Newest Homes for Sale in Winchester, VA

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  /47

  $1,099,900

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

  Lot 1 Keval Gyan Way, Winchester, VA 22603

  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 single-level living in this

  Jim Thomson Realty ONE Group Old Towne

  Lot 1 Keval Gyan Way, Winchester, VA 22603
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  /45

  $950,000

  • 3 Beds
  • 2.5 Baths
  • 3,100 Sq Ft

  Lot 12 Keval Gyan Way, Winchester, VA 22603

  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 single-level living in this immaculate,

  Jim Thomson Realty ONE Group Old Towne

  Lot 12 Keval Gyan Way, Winchester, VA 22603
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  /4

  $849,999

  • 3 Beds
  • 2 Baths
  • 2,488 Sq Ft

  Lot 11 Keval Gyan Way, Winchester, VA 22603

  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 (new PIN OAK model); 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 single-level living

  Jim Thomson Realty ONE Group Old Towne

  Lot 11 Keval Gyan Way, Winchester, VA 22603
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  /23

  $374,990 New Construction

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

  105 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

  105 Castaway Place, Winchester, VA 22603
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  /15

  $55,000

  • Land
  • 1.3 Acres
  • $42,308 per Acre

  LOT 152 Bobcat Trail, Winchester, VA 22602

  This lot is your perfect building spot if you are looking for the best views! Overlooking the mountain and plenty of semi cleared softly, sloped land, this lot is already perked for a 3 bedroom home and well site located. Originally three separate lots, it has been combined into a 1.3acre lot and is waiting for you to build your mountain retreat on.

  

  Kimberly Schroeder

  Long & Foster Real Estate, Inc.

  (540) 782-3211

  LOT 152 Bobcat Trail, Winchester, VA 22602
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  /16

  $299,990

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

  405 1/2 Elm St, Winchester, VA 22601

  This is a two level house 3 bedrooms 2 full bathrooms good for fist time buyers or investment property, ready to move in , house is sold as is. Thank you for showing.

  Virgilio & Maria Vasquez The Vasquez Group LLC

  405 1/2 Elm St, Winchester, VA 22601
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  /11

  $269,000

  • 2 Beds
  • 1.5 Baths
  • 1,116 Sq Ft

  518 Yorktowne Place, Winchester, VA 22601

  This exquisite end-of-row townhouse, underwent a major renovation in 2025, offers a perfect blend of modern luxury and timeless comfort. With two spacious bedrooms and one and a half elegantly appointed bathrooms, this home is designed for both relaxation and entertaining. Step inside to discover a gourmet kitchen that will inspire your culinary adventures. Featuring upgraded granite countertops,

  Brandon Pifer Pifer Realty, LLC

  518 Yorktowne Place, Winchester, VA 22601
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  /2

  $476,500 Coming Soon

  • 3 Beds
  • 3 Baths
  • 2,568 Sq Ft

  407 Jefferson St, Winchester, VA 22601

  COMING SOON! Your PERFECT TURN KEY classic colonial, fully UPDATED, and PHENOMENALLY LOCATED! Stroll to the restaurants in Old Town, enjoy the activities at Handley, or walk to the trails at MSV! NEW, NEW, NEW! New roof, HVAC, privacy fencing, custom paint and built-in cabinetry, plus new stainless steel appliances, including washer/dryer. GET CREATIVE in your FINISHED lower level walk-out!

  Gillian Greenfield Coldwell Banker Premier

  407 Jefferson St, Winchester, VA 22601
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  /34

  $399,000

  • 4 Beds
  • 1.5 Baths
  • 1,953 Sq Ft

  318 E Piccadilly St, Winchester, VA 22601

  This delightful brick Colonial, perfectly situated in the heart of downtown Winchester, combines classic architecture with modern updates and an unbeatable location close to every downtown amenity, including restaurants, schools, shopping, parks, and major commuter routes. The home welcomes you with a large foyer featuring newly refinished hardwood floors that extend throughout the entire

  Dan Whitacre Colony Realty

  318 E Piccadilly St, Winchester, VA 22601
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  /49

  $655,000

  • 4 Beds
  • 4.5 Baths
  • 4,354 Sq Ft

  218 Flanagan Dr, Winchester, VA 22602

  This stunning home in Raven Wing offers over 4,100 sq. ft. of living space and was extensively updated in 2020. The main level features hardwood flooring, an open-concept kitchen with an island, recessed lighting, and stainless-steel appliances. You’ll also find a formal dining room and a spacious living room complete with a gas fireplace. The kitchen has been upgraded with shaker-style,

  Robert Mann Burch Real Estate Group, LLC

  218 Flanagan Dr, Winchester, VA 22602
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  /2

  $3,500

  • Land
  • 0.25 Acre
  • $14,000 per Acre

  107 Fox Trail, Winchester, VA 22602

  Babak Taghavi Venture Realty

  107 Fox Trail, Winchester, VA 22602
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  /6

  $699,999 New Construction

  • 5 Beds
  • 4 Baths
  • 3,850 Sq Ft

  Preston Plan at Abrams Pointe, Winchester, VA 22602

  The Preston plan greets guests with an inviting covered porch, and continues to impress with a formal dining room, spacious great room and well-appointed kitchen featuring a center island, walk-in pantry and nook. A mudroom, powder room and private study round out the main floor. Upstairs, discover a central laundry, a large loft, three secondary bedrooms with a shared bath and an elegant primary

  Richmond American Homes Builder

  101 Abrams Pointe Blvd Unit 38693285, Winchester, VA 22602
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  /73

  $849,900

  • 5 Beds
  • 4.5 Baths
  • 3,767 Sq Ft

  199 Meeting House Dr, Winchester, VA 22602

  Welcome to this spacious 5-bedroom, 4.5-bath home offering over 3,700 sq. ft. of finished living space seated on almost 3 and 1/2 acres . This property has been thoughtfully updated throughout, with new bathrooms, updated kitchen, new carpet, fresh paint, and numerous additional improvements—too many to list. The main-level primary suite features an en-suite bath with a soaking tub, dual vanity,

  Katie Deskins Century 21 Redwood Realty

  199 Meeting House Dr, 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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  /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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  /14

  $404,990 New Construction

  • 3 Beds
  • 1.5 Baths
  • 2,433 Sq Ft

  106 Heirloom Way, 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

  106 Heirloom Way, Winchester, VA 22603
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  /21

  $499,990 New Construction

  • 2 Beds
  • 1 Bath
  • 1,564 Sq Ft

  110 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

  110 Carnation Way, Winchester, VA 22603
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  /27

  $414,990 New Construction

  • 3 Beds
  • 1.5 Baths
  • 2,433 Sq Ft

  119 Heirloom Way, 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

  119 Heirloom Way, Winchester, VA 22603
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  /46

  $359,000

  • 3 Beds
  • 2.5 Baths
  • 1,719 Sq Ft

  415 Quail Dr, Winchester, VA 22602

  Beautiful 3 bed, 2.5 bath split foyer on a gorgeous .52-acre lot backing to mature trees. Enjoy outdoor living on the paver patio with built-in firepit, surrounded by thoughtful landscaping that enhances curb appeal and privacy. Spacious interior layout, bright natural light, and a peaceful setting make this home an ideal blend of comfort and convenience. Enjoy granite countertops, table space,

  Sheila Pack RE/MAX Roots

  415 Quail Dr, Winchester, VA 22602
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  /20

  $439,900 New Construction

  • 3 Beds
  • 3 Baths
  • 1,935 Sq Ft

  109 Glen Ridge Rd, Winchester, VA 22602

  New construction! Pictures are if similar model. Conveniently located just minutes from town, this home offers comfort and style. With 3 bedrooms and 3 full baths, you will find many features such as beautiful hardwood floors throughout the main level, primary bedroom with walk in closet and bath with walk in shower, crown molding, granite counter top, 2 car garage and so much more! Don't miss

  Pamela Russell CENTURY 21 New Millennium

  109 Glen Ridge Rd, Winchester, VA 22602
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  /16

  $450,000

  • Land
  • 77 Acres
  • $5,844 per Acre

  92 Bobcat Trail, Winchester, VA 22602

  Calling all hunters or just someone who wants seclusion! This property has amazing views and already has a structure perfect to finish your way! Perfect for getting away from it all or long hunting trips. No septic or power to structure yet. Gate to enter property. Property has 2 pink flags at the beginning of property and runs all the way to the power lines.

  Daryl Stout RE/MAX Real Estate Connections

  92 Bobcat Trail, Winchester, VA 22602
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  /29

  $356,000 Open Sun 12PM - 2PM

  • 3 Beds
  • 1.5 Baths
  • 1,164 Sq Ft

  111 Meadowview Ct, Winchester, VA 22602

  Step into this well-cared-for home in the peaceful Greenwood Heights neighborhood convenient to Route 50, Route 7, and Winchester. This easy single-floor layout features 3 bedrooms and 1.5 baths and is ideal for those just starting out or looking to downsize. The comfortable floor plan is ready for your personal touch, and the spacious fenced backyard with deck and storage shed are perfect for

  Kathleen Hobbs ERA Oakcrest Realty, Inc.

  111 Meadowview Ct, Winchester, VA 22602
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  /12

  $165,000

  • Land
  • 7.4 Acres
  • $22,297 per Acre

  0 Back Mountain Road Lot 11, Winchester, VA 22602

  Enjoy beautiful views of the valley from this 7.4-acre private lot! Located just 15-20 minutes from downtown Winchester. Build a weekend getaway or the dream home you have always wanted. Easement to property from Back Mountain Road. See property docs attached.

  Sheila Pack RE/MAX Roots

  0 Back Mountain Road Lot 11, Winchester, VA 22602
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  /45

  $285,000

  • 2 Beds
  • 1 Bath
  • 997 Sq Ft

  108 Martin Dr, Winchester, VA 22602

  Charming brick rambler situated on a spacious corner lot, just minutes from Route 7 and I-81—an ideal location for commuters. The property offers a driveway and a carport, perfect for convenient parking or doubling as a shaded outdoor space for entertaining, along with generous storage space. Inside, you’ll find an open-concept living room and eat-in kitchen with large windows that let in plenty

  Heloisa Amar Samson Properties

  108 Martin Dr, Winchester, VA 22602
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  /24

  $265,000

  • 2 Beds
  • 1 Bath
  • 882 Sq Ft

  204 Shenandoah Ave, Winchester, VA 22601

  Great opportunity to own this 2-bed, 1-bath Winchester City charmer that sits just minutes from Shenandoah University and the Old Town walking mall. Main level living with a bright comfortable living area, an eat-in kitchen home that includes a bonus room providing flexible space for an office, playroom, fitness area, or guest room, central air and the convenience of an in-home washer & dryer

  Janet Flaherty Keller Williams Realty

  204 Shenandoah Ave, Winchester, VA 22601
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  /3

  $3,025,000

  • Land
  • 27.09 Acres
  • $111,665 per Acre

  0 Renaissance Dr, Winchester, VA 22602

  27.09 +/- acres in the direct path of Light Industrial-Zoned land. The subject property is in the comprehensive plan to be zoned Light Industrial for warehousing, distribution, self-storage warehousing or light manufacturing. The 27.09 +/- acre site has excellent proximity and access to US 11, Route 37. and I-81. The property provides location, visibility, and exposure. All utilities are

  H. Paige Manuel Oakcrest Commercial LLC.

  0 Renaissance Dr, Winchester, VA 22602
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  /36

  $365,000

  • 4 Beds
  • 2 Baths
  • 1,780 Sq Ft

  127 Shirley St, Winchester, VA 22601

  Comfortable living at this split-foyer home located in the heart of the City of Winchester. On the main level, you’ll find three bedrooms and a full bath. The lower level features a fourth bedroom plus a second full bath — ideal for guests, or a home office. Location is a standout. You’re just minutes from downtown dining, shopping, and community events, and enjoy easy access to schools, parks,

  

  Bradley Comstock

  ERA Oakcrest Realty, Inc.

  (540) 802-5087

  127 Shirley St, Winchester, VA 22601
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  /30

  $329,900

  • 4 Beds
  • 1.5 Baths
  • 1,456 Sq Ft

  126 Plainfield Dr, Winchester, VA 22602

  Live in town on south end with a viable yard with two sheds, 4 bedrooms, some simple updates mostly from 2020, hardwood floors, over 1400sqft, no hoa, and close proximity to major road arteries. Utilities are public water, septic, and electric. Dbox and lines were replaced in 2012 (Septic number of bedrooms). Owner is licensed VA real estate agent.

  Dave Spence RE/MAX Roots

  126 Plainfield Dr, Winchester, VA 22602
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  /2

  $409,990 New Construction

  • 3 Beds
  • 2 Baths
  • 2,060 Sq Ft

  Deep Creek II Plan at Village at Valor Crossing - Townhomes, Winchester, VA 22601

  The Largest New Construction Townhome In Winchester! Attached 1-car garage or flex option. Open concept kitchen with optional island opens to country kitchen, sun room, and living room. Alternative main level option available. Optional choices available include a study and a fireplace. Owner’s suite with a generous walk-in closet, dual vanity, and seated shower. Four-foot rear extension

  DRB Homes Builder

  0 Tbd Weems Ln Unit 38608305, Winchester, VA 22601
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  /98

  $699,900

  • 6 Beds
  • 4.5 Baths
  • 4,124 Sq Ft

  461 Skylar Lanes Way, Winchester, VA 22603

  Welcome to 461 Skylar Lanes Way, a stunning home nestled on over 2 acres in the upscale & sought after Walnut Springs Estates community, with just minutes from downtown Winchester! This spacious residence offers 6 bedrooms, 4.5 bathrooms, finished basement and a 3-car side load garage with a circular paved driveway, providing plenty of room for family, guests, and entertaining. Step inside the

  Michele Gibson Samson Properties

  461 Skylar Lanes Way, Winchester, VA 22603
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  /32

  $379,000

  • 2 Beds
  • 2 Baths
  • 1,590 Sq Ft

  203 Crestwood Ln, Winchester, VA 22602

  Welcome home to this well-maintained property located in an established Winchester neighborhood. The property features a functional main-level layout with a bright living area and a sunroom that adds additional usable space. Recent updates include a roof installed around 5 years ago, new kitchen appliances, a new hot water heater, and new wood flooring. The kitchen offers ample cabinet and

  Jen Richards MarketPlace REALTY

  203 Crestwood Ln, Winchester, VA 22602
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  /52

  $649,900 Open Sat 1PM - 3PM

  • 4 Beds
  • 2.5 Baths
  • 3,514 Sq Ft

  121 Poe Dr, Winchester, VA 22602

  ***OPEN HOUSE- Sunday December 21**** Don’t miss this stunning and truly one-of-a-kind home, thoughtfully designed for modern living and entertaining located in desirable Raven Oaks community. Like new with large, open floor plan! Main foyer entrance greets you with impeccable detail, from the upgraded lighting to the custom wall paneling- unLike any other. The spacious, gourmet kitchen serves as

  Rheema Ziadeh Redfin Corporation

  121 Poe Dr, Winchester, VA 22602
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  /65

  $405,000 Open Sat 11AM - 1PM

  • 3 Beds
  • 2 Baths
  • 1,802 Sq Ft

  414 S Cameron St, Winchester, VA 22601

  Located in Winchester’s Historic District, 414 S Cameron Street offers a thoughtful blend of character, modern improvements, and a spacious outdoor setting just blocks from Old Town. Inside, the main level features beautifully refinished hardwood floors, fresh interior and exterior paint, and unique architectural touches including exposed brick, built-ins, and exposed log details in select rooms

  Natasha Roberts Realty ONE Group Old Towne

  414 S Cameron St, Winchester, VA 22601
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  /13

  $605,990 New Construction

  • 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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  /23

  $585,990 New Construction

  • 4 Beds
  • 2.5 Baths
  • 2,682 Sq Ft

  199 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 Somerset Floorplan is a beautiful 4-bedroom, 2.5-bath home that offers up to 3,514 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

  Dorelba Estrada New Home Star Virginia, LLC

  199 Malbec Ct, Winchester, VA 22602
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  /12

  $598,990 New Construction

  • 3 Beds
  • 2 Baths
  • 3,056 Sq Ft

  24 Williamson Rd, 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 Drexel Floorplan 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

  Dorelba Estrada New Home Star Virginia, LLC

  24 Williamson Rd, Winchester, VA 22602
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  /34

  $1,485,000

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

  Lot 18 Honeycrisp Way, Winchester, VA 22603

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

  JP Carr Merrifield Realty, LLC

  Lot 18 Honeycrisp Way, Winchester, VA 22603
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  /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

  $385,000

  • 3 Beds
  • 2.5 Baths
  • 1,678 Sq Ft

  100 Maury Way, Winchester, VA 22602

  Welcome to this Former Model Home for the Grand Nassau model by Ryan Homes - once the Winchester Landing 55+ community's showcase villa, thoughtfully designed to highlight elegant architecture, stylish finishes, and countless upgrades. Perfectly positioned on a desirable corner lot with expanded green space, this home blends sophistication with comfort, creating a lifestyle that feels both

  Matt Boyer Keller Williams Realty

  100 Maury Way, Winchester, VA 22602
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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

Showing Results 81 - 120, Page 3 of 9