Historic District, VA homes for sale & real estate

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ABOUT THIS HOME
Historic District, VA Homes for Sale
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 square feet is designed for comfort and coziness accented by 9ft ceilings, sunlit formal rooms, a well appointed kitchen, spacious bedrooms, adorable loft on 3rd level for a playroom/den/office, and the best part is entering your private courtyard for relaxation, green thumb activity, and entertaining friends and family. Semi-circle driveway and plenty of storage in the basement make a case for you to definitely consider this your downtown home.

$550,000

3 beds1.5 baths2,177 sq ft

216 Fairmont Ave, Winchester, VA 22601

Semi-circle driveway • Storage in basement • Private courtyard

(540) 686-7362

COMING SOON

ABOUT THIS HOME
Historic District, VA Homes for Sale
Classic 2100 square foot brick “American Foursquare” house in Winchester’s historic district. This very well maintained 1928 home was designed and built by “ole time” craftsmen who had an appreciation for solid, quality construction. What better way to spend wonderful lazy evenings or morning coffee than on the expansive 23-foot long front porch with a ceiling fan. This 4 bedroom, 2 bath home is located in the historic Winchester “Potato Hill” neighborhood and just a few blocks from old town’s vibrant Loudoun Street mall. Enjoy numerous locally owned shops, historic attractions, street festivals, city sponsored activities, museums and restaura

$430,000

4 beds2 baths2,100 sq ft

17 E Leicester St, Winchester, VA 22601

4,138 sq ft lot • Garage • Very walkable

(540) 450-2747

ABOUT THIS HOME
Historic District, VA Homes for Sale
Step back in time with this Beautifully preserved VICTORIAN Brick Home Built in 1880, a true piece of Winchester's history. This is a Registered Historic Property that showcases original architectural details, high ceilings, ornate trim, and original wood floors that reflect the artistry of a bygone era. A Well Designed Addition has allowed for generous space along with modern comfort and functionality. Almost 3500 sq ft above grade, this home offers 4 bedrooms and 3.5 bath. The 3 HVAC units have been replaced within last 7-8 years. Did I mention there is a Main Level Bedroom with lovely French doors leading you to your Trex deck? Relax there with your coffee to experience a peaceful retre

$745,000

4 beds3.5 baths3,475 sq ft

132 Amherst St, Winchester, VA 22601

5,297 sq ft lot • 4 parking spots • Built 1900

(540) 665-0360

ABOUT THIS HOME
Historic District, VA Homes for Sale
This charming traditional brick home, nestled in the historic Winchester District, has a new minimalist European-inspired kitchen, a new full bath, and a new half bath. Featuring three spacious bedrooms, hardwood flooring and a welcoming dining area, perfect for gatherings. An entry-level bedroom adds convenience and flexibility to the layout. The house is 2 minutes walk to the apple blossom parades route, 3 minutes walk to downtown mall, 10 minutes walk to the court house. The 0.06-acre lot offers a manageable outdoor space, while on-street parking ensures easy access. With its blend of historic charm and modern updates, experience the best of city living in a community rich with amenities

$385,000

3 beds1.5 baths1,435 sq ft

20 W Clifford St, Winchester, VA 22601

On-street parking • 2,614 sq ft lot • Built 1900

(571) 408-8862

ABOUT THIS HOME
Historic District, VA Homes for Sale
Charming Remodeled Colonial in Historic Old Town Winchester You’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 hardwood floors throughout • 🍽️ Newly remodeled kitchen with modern cabinetry & appliances • ❄️ Modern HVAC system • 🧺 Laundry room off the kitchen • 🌳 Spacious backyard perfect for entertaining or relaxing • 🚶‍♂️ Walkable to downtown, Handley High, a

$315,000

4 beds1.5 baths1,199 sq ft

118 E Monmouth St, Winchester, VA 22601

3,480 sq ft lot • Built 1900 • Listed 73 days

(540) 504-0787

Property at 510 N Loudoun St, Winchester, VA 22601, 4 beds

$449,900

4 beds— baths2,376 sq ft

510 N Loudoun St, Winchester, VA 22601

(540) 686-7362

Property at 506 Fairmont Ave, Winchester, VA 22601

$235,000

— beds— baths— sq ft

506 Fairmont Ave, Winchester, VA 22601

(540) 662-0323

Property at 1 N Braddock St, Winchester, VA 22601

$549,900

— beds— baths— sq ft

1 N Braddock St, Winchester, VA 22601

(540) 662-9937

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COMING SOON

ABOUT THIS HOME
Historic District, VA Homes for Sale
Classic Stone Cape Cod Charm Meets Modern Luxury This stunning, remodeled 1940s Stone Cape Cod offers the perfect blend of timeless architecture and contemporary comfort on one of Winchester's most coveted, quiet neighborhood streets. Enjoy the unique lifestyle of being walkable to vibrant downtown, all while relaxing in your own almost half-acre, garden oasis. Step inside to discover a home meticulously updated home. The refinished hardwood flooring and an abundance of natural light lead you through a classic Better Homes and Gardens floor plan, now complemented by upgraded light fixtures and a remodeled powder room. The living room features a beautiful custom-made fireplace mantle with a

$679,900

3 beds2.5 baths3,278 sq ft

316 W Whitlock Ave, Winchester, VA 22601

0.45 acre lot • Somewhat walkable

(571) 386-1075

ABOUT THIS HOME
Historic District, VA Homes for Sale
Welcome to this beautifully preserved American brick Foursquare, an exceptional home that perfectly blends early 20th-century charm with modern updates. Nestled in one of Winchester’s most sought-after neighborhoods, this home is just two blocks from the annual Apple Blossom Parade , a short stroll to Old Town Winchester’s historic walking mall, and Handley High School. From the moment you arrive, you’ll be captivated by the classic architecture, large covered front and rear porches, and the lovingly landscaped yard featuring mature azaleas, crepe myrtles, and perennial blooms—a low-maintenance garden that bursts with color year after year. On the Main level, the hom

$629,000

3 beds2.5 baths2,575 sq ft

400 Handley Ave, Winchester, VA 22601

3,951 sq ft lot • Garage • Somewhat walkable

(540) 662-3484

ABOUT THIS HOME
Historic District, VA Homes for Sale
✨ Charming Winchester Home – Don’t Let This One Slip Away! Welcome to this beautifully refreshed home in the heart of Winchester, offering exceptional value, versatility, and convenience. Thoughtfully updated throughout, this property is move-in ready while still leaving room to make it your own. 💰 Seller is motivated and offering $7,000 in closing cost assistance — making this an incredible opportunity for qualified buyers! Enjoy ample off-street parking with rear-alley access, fresh renovations, brand-new vinyl flooring on the main level, and a new upstairs deck—perfect for morning coffee or evening relaxation. Property Highlights: 🛏️ 3 spacious bedrooms filled wit

$295,000

3 beds2 baths1,300 sq ft

423 Highland Ave, Winchester, VA 22601

3,746 sq ft lot • Very walkable

(540) 348-4911

COMING SOON

$365,000

4 beds2 baths1,780 sq ft

127 Shirley St, Winchester, VA 22601

4,996 sq ft lot • Somewhat walkable

(540) 665-0360

ABOUT THIS HOME
Historic District, VA Homes for Sale
Beautiful and affordable Gem in the middle of Winchester City. Private, fully fenced yard with extra parking and storage. Updated A/C and two year old roof.

$299,900

2 beds1 bath858 sq ft

525 E Cork St, Winchester, VA 22601

Garage • Somewhat walkable

(540) 662-3484

ABOUT THIS HOME
Historic District, VA Homes for Sale
Charming Downtown Winchester Home with Four Finished Levels. Welcome to 227 Miller Street, where timeless character and abundant living space come together in the heart of downtown Winchester. This inviting 3-bedroom, 4-bathroom home offers four fully finished levels that radiate warmth, comfort, and a true sense of home. Step onto the spacious covered front porch, a perfect spot to enjoy your morning coffee or watch the world go by on a quiet afternoon. Inside, a welcoming foyer leads you to a bright living room, a formal dining area ideal for family gatherings, and a sun-drenched enclosed sunroom that invites you to slow down and savor the light. The second level includes a bonus room, 2

$499,900

3 beds4 baths3,359 sq ft

227 Miller St, Winchester, VA 22601

8,668 sq ft lot • Somewhat walkable

(540) 773-8475

Property at 501 Jefferson St, Winchester, VA 22601, 5 beds, 2.5 baths

$659,000

5 beds2.5 baths3,420 sq ft

501 Jefferson St, Winchester, VA 22601

(540) 662-0323

Property at 553 Highland Ave, Winchester, VA 22601, 3 beds, 2 baths

$334,000

3 beds2 baths1,362 sq ft

553 Highland Ave, Winchester, VA 22601

(540) 687-6321

Property at 1400 Valley Ave, Winchester, VA 22601, 6 beds, 3 baths

$654,000

6 beds3 baths3,511 sq ft

1400 Valley Ave, Winchester, VA 22601

(844) 551-7325

Property at 420 W Cork St, Winchester, VA 22601, 4 beds, 1.5 baths

$499,900

4 beds1.5 baths1,932 sq ft

420 W Cork St, Winchester, VA 22601

(540) 662-0323

Property at 106 W Southwerk St, Winchester, VA 22601, 3 beds, 1.5 baths

$299,500

3 beds1.5 baths1,144 sq ft

106 W Southwerk St, Winchester, VA 22601

(540) 686-7362

Property at 580 N Braddock St, Winchester, VA 22601, 4 beds, 2 baths

$400,000

4 beds2 baths2,200 sq ft

580 N Braddock St, Winchester, VA 22601

(540) 299-6001

Property at 20 E Hart St, Winchester, VA 22601, 2 beds, 1 bath

$299,900

2 beds1 bath950 sq ft

20 E Hart St, Winchester, VA 22601

(540) 450-0142

Property at 369 Charles St, Winchester, VA 22601, 3 beds, 2 baths

$265,000

3 beds2 baths1,526 sq ft

369 Charles St, Winchester, VA 22601

(540) 665-0360

Property at 1004 S Cameron St, Winchester, VA 22601, 3 beds, 2.5 baths

$354,000

3 beds2.5 baths1,536 sq ft

1004 S Cameron St, Winchester, VA 22601

(703) 677-5889

Property at 201 Parkway St, Winchester, VA 22601, 4 beds, 4 baths

$474,500

4 beds4 baths1,627 sq ft

201 Parkway St, Winchester, VA 22601

(703) 445-9100

Average home prices near Historic District, VA

Cities

Neighborhoods

Kernstown homes for sale
$449,995

Historic District, VA real estate trends

$455K

Sale price

-15.0%
since last year

$243

Sale $/sq ft

+25.9%
since last year

Under list price

3.9%

Days on market

Down payment

3.0%

Total homes sold

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