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
$329
Avg. $ / Sq.Ft.
$549,729
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

296 Properties Found. Page 8 of 20.

Nestled in the prestigious community of The Legends, this exquisite traditional home offers a harmonious blend of luxury and comfort, perfect for those seeking an elevated lifestyle. Set on a desirable corner lot, this residence boasts an impressive 2,700 square feet of thoughtfully designed living space, ensuring ample room for relaxation and entertainment. As you step inside, you are greeted by a warm and inviting atmosphere, enhanced by rich hardwood flooring that flows seamlessly throughout the main areas. The kitchen has plenty of cabinet space with roll out shelves, Granite countertop, backsplash and stainless appliances with a double oven. The upstairs has a spacious layout and features four generously sized bedrooms, providing a tranquil retreat for everyone. The master suite is a true sanctuary, complete with an en-suite bathroom that exudes elegance and functionality. The heart of the home is undoubtedly the cozy living area, where a charming fireplace serves as a focal point, inviting you to unwind after a long day. With main floor laundry facilities, convenience is at your fingertips, allowing you to focus on what truly matters-creating memories in your new home. A 12x14 screened in deck area leads to the outside. The outside: the property features a well-maintained yard, perfect for outdoor activities or simply enjoying the serene surroundings. The attached garage and driveway provide ample parking space, ensuring that you and your guests are always accommodated. Built in 2001, this home combines modern amenities with timeless architectural charm, featuring durable vinyl siding and stucco that enhance its curb appeal. The full basement with a full bath Rough In offers endless possibilities for customization, whether you envision a home gym, entertainment space, or additional storage. Living in The Legends means embracing a lifestyle of exclusivity and comfort, with access to nearby amenities that cater to your every need. This corner lot residence is not just a house; it's a place where you can create lasting memories and enjoy the finer things in life. Experience the perfect blend of luxury and comfort in this stunning home-your dream lifestyle awaits.
#DENC2092438

MIDDLETOWN

1 HOGAN CIRCLE

4 Beds

2 Baths

2,700 Sq.Ft.

$599,900

MLS#: DENC2092438

Step inside-You'll love it! This is a home designed to impress and it can be your new home before the Holidays! Spacious and beautifully updated 6-bedroom is perfect for multigenerational living. A rare find- two master suites, dual family rooms and high-end upgrades throughout. The home offers flexible space ideal for large families, guests, or home offices. Recent updates include a new roof, gleaming hardwood floors and one new ceramic bath. The updated kitchen shines with granite countertops, stainless steel appliances. Having multiple gathering areas this home has a perfect layout for entertaining. The inviting layout makes this home ideal for family events, relaxation or hosing guest. You won't be disappointed by the stunning landscape, multiple decks and it even has a handicap access ramp! Additionally, the Home is conventionally located near the well-known Middletown Park. Don't miss your chance to make it yours-schedule your private showing today!
#MDFR2066902

MIDDLETOWN

4311 ZIRCON ROAD

6 Beds

4 Baths

3,072 Sq.Ft.

$599,000

MLS#: MDFR2066902

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

* BUILDER'S END-OF-YEAR CLOSEOUT! LIMITED TIME OFFER…. CALL TODAY for details! * 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.

$599,000

MLS#: PADA2048296

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

VILLAGE OF BAYBERRY NORTH – Immaculate 4-Bedroom, 2.5-Bathroom Colonial home with a 2-CAR GARAGE and a fully fenced yard. Built just 5 years ago, this home is LIKE NEW! Enter into the foyer where you will notice HANDSCRAPED HARDWOOD FLOORS that run throughout the majority of the first floor. An open layout exists between the formal dining area and living room. Upgraded light fixtures have been added here & throughout the entire home. Straight ahead, you’ll find the kitchen, family room, and breakfast room. The kitchen features: GRANITE countertops, STAINLESS STEEL APPLIANCES, tile backsplash, recessed lighting, and a pantry. Sliders from the breakfast room lead to the huge maintenance-free TREX DECK. The deck steps down to the fully fenced yard with a shed included for your outdoor storage needs. Back inside and also on the first floor is the powder room and the laundry room. Head upstairs to find 4 bedrooms and 2 full baths. Double doors lead to the master suite which boasts a WALK-IN CLOSET, a 2nd closet, and a full master bath. The 5-piece master bathroom features 2 vanities, a jacuzzi tub, & a stall shower. A full, open unfinished basement offers the option to finish for added living space or simply use for storage. The unfinished basement includes a plumbing rough-in for a 3rd full bathroom. This is The Gable Floorplan, premium Colonial Elevation with a stone water table. Several builder upgrades were selected, including the Luxury Master Bath w/ 4’ fiberglass shower, 6x6 tiled tub deck, jetted tub, & granite vanity top. Other notable features include: FRESH PAINT throughout, security system with surveillance cameras included, & smart doorbell included. Located in a lively community that offers a modern clubhouse, numerous playgrounds, pavilions, walking trails, a dog park, biking trails, and picnic areas. The 3,400 sq. ft. clubhouse is located on a private lake that can be used by residents for boating and fishing. Conveniently close to major roadways (DE-1, DE-13, DE-301) for ease of commute. Don’t wait, schedule your tour today!
#DENC2094370

MIDDLETOWN

755 STANFORD WHITE WAY

4 Beds

2 Baths

2,650 Sq.Ft.

$594,000

MLS#: DENC2094370

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

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

NEW FLOOR PLAN - CHARLESTON -TO BE BUILT. This 4 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

Welcome to 3151 Schuman Drive, a stunning Cooper Model home situated on a premier lot in the Village of Bayberry South, Middletown. This elegant residence, one of the few backing to serene woodlands, offers an expansive backyard with unobstructed views, providing unparalleled privacy. Encompassing 2,050 square feet of sophisticated living space, this home boasts three spacious bedrooms and two well-appointed bathrooms. The primary bedroom features a luxurious two-foot extension for additional comfort. Notably, the third bedroom, currently styled as an office, is graced with charming bay windows. Culinary enthusiasts will delight in the kitchen, complete with upgraded granite countertops and a state-of-the-art induction cooktop. The adjacent four-season sunroom seamlessly connects to the back deck, equipped with an electric retractable awning. This home is further enhanced by modern conveniences and upgrades such as hardwood flooring, remote-controlled blinds across three zones, recessed lighting, and a top-tier Bosch electric heat pump. A full unfinished basement with an egress window and sump pump offers endless possibilities for additional living and entertainment spaces. Energy efficiency is prioritized with owned solar panels rated at an impressive 10,000 kW, often nullifying electricity costs outside of the coldest winter months. The property also includes a WiFi-controlled irrigation system, a paving pad with discreet trash storage, and three ceiling fans for added comfort. Experience the perfect blend of elegance, modernity, and privacy in this exquisite home.
#DENC2093704

MIDDLETOWN

3151 SCHUMAN DRIVE

3 Beds

2 Baths

2,050 Sq.Ft.

$589,900

MLS#: DENC2093704

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. Be in your new home before the holidays.
#DENC2088128

MIDDLETOWN

30 CANTWELL DRIVE

4 Beds

2 Baths

3,342 Sq.Ft.

$585,000

MLS#: DENC2088128

New on site 4 days ago
Middletown’s fastest-selling active adult community is selling quickly—and opportunities like this don’t come around often. Venue at Winchelsea is in its final stretch of Phase One single-family homes, so now is the time to secure an incredible home at an exceptional value before it’s gone. Welcome to 2918 Cordwainers Lane, featuring the highly sought-after Mendocino Luxe floorplan. This beautifully designed home offers 2 bedrooms, 3 bathrooms, and a finished basement, checking every box for comfort, style, and flexibility. The inviting foyer opens to a rare and valuable flex space, ideal for a home office or hobby room, along with a formal dining room perfect for entertaining. The bright white, open-concept kitchen shines with a large center island, abundant cabinetry, a wall oven, and gas cooktop—making hosting effortless. Sunlight fills the family room, which flows seamlessly to a spacious covered patio, the perfect place to unwind and enjoy sunset views. The owner’s suite is a true retreat with two walk-in closets and a spa-like en-suite bath featuring a double vanity and walk-in shower. Upstairs, a finished loft offers endless possibilities—crafting, hobbies, or a cozy getaway for visiting grandchildren. The finished basement with a full bath adds even more space for guests, entertaining, or relaxation. About the Community: This vibrant 55+ active adult community is designed for living your best life. Residents will enjoy a 5,400-square-foot clubhouse, pickleball and tennis courts, bocce, a resort-style pool, a state-of-the-art fitness center, and a full calendar of activities—so there’s always something to look forward to. Best of all, lawn care, snow removal, and trash and recycling are included, giving you the freedom to spend your time exactly how you choose. Homes are selling quickly, and Phase One is almost gone—don’t wait to claim your place at Venue at Winchelsea. This is your chance to get in before it’s too late. *Please see New Home Consultant for details. 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. For appointments and open houses, please visit the model home located at 2405 Greyfriar Loop.
#DENC2094580

MIDDLETOWN

2918 CORDWAINERS LANE

2 Beds

3 Baths

3,422 Sq.Ft.

$584,990

MLS#: DENC2094580

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

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

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

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