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221 Opequon Ave, Winchester
$249,900
2 Beds ⋅ 1 Baths
Charming 2-bedroom, 1-bath bungalow just blocks from the heart of downtown Winchester! This beautifully maintained home offers the character and convenience you're looking for, with gorgeous hardwood floors, a spacious fenced yard, and inviting covered front and side porches. The bright, comfortable interior offers a functional layout with two bedrooms and one full bath, while the full unfinished basement provides excellent storage and potential for future use. An updated roof adds peace of mind. Outside, enjoy the surprisingly spacious lot, with plenty of room for gardening, pets, entertaining, or simply relaxing outdoors. The backyard includes a shed for additional storage, while off-street parking adds everyday convenience. Located just a few blocks from Winchester's vibrant walking mall, you'll be close to local restaurants, coffee shops, boutiques, parks, entertainment, and community events. A wonderful opportunity to enjoy the charm of an established downtown neighborhood with the convenience of having so much right outside your door. All at an affordable price!

221 Opequon Ave, Winchester

Listing courtesy of ERA Oakcrest Realty, Inc.. Contact:

Selling Office: ERA Oakcrest Realty, Inc..

1202 Handley Ave, Winchester
$540,000
3 Beds ⋅ 4 Baths
Nestled on one of Winchester's most sought-after streets, this distinctive mid-century contemporary home offers a rare blend of character, space, and convenience just moments from downtown dining, shopping, and entertainment. Designed for comfortable main-level living, the home combines timeless architectural appeal with thoughtful functionality. The main level features a spacious primary suite with an expansive walk-in closet and private en-suite bath. The bright and inviting living room flows seamlessly into the kitchen, complete with granite countertops, abundant cabinetry, and a charming pass-through to the separate dining area. Just off the kitchen, you'll find a conveniently located laundry area with additional cabinetry and countertop workspace. Step outside to a private patio, perfect for entertaining or relaxing after an evening downtown. A fenced side yard provides additional outdoor space for pets, gardening, or play. Upstairs, an open loft creates the perfect reading nook, home office, or cozy sitting area, alongside two additional bedrooms and a full bath. The expansive partially finished basement provides exceptional flexibility, featuring a bonus room, full bathroom, second laundry area, and abundant storage, with plenty of room for future customization. Combining architectural character, flexible living spaces, and an exceptional location, this home presents a unique opportunity in the heart of Winchester.

1202 Handley Ave, Winchester

Listing courtesy of Realty ONE Group Old Towne. Contact:

Selling Office: Pearson Smith Realty, LLC.

820 Appleseed Ct, Winchester
$375,000
3 Beds ⋅ 3 Baths
Welcome to this beautifully maintained all brick 3 level duplex in the sought-after Orchard Hill neighborhood of Winchester City. With tree-lined sidewalks, street lighting, and Park Place Park just a short stroll away, this home offers a wonderful blend of comfort, convenience, and neighborhood charm. The home features three finished levels with plenty of space to spread out. The main level welcomes you with a cozy living room highlighted by a wood-burning fireplace, along with a separate formal dining room that’s perfect for hosting family and friends. The functional kitchen features stainless steel appliances and ample space for everyday meal preparation. Upstairs, you’ll find three bedrooms, along with a spacious full bathroom. The finished walkout lower level adds even more versatility, offering a spacious family room with a gas fireplace and builtins —perfect for entertaining, relaxing, game nights, or movie evenings plus a full bath. A dedicated laundry room with washer and dryer adds to the home’s practicality. Outside, enjoy the peaceful backyard and patio with mature trees, creating a private and relaxing setting and backing to Park Place Park Conveniently located near parks, shopping, dining, and major commuter routes, this Orchard Hill gem offers the space, location, and lifestyle you’ve been looking for. Come see all this inviting home has to offer!

820 Appleseed Ct, Winchester

Listing courtesy of ERA Oakcrest Realty, Inc.. Contact:

Selling Office: Samson Properties.

310 Longview Ave, Winchester
$450,000
3 Beds ⋅ 3 Baths
Discover a stunning blend of Colonial and Contemporary architecture in this exquisite 3-bedroom, 2.5-bathroom residence, built in 2024. Step inside to find luxurious vinyl plank flooring and plush carpeting that exude warmth and sophistication. The gourmet kitchen is a chef's dream, equipped with high-end appliances including a sleek wall oven, cooktop, and energy-efficient refrigerator, ensuring culinary excellence at every turn. Recessed lighting and elegant window treatments enhance the ambiance, creating a serene retreat. The exterior boasts tasteful features such as exterior lighting and a well-designed gutter system, while the expansive half-acre lot offers ample space for outdoor activities. Enjoy evenings on the spacious deck, perfect for al fresco dining or simply soaking in the tranquility of your surroundings. Additional highlights include an attached two-car garage with a front entry and convenient asphalt driveway, ensuring ease of access. Safety is paramount with smoke and carbon monoxide detectors installed throughout. This property is not just a home; it's a lifestyle of luxury and comfort, where every detail has been thoughtfully curated for your enjoyment. Embrace the opportunity to elevate your living experience in this exceptional residence.

310 Longview Ave, Winchester

Listing courtesy of Coldwell Banker Realty. Contact:

Selling Office: Casals Realtors.

420 E Pall Mall St, Winchester
$334,900
2 Beds ⋅ 2 Baths
"Beautifully Renovated On Pall Mall St." This 2-bedroom, 2-full bath ranch style home is ready for you to move right in! Home has been completely painted on the inside, and the outside brick/concrete, side handrails, outside/inside of doors have been freshly painted. The kitchen has new granite counters, new sink & faucet, new LVP flooring and new stainless-steel appliances. Huge family room with a large wood burning fireplace, two new windows, a new storm door, new LVP flooring, new baseboard heaters, new window A/C unit and remodeled full bathroom off of it. Both bedrooms have gorgeous, refinished hardwood floors that continue down the hall area and into a living room and dining room. Hallway bathroom has new LVP flooring, new window, new toilet and tile around the tub/shower. Large laundry room with new LVP flooring, new baseboard heater and new window. Huge deck out back with new floorboards, new top railings and new step/concrete pad down to the yard. Two great sized sheds (One with new doors). New HVAC, new thermostat and new water heater! Both Crawl Spaces have new insulation, new moisture barriers and new entrance doors. Roof was replaced in October of 2019. Chimney was inspected, cleaned and repaired as recommended so it's ready for you to enjoy! New switches, receptacles, smoke detectors, doorknobs and light fixtures throughout the home. Home has been power washed and fresh mulch put down. Agent/Owner

420 E Pall Mall St, Winchester

Listing courtesy of Samson Properties. Contact:

Selling Office: Samson Properties.

1845 Rosser Ln, Winchester
$365,000
2 Beds ⋅ 2 Baths
Beautifully maintained 2-bedroom, 2-bath Ranch home in the desirable Willow Lawn Cottages 55+ Community. The main-level features an open floor plan, vaulted ceiling, ceiling fan, gas fireplace, large concrete patio, and 1-car garage. 2026 updates include a new HVAC system. The primary suite offers a walk-in closet, private full bath, and laundry. Low maintenance living includes lawn and landscape care, snow and trash removal, allowing more time to enjoy the community’s clubhouse, exercise room, and scenic paths. Conveniently located near shopping, dining, and healthcare– Winchester Medical Center and close to local attractions like the galleries at the Museum of the Shenandoah Valley.

1845 Rosser Ln, Winchester

Listing courtesy of The Greene Realty Group. Contact:

Selling Office: Century 21 Redwood Realty.

2104 Stoneleigh Dr, Winchester
$367,000
3 Beds ⋅ 4 Baths
Situated in the charming Orchard Hill subdivision, this delightful twin home offers a perfect blend of comfort and functionality. Built in 1987, this Colonial-style residence boasts a classic brick exterior that exudes warmth and character. With over 2,000 square feet of thoughtfully designed living space, this home is ideal for those seeking a cozy retreat. As you approach the property, you'll appreciate the inviting sidewalks that lead you to the entrance, enhancing the neighborhood's friendly atmosphere. The well-maintained lot, spanning 0.1 acres, provides a manageable outdoor space, perfect for gardening or enjoying a quiet afternoon in the sun. An outbuilding adds extra storage or workspace, catering to your organizational needs. Step inside to discover a fully finished walkout basement, offering versatile space that can be transformed into a recreation room, home office, or guest suite. The interior features a harmonious blend of carpet, luxury vinyl plank, and vinyl flooring, ensuring both style and comfort throughout the home. The heart of the home is the spacious kitchen, equipped with modern appliances including a dishwasher, smooth top range, refrigerator, microwave, and range hood. The adjoining dining area flows seamlessly into the living space, where a fireplace creates a cozy ambiance for those chilly evenings. With three generous bedrooms and three full bathrooms plus an additional half bath, this home provides ample space for relaxation and privacy. The convenience of upper-floor laundry adds to the home's appeal, making daily chores a breeze. Parking is easy with a driveway accommodating two vehicles, ensuring you and your guests have easy access. This property is not just a house; it's a place where memories are made. Whether you're hosting friends for a barbecue in the backyard or enjoying a quiet evening on the incredible screened in porch this home offers the perfect backdrop for your lifestyle. Experience the charm and comfort of Orchard Hill living-your new home awaits!

2104 Stoneleigh Dr, Winchester

Listing courtesy of MarketPlace REALTY. Contact:

Selling Office: Coldwell Banker Elite.

1306 Vanceright Cir, Winchester
$480,000
4 Beds ⋅ 2 Baths
Filled with storybook charm and timeless character, this enchanting cottage-style home is much larger than it appears! Newly refinished hardwood floors flow throughout the home, blending warmth and elegance with everyday comfort. The updated kitchen offers modern convenience while maintaining the home's inviting charm. The partially finished basement provides flexible space for a family room, home office, fitness area, or hobby room. Outside, you'll find a partially fenced backyard, a storage shed, and a versatile carport that can serve as covered parking or the perfect outdoor entertaining space. Nestled on a quiet cul-de-sac in one of Winchester's most desirable in-town neighborhoods, this charming home offers the best of city living. Enjoy the convenience of being within walking distance to downtown Winchester's shops, restaurants, parks, and local events. With its fairy-tale curb appeal, thoughtful updates, and surprisingly spacious interior, this home is a rare gem waiting to be discovered.

1306 Vanceright Cir, Winchester

Listing courtesy of ERA Oakcrest Realty, Inc.. Contact:

Selling Office: MarketPlace REALTY.

1004 Pennsylvania Ave, Winchester
$365,000
3 Beds ⋅ 2 Baths
Charming, Updated Rancher in the Heart of Winchester! Welcome home to this impeccably maintained 3-bedroom, 2-bath ranch offering the perfect blend of comfort, character, and convenience—all on one level! From the moment you arrive, you'll appreciate the pride of ownership and thoughtful updates throughout. The spacious kitchen is the heart of the home, offering abundant cabinetry and room to gather with family and friends. Multiple living areas provide the flexibility to create a cozy family room, home office, playroom, or hobby space—giving everyone room to spread out. Major updates provide peace of mind, including a new roof, siding, and side porch—all completed within the last year. Other updates include added storage, updated bathrooms, updated flooring, and lots of other touches throughout. Additional features include a gas furnace, central air conditioning, and an abundance of storage rarely found in homes of this size. Located within the City of Winchester, you'll enjoy the convenience of nearby shopping, dining, parks, and commuter routes while coming home to a property filled with warmth, charm, and timeless character. This lovingly cared-for home is a true hidden gem that's move-in ready and waiting for its next owner. Schedule your private tour today before this one is gone!

1004 Pennsylvania Ave, Winchester

Listing courtesy of Samson Properties. Contact:

Selling Office: Re/Max Roots.

328 Longview Ave, Winchester
$315,000
3 Beds ⋅ 2 Baths
Price Reduced $15,000! Highly Motivated Seller! Welcome to this meticulously maintained, 3 bedroom, move-in-ready ranch home located within Winchester City limits. Perfectly situated on a premium, near-half-acre lot (.46 acres) off Papermill Road, this property offers the ultimate blend of city convenience and peaceful privacy with no backyard neighbors. Property Highlights: 3 bedrooms on main level of home. Wonderful natural lighting throughout. Expansive Basement: 75% finished lower level with carpet offers endless possibilities for a rec room, gym, or home office. The remaining 25% provides excellent storage space and a dedicated workshop area. Recent Upgrades: Complete peace of mind with a new HVAC system (2019), a brand-new water heater (2025), and newer energy-efficient windows throughout. Outdoor Oasis: Relax on your covered back patio overlooking a massive backyard that borders Buffalo Lick Run. Perfect for watching local wildlife! Includes a handy storage shed. Perks & Location: No HOA fees (and city trash pickup is included!). Walk to the scenic paths at Weaver Park, and enjoy prime shopping and dining less than a mile away. Don't miss out on this city gem with a country feel—schedule your tour today!

328 Longview Ave, Winchester

Listing courtesy of Coldwell Banker Premier. Contact:

Selling Office: ERA Oakcrest Realty, Inc..

817 Chelsea Dr, Winchester
$700,000
6 Beds ⋅ 4 Baths
Spacious 5-6-bedroom, 4-bath brick-front rancher with a fully finished basement, offering flexible living space for today’s needs. The main level features a welcoming living room with a tray ceiling & a gas fireplace, a formal dining room with crown molding & chair rail, and a well-appointed kitchen with Corian countertops and a walk-in pantry. The primary suite is conveniently located on the main level and includes crown molding and a spacious walk-in shower and 2 walk-in closets with custom shelving. A dedicated main-level office provides the perfect work-from-home setup. Designed for everyday ease, this home offers two main-level laundry areas—one with a utility sink. The finished lower level expands your living space with an additional bedroom & full bath, and a family room with a second gas fireplace. Enjoy outdoor living with a large covered patio, screened porch, and a deck overlooking a fenced backyard. Extensive front landscaping and a sprinkler system. A 2-car garage with a terrazzo floor and built-in cabinets adds extra storage and functionality. This home has it all and in a desirable Winchester setting! Electronic air filters, humidifier, lawn sprinkler system. HVAC 2016 (main/basement level), HVAC 2018 (upper level), appliances updated 2025, sump pump 2026, upgraded bathroom with walk-in shower. Check out our 3-D tour attached to the listing!

817 Chelsea Dr, Winchester

Listing courtesy of RE/MAX Roots. Contact:

Selling Office: Coldwell Banker Premier.

1813 Sloane St, Winchester
$388,000
4 Beds ⋅ 4 Baths
1813 Sloane St. is an attractive new 3 level townhome with full brick front in Winchester, VA for September move-in. Included Deck for first 3 homebuyers! Our modern Adams floorplan features a 1-car garage, and a bedroom and full bathroom on the first floor. The main level with LVP Floors features a kitchen equipped with beautiful Quartz countertops, white cabinets, and stainless-steel appliances. The upper floor offers 3 bedrooms including a spacious owner's suite with a private bath and large walk-in closet and a convenient bedroom level laundry. Abrams Crossing at Meadow Branch features a fully walkable location and offers convenient access to I-81 and all major commute routes. It's close to shopping, restaurants, and Winchester Medical Center. Featuring America's Smart Home, D.R. Horton keeps you close to the people and places you value most. Simplify your life with a dream home that features hands-free communication, remote keyless entry, video doorbell, and so much more! It’s a home that adapts to your lifestyle. And with D.R. Horton's simple buying process and ten-year limited warranty, there's no reason to wait. Up to $7,500 total closing cost is tied to the use of DHI Mortgage. *Photos, 3D tours, and videos are representative of plan only and may vary as built.

1813 Sloane St, Winchester

Listing courtesy of D R Horton Realty of Virginia LLC. Contact:

Selling Office: Non Subscribing Office.

338 Lanny Dr, Winchester
$430,000
3 Beds ⋅ 2 Baths
Come home to Whittier Acres and this well maintained Rancher with 1-car garage just minutes from Winchester Medical Center. You'll love the cozy living room with wood burning fireplace, crown molding & built in bookshelves. Gleaming hardwood floors grace the main level (just refinished). The kitchen has a French door refrigerator, electric range, built-in microwave, dishwasher, a built-in spice rack & a tile backsplash. The primary suite includes a remodeled primary bath (2023). There is a cozy sun porch on the rear of the home. Enjoy your morning coffee on the inviting front porch or out on the rear deck. The partially finished basement offers a large recreation room with wood stove for all your favorite hobbies. There is also a spacious storage room for your holiday decor, etc. The fenced backyard has a fire pit perfect for cooler fall evenings. There is also a shed for storing your gardening tools.

338 Lanny Dr, Winchester

Listing courtesy of Century 21 Redwood Realty. Contact:

Selling Office: Pearson Smith Realty, LLC.

2917 First St, Winchester
$310,000
3 Beds ⋅ 1 Baths
Welcome home to this charming stone rancher, perfectly situated on a fantastic lot adorned with gorgeous, mature trees and a lush, expansive yard. Step inside to find a spacious living room bathed in natural light, featuring rich hardwood flooring and a cozy stone fireplace that serves as the room's centerpiece. The effortless layout flows seamlessly into the kitchen and formal dining room, making it ideal for both daily living and entertaining. A bright, inviting sunroom offers a serene retreat for year-round enjoyment, overlooking your private outdoor oasis. The main level is completed by three generously sized bedrooms—all boasting beautiful hardwood floors—and a well-appointed full bath. Downstairs, the unfinished partial basement provides excellent room for storage or can be finished for additional living quarters. This home features a brand new HVAC system and water heater, alongside a newer roof, making it entirely move-in ready. Complete with a convenient one-car attached garage and a handy outdoor shed, this Winchester gem offers the perfect blend of character and comfort, all while being just minutes away from the vibrant dining, boutique shopping, and popular local hotspots of historic Old Town Winchester.

2917 First St, Winchester

Listing courtesy of Colony Realty. Contact:

Selling Office: Realty ONE Group Old Towne.

304 Shenandoah Ave, Winchester
$260,000
3 Beds ⋅ 2 Baths
Classic charm in this brick Cape Cod located in Winchester City, just minutes from shopping, dining, and commuter routes. Set in a sidewalk-lined neighborhood, this home is full of character with arched doorways, hardwood floors throughout, and a wood-burning fireplace that creates a warm focal point in the living room. The kitchen features white cabinetry, stainless steel appliances, and granite countertops, offering both style and functionality. A bright sunroom provides additional living space overlooking the backyard, while the deck is perfect for relaxing or entertaining outdoors. A detached one-car garage in the backyard adds convenient parking and extra storage, making this home an exceptional opportunity.

304 Shenandoah Ave, Winchester

Listing courtesy of Re/Max Roots. Contact:

Selling Office: Jim Barb Realty, Inc..

528 Battle Ave, Winchester
$310,000
3 Beds ⋅ 1 Baths
Adorable Cape Cod in the heart of Winchester! Beautifully appointed with hardwood floors, signature arched doorways from that era adding tons of charm to this lovely home. Two main floor bedrooms, renovated and updated bath, living room with gas fireplace and brick surround, kitchen with brand new gas range, expanded space perfect for dining and entertaining with doors to the front and rear yards. Upper level is open for a bedroom or recreation room, tons of storage on either side of the room. Lower level with a workshop, built in corner cupboards, laundry, back room with shelving, separate lower level space with walkout to the front yard and driveway. The rear yard is HUGE! Fully fenced with two large storage sheds, covered back patio perfect for entertaining and all anchored by a gorgeous old Magnolia tree. New main roof in 2022, Roof on addition replaced in 2025, new water heater in 2025.

528 Battle Ave, Winchester

Listing courtesy of Carter Braxton Preferred Properties. Contact:

Selling Office: Realty ONE Group Old Towne.

802 E Cork St, Winchester
$309,000
4 Beds ⋅ 2 Baths
Motivated Seller! Check out the Virtual Tour! Rich with character and steeped in history, this spacious vintage home sits proudly on a corner lot, offering timeless appeal with many original features still intact. From the moment you enter, you’ll appreciate the craftsmanship of a bygone era—complete with built-in bookshelves, a charming upper-level sleeping porch, and a traditional canning storage area in the unfinished basement. Ideally situated in scenic downtown Winchester, the home offers easy walkability. Enjoy a pleasant stroll through Jim Barnett Park to Shenandoah University, or wander past historic Mt. Hebron into the heart of Old Town Winchester, where you’ll find an array of local shops and dining. Commuters will also appreciate quick access to I-81, Route 50, and Route 7. Inside, the home offers nearly 2,000 square feet of living space, filled with natural light and generous storage throughout. With four bedrooms and two full baths—including a flexible main-level bedroom or office—there’s room to suit a variety of needs. Step outside from the kitchen into a private, fenced backyard designed for both relaxation and productivity. A dedicated driveway adds valuable off-street parking—an uncommon convenience in Old Town. Additional highlights include brand new HVAC, solid wood kitchen cabinetry, durable countertops, a spacious walk-in storage area on the second floor, newer windows, an upgraded 200-amp electrical panel, freshly painted metal roofing, newer siding, and beautiful hardwood floors. Classic charm and a prime location—this is a home that truly stands the test of time.

802 E Cork St, Winchester

Listing courtesy of Samson Properties. Contact:

Selling Office: Samson Properties.

317 Fairview Ave, Winchester
$255,000
3 Beds ⋅ 2 Baths
Price improvement - Motivated sellers - bring offers!🏡✨ Fully Renovated SFH in Historic Winchester! ✨🏡 📍Prime location. Just minutes from charming Historic Downtown Winchester featuring local shops, restaurants, entertainment, and more! 🍽️🛍️☕ 💥 Beautifully Updated throughout. This charming home offers bright, inviting living spaces with modern finishes and thoughtfully updates designed for comfortable everyday living. w 🔨 Just Move Right In! Major improvements include: ✔️ New roof ✔️ New siding ✔️ New flooring ✔️ Fresh drywall ✔️ New appliances ✔️ New A/C mini splits ✔️ Updated systems throughout ✔️ Practically everything has been replaced! 🛏️ Rare Upper-Level Layout ✔️ 3 bedrooms upstairs ✔️ Full bath on upper level ✔️ Convenient half bath on main level ☀️ Outdoor Features You'll Love 🌿 Relaxing front porch — perfect for your morning coffee or evening beverage 🐾 Fenced yard for pets, play, or entertaining 🚗 Plenty of street parking nearby 💡 Perfect Opportunity For: 🏠 First-time home buyers 🎓 Students 💰 Investors seeking a turnkey property low maintenance property 📍 Don't miss this beautifully renovated gem in one of Winchester’s most desirable historic locations!

317 Fairview Ave, Winchester

Listing courtesy of Real Broker, LLC. Contact:

Selling Office: Treck Realty LLC.

632 Watson Ave, Winchester
$325,000
3 Beds ⋅ 2 Baths
*The previous contract terminated solely because the buyer's home sale contingency was not satisfied. The appraisal and pest inspection were completed successfully, and the seller has completed all agreed-upon home inspection repairs. A summary of the completed repairs and supporting contractor invoices are available upon request. This home is move-in ready * Nestled in Orchard Terrace, this beautifully updated Colonial home is ideally located within Winchester city limits, just a short walk to the vibrant downtown walking mall with its shops, dining, and entertainment. The updated kitchen features granite countertops, new stainless steel appliances, and new vinyl plank flooring. The bathrooms includes new vanities, faucet, tub, shower and new vinyl plank flooring. Major updates include a new HVAC system , new vinyl siding and gutters, and new windows. Fresh new interior paint throughout with updated lighting, outlets, and switches throughout the home. Storage shed conveys AS-IS. *Agent is related to owner* The information contained herein is for informational purposes only. RE/MAX Roots makes no representation as to the accuracy or reliability of the information. The buyer is to verify information provided and related to the property that is material to a buyer’s decision to purchase the property. All documents and other information attached to this listing are provided as a courtesy and should be researched and verified by the buyer agent.

632 Watson Ave, Winchester

Listing courtesy of RE/MAX Roots. Contact:

Selling Office: Berkshire Hathaway HomeServices PenFed Realty.

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