CHARIS REALTY GROUP
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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
243
# of Listings
3
Avg # of Bedrooms
$266
Avg. $ / Sq.Ft.
$640,253
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

243 Properties Found. Page 8 of 17.

Discover the charm of this stunning traditional home nestled in the desirable subdivision of The Legends. This beautifully maintained residence, built in 2001, boasts a generous 2,700 sq. ft. of finished living space, perfect for creating lasting memories. Situated on a spacious corner lot, this property offers both privacy and a welcoming atmosphere. Step inside to find a harmonious blend of comfort and style, featuring elegant hardwood, ceramic tile flooring and carpet throughout. The heart of the home is the inviting kitchen, equipped with modern stainless steel appliances and a double oven, ideal for culinary enthusiasts and entertaining guests. The open layout seamlessly connects the kitchen to the cozy living area, complete with a charming fireplace that sets the perfect ambiance for gatherings. With four well-appointed bedrooms and 2.5 bathrooms, this home provides ample space for relaxation and rejuvenation. The convenience of a main floor laundry adds to the ease of daily living. The full basement, with rough bath plumbing, offers endless possibilities for customization—think home gym, playroom, or additional living space. Enjoy the convenience of an attached front-entry garage with space for two vehicles, along with additional driveway parking. The outdoor space is perfect for enjoying sunny days and evening strolls in the neighborhood. This property is not just a house; it’s a place to call home. ALSO a New Furnace was just installed. Experience the perfect blend of comfort, style, and location—schedule your private tour today!
#DENC2092438

MIDDLETOWN

1 HOGAN CIRCLE

4 Beds

2 Baths

2,700 Sq.Ft.

$599,900

MLS#: DENC2092438

New on site 4 days ago
Welcome to 230 Anglesey Drive, a stunning home where luxury and thoughtful design meet everyday comfort. Step inside and be greeted by soaring 9-foot ceilings and rich 6-inch hardwood planks that flow throughout the main living areas, setting the tone for the elegance that awaits within. The open-concept floor plan creates a seamless transition between living, dining, and entertaining spaces, anchored by a warm gas fireplace and framed with timeless plantation shutters. At the heart of the home lies a chef-inspired kitchen, beautifully appointed with porcelain backsplash, quartzite countertops, and a striking 8.5-foot island perfect for gathering. GE stainless steel gas appliances – including an electric wall oven, built-in microwave, and full gas stove – ensure that both cooking and hosting are effortless. This home offers two spacious bedrooms along with a sophisticated office featuring designer grass cloth wallpaper, easily transformable into a third bedroom if desired. The primary suite is a true retreat with a dramatic trey ceiling and a spa-like bath showcasing a floating vanity, walk-in porcelain shower with mother-of-pearl accents, brushed gold fixtures, complemented by an anti-steam mirror with a mini heater above the shower. A custom-built linen closet adds both convenience and luxury. Two additional full bathrooms provide convenience and style for guests and family alike. A laundry room off the primary bedroom includes a Maytag washer and dryer (gas). The living space extends into the finished, wide-open basement, offering incredible flexibility with its own full bath and endless possibilities for recreation, hobbies, or guest accommodations. Storage is thoughtfully integrated throughout the home, complemented by modern recessed LED lighting and a tankless Noritz water heater that ensures energy efficiency and endless comfort as well as a whole house water purifier and whole house blue light air filtration. Leading to the outside is a tinted sliding glass door, a fenced-in backyard invites relaxation and entertaining with a covered, composite deck – your private outdoor oasis. An attached two-car garage completes this exceptional home and adds everyday practicality. Located in the 55+ section of the Preserve at Deep Creek known as Legacy, homeowners enjoy exclusive access to the 55+ pool, clubhouse, and fitness center, plus full use of community-wide amenities. While only two streets are age-restricted, all residents in Legacy enjoy shared benefits, with added exclusivity reserved for 55+ homeowners. Commuting and convenience are effortless thanks to the home’s central location – with quick access to I-95, Route 1, Delaware and New Jersey beaches, shopping, dining, and the bonus of tax-free retail in Delaware. With its blend of luxury finishes, modern comforts, and flexible living spaces, 230 Anglesey Drive offers the perfect home for your next chapter.
#DENC2095556

MIDDLETOWN

230 ANGLESEY DRIVE

2 Beds

3 Baths

2,475 Sq.Ft.

$599,900

MLS#: DENC2095556

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

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

This home is a To-Be- Built. The Fayetteville offers a private home office just off the foyer, perfect for working from home in comfort. The striking modern kitchen features Looks interior options and opens to a spacious great room filled with natural light from abundant windows. The luxurious primary suite includes a generous walk-in closet and a relaxing primary bath with dual sinks. Upstairs, a versatile loft provides flexible space ideal for a game room, playroom, home theater, or additional living area. For a full list of features for this home, please contact our sales representatives. Photos are for illustrative purposes only and may not represent the exact home or finishes available.
#DENC2095730

MIDDLETOWN

128 PATTERSON COURT

3 Beds

3 Baths

2,307 Sq.Ft.

$598,990

MLS#: DENC2095730

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.

$596,000

MLS#: DENC2091784

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

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.
#DENC2079210

MIDDLETOWN

530 WHEELMEN STREET 1 EDMONSTON

4 Beds

2 Baths

2,716 Sq.Ft.

$591,000

MLS#: DENC2079210

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

CHARLESTON -TO BE BUILT. This 4 bedroom (OPTIONAL 1ST FLOOR 5TH BEDROOM) open floor plan welcomes homeowners and visitors alike in a space that flows effortlessly from one room to the next. There is a spacious kitchen with hardwood floors, along with 42" maple cabinets, granite countertops, and so much more! Be the first to build this floor plan and get a special incentive off any upgrades. Ask the sales manager for details. 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.
#DENC2079248

MIDDLETOWN

530 WHEELMEN STREET 6 CHARLESTON

4 Beds

2 Baths

2,730 Sq.Ft.

$590,000

MLS#: DENC2079248

New on site 3 days ago
Welcome to 30 Cantwell Drive in the sought after community of Cantwell Ridge. You are invited in by a two-story foyer with high ceilings and tons of natural light. Just off the entry there is a home office to the left, with glass doors, perfect for a private meeting or working from home. To the right of the entry is a dining room. As you continue down the hall you will find a generously sized powder room. The kitchen is open concept, overlooking the family room, which has a fireplace, so you don't miss out on the action when you have guests over. There is a large sunroom lined with floor to ceiling windows that overlooks the backyard. On the second floor you will find a huge owner's suite with a private sitting room, two walk-in closets that will not disappoint! And wait, the owner's bathroom is a retreat, with two vanities, a walk-in shower, and the soaking tub is a dream! Down the hall is three additional bedrooms and one full hall bathroom. There is a full basement, unfinished, waiting for your ideas to come to life. This home is in the Award-Winning school district of Appoquinimink School District.
#DENC2096660

MIDDLETOWN

30 CANTWELL DRIVE

4 Beds

2 Baths

3,342 Sq.Ft.

$585,000

MLS#: DENC2096660

Welcome to 1909 Gladys Street in the highly sought-after Town of Whitehall! Whitehall is a community that offers fantastic amenities, quality craftsmanship, and a warm welcome. This home's wow factor is abundant, from the curb appeal outside to the model home vibes inside. You will notice the beautiful landscaping and striking deep blue hardi-plank siding as you approach the home. Get ready to decorate the charming front porch for every season! Upon entering the front door, you will be greeted with a large living room to your right and a den to your left, which can be used for various purposes. The foyer, bathrooms, and kitchen have hardwood flooring, which gives the home a warm and welcoming feel. Moving forward, you will pass a hall closet and powder room and enter the main living space with an open floor concept. The kitchen is equipped with a large island, stainless appliances, beautiful 42" white cabinetry, and granite countertops. The family room and dining room are just off the kitchen. This model features a first-floor primary bedroom with double closets and en-suite bathroom, which includes a double sink vanity and a stand-up shower with glass doors. The laundry room is also on the main level, with tile flooring and access to the backyard and the garage. The massive garage can easily accommodate two large vehicles and provide ample storage space (including overhead storage). Upstairs, (iron balusters on the staircase) you will find an extra large loft perfect for various purposes, three spacious bedrooms, and a full bathroom! The unfinished basement is a vast space with an egress window, providing endless customization possibilities. The backyard has a brand-new vinyl fence, and the light fixtures and ceiling fans were just installed throughout the home. 1909 Gladys St. has a tree-lined view in the backyard and is tucked away in the neighborhood for extra privacy. A couple of NEW updates include new carpet in the lower level and fresh paint in several rooms and bathrooms. This home is conveniently located near the recreation center, where you can enjoy various activities such as Zumba, yoga, and self-defense classes. Additionally, the chiropractor, Christiana Care, and Wellness Center are located on-site. Lorewood Grove Elementary is within walking distance, and many shops have just opened and are coming soon! Convenience is just outside your door.
#DENC2096390

MIDDLETOWN

1909 GLADYS STREET

4 Beds

2 Baths

2,775 Sq.Ft.

$585,000

MLS#: DENC2096390

Beautiful 5-Bedroom Home with Finished Basement & Backyard Oasis - Prime Location Welcome to this spacious and well-maintained 5-bedroom, 3.5-bath home offering comfort, versatility, and modern open-concept living. The main level features a bright living room, kitchen, and dining area, ideal for entertaining and everyday living. A finished basement adds flexible space for a home theater, gym, or guest suite. Upstairs includes a versatile loft, perfect for a home office, playroom, or relaxation space. The home also offers a two-car garage and ample off-street parking. Enjoy outdoor living in the fully fenced yard featuring a peaceful koi pond, beautiful gardens, and mature fruit trees including pear, peach, plum, fig, and blueberry, along with roses, honeysuckle, grapevine, and wisteria —a true backyard retreat. Conveniently located near Route 1 and Route 13, and just minutes from the new Weis Market, offering easy access to shopping, dining, and commuting routes. Schedule your private showing today! Home inspection available via request from listing agent.
#DENC2095244

MIDDLETOWN

510 CILANTRO COURT

5 Beds

3 Baths

4,275 Sq.Ft.

$580,000

MLS#: DENC2095244

Welcome to the Cayot Model, in the desirable 55+ community of Traditions at Whitehall. This charming 3-bedroom home has a great open concept floor plan which offers all one floor living and a welcoming dining room and great room upon entry. At the rear of the home, you will find the luxurious owner's suite complete with walk-in closet and an en-suite bath, including a 5-foot tile shower. With a variety of structural and decorative options available, this home can be customized to perfectly fit your style and needs. Make this your dream home today! As a resident of this vibrant active adult community, you'll enjoy access to a wealth of amenities, including a state-of-the-art clubhouse, fitness facilities, sparkling swimming pools, walking trails, and a full calendar of social events to keep you engaged and connected with neighbors.
#DENC2080204

MIDDLETOWN

204 BALDY LANE CAYOT

3 Beds

2 Baths

2,004 Sq.Ft.

$579,000

MLS#: DENC2080204

* $15,000 builder incentive; thru 2/28/26 * 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.

$579,000

MLS#: PADA2048296

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