55+ Communities in Winchester, VA
Retiring in Winchester?
Winchester, VA offers a welcoming selection of 55+ retirement communities designed for comfort, convenience, and connection. Nestled in the beautiful Shenandoah Valley, these neighborhoods combine relaxed living with small-town charm and scenic surroundings. Whether you’re searching for low-maintenance living, resort-style amenities, or a peaceful community close to historic downtown Winchester, you’ll find the perfect place to enjoy your next chapter.
See the Latest Homes & Condos for Sale in 55+ Communities
Meet RoxAnn, Your Trusted REALTOR in Winchester, VA
FIVE-STAR SERVICE YOU CAN COUNT ON
"With over two decades in real estate, I've learned that listening is just as important as experience. My team and I know the Front Royal market inside and out, and we’re here to help you every step of the way. Whether you're buying, selling, or just exploring your options. When you work with us, your goals become our mission." — RoxAnn Grimes
Over 130+ 5-Star Reviews!
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"I highly recommend RoxAnn Grimes as a real estate agent. Living out of state, it was crucial to have a reliable and knowledgeable agent and she exceeded all my expectations."
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"RoxAnn & her team are the Best I’ve ever worked with. She has been great for multiple projects purchasing, renting and selling."
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"RoxAnn is absolutely an amazing realtor! She goes above and beyond her job and always looked out for my very best interest. She treated me just like family the whole way."
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"Her attention to detail and commitment to finding the perfect home truly set her apart. She was always available every step of the way."
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"I can't say enough about how much I appreciate everything that Roxann did for us with the sale of our home and the purchase of a new one."
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"Amazing from start to finish! As first-time homebuyers navigating a new construction build, we couldn’t have asked for a better advocate. "
Rachel R.
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"You will not find a better real estate agent in the area than Roxann. Knowledgeable, caring, attentive and always willing to go the extra mile."
Bruce B.
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"RoxAnn was professional, very communicative, flexible with scheduling, & knowledgeable. She helped me find a great house."
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"With her knowledge and expertise of the local area and market trends, She was able to match us with the perfect starter home."
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"She is a team player! She will tell you everything you need to know and walk you through every step."
Jordyn S.
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"We were first time buyers so we are very inexperienced with home buying and the process. She went above and beyond."
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"I was thrilled to get to work with her!"
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"Her team was amazing. They understood my goals and stopped at nothing to help me check every box."
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"She is hands down the best realtor in the area!"
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"She was very thorough and very responsive to any question in any call that we made to her."
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Listings in Cedar Meadows 55+ Community
Cedar Meadows is a highly sought-after 55+ community located just minutes from historic downtown Winchester, VA. This peaceful, gated neighborhood offers low-maintenance living with beautifully designed single-level homes, perfect for those looking to simplify without sacrificing comfort. Residents enjoy scenic walking paths, a private clubhouse, and a welcoming, neighborly atmosphere. With its convenient location near shopping, dining, and medical facilities, Cedar Meadows provides the ideal blend of tranquility and accessibility for active adults ready to enjoy their next chapter in the Shenandoah Valley.
Listings in Lake Frederick 55+ Community
Lake Frederick is a vibrant 55+ community just outside Winchester, VA, offering resort-style living surrounded by the natural beauty of the Shenandoah Valley. Centered around a scenic 117-acre lake, this master-planned community features stunning single-family homes, walking trails, and a wealth of amenities designed for active adults. Residents enjoy access to the Shenandoah Lodge & Athletic Club, complete with dining, fitness facilities, and social activities. With its peaceful lake views, modern homes, and engaging lifestyle, Lake Frederick is the perfect place to enjoy retirement in comfort and style.
Listings in Cross Creek Village 55+ Community
Cross Creek Village is a welcoming 55+ community in Winchester, VA, offering relaxed, low-maintenance living in a convenient location. This friendly neighborhood features well-designed single-level homes with modern amenities and thoughtful layouts perfect for easy everyday living. Residents enjoy quiet surroundings, a close-knit atmosphere, and easy access to nearby shopping, dining, and healthcare. With its blend of comfort, convenience, and community spirit, Cross Creek Village is an excellent choice for active adults seeking a peaceful lifestyle in the heart of the Shenandoah Valley.
Listings in Hiatt Pointe at Snowden Bridge 55+ Community
Hiatt Pointe at Snowden Bridge is a premier 55+ community located within the popular Snowden Bridge development in Winchester, VA. Designed for active adults, this neighborhood offers stylish, low-maintenance homes with modern finishes and open floor plans. Residents enjoy access to an impressive array of amenities, including walking trails, a community pool, fitness center, sports courts, and gathering spaces perfect for socializing. With its convenient location near shopping, dining, and downtown Winchester, Hiatt Pointe at Snowden Bridge combines resort-style living with the charm and comfort of the Shenandoah Valley.
Listings in Village at Harvest Ridge 55+ Community
The Village at Harvest Ridge is a charming 55+ community in Winchester, VA, offering a peaceful, low-maintenance lifestyle for active adults. This thoughtfully planned neighborhood features beautifully built single-level homes with open layouts and modern conveniences designed for comfort and ease. Residents enjoy a friendly, close-knit atmosphere with easy access to local shops, restaurants, and medical facilities. Surrounded by the scenic beauty of the Shenandoah Valley, the Village at Harvest Ridge provides the perfect blend of relaxation, convenience, and community for those looking to enjoy their next chapter in Winchester.
Listings in Willow Lawn Cottages 55+ Community
Willow Lawn Cottages is a delightful 55+ community in Winchester, VA, offering comfortable, low-maintenance living in a peaceful setting. Featuring charming cottage-style homes with open layouts and modern touches, this community is perfect for those seeking simplicity and style. Residents appreciate the quiet atmosphere, friendly neighbors, and convenient location just minutes from shopping, dining, and medical facilities. With its combination of comfort, convenience, and small-town charm, Willow Lawn Cottages provides an ideal environment for active adults to enjoy life in the beautiful Shenandoah Valley.
Listings in Woodbrook Villages 55+ Community
Woodbrook Village is a welcoming 55+ community in Winchester, VA, known for its peaceful atmosphere and convenient location. This well-established neighborhood features attractive single-level homes designed for comfort and easy living, perfect for active adults looking to downsize without compromise. Residents enjoy beautifully maintained surroundings, friendly neighbors, and proximity to shopping, dining, and healthcare services. With its blend of serenity and accessibility, Woodbrook Village offers an ideal setting to enjoy a relaxed, fulfilling lifestyle in the heart of the Shenandoah Valley.
Listings in Abrams Chase 55+ Community
Abrams Chase is one of Winchester’s premier 55+ communities, offering a blend of modern comfort and classic charm. Designed for low-maintenance living, this gated neighborhood features beautifully crafted single-level homes with open floor plans, high-quality finishes, and thoughtful details throughout. Residents enjoy a quiet, friendly atmosphere and easy access to Winchester’s shopping, dining, and healthcare options. With its convenient location and scenic Shenandoah Valley surroundings, Abrams Chase provides the perfect balance of relaxation, community, and active adult living.
Listings in Willow Run 55+ Community
Willow Run is a peaceful 55+ community in Winchester, VA, offering relaxed, low-maintenance living for active adults. This inviting neighborhood features beautifully designed single-level homes with modern amenities and spacious layouts that make everyday living easy and comfortable. Residents appreciate the quiet surroundings, friendly atmosphere, and convenient access to shopping, dining, and healthcare nearby. With its combination of comfort, convenience, and small-town charm, Willow Run provides the perfect place to enjoy a carefree lifestyle in the scenic Shenandoah Valley.
Listings in Winchester Landing 55+ Community
Winchester Landing is a desirable 55+ community offering comfortable, low-maintenance living in the heart of Winchester, VA. Designed for convenience and connection, this neighborhood features elegant single-level homes with open floor plans and modern finishes. Residents enjoy a welcoming, close-knit atmosphere along with easy access to shopping, dining, and medical facilities just minutes away. With its peaceful setting and thoughtful design, Winchester Landing provides the ideal environment for active adults to enjoy a relaxed and fulfilling lifestyle in the beautiful Shenandoah Valley.
Why Retire in Winchester, VA?
If you’re thinking about retiring in Winchester, VA, you’ll discover a lifestyle that’s relaxed, scenic, and full of charm. Set in the heart of the Shenandoah Valley, Winchester offers a wonderful variety of 55+ communities designed for comfort, connection, and carefree living. From peaceful neighborhoods with mountain views to communities offering clubhouses, walking trails, and social events, there’s something for every retirement style.
Popular options in the Winchester area feature low-maintenance homes, friendly neighbors, and easy access to shopping, dining, and healthcare. Whether you’re looking for an active adult community, a quiet retreat near historic downtown Winchester, or a neighborhood with resort-style amenities, this area offers it all. No matter your pace or preferences, Winchester is a beautiful place to enjoy your next chapter.
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Real Estate Services in Winchester, VA
When you're searching for a REALTOR in Front Royal, VA, you want someone who brings knowledge, honesty, and local expertise to the table. My team and I are proud to offer personalized support, expert guidance, and real results.
Seller's Agent Services
Ready to sell your home in Front Royal? We’ll take the stress out of the process. From pricing and prep to marketing and negotiations, we handle every detail so you can focus on your next chapter. Our goal is to help you sell quickly and confidently with the best possible outcome.
Buyer's Agent Services
Buying a home in Front Royal? We’re here to make it easier. We’ll help you find the right property, navigate local market conditions, and manage the entire process from offer to closing. Whether it's your first home or your forever home, we’re here to guide you.
Appraisals
Knowing the true value of a home matters. We offer comparative market analysis reports tailored specifically to Front Royal’s housing trends. Whether you're buying or selling, you'll have the data you need to make smart, informed decisions.
Listing Service
Your home deserves to shine. We'll create a compelling listing that stands out in the MLS, with high-quality photos and descriptions that highlight what makes your property special. We focus on reaching the right buyers and getting results.
First-time Home Buyer Services
New to homeownership? We’ll walk you through every step—explaining your options, helping you secure financing, and answering your questions along the way. With us by your side, buying your first home in Front Royal will feel exciting, not overwhelming.
Frederick County, VA
Explore some the most well known areas of Frederick County, VA and see why it is so well loved. Discover new homes in Winchester, Stephen City and Middletown.
Clarke County, VA
Find out more about the charming small towns and beautiful country life in Clarke County, VA. Discover new homes in Berryville, Boyce and Whitepost.
