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$3,175,000
6 Beds ⋅ 7 Baths
A Once-in-a-Generation Opportunity: 1765 Heritage Meets Modern Luxury Rarely does a property of this caliber, history, and scale become available within Winchester city limits. Perfectly positioned on 5.49 acres of breathtaking, park-like grounds, this historic masterpiece is a true private oasis. Painstakingly and lovingly renovated, the estate offers an unparalleled blend of 18th-century charm and contemporary convenience across 8,593 finished square feet, featuring 6 bedrooms, 5 full baths, and 2 half baths. The heart of the residence is the original 1765 portion, which stands as a museum-quality testament to early American craftsmanship. It showcases meticulously preserved original flooring, windows, doors, period hardware, stately mantles, and staircase. As the estate evolved, a first major addition was seamlessly introduced in 1940, followed by a second grand addition in 2000. True to the property's legacy of excellence, the 1940 wing underwent a major, high-end renovation in 2019 to ensure flawless modern style. Yet, behind the historic craftsmanship lies a completely modernized infrastructure: the entire home boasts fully updated plumbing, electrical, and central heating and A/C. Step outside to find your own secluded sanctuary, complete with a natural spring and a picturesque pond. This is a living piece of art, offering the perfect synergy of historical beauty, absolute privacy, and contemporary convenience. For additional information, full ownership history starting in 1735 and comprehensive renovation highlights please view the accompanying documents. Schedule your private tour to experience this once-in-a-lifetime legacy property. See accompanying files for full Historical Lineage starting in 1735, and details about the architecture and features.

730 Merrimans Ln, Winchester

Listing courtesy of Berkshire Hathaway HomeServices PenFed Realty. Contact:

$495,000
3 Beds ⋅ 2 Baths
OPEN HOUSE 08/30/2026 FROM 1:00 PM - 3:00 PM Welcome to this charming historic home in Old Town Winchester. This spacious 3-bedroom Colonial blends timeless character with modern comfort in a convenient downtown location. Thoughtfully updated with today’s buyer in mind, this inviting residence offers upgraded amenities while preserving its classic appeal. Ideally situated within walking distance from the heart of historic Old Town Winchester, you’ll enjoy the convenience of being close to local shops, restaurants, entertainment, downtown amenities, Shenandoah Valley Museum, and Valley Health Medical Facilities. Adding to the appeal, the home is tucked along a private one-way street, offering a quieter, more peaceful setting while keeping you just steps from everything downtown Winchester has to offer. Outside, the detached garage offers exceptional versatility for parking, storage, hobbies, home gym, or a workshop.

108 Morgan St, Winchester

Listing courtesy of Real Broker LLC- Winchester. Contact:

$1,239,000
4 Beds ⋅ 8 Baths
This amazing property is ready for you! Located close to Winchester Medical Center, Churches, Shopping, Historic Downtown Winchester, John Kerr Elementary School, and John Handley High School. This property is beautifully landscaped with plush gardens, a koi pond, waterfalls, a large pool, pool room, large deck overlooking the property, and a fenced backyard lined with mature trees for privacy. Inside, you will find a stunning kitchen with top-of-the-line appliances and pull-out drawers throughout the cabinets. The great room is a 2 story ceiling and fireplace leading to the deck and wet bar with ice machine and wine racks. The main level office has a full bath attached if you would like to use it as a main level bedroom. The living and dining rooms are open to each other leading to a sunroom off the deck. The primary bedroom as a gas fireplace, a balcony , 2 walk in closets and an updated spa like bathroom. The second bedroom has it's own bath and the 3rd and 4th bedrooms share a full bath with updated tile and floors. The basement also has a fireplace, a full bath, exercise room and plenty of storage. The pool room (in the basement leading to the pool) has a refrigerator, storage for towels and a 1/2 bath. The 3 car garage has a ton of storage, as the original kitchen cabinets are on the wall...This home is truly a showcase!

1022 Heth Pl, Winchester

Listing courtesy of Samson Properties. Contact: (540) 348-4911
$420,000
3 Beds ⋅ 3 Baths
Welcome to the neighborhood of Apple Ridge in Eastern Frederick County. You won't find a nicer home or more quiet cul-d-sac anywhere let alone one that has been more tastefully remodeled. The owners have completed so much updating here, including a brand new tub, faucet annd surround in the primary bedroom. It has a transferable lifetime warranty. This 3 bedroom 2.5 bath home has a welcoming front porch & overlooks the woods and open field of the private common ground area. Picnics, walks,sports and quiet time will be enjoyed there. So much has been updated here. There are new LVP floors, new wall to wall carpet, new granite counter tops, fresh paint, new light fixtures, newer architectural roof, water heater, HVAC and more. You will love the large kitchen which includes an island and a good sized breakfast room with sliders to the large rear deck with steps to the garage. Step down into the 20X12 family room with a real woodburning brick fireplace to enjoy on those colder winter nights. The formal dining room is large and your dining room furniture will find a home here. There are three bedrooms including a large primary with a walk in closet and private bath. The bathrooms have new modern vanities, toilets and new vinyl plank flooring. The owner has made a large investment to install a new Primary Bath "Bath Fitters" soaking tub with all new plumbing fixtures and tub surround. The new tub has a transferable warranty. There is a one car attached garage with a pull down staircase to the floored and lighted storage attic. This home is full of sunshine that pours through the windows. The private cul-d- sac make you feel at home, safe, and somehow removed from the day to day hussle & bussle. The top of the driveway provides a perfect spot for a parking area. Being just minutes from Rt. 7E and Downtown Winchester adds to the unique and special nature of this very special place that you will want to call home. Come and have a visit. You will be glad that you did.

104 Kapok Cir, Winchester

Listing courtesy of Century 21 Redwood Realty. Contact:

$350,000
3 Beds ⋅ 2 Baths
Welcome to this beautiful 3-bedroom, 2-bathroom split-level home, a brand-new build nestled on a spacious 0.26-acre lot in the Mountain Falls Park community. Enjoy a warm welcome with a cozy covered porch. Inside, the home features luxury vinyl plank flooring throughout, providing a modern, durable finish. The kitchen is a chef's delight, with stainless steel appliances, premium shaker-style cabinets, and sleek granite countertops that add both style and functionality. The primary bath offers a touch of luxury, with granite countertops and a convenient stall shower. Each bedroom has thoughtfully designed built-in shelving in the closets, adding extra storage and organization. The lower level boasts a spacious family room, perfect for gatherings, as well as a convenient laundry room. For vehicle storage and projects, the oversized 20'10" x 23'2" two-car garage provides ample space. Outside, the Mountain Falls Park community offers amenities, including a common area, lake, picnic area, playground, and more—ideal for outdoor recreation and family fun. This stunning new home combines comfort, style, and a scenic location—schedule your visit today to experience it for yourself! Check out the video attached to this listing!

604 Gatling Dr, Winchester

Listing courtesy of RE/MAX Roots. Contact: (540) 686-7362
$649,900
3 Beds ⋅ 2 Baths
**HUGE PRICE REDUCTION** Nearly new and designed for easy main-level living, this beautifully maintained Winchester ranch offers 2,242 finished square feet on the main level plus a full 2,242-square-foot walkout lower level—more than 4,400 total square feet of space and opportunity. Built in 2024, the warm, open floor plan features 9-foot ceilings, abundant natural light, durable LVP flooring and a spacious family room that flows seamlessly into the kitchen. The kitchen is finished with quartz countertops, stainless steel appliances, a large center island with seating and a separate sun-filled breakfast area. Just off the kitchen, glass doors open to the covered rear porch overlooking the fenced backyard and protected wooded setting beyond. The spacious primary suite offers a peaceful retreat with a spa-inspired bath featuring dual vanities, soaking tub and separate glass shower. Additional main-level spaces provide flexibility for bedrooms, guests or a dedicated home office. A mudroom with built-ins and desk space, along with an oversized walk-in pantry featuring custom real-wood shelving, adds exceptional everyday functionality. The full walkout lower level nearly doubles the home's total footprint and provides approximately 2,242 additional square feet ready to customize for a recreation room, guest suite, home gym, theater, office or additional living space. Enjoy the benefits of a nearly new home without the construction process, including an established fenced yard, covered outdoor living space, low HOA and a private setting backing to protected land. Conveniently located in Abrams Pointe with easy access to Winchester amenities, shopping, dining and commuter routes.

132 Triangle Ct, Winchester

Listing courtesy of RE/MAX Gateway, LLC. Contact: (703) 652-5777
$549,000
5 Beds ⋅ 3 Baths
Welcome home to this stunning 5-bedroom, 3-bath, 3-story Colonial located in the highly desirable Sovereign Village community on the east side of Winchester. Offering space, comfort, and thoughtful updates throughout, this home is designed to fit every stage of life. Step inside to find beautiful hardwood floors and a warm, inviting living room featuring a gas fireplace just off the kitchen—perfect for gathering and everyday living, office and dining room also complement the main floor. The main level offers a convenient bedroom and full bathroom, ideal for guests, multi-generational living, or a home office. Upstairs, you’ll find a spacious primary bedroom complete with an en suite bath and walk-in closet, three additional bedrooms, a full hall bathroom, and an upper-level laundry room for added convenience.Recent updates provide peace of mind, including HVAC (2023) with whole house humidifier, natural gas tankless hot water heater (2024), built-in microwave and dishwasher (2024), and refrigerator (2025). Outside the garage there is 30-amp RV electricity and is already wired for a future 50-amp upgrade. Enjoy your own private backyard retreat backing to open field views, where roaming deer are an occasional bonus. Outdoor living shines with a large deck, impressive stone patio, and oversized storage shed. Need more space? The spacious unfinished walk-up basement offers endless possibilities for future expansion, recreation, or customization. Conveniently located near schools, shopping, and commuter routes—this exceptional home truly has it all.

440 Canyon Rd, Winchester

Listing courtesy of ERA Oakcrest Realty, Inc.. Contact: (540) 665-0360
$290,000
3 Beds ⋅ 2 Baths
Professional photos coming soon. Welcome home to 132 Geronimo Trail! Situated in a quiet and highly desirable neighborhood, this charming single-family home is perfect for first-time buyers, downsizers, or anyone seeking a peaceful retreat. This 1,232 square-foot rancher features 3 bedrooms, 2 full bathrooms, eat-in kitchen, living room, a brick fireplace with highly a efficient wood-burning insert, and laminate flooring throughout. Enjoy sun and shade from the comfortable deck and spacious yard with plenty of room for outdoor gatherings, gardening, or creating your own private oasis. The community features acres of greenspace, a large lake, several ponds, and playgrounds. Don't miss the opportunity to make this cozy retreat your own!

132 Geronimo Trl, Winchester

Listing courtesy of Long & Foster Real Estate, Inc.. Contact: (304) 263-7800
$409,900
4 Beds ⋅ 3 Baths
Well-maintained split foyer in a spectacular commuter location, just minutes from I-81 and a short drive to Old Town Winchester. This inviting home features hardwood floors throughout the main living areas, an open-concept floor plan, a cozy fireplace in the living room, and a spacious kitchen with a center island. The main level offers new carpet in the bedrooms, including a generous primary suite with a walk-in closet and an attached private bath. The finished lower level provides exceptional additional living space with a large den, a full bathroom, a bedroom with a walk-in closet, a laundry room complete with a utility sink, and a separate storage room. Step outside to enjoy the Trexx deck overlooking the fully fenced backyard—perfect for entertaining, relaxing, or letting pets play. Combining comfort, functionality, and an unbeatable location, this home is ready for you to move in and enjoy.

117 Old Dominion Dr, Winchester

Listing courtesy of Samson Properties. Contact: (540) 348-4911
$739,900
5 Beds ⋅ 5 Baths
Nestled towards the end of a quiet dead-end street in the sought-after Raven Pointe community, this stunning 5-bedroom, 4.5-bath home offers the perfect blend of elegance, functionality, and convenience. Ideally located for commuters with easy access to major routes, you’ll enjoy peaceful neighborhood living without sacrificing accessibility. Designed with flexibility in mind, the highly desirable main-level owner’s suite features a spacious walk-in closet and spa-like bath with a soaking tub and separate shower, making one-level living a breeze. With generous living space throughout, this home is also perfectly suited for multigenerational living, offering room for parents, in-laws, grandparents, or extended family. Inside, you’ll find rich hardwood floors and spacious living areas filled with natural light. The gourmet kitchen features stainless steel appliances, a six-burner commercial-style range, built-in microwave, upgraded countertops, abundant cabinetry, and a cozy breakfast area. The adjoining family room creates the perfect gathering space, while the formal dining room is ideal for holidays and entertaining. The fully finished basement provides additional living space for a recreation room, home theater and gym. The oversized attached garage includes built-in storage, space for a workshop and an additional refrigerator/freezer, while the expansive driveway offers plenty of parking. Additional upgrades include a tankless water heater, whole-house generator, battery backup sump pump, and an upgraded water treatment system for added comfort and peace of mind. This exceptional home combines timeless style, flexible living, and an unbeatable commuter-friendly location on one of Raven Pointe’s most desirable streets.

136 Cahille Dr, Winchester

Listing courtesy of Century 21 Redwood Realty. Contact:

$629,000
4 Beds ⋅ 3 Baths
Seller is offering a $2,500 credit toward the purchaser's closing costs, mortgage rate buy-down, prepaid expenses, moving costs, or other allowable buyer expenses. Situated on approximately 2.57 acres in Frederick County, this beautifully maintained 4-bedroom, 2.5-bath Traditional home offers nearly 3,000 square feet of thoughtfully designed living space. Built in 2020, the home features a sought-after main-level primary suite, solid oak flooring throughout most of the main level, and a bright, open floor plan designed for everyday living and entertaining. The kitchen is the heart of the home, featuring a brand new refrigerator, double oven (2024), dishwasher, microwave, generous workspace, and seamless flow into the adjoining living and dining areas. Upstairs, you'll find three additional bedrooms, a full bath, a versatile bonus room, and an additional sitting area, offering flexible space for guests, a home office, hobbies, or playroom. Outside, enjoy the large covered front porch, covered rear deck, patio, fenced area, recently paved driveway (2025), and over 2.5 acres of space to relax, garden, or simply enjoy the peaceful surroundings. This home has been exceptionally well maintained and includes new storm doors (2026), a recently serviced HVAC system with a new condensate pump, freshly painted upstairs bathroom, water softener, water filtration system, annual UV water treatment, and a recently inspected alternative septic system. Conveniently located just outside Winchester, you'll enjoy the perfect balance of country living with easy access to shopping, dining, commuter routes, and outdoor recreation.

115 Marion Dr, Winchester

Listing courtesy of Preslee Real Estate. Contact: 5402274416
$384,000
3 Beds ⋅ 2 Baths
This is the one you’ve been waiting for — a beautifully maintained ranch‑style home with thoughtful updates and a bright, comfortable layout throughout. A newer roof, updated HVAC, and fresh carpet provide peace of mind and move‑in readiness from day one. The primary ensuite serves as a true retreat, featuring a spa‑like bath and a walk‑in closet. Two additional bedrooms offer flexible living options with well‑planned closet storage. The large family room flows into the dining area, creating an open, welcoming space filled with natural light. Step outside to a level yard perfect for everyday enjoyment, complete with a storage shed for added convenience. The location is ideal for commuters, with quick access to Route 7, Route 50, and other major routes. Historic downtown Winchester, nearby schools, and shopping are all just minutes away. Don’t miss the chance to make this home yours

103 Elaine Drive, Winchester

Listing courtesy of Long & Foster Real Estate, Inc.. Contact: (540) 662-3484
$495,990
4 Beds ⋅ 4 Baths
The Glendale is a 2,216 square foot corner homesite, open concept two-story home with a finished basement that offers four bedrooms, three and a half bathrooms with a two-car garage. You will immediately feel at home as you enter the foyer and make your way into the spacious family room. This living space flows nicely into the eat-in kitchen with plenty of cabinets and island overlooking the family room, so you’ll never miss a beat! The large sliding glass door in the kitchen allows an abundance of natural light to brighten this home and gives easy access to the backyard. The convenient powder room along with access to the garage is tucked away off the kitchen. Upstairs, the spacious owner's suite boasts a private bathroom with dual vanity and a walk-in closet. The three sizeable secondary bedrooms provide space for everyone and the hall bathroom is conveniently located nearby along with a hall linen closet. The second-floor laundry room simplifies an everyday chore! The basement is finished with a full bathroom for additional space for movie nights, play zones, or a cozy guest suite. Ready for 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.

101 Seminole Dr, Winchester

Listing courtesy of D R Horton Realty of Virginia LLC. Contact: 8045109139
$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:

$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
$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