Historic District, VA homes for sale & real estate

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720 S Kent St, Winchester, VA 22601
720 S Kent St, Winchester, VA 22601
720 S Kent St, Winchester, VA 22601
ABOUT THIS HOME
Historic District, VA Homes for Sale
Welcome to the beautifully preserved American Foursquare where music legend Patsy Cline once lived with her mother—and later, with her husband, Charlie Dick. Built in 1931, this four-bedroom, one-and-a-half-bath home blends timeless character with thoughtful updates, all wrapped in the charm of one of Winchester’s most historic neighborhoods. Inside, you’ll find nearly 1,800 square feet of living space filled with original details, including stunning hardwood floors with an intricate decorative apple blossom inlay, classic trim, original bedroom door hardware, and the beloved three-over-one Craftsman-style sash windows. The main living areas are graced with built-in colonn

$550,000

4 beds2.5 baths1,798 sq ft

720 S Kent St, Winchester, VA 22601

4,996 sq ft lot • Very walkable

(571) 386-1075

COMING SOON

209 S Braddock St, Winchester, VA 22601
209 S Braddock St, Winchester, VA 22601
209 S Braddock St, Winchester, VA 22601
ABOUT THIS HOME
Historic District, VA Homes for Sale
Opportunity is knocking! Here's your chance to purchase a unique home in the beautiful Winchester Historic district. Step inside to hardwood flooring to your left is the formal living room with a brick fireplace with a mantel to display your treasures, on the main level you will find a full bath, laundry, and kitchen with Tiled Floors- off the kitchen is a door that leads to a patio and your backyard ready to design to your taste, imagine the possibilities! Upstairs you will find 2 bedrooms- the Primary Bedroom has an exposed stone wall, and a door leading to a landing. The upper level bath has a jetted tub and double sinks. Winchester's Historic district offers Parades which you can watch

$300,000

2 beds2 baths1,446 sq ft

209 S Braddock St, Winchester, VA 22601

4,561 sq ft lot • Very walkable

(540) 349-1400

214 S Braddock St, Winchester, VA 22601
214 S Braddock St, Winchester, VA 22601
214 S Braddock St, Winchester, VA 22601
ABOUT THIS HOME
Historic District, VA Homes for Sale
This property is currently zoned as fully commercial but has the potential to be changed to: Mixed Use or Fully Residential with proper city approval. Additional information from city located in documents. This home will need a Kitchen. Situated in Downtown Winchester, 214 S Braddock is waiting for your ideas! Built in 1865, this home features historic charm including exposed brick walls, beautiful hardwood floors, crown molding, original fireplaces, and super high ceilings, this space is sure to impress! This home is a lot larger than it appears from the outside! Large front porch leads to a space that would be ideal for a enjoying your coffee in the morning or relaxing after a long day!

$439,000

5 beds2 baths2,186 sq ft

214 S Braddock St, Winchester, VA 22601

3,951 sq ft lot • Very walkable

(703) 679-1700

112 W Germain St, Winchester, VA 22601
112 W Germain St, Winchester, VA 22601
112 W Germain St, Winchester, VA 22601
ABOUT THIS HOME
Historic District, VA Homes for Sale
100-Year-Old Downtown Winchester Charmer – Brought Back to Life in 2025! This beautifully restored century-old home has been completely reimagined from the ground up, blending timeless character with top-tier modern upgrades. Located in the heart of historic downtown Winchester, this home underwent a full-gut renovation in 2025—everything is new. From the all-new electrical wiring and replaced plumbing to brand-new ductwork, no system was left untouched. The structure itself was carefully reinforced with professionally engineered beams and supports, designed by a structural engineer. No corners were cut in this meticulous rebuild. Inside, you’ll find two brand-new HVAC sy

$665,000

3 beds2.5 baths1,650 sq ft

112 W Germain St, Winchester, VA 22601

3,999 sq ft lot • Very walkable

(540) 686-7362

107 E Monmouth St, Winchester, VA 22601
107 E Monmouth St, Winchester, VA 22601
107 E Monmouth St, Winchester, VA 22601
ABOUT THIS HOME
Historic District, VA Homes for Sale
Price Reduction!! Charming Historic Home in Downtown Winchester – Move-In Ready! If you love timeless craftsmanship—think original wood floors, custom built-ins, and vintage doors—but still want the ease of modern living, this beautifully updated downtown Winchester home is calling your name! From the moment you step onto the inviting covered porch and through the front door, you’ll feel right at home. Warm wood tones complement freshly painted crisp white walls, creating a perfect blend of cozy and fresh. The living room showcases a gorgeous staircase, beautifully refinished white oak floors, and an eye-catching wall of custom built-in shelving—ideal for your

$344,900

3 beds1.5 baths1,178 sq ft

107 E Monmouth St, Winchester, VA 22601

1,464 sq ft lot • Very walkable

(540) 662-0323

Property at 16 W Clifford St, Winchester, VA 22601, 3 beds, 2 baths

$275,000

3 beds2 baths1,804 sq ft

16 W Clifford St, Winchester, VA 22601

(703) 378-8810

Property at 230 W Boscawen St, Winchester, VA 22601

$649,000

— beds— baths7,650 sq ft

230 W Boscawen St, Winchester, VA 22601

(540) 662-9937

Property at 413 S Braddock St, Winchester, VA 22601, 2 beds, 1 bath

$249,000

2 beds1 bath1,542 sq ft

413 S Braddock St, Winchester, VA 22601

(540) 662-0400

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

$599,000

— beds— baths— sq ft

1 N Braddock St, Winchester, VA 22601

(540) 662-9937

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Nearby homes that match your criteria

553 Highland Ave, Winchester, VA 22601
553 Highland Ave, Winchester, VA 22601
553 Highland Ave, Winchester, VA 22601
ABOUT THIS HOME
Historic District, VA Homes for Sale
Completely remodeled! Come enjoy ALL new everything, new electric, new windows, luxury floors, freshly painted walls and brand-new custom kitchen and bathrooms, and all new plumbing and electric throughout, nothing has been left untouched! New Mini Split HVAC system. Large living room opens into a gorgeous wrap around peninsula kitchen with brand new Samsung appliances, granite countertop. Dining room is across the kitchen bar. Upstairs shas master bedroom 1, bedroom 2, Bedroom 3 and full bathroom with a huge closet. Don't miss this completely renovated gem, come tour today before it's gone.

$365,000

3 beds2 baths1,500 sq ft

553 Highland Ave, Winchester, VA 22601

3,999 sq ft lot • Somewhat walkable

(301) 355-6104

OPEN SAT, 11AM TO 2PM

912 Opequon Ave, Winchester, VA 22601
912 Opequon Ave, Winchester, VA 22601
912 Opequon Ave, Winchester, VA 22601
ABOUT THIS HOME
Historic District, VA Homes for Sale
Welcome to 912 Opequon Ave- Spacious, Updated & Perfectly Located in Winchester ! Opportunity meets versatility in this beautifully updated 5 bedrooms, 2 bath home nestled in one of Winchester most walkable and convenient neighborhoods! Whether you're a homeowner seeking flexible living space or an investor eyeing income potential, this property checks every box . Freshly painted interior with a bright, open living and dining area that flows seamlessly onto a large rear deck- perfect for relaxing or entertaining. The kitchen comes fully equipped with stainless steel appliances including a smooth -top range, double -door refrigerator , dishwasher, & trash compactor. The main level

$425,000

5 beds2 baths1,710 sq ft

912 Opequon Ave, Winchester, VA 22601

7,492 sq ft lot • Car-dependent

(703) 752-8660

1006 S Cameron St, Winchester, VA 22601
ABOUT THIS HOME
Historic District, VA Homes for Sale
Calling all investors! Don't miss out on this opportunity to restore this 5 bedroom/1 bath home. Hardwood flooring throughout. Large, covered front porch and rear deck. Less than a mile from , downtown Winchester & the Handley Library. Close to schools. Off-street parking and a spacious backyard.

$289,500

4 beds1 bath1,732 sq ft

1006 S Cameron St, Winchester, VA 22601

7,797 sq ft lot • Very walkable

(540) 686-7362

121 E James St, Winchester, VA 22601
121 E James St, Winchester, VA 22601
121 E James St, Winchester, VA 22601
ABOUT THIS HOME
Historic District, VA Homes for Sale
If your goal is to have an easy walk to Old Town Winchester, this is the home for you! Built in the early 1900's and full of charm!! The family room addition was done in1971 and is absolutely amazing!! Featuring 4 bedroom and 2 baths with approximately 2200 finished square feet!! Heating and air conditioning has been recently updated. The downstairs openness and light is incredible for this age home. In addition the lot has been extended to include the shed in the rear of the home along with additional sq footage. This is reflected on the survey in the documents. Great city location and fabulous price!!! Owner is a licensed real estate agent .

$399,900

4 beds2 baths2,200 sq ft

121 E James St, Winchester, VA 22601

4,729 sq ft lot • Very walkable

(540) 665-0360

257 Jefferson St, Winchester, VA 22601
257 Jefferson St, Winchester, VA 22601
257 Jefferson St, Winchester, VA 22601

$535,000

3 beds2 baths1,809 sq ft

257 Jefferson St, Winchester, VA 22601

9,147 sq ft lot • Garage • Somewhat walkable

(888) 400-2513

516 Hollingsworth Dr, Winchester, VA 22601
516 Hollingsworth Dr, Winchester, VA 22601
516 Hollingsworth Dr, Winchester, VA 22601
ABOUT THIS HOME
Historic District, VA Homes for Sale
Location & Lifestyle Highlights for 516 Hollingsworth Drive, Winchester, VA Nestled in one of Winchester’s most sought-after neighborhoods, 516 Hollingsworth Drive offers more than just a beautiful home; it offers a lifestyle. Enjoy direct access to scenic walking and biking trails, including the popular Green Circle Trail, which winds through town and links several parks and historic districts. Just minutes away, you’ll find Jim Barnett Park, a 170+ acre community destination featuring a recreation center, walking paths, playgrounds, a dog park, picnic shelters, a disc golf course, and an outdoor pool. It’s a perfect space for all ages and activity levels. Residents

$299,900

2 beds1 bath813 sq ft

516 Hollingsworth Dr, Winchester, VA 22601

8,276 sq ft lot • Car-dependent

(571) 386-1075

Property at 230 Allison Ave, Winchester, VA 22601, 3 beds, 1 bath

$344,900

3 beds1 bath1,376 sq ft

230 Allison Ave, Winchester, VA 22601

(540) 635-8000

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

$499,900

4 beds4 baths1,627 sq ft

201 Parkway St, Winchester, VA 22601

(703) 445-9100

Property at 509 W Cork St, Winchester, VA 22601, 3 beds, 1 bath

$369,000

3 beds1 bath1,024 sq ft

509 W Cork St, Winchester, VA 22601

(540) 662-0323

Property at 341 Opequon Ave, Winchester, VA 22601, 3 beds, 1.5 baths

$304,900

3 beds1.5 baths1,299 sq ft

341 Opequon Ave, Winchester, VA 22601

(540) 686-7362

Property at 320 Highland Ave, Winchester, VA 22601, 3 beds, 2 baths

$299,900

3 beds2 baths1,313 sq ft

320 Highland Ave, Winchester, VA 22601

(540) 348-4911

Property at 1321 Vanceright Cir, Winchester, VA 22601, 3 beds, 3.5 baths

$970,800

3 beds3.5 baths3,793 sq ft

1321 Vanceright Cir, Winchester, VA 22601

(540) 662-0323

Property at 520 Highland Ave, Winchester, VA 22601

$120,000

— beds— baths— sq ft

520 Highland Ave, Winchester, VA 22601

(540) 773-8475

Average home prices near Historic District, VA

Cities

Neighborhoods

Old Town homes for sale
$369,500
Kernstown homes for sale
$405,000

Historic District, VA real estate trends

$270K

Sale price

-34.1%
since last year

$272

Sale $/sq ft

+21.4%
since last year

Under list price

2.6%

Days on market

Down payment

3.0%

Total homes sold

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