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Browse All Winchester VA Historical Properties for Sale

1057 Foreman Ln, Winchester image
1057 Foreman Ln, Winchester $219,900

MUST SEE TO APPRECIATE THIS OFFBEAT RAISED FLAT, 1 BEDROOM 1 BATH, 4 ROOMS FRESHLY PAINTED. EAT IN KITCHEN COMES WITH A STOVE, REFRIGERATOR, MICROWAVE, LOTS OF CABINET S...

  • 1 Beds
  • 1 Baths
  • None Available SubDv.
  • 22603 Zip Code
  • COMING SOON Status
1310 Whittier Ave, Winchester image
1310 Whittier Ave, Winchester $429,000

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
912 Allen Dr, Winchester image
912 Allen Dr, Winchester $329,000

Charming, meticulously maintained brick rancher in the heart of Winchester City! This move-in-ready home features 3 spacious bedrooms, 1 full bath, and a convenient half ...

  • 3 Beds
  • 2 Baths
  • Eastview Subdivision SubDv.
  • 22601 Zip Code
  • ACTIVE Status
269 Poorhouse Rd, Winchester image
269 Poorhouse Rd, Winchester $229,000

Set on 1.4 acres with beautiful long-range views, this well-built home is ready for someone to bring it back to life. A strong structure, a covered front porch, and a gen...

  • 3 Beds
  • 1 Baths
  • None Available SubDv.
  • 22603 Zip Code
  • ACTIVE Status
117 E Pall Mall St, Winchester image
117 E Pall Mall St, Winchester $360,000

Welcome home to 117 E Pall Mall St! Ideally located within a mile of Shenandoah University and historic downtown Winchester! This 3 bedroom, 2.5 bath has lots of update...

  • 3 Beds
  • 3 Baths
  • Winchester SubDv.
  • 22601 Zip Code
  • ACTIVE Status
3424 Papermill Rd, Winchester image
3424 Papermill Rd, Winchester $229,900

Great location! Convenient to Town and Shopping. The property offers 2 bedrooms, and a full bath Tub/Shower. Detached Garage -left side for storage, other side vehicle....

  • 2 Beds
  • 1 Baths
  • No SubDv.
  • 22602 Zip Code
  • ACTIVE UNDER CONTRACT Status
420 W Cork St, Winchester image
420 W Cork St, Winchester $449,000

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...

  • 4 Beds
  • 2 Baths
  • Carter & Glaize SubDv.
  • 22601 Zip Code
  • ACTIVE Status
554 N Kent St, Winchester image
554 N Kent St, Winchester $230,000

Conveniently located in the heart of the City of Winchester, this charming home is just a short walk to the shops, restaurants, entertainment, and events of historic Old ...

  • 3 Beds
  • 1 Baths
  • Liberty Heights SubDv.
  • 22601 Zip Code
  • ACTIVE Status
1314 S Braddock St, Winchester image
1314 S Braddock St, Winchester $295,000

1314 S Braddock St is a one-story Winchester single-family home with a functional single-level layout. The kitchen is equipped with stainless steel appliances for everyda...

  • 3 Beds
  • 1 Baths
  • None Available SubDv.
  • 22601 Zip Code
  • ACTIVE Status
338 Lanny Dr, Winchester image
338 Lanny Dr, Winchester $435,000

Come home to Whittier Acres and this well maintained Rancher with 1-car garage just minutes from Winchester Medical Center. You'll love the cozy living room with wood bur...

  • 3 Beds
  • 2 Baths
  • Whittier Acres SubDv.
  • 22601 Zip Code
  • ACTIVE Status
361 E Piccadilly St, Winchester image
361 E Piccadilly St, Winchester $300,000

In the heart of Winchester with 3 bedrooms and 1 full bath. Hardwood floors, fresh paint, kitchen with granite countertops, appliances, including full-sized washer and d...

  • 3 Beds
  • 1 Baths
  • None Available SubDv.
  • 22601 Zip Code
  • COMING SOON Status
1311 Handley Ave, Winchester image
1311 Handley Ave, Winchester $600,000

Nestled in the charming City of Winchester, this delightful Colonial home, built in 1952, exudes warmth and character. With its classic brick exterior and excellent condi...

  • 3 Beds
  • 2 Baths
  • City Of Winchester SubDv.
  • 22601 Zip Code
  • ACTIVE Status
582 Miller Rd, Winchester image
582 Miller Rd, Winchester $1,650,000

Built in 1774, before America was America, this remarkable 31-acre estate has stood through the birth of a nation, and today it's ready for its next chapter. This is his...

  • 4 Beds
  • 5 Baths
  • Belleville Farm SubDv.
  • 22602 Zip Code
  • ACTIVE Status
135 S Kent St Unit #202, Winchester image
135 S Kent St Unit #202, Winchester $275,000

Step into the charm of Historic Downtown Winchester with this beautifully renovated Urban Lofts Condominium, where history and modern living come together. Located in a h...

  • 1 Beds
  • 1 Baths
  • None Available SubDv.
  • 22601 Zip Code
  • ACTIVE Status
434 Millwood Ave, Winchester image
434 Millwood Ave, Winchester $795,000

Well established, reputable, and long-standing auto service center in a prime location at the intersection of Millwood Avenue and Pleasant Valley Road directly across fro...

  • 22601 Zip Code
  • ACTIVE Status
21 E Germain St, Winchester image
21 E Germain St, Winchester $435,000 ▼

Seller offering closing cost assistance on select offers—contact the listing agent for details. Welcome to this beautifully renovated historic home in the heart of Old To...

  • 4 Beds
  • 2 Baths
  • Old Town Winchester SubDv.
  • 22601 Zip Code
  • ACTIVE Status
3764 Northwestern Pike, Winchester image
3764 Northwestern Pike, Winchester $750,000

RARE FIND! Discover the freedom and possibilities that come with 12.17 wooded acres—no HOA, no restrictions, just endless opportunity. Whether you're dreaming of creating...

  • 4 Beds
  • 3 Baths
  • None Available SubDv.
  • 22603 Zip Code
  • ACTIVE Status
145 Wilkins Dr, Winchester image
145 Wilkins Dr, Winchester $424,900

✨ Rare Opportunity on Winchester's East Side with a LOWER-LEVEL IN-LAW SUITE! 🏡 Welcome home to this spacious 4-bedroom, 2-bath beauty offering a warm, inviting layout a...

  • 4 Beds
  • 2 Baths
  • Green Acres SubDv.
  • 22602 Zip Code
  • ACTIVE Status
730 Merrimans Ln, Winchester image
730 Merrimans Ln, Winchester $3,175,000

A Once-in-a-Generation Opportunity: 1765 Heritage Meets Modern Luxury Rarely does a property of this caliber, history, and scale become available within Winchester city ...

  • 6 Beds
  • 7 Baths
  • None Available SubDv.
  • 22601 Zip Code
  • ACTIVE Status
108 Morgan St, Winchester image
108 Morgan St, Winchester $530,000

Welcome to this charming historic home in Old Town. A spacious 3-bedroom Colonial, where timeless character meets modern comfort in the heart of Winchester. Thoughtfull...

  • 3 Beds
  • 2 Baths
  • Winchester Historic District SubDv.
  • 22601 Zip Code
  • ACTIVE Status
384 National Ave, Winchester image
384 National Ave, Winchester $270,000 ▼

Discover the potential of this 4-bedroom, 2-bath multi-family property offering 1,730 sq ft of living space on a 2,684 sq ft lot. Built in 1930, this property is a great ...

  • 22601 Zip Code
  • ACTIVE Status
48 W Boscawen, Winchester image
48 W Boscawen, Winchester $1,724,000

Beautifully restored and fully modernized mixed-use building in the heart of historic Winchester. This exceptional offering includes a fully leased commercial building wi...

  • Winchester SubDv.
  • 22601 Zip Code
  • ACTIVE Status
143 E Dowell J Cir E, Winchester image
143 E Dowell J Cir E, Winchester $265,000 ▼

Charming Rancher with Prime Location and Endless Potential! This well-built, single-level rancher offers 3 bedrooms and 1 full bath across 1,000 square feet of smartly d...

  • 3 Beds
  • 1 Baths
  • Valley Mill Heights SubDv.
  • 22602 Zip Code
  • ACTIVE UNDER CONTRACT Status
135 & 171 Bufflick Rd, Winchester image
135 & 171 Bufflick Rd, Winchester $900,000

A rare commercial development opportunity awaits at 135 & 171 Bufflick Road, featuring nearly 8 acres of prime, strategic real estate in Winchester. Perfectly positioned ...

  • 22602 Zip Code
  • ACTIVE Status
124 S Braddock St, Winchester image
124 S Braddock St, Winchester $487,900

Circa 1920 office building in downtown Winchester. Currently used as a lawyer's office, but could easily be an office-and-residential space or a single-family home. Off-s...

  • 22601 Zip Code
  • ACTIVE Status
211, 213-215 E Clifford St, Winchester image
211, 213-215 E Clifford St, Winchester $350,000

Exceptional investment opportunity in the heart of Winchester! This unique offering includes three income-producing rental units for one price: one duplex and one single-...

  • 22601 Zip Code
  • ACTIVE Status
419 Van Fossen St, Winchester image
419 Van Fossen St, Winchester $380,000

. Vintage 1950's Build, In The City of Winchester. Perfect City living, across from Virginia Avenue Elementary and Post Office! Walking Distance from Old Town Winchester ...

  • 4 Beds
  • 2 Baths
  • None Available SubDv.
  • 22601 Zip Code
  • PENDING Status
101 Locust Ave, Winchester image
101 Locust Ave, Winchester $349,000

Welcome to 101 Locust Avenue in the heart of Winchester on a spacious corner lot! This solid brick ranch home offers 3 bedrooms, 2.5 bathrooms, and comfortable one-level ...

  • 3 Beds
  • 3 Baths
  • F A Crisman SubDv.
  • 22601 Zip Code
  • ACTIVE Status
305 Amherst St, Winchester image
305 Amherst St, Winchester $489,900

Downtown Winchester, circa 1926 foursquare. Kitchen addition, 3 bedrooms and two full baths. Walk Up attic, full basement , great yard.

  • 3 Beds
  • 2 Baths
  • Downtown Winchester SubDv.
  • 22601 Zip Code
  • ACTIVE UNDER CONTRACT Status
106 Blackfeet Trl, Winchester image
106 Blackfeet Trl, Winchester $215,000 ▼

Charming mountain retreat nestled on a full acre in Shawneeland! This cozy 1-bedroom, 1-bath cabin offers the perfect blend of privacy, nature, and modern comfort. Situat...

  • 1 Beds
  • 1 Baths
  • Shawneeland SubDv.
  • 22602 Zip Code
  • ACTIVE Status
719 National Ave, Winchester image
719 National Ave, Winchester $325,000 ▼

Priced to sell! A true Federal‑style gem, this solid brick home offers the chance to restore a piece of architectural history. Rich with original craftsmanship, it featu...

  • 4 Beds
  • 3 Baths
  • City Of Winchester SubDv.
  • 22601 Zip Code
  • ACTIVE Status
415 Puma Trl, Winchester image
415 Puma Trl, Winchester $125,000

Ranch cabin-style home nestled in the woods on a private ½-acre lot. Featuring 1-bedroom, additional room but not technically a bedroom, and 1 full bath, this property o...

  • 1 Beds
  • 1 Baths
  • Wilde Acres SubDv.
  • 22602 Zip Code
  • ACTIVE Status
225 Fox Dr, Winchester image
225 Fox Dr, Winchester $399,900

Welcome to 225 Fox Dr.! A very well maintained all brick ranch rambler. Has a fully updated kitchen with stainless steel appliances, quartz countertops, updated cabinetry...

  • 3 Beds
  • 2 Baths
  • Winchester SubDv.
  • 22601 Zip Code
  • ACTIVE Status
616 Opossum Trl, Winchester image
616 Opossum Trl, Winchester $165,000

Escape to the peace and privacy of Wilde Acres with this charming 2-bedroom, 1-bath cabin situated on four lots for a total of 1 acre, offering extra space and the possib...

  • 2 Beds
  • 1 Baths
  • Wild Acres SubDv.
  • 22602 Zip Code
  • ACTIVE Status
466 Merrimans Ln, Winchester image
466 Merrimans Ln, Winchester $899,000

Your long search is over! Beautifully renovated all-brick ranch home situated on a secluded 2.03-acre lot in the city of Winchester, just a short walk to Valley Health. O...

  • 3 Beds
  • 4 Baths
  • Winchester SubDv.
  • 22601 Zip Code
  • ACTIVE Status
102 N Purcell Ave, Winchester image
102 N Purcell Ave, Winchester $289,900

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
  • ACTIVE UNDER CONTRACT Status
1202 Handley Ave, Winchester image
1202 Handley Ave, Winchester $595,000 ▼

Nestled on one of Winchester's most sought-after streets, this distinctive mid-century contemporary home offers a rare blend of character, space, and convenience just mom...

  • 3 Beds
  • 4 Baths
  • Handley SubDv.
  • 22601 Zip Code
  • ACTIVE Status
410 S Cameron St, Winchester image
410 S Cameron St, Winchester $320,000

Step into a home where timeless character and modern opportunity come together. This spacious property is filled with antique charm and unique details throughout. Featuri...

  • 4 Beds
  • 2 Baths
  • None Available SubDv.
  • 22601 Zip Code
  • ACTIVE Status
140 Graywolf Trl, Winchester image
140 Graywolf Trl, Winchester $380,000

This fully finished 1,840 sq. ft. home offers the space, updates, and setting buyers are looking for. Featuring a fully finished walkout-level basement, newer hardwood fl...

  • 4 Beds
  • 2 Baths
  • Shawneeland SubDv.
  • 22602 Zip Code
  • PENDING Status
936 Allen Dr, Winchester image
936 Allen Dr, Winchester $319,900

Charming, beautifully maintained ranch home in a well-established Winchester neighborhood! Meticulously maintained and thoughtfully updated over the years, this special p...

  • 3 Beds
  • 2 Baths
  • Eastview Subdivision SubDv.
  • 22601 Zip Code
  • ACTIVE Status
302 Wentworth Dr, Winchester image
302 Wentworth Dr, Winchester $348,000 ▼

Enjoy one-level living in this spectacularly located brick rambler, nestled in a quiet residential neighborhood while remaining conveniently close to Route 11 with easy a...

  • 3 Beds
  • 2 Baths
  • None Available SubDv.
  • 22601 Zip Code
  • ACTIVE Status
405 Shenandoah Ave, Winchester image
405 Shenandoah Ave, Winchester $295,000

Ideally situated just minutes from I-81 and a short drive to historic Old Town Winchester, this centrally located rambler offers both convenience and investment potential...

  • 3 Beds
  • 1 Baths
  • Forest Hills SubDv.
  • 22601 Zip Code
  • COMING SOON Status
1306 Vanceright Cir, Winchester image
1306 Vanceright Cir, Winchester $480,000

Filled with storybook charm and timeless character, this enchanting cottage-style home is much larger than it appears! Newly refinished hardwood floors flow throughout th...

  • 4 Beds
  • 2 Baths
  • Himelright/Vanceright SubDv.
  • 22601 Zip Code
  • ACTIVE UNDER CONTRACT Status
622 Tennyson Ave, Winchester image
622 Tennyson Ave, Winchester $725,000

Available now in One of Winchester's Most Sought-After Locations. Opportunities like this don't come along often. Nestled on one of the most desirable streets in Winches...

  • 4 Beds
  • 3 Baths
  • Handley Board Of Trustees SubDv.
  • 22601 Zip Code
  • ACTIVE UNDER CONTRACT Status
2561 Apple Pie Ridge Rd, Winchester image
2561 Apple Pie Ridge Rd, Winchester $349,900

Welcome home to this beautifully updated rambler, offering comfort, character, and room to grow. The spacious front living room features gleaming hardwood floors and a la...

  • 3 Beds
  • 2 Baths
  • None Available SubDv.
  • 22603 Zip Code
  • ACTIVE Status
443 Fairmont Ave, Winchester image
443 Fairmont Ave, Winchester $449,900

So much potential !!! Great location, private yard, lots of square feet. Lot is 3/4 acre !Needs TLC. Listed $120,000 under tax assessment to allow room for updating. Kitc...

  • 2 Beds
  • 2 Baths
  • Fairmont Avenue SubDv.
  • 22601 Zip Code
  • PENDING Status
186 Wincrest Dr, Winchester image
186 Wincrest Dr, Winchester $3,100,000

Two 7800 SF metal buildings on 4.4 AC B3 land. 2 AC are Fenced in with a lockable gate. Currently used as auto repair shop with 3 lifts. Lifts and other auto related e...

  • None Available SubDv.
  • 22602 Zip Code
  • ACTIVE Status
3105 Apple Pie Ridge Rd, Winchester image
3105 Apple Pie Ridge Rd, Winchester $699,999

Situated on a beautiful tract of land with scenic views in every season, this charming farmhouse offers the space, tranquility, and rural lifestyle that buyers dream abou...

  • 4 Beds
  • 2 Baths
  • None Available SubDv.
  • 22603 Zip Code
  • COMING SOON Status
206 Dogwood Rd, Winchester image
206 Dogwood Rd, Winchester $425,000

Welcome to 206 Dogwood Rd. Well maintained 5 Bedroom 2 Bath Cape Cod in a quiet neighborhood conveniently located a short distance from the downtown area. HVAC has just b...

  • 5 Beds
  • 2 Baths
  • Shenandoah Hills SubDv.
  • 22602 Zip Code
  • ACTIVE Status
703 S Loudoun St, Winchester image
703 S Loudoun St, Winchester $450,000

Located in the heart of Winchester’s Historic District, this remarkable property offers a rare opportunity to own a piece of the city’s rich architectural heritage just m...

  • Winchester Historic District 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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