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$515,000
4 Beds ⋅ 3 Baths ⋅ COMING SOON Status
A little bit of country feel, a lot of usable space, and a location that is increasingly hard to find. Tucked at the end of a cul-de-sac on more than half an acre, this charming 4-bedroom, 2.5-bath cape cod offers a private, tree-lined setting in the sought-after Middletown school district. Inside, the home has been thoughtfully refreshed while retaining the warmth and character that make this style of home so inviting. The updated kitchen features warm wood cabinetry, stainless steel appliances, a farmhouse-style sink, generous storage, and an easy connection to the adjoining living spaces. Fresh paint, carpet, and lighting add to the home’s comfortable, move-in-ready feel. The flexible floor plan includes a bedroom and full bath on the main level, which is ideal for guests, a home office, or those looking for the convenience of main-level living, along with three additional bedrooms and another full bath upstairs. Downstairs, the finished walkout lower level provides valuable additional living space with plenty of flexibility for a recreation room, media space, gym, playroom, or home office, while unfinished space offers additional storage. Outside is where this property really sets itself apart. The large deck overlooks a wooded backdrop and offers a peaceful place to entertain, dine outdoors, or simply enjoy the privacy of the setting. The spacious .52-acre lot provides plenty of room to spread out, while mature trees give the property an established, tucked-away feel. An oversized detached two-car garage with additional storage, along with a generous driveway, provides exceptional parking and versatility. With four bedrooms, multiple living spaces, a finished walkout lower level, detached garage, more than half an acre, and a cul-de-sac setting backing to woods, this is a rare opportunity to enjoy space and privacy without giving up the convenience of Middletown. This one-of-a-kind property is located within close distance to Middletown Park, downtown shopping and dining, grocery stores, and all of Middletown’s charm on Main Street.

7 Eastern Cir, Middletown

Listing courtesy of Compass. Contact: (240) 335-7355
$539,900
4 Beds ⋅ 3 Baths ⋅ ACTIVE Status
Welcome to 4492 Jade Court, where a complete interior and exterior renovation meets an exceptional private backyard retreat. Situated on a generous .55-acre lot, this truly move-in-ready home offers 4 bedrooms, 2.5 bathrooms, approximately 2,200 square feet of finished living space, and an extensive list of major improvements. The exterior has been completely refreshed with a new architectural-shingle roof, brand-new vinyl siding, new gutters and shutters, and all-new double-hung, double-pane replacement windows. The fully fenced backyard is designed for both relaxation and entertaining, featuring an impressive 40-by-20-foot in-ground pool with a diving board and slide, a spacious concrete entertaining area, and a gazebo that conveys with the property. A matching storage shed provides additional convenience, while the brand-new two-level deck creates multiple outdoor living spaces overlooking the private backyard. Inside, beautifully refinished original hardwood floors add warmth and character throughout the main living areas. The completely renovated kitchen features quartz countertops, brand-new stainless-steel appliances, a true exterior-vented range hood, and a center island with overhang seating. A new sliding glass door provides direct access from the kitchen to the lower deck, making indoor-outdoor entertaining effortless. The entry level includes a primary bedroom with an en-suite full bathroom and its own private exterior access to the backyard. The main living area is highlighted by a natural wood-burning stove, creating a warm and inviting setting for colder evenings. Upstairs, you will find three additional bedrooms and a second full bathroom. One of the upper-level bedrooms offers direct access to the bathroom and could serve as an additional primary bedroom. A second new sliding glass door opens onto the upper deck, where you can enjoy elevated views of the pool and backyard. The fully finished lower level adds even more versatile living space with brand-new vinyl plank flooring, a convenient half bathroom, and walkout access to the exterior. Additional improvements include new recessed lighting throughout and a brand-new HVAC system. With the major systems, exterior, interior finishes, kitchen, bathrooms, windows, decks, and outdoor entertaining areas already completed, this home is the definition of move-in ready. Simply unpack, settle in, and enjoy your beautifully renovated home and private backyard oasis.

4492 Jade Ct, Middletown

Listing courtesy of Coldwell Banker Realty. Contact: (717) 757-2717
$584,900
3 Beds ⋅ 3 Baths ⋅ ACTIVE Status
Escape the ordinary with this one-of-a-kind mountain-inspired retreat set on more than 5 secluded acres of mature woodland. Designed to embrace its natural surroundings, this distinctive chalet welcomes the outdoors in with dramatic vaulted ceilings, walls of windows, and multiple skylights that fill the home with sunlight while showcasing peaceful forest views from nearly every room. The inviting great room is centered around a beautiful fireplace, creating the perfect gathering place, while rich hardwood flooring and natural finishes enhance the home's warm, rustic charm. Step outside onto the expansive wraparound deck, where you can enjoy the sights and sounds of nature, entertain guests, or simply relax in complete privacy. The updated kitchen features granite countertops and stainless-steel appliances including gas cooking, offering modern functionality without sacrificing the home's unique character. An oversized detached two-car garage provides exceptional space for vehicles, a workshop, outdoor equipment, or additional storage. Offering the rare combination of privacy, distinctive architecture, and everyday convenience, this exceptional property feels like a secluded woodland retreat while remaining only about 15 minutes from Middletown's restaurants, shopping, and Middletown schools. Recent improvements include a new roof and skylights (2020), stove and microwave (2021), water softener and neutralizer (2022), and refrigerator (2025). Better see it soon before someone else gets to call it home!

6838 Mountain Church Rd, Middletown

Listing courtesy of Long & Foster Real Estate, Inc.. Contact: 3016441086
$625,000
3 Beds ⋅ 3 Baths ⋅ ACTIVE Status
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

Listing courtesy of Corner House Realty. Contact: (443) 499-3839
$699,000
5 Beds ⋅ 3 Baths ⋅ ACTIVE Status
This home is an absolute MUST SEE. This home has been immaculately maintained and features all of it's original charm. You will fall in love with the beautiful hardwood floors throughout this spacious 5 bedroom, 3 full bath colonial that features 3,200 square feet of living space along with a large 832 square foot basement, with outside entrance. This classic beauty is situated on a large, beautifully landscaped and manicured, corner lot of .64 acres in Middletown's Historic District. You will fall in love with all of the historic charm and craftsmanship that blends seamlessly with modern upgrades such as vinyl siding and replacement windows. There are several bonus areas that provide added charm to this already captivating home. There is a family room that was crafted from a former garage, a second floor sunroom area for relaxing, a bonus room that could be a home office and a sitting area off of the formal dining room. This is a true gem and you will be amazed at the incredible condition.

200 Prospect St, Middletown

Listing courtesy of Coldwell Banker Realty. Contact: 4105434545
$499,900
4 Beds ⋅ 3 Baths ⋅ ACTIVE Status
*One or more photos in this listing have been virtually staged using AI* Completely Renovated & Move-In Ready! Welcome to this beautifully updated ranch-style home situated on a picturesque 2-acre lot in the heart of Middletown Valley. Every detail has been thoughtfully renovated, offering a bright, modern interior with quality finishes throughout. The open and inviting floor plan is perfect for everyday living and entertaining. Step outside to enjoy the spacious backyard, offering endless possibilities for outdoor gatherings, recreation, gardening, or simply relaxing while taking in the peaceful surroundings. Enjoy the tranquility of country living while remaining just minutes from downtown Middletown, Frederick, shopping, dining, schools, parks, and major commuter routes. Whether you're looking for your forever home or a quiet retreat with modern comforts, this exceptional property is ready for its new owner. Don't miss this rare opportunity!

9001 Hollow Rd, Middletown

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

$575,000
3 Beds ⋅ 3 Baths ⋅ ACTIVE Status
Welcome to your own private retreat! This 3-bedroom, 3 full bath home offers nearly 2,500 square feet of finished living space and comes with not one, but two parcels totaling approximately 7.63 acres. The home is situated on 5.90 acres and includes an additional 1.73-acre wooded lot located directly behind the property, providing even more privacy and future possibilities, and even hunt on your own property. Inside, you'll find beautiful wood flooring throughout the main level and a spacious layout designed for comfortable living. The primary suite features its own private full bath and direct access to a deck overlooking the peaceful surroundings. Two additional bedrooms and a full bath complete the main level. Enjoy the outdoors from the wraparound rear porch or entertain guests on the expansive two-tier deck. During the colder months, cozy up beside one of the home's two wood-burning fireplaces. The lower level offers additional living space along with a third full bath, making it ideal for a recreation room, guest area, or home office. With plenty of driveway parking and a 2-car attached garage, there is ample room for vehicles, equipment, and guests. Conveniently located just minutes from downtown Middletown and within the highly sought-after Middletown School District, this property offers the perfect combination of privacy, acreage, and accessibility.

2748 Bennies Hill Rd, Middletown

Listing courtesy of Long & Foster Real Estate, Inc.. Contact:

$924,500
3 Beds ⋅ 3 Baths ⋅ ACTIVE Status
HOME TO BE BUILT. Nestled on a beautiful, wooded 2.25-acre lot, this to-be-built home by Grossnickle Construction offers the perfect blend of luxury and comfort. The home features 3 spacious bedrooms, including a private primary suite, 2 full bathrooms, and a convenient powder room. This plan also includes 400 sqft rec room in the basement and the option for an upstairs bonus room. Enjoy the peaceful, natural setting with mature trees and scenic surroundings while still having the opportunity to personalize your new home. This featured plan can be built as-is, tweaked to your preferences, or you can choose a completely different custom plan to fit this homesite. Don’t miss this chance to build your dream home in a truly serene location.

Mountain Church Rd, Middletown

Listing courtesy of Real Estate Teams, LLC. Contact: 3016953020
$989,000
3 Beds ⋅ 3 Baths ⋅ ACTIVE Status
Escape the subdivision life for a residence defined by scale, privacy, and rugged utility. Set on 32.39+/- acres, this cabin-style estate is built for those who want their permanent home to feel like a fortress of solitude without sacrificing modern comforts. The interior features a recently updated kitchen equipped with new appliances and granite countertops. While there is a propane furnace, there is also a classic woodstove that provides a high-efficiency heating source and a focal point for the entertainment area in the basement. The home’s footprint is anchored by an expansive rear deck designed for four-season use; whether you’re hosting or decompressing, the integrated hot tub offers total privacy, screened by a dense canopy of mature timber to create an outdoor living room that feels completely removed from the outside world. This isn't just a woodlot; it's a gateway. The property borders Gambrill State Park, providing exploration and recreational opportunities right out your back door. For the serious outdoorsman or the family seeking an active lifestyle, the land offers endless utility for hiking, scouting, and wildlife management. The long, wooded approach ensures a level of seclusion and security that is increasingly rare, making this an ideal primary residence for those seeking a quiet, secure environment. Practicality meets potential inside and out, with a walkout basement that provides the ideal entertainment area or can be converted into a home office, gym, or additional bedrooms to grow with your needs. An existing shed provides organized storage for ATVs and maintenance equipment, keeping your primary living spaces clutter-free. Shown by appointment only, this is more than a getaway—it is a rare opportunity to own a significant piece of acreage with your ideal mountain retreat on your own recreational land in the Catocin Mountains.

8939 Hawbottom Rd, Middletown

Listing courtesy of Whitetail Properties Real Estate, LLC. Contact: