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Browse All Winchester City Properties for Sale

338 E Piccadilly St, Winchester image
338 E Piccadilly St, Winchester $399,900

Welcome to 338 E Piccadilly Street, a beautifully updated 3-bedroom, 2-bathroom home perfectly positioned in a highly convenient Winchester location. Overflowing with nat...

  • 3 Beds
  • 2 Baths
  • Winchester City SubDv.
  • 22601 Zip Code
  • ACTIVE Status
828 Woodland Ave, Winchester image
828 Woodland Ave, Winchester $298,900

PRICED TO SELL!!! This all-brick Ranch 2-3 bedrooms, 1.5 bathrooms, kitchen has been updated with granite countertops. Full basement partly finished basement, with works...

  • 2 Beds
  • 2 Baths
  • Winchester City SubDv.
  • 22601 Zip Code
  • ACTIVE UNDER CONTRACT Status
2817 Papermill Rd, Winchester image
2817 Papermill Rd, Winchester $325,000

Welcome to 2817 Papermill Road, a beautifully maintained home that reflects true pride of ownership from the moment you arrive. Situated on an impressive approximately 0....

  • 3 Beds
  • 2 Baths
  • Winchester City SubDv.
  • 22601 Zip Code
  • ACTIVE Status
1414 S Braddock St, Winchester image
1414 S Braddock St, Winchester $349,900 ▼

Come Check out this charming Cape Cod home in Winchester City, built in 1950 and beautifully renovated in 2026, offers a perfect blend of classic character and modern con...

  • 2 Beds
  • 2 Baths
  • Winchester City SubDv.
  • 22601 Zip Code
  • PENDING Status
102 N Purcell Ave, Winchester image
102 N Purcell Ave, Winchester $285,000

Charming home ideally located just minutes from the heart of historic Winchester! Whether you're looking for convenient access to shopping, dining, entertainment, or comm...

  • 2 Beds
  • 1 Baths
  • Winchester City SubDv.
  • 22601 Zip Code
  • CLOSED Status
406-408 S Cameron St, Winchester image
406-408 S Cameron St, Winchester $429,000

Opportunity is knocking! This 3-unit multifamily property is centrally located in downtown Winchester, just minutes from the Walking Mall. The property is fully occupied ...

  • Winchester City SubDv.
  • 22601 Zip Code
  • CLOSED Status
629 National Ave, Winchester image
629 National Ave, Winchester $326,000

Beautifully charming and completely move-in ready, this updated 4-bedroom, 2-bath home offers the perfect blend of style, comfort, and functionality. Step inside to find...

  • 4 Beds
  • 2 Baths
  • Winchester City SubDv.
  • 22601 Zip Code
  • CLOSED Status
244 Parkway St, Winchester image
244 Parkway St, Winchester $459,000

Discover the perfectly updated turnkey home you’ve been searching for in Historic Winchester. This beautifully maintained property offers 3 bedrooms and 2.5 bathrooms, in...

  • 3 Beds
  • 3 Baths
  • Winchester City SubDv.
  • 22601 Zip Code
  • CLOSED Status
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543 Gray Ave, Winchester $175,000

2 BD 1.5 Bath- Located near downtown Pedestrian walking mall, Hardwood floors, well maintained unit, fenced yard. Opportunity for first time home owner Or Investors Delig...

  • 2 Beds
  • 2 Baths
  • Winchester City SubDv.
  • 22601 Zip Code
  • CLOSED Status
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503 National Ave, Winchester $315,000

Come see this lovely home with great potential and convenience being located in downtown Winchester. The detached garage and off-street parking are definitely appealing f...

  • 3 Beds
  • 3 Baths
  • Winchester City SubDv.
  • 22601 Zip Code
  • CLOSED Status
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2428 Massanutten Ter, Winchester $314,000

Step into this inviting 3- bedroom, 1- bathroom property situated in the desirable Winchester area. With its classic brick exterior and charming covered front porch, this...

  • 3 Beds
  • 1 Baths
  • Winchester City SubDv.
  • 22601 Zip Code
  • CLOSED Status
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377 Pine St, Winchester $230,500

None

  • 3 Beds
  • 2 Baths
  • Winchester City SubDv.
  • 22601 Zip Code
  • CLOSED Status
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803 Woodland Ave, Winchester $180,000

None

  • 2 Beds
  • 1 Baths
  • Winchester City SubDv.
  • 22601 Zip Code
  • CLOSED Status
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2947 S Pleasant Valley Rd, Winchester $315,000

Cute Cottage vibes from this Winchester City ranch style home in a convenient location to all major area commuter routes, retail area, and medical facilities. A tradition...

  • 3 Beds
  • 2 Baths
  • Winchester City SubDv.
  • 22601 Zip Code
  • CLOSED Status
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119 W Cork St, Winchester $322,000

Have you been wanting to buy a place in downtown Winchester? Well, here is your chance! Views of the Apple Blossom parade from your front porch, a stone's throw from the...

  • 3 Beds
  • 2 Baths
  • Winchester City SubDv.
  • 22601 Zip Code
  • CLOSED Status
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618 S Washington St, Winchester $525,000

3 Bedrooms, 2.5 bath all brick home built in 1938 located in the Historic District with frontage on the Parade Route. Extra-large corner lot cannot be subdivided. Beaut...

  • 3 Beds
  • 3 Baths
  • Winchester City SubDv.
  • 22601 Zip Code
  • CLOSED Status
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115 E Monmouth St, Winchester $380,000

You have to see this house!! Tons of Charm!! Newly remodeled Colonial with a large backyard in the historic district with updated EVERYTHING!! The location is wonderful...

  • 4 Beds
  • 2 Baths
  • Winchester City SubDv.
  • 22601 Zip Code
  • CLOSED Status
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2939 S Pleasant Valley Rd, Winchester $310,000

This move-in ranch style home, on a quiet street in Winchester City with no HOA and a nice, flat yard is sure to please. The kitchen offers a laundry closet AND pantry. ...

  • 3 Beds
  • 2 Baths
  • Winchester City SubDv.
  • 22601 Zip Code
  • CLOSED Status
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313 Gray Ave, Winchester $247,000

Great older home so very close to downtown Winchester. Current owner working on so many improvements to include a brand new roof and newly installed 220 breaker box. T...

  • 3 Beds
  • 1 Baths
  • Winchester City SubDv.
  • 22601 Zip Code
  • CLOSED Status
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2927 S Pleasant Valley Rd, Winchester $309,900

One-level living in Winchester City, updated and move-in ready, with NO HOA on nearly half an acre. The list of "new" is hard to beat: brand new roof with architectural s...

  • 3 Beds
  • 2 Baths
  • Winchester City SubDv.
  • 22601 Zip Code
  • CLOSED Status
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425 Tevis St, Winchester $315,000

***New Home Sold***

  • 3 Beds
  • 3 Baths
  • Winchester City SubDv.
  • 22601 Zip Code
  • CLOSED Status
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31 W Southwerk St, Winchester $282,000

Brand new renovation only 2 blocks from Handley High School or Quarles Elementary School! Southwerk St has multiple homes that have recently been renovated, giving this ...

  • 3 Beds
  • 2 Baths
  • Winchester City SubDv.
  • 22601 Zip Code
  • CLOSED Status
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2959 S Pleasant Valley Rd, Winchester $290,000

This move-in ranch style home, on a quiet street in Winchester City with no HOA and a nice, flat yard is sure to please. The kitchen offers a laundry closet AND pantry wi...

  • 3 Beds
  • 2 Baths
  • Winchester City SubDv.
  • 22601 Zip Code
  • CLOSED Status
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911 Berryville Ave, Winchester $301,000

Discover the warmth of ample living space in this charming home. Relax on the tranquil private porch, unwind on the side deck, and enjoy the expansive yard. Conveniently ...

  • 3 Beds
  • 2 Baths
  • Winchester City SubDv.
  • 22601 Zip Code
  • CLOSED Status
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550 Gray Ave, Winchester $365,000

Seller offering $10K towards closing costs or lower interest rate and use it towards 2-1 buy down on your interest rate, ask agent for details! Check out this over 2100 s...

  • 4 Beds
  • 3 Baths
  • Winchester City SubDv.
  • 22601 Zip Code
  • CLOSED Status
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627 Fort Collier Rd, Winchester $260,000

This nice home is located close to just about everything, Shopping, Schools, highways, and downtown dining a perfect location for commuters or anyone who desires to be cl...

  • 3 Beds
  • 2 Baths
  • Winchester City SubDv.
  • 22601 Zip Code
  • CLOSED Status
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518 N Braddock St, Winchester $255,000

Introducing a charming property in highly sought after historic Old Towne Winchester. Situated on a spacious lot, this property boasts a large backyard providing ample s...

  • 4 Beds
  • 2 Baths
  • Winchester City SubDv.
  • 22601 Zip Code
  • CLOSED Status
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1604 Pondview Dr, Winchester $399,990

PRICED TO SELL QUICKLY! They don’t make them like this anymore. This beautiful split-level has been lovingly-maintained by the original owner – and now it can be yours! S...

  • 3 Beds
  • 2 Baths
  • Winchester City SubDv.
  • 22601 Zip Code
  • CLOSED Status
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2817 Papermill Rd, Winchester $280,000

This Winchester City home sits on a lovely 1/3 of an acre with mature trees, huge back deck, garden area and no HOA. Located just around the corner from retail shops and ...

  • 3 Beds
  • 2 Baths
  • Winchester City SubDv.
  • 22601 Zip Code
  • CLOSED Status
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209 N Washington St, Winchester $532,000

Living on Washington Street isn't just purchasing a home, it is a lifestyle. This historic property was constructed in 1853. The charm and character throughout are unpar...

  • 4 Beds
  • 3 Baths
  • Winchester City SubDv.
  • 22601 Zip Code
  • CLOSED Status
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609 Watson Ave, Winchester $220,000

Perfectly situated on a quiet street in downtown Winchester! This home has been recently remodeled and is move-in ready. Featuring an open concept on the main level with...

  • 3 Beds
  • 1 Baths
  • Winchester City SubDv.
  • 22601 Zip Code
  • CLOSED Status
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99 Bellview Ave, Winchester $350,000

COMPLETELY RENOVATED!! 3 bedroom 2 full bath, 3 story home in the heart of Winchester! Brand new kitchen with quartz countertops and full height quartz backsplash, polish...

  • 3 Beds
  • 2 Baths
  • Winchester City SubDv.
  • 22601 Zip Code
  • CLOSED Status
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623 Battle Ave, Winchester $359,900

Welcome to 623 Battle Avenue, a delightful 4-bedroom, 2-bathroom ranch nestled in the heart of Winchester, VA. This meticulously maintained home offers an array of featur...

  • 4 Beds
  • 2 Baths
  • Winchester City SubDv.
  • 22601 Zip Code
  • CLOSED Status
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135 Kent St S Unit 202, Winchester $239,000

SELLER WILL GIVE $2,500 CREDIT TO BUYER TO BUY DOWN THE RATE!!!!! Welcome to your dream condo in the heart of downtown Winchester! Light, bright, adorable and move-in rea...

  • 1 Beds
  • 1 Baths
  • Winchester City SubDv.
  • 22601 Zip Code
  • CLOSED Status
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4 E Southwerk St, Winchester $310,000

Huge Price Reduction! A Stunning 3 Bedroom, 2.5 bath home from a bygone era. Many original features have been preserved including the heart of pine floors, fireplaces and...

  • 3 Beds
  • 3 Baths
  • Winchester City SubDv.
  • 22601 Zip Code
  • CLOSED Status
3042 Valley, Unit 102, Winchester image
3042 Valley, Unit 102, Winchester $180,000

Office / Retail space in the Opequon Center on Valley Ave. in South Winchester. Unit fronts on main project entry way. 963 square feet with open area, small office, kitch...

  • Winchester City SubDv.
  • 22601 Zip Code
  • CLOSED Status
514 Cather Ave, Winchester image
514 Cather Ave, Winchester $335,000

Welcome to this home where classic charm meets modern versatility! Built in 1948, this property offers warmth, character, and flexible living spaces designed to fit today...

  • 3 Beds
  • 2 Baths
  • Winchester City SubDv.
  • 22601 Zip Code
  • CLOSED Status
520 N Braddock St, Winchester image
520 N Braddock St, Winchester $330,000

Welcome to this charming home in the heart of Winchester offering character, natural light, and a highly walkable location. This home features 3 bedrooms and 2 full bathr...

  • 3 Beds
  • 2 Baths
  • Winchester City SubDv.
  • 22601 Zip Code
  • CLOSED Status
704 Watson Ave, Winchester image
704 Watson Ave, Winchester $280,000

Beautifully Maintained Bungalow in a Prime Location! SELLER MOTIVATED! This home offers 2 bedrooms and 1 full bath on the main level, showcasing pride of ownership throu...

  • 2 Beds
  • 2 Baths
  • Winchester City SubDv.
  • 22601 Zip Code
  • CLOSED Status
317 Gray Ave, Winchester image
317 Gray Ave, Winchester $374,900

Welcome to 317 Gray Ave in Winchester, Virginia. This charming Colonial blends historic character with extensive modern updates, creating the perfect balance of vintage ...

  • 4 Beds
  • 3 Baths
  • Winchester City SubDv.
  • 22601 Zip Code
  • CLOSED Status
19 W Germain St, Winchester image
19 W Germain St, Winchester $337,000

Life in Historic Winchester just got easier with this modern construction. Built in 2004, this Charming 3 Bedroom, 1.5 Bath home is the best of all worlds. This home ha...

  • 3 Beds
  • 2 Baths
  • Winchester City SubDv.
  • 22601 Zip Code
  • CLOSED Status
743 Berryville Ave, Winchester image
743 Berryville Ave, Winchester $425,000

Welcome to 743 Berryville Ave in the heart of Downtown Winchester! This unique and versatile property offers exceptional space and flexibility with two fully equipped liv...

  • 4 Beds
  • 2 Baths
  • Winchester City SubDv.
  • 22601 Zip Code
  • CLOSED Status
232 Myrtle Ave, Winchester image
232 Myrtle Ave, Winchester $398,000

Must see this Newly Renovated 4–5-bedroom 2 Full bath, Main level has Brand New Kitchen Cabinets with Granite Counters & Stainless-Steel Appliances. Living room and two G...

  • 4 Beds
  • 2 Baths
  • Winchester City SubDv.
  • 22601 Zip Code
  • CLOSED Status
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7 W Hart St, Winchester $185,000

Welcome to this affordable Winchester bungalow! This cozy 2-bedroom, 1-bathroom home with 847 sq ft of living space is perfect for first-time homebuyers or savvy investor...

  • 2 Beds
  • 1 Baths
  • Winchester City SubDv.
  • 22601 Zip Code
  • CLOSED Status
13 E Hart St, Winchester image
13 E Hart St, Winchester $270,000

Estate sale, professionally cleaned and ready for move -in located between Loudoun & Cameron Streets, convenient to old town Winchester, shopping, restaurants, fun old t...

  • 3 Beds
  • 2 Baths
  • Winchester City SubDv.
  • 22601 Zip Code
  • CLOSED Status
407 Jefferson St, Winchester image
407 Jefferson St, Winchester $464,000

READY FOR BUYER! TURN KEY classic colonial, fully UPDATED, and WALKABLE to downtown! *3 LEVELS totalling 2568 SF* Stroll to the restaurants in Old Town, enjoy the activit...

  • 3 Beds
  • 3 Baths
  • Winchester City SubDv.
  • 22601 Zip Code
  • CLOSED Status
216 Fairmont Ave, Winchester image
216 Fairmont Ave, Winchester $512,000

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...

  • 3 Beds
  • 2 Baths
  • Winchester City SubDv.
  • 22601 Zip Code
  • CLOSED Status
27 Jackson Ave, Winchester image
27 Jackson Ave, Winchester $181,000

Great investor opportunity in the heart of Winchester! The LOWEST priced detached house within a 10-mile radius!! This 3-level home with a 2-car detached garage on a leve...

  • 2 Beds
  • 1 Baths
  • Winchester City SubDv.
  • 22601 Zip Code
  • CLOSED Status
320 Linden Dr, Winchester image
320 Linden Dr, Winchester $620,000

Experience generational refined living in this stunning luxury home just minutes from Winchester Medical Center. Designed for both elegance and comfort, this residence bo...

  • 4 Beds
  • 3 Baths
  • Winchester City SubDv.
  • 22601 Zip Code
  • CLOSED Status
2964 Grace St, Winchester image
2964 Grace St, Winchester $295,000

Wonderful Light filled 2 story Mid-Century Bungalow Updated for Modern Living while Maintaining its Original Charm and Style. An inviting Front Porch with Fabulous Wood ...

  • 2 Beds
  • 1 Baths
  • Winchester City SubDv.
  • 22601 Zip Code
  • CLOSED Status

Winchester City Real Estate & Homes

Our website features the best real estate search for homes, condos, land and foreclosure properties available in Winchester City, Winchester VA. It is the only site you will ever need! It is easy-to-use and updated by the official Realtor®’s database every 15 minutes. 

You can save searches, and get daily email alerts of new listings, price changes, sold data, and market reports. Our Interactive Map Search allows you to view properties on a map or refine your search by drawing the boundaries around the area you desire. 

Curious about what’s happening in your neighborhood? You can create a custom market report to see what’s active, under contract, and sold in your neighborhood! 

Considering selling or refinancing your home? Get an INSTANT property valuation now!

Contact us today to find out how we can be of assistance to you!

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Anne Nouri

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1.888.840.5553
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