Windsor Estates Homes under $500,000

Windsor Estates Homes under $500,000

Welcome to Windsor Estates, a charming subdivision nestled in the heart of Frederick, Maryland. This vibrant community offers an exceptional blend of suburban tranquility and urban convenience, making it an ideal choice for families, young professionals, and retirees alike. With its picturesque tree-lined streets and beautifully landscaped lawns, Windsor Estates exudes a warm, welcoming atmosphere that feels like home from the moment you arrive.

One of the standout features of Windsor Estates is the affordability of its homes. With a selection of properties available for under $500,000, this subdivision presents a fantastic opportunity for those looking to invest in their dream home without breaking the bank. These well-designed residences boast modern amenities, spacious layouts, and inviting outdoor spaces, perfect for entertaining or enjoying a peaceful evening under the stars.

Residents of Windsor Estates enjoy easy access to an array of local attractions, including parks, shopping centers, and dining options that cater to every palate. Families will appreciate the proximity to highly-rated schools, ensuring a quality education for their children. For those who love the outdoors, the nearby Catoctin Mountain Park offers hiking trails and stunning views, while the historic charm of downtown Frederick is just a short drive away, providing a delightful mix of culture and community.

In Windsor Estates, you’ll find not just a house, but a place to create lasting memories. Explore the possibilities of homeownership in this delightful subdivision, where your dream home awaits!

Newest Windsor Estates Homes under $500,000

4314 Dover Dr, Frederick

4314 Dover Dr, Frederick

3 Beds ⋅ 3 Baths

The old real estate sayings definitely apply here — good bones and a great location! This well-built rancher sits on 1.33 acres just outside Frederick City, offering the convenience of being close to major commuter routes, shopping, dining and everyday necessities without the city taxes or an HOA. The main level features three bedrooms, one full bath and one half bath, along with hardwood floors throughout much of main level. The full bathroom remodel was started but not completed when the owner became ill, and materials for the project remain at the property. The lower level offers even more usable space with a built-in bar, woodstove, additional room, and an office/workshop area with a level walkout. The former owner also operated a licensed home-based business from the property, giving buyers an idea of the possibilities this space may offer. Buyers should verify any intended business use with the appropriate authorities.

4314 Dover Dr, Frederick

Listing courtesy of J&B Real Estate. Contact:

5601 Calvert Dr, Frederick

5601 Calvert Dr, Frederick

3 Beds ⋅ 3 Baths

Set on just over half an acre, 5601 Calvert Drive offers a combination of features that can be difficult to find this close to Frederick. The home includes 3 bedrooms, a walkout lower level with its own full bathroom and exterior entrance, an oversized two-car garage with additional workshop area, and several major recent improvements—including a brand-new roof (to be installed shortly), new HVAC system, and solar panels. The walkout lower level is one of the home’s biggest advantages. With a full bathroom and direct exterior access, it can easily serve as a guest area, home office, recreation room, gym, hobby area, or extended living quarters. The separate entrance also creates the possibility for a more independent living arrangement or potential rental use. The oversized two-car garage goes well beyond basic vehicle storage. In addition to parking, there is dedicated workshop and storage area that could be used for tools, equipment, projects, bikes, lawn equipment, or just about anything else you would rather keep out of the house. Outside, the just-over-half-acre lot provides plenty of usable yard while offering more separation from neighboring homes than you typically find in many Frederick communities. There is room for outdoor entertaining, gardening, pets, recreation, or simply enjoying a larger property without giving up the convenience of being close to town. With the roof and HVAC already replaced, solar panels in place, a lower level that can serve several different purposes, and a garage built for more than just parking, 5601 Calvert Drive offers practical features that make a noticeable difference in how the home can be used. All of this is conveniently located near shopping, dining, commuter routes, and Downtown Frederick.

5601 Calvert Dr, Frederick

Listing courtesy of RE/MAX Realty Centre, Inc.. Contact:

5615 Calvert Dr, Frederick

5615 Calvert Dr, Frederick

4 Beds ⋅ 2 Baths

Coming Soon! The finishing touches are being put on this like new Four Bedroom, One and a Half bathroom home. Wood floors throughout main level, stainless steel appliances, and flat open lot close to town. Available this Fall.

5615 Calvert Dr, Frederick

Listing courtesy of Keller Williams Realty Centre. Contact:

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Kathleen McMahan

For Kathleen McMahan, real estate has always been about more than buying and selling homes. It’s about people, relationships, and helping clients feel confident during some of the biggest transitions of their lives. With more than a decade of experience in Maryland and Washington, D.C. real estate, Kathleen has built her business around a simple philosophy: stay positive, work hard, communicate honestly, and treat every client’s move as if it were her own. Positivity has long been Kathleen’s “north star,” both personally and professionally. When her oldest son spent time in the NICU, she focused on learning everything she could from his nurses so she would feel prepared when it was finally time to bring him home. That experience reinforced something she carries into her work today: even during stressful and uncertain moments, knowledge, preparation, and the right perspective can make all the difference. That mindset has helped Kathleen build a successful real estate career based largely on relationships, referrals, and clients who return to her as their lives and real estate needs evolve. Now, as the agent behind McMahan Homes at Real Broker, she brings the experience of more than a decade in the industry together with the personal attention and flexibility of an independent real estate business. Originally from New Jersey, Kathleen came to Maryland to attend Salisbury University. Her studies in sociology and marketing helped spark a lasting curiosity about people—what motivates them, what matters to them, and what makes a place truly feel like home. Today, that curiosity is one of her greatest strengths as an agent. Kathleen takes the time to understand not just what her clients are looking for on paper, but what they want their lives to look like. Whether she’s preparing a home for the market, negotiating on behalf of a seller, helping a buyer find the right community, or simply answering the questions that come up along the way, her goal is to make the process feel informed, personal, and manageable. Kathleen lives in Maryland with her husband and two sons. When she isn’t working, you’ll most likely find her spending time with her family, dreaming about her next trip to the Florida Keys, or planning her next home project.

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