Winchester Real Estate, Homes and Condos for sale

All Winchester homes currently listed for sale in Winchester as of 08/20/2019 are shown below.  You can change the search criteria at any time by pressing the 'Change Search' button below.

If you have any questions or you would like more information about any Winchester homes for sale or other Winchester real estate, please contact us and one of our knowledgeable Winchester REALTORS® would be pleased to assist you.


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$2,500,000
690 SHADY ELM RD, Winchester VA 22602
2
BEDS
2
BATHS
1,750
SQFT
$1,429
$/SQFT
61.20
ACRES
2000
BUILT
"Don't miss out on this extremely rare opportunity for your family or business to own this amazing farm filled with country atmosphere and less than 10 minutes from downtown Winchester. The panoramic scenic views of the Shenandoah Valley and the mountains will make you never want to leave. The sun rises and sunsets will take your breath away. The uses for this one of a kind opportunity are abundant! This location could be used for the family farm w/ 3 homes located on it or to be turned into the best business decision you've ever made. Could potentially be used as an Event Center, Brewery, Winery, Orchards, etc. The possibilities are endless! This farm has been owned and operated by The Robert Hockman Family since 1906. This property consists of 4 parcels being sold as one, totalling 61.2 acres. Currently, The Herds Inn is in use as a very successful Bed & Breaskfast w/ 75% occupancy through the year. The Historic Manor home that was built in 1907 is full of charactor and family warmth. In addition there is another log home on the property built in 2007 that could be used for family or as another Bed & Breakfast. The Herds is was built with all reclaimed items from the farm land to historic properties near and far. It boasts stain glass windows, limestone from the farm, flooring from vinegar vats, front door from an 1806 historic property located in downtown Winchester, banister from apple processing plant and the list goes on. There is income on this property from Shentel and WXVA AM/FM (102.9), with approximately 15 years remaining on the contract. This land has been used for years to supply individuals and the community with fresh raw milk, raw milk cheese, eggs, grass fed feed beef, pork and lamb. All hormone and antibiotic free and grass fed only. In years past this farm was used for yogurt business, apple orchards, dairy (since 1948), school field trips, events throughout the year, community garden. When visiting this beautiful farm, the 100+ ye"
* NEW LISTING 
$2,400,000
4255 MIDDLE ROAD RD, Winchester VA 22602
2
BEDS
2
BATHS
2,442
SQFT
$983
$/SQFT
320.00
ACRES
1889
BUILT
"320 acres of picturesque fertile farmland can be subdivided or used as a working farm some orchard some Woodland plus tillable land two houses one a remodel farmhouse and plus a smaller tent house frontage on middle Road and Spring Dale Road behind orchard view elementary school 4 tax map parcels.74-A-4, 74-A-4A, 74-A-4C, and 62-A-38"
* LISTED OVER 120 DAYS  * PRICE LOWERED - $2,560,000 TO $2,400,000 
$1,500,000
RITTER RD, Winchester VA 22602
1
BEDS
1
BATHS
203.79
ACRES
* LISTED OVER 120 DAYS 
$1,300,000
1579 CEDAR CREEK GRADE, Winchester VA 22602
5
BEDS
6
BATHS
6,832
SQFT
$190
$/SQFT
33.68
ACRES
1997
BUILT
"TIMELESS ARCHITECTURE! Welcome home to Cedar Crest....a rare opportunity to own a Virginia Manor House ready for your creativity to begin a new chapter in 21st Century! Architecturally inspired from the renowned works of William Lawrence Bottomley's Richmond, Virginia homes, Cedar Crest was commissioned to take advantage of the spectacular pastoral and mountain views of Frederick County. Conveniently located just outside the charming town of Winchester and convenient to Route 37 and Interstate 81, Cedar Crest was built in 1996, but gives the impression of age and Old World charm. Built on land steeped in Civil War history with the First Battle of Kernstown beginning across the field on the Glass Farm on March 23, 1862. This home was built for living well...gracious enough to host the most influential for dinner, but family-centered enough to play Crazy8s in any room."
* PRICE LOWERED - $1,400,000 TO $1,300,000 
$1,259,900
155 ROBINSON DRIVE, Winchester VA 22602
5
BEDS
8
BATHS
7,396
SQFT
$170
$/SQFT
5.06
ACRES
1999
BUILT
"Every detail of this home is exquisite and precisely refined from the magnificently landscaped 5 acre lot to the spacious main floor master featuring a marble bath tub, double vanities and a large walk-in closet. 5 bedrooms each with their own bath. The gourmet kitchen provides top of the line stainless steal appliances and walk-in pantry. The finished basement features a media room, kitchenette, full bath, and storage. Relax on the terrace by the salt water cocktail pool and serve lunch in the luxurious pool house. Ample parking w/ a 3 car garage and a separate 2 car garage. The guest house offers 3 bedrooms, 2 bathrooms, a full kitchen, laundry, and its own garage."
* LISTED OVER 120 DAYS  * PRICE LOWERED - $1,369,000 TO $1,259,900 
$974,900
400 GLEN LEA CT, Winchester VA 22601
4
BEDS
6
BATHS
6,017
SQFT
$162
$/SQFT
1.00
ACRES
2003
BUILT
"Masterful design & modern luxury are embodied in this one-of-a-kind Contemporary Craftsman home. The secluded lot borders 10 wooded acres, yet a few blocks walk to Old Town. Highlights of this amazing property are Chef's Kitchen with Z-Island, Serene Owners Suite and Sauna, Media Room, Slate Walls, Cedar Porch with Mexican Tile, a large game room with Red Quartz Bar and stunning Mosiac tile. Your DREAM home awaits Tap 1st virtual tour for FLOOR PLANS and PHOTOS"
$925,000
1107 CEDAR CREEK GRADE, Winchester VA 22602
4
BEDS
4
BATHS
5,725
SQFT
$162
$/SQFT
5.00
ACRES
1986
BUILT
"This spacious contemporary with almost 6000 sq ft of living space hosted Apple Blossom Events. Three large bedrooms each with private bath, plus a walk out basement apartment with private entrance. Open kitchen with skylights. Kitchen flows out to the large front deck for entertaining. Large living and dining room with a wood burning fireplace. Glass sunroom with HVAC for those spring and summer days. Private downstairs apartment has full bathroom, kitchen, and laundry. For possible additional income. Property sits on 5 acres (Agricultural Zoned) with additional revenue from Farmers Market (3200 sq. ft.) under a conditional use permit. The market has a half bath,30x60 kitchen and retail space. Run in barn (28X30)could be converted to stables for a horse or farm equipment shed. The shed has running water. For those adventurers there is a hook up on property for an RV. Beautiful Garden in the private backyard. Offering a quiet retreat hard to find so close to town."
* LISTED OVER 120 DAYS 
$917,700
217 BOSCAWEN STREET WEST, Winchester VA 22601
6
BEDS
6
BATHS
4,820
SQFT
$190
$/SQFT
0.30
ACRES
1840
BUILT
"Historic property in Old Town Winchester, completely renovated, ZONED COMMERCIAL, new electric and much more. Beautiful detail throughout. FRESHLY PAINTED IN AND OUT. CAC 3 zones, 7 heat zones. 2 story windows in foyer, private off street parking, Butlers Pantry .English terrace, 60+ boxwoods, brick, slate roof, double porches, elegant staircase, 8 fireplaces, Currently upscale B&B, R.E. Only"
* LISTED OVER 120 DAYS 
$895,000
1121 N HAYFIELD RD, Winchester VA 22603
4
BEDS
4
BATHS
5,451
SQFT
$164
$/SQFT
10.25
ACRES
2003
BUILT
"Gorgeous Country Estate on 10.5 Acres. Less than 8Miles away from Winchester Medical Center! Prepare to fall in love with the gourmet kitchen, two main level master suites and generous upscale finishes throughout. The neutral and modern color scheme makes this house a genuine pleasure to call home. This meticulously kept brick colonial features plenty of room for all your entertaining needs. Enjoy year-round fitness and fun in the indoor heated saltwater pool. Custom mature landscaping offers plenty of curb appeal, and is the frosting on the cake! Property has Comcast! Set up your private tour today! No HOA!"
* LISTED OVER 120 DAYS 
$895,000
343 WINDSOR LN, Winchester VA 22602
5
BEDS
6
BATHS
7,905
SQFT
$113
$/SQFT
5.00
ACRES
1994
BUILT
"Truly one-of-a-kind quality built all brick home that sits on 5 acres and has approx. 7,905 finished SF of space including 5 bedrooms, 4 full and 2 half baths. This home has 3 levels of living space, each with its own zoned heat/air, an in-ground heated pool with cover, tiered decking in the rear, an elevator, a 3-bay garage, 4 fireplaces, a fire pit, plus a floored attic for additional storage. All this on a magnificently secluded lot with extensive landscaping and hardscaping giving you a private home to relax in! When you enter the grounds, you drive up around the paved circular driveway and exit to the portico shielding you from the elements as you walk inside. The grand two-story foyer will wow you with beautiful inlaid hardwoods, a sparkling chandelier giving you plenty of light to see the spectacular staircase or a view through to the great room in the rear of the home. On the main level, you will find a two-story great room with a gas fireplace, a formal dining room, and the huge master bedroom with walk-in closet, an attached study with built-in cabinets & a gas fireplace, and a master bath with jetted tub, separate shower & water closet, plus a two-bowl vanity with seating. The gourmet kitchen has double wall ovens, a cooktop with downdraft venting, corian counters, an island, a paneled fridge to match all those rows of cabinets, a DW, an additional prep sink, plus recessed lighting and a desk area for study. All this next to a breakfast/sitting area that has a wood-burning fireplace, built-in cabinets/shelving, and a door leading out onto the deck for eating or enjoying the views! When outside, you can either swim in the heated pool or stroll down to the fire pit on those chilly evenings to sit around the fire and make smores!! Downstairs there is a wonderfully large family/rec room with more built-ins, a gas fireplace, a bar/wet bar area, plus a full bath that is handicap friendly with a roll-in shower, and roll under vanity. The laundry is lo"
$889,000
613 STONYMEADE DR, Winchester VA 22602
5
BEDS
6
BATHS
6,603
SQFT
$135
$/SQFT
5.00
ACRES
2005
BUILT
"Turn key ready with fresh paint and refinished floors. Grand home includes 1st floor suite. Master suite and 3 other Large bedrooms on upper level boast walk in closets and en-suites. Finished basement with theater room as well. Entertain all four season with heated salt water pool and gas fire pit. Wrap around porch to enjoy mountain views. 3 car heated garage. Plus convenience to town."
* NEW LISTING 
$889,000
1004 HETH PL, Winchester VA 22601
4
BEDS
5
BATHS
5,184
SQFT
$171
$/SQFT
0.44
ACRES
2007
BUILT
"Remarkable Brick Colonial sitting amid meticulously sculptured gardens and mature plantings that envelope the property in serenity and privacy. Loaded with amenities, all three finished floors reflect the quality and care given the gardens. Spacious rooms and abundant ambient light augment the open, airy entertaining areas that spill out onto the large patio, koi pond and rose garden."
$879,000
LACOSTA COURT, Winchester VA 22602
4
BEDS
4
BATHS
3,052
SQFT
$288
$/SQFT
2.14
ACRES
2019
BUILT
"This Modern Farmhouse is highlighted with a gorgeous exterior. An amazing array of lovely architectural details are featured on the exterior of the home and include a courtyard entry, three-car garage. There are gorgeous window views, overhead dormer shed windows, wide eaves on the gables, and a front covered porch. The porch design is expansive and adds charm and texture to the home's visual appeal as well as a nice gathering spot for family and friends. The home's interior floor plan features in excess of 3,050 square feet of living space with 4 bedrooms and 3.5 baths in 2 stories. The home will be situated on a walk-out basement foundation for future expansion possibilities. Front porch entry leads into the open floor plan where there is a large vaulted great room with surrounding picturesque window views, a warming fireplace and slider access to the rear porch. The open floor plan is completed with kitchen and dining room views. The gourmet kitchen features a center island, double pantries, and large amounts of counter and cabinet space. The upper level features a host of secondary bedrooms, a loft space, and bathrooms. The loft space is located at the end of the hallway and features a good amount of space for a playroom, lounge, or as a possible media room. The three upstairs bedrooms are similar in size and each features window views, generous closet space and bathroom access. Bedroom #4 is the largest of the three, and is highlighted with a private bathroom, while bedrooms #2 and #3 share a Jack-and-Jill bathroom. This beautiful Modern Farmhouse design is luxuriously detailed on both the exterior and interior making it a wonderful house plan!"
$839,000
308 SAINT ANDREWS CT, Winchester VA 22602
4
BEDS
5
BATHS
4,532
SQFT
$185
$/SQFT
2.26
ACRES
2015
BUILT
"Elegant Stone and Stucco Colonial loaded with amenities--hardwood floors, gourmet kitchen w/ wine cooler, wet bar with dishwasher and refrigerator, generously sized rooms, 24 x 24 Trex deck, level basement walkout onto large patio perfect for entertaining. Panoramic golf course views. Located minutes from the Medical Center and with easy access to commuter routes. Impressive upscale neighborhood"
* PRICE LOWERED - $850,000 TO $839,000 
$809,900
901 ARMISTEAD ST, Winchester VA 22601
6
BEDS
6
BATHS
5,811
SQFT
$139
$/SQFT
1.38
ACRES
1993
BUILT
"Owner has moved and says sell it. Huge price reduction. Priced way below the Zillow zestimate. Custom built all bring on 1.3 acre lot near Valley Health. Gorgeous yard and landscaping compliment this home of 6,134 sq. ft. Master on the main level, tons of storage and a great workshop. Fully finished walk-out basement w/ a kitchen and additional bedroom & bath. First floor brick patio, gourmet kitchen. Priced to sell. Do not miss this opportunity."
* LISTED OVER 120 DAYS  * PRICE LOWERED - $849,900 TO $809,900 
$789,900
1023 HETH PL, Winchester VA 22601
5
BEDS
5
BATHS
5,960
SQFT
$133
$/SQFT
0.41
ACRES
2002
BUILT
"Custom built by local builder, Don Packard Jr., this quality all brick home definitely has the wow factor. Dramatic entry foyer, huge main level master w/ sitting room, over the top bathroom and large closets. Formal living room, sensational 2 story family room with a fireplace, and 2 staircases. This one of a kind home also features a large fully finished walk-out basement with a rec room, fireplace, wet bar, bedroom, full bath, and plenty of storage. Close to shopping, Valley Health, and an elementary school."
$725,000
220 SPARTAN CT, Winchester VA 22603
7
BEDS
6
BATHS
6,238
SQFT
$116
$/SQFT
7.00
ACRES
2006
BUILT
"OPEN HOUSE Sun, Jul 28 1:00 PM - 3:00 PM - Swim, Fish, Hike, ride ATV's- all on your own property! Phenomenal opportunity to own your own piece of paradise. Gorgeous views surrounding this home- offering exceptional exterior features; sparkling swimming pool with waterfall, stone fire pit, pool house with convenient bath and drive-in shed, hot tub pad & outlet. Explore the wooded acreage in back boasting a Spring fed Stocked Pond - Bass, Bluegill & Koi. Welcoming wrap around front porch is just perfect for sipping your favorite beverage while gazing at the peaceful mountain and pastoral views. Two story foyer leads in to an amazingly immaculate open main level & the heart of the home- a spacious,beautifully equipped gourmet kitchen with sprawling granite counter tops, cook-top island, double ovens, bar and large breakfast room that leads out to the screened porch and sunny deck. The main level also boasts an office with French doors, family room off kitchen with a handsome floor to ceiling Kentucky cut stacked stone fireplace and sunny solarium. Upper level presents 5 spacious bedrooms and 3 full baths- each with unique views. Master suite with tray ceiling, walk in closet with custom shelving, cedar closet and luxurious bath offering a vanity area, Jacuzzi soaking tub and bench seat double shower. Fully finished basement is perfect for completely separate living quarters - equipped with a convenient full second kitchen, 2 bedrooms and a full bath and a second stacked stone fireplace. Walk right out to the patio, decks, fire pit and fenced pool area. Enjoy the Mountain views & Gorgeous Sunsets- from the covered front porch, screened porch or the Upper & Lower trex decks with Azek low maintenance railing. Electric Fencing & Generator. Have your very own Family KOA with riding trails- vacation at home! Contractor owned Custom-Built home is truly special! Don't forget to check out the Matterport Virtual Tour!"
* PRICE LOWERED - $750,000 TO $725,000 
$724,900
220 ANNA MARGARET DR, Winchester VA 22602
4
BEDS
4
BATHS
5,000
SQFT
$145
$/SQFT
2.74
ACRES
2006
BUILT
"PRISTINE 5000 SQ FT ALL BRICK CUSTOM HOME IN PRESTIGIOUS GRANVILLE ESTATES WILL WOW YOU! Just 7 miles from town and in rural and sought after neighborhood, this beauty consists of a main floor master plus 2nd bedroom/office on main floor. Gourmet kitchen includes granite, stainless steel appliances, kitchen bar and breakfast nook, as well as 2 pantries! Grand 2 story foyer and great room with built in cabinetry and fireplace. Hardwood floors throughout main and upstairs levels. Separate dining room has crown and chair railing. Master en suite features a tray ceiling, double walk in closets, well appointed bath with double vanities, air jetted tub and tiled walk in shower. Upstairs has 2 additional bedrooms and a huge bonus room with vaulted ceilings. Fully finished basement has family room, game area, granite bar for entertaining! DON'T MISS THE DETACHED 4 CAR GARAGE WITH SEPARATE GUEST QUARTERS! This space consists of huge gourmet kitchen and great room combo, 23 x 21 ft master suite with tiled shower and separate air jetted tub, laundry room, built ins and deck. The 4 car detached garage has 4 bays including a 12 ft garage door, and three 10 ft doors. Many upgrades including 50 year shingles and icynene spray foam insulation."
$700,000
811 FOX DR, Winchester VA 22603
4
BEDS
2
BATHS
2,091
SQFT
$335
$/SQFT
4.67
ACRES
1971
BUILT
"4.67 Acres zoned RP with potential conversion for Mixed Use. Frontage on Fox Drive close to Winchester Medical Center. Adjacent to Sunnyside Plaza Shopping Center and Fox Ridge Townhouse Community. 809-811 Fox Dr. is a brick duplex currently leased on the property. The balance of the 4.6 acres on Fox Dr. and Redoubt Lane is clear. Call for Plat and more info."
* LISTED OVER 120 DAYS 
$675,000
196 CRISPIN TRL, Winchester VA 22603
5
BEDS
5
BATHS
6,745
SQFT
$100
$/SQFT
12.21
ACRES
2006
BUILT
"You're invited to enjoy the mountain views on your 12 acre homestead that includes a pond. Glorious home price to sell $62,000. Below assessment."
$675,000
196 CRISPIN TRL, Winchester VA 22603
4
BEDS
5
BATHS
6,745
SQFT
$100
$/SQFT
12.21
ACRES
2006
BUILT
"Custom built home with every upgrade imaginable. Situated on 12 acres with a pond and mountain views. Yet only 15 mins to town! Large family room w/double sided fire place leading to sun room and coffered ceilings to top it off. Gourmet Kitchen made to entertain with butlers pantry. Love the 2nd floor loft, and 3 large bedrooms each with attached bath. Enjoy the finishing touches in the basement with Loads of space including full bar and theater room. Totaling over 6000 sqft, Turn key ready and priced to sell below assessment! Get instant equity."
$674,999
1517 BROOKDALE CT, Winchester VA 22601
4
BEDS
5
BATHS
5,420
SQFT
$125
$/SQFT
2004
BUILT
"Wow! Incredible find tucked away in one of the most desirable neighborhoods in Winchester! This 4 bed/4.5 bath home is located on the best lot in the neighborhood! So many upgrades ~ Hardwoods throughout main level, Great room with two story ceilings w/ gas FP, Gourmet kitchen w/ DBL ovens, gas cooktop, built-in microwave, SS appliances ~ huge pantry! Two Main level offices, Master retreat to come home to w/ soaking tub, dbl vanities, separate large shower ~ 4 (yes FOUR) Walk-in closets ~ Guest room w/ private bath & 2 additional guest rooms w/ shared bath (upper level) ~ Sunroom ~ Natural light throughout this entire home! Windows galore! ~ Finished Basement with a full bathroom, Media Room, PLUS two additional rooms that can be finished along with ample storage in utility room! ~ The home is on a cul-de-sac and overlooks a 45 Acre wetland preserve! There is a train track behind this house but not to worry~ It's one of the last privately owned railroads in existence in the US! A unique piece of history!!it doesn~t run often either.....Call today to schedule a tour!"
$670,000
1105 REDBUD RD, Winchester VA 22603
4
BEDS
3
BATHS
3,194
SQFT
$210
$/SQFT
25.90
ACRES
1967
BUILT
"Unique Property! 25.9 beautiful acres. Open and wooded with frontage on Red Bud Road. 4 bedrooms, 3 full baths. 1,000 sq foot addition added in 2001 w/Large master suite on main level. Eat-in kitchen and separate dining room with fireplace. Spacious Livingroom with hardwood flooring. Family room in lower level, fireplace w/woodstove insert. Large Sunroom. 25 x 50 Inground pool. Two car attached garage. 1/2 acre stocked pond. A five stall open pole barn. Convenient Access to I81/ Rt37 and minutes from shopping and Winchester Medical Center.Property is in Land Use and Red Bud Agricultural District."
* PRICE LOWERED - $690,000 TO $670,000 
$659,000
BELLEVILLE CT., Winchester VA 22602
4
BEDS
4
BATHS
2.28
ACRES
"Currently a lot in Belleville Farm. To be built custom rancher with upgrades galore. Double hung windows, Insulated Garage door with Openers, 30 year Architectural shingles, Soaking Tub with Tile surround in Master Bathroom, Crown Molding, Built-in Cabinetry, Barn door from Master bedroom to Master bathroom, Shiplap, Hardwoods throughout, Tiled Laundry and Baths, so much more! Located in picturesque Belleville Estates just a short distance down Cedar Creek Grade. Level cleared lot. Surrounded by beautiful custom homes and a horse farm! Close to Route 37 and I 81 for commuters. Just a few minutes from Historic Winchester, shopping, schools and Valley Health."
 
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