Winchester Real Estate

Winchester Real Estate

Welcome to Winchester, Virginia – a charming city steeped in history and surrounded by the breathtaking beauty of the Shenandoah Valley. Nestled in the northern part of the state, Winchester boasts a rich tapestry of culture, heritage, and modern amenities that make it an ideal place to call home.

Founded in 1744, Winchester is renowned for its historic significance, particularly during the Civil War. The city is home to numerous well-preserved landmarks, including the Old Court House and the George Washington Hotel, which tell stories of a bygone era. Strolling through the quaint streets of Old Town, you'll discover an array of boutique shops, delightful cafes, and local eateries, all set against a backdrop of stunning 18th and 19th-century architecture.

Nature enthusiasts will appreciate Winchester's proximity to the picturesque Shenandoah National Park and the Appalachian Trail, offering endless opportunities for hiking, camping, and exploring the great outdoors. The city also hosts a vibrant arts scene, with galleries, theaters, and music festivals that celebrate local talent and culture.

Education and community are at the heart of Winchester, with a strong emphasis on quality schools and family-friendly neighborhoods. The city’s welcoming atmosphere and diverse population create a sense of belonging that is hard to replicate.

Whether you're looking for a historic home, a modern apartment, or a spacious family house, Winchester offers a variety of real estate options to suit your lifestyle. Come experience the warmth and charm of Winchester, where history meets modern living in a picturesque setting!

Newest Listings in Winchester

$719,000
5 Beds ⋅ 5 Baths
Warm, elegant, and beautifully maintained, this 5-bedroom, 4.5-bath home offers gracious living in a desirable City of Winchester neighborhood with no HOA. Step into the spacious foyer, where refined crown molding and a striking staircase create a memorable first impression. Just beyond, a private office with built-in shelving and a cleverly concealed Murphy bed offers exceptional versatility, while the formal living room flows gracefully into a column-framed dining room designed for memorable gatherings. At the heart of the home, the bright and welcoming kitchen features an island cooktop and an adjoining breakfast area with double doors opening to a hardscaped patio - a lovely setting for morning coffee in the eastern sun. The family room invites you to settle in beneath vaulted ceilings beside the warmth of the gas fireplace, while a second staircase provides convenient access to the upper level. Upstairs, four generously sized bedrooms offer comfort and privacy, including two with en-suite baths, plus an additional full bath. The serene primary suite features two walk-in closets and a spacious bath with a soaking tub and separate walk-in shower. The finished lower level provides abundant space for entertaining, exercising, playing, or relaxing, along with generous storage, a half bath, and walk-up access to the backyard. Thoughtful updates include a new roof (2024), main-level HVAC (2026), upper-level HVAC (2023), updated carpeting (2018), and a kitchen refresh (2019). Immaculate, spacious, and wonderfully inviting, this exceptional home is ready to welcome its next owner. Schedule your private tour today.

961 Meadow Ct, Winchester

Listing courtesy of Colony Realty. Contact:

$298,900
2 Beds ⋅ 2 Baths
PRICED TO SELL!!! This all-brick Ranch 2-3 bedrooms, 1.5 bathrooms, hardwood floors, kitchen has been updated with granite countertops. Full basement partly finished basement, with workshop on a walk out to back yard. The outside shop is ready to set up shop with plenty of room for storage, and it has Electric! Great yard to enjoy all the seasons and relaxing. All this and so much more for $298,900.00.

828 Woodland Ave, Winchester

Listing courtesy of Samson Properties. Contact:

$650,000
4 Beds ⋅ 2 Baths
Welcome to peaceful country living on sought-after Apple Pie Ridge. This farmette situated on approximately 6.34 acres, offers the space, privacy, and charm that make Shenandoah Valley living so desirable. The home features four bedrooms, two bathrooms, warm knotty pine flooring, generous living space, and numerous practical improvements that create a comfortable country lifestyle. With one bedroom and bathroom on the main level, the home is conveniently set up for all stages of life. Outside, enjoy open acreage with room for gardening, recreation, or simply taking in the surrounding countryside. A detached garage with a wood stove provides excellent workshop or hobby space, while the basement and attic offer additional storage and flexibility. Whether you're looking for room to spread out, a place to enjoy quiet evenings, or a property that balances rural living with convenient access to Winchester, this home offers a wonderful opportunity. Experience the beauty of Apple Pie Ridge while enjoying the comfort of a well-maintained country home.

4208 Apple Pie Ridge Rd, Winchester

Listing courtesy of Virginia Real Estate. Contact:

$774,900
4 Beds ⋅ 4 Baths
Welcome to 159 Lavender Hills Lane, where space, comfort, and a peaceful setting come together in a home designed for both everyday living and entertaining. With approximately 4,600+ finished square feet across three finished levels, this spacious home offers plenty of room to spread out. The main level features an open floor plan with formal living and dining areas, an updated kitchen with upgraded cabinetry, countertops and stainless steel appliances, a breakfast area, and a large family room perfect for gathering. Upstairs, the spacious primary suite offers a relaxing retreat with a large walk-in closet and private bath featuring a soaking tub and tiled shower. Two additional bedrooms share a Jack-and-Jill bath, while a fourth bedroom includes its own private bath, ideal for guests or family. The finished walkout basement provides even more flexible living space with plenty of possibilities for a recreation room, home gym, office, media room, or guest space. Outside, enjoy the peaceful surroundings from the back deck with a screened canopy, creating a wonderful spot for morning coffee, quiet evenings, or outdoor entertaining. The fenced backyard adds another layer of functionality for pets, play, or simply enjoying your own outdoor space. The home has also benefited from numerous significant updates, including newer AC units, an upgraded 80-gallon water heater, high-speed Starlink internet, a newer microwave, upgraded sump pump, new laundry room cabinets, upgraded garage doors, a new furnace in 2025, new heat pump in 2026, and septic service and pump replacement in 2026. With generous living space, a finished walkout lower level, a peaceful outdoor setting, and extensive system updates already completed, **159 Lavender Hills Lane offers the space to live, work, relax, and entertain—all in one place.**

159 Lavender Hills Ln, Winchester

Listing courtesy of Realty ONE Group Old Towne. Contact:

$399,900
4 Beds ⋅ 3 Baths
Privacy, location, and plenty of room to make it your own. Welcome to 111 Glendale Cir! Situated in one of Winchester’s established and well-loved communities, this home puts you close to so much of what the area has to offer, including downtown Winchester, Winchester Country Club, Jim Barnett Park, schools, shopping, restaurants, and more. And the location gets even better once you arrive home. Tucked into a quiet cul-de-sac, this property backs to a large wooded, undeveloped parcel, while the entire left side of the street is free of neighboring homes, creating a rare sense of privacy and space. The backyard is truly an extension of the home and offers plenty of opportunity to create your own outdoor retreat beginning around the brick firepit. The property extends beyond the existing brick retaining wall, providing additional usable space for a playset, expanded landscaping, garden area, or whatever fits your vision. A peaceful stream also runs alongside the property, adding to the natural setting and creating a backyard that feels tucked away from it all. Inside, the main level offers a comfortable layout with three generously sized bedrooms, each with good closet space. One bedroom features an entire wall of built-in shelving, while the primary bedroom includes its own convenient half bath. The updated kitchen features stainless steel appliances and butcher block countertops, while the bathrooms retain timeless tilework that blends easily with a variety of styles. Downstairs, the finished basement adds another level of possibilities. A spacious area centered around a large fireplace and mantle with a gas fireplace provides a great space for a family room, recreation area, home office, or future fourth bedroom. The basement also includes the laundry area with the washing machine and new dryer, along with side exterior entrance for added convenience and flexibility. Several of the home's major, cost-saving improvements have already been completed, including a new roof in 2019, HVAC system in 2022, water heater in 2020, and updated electrical panel and breakers in 2015. A Tesla electric vehicle charging station is also already in place. With its exceptional location, cul-de-sac setting, privacy, usable outdoor space, and important updates already completed, 111 Glendale Cir offers a combination that is increasingly hard to find. Come explore the property, see the possibilities, and discover how easily you can make this Winchester home your own.

111 Glendale Cir, Winchester

Listing courtesy of Realty ONE Group Old Towne. Contact:

$399,999
4 Beds ⋅ 4 Baths
🏡 Winter Delivery – St. Paul LAST END UNIT!! 4 Bedrooms | 3.5 Bathrooms | Finished Lower Level | Larger Composite Deck | 🔥 Beautiful wooded homesites are available! Enjoy up to 2,250 sq. ft. of modern, open-concept living. Customize the home to fit your style, or keep the included selections as-is at the advertised price—including the fourth bedroom and full bathroom on the lower level. ✨ Home Highlights 🍽 Open-concept main level—perfect for entertaining 🪨 Granite countertops 🧰 Stainless steel appliances 🪵 Luxury vinyl plank flooring 🛌 Upper-Level Retreat 🚿 Deluxe Silver primary bathroom with rain shower 👕 Spacious walk-in closet 🧺 Bedroom-level laundry 🛏 Two additional bedrooms and a full bathroom 🎬 Finished Lower Level 🛏 Fourth bedroom 🛁 Full bathroom 💼 Ideal for guests, a home office, gym, or media room 🌟 Additional Features 🌳 Townhome landscaping package 🔌 Deako smart light switches and smart-home features 🌅 Larger composite deck 🏦 Special financing programs available 💰 Builder incentives available when using the preferred lender 📅 Projected delivery: WINTER 📲 Contact the listing agent for current pricing and incentives. 📸 Photos are representative and may show optional features.

Homesite 40 Shuoner Court, Winchester

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

$374,990
3 Beds ⋅ 3 Baths
🏡 MOVE IN READY NOW ✨ St. Paul Townhome TBB | 3 BR | 2.5 BA | 🚗 1-Car Garage | Finished Lower Level 🔥 Beautiful wooded homesites available! Offering up to 2,000 sq. ft. of modern, open-concept living designed for today's lifestyle. ✨ Home Highlights 🍽 Open-concept main level — perfect for entertaining family and friends 🪨 Granite countertops 🧰 Stainless steel appliances 🪵 Luxury vinyl plank flooring throughout the main level 🛌 Upper Level Retreat 🚿 Deluxe Silver primary bath with spa-inspired rain shower 👕 Spacious walk-in closet 🧺 Convenient bedroom-level laundry 🛏 Two additional bedrooms and a full bath 🎬 Finished Lower Level 🛁 Finished recreation room 🛏 Beautiful 12" x 24" tile in all full bathrooms and laundry room 💼 Perfect space for guests, a home office, gym, media room, or playroom 🌟 Additional Features 🌳 Professionally designed townhome landscaping package 🔌 Deako smart light switches and smart home features 🏡 Energy-efficient construction and modern finishes throughout 🏦 Special financing programs available 💰 Builder incentives available with preferred lender 📅 MOVE IN READY NOW 📲 Contact Jimmy Thomas for current pricing, available homesites, and incentives. 📸 Photos are representative and may show optional features.

118 Shuoner Ct, Winchester

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

$225,000
2 Beds ⋅ 1 Baths
As Is Property! Nestled on a sprawling 6.37-acre lot, this charming cabin-style home offers a unique investment opportunity with significant potential for returns. Built in 1971, this detached residence combines rustic charm with modern possibilities, making it an ideal choice for savvy investors looking to capitalize on the growing demand for cozy retreats. Featuring two spacious bedrooms and a full bathroom, this home provides a warm and inviting atmosphere perfect for relaxation. The vinyl siding ensures low maintenance, while the expansive outdoor space invites creativity-think gardens, outdoor entertainment areas, or even additional structures to enhance rental income. The property includes a detached garage with ample storage, providing convenience for both personal use and potential rental opportunities. With a dirt driveway leading to the home, the property offers a sense of seclusion while remaining accessible. Investors will appreciate the potential for short-term rentals or long-term leases, especially given the increasing popularity of cabin getaways. The serene surroundings and ample land create an appealing escape for those seeking tranquility, making it a prime candidate for vacation rentals. This property is not just a home; it's a canvas for your investment dreams. With the right vision, this cabin can become a lucrative asset in your portfolio, offering both comfort and financial growth. Don't miss out on this exceptional opportunity to invest in a piece of tranquility!

132 White Pine Ln, Winchester

Listing courtesy of Long & Foster Real Estate, Inc.. Contact:

$299,900
3 Beds ⋅ 2 Baths
Updated, move-in ready, and waiting for you to make it your own! Welcome to 1013 Orchard Hill Dr. Tucked away in a charming, established Winchester neighborhood with no HOA, this inviting townhome combines a clean, comfortable style with many of the big-ticket improvements already taken care of. Outside, you'll find a brand-new roof and vinyl siding, fresh landscaping, and an updated rear deck complete with durable vinyl railing. Step inside to a spacious main level with an easy, open flow between the living and dining areas. The living room is warm and welcoming, centered around a wood-burning fireplace with built-in cabinetry on both sides, the perfect spot to settle in on a cool evening. The adjoining galley-style kitchen offers plenty of functionality with the laundry conveniently located just off the kitchen. Beyond the dining area, the home gets even better with a large bonus sunroom, complete with additional built-ins and an entire wall of pantry storage. Whether you envision it as a casual gathering space, home office, hobby area, or simply a place to enjoy the extra room, this flexible space adds even more versatility to the home. Upstairs, new carpeting runs throughout, complemented by fresh paint in the entire home. The brand-new full bathroom features a tub/shower combination and new vanity, giving the space a crisp, updated feel. The best part? The major exterior work has already been done, the home is clean and move-in ready, and there's still plenty of opportunity to bring your own style to the interior. Priced competitively, 1013 Orchard Hill Dr offers an opportunity to enjoy a desirable Winchester setting, the freedom of no HOA, and a home where the important updates have already been taken care of. Come see it for yourself and imagine what you'll do with the rest!

1013 Orchard Hill Dr, Winchester

Listing courtesy of Realty ONE Group Old Towne. Contact:

$339,000
2 Beds ⋅ 2 Baths
Welcome to this 2 bedroom, 1.5-bath brick rancher in Bufflick Heights in Winchester, VA. The home features hardwood flooring in the living room and bedrooms, with an inviting living room offering an electric fireplace and plenty of natural light. The kitchen provides ample cabinet and storage space and is equipped with double sinks, a wall oven, and cooktop. The primary bedroom offers two closets plus a convenient makeup desk area. Outside, enjoy a nicely landscaped yard and a brick walkway leading to the front porch, a great spot to sit and enjoy your morning coffee or relax at the end of the day. A covered walkway provides easy access to the attached garage, which includes a walk-up storage area. Several additional storage buildings provide plenty of room for tools, hobbies, and extra storage. An asphalt driveway completes the property, offering comfortable one-level living with plenty of storage and classic brick exterior appeal.

121 Elmwood Rd, Winchester

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

$724,900
5 Beds ⋅ 5 Baths
***SELLER IS WILLING TO CONTRIBUTE UP TO $20,000.00 IN CONCESSIONS TOWARD BUYER CLOSING COSTS OR POINT BUY-DOWN WITH AN ACCEPTABLE OFFER.*** Better than new in coveted Abrams Pointe! This pristine 5-bed, 4.5-bath home offers effortless luxury with gleaming hardwoods on two levels, and smart-home tech throughout. Highlights include a dramatic 2-story foyer, a main-level office behind French doors, and an upgraded gourmet kitchen with GE Café appliances and quartz counters. Unwind in the grand primary suite featuring a private sitting room, double-sided fireplace, and spa-inspired bath. The fully finished lower level adds a recreation room, the 5th bedroom, and a full bath. Minutes from historic Old Town Winchester, local shops, and dining. Why wait for a new build when this showstopper has it all? Schedule your personal tour today!

159 Abrams Pointe Blvd, Winchester

Listing courtesy of Keller Williams Realty. Contact:

$409,990
4 Beds ⋅ 4 Baths
BUILDER OFFERING BELOW MARKET RATE FINANCING OPTION ON THIS QUICK MOVE IN HOME!! Brand-New 4-Bedroom Townhome under construction for Move-In soon! Enjoy stylish, low-maintenance living in Snowden Bridge's newest section. This thoughtfully designed home features a convenient entry-level bedroom, oak stairs with upgraded railings, and luxury vinyl plank flooring throughout the main level. The bright gourmet kitchen showcases elegant cabinetry, quartz countertops, and stainless steel appliances, flowing seamlessly into the open living spaces. Upstairs, the spacious primary suite provides a private retreat. Located in a vibrant community with resort-style amenities including a pool, playgrounds, trails, and more to come. Ask about builder incentives! Photos are of a similar home while construction is ongoing.

132 Swansong Pl, Winchester

Listing courtesy of Brookfield Mid-Atlantic Brokerage, LLC. Contact:

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