Winchester City Homes for Sale

Winchester City Home Listings

3 Beds 3 Baths VAWI2004992 MLS ACTIVE Status
The Historic Downtown Winchester home you’ve been waiting for! Only 2 blocks from the outdoor Downtown Mall. Old world charm and character meets modern conveniences in this exquisitely renovated home! Many of the original features have been brought back to life, such as the gorgeous staircase that greets you as you enter the spacious foyer. All original plaster walls have been refurbished and original functioning pocket doors w/ original brass hardware remain. Custom trim newly added throughout the entire home including period appropriate window trim & beautiful new custom coffered ceiling on main level. New Oak Hardwood flooring was installed on the main level and the original wood staircase railings and upstairs landing were refinished, bringing them back to their former glory. The formal living and dining room lead you back into the fully renovated kitchen, featuring white American Woodmark cabinets, brushed nickel appliances, Quartz countertops, accent colored center island w/ microwave and integrated trash/recycle drawer, and a full wall of tall pantry cabinets that provide an abundance of storage. Conveniently located on the main level is a renovated half bath and a spacious laundry and mud room, with direct access to the back of the house. But this is no ordinary laundry room and mud room. With tile flooring, barn style interior doors, coat closet, wall cabinets, new Samsung Washer & Dryer, and the original 100-year-old farm sink relocated from the prior kitchen, you might almost enjoy doing laundry! Plenty of warm, natural light from the brand new French doors that open to your private rear patio and large yard that’s full of charm. Upstairs are 3 spacious bedrooms, all with new oak hardwood flooring. The hall bathroom has been fully renovated with an oversized tiled shower, double vanities and all new fixtures, mirrors, lighting and toilet. The primary bedroom will be your own private oasis, with a fully tiled walk-in shower, freestanding tub with waterfall faucet and a spacious walk-in closet. The basement offers endless possibilities for additional living space such as a den, office, theatre room, etc. With new carpet, HVAC, recessed lighting, original cabinets & dry bar area with new custom stone countertop, natural lighting and separate exterior access, this makes for the perfect place to entertain family and friends. The flat and spacious yard has a private garden feel and offers a patio with a gazebo that provides shade, and access to the detached 4 car garage. This extra large garage has so many possibilities, large enough to accommodate a workshop, office, or studio of any kind. If all of this was not enough, you will live worry-free with all new electric, wiring, outlets, lighting fixtures & service updated to 200-Amp w/ new electric panel. All new HVAC (two-zone) – converted to Central Air - A/C on all levels & new Gas furnace for main & basement levels / new electric furnace upstairs. All new Plumbing in home, including new water heater. New Shingled Roof(s) & Gutters on home & separate garage and more! Plus a spectacular location in the heart of Winchester and just minutes to the vibrant shops and restaurants on the Old Towne Mall.

439 N Braddock St, Winchester

5 Beds 4 Baths VAWI2005030 MLS ACTIVE Status
Welcome Home in High Demand Meadow Branch neighborhood in Winchester! This custom built home was made for you by local builder, The Princeton Companies! As you approach the home and enter, upgrades all around, 9" Luxury Vinyl Floors, 9' ceilings, Office / Study to your left, make your way to the Chef's Dream Gourmet Kitchen, 42" cabinets, Quartz Counters, large island to prepare meals or entertain from, Stainless Steel GE Smart Energy Appliances, high vaulted ceiling in Living Room with an electronic start Gas Fireplace, Breakfast Room finishes the open floor plan, Formal Dining room as well. Laundry and mud rooms off garage. Upper Level has 4 bedrooms including the enormous Primary Suite with Walk In Closet and fully loaded Primary Bath to include freestanding tub, dual vanity sinks, and upgraded tile shower. Head down stairs to the finished / walkout basement with Bedroom, full bath (additional room for another potential bedroom or den space), can upgrade for a bar, open rec room space, and plenty of storage space. Possibilities are unlimited. Make your way outside to the covered patio and spacious outdoor space, perfect to unwind or entertain. Hardi Board Siding and 25 year shingles provide long term comfort in the exterior quality of the home. Location-Location-Location, close to shopping, dining, Old Town Winchester, Schools, University, Hospital, I-81 for easy commute. Upgrades are available at added cost. Documents and Floor Plans in Bright. Schedule your private showing today, don't hesitate!! Seller/Builder Offering $10,000 credit towards closing costs on full price offer!

1910 Harvest Dr, Winchester

4 Beds 2 Baths VAWI2005004 MLS ACTIVE Status
***ESTIMATED TOTAL LIVING AREA 1,515 sqft.*** Excellent location on an in-town City Street. This four bedrooms, two-bathroom home has been recently renovated in October 2023, with a modern style throughout. Newer heating and air conditioning systems provide peace of mind and energy efficiency. Brand new finished basement by adding a bedroom and full bathroom with county permits. Upgraded Electrical panel with permit. As you enter the home, you'll be greeted by beautifully refinished hardwood floors that add warmth and character. A modern living room with beautiful fireplace. The kitchen has been completely updated with tall kitchen cabinets, new appliances and a kitchen island make cooking a pleasure. The granite countertops and VLP flooring elevate the overall look and feel of the kitchen. The lower level has also been finished and includes a master suite with brand-new full bathroom, a walk-in closet and a living room with another fireplace which provides additional living space and convenience. This property offers ample outdoor space for relaxation and recreation. Whether you have pets or children who love to run and play or simply enjoy gardening, this expansive lot provides the perfect canvas. Convenient location to shopping, schools, historic downtown Winchester, and Valley Health Hospital all within easy reach. Don't miss out on the opportunity to make this peaceful retreat your own. ***Washer & Dryer Convey AS-IS***

149 Fox Dr, Winchester

4 Beds 1 Baths VAWI2004962 MLS ACTIVE Status
WELCME TO "THE CLASSIC MEETS MODERN: 2-STORY BRICK COLONIAL RENOVATED BEAUTY"! Embrace the joy of a walkable lifestyle, where everything you need is within reach. Experience the pulse of the city while enjoying the comfort and privacy of your impeccably designed home. Nestled in a serene neighborhood, this meticulously remodeled end of 2023, 4-bedroom, 1-full bath colonial 2-story home seamlessly blends classic charm with contemporary upgrades, offering a perfect fusion of style and functionality. Step into a world of refined living where every detail has been thoughtfully curated to enhance your lifestyle. Enter through a charming foyer, leading to an expansive living area bathed in natural light. Gleaming refinished hardwood floors throughout create an inviting atmosphere. Prepare to be captivated by the heart of this home – a kitchen that seamlessly marries history with contemporary elegance. The brick focal point, once an old chimney, now stands as a testament to the home's rich past, creating a unique and charming ambiance plus a great conversation starter. Revel in the beauty and functionality of the kitchen's butcher block countertops, new top-of-the-line SS appliances, LV tile flooring, strategically placed island w/cabinetry. Ascend to the second floor of this enchanting home, where a private haven awaits with 4 bedrooms and 1 full bath, each space meticulously designed to offer comfort and character. One of the bedrooms extends its allure beyond its four walls, featuring an outdoor porch with a balcony that overlooks the backyard. The outdoor balcony provides a captivating view of the backyard, creating a seamless connection between indoor and outdoor living. The shared full bath on the second floor has undergone a complete transformation, offering a spa-like sanctuary. The barn door in the bathroom adds a touch of character and ensures convenient storage for linens and essentials .A canvas for your imagination, the large backyard invites you to create the garden of your dreams, host gatherings, or simply enjoy the tranquility of nature. Say goodbye to parking woes as this residence offers the convenience of off-street parking. Enter from Lafayette alley and park in the rear. Embrace the vibrancy of downtown living with convenient access to eateries, shopping, and more. Explore the rich cultural scene and entertainment options just steps away from your front door. Perfectly situated within walking distance to a myriad of eateries, boutique shops, and cultural attractions. Convenient access to public transportation and major thoroughfares for easy commuting. Just blocks away from Downtown Winchester Walking Mall 0.3 miles away and all it has to offer. Winchester Medical Center is 2 miles away and Valley Health Offices within surrounding areas. Pizzozo Pizza is on the corner and has indoor/outdoor dining 456 ft away. The home's location enhances its value with potential for future growth and investment. Seize the opportunity to reside in a prime downtown location where the heartbeat of the city becomes the backdrop to your everyday life. Schedule a showing today and envision the unparalleled lifestyle that awaits you in this urban sanctuary. Roof 2018, Custom wrought Iron Railing front steps 2020, New Water heater and whole house shut off 2020, washer plumbing 2021, chimney 2017, replaced overhead service cable for electric 2019, extensive whole home reno 2023 see invoices. Alley access for off street parking i the rear has right of way in the deed.

431 N Loudoun St, Winchester

3 Beds 2 Baths VAWI2004764 MLS ACTIVE Status
Imagine you are awakened in the pre-dawn hours by the distant roar of cannon fire, and before you are fully awake, the sound of rushing horses thunder outside your front door as soldiers charge toward the cannon fire. This 1852 home sits a couple blocks from the courthouse in downtown Winchester. The city of Winchester, VA was said to have changed hands 72 times during the Civil War. The sounds of soldiers, horses and conflict would have been an unfortunate consequence of those days. But, today, it sits within a few minutes of the downtown walking mall which offers dozens of unique and locally owned restaurants and a wide array of delicious delights for your dining pleasure. The home boasts of glistening period floors that lead you through the large parlor space to an entertainer’s ideal dining room and ending in a foodie’s dream kitchen. The home has been skillfully tweaked to keep the period allure while adding modern conveniences without losing the 1800s charm. The kitchen island countertop is a restored door from the property, adding a sense of designer whimsey. An antique French grain sack fabric runner from the 1800s leads to the second-floor bedrooms and bath. The second-floor bedrooms bring spacious accommodations, and the second-floor bath has been recently remodeled to maintain the era vibe with all the conveniences of a new-build. The exterior shutters are closable just like they would have been in the 1800s. Be sure to look at the notes to see what the current owner has accomplished over her years of ownership. It is just stunning. The home was also one of the featured homes on the Parade of Homes 2022. Cornerstone encourages all potential buyers and their agents to verify the information provided. Cornerstone makes no representation as to the accuracy or reliability of the information that is contained herein. Buyers are encouraged to confirm the information prior to making an offer.

119 E Clifford St, Winchester

4 Beds 6 Baths VAWI2004674 MLS ACTIVE Status
Introducing a stunning custom-built home that embodies luxury, elegance, and comfort, now available for sale. Nestled on a sprawling over half-acre lot and one of the best lots in the neighborhood, this exquisite property offers a truly exceptional living experience. Boasting a brand new roof installed in 2020, this home ensures peace of mind and protection for years to come. Step inside and be captivated by the meticulous attention to detail and the finest craftsmanship evident throughout. Every aspect of this residence has been carefully designed to create a harmonious blend of style and functionality. The heart of this magnificent home is the gourmet kitchen, equipped with top-of-the-line appliances that cater to the culinary enthusiast's every need. Whether you're hosting a grand dinner party or preparing a casual meal for loved ones, this kitchen is a haven for culinary creativity. This one of a kind home offers an abundance of room for both relaxation and entertainment. The thoughtfully designed layout encompasses four spacious bedrooms, each providing a private sanctuary for rest and rejuvenation. Additionally, the home features 5 1/2 baths, ensuring convenience and privacy for all occupants. Situated in a highly sought-after neighborhood. Whether you're seeking a peaceful retreat or a space to entertain guests, this custom-built home is the epitome of luxury living. Immerse yourself in the grandeur of this residence, where every detail has been carefully curated to create an atmosphere of sophistication and refinement. Don't miss the opportunity to make this extraordinary property your own. Experience the allure of this custom-built home, where timeless elegance meets modern convenience. Schedule a viewing today and prepare to be enchanted by the sheer beauty and grace that awaits within these walls.

1018 Heth Pl, Winchester

Start Your Search

Winchester City, VA, Homes for Sale

Winchester City, located in the northern Shenandoah Valley of Virginia, is a historic and vibrant community with a rich past and a promising future. With a population of around 27,000, the city offers a small-town feel with all the amenities of a larger city. The Winchester City real estate market is welcoming and friendly, with a strong sense of community. The downtown area is filled with charming shops, cafes and restaurants, and residents of Winchester City homes can enjoy events like the annual Apple Blossom Festival and the First Friday Night Live concert series.

One of the biggest draws of living in Winchester City homes is their location. Nestled in the heart of the Shenandoah Valley, residents have easy access to various outdoor activities, including hiking, biking and fishing. The area is also home to several parks and nature preserves, including the Shenandoah National Park and the Sky Meadows State Park.

Winchester City has a rich history dating back to the colonial era, and the area played a significant role in both the Revolutionary and Civil Wars. Visitors can learn about the city's past by visiting historic sites like Stonewall Jackson's Headquarters Museum and the George Washington's Office Museum.

Residents of Winchester City homes can also enjoy a variety of amenities, including excellent schools, healthcare facilities, and cultural institutions. The city is home to Shenandoah University, which offers a range of academic programs and cultural events, including theater productions and music concerts. The Museum of the Shenandoah Valley is another popular cultural attraction featuring exhibits on local history and art.

Public Transportation Options

The Winchester City real estate market offers several public transportation options for residents and visitors to get around the city and the surrounding area. Whether you prefer to take the bus, train or a ride-sharing service, options are available to meet your needs.

Winchester Transit: The city operates a public bus service called Winchester Transit, which provides fixed-route and paratransit services within the city limits. The bus routes cover most of the city, including major shopping areas, medical facilities, and government offices. The paratransit service is available for eligible individuals who cannot use fixed-route buses due to a disability.

Virginia Regional Transit: Virginia Regional Transit (VRT) is a regional public transportation system that serves Winchester City homes and the surrounding counties. VRT operates several bus routes that connect Winchester City to other cities and towns in the area, including Front Royal, Stephens City, and Berryville. The bus routes are designed to meet the needs of commuters, students and other passengers traveling to work, school or other destinations.

Amtrak: Winchester City is served by Amtrak's Capitol Limited and Cardinal train services, which connect the city to major cities on the east coast, including Washington D.C., Baltimore, Pittsburgh and Chicago. The city's Amtrak station is downtown and offers daily departures and arrivals.

Taxi and Ride-Sharing Services: The Winchester City real estate market also has several taxi and ride-sharing services, including Uber and Lyft, which provide on-demand transportation services within the city and the surrounding area. Taxis can be hailed on the street or by a local taxi company.

Shopping Centers

Residents of Winchester City homes can visit a variety of shopping centers that cater to the needs and preferences of different shoppers. There is something for everyone in this vibrant city, from small boutiques to large shopping malls. Whether you're looking for the latest fashion trends, home decor, or a bite to eat, there is sure to be a shopping center in Winchester that suits your needs. Here are some of the notable shopping centers near Winchester City homes for sale:

Apple Blossom Mall: Located at 1850 Apple Blossom Dr, Winchester, VA, Apple Blossom Mall is one of the largest shopping centers in the area. The mall features more than 80 stores, including Macy's, JCPenney and Belk, as well as a food court and a cinema.

Creekside Station: Creekside Station is a shopping center at 3103 Valley Ave, Winchester, VA. It features several retailers, including Target, Bed Bath & Beyond, and Michaels, as well as various restaurants and services.

Downtown Winchester: The downtown area of the Winchester City real estate market offers a unique shopping experience with a mix of small boutiques, antique shops, and specialty stores. Visitors can stroll through the pedestrian-friendly streets and discover hidden gems, such as the Shenandoah Valley Discovery Museum and the Old Court House Civil War Museum.

Winchester Gateway: Winchester Gateway is a shopping center at 1900 S Pleasant Valley Rd, Winchester, VA. The shopping center features several retailers, including Walmart, Marshalls, Ross Dress for Less, and restaurants and services.

Jubal Square Shopping Center: Jubal Square Shopping Center is at 2144 S. Pleasant Valley Rd, Winchester, VA. It features a variety of stores, including Kohl's, Petco and Dollar Tree, as well as several restaurants and services.


The Winchester City real estate market is a vibrant and welcoming community that offers a small-town feel with all the amenities of a larger city. With its stunning natural beauty, rich history, and cultural attractions, homes for sale in Winchester City are a great choice. Whether you're interested in outdoor activities, cultural events, or simply soaking up the local atmosphere, there is something for everyone in this charming community of Winchester City homes.

Set Up a Time to View a Winchester City Home!

Call us at 703-462-0700 or email us at to schedule a time to see an available property in this Shenandoah Valley community.

Thinking of Selling Your Winchester City Home?

Contact us to request a free property valuation, which will give you a good idea of how much you could expect to sell your property for in the current market.