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
232
# of Listings
3
Avg # of Bedrooms
$269
Avg. $ / Sq.Ft.
$651,246
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

232 Properties Found. Page 5 of 16.

Build Your Dream Home in Middletown with Schaeffer Homes! Home is to be built. Photos and virtual tours show the same base model with optional upgrades. Discover our most quintessential rancher with the Weatherby! This generously-sized home starts at 2,498 square feet of living space. The Weatherby includes 3 bedrooms, 2 ½ bathrooms, 2-car garage, as well as a study! With one of our most sizable footprints, this remarkable abode gives plenty of room to spread out in this one-story home. This model also includes the option to upgrade to a larger front porch, perfect for relaxing out front with a warm cup of coffee. The Weatherby is ideal for those seeking ample space to expand and live comfortably. Pricing Overview Land Asking Price: $230,000 Home (The Ravello): $355,900 Estimated land development: $120,000* *Land development costs may be higher or lower. Seller and Builder make no representation of feasibility or final costs. The buyer should request a due diligence period to investigate. Schaeffer Homes will assist you throughout the due diligence process. Additional Details: It is unknown whether a basement foundation can be built on this property at this time. Other Schaeffer floorplans are available to be built here. Note: Home is to be built. Photos and virtual tours show the same base model with optional upgrades.
#DENC2089760

MIDDLETOWN

1487 BUNKER HILL ROAD

3 Beds

2 Baths

2,498 Sq.Ft.

$705,900

MLS#: DENC2089760

Stunning 4BR/3.5BA Duncaneshire Colonial Model by L.C. Homes in the sought-after Estates at St. Anne’s! Located in the Appoquinimink School District, this spacious home offers over 4,475 sq. ft. of living space on a premium .51-acre corner lot with a two-car side-entry garage. Enter the home through the grand two-story foyer featuring hardwood floors and a beautiful turned staircase. The formal living room offers an eye-catching bay window and crown molding, while the formal dining room features crown molding and an open box bay window. French doors off the foyer lead to a private home office or guest room. The two-story family room with a double-sided gas fireplace opens to the eat-in kitchen, complete with a spacious island, recessed lighting, and a walk-in pantry. A bonus sunroom/solarium provides flexible use as a playroom, gym, or game room and opens directly to the backyard. A powder room and convenient first-floor laundry complete the main level. The full unfinished basement is framed for a workshop and includes plumbing rough-in for a fourth full bathroom, offering endless customization potential total below grade 2,304 sq.ft. Upstairs, a loft overlooks the family room below. The expansive primary suite features two walk-in closets, a sitting area, and a luxurious 5-piece bath with dual vanities, large soaking tub, walk-in shower, private water closet, and space ideal for lounging, reading, quiet work, or workouts. Three additional bedrooms, including one with its own private full bath, plus a full hall bath complete the upper level. The Estates at St. Anne’s offers resort-style amenities, including walking trails, playgrounds, basketball and volleyball courts, a gazebo, community pool, clubhouse, banquet facilities, and a semi-private 18-hole links-style golf course with Highlands Whiskey Bar and Lore Modern Woodfyre restaurant. Conveniently located minutes from tax-free shopping, recreation, dining, and major highways. Walking distance to MOT Charter and just minutes from Routes 1, 13, and 301 for easy access to beaches and the city.
#DENC2092878

MIDDLETOWN

14 HAGGIS ROAD

4 Beds

3 Baths

4,475 Sq.Ft.

$699,999

MLS#: DENC2092878

The Carver offers a thoughtfully designed open floorplan with classic design touches, with a projected settlement of June 2026. This spacious home includes 3 bedrooms and 3.5 baths, featuring a finished basement complete with a private bedroom and full bath—perfect for guests, extended family, or a flexible retreat. A shiplap-accented fireplace anchors the main living space, while feature walls in the foyer and primary bedroom add character and charm. The screened porch overlooks community open space, and the large homesite tucked at the end of a cul-de-sac provides added privacy and curb appeal. The kitchen shines with a smart appliance upgrade, quartz countertops, and flows seamlessly into the main living areas finished with laminate flooring throughout the first floor. The primary bath is a relaxing escape with a tiled shower enclosure and rain shower head. A 2.5-car garage offers extra room for storage or hobbies. 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.
#DENC2096346

MIDDLETOWN

1525 LESTERFIELD WAY

3 Beds

3 Baths

2,493 Sq.Ft.

$699,990

MLS#: DENC2096346

WOW!!!! SELLER JUST MADE A $25,000 PRICE DROP!! OPEN HOUSE SAT, JAN 17TH 11am-1pm...............Don’t miss this opportunity to own a brand-new custom home on a 1-acre established neighborhood in Middletown, (you will not have to live through construction surrounding your home!) Offering 3,428 sq. ft. of thoughtfully designed living space. This home blends luxury, functionality, and space for the modern lifestyle. Enter through the double front doors into an impressive two-story foyer, & stained oak stairs that sets the tone for the rest of the home. To the right, a formal dining room provides ample space for large gatherings and includes a butler’s pantry for added convenience. The main living area features a bright and open-concept kitchen and family room, complete with a propane fireplace and picturesque views of the surrounding land. The kitchen boasts a hidden walk-in pantry designed to impress and accommodate all your storage needs. Granite countertops, stainless steel appliances and a gorgeous island make this kitchen perfect. A first-floor bedroom or home office with a full bath adds flexibility for guests or remote work. Upstairs, the primary suite is a true retreat with a spacious layout, stand-up shower, soaking tub, double bowl vanity, and an 8’ x 8’ walk-in closet. Two additional generously sized bedrooms (with walk in closets), and a full hall bath complete the second level. The finished basement includes a half bath, walk-out access, and the option to customize a large family or recreation room while still offering ample storage space. Propane gas and a 2 zone heating/Cooling system make for a comfortable home. A rear-facing 2-car garage adds both privacy and curb appeal. Located only 6 minutes from the St Georges Bridge gives you the luxury to take RT 1 wherever you need to go. This home combines high-end features with peaceful surroundings—perfect for those looking for new construction with room to grow.
#DENC2089908

MIDDLETOWN

704 BULLEN

4 Beds

3 Baths

3,428 Sq.Ft.

$699,900

MLS#: DENC2089908

FINAL HOME AT COPPERLEAF AVAILABLE IN 2026!!!! 411 Crownleaf Dr., the beautiful Montgomery Farmhouse! Off your front porch, you are greeted by a grand double story entry way with your formal dining room off to the side. Moving inward, an open layout seamlessly connects the family room with cozy fireplace, gourmet kitchen (complete w/ quartz counters, tile backsplash, and upgraded cabinetry), and included sunroom, creating an ideal setting for gatherings. Additionally, on the first level you will find your very own home office, as well as a spacious mudroom and walk-in pantry. The upper-level features 3 guest bedrooms, a hall bath, laundry room, and luxurious owner's suite. The owner’s suite offers a tranquil retreat area, perfect for relaxation. On the lower level, a large unfinished basement equipped with walk-up steps is ready for your personal touch—whether it’s a home theater, gym, additional living space, or storage. Enjoy luxurious living with convenient access to top-rated schools, shopping, dining, and recreation. This is more than just a home—it's a lifestyle. Contact us today to schedule a private tour. Prices, dimensions, and features may vary and are subject to change. Photos are for illustrative purposes only. Please see sales team for final details and finishes. Taxes to be assessed after settlement. If using a Realtor, the agent's client must acknowledge on their first interaction with Lennar that they are being represented by a Realtor, and the Realtor must accompany their client on their first visit.*
#DENC2081304

MIDDLETOWN

411 CROWNLEAF DRIVE

4 Beds

2 Baths

2,955 Sq.Ft.

$699,515

MLS#: DENC2081304

None
#DENC2093478

MIDDLETOWN

3032 BARBER LANE

3 Beds

2 Baths

N/A

$699,000

MLS#: DENC2093478

EXTREME PRICE IMPROVEMENT! Motivated Sellers! Be the lucky one to OWN this previous MODEL HOME and move in before Holiday season. Welcome to 712 Wallasey Drive! This beautiful 3 years young home by Ryan Homes is located in Middletown, Delaware, in the popular Preserve at Deep Creek. 712 Wallasey Dr is in the sought out Appoquinimink School District, conveniently located off of 301. You can enjoy this spacious new construction, with all the bells and whistles of a model home. This Seneca model offers 4450 square feet of living space with three gorgeous levels, boasting a finished basement with a full bathroom on a great lot. As you drive to the house, you are greeted with a beautiful upgraded front elevation, lovely landscaping, and a full size porch. As you enter the foyer, you will find a spacious study/office on your right and a powder room. As you continue your tour, you'll find that the home opens up to a big open family entertainment space – complete with a comfortable dining room, a warm family room, an expansive kitchen with a huge island, and another beautiful dining area. The entire first level has upgraded LVP flooring. You will love the white on white modern kitchen featuring quartz countertops, plentiful 42” crown cabinetry, updated hardware, new light fixtures, stainless appliances, gas cooking, vented out hood, a large island, an eat-in dining area, and a walk-in pantry. From the kitchen, you can walk out to a large, accessible, no maintenance deck and leveled lot, perfect for entertaining and for outdoor gatherings. The huge family room has a gas fireplace to keep you warm and cozy in all seasons. By the side of the family room, you'll find a convenient garage entrance which has an arrival center for all your accessories. From the family room, take the stairs to the second level where you'll find the enormous primary bedroom with a luxurious en-suite, featuring a large tile shower and two walk-in closets. You will have plenty of room for your family with three additional bedrooms, two of which share a Jack and Jill bath and a third, potentially a guest bedroom, that offers an en-suite bath. All bedrooms have walk-in closets, all bathrooms have easily maintained and aesthetically pleasing tiled floors. There is also a spacious center loft in this level for upper level entertainment. Upper level laundry completes the tour of second level. The finished lower level has three different entertaining areas for family to enjoy different activities. This gorgeous basement also has a full bath with finishes similar to the stylish bathrooms upstairs. There is a good size unfinished section in the basement for all your storage needs. All three levels have ample recess lighting and plenty windows to keep your home bright yet cozy. Other special features unique to this house are side entrance door for the garage, irrigation system for your lawn. Carrier HVAC system with two zone thermostat and tankless water heater are features that are done with functional convenience in mind. Schedule your tour today. House comes with no furniture. Pictures give idea of the size and furniture option visualization. Any questions contact listing agent.
#DENC2089228

MIDDLETOWN

712 WALLASEY DRIVE

4 Beds

4 Baths

4,450 Sq.Ft.

$699,000

MLS#: DENC2089228

Rothwell Estates from Benchmark Builders. The GRANDVIEW (to be built) is the larger of our 2 ranch floor plans. It has an optional 2nd floor loft/bedroom area, but is spacious without it. The large kitchen & vaulted ceiling in the great room are some of the stand out features in this home. We encourage you to take the virtual tour to see this floor plan. Rothwell Estates is endowed with a rich variety of two-story and ranch models, which include basements and an abundance of standard features such as a stone water table, hardwood standard in the foyer, kitchen and breakfast area,& powder room. Granite counter tops in the kitchen, stainless steel appliances, an island, 42" maple cabinets, gas fireplace, recessed lights, tile baths, fully sodded yard and much, much more! With an emphasis on open and versatile floor plans, you are certain to find the home of your dreams. Residences are situated on perfectly sized home sites, most of which back up to open space. And, you'll love the comfort and peace of mind these energy-efficient homes provide. Located in the highly regarded Appoquinimink School District, families will find much to appreciate. Whether you're looking for a home that offers first-floor living or a grand two-story design, Rothwell Estates has something for everyone! Please visit the model home at 126 Green Forest Drive, Middletown, DE 19709. Agent must accompany buyer on first visit or pre-register prior to first visit on builder website
#DENC2079882

MIDDLETOWN

126 GREEN FOREST DRIVE 3 GRANDVIEW

3 Beds

2 Baths

2,822 Sq.Ft.

$694,000

MLS#: DENC2079882

Welcome to this beautiful 5 bedroom home located in the highly desirable Estates of St. Annes. This home has been impeccably maintained by its original owners. As you enter the home you have a formal dining area to your right, and a living room or office space to your right. Continuing down the hall you will enter the open kitchen and living room area with a gorgeous fireplace. There is also a morning room that leads out to the lovely patio with no homes behind you! Upstairs you have all 5 bedrooms, including the massive primary suite with vaulted ceilings, a spa like bathroom, and walk in closets! Downstairs you have an amazing wet bar and tons of finished space for entertaining. We can't wait for you to see this home!
#DENC2086432

MIDDLETOWN

50 HAGGIS ROAD

5 Beds

2 Baths

4,700 Sq.Ft.

$689,999

MLS#: DENC2086432

This move-in ready, 3-year-old D.R. Horton home is a spacious two-story with five bedrooms, three and a half bathrooms. It also includes a game room with a wet bar, a media room, a workshop or exercise room, a full bathroom, and plenty of storage space in the basement, as well as a two-car garage and an oversized deck. The foyer features a coat closet and creates a welcoming flow for greeting guests. The front room is filled with natural light and is large enough to accommodate both a living and dining area. The spacious kitchen boasts beautiful birch cabinetry, granite countertops, stainless steel appliances, a pantry, and an island with seating. It opens to both the breakfast area and a sizable family room. A convenient powder room is located on the first floor, and the stairs to the second floor are tucked away in the family room, which also includes a cozy fireplace. Upstairs, the owner’s suite offers a large bedroom, two walk-in closets, and an oversized ensuite bathroom. The four additional generously sized bedrooms and a hall bathroom provide ample space for everyone. The first-floor laundry room is conveniently located near the garage, along with an additional coat closet. The property is vacant and ready to move in for the holiday.
#DENC2089762

MIDDLETOWN

1245 PIMPERNELL PATH

5 Beds

3 Baths

3,175 Sq.Ft.

$689,000

MLS#: DENC2089762

IMMEDIATE AVAILABILITY!!! Introducing the CHELSEA model 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, 9 ft ceilings, formal dining area, great room w/fireplace & an additional sunroom that flows into the kitchen perfect for entertaining. The Owner’s Suite includes a large walk-in closet and en-suite bath with a double vanity and standard tile shower. The gourmet kitchen comes w/stainless steel appliances, granite countertops, a large island, 1st floor laundry, and butlers pantry. In addition to your true one floor living this home also has a 2-car attached garage and unfinished full basement. The Chelsea Model offers the perfect combination of comfort and style. 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, and a full calendar of social events to keep you engaged and connected with neighbors.
#DENC2088952

MIDDLETOWN

548 LONGHORN LOOP LOT 33 CHELSEA

3 Beds

2 Baths

2,296 Sq.Ft.

$688,893

MLS#: DENC2088952

Last lots available. 7 month build time. See this model any day through the NTernow app. Rothwell Estates from Benchmark Builders. The HOUSTON (to be built) is our main decorated model. The 2 story foyer & great room, and a 2nd floor bridge are some of the stand out features in this home. We encourage you to take the virtual tour to see this floor plan. Rothwell Estates is endowed with a rich variety of two-story and ranch models, which include basements and an abundance of standard features such as a stone water table, hardwood standard in the foyer, kitchen and breakfast area,& powder room. Granite counter tops in the kitchen, stainless steel appliances, an island, 42" maple cabinets, gas fireplace, recessed lights, tile baths, fully sodded yard and much, much more! With an emphasis on open and versatile floor plans, you are certain to find the home of your dreams. Residences are situated on perfectly sized home sites, most of which back up to open space. And, you'll love the comfort and peace of mind these energy-efficient homes provide. Located in the highly regarded Appoquinimink School District, families will find much to appreciate. Whether you're looking for a home that offers first-floor living or a grand two-story design, Rothwell Estates has something for everyone! Please visit the model home at 126 Green Forest Drive, Middletown, DE 19709. Agent must accompany buyer on first visit or pre-register prior to first visit on builder website
#DENC2079892

MIDDLETOWN

126 GREEN FOREST DRIVE 5 HOUSTON

4 Beds

2 Baths

3,368 Sq.Ft.

$685,000

MLS#: DENC2079892

Rothwell Estates from Benchmark Builders. The JAMISON (to be built) is available to see in person until mid May, so contact the sales manager to book a walk through. The large kitchen, great room, and Extra Large Primary Suite are some of the stand out features in this home. We encourage you to take the virtual tour to see this floor plan. Rothwell Estates is endowed with a rich variety of two-story and ranch models, which include basements and an abundance of standard features such as a stone water table, hardwood standard in the foyer, kitchen and breakfast area,& powder room. Granite counter tops in the kitchen, stainless steel appliances, an island, 42" maple cabinets, gas fireplace, recessed lights, tile baths, fully sodded yard and much, much more! With an emphasis on open and versatile floor plans, you are certain to find the home of your dreams. Residences are situated on perfectly sized home sites, most of which back up to open space. And, you'll love the comfort and peace of mind these energy-efficient homes provide. Located in the highly regarded Appoquinimink School District, families will find much to appreciate. Whether you're looking for a home that offers first-floor living or a grand two-story design, Rothwell Estates has something for everyone! Please visit the model home at 126 Green Forest Drive, Middletown, DE 19709. Agent must accompany buyer on first visit or pre-register prior to first visit on builder website
#DENC2079886

MIDDLETOWN

126 GREEN FOREST DRIVE 4 JAMISON

3 Beds

2 Baths

2,225 Sq.Ft.

$685,000

MLS#: DENC2079886

Welcome to 321 Ellenwood Drive, located in the sought out neighborhood of PARKSIDE. What an unique home!!!! a semi custom home built by Lifestyle by the original owners. This inviting 4 bedroom, 3.1 bathroom home is very special....first floor very large primary suite...Beautiful kitchen with all new appliances including a double oven, great counter space and eat in area with sliding doors out to a lovely paver patio with real wrought iron railing. The family room just had their hardwoods refinished and WOW ... did they come out beautiful, a gas fireplace a 4 windows pouring in with natural sunlight. 2nd floor has a large loft, 2 bedrooms and 1 full bathroom and then a large office/playroom/flex room that has an opening to the the family room below....and a cute balcony to sit our on and stare out the stunning tree lined street..... then a third floor with another loft, large bedroom and full bathroom....wait, so much more.... a 3 season room that has 3 points of exits... one to side yard, one to the other side yard that is fenced and one off the back of the house connecting to the 2 car garage. Now, if that is not enough, there is a large unfinished basement waiting for you to finish if you wish with a rough in and 9 foot ceilings... also a walkup bilco door... radon remediation added... a generator...beautiful landscaping...upgraded and maintained so well.... Now for the best news...brand new roof and the solar panels are being put back up 12/1 and will be owned up until March of 2036....Sellers bought out the lease for your savings!!!! Parkside has so much to offer... the community pool, where you can soak up the sun and enjoy a refreshing swim during warm summer days. The gym..... the club house.... and all our beautiful pocket parks. Don't miss your chance to call this charming home in a sought-after neighborhood yours. Schedule a viewing today to experience the comfort and convenience this property has to offer in person.
#DENC2092224

MIDDLETOWN

321 ELLENWOOD DRIVE

4 Beds

3 Baths

3,175 Sq.Ft.

$685,000

MLS#: DENC2092224

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 Mayberry is a ranch home starting at 2,254 sq. ft., with 3 bedrooms, 2 baths, and a flex space. Split-bedroom design offers privacy; open kitchen with walk-in pantry flows to great room and dining. Options available for extra bedrooms, baths, and outdoor spaces.
#DENC2093526

MIDDLETOWN

2206 EARLY COURT

3 Beds

2 Baths

2,254 Sq.Ft.

$679,900

MLS#: DENC2093526

1 ... 3 4 5 6 7 ... 16

properties found. properties found. Page of .

- property

Send a message

Message successfully sent.

Your message

What is 3 + 4 ?

Reason for contacting?

Sign Out

Virtual Assistant

Would you like to take the next step with this property? We can help you schedule a showing or virtual tour, or send you more details.

Yes, I would like more information.

Thank You for Your Reply, One of Our Agents will contact you as soon as possible

No, maybe later.

Thank you, you can always contact me via email, phone number or through the contact form.

Realhub AI

Lucy - Your AI-Powered Realtor

Update Your Temporary Password

Personalize your search

Enter your email and we'll notify you immediately when new listings match what you're looking for.

or enter email address

Already have an account ? Login here

Continue your home search

Already have an account ? Login here

We use cookies

We use cookies primarily for analytics to enhance your experience. By accepting, you agree to our use of these cookies. You can manage your preferences or learn more about our cookies policy.

Privacy Policy Terms of Service