Winchester, VA Homes for Sale under $500,000

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  /57

  $449,900

  • 4 Beds
  • 3.5 Baths
  • 1,676 Sq Ft

  125 Alliance Ct, Winchester, VA 22602

  Welcome to this beautifully maintained home located in the highly sought-after Freedom Manor community in Winchester, VA! Ideally situated just minutes from shopping, dining, and everyday conveniences—with quick access to I-81—this home offers the perfect combination of comfort, functionality, and location.Inside, the main level features stylish and durable luxury vinyl plank (LVP)

  

  Rhonda Shade

  ERA Oakcrest Realty, Inc.

  (540) 619-5307

  125 Alliance Ct, Winchester, VA 22602
• Explore Winchester

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  /54

  $489,000

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

  101 Delaware Trail, Winchester, VA 22602

  Huge Price Reduction! Motivated Seller.Fabulous remodel featuring the finest materials from around the world. Outdoor activities are everywhere you turn at this completely renovated home in Winchester. Hiking, swimming, biking, kayaking, and skiing are all close by. As you sit on the beautiful deck, you can listen to the birds while you have your coffee. There are stunning views out of every

  

  Kimberly Pace

  EXP Realty, LLC

  (540) 240-9877

  101 Delaware Trail, Winchester, VA 22602
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  /34

  $499,900 Open Sun 11AM - 1PM

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

  1420 Fishel Rd, Winchester, VA 22602

  Nestled away in the trees, this updated retreat on 2.67 acres offers the perfect blend of peace, privacy, and one-level living. Inside, you’ll find 3 bedrooms, 2 renovated baths, brand-new flooring, and fresh paint throughout. The bright eat-in kitchen with island and stainless appliances flows into a spacious sitting room, enclosed rear porch with A/C, and a covered front porch for year-round

  

  Katherine (Kat) Wetzel

  Century 21 Redwood Realty

  (540) 779-1383

  1420 Fishel Rd, Winchester, VA 22602
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  /66

  $450,000 Open Sat 1PM - 3PM

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

  580 N Braddock St, Winchester, VA 22601

  Now $450,000 — Motivated Sellers + Huge Monthly Savings with 2-1 Rate Buydown!Step inside this beautifully restored 4-bedroom, 2.5-bath 1920s home and experience where historic charm meets modern luxury. Offering over 2,200 sq ft across three finished levels, 580 N Braddock delivers light, space, and thoughtful design—just blocks from Old Town Winchester’s walking mall.The main

  Payton Polychrones Samson Properties

  580 N Braddock St, Winchester, VA 22601
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  /44

  $496,129 New Construction

  • 3 Beds
  • 2.5 Baths
  • 2,195 Sq Ft

  117 Wagtail Ln, Winchester, VA 22603

  Embrace the Vera 30-F2 – Homesite 1031 at Hiatt Pointe—a two-car, front-load garage VILLA with three bedrooms, two full bathrooms, and one half bathroom will be ready IMMEDIATELY. Built for the way you live, this factory-framed floorplan makes room for moments big and small. Be welcomed by 9’ ceilings on both levels, oak main stairs, and expertly selected finishes that make this villa feel

  Shannon L Bray Pearson Smith Realty, LLC

  117 Wagtail Ln, Winchester, VA 22603
• 

  $409,855 New Construction

  • 3 Beds
  • 3.5 Baths
  • 1,658 Sq Ft

  210 Monteith Dr, Winchester, VA 22601

  OPEN HOUSE: Saturday - Monday 12pm - 3pm Beautiful open concept living 3 level townhome built on concrete slab with a walk-out lower level! The Bedford II 3 level interior town home with a box bay window with 1 car garage featuring 3 Bedrooms and 3.5 Baths and 1,658 square feet. It is fully finished top to bottom. The front door with the electronic Ring door camera leads directly into the

  

  DRB Homes

  Builder

  210 Monteith Dr, Winchester, VA 22601
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  /6

  $432,539 New Construction

  • 3 Beds
  • 3.5 Baths
  • 1,658 Sq Ft

  201 Monteith Dr, Winchester, VA 22601

  End Of Row Townhome With 1 Car Garage, Gourmet Kitchen & Rear Deck! MOVE-IN READY! The Bedford II 3 level END OF ROW town home that backs to TREES with a stone water table on the front and side of the home along with a box bay window and a 1 car garage featuring 3 Bedrooms and 3.5 Baths and 1,658 square feet. The front door with the electronic Smart Home Technology package leads directly into the

  

  DRB Homes

  Builder

  201 Monteith Dr, Winchester, VA 22601
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  /18

  $444,990 New Construction

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

  216 Munsee Cir, Winchester, VA 22602

  The Cabral offers 1,657 square feet of thoughtfully designed living space, featuring 3 spacious bedrooms, 2.5 bathrooms, and a versatile loft on the bedroom level—perfect for a home office, playroom, or additional lounge area. This home features a beautiful cypress green exterior with stone accents, and inside, you’ll find stylish white kitchen and bathroom cabinets paired with modern finishes

  

  D.R. Horton

  Builder

  216 Munsee Cir, Winchester, VA 22602
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  /44

  $492,669 New Construction

  • 3 Beds
  • 2.5 Baths
  • 2,187 Sq Ft

  114 Keystone, Winchester, VA 22603

  Embrace the Vera 30-F2 – Homesite 1096 at Hiatt Pointe—a two-car, front-load garage VILLA HOME with three bedrooms, two full bathrooms, and one half bathroom will be ready IMMEDIATELY. Built for the way you live, this factory-framed floorplan makes room for moments big and small. Be welcomed by 9’ ceilings on both levels, oak main stairs, and expertly selected finishes that make this villa feel

  Shannon L Bray Pearson Smith Realty, LLC

  114 Keystone, Winchester, VA 22603
• 

  

  /18

  $454,990 New Construction

  • 3 Beds
  • 2.5 Baths
  • 1,665 Sq Ft

  226 Munsee Cir, 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 Linen siding exterior with brick accents, while the interior boasts sleek gray kitchen and bathroom cabinets paired with modern finishes throughout. Enjoy

  

  D.R. Horton

  Builder

  226 Munsee Cir, Winchester, VA 22602
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  /24

  $454,990 New Construction

  • 3 Beds
  • 2.5 Baths
  • 1,665 Sq Ft

  CABRAL Plan at Retreat at Winding Creek - Single Family, Winchester, VA 22602

  The Cabral, a 1,657 square foot open concept two-story home, offers three bedrooms, two and a half bathrooms, a loft and a two-car garage. As you make your way from the front porch into the foyer you will find a convenient first-floor powder room and coat closet. Past the foyer is the large, open concept living room that flows nicely into the eat-in kitchen that overlooks the casual dining area

  

  D.R. Horton

  Builder

  137 Seminole Dr Unit 36203778, Winchester, VA 22602
• 

  $418,880 New Construction

  • 3 Beds
  • 3.5 Baths
  • 1,658 Sq Ft

  HOMESITE 117 Monteith Dr, Winchester, VA 22601

  3 Level End of Row Townhome With 1 Car Garage & Rear Deck! The Bedford II 3 level town home with a box bay window with 1 car garage End Unit featuring 3 Bedrooms and 3.5 Baths and 1,658 sq. ft. and will deliver the end of September or beginning of October 2025. It is fully finished top to bottom. The front door with the electronic Ring door camera leads directly into the spacious lower-level

  

  DRB Homes

  Builder

  HOMESITE 117 Monteith Dr, Winchester, VA 22601
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  /19

  $450,000 Open Sat 11AM - 2PM

  • 4 Beds
  • 2.5 Baths
  • 1,904 Sq Ft

  123 Etnam St, Winchester, VA 22602

  Come see this beautiful home located just off of Rt 50 to the East side of Winchester, great location for commuters, 4br, 2.5 bath with lots of room and storage space. Fenced in backyard with nice 20x16 deck and 8x10 additional deck space off of that for great entertaining. Call agent for combo to visit this listing.

  Heather Sutphin Coldwell Banker Realty

  123 Etnam St, Winchester, VA 22602
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  /24

  $449,900

  • 3 Beds
  • 2 Baths
  • 1,890 Sq Ft

  341 Wood Ave, Winchester, VA 22601

  Location, Location. Brick Rancher offers Walkout Basement, 4 Bedrooms, Two Full Baths. Hardwood Floors throughout. Front Entry Ceramic Tiled. Kitchen Luxury Vinyl Floor, New Dishwasher,Disposal, Refrigerator with Ice-maker( Not Hooked Up) and Electric Range. Basement Partially Finished with Brick Fireplace with Timberline Wood Stove Insert, Fourth Bedroom, Laundry and Storage Area. Rear 15x12

  George Johnson Jim Barb Realty Inc.

  341 Wood Ave, Winchester, VA 22601
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  /43

  $449,900

  • 3 Beds
  • 2 Baths
  • 2,018 Sq Ft

  2808 Saratoga Dr, Winchester, VA 22601

  Unbeatable location on quiet street with oversized parcel in city limits within walking distance of Creekside Station and Kernstown Battlefield. This property does not have covenants or restrictions and the detached carport can handle a slew of large vehicles. Interior has the necessary accommodations with sunroom, office/den and family room. Partial basement adds some storage but also a rec

  Dave Spence RE/MAX Roots

  2808 Saratoga Dr, Winchester, VA 22601
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  /14

  $469,700 Open Sat 11AM - 2PM

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

  421 Superior Ave, Winchester, VA 22601

  Renovated and move in ready! Let's start with the new mailbox, new 16' wide asphalt driveway, new 8'x13' concrete patio, and carport with bolts in ceiling for your swing to overlook the large back yard. Then inside, new heat pump and central a/c system, new appliances with fingerprint resistant stainless-steel exterior, stainless steel liner inside the dishwasher, large cu ft counter depth

  Leo Smith CENTURY 21 New Millennium

  421 Superior Ave, Winchester, VA 22601
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  /47

  $459,900

  • 3 Beds
  • 3.5 Baths
  • 2,686 Sq Ft

  106 Foxglove Dr, Winchester, VA 22602

  This 3BD/3.5BA Colonial combines modern upgrades with a versatile layout. The upper level showcases a spacious primary suite with dual walk-in closets and a bath featuring a soaking tub, glass-enclosed shower, and skylight. Two additional bedrooms with walk-in closets and a laundry room complete the floor. The main level offers a welcoming living room with fireplace, an updated kitchen with

  Matt Baer MarketPlace REALTY

  106 Foxglove Dr, Winchester, VA 22602
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  /46

  $468,000

  • 4 Beds
  • 3 Baths
  • 2,654 Sq Ft

  219 Milam Dr, Winchester, VA 22602

  Welcome to 219 Milam Drive, a spacious and updated all-brick rancher tucked in a quiet neighborhood just minutes from downtown Winchester, Route 7, and I-81. This four-bedroom, three-bath home offers over 2,700 square feet of finished living space, including a partially finished basement and additional storage or hobby rooms to suit your needs. Inside, you’ll find warm hardwood flooring, modern

  Kira Grubb Realty ONE Group Old Towne

  219 Milam Dr, Winchester, VA 22602
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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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  /32

  $475,000

  • 4 Beds
  • 4 Baths
  • 1,627 Sq Ft

  201 Parkway St, Winchester, VA 22601

  Freshly Renovated Charmer in Winchester!Welcome to 201 Parkway Street, a freshly updated home in the heart of Winchester! Previously tenant-occupied, this property has been thoughtfully refreshed and is ready for new owners. Recent Updates Include:Fresh interior paint throughoutRenovated kitchen and bathUpdated fixtures and finishesClean, move-in

  Cherish Green Coldwell Banker Elite

  201 Parkway St, Winchester, VA 22601
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  /23

  $449,900

  • 3 Beds
  • 2.5 Baths
  • 2,250 Sq Ft

  104 Primrose Place, Winchester, VA 22602

  Moe Gahche Long & Foster Real Estate, Inc.

  104 Primrose Place, Winchester, VA 22602
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  /6

  $432,539 New Construction

  • 3 Beds
  • 3.5 Baths
  • 1,658 Sq Ft

  HOMESITE 20 Monteith Dr, Winchester, VA 22601

  *OFFERING UP TO 15K IN FLEX CASH FOR PRIMARY RESIDENCE WITH USE OF APPROVED LENDER AND TITLE. CONTACT CO LISTING AGENT/CONSULTANT FOR DETAILS* The Bedford II 3 level END UNIT town home that backs to TREES with a stone water table on the front and side of the home along with a box bay window with 1 car garage featuring 3 Bedrooms and 3.5 Baths and 1,658 square feet. It is fully finished top

  Brittany Newman DRB Group Realty, LLC

  HOMESITE 20 Monteith Dr, Winchester, VA 22601
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  /50

  $445,000

  • 2 Beds
  • 1 Bath
  • 864 Sq Ft

  220 Chestnut Grove Rd, Winchester, VA 22603

  Experience the best of country living with this charming 2-Bedroom, 1-Bath Rancher nestled on 15 unrestricted acres in beautiful Frederick County, VA. Perfect as a full-time residence, weekend retreat, or potential farm, this property offers the peace and privacy of rural life while still being within easy reach of town conveniences.Step inside to find a cozy and move-in ready Home featuring

  Laura King MarketPlace REALTY

  220 Chestnut Grove Rd, Winchester, VA 22603
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  /56

  $424,900

  • 3 Beds
  • 2 Baths
  • 2,326 Sq Ft

  138 Country Club Cir, Winchester, VA 22602

  Charming All-Brick Rancher with Pool Across from Winchester Country ClubThis beautifully maintained 3-bedroom, 2-bath all-brick rancher offers classic charm and modern updates in one of Winchester’s most desirable east-side locations. Featuring a brand-new roof and new windows throughout, this home is move-in ready and designed for both comfort and entertainment.The main level

  Traci Shoberg RE/MAX Roots

  138 Country Club Cir, Winchester, VA 22602
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  /42

  $439,900

  • 3 Beds
  • 3 Baths
  • 1,732 Sq Ft

  275 Greenwood Rd, Winchester, VA 22602

  Charming split-foyer home situated on a generous 13,000 sq. ft. lot with convenient access to routes 7 and 81. No HOA. The main level boats neutral-toned walls and a distinctive dual-sided fireplace, seamlessly connecting the living and dining areas. The dining room and well-appointed kitchen feature elegant hardwood flooring and an abundance of natural light, enhanced by a full-size window and

  Jose Ugaz Gates Smart Realty, LLC

  275 Greenwood Rd, Winchester, VA 22602
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  /36

  $410,000

  • 4 Beds
  • 3.5 Baths
  • 2,261 Sq Ft

  125 Cheshire Ct, Winchester, VA 22602

  Beautiful and well-maintained 4 bedroom, 3.5 bath townhouse at the end of a quiet cul-de-sac on the east side of Winchester. Conveniently located to Rt 7 and I-81 and historic downtown Winchester. The 3-level townhouse backs to a wooded tree area and has a fenced rear yard. New luxury vinyl floor installed in majority of the home. As you enter, you will be welcomed into a large foyer with

  Eric Kronenwetter RE/MAX Roots

  125 Cheshire Ct, Winchester, VA 22602
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  /65

  $420,000 Open Sat 11AM - 1PM

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

  707 E Cork St, Winchester, VA 22601

  Centrally located colonial with gorgeous hardwood flooring and trim throughout! Step back in time, but enjoy all of the modern amenities with easy access to Jim Barnett Park just down the street, downtown walking mall and commuter roads, and even views of all city fireworks! The main level features a large living room with wood floor inlay, formal dining room with built-ins, kitchen with HUGE

  Misty Weaver Samson Properties

  707 E Cork St, Winchester, VA 22601
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  /50

  $415,000

  • 4 Beds
  • 3 Baths
  • 2,255 Sq Ft

  290 Green St, Winchester, VA 22601

  Life just got easier in this Beautiful Home. Here is a wonderfully maintained property offering 4 Bedrooms and 3 Full Baths with fresh neutral paint, a private lot, handy 1 car garage with sparkling stamped concrete driveway, sidewalk and 2 finished levels. There is so much room! Step into the sunny upper level to find a nice open floor plan. Kitchen, living and dining flow easily into one

  Angela Duncan MarketPlace REALTY

  290 Green St, Winchester, VA 22601
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  /42

  $459,000

  • 3 Beds
  • 2 Baths
  • 2,648 Sq Ft

  1332 Ramseur Ln, Winchester, VA 22601

  Welcome home to a rare find in the Mews of Meadow Branch - this exceptional all-brick exterior condo offering 3 bedrooms and 2 full baths. Rich hardwood floors flow throughout the home. The primary bedroom includes a cozy fireplace perfect for relaxing evenings. Updated appliances, such as washer, dryer, refrigerator, stove and microwave. Enjoy the ease of your own private elevator within the

  James King RE/MAX Roots

  1332 Ramseur Ln, Winchester, VA 22601
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  /60

  $425,000

  • 3 Beds
  • 1 Bath
  • 2,050 Sq Ft

  3634 Wardensville Grade, Winchester, VA 22602

  Country charm meets convenience at 3634 Wardensville Grade—just minutes to Rt 50, Rt 37 and I 81— and less than 20 minutes to Winchester Medical Center! Set on just under 9 acres with 2,572 sq ft, 3 bedrooms, and 1 bath, this light-filled home offers an easy-flow layout with generous gathering spaces, a bright kitchen, and flexible rooms ideal for a home office or hobby area. Cozy warmth comes

  Kira Grubb Realty ONE Group Old Towne

  3634 Wardensville Grade, Winchester, VA 22602
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  /42

  $499,900

  • 4 Beds
  • 1.5 Baths
  • 1,932 Sq Ft

  420 W Cork St, Winchester, VA 22601

  Discover the perfect blend of historic charm and modern convenience at 420 W Cork Street. This captivating four-level brick home offers 4 bedrooms and 1.5 baths, boasting beautiful hardwood floors, gorgeous trim and plenty of space for you and yours. The main level offers a spacious living room, dining room and kitchen. Upstairs you will find 4 sizable bedrooms and a full bath. The top level is

  Dan Whitacre Colony Realty

  420 W Cork St, Winchester, VA 22601
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  /17

  $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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  /56

  $489,999

  • 3 Beds
  • 2.5 Baths
  • 2,412 Sq Ft

  109 Shelby Ct, Winchester, VA 22602

  Welcome to this beautiful colonial home in the sought-after Chapel Hill community. Set on a flat, quarter-acre lot, it pairs a fully fenced, beautifully landscaped backyard with the convenience of a two-car garage. Inside, the main level is warm and welcoming: a separate dining room for gatherings and a bright family room anchored by a gas fireplace and plenty of natural light.The kitchen

  Omar Khatib DMV Realty, INC.

  109 Shelby Ct, Winchester, VA 22602
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  /38

  $409,000

  • 3 Beds
  • 2 Baths
  • 1,176 Sq Ft

  163 Margaret Ln, Winchester, VA 22603

  (Magnificent Margaret) This home has a lot to offer: All bedrooms and bathrooms on the main level, fully updated kitchen with Stainless Steel Appliances (Fridge, Dishwasher, Stove, Microwave) Quartz counter top, built in pantry, remodeled bathrooms with a double vanity in the primary bathroom and a walk-in tile shower, Central Heating & Air, New windows, Laundry room, large driveway, two car

  Michael Sprague Samson Properties

  163 Margaret Ln, Winchester, VA 22603
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  /41

  $430,000 Open Sat 1PM - 4PM

  • 3 Beds
  • 1 Bath
  • 1,925 Sq Ft

  103 Blue Ridge Ln, Winchester, VA 22602

  Welcome to this beautifully renovated brick rancher on a spacious 0.55-acre lot in a quiet neighborhood just outside Stephens City and Winchester. This move-in-ready 3-bedroom 1-bathroom home offers a perfect blend of modern updates and comfortable living. Step inside to find luxury vinyl plank flooring throughout, fresh lighting fixtures, and a completely updated kitchen featuring quartz

  Jon Fleming Weichert Realtors - Blue Ribbon

  103 Blue Ridge Ln, Winchester, VA 22602
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  /20

  $499,000

  • Studio
  • 2,376 Sq Ft

  510 N Loudoun St, Winchester, VA 22601

  All brick 3 unit complex with off street parking and near Old Town Mall..2nd floor has 2BD/1BA with unfinished attic, main floor is 1BR/1BA (Both have rear balcony) and basement unit has access to storage area and includes1BD/1BA. All units have washer/dryer (Basement unit washer/dryer belongs to tenant). Owner/Agent and home inspection report available upon request.

  Dave Spence RE/MAX Roots

  510 N Loudoun St, Winchester, VA 22601
• 

  

  /25

  $445,000

  • 4 Beds
  • 3.5 Baths
  • 2,892 Sq Ft

  112 Hites St, Winchester, VA 22602

  No HOA! Discover the expanded comfort of this charming home, featuring a spacious addition completed in 2011. Two master suites: one upstairs and the other one at the main level—it’s ideal for multigenerational living or a private in-law suite. Enjoy a fenced backyard, attached single-car garage, and updates including a newer roof (2015) and HVAC system with heat pump and gas furnace (2011). The

  Rocio Benavides Orus Realty Inc

  112 Hites St, Winchester, VA 22602
• 

  

  /39

  $419,900

  • 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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  /29

  $409,900

  • 3 Beds
  • 2.5 Baths
  • 1,962 Sq Ft

  117 Tye Ct, Winchester, VA 22602

  Modern, Move-In Ready Townhome with Premium UpgradesIdeally located just outside the bustle of Winchester with an easy commute to the DC Metro area, this 2023-built townhome offers the perfect balance of comfort, convenience, and style.Freshly and professionally painted throughout, the home features an open-concept main level with durable LVP flooring, granite countertops,

  Rick Cockrill Keller Williams Realty

  117 Tye Ct, Winchester, VA 22602
• 

  

  /49

  $494,970

  • 5 Beds
  • 3 Baths
  • 3,116 Sq Ft

  110 Carter Place, Winchester, VA 22602

  Contract fell through! Interest rates have gone down! Extensive Renovations: The home has been fully renovated in 2025, including updates to kitchen, bathrooms, flooring, and fresh paint throughout. Designed to accommodate two families comfortably, featuring large rooms that are flooded with natural light like the entire house. The lower level is equipped with wheelchair-accessible features,

  Rodrigo Cruz Long & Foster Real Estate, Inc.

  110 Carter Place, Winchester, VA 22602

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