Looking to Buy or Sell a Home in Middletown?
Check Out These Homes for Sale in Middletown, VA
Meet RoxAnn, Your Trusted REALTOR for Middletown, 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 Middletown area, 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."
Calvin G.
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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."
Erica P.
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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."
Stephanie A.
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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."
Mina S.
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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."
Amy B.
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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."
Corinne S.
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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."
Irving P.
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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."
Matt N.
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"I was thrilled to get to work with her!"
Julianne C.
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"Her team was amazing. They understood my goals and stopped at nothing to help me check every box."
Joshua S.
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"She is hands down the best realtor in the area!"
Carissa P.
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"She was very thorough and very responsive to any question in any call that we made to her."
Carl T.
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Why Move to Middletown, VA?
Thinking about making Middletown your next home? Many people are drawn to this charming Shenandoah Valley town for its peaceful atmosphere, scenic surroundings, and strong sense of community.
Middletown, VA blends historic character with small-town comfort. Nestled between rolling farmland and mountain views, it offers a relaxed lifestyle with easy access to outdoor recreation. Whether you enjoy walking local trails, taking in the views around Cedar Creek & Belle Grove National Historical Park, or simply appreciating the quiet, open landscapes, Middletown gives you space to breathe and enjoy the beauty of the Valley.
Yet, it’s more than just a scenic place to live. Middletown has a warm, hometown feel, with local restaurants, small businesses, and community events that bring neighbors together throughout the year. From seasonal festivals to locally owned shops, it’s the kind of place where people enjoy connecting and supporting their community.
For commuters, Middletown offers convenience without the crowds. With quick access to I-81 and Route 11, you’re only minutes from Winchester, Stephens City, and other regional hubs, making it easy to balance work, school, and daily life. Whether you work locally or travel for your career, Middletown provides a quieter home base without sacrificing accessibility.
Many homebuyers appreciate Middletown for its thoughtful pace of life, local amenities, and the variety of housing options available. It’s a town where you can feel comfortable putting down roots and creating a home that matches your lifestyle. As your dedicated REALTOR in Middletown, VA, our team is here to help you explore the area and discover what makes this community such a wonderful place to live.
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Compared to many regions in Virginia and the surrounding metropolitan areas, Middletown is generally considered more affordable. Housing prices vary depending on the type of home, location, and current market trends, but many buyers find Middletown offers strong value for their investment. Working with a knowledgeable REALTOR in Middletown, VA can help you understand local pricing, explore available options, and find a home that fits your budget and goals.
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Yes, Middletown, VA is a great place to live for those who appreciate a peaceful small-town atmosphere with convenient access to nearby cities like Winchester and Front Royal. The community offers scenic surroundings, local parks, historic landmarks, and a relaxed pace of life. Residents value the town’s blend of rural charm and modern convenience, along with its proximity to outdoor recreation throughout the Shenandoah Valley.
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Middletown is known for its rich history, scenic Shenandoah Valley landscape, and its connection to key Civil War landmarks, including the well-known Cedar Creek & Belle Grove National Historical Park. The town also hosts family-friendly community events and is home to local restaurants, farms, and historic sites that highlight the area’s heritage. With a charming main street and easy access to outdoor activities, Middletown offers a unique blend of history and natural beauty. Qualities that make it a special place for residents and visitors alike.
Recent Listings We’ve Sold
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Real Estate Services in Middletown, VA
As dedicated REALTORS® serving Middletown, VA, our team provides professional guidance for local buyers and sellers. We pride ourselves on offering honest insights, market expertise, and personalized support throughout every step of your real estate journey.
Seller's Agent Services
Our seller representation focuses on strategic pricing, effective marketing, and professional guidance from listing to settlement. We work to showcase your property with high-quality presentation, targeted exposure, and clear communication to help you achieve a successful sale.
Buyer's Agent Services
Whether you’re searching for your first home or your next one, we help you navigate the Middletown market with confidence. Our buyer services include personalized home searches, local market knowledge, skilled negotiation, and support throughout the entire process.
Appraisals
We provide access to trusted appraisal resources to help you understand your property’s value based on market conditions and comparable homes. Accurate valuation is an essential step for both buying and selling in Middletown.
Listing Service
Our full listing service includes professional marketing, property preparation guidance, photography coordination, MLS exposure, and ongoing communication. We aim to present your home in its best light and reach motivated buyers effectively.
First-time Home Buyer Services
We enjoy supporting first-time home buyers by offering clear explanations, patient guidance, and local knowledge. From understanding financing options to touring homes and writing offers, we help make the experience smooth, informed, and enjoyable.
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.
