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
225
# of Listings
3
Avg # of Bedrooms
$270
Avg. $ / Sq.Ft.
$661,597
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

122 Properties Found. Page 7 of 9.

New on site 1 day 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

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.
#DENC2088128

MIDDLETOWN

30 CANTWELL DRIVE

4 Beds

2 Baths

3,342 Sq.Ft.

$585,000

MLS#: DENC2088128

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

Welcome to the Village of Bayberry South — an exceptional 55+ community where resort-style amenities and low-maintenance living come together to create a truly elevated lifestyle. This impeccably maintained home is move-in ready and positioned on one of the largest lots in the neighborhood, peacefully tucked away on a quiet, tree-lined street. Designed for effortless single-level living, the open-concept layout blends sophistication, comfort, and everyday practicality. Step inside to a warm and inviting foyer that flows into a bright and flexible living space, easily adaptable to multiple seating or dining configurations. The living room is filled with natural light from twin sets of double windows, creating a cheerful, airy atmosphere that sets the tone for the rest of the home. At the heart of the residence is the beautifully appointed chef’s kitchen, featuring granite countertops, upgraded cabinetry, and a generous center island perfect for both casual meals and stylish entertaining. A charming breakfast nook sits just beyond, with sliding glass doors that open to a private TREX deck overlooking the beautifully manicured backyard — the ideal spot for morning coffee, alfresco dining, or a quiet evening unwind. This thoughtfully designed home offers three spacious bedrooms, 2.5 bathrooms, and an additional flex room that can serve as an office, den, or even a fourth bedroom. Two of the bedrooms offer private en-suite bathrooms, providing comfort and convenience for both owners and guests. The third bedroom offers excellent versatility, whether used for visitors or a dedicated workspace. The full basement, complete with an egress window, provides exceptional storage and offers the potential to create additional living space tailored to your needs. For added peace of mind, the home is equipped with a whole-house generator, ensuring comfort and security in any weather. Life at Bayberry South is truly maintenance-free — lawn care, landscaping, and snow removal are all handled for you, allowing more time to enjoy the community’s impressive amenities. The clubhouse serves as the vibrant social hub of the neighborhood, offering a resort-style pool with tranquil pond views, a state-of-the-art fitness center, game and billiards rooms, and tennis/pickleball courts. With a robust calendar of clubs, activities, and events, you’ll find endless opportunities to stay active, engaged, and connected.
#DENC2091776

MIDDLETOWN

4116 LAUGHTON LANE

4 Beds

2 Baths

2,650 Sq.Ft.

$579,000

MLS#: DENC2091776

Below market value & PRICED TO SELL!!!!! This meticulously maintained home reflects true pride of ownership, both inside and out. Thoughtfully priced and offering exceptional value, this home is ideally situated in the prestigious community of The Legends in Middletown, enjoying convenient access to shopping, dining, and everyday amenities while offering a peaceful, scenic setting overlooking the golf course. Upon entry, a grand two-story foyer welcomes you with soaring ceilings and an elegant turned staircase, immediately setting a tone of sophistication. The thoughtfully designed, flowing floor plan leads to a stunning two-story family room, highlighted by a gas fireplace that creates a warm and inviting focal point—perfect for cozy evenings or refined entertaining. The spacious kitchen is designed for both function and style, featuring abundant cabinetry and counter space, a center island for added storage, and sliding glass doors that open to the deck—seamlessly blending indoor and outdoor living. The rear fenced yard offers privacy and generous space for entertaining, gardening, or simply unwinding while enjoying tranquil golf course views. Enhancing the home’s functionality, the main level also features a private office, ideal for today’s work-from-home lifestyle, as well as a convenient main-level laundry room with direct access to the garage, adding everyday ease and practicality. The primary suite serves as a private retreat, complete with a walk-in closet, linen closet, and a beautifully appointed en-suite bath. Three additional generously sized bedrooms and a well-appointed hall bath complete the upper level, offering comfort and flexibility for family, guests, or home office needs. A true highlight of this home is the fully finished basement, providing exceptional bonus space. It features two additional rooms with closets, a full bath, a counter and cabinet area ideal for entertaining, a dedicated theater area, and a large unfinished space for ample storage—perfect for multi-generational living, recreation, or extended guest accommodations. This home is a MUST SEE!!!
#DENC2093134

MIDDLETOWN

241 PORKY OLIVER DRIVE

4 Beds

2 Baths

2,650 Sq.Ft.

$578,000

MLS#: DENC2093134

TO BE BUILT - The Oxford - Whether you're looking for a detached homes home large enough to raise a growing family, an intelligently designed attached carriage home, or a modern townhome with tons of living space, it's all here at the Reserve at Ponds of Odessa. Our homes feature 2-4 bedrooms with optional first floor owner's bedroom, 2 car garage, 2/2.5 baths, 42" cabinets, wall to wall carpeting, spacious open- concept main level, public sewer and water, underground utilities, blacktop driveway, streetlights, sidewalks and curb lined streets. Located in Appoquinimink School district. This beautiful home features 4 bedrooms, 2.5 full baths, 2 car garage. Standard features include a partially finished basement, Granite kitchen countertops, 42" maple cabinets, stainless steel appliances, hardwood floors in foyer, kitchen & breakfast area & a stone water table on the exterior. Builder Splits Transfer Tax
#DENC2079326

MIDDLETOWN

400 REDERICK LANE 2 OXFORD

4 Beds

2 Baths

2,357 Sq.Ft.

$576,500

MLS#: DENC2079326

TO BE BUILT - The Sassafras II- This beautiful ranch home features 3 bedrooms, 2 full baths, 2 car garage. Standard features include a full unfinished basement, Granite kitchen countertops, 42" maple cabinets, stainless steel appliances, hardwood floors in foyer, kitchen & breakfast area & a stone water table on the exterior. Appoquinimink School district! *Photos shown are of similar home, not listed property. Agent must accompany buyer on first visit or preregister prior to first visit on builder website.
#DENC2079330

MIDDLETOWN

400 REDERICK LANE 4 SASSAFRAS II

3 Beds

2 Baths

2,200 Sq.Ft.

$576,000

MLS#: DENC2079330

Welcome to 321 Jessica Drive, a spacious five bedroom, three and a half bathroom home offering a remarkable blend of generous living space and everyday convenience. Located in the highly sought after Appoquinimink School District, this residence sits on a 0.65 acre lot and provides plenty of room for outdoor enjoyment and personal expression. Inside you will find a thoughtful layout with large rooms that invite comfortable daily living and effortless entertaining. The open and connected living areas create a sense of flow while leaving plenty of room for privacy and separation. The property’s location gives you easy access to Route 1 for beach bound travel and Christiana Mall, as well as convenient connections to I-95 north toward the Philadelphia airport and south toward Baltimore and the Baltimore airport. Route 301 is nearby for travel toward Annapolis. Offered as a short sale, this home represents a rare opportunity to own a substantial residence in one of Middletown’s premier locations with long term potential.
#DENC2094594

MIDDLETOWN

321 JESSICA DRIVE

5 Beds

4 Baths

5,250 Sq.Ft.

$575,000

MLS#: DENC2094594

This charming brick rancher is located at the end of a cul-de-sac in sought after Middletown and sits on a peaceful 1.72 acre level lot. The first floor features an open floor plan complete with hardwood floors throughout, formal living room, formal dining room, family room with brick fireplace, breakfast nook leads to a relaxing Trex deck and patio overlooking the large backyard. 1st floor laundry room leads to a oversized 2 car garage. 3 bedrooms and 2 full baths. The fully finished walkout lower level features another full bathroom and large storage room. Some recent upgrades include 20 SEER heat pump (2023), new septic field (2023), electric fireplace (2024), well pump (2020), Ecobee smart thermostat (2023).
#MDFR2073664

MIDDLETOWN

6527 MORNINGSIDE COURT

3 Beds

3 Baths

2,275 Sq.Ft.

$574,900

MLS#: MDFR2073664

Benchmark Builders at The Town of Whitehall, Chadwick Floor Plan. TO BE BUILT. The hometown is finally getting its come back. 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. Whitehall has it all! Chadwick floor plan feature 4bedrooms, 2.5 baths, 2nd floor laundry, 2 car attached rear entry garage, an open floor plan for entertainment with a huge great room! **Optional Chadwick front porch shown in photo**.Agent must accompany client on first visit or pre-register client on builder website prior to first visit
#DENC2079246

MIDDLETOWN

530 WHEELMEN STREET 5 CHADWICK

4 Beds

2 Baths

2,456 Sq.Ft.

$570,500

MLS#: DENC2079246

This well built, all brick rancher sits on a corner lot and is in excellent condition. It has 4 generous sized bedrooms and 3 full bathrooms (every bedroom has direct access to a full bath) and an in-law suite with 2 separate entrances. Gas fireplace on main level and wood burning fireplace in finished basement. Beautiful hardwood floors in the foyer, hallway, dining room, living room and 3 bedrooms. Huge finished walk-out basement with large storage area. Floors in basement (rec room and basement bedroom) were recently replaced. Circular driveway and 2 car garage with a hot tub!
#MDFR2074538

MIDDLETOWN

215 BROAD STREET

4 Beds

3 Baths

2,580 Sq.Ft.

$570,000

MLS#: MDFR2074538

Welcome to 505 Cherry Bark Road in Four Seasons at Baymont Farms, a premier 55+ active adult community in Middletown, Delaware. This nearly new Eastwood Loft Floorplan, just 2 years young, offers low-maintenance, resort-style living with thoughtful design and modern upgrades throughout. Step inside to an open ranch-style floor plan featuring 2 bedrooms and 2 full baths on the main level—with an additional home office—plus a bonus second level with an additional bedroom, full bath, and a spacious loft living area, ideal for grandkids and guest. The home’s inviting exterior showcases a front porch with stone and shiplap accents. Inside, enjoy luxury vinyl plank flooring, a cozy gas fireplace, and a gourmet kitchen complete with soft-close cabinetry, GE Profile appliances, gas cooking, and a large quartz island and countertops. A sunroom bump-out fills the space with natural light, while the primary suite offers a private retreat with a large walk-in closet, dual vanities, and a spa-like walk-in shower. Additional highlights include a full basement with poured concrete foundation and egress window—partially started as a craft room, with rough-in for a future full bath—plus a sprinkler system for easy lawn care. Life at Four Seasons at Baymont Farms centers around connection and convenience. Residents enjoy a 6,000 sq. ft. clubhouse, resort-style pool with tiki hut, state-of-the-art fitness center, kayak launch, bocce and pickleball courts, and a vibrant calendar of events led by the community lifestyle director. From yoga and Zumba to billiards and social gatherings, there’s always something to enjoy. Located just minutes from downtown Middletown with quick access to Rt. 1, Baymont Farms offers the perfect blend of serenity and accessibility. With landscaping and community upkeep included through the HOA, you’ll have more time to focus on hobbies, friendships, and the lifestyle you deserve. Come see why 505 Cherry Bark Road is more than just a house—it’s the start of your next chapter in resort-style living.
#DENC2089330

MIDDLETOWN

505 CHERRY BARK ROAD

3 Beds

3 Baths

2,650 Sq.Ft.

$565,000

MLS#: DENC2089330

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