Winchester County VA Homes for Sale

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  /53

  $633,000

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

  320 Linden Dr, Winchester, VA 22601

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

  

  Kimberly Schroeder

  Long & Foster Real Estate, Inc.

  (540) 274-0212

  320 Linden Dr, Winchester, VA 22601
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  /2

  $279,000 Open Sat 10AM - 12PM

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

  423 Highland Ave, Winchester, VA 22601

  Charming Winchester Home –Don't let this property slip away!This freshly updated home in the heart of Winchester offers incredible potential and versatility. Featuring off-street parking from the rear alley, a fresh coat of paint, and newly installed vinyl flooring downstairs, this property is move-in ready while leaving room for your personal touches.Highlights include:3

  

  Carlos Soares

  Samson Properties

  (540) 584-8746

  423 Highland Ave, Winchester, VA 22601
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  /42

  $344,900

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

  107 E Monmouth St, Winchester, VA 22601

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

  

  Jeanne Mezzatesta

  Colony Realty

  (540) 619-5037

  107 E Monmouth St, Winchester, VA 22601
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  $549,900 Open Sat 12PM - 2PM

  • 4 Beds
  • 3 Baths
  • 2,614 Sq Ft

  1729 Handley Ave, Winchester, VA 22601

  This immaculate 4-bedroom, 3-bath Cape Cod in sought-after Meadow Branch is move-in ready and full of thoughtful updates! From the welcoming foyer, the home flows seamlessly into a bright living room, spacious kitchen, and dedicated dining room. On the main level you'll also find two bedrooms and a full bath, perfect for guests or convenient one-level living.From the kitchen, step outside

  

  Jeanne Mezzatesta

  Colony Realty

  (540) 698-5892

  1729 Handley Ave, Winchester, VA 22601
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  /9

  $225,000

  • Land
  • 6 Acres
  • $37,563 per Acre

  Lot 3 Cedar Creek Grade, Winchester, VA

  Beautiful lot in a small neighborhood on the very desirable west side of Winchester off Cedar Creek Grade! Lot is already perked for an alternative septic system. This opportunity doesn’t come along often! Rolling hills with beautiful surroundings and views. The location is less than 10 minutes to grocery stores, downtown Winchester, or Winchester Medical Center. It’s also located within 2

  

  Lori Bales

  Keller Williams Realty

  (540) 974-1542

  Lot 3 Cedar Creek Grade, Winchester, VA
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  /99

  $869,500

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

  1517 Brookdale Ct, Winchester, VA 22601

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

  

  Brock Harris

  Samson Properties

  (540) 596-5570

  1517 Brookdale Ct, Winchester, VA 22601
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  $433,880 New Construction

  • 3 Beds
  • 3.5 Baths
  • 1,630 Sq Ft

  0 Homesite 117 Monteith Dr Unit 36422335, Winchester, VA 22601

  3 Level End of Row Townhome With 1 Car Garage & Rear Deck! Beautiful open concept living 3 level town home built on concrete slab with a walk-out lower level. Finished Rec Room - 13 ft. 1 in. x 11 ft. 1 in. with a door to the outside/backyard. The living room area is 15 ft. 3 in. x 17 ft., open kitchen layout with an extended island, a box bay window and 10 ft. x 14 ft. deck in the rear of home.

  

  DRB Homes

  Builder

  0 Homesite 117 Monteith Dr Unit 36422335, Winchester, VA 22601
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  $429,340 New Construction

  • 3 Beds
  • 3.5 Baths
  • 1,630 Sq Ft

  0 Homesite 114 Monteith Dr Unit 36422292, Winchester, VA 22601

  3 Level Townhome With Over 1,600 Finished sq. ft., 1 Car Garage & Rear Deck! Bedford II, 3 level townhome features a partial stone front with 1 car garage. This home features 3 Bedrooms and 3.5 Baths. It is fully finished top to bottom. The front door leads directly into the spacious lower level including 9 ft. ceilings, foyer with a double coat closet, access to the garage with a garage door

  

  DRB Homes

  Builder

  0 Homesite 114 Monteith Dr Unit 36422292, Winchester, VA 22601
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  $515,000 Open Sat 12PM - 2PM

  • 4 Beds
  • 2 Baths
  • 2,200 Sq Ft

  580 N Braddock St, Winchester, VA 22601

  Step into the charm of 1920s architecture seamlessly blended with today’s comforts. This beautifully restored 4-bedroom, 2.5-bath home offers over 2,200 sq ft of finished living space across three levels.Inside, you’ll find a bright, open main level with wide-plank flooring, a cozy family room with stacked stone gas fireplace, and a gourmet kitchen featuring a massive island, stainless

  Payton Polychrones Samson Properties

  580 N Braddock St, Winchester, VA 22601
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  /2

  $399,990 New Construction

  • 3 Beds
  • 3.5 Baths
  • 1,630 Sq Ft

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

  Covered front porch leads into the foyer. Attached 1 car garage or optional flex room or study. Open concept kitchen located next to the country kitchen and living room. Box bay rear window and 10' x 14' deck. Owner’s suite with large walk-in closet, dual vanity, and oversized seated shower in owner’s bath. Fireplace option available in select homes.

  

  DRB Homes

  Builder

  0 Tbd Weems Ln Unit 36470375, Winchester, VA 22601
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  /13

  $499,990 New Construction

  • 3 Beds
  • 2.5 Baths
  • 2,451 Sq Ft

  3131 Eton Place, Winchester, VA 22601

  End of Group, 4 Level Townhome with Deck and 4 ft. Rear Extension! Stunning Fully Upgraded Model Home – Don’t Miss Out! This gorgeous end of group model home at The Lofts at Creekside is a must-see! The Upton II features a gourmet kitchen with stainless steel appliances, quartz countertops, upgraded cabinets, and lighting. Oak staircases, a spacious fourth-level loft, and nine-foot ceilings add

  

  DRB Homes

  Builder

  3131 Eton Place, Winchester, VA 22601
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  $452,539 New Construction

  • 3 Beds
  • 3.5 Baths
  • 1,630 Sq Ft

  0 Homesite 20 Monteith Dr Unit 36425637, Winchester, VA 22601

  End Of Row Townhome With 1 Car Garage, Gourmet Kitchen & Rear Deck! This home has a Gourmet Kitchen: cooktop with chimney style hood, wall microwave, wall oven, upgraded gourmet Energy Star stainless steel appliances, Refrigerator is a French 2 door style, the kitchen island is extended to comfortably seat 4, a box bay window in the rear of the home for extra lighting, and a 10 ft. x 14 ft. deck.

  

  DRB Homes

  Builder

  0 Homesite 20 Monteith Dr Unit 36425637, Winchester, VA 22601
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  /80

  $595,000

  • 4 Beds
  • 3.5 Baths
  • 2,976 Sq Ft

  2812 Ridgetop Ct, Winchester, VA 22601

  Welcome to this beautiful "picture perfect" brick front 4-bedroom, 3.5-bath home in the desirable Rolling Hills community of Winchester, VA. Perfectly located at the end of a cul-de-sac in an established (and sought after) neighborhood, this one-owner property has been meticulously maintained and is ready for its next chapter.Inside, you’ll find a spacious and inviting layout that includes a

  Sara Duncan RE/MAX Distinctive Real Estate

  2812 Ridgetop Ct, Winchester, VA 22601
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  /36

  $574,900

  • 3 Beds
  • 3 Baths
  • 2,726 Sq Ft

  2723 Windwood Dr, Winchester, VA 22601

  Premier Single-Level Living on a Private Cul-de-Sac! Nestled at the end of a quiet, prestigious cul-de-sac, this exquisite one-level ranch home presents a rare opportunity to acquire a property where meticulous maintenance meets masterful design. Shielded from through-traffic and enveloped by landscaped gardens. The home offers an immediate sense of arrival and tranquil privacy. A Grand and

  LESLIE WEBB Long & Foster Real Estate, Inc.

  2723 Windwood Dr, Winchester, VA 22601
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  /60

  $550,000

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

  121 N Washington St, Winchester, VA 22601

  A MUST SEE INSIDE!!!! This 2.5 story historic gem offers 3-4 beds, 2.5 baths and gourmet kitchen with brand new state of art appliances includes wine fridge, drawer style microwave, and pot filler. Formal living/dining room(s). Extras include den, office(s), nooks, and 3rd floor bonus room (perfect for kid's getaway). Laundry hook-ups on both main level and 2nd level. This home has been

  M. Kelly Walker RE/MAX Roots

  121 N Washington St, Winchester, VA 22601
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  /42

  $479,900

  • 3 Beds
  • 2.5 Baths
  • 1,976 Sq Ft

  703 National Ave, Winchester, VA 22601

  Fully renovated in 2025, this 3-bedroom, 2.5-bath home is ideally located within Winchester city limits—just a short walk to the vibrant downtown walking mall with its shops, dining, and entertainment, as well as Jim Barnett Park for outdoor recreation. Thoughtful updates and fresh landscaping enhance its curb appeal. Inside, you’ll find brand-new bathrooms with updated lighting, vanities,

  Jennifer Sacco RE/MAX Roots

  703 National Ave, Winchester, VA 22601
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  /87

  $650,000

  • 4 Beds
  • 2.5 Baths
  • 3,232 Sq Ft

  107 Roszel Rd, Winchester, VA 22601

  Spacious 4-bedroom, 2.5-bath home located in a desirable neighborhood just minutes from downtown. The main level features a family room, large eat-in kitchen with fireplace and bay window looking over the rear yard. The lower level features a game room with fireplace and opens onto the rear deck overlooking the pool. Upstairs offers four bedrooms, including a private owner’s suite. Outdoor

  John Scully Colony Realty

  107 Roszel Rd, Winchester, VA 22601
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  /50

  $450,000

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

  25 E Hart St, Winchester, VA 22601

  Welcome to 25 E Hart Street! Nestled in the heart of downtown Winchester, this beautifully updated 5-bedroom, 3-bath home is the perfect mix of charm, space, and convenience. Step inside to a bright, spacious living room where a wood-burning fireplace provides the perfect spot to relax and unwind. The updated kitchen is a dream with quartz countertops, stainless steel appliances, crisp white

  Liz Owings RE/MAX Roots

  25 E Hart St, Winchester, VA 22601
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  /39

  $419,900 Open Sun 1PM - 3PM

  • 5 Beds
  • 2 Baths
  • 2,363 Sq Ft

  707 S Braddock St, Winchester, VA 22601

  Welcome to this charming, fully remodeled home located in the heart of Winchester.Experience the timeless appeal of Old Winchester charm, just minutes from the vibrant walking mall, shops, restaurants, and the famous Apple Blossom Parade route. This beautifully remodeled home features LVP flooring throughout and a light-filled open floor plan that seamlessly blends historic character with

  Heloisa Amar Samson Properties

  707 S Braddock St, Winchester, VA 22601
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  /40

  $450,000

  • 4 Beds
  • 2 Baths
  • 1,092 Sq Ft

  1709 Reaves St, Winchester, VA 22601

  Please take off shoes and give feedback. Step into this beautifully cared-for home featuring new roof (2023) New HVAC System (2024) new LVP floors throughout the basement a spacious, inviting layout. The large kitchen offers plenty of room for meal prep and flows effortlessly into the dining and living rooms — perfect for family gatherings and entertaining. The finished basement boasts a

  Alexandra Brown Berkshire Hathaway HomeServices PenFed Realty

  1709 Reaves St, Winchester, VA 22601
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  /26

  $479,900

  • 6 Beds
  • 3 Baths
  • 3,900 Sq Ft

  811 Berryville Ave, Winchester, VA 22601

  PRICE REDUCED .....DO YOU HAVE A LARGE FAMILY AND NEED YOUR OWN SPACE. HERE IS A 6 BEDROOMS 3 BATHROOMS WITH A IN-LAW SUITE. OVER 3900+ SQ. FT FINISHED. OFF STREET PARKING FOR 6 CARS. SHED AND STILL ROOM TO RELAX OUTBACK.

  Richard Kozlowski Long & Foster Real Estate, Inc.

  811 Berryville Ave, Winchester, VA 22601
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  /6

  $432,539 New Construction

  • 3 Beds
  • 3.5 Baths
  • 1,630 Sq Ft

  HOMESITE 20 Monteith Dr, Winchester, VA 22601

  *OFFERING UP TO 15K IN CLOSING COST ASSISTANCE FOR PRIMARY RESIDENCE WITH USE OF APPROVED LENDER AND TITLE.*This home has a Gourmet Kitchen: cooktop with chimney style hood, wall microwave, wall oven, upgraded gourmet Energy Star stainless steel appliances, Refrigerator is a French 2 door style, the kitchen island is extended to comfortably seat 4, and a box bay window in the rear of the home

  Brittany Newman DRB Group Realty, LLC

  HOMESITE 20 Monteith Dr, Winchester, VA 22601
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  /6

  $418,880 New Construction

  • 3 Beds
  • 3.5 Baths
  • 1,630 Sq Ft

  HOMESITE 117 Monteith Dr, Winchester, VA 22601

  *OFFERING UP TO 15K IN CLOSING COST ASSISTANCE FOR PRIMARY RESIDENCE WITH USE OF APPROVED LENDER AND TITLE.*Beautiful open concept living 3 level town home built on concrete slab with a walk-out basement. Finished Rec Room - 13'1" x 11'1" with a door to the outside/backyard. The living room area is 15'3" x 17', open kitchen layout with an extended island, and a box bay window in the rear of

  Brittany Newman DRB Group Realty, LLC

  HOMESITE 117 Monteith Dr, Winchester, VA 22601
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  /44

  $399,999

  • 4 Beds
  • 1.5 Baths
  • 1,820 Sq Ft

  501 National Ave, Winchester, VA 22601

  National avenue is getting an upgrade and you will enjoy the renovations in this 4 square colonial with plenty of space, high ceilings, modernized baths and kitchen to the upgraded electrical, plumbing, and lighting. Parking for two in the rear gives you swift access to your back porch and straight into the kitchen and two short steps to main level laundry. Double rear porches is a rare but you

  Dave Spence RE/MAX Roots

  501 National Ave, Winchester, VA 22601
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  /53

  $679,000

  • Studio
  • 3,511 Sq Ft

  1400 Valley Ave, Winchester, VA 22601

  Versatile on Valley!So many possibilities! This versatile duplex is full of charm and opportunity! The original 1936 home features beautiful wood floors, tall ceilings, fireplace, sunroom, and a stunning staircase that adds timeless character. The front unit is perfect for an owner-occupant who wants to enjoy historic charm while generating income from the back unit, or you can rent out

  Danielle Spriggs Real Broker LLC

  1400 Valley Ave, Winchester, VA 22601
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  /28

  $289,900

  • 2 Beds
  • 2 Baths
  • 897 Sq Ft

  939 Woodland Ave, Winchester, VA 22601

  If you're looking to Downsize or Just Starting Out, Come Checkout this 1–2-bedroom 2 full bath home on 3 Levels Updated Kitchen with Stainless Steel Appliances, a Living room Dining room or Main level Bedroom with a Full bath attached. Stackable Washer & Dryer 2nd Level has a Bedroom Full bathroom and a loft area. Theres a unfinished Basement. Outside has a detach one car garage or Workshop with

  Richard Kozlowski Long & Foster Real Estate, Inc.

  939 Woodland Ave, Winchester, VA 22601
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  /30

  $220,000

  • 3 Beds
  • 1 Bath
  • 1,232 Sq Ft

  376 Charles St, Winchester, VA 22601

  Welcome home to laid-back charm in Winchester, VA! This inviting 3-bedroom, 1-bath home offers character, comfort, and plenty of breathing room to make your own. Inside, rich hardwood floors add warmth and continuity from the living room through the main level, while oversized windows flood the spacious bedrooms with natural light. The kitchen has plenty of cabinet space and a layout that

  Chris Craddock EXP Realty, LLC

  376 Charles St, Winchester, VA 22601
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  /3

  $2,300,000

  • Land
  • 3.51 Acres
  • $655,271 per Acre

  1721 Amherst St, Winchester, VA 22601

  3.51 AC of premier commercial land. Directly across the street from the main hospital campus on one of Winchester's main commercial corridors. Ideal for banks, medical offices, retail or restaurants.

  Marie DiLorenzo Oakcrest Commercial LLC.

  1721 Amherst St, Winchester, VA 22601
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  /17

  $399,990

  • 3 Beds
  • 3.5 Baths
  • 1,630 Sq Ft

  TBB Monteith Dr Unit BEDFORD II, Winchester, VA 22601

  **SPECIAL OFFER! Receive Up to 15K IN FLEX CASH FOR PRIMARY RESIDENCE WITH USE OF APPROVED LENDER AND TITLE!**Featuring Bedford II in Valor Crossing! Open concept kitchen located next to the country kitchen and living room. Optional features include box bay rear window and 10' x 14' deck. Primary suite with large walk-in closet, dual vanity, and oversized seated shower in primary bath.

  Brittany Newman DRB Group Realty, LLC

  TBB Monteith Dr Unit BEDFORD II, Winchester, VA 22601
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  /30

  $349,900

  • 3 Beds
  • 2 Baths
  • 1,529 Sq Ft

  966 Woodstock Ln, Winchester, VA 22601

  Beautiful 3-bedroom, 2-bath split-foyer home in the heart of Winchester City! The main level features hardwood floors, an open kitchen/dining/living layout, and an eat-in kitchen with stainless steel appliances and upgraded countertops. The upper-level bath includes a tiled floor, vanity, and tub surround. The finished basement offers a spacious family room with a brick hearth, third bedroom,

  Anselm Tamasang Weichert Realtors - Blue Ribbon

  966 Woodstock Ln, Winchester, VA 22601
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  /11

  $1,100,000

  • Land
  • 2.83 Acres
  • $388,693 per Acre

  2725 S Pleasant Valley Rd, Winchester, VA 22601

  Location, location, location. Here is your chance to own one of the few commercial/industrial lots located in the highly desirable Winchester City. This cleared, blank slate is ready for your next business endeavor. Currently zoned as CM-1 (Commercial/Industrial), the property offers roughly 465 ft of prime road frontage, perfect for displaying your establishment.Current use regulations

  Kaitlyn Behr RE/MAX Roots

  2725 S Pleasant Valley Rd, Winchester, VA 22601
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  /69

  $369,900

  • 3 Beds
  • 2 Baths
  • 1,293 Sq Ft

  301 Liberty Ave, Winchester, VA 22601

  Welcome to 301 Liberty Ave, FALL IN LOVE with this charming all brick colonial residence situated in the heart of downtown Winchester. Just blocks away from the scenic walking mall you’ll discover an array of quaint shops, restaurants and the renowned Apple Blossom Parade route. This meticulously fully remodeled home boasts three spacious bedrooms and two luxurious bathrooms and is ready for a

  John Ashton Equity Realty

  301 Liberty Ave, Winchester, VA 22601
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  /16

  $299,900

  • 2 Beds
  • 1 Bath
  • 950 Sq Ft

  20 E Hart St, Winchester, VA 22601

  This is a completely restored Winchester classic within walking distance to the downtown area and Handley High school. Located at the end of street. Home improvements include new HVAC, plumbing, electric and appliances. Interior pictures will follow as soon as painting has been completed.

  Meridee Powars Link Realty Services LLC

  20 E Hart St, Winchester, VA 22601
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  /35

  $375,000

  • 4 Beds
  • 2 Baths
  • 1,800 Sq Ft

  3 N Purcell Ave, Winchester, VA 22601

  This charming 4-bedroom bungalow, beautifully renovated in 2015, offers a perfect blend of modern comfort and classic appeal. Step inside to discover hardwood floors and crown moldings that enhance the inviting atmosphere. The country-style kitchen features ample table space, ideal for gatherings. With two full bathrooms and an entry-level bedroom, convenience is at your fingertips. Outside,

  mary kakouras On The Market Properties

  3 N Purcell Ave, Winchester, VA 22601
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  /66

  $699,999

  • 4 Beds
  • 5 Baths
  • 5,903 Sq Ft

  2530 Goldenfield Ln, Winchester, VA 22601

  Gorgeous home in the sought after Harvest Ridge neighborhood. Make this immaculately kept and updated home yours. Walk through the front door and be welcomed by a grand staircase. Follow it to the dining room or sitting room. Enjoy preparing a meal in the gourmet kitchen which is perfect for family meals or entertaining. Upstairs features 4 spacious bedrooms, including a master suite and 3

  Dave Spence RE/MAX Roots

  2530 Goldenfield Ln, Winchester, VA 22601
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  /49

  $325,000

  • 4 Beds
  • 1.5 Baths
  • 1,199 Sq Ft

  118 E Monmouth St, Winchester, VA 22601

  Charming Remodeled Colonial in Historic Old Town WinchesterYou’ll fall in love with this beautifully updated Colonial located in the heart of Winchester’s Historic District. Just steps from the Downtown Pedestrian Mall, Handley High School, and local shops and restaurants, this home blends timeless character with modern convenience.• 4 Bedrooms 1.5 Bathrooms• Restored original

  Scott Dawson Oakcrest Commercial LLC.

  118 E Monmouth St, Winchester, VA 22601
• 

  

  /41

  $349,900 Open Sat 12PM - 2PM

  • 3 Beds
  • 1 Bath
  • 1,192 Sq Ft

  316 Virginia Ave, Winchester, VA 22601

  Well maintained Colonial offering timeless character and modern potential in the heart of Winchester. This 3-bedroom, 1 1/2 bath home features beautiful hardwood floors, a spacious living area, formal dining room, and a well-sized kitchen with ample pantry storage. Finished basement with lots of space and also huge attic space with room for storage or play room. 15 Year old roof, new

  Berta Vasquez Samson Properties

  316 Virginia Ave, Winchester, VA 22601
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  /25

  $300,000

  • 3 Beds
  • 1 Bath
  • 1,710 Sq Ft

  428 Imperial St, Winchester, VA 22601

  Enjoy the ease of one-level living in the heart of Winchester City thats ready for your personal touches! Ideally located just minutes from shopping, dining, and local conveniences, this charming all-brick rancher with a full walk-up basement offers both comfort and functionality. The kitchen features space for a dining table, while the inviting living room boasts a cozy fireplace with a lovely

  Leah Clowser RE/MAX Roots

  428 Imperial St, Winchester, VA 22601
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  /35

  $349,990

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

  1005 Pennsylvania Ave, Winchester, VA 22601

  A classic brick ranch in Winchester, VA, has three bedrooms and two full bathrooms. The basement includes a separate entrance, a laundry area, a full bathroom, and an additional bonus room. Recent updates include: finished basement, new HVAC system, complete renovations of both bathrooms, new hardwood flooring, and an updated kitchen with new cabinets and countertops. No HOA restrictions.

  Nathalie Acosta Spring Hill Real Estate, LLC.

  1005 Pennsylvania Ave, Winchester, VA 22601
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  /34

  $469,900

  • 3 Beds
  • 3.5 Baths
  • 2,052 Sq Ft

  711 S Braddock St, Winchester, VA 22601

  This well-maintained 3-bedroom, 3.5-bath home offers bright, open living spaces with plenty of natural light. The main level features a spacious living room, an updated kitchen with stainless steel appliances, and a dining area. The back patio features an open area and green space with a fenced backyard—great for relaxing or entertaining. Upstairs, you’ll find a generous primary suite with a full

  Dave Spence RE/MAX Roots

  711 S Braddock St, Winchester, VA 22601

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