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201 Nathaniel Dr, Winchester
$699,900
3 Beds ⋅ 4 Baths
100K PRICE DROP!!! Stunning new construction modern contemporary home situated on nearly 6 private wooded acres, offering the perfect balance of privacy and convenience. This thoughtfully designed home features an open-concept layout filled with abundant natural sunlight and beautiful wooded views throughout. The main living area showcases engineered hardwood flooring, a spacious living room and dining area, and a stylish kitchen complete with granite countertops, stainless steel appliances, and a convenient butler’s pantry—perfect for entertaining and everyday living. The fully finished basement expands the living space and includes a full bathroom, providing endless possibilities for a game room, family room, recreation space, or guest area. Ideally located just off Route 522, this property offers quick access to restaurants, shopping, and commuter routes, while still providing the peaceful setting of a large wooded lot. A rare opportunity to own a modern home with acreage in a prime location.

201 Nathaniel Dr, Winchester

Listing courtesy of Samson Properties. Contact:

110 Duwamish Trl, Winchester
$285,000
3 Beds ⋅ 2 Baths
Possible Owner Financing! Welcome home to this beautifully refreshed single-level ranch nestled on a spacious, tree-lined lot. This inviting home features a bright and functional layout with updated finishes throughout. The kitchen offers grey cabinetry, granite countertops, and stainless steel appliances, creating a clean and modern space perfect for everyday living and entertaining. The home boasts fresh paint, updated flooring, and abundant natural light that flows throughout the living areas. Comfortable bedrooms and a well-appointed bathroom provide a practical and cozy living environment. Step outside to enjoy the porch overlooking a peaceful yard surrounded by mature trees, offering privacy and a relaxing outdoor setting. A storage shed provides additional space for tools or equipment and is equipped with electric. Perfect for first-time buyers, downsizers, or anyone seeking quiet living with modern updates, this move-in-ready home combines charm, comfort, and convenience.

110 Duwamish Trl, Winchester

Listing courtesy of Main Street Realty. Contact:

219 Lehigh, Winchester
$615,000
5 Beds ⋅ 4 Baths
This nearly new Lennar home offers the advantages of modern construction combined with thoughtful upgrades and future expansion potential in a location that keeps you connected to everything Winchester has to offer. Built just two years ago, the home provides the confidence of newer systems and energy efficiency, enhanced by a complete security system and water softener for added comfort and peace of mind. The main level is designed for seamless everyday living, featuring a spacious open concept kitchen and living area that encourages connection and effortless entertaining. A six foot rear bump out extends the living space, creating additional room for gatherings, work from home flexibility, or quiet evenings in. The custom stone fireplace serves as a striking focal point, adding warmth and architectural character to the heart of the home. Natural light flows through the main living areas, complementing the open layout and enhancing the sense of space. The kitchen is positioned to function as both a workspace and a central hub, allowing interaction with guests while preparing meals. Whether hosting celebrations or enjoying a relaxed night at home, the layout adapts easily to a variety of needs. The basement is fully finished with LVT floors and custom modernization. Located within Frederick County, the home offers convenient access to Route 7, Route 50, and Interstate 81, making commuting and travel straightforward. Old Town Winchester’s shops, dining, and community events are just a short drive away, along with everyday conveniences such as grocery, retail, and services. Photos may be virtually staged

219 Lehigh, Winchester

Listing courtesy of Keller Williams Realty. Contact:

Lot 16 Hodges, Winchester
$131,500
Own a piece of the beautiful Back Creek Heights community in Cross Junction. Located just minutes north of Winchester in the Dehaven part of the county. Access is secured via road frontage on Hodges Lane. Experience exciting hunting as many types of wildlife call this property home including deer, turkey, and many small game species. This tract is currently being used for recreation and is the next to last lot on Hodges Lane. Stellar views of the surrounding countryside are attainable with some tree clearing. This property features mildly sloping topography and a wet weather stream. Remote, fully wooded, and zoned Rural Areas (RA). Enjoy hiking, camping, and recreation of all types on this land. A short drive from all the amenities and attractions Winchester has to offer. ***Additional adjoining acreage available for purchase. See aerials for details.***

Lot 16 Hodges, Winchester

Listing courtesy of Whitetail Properties Real Estate, LLC. Contact:

38 Rouss Ave, Winchester
$995,000
Yost Building Positioned in the heart of downtown, this distinguished office building—formerly the executive wing of F&M National—offers an outstanding opportunity for businesses seeking a prestigious and highly walkable location. Multiple suite sizes are available, making it ideal for professional firms, government-adjacent services, or organizations looking to establish a prominent presence in the city’s core. Situated adjacent to City Hall and steps from the Historic Walking Mall, this property provides unparalleled convenience for employees and clients alike. Within a quick walk, you’ll find the Frederick County Administrative Buildings, the Courthouse, and numerous public parking structures, ensuring seamless access for daily operations. With its prime location, flexible floorplan offerings, and proximity to key civic and commercial amenities, this downtown office building represents a rare opportunity to secure space in one of the most strategic and sought-after areas of the city. ALSO LISTED FOR LEASE

38 Rouss Ave, Winchester

Listing courtesy of Colony Realty. Contact:

227 Hydrangea Way, Winchester
$607,990
3 Beds ⋅ 3 Baths
Experience effortless living in our Willow Run Active Adult community! Our Bristol floorplan is a thoughtfully designed ranch home, blending style and functionality in a single-level open layout. The moment you step inside the home; you will be greeted by an inviting foyer leading you into the heart of the home. The dining room seamlessly connects with the living room and kitchen, ideal for entertaining. The chef’s kitchen boasts stainless steel appliances, a walk-in pantry, and a breakfast bar. From the breakfast nook, step through the sliding glass door to a covered porch, perfect for outdoor gatherings or morning coffee. The main level also features three generously sized bedrooms and two modern bathrooms - including a serene owner’s suite with dual vanities, a tiled walk-in shower, and generously sized walk-in closet. The finished basement adds 1,070 finished square feet with a recreation room, bedroom, and bathroom included. Completed with a large laundry room, two-car garage, and a low-maintenance lifestyle, the Bristol offers comfort and convenience. Embrace one-story living and make The Bristol your perfect new home. November delivery. *Photos, 3D tours, and videos are representative of plan only and may vary as built. *Photos, 3D tours, and videos are representative of plan only and may vary as built.

227 Hydrangea Way, Winchester

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

314 N Braddock St, Winchester
$1,250,000
Located in the heart of the historic downtown district, this versatile B1-zoned property offers a rare blend of immediate income and long-term upside. The building features approximately 7,000 SF of office space complemented by 2,000 SF of ground-level shop, supported by 12 on-site parking spaces, important in the urban core. Beyond its current use, the property presents exceptional redevelopment potential, it could be conversion to nine residential units on a single floor and the ability to add up to two additional stories, creating a total of 27 residential units. Ideal for investors or developers seeking a high-visibility downtown location with historic character, flexible zoning, and significant value-add potential.

314 N Braddock St, Winchester

Listing courtesy of Colony Realty. Contact:

Northwestern Pike, Winchester
$3,200,000
Prime opportunity on 13.05 acres in an unbeatable high-visibility location along Route 50 in Winchester, VA. Positioned directly across from major retailers and conveniences—including Walmart, Sheetz, Tractor Supply, Applebee’s, Dunkin’, Bojangles, and the Winchester Medical Center campus—this property offers exceptional exposure and accessibility. Zoned for multiple development possibilities, with previous concept plans by Greenway Engineering that included options such as a retail strip center with a drive-through end cap and medical office buildings. The area’s strong demand for affordable housing also presents an excellent residential development opportunity. With thousands of daily commuters traveling from West Virginia into Virginia along this corridor, the site benefits from consistent, high-volume traffic flow. This is a rare chance to bring a high-impact commercial or mixed-use project to one of Winchester’s most dynamic and growing areas. Photos may be virtually staged

Northwestern Pike, Winchester

Listing courtesy of Keller Williams Realty. Contact:

832 Winder Ct, Winchester
$465,000
3 Beds ⋅ 2 Baths
Listed below recent appraised value. All-brick rancher located in the sought-after Early’s Green at Meadow Branch community, offering 1,974 finished square feet with 9-foot ceilings and true one-level living. The open floor plan provides excellent flow and is ideal for both everyday living and entertaining. Recent interior updates include new hardwood flooring in the main living room, and new carpet in all bedrooms. Tile flooring has been thoughtfully retained in the kitchen, entry, and guest bath. Recessed lighting has been added to the main living area, along with multiple updated light fixtures, creating a bright and welcoming feel. The kitchen features a breakfast nook with a bay window and now includes custom built pantry storage, while the living room has been enhanced with a custom built-in with integrated lighting. A former bar area was removed and replaced with a large storage closet, significantly improving functionality. The primary bathroom has been fully gutted and completely redesigned, featuring a modern walk-in shower, contemporary fixtures, and an aging-in-place–friendly layout with grab bars and improved accessibility. The sunroom has been reconfigured for better flow, with the original sliding doors removed, a new cased opening added, and HVAC extended to the space, allowing it to be enjoyed year-round. A rear deck extends the living space outdoors. Exterior improvements include over $10,000 in rear landscaping designed to buffer Meadow Branch Avenue, featuring Crepe Myrtles, Emerald Green Arborvitae, and Hollies. A crawlspace fan/radon-style ventilation system has also been installed. Situated on a cul-de-sac and conveniently located near hospitals, shopping, dining, fitness facilities, walking trails, coffee shops, and Old Town Winchester. HOA covers lawn maintenance, snow removal, pool, and tennis courts. Not a 55+ community. Homes offering this level of care, thoughtful upgrades, and low-maintenance living in this location are rarely available.

832 Winder Ct, Winchester

Listing courtesy of Realty ONE Group Old Towne. Contact:

TO BE BUILT - To Be Built Williamson Rd, Winchester
$529,990
3 Beds ⋅ 2 Baths
TO-BE-BUILT HOME Build your dream home in the established Abrams Pointe community, just minutes from historic Downtown Winchester. Enjoy the best of both worlds: a peaceful, established neighborhood with easy access to local restaurants, boutiques, entertainment, parks, wineries, and commuter routes. Here, you choose your homesite and build the Avalon your way. The Avalon is a stunning 3-bedroom, 2-bath ranch-style single-family home offering up to 2,538 square feet of thoughtfully designed living space, with the option to add a 4th bedroom in the finished lower level. Designed for comfortable main-level living, the Avalon features an open-concept floor plan that brings together a spacious great room, a bright and airy kitchen, and a welcoming breakfast area. The main level includes three bedrooms and two full baths, with the flexibility to transform one of the bedrooms into a versatile flex space, perfect for a home office or den. Personalize the Avalon to fit your lifestyle with available options such as a sunroom, a finished basement with an additional bedroom, and a three-car garage. Make the Avalon truly your own by choosing your homesite, finishes, and options to create a home that fits your lifestyle. Schedule your private tour today! Pictures are representative.

TO BE BUILT - To Be Built Williamson Rd, Winchester

Listing courtesy of New Home Star Virginia, LLC. Contact:

403 Keval Gyan Way, Winchester
$950,000
3 Beds ⋅ 3 Baths
Four months build time from contract. Seize a rare opportunity to own one of just fifteen premier lots within the prestigious, upper-scale Keplinger Estates near the Apple Pie Ridge area. This is not just a house; it is a bespoke sanctuary offering a sophisticated lifestyle with the ultimate convenience of being close to town, yet free from the constraints of an HOA. Experience the pinnacle of single-level living in this immaculate, brand-new residence, meticulously designed with a flowing 3,100 sq. ft. open floor plan. The builder has redefined "standard features," integrating premium elements throughout the home that others typically label as costly upgrades. Key Permitted and built time 4 months. Features & Elegant Finishes: Striking Curb Appeal: A distinguished full brick front complemented by durable cement siding creates a timeless exterior, highlighted by a large, welcoming concrete front porch and lead walk. Exquisite Main Level: Rich, stained Early American hardwood flooring flows seamlessly across the entire main level, excluding the elegant tiled bathrooms and laundry room, creating a warm, inviting atmosphere. Seamless Indoor/Outdoor Entertaining: Step through to your private outdoor oasis. A covered and screened deck provides an ideal spot for year-round relaxation, extending onto an attached open deck perfect for grilling and sunbathing. The Ultimate Future Lower Level Retreat: basement opening onto a full-length concrete patio that spans the entire back of the house, offering versatile entertainment possibilities. This exquisite home represents a unique blend of craftsmanship, luxury, and exclusivity. Don't miss the chance to claim your spot in this premier community. Full side deck and associated patio are optional

403 Keval Gyan Way, Winchester

Listing courtesy of Realty ONE Group Old Towne. Contact:

Lot 11 Keval Gyan, Winchester
$899,900
3 Beds ⋅ 2 Baths
Four months build time from contract. Seize a rare opportunity to own one of just fifteen premier lots within the prestigious, upper-scale Keplinger Estates near the Apple Pie Ridge area. This is not just a house (new PIN OAK model); it is a bespoke sanctuary offering a sophisticated lifestyle with the ultimate convenience of being close to town, yet free from the constraints of an HOA. Experience the pinnacle of single-level living in this immaculate, brand-new residence, meticulously designed with a flowing 2,488 sq. ft. open floor plan. The builder has redefined "standard features," integrating premium elements throughout the home that others typically label as costly upgrades. Key Features & Elegant Finishes: Striking Curb Appeal: A distinguished full brick front complemented by durable cement siding creates a timeless exterior, highlighted by a large, welcoming concrete front porch and lead walk. Exquisite Main Level: Rich, stained Early American hardwood flooring flows seamlessly across the entire main level, excluding the elegant tiled bathrooms and laundry room, creating a warm, inviting atmosphere. Seamless Indoor/Outdoor Entertaining: Step through to your private outdoor oasis. A covered and screened deck provides an ideal spot for year-round relaxation, extending onto an attached open deck perfect for grilling and sunbathing. This exquisite home represents a unique blend of craftsmanship, luxury, and exclusivity. Don't miss the chance to claim your spot in this premier community.

Lot 11 Keval Gyan, Winchester

Listing courtesy of Realty ONE Group Old Towne. Contact:

Lot 10 Desant, Winchester
$849,900
5 Beds ⋅ 3 Baths
Four month build time from contract. Seize a rare opportunity to own one of just fifteen premier lots within the prestigious, upper-scale Keplinger Estates near the Apple Pie Ridge area. This is not just a house; it is a bespoke sanctuary offering a sophisticated lifestyle with the ultimate convenience of being close to town, yet free from the constraints of an HOA. Experience the pinnacle of a large family living in this immaculate, brand-new residence, meticulously designed with a flowing over 3,100 sq. ft. open floor plan. The builder has redefined "standard features," integrating premium elements throughout the home that others typically label as costly upgrades. Key Features & Elegant Finishes: Striking Curb Appeal: A distinguished full brick front complemented by durable cement siding creates a timeless exterior, highlighted by a large, welcoming concrete front porch and lead walk. Rich, stained Early American hardwood flooring flows seamlessly across the entire home, excluding the elegant tiled bathrooms and laundry room, creating a warm, inviting atmosphere. Seamless Indoor/Outdoor Entertaining: Step through to your private outdoor oasis. A covered and screened deck provides an ideal spot for year-round relaxation, extending onto an attached open deck perfect for grilling and sunbathing. This exquisite home represents a unique blend of craftsmanship, luxury, and exclusivity. Don't miss the chance to claim your spot in this premier community.

Lot 10 Desant, Winchester

Listing courtesy of Realty ONE Group Old Towne. Contact:

121 Keval Gyan Way, Winchester
$1,150,000
4 Beds ⋅ 4 Baths
Four months build time from contract. Foundation dug and construction to begin soon. To have finished basement. Seize a rare opportunity to own one of just fifteen premier lots within the prestigious, upper-scale Keplinger Estates near the Apple Pie Ridge area. This is not just a house; it is a bespoke sanctuary offering a sophisticated lifestyle with the ultimate convenience of being close to town, yet free from the constraints of an HOA. Experience the pinnacle of single-level living in this immaculate, brand-new residence, meticulously designed with a flowing 3,100 sq. ft. open floor plan. The builder has redefined "standard features," integrating premium elements throughout the home that others typically label as costly upgrades. Key Features & Elegant Finishes: Striking Curb Appeal: A distinguished full brick front complemented by durable cement siding creates a timeless exterior, highlighted by a large, welcoming concrete front porch and lead walk. Exquisite Main Level: Rich, stained Early American hardwood flooring flows seamlessly across the entire main level, excluding the elegant tiled bathrooms and laundry room, creating a warm, inviting atmosphere. Seamless Indoor/Outdoor Entertaining: Step through to your private outdoor oasis. A covered and screened deck provides an ideal spot for year-round relaxation, extending onto an attached open deck that wraps all the way around the side of the house.perfect for grilling (quick connect propane) and sunbathing. Walk-Out Access: The finished basement boasts convenient double-door walk-out access, opening onto a full-length concrete patio that spans under all decking, offering versatile entertainment possibilities. This exquisite home represents a unique blend of craftsmanship, luxury, and exclusivity. Don't miss the chance to claim your spot in this premier community.

121 Keval Gyan Way, Winchester

Listing courtesy of Realty ONE Group Old Towne. Contact:

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