITE Duke Ct, Winchester, VA 22602
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  /70

  $749,500

  • 6 Beds
  • 4 Baths
  • 4,672 Sq Ft

  817 Chelsea Dr, Winchester, VA 22601

  Spacious 5-6-bedroom, 4-bath brick-front rancher with a fully finished basement, offering flexible living space for today’s needs. The main level features a welcoming living room with a tray ceiling & a gas fireplace, a formal dining room with crown molding & chair rail, and a well-appointed kitchen with Corian countertops and a walk-in pantry. The primary suite is conveniently located on the

  Sheila Pack RE/MAX Roots

  817 Chelsea Dr, Winchester, VA 22601
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  /11

  $75,000

  $15K PRICE DROP

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

  152 Fiddler Ave Unit C318, Winchester, VA 22603

  Welcome to Regency Lakes a all age active and vibrant community, where you can find yourself in your dream home. We have updated 2001 3 bed, 2 bath home featuring a large open floor plan. Step inside to find a bright and airy open floor plan, stone wood burning fireplace and updated bathrooms. The spacious kitchen boasts a multi level center island and a pass through, perfect for both everyday

  Kristina Kelly Regency Lakes

  152 Fiddler Ave Unit C318, Winchester, VA 22603
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  /2

  $3,500

  • Land
  • 10,890 Sq Ft
  • $14,000 per Acre

  107 Fox Trail, Winchester, VA 22602

  Babak Taghavi Venture Realty

  107 Fox Trail, Winchester, VA 22602
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  /8

  $760,000

  New Construction $15K PRICE INCREASE

  • 3 Beds
  • 3.5 Baths
  • 2,550 Sq Ft

  0 Tumble Leaf Ln, Winchester, VA 22602

  CARRINGTON HOMES AT FALL RIDGE ESTATES- 5 Acre Wooded LOTS WITH MOUNTAIN VIEWS. Choose from 7 different floorplans including our Dogwood model ( One Story Living ) with standard 10' main level ceilings and 13' ceilings in the Family Room. Model Home Open on Weekends from 11-5 at 156 Covey Lane Winchester Va

  Daniel Boris Pearson Smith Realty, LLC

  0 Tumble Leaf Ln, Winchester, VA 22602
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  /3

  $755,320

  New Construction

  • 3 Beds
  • 2.5 Baths
  • 2,380 Sq Ft

  120 Malbec Ct, 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 3,194 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 to a

  Maronda Homes Builder

  120 Malbec Ct, Winchester, VA 22602
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  /39

  $498,000

  New Construction Coming Soon

  • 4 Beds
  • 2.5 Baths
  • 2,023 Sq Ft

  39 Rossmann Blvd, Winchester, VA 22602

  To be built-choose your colors and upgrades! Photos are similar and include upgrades. Beautifully crafted new home by a respected local builder, offering over 2,000 square feet of thoughtfully designed living space in the desirable Sovereign Village community. The inviting, open-concept main level features a spacious kitchen with a large island, perfect for gathering and entertaining, that

  Marisa Varley ERA Oakcrest Realty, Inc.

  39 Rossmann Blvd, Winchester, VA 22602
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  /24

  $25,000

  • Land
  • 1.43 Acres
  • $17,483 per Acre

  LOT 5A Fox Trail, Winchester, VA 22602

  Beautiful building lot located in Mountain Falls Park – Wilde Acres. This is the last lot on the right on Fox Trail, offering excellent privacy and seclusion. The property backs to permanent open space, providing a peaceful setting with mountain views and abundant wildlife. Approved for a 3-bedroom septic system with a certification letter on file. A current survey is also available. This is an

  Nadeem Helfer Samson Properties

  LOT 5A Fox Trail, Winchester, VA 22602
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  /27

  $399,900

  New Construction

  • 3 Beds
  • 3 Baths
  • 1,914 Sq Ft

  208 Beaver Trail, Winchester, VA 22602

  Hardwoods down. Painted. Cabinets going in. To be completed soon.Current Shawneeland Inventory208 Beaver Trail (split foyer)210 Beaver Trail (split foyer)212 Falcon Tarail (colonial)211 Inca Trail (colonial)103 Tonto Trail (split foyer)123 Killbuck Trail (colonail)Stunning 3BR/3BA home on 0.33+ acre lot with public water & available Xfinity internet. Easy entrance

  Jim Thomson Realty ONE Group Old Towne

  208 Beaver Trail, Winchester, VA 22602
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  /15

  $435,000

  • 5 Beds
  • 4 Baths
  • 2,014 Sq Ft

  122 Cherry Hill Cir, Winchester, VA 22602

  Nestled in the charming Green Acres subdivision, this delightful split-level home offers a perfect blend of comfort and functionality. With five spacious bedrooms and four full bathrooms, there's ample room for everyone to unwind and thrive. The heart of the home features a cozy fireplace, inviting you to gather with loved ones during chilly evenings. The fully finished basement, complete with

  Jen Moore ERA Oakcrest Realty, Inc.

  122 Cherry Hill Cir, Winchester, VA 22602
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  /20

  $299,999

  • 3 Beds
  • 2 Baths
  • 1,362 Sq Ft

  553 Highland Ave, Winchester, VA 22601

  Awesome Colonial Revival just four blocks from Winchester's beloved walking mall! This 1921 charmer has been completely transformed with a total make-over you'll love. Brand new stainless steel appliances make cooking a joy, while fresh vinyl laminate flooring flows throughout for easy living. New LED fixtures brighten every room, and classy bathroom updates add that spa-like touch. Tucked away

  Teri Domanski Your Home Sold Guaranteed Realty - East LLC

  553 Highland Ave, Winchester, VA 22601
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  /22

  $309,900

  New Construction $10K PRICE DROP

  • 3 Beds
  • 2 Baths
  • 1,032 Sq Ft

  429 Bluebird Trail, Winchester, VA 22602

  It is done and ready for you! New Home Private Retreat with Views & Premium UpgradesNestled on over half an acre with views and open 3 acre lots to the rear, this new home offers the high-end feel you want at an affordable price point. The interior boasts an open-concept design with a private primary suite separated from the guest bedrooms. Quality shines in the details: white wood cabinetry

  Jim Thomson Realty ONE Group Old Towne

  429 Bluebird Trail, Winchester, VA 22602
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  /42

  $625,000

  • 4 Beds
  • 3 Baths
  • 2,996 Sq Ft

  1564 Perry Rd, Winchester, VA 22602

  Discover the perfect blend of comfort and contemporary living in this stunning detached home, nestled on a generous 1.35-acre lot. Built in 2009, this residence boasts a modern architectural style that harmonizes with its serene surroundings, offering a peaceful retreat from the hustle and bustle of everyday life. Step inside to find a spacious layout that invites you to create lasting memories.

  Nate Vogel Century 21 Redwood Realty

  1564 Perry Rd, Winchester, VA 22602
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  /79

  $850,000

  • 5 Beds
  • 5.5 Baths
  • 6,256 Sq Ft

  150 Ewell Dr, Winchester, VA 22602

  Welcome to Equestrian Estates, a highly sought-after Winchester community with no HOA, where space, style, and flexibility come together beautifully. This stately 5-bedroom, 6-bath Colonial offers over 6,700 square feet of finished living space on nearly 3 private acres, creating the perfect setting for both everyday living and entertaining. The home was not available for showings over the past

  Sherry Santmyer Hunt Country Sotheby's International Realty

  150 Ewell Dr, Winchester, VA 22602
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  /38

  $561,990

  New Construction

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

  BRISTOL Plan at Willow Run, Winchester, VA 22601

  We're excited to introduce the Bristol, our stunning new ranch design! This floorplan starts at 1,748 square feet and features 3 bedrooms, 2 bathrooms, and a 2-car garage. Step into a welcoming foyer that guides you past two cozy secondary bedrooms and into the main living area, where the family room, charming dining nook, and beautifully designed kitchen come together. The kitchen boasts ample

  D.R. Horton Builder

  105 Trellis View Ln Unit 36406038, Winchester, VA 22601
• 

  

  /23

  $389,760

  New Construction Open Wed 12PM - 3PM

  • 4 Beds
  • 3.5 Baths
  • 2,000 Sq Ft

  112 Shuoner Ct, Winchester, VA 22602

  June 2026 Delivery 4 BR | 3.5 BA | 1-Car Garage | Finished Lower Level | Larger Deck Beautiful wooded homesites available!Offering up to 2,000 sq. ft. of modern, open-concept living. Home Highlights Open-concept main level – perfect for entertaining Granite countertops Stainless steel appliances Luxury vinyl plank flooring Upper Level Retreat Deluxe Silver primary bath with rain shower

  Jimmy Thomas New Home Star Virginia, LLC

  112 Shuoner Ct, Winchester, VA 22602
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  /28

  $399,000

  $16K PRICE DROP

  • 3 Beds
  • 1 Bath
  • 1,260 Sq Ft

  307 Fox Run Ln, Winchester, VA 22602

  Wake up to breathtaking views of the Shenandoah Valley every day in this peaceful, beautifully renovated cottage. Completely updated in 2024, the home blends modern amenities with warm, inviting charm.The bright, open living space features a vaulted ceiling and abundant natural light, creating an airy, welcoming atmosphere. The living room showcases large windows, custom built-ins, and a

  Karen Sparks Corcoran McEnearney

  307 Fox Run Ln, Winchester, VA 22602
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  /51

  $399,999

  • 3 Beds
  • 2 Baths
  • 2,131 Sq Ft

  204 Ridge Rd, Winchester, VA 22602

  Well maintained brick Rancher(upgraded vinyl clad tilt windows,newer architectural roof) on a full basement on the east side of Winchester featuring over 2100 sqft of finished living space that offers true hardwood flooring on the main level with 3 bedrooms and 1 full bath. Spacious living room that features a gas log fireplace that has a woodstove insert included. Basement is 90% finished with a

  James Amick RE/MAX Roots

  204 Ridge Rd, Winchester, VA 22602
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  /27

  $449,990

  New Construction

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

  FREEPORT DUPLEX Plan at Willow Run - Duplexes, Winchester, VA 22601

  Looking for a beautiful home that meets all your needs? Look no further than the Freeport! This stunning 1,492 square foot residence features three bedrooms, two baths, and a convenient two-car garage, all designed with your active adult lifestyle in mind. As you step into the foyer, you are greeted by the open-concept kitchen and living area with plenty of space for cooking, dining, and

  D.R. Horton Builder

  105 Trellis View Ln Unit 36406838, Winchester, VA 22601
• 

  

  /39

  $421,000

  • 3 Beds
  • 2.5 Baths
  • 2,277 Sq Ft

  422 S Loudoun St, Winchester, VA 22601

  Welcome home to this beautifully maintained historic log home in the heart of Winchester. Thoughtfully updated while maintaining the charm of yesteryear this home offers the conveniences of modern living. Traditionally appointed, the main level of the home provides the perfect separation of spaces with a large formal living room, dining room, gourmet kitchen, additional full bath and main level

  Dana Cloud Realty ONE Group Old Towne

  422 S Loudoun St, Winchester, VA 22601
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  /38

  $319,000

  $26K PRICE DROP

  • 2 Beds
  • 2 Baths
  • 1,382 Sq Ft

  31 E Germain St, Winchester, VA 22601

  IMPROVED PRICING! Nestled in the heart of Winchester City’s Historic District and walkable to shops and restaurants, this charming 2-bedroom, 2-bathroom gem is a rare find! The large front porch has great curb appeal and is the perfect place for outdoor lounging. The home is filled with natural light that illuminates the clean white walls and warm hardwood flooring. The living room flows into the

  Sue-Anne DeBergh Compass

  31 E Germain St, Winchester, VA 22601
• 

  

  /3

  $1,200,000

  • Land
  • 2.38 Acres
  • $504,202 per Acre

  0 Prosperity Dr, Winchester, VA 22602

  2.38 Acres at the intersection of Valley Pike and Prosperity Drive. Located in the Kernstown area of Frederick County/Winchester. Property is located across from the street from CMA Honda, Aldi Supermarket, Outback Steakhouse, and Carrabba's Italian Grill & Restaurant. Located in close proximity to the intersection of I-81, US Route 37, and US Route 11. Excellent signage opportunities,

  H. Paige Manuel Oakcrest Commercial LLC.

  0 Prosperity Dr, Winchester, VA 22602

Showing Results 201 - 240, Page 6 of 11