Winchester County VA Homes for Sale

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  $434,990 New Construction

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

  1802 Blythe Way, Winchester, VA 22601

  1802 Blythe Way is an attractive new 3 level end townhome with full brick front in Winchester, VA scheduled for a November move-in. Our modern Adams floorplan features a 1-car garage, and along with a bedroom and full bathroom on the first floor. Stained oak stairs lead you to the main level with LVP floors. The kitchen is equipped with beautiful quartz countertops, white cabinets, and

  D.R. Horton Builder

  1802 Blythe Way, Winchester, VA 22601
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  /2

  $269,000 Coming Soon

  • 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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  $385,000

  • 3 Beds
  • 1.5 Baths
  • 1,435 Sq Ft

  20 W Clifford St, Winchester, VA 22601

  Discover a unique investment opportunity in the heart of the Winchester Historic District! This charming 3-bedroom, 1.5-bathroom traditional brick home, built in 1900, offers a blend of historic character and modern potential. With a compact lot size of just 0.06 acres, maintenance is minimal, allowing for a focus on maximizing rental income or resale value. The detached structure features a

  Minh-Thieng Le Levi Clarke, LLC

  20 W Clifford St, Winchester, VA 22601
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  /54

  $395,000

  • 3 Beds
  • 1.5 Baths
  • 1,274 Sq Ft

  225 Fox Dr, Winchester, VA 22601

  Welcome to 225 Fox Drive — a beautifully maintained all-brick rancher offering comfort, efficiency, and convenience in one ideal package. This 3-bedroom, 1.5-bath home features a bright and upgraded kitchen with quartz countertops, new cabinetry, stainless steel appliances, and an induction stove. Hardwood floors flow throughout the main level, adding warmth and timeless charm. A full walk-up

  Laura White ERA Oakcrest Realty, Inc.

  225 Fox Dr, Winchester, VA 22601
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  /4

  $469,900 Coming Soon

  • 3 Beds
  • 1.5 Baths
  • 1,698 Sq Ft

  312 W Cecil St, Winchester, VA 22601

  Coming Soon! Don’t miss your chance to live on sought-after W. Cecil in this charming, beautifully maintained historic home. Light-filled and inviting, this home welcomes you with a classic covered front porch and warm hardwood floors that set the tone for the character throughout. The cozy living room features a recently converted gas fireplace, lovely built-ins, and crown molding. This space

  

  Jeanne Mezzatesta

  Colony Realty

  (540) 413-0699

  312 W Cecil St, Winchester, VA 22601
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  $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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  /11

  $409,990 New Construction

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

  TBB Monteith Dr Unit DEEP CREEK II, Winchester, VA 22601

  ***OFFERING UP TO $7K IN CLOSING COST ASSISTANCE FOR PRIMARY RESIDENCE WITH USE OF APPROVED LENDER AND TITLE!** SPECIAL INTEREST RATES AVAILABLE** CONTACT SALES CONSULTANT FOR DETAILS*The only amenity-filled community within Winchester City! Discover modern living in this 3-4-bedroom, 2-3.5-bath home designed for comfort, style, and functionality. The open-concept main level features an

  Brittany Newman DRB Group Realty, LLC

  TBB Monteith Dr Unit DEEP CREEK II, Winchester, VA 22601
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  /35

  $409,990 New Construction

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

  1814 Blythe Way, Winchester, VA 22601

  1814 Blythe Way is an attractive new 3 level townhome with full brick front in Winchester, VA for November move-in. Our modern Adams floorplan features a 1-car garage, and along with a bedroom and full bathroom on the first floor. Stained Oak stairs lead you to the main level with LVP Floors. The kitchen is equipped with beautiful Quartz countertops, Stone Grey cabinets, and stainless-steel

  D.R. Horton Builder

  1814 Blythe Way, Winchester, VA 22601
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  $479,990 New Construction

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

  1829 Harvest Dr, Winchester, VA 22601

  1829 Harvest Drive is an attractive end unit new 3 level townhome with full brick front in Winchester, VA for December move-in. Our modern Adams II floorplan features a 1-car garage, and a bedroom and full bathroom on the first floor. Stained Oak stairs lead you to the main level with LVP Floors. The kitchen is equipped with beautiful quartz countertops, white cabinets, and stainless-steel

  Brooks Sears D R Horton Realty of Virginia LLC

  1829 Harvest Dr, Winchester, VA 22601
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  /38

  $459,990 New Construction

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

  1805 Harvest Dr, Winchester, VA 22601

  1805 Harvest Drive is an attractive new 3 level townhome with full brick front in Winchester, VA for December move-in. Our modern Adams II floorplan features a 1-car garage, and a bedroom and full bathroom on the first floor. Stained Oak stairs lead you to the main level with LVP Floors. The kitchen is equipped with beautiful quartz countertops, white cabinets, and stainless-steel appliances. The

  Brooks Sears D R Horton Realty of Virginia LLC

  1805 Harvest Dr, Winchester, VA 22601
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  /35

  $449,990 New Construction

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

  1822 Blythe Way, Winchester, VA 22601

  1822 Blythe Way is an attractive new 3 level end townhome with full brick front in Winchester, VA for November move-in. Our modern Adams floorplan features a 1-car garage, and along with a bedroom and full bathroom on the first floor. Stained Oak stairs lead you to the main level with LVP Floors. The kitchen is equipped with beautiful quartz countertops, white cabinets, and stainless-steel

  D.R. Horton Builder

  1822 Blythe Way, Winchester, VA 22601
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  /38

  $459,990 New Construction

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

  1817 Harvest Dr, Winchester, VA 22601

  1817 Harvest Drive is an attractive new 3 level townhome with full brick front in Winchester, VA for December move-in. Our modern Adams II floorplan features a 1-car garage, and a bedroom and full bathroom on the first floor. Stained Oak stairs lead you to the main level with LVP Floors. The kitchen is equipped with beautiful quartz countertops, white cabinets, and stainless-steel appliances. The

  Brooks Sears D R Horton Realty of Virginia LLC

  1817 Harvest Dr, Winchester, VA 22601
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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

  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 fireplace. Owner’s suite with generous walk-in closet, dual vanity, and seated shower. Four foot rear extension available. Finished lower level option available.

  DRB Homes Builder

  0 Tbd Weems Ln Unit 38608305, Winchester, VA 22601
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  $650,000 Open Sat 2PM - 4PM

  • 5 Beds
  • 3.5 Baths
  • 3,552 Sq Ft

  2708 Cassidy Ct, Winchester, VA 22601

  **** OPEN HOUSE **** SATURDAY, DECEMBER 13TH FROM 2:00-4:00 PM**** IT IS THE PERFECT TIME TO TOUR **** Rolling Hills Estates located in the Winchester City area, this beautifully maintained 5-bedroom, 3.5-bath home offers 3,552 sq ft of finished living space on a .35-acre cul-de-sac lot. Featuring a 3-car garage w/220 Car Charger, fully fenced backyard, covered front porch, and a rear Trex deck

  Geri Deane Hunt Country Sotheby's International Realty

  2708 Cassidy Ct, Winchester, VA 22601
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  /25

  $379,990 New Construction

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

  230 Monteith Dr, Winchester, VA 22601

  OPEN HOUSE: Saturday - Sunday 1pm - 3pm 3 Level Home with Deck! MOVE-IN READY! 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

  DRB Homes Builder

  230 Monteith Dr, Winchester, VA 22601
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  $379,990 New Construction

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

  222 Monteith Dr, Winchester, VA 22601

  OPEN HOUSE: Saturday - Sunday 1pm - 3pm 3 Level Condo with Box Bay Windows! 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. Inside, the kitchen stands out with an extended island that seats four at counter height. The first

  DRB Homes Builder

  222 Monteith Dr, Winchester, VA 22601
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  /30

  $379,990 New Construction

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

  209 Monteith Dr, Winchester, VA 22601

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

  DRB Homes Builder

  209 Monteith Dr, Winchester, VA 22601
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  $375,000

  • 3 Beds
  • 3 Baths
  • 2,016 Sq Ft

  7 N Purcell Ave, Winchester, VA 22601

  Welcome to this thoughtfully updated, truly move-in-ready Cape Cod at 7 N Purcell Ave in Winchester! As you step inside, you’ll be greeted by beautiful hardwood floors flowing through the spacious and light-filled living room. The charming eat-in kitchen features modern quartz countertops, a farmhouse-style sink, and plenty of cabinet space—perfect for everyday meals or entertaining. Retreat to

  

  Jodi Cilley

  Realty ONE Group Old Towne

  (540) 559-5146

  7 N Purcell Ave, Winchester, VA 22601
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  $564,900

  • 3 Beds
  • 4 Baths
  • 2,489 Sq Ft

  687 Woodland Ave, Winchester, VA 22601

  Experience refined living in this stunning two-level brick residence, designed with an open-concept layout that seamlessly blends sophistication and comfort. The home features 4 spacious bedrooms, each with a private full bathroom.The kitchen boasts granite countertops and elegant finishes, flowing effortlessly into the dining and living areas — perfect for entertaining or relaxing by the gas

  Mauricio Argandona Fairfax Realty Select

  687 Woodland Ave, Winchester, VA 22601
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  /34

  $500,000

  • 3 Beds
  • 2.5 Baths
  • 1,978 Sq Ft

  236 Miller St, Winchester, VA 22601

  Charming 3 Bedroom, 2.5 Bath Colonial just blocks from Old Town Winchester, offering easy access to dining, entertainment, and shopping! Enjoy outdoor living on the spacious covered front porch or in the fenced backyard. The landscaping features beautiful lilac and rose bushes. The eat-in kitchen features granite countertops, a tile backsplash, hardwood floors, and newer stainless steel

  Sheila Pack RE/MAX Roots

  236 Miller St, Winchester, VA 22601
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  $389,880 Open Wed 12PM - 4PM

  • 3 Beds
  • 4 Baths
  • 1,989 Sq Ft

  117 Boone Ct, Winchester, VA 22602

  Immediate Move-in at Rossum Crossing! Winchester's newest and most popular townhome community, conveniently located near shopping and dining options. The St. Paul Townhome features three bedrooms, two and a half baths, and a one-car garage. The main floor boasts an open-concept floor plan, with a spacious family room that flows into a fully equipped kitchen. The kitchen includes an island, a

  Dorelba Estrada New Home Star Virginia, LLC

  117 Boone Ct, Winchester, VA 22602
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  /21

  $384,880 Open Wed 12PM - 4PM

  • 3 Beds
  • 4 Baths
  • 1,989 Sq Ft

  105 Boone Ct, Winchester, VA 22602

  Move in ready at Rossum Crossing townhome community, conveniently located near shopping and dining options. The St. Paul Townhome features three bedrooms, two and a half baths, and a one-car garage. The main floor boasts an open-concept floor plan, with a spacious family room that flows into a fully equipped kitchen. The kitchen includes an island, a pantry closet, and a breakfast nook. This

  Dorelba Estrada New Home Star Virginia, LLC

  105 Boone Ct, Winchester, VA 22602
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  $299,990

  • 3 Beds
  • 1 Bath
  • 1,205 Sq Ft

  627 Watson Ave, Winchester, VA 22601

  CLASSIC CHARM MEETS CONTEMPORARY COMFORT IN THIS FANTASTIC DUPLEX UNIT! This charming Winchester duplex unit seamlessly blends timeless character with modern conveniences, offering the perfect balance of historic flair and contemporary living. Nestled just minutes from the vibrant heart of downtown Winchester, this inviting property combines an unbeatable location with a thoughtfully-updated

  Kristin Crosby Samson Properties

  627 Watson Ave, Winchester, VA 22601
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  /95

  $660,000

  • 4 Beds
  • 3.5 Baths
  • 4,101 Sq Ft

  608 Kernstown Ct, Winchester, VA 22601

  Discover the charm and serenity of suburban living at 608 Kernstown Court, nestled in the storied landscape of Winchester, Virginia. This picturesque address offers an ideal blend of history, convenience, and modern comfort, an inviting sanctuary for families, professionals, or anyone seeking a peaceful yet well connected lifestyle.This desirable property features a beautifully appointed

  Aaron Richert Realty FC, LLC

  608 Kernstown Ct, Winchester, VA 22601
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  /43

  $849,990 Open Sun 1PM - 3PM

  • 5 Beds
  • 4.5 Baths
  • 5,254 Sq Ft

  1504 Brookdale Ct, Winchester, VA 22601

  This home generates income from solar energy sales averaging over $2k a year! The Solar panels and system are OWNED by the homeowner NOT leased. There are no monthly fees or payments for the system. System is “Grandfathered” with a licensing agreement that allows homeowner to sell excess electricity produced. Lower your energy costs and receive cash earnings! Recent updates over $40k in this

  Julie Shiley Coldwell Banker Realty

  1504 Brookdale Ct, Winchester, VA 22601
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  /35

  $434,990 New Construction

  • 4 Beds
  • 3.5 Baths
  • 1,923 Sq Ft

  1818 Blythe Way, Winchester, VA 22601

  1818 Blythe Way is an attractive new 3-level townhome with full brick front in Winchester, VA scheduled for a November move-in. Our modern Adams floorplan features a 1-car garage, and along with a bedroom and full bathroom on the first floor. Stained Oak stairs lead you to the main level with LVP Floors. The kitchen is equipped with beautiful quartz countertops, sarsaparilla cabinets, and

  D.R. Horton Builder

  1818 Blythe Way, Winchester, VA 22601
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  /16

  $279,900

  • 3 Beds
  • 1.5 Baths
  • 1,332 Sq Ft

  2901 Sorrell Ct, Winchester, VA 22601

  *Investor Opportunity, current tenants have a lease until May of 2027* Welcome to your new home! This beautifully maintained 3 -bedroom, 1.5 bath townhome offers comfort, convenience, and style in a great location. On the main level you will find a spacious kitchen with ample cabinetry and a breakfast area, the living room offers plenty of natural light, off the living room is a convenient half

  Amber Jenkins Century 21 Redwood Realty

  2901 Sorrell Ct, Winchester, VA 22601
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  /23

  $279,000

  • 3 Beds
  • 1 Bath
  • 907 Sq Ft

  208 Shenandoah Ave, Winchester, VA 22601

  Welcome home to 208 Shenandoah Ave in Winchester, VA! This updated ranch home offers the coveted simplicity of easy, one-level living and is perfectly situated in a prime, convenient Winchester location. Featuring 3 bedrooms and 1 full bath, the interior is turn-key with newer flooring and fresh paint throughout. The living spaces are bright and inviting with lots of natural light, creating a

  Dan Whitacre Colony Realty

  208 Shenandoah Ave, Winchester, VA 22601
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  /17

  $330,000

  • 3 Beds
  • 1 Bath
  • 1,237 Sq Ft

  117 W Oates Ave, Winchester, VA 22601

  This charming bungalow, nestled in the heart of the Arthur C Oates Estate, offers a delightful blend of comfort and community. Built in 1953, this home features 3 cozy bedrooms, 1 full bathrooms, and an upstairs loft perfect for relaxation. The inviting kitchen is equipped with essential appliances, including a single oven and refrigerator, making meal preparation a breeze. The unfinished

  Jeffrey Konrady Realty ONE Group Old Towne

  117 W Oates Ave, Winchester, VA 22601
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  /2

  $399,000

  • 10 Beds
  • 6 Baths
  • 12,128 Sq Ft

  910 Franklin St, Winchester, VA 22601

  What a remarkable and unique opportunity!Assessed for $571630.00 Brand new roof on entire building, newly demolished warehouse has made way to enormous area for expansion and or parking. SOOO MUCH potential - Upper level has two apartments -However only one is approved for rental unitLower level is ready for its new transformation as residential or allowed commercial use - Conditional use

  Pakeeza Akhtar The KOR Group, Inc.

  910 Franklin St, Winchester, VA 22601
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  /47

  $289,500

  • 4 Beds
  • 1 Bath
  • 1,732 Sq Ft

  1006 S Cameron St, Winchester, VA 22601

  Welcome home to this charming 4-bedroom, 1-bath colonial perfectly situated with walking distance from downtown Winchester. Warm hardwood floors flow throughout the home, complemented by a large covered front porch and a spacious rear deck—ideal for morning coffee or evening gatherings. Recent updates include a new water heater (2025), new water tank (2025), and an updated furnace and bath for

  Laura White ERA Oakcrest Realty, Inc.

  1006 S Cameron St, Winchester, VA 22601
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  /25

  $625,000

  • 5 Beds
  • 4 Baths
  • 3,550 Sq Ft

  681 Hillman Dr, Winchester, VA 22601

  No HOA! Only 2 years young! Main floor bedroom + full bath! Thoughtfully designed and meticulously maintained, this property blends comfort, style, and functionality across every level. The attached 2-car garage provides convenience and additional storage. Designer finishes, a spacious custom shower, and elegant details that create a spa-like experience. Third floor has a large entertaining loft

  Sarah Reynolds Keller Williams Realty

  681 Hillman Dr, Winchester, VA 22601
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  /47

  $519,900

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

  216 Fairmont Ave, Winchester, VA 22601

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

  Dave Spence RE/MAX Roots

  216 Fairmont Ave, Winchester, VA 22601
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  $269,000

  • 3 Beds
  • 2 Baths
  • 1,300 Sq Ft

  423 Highland Ave, Winchester, VA 22601

  Charming Winchester Home – Don’t Let This One Slip Away! Welcome to this beautifully refreshed home in the heart of Winchester, offering exceptional value, versatility, and convenience. Thoughtfully updated throughout, this property is move-in ready while still leaving room to make it your own. Enjoy ample off-street parking for up to 8 cars with rear access from West Lane, fresh renovations,

  

  Carlos Soares

  Samson Properties

  (540) 924-3305

  423 Highland Ave, Winchester, VA 22601
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  /9

  $269,900

  • 2 Beds
  • 1.5 Baths
  • 1,251 Sq Ft

  2918 Sorrell Ct, Winchester, VA 22601

  Welcome to your new home! This beautifully maintained 2 -bedroom, 1.5 bath townhome offers comfort, convenience, and style in a great location. On the main level you will find a spacious kitchen with ample cabinetry and a breakfast area, the living room offers plenty of natural light, off the living room is a convenient half bath. Upstairs you will find two generously sized bedrooms with large

  Amber Jenkins Century 21 Redwood Realty

  2918 Sorrell Ct, Winchester, VA 22601
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  /2

  $850,000 Coming Soon

  • 4 Beds
  • 4 Baths
  • 4,417 Sq Ft

  1006 Armistead St, Winchester, VA 22601

  This spacious 4-bedroom, 4-bath home is full of opportunity for buyers ready to make it their own. Priced below tax value, it’s a rare find for those looking to build equity while creating the home of their dreams. Featuring a generous floor plan with a two-story foyer, hardwood floors on the main level, and a large family room with a fireplace, the home provides a solid foundation for future

  Chris Craddock EXP Realty, LLC

  1006 Armistead St, Winchester, VA 22601
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  /35

  $290,000

  • 2 Beds
  • 1 Bath
  • 1,176 Sq Ft

  239 Chestnut St, Winchester, VA 22601

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

  William Wertz Wildhawks Realty LLC

  239 Chestnut St, Winchester, VA 22601
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  /59

  $635,000

  • 4 Beds
  • 3.5 Baths
  • 4,632 Sq Ft

  930 Wayne Dr, Winchester, VA 22601

  Beautiful brick-front Colonial in a prime location! Nestled in a quiet neighborhood yet just minutes from I-81 and local amenities, this stunning home offers the perfect blend of convenience and tranquility.Step into the grand two-story foyer, flanked by a formal living room and dining room accented with elegant columns and a cozy fireplace. To the right, you’ll find a spectacular

  Elizabeth Flood Keller Williams Realty

  930 Wayne Dr, Winchester, VA 22601
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  /69

  $605,000

  • Studio
  • 4,396 Sq Ft

  540 Monticello St, Winchester, VA 22601

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

  Laura King MarketPlace REALTY

  540 Monticello St, Winchester, VA 22601
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  /20

  $455,000

  • 6 Beds
  • 3 Baths
  • 1,552 Sq Ft

  2250 Roosevelt Blvd, Winchester, VA 22601

  Sellers are highly motivated and ready to make a deal!Beautifully Renovated Single-Family Home with a little Pool, Workshop, and Detached GaragesWelcome to this stunning fully renovated 4-bedroom, 3-bathroom single-family home that perfectly blends comfort, style, and functionality. Step inside to find an open-concept layout filled with natural light, ideal for both everyday living and

  Silvana Rojas Spring Hill Real Estate, LLC.

  2250 Roosevelt Blvd, Winchester, VA 22601

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