Winchester Homes for Sale

Winchester Homes for Sale

Welcome to Winchester, Virginia—a charming city steeped in history and surrounded by breathtaking natural beauty. Nestled in the heart of the Shenandoah Valley, Winchester boasts a vibrant community with a rich heritage that dates back to the 18th century. Known for its picturesque landscapes and historic architecture, this city offers a perfect blend of small-town charm and modern amenities.

Winchester is home to a variety of cultural attractions, including the Museum of the Shenandoah Valley, the historic Old Town district with its boutique shops and gourmet dining, and the stunning Shenandoah National Park nearby, perfect for outdoor enthusiasts. The city hosts numerous festivals and events throughout the year, fostering a strong sense of community and connection among its residents.

For those looking to call Winchester home, the real estate market is thriving with an array of homes for sale that cater to diverse tastes and budgets. Whether you’re seeking a cozy single-family home with a white picket fence, a modern townhouse in a vibrant neighborhood, or a sprawling estate with stunning views, Winchester has something for everyone. The local real estate market is characterized by its affordability, making it an attractive option for first-time buyers, families, and retirees alike.

With its friendly atmosphere, excellent schools, and convenient access to major highways, Winchester is not just a place to live; it’s a place to thrive. Explore the homes for sale in this enchanting city and discover the perfect backdrop for your next chapter!

Newest Winchester Homes for Sale

$471,000
3 Beds ⋅ 3 Baths ⋅ VAWI2011610 MLS
A must see property! This is a beautifull well kept colonial house with 3 bedrooms, 2 full bath and 1 half bath. The basement is unfinish but is ready to be build. As you enter the main level, you will see a nice welcoming livingroom, diningroom and beautiful granite countertops in the kitchen, with stainless steel appliances and high effitiency washer and dryer to the side. From the kitchen you can easily walkout to huge concrete patio for a great family cookout and enjoy the huge backyard. The back yard is infenced with 6ft tall white vinyl privacy fence that makes it look very elegant and secure...In the upper level of the house, you will find the masterbedroom with a masterbath, and a second bath for the 2 other bedroom. This property is minutes away from the Winchester Historic downtown and a short drive to Shenandoah University. This is a well kept property and is waiting for you to make it yours! Schedule your showing online and allow time since the seller has two little dogs to take care off when you go show it. There are video cameras at the property.

421 Longview Ave, Winchester
$525,000
4 Beds ⋅ 4 Baths ⋅ VAFV2044810 MLS
Offering three luxuriously finished levels, extensive upgrades, and a backyard designed for entertaining, this 4 bed/3.5 bath colonial is a MUST-SEE! Step inside to a grand foyer with soaring 12-foot ceilings and walls of windows flooding the home with natural light throughout. The main level features a dedicated study room accented by striking arched windows, spacious living and dining areas, an open kitchen with a window overlooking the serene backyard, and a showstopping family room wrapped in eight oversized windows with transoms that frame views of the outdoors and create a bright, airy gathering space centered around a cozy fireplace. Step outside to your own backyard retreat—an entertainer’s dream with an expansive, fully fenced lawn, large low-maintenance composite deck, spacious brick patio, and custom-built outdoor brick fireplace. Imagine summer cookouts on the deck, evenings around the fire, or simply enjoying the abundance of your own private open space. Upstairs, the expansive primary suite feels like a retreat of its own, featuring a separate sitting area perfect for a reading nook or quiet place to unwind, and two walk-in closets, including one conveniently located within the ensuite bath. The spacious primary bath features dual vanities, an oversized walk-in shower, private water closet, and dedicated space ready to add the relaxing soaking tub of your dreams. The upper level is completed by three additional spacious bedrooms with ample closet space, including one with its own walk-in closet, plus an LG washer and dryer conveniently tucked behind closed doors in the hallway for out-of-sight laundry. Head downstairs to the fully finished basement, offering even more versatile living space with a spacious recreation room and full bathroom next to a bonus room with generous closet space—giving you the flexibility to create the guest space, media room, playroom, home gym, or hobby space that fits your lifestyle. The home’s biggest-ticket improvements have already been taken care of, saving you thousands in future costly upgrades! Updates include a newer roof and siding, HVAC systems, water heater, upgraded insulation, sump pump, irrigation system, water softener, radon mitigation system, and whole-house generator, providing the ultimate peace of mind and backup power when the neighborhood experiences an outage. This home presents a RARE OPPORTUNITY, priced significantly below the tax assessed value. Seller welcomes ALL offers—bring yours and make this home your own!

114 Nassau Dr, Winchester
$349,999
4 Beds ⋅ 2 Baths ⋅ VAFV2044756 MLS
Welcome to 120 Comanche Trail in Shawneeland! Offering over 1,800 finished sq. ft., this 4-bedroom, 2-bath home combines thoughtful updates with plenty of space inside and out. Recent improvements include a NEW roof, newer HVAC, new flooring, fresh paint, updated lighting, and updated bathrooms. The primary bedroom features a walk-in closet and private en-suite bath, creating a comfortable retreat. The fully finished walkout basement expands the living space with a huge additional bedroom, bonus room and plenty of storage. Ideal for guests, a home office, recreation space, or multi-generational living. Outside, enjoy a large private lot surrounded by mature trees with established garden beds and a fire pit. A 1-car garage and spacious driveway provide plenty of parking for guests. Located on the lower end of Shawneeland, approximately 15 minutes from Winchester Medical Center, Downtown Winchester, shopping, dining, and major commuter routes. Community amenities include a lake, private beach, playgrounds, sports fields, and more. NO HOA - Shawneeland is a sanitary district maintained by Frederick County. The septic system was completely redone in November of 2024 for additional buyer peace of mind. Updated, spacious, private, and conveniently located—this home is ready for its next owner!

120 Comanche Trl, Winchester
$479,900
5 Beds ⋅ 3 Baths ⋅ VAFV2044802 MLS
This lovingly maintained two-owner Colonial has been thoughtfully cared for and improved since 1994, offering the character of an established home with many of the updates today's buyers are looking for. Homes in this sought-after neighborhood rarely come to market, making this a special opportunity in one of the area's most convenient commuter locations. Inside, you'll find a comfortable blend of hardwood, tile, and carpet flooring, built-in shelving, fresh paint in many areas, and charming details including chair rail and crown molding in select rooms. The living area features an antique stained-glass mantle that has been beautifully refinished and incorporated above the gas fireplace, creating a distinctive focal point. Upstairs, four large bedrooms provide plenty of comfortable living space, including a spacious primary bedroom with its own private bathroom. A finished and conditioned third-floor loft adds a huge, flexible bonus space ready to meet your needs; perfect for a 5th bedroom, playroom, office, game room, or additional living area. Storage abounds throughout this versatile space, offering possibilities to suit a variety of lifestyles. The kitchen is designed for both everyday living and entertaining, with an oversized island offering abundant storage, a butcher block top, and an eat-up bar area. Granite countertops are complemented by a white subway tile backsplash and a dramatic floor-to-ceiling accent wall. Recent improvements include a new water softener, a 2018 water heater, and a new washer and dryer installed in 2026. The HVAC systems are approximately two and three years old and have been recently serviced. The roof is less than five years old, while newer HardieBoard siding and windows provide additional peace of mind. Step outside to the large covered rear porch, finished with beadboard and a ceiling fan, overlooking the spacious fenced backyard. Mature trees and established landscaping create a private setting that is ideal for relaxing, entertaining, or enjoying outdoor time. The paved driveway adds convenience, while the no-HOA neighborhood provides added flexibility. Perfectly positioned close to town, schools, and everyday amenities while offering quick access to Route 7 for commuters, this home combines a well-established neighborhood setting with an exceptionally convenient location. A home with genuine character, meaningful improvements, and a level of care that is evident throughout.

109 Julee Dr, Winchester
$459,900
3 Beds ⋅ 2 Baths ⋅ VAFV2044768 MLS
Enjoy easy one-level living in this well-maintained ranch home conveniently located in Winchester, close to commuter routes, shopping, restaurants, and everyday amenities. The inviting front porch is the perfect spot to relax and enjoy warm evenings. Inside, hardwood floors flow through the living room, kitchen, and dining area, while the bedrooms feature comfortable carpeting. A dedicated laundry room adds convenience, and the unfinished basement provides plenty of storage and future possibilities. Step outside to the backyard, where a deck offers the perfect setting for entertaining, relaxing, or enjoying outdoor gatherings. A shed provides additional storage, while the two-car garage offers plenty of parking and workspace. A great combination of comfort, convenience, and outdoor living!

991 Front Royal Pike, Winchester
$325,000
4 Beds ⋅ 2 Baths ⋅ VAWI2011592 MLS
Welcome home! This beautifully maintained two-level home offers 4 bedrooms and 2 full bathrooms in the heart of Winchester. Warm and inviting, the home features a comfortable, functional layout with classic charm and thoughtful updates throughout. Pride of ownership is evident in every detail, both inside and out. Enjoy spacious living areas, a fully fenced yard perfect for relaxing or entertaining, and a private driveway for convenient off-street parking. Ideally located close to downtown Winchester, shopping, dining, and commuter routes. Move-in ready and waiting for you to make it your own!

805 S Kent St, Winchester
$552,000
4 Beds ⋅ 3 Baths ⋅ VAFV2044754 MLS
Beautifully remodeled Colonial in Pioneer Heights. Designed with primary suite; ideal home office configuration. All large bedrooms, large hardwood living room with stone wood fireplace, new natural gas upstairs furnace and a/c, upgraded insulation in attic, oversized garage and large deck. New paint, LVPk flooring in baths and kitchen. Must see.

100 Winns Cir, Winchester
$395,600
4 Beds ⋅ 2 Baths ⋅ VAFV2044446 MLS
You are going to love this spacious, one-level ranch located on a half-acre lot in a great location! Here are some of the key features and recent updates: - Huge 20x26 family room with Red Oak hardwood floors, a brick fireplace, and newly replaced French doors that open onto a large L-shaped front deck. - Bedrooms & Baths: New paint and new flooring throughout bedrooms and bathrooms master bath features a new vanity and new ceramic tile flooring, which is also featured in the hallway bath. master bedroom has full bath -Laundry: 8x8 laundry room complete with washer, dryer, cabinets, and counter space. -Kitchen and living room has Bruce flooring All new painting through out house - Upgrades: New ceiling fans in all rooms. The water pump, septic tank, and attic air handler for the AC unit have all been replaced. Both decks have been recently remodeled and resealed. - Garaging & Parking: you are going to love the Oversized 20x28 garage with front and back entry doors, plus a second attached 12×20 garage with entry door from the main garage! Large driveway with a 10+ car capacity and turnaround area. - Outdoor Space: Fenced backyard with a 10x12 back deck and beautiful pastoral views in both the front and back. Large L-shaped deck on front of house This home offers peaceful country living while remaining convenient to local grocery stores, restaurants, gas stations, schools, and major commuter routes this ranch offers the space & amenities you been dreaming of....... LOOK NO FURTHER!

178 Payne Rd, Winchester
$549,900
5 Beds ⋅ 4 Baths ⋅ VAFV2044748 MLS
“Pioneer Heights Colonial” - Welcome to this beautifully maintained colonial in the desirable Pioneer Heights neighborhood, ideally situated just off Route 7 for easy commuter access. Offering five bedrooms and 3.5 baths, this spacious home has been thoughtfully updated and improved over the years, providing a comfortable blend of classic character and modern convenience. The heart of the home is the updated kitchen, featuring custom cabinetry, granite countertops, stainless steel appliances, and plenty of workspace for everyday living and entertaining. Throughout the home, you'll find updated bathrooms, newer carpeting, and numerous additional improvements that make this home truly move-in ready. The finished basement adds valuable living space and versatility, complete with a walkout, comfortable living area, fifth bedroom, and full bathroom. Ample storage space provides plenty of room for seasonal items, hobbies, or household needs. Step outside and enjoy multiple spaces designed for relaxing and entertaining. A rear porch leads to a deck and backyard patio, creating an easy flow for outdoor gatherings, morning coffee, or quiet evenings. The meticulously manicured front yard is a standout, featuring lush green grass, thoughtfully maintained mulch beds, and beautiful flower gardens—all complemented by an underground sprinkler system for easy lawn care. With generous living space, numerous updates, attractive outdoor amenities, and a convenient location close to Route 7, this Pioneer Heights home offers the space, comfort, and accessibility you've been looking for. Schedule your appointment to see it today!

223 Asbury Rd, Winchester
$355,000
2 Beds ⋅ 2 Baths ⋅ VAWI2011574 MLS
Come see what makes Willow Lawn, a 55+ community, such a desirable place to call home! This inviting one owner Winchester home offers a comfortable blend of charm, functionality, and everyday convenience. The Floorplan is open and contemporary. The Great Room has Cathedral Ceilings and is very spacious. The grounds are taken care of by the community so life is easy. One level living w/ newer HVAC, a 4 year old roof, LVP flooring, updated bath, 2 bedrooms + 2 full bath. The 1 car garage is heated and cooled for year round comfort. There is space for a car and small workshop. You'll feel welcomed in this neighborly community where people walk, socialize and have planned activities at the well appointed Community Center. It is right around the corner from this home. Also, this home is located near the Abrams Creek Wetlands Preserve, perfect for walking + biking. Hospital + Down Town Winchester are 10 minutes away. Priced well and ready for you, come take a look today.

1847 Melvor Ln, Winchester
$375,000
3 Beds ⋅ 2 Baths ⋅ VAFV2044758 MLS
265 McDonald Rd is a 1-story Winchester home built in 1974 with a lower level and connected outdoor spaces. The kitchen includes cabinet storage, a preparation counter, and an adjoining area for dining. The main living room provides space for seating, with an additional finished room on the lower level. The primary bedroom includes a walk-in closet with shelving for organization and an adjoining bathroom with a shower and vanity. A rear deck connects to the home through sliding doors, extending the usable space outdoors. A dedicated laundry area includes cabinetry and a folding counter. The layout combines everyday living with practical storage.

265 Mcdonald Rd, Winchester
$409,000
4 Beds ⋅ 1 Baths ⋅ VAWI2011520 MLS
Welcome to a Mid‑Century Modern Home Where Timeless Character Meets Modern Sophistication. This beautifully updated 3–4 bedroom mid‑century modern home, where timeless character meets modern sophistication in one of Winchester’s most convenient and walkable locations. The large covered front porch immediately sets the tone—an inviting space for morning coffee or relaxed evening conversation. Inside, natural light fills the home, highlighting refinished hardwood floors, fresh interior and exterior paint, and preserved architectural details including original wide wood baseboard trim and classic pocket doors. The well‑proportioned bedrooms offer comfortable retreats with the same warm character found throughout the home. Also added for efficient heating and cooling year‑round, a new ductless mini‑split system has been installed for your comfort. The renovated kitchen features new cabinetry, granite countertops, trending black stainless‑steel appliances, and a pantry with built‑in cabinetry, providing excellent storage and everyday functionality. Thoughtful upgrades and custom touches enhance each living space, creating an atmosphere that is both refined and inviting. Step outside to a covered back porch with new maintenance‑free decking, overlooking an open backyard ideal for relaxing, entertaining, gardening, or unwinding at the end of the day. Additional conveniences include off‑street parking and an oversized single‑car detached garage. The neighborhood continues to shine with recent street repaving and new sidewalks, enhancing curb appeal and walkability. Ideally located just a short stroll from Winchester’s vibrant downtown pedestrian mall, you’ll enjoy easy access to restaurants, coffee shops, boutiques, breweries, and community events. Mature trees, walkable streets, and proximity to commuter routes, parks, schools, and everyday amenities make this location truly exceptional. This is a rare opportunity to own a handsome, thoughtfully updated home that captures the best of Winchester living—where character, comfort, and location come together beautifully.

322 E Piccadilly, Winchester
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