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111 Old Wagon Rd, Winchester
$553,847
4 Beds ⋅ 3 Baths
Welcome to 111 Old Wagon Rd, a beautifully maintained traditional-style home offering the perfect blend of comfort, charm, and convenience. This spacious residence features 4 bedrooms, 2.5 remodeled baths, a 2-car garage, and a full basement with endless possibilities for storage, recreation, or future finished space. The remodeled kitchen is designed for both functionality and style, while the inviting family room with a fireplace creates the perfect gathering space for relaxing evenings at home. Recent updates include a new roof in 2018 and a new HVAC system installed in 2024, providing added peace of mind. Step outside to enjoy the brick patio and large fenced backyard, ideal for entertaining, pets, gardening, or outdoor activities. Conveniently located just off Rt. 7, this home offers easy access to shopping, dining, schools, parks, and commuter routes. Enjoy nearby attractions including Historic Downtown Winchester, Shenandoah University, Apple Blossom Mall, Winchester Country Club, Jim Barnett Park, local wineries and breweries, and easy access to the Shenandoah Valley’s outdoor recreation, hiking trails, and scenic countryside. This exceptional property combines timeless appeal with an unbeatable location. More photos coming soon.

111 Old Wagon Rd, Winchester

Listing courtesy of RE/MAX Roots. Contact:

Selling Office: Keller Williams Realty.

223 Asbury Rd, Winchester
$540,000
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:

Selling Office: Samson Properties.

223 Cavalry Dr, Winchester
$515,000
5 Beds ⋅ 4 Baths
Nestled in a prestigious eastside enclave, this exquisite residence offers an unparalleled blend of sophistication and convenience, mere minutes from Winchester’s vibrant core—perfect for discerning commuters. A meticulously landscaped exterior ushers you into a breathtaking open-concept interior, where timeless elegance meets modern comfort. ***MAIN LEVEL: The heart of the home is a soaring two-story living room, where a gas fireplace casts a warm glow, creating an inviting ambiance for both intimate gatherings and grand entertaining. Seamlessly connected, the gourmet kitchen—a culinary masterpiece—boasts premium finishes and flows effortlessly into a radiant four-season room, bathed in natural light and designed for year-round serenity. This level is completed by a versatile bedroom or office, a full bath, and a thoughtfully appointed laundry room. ***UPPER LEVEL: Ascend to a haven of tranquility, where two spacious bedrooms and a full bath await, and also a luxurious owner’s suite—a true retreat with its own full bath. ***LOWER LEVEL: The finished lower level offers boundless possibilities, featuring a generous family room equipped with a state-of-the-art entertainment system, a full bath, a bedroom, and a workshop wired with 220-volt outlets, ideal for ambitious projects or creative pursuits. *** This distinguished home harmonizes refined craftsmanship, functional design, and an enviable location, delivering the elevated lifestyle you’ve always envisioned.

223 Cavalry Dr, Winchester

Listing courtesy of Coldwell Banker Premier. Contact:

Selling Office: NextHome Realty Select.

129 Old Wagon Rd, Winchester
$499,000
4 Beds ⋅ 3 Baths
*Sellers are offering $850 towards a home warranty of the buyer's choice* "Outstanding On Old Wagon" This 4 bedroom, 2 1/2 bath colonial style home sits in a cul-de-sac in the highly desirable Pioneer Heights Neighborhood. This home has had a ton of upgrades over the years! Gorgeous, updated custom kitchen with Frigidaire Gallery Appliances, custom built cabinets with pull out shelves, extra depth cabinet over the refrigerator, Corian Quartz Countertops, large undermount sink, under cabinet rechargeable lighting, pantry with lighting, ceiling fan and recessed lighting! Main level also includes a spacious family room, dining room, living room, eating area and a remodeled powder room with a custom vanity that has a Corian Quartz Countertop, new lighting and a comfort height toilet. Primary bedroom recently painted, updated electrical outlets/switches, updated fan and private bathroom with the following updates: Barn door, custom tiled shower with 24-inch niche, rain head & handheld sprayer, barn style shower door, wolf bottom & Kitchen Maid tower cabinet with Caesarstone Quartz Countertop, 2 undermount sinks with brushed gold faucets, updated lights, LVT marble style flooring and comfort height toilet. Three additional bedrooms on the upper level and a hallway bathroom with the following updates: Custom vanity with Quartz's Countertops, undermount sink, updated lighting, custom wrought iron accessories, comfort height toilet and LVT flooring. Hardwood throughout the home besides the upstairs bathrooms. Unfinished walk-out basement with plenty of space if you need to add extra sq footage. First floor laundry room. Step out back and enjoy the spacious Trex deck (With 20-year Baer Stain on posts/wood & bar height wide top) and mature trees for privacy. Two car garage to keep your vehicles dry or store your yard equipment. Additional upgrades include French doors installed in the basement, the basement floor has been epoxied, front storm door installed, laundry room cabinets installed and deadbolt in the laundry room/garage replaced. Water softener is 2025, Windows upstairs & kitchen were replaced in 2024, Roof is 2019, Water heater is 2019 and upstairs A/C was replaced in 2013. You won't want to miss this one!

129 Old Wagon Rd, Winchester

Listing courtesy of Samson Properties. Contact:

Selling Office: Coldwell Banker Realty.

102 Settlers Cir, Winchester
$497,000
3 Beds ⋅ 3 Baths
This classic Colonial home, ideally situated in a desirable Winchester neighborhood, offers 3 spacious bedrooms and 2.5 baths. Rich in charm, this home boasts a traditional layout with over 3300 sq feet on 3 levels. There is a Bonus room that would be perfect for use as a 4th bedroom, home office, or guest space. Improvements include a Brand new architectural shingle roof, newer water heater, and a well maintained dually zoned HVAC system with a new condenser unit. You will LOVE the Gleaming wood floors throughout the main level! Bathrooms are updated with luxury vinyl plank and tile flooring. The Kitchen is elegant with vintage style cabinetry, granite countertops, gas stove cooking, a roomy pantry, and an island, all overlooking the large landscaped backyard. A great place to entertain, the rear outdoor space has a stunning patio with a cozy pergola, relaxing water fountains, and a warm fire pit area to gather around. Not to mention the Fully fenced rear has lots of majestic trees for a feeling of privacy and peace. The Unnfinished basement has a rough-in and it's just waiting for your dream project! This location has effortless access to vibrant downtown, with a variety of restaurants, entertainment, and cultural attractions! Ideal location for commuters! A Must See Schedule a Showing Today!

102 Settlers Cir, Winchester

Listing courtesy of ERA Oakcrest Realty, Inc.. Contact:

Selling Office: Burch Real Estate Group, LLC.

107 Tucks Cir, Winchester
$489,000
4 Beds ⋅ 2 Baths
Welcome to this truly special, lovingly maintained one-level home in desirable Pioneer Heights, ideally located just minutes from Route 7 East for an easy commute. Situated on a quiet cul-de-sac, this well-built residence blends timeless charm with thoughtful updates throughout. Major improvements include new granite countertops in the kitchen, updated bathrooms with new vanities, specialty tile flooring, new lighting and mirrors, new hardwood floors in most rooms, and refinished existing hardwoods. Additional upgrades include new foam insulation in the attic, new insulation in the crawl space, a roof approximately 12 years old, and an HVAC system approximately 11 years old. The home sits on a beautiful, large, and shaded lot with mature trees and plantings, including a crepe myrtle and magnolia. The inviting outdoor space features a charming picket fence and a spacious deck that offers the perfect balance of sunlight and shade beneath mature pine trees. The front brick façade showcases distinctive corner detailing, adding to the home’s curb appeal. Inside, gleaming hardwood floors welcome you into a traditional formal entry, while the rear of the home opens into a bright, contemporary layout. The open-concept living area includes a spacious great room, sunny breakfast room, and large kitchen with a built-in desk. The breakfast room features a graceful floor-to-ceiling bump-out with peaceful views of the backyard. The thoughtfully designed bedroom layout offers privacy, with the primary suite set apart from the additional bedrooms. The generously sized primary bedroom features refinished hardwood floors, a tray ceiling, space for a reading nook, and a large walk-in closet. The recently remodeled primary bath includes a double vanity, soaking tub, separate shower, and a large window overlooking the serene outdoor setting. This exceptional home offers comfortable one-level living, abundant upgrades, and a tranquil setting. A truly special property—don’t miss the opportunity to show your buyers this wonderful home. Also house has a whole home water softening system and a level 2 EV charger.

107 Tucks Cir, Winchester

Listing courtesy of Keller Williams Realty. Contact:

Selling Office: Redfin Corporation.

237 Asbury Rd, Winchester
$475,000
4 Beds ⋅ 3 Baths
Welcome to 237 Asbury Road in Winchester tucked away on a quiet cul-de-sac yet perfectly located just off Rt. 7 for an easy commute. This 4-bedroom, 2.5 bath home offers a spacious, functional layout with multiple living areas, including a living room, separate dining room, and a family room with fireplace. The custom kitchen features granite countertops, a center island with prep sink, ample cabinet space, a pantry for additional storage and a breakfast nook. The spacious primary suite includes a walk-in closet and a private bath with double vanities, a jetted tub, and a stand-up shower. In addition to the primary suite, there are three spacious bedrooms offering flexibility for family, guests, or home office space. Also, has a huge full unfinished basement that walks out to the wooded backyard and offers endless possibilities for storage, recreation space, or future expansion. Step outside to enjoy a private, tree-lined backyard that backs to woods—giving you both space and privacy. The rear deck connects seamlessly from the wraparound porch, creating a great flow for outdoor entertaining or simply enjoying the peaceful setting. If you’ve been looking for space, privacy, and a commuter-friendly location all in one this home checks the boxes!

237 Asbury Rd, Winchester

Listing courtesy of ERA Oakcrest Realty, Inc.. Contact:

Selling Office: Real Broker, LLC.

228 Cavalry Dr, Winchester
$475,000
4 Beds ⋅ 3 Baths
Cul-de-sac setting, a front porch you’ll actually use, and a backyard designed to enjoy—this home makes everyday living easy. Located in Pioneer Heights on the east side of Winchester, this home offers a practical layout with thoughtful updates throughout. The kitchen is both functional and inviting with granite countertops, a 5-burner gas cooktop, stainless steel appliances, and an island for extra storage. A bright breakfast area overlooks the fenced backyard, keeping everything connected for everyday living. Upstairs, you’ll find four bedrooms, including a primary suite with vaulted ceilings, a walk-in closet with window, and a private bath with dual vanities, soaking tub, and separate shower. Out back, the Trex deck (2022) extends your living space and leads to a patio—offering flexibility for relaxing or gathering. The yard is fenced with mature landscaping, and the playset conveys. Additional updates include refrigerator (2023), dishwasher (2025), washer and dryer (2025), updated downstairs bath (2021), front porch improvements, and architectural roof (2019 per previous listing). Set in an established neighborhood with convenient access to commuter routes, shopping, and everyday essentials.

228 Cavalry Dr, Winchester

Listing courtesy of ERA Oakcrest Realty, Inc.. Contact:

Selling Office: Realty ONE Group Old Towne.

303 Asbury Rd, Winchester
$475,000
3 Beds ⋅ 2 Baths
Nestled in the charming Pioneer Heights, this delightful one level ranch custom home offers a perfect blend of comfort and functionality. With 1,771 square feet of living space, this residence invites you to create lasting memories. The warm ambiance is enhanced by a cozy fireplace, perfect for those chilly evenings spent with loved ones. Set on a generous half acre lot, with a fully fenced in outdoor space with a covered deck, provides endless possibilities for gardening, play, or simply enjoying nature. The kitchen has granite counter tops, two panties, a stand mixer lift, and and vast custom cabinetry for extra storage , any chef's dream. The living space has plenty of natural light shining through the skylights. The master bedroom has a large master closet and there is a separate room for the washer and dryer. The attached two-car garage ensures convenience and ample storage. Built in 1994, this home boasts classic vinyl siding and a timeless design that stands the test of time. Experience the tranquility of suburban living while being just a short drive from local amenities. This property is not just a house; it's a place to call home. Don't miss the opportunity to make it yours!

303 Asbury Rd, Winchester

Listing courtesy of Samson Properties. Contact:

Selling Office: Coldwell Banker Premier.

100 Winns Cir, Winchester
$405,000
4 Beds ⋅ 3 Baths
OPEN HOUSE UPDATE!!! Saturday's open house has been canceled, please visit Jennifer Warnock, hosting on Sunday, 3/22 from 10am - 2pm!!! ***///*** Welcome home to Winns Circle! This is a fantastic opportunity for future homeowners to live in a bright, spacious home on the east side of Winchester, as the home is listed under the tax assessed value, as well as the most recently appraised value of $487,700 (completed 1/21/2026 and available to qualified buyers upon request) and the After Repair Value of $522, 700, as noted on the appraisal. This home is ready to move in and become the showpiece you envision with some updates and upgrades throughout. With lots of space for entertaining, hobbies, and anything you can imagine, this beautiful Colonial is simply waiting for its next homeowner.

100 Winns Cir, Winchester

Listing courtesy of Coldwell Banker Premier. Contact:

Selling Office: Unrepresented.

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