Winchester VA Real Estate & Homes for Sale

Charming All-Brick Ranch with Endless Potential in Established Neighborhood! Don't miss this solid 3+ bedroom, 1.5 bath all-brick ranch offering timeless appeal and the opportunity to make it your own. Nestled in a well-established neighborhood, this home features original hardwood floors, a cozy fireplace for chilly evenings, and radiant ceiling heat for comfortable, energy-efficient warmth throughout the seasons. The mostly finished basement provides substantial additional living space, perfect for bedrooms, a rec room, home office, and additional storage. Step out to the fully fenced backyard-ideal for pets, gardening, or weekend entertaining. While this home needs some updates and renovations, its packed with potential and ready for your vision. Whether you're an investor, first-time buyer, or looking for a renovation project, this is your chance to create something truly special. Schedule your private showing today and see the possibilities for yourself!

Welcome to 306 Canyon Road! This well-maintained 4-bedroom, 2.5-bath home is located in one of Winchesters most desirable east side neighborhoods. Enjoy the convenience of being just minutes from schools, shopping, and major commuter routes. Step inside and youre greeted by a bright and welcoming living room to the right and a formal dining room to the left, offering an ideal layout for both everyday living and entertaining. Continue into the heart of the home-an open kitchen with an expansive eat-in area, perfect for casual meals or gatherings. A convenient half bath is located in the main level entrance way. The attached two-car garage offers easy access directly into the kitchen, making unloading groceries a breeze. Step out onto the back deck, ideal for grilling out and enjoying warm summer evenings, and enjoy the fully fenced backyard. Upstairs, retreat to a spacious primary suite complete with a walk-in closet and en-suite bath. Three additional bedrooms, a full hall bath, and an upper-level laundry room offer functionality and space for the whole household. The spacious layout offers comfortable living with plenty of room to grow, and the home's pride of ownership shows throughout. Homes like this dont stay on the market for long-schedule your showing today before its gone!

Welcome to this beautiful one owner, 3 level Colonial in the City of Winchester! Homes available in this fantastic neighborhood don't hit the market often! NO HOA! NEW ROOF in 2024! This custom built home boasts beautiful hardwood floors on the main and upstairs level (NO CARPET). There is a main level bedroom with attached 3 piece bath. Would make an excellent guest bedroom, or full time office space. You will find an additional half bath on the main level perfect for your guests. Enjoy the gas fireplace with surrounding built ins within the family room with easy access to your outside two tier deck. The kitchen has stainless steel appliances, under cabinet lighting, bar seating, and there is a large eat in area that over looks the backyard. From the kitchen you have easy access to the formal Dining Room. Built in desk/work station right off the kitchen makes a great place for homework, crafts, and storage. You will LOVE the mudroom off of the 2 car garage. LARGE walk in Coat Closet, LARGE Pantry with shelves, Washer, Dryer and a mop station! Upstairs has 3 very large bedrooms. On the way to the primary, there is a large linen closet with double doors. The primary has a sitting room, access to two floored attic storage spaces. New Ceiling fan installed (2025), and a LARGE walk-in Closet! The master bath is extra roomy! Not only does it have TWO linen/storage closets, but there are additional built-ins that surround the large jetted tub! The extra long vanity has double sinks and plenty of storage. The second bedroom has built-ins that surround the window and connecting them is a bench with additional storage. There is a cathedral ceiling in this room, large walk-in closet, and access to the Jack & Jill Bathroom (the 2 and 3 bedroom each have their own sink and share the toilet and shower). The surround tub shower, was replaced in 2024! The second bedroom's sink area also has a vanity. The third bedroom is large enough for an additional sitting area, play area, large walk in closet and access to the Jack and Jill bath. The finished living areas in the lower level have tile. There is a large open area with plenty of room for an additional family room, game room, or it would make a fantastic play area. There is a walk-up access to the side yard. Water heater (replaced in 2022), is located in this lower level with easy access tucked behind a door. There is an additional room with a door that the previous owner used as an office. You will find two additional storage rooms on this level, on either side of the stairs. One houses the whole house filter system! The rear yard is completely fenced in. There are gardening opportunities, plenty of room for grilling and enjoying your private oasis amongst the mature plantings! Upstairs HVAC system was replaced about 3 years ago and Barrett Pest Control has managed this property from day one! The main and upper floor walls freshly painted (2025)! You will appreciate this layout and all this home has to offer. If you are needing space, especially storage space, you need to check this one out! Make an appointment today or come see it during one of our upcoming open houses!

Welcome to this spacious farmhouse on FIVE acres! Newer high efficiency oil furnace. NEW hot water heater! NEWER windows throughout. Metal roof - large detached two car garage with large work area. Pole barn and garden shed! Apple trees, peach tree - 15 minutes to town!

Welcome to 800 Kennedy Drive, a spacious Colonial by Richmond American Homes located in the desirable Rolling Hills Estates. This home offers three finished levels with a smart, open layout-perfect for everyday living and entertaining. The main level flows seamlessly from room to room, featuring beautiful hardwood floors and fresh new carpet throughout. The large family room, featuring a stone fireplace, is a warm and inviting space and serves as a beautiful focal point of the home. The kitchen is well-equipped with extensive counter space, a walk-in pantry, new refrigerator, double wall ovens, and a gas cooktop. A sunroom off the kitchen adds valuable living space on the main floor and structurally extends to the basement, increasing usable square footage below. Originally designed by the builder as an office, the main-level bedroom was upgraded during construction to include a closet and a full bath, offering excellent flexibility for office space, guests or multi-generational living. Upstairs, youll find four generously sized bedrooms, including a spacious primary suite with a large sitting room-an ideal space to read and relax-and an en suite bath. The walk-up lower level features an expansive recreation room, a den, a full bath, and generous storage areas, offering a flexible footprint for future customization. This home is located just 1.5 miles from the future Wards Plaza Redevelopment Project, which includes a 50,325-square-foot Publix supermarket expected to open in late 2026, bringing approximately 150 jobs to the area. The project also features planned infrastructure improvements such as new streets, upgraded stormwater, water, and sewer systems. A portion of Hope Drive is also proposed for vacation to create green space or a linear park. Located in the sought-after Handley School District and with easy access to Routes 37, I-66, and I-81, this move-in-ready home offers comfort, functionality, and long-term value. You can view the marketing brochure here: https://buy800kennedy.my.canva.site/

"Bring Your Vision To W Pall Mall" This 4 bedroom, 1 full bath home is perfect if you're looking for a renovation! Right in the heart of Winchester City within walking distance to the Old Town Walking Mall where you can enjoy excellent food, shopping and more! The first floor has a great sized living room, dining room and kitchen. 4 bedrooms on the upper level, full bathroom, walk-up attic and an additional bonus room that would make a great home office. Fenced in back yard, shared driveway/shed, front porch and back porch. Roof was repainted in 2021. Home is sold as is where is.

Welcome to your brand-new, private retreat in Mountain Falls! This thoughtfully designed three-story home features open-concept living on the main level, including a spacious kitchen, dining area, family room, convenient main-level laundry, and a half bath. Upstairs, youll find a generous primary suite with its own full bath, along with two additional bedrooms and another full bathroom. The unfinished basement offers a blank canvas for your personal touch-perfect for added living space, a home gym, or storage. Dont miss the chance to make this beautiful new construction your own!

Located in a quiet and well-established Area convenient to shopping, Historic downtown Winchester, Valley Health and Schools. The ease of one-level living, a flexible floor plan, and a generous 2+ Acre lot with a pond make this house a home! This 3-bedroom, 2-bath ranch-style home features a traditional layout with defined living spaces, including a front living room, and a dedicated dining area. Off from the Kitchen is an additional Sunroom/Den/Office, the Space has unlimited potential. The kitchen offers ample cabinetry and a functional layout that connects easily to the main living areas. All three bedrooms are located off the main hallway, the Primary bedroom has its own bath, the additional bedrooms share access to a centrally located full bath. The lower level is ready for your finishing touches. Outside, the property includes a sizable backyard offering space to enjoy the outdoors, no HOA, the neighborhood offers a sense of freedom and individuality while maintaining a peaceful, residential atmosphere. Its the perfect blend of privacy and proximity to everyday amenities. Outdoor recreation options abound! Call the listing agent for a tour today!

Beautiful 3 level garage townhome in Freedom Manor. Built in 2021 with over 2,200 finished square feet of living space freshly painted and appointed with vinyl flooring and new carpeting. This property features 3 Beds, 2 Full Baths, 2 Half Baths and boasts an open floor plan with a spacious island kitchen with granite countertops and stainless steel appliance. This property is conveniently located to commuter routes, hiking trails, shopping, dining and downtown Winchester.

Nestled about 20 minutes from downtown Winchester, this charming two-bedroom home may be just what you need to escape city life! Perfect for a primary residence or a part-time getaway, the property is nestled on two lots equaling nearly one acre. Once inside, you'll feel right at home with warm and inviting wood tones. The open living-dining area provides a comfortable space to relax while tranquil treetop views await just outside on the beautiful, screened porch. You can actually choose which outdoor space feels right to unwind! In the mornings, the inviting front porch would be the perfect place to savor a cup of coffee or tea. In the evenings, you can dine alfresco on the back porch while enjoying the serenity and privacy of the property. This well-maintained home is ready for you! From the water softener/conditioning system to the thoughtful washer/dryer combo, you'll feel like you're on vacation year-round at this peaceful retreat. Sit back and schedule your showing today!!

This beautiful cottage, nestled on the very sought after Miller St, supplies the utmost convenience for what Winchester has to offer. From walking distance to eateries and Old Town entertainment, a quick drive to supermarkets all around and Handley High School just one street away! Supplying 3 bedrooms 2 1/2 bathrooms across three levels you can appreciate the character of an older home with touches of modern amenities. This home offers one level living with the spacious primary suite on the main level. Updated kitchen with granite countertops and stainless appliances. Along with pristine hardwood floors flowing through a majority of the home. This home boasts a very cozy living room conveying a wood burning fireplace. The basement offers more entertainment area along with much needed storage and a full bath roughed in, ready for your finishing. The enclosed sunroom is perfect for morning coffee or an afternoon beverage and overlooks the private oasis of a spectacular backyard with much privacy and gas fireplace. An entertainers dream!! Dont miss this opportunity!

â??Classic and Contemporaryâ? - Welcome to this beautifully maintained contemporary home nestled in one of Winchester's most hidden but premium neighborhoods. Offering nearly 4,000 square feet of finished living space across three thoughtfully designed levels, this 4-bedroom, 3-bath residence combines stylish updates with unique architectural details. Step inside to discover a warm and inviting floorplan, where distinct living areas create both flow and flexibility-perfect for entertaining or enjoying quiet moments at home. The main level boasts elegant wood flooring, custom built-in bookcases, and a cozy gas fireplace (2019), adding character and function to the space. The kitchen features a central island ideal for casual dining and open to the family room, making it a versatile space for work or relaxation. An adjacent first floor office includes a wet bar to enhance your entertaining experiences. Upstairs, youll find spacious bedrooms filled with natural light, while the fully finished basement offers expansive recreational space, a separate theater room, and a private fourth bedroom-ideal for guests or multi-generational living. Enjoy the outdoors on the large backyard deck, surrounded by mature trees that provide privacy and shade. Fruit trees add charm and seasonal delight, creating a peaceful retreat just steps from home. Situated across the street from Winchester Medical Center and just minutes from historic downtown, this home offers unbeatable convenience to walking paths, parks, and local trails. Recent upgrades include a new roof (2018), vinyl siding (2020), gas water heater (2021), and a new HVAC heat pump with gas backup (2023), ensuring comfort and efficiency for years to come. This is the perfect blend of location, space, and personality-your next chapter begins here!

Conveniently located near Route 7 and I-81, this beautiful all-brick home offers easy access to everything Winchester has to offer. Situated in the heart of the city, you're just minutes from downtown, schools, shopping, Jim Barnett Park, and a variety of entertainment options. Inside, the main level features classic hardwood floors, a full bathroom, and a cozy wood-burning fireplace - perfect for relaxing evenings. The upper level includes three spacious bedrooms and a full bath with a tub/shower combo, tile flooring, and dual sinks. An additional finished attic space with heating and A/C provides the perfect setting for a home office or creative studio. The partially finished basement offers a versatile recreation room, along with a laundry area equipped with built-ins and a utility sink. Outdoor living is just as inviting with a covered front porch, a rear deck, and a brick patio - ideal for entertaining or unwinding. The fully fenced backyard includes a storage shed and the paved driveway provides ample off-street parking. This home blends comfort, convenience, and charm - a must-see in the City of Winchester! Updates are approximate and include a roof 2021, sump pump & stainless steel appliances 2022, updated electric, updated plumbing, attic windows 2025, new deck 2021, new back door 2022, regularly serviced/maintained HVAC system.

Experience refined living in this stunning luxury home just minutes from Winchester Medical Center. Designed for both elegance and comfort, this residence boasts exquisite crown moldings, rich wood floors, wainscoting, and cathedral ceilings throughout. The main level offers one-level living with an entry-level bedroom, a spacious gourmet kitchen with upgraded quartz countertops, and a gas fireplace framed by a marble mantel for cozy evenings. Entertain effortlessly with a wet/dry bar, complete with a wine cooler, and a fully finished walkout basement ideal for a separate living space or guest suite. Step outside to a newly built fire pit and patio, or relax on the back deck surrounded by serene views. The oversized garage features a coated floor and ample storage. Smart-home touches like the front door smart lock enhance both convenience and security. This home seamlessly combines luxury, function, and location. Outside pictures will be updated after deck install and landscaping is completed - weather allowing! Progress pictures and final plans provided upon request

Welcome home to effortless living! This stunning open-concept design is perfect for both daily enjoyment and entertaining. The main level shines with 10 ft ceilings, gleaming hardwood floors, and a gourmet kitchen featuring 42" cabinets, stainless steel appliances, and a show-stopping 10-foot granite island. Step out to your private 10' x 20' deck and savor beautiful sky views. Upstairs, discover 9 ft ceilings, a spacious owner's suite with walk-in closet, and an upgraded master bath boasting a walk-in shower with seating and dual comfort-height vanity. Two more bedrooms, a hall bath with dual vanity, and laundry complete this level. Enjoy summer cookouts at the community covered pavilion, shoot hoops on the basketball court, or relax at the tot lot. Excellent commuter location with quick access to Route 7 and Dont mist the opportunity to make this your home.

This charming all-brick rancher is perfectly located within walking distance to Handley High School, the Old Town Mall, and the Apple Blossom Festival-putting you right in the center of Winchesters most loved events and amenities. Bursting with character, this home features original hardwood floors, built-ins, a cozy fireplace, and quaint details that reflect its historic roots. Enjoy outdoor living in the fully fenced backyard or relax on the fantastic screened-in porch. Fresh exterior paint and newly mulched landscaping offer great curb appeal. The full, unfinished basement includes a workshop area and provides endless potential to make the space your own. Dont miss this rare downtown gem at an incredible value-full of potential and ready for your personal touch to truly make it your own!

**This is a To Be Built Home in the Meadow Branch Section of Winchester City*** Experience the perfect blend of timeless farmhouse charm and modern luxury in this beautiful new construction home built by respected local custom builder Dave Hepler. With 3 bedrooms and 3 full bathrooms, this thoughtfully designed residence offers quality craftsmanship, stylish finishes, and a layout ideal for both daily living and entertaining. All images are similar, and pricing varies on purchaser's selections - The sale includes the lot, which is under separate ownership and will require a separate purchase contract. The lot must be closed on prior to construction of the new home. This streamlined process ensures everything is in place before your custom-built farmhouse begins to take shape. ***Tax rate is estimated and should be verified w/ city of Winchester. **Price does not include bonus room

Welcome to your own spot on Great North Mountain. This fully renovated home in Shawneeland offers the kind of space, freedom, and natural setting thats getting harder to find. It sits on two separate parcels totaling 0.68 acres, giving you breathing room and flexibility for the future. Whether you want a larger yard, extra privacy, or room for something else down the line, youve got it. The house was fully renovated in 2022: roof, siding, windows, HVAC, kitchen, bathrooms, and flooring. The hot water heater and washer were replaced in 2024. In other words, the major updates are done. Its move-in ready without the usual list of â??somedayâ? projects. Inside, the layout is simple and open, with natural light throughout. Step outside and youre in the woods, with the kind of quiet that just doesnt come with close neighbors. And while it feels tucked away, youre only 15 minutes from Winchester Medical Center and about 20 minutes from downtown Winchester. Its quiet, but not isolated. One of the best things about living here is the access to the community lake and several ponds. You can swim, fish, canoe, or just sit on the beach and unwind. There are also playgrounds nearby and a well-loved farmers market just a short drive away.Theres no HOA. Shawneeland is a sanitary district managed by Frederick County, with an annual fee that covers road maintenance and access to the trash and recycling center on Shawnee Trail. Xfinity internet is available. The house lot has an existing well and septic system, and both parcels qualify for public water hookup through Aqua if you ever want to build or connect later. Its hard to explain what living here feels like until you do it. Morning walks where the only sound is the wind in the trees. Evenings where the stars are actually visible. A little more space. A little quieter. A little more breathing room. Thats what this place offers. If that sounds like the kind of setting youve been looking for, come take a look

Beautifully Maintained End-Unit Townhome in the City of Winchester Dont miss this rare opportunity to own a stunning 3-level end-unit townhome, impeccably maintained by its original owner. Located in the City of Winchester, this home offers timeless charm and modern updates throughout. The main level features gleaming hardwood floors, elegant crown molding, and an open-concept layout that's perfect for entertaining. Enjoy cozy evenings by the gas fireplace or step through the glass doors onto your brand new deck (2025) with a retractable awning-ideal for outdoor dining and relaxation. The updated kitchen is a chefs dream, complete with granite countertops, stainless steel appliances, a spacious pantry, and a convenient motion-sensor faucet. The seamless flow between the kitchen, dining, and living areas makes hosting a breeze. Upstairs, you'll find a spacious primary suite with a walk-in closet and updated ensuite bath. Two additional bedrooms and a stylish hall bathroom with a jetted tub offer comfort for family or guests. The lower level includes a generous laundry area, extra storage, and access to the attached one-car garage. This move-in-ready home truly has it all-style, functionality, and a prime location. Homes like this in Winchester dont last long. Schedule your private showing today!

Charming Split Foyer Home in Shawneeland - 144 Falcon Trail, Winchester, VA Welcome to 144 Falcon Trail, a delightful 3-bedroom, 2.5-bathroom split foyer residence nestled in the serene Shawneeland community of Winchester, VA. Built in 2009, this 1,566 sq ft home offers a perfect blend of comfort and potential, making it an ideal choice for first-time buyers or savvy investors. Enjoy a traditional floor plan featuring a cozy living room, a family room, and a dining room. Three main-level bedrooms, including a primary suite with an en-suite bathroom, provide ample space for relaxation. The full basement offers additional living space, perfect for a home office, gym, or entertainment area. Step outside to a private deck, ideal for outdoor dining or simply enjoying the peaceful surroundings. A two-car attached garage and gravel driveway ensure plenty of parking space. Shawneeland is a picturesque community located on the eastern slopes of Great North Mountain. Residents have access to a private beach, playgrounds, walking trails, and lakes suitable for fishing, swimming, and non-powered boating. The community's tranquil setting offers a perfect retreat from the hustle and bustle of city life.

Dont miss your chance to own a Winchester classic in the heart of downtown! This beautifully renovated home boasts a brand-new kitchen with granite counters, stainless steel appliances, and white shaker cabinets. Enjoy modern bathrooms, stylish LVP flooring, and fresh paint throughout. The open-concept layout offers great flow for entertaining. Upstairs features spacious bedrooms and access to a private upper deck. Brand new HVAC system has been installed ! Large fenced backyard offers privacy and potential for off-street parking. Because the property has a large private backyard, there is potential to create additional parking in the backyard. The upper-level rear deck has stairs to the yard, or a quiet spot to enjoy your morning cup of coffee. You'll love the location--only two blocks from Handley High School, and just off the Apple Blossom parade route.

Location, Location, Location! Come and take a look at this freshly updated END-UNIT townhome in highly sought Huntington Meadows Subdivision! The space will amaze you at this 2-sided BRICK townhome that features a very large fully fenced backyard with a fabulous deck perfect for outdoor entertaining. The interior features may NEW updates, including: FRESH paint, NEW luxury vinyl plank flooring, NEW light fixtures, a NEW roof (just installed May 2025), and NEW windows (to be installed by beginning of June)! The heat pump/AC was installed in 2022 & hot water heater in 2024! Enter into a spacious Living Room with chair rail, crown molding, french doors to the Kitchen, plus a large bay window allowing natural light to flow in. The Kitchen with table space includes tile backsplash, a double-bowl sink, and ceramic tile flooring. Additionally, you'll also find a powder room, laundry closet, utility closet and cost/storage closet on the main level. Brand new carpet on the steps lead you to the upper level, which features new luxury vinyl plank flooring throughout. 3 Bedrooms, a nicely REMODELED full bathroom and a linen closet finish off the upper level. You'll enjoy the modern conveniences nearby - shopping, restaurants, schools, commuter routes such as Route 7 and I-81; along with Shenandoah University, Valley Health Systems, Rubbermaid, Amazon, and Laurel Ridge Community College!

*OFFERING UP TO 15K IN CLOSING COST ASSISTANCE FOR PRIMARY RESIDENCE WITH USE OF PREFERRED LENDER AND TITLE.* This home has a Gourmet Kitchen: cooktop with chimney style hood, wall microwave, wall oven, upgraded gourmet Energy Star stainless steel appliances, Refrigerator is a French 2 door style, the kitchen island is extended to comfortably seat 4, and a box bay window in the rear of the home for extra lighting located in the kitchen. You are going to love the large single bowl sink in the kitchen, upgraded cabinets with upgraded quartz countertop in the kitchen. Crown molding is the finishing touch for the upgraded cabinets. This is a chef's kiss kitchen!!!!Upstairs you'll find all three bedrooms and two full bathrooms. The primary bath also has upgraded countertops. The bedrooms and living room have been prewired for a ceiling fans. *Photos may not be of actual home. Photos may be of similar home/floorplan if home is under construction or if this is a base price listing.

*OFFERING UP TO 15K IN CLOSING COST ASSISTANCE FOR PRIMARY RESIDENCE WITH USE OF PREFERRED LENDER AND TITLE.* Beautiful open concept living 3 level town home built on concrete slab with a walk-out basement. Finished Rec Room - 13'1" x 11'1" with a door to the outside/backyard. The living room area is15'3" x 17', open kitchen layout with an extended island, and a box bay window in the rear of home. Separate pantry and LVP throughout the main level. The primary bedroom is 13' x 11'6" with a walk-in closet, double bowl vanity in primary bathroom, and a walk-in shower with seat. 3rd floor laundry room for convenience and a hallway Linen closet. Bedroom #2 is 9'3"x 10'8" with a double door closet and bedroom #3 is 0'4"x10'5" with a closet. All homes have a backyard that can be fenced with approval from HOA White Vinyl stockade with gate. *Photos may not be of actual home. Photos may be of similar home/floorplan if home is under construction or if this is a base price listing.

*OFFERING UP TO 15K IN CLOSING COST ASSISTANCE FOR PRIMARY RESIDENCE WITH USE OF PREFERRED LENDER AND TITLE. CONTACT CO LISTING AGENT/CONSULTANT FOR DETAILS* Late Summer Delivery in Winchester featuring walking trails, lush landscaping multi sport court for basketball and pickleball a welcoming pavilion and tot lot. Bedford II, 3 level townhome features a partial stone front with 1 car garage. This home features 3 Bedrooms and 3.5 Baths. It is fully finished top to bottom. The front door leads directly into the spacious lower level including 9 ft. ceilings, foyer with a double coat closet, access to the garage with a garage door opener. Continuing into the fully finished lower level recreation room with a full bath and walkout access to rear yard with privacy fencing. Open concept main level with 9 ft. ceilings. The kitchen has stainless steel appliances, a large 8 plus island, and quartz countertops. The kitchen leads directly into living room with powder room. The primary suite includes a large walk-in closet and the primary bathroom has dual vanities with tiled shower with a seat. Laundry is located on the bedroom level. Home and community information, including pricing, included features, terms, conditions, availability and sales procedures related to appointments subject to change without notice. All images are for illustrative purposes only and individual homes, amenities, features, and views may differ. Images may be subject to copyright.