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$471,000
3 Beds ⋅ 3 Baths
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

Listing courtesy of Samson Properties. Contact: (571) 921-9755
$325,000
4 Beds ⋅ 2 Baths
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

Listing courtesy of Weichert, REALTORS. Contact: (703) 850-4771
$355,000
2 Beds ⋅ 2 Baths
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

Listing courtesy of Century 21 Redwood Realty. Contact:

$409,000
4 Beds ⋅ 1 Baths
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

Listing courtesy of Long & Foster Real Estate, Inc.. Contact: (540) 662-3484
$699,000
7 Beds ⋅ 5 Baths
Welcome to 2700 Loyalty Court—a beautifully maintained showcase home offering nearly 5,000 square feet of unmatched versatility in one of Winchester City’s most coveted locations. Commanding a prime corner lot on a peaceful cul-de-sac, this residence immediately captivates with its timeless stone-and-vinyl exterior, inviting covered front porch, and unmistakable curb appeal. Step inside to a soaring two-story foyer flowing into a light-filled interior boasting fresh paint, newer carpet, refined architectural details, and abundant natural light throughout. Designed for both grand scale entertaining and effortless everyday living, the main level features a dedicated office behind French doors, a formal dining room accented by elegant wainscoting, a den and a full bath. At the heart of the home, the sprawling family room makes a bold statement with architectural pillars and a floor-to-ceiling stone gas fireplace. It connects seamlessly to a chef-friendly kitchen complete with granite countertops, upgraded cabinetry, stainless steel appliances, a center island, pantry, built-in desk area, and a bright breakfast nook opening directly to the rear deck. A handy mudroom with laundry off the garage completes this level's intuitive floor plan. The impressive layout continues upstairs, offering abundant accommodations for family and guests across five generously sized bedrooms. The massive primary retreat serves as a true private sanctuary, complete with a dedicated sitting area, large walk-in closet, and a spa-like ensuite bath featuring a glass walk-in shower and a corner soaking tub. Two bedrooms are connected by a convenient Jack-and-Jill bath, alongside two more spacious bedrooms and another full bathroom. The real showstopper continues downstairs in the fully finished, walkout lower level—a massive multi-functional footprint that expands your living options exponentially. This lower level provides endless flexibility, featuring an expansive recreation room for hosting game days or movie nights, a full bath and two additional bedrooms perfect for guests, and multiple finished rooms ready to serve as a home gym, playroom, or hobby space—plus a storage area to keep it all organized. Offering extraordinary scale on a premier corner cul-de-sac lot, this move-in-ready home represents Winchester living at its finest and stands ready to welcome its next proud owners.

2700 Loyalty Ct, Winchester

Listing courtesy of Colony Realty. Contact:

$350,000
3 Beds ⋅ 2 Baths
Nestled in a charming neighborhood, this delightful ranch-style home offers a perfect blend of comfort and convenience. Built in 1954, this brick beauty exudes timeless appeal while providing modern living spaces that cater to today's lifestyle. With 1,507 square feet of thoughtfully designed space, this residence features three cozy bedrooms and one and a half bathrooms, making it an ideal retreat for anyone seeking a warm and inviting atmosphere. As you step inside, you'll be greeted by a spacious layout that encourages both relaxation and entertaining. The partially finished basement offers endless possibilities-whether you envision a cozy family room, a home office, or a play area, the choice is yours! The main living areas are bathed in natural light, creating a welcoming ambiance that feels like home. The exterior of the property is equally inviting, with a classic brick façade that stands the test of time. Enjoy the convenience of on-street parking, ensuring that you and your guests always have a place to park. The surrounding neighborhood is a tapestry of tree-lined streets and friendly faces, fostering a sense of community that is hard to find. Location is key, and this home does not disappoint. Situated in a vibrant area, you'll find an array of local amenities just a stone's throw away. Explore nearby parks for leisurely strolls or picnics, and take advantage of local shops and eateries that add character to the community. Whether you're grabbing a morning coffee or enjoying a weekend brunch, the neighborhood offers a delightful selection of options to satisfy your cravings. For those who appreciate the outdoors, the proximity to parks and recreational areas provides ample opportunities for hiking, biking, and enjoying nature. The community is well-connected, making it easy to access nearby attractions and essential services. This charming ranch-style home is more than just a property; it's a place where memories are made and cherished. With its inviting atmosphere, convenient location, and potential for personalization, this residence is ready to welcome you home. Don't miss the chance to make this delightful space your own!

1048 Woodland Ave, Winchester

Listing courtesy of Re/Max Roots. Contact: (540) 686-7362
$429,000
3 Beds ⋅ 2 Baths
Awesome Interior Photo's Coming Soon! Step inside this tastefully renovated brick ranch and feel instantly at home. Offering three comfortable bedrooms and two full baths, this property blends classic charm with thoughtful updates throughout. The main level features a bright, welcoming layout perfect for everyday living, while the lower level opens the door to exceptional flexibility — complete with its own entrance, a full bath, and a kitchenette. It’s an ideal setup for multi‑generational living, extended guests, or a turnkey investment opportunity ready for rental income. Outside, the large fenced yard provides space to relax, play, garden, or gather, and the off‑street parking adds everyday convenience. The location couldn’t be better: close to schools, the college campus, Historic Downtown Winchester, and a wide range of shopping and commuter routes. A move‑in‑ready home with options, comfort, and character — schedule your tour today and see how perfectly it fits your needs. Schedule your tour today!Awe

1412 S Loudoun St, Winchester

Listing courtesy of Long & Foster Real Estate, Inc.. Contact: (540) 662-3484
$308,000
2 Beds ⋅ 2 Baths
This charming cottage in the heart of the City of Winchester is poised for a remarkable transformation with major renovations slated for 2026. Built in 1950, this detached home offers a unique opportunity for investors seeking to capitalize on a revitalized property in a desirable location. With two spacious bedrooms and two full bathrooms, the layout is perfect for modern living. The full basement provides ample storage or potential for additional living space, enhancing the property's value. Set on a generous 0.34-acre lot, there's plenty of room for outdoor enjoyment or future enhancements. The vinyl siding ensures low maintenance, while the inviting architectural style adds character. Investors will appreciate the potential for significant returns as the renovations breathe new life into this home, making it an attractive option for renters or future buyers. With its warm ambiance and promising upgrades, this property is a sound investment in a thriving community. Don't miss the chance to be part of its exciting journey!

2519 Hockman Ave, Winchester

Listing courtesy of Link Realty Services LLC. Contact:

$379,900
2 Beds ⋅ 2 Baths
This charming Cape Cod home in Winchester City, built in 1950 and beautifully renovated in 2026, offers a perfect blend of classic character and modern convenience. With 2 spacious bedrooms and 2 full bathrooms, including a luxurious walk-in shower, this residence is designed for comfort. The heart of the home features a bright kitchen equipped with stainless steel appliances, including a refrigerator, dishwasher, microwave, and stove, making meal prep a delight. A generous size family room just off the kitchen. Enjoy the convenience of main-floor laundry and a partially finished basement, perfect for a cozy retreat on gameday, or even possible 3rd bedroom, & couple extra rooms for storage. The attic could also add potential living space.(possible 4th) The inviting outdoor space is ideal for relaxation, Brand New Garage while the driveway provides ample off-street parking. Nestled in a vibrant community, residents benefit from nearby parks, excellent schools, Shenandoah University and convenient public services. Experience the warmth of neighborhood gatherings and the charm of local shops. This home is not just a place to live; it's a place to thrive. Embrace the lifestyle you've been dreaming of!

1414 S Braddock St, Winchester

Listing courtesy of Long & Foster Real Estate, Inc.. Contact: (540) 662-3484
$250,000
2 Beds ⋅ 1 Baths
Welcome to 1125 Conway Ave, a charming bungalow in Winchester City that's move-in ready and full of character! This cozy 2-bedroom, 1-bath home features beautiful hardwood floors and numerous recent updates, including a new roof, fresh interior paint, kitchen remodel, hallway and bathroom flooring, and a new stainless steel refrigerator. The deck has also been restored, providing a great spot to relax or entertain. Conveniently located near shopping, dining and everyday amenities, with quick access to I-81 from Winchester's east side—making it an excellent option for commuters. Whether you're a first-time buyer, downsizing, or looking for a low-maintenance home in the city, this bungalow is worth a look. Schedule your showing today!

1125 Conway St, Winchester

Listing courtesy of NextHome Realty Select. Contact: (540) 667-9097
$359,000
3 Beds ⋅ 2 Baths
You've been dreaming of main-level living, and this is IT! Check all your boxes: ✅ 3 bedrooms ✅ 2 full bathrooms ✅ Open-concept family room ✅ Beautifully updated kitchen ✅ Spacious kitchen island ✅ Primary suite with private bath, walk-in shower, and walk-in closet ✅ Charming front porch - perfect for morning coffee ��� Roof replaced 2018 ✅ Private back deck ✅ Fenced backyard ✅ Storage shed ✅ Beautiful perennial flowers ✅ Convenient to shopping, hardware stores, pharmacy, and downtown Winchester ✅ Easy access to Route 7 and I-81 - ideal for commuters Comfort, convenience, and single-level living come together in one wonderful, updated home! PHOTOS COMING SOON!!

700 Green St, Winchester

Listing courtesy of Colony Realty. Contact:

$394,900
3 Beds ⋅ 2 Baths
Nestled in the charming Morganside community, this delightful split-level home offers a perfect blend of comfort and functionality. Built in 1997, this well-maintained residence boasts 2,300+ square feet of inviting living space, ideal for creating lasting memories. Step inside to discover a warm and welcoming atmosphere, featuring three spacious bedrooms and two full bathrooms. The thoughtfully designed layout provides ample room for relaxation and entertaining, with a cozy living area that flows seamlessly into the dining space. Outside, the 0.18-acre lot offers a private retreat, perfect for enjoying sunny afternoons or evening barbecues. The driveway accommodates two vehicles, ensuring convenience for you and your guests. Located in a peaceful neighborhood, this home is just a short distance from local amenities, parks, and recreational opportunities, making it an ideal spot for those seeking a balanced lifestyle. With its inviting charm and practical features, this residence is more than just a house; it's a place to call home. Don't miss the chance to make this lovely property your own and start creating the life you've always envisioned!

63 Riflemen Ln, Winchester

Listing courtesy of RE/MAX Roots. Contact: (540) 686-7362
$615,000
5 Beds ⋅ 4 Baths
Welcome home to this beautifully updated brick-front residence in the City of Winchester, where a thoughtful floor plan, generous living spaces with 9' ceilings on the main and upper levels, and meaningful improvements come together across three finished levels. The main level is designed for connection and comfort, beginning with a two-story foyer that opens into an airy, open-concept layout. The kitchen flows seamlessly into the main living area, creating an ideal space for everyday living and entertaining, while offering defined rooms for flexibility. Just off the kitchen, the mudroom connects to the garage and provides ample storage and seating when entering and exiting the home. A dedicated office provides a quiet place to work, and the formal dining room—enhanced with beautiful moldings—offers an elegant setting for gatherings. A separate music room adds space to relax or unwind. Throughout the main level, new crown molding, freshly painted walls and ceilings, and bamboo flooring create a cohesive feel, while brushed nickel finishes add a modern touch. The fireplace with new gas logs serves as an inviting focal point for the living area. From the main level, step through one of the new sliding glass doors onto the newly built deck, with stairs leading directly to the yard. This outdoor space is ideal for morning coffee, summer dinners, or entertaining friends. Upstairs, new oak hardwood flooring enhances the main stairs, landing, hallway, and primary suite, including a large double-sided walk-in closet. The entire upper level has freshly painted walls and ceilings, while new crown molding extends from the two-story foyer into the hallway. The primary bathroom has been updated and features heated flooring with app control for added comfort. The additional upstairs bathroom has also been updated, and the other three upstairs bedrooms feature new carpeting, giving the entire level a fresh, cohesive feel. One of the most convenient features of the upper level is the dedicated laundry room—no more carrying baskets between floors. Finished with waterproof LVT flooring, cabinetry, a countertop, walk-in closet shelving, and included Consumer Reports top-rated high efficiency washer and dryer, it is both practical and well-appointed. The lower level expands the home even further with nearly 1,000 additional finished square feet. Fresh paint and new carpeting throughout give this level a clean, updated feel. This space includes a large recreation room with a separate entry, offering excellent flexibility for entertaining or everyday living. It also features a fifth bedroom (non-legal egress) and a full bathroom, and an additional washer and dryer hookup - making it ideal for guests, extended stays, or multi-use living arrangements. Behind the scenes, the home has been carefully maintained and upgraded for long-term comfort and efficiency. The roof, washer and dryer, and HVAC system are all approximately four years old. The HVAC system is a Carrier air handler paired with a Carrier air-conditioning unit featuring a variable-speed inverter compressor, providing exceptional efficiency and helping keep energy costs low. Additional improvements include upgraded R-52 attic insulation, Honeywell Home app controls, and a Tamko Titan architectural shingle roof rated for 50 years. The attached 2-car garage has also been enhanced with highly insulated Lewin-Yount doors and Aladdin Connect smartphone control. With approximately 2,700 square feet above grade plus nearly 1,000 finished square feet in the basement, this 5-bedroom, 3½-bath Winchester City home offers a rare combination of space, versatility, and move-in-ready convenience. From its open and functional floor plan to its hardwood and bamboo flooring, updated systems, flexible living spaces, and thoughtful upgrades throughout, this is a home designed for both everyday living and memorable gatherings. Come inside, take your time, and imagine making it yours. Welcome HOME!

922 Wayne Dr, Winchester

Listing courtesy of Samson Properties. Contact: (540) 348-4911
$434,000
3 Beds ⋅ 3 Baths
Priced at recent appraised value. Welcome home to this beautifully maintained historic log home in the heart of Winchester. Thoughtfully updated while maintaining the charm of yesteryear this home offers the conveniences of modern living. Traditionally appointed, the main level of the home provides the perfect separation of spaces with a large formal living room, dining room, gourmet kitchen, additional full bath and main level washer/dryer. The second level of the home offers a sitting area, primary bedroom with its own half bath and two addtional bedrooms with a shared bathroom. Accessed by the third bedroom, the attic offers a blank canvas and could be easily transformed into a secondary living area, home office, or a recreation and fitness room. Wide plank pine flooring remains throughout most of the home along with many traditional fiixtures. Recent improvements include a new gourmet kitchen with SS appliances, hvac, water heater, exterior clapboard cedar siding replaced where needed and new tile floors in the kitchen, main level bath and utility room. Step outside to the quaint backyard which offers an oasis for relaxation, play and gardening. The location of the home can't be beat. Just a few blocks to the pedestrian mall, one can experience a plethora of dining options, coffee shops, boutique stores, galleries and local social activities.

422 S Loudoun St, Winchester

Listing courtesy of Realty ONE Group Old Towne. Contact: 5407738475
$1,100,000
6 Beds ⋅ 6 Baths
Welcome to this inviting, beautifully maintained 6-bedroom, 4-full-bathroom, 2-half-bathroom all-brick home in the desirable Meadow Branch subdivision in Winchester, Virginia. Offering over 6,000 square feet of finished living space, this impressive residence combines generous room sizes, timeless construction, exceptional storage, and comfortable living spaces designed for both everyday life and entertaining. Set on approximately half a lot, the property features a welcoming U-shaped driveway, mature landscaping, and wonderful curb appeal. With no HOA, you have the freedom and flexibility to enjoy the property on your terms. Inside, the home offers an abundance of built-in cabinetry, custom closet storage, and storage solutions throughout, making it easy to keep even a large household organized. The spacious layout provides plenty of room for family, guests, work-from-home spaces, hobbies, and entertaining. The walk-out basement adds another valuable level of living and recreational space, with convenient access to the outdoors. With six bedrooms, four full bathrooms, and two half bathrooms, there is plenty of flexibility for a growing family or those who simply want room to spread out. Meticulously cared for and move-in ready, this substantial brick home offers the space, storage, privacy, and location that are increasingly hard to find. Enjoy the established beauty of Meadow Branch while being conveniently located in Winchester, with easy access to shopping, dining, schools, commuter routes, and all that the area has to offer. A rare opportunity to own a spacious, established home with exceptional storage and flexibility in one of Winchester's sought after communities.

1030 Breckinridge Ln, Winchester

Listing courtesy of Samson Properties. Contact: 3049305621
$649,500
3 Beds ⋅ 2 Baths
One level living in The Downs at Meadow Branch, a sought after community convenient to shopping, medical center, and Old Town Winchester. Expansive all-brick home offers 3 bedrooms, 2 bathrooms, attached 2-car garage and 2450 square feet of living space! What's better than an idyllic 1/5 acre corner lot... how about an idyllic 1/5 acre corner lot you don't have to mow? HOA fees include lawn mowing, mulching, leaf clean up, and tree and shrub maintenance! Six-panel front door with sidelights opens into a welcoming tiled foyer. Hardwood floors run through the kitchen, living and dining rooms, as well as the 2nd and 3rd bedrooms. Charming country kitchen features granite counters and stainless steel appliances, as well as a cozy breakfast nook, and access to the screened porch with ceiling fan. Large living room with gas fireplace. Formal dining room boasts chair and crown molding (note, chandelier does not convey, lighting fixture has been ordered for replacement). Primary bedroom has walk in closet and en-suite bath with double vanity, jetted tub and separate shower. Property is being sold AS-IS but this is a great opportunity to own in a desirable rarely-available City of Winchester community! Showings start Friday 8/21.

1400 Gordon Pl, Winchester

Listing courtesy of Berkshire Hathaway HomeServices PenFed Realty. Contact:

$274,000
3 Beds ⋅ 2 Baths
This charming house has great potential. It is located directly across from the Virginia Avenue School campus, close to downtown Winchester. The exterior was recently painted and a new roof installed in 2025. This home would be great "Handyman's Delight" as the interior needs quite a bit of attention as the bath and kitchen are outdated. The 100 amp electric service was updated in 1993, water heater installed in 2012 and the oil furnace is a newer model. This house currently is winterized and electricity shut off. (There is no lighting in the basement.)

519 Virginia Ave, Winchester

Listing courtesy of Colony Realty. Contact:

$369,999
3 Beds ⋅ 2 Baths
Home Warranty for the Buyer + Bonus for the Buyer’s Agent with a Ratified Contract in September! Welcome to this adorable and beautifully refreshed Cape Cod, ideally located on a quiet street in Winchester City with no HOA! This move-in-ready home offers a comfortable and versatile floor plan, featuring a primary suite on the main level, plus two spacious bedrooms and a second full bathroom upstairs. Enjoy the peace of mind that comes with numerous recent updates and renovations completed in 2024, including architectural shingles, carport soffit, central heating and air conditioning with a dual-zone electric heat pump, crawl space sump pump and poly, and fresh paint throughout. Inside, you’ll find refinished real hardwood floors in the living areas and bedrooms, updated flooring in the kitchen and bathrooms, and numerous updated plumbing and light fixtures, vanities, outlets and switches. The Kitchen and primary bathroom feature a quartz countertop, an undermount sink with beautiful tiled shower with a glass door. This home offers a wonderful opportunity to move right in and enjoy.

2919 S Pleasant Valley Rd, Winchester

Listing courtesy of Keller Williams Realty Dulles. Contact:

$499,999
4 Beds ⋅ 4 Baths
Location, Location, Location! NO HOA!!! Priced below assessed value! Hardwood floors on the main level. Formal living and dining room leads to the Family room with stone fireplace, breakfast nook and kitchen. Step out on to the deck to enjoy the views. Large fenced level backyard. Large Primary suite with sitting room and luxury bath. Good sized bedrooms, one with an attached bath. Lower level leads to a patio and backyard. Seller transferred. Opportunity to expand to a rental suite; seller had started the framing.... Near Shenandoah College, Publix new shopping center and major routes.

2643 Middle Rd, Winchester

Listing courtesy of Berkshire Hathaway HomeServices PenFed Realty. Contact:

$530,000
5 Beds ⋅ 4 Baths
Fort Braddock Heights (Winchester City) - Detached Two-Level Home with Five (5) Bedrooms + Three (3) Full Bathrooms + One (1) Half Bathroom *Approx. 2,417 Finished Square Feet Across Two (2) Levels *Built 1992 *0.23 Acre Lot (Approx. 10,019 Square Feet) *One (1) Car Attached Front-Loading Garage + Paved Driveway *Second Garage Bay Converted to Oversized Main Level Laundry and Storage with Bonus Area Across the Front *Washer and Dryer Convey with the Property *Oversized Front Porch *Fully Fenced Rear Yard *Mature Landscaping *8' x 10' Outside Storage Shed *All Five (5) Bedrooms on the Upper Level *Two (2) Primary Suites *Primary Bathroom with Soaking Garden Tub + Separate Shower *Walk-In Closets *Vaulted Ceiling in Family Room Off the Kitchen *Wood-Burning Fireplace *Crown Moulding *Ceiling Fans *Additional Storage in Floored Attic Space *Updated Kitchen (2020) with Wood Cabinetry, Quartz Countertops and Stainless Steel Appliances *Luxury Vinyl Plank Flooring in Foyer and Kitchen *Architectural Shingle Roof (2009) *Tankless On-Demand Water Heater *Two (2) Zone Heating and Air Conditioning *No Homeowners Association *Cul-de-Sac Setting with No Through Street *Inside the City Limits of Winchester *Winchester City Public School Assignments *Close to Old Town Winchester *Minutes to Winchester Medical Center and the Shenandoah University Health Professions Campus *Convenient to Route 37 and Interstate 81 Commuter Routes.

1605 Fort Braddock Ct, Winchester

Listing courtesy of Long & Foster Real Estate, Inc.. Contact:

$450,000
4 Beds ⋅ 2 Baths
Welcome to this beautifully updated 4 bedroom, 2 full bath home in the heart of Winchester City! This move in-ready property offers fresh paint throughout, newly installed laminate flooring, new carpet in the bedrooms and new ceiling fans, and a fully finished basement providing additional living space. The kitchen features a new dishwasher, while recent updates include a new dryer, toilet, and bathroom sink and cabinet. Outside, enjoy a landscaped yard, convenient carport, two storage sheds with one currently being installed, and a freshly pressure washed exterior. Ideally located right in town with easy access to shopping, dining, and all that downtown Winchester has to offer. Don't miss the opportunity to make this updated home your own! Basement bedroom and bathroom work is in progress!

501 Fox Dr, Winchester

Listing courtesy of Coldwell Banker Premier. Contact:

$425,000
3 Beds ⋅ 2 Baths
This beautiful rancher sits on 0.38 acres with an expansive, level backyard that is fully fenced and shaded by gorgeous mature trees. A large deck spans the back of the home and incorporates a charming stock-tank plunge pool with liner and filtration system, creating a fantastic space for relaxing and entertaining. Inside, the beautifully renovated kitchen is a standout, while the primary suite offers a walk-in closet and a stylishly remodeled en suite full bath with walk-in shower. The lower level adds even more living and entertaining space, with over half of the basement finished, a wet bar, and convenient walk-up access to the backyard. A carport and high-speed internet round out the home's practical features. Tucked into an established Winchester neighborhood with incredible convenience, you’re just minutes from shopping, dining, Shenandoah University, Winchester Medical Center and historic Old Town, with easy access to I-81 and Route 37.

413 Superior Ave, Winchester

Listing courtesy of Samson Properties. Contact: (540) 348-4911
$319,900
3 Beds ⋅ 1 Baths
Welcome to 12 N Purcell Ave, a classic white bungalow offering standout curb appeal, a well-kept lawn and landscaping, and an unbeatable central location. Relax on the covered front porch before stepping inside to a bright and inviting main level featuring rich hardwood floors and a spacious eat-in kitchen with plentiful cabinet space. Two sizable bedrooms and a full bath round out the main floor for comfortable, easy living. The upper level serves as an expansive additional bedroom full of original charm, showcasing warm hardwood floors and classic wood-accented walls alongside custom built-in shelving, an integrated dresser, and a cedar-lined closet. This versatile space offers endless possibilities to suit your lifestyle—whether you want a private primary suite, home office, or hobby room. The full, unfinished basement offers massive storage capacity, laundry facilities, chairlift access, and a dedicated workshop space perfect for tools and DIY projects. Outside, the large, fully fenced backyard is a rare find for a city lot—giving you plenty of room to garden, host, or let pets play freely, as well as a shed for handy outdoor storage. All of this is situated just blocks from Jim Barnett Park and Daniel Morgan Middle School, with quick access to local shopping, dining, historic downtown Winchester, and major commuter routes.

12 N Purcell Ave, Winchester

Listing courtesy of Colony Realty. Contact:

$357,500
4 Beds ⋅ 3 Baths
CHARMING CAPE COD IN AN IDEAL IN‑TOWN LOCATION, THIS HOME HAS A WELCOMING EASE TO IT, OFFERING 3–4 BEDROOMS AND 2.5 BATHROOMS WITH A LAYOUT THAT ADAPTS BEAUTIFULLY TO EVERYDAY LIVING. THE MAIN LEVEL INCLUDES TWO CONVENIENT BEDROOMS, A COMFORTABLE, LIGHT‑FILLED LIVING ROOM, A SEPARATE DINING AREA, AND A RENOVATED KITCHEN FEATURING NEW CABINETS AND STAINLESS‑STEEL APPLIANCES. IN 2021, THE HOME RECEIVED A THOUGHTFUL REFRESH: NEW VINYL PLANK FLOORING THROUGHOUT, RENOVATED BATHROOMS, NEW LIGHT FIXTURES, NEW RECEPTACLES/SWITCHES/COVERS, A NEW ROOF, AND MORE PAIRED WITH UPDATED PLUMBING FOR ADDED PEACE OF MIND. UPSTAIRS, YOU’LL FIND TWO ADDITIONAL ROOMS AND A BATHROOM, INCLUDING A POTENTIAL FOURTH BEDROOM OR BONUS ROOM IDEAL FOR AN OFFICE OR EXTRA SPACE. WITH OVER 2,000 SQ FT OF FINISHED LIVING SPACE, THE HOME ALSO INCLUDES A FINISHED BASEMENT WITH A FULL BATH AND A DOOR LEADING DIRECTLY TO THE BACKYARD, OFFERING ROOM TO EXPAND, UNWIND, OR CREATE A SECOND LIVING AREA. OUTSIDE YOU WILL FIND A SPACIOUS DECK AND FULLY FENCED BACKYARD WITH PRIVACY FENCING CREATING A COMFORTABLE OUTDOOR RETREAT—PERFECT FOR RELAXED EVENINGS, WEEKEND GRILLING, AND EASY GATHERINGS. ALL OF THIS IN A DOWNTOWN WINCHESTER LOCATION, CLOSE TO SHOPPING, RESTAURANTS, AND EVERYDAY CONVENIENCES. FOR ANYONE SEARCHING FOR A PLACE THAT SIMPLY FEELS RIGHT THE MOMENT YOU ARRIVE—A REMINDER THAT HOME ISN’T JUST A PLACE, IT’S A FEELING—THIS ENCHANTING CAPE COD CAPTURES IT. SCHEDULE YOUR TOUR TODAY

621 Patterson Ave, Winchester

Listing courtesy of Long & Foster Real Estate, Inc.. Contact: (540) 662-3484
$370,000
4 Beds ⋅ 2 Baths
Live just minutes from historic Old Town Winchester, where charming boutiques, local restaurants, and picturesque streets are all close at hand. This beautifully maintained two-story home seamlessly blends the timeless character of the 1930s with the modern updates today’s buyers appreciate. A classic covered front porch welcomes you home and offers the perfect place to enjoy your morning coffee or relax at the end of the day. Inside, beautifully restored hardwood floors, high ceilings, elegant crown and baseboard molding, and stunning original built-in cabinetry between the living and formal dining rooms showcase the home’s historic charm. Thoughtful updates provide added comfort and convenience, including a renovated kitchen, updated bathrooms, bedroom-level laundry, new windows (2023), a new water heater (2023), and a new roof (2024). Situated on one of the larger lots in the neighborhood, this property also offers incredible outdoor potential. With convenient alley access from both the side and rear, there’s plenty of room to add a garage, oversized workshop, or storage shed while still maintaining a spacious backyard for entertaining, gardening, or simply relaxing outdoors. Full of character, thoughtfully updated, and ideally located near all that Old Town Winchester has to offer, this special home is one you won’t want to miss!

1008 S Cameron St, Winchester

Listing courtesy of Redfin Corporation. Contact:

$760,000
5 Beds ⋅ 5 Baths
Welcome to 769 Seldon Drive—an elegant brick-front colonial situated on nearly half an acre in one of Winchester’s most desirable neighborhoods. Offering over 4,500 finished square feet, this spacious 5-bedroom, 4.5-bath home is designed for comfort, flexibility, and multi-generational living. Create wealth with this income producing opportunity. The main level features a generously sized primary suite with a walk-in closet and en-suite bath, along with formal living and dining rooms, a warm and inviting family room with fireplace, and a well-equipped kitchen with center island and breakfast area. Hardwood floors and detailed trim work add classic character throughout. A standout feature of this home is the private ground-level apartment with its own entrance—complete with a full kitchen, bedroom, bathroom, living space, and dedicated laundry. Perfect for guests, extended family, or potential rental income. Upstairs, you'll find additional spacious bedrooms and full baths, offering plenty of room for everyone. Enjoy the outdoors from your beautifully landscaped yard with space to garden, entertain, or relax. A two-car garage and extended driveway provide ample parking. Conveniently located just minutes to downtown Winchester, parks, shopping, dining, and commuter routes—this home offers the space and versatility you've been searching for. Priced below appraisal. Schedule your private showing today!

769 Seldon Dr, Winchester

Listing courtesy of Keller Williams Realty. Contact: 7036690099
$439,900
3 Beds ⋅ 2 Baths
Welcome home to this beautifully maintained 3-bedroom, 2-bath home offering comfort, convenience, and exceptional outdoor living. Ideally located just minutes from shopping, schools, the hospital, and other everyday amenities, this home combines a prime location with thoughtful updates. Inside, you'll find two recently remodeled bathrooms featuring modern finished and stylish upgrades. The functional layout provides comfortable living spaces perfect for everyday life. The basement has also been professionally waterproofed, and the existing waterproofing warranty will transfer to the new owner, providing added peace of mind. Step outside to enjoy the fully fenced backyard, offering privacy and plenty of space for children, pets, or entertaining. The extensive hardscaping creates a beautiful, low-maintenance outdoor retreat, while the paver driveway adds outstanding curb appeal. An above-ground pool provides the perfect place to cool off on warm summer days, and the storage shed offers ample space for lawn equipment, tools, and seasonal items. Move-in ready and conveniently located, this home offers the perfect blend of comfort, style. and accessibility. Don't miss your opportunity to make it yours-schedule your private showing today!

153 Fox Dr, Winchester

Listing courtesy of Century 21 Redwood Realty. Contact:

$399,000
3 Beds ⋅ 2 Baths
OPEN HOUSE SATURDAY SEPTEMBER 12 FROM 11AM-1PM. Charming 1932 Craftsman Near Downtown Winchester! Step into this classic 1932 Craftsman home, where timeless historic character perfectly meets modern updates. Stunning original craftsman style windows in every room. Boasting an abundance of original woodwork and original wood floors throughout, this home radiates warmth, style, and craftsmanship. The main level highlights Large, open rooms designed for seamless living and entertaining. Bright and open kitchen enjoys newer double ovens, dishwasher, new cooktop and SS hood, new kitchen sink, faucet and new butcher block countertops! The Sunroom features beautiful, heated terracotta tile floors and new double pane windows that flood the space with natural light. Outdoor boasts your classic front porch spanning the width of the house, perfect for relaxing with your favorite beverage. The main floor hosts a 1/2 bath and convenient laundry room. The second level with three generous bedrooms, each equipped with spacious closets, also features a large hall linen closet. The renovated Full Bath comes with custom tile flooring and a sleek, walk-in glass shower. Enjoy the perfect blend of neighborhood charm and urban convenience. If outdoors is your vibe, relaxing on the stone patio with plenty of room for outdoor furniture and a deep, fully fenced yard for kids and pets to enjoy! This home sits just minutes from vibrant downtown restaurants, shopping, and entertainment. Don't miss the opportunity to own a piece of history featuring the perfect balance of original 1930s details and thoughtful modern updates! Call me today to arrange your private showing. PROFESSIONAL PHOTOS COMING SOON. Agent Related to Seller.

633 Pennsylvania Ave, Winchester

Listing courtesy of Colony Realty. Contact:

$359,000
3 Beds ⋅ 1 Baths
Lovingly maintained, this charming brick rancher is the perfect starter home or investment opportunity! The main level offers three comfortable bedrooms, one full bath, a bright eat-in kitchen, and a spacious living room filled with natural light. The full unfinished basement provides endless potential for additional finished living space, while an existing hobby room is already in place—perfect for sewing, crafts, a workshop, or a home office. A unique bonus is the custom-built "catio" just off the back of the home, creating a safe outdoor retreat for your feline friends. Outside, enjoy a private backyard with mature landscaping and a detached one-car garage. Ideally located just minutes from Old Town Winchester, the Walking Mall, the Museum of the Shenandoah Valley, Winchester Medical Center, shopping, dining, and commuter routes, this home offers both convenience and charm. Major updates completed in 2016 include new windows, HVAC, roof, driveway, and beautifully refinished hardwood floors. The home is served by public water and a private septic system.

805 Pennsylvania Ave, Winchester

Listing courtesy of Hunt Country Sotheby's International Realty. Contact: (540) 687-8500
$400,000
2 Beds ⋅ 2 Baths
Welcome to easy one-level living in Willow Lawn Cottages, a popular 55+ community in Winchester! This well-maintained home has been freshly painted and offers 2 bedrooms and 2 full bathrooms. The open floor plan feels bright and spacious, with vaulted ceilings, plenty of natural light, and luxury vinyl plank flooring throughout. The kitchen includes granite countertops, updated cabinets, stainless steel appliances, and a built-in microwave. The primary bedroom has a walk-in closet and a private bathroom with a walk-in shower. You’ll also find main-level laundry, an attached one-car garage, a covered front porch, and a rear patio where you can relax outdoors. The HOA takes care of lawn maintenance and snow removal and provides access to the community clubhouse, gathering spaces, and sidewalks. Located close to Winchester Medical Center, shopping, restaurants, and historic downtown Winchester, this home offers comfort and convenience in a welcoming community.

1853 Rosser Ln, Winchester

Listing courtesy of Realty FC. Contact: (540) 931-0144