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 Charis Realty Group 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
254
# of Listings
3
Avg # of Bedrooms
$268
Avg. $ / Sq.Ft.
$654,976
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

254 Properties Found. Page 9 of 17.

Back on the market due to buyer’s home sale contingency not being satisfied. No fault of the seller or property. Inspections have been done and repairs completed so this home is ready for your buyers! Pride of ownership shines throughout this beautifully maintained home in the desirable Chesapeake Meadows community, located within the Appoquinimink School District. Set on just over an acre of meticulously landscaped grounds, this 4-bedroom, 2.5-bath residence offers privacy, space, and timeless comfort. As you enter, you’re welcomed by a stunning two-story foyer featuring a graceful turned staircase, complete with a chairlift for added accessibility. Formal living and dining rooms offer elegant spaces for entertaining, while the open-concept family room provides a comfortable retreat with the warmth of a natural gas fireplace. At the heart of the home, the gourmet kitchen features granite countertops, a center island, stainless steele appliances, and a sliding glass door that opens to a sprawling, level backyard—your own private outdoor oasis, perfect for gatherings, play, or peaceful evenings at home. The main level also offers a versatile fourth bedroom or home office, ideal for today’s flexible lifestyles. Laundry is located in a closet on the main floor. Upstairs, the oversized primary suite is a true retreat, complete with a sitting area and a spa-like primary bath designed for relaxation. Additional bedrooms are generously sized and thoughtfully laid out. Major updates have already been completed, including a newer roof, HVAC system, radon remediation system, windows, front door, and patio door, allowing the next owner to focus on cosmetic updates and personal touches. Home has been freshly painted. Additional highlights include an electric fence for pets and a home that has been lovingly cared for inside and out.
#DENC2094560

MIDDLETOWN

54 MEADOW DRIVE

4 Beds

2 Baths

2,879 Sq.Ft.

$599,900

MLS#: DENC2094560

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

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

Nestled in the prestigious Canal View subdivision, this exquisite Colonial-style residence embodies luxury and comfort. Built in 2016, the home boasts a stunning exterior with elegant vinyl siding, complemented by tasteful landscaping that invites you to explore its charm. The property features a beautifully maintained yard, complete with sidewalks and street lighting, creating a warm and welcoming atmosphere. Step outside to discover the community's exclusive amenities, including a sparkling outdoor pool and a sophisticated clubhouse, perfect for social gatherings or leisurely afternoons. The meticulously maintained grounds are enhanced by the association's commitment to lawn care, snow removal, and common area maintenance, ensuring a pristine environment year-round. Inside, the home offers a generous 4,100 square feet of living space, featuring a cozy gas fireplace that serves as a focal point in the inviting living area. With four spacious bedrooms and two and a half bathrooms, this residence is designed for both relaxation and entertaining. The upper-floor laundry adds convenience to your daily routine, while the walkout basement provides additional space for recreation or storage. Parking is a breeze with an attached two-car garage and ample driveway space. This property is not just a home; it's a lifestyle, offering the perfect blend of luxury, comfort, and community. Experience the best of Canal View living today!
#DENC2097228

MIDDLETOWN

331 ACASTA DRIVE

4 Beds

2 Baths

4,100 Sq.Ft.

$595,000

MLS#: DENC2097228

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

This spacious 3-bedroom home with a VERSATILE BONUS ROOM offers a thoughtfully designed layout and numerous updates throughout. The inviting family room with fireplace opens seamlessly to the center-island kitchen with a bar area at the island , now updated with a new stove, microwave, dishwasher, refreshed countertops, and a stylish backsplash, making it perfect for both everyday living and entertaining. Just off the kitchen you’ll find a convenient mudroom, pantry closet, half bath, and garage entry. Upstairs, the spacious primary suite boasts a tray ceiling, double vanities, his and her walk-in closets, and a beautifully tiled shower. Two additional bedrooms are generously sized, and the bonus room can be used as a den, home office, or playroom. The laundry room is conveniently located on this level. The full basement provides exceptional additional living space with a second family room, a large storage area, and a utility room. Plumbing is already roughed in for a future bathroom, and the water heater was replaced in 2019. Location Location Location!! Minutes from Routes 1, 13, and 301 with no tolls to go north and a grocery store 5 minutes away! Best of all—no grass to cut. The HOA handles lawn care, allowing you to enjoy your weekends relaxing by the community pool. HOA fees also include common area maintenance and snow removal.
#DENC2095628

MIDDLETOWN

336 ACASTA DRIVE

3 Beds

2 Baths

3,100 Sq.Ft.

$580,000

MLS#: DENC2095628

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

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

Priced to Sell!! 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.

$575,000

MLS#: DENC2096390

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

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