540 Homes For Sale in Winchester, VA

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$209,900Est. Payment
2 Beds | 1 Bath | 1,085 Sqft

4936 Northwestern Pike, Winchester, VA 22603

House For Sale

Move in ready! Beautifully renovated 2 bedroom 1 bath home just minutes from Rt. 37, Winchester Hospital, schools and shopping. New kitchen with open living room floor plan with gorgeous hardwood floors throughout. This home features main level bedroom, bath, laundry room and upstair loft perfect for an office or kids space. New windows, vinyl siding, roof, HVAC and freshly painted all on .42 of an acre.

$536,450Est. Payment
4 Beds | 3 Baths | 2,357 Sqft

Lot 2 Covey Ln, Winchester, VA 22602

House For Sale

Location, Location, Location! New wooded 19 lot subdivision 10 minutes to Winchester 3 minutes to Clarke County. Sits off road and very private! See standard features sheet as they would be upgrades for many others. VDOT road, no HOA, basic restrictions. Several plans to choose from or have one altered or designed by builder's architect. EcoWater treatment system now included as standard by builder.

Let's get you that Dream Home!

Matt Ridgeway

(304) 676-2904
$125,000Est. Payment
11.19 Acres

200 Shaffer Ln, Winchester, VA 22602

Lots Land For Sale

Mostly wooded tract on east side of Winchester...Being sold strictly as land..Some abandoned structures on property are of no value...There is a well on the property but conveying "as is"...The Frederick County Health Dept has no septic records on this property. Survey of Tract 2 showing 11.192 Acres is in documents.

$79,000Est. Payment
5 Acres

Pine Crest Lane Lot 15, Winchester, VA 22603

Lots Land For Sale

Beautiful 5 acre lot in Frederick County. Chestnut Grove EST L15 5.00 Acres. Purchase the two adjacent lots and have a nice 15 acre (approx) estate.

$79,000Est. Payment
5.06 Acres

Pine Crest Lane Lot 25, Winchester, VA 22603

Lots Land For Sale

What a beautiful lot to build on! There are 2 adjacent lots if you'd like a larger estate! Map # 20 2 25. Owner said this lot previously perked. Please verify. Legal: CHESTNUT GROVE EST L25 5.06 ACRES

$79,000Est. Payment
5.03 Acres

Pine Crest Lane Lot 24, Winchester, VA 22603

Lots Land For Sale

Beautiful lot in Frederick County. Nice roads! CHESTNUT GROVE EST L24 5.03 ACRES There are 2 additional lots available for purchase Lot 25 and 15.

$274,999Est. Payment
3 Beds | 2 Baths | 2,243 Sqft

444 N Braddock St, Winchester, VA 22601

House For Sale

Featuring 3 beds and 2 baths this home has original details in every room! Beautiful wood floors through out, charming built ins, window seats, and beautiful wainscoting are just some of the original details found in this home. The kitchen is spacious and light and bright. There are three bedrooms and a full bath on the second level. The basement is unfinished and perfect for a workshop. Relax on warm days on the front porch or entertain in the shaded back yard!

$359,900Est. Payment
4 Beds | 3 Baths | 2,769 Sqft

155 Morning Glory Dr, Winchester, VA 22602

House For Sale

"Dreams of Morning Glory" - Have you been looking for a fully renovated house on the east side of town with a pool? Look no further - this is a house you won't want to miss! You'll be impressed with the custom renovation to this home, not missing out on any detail...all new carpeting throughout, complete new paint, custom light fixtures, stainless appliances, granite countertops, subway tile backsplash, sleek tile flooring, along with a fully finished basement. The backyard is an oasis filled with multi-layered decking, a fabulous pool ready to be used, a pond with fountains, and a huge landscaped backyard - the home is on a double lot! Nearly half an acre in a neighborhood where you normally get less less than a quarter of an acre. And here's the bonus...an oversized "man-cave" shed complete with full electricity, workbenches, and storage space. This is a one-of-a-kind house in a location ideal for commuters. Make your appointment to see it today...it won't last long! *Note that the agent is affiliated with the selling LLC*

$359,000Est. Payment
3 Beds | 2 Baths | 1,628 Sqft

1628 Valley Ave, Winchester, VA 22601

House For Sale

Welcome Home To This Stunning Chic Updated Bungalow! Walk To Old Town Farmers Market, shops & restaurants. The Front Porch Welcomes You To The Original Charm Yet Updated Home.Features Hardwood throughout, Living Room With Fireplace Opens To Formal Dining Room. Updated Kitchen With Ss Appliances, Ss Farm Sink, Granite Countertops and life proof flooring. A bright and cheerful sunroom welcome you as you enter through the rear of the home. This 3 bedroom, 2 bath home has been completely renovated. New dual HVAC, New Roof 2020, completely rewired. Enjoy The backyard Fire Pit. Fully Fenced Backyard Gives You Loads Of Room To Entertain. Plenty of off street parking that includes a 2 car detached garage and paved driveway. The detached garage windows have new glass, new windows in the sunroom.

$539,000Est. Payment
3 Beds | 2 Baths | 2,400 Sqft

227 Taggart Dr, Winchester, VA 22602

House For Sale

Starting Construction Now, Available in the Fall. The Fraser model is what one-level living should be: open, easily accessible and features amenities galore. This listing includes, hardwood floors, stainless appliances, vaulted ceiling, large master with tile shower. Buyer can choose exterior colors, cabinets, stone, tile and myriad upgrade options on granite, appliances, fixtures, Trex decking, etc. Basement can be finished to buyer's specs. Come see the difference in quality. Houses available to view.

$349,900Est. Payment
4 Beds | 2 Baths | 1,920 Sqft

3591 Apple Pie Ridge Rd, Winchester, VA 22603

House For Sale

PRIVATE AND RUSTIC. ESCAPE TO THIS LOVELY 3-ACRE RETREAT ON APPLE PIE RIDGE. Circa 1899 home with 4 bedrooms and 1 1/2 baths. The 4-stall barn and large garden shed make it a perfect place to relax while raising vegetables and a few animals. Horses, goats, sheep, llamas, cows and chickens are among the possibilities. Step inside the two-story house and step back in time. Among the house's features are its beautiful antique pine floors, decorative beams and a wood-burning fireplace with a brick hearth. There's even a claw foot tub! Partially covered 10x26 deck. Extensive landscaping. Picket fence in the front yard. Also black board fence and some wire fencing. Zoned agricultural. There's no HOA and it's not in a subdivision! The barn is L-shaped, 36x32 and the shed is 8x10. The septic perc is for 3 bedrooms.

$335,000Est. Payment
6 Beds | 3 Baths | 2,268 Sqft

401 Green Spring Rd, Winchester, VA 22603

House For Sale

Looking for the Apple Pie Ridge Area? This meticulously well maintained home is just 15 -20 minutes to hospital, shopping, schools, major roads and Winchester City. Own a piece of the country with this unique fully renovated, in 2016, raised ranch with multiple levels. Over 2200 sq ft of living space this home has room to grow for anyone. There is a living, dining, and kitchen open floor plan and two bedrooms and hall bath on the main level. Just a few steps down to another level where the master bedroom, master bath and laundry are located. The home boasts walk in closets, upgraded baths. On the opposite side of the home is a family room and another guest bedroom for entertaining or could be an in law quarters. The family room has a slider that walks out to a rear patio. Kitchen has an exit door to a large deck for those outdoor family gatherings. This kitchen has beautifully appointed cherry cabinets. All appliances are 4 years old. Sellers have added a UV light for fresh clear drinking water. Bring your horse, chickens, goats. This property is zoned Agricultural. With a fenced yard, several magnolia trees, 2 apples trees and a pear tree. There is a fenced paddock area and a run in shed. A Home Premium Warranty is offered as part of the sale. Don't miss your opportunity to be at home on this sweet property.

$249,500Est. Payment
3 Beds | 2 Baths | 1,500 Sqft

2933 Second St, Winchester, VA 22601

House For Sale

Built in 2015. Great location on a quiet street but minutes to downtown. Large rooms. Large level yard perfect for pets or relaxing evening fire pits and with room to add a garage or screened porch and large patio. The main floor master bedroom with walk-in closet and full bath can serve as large family room as it is now with two bedrooms and full bath upstairs. New carpet this past winter. Sunny eat-in kitchen. Third acre lot backs to trees. Covered entry. Sellers relocating out of state. 100% financing may be possible with some lenders.

$249,900Est. Payment
3 Beds | 3 Baths | 1,536 Sqft

2676 Limestone Ct, Winchester, VA 22601

Condominium For Sale

It's as good as it gets!! As if the prime Winchester City location alone isn't already enough to sell itself...This brick end-unit has also been meticulously maintained, thoughtfully remodeled & tastefully updated. Now featuring THREE fully finished levels, an additional 3rd bedroom & full bathroom in the basement, upstairs laundry, a total kitchen renovation with all new appliances, cabinets, countertops & bar seating, brand new roof, a HUGE brand new back deck and so much more. This small community is in big demand with historically very little available inventory for purchase - Don't let this one pass you by! Come see for yourself.

$210,000Est. Payment
3 Beds | 2 Baths | 1,384 Sqft

242 Liberty Ave, Winchester, VA 22601

House For Sale

INVESTMENT OPPORTUNITY in the heart of Winchester. Currently leased. This is a 3 bed, 1.5 bath home with a basement. Home has newer roof, siding, and floors in kitchen. Seller very motivated. Owner is selling 4 single family homes and 1 duplex. All properties are currently being leased. Property being sold As-Is. 24 hours to show. Agent or Owner will accompany at showing. Bring an offer!

$191,000Est. Payment
3 Beds | 2 Baths | 1,203 Sqft

318 Liberty Ave, Winchester, VA 22601

House For Sale

INVESTMENT OPPORTUNITY in the heart of Winchester. Currently leased. This is a 3 bed, 1.5 bath home with a fireplace and a fenced in yard. Seller very motivated. Owner is selling 4 single family homes and 1 duplex. All properties are currently being leased. Property being old As-Is. 24 hours to show. Agent or Owner will accompany at showing. Bring us an offer!

$158,000Est. Payment
2 Beds | 1 Bath | 687 Sqft

322 Liberty Ave, Winchester, VA 22601

House For Sale

INVESTMENT OPPORTUNITY in the heart of Winchester. Currently leased. This is a 2 bed, 1 bath home with a basement and a nice sized fenced in yard. Seller very motivated. Owner is selling 4 single family homes and 1 duplex. All properties are currently being leased. Property being sold As-Is. 24 hours to show. Agent or Owner will accompany at showing. Bring an offer!


Winchester is located in the Shenandoah Valley region of Virginia. This suburb boasts a rich history, as while working as a land surveyor, George Washington made his first trip here at age 16. With a population just over 27,000, the suburb offers a blend of historic charm, modern-day amenities and family-friendly events. There’s a home for you here, whether it’s located in the historic Clifford neighborhood, sits on three acres of land or is within walking distance of Winchester’s Old Town Mall.

Downtown Winchester (aka Old Town Winchester) values its heritage. This Virginia Main Street community is an important marketplace with a 250-year history and features a 45-block pedestrian walking mall. You will experience an eclectic mixture of antique shops, upscale furnishings, gift items, local and regional artwork, and fine clothing stores. The restaurants include indoor and outdoor café dining. Instead of strolling through downtown, you can use the city’s public transit system Monday through Friday. You have the option of travelling by bus or trolley. For travels outside of Winchester, there’s the Winchester Regional Airport, which is 70 miles from Dulles International Airport, and seven major roadways to get you where you need to go.

The signature Winchester event is the annual Shenandoah Apple Blossom Festival. Started in 1924, the festival has expanded into a ten-day extravaganza. Every year, hundreds of thousands of folks celebrate the arrival of apple blossoms while adorning the city in green and pink. There are over 30 events, including concerts, dances, a 10k race, golf tournament, wine festival, two massive parades, and more. Speaking of apples, the local farm market is a family favorite where residents pick fruit, take wagon rides or hang out at the playground. The Jim Barnett Park is the spot where you can enjoy a picnic lunch, chill by the swimming pool, play golf, basketball or tennis, hike, fish or go horseback riding. The other major events include Rockin’ Independence Eve, October Fest, KidzFest and Family Movies on the Mall, just to name a few. Winchester is a hard-working community in which 71 percent of its residents hold blue-collar jobs. There are four elementary schools, a middle school and high school serving the children of these hard-working families. In addition, there are two institutions of higher learning - Lord Fairfax Community College and Shenandoah University. If you work hard, play harder and relish a family atmosphere, then browse our selection of homes for sale in Winchester. Filter the listings and find your ideal property.

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