Middletown Homes with Lighted Parking features

Welcome to Middletown, a hidden gem nestled in the heart of Frederick County, Maryland. This charming town is known for its picturesque landscapes, rich history, and vibrant community spirit. With its quaint downtown, friendly neighbors, and stunning views of the surrounding mountains, Middletown offers a delightful blend of small-town charm and modern amenities.

Middletown is not just a place to live; it’s a lifestyle. The town is surrounded by lush parks, scenic trails, and recreational areas, making it a perfect haven for outdoor enthusiasts. Whether you enjoy hiking, biking, or simply taking a leisurely stroll, the natural beauty of this area will captivate you. Plus, with its close proximity to major highways, you can easily access the bustling cities of Frederick and Washington, D.C., while still enjoying the tranquility of suburban life.

For those considering a move to this lovely town, homes in Middletown often feature modern conveniences, including lighted parking options. Imagine returning home after a long day to a well-lit driveway that welcomes you with warmth and safety. This thoughtful feature not only enhances the aesthetics of your property but also provides peace of mind, especially during those dark winter months.

With a diverse selection of homes available, ranging from charming historic houses to contemporary builds, you’re sure to find the perfect fit for your lifestyle. Embrace the Middletown community, where friendly faces and beautiful homes await you. Come and discover why so many are proud to call this enchanting town home!

Newest Middletown Homes with Lighted Parking features

$600,000

3 Beds ⋅ 3 Baths ⋅ MDFR2086228 MLS

PRICE DROP $25K! SELLER SAYS GET IT SOLD! Welcome to 7 Derr Lane in the sought-after Villages at Foxfield—Middletown’s premier 55+ community—where Original Owners have meticulously maintained and thoughtfully upgraded this beautiful home, showcasing true pride of ownership everywhere you look. Perfectly positioned within walking distance to Middletown Park and its many amenities, this home also backs to serene woods, walking/jogging paths, and open green space—offering both convenience and some privacy. Enjoy peaceful mornings on the covered front porch or unwind in the backyard retreat featuring a walkout patio, koi pond, and a hidden “secret garden” be sure not to miss. Inside, the home blends comfort and modern updates. The kitchen is a standout with a Corian island, mosaic tile backsplash, stainless steel appliances (replaced 2019), induction downdraft cooktop, double oven, and ceramic flooring—ideal for both everyday living and entertaining. The main level boasts hardwood flooring (2018) and a warm, inviting family room with a propane fireplace and direct access to the newer, enlarged Trex deck (2022, with updated door in 2025). The spacious layout includes vaulted ceilings, a tray ceiling in the primary suite, and a dramatic two-story overlook with loft above. The primary bath was beautifully renovated in 2017, and the upper level features new carpet (2019). Additional updates include leased solar panels for energy efficiency (2018), washer and dryer (2021), vinyl fencing (2022), new roof and ventilation (2024), HVAC (2015), and water heater (2018). The unfinished lower level offers a walkout to the backyard, rough-in for a full bath, and a wide-open layout ready to be customized to your needs. Garage is equipped with a 200 amp 240 volt EV charging circuit and a newer garage door opener (2021). This is a rare opportunity to own a truly move-in-ready home in Middletown’s most desirable active adult communities—combining thoughtful upgrades, natural beauty, and a vibrant lifestyle.

7 Derr Ln, Middletown

$2,249,999

MDFR2082478 MLS

Experience the flow of space and harmony a private 5-acre sanctuary where mid-century soul meets meticulous architectural restoration. Set among park-like grounds and hundreds of flowering trees, this retreat-like residence is wrapped by protected conservation land on two sides, delivering incomparable privacy and a serene stage for entertaining, work, and retreat. From the views of Middletown Valley and South Mountain to 1960s design roots, to modern comfort, the home embodies seclusion without sacrificing accessibility. At the heart of the living spaces, a grand fireplace anchors the flow, guiding the eye and gathering rooms into a seamless continuum. The layout invites conversations to drift from indoor to outdoor and back again, with spaces merging around this warm, sculptural anchor. From Kentucky pink sandstone and cedar exteriors to warm interior touches—wood floors, custom concrete sinks, maple doors and trim, and a well-organized mudroom and laundry area—every surface speaks to craft and longevity. On the main level the Center Room is designed for living and entertaining. It is enriched by commissioned art, beautiful Kentucky sandstone fireplace and huge windows that look out over the Middletown Valley. A wrap around deck allows transition from the indoors to out, with just a few footsteps. A dedicated library with custom maple shelving creates a quiet, sunlit mezzanine of ideas—is a perfect retreat for reading, group study, or inspiration. The stunning kitchen was designed in collaboration with local architect, Clyde Burger. The two 12’ long walnut islands and all the kitchen cabinetry is hand-built Mennonite woodwork. The work surfaces are polished concrete, and the built-in appliances are professional grade. A kitchen lounge houses built-in cabinetry and encourages family and social time as meals are prepared and enjoyed. An 18-foot NanaWall opens to dissolve the boundary between inside and outdoor. The main level laundry has clean lines, beautiful carpentry, wonderful hand built floating shelves, custom concrete surfaces and sink as well as a wet floor and direct access to the decks and yard. The mudroom and powder room also feature custom cabinetry and specially designed features, such as the concrete sink and the floating concrete benches. The primary suite is un-filled, architectural artistry with an imported floor, two walk-in closets (one cedar-lined), and a bath featuring terrazzo floors and a standout view. Two en-suite bedrooms, renovated December 2025, have wood floors with custom Navajo-inspired wood inlays. Commissioned furnishings fill of the rooms and both enjoy nature views. The lower-level spaces are also remarkable. The second grand room has a vibrant MCM fireplace and is ideal for family activities, mediation or intimate gatherings. The windows showcase the valley view, and the doors open directly to the saltwater pool. Two private rooms are ready to use as bedrooms or office spaces. The full bathroom also has a custom concrete vanity and floor and warm cork tiling. This wing of the lower-level embraces angles and has built floating shelves in the lower library. Additionally, this level offers a bright, versatile studio providing space for creativity of all types—art, writing, design, or restorative projects— to inspire and nurture imagination. The exterior grounds are a living landscape. The 5-acre parcel unfolds as a natural paradise with park-like landscaping and hundreds of flowering trees seen from every window. The long drive lined with light poles and the parking area edged by planters sets a welcoming tone as you approach the home. A multi-level Brazilian hardwood deck overlooks a heated saltwater pool; a detached barn houses a traditional Scandinavian sauna and a lounge for year-round wellness. The homes systems are wellness-oriented including geothermal HVAC, a brand-new roof with a 50-year warranty, a multi-stage water softening system.

9237 Frostown Rd, Middletown

$2,249,999

4 Beds ⋅ 5 Baths ⋅ MDFR2082166 MLS

Five private acres above the Middletown Valley, with South Mountain on the horizon and protected conservation land on two sides. This is a home built around how you want to spend your days: coffee in a kitchen with two 12-foot walnut islands and an 18-foot NanaWall that opens straight to the deck, afternoons at the heated saltwater pool, evenings by the Kentucky sandstone fireplace with the whole valley in the windows. When the day is done, the detached barn holds a Scandinavian sauna and a lounge for year-round unwinding. The layout works for daily life and for hosting. Three bedrooms are on the main level, including a primary suite with two walk-in closets (one cedar-lined) and a terrazzo bath. Two en-suite bedrooms were renovated in December 2025. A sunlit library with custom maple shelving sits above the main living space. Downstairs, a second great room with its own fireplace opens to the pool. Two flex rooms suit guests or a home office, and a bright studio is ready for art, writing, or design work. The main-level laundry and mudroom open directly to the deck and yard. It's built to last: geothermal heating and cooling, a brand-new roof with a 50-year warranty 2026, multi-stage water softening, hand-built Mennonite cabinetry, polished concrete surfaces, and a two-car attached garage. A long, lighted drive leads to complete privacy, yet 3 minutes to Middletown, 10 to Frederick, and 5 to [I-70/major commuter route].

9237 Frostown Rd, Middletown

$1,300,000

VAFV2019018 MLS

Unlock the potential of a timeless landmark with the Wayside Inn, a historic gem nestled in the heart of Middletown, Virginia. This unique property not only boasts a rich history dating back to the 18th century but also offers 22 suites all with bathrooms, 3 bars (tavern, bourbon & Speakeasy, The RED HAT), huge entertaining space for events. This is a prime commercial opportunity with an expansive land for expansion. Just under 4 acres zoned B1. With 4 acres of commercially-zoned land at your disposal, envision the expansion possibilities that could elevate this historic landmark into a thriving hub of activity. Take advantage of the ample space to create a vibrant commercial district that complements the historic character of the Wayside Inn, making it a destination for locals and tourists alike. Situated in the picturesque Shenandoah Valley, the Wayside Inn offers a scenic backdrop that enhances the allure of any commercial venture. The expansive grounds provide ample room for outdoor amenities, gardens, or additional structures to further enhance the property's appeal. Benefit from the strategic location of Middletown, with easy access to major transportation routes. The Wayside Inn's proximity to popular attractions, historic sites, and a supportive local community makes it an ideal location for a successful and sustainable business venture. Don't miss the chance to own a piece of history with a promising future. The Wayside Inn presents a rare investment opportunity where historic charm meets commercial potential. Whether you're an entrepreneur seeking a unique venture or a developer with a vision, this property is your canvas to create something extraordinary. Seize the moment and transform the future of the Wayside Inn. Embrace the legacy, write the next chapter, and make this historic landmark a cornerstone of Middletown's thriving community. Fully running and doing great, we have changed management and its now positive cash flow. its prime for an owner occupant. call for details and appointments. Open to lease option and owner financing available. Kitchen and tavern are leased. Have grants applied for in the millions to renovate it. Have insurance claim coming for a new roof as well.

7783 Main St, Middletown

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