CHARIS REALTY GROUP
One of the most popular communities provided by {{page_data.agentName}}

MIDDLETOWN

One of the most popular communities provided by Charis Realty Group

MIDDLETOWN

About MIDDLETOWN

Discover Middletown, MD Real Estate

Welcome to Middletown, Maryland! Nestled in the heart of Frederick County, Middletown offers a charming blend of small-town atmosphere and modern amenities. If you’re searching for a place where community, convenience, and natural beauty meet, Middletown, MD real estate is the perfect choice.

Why Choose Middletown, MD?

Located just minutes west of Frederick, Middletown boasts picturesque landscapes, historic landmarks, and a warm, welcoming community. Here’s why so many homebuyers are looking for houses for sale in Middletown, MD:

  • Stunning Mountain Views: Surrounded by the scenic Catoctin Mountains and rolling farmland, this area provides breathtaking vistas year-round.
  • Top-Rated Schools: Middletown is renowned for its excellent public schools, including Middletown High School.
  • Charming Downtown: Explore locally-owned shops, cafes, and eateries along Main Street for a classic small-town experience.
  • Nearby Recreation: Enjoy outdoor activities at Middletown Park, South Mountain State Park, and local golf courses.
  • Easy Access: Quick commutes to Frederick, Hagerstown, and even Washington, DC make Middletown ideal for professionals and families alike.

Middletown, MD Housing Market Overview

The Middletown, MD real estate market features a wide variety of properties, from historic Victorian homes to modern new constructions. Whether you’re a first-time buyer, looking to upgrade, or seeking a peaceful place to retire, Middletown offers:

  • Single-family homes
  • Townhouses
  • New builds and developments
  • Spacious lots and acreage

Interested in recent listings? Check current homes for sale in Middletown, MD for up-to-date market trends and pricing.

Live in the Heart of Frederick County

Relocating to Middletown, MD means you’ll experience:

  • A strong sense of community and friendly neighbors
  • Highly walkable streets with beautiful historic architecture
  • Year-round events, including the popular Middletown Heritage Festival
  • An unbeatable blend of rural charm and convenient suburban living

Ready to Find Your Dream Home in Middletown?

From stately colonials to custom-built estates, Middletown, Maryland real estate delivers exceptional value and quality of life. If you’re considering a move, now is the perfect time to contact a trusted Middletown, MD real estate agent to start your search.

Start living the life you’ve always dreamed of in Middletown, Maryland—where homes are more than houses; they’re part of a vibrant, enduring community.

One of the most popular communities provided by Charis Realty Group
107
# of Listings
3
Avg # of Bedrooms
$329
Avg. $ / Sq.Ft.
$549,729
Med. List Price

Browse MIDDLETOWN Real Estate Listings

All listings

Under $250,000

$250,000 - $500,000

$500,000 - $1M

$1M - $3M

$3M - $5M

Over $5M

124 Properties Found. Page 6 of 9.

To be built - New Construction! Monarch offers resort-style living featuring high-end finishes and flexible floor plans. At the heart of the community, residents will enjoy an amenity-rich clubhouse complete with a resort-style pool, pickleball and sports courts, and inviting indoor lounge spaces perfect for relaxation or connection. Combining the sophistication of luxury homes with the laid-back charm of Delaware living, Monarch delivers the perfect balance of comfort, style, and convenience—all just minutes from Middletown’s shopping, dining, and entertainment The Whimbrel is a ranch home starting at 1,971 sq. ft., with 3 bedrooms, 2 baths, and a flex space ideal for a home office. Open kitchen with island flows to dining and great room. Options available for extra bedrooms, baths, loft, and outdoor living.
#DENC2093528

MIDDLETOWN

2204 EARLY COURT

3 Beds

2 Baths

1,971 Sq.Ft.

$609,900

MLS#: DENC2093528

TO BE BUILT-The Eden II is our largest four-bedroom model with a lot of versatility. It can easily accommodate a fifth bedroom if needed. The owner's suite has a separate sitting area, and two walk-in closets. All bedrooms are generously sized. The eat-in kitchen is well laid out with an open flow to the rest of the living space. This floor plan is outstanding. Standard features include stone water table, stainless steel appliances, granite counter tops, hardwood in foyer, kitchen & breakfast.
#DENC2079332

MIDDLETOWN

400 REDERICK LANE 5 EDEN II

4 Beds

2 Baths

3,195 Sq.Ft.

$608,000

MLS#: DENC2079332

This Santa-approved home now offers a new holiday price! What would make the best present this year - keys to your beautiful new home!!!! This meticulously maintained property boasts pride of ownership both inside & out! Situated in the prestigious community of The Legends in Middletown, conveniently located moments from shopping, dining and everyday conveniences. This spacious residence offers an unparalleled blend of comfort and scenic beauty, set against a tranquil backdrop that overlooks the golf course. As you enter the grand entryway greets you with a soaring ceiling and impressive turned staircase that sets a sophisticated tone from the moment you arrive. The flowing floor plan features a striking two-story family room that showcases a gas fireplace for those chilly evenings. This floor plan creates an inviting atmosphere for both intimate gatherings and elegant entertaining. The spacious kitchen offers abundant cabinet/counter space, center island for additional storage & convenient access to the deck through sliding glass doors—perfect for effortless indoor-outdoor living. The spacious rear fenced yard provides both privacy and space, ideal for entertaining, gardening, or simply relaxing while enjoying serene golf course views. The primary suite serves as a private sanctuary, complete with a spacious walk-in closet, linen closet and beautifully designed en-suite bath. Three additional generously sized bedrooms & tastefully appointed hall bath complete the upper level, offering comfort and versatility for guests, family or friends. THE BONUS TO THIS HOME IS THE FINISHED BASEMENT ------ The finished basement features two additional rooms with closets, full bath, counter/cabinet area ideal for entertaining, theater area & large unfinished area for additional storage.
#DENC2093134

MIDDLETOWN

241 PORKY OLIVER DRIVE

4 Beds

2 Baths

2,650 Sq.Ft.

$605,000

MLS#: DENC2093134

Very unusual historic home in the heart of Middletown. Just blocks from new YMCA. Home was assembled in 1944-1948 from parts of multiple historic homes being demolished to make room for post war housing. The front facade and much of the brick exterior were transported and re-assembled on site, proudly boasting 1736 construction. Add various plank floors, beamed ceiling, fireplaces with Mable surround or beautiful delft tiles, decorative moldings, beautiful wood doors.... You may think you can visualize how beautiful this house is, but it will still surprise you, now add recent kitchen, a first floor primary suite with spacious en-suite, large closets and room for washer and dryer. Wait there's more!! Recent HVAC (2 zone) a large Amish built workshop shed , a carriage house/pool house with full bathroom. Ornate gardens and landscaping, a koi pond, brick walkways encased with privacy fencing , yet walking distance to schools, stores , dining and entertainment. A Must see to imagine. Book your private tour as soon as possible.
#DENC2091784

MIDDLETOWN

12 E COCHRAN STREET

4 Beds

2 Baths

2,275 Sq.Ft.

$605,000

MLS#: DENC2091784

This home is a To-Be- Built. The Amadora offers a private home office off the foyer, a beautiful kitchen with a large island overlooking the dining area, and a spacious great room. In addition, a luxurious primary suite with triple windows and a relaxing primary bath with dual sinks and walk-in closet. This community includes a tot lot, walking trails and a dog park and is located in the Appoquinimink School District. Choose from 7 distinct floorplans including a mix of ranch, 1st floor bedrooms and up to 5 bedroom homes. To schedule a tour please and to receive a full brochure of all features in this home please contact our sales representatives.
#DENC2053844

MIDDLETOWN

125 PATTERSON COURT

3 Beds

2 Baths

2,167 Sq.Ft.

$603,990

MLS#: DENC2053844

Edmonston -TO BE BUILT. Come tour our decorated model during business hours. This 4 bedroom open floor plan welcomes homeowners and visitors alike in a space that flows effortlessly from one room to the next. This plan offers 2 version, the standard offering a first floor owner's suite, and the alternate offering a larger great room and secondary bedroom on the first floor. There is a spacious kitchen with hardwood floors, along with 42" maple cabinets, granite countertops, and so much more! The picture shown is of our largest porch option, but there are several sizes to choose from. If you are looking for a community with planned amenities, retail, school and everything else you can imagine, visit the first new urbanism concept community in Delaware, The Town of Whitehall. Agents must accompany buyer on first visit or pre-register on builder's website prior to first visit.
#DENC2079252

MIDDLETOWN

530 WHEELMEN STREET 8 WENTWORTH

4 Beds

2 Baths

2,680 Sq.Ft.

$602,000

MLS#: DENC2079252

Brand New 55+ Community in Middletown, DE - Four Seasons at Pennfield. Coming This November: Aberdeen II Home Design Blending classic charm with open-concept living, this Aberdeen II home offers 3 bedrooms, 2 baths, and a 2-car garage on a spacious ¼-acre lot. From the welcoming screened porch to the finished basement, there’s room to relax, entertain, and grow. The main living area showcases stylish laminate flooring throughout, anchored by a fireplace with custom paneling trim. In the kitchen, Profile appliances pair with quartz countertops to create a beautiful and functional culinary space. The primary bath features a large walk-in shower with multiple shower heads—your own private retreat. For a full list of features, please contact our sales representatives. Photos are for illustrative purposes only and may show optional features and upgrades.
#DENC2086764

MIDDLETOWN

1521 LESTERFIELD WAY

4 Beds

2 Baths

2,148 Sq.Ft.

$599,990

MLS#: DENC2086764

This ranch home located in a quiet Middletown neighborhood is a gem hidden in plain sight and full of surprises. First, it has 4,000 resplendent finished square feet, and second, it offers two levels of independent living. The floorplan flows seamlessly, providing the kind of breathing room you’ll appreciate, enhanced with an elegant color palette, natural light, and stunning hardwood floors that pull it all together. The living room easily provides the space for various seating configurations and offers a fireplace along the main wall to center around. It opens to the renovated kitchen, inviting with its pristine white cabinetry, backsplash, and eat-in island—and where you’ll find ample workspace and storage plus high-end stainless appliances and fixtures. The dining room sits adjacent with space for extras such as china cupboards or buffets. A bonus room affords decent space for an office, playroom, crafts or hobbies, etc. Conveniently located next to the kitchen, a mudroom combines with the laundry area with storage cabinets and a utility sink. This level boasts four bedrooms and three full baths. The primary suite shines with the addition of a sliding barn door to separate the appealing attached bath plus a walk-in closet. The other bedrooms and baths are all lovely, matching the theme. The downstairs is a complete floor designed as an in-law suite or rental. It boasts a full kitchen, comfortable living/dining area, bedroom, bath, and dedicated laundry room. The aesthetic matches the upstairs to a backdrop of LVP plank-style flooring. It contains a private separate entrance, and even its own parking. The home rests on .31 acres with a view of the mountains, along with plenty of trees and landscaped shrubs to enjoy. A screened-in porch adds another tranquil respite, as does a covered porch stretching along the front of the home. A two-car attached garage provides space for vehicles or storage. This home has been updated, renovated, and carefully maintained—and presents a unique opportunity. But also, this residence is the ticket to enjoy Middletown’s quaint, historic downtown, well-rated schools, and peaceful atmosphere plus proximity to Winchester, Shenandoah Valley, and all the area has to offer.
#VAFV2037492

MIDDLETOWN

2140 SIXTH STREET

5 Beds

4 Baths

4,006 Sq.Ft.

$599,900

MLS#: VAFV2037492

Nestled in the prestigious community of The Legends, this exquisite traditional home offers a harmonious blend of luxury and comfort, perfect for those seeking an elevated lifestyle. Set on a desirable corner lot, this residence boasts an impressive 2,700 square feet of thoughtfully designed living space, ensuring ample room for relaxation and entertainment. As you step inside, you are greeted by a warm and inviting atmosphere, enhanced by rich hardwood flooring that flows seamlessly throughout the main areas. The kitchen has plenty of cabinet space with roll out shelves, Granite countertop, backsplash and stainless appliances with a double oven. The upstairs has a spacious layout and features four generously sized bedrooms, providing a tranquil retreat for everyone. The master suite is a true sanctuary, complete with an en-suite bathroom that exudes elegance and functionality. The heart of the home is undoubtedly the cozy living area, where a charming fireplace serves as a focal point, inviting you to unwind after a long day. With main floor laundry facilities, convenience is at your fingertips, allowing you to focus on what truly matters-creating memories in your new home. A 12x14 screened in deck area leads to the outside. The outside: the property features a well-maintained yard, perfect for outdoor activities or simply enjoying the serene surroundings. The attached garage and driveway provide ample parking space, ensuring that you and your guests are always accommodated. Built in 2001, this home combines modern amenities with timeless architectural charm, featuring durable vinyl siding and stucco that enhance its curb appeal. The full basement with a full bath Rough In offers endless possibilities for customization, whether you envision a home gym, entertainment space, or additional storage. Living in The Legends means embracing a lifestyle of exclusivity and comfort, with access to nearby amenities that cater to your every need. This corner lot residence is not just a house; it's a place where you can create lasting memories and enjoy the finer things in life. Experience the perfect blend of luxury and comfort in this stunning home-your dream lifestyle awaits.
#DENC2092438

MIDDLETOWN

1 HOGAN CIRCLE

4 Beds

2 Baths

2,700 Sq.Ft.

$599,900

MLS#: DENC2092438

Step inside-You'll love it! This is a home designed to impress and it can be your new home before the Holidays! Spacious and beautifully updated 6-bedroom is perfect for multigenerational living. A rare find- two master suites, dual family rooms and high-end upgrades throughout. The home offers flexible space ideal for large families, guests, or home offices. Recent updates include a new roof, gleaming hardwood floors and one new ceramic bath. The updated kitchen shines with granite countertops, stainless steel appliances. Having multiple gathering areas this home has a perfect layout for entertaining. The inviting layout makes this home ideal for family events, relaxation or hosing guest. You won't be disappointed by the stunning landscape, multiple decks and it even has a handicap access ramp! Additionally, the Home is conventionally located near the well-known Middletown Park. Don't miss your chance to make it yours-schedule your private showing today!
#MDFR2066902

MIDDLETOWN

4311 ZIRCON ROAD

6 Beds

4 Baths

3,072 Sq.Ft.

$599,000

MLS#: MDFR2066902

Introducing the CHELSEA Model, to be built in the highly desirable 55+ community of Traditions at Whitehall. This thoughtfully designed 3-bedroom, 2-bath home features an open-concept floor plan, with a spacious foyer, formal dining area, and a large great room that flows into the kitchen perfect for entertaining. The Owner’s Suite includes a walk-in closet and an en-suite bath with a double vanity and standard tile shower. The home also offers flexible options to add a 4th bedroom, loft, and third bathroom on the second floor. The gourmet kitchen is a highlight, with stainless steel appliances, granite countertops, and a large island. The community offers a clubhouse, fitness center, swimming pool, walking trails, and plenty of social activities. With a 2-car garage and low-maintenance living, the Chelsea Model offers a perfect combination of comfort and style.
#DENC2080208

MIDDLETOWN

204 BALDY LANE CHELSEA

3 Beds

2 Baths

2,296 Sq.Ft.

$599,000

MLS#: DENC2080208

* BUILDER'S END-OF-YEAR CLOSEOUT! LIMITED TIME OFFER…. CALL TODAY for details! * The home you have been admiring is now available! There are so many beautiful features in this Woodland Hills model home and they can be yours without the wait time of a new home build. The Osprey model has 2,898 sq ft with 4 bedrooms and two and a half bathrooms. With ample storage and counter space, the kitchen will be where the family and guests will want to gather. The beautiful granite counters, oversized island and under-cabinet lighting are a few of the custom features that you will enjoy. Soak up the sun all year round in the 12x14 sunroom that is situated just off the great room area. A gas fireplace and built-in bookshelves are the natural focal point of the living room area. Also on the 1st floor is the flex room, study, laundry room, powder room and a mudroom area with a bench seat, coat hooks and lockers. The second floor has 4 larger bedrooms and 2 bathrooms. The master bath, with it's ceramic tile floor, tiled shower and soaking tub, will be your place to retreat and pamper yourself at the end of the day. The hall bath has a tub/shower. The unfinished basement features 9' poured concrete walls. You also have the convenience of a central vac system. This home is situated on a corner homesite and has easy access to Vine Street and I-283. Although loaded with custom features, this home is priced well below replacement cost.
#PADA2048296

MIDDLETOWN

195 MAGNOLIA DRIVE

4 Beds

2 Baths

2,898 Sq.Ft.

$599,000

MLS#: PADA2048296

Prime commercial site. This 1.54-acre property boasts a coveted B-2 zoning, making it an ideal location for business ventures. Conveniently positioned just off Interstate 81 and a short drive from Interstate 66, this site offers excellent visibility, ensuring maximum exposure for any enterprise. Situated between two well-known establishments, McDonald's and Econo Lodge, it benefits from high traffic and customer flow. With public utilities readily available, the infrastructure is in place to support a wide range of commercial activities. Moreover, the surrounding area is experiencing substantial residential growth, indicating a thriving market and potential customer base. This commercial site's strategic location, zoning, excellent visibility, proximity to major highways, and supportive infrastructure make it an enticing prospect for entrepreneurs looking to establish or expand their businesses in a rapidly developing area.
#VAFV2013246

MIDDLETOWN

RELIANCE ROAD

None Beds

None Baths

1.38 acres

$595,000

MLS#: VAFV2013246

VILLAGE OF BAYBERRY NORTH – Immaculate 4-Bedroom, 2.5-Bathroom Colonial home with a 2-CAR GARAGE and a fully fenced yard. Built just 5 years ago, this home is LIKE NEW! Enter into the foyer where you will notice HANDSCRAPED HARDWOOD FLOORS that run throughout the majority of the first floor. An open layout exists between the formal dining area and living room. Upgraded light fixtures have been added here & throughout the entire home. Straight ahead, you’ll find the kitchen, family room, and breakfast room. The kitchen features: GRANITE countertops, STAINLESS STEEL APPLIANCES, tile backsplash, recessed lighting, and a pantry. Sliders from the breakfast room lead to the huge maintenance-free TREX DECK. The deck steps down to the fully fenced yard with a shed included for your outdoor storage needs. Back inside and also on the first floor is the powder room and the laundry room. Head upstairs to find 4 bedrooms and 2 full baths. Double doors lead to the master suite which boasts a WALK-IN CLOSET, a 2nd closet, and a full master bath. The 5-piece master bathroom features 2 vanities, a jacuzzi tub, & a stall shower. A full, open unfinished basement offers the option to finish for added living space or simply use for storage. The unfinished basement includes a plumbing rough-in for a 3rd full bathroom. This is The Gable Floorplan, premium Colonial Elevation with a stone water table. Several builder upgrades were selected, including the Luxury Master Bath w/ 4’ fiberglass shower, 6x6 tiled tub deck, jetted tub, & granite vanity top. Other notable features include: FRESH PAINT throughout, security system with surveillance cameras included, & smart doorbell included. Located in a lively community that offers a modern clubhouse, numerous playgrounds, pavilions, walking trails, a dog park, biking trails, and picnic areas. The 3,400 sq. ft. clubhouse is located on a private lake that can be used by residents for boating and fishing. Conveniently close to major roadways (DE-1, DE-13, DE-301) for ease of commute. Don’t wait, schedule your tour today!
#DENC2094370

MIDDLETOWN

755 STANFORD WHITE WAY

4 Beds

2 Baths

2,650 Sq.Ft.

$594,000

MLS#: DENC2094370

Savannah -To be built. This floor plan feature 4 bedrooms, 2.5 baths, second floor laundry, 2 car attached or detached rear entry garage, and an open floor plan for entertainment with a huge great room. Welcome to your new hometown! At Whitehall, the hometown is finally getting its comeback. It's the first town to be founded in Delaware in over a century, and it's planned for all homes, businesses and community traditions that make real towns real places. Walk to the park, doctor's office, or to school. Whitehall will have it all! Agent must accompany client on first visit or pre-register client on builder website prior to first visit.
#DENC2079250

MIDDLETOWN

530 WHEELMEN STREET 7 SAVANNAH

4 Beds

2 Baths

2,854 Sq.Ft.

$591,000

MLS#: DENC2079250

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