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$549,900
5 Beds ⋅ 4 Baths
“Pioneer Heights Colonial” - Welcome to this beautifully maintained colonial in the desirable Pioneer Heights neighborhood, ideally situated just off Route 7 for easy commuter access. Offering five bedrooms and 3.5 baths, this spacious home has been thoughtfully updated and improved over the years, providing a comfortable blend of classic character and modern convenience. The heart of the home is the updated kitchen, featuring custom cabinetry, granite countertops, stainless steel appliances, and plenty of workspace for everyday living and entertaining. Throughout the home, you'll find updated bathrooms, newer carpeting, and numerous additional improvements that make this home truly move-in ready. The finished basement adds valuable living space and versatility, complete with a walkout, comfortable living area, fifth bedroom, and full bathroom. Ample storage space provides plenty of room for seasonal items, hobbies, or household needs. Step outside and enjoy multiple spaces designed for relaxing and entertaining. A rear porch leads to a deck and backyard patio, creating an easy flow for outdoor gatherings, morning coffee, or quiet evenings. The meticulously manicured front yard is a standout, featuring lush green grass, thoughtfully maintained mulch beds, and beautiful flower gardens—all complemented by an underground sprinkler system for easy lawn care. With generous living space, numerous updates, attractive outdoor amenities, and a convenient location close to Route 7, this Pioneer Heights home offers the space, comfort, and accessibility you've been looking for. Schedule your appointment to see it today!

223 Asbury Rd, Winchester

Listing courtesy of Real Broker LLC- Winchester. Contact:

$355,000
2 Beds ⋅ 2 Baths
Come see what makes Willow Lawn, a 55+ community, such a desirable place to call home! This inviting one owner Winchester home offers a comfortable blend of charm, functionality, and everyday convenience. The Floorplan is open and contemporary. The Great Room has Cathedral Ceilings and is very spacious. The grounds are taken care of by the community so life is easy. One level living w/ newer HVAC, a 4 year old roof, LVP flooring, updated bath, 2 bedrooms + 2 full bath. The 1 car garage is heated and cooled for year round comfort. There is space for a car and small workshop. You'll feel welcomed in this neighborly community where people walk, socialize and have planned activities at the well appointed Community Center. It is right around the corner from this home. Also, this home is located near the Abrams Creek Wetlands Preserve, perfect for walking + biking. Hospital + Down Town Winchester are 10 minutes away. Priced well and ready for you, come take a look today.

1847 Melvor Ln, Winchester

Listing courtesy of Century 21 Redwood Realty. Contact:

$375,000
3 Beds ⋅ 2 Baths
265 McDonald Rd is a 1-story Winchester home built in 1974 with a lower level and connected outdoor spaces. The kitchen includes cabinet storage, a preparation counter, and an adjoining area for dining. The main living room provides space for seating, with an additional finished room on the lower level. The primary bedroom includes a walk-in closet with shelving for organization and an adjoining bathroom with a shower and vanity. A rear deck connects to the home through sliding doors, extending the usable space outdoors. A dedicated laundry area includes cabinetry and a folding counter. The layout combines everyday living with practical storage.

265 Mcdonald Rd, Winchester

Listing courtesy of Open Door Brokerage, LLC. Contact: 4804625392
$409,000
4 Beds ⋅ 1 Baths
Welcome to a Mid‑Century Modern Home Where Timeless Character Meets Modern Sophistication. This beautifully updated 3–4 bedroom mid‑century modern home, where timeless character meets modern sophistication in one of Winchester’s most convenient and walkable locations. The large covered front porch immediately sets the tone—an inviting space for morning coffee or relaxed evening conversation. Inside, natural light fills the home, highlighting refinished hardwood floors, fresh interior and exterior paint, and preserved architectural details including original wide wood baseboard trim and classic pocket doors. The well‑proportioned bedrooms offer comfortable retreats with the same warm character found throughout the home. Also added for efficient heating and cooling year‑round, a new ductless mini‑split system has been installed for your comfort. The renovated kitchen features new cabinetry, granite countertops, trending black stainless‑steel appliances, and a pantry with built‑in cabinetry, providing excellent storage and everyday functionality. Thoughtful upgrades and custom touches enhance each living space, creating an atmosphere that is both refined and inviting. Step outside to a covered back porch with new maintenance‑free decking, overlooking an open backyard ideal for relaxing, entertaining, gardening, or unwinding at the end of the day. Additional conveniences include off‑street parking and an oversized single‑car detached garage. The neighborhood continues to shine with recent street repaving and new sidewalks, enhancing curb appeal and walkability. Ideally located just a short stroll from Winchester’s vibrant downtown pedestrian mall, you’ll enjoy easy access to restaurants, coffee shops, boutiques, breweries, and community events. Mature trees, walkable streets, and proximity to commuter routes, parks, schools, and everyday amenities make this location truly exceptional. This is a rare opportunity to own a handsome, thoughtfully updated home that captures the best of Winchester living—where character, comfort, and location come together beautifully.

322 E Piccadilly, Winchester

Listing courtesy of Long & Foster Real Estate, Inc.. Contact: (540) 662-3484
$435,000
3 Beds ⋅ 2 Baths
No HOA in the heart of Winchester! This charming brick rancher features three bedrooms, two baths, tall ceilings, fresh paint, hardwood floors, and a fireplace on the main level. The layout includes a versatile sunroom with a private entrance and a kitchen equipped with stainless steel appliances. The basement expands your living space with a wet bar, separate entrance, and another fireplace! This home provides timeless construction and incredible potential. Walk outside to the spacious, fully fenced backyard with a storage shed. Enjoy ample parking with an oversized attached garage. Don’t miss the opportunity to own this home in an excellent location, just steps from Winchester Country Club and minutes to shopping, dining, and commuter routes. *Seller is also offering a one-year Home Warranty with the sale of the property!

131 Country Club Cir, Winchester

Listing courtesy of Berkshire Hathaway HomeServices PenFed Realty. Contact:

$317,265
3 Beds ⋅ 2 Baths
Welcome to this charming three-bedroom, two-bathroom raised ranch nestled on a quiet, tree-lined street in one of the area’s most close-knit neighborhoods. Full of character and potential, this home boasts a classic floor plan just waiting for your cosmetic updates and personal design vision. The main level features a bright living area filled with natural light, a dedicated dining space, and original hardwood flooring. Three comfortably sized bedrooms complete the upper level, including a primary bedroom with its own private en-suite bath. The full basement offers so much room to expand with a laundry area, a finished area for a possible sleeping room, ample heavy shelving units for crafting, storage or a workshop, and a walkout with sliding doors. Beyond the front door lies a vibrant, amenity-rich community known for its warm atmosphere. Neighborhood residents enjoy access to a spring-fed/man-made lake featuring a sandy beach area, swimming, fishing, and a boat ramp (gas motors are not permitted). Cherokee Beach is open to residents without a beach pass, additional smaller ponds and scenic streams located throughout the community, two community playgrounds, wooded nature walks and trails, pavilion spaces, open sports areas, and picnic spots, and covered/lighted mailbox stations and covered school bus stops.

148 Doe Trl, Winchester

Listing courtesy of Keller Williams Realty Advantage. Contact: 3049014886
$515,000
2 Beds ⋅ 3 Baths
Welcome to 100 Gooseberry Drive, located in Winchester's established Cross Creek Village community! This meticulously maintained brick rancher offers true main-level living in one of the communities most spacious and sought-after floor plans. The main level features formal living and dining rooms, a kitchen with breakfast nook, and a bright bonus sunroom. The generous primary suite is filled with natural light and features its own cozy gas fireplace, spacious en-suite bath, and walk-in closet. A guest bedroom, additional full-bath, and dedicated laundry complete the main level. The attached two-car garage provides direct access to the home as well as a private side-entrance leading upstairs to a thoughtfully designed guest suite- ideal for visitors, a home studio or additional climate controlled storage! Enjoy easy outdoor living on a quiet corner lot, with a private fenced in back-patio perfect for enjoying morning coffee or summer grilling! Set within a vibrant 55+ community, this home offers comfort, convenience and low-maintenance living just minutes from major shopping, dining & more! Schedule your private tour today!

100 Gooseberry Dr, Winchester

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

$805,000
4 Beds ⋅ 4 Baths
CARRINGTON HOMES AT FALL RIDGE ESTATES- 5 Acre Wooded LOTS WITH MOUNTAIN VIEWS. Choose from 7 different floorplans including our Main Level Owners Suite floorplan the Boxwood Farm model with standard 10' Main Level Ceilings Model Home Open on Weekends from 11-5 at 156 Covey Lane Winchester Va

Tumble Leaf Lane, Winchester

Listing courtesy of Pearson Smith Realty, LLC. Contact: listinginquires@pearsonsmithrealty.com
$439,000
5 Beds ⋅ 3 Baths
Welcome to this newly renovated and thoughtfully designed 5-bedroom, 3-full-bath home offering exceptional flexibility for modern living or rental income. Featuring two full kitchens, two dining areas, and potentially two separate living spaces, this home provides a unique opportunity to create two distinct living areas under one roof. Bottom level has two separate entrances in front and rear and for privacy and convenience, the layout ideal for extended family, guests, roommates, or potential rental use. Newly renovated, this home combines the comfort of modern updates with the versatility buyers are looking for. Whether you're seeking a spacious primary residence or an investment opportunity with potential rental income, this property offers the space and flexibility to make it your own. Don't miss this rare opportunity to own a beautifully renovated home with multiple living possibilities!

300 Pembridge Dr, Winchester

Listing courtesy of ERA Oakcrest Realty, Inc.. Contact: (540) 665-0360
$699,000
7 Beds ⋅ 5 Baths
Welcome to 2700 Loyalty Court—a beautifully maintained showcase home offering nearly 5,000 square feet of unmatched versatility in one of Winchester City’s most coveted locations. Commanding a prime corner lot on a peaceful cul-de-sac, this residence immediately captivates with its timeless stone-and-vinyl exterior, inviting covered front porch, and unmistakable curb appeal. Step inside to a soaring two-story foyer flowing into a light-filled interior boasting fresh paint, newer carpet, refined architectural details, and abundant natural light throughout. Designed for both grand scale entertaining and effortless everyday living, the main level features a dedicated office behind French doors, a formal dining room accented by elegant wainscoting, a den and a full bath. At the heart of the home, the sprawling family room makes a bold statement with architectural pillars and a floor-to-ceiling stone gas fireplace. It connects seamlessly to a chef-friendly kitchen complete with granite countertops, upgraded cabinetry, stainless steel appliances, a center island, pantry, built-in desk area, and a bright breakfast nook opening directly to the rear deck. A handy mudroom with laundry off the garage completes this level's intuitive floor plan. The impressive layout continues upstairs, offering abundant accommodations for family and guests across five generously sized bedrooms. The massive primary retreat serves as a true private sanctuary, complete with a dedicated sitting area, large walk-in closet, and a spa-like ensuite bath featuring a glass walk-in shower and a corner soaking tub. Two bedrooms are connected by a convenient Jack-and-Jill bath, alongside two more spacious bedrooms and another full bathroom. The real showstopper continues downstairs in the fully finished, walkout lower level—a massive multi-functional footprint that expands your living options exponentially. This lower level provides endless flexibility, featuring an expansive recreation room for hosting game days or movie nights, a full bath and two additional bedrooms perfect for guests, and multiple finished rooms ready to serve as a home gym, playroom, or hobby space—plus a storage area to keep it all organized. Offering extraordinary scale on a premier corner cul-de-sac lot, this move-in-ready home represents Winchester living at its finest and stands ready to welcome its next proud owners.

2700 Loyalty Ct, Winchester

Listing courtesy of Colony Realty. Contact:

$525,000
4 Beds ⋅ 4 Baths
Welcome to a home that gives you room for all the things that matter—working from home, hosting friends, relaxing at the end of the day, and making the space truly your own. Located in Senseny Glen, this 4-bedroom, 3.5-bath, three-level Colonial offers an ideal blend of comfort, flexibility, and location. The recently remodeled main level features luxury vinyl plank flooring throughout, along with a dedicated office, dining room, breakfast area, and inviting family room with a gas fireplace and updated kitchen. And then there’s the front porch—the perfect spot for morning coffee, an evening glass of wine, or simply enjoying the neighborhood. Upstairs, the spacious primary suite offers a private retreat with double vanity, separate shower, and jetted tub. Three additional bedrooms, a full bath, plus access to a floored attic provide plenty of space for guests, hobbies, or storage. The lower level takes entertaining to another level with a generous rec room, built-ins, wet bar, windows, and walk-up access to the backyard. Think movie nights, game nights, a home gym, creative space—or simply a place to spread out. Outside, the fully fenced backyard features a deck and mature trees, creating a private setting for outdoor dining, relaxing, gardening, or spending time with friends and family. This location makes life easy. Senseny Glen is close to schools, shopping, restaurants, and everyday conveniences, giving you the space of a neighborhood without feeling far from everything. A home with room to work, relax, entertain, and grow—while still feeling connected to the things you love. This is more than having more space. It’s having the flexibility to make the space work for you.

302 Canyon Rd, Winchester

Listing courtesy of ERA Oakcrest Realty, Inc.. Contact: (540) 665-0360
$430,000
3 Beds ⋅ 2 Baths
This is the one you have been waiting for!! Well cared for home, one story living in desirable Briarwood Estates...east side location convenient to commuter routes, shopping and Old Towne Winchester. Open floor plan with close to 1700 square feet. Three bedrooms, two full baths with hardwood floors in living/family room and dining area. Gas fireplace in family room, two walk in closets in master suite. Two car garage, two decks (enjoy your morning coffee on deck off of master bedroom!!) and large fenced backyard with storage shed.

310 Goldenrod Rd, Winchester

Listing courtesy of Hunt Country Sotheby's International Realty. Contact: (540) 687-8500
$550,000
4 Beds ⋅ 4 Baths
Welcome to 128 Alliance Court, a beautifully maintained, move-in-ready home built in 2021 and offering over 3,200 finished square feet across three spacious levels. The open-concept main level features new flooring and a bright, inviting layout ideal for both everyday living and entertaining. Upstairs, you’ll find generously sized bedrooms and conveniently located laundry with the washer and dryer included. The finished lower level provides flexible space for a recreation room, home office, gym, or guest area—and the treadmill conveys! Automatic window treatments add modern convenience and effortless light control throughout the home. Complete with an attached two-car garage and easy access to I-81, shopping, dining, and schools, this home combines space, comfort, and convenience in a desirable Winchester location.

128 Alliance Ct, Winchester

Listing courtesy of Samson Properties. Contact: 7033788810
$300,000
3 Beds ⋅ 1 Baths
Charming 3-Bedroom Rambler on a Spacious Lot! Welcome to 111 Haven Terrace, a conveniently located 3-bedroom, 1-bath rambler situated on approximately 0.26 acres. This single-level home offers a practical layout with comfortable living spaces and plenty of potential to make it your own. The main-level living design provides easy access throughout the home, making this property a great fit for first-time buyers, downsizers, or anyone looking for a manageable home without stairs. The level lot offers space for outdoor enjoyment, gardening, entertaining, or future improvements. With three bedrooms, a full bath, and a manageable footprint, this home offers an excellent opportunity for a buyer looking for affordability and convenience. Bring your vision and add your personal touches to create the home you've been looking for.

111 Haven Ter, Winchester

Listing courtesy of EXP Realty, LLC. Contact: 8668257169
$230,000
2 Beds ⋅ 1 Baths
Investor opportunity in Winchester! This 2-bedroom, 1-bath home offers 1,112 finished square feet above grade, plus a full unfinished basement with additional space for storage, renovation, or future improvements. The home also features two fireplaces and a convenient carport. Located within the City of Winchester, this property presents an excellent opportunity for an investor, renovator, or buyer looking to bring their vision to life. With the right updates, this home has the potential to shine. Property is being sold strictly AS-IS. Seller will make no repairs.

214 Molden Dr, Winchester

Listing courtesy of Real Broker, LLC. Contact: 8504500442
$380,000
4 Beds ⋅ 3 Baths
Nestled in the serene Wilde Acres community, this exquisite Colonial-style residence offers a harmonious blend of luxury and comfort, perfect for those seeking an elevated lifestyle. Built in 2007 and thoughtfully renovated in 2019, this home boasts a pristine condition and modern amenities that cater to the discerning homeowner. Step inside to discover an inviting open floor plan that seamlessly connects the family room, dining area, and gourmet kitchen. The heart of the home features upgraded countertops, a spacious pantry, and energy-efficient appliances, including a self-cleaning oven and an ENERGY STAR dishwasher. The kitchen's breakfast area is bathed in natural light, making it an ideal spot for morning coffee or casual meals. Recessed lighting and ceiling fans throughout enhance the ambiance, while the cozy gas fireplace with glass doors in the family room invites relaxation on cooler evenings. With four generously sized bedrooms, including a primary suite complete with a luxurious en-suite bathroom and walk-in closet, this home provides ample space for both privacy and togetherness. The additional bathrooms are elegantly designed, featuring a tub shower combination that adds a touch of sophistication. The exterior of the property is equally impressive, situated on a corner lot of 0.3 acres that adjoins open space, offering both tranquility and scenic mountain views. Enjoy outdoor living on the expansive deck, perfect for entertaining or unwinding in the fresh air. The property is equipped with secure storage options and exterior lighting, ensuring both convenience and safety. Additional features include a full unfinished basement with outside and side entrances, providing endless possibilities for customization, whether as a workshop or additional living space. The gravel driveway accommodates up to six vehicles, making hosting gatherings effortless. Residents of Wilde Acres enjoy exclusive access to community amenities, including a community center, picnic area, and a picturesque lake, fostering a sense of community and connection. The association also takes care of road maintenance and snow removal, allowing you to focus on enjoying your home. This property is not just a house; it's a lifestyle. Experience the perfect blend of luxury, comfort, and community in this stunning Wilde Acres residence, where every detail has been thoughtfully curated for your enjoyment.

900 Enfield Dr, Winchester

Listing courtesy of Spring Hill Real Estate, LLC.. Contact: 7038914520
$350,000
3 Beds ⋅ 2 Baths
Nestled in a charming neighborhood, this delightful ranch-style home offers a perfect blend of comfort and convenience. Built in 1954, this brick beauty exudes timeless appeal while providing modern living spaces that cater to today's lifestyle. With 1,507 square feet of thoughtfully designed space, this residence features three cozy bedrooms and one and a half bathrooms, making it an ideal retreat for anyone seeking a warm and inviting atmosphere. As you step inside, you'll be greeted by a spacious layout that encourages both relaxation and entertaining. The partially finished basement offers endless possibilities-whether you envision a cozy family room, a home office, or a play area, the choice is yours! The main living areas are bathed in natural light, creating a welcoming ambiance that feels like home. The exterior of the property is equally inviting, with a classic brick façade that stands the test of time. Enjoy the convenience of on-street parking, ensuring that you and your guests always have a place to park. The surrounding neighborhood is a tapestry of tree-lined streets and friendly faces, fostering a sense of community that is hard to find. Location is key, and this home does not disappoint. Situated in a vibrant area, you'll find an array of local amenities just a stone's throw away. Explore nearby parks for leisurely strolls or picnics, and take advantage of local shops and eateries that add character to the community. Whether you're grabbing a morning coffee or enjoying a weekend brunch, the neighborhood offers a delightful selection of options to satisfy your cravings. For those who appreciate the outdoors, the proximity to parks and recreational areas provides ample opportunities for hiking, biking, and enjoying nature. The community is well-connected, making it easy to access nearby attractions and essential services. This charming ranch-style home is more than just a property; it's a place where memories are made and cherished. With its inviting atmosphere, convenient location, and potential for personalization, this residence is ready to welcome you home. Don't miss the chance to make this delightful space your own!

1048 Woodland Ave, Winchester

Listing courtesy of Re/Max Roots. Contact: (540) 686-7362
$710,000
5 Beds ⋅ 4 Baths
Welcome to 110 Betpath Ct, nestled within the premier Twin Lakes Overlook (TLO) enclave of exclusively single-family homes by Toll Brothers and Richmond American, this exceptional 2019-built executive estate offers an unmatched lifestyle in Winchester. Spanning nearly 4,000 square feet of refined living space, this property combines high-end craftsmanship with an extraordinary, functional layout. The Main & Upper Levels Designed for effortless entertaining and daily comfort, the main level features an expansive formal dining room and a sophisticated living room. The heart of the home is a gourmet chef's kitchen showcasing sleek silver appliances, abundant custom cabinetry, and premium granite countertops throughout. This space flows seamlessly into a sprawling great room and family room framing serene views of the private, tree-lined backyard. Upstairs, the residence offers five spacious bedrooms, highlighted by a true primary sanctuary featuring an expansive master suite complete with a luxurious ensuite bath, indulgent Jacuzzi soaking tub, and a separate stand-up shower. The Lower Level & Outdoor Living The fully finished lower level functions as a self-contained apartment space, offering ultimate flexibility for guests or multi-generational living. It includes an expansive sixth bedroom (NTC), a luxury full bath with a soaking tub, a practical kitchenette equipped with a sink and refrigerator, and convenient all-in-one laundry hookups. A private walk-up leads directly out to the generous, beautifully treed backyard, creating a secluded outdoor haven. Residents of TLO also enjoy exclusive neighborhood perks, including private community lake access and scenic walking/running trails just steps from your door. Prime Location Conveniently situated just minutes from historic downtown Winchester’s vibrant shops and dining, this home places you in close proximity to the renowned Winchester Hospital and the expansive 170-acre Jim Barnett Park and Family Sports facilities. Blending executive elegance with everyday practicality, this property delivers a premier Northern Virginia living experience. Schedule your private tour today!

110 Bentpath Ct, Winchester

Listing courtesy of Realty Aspire. Contact: 7034290188
$429,000
3 Beds ⋅ 2 Baths
Awesome Interior Photo's Coming Soon! Step inside this tastefully renovated brick ranch and feel instantly at home. Offering three comfortable bedrooms and two full baths, this property blends classic charm with thoughtful updates throughout. The main level features a bright, welcoming layout perfect for everyday living, while the lower level opens the door to exceptional flexibility — complete with its own entrance, a full bath, and a kitchenette. It’s an ideal setup for multi‑generational living, extended guests, or a turnkey investment opportunity ready for rental income. Outside, the large fenced yard provides space to relax, play, garden, or gather, and the off‑street parking adds everyday convenience. The location couldn’t be better: close to schools, the college campus, Historic Downtown Winchester, and a wide range of shopping and commuter routes. A move‑in‑ready home with options, comfort, and character — schedule your tour today and see how perfectly it fits your needs. Schedule your tour today!Awe

1412 S Loudoun St, Winchester

Listing courtesy of Long & Foster Real Estate, Inc.. Contact: (540) 662-3484
$499,900
3 Beds ⋅ 2 Baths
Looking for one-level living with acreage, a detached workshop/garage, RV/camper parking, and no HOA? Welcome to 1960 Siler Road, a custom-built ranch situated on 5 fenced acres in Winchester. The home offers a comfortable and functional floor plan with hardwood flooring throughout much of the home, Corian countertops, stainless steel appliances, and a sunroom located just off the primary bedroom. Outside, the property offers plenty of versatility with an attached two-car garage plus an approximately 23'6" x 29'11" detached workshop/garage with its own electric service, roll-up door, covered storage areas, dedicated RV parking, and a 30-amp RV hookup. With no HOA or restrictive covenants, there’s room to make the acreage your own. Bring the chickens, create a garden, or simply enjoy the extra space. Recent improvements include an updated shower, new dishwasher, new mini blinds, and a LeafFilter gutter protection system. Additional features include a tankless water heater, owned propane tank, and whole-house generator. With one-level living, 5 fenced acres, no HOA, RV/camper accommodations, and substantial garage and workshop space, 1960 Siler Road offers a combination of features that can be difficult to find in the Winchester area.

1960 Siler Rd, Winchester

Listing courtesy of Realty ONE Group Old Towne. Contact: 5407738475
$549,900
4 Beds ⋅ 3 Baths
Fully Renovated Winchester-Area Retreat on 3.24 Acres with Two Garages! Rarely does a property come along that offers this combination of extensive renovations, usable acreage, incredible storage, multiple garages, and a peaceful established neighborhood, all just minutes from everything Winchester has to offer. Welcome to 127 Mountain View Rd, where quiet living meets modern convenience, and nearly everything has been thoughtfully updated for today's buyer. Inside, extensive updates include fresh paint, new LVP flooring, refinished hardwood floors, updated fixtures and lighting, and 2-inch recessed lighting. The luxury kitchen features a large 5-foot island, quartz countertops, stainless-steel appliances, and under-cabinet lighting, plus a convenient pop-up electrical outlet/device charger in the island. Major improvements provide exceptional peace of mind, including a new roof (2025), new Rheem HVAC system (2026), new baseboard heat (2026), new water heater (2026), and completely new septic system with tank, distribution box, and lines (2026). Newer windows add to the home's efficiency and appeal. Enjoy outdoor living on the freshly stained 48' x 12' deck, perfect for entertaining, grilling, or relaxing. The oversized attached garage offers abundant storage and features a new garage door and opener. A second 26' x 17' detached garage with its own basement provides exceptional workshop, hobby, equipment, and storage space. With the right vision, the detached structure offers a variety of opportunities. Fresh landscaping and a newly graded oversized driveway provide plenty of parking and a welcoming approach. Located just minutes from downtown Winchester, shopping, restaurants, the hospital, gyms, and schools. Enjoy a quiet neighborhood setting with an established community feel while remaining close to everything you need. Homes in this great neighborhood are a rarity, don't miss your opportunity to see this one. 3.24 acres | Extensive 2025–2026 updates | Luxury kitchen | Two garages | Workshop potential | New septic | New HVAC | New roof | Large deck | No HOA | Minutes to Winchester.

127 Mountain View Rd, Winchester

Listing courtesy of Realty ONE Group Old Towne. Contact: 5407738475
$175,000
1 Beds ⋅ 1 Baths
Cozy 1-bedroom, 1-bathroom cabin located on a level, nicely shaded lot, ready for your enjoyment. Offering the perfect combination of rustic character, comfort, and natural beauty. Step outside onto the screened-in porch and enjoy your morning coffee, unwind with a good book, or simply take in the sights and sounds of the surrounding woods. This peaceful setting offers a wonderful opportunity to slow down and enjoy nature while still having all the comfort you need. Whether you're searching for a weekend getaway, a cozy full-time residence, or an investment property with rental potential, this versatile cottage is full of possibilities. Newer upgrades include an electrical panel, UV light, and exterior and interior painting/siding. Won’t last long at this price point!

305 Raccoon Dr, Winchester

Listing courtesy of Dandridge Realty Group, LLC. Contact: 3048857645
$984,900
4 Beds ⋅ 4 Baths
Nestled in the prestigious Midland Heights community, this exquisite Colonial-style residence offers a harmonious blend of luxury and comfort, set against a breathtaking mountainous backdrop. Built in 2019, this home boasts an impressive 3,317 square feet of meticulously designed living space, perfect for those who appreciate both elegance and functionality. The kitchen is a culinary dream, featuring high-end appliances including a built-in microwave, electric cooktop, and self-cleaning wall oven, all complemented by ample table space and a cozy eat-in area. Beautiful built-ins and walk-in closets provide both style and practicality, ensuring that every inch of this home is utilized to its fullest potential. The main level also features a thoughtfully designed entry-level bedroom and a luxurious bathroom with a walk-in shower, catering to convenience and comfort. Ascend to the upper levels to find two additional spacious bedrooms with its own spacious full bathroom, promising tranquility and relaxation. The fully finished basement offers endless possibilities, a forth bedroom or office with a full bathroom, daylight windows and walkout access to the serene outdoors, making it perfect for a home gym, media room, or additional living space. There is also an expansive storage area for all your needs. Outside, the property spans over 5 acres of beautifully cleared and landscaped grounds, providing a private oasis that backs to lush trees. Enjoy the tranquility of nature from your beautiful wrap-around porch, where you can unwind and soak in the stunning mountain views. The lower level offers a concrete area with a hot tub. There is a beautiful large detached 3 car garage for all of your cars, motorcycles or mowers. This home is not just a residence; it's a lifestyle. Experience the luxury of modern living in a serene mountain setting, where every detail has been thoughtfully curated to create a warm and inviting atmosphere. With its exceptional features and prime location, this property is a rare gem that promises to be a cherished sanctuary for years to come. Generator hook up wired for electric outages and Outside water bib running hot and cold water for dog baths and other use. Come see it today!

236 Delmas Trl Trl, Winchester

Listing courtesy of Keller Williams Realty. Contact: 7036690099
$595,390
3 Beds ⋅ 3 Baths
NEW BUILD, move in ready single-family home at Hiatt Pointe, 55+ community at Snowden Bridge by Van Metre Homes! The Sierra 39-F2 at Hiatt Pointe is stunning! This home offers 3 bedrooms, 3 full bathrooms, a 2-car front load garage, a finished basement and much more! As you enter the home you are greeted with 9' ceilings, luxury vinyl plank flooring, recessed lighting throughout, programmable thermostat, tankless gas water heater, solar panel ready, open floor plan, huge rec room on the lower level, all spanning over 3200 sq ft. The kitchen is a chef's dream with all stainless-steel appliances, white quartz counters, a spacious island and a walk-in pantry with solid shelving. Off the great room is your 20x12 deck, making it easy to entertain your family and friends! Cozy up by your electric fireplace to unwind or enjoy a good book. The primary suite offers a large bath with quartz counters, dual vanities, soaking tub and a roll -in frameless tile shower. On the lower level of the home, you will find a finished rec room, the third bedroom and the third full bath. Don't miss your opportunity to live in Hiatt Pointe at Snowden Bridge, a gated 55+ active adult community! Enjoy all the amenities to include a full clubhouse, fitness center, pickleball, outdoor pool and hot tub, fire tables and outdoor kitchens! Located near restaurants, shopping and downtown Winchester. Close to Rt 7, I-81 and I-66, making it a great commuter location. Schedule your showing today!

116 Magpie Ln, Winchester

Listing courtesy of Long & Foster Real Estate, Inc.. Contact: (540) 662-3484
$295,000
2 Beds ⋅ 3 Baths
**Investor & Fixer-Upper Special Endless Potential on Nearly 1 Acre!** Calling all visionaries, weekend warriors, and Airbnb hosts! This secluded retreat in Shawneeland is your chance to create the mountain getaway, rental, or private homestead you've been dreaming of customized entirely to your style. Offering an estimated 2,000+ sq ft of finished living space with the potential for over 2,400 total sq ft, this home has great bones to build on: new foundation repairs, porch, roof, HVAC, and well pump/bladder (all 2012), hot water heater (2019), and washer/dryer (2016). The spacious porch was even framed with a hot tub in mind just add your finishing touches! A walk-out basement leads to an oversized attached 2-car garage, offering great flexibility for storage, a workshop, or extra living space. Set on a corner lot that was once two separate parcels and is now combined into just shy of 1 acre, this is one of the largest lots you'll find in Shawneeland with room to roam and privacy to spare. And despite the tranquil, wooded setting, you're only about 15 miles from historic, charming downtown Winchester, a destination growing fast in popularity. Bring your tools, your creativity, and your vision, this one is priced for opportunity and sold strictly As Is. No HOA

159 Aspen Trl Trl, Winchester

Listing courtesy of EXP Realty, LLC. Contact: 8668257169
$287,000
3 Beds ⋅ 1 Baths
Located in the desirable Shawneeland community, this freshly updated three bedroom home is situated on a great corner lot with scenic views and plenty of possibilities to make it your own. The home features an updated kitchen, breakfast area, along with a detached two story garage/shed offering additional parking and storage. Step outside and enjoy relaxing evenings on the deck while taking in peaceful surroundings. Shawneeland offers an array of community amenities, including fishing, private access, playgrounds, and a four-hole golf course. With it's spacious lot, thoughtful updates, versatile outdoor space, and inviting setting, this quaint home is ready for it's next owner to make it their very own.

700 Tomahawk Trl, Winchester

Listing courtesy of Berkshire Hathaway HomeServices PenFed Realty. Contact: 5403717653
$385,000
3 Beds ⋅ 2 Baths
Coming soon in Winchester! Welcome to this beautifully maintained 3-bedroom, 2-bath brick rambler in a convenient location. This move-in-ready home offers comfortable one-level living and features an updated kitchen with quartz countertops and stainless steel appliances, updated bathrooms, attractive flooring throughout, and a detached side-entry garage. The current owner has carefully maintained the property, making it ready for its next owner to enjoy. Conveniently located near shopping, dining, commuter routes, and everyday amenities. Professional photos and showing availability coming soon!

108 Williamson Rd, Winchester

Listing courtesy of Spring Hill Real Estate, LLC.. Contact: 7038914520
$334,000
3 Beds ⋅ 3 Baths
Nestled in the charming Wilde Acres community, this delightful Colonial home offers a perfect blend of comfort and style. Built in 2009, this residence features 3 spacious bedrooms and 2.5 bathrooms, providing ample space for relaxation and daily living. The inviting layout encompasses 1,680 sq. ft. of thoughtfully designed living space, ideal for both entertaining and quiet evenings at home. Enjoy the serene outdoor setting on a generous 0.65-acre lot, perfect for gardening or outdoor activities. The detached garage and driveway provide convenient parking options. Inside, the home boasts a warm ambiance, ready for your personal touch. Experience the tranquility of Wilde Acres while being just a short drive from local amenities. This home is not just a place to live; it's a place to thrive. Don't miss the opportunity to make it yours!

308 Fawn Dr, Winchester

Listing courtesy of Coldwell Banker Premier. Contact: 990007.lead@leads.leadrouter.com
$675,000
2 Beds ⋅ 1 Baths
Discover a rare opportunity to own a piece of Frederick County history with this unique farmette property offering approximately 9.79 acres, a charming farmhouse, extensive outbuildings, and an established farm market setup. Originally built in the 1800s with later additions, the home offers character that is difficult to replicate while providing the space and functionality today's buyers appreciate. Beyond the residence, this property truly shines through its improvements, including a large approximately 2,400-square-foot wooden barn with three stalls, multiple storage buildings, workshop space, greenhouse/storage building, orchard and garden area, and a separate farm market building. The farm market features separate electric service, insulation, gas heaters, refrigerators, counters, shelving, and a layout that has supported farm market operations. (Buyer to verify all intended uses with Frederick County.) Whether your vision includes homesteading, raising animals, growing produce, operating a farm market, or simply enjoying the beauty of country living, this property offers exceptional flexibility. Located just minutes from Winchester while providing the privacy and space of rural living, this is a property where history, agriculture, and opportunity come together. Properties offering this combination of history, acreage, agricultural infrastructure, and farm market potential rarely become available. Schedule your private showing and experience everything this unique property has to offer. Highlights Approximately 9.79 acres Historic farmhouse 2,400± sq ft barn with 3 stalls Separate farm market building Orchard & garden area Multiple outbuildings Workshop Greenhouse/storage Convenient Winchester location

531 Cedar Grove Rd, Winchester

Listing courtesy of Virginia Real Estate. Contact: 5406452999
$759,900
5 Beds ⋅ 5 Baths
This spectacular, move-in-ready home shows like a professional model, showcasing exquisite designer touches, custom window treatments (included), and premium finishes throughout. Built in 2023, the residence offers the ultimate convenience of main-level living with a bright, open-concept layout that beautifully blends comfortable luxury with timeless appeal. Nestled on a spacious .28-acre lot with a deep setback from the street, the property provides a serene sense of arrival and added privacy. The fully finished lower level significantly expands your living space, offering a versatile recreation area, a private guest suite, and an additional room perfect for a home office or extra bedroom. Step outside to the beautiful patio, ideal for relaxing or entertaining. Every detail of this home reflects extraordinary care and pristine taste—truly a model-home experience ready for its new owners. *Also offering a one-year Home Warranty with the sale of the home.

174 Williamson Rd, Winchester

Listing courtesy of Berkshire Hathaway HomeServices PenFed Realty. Contact: