Winchester Condos for Sale

Winchester Condos for Sale

Welcome to Winchester, Virginia – a charming city steeped in history and nestled in the picturesque Shenandoah Valley. Known for its rich Civil War heritage, Winchester offers a delightful blend of small-town charm and modern amenities. With its vibrant downtown area, residents can enjoy a variety of boutique shops, delightful eateries, and cultural attractions, including the renowned Museum of the Shenandoah Valley. The city is also home to beautiful parks and outdoor spaces, perfect for those who appreciate nature and an active lifestyle.

If you’re considering making Winchester your home, you’ll be pleased to discover an array of stunning condos for sale. These properties offer a unique opportunity to enjoy the convenience of modern living while being surrounded by the area's natural beauty and historic charm. Many of the condos feature contemporary designs, spacious layouts, and desirable amenities such as fitness centers, pools, and community gathering spaces.

Living in a condo in Winchester means you can enjoy a low-maintenance lifestyle without sacrificing comfort or style. Whether you’re a first-time homebuyer, a busy professional, or looking to downsize, these condos provide the perfect balance of affordability and luxury. Plus, with easy access to major highways, commuting to nearby cities like Washington D.C. is a breeze.

Explore the diverse selection of condos for sale in Winchester today, and discover the perfect place to call home in this vibrant and welcoming community. Your dream lifestyle awaits in this enchanting Virginia city!

Newest Winchester Condos for Sale

$275,000
1 Beds ⋅ 1 Baths
Step into the charm of Historic Downtown Winchester with this beautifully renovated Urban Lofts Condominium, where history and modern living come together. Located in a home built in 1825, this unique property is just a short stroll to Winchester's favorite restaurants, boutique shopping, coffee shops, museums, and downtown events. Renovated in 2021, the condo offers stylish updates while preserving its historic character. The kitchen features quartz countertops, stainless steel appliances, a new refrigerator, and a new island with an integrated sink that creates the perfect gathering space. Fresh paint, modern lighting, a beautifully updated bathroom, and a built-in bookcase add to the home's appeal. The exposed brick fireplace serves as a striking architectural feature, adding warmth and character to the living room. (Fireplace is decorative only.) Whether you're looking for your own place in the heart of downtown or an investment opportunity, this low-maintenance condo offers the best of both worlds; historic charm, modern finishes, and an unbeatable location where you can leave the car behind and enjoy everything Winchester has to offer.

135 S Kent St Unit #202, Winchester

Listing courtesy of Realty ONE Group Old Towne. Contact: 5407738475
$254,900
2 Beds ⋅ 2 Baths
Discover the charm of Parkplace Condominiums, where comfort meets convenience in a vibrant community. This inviting 2-bedroom, 2-bathroom unit features modern stainless steel appliances, including a built-in microwave, dishwasher, and electric oven, making meal prep a delight. Enjoy the ease of in-unit laundry with washer and dryer hookups, ensuring your daily routines are seamless. Nestled in a friendly neighborhood, residents benefit from well-maintained grounds with included lawn care, snow removal, and trash services. The community is close to local parks, perfect for leisurely strolls or weekend picnics. Excellent schools are just a stone's throw away, providing quality education options for all ages. With a strong sense of community and convenient access to public services, Parkplace is more than just a home; it's a place to create lasting memories. Experience the warmth and comfort of this lovely unit, where every detail is designed for your enjoyment.

136 Brookland Ct Unit #6, Winchester

Listing courtesy of Realty ONE Group Old Towne. Contact: 5407738475
$249,000
2 Beds ⋅ 2 Baths
Fantastic location! This spacious second-floor condo offers more square footage than most units in the community and features an open, light-filled layout, and durable flooring throughout with NO carpet. The thoughtfully designed floor plan includes a large living room, separate dining area, two generously sized bedrooms, and two full bathrooms. The primary suite offers a private bath, a large closet, and plenty of room for a king-sized bed. The kitchen was remodeled in recent years with quality cabinets, quartz countertops, undercabinet lighting, and new appliances. A separate laundry room with a full-size washer and dryer adds everyday convenience. Step outside to the private deck overlooking the common area and mature trees, creating a peaceful outdoor retreat. An additional private storage unit, conveniently located right next to the condo, provides valuable extra space for seasonal items, bicycles, or other belongings. Condo fee covers common area maintenance, trash, water, sewer and snow removal. One assigned parking space per unit.

157 Brookland Ter Unit #6, Winchester

Listing courtesy of MarketPlace REALTY. Contact:

$240,000
2 Beds ⋅ 2 Baths
Fantastic location! This spacious second-floor condo offers vaulted ceilings, generously sized rooms, and a bright, open feel throughout. Enjoy relaxing on the private deck overlooking the common area and mature trees. The floor plan features a large living room, separate dining room, two spacious bedrooms, and two full bathrooms. The primary suite includes a private bath, a large closet, and plenty of space for a king-sized bed. A separate laundry room with a full-size washer and dryer adds everyday convenience.

127 Brookland Ter Unit #8, Winchester

Listing courtesy of Realty ONE Group Old Towne. Contact: 5407738475
$299,900
2 Beds ⋅ 2 Baths
Welcome home to this one-of-a-kind, fully renovated penthouse condo that has been transformed right down to the studs! Offering luxury finishes rarely found at this price point, this stunning residence is unlike anything else available in Frederick County under $300,000. Every detail has been thoughtfully updated, including a new gas furnace, new HVAC system, new flooring throughout, neutral designer paint, custom molding, and a beautiful custom stone gas fireplace that serves as the centerpiece of the living space. The spectacular kitchen features granite countertops, upgraded soft-close cabinetry, and all-new stainless steel appliances, creating the perfect space for both everyday living and entertaining. Impeccably designed and professionally decorated, this home has the look and feel of a luxury Loudoun County property—without the Loudoun County price tag. As an added bonus, this condo can be purchased fully furnished for just $329,000, making it truly move-in ready or an incredible turnkey investment opportunity. Its convenient location also makes it an ideal home for a Shenandoah University student, faculty member, or anyone looking for low-maintenance luxury living. Don't miss this rare opportunity to own a completely renovated penthouse condo that perfectly blends style, comfort, and value!

110 Brookland Ct Unit #10, Winchester

Listing courtesy of Samson Properties. Contact: (540) 348-4911
$559,900
2 Beds ⋅ 3 Baths
Experience a rare opportunity to own a piece of Winchester history at The Fort, one of Old Town's most distinctive residential communities. Located just blocks from the vibrant Walking Mall, this beautifully renovated 2-bedroom, 2.5-bath condominium seamlessly blends historic character with modern luxury. Unit 105 features an open-concept floor plan with soaring ceilings, rich architectural details, and abundant natural light. The gourmet kitchen is equipped with stainless steel appliances, gas cooking, granite countertops, and a spacious island perfect for entertaining. A cozy library with fireplace, elegant living spaces, and a convenient main-level powder room add to the home's charm and functionality. Upstairs, the spacious primary suite offers a spa-inspired custom shower, and double vanity. A generous second bedroom and full bath with soaking tub provide comfort for guests or family. Additional highlights include a covered porch, dedicated parking space, detached private garage, and beautifully maintained common grounds. Originally the site of Fort Loudoun and later a historic girls' school dating to the 1830s, The Fort offers a truly unique living experience steeped in local history. Enjoy walkable access to Winchester's finest restaurants, shops, breweries, museums, and local attractions while residing in one of the city's most iconic addresses.

411 N Loudoun St Unit #105, Winchester

Listing courtesy of MarketPlace REALTY. Contact:

$249,900
2 Beds ⋅ 2 Baths
✨ Fully Renovated 2026 | Turnkey 2BR/2BA Condo in Park Place ✨ Welcome to 136-8 Brookland Ct—where style, comfort, and convenience come together. This stunning second-floor condo has been completely renovated in 2026, offering a like-new feel without the wait! Step inside to discover all-new flooring, appliances, lighting, fixtures, vanities, doors, and countertops—every detail thoughtfully updated for modern living. The bright, open floorplan is perfect for both everyday life and entertaining, featuring a cozy electric fireplace that adds warmth and charm. The spacious primary suite boasts a walk-in closet and private en-suite bath, while the second bedroom offers flexibility for guests, a home office, or more. Enjoy the ease of one-level living with in-unit laundry and step out onto your private balcony—perfect for morning coffee or unwinding at the end of the day. Located in the sought-after Park Place community, you’ll love the peaceful setting with plenty of parking, all just minutes from shopping, dining, Route 7, and I-81.

136 Brookland Ct Unit #8, Winchester

Listing courtesy of Re/Max Roots. Contact: (540) 686-7362
$229,000
2 Beds ⋅ 2 Baths
2 Bed, 2 bath condominium. New appliances, including water heater and heat pump. Gas fireplace, open concept with separate dining room. Patio/ porch with french doors and skylights in living room allow tons of natural light. Primary suite includes walk-in closet. Conveniently located off rt 7 and 81.

121 Brookland Ct Unit #8, Winchester

Listing courtesy of Re/Max Roots. Contact: (540) 686-7362
$314,900
2 Beds ⋅ 2 Baths
Welcome to refined 55+ living in the highly sought-after Winchester Landing Commons. This exceptional ground-floor residence offers two bedrooms and two full baths, showcasing model-quality finishes and sun-drenched interiors with beautiful views. Designed for both comfort and convenience, this unit features a rare private entrance in addition to the main building access. The thoughtfully designed open-concept kitchen, dining and living area create a seamless space for both everyday living and entertaining. Natural light pours through every room, enhanced by elegant top-down, bottom-up privacy blinds on all windows and recessed lighting throughout, creating a bright and welcoming ambiance. Step outside to your private patio — a peaceful retreat perfect for morning coffee or relaxing while enjoying the surrounding views. Ideally located near the heart of downtown Winchester, you’ll enjoy easy access to parks, museums, restaurants, and shopping. The well-lit exterior and beautifully maintained grounds provide a safe, inviting, and accommodating community environment. Photos will be uploaded Thursday, March 5

151 Mccormick Circle Unit #105, Winchester

Listing courtesy of EXP Realty, LLC. Contact: 8668257169
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