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
107
# of Listings
3
Avg # of Bedrooms
$330
Avg. $ / Sq.Ft.
$549,939
Med. List Price

Browse MIDDLETOWN Real Estate Listings

All listings

Under $250,000

$250,000 - $500,000

$500,000 - $1M

$1M - $3M

$3M - $5M

Over $5M

124 Properties Found. Page 4 of 9.

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

Beautiful Stone Front Colonial in Sought-After Pineland Park 3,887 total finished square feet offering 6 bedrooms and 3.5 baths on a 1-acre lot. Located in the desirable Pineland Park neighborhood of Warren County, ideal for commuting via I-66 and I-81. Minutes to golf, wineries, hiking, shopping, and downtown Front Royal. The Jefferson III model by H & H Builders features a stone front exterior, wide trim, interior columns, and 9-ft ceilings. Main level includes newly refinished hardwood floors throughout, a formal living room, and a formal dining room with chair rail and box ceiling detail. Spacious family room with corner gas fireplace opens to the kitchen with abundant cabinetry, countertop space, and breakfast area. Covered wrap-around front porch and rear covered porch provide great outdoor living spaces. Upper level offers hardwood hallway floors and new carpet in bedrooms. Newly remodeled primary suite includes vinyl plank flooring, tiled bath with soaking tub, separate shower, and walk-in closet. Three additional bedrooms and upper-level laundry for added convenience. Fully finished walk-out basement features tile flooring, kitchenette/wet bar, family room, two bedrooms, full bath, and ample storage—perfect in-law or guest suite. New AC units; furnace less than 5 years old. 2-car front-load garage with concrete driveway and plenty of off-street parking. Over 1 acre of open yard to enjoy.
#VAWR2012638

MIDDLETOWN

76 KATIE LANE

6 Beds

3 Baths

3,888 Sq.Ft.

$685,000

MLS#: VAWR2012638

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

Nestled in the Brighton subdivision, this exquisite Colonial-style residence, built by Toll Brothers in 2023 on a corner lot, embodies the pinnacle of modern luxury living. Spanning approximately 2,650 square feet, this detached home offers a harmonious blend of elegance and functionality, perfect for those who appreciate high-end finishes and thoughtful design. Step inside the front door from the covered porch to discover an open floor plan that seamlessly integrates living spaces, accentuated by luxury vinyl plank flooring and strategically placed recessed lighting that enhances the ambiance of the 9' ceilings. The heart of the home is the gourmet kitchen, featuring granite countertops and a spacious island that invites culinary creativity. Equipped with top-of-the-line appliances, including a smart refrigerator, smart double oven, built-in microwave, and sleek induction cooktop, this kitchen is a chef's dream. The adjoining flex space serves perfectly as a dining area providing an ideal setting for entertaining naturally extending between the kitchen, dining, and great room areas. The large pantry ensures ample storage for all your culinary essentials coupled with a second closet space off the kitchen which can feature as an additional pantry or kitchen appliance storage to keep those granite countertops clear of clutter! The great room is a natural gathering space lit by abundant natural light. The far wall features sound absorbing slated Sonolok by Artika paneling making movie night an experience! Around the corner on the main level the home office is easily accessible without feeling overly pronounced striking the perfect balance for those who want to separate work in the office from living in the home. The main level powder room includes the PEX plumbing ran to convert to a full bath should you wish to do so in the future. Upstairs the primary suite ties together the same luxury vinyl plank from the main level. The suite includes a generous walk-in closet with extensive built-in shelving offering a dream wardrobe organization system. The en-suite tile floored bathroom is a haven showcasing a walk-in shower compatible with voice control through Anthem by Kohler and enriched by green porcelain tile and gold colored fixtures that promises relaxation and rejuvenation. A designated electrical outlet provides the opportunity for smart toilet or electronic bidet options should the future owners wish to continue adding to the modern oasis. Three additional spacious bedrooms adorn the upper level each featuring soft carpet flooring and ceiling fans. These bedrooms are complemented by a stylish full bathroom. The upper-floor laundry room adds a touch of practicality, making everyday chores a breeze and easily keeping laundry out of view when entertaining. Security is paramount, with a Ring camera as well as an advanced Reolink security system of exterior cameras ensuring peace of mind. Outside, the fenced-in corner lot enhances privacy and curb appeal, while the rear-entry detached two car garage continues to elevate with an electric vehicle charger and additional storage space. Additionally, the asphalt driveway accommodates multiple vehicles. A charming small greenhouse easily accessed from the basement walkout adds a unique touch, perfect for gardening enthusiasts. When finished gardening, the gorgeous backyard patio provides space to relax and unwind enjoying fresh air. In addition to the walkout stairs the basement includes storage shelving, an active radon mitigation system, and rough-in plumbing. This property is not just a home; it's a lifestyle featuring intentional upgrades and boundless potential. Experience the luxury of modern living where every detail has been meticulously crafted for comfort, style and functionality. This is more than a residence; it's an invitation to elevate your everyday life allowing you to focus on what truly matters - and all in the renowned Appoquinimink School District.
#DENC2092354

MIDDLETOWN

141 S LORES LANDING ROAD

4 Beds

2 Baths

2,650 Sq.Ft.

$679,999

MLS#: DENC2092354

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 Jameson, a two-story home with a first-floor owner’s suite and 2,568+ sq. ft. Includes 3 bedrooms and 2.5 baths. Features a tandem 3-car garage, open kitchen with island seating, breakfast nook, spacious great room, flex room, and walk-in pantry. Upstairs offers 2 bedrooms, loft, full bath, and two unfinished bonus rooms. Options include additional bedrooms, baths, a second owner’s suite, and outdoor living spaces.
#DENC2093484

MIDDLETOWN

1143 MAJESTY LANE

3 Beds

2 Baths

2,705 Sq.Ft.

$679,900

MLS#: DENC2093484

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 Kingfisher, a two-story home with a first-floor owner’s suite and 2,566+ sq. ft. Includes 3 bedrooms and 2.5 baths. Features an open kitchen with island seating, breakfast nook, spacious great room, and flex room. Upstairs offers 2 bedrooms, a loft, full bath, and unfinished bonus room. Options include additional bedrooms, baths, and outdoor living spaces. Schedule your appointment today for details and incentives.
#DENC2093362

MIDDLETOWN

1145 MAJESTY LANE

3 Beds

2 Baths

2,566 Sq.Ft.

$669,900

MLS#: DENC2093362

This is a builder model home sale. This beautiful Calloway Queen Anne offers 2,657 square feet of living space. The abundance of windows floods the family room and kitchen with natural light. Upgraded luxury vinyl plank runs throughout the first floor, the upstairs hall, and primary bedroom. The kitchen boasts an oversized island, quartz countertops, and a tiled backsplash. Both bathrooms offer quartz vanity tops.
#DENC2088810

MIDDLETOWN

5605 S BAYBERRY PKY

4 Beds

2 Baths

N/A

$669,300

MLS#: DENC2088810

Brand New 55+ Community in Middletown, DE The Morse home design blends a spacious open floorplan with classic architectural details, creating a timeless yet modern living experience. With 3 bedrooms (including one in the finished basement), 3.5 baths, and a 2.5-car garage, this home offers both functionality and refined style. Highlights include a fireplace with shiplap surround, feature walls in the foyer and owner’s suite, and a screened porch that overlooks beautiful community open space—perfect for relaxing or entertaining. The finished basement adds extra versatility, complete with a full bedroom and bath ideal for guests or extended family. The kitchen is designed for convenience and style, featuring smart appliance upgrades and quartz countertops for a sleek, modern finish. Laminate flooring throughout the first floor enhances the flow of the open-concept layout while offering easy maintenance. In the owner’s bath, a tiled shower enclosure with a rain shower head brings a spa-like touch to everyday living. For a full list of included features, please contact our sales representatives. Photos are for illustrative purposes only and may not represent the exact home or finishes available.
#DENC2091996

MIDDLETOWN

1602 JAYMES CIRCLE

3 Beds

2 Baths

2,349 Sq.Ft.

$664,900

MLS#: DENC2091996

Welcome to 1236 Pimpernell Path! This beautifully maintained, move-in ready 4-year-old D.R. Horton home offers exceptional space and modern design throughout. This amazing home feels and smells like brand-new construction! Don’t miss this rare opportunity to own a home in one of the most desirable communities. This spacious two-story residence offers nearly 2,600 sq. ft. of living space featuring 5 bedrooms and 3 bathrooms. The clean, ready-to-finish basement provides incredible potential — complete with a game room and wet bar, media room, workshop or exercise area, full bathroom, and ample storage space. The main level showcases an inviting foyer with a coat closet, leading to a bright and open living and dining area filled with natural light. The kitchen includes birch cabinetry, granite countertops, stainless steel appliances, a pantry, and a large island with seating, opening to both the breakfast area and family room featuring a cozy fireplace. A convenient powder room completes the first floor. Upstairs, the owner’s suite features a spacious bedroom, two walk-in closets, and a large ensuite bathroom. Additional well-sized bedrooms and a hall bathroom offer comfort for family or guests. Additional highlights include a first-floor laundry room adjacent to the garage entry, an oversized deck perfect for outdoor entertaining, and a two-car garage. This home combines thoughtful design, functionality, and quality finishes—ready for you to move right in!
#DENC2092178

MIDDLETOWN

1236 PIMPERNELL PATH

5 Beds

3 Baths

2,550 Sq.Ft.

$662,000

MLS#: DENC2092178

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 Cassidy is a ranch home starting at 2,528 sq. ft., featuring 4 bedrooms, 3.5 baths, and an unfinished bonus room. Open kitchen with walk-in pantry flows to great room and dining. Options available for extra bedrooms, baths, and outdoor living.
#DENC2093486

MIDDLETOWN

2205 EARLY COURT

4 Beds

3 Baths

2,528 Sq.Ft.

$659,900

MLS#: DENC2093486

New construction without the wait. This gorgeous estate home has everything you could want and more! With four bedrooms and 2.5 baths, it ensures enough space for the whole family - and that includes a modern Study/Laundry Upgrade. Additional features include an upgraded kitchen with island, gas range & granite counters; a 1st-floor powder room; a 3-piece basement rough-in with partially finished basement, and a roomy two-car garage. Make an appointment to tour it now.
#DENC2091264

MIDDLETOWN

642 GORDON HOUSE WAY

4 Beds

2 Baths

2,889 Sq.Ft.

$657,712

MLS#: DENC2091264

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