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$339,000
Exceptional investment opportunity in the heart of Winchester! This unique offering includes three income-producing rental units for one price: one duplex and one single-family home located at 211, 213, and 215 E. Clifford Street. The duplex features two separate 2-bedroom, 1-bath units, while the single-family home also offers 2 bedrooms and 1 full bath. The properties are deeded separately as two parcels (tax #193-01-T-9 & 193-01-T-8) , providing added flexibility for future investment strategies. All occupied units are currently rented on month-to-month leases, offering the new owner maximum flexibility to adjust rents, renovate, or continue operating as investment properties. As of the listing date, one unit is vacant, presenting an immediate opportunity to place a new tenant at market rent or occupy the property. Prospective buyers are welcome to drive by and walk the exterior of the properties. Interior showings are by appointment only. Whether you're looking to expand your rental portfolio or invest in a property with immediate income potential and future upside, this is a rare opportunity within Winchester City limits.

211, 213-215 E Clifford St, Winchester

Listing courtesy of ERA Oakcrest Realty, Inc.. Contact: (540) 665-0360
$182,000
2 Beds ⋅ 2 Baths
Newly remodeled 2-level townhouse located in a quiet, established neighborhood! This move-in ready home features a bright, sun-filled kitchen with a spacious eat-in dining area, two generously sized bedrooms, and 1.5 bathrooms. Enjoy the convenience of one assigned parking space directly in front of the home, plus a guest parking pass for unmarked spaces. Relax on the private rear deck or take a short, less than 5-minute walk to Frederick Douglass Park. Additional conveniences include central A/C and an in-unit washer and dryer. Recent updates include: New dishwasher New stove New microwave New kitchen faucet New toilets in both bathrooms New bathroom faucets New upstairs carpet New quartz kitchen countertops Major systems have also been updated: Updated refridgerator with added water line Washer and dryer are less than 3 years old HVAC system and water heater are less than 5 years old Whether you're looking for your next home or an excellent investment opportunity, this property offers great value and rental potential. Property is being sold As-Is. Home inspection is for informational purposes only. *Conventional Loan and Cash only. FHA does not qualify for this property*

313 Avon Ct, Winchester

Listing courtesy of AMN Realty, LLC.. Contact:

$624,900
4 Beds ⋅ 3 Baths
Welcome to this beautifully maintained 3-level Colonial tucked away on a quiet cul-de-sac in sought-after Oakdale Crossing. With 4 bedrooms, 2.5 baths, a remodeled kitchen, spacious living areas, and room to make the home your own, this is the kind of place that checks the boxes for today—and gives you plenty of space for whatever comes next. The main level is made for living, hosting, and everyday moments. Hardwood floors, crown molding, and chair rail details add timeless character to the living and dining rooms, while the family room brings a more relaxed feel with hardwood flooring, custom built-ins, crown molding, and a cozy gas fireplace. At the center of it all is the beautifully remodeled 2023 kitchen, featuring new cabinetry, upgraded countertops, ceramic tile flooring, double wall ovens, gas cooking, and tons of storage and prep space. The bright adjoining breakfast area opens directly to the covered rear porch, making morning coffee, weekend brunch, and summer entertaining feel effortless. Outside, you’ll find two inviting porches and a fully fenced backyard with low-maintenance vinyl fencing and a swing set. Whether you’re enjoying a quiet morning on the front porch or gathering with friends in the backyard, there’s room to enjoy the outdoors without the upkeep of a huge property. Upstairs, the spacious primary suite is your private retreat, complete with two walk-in closets and a spa-like bath featuring a jetted soaking tub, walk-in shower, and double vanity. Three additional bedrooms provide flexibility for guests, a home office, gym, or whatever fits your lifestyle. A full hall bath, versatile loft, and the convenience of an upper-level laundry room round out the second floor. And there’s even more potential downstairs. The unfinished walk-up basement is ready for your vision, with multiple windows bringing in natural light and a bathroom rough-in already in place. Create the ultimate rec room, home gym, office, guest suite, or additional living space when the time is right. With its cul-de-sac setting, modern kitchen, generous living space, outdoor entertaining areas, and room to grow, this Oakdale Crossing home offers the lifestyle today's buyers are looking for—with plenty of opportunity to make it uniquely yours. Move-in ready, thoughtfully updated, and ready for its next chapter. Come see why this one belongs at the top of your list.

104 Bramble Ct, Winchester

Listing courtesy of ERA Oakcrest Realty, Inc.. Contact: (540) 665-0360
$330,000
3 Beds ⋅ 3 Baths
Welcome to 101 Locust Avenue in the heart of Winchester on a spacious corner lot! This solid brick ranch home offers 3 bedrooms, 2.5 bathrooms, and comfortable one-level living with additional space in the lower level. The bright and spacious living room serves as the centerpiece of the home, featuring a large bay window that fills the space with natural light. On the main level there are three bedrooms, a full bath, and a convenient half bath. The lower level offers interior access and includes a finished room and full bathroom, providing flexible space for a home office, recreation room, hobby area, or additional living space, while the unfinished portion offers excellent storage potential. Outside, enjoy a fully fenced backyard and a covered carport for one vehicle on a spacious lot. Recent updates include a freshly painted interior completed in June 2026 and the addition of a full bathroom in the lower level in 2022/2023 Ideally located with easy access to I-81, this property is approximately 10 minutes from Shenandoah University and just minutes from shopping, dining, and other everyday conveniences. Successfully maintained as a rental property for the past four years, this home presents an excellent opportunity for both owners and investors seeking a well-cared-for property in a convenient location.

101 Locust Ave, Winchester

Listing courtesy of MarketPlace REALTY. Contact:

$410,000
3 Beds ⋅ 3 Baths
Luxury upgrades and thoughtful custom features make this exceptional end-unit townhome a standout in the desirable Winchester Landing 55+ community. With over $80,000 in owner-added upgrades, this beautifully appointed residence offers 3 bedrooms, 2.5 baths, and the convenience of main-level living with premium finishes throughout. The spacious main-level primary suite provides a private retreat, featuring a luxurious bath with a walk-in shower, dual vanities, and a walk-in closet enhanced with custom-built organization systems. At the heart of the home, the gourmet kitchen is designed for both everyday living and entertaining, showcasing granite countertops, a large center island, gas cooking, and abundant workspace. The open-concept floor plan flows seamlessly into the dining and living areas, creating an inviting atmosphere for gathering with family and friends. Step outside to a backyard transformed into a private outdoor oasis. The screened porch overlooks professionally installed turf, vinyl fencing, landscape lighting, and a custom fire pit area, creating the perfect setting for relaxing or entertaining while enjoying a truly low-maintenance lifestyle. Modern smart-home technology has been thoughtfully integrated throughout the home, adding convenience, efficiency, and peace of mind. The attached garage is equally impressive, featuring epoxy-coated floors and wall protection systems that create a clean, polished, and highly functional space rarely found in townhome living. Meticulously maintained and move-in ready, this home offers one of the finest opportunities in Winchester Landing. Combining a premium end-unit location, sophisticated finishes, and more than $80,000 in upgrades, this is luxury low-maintenance living at its best. Schedule your private showing today.

113 Wertland Pl, Winchester

Listing courtesy of ERA Oakcrest Realty, Inc.. Contact: (540) 665-0360
$289,000
2 Beds ⋅ 2 Baths
Welcome home to this one-of-a-kind, fully renovated penthouse condo that has been transformed right down to the studs! Offering luxury finishes rarely found at this price point, this stunning residence is unlike anything else available in Frederick County under $300,000. Every detail has been thoughtfully updated, including a new gas furnace, new HVAC system, new flooring throughout, neutral designer paint, custom molding, and a beautiful custom stone gas fireplace that serves as the centerpiece of the living space. The spectacular kitchen features granite countertops, upgraded soft-close cabinetry, and all-new stainless steel appliances, creating the perfect space for both everyday living and entertaining. Impeccably designed and professionally decorated, this home has the look and feel of a luxury Loudoun County property—without the Loudoun County price tag. As an added bonus, this condo can be purchased fully furnished for just $329,000, making it truly move-in ready or an incredible turnkey investment opportunity. Its convenient location also makes it an ideal home for a Shenandoah University student, faculty member, or anyone looking for low-maintenance luxury living. Don't miss this rare opportunity to own a completely renovated penthouse condo that perfectly blends style, comfort, and value!

110 Brookland Ct Unit #10, Winchester

Listing courtesy of Samson Properties. Contact: (540) 348-4911
$299,000
4 Beds ⋅ 3 Baths
Priced to sell! A true Federal‑style gem, this solid brick home offers the chance to restore a piece of architectural history. Rich with original craftsmanship, it features high ceilings, original hardwood floors, solid wood doors and trim, and a beautiful covered front porch—timeless details that showcase the home’s enduring character. Designed with good bones and a layout that adapts to many visions, this property is the ideal project for someone ready to create something extraordinary. The home was once configured with an upper‑level apartment, complete with a private entrance, back stairway, and space for a second kitchen and bath—perfect for multi‑generational living, rental income, or reimagining the entire second floor into a spacious primary suite. Updated vinyl, energy‑efficient windows and a durable metal roof provide a strong start for renovation. A walk‑up attic offers excellent storage and the potential to be finished for additional living space. The upper level could accommodate three full bathrooms, allowing for a highly functional and modern second floor once renovated. An unfinished basement with both interior access and a walk‑up exit is even more space for storage. New electrical and plumbing updates are needed giving the next owner the opportunity to modernize the home exactly to their taste. With its architectural pedigree, adaptable layout, and solid structural foundation, this property is a rare chance to bring a historic home back to life and create something truly special.

719 National Ave, Winchester

Listing courtesy of Hunt Country Sotheby's International Realty. Contact:

$550,000
3 Beds ⋅ 3 Baths
Modern craftsman home in one of Winchester’s newer communities. Easy access to RT 50 and I81, Shenandoah University, Jim Barnett Park, shopping, and restaurants. Old Town Winchester three miles away. This ranch home offers an open-floor concept with custom living upgrades. Dining room includes a coffee station/wet bar with a refrigerator and the living room has an electric fireplace with a great entertainment flow that carries onto the covered deck with stairs to the fenced-in backyard for added family fun. Finished garage with heating and cooling, recessed lighting, utility sink, and epoxy flooring makes for a great gym or multipurpose space. Master bedroom ensuite includes a bedroom-sized walk-in closet and added storage area. For an expanded living area, the full unfinished walkout basement with a full-size window and bathroom rough-in await your creative design. Other Upgrades include: Whole house water filtration system and water softener. Reverse osmosis faucet in the wet bar. LVP throughout the entire home. Adjustable Elfa-shelving in all of the closets. Smart home features allow you to control security features, garage, and thermostat from an app, including ADT alarm system and auto-lock doors; Ring cameras and doorbell; NEST thermostat; and MyQ garage door opener. Community amenities include a pool with pool house, a multipurpose court (basketball/ pickleball), two playgrounds, and a short trail.

140 Poe Dr, Winchester

Listing courtesy of Samson Properties. Contact: 7033788810
$125,000
1 Beds ⋅ 1 Baths
Ranch cabin-style home nestled in the woods on a private ½-acre lot. Featuring 1-bedroom, additional room but not technically a bedroom, and 1 full bath, this property offers endless potential as a full-time residence, weekend retreat, or investment opportunity. Enjoy the tranquility of the wooded surroundings while remaining conveniently located just 25 minutes from Winchester. The home is served by a pump-and-haul septic system. Sold strictly As-Is.

415 Puma Trl, Winchester

Listing courtesy of RE/MAX Real Estate Connections. Contact: 5406354900
$330,000
3 Beds ⋅ 2 Baths
Opportunity is knocking! The Sellers are Motivated and open to reasonable offers. If your considering making a move, now is the time to take a closer look! Escape to the peaceful mountain community of Wilde Acres and discover this charming 3-bedroom, 2-bath home situated on a spacious ½-acre lot. This well-maintained property offers privacy, tranquility, and numerous recent upgrades throughout. The entire home has been freshly repainted, featuring brand-new flooring in the foyer and basement landing, all new locks, and new door handles on every door. Enjoy outdoor living with a brand-new front porch, deck boards replaced less than a year ago, and a freshly painted front door that enhances curb appeal. A new heat pump installed less than a year ago provides energy-efficient comfort and peace of mind. The driveway has been expanded to allow for additional parking, perfect for guests or multiple vehicles. Surrounded by nature, the large yard is ideal for outdoor entertaining, relaxing, or enjoying the serene mountain setting. The unfinished basement offers endless potential for future living space, storage, or a workshop. Whether you’re looking for a full-time residence or a mountain retreat, this move-in-ready home is full of potential and ready to be enjoyed.

544 Bluebird Trl, Winchester

Listing courtesy of ERA Oakcrest Realty, Inc.. Contact: (540) 665-0360
$559,990
6 Beds ⋅ 4 Baths
The Hayden is a spacious two-story home offering 6 bedrooms, 4 bathrooms, and over 3,100 square feet of thoughtfully designed living space, perfect for both everyday living and entertaining. The main level features a versatile flex room off the foyer, ideal for a formal dining room, home office, or additional living space. The gourmet kitchen includes an oversized island with seating, a large pantry, and opens seamlessly to the dining area and expansive living room. A main-level bedroom with a full bathroom provides an ideal setup for guests or multi-generational living. Upstairs, the owner’s suite serves as a private retreat with a luxurious bath featuring a soaking garden tub, separate shower, private water closet, dual vanities, and a spacious walk-in closet. The upper level also includes three additional bedrooms, a full bathroom, a walk-in laundry room, and a loft area for added flexibility. The finished walkout basement expands the home even further, offering an additional bedroom and full bathroom—perfect for guests, recreation, or private living quarters. Situated on a homesite backing to mature trees, this home provides added privacy and a peaceful setting. Quality craftsmanship and attention to detail shine throughout, along with a one-year builder’s warranty. September delivery! Up to $10,000 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.

133 Wappinger Ter, Winchester

Listing courtesy of D R Horton Realty of Virginia LLC. Contact: 8045109139
$489,990
5 Beds ⋅ 3 Baths
Discover the perfect blend of space, function, and style in the Elm—a thoughtfully designed 2,415 sq. ft. two-story home featuring 5 bedrooms, 3 full bathrooms, a versatile loft, and a 2-car garage. Step into a welcoming foyer that opens to a bright, open-concept living area. The heart of the home is the spacious kitchen, complete with stainless steel appliances, generous cabinet storage, a pantry, and a large island with seating—perfect for daily living and entertaining. The dining area flows effortlessly into the living room, creating a warm and inviting space for gatherings. A private first-floor bedroom, tucked away at the rear of the home, is ideal for guests, in-laws, or a home office. A nearby full bath and linen closet add everyday convenience, while a coat closet near the garage entry keeps things organized. Upstairs, you’ll find a large loft, perfect for a second living room, play area, or home gym. Four additional bedrooms, including a luxurious owner’s suite, provide ample space for everyone. The owner’s suite features two walk-in closets and an oversized bathroom with a double vanity. Also upstairs are a hall bathroom with dual sinks, a laundry room, and a spacious linen closet. MOVE IN READY THIS September —this is your opportunity to own a home that checks every box. Up to $10,000 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.*

130 Wappinger Ter, Winchester

Listing courtesy of D R Horton Realty of Virginia LLC. Contact: 8045109139
$899,000
3 Beds ⋅ 4 Baths
Your long search is over! Beautifully renovated all-brick ranch home situated on a secluded 2.03-acre lot in the city of Winchester, just a short walk to Valley Health. Offering an exceptional combination of privacy, convenience, and quality. This home features spacious living areas, three fireplaces, including one in the primary bedroom. The finished lower level provides outstanding flexibility with a large rec room, full kitchen, and full bath-ideas for guests, extended family, or entertaining. Outdoor living is a grand feature, with multiple brick patios and private spaces designed to take full advantage of the tranquil park setting. The property also has a unique barn for storage or a workshop. Recent improvements include a newer metal roof, while the expansive lot offers a rare sense of seclusion within the City limits. A truly unique property that combines timeless all-brick construction, modern renovations, and an unbeatable location near medical facilities, shopping, dining, downtown Winchester, and the Museum of the Shenandoah Valley.

466 Merrimans Ln, Winchester

Listing courtesy of Colony Realty. Contact:

$784,900
5 Beds ⋅ 5 Baths
This beautiful, well-cared-for home occupies a peaceful setting overlooking a lake and stream directly behind the house. The well-stocked lake has an easily accessible walking trail near the back of the house. The owners have painted the entire interior and added new lighting fixtures, blinds, and window treatments, all of which convey. The main-floor half bath has new wallpaper, a new vanity & tile floor. The newly modernized fireplace has tile & mantle & is wired for TV. The TVs convey. New washer and dryer in the laundry room and new shelving in the laundry closet. New hot water heater. The kitchen is a dream, including a double oven, a large cooktop, and an oversized island. The morning room overlooking the lake has beautiful sunrise views. A new refrigerator and microwave have been installed in the kitchen, along with a new pantry door and shelving. The lower living area bathroom has a new vanity and mirror. With the exception of furniture in the living room and a large table, all the remaining furniture comes with the house, including the bedrooms. This is nearly a "turnkey" value; just pack your clothes and move in. The furniture that is staying in the house was purchased in the last three years. Upstairs, there are four nice bedrooms and three full baths. One of the secondary bedrooms has an en suite that is perfect for in-laws or older children. Outside, the lower-level patio area features new landscaping and swings for enjoying the view. The deck has a new railing. The front yard shrubbery was also enhanced.

118 Aulee Ct, Winchester

Listing courtesy of George W. Glaize, Jr., Inc. REALTOR. Contact: 540-662-5058
$415,000
4 Beds ⋅ 3 Baths
NEW PRICE! Welcome to 101 Charlton Road, a charming 4-bedroom, 2.5-bath Cape Cod situated on a desirable corner lot. This well-maintained home features a main-level primary suite and beautiful hardwood floors throughout the main living areas. The spacious kitchen is equipped with stainless steel appliances, a center island, breakfast nook, and flows seamlessly into the separate dining room and inviting living room, perfect for everyday living and entertaining. Upstairs, you'll find three additional bedrooms, 1.5 baths, and the convenience of an upper-level laundry room. Enjoy outdoor living in the fenced backyard complete with a storage shed, rear deck, and plenty of space for pets, gardening, or gatherings. Relax on the welcoming covered front porch and enjoy the convenience of being just minutes from Historic Old Town Winchester, Shenandoah University, Winchester Medical Center, shopping, dining, local wineries, parks, and easy access to Routes 7, 50, and I-81 for commuting. All sizes are approximate.

101 Charlton Rd, Winchester

Listing courtesy of RE/MAX Roots. Contact: (540) 686-7362
$989,000
4 Beds ⋅ 4 Baths
Nestled in the highly sought-after Stonebrook neighborhood, this incredibly quiet wooded property offers the perfect blend of privacy and convenience. This 2.6 acre estate provides a peaceful country setting while remaining close to modern amenities. Step inside and discover a thoughtfully updated home featuring 4 bedrooms and 3.5 bathrooms. The inviting living spaces include a warm and welcoming family room with a classic brick fireplace and a spacious sunroom with floor-to-ceiling windows overlooking the backyard oasis. The main floor offers an open layout ideal for both everyday living and entertaining, with a bright dining area and an expanded kitchen boasting new appliances, ample counter space, and abundant cabinetry. The outdoor space is equally impressive. Enjoy summer days by the in-ground pool, unwind on the patio, or simply take in the serene views and sounds of nature from your private retreat. With multiple fireplaces throughout the home, including one in the main living area and another in the cozy lower-level family room, comfort and charm can be found in every season. Recent updates and tasteful finishes throughout make this home truly move-in ready. Whether you're hosting gatherings, relaxing with family, or seeking a peaceful escape, this exceptional property offers the best of country living with all the conveniences of modern life. A rare opportunity to own a breathtaking private retreat where elegance, comfort, and nature come together.

137 Old Forest Cir, Winchester

Listing courtesy of Century 21 Redwood Realty. Contact:

$610,000
4 Beds ⋅ 4 Baths
Pictures coming soon. Prime Location in Raven Wing! This beautiful Colonial home offers the perfect combination of comfort, convenience, and modern updates. Located in the desirable Raven Wing community, you'll enjoy easy access to schools, shopping, restaurants, and commuter routes. Recent improvements include a new roof (2025), hot water heater (3 years old), sump pump (1.5 years old), and new dishwasher and stove, providing peace of mind for years to come. Inside, the home features 4 bedrooms and 3.5 bathrooms with an open floor plan designed for both everyday living and entertaining. The spacious family room includes a cozy gas fireplace, while the kitchen boasts upgraded cabinetry, granite countertops, and a bright breakfast area. Additional main-level features include formal dining and living rooms (or a home office), hardwood flooring, and ceramic tile flooring in all bathrooms. The spacious primary suite offers a large walk-in closet and a luxurious private bath. The fully finished basement provides a large recreation room, full bathroom, and abundant storage space. Enjoy outdoor living from the covered front and rear porches overlooking the large, fully fenced backyard, complete with a spacious patio and storage shed. High-speed internet is available. All measurements are approximate.

211 Flanagan Dr, Winchester

Listing courtesy of Berkshire Hathaway HomeServices PenFed Realty. Contact:

$289,000
3 Beds ⋅ 1 Baths
Beautifully newly remodeled ranch-style home set on a spacious 0.62-acre flat lot. This move-in ready residence features a fully updated interior with a modern kitchen complete with granite countertops, brand-new stainless steel appliances, and all-new cabinetry. The home showcases rich hardwood flooring throughout and has been thoughtfully upgraded with new windows and a newer metal roof for long-term durability and efficiency. Offering single-level living and a large usable yard, this property blends comfort, function, and value in a desirable setting.

211 Fair Ln, Winchester

Listing courtesy of Samson Properties. Contact: (540) 348-4911
$690,000
4 Beds ⋅ 5 Baths
Welcome home to Norfolk Ct!!! Oh my, where to begin? If you're looking for a turnkey home with ample space and lots of room for your dreams, then this is the home for you! Located on a quiet Cul-de-Sac, this beautiful brick home welcomes you with an impressive foyer and high ceilings. The first floor of this home houses a lovely kitchen with an ample great room, combination formal living/dining and a beautiful office/flex space with french doors. On the second floor you will find not one, but two en suite bedrooms, both quite sizeable, as are all the rooms in this lovely home. The primary suite hosts a large living space that was optioned when built, but set up to easily create an additional bedroom, if needed. The primary suite bathroom is a true sanctuary, bright, white and welcoming for your daily routine. With ample closet space, bright rooms and an additional bathroom to the two en suite bathrooms, the second floor is quite impressive. More space? OK! The basement has been completely finished with an additional full bathroom and flex room, bright recessed lighting and spacious with with walkout stairs. This home has been maintained beautifully and has a number of upgrades including, but not limited to, a full powder room remodel (2026), full basement finishing and bathroom (2025), laundry room remodel (2025), new decking (2025)... and more! With ample space for anything you can dream, whether hobbies or crafts, or entertaining friends and family, to game rooms and beyond, Norfolk Ct is waiting for you. Ideally located to commuter roads and a quick jaunt to downtown Winchester, the location is simply a bonus to all this beautiful home has to offer. *** ATTENTION BUYERS!!! This property qualifies for a reduced rate through a temporary rate buy-down program with Success Mortgage for qualified purchasers.

108 Norfolk Ct, Winchester

Listing courtesy of Coldwell Banker Premier. Contact: 990007.lead@leads.leadrouter.com
$4,000
.31 acre wooded lot on an incline. No septic or well tests have been done. Seller doesn't know if it's buildable. Drive by any time to show.

Fox Trl Unit #LOT 1, Winchester

Listing courtesy of RE/MAX Roots. Contact: (540) 686-7362
$647,000
7 Beds ⋅ 4 Baths
Welcome to this beautifully maintained home in the highly sought-after Walnut Springs Estates subdivision, offering exceptional space,comfort, and versatility on a private 2-acre lot. With up to 7 bedrooms and 3.5 bathrooms, this property is ideal for growing families, multi-generationalliving, or those who simply desire room to spread out. The inviting living room features a cozy electric fireplace, creating a warm and welcomingatmosphere for gatherings and everyday living. The thoughtfully designed floor plan provides generous living spaces throughout, while the basementapartment offers excellent flexibility for guests, extended family, rental income, or a private home office. Enjoy the outdoors year-round from thescreened-in back porch overlooking the expansive property. Additional highlights include a large attached garage, abundant attic storage, and plenty ofroom both inside and out for all your needs.

256 Skylar Lanes Way, Winchester

Listing courtesy of Old Dominion Realty. Contact:

$949,000
4 Beds ⋅ 5 Baths
Exceptional All-Brick Custom Home with Panoramic Mountain Views! Nestled on a private 2-acre cul-de-sac lot in prestigious Butler Estates, this exceptional all-brick 4-bedroom, 4.5-bath custom home offers over three finished levels, timeless craftsmanship, and breathtaking Appalachian Mountain and pastoral views. A brand-new roof adds even more peace of mind. The main level features beautiful hardwood floors and an easy flow between the gourmet kitchen and spacious family room. The kitchen offers granite countertops, center island, propane cooktop, and reverse osmosis water filtration. The family room includes custom built-ins and a fireplace. A versatile front room can serve as a library, sitting area, playroom, second office, or additional entertaining space, while a dedicated home office provides a private workspace. Upstairs, the spacious primary suite features two walk-in closets, a private balcony with stunning views, and a spa-inspired bath with double vanities, jetted tub, and tiled walk-in shower. Three additional bedrooms include a private ensuite and Jack-and-Jill bath. The finished walkout lower level is perfect for entertaining with a recreation room, gas fireplace, media room, built-ins, wet bar, and electric fireplace. An exercise room, flexible fifth-bedroom space, and full bath complete the level. Media equipment and television convey. Enjoy outdoor living on the TimberTech deck and two brick patios surrounded by professionally landscaped grounds, invisible fencing, and spectacular views. Just 10 minutes from Winchester Medical Center and minutes from Route 37 and Interstate 81, this rare all-brick Butler Estates home offers privacy, incredible views, exceptional living space, and the convenience today's buyers are looking for.

144 Widener Dr, Winchester

Listing courtesy of ERA Oakcrest Realty, Inc.. Contact: (540) 665-0360
$320,000
4 Beds ⋅ 2 Baths
Step into a home where timeless character and modern opportunity come together. This spacious property is filled with antique charm and unique details throughout. Featuring 4 bedrooms, 2 full bathrooms, and several versatile flex spaces, this home can easily adapt to your needs or offer increased income potential with a renovation. Enjoy the outdoor living opportunities with a private second-floor balcony and a shared first-level patio, perfect for relaxing or gathering with friends and family. Whether you're searching for a primary residence, an owner-occupied investment, or a property with income potential, this home offers exceptional flexibility in a highly desirable location. Ideally situated in the heart of Winchester, you'll be just minutes from the popular Old Town Winchester Walking Mall, with convenient access to shopping, dining, entertainment, and local attractions. Don't miss this opportunity to own a distinctive property in one of Winchester's most sought-after locations

410 S Cameron St, Winchester

Listing courtesy of Samson Properties. Contact: (540) 348-4911
$499,900
4 Beds ⋅ 3 Baths
Nestled in the established Cedarmeade community, this beautifully updated 4-bedroom, 3-bath ranch home offers the perfect combination of comfort, style, and functionality. With over 2,000 square feet of finished living space, this home is designed to accommodate both everyday living and effortless entertaining. Step inside to find warm hardwood flooring, abundant natural light, and thoughtfully renovated spaces throughout. The updated kitchen serves as the centerpiece of the home, featuring a large island, pantry, recessed lighting, and a seamless connection to the dining area. Two charming brick fireplaces add character and create inviting spaces to gather with family and friends. The finished lower level provides even more room to spread out, complete with a spacious recreation area, built-in bar, full bathroom, garage access, and a separate exterior entrance. Whether you’re hosting game day, creating a home office, or setting up a guest retreat, this versatile space offers endless possibilities. Outside, enjoy a spacious backyard ideal for entertaining, gardening, or simply relaxing in your own private outdoor oasis. The welcoming front porch and mature neighborhood setting enhance the home’s curb appeal and charm. Ideally located near schools, parks, shopping, dining, and commuter routes, this move-in ready home offers modern updates, generous living space, and a prime location. Don’t miss the opportunity to make this Cedarmeade gem your next home.

110 Russellcroft Rd, Winchester

Listing courtesy of Coldwell Banker Premier. Contact: 990007.lead@leads.leadrouter.com
$110,000
The rural America many people desire is available on state maintained Pack Horse Road. There are 3 lots being sold separately and this 6.42 lot C is wooded, has septic already installed, has a Frederick County cert letter (see documents from health department however buyer should do due diligence). Unrestricted and so think about the possibilities for a homestead, simple get away to enjoy quiet and tranquility, and/or the new concept of a tiny home! Driveway is a little washed out so recommend 4 wheel drive or walk up from Pack Horse Road.

Pack Horse Road Lot C, Winchester

Listing courtesy of RE/MAX Roots. Contact: (540) 686-7362
$89,000
The rural America many people desire is available on state maintained Pack Horse Road. There are 3 lots being sold separately and this 5 acre lot B is wooded, has an old cabin (do not enter and at one time had electric), has a Frederick County cert letter (see documents from health department however buyer should do due diligence). Unrestricted and so think about the possibilities for a homestead, simple get away to enjoy quiet and tranquility, and/or the new concept of a tiny home! Driveway is a little washed out so recommend 4 wheel drive or walk up from Pack Horse Road.

Pack Horse Road Lot B, Winchester

Listing courtesy of RE/MAX Roots. Contact: (540) 686-7362
$89,000
The rural America many people desire is available on state maintained Pack Horse Road. There are 3 lots being sold separately and this 6.11 lot A is wooded, has a Frederick County cert letter (see documents from health department however buyer should do due diligence). Unrestricted and so think about the possibilities for a homestead, simple get away to enjoy quiet and tranquility, and/or the new concept of a tiny home! Driveway is a little washed out so recommend 4 wheel drive or walk up from Pack Horse Road.

Pack Horse Road Lot A, Winchester

Listing courtesy of RE/MAX Roots. Contact: (540) 686-7362
$329,900
3 Beds ⋅ 2 Baths
Charming, beautifully maintained all-brick ranch home at 936 Allen Drive! Built in 1965 by Kingsberry Homes using the sought-after Belden model, this special property has been lovingly cared for by one family since its construction and even includes the original architectural floor plans. Inside, the move-in-ready home offers stunning hardwood floors and an enclosed carport seamlessly converted into a spacious family room. The main-level layout features 3 bedrooms and 1.5 baths, including a fully renovated hallway bath with a modern walk-in shower. A full, unfinished basement provides massive storage potential, while the covered rear deck and patio overlook a beautifully landscaped backyard oasis. The sellers have recently invested in numerous proactive improvements, including completed foundation work, radon mitigation, electrical panel optimization, and recent HVAC service (supporting documentation available). Excellent location just minutes from historic downtown Winchester shops and dining, with effortless commuter access to Interstate 81 and Route 50 into Northern Virginia. A wonderful opportunity with important updates already addressed!

936 Allen Dr, Winchester

Listing courtesy of Dream Real Estate. Contact: 5408692964
$348,000
3 Beds ⋅ 2 Baths
Enjoy one-level living in this spectacularly located brick rambler, nestled in a quiet residential neighborhood while remaining conveniently close to Route 11 with easy access to I-81. The property currently has a long term month-to-month tenant paying under market value, offering flexibility for an owner-occupant or an investor seeking rental income with potential for increased rent. Situated on a desirable corner lot, the home features ample driveway parking and presents a variety of opportunities to suit your needs.

302 Wentworth Dr, Winchester

Listing courtesy of Samson Properties. Contact: (540) 348-4911
$295,000
3 Beds ⋅ 1 Baths
Ideally situated just minutes from I-81 and a short drive to historic Old Town Winchester, this centrally located rambler offers both convenience and investment potential. Situated on a desirable corner lot, the property features a fenced yard and a storage shed for added functionality. The home has been recently refreshed with new paint and landscaping, providing excellent curb appeal and a well-maintained appearance. Whether you're looking to expand your investment portfolio or secure a future owner-occupied residence, this property presents a great opportunity. A tenant is currently in place through November 8, 2026, paying below market value, with potential for future rent increases. Enjoy immediate rental income and long-term upside in a sought-after location.

405 Shenandoah Ave, Winchester

Listing courtesy of Samson Properties. Contact: (540) 348-4911