Winchester Condos for Sale

Winchester Condos for Sale

Welcome to Winchester, Virginia, a charming city steeped in history and surrounded by breathtaking natural beauty. Nestled in the picturesque Shenandoah Valley, Winchester is known for its vibrant downtown, rich heritage, and welcoming community. With its historic architecture, delightful shops, and an array of dining options, this city offers a unique blend of small-town charm and modern amenities.

Winchester is not only a great place to explore but also an ideal location for those seeking a new home. The real estate market here is diverse, with a variety of options to suit every lifestyle. Among these options, you’ll find a selection of stunning condos for sale that cater to both first-time buyers and seasoned investors alike. These condos offer the perfect balance of comfort and convenience, featuring modern designs and amenities that make daily living a breeze.

Imagine waking up in your stylish condo, just moments away from the historic landmarks that tell the story of the city. Enjoy leisurely strolls through the lush parks or take advantage of the outdoor activities that the nearby mountains and rivers provide. With easy access to major highways, commuting to nearby cities is a breeze, making Winchester an ideal spot for both work and play.

Whether you’re looking for a cozy retreat or a vibrant community to call home, Winchester's condos for sale offer a fantastic opportunity to embrace a lifestyle filled with culture, history, and adventure. Discover your dream home in this enchanting city today!

Newest Winchester Condos for Sale

2 Beds ⋅ 2 Baths

Welcome to Winchester Landing, a 55+ condominium community offering comfort, convenience, and low-maintenance living. This secured building provides added peace of mind for residents. This well-designed 2-bedroom, 2-bath condo features a combined kitchen and dining area that opens to a spacious family room—perfect for everyday living. The primary suite features a walk-in shower and ample closet space, complemented by recessed lighting that adds a modern touch throughout. Step outside to your private deck just off the family room and relax. Residents enjoy beautifully maintained common grounds with walking paths and a charming gazebo, along with elevator access for ease and convenience. Community services include lawn care, snow removal, and trash collection, allowing for truly carefree living. Ideally located just minutes from Old Town Winchester, parks, Valley Health, shopping, and restaurants, with quick access to I-81 and VA-7 for easy commuting. All sizes are approximate.

151 Mccormick Unit #203, Winchester

Listing courtesy of RE/MAX Roots. Contact: (540) 686-7362

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

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

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. Seller to provide a credit towards painting of $3,000.

157 Brookland Ter Unit #6, Winchester

Listing courtesy of MarketPlace REALTY. Contact:

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

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:

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

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

Start Your Search

Jessica Sauls | Realtor | Memory Lane Property Group

With over two decades of experience and thousands of successful home sales, I provide calm, confident guidance through every stage of the real estate journey. Since 2003, I’ve helped buyers, sellers, investors, military families, and those navigating major life transitions make smart, well informed decisions. I do this with clarity, integrity, and strong advocacy. Real estate is more than a transaction, it’s deeply personal. I’m known for creating a steady, reassuring experience during what can often feel overwhelming. My clients value my ability to listen closely, communicate clearly, and protect their interests at every step. Whether negotiating complex terms, preparing a home for market, or navigating unexpected challenges, I lead with professionalism, transparency, and care. As a top performing Realtor in Maryland and Pennsylvania, I combine deep market expertise with a strategic, hands on approach. I help sellers maximize value through thoughtful preparation, including repairs and upgrades with payment deferred until closing. For buyers, I provide honest insight, strong negotiation, and a no-pressure approach. I want all of my Clients to move forward with confidence. Having successfully navigated multiple market cycles, I understand how to adapt strategies in changing conditions while keeping my clients’ goals front and center. Beyond real estate, I am deeply committed to my community, supporting scholarships, housing initiatives, and local education. That commitment to service carries into my work, showing up fully, advocating fiercely, and always doing what’s right for my Clients. If you’re looking for an experienced, steady professional who will treat your goals with care and deliver a strong, strategic outcome, I would be honored to work with you. It's my Mission to provide strategic, ethical, and compassionate real estate guidance that empowers people to build stability, wealth, and a life they love. We create calm, clear, and trustworthy experiences, and we strengthen our community through service, connection, and integrity. I believe in building futures, relationships, and legacies that last.

Learn More

Brian Sauls | Realtor | Memory Lane Property Group

Brian brings a thoughtful, detail-oriented approach to every real estate transaction. He helps clients understand the true condition and quality of a home beyond surface details, offering valuable insight during showings and throughout the decision-making process. Known for his calm demeanor, reliability, and strong attention to detail, Brian ensures clients feel comfortable, informed, and well supported from start to finish. He answers questions in real time, offers practical perspective, and helps buyers assess homes with confidence and clarity. Brian’s approach is grounded, professional, and service-oriented. His ability to provide meaningful guidance while keeping the process smooth and stress-free makes him a trusted advocate for his clients every step of the way.

Learn More

Christina Jones | Client Care | Memory Lane Property Group

Christina is the heart of our client experience and serves as our Director of Client Care. From the moment a client enters our world to well beyond the closing table, Christina ensures every detail is handled with care, clarity, and consistency. With a calm, organized, and compassionate approach, Christina manages communication, timelines, and behind-the-scenes coordination so our clients feel supported and informed at every step. She is often the friendly voice checking in, the steady hand keeping everything on track, and the person making sure nothing slips through the cracks. Christina is deeply committed to creating a smooth, low-stress experience for buyers and sellers alike. She understands that real estate transactions often come during significant life moments, and she brings patience, empathy, and professionalism to each interaction. Her focus on service, follow-through, and genuine care allows our team to deliver a thoughtful, high-level experience — one where clients feel heard, respected, and confident throughout the process.

Learn More

Payson Clausen Realtor

Payson Clausen | Realtor | Memory Lane Property Group

Payson Clausen brings together years of experience in real estate, media production, and marketing to support our team and elevate the client experience. With a strong background in both the real estate industry and creative media, Payson plays a key role in how properties, brands, and stories are presented. His expertise in video production, marketing strategy, and digital content helps ensure our listings and messaging are clear, compelling, and thoughtfully executed. Beyond his professional skill set, Payson is deeply committed to serving his community. He regularly volunteers his time working with local students and is actively involved in raising funds for SkillsUSA, supporting career and technical education programs that prepare young people for future success. Payson’s blend of industry knowledge, creative talent, and community involvement reflects our team’s values — using our work not just to serve clients, but to make a meaningful impact beyond the transaction. (function() { var rg = document.createElement('script'); rg.type = 'text/javascript'; rg.async = true; rg.src = 'https://widgets.realgeeks.com/static/js/search_widget_new.js?v=3'; var s = document.getElementsByTagName('script')[0]; s.parentNode.insertBefore(rg, s); })();

Learn More