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$439,900
2 Beds ⋅ 2 Baths
Set on nearly two acres just minutes from historic downtown Winchester, this beautifully maintained one-level home delivers the rare combination of open country space and everyday convenience. A classic covered front porch welcomes you in, opening to a bright, open-concept kitchen and living with 10' ceilings. This central living area is designed for easy flow — cooking, gathering, and relaxing all in one connected space. Two comfortable bedrooms and two full baths include a spa-inspired retreat. One with a luxurious walk-in shower and the other with a step-up soaking tub. Out back, a covered patio overlooks the wide, level lawn — a quiet spot for morning coffee or evening entertaining, framed by mature trees and open sky. Storage and workspace are never an issue here: a two-car attached garage plus a separate detached garage offer room for vehicles, tools, hobbies, or a workshop. Manicured landscaping, crisp white siding, and a white-fenced property line complete the picture. Move-in ready, meticulously cared for, and surrounded by room to breathe — all within a short drive of Winchester's shops, dining, and Old Town district.

211 Marple Rd, Winchester

Listing courtesy of Century 21 Redwood Realty. Contact: (301) 365-0664
$849,900
3 Beds ⋅ 2 Baths
Permitted and delivery 4 months. 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 12 Keval Gyan Way, Winchester

Listing courtesy of Realty ONE Group Old Towne. Contact: 5407738475
$375,000
3 Beds ⋅ 1 Baths
Lovingly maintained, this charming brick rancher is the perfect starter home or investment opportunity! The main level offers three comfortable bedrooms, one full bath, a bright eat-in kitchen, and a spacious living room filled with natural light. The full unfinished basement provides endless potential for additional finished living space, while an existing hobby room is already in place—perfect for sewing, crafts, a workshop, or a home office. A unique bonus is the custom-built "catio" just off the back of the home, creating a safe outdoor retreat for your feline friends. Outside, enjoy a private backyard with mature landscaping and a detached one-car garage. Ideally located just minutes from Old Town Winchester, the Walking Mall, the Museum of the Shenandoah Valley, Winchester Medical Center, shopping, dining, and commuter routes, this home offers both convenience and charm. Major updates completed in 2016 include new windows, HVAC, roof, driveway, and beautifully refinished hardwood floors. The home is served by public water and a private septic system.

805 Pennsylvania Ave, Winchester

Listing courtesy of Hunt Country Sotheby's International Realty. Contact: (540) 687-8500
$675,000
5 Beds ⋅ 3 Baths
Spacious ranch home on a beautiful 1-acre lot in the highly desirable Stonebrook Farms community! Surrounded by mature trees and offering a peaceful setting, this home combines the space of country living with the convenience of being just minutes from shopping, dining, medical facilities, and all that Winchester has to offer. Designed with flexibility in mind, this home features 5 bedrooms and 3 full baths, including a private wing tucked behind the garage with a bedroom, full bath, and adjoining den. Located just off the kitchen, this space is ideal for an in-law suite, guest quarters, home office, or multi-generational living. The finished lower level provides even more living space with an additional bedroom, full bath, kitchen, and dining area, creating endless possibilities for recreation, extended family, or entertaining. Step outside to enjoy the spacious backyard, mature landscaping, and patio, offering plenty of room to relax, garden, or host gatherings. Stonebrook Farms is one of Winchester's most sought-after neighborhoods, offering the opportunity to join the optional Stonebrook Club, featuring swimming, tennis, pickleball, and social activities. With its combination of generous living space, a beautiful setting, and an exceptional location, this home is ready for its next chapter.

146 Stonebrook Rd, Winchester

Listing courtesy of ERA Oakcrest Realty, Inc.. Contact: (540) 665-0360
$400,000
2 Beds ⋅ 2 Baths
Welcome to easy one-level living in Willow Lawn Cottages, a popular 55+ community in Winchester! This well-maintained home has been freshly painted and offers 2 bedrooms and 2 full bathrooms. The open floor plan feels bright and spacious, with vaulted ceilings, plenty of natural light, and luxury vinyl plank flooring throughout. The kitchen includes granite countertops, updated cabinets, stainless steel appliances, and a built-in microwave. The primary bedroom has a walk-in closet and a private bathroom with a walk-in shower. You’ll also find main-level laundry, an attached one-car garage, a covered front porch, and a rear patio where you can relax outdoors. The HOA takes care of lawn maintenance and snow removal and provides access to the community clubhouse, gathering spaces, and sidewalks. Located close to Winchester Medical Center, shopping, restaurants, and historic downtown Winchester, this home offers comfort and convenience in a welcoming community.

1853 Rosser Ln, Winchester

Listing courtesy of Realty FC. Contact: (540) 931-0144
$225,000
3 Beds ⋅ 2 Baths
**Unlimited Potential on 1.78 Unrestricted Acres!** If you've been searching for a home on acreage that's just minutes from town, offering mature trees, level topography, and no HOA, your search ends here. Situated on 1.78 beautiful, unrestricted acres, this well-maintained 3-bedroom, 2-bath manufactured home provides the perfect opportunity to add your own personal style while enjoying comfortable, move-in-ready living. The home features central heating and air conditioning, a spacious kitchen with ample cabinet and counter space, and includes a washer and dryer. The generously sized primary suite offers a walk-in closet and a private ensuite bath with a walk-in shower. Two additional bedrooms share a full hall bath with a tub/shower combination. A separate mudroom/laundry room with its own rear entrance is a practical feature, especially for those who enjoy gardening, outdoor projects, or simply making the most of nearly two acres of land. Major updates include a roof replaced within the past five years and a recently installed water softener system, providing added peace of mind. As you enter the property, you'll find a charming garage/barn with electricity, offering endless possibilities as a workshop, hobby space, equipment storage, or additional garage. An additional storage shed provides even more room for tools and outdoor equipment. The true highlight of this property is the picturesque setting. Mature trees, open lawn, and a peaceful atmosphere create the perfect balance of privacy and usable outdoor space without feeling isolated. Conveniently located on the east side of I-81 and less than one mile from Route 50, this property offers an ideal location for commuters while remaining close to shopping, dining, and everyday conveniences. Whether you're looking for your first home, a place to expand, or an investment with incredible potential, this property is ready for your vision.

116 Waterloo Ct, Winchester

Listing courtesy of Samson Properties. Contact: (540) 348-4911
$360,000
3 Beds ⋅ 2 Baths
NEW CONSTRUCTION built by a trusted local builder with over 20 years of experience! This beautifully crafted 3-bedroom, 2-bath ranch home offers the perfect blend of quality construction and modern finishes. Built using the ZIP System® exterior sheathing for enhanced weather protection and durability, this home was designed with attention to detail from the ground up. Inside, you’ll find an open-concept floor plan featuring luxury vinyl plank flooring throughout, soft-close cabinetry, stainless steel appliances, and a spacious center island that anchors the kitchen and living area. The private primary suite includes a full bath, while two additional bedrooms and a second full bath provide comfortable living for family or guests. The unfinished basement is equipped with a rough-in for a future full-bath and offers limitless potential! Step outside onto the rear deck overlooking a wooded backdrop and enjoy the peaceful setting. The full walkout basement offers an additional 1,232 square feet ready for storage, a workshop, or future finished living space. The covered front porch, sizable back deck and thoughtful craftsmanship complete this exceptional new home. Enjoy the benefits of mountain living with community amenities including lake access, walking trails, picnic areas, playgrounds, and recreational courts—all while remaining within a convenient drive of Winchester. Why settle for someone else’s worn finishes when you can enjoy the confidence and peace of mind that comes with brand-new construction? Schedule your private showing today!

302 Pheasant Dr, Winchester

Listing courtesy of Virginia Real Estate. Contact: 5406452999
$598,895
3 Beds ⋅ 4 Baths
Enjoy the ease of true main-level living in this meticulously maintained ranch home offering more than 4,300 finished square feet on an oversized 0.37-acre lot in Winchester's desirable Star Fort community | NO HOA | With nearly 2,300 square feet on the main level and an additional 2,100+ finished square feet in the walk-out basement, this home offers an abundance of flexible living space, all complemented by breathtaking panoramic valley views from the expansive 63-foot deck | Covered Front Porch Leads to Welcoming Foyer | Spacious Dining Room w/Triple Window has Room for a Crowd as does the 17' x 15' Family Room w/Gas Fireplace | Immaculate Kitchen w/Updated Appliances, Recessed Lighting, Pantry & Breakfast Nook w/Sliding Doors to Deck | Main Level Primary Suite w/2 Huge Walk-In Closets + French Doors to the Deck + En Suite Bath with Walk-In Jetted Soaking Tub & Separate Shower | 2 Additional Bedrooms w/Great Closet Space on Main Level Share the 2nd Full Bath + 13' x 12' Flex Room for Guests or Home Office | Convenient Main Level Laundry/Mudroom + 2-Car Side-Load Garage | Fully Finished Walkout Basement has Tremendous Space for Anything! 35' x 33' Rec Room w/Built-in Cabinet Storage + 2 Additional Rooms (27' x 16' & 27' x 26') with Endless Possibilities + 3rd Full Bath | Delightful Fenced Back Yard + Covered Storage Under Deck | Numerous recent improvements including Painted Porch/Lead Walk, Interior Paint, New Flooring + Carpet/Padding & Updated Kitchen Appliances as well as a Resealed Deck (2026) + Replaced Deck Surface (2024), New Attic Insulation (2025), New Insulated Garage Door (2023), New Roof (2018), Washer & Dryer (2018/2017) Additional features include a whole-house generator, whole-house water softener, invisible fence + fully fenced back yard, and walk-in bathtub | Fantastic Winchester Location Convenient to Old Town Winchester & 81 + Shopping, Dining & Recreation

142 Fortress Dr, Winchester

Listing courtesy of RE/MAX Distinctive Real Estate, Inc.. Contact: (703) 858-9108
$375,000
3 Beds ⋅ 2 Baths
Charming, Updated Rancher in the Heart of Winchester! Welcome home to this impeccably maintained 3-bedroom, 2-bath ranch offering the perfect blend of comfort, character, and convenience—all on one level! From the moment you arrive, you'll appreciate the pride of ownership and thoughtful updates throughout. The spacious kitchen is the heart of the home, offering abundant cabinetry and room to gather with family and friends. Multiple living areas provide the flexibility to create a cozy family room, home office, playroom, or hobby space—giving everyone room to spread out. Major updates provide peace of mind, including a new roof, siding, and side porch—all completed within the last year. Other updates include added storage, updated bathrooms, updated flooring, and lots of other touches throughout. Additional features include a gas furnace, central air conditioning, and an abundance of storage rarely found in homes of this size. Located within the City of Winchester, you'll enjoy the convenience of nearby shopping, dining, parks, and commuter routes while coming home to a property filled with warmth, charm, and timeless character. This lovingly cared-for home is a true hidden gem that's move-in ready and waiting for its next owner. Schedule your private tour today before this one is gone!

1004 Pennsylvania Ave, Winchester

Listing courtesy of Samson Properties. Contact: (540) 348-4911
$969,000
5 Beds ⋅ 4 Baths
A rare opportunity to live on Lake Serene - Welcome to your private waterfront retreat on Lake Serene, where resort-style outdoor living meets timeless modern craftsmanship. Rarely does an opportunity like this come along. Tucked among the trees on one of Frederick County's most sought-after private lakes, this beautifully renovated waterfront home offers the perfect balance of luxury, recreation, and everyday comfort. Completely transformed in 2016 with a 2-story addition along with thoughtful updates & remodeling, the home features a stunning custom Chef's kitchen with rich cherry cabinetry, elegant soapstone countertops, and quality finishes include KitchenAid gas range and Viking range hood. Designed for gathering with family and friends we have 5 bedrooms and 3.5 beautifully remodeled bathrooms, numerous living areas on two spacious levels making this THE gathering place! Offering one level living for all daily activity the main level is host to gorgeous family room with soaring ceilings, kitchen, dining room, living room with fireplace, laundry, 3 bedrooms & 2.5 baths. The lower level offers additional space to spread out with game room, recreation room, wet bar and two additional bedrooms and storage. Step outside and discover your own private retreat. Extensive hardscaping, an oval in-ground heated pool, multiple outdoor entertaining spaces, and mature landscaping create a resort-like setting that's perfect for summer afternoons or evening sunsets with views of the lake. A detached 2-bay garage also has a finished area w/ fireplace which was originally utilized as an office now acts as a pool house. Life at Lake Serene is about more than the home itself. Enjoy boating, kayaking, fishing, paddleboarding, or simply relaxing by the water. Inventory on Lake Serene is exceptionally limited, with many properties remaining in the same families for generations. Even more uncommon is finding a home that has already been tastefully updated—allowing you to begin enjoying the lake lifestyle immediately instead of planning years of renovations. Whether you're searching for a full-time residence or the ultimate weekend escape, this exceptional waterfront property offers a rare opportunity to own one of the area's most desirable lake homes. Come experience why life is simply better at Lake Serene.

485 Lake Serene Dr, Winchester

Listing courtesy of MarketPlace REALTY. Contact:

$385,000
3 Beds ⋅ 2 Baths
New construction one-level home on a spacious 1-acre lot! Currently under construction and anticipated to be completed in early October 2026, this thoughtfully designed 3-bedroom, 2-bath ranch offers the ease of single-level living with an open-concept floor plan, luxury vinyl plank flooring, granite countertops, upgraded stainless steel appliances, and an attached two-car garage. The open kitchen flows seamlessly into the dining and living areas, creating a bright, welcoming space that's ideal for everyday living and entertaining. The private primary suite, spacious secondary bedrooms, modern finishes, and abundant cabinet space combine comfort, style, and functionality throughout the home. Whether you're buying your first home, downsizing, retiring, or simply looking for the convenience of one-level living, this home offers a comfortable, low-maintenance lifestyle on a beautiful 1-acre lot with room to enjoy the outdoors. Construction is anticipated to be completed in early October 2026. Buyers may still have the opportunity to make certain finish selections, depending on the stage of construction. Contact the listing agent for current construction updates, available selections, and additional details. Taxes currently reflect the land only.

300 Panther, Winchester

Listing courtesy of Preslee Real Estate. Contact: 5402274416
$399,000
3 Beds ⋅ 2 Baths
Situated directly across from historic Third Battle of Winchester Park, this charming brick ranch offers a rare opportunity to enjoy more than six miles of scenic walking trails, interpretive markers, and historic monuments just steps from your front door. Conveniently located with quick access to Routes 7, 11, and I-81, the property combines peaceful surroundings with exceptional accessibility. Set on approximately 2.37 mostly level, usable acres, the property provides plenty of space for gardening, outdoor recreation, or future expansion. The home features more than 1,300 square feet of living space on the main level, plus an additional 1,300-square-foot basement, offering endless possibilities. Inside, you'll find three bedrooms, one and half bath's, and original hardwood floors in the family room and bedrooms, all ready for your personal updates and finishing touches. The full walk-out basement, with its separate exterior entrance, expands the home's potential for additional living space, a recreation room, home office, or workshop. Partially finished and previously used as a recreation area, it also includes a large unfinished section with built-in shelving for exceptional storage or hobby space. Owned by the same family since it was built, this well-constructed home features a timeless brick exterior, an attached carport, a spacious rear deck, and several outbuildings ideal for storing lawn equipment, gardening tools, or outdoor gear. With solid construction, a functional layout, beautiful acreage, and an unbeatable location across from one of the area's most treasured historic parks, this property is brimming with potential and ready for its next chapter. Whether you're looking for a peaceful place to call home or an opportunity to create your dream property, this is one you won't want to miss.

735 Redbud, Winchester

Listing courtesy of Long & Foster Real Estate, Inc.. Contact: (540) 662-3484
$399,000
3 Beds ⋅ 2 Baths
This charming brick ranch-style home, built in 1971, offers a perfect blend of comfort and functionality. With 2,198 sq. ft. of thoughtfully designed space, this residence features three inviting bedrooms plus a bonus room and two full bathrooms, ideal for relaxation and privacy. The traditional floor plan is enhanced by beautiful hardwood and ceramic tile flooring, creating a warm and welcoming atmosphere throughout. The heart of the home is the eat-in kitchen, including a built-in microwave, dishwasher, and electric oven/range. Enjoy cozy meals at the kitchen table or gather around the wood-burning/woodstove & propane fireplace in the living area, perfect for creating lasting memories. Additional features include built-ins, ceiling fans, and a convenient main floor laundry area. Step outside to discover a generous 0.74-acre lot, beautifully landscaped and backing onto serene trees, providing a peaceful retreat. The exterior boasts several porches and ample parking with an oversized attached 5-bay garage and paved/gravel driveway, which is fantastic for car enthusiasts! Located in a rural setting, this home offers picturesque views of the garden and surrounding woods, making it an ideal escape from the hustle and bustle. With its combination of comfort, space, and natural beauty, this property is ready to welcome you home. This is a Special Warranty Deed sale. Call for details on garage measurements!

820 Cedar Grove Rd, Winchester

Listing courtesy of Coldwell Banker Premier. Contact: 990007.lead@leads.leadrouter.com
$375,000
3 Beds ⋅ 1 Baths
Enjoy one-level living with 6.44 partly wooded acres. All-brick 3-bedroom, 1-bath home offering a peaceful country setting with plenty of room to enjoy the outdoors. Relax on the covered rear porch overlooking the property. The home features a paved driveway and a full unfinished basement, providing excellent storage or future expansion potential. New water heater installed in 2022, roof approximately ten years old. A wonderful opportunity for those seeking privacy, acreage, and the durability of an all-brick home. Be sure to check out our 3-D tour attached to this listing!

1480 Chestnut Grove Rd, Winchester

Listing courtesy of RE/MAX Roots. Contact: (540) 686-7362
$435,000
3 Beds ⋅ 2 Baths
Come home to Whittier Acres and this well maintained Rancher with 1-car garage just minutes from Winchester Medical Center. You'll love the cozy living room with wood burning fireplace, crown molding & built in bookshelves. Gleaming hardwood floors grace the main level (just refinished). The kitchen has a French door refrigerator, electric range, built-in microwave, dishwasher, a built-in spice rack & a tile backsplash. The primary suite includes a remodeled primary bath (2023). There is a cozy sun porch on the rear of the home. Enjoy your morning coffee on the inviting front porch or out on the rear deck. The partially finished basement offers a large recreation room with wood stove for all your favorite hobbies. There is also a spacious storage room for your holiday decor, etc. The fenced backyard has a fire pit perfect for cooler fall evenings. There is also a shed for storing your gardening tools.

338 Lanny Dr, Winchester

Listing courtesy of Century 21 Redwood Realty. Contact:

$599,990
4 Beds ⋅ 3 Baths
The Dover by D.R. Horton offers 1,958 square feet of thoughtfully designed, main floor living with 3 bedrooms, 2 full baths, and a 2-car garage. A private flex room with LVP flooring sits just off the foyer – ideal for a home office or craft room.<br><br> 9-foot ceilings lead into the open-concept kitchen, dining, and family room. The kitchen features quartz countertops, soft-close cabinet doors, a gas range, and modern island perfect for gathering. Sliding glass doors off the dining area fill the home with natural light and open to a covered patio – ideal for morning coffee or relaxed evenings outdoors.<br><br> The owner’s suite includes a spacious bath with split dual vanities, a large walk-in closet, and direct access to the laundry room for added convenience. This home also has 750 square feet of loft including an open living space, another bedroom, full bath, and extra storage.<br><br> Located in the serene and amenity-rich Willow Run community, residents will enjoy a clubhouse, outdoor pool, tennis and pickleball courts, and more. Move in this August/September and experience low-maintenance, active adult living at its best!

245 Hydrangea Way, Winchester

Listing courtesy of Keller Williams Realty. Contact: 7034309008
$349,900
3 Beds ⋅ 2 Baths
Enjoy the ease of one-level living in this beautifully maintained all-brick ranch, conveniently located just minutes from Historic Downtown Winchester's shops, restaurants, and local events. Freshly painted and move-in ready, this home offers comfortable living with thoughtful updates throughout. The spacious living room features a beautiful stone accent wall that adds warmth and character, while the bonus room addition provides flexible space for a family room, home office, playroom, or whatever fits your lifestyle. Step outside and you'll find one of this home's best features, a large backyard with an expansive Trex deck and a sun porch that can be enjoyed year-round, making it the perfect place to relax or entertain. The crawl space has been professionally encapsulated and includes a commercial-grade dehumidifier, providing added protection and peace of mind. If you're looking for a home that's been well cared for, offers great outdoor living, and is close to everything Winchester has to offer, this one is ready for you!

111 Huntcrest Cir, Winchester

Listing courtesy of Realty ONE Group Old Towne. Contact: 5407738475
$489,900
3 Beds ⋅ 2 Baths
Welcome to this beautifully refreshed 3-bedroom, 2-bath rancher in Chapel Hill. After hearing buyer feedback that the home felt dated, the sellers invested thousands of dollars and brought in a builder and design team to thoughtfully update the property for its next owner. The kitchen received a complete refresh with quartz countertops, a redesigned single-level peninsula, stainless steel appliances, a porcelain sink, tile backsplash, updated hardware, modern fixtures, and fresh lighting. The result is a bright, current space that feels both functional and inviting. Additional improvements include a new hall bathroom vanity with a quartz top, new switch plates and outlets throughout, a serviced and inspected HVAC system, a fully functioning gas fireplace, and a new vapor barrier in the crawl space. The sellers also addressed the items identified in a prior home inspection. Outside, the home has been power-washed, the landscaping has been trimmed, and the storage shed was updated with new plywood, shingles, and a ridge vent. The home's roof is approximately 8 to 10 years old, and the covered front porch adds classic curb appeal. With substantial improvements already completed, this home offers a refreshed interior, important maintenance updates, and the opportunity to move in and enjoy from day one. Conveniently located off Route 522 South, approximately two miles beyond Costco, the home provides easy access to shopping, dining, and everyday conveniences.

231 Bentley Ave, Winchester

Listing courtesy of ERA Oakcrest Realty, Inc.. Contact: (540) 665-0360
$310,000
3 Beds ⋅ 2 Baths
Adorable rancher in Shawneeland with access to a lake, trails, beach, and fishing. Ideally you wish for spacious living quarters,3 bedrooms, 2 full baths, and a walkout basement with a finished room for gym/office/den..well we have all that and more so come take a gander and make it your own before the summer ends. Septic is 1 bedroom (2 person occupancy)

204 Cochise Trl, Winchester

Listing courtesy of RE/MAX Roots. Contact: (540) 686-7362
$420,000
2 Beds ⋅ 2 Baths
Welcome to 1826 Kershaw Lane in Willow Lawn Cottages, one of Winchester, Virginia's most sought-after 55+ active adult communities, offering low-maintenance, single-level living just minutes from Historic Old Town Winchester. This beautifully maintained 2-bedroom, 2-bath ranch home showcases exceptional pride of ownership with beautiful hardwood flooring, soaring vaulted ceilings, and an open floor plan filled with natural light. The kitchen features a decorative ceramic tile backsplash, an updated Moen faucet, a new refrigerator, and a new microwave, combining style and functionality for the home chef. The spacious primary suite offers a relaxing retreat with a private en-suite bath and generous closet space. A second bedroom and full bathroom provide comfortable accommodations for family and guests. The inviting sunroom is bathed in natural light, creating the perfect space for morning coffee, reading, hobbies, or a home office. Additional updates include new gas fireplace logs, adding warmth and charm to the living area. Outside, you'll enjoy a beautifully landscaped garden that creates a peaceful setting for relaxing or entertaining. French drains have also been installed to enhance drainage and provide added peace of mind. Residents of Willow Lawn Cottages enjoy a friendly community atmosphere with convenient access to Historic Old Town Winchester, Shenandoah University, Winchester Medical Center, Jim Barnett Park, the Museum of the Shenandoah Valley, and the Winchester Green Circle Trail. Shopping, dining, healthcare, and year-round events are just minutes away.

1826 Kershaw Ln, Winchester

Listing courtesy of RE/MAX Roots. Contact: (540) 686-7362
$750,000
4 Beds ⋅ 3 Baths
RARE FIND! Discover the freedom and possibilities that come with 12.17 wooded acres—no HOA, no restrictions, just endless opportunity. Whether you're dreaming of creating a self-sufficient homestead, establishing a hobby farm, enjoying outdoor recreation, or simply escaping to your own private retreat, this exceptional property is ready to make it happen. The outdoor amenities are truly unmatched. A paved driveway leads to the home with both asphalt and gravel parking areas. Three powered outbuildings provide incredible flexibility, including a 20' x 40' insulated building complete with a chimney and lean-to, plus two additional sheds, one with its own lean-to. The established goat pen and chicken pen are equipped with both water and electric, making it easy to begin or expand your homesteading lifestyle. Outdoor enthusiasts will appreciate the private shooting range with berm, existing ATV trails winding through the woods, a 50-amp RV hookup, covered carport, and a relaxing hot tub to unwind after a day spent enjoying your land. The well-maintained brick rancher offers over 3,096 square feet of thoughtfully designed living space with 4 bedrooms and 3 full bathrooms. The beautifully updated kitchen is both stylish and functional, featuring luxury vinyl plank flooring, recessed lighting, rich earth-toned cabinetry and countertops, and an LG stainless steel appliance package less than one year old. Crown molding enhances the main-level living areas, while the formal dining room provides the perfect setting for holiday gatherings, complete with a cozy fireplace for added ambiance. Large windows fill the spacious living room with natural light, and a second fireplace creates a warm and inviting atmosphere during cooler months. The main level also includes three generously sized bedrooms and two full bathrooms. The fully finished lower level expands your living space with a spacious recreation room featuring tile flooring and an impressive stone fireplace with a wood stove that has a stainless steel liner. This level also offers a private bedroom suite with a full bathroom, bonus room, and separate laundry room—ideal for guests, multi-generational living, or additional workspace. Laundry hookups are conveniently located on both levels, and there is a water treatment system and sump pump in the basement. This property is highly accessible, located just minutes from major highways and everyday conveniences, with an airport and top-tier medical care within a 15-minute drive. Properties offering this combination of unrestricted acreage, move-in-ready living, functional outbuildings, and exceptional outdoor amenities are becoming increasingly difficult to find. Whether you're looking to homestead, raise animals, enjoy outdoor recreation, or simply embrace country living without restrictions, this property offers the lifestyle you've been searching for. Don't miss this rare opportunity to own a truly one-of-a-kind property with room to live, work, play, and grow!

3764 Northwestern Pike, Winchester

Listing courtesy of Touchstone Realty, LLC. Contact:

$424,900
4 Beds ⋅ 2 Baths
✨ Rare Opportunity on Winchester's East Side with a LOWER-LEVEL IN-LAW SUITE! 🏡 Welcome home to this spacious 4-bedroom, 2-bath beauty offering a warm, inviting layout and thoughtful updates throughout! ❤️ The main level features a generous living room, dining room, and a bright kitchen with stainless steel appliances, plus three bedrooms and a full bath—all highlighted by beautiful hardwood floors. ✨ The finished lower level is a standout feature with a private in-law suite 🏠 featuring a huge rec room, kitchenette, bedroom, full bath, abundant natural light ☀️, and convenient walk-out access. Step outside to enjoy your morning coffee on the covered front porch or unwind on the back deck. The large corner lot offers plenty of yard space for gardening, pets, or play! 📍 Perfectly located near Jim Barnett Park, Shenandoah University, schools, commuter routes, and just 1 mile from Old Town Winchester for shopping, dining, and entertainment! ✨ Recent Updates Include: 🏠 New roof (2026) with transferable warranty 🔥 Brand-new boiler (2025) 🎨 Fresh paint throughout for a bright, clean feel 🛏️ Beautifully updated lower-level bedroom 🚿 New bath & kitchen hardware for a fresh finishing touch 👕 New dryer for added convenience ⏳ Don't miss this incredible opportunity! Homes with this much space, flexibility, and location don't come along often—schedule your showing today before it's gone! 🔑🏡💕

145 Wilkins Dr, Winchester

Listing courtesy of Colony Realty. Contact:

$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
$389,000
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. Schedule your tour today.

103 Elaine Drive, Winchester

Listing courtesy of Long & Foster Real Estate, Inc.. Contact: (540) 662-3484
$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:

$575,000
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
$379,000
3 Beds ⋅ 2 Baths
UPDATED PRICE!! NEW ROOF!!. SEPTIC INSPECTION AND REPAIRS COMPLETED!! This beautifully remodeled home showcases quality and attention to detail from the moment you step inside. The kitchen has been completely transformed with abundant cabinetry, generous counter space, and brand-new stainless steel appliances, creating both style and functionality. Throughout the home, you will find new flooring, doors, trim, and fresh paint, giving every room a clean, modern feel. Both bathrooms have been fully renovated with new vanities, toilets, and tiled tub surrounds. A standout feature is the brand-new HVAC system, providing comfort and efficiency year-round. The finished lower level offers a spacious and versatile living area—created with the intent for it to be a primary bedroom complete with an adjoining full bath and separate rear entrance, but also perfect for a media room or game space. The conditioned utility room includes a water heater, water softener, and washer/dryer hookups. For those working from home, the layout offers multiple office possibilities, including a room off the kitchen, an upstairs bedroom, or a flexible space at the base of the stairs. Additional highlights include approximately 400 sq.ft. of storage space beneath the garage, accessible through new double doors—ideal for lawn equipment, tools, a workshop, or hobby space. Be sure to explore the peaceful stream that borders the rear of the property, adding a natural touch to this thoughtfully updated home. Please note: chimney is nonfunctional.

1355 Perry, Winchester

Listing courtesy of NextHome Realty Select. Contact: (540) 667-9097
$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:

$305,000
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