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Browse All Winchester VA Historical Properties for Sale

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621 Watson Ave, Winchester $299,500

Fresh, stylish, and move-in ready! Welcome to 621 Watson Avenue, a beautifully refreshed 3-bedroom, 1.5-bath duplex offering a wonderful blend of classic character and mo...

  • 3 Beds
  • 2 Baths
  • City Of Winchester SubDv.
  • 22601 Zip Code
  • COMING SOON Status
805 S Kent St, Winchester image
805 S Kent St, Winchester $325,000

Welcome home! This beautifully maintained two-level home offers 4 bedrooms and 2 full bathrooms in the heart of Winchester. Warm and inviting, the home features a comfort...

  • 4 Beds
  • 2 Baths
  • City Of Winchester SubDv.
  • 22601 Zip Code
  • ACTIVE Status
322 E Piccadilly, Winchester image
322 E Piccadilly, Winchester $409,000

Welcome to a Mid‑Century Modern Home Where Timeless Character Meets Modern Sophistication. This beautifully updated 3–4 bedroom mid‑century modern home, where timeless ch...

  • 4 Beds
  • 1 Baths
  • None Available SubDv.
  • 22601 Zip Code
  • ACTIVE Status
131 Country Club Cir, Winchester image
131 Country Club Cir, Winchester $435,000

No HOA in the heart of Winchester! This charming brick rancher features three bedrooms, two baths, tall ceilings, fresh paint, hardwood floors, and a fireplace on the ma...

  • 3 Beds
  • 2 Baths
  • A Melvin Lewis SubDv.
  • 22602 Zip Code
  • COMING SOON Status
435 N Cameron St, Winchester image
435 N Cameron St, Winchester $900,000

This building located at 435 N. Cameron Street in Winchester, Virginia, formerly housed the Winchester Rescue Mission. Architecturally, it is a two-story, brick commercia...

  • 22601 Zip Code
  • ACTIVE Status
Winchester image
Winchester $1,450,000

5900 sf of Old Town elegance located in the middle of the walking mall at the fountain. 2 floors of finished space that currently is used for retail on the mail level an...

  • 22601 Zip Code
  • ACTIVE Status
214 Molden Dr, Winchester image
214 Molden Dr, Winchester $230,000

Investor opportunity in Winchester! This 2-bedroom, 1-bath home offers 1,112 finished square feet above grade, plus a full unfinished basement with additional space for s...

  • 2 Beds
  • 1 Baths
  • None Available SubDv.
  • 22601 Zip Code
  • ACTIVE Status
1048 Woodland Ave, Winchester image
1048 Woodland Ave, Winchester $350,000

Nestled in a charming neighborhood, this delightful ranch-style home offers a perfect blend of comfort and convenience. Built in 1954, this brick beauty exudes timeless a...

  • 3 Beds
  • 2 Baths
  • None Available SubDv.
  • 22601 Zip Code
  • ACTIVE Status
1412 S Loudoun St, Winchester image
1412 S Loudoun St, Winchester $429,000

Awesome Interior Photo's Coming Soon! Step inside this tastefully renovated brick ranch and feel instantly at home. Offering three comfortable bedrooms and two full baths...

  • 3 Beds
  • 2 Baths
  • None Available SubDv.
  • 22601 Zip Code
  • ACTIVE Status
305 Raccoon Dr, Winchester image
305 Raccoon Dr, Winchester $175,000

Cozy 1-bedroom, 1-bathroom cabin located on a level, nicely shaded lot, ready for your enjoyment. Offering the perfect combination of rustic character, comfort, and natur...

  • 1 Beds
  • 1 Baths
  • Wilde Acres SubDv.
  • 22602 Zip Code
  • ACTIVE Status
700 Tomahawk Trl, Winchester image
700 Tomahawk Trl, Winchester $287,000

Located in the desirable Shawneeland community, this freshly updated three bedroom home is situated on a great corner lot with scenic views and plenty of possibilities to...

  • 3 Beds
  • 1 Baths
  • Shawneeland SubDv.
  • 22602 Zip Code
  • ACTIVE Status
452 Valley Mill Rd, Winchester image
452 Valley Mill Rd, Winchester $299,900

SOLD AS IS, CASH ONLY! Investor special on this great home that is on .55 Acre lot (2 lots make this up). Outbuildings, wood floors, fireplace, 3 generous size bedrooms,...

  • 3 Beds
  • 1 Baths
  • None Available SubDv.
  • 22602 Zip Code
  • PENDING Status
531 Cedar Grove Rd, Winchester image
531 Cedar Grove Rd, Winchester $675,000

Discover a rare opportunity to own a piece of Frederick County history with this unique farmette property offering approximately 9.79 acres, a charming farmhouse, extensi...

  • 2 Beds
  • 1 Baths
  • Cedar Grove Road SubDv.
  • 22603 Zip Code
  • ACTIVE Status
2519 Hockman Ave, Winchester image
2519 Hockman Ave, Winchester $308,000

This charming cottage in the heart of the City of Winchester is poised for a remarkable transformation with major renovations slated for 2026. Built in 1950, this detache...

  • 2 Beds
  • 2 Baths
  • City Of Winchester SubDv.
  • 22601 Zip Code
  • ACTIVE Status
124 Dinkle Dr, Winchester image
124 Dinkle Dr, Winchester $345,000

Amazing and ready for new owner. New kitchen, new baths, newly refinished hardwood floors, new appliances, new HVAC. Come and check out this great 3 bedroom/2 bath home...

  • 3 Beds
  • 2 Baths
  • Shannon Hills SubDv.
  • 22601 Zip Code
  • ACTIVE UNDER CONTRACT Status
1414 S Braddock St, Winchester image
1414 S Braddock St, Winchester $379,900

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 convenience. With ...

  • 2 Beds
  • 2 Baths
  • Winchester City SubDv.
  • 22601 Zip Code
  • ACTIVE Status
1125 Conway St, Winchester image
1125 Conway St, Winchester $250,000

Welcome to 1125 Conway Ave, a charming bungalow in Winchester City that's move-in ready and full of character! This cozy 2-bedroom, 1-bath home features beautiful hardwoo...

  • 2 Beds
  • 1 Baths
  • Shannon Hill SubDv.
  • 22601 Zip Code
  • ACTIVE Status
394 Old Baltimore Rd, Winchester image
394 Old Baltimore Rd, Winchester $625,000

Coming Soon! A truly special property in a gorgeous, peaceful setting! This charming 1911 farmhouse sits on 2.75 acres and offers the perfect opportunity for a small farm...

  • 4 Beds
  • 4 Baths
  • None Available SubDv.
  • 22603 Zip Code
  • ACTIVE Status
182 Mason St, Winchester image
182 Mason St, Winchester $349,990

Welcome to this adorable 3-bedroom, 2-full-bath cottage rancher home located on the East side of Winchester with NO HOA! Offering approximately 1,024 finished square feet...

  • 3 Beds
  • 2 Baths
  • C M Lockhart SubDv.
  • 22602 Zip Code
  • ACTIVE Status
1077 Carpers Dr, Winchester image
1077 Carpers Dr, Winchester $354,900 ▼

Welcome home to this charming 3-bedroom, 2-bath house nestled on .32 acres, where comfortable living spaces and inviting outdoor areas come together to create a place tha...

  • 3 Beds
  • 2 Baths
  • None Available SubDv.
  • 22603 Zip Code
  • ACTIVE Status
224 Sharp St, Winchester image
224 Sharp St, Winchester $750,000

Rare Historical Winchester Investment Opportunity – Three Properties in One Location An outstanding investment opportunity awaits in the heart of Winchester City. This un...

  • 22601 Zip Code
  • ACTIVE Status
1019 Berryville Ave, Winchester image
1019 Berryville Ave, Winchester $499,000

1019 Berryville Ave, Winchester, VA 22601 | Prime Winchester location! This approximately 3,000+ square foot finished property offers flexibility, with three full, indep...

  • 22601 Zip Code
  • ACTIVE Status
187 Valley Mill Rd, Winchester image
187 Valley Mill Rd, Winchester $240,000

Great investment opportunity for this centrally located rambler! Just minutes from Route 7 and I-81, this property offers convenient access to shopping, restaurants, and ...

  • 2 Beds
  • 1 Baths
  • None Available SubDv.
  • 22602 Zip Code
  • ACTIVE Status
17 Glaize Ave, Winchester image
17 Glaize Ave, Winchester $240,000

Welcome to this charming Winchester home, coming soon! This adorable 2-bedroom, 1-bath property offers 757 square feet of cozy living space and plenty of character. Enjo...

  • 2 Beds
  • 1 Baths
  • None Available SubDv.
  • 22601 Zip Code
  • ACTIVE UNDER CONTRACT Status
221 Opequon Ave, Winchester image
221 Opequon Ave, Winchester $249,900

Charming 2-bedroom, 1-bath bungalow just blocks from the heart of downtown Winchester! This beautifully maintained home offers the character and convenience you're lookin...

  • 2 Beds
  • 1 Baths
  • Haddox Terrace SubDv.
  • 22601 Zip Code
  • PENDING Status
422 S Loudoun St, Winchester image
422 S Loudoun St, Winchester $434,000

Priced at recent appraised value. Welcome home to this beautifully maintained historic log home in the heart of Winchester. Thoughtfully updated while maintaining the cha...

  • 3 Beds
  • 3 Baths
  • City Of Winchester SubDv.
  • 22601 Zip Code
  • ACTIVE Status
414 N Braddock St, Winchester image
414 N Braddock St, Winchester $550,000

This charming farmhouse-style home,with off street parking, originally built in 1890 and beautifully renovated in 2018 (new windows, doors, HVAC, plumbing, drywall & ins...

  • 3 Beds
  • 3 Baths
  • None Available SubDv.
  • 22601 Zip Code
  • ACTIVE UNDER CONTRACT Status
14-16 S Loudoun St, Winchester image
14-16 S Loudoun St, Winchester $747,000

Rare opportunity to own a historic landmark in the heart of Old Town Winchester’s iconic Walking Mall. This impressive three-story commercial building offers approximatel...

  • 22601 Zip Code
  • ACTIVE Status
519 Virginia Ave, Winchester image
519 Virginia Ave, Winchester $274,000 ▼

This charming house has great potential. It is located directly across from the Virginia Avenue School campus, close to downtown Winchester. The exterior was recently pa...

  • 3 Beds
  • 2 Baths
  • None Available SubDv.
  • 22601 Zip Code
  • ACTIVE Status
334-338 Amherst St, Winchester image
334-338 Amherst St, Winchester $600,000

Long-established income producing investment property on Amherst Street. Two buildings including the historic Amherst Diner. The dinner leases for $3,500.00 monthly. T...

  • 22601 Zip Code
  • ACTIVE UNDER CONTRACT Status
501 Fox Dr, Winchester image
501 Fox Dr, Winchester $450,000

Welcome to this beautifully updated 4 bedroom, 2 full bath home in the heart of Winchester City! This move in-ready property offers fresh paint throughout, newly installe...

  • 4 Beds
  • 2 Baths
  • Walker Mcc Bond SubDv.
  • 22601 Zip Code
  • ACTIVE Status
413 Superior Ave, Winchester image
413 Superior Ave, Winchester $425,000 ▼

This beautiful rancher sits on 0.38 acres with an expansive, level backyard that is fully fenced and shaded by gorgeous mature trees. A large deck spans the back of the h...

  • 3 Beds
  • 2 Baths
  • Wea-Villa SubDv.
  • 22601 Zip Code
  • ACTIVE Status
12 N Purcell Ave, Winchester image
12 N Purcell Ave, Winchester $319,900

Welcome to 12 N Purcell Ave, a classic white bungalow offering standout curb appeal, a well-kept lawn and landscaping, and an unbeatable central location. Relax on the co...

  • 3 Beds
  • 1 Baths
  • None Available SubDv.
  • 22601 Zip Code
  • ACTIVE Status
1024 Front Royal Pike, Winchester image
1024 Front Royal Pike, Winchester $239,000

A great lot in a great location! 1024 Front Royal Pike is a prime opportunity packed with potential on a huge, nearly one-acre lot! Located in a highly desirable and con...

  • 2 Beds
  • 1 Baths
  • None Available SubDv.
  • 22602 Zip Code
  • ACTIVE Status
179 Westwood Dr, Winchester image
179 Westwood Dr, Winchester $324,900

All brick ranch home in an excellent location. The property is adorned with mature landscaping and flowers, trees and bushes that bloom all year long to constantly keep ...

  • 3 Beds
  • 3 Baths
  • Westwood SubDv.
  • 22602 Zip Code
  • ACTIVE UNDER CONTRACT Status
621 Patterson Ave, Winchester image
621 Patterson Ave, Winchester $357,500 ▼

CHARMING CAPE COD IN AN IDEAL IN‑TOWN LOCATION, THIS HOME HAS A WELCOMING EASE TO IT, OFFERING 3–4 BEDROOMS AND 2.5 BATHROOMS WITH A LAYOUT THAT ADAPTS BEAUTIFULLY TO EVE...

  • 4 Beds
  • 3 Baths
  • Glaize SubDv.
  • 22601 Zip Code
  • ACTIVE Status
201 Marple Rd, Winchester image
201 Marple Rd, Winchester $349,900 ▼

2.44 Acres with 1-Car Attached + 3-Bay Detached Workshop Garage — Close to Winchester Solid 1953 stucco home on 2.44 acres with a small wet weather pond and livestock fe...

  • 3 Beds
  • 1 Baths
  • None Available SubDv.
  • 22603 Zip Code
  • ACTIVE UNDER CONTRACT Status
407 S Loudoun St, Winchester image
407 S Loudoun St, Winchester $625,000

Historic office building located just south of the Old Town Walking Mall and the Government and Judicial Center. The 3,618 sq ft property includes two finished floors tha...

  • 22601 Zip Code
  • ACTIVE Status
1008 S Cameron St, Winchester image
1008 S Cameron St, Winchester $370,000

Live just minutes from historic Old Town Winchester, where charming boutiques, local restaurants, and picturesque streets are all close at hand. This beautifully maintain...

  • 4 Beds
  • 2 Baths
  • None Available SubDv.
  • 22601 Zip Code
  • ACTIVE Status
328 Smithfield Ave, Winchester image
328 Smithfield Ave, Winchester $260,000

"Investors take Notice" Here's a 2 unit with long term tenants on a month to month. There is much room for growth. 1 bedroom 1 bath in the back lower level has a Brand-Ne...

  • 22601 Zip Code
  • PENDING Status
153 Fox Dr, Winchester image
153 Fox Dr, Winchester $439,900

Welcome home to this beautifully maintained 3-bedroom, 2-bath home offering comfort, convenience, and exceptional outdoor living. Ideally located just minutes from shopp...

  • 3 Beds
  • 2 Baths
  • B P Myers SubDv.
  • 22601 Zip Code
  • ACTIVE Status
633 Pennsylvania Ave, Winchester image
633 Pennsylvania Ave, Winchester $399,000

OPEN HOUSE SATURDAY SEPTEMBER 12 FROM 11AM-1PM. Charming 1932 Craftsman Near Downtown Winchester! Step into this classic 1932 Craftsman home, where timeless historic ch...

  • 3 Beds
  • 2 Baths
  • Loudoun Manor SubDv.
  • 22601 Zip Code
  • ACTIVE Status
805 Pennsylvania Ave, Winchester image
805 Pennsylvania Ave, Winchester $359,000 ▼

Lovingly maintained, this charming brick rancher is the perfect starter home or investment opportunity! The main level offers three comfortable bedrooms, one full bath, a...

  • 3 Beds
  • 1 Baths
  • North Loudoun SubDv.
  • 22601 Zip Code
  • ACTIVE Status
2346 Welltown Rd, Winchester image
2346 Welltown Rd, Winchester $300,000

Charming Country Farmhouse with Modern Updates & Unrestricted Property! Welcome to this charming 1940's farmhouse, thoughtfully renovated and expanded in 2006 to blend ti...

  • 3 Beds
  • 3 Baths
  • None Available SubDv.
  • 22603 Zip Code
  • PENDING Status
2122 Jones Road, Winchester image
2122 Jones Road, Winchester $749,900 ▼

Beautifully renovated 1918 farmhouse situated on 10 scenic acres with views of Opequon Creek, accessible creek frontage, a picturesque pond, and some fenced acreage. Conv...

  • 3 Beds
  • 3 Baths
  • None Available SubDv.
  • 22602 Zip Code
  • ACTIVE Status
2810 N Frederick Pike, Winchester image
2810 N Frederick Pike, Winchester $280,000

Recently renovated and move-in ready! This updated 3-bedroom, 1-bath home offers the perfect combination of modern finishes and worry-free living with major upgrades alre...

  • 3 Beds
  • 1 Baths
  • None Available SubDv.
  • 22603 Zip Code
  • ACTIVE Status
403 Stag Trl, Winchester image
403 Stag Trl, Winchester $115,000

Ever dreamed of owning your own private A-frame cabin in the woods? Whether you're searching for the perfect weekend retreat, a unique short-term rental opportunity, or a...

  • Wilde Acres SubDv.
  • 22602 Zip Code
  • ACTIVE Status
567 N Cameron St, Winchester image
567 N Cameron St, Winchester $1,495,000

Great Warehouse in the City of Winchester, approximately 13,000 sq. ft. will be vacant by end of October

  • 22601 Zip Code
  • ACTIVE Status
735 Redbud, Winchester image
735 Redbud, Winchester $375,000 ▼

Situated directly across from historic Third Battle of Winchester Park, this charming brick ranch offers a rare opportunity to enjoy more than six miles of scenic walking...

  • 3 Beds
  • 2 Baths
  • None Available SubDv.
  • 22603 Zip Code
  • ACTIVE Status
1310 Whittier Ave, Winchester image
1310 Whittier Ave, Winchester $400,000 ▼

Turn-key and move-in ready! This beautifully updated 4-bedroom, 2-bath home features a modern kitchen with recently updated appliances, a new HVAC system, and a new hot w...

  • 4 Beds
  • 2 Baths
  • Northwestern Hills SubDv.
  • 22601 Zip Code
  • ACTIVE Status

Winchester Historical Real Estate

Our website features the best real estate search for historical properties available in Winchester and surrounding areas. 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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