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
239
# of Listings
3
Avg # of Bedrooms
$269
Avg. $ / Sq.Ft.
$652,041
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

239 Properties Found. Page 9 of 16.

* $15,000 builder incentive; thru 2/28/26 * The home you have been admiring is now available! There are so many beautiful features in this Woodland Hills model home and they can be yours without the wait time of a new home build. The Osprey model has 2,898 sq ft with 4 bedrooms and two and a half bathrooms. With ample storage and counter space, the kitchen will be where the family and guests will want to gather. The beautiful granite counters, oversized island and under-cabinet lighting are a few of the custom features that you will enjoy. Soak up the sun all year round in the 12x14 sunroom that is situated just off the great room area. A gas fireplace and built-in bookshelves are the natural focal point of the living room area. Also on the 1st floor is the flex room, study, laundry room, powder room and a mudroom area with a bench seat, coat hooks and lockers. The second floor has 4 larger bedrooms and 2 bathrooms. The master bath, with it's ceramic tile floor, tiled shower and soaking tub, will be your place to retreat and pamper yourself at the end of the day. The hall bath has a tub/shower. The unfinished basement features 9' poured concrete walls. You also have the convenience of a central vac system. This home is situated on a corner homesite and has easy access to Vine Street and I-283. Although loaded with custom features, this home is priced well below replacement cost.
#PADA2048296

MIDDLETOWN

195 MAGNOLIA DRIVE

4 Beds

2 Baths

2,898 Sq.Ft.

$579,000

MLS#: PADA2048296

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

MIDDLETOWN

4116 LAUGHTON LANE

4 Beds

2 Baths

2,650 Sq.Ft.

$579,000

MLS#: DENC2091776

New on site 4 days ago
Welcome home to 1218 N Olmsted Pkwy located in the sought-after Village of Bayberry North. Upon arrival, you’ll immediately notice the beautiful stone veneer exterior, offering timeless curb appeal and setting the tone for this well-maintained, 5-year-old ranch home. An inviting covered front porch welcomes you in, perfect for morning coffee, evening relaxation, or connecting with neighbors.. Step inside to an OPEN -CONCEPT LAYOUT filled with natural light and hardwood flooring . The spacious living room flows seamlessly into the dining area and continues into the kitchen, creating an ideal space for everyday living and entertaining.The kitchen features a CENTER ISLAND, GRANITE COUNTERTOPS, STAINLESS STEEL APPLIANCES, A DOUBLE OVEN, and a sunny BUMP- OUT BREAKFAST area that fills the home with natural light. Step outside to the fully fenced backyard, offering endless possibilities for entertaining, relaxing, or outdoor activities. Back inside, the home offers a convenient laundry room with access to the two-car garage. You’ll find generously sized bedrooms, along with a versatile additional room that can be used as a third bedroom, home office, or playroom. The primary suite boasts a spacious walk-in closet and a private bath with double vanity and a glass stand-up shower. An additional full bathroom serves family and guests. The spacious unfinished basement offers exceptional ceiling height and a blank canvas for future customization, ideal for creating additional luxury living space, a home theater, fitness area, or private retreat. A two-car garage and ample driveway parking complete the home. With new shopping centers, grocery stores, dining, and major commuter routes just minutes away, this home offers the perfect balance of suburban charm and modern convenience. This move-in-ready home is ideal for families ready to connect and enjoy everything Bayberry North has to offer. Schedule your tour today and imagine the possibilities.
#DENC2096488

MIDDLETOWN

1220 N OLMSTED PARKWAY

2 Beds

2 Baths

1,850 Sq.Ft.

$579,000

MLS#: DENC2096488

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

MIDDLETOWN

400 REDERICK LANE 2 OXFORD

4 Beds

2 Baths

2,357 Sq.Ft.

$576,500

MLS#: DENC2079326

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

MIDDLETOWN

400 REDERICK LANE 4 SASSAFRAS II

3 Beds

2 Baths

2,200 Sq.Ft.

$576,000

MLS#: DENC2079330

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

MIDDLETOWN

321 JESSICA DRIVE

5 Beds

4 Baths

5,250 Sq.Ft.

$575,000

MLS#: DENC2094594

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

MIDDLETOWN

6527 MORNINGSIDE COURT

3 Beds

3 Baths

2,275 Sq.Ft.

$574,900

MLS#: MDFR2073664

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

MIDDLETOWN

241 PORKY OLIVER DRIVE

4 Beds

2 Baths

2,650 Sq.Ft.

$572,000

MLS#: DENC2093134

Benchmark Builders at The Town of Whitehall, Chadwick Floor Plan. TO BE BUILT. The hometown is finally getting its come back. It's the first town to be founded in Delaware in over a century, and it's planned for all homes, businesses and community traditions that make real towns real places. Whitehall has it all! Chadwick floor plan feature 4bedrooms, 2.5 baths, 2nd floor laundry, 2 car attached rear entry garage, an open floor plan for entertainment with a huge great room! **Optional Chadwick front porch shown in photo**.Agent must accompany client on first visit or pre-register client on builder website prior to first visit
#DENC2079246

MIDDLETOWN

530 WHEELMEN STREET 5 CHADWICK

4 Beds

2 Baths

2,456 Sq.Ft.

$570,500

MLS#: DENC2079246

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

MIDDLETOWN

215 BROAD STREET

4 Beds

3 Baths

2,580 Sq.Ft.

$570,000

MLS#: MDFR2074538

Welcome to the Dorchester home design. An open, ranch style home slated for an October delivery. The popular model features first floor living with bright spaces. Its three bedrooms and 2 full baths are conveniently on one level. Plenty of storage with a 2-car garage and unfinished basement. A wide screen porch overlooking open space is perfect for outdoor dining. The home also features a large front porch, a nice spot to enjoy your morning coffee. In the well-appointed kitchen, you will find GE Profile appliance, gas cooking and a large, quartz covered island that pair perfectly with the gray island cabinets and white wall cabinets. Luxury vinyl plank flooring extends throughout most of the home, with large ceramic tiles in the owner’s bedroom. To schedule a tour please and to receive a full brochure of all the features in this home please contact our sales representatives. *Pictures are of a similar home* For a full list of features please contact our sales consultants. Welcome to Four Seasons at Baymont Farms, a new active adult 55+ community in Middletown, DE, offering low-maintenance, resort-style living. With spacious home designs and access to countless amenities, come enjoy the best that active living has to offer. Residents can take advantage of the community's 6,000 sq. ft. clubhouse, a pool with tiki hut, a state-of-the-art fitness center, a kayak launch, and multiple bocce and pickleball courts. With a full-time lifestyle director on site, Baymont Farms also features a well-maintained calendar of activities such as Zumba classes, yoga sessions, billiards and more. At Four Seasons at Baymont Farms, the focus is on community. Make friends and enjoy the company of people who have worked hard and now want to enjoy all that a luxury 55+ active adult community has to offer. Just minutes from downtown Middletown, DE with access to Delaware Rt. 1, Baymont Farms offers great convenience while preserving the serenity of its picturesque landscape. At this beautiful active lifestyle community, the relationships that you make and the people you spend time with will create memories that last a lifetime.
#DENC2075684

MIDDLETOWN

15 GOLDEN RAINTREE COURT

2 Beds

2 Baths

1,859 Sq.Ft.

$569,900

MLS#: DENC2075684

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

MIDDLETOWN

505 CHERRY BARK ROAD

3 Beds

3 Baths

2,650 Sq.Ft.

$565,000

MLS#: DENC2089330

Welcome to this beautifully maintained Dulaney model by ADMAR Custom Homes, located in the sought-after 55+ section of the Foxfield subdivision in picturesque Middletown. Pride of ownership is evident throughout this home, lovingly cared for by its original owner. Step inside to a welcoming ceramic-tiled foyer, offering easy access to the attached two-car garage and a conveniently placed powder room. The kitchen features an abundance of cabinet space and overlooks the living room. Two large corner windows bathe the breakfast nook in natural light, making it a cozy space to start your day. The main level boasts gorgeous hardwood flooring throughout the spacious living room and primary bedroom. A set of sliding glass doors in the living room leads to a private outdoor patio — perfect for relaxing or entertaining guests. You'll also appreciate the main-level washer and dryer, offering convenient single-level living. Upstairs, you'll find two additional bedrooms and a full bath, ideal for guests, hobbies, or a home office. The fully finished basement adds even more living space, featuring wall-to-wall wood flooring, recessed lighting, and a warm, open atmosphere perfect for entertaining, game nights, or even dancing. A large utility room with ceramic tile, utility sink, and dedicated deep freezer outlet adds function, while a roughed-in bathroom is nearly complete — just waiting for your final touch. The walk-out basement stairs lead to a lush green yard. This backyard oasis offers both charm and seclusion — a perfect retreat. Don’t miss your chance to own this exceptional home — homes like this don’t stay on the market for long!
#MDFR2071176

MIDDLETOWN

1 KELLER LANE

3 Beds

2 Baths

3,161 Sq.Ft.

$564,900

MLS#: MDFR2071176

*Move-in ready home! New construction without the typical wait* This beautifully designed 3BR/3BA home is ready for immediate occupancy and offers both comfort and style. Enter into a bright and airy office, perfect for work-from-home or hobby space. Just beyond, a formal dining room sets the stage for holiday gatherings and meals. The heart of the home is truly stunning — the kitchen features quartz countertops, 42" cabinetry, and a refrigerator included, all seamlessly flowing into a casual dining area and a spacious great room with a cozy fireplace. A sunroom with glass doors brings in abundant natural light and leads to a private deck, ideal for indoor-outdoor living. The first-floor primary suite boasts a large walk-in closet and a luxurious en suite bath. Upstairs, guests can enjoy their own space with a comfortable loft, an additional bedroom, and a full bathroom — perfect for media, visitors, or multi-use living. This home also has an unfinished basement, offering endless possibilities for future living space, storage, or your favorite hobbies. Don’t miss your chance to live in one of the area’s most desirable communities — schedule your tour today! About the Community: This vibrant 55+ 𝐚𝐜𝐭𝐢𝐯𝐞 𝐚𝐝𝐮𝐥𝐭 neighborhood is designed for your best life, offering everything you need to stay active, connected, and relaxed. The community will have a 5,400-square-foot clubhouse, pickleball and tennis courts, bocce, a sparkling swimming pool, a state-of-the-art fitness center, and more, there will be no shortage of activities to enjoy. Plus, with lawn care, snow removal, and trash and recycling included, you can spend your time doing what you love instead of worrying about upkeep! *Pictures of the model home - actual options and finishes vary per homesite. 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.
#DENC2096310

MIDDLETOWN

3027 IVYHOUSE LANE

3 Beds

3 Baths

2,356 Sq.Ft.

$559,495

MLS#: DENC2096310

The Asheville - with over 2,800 finished sq. ft. - delivers modern design and comfortable living with spaces made for both entertaining and everyday relaxation. The contemporary kitchen is the heart of the home, featuring a large island, walk-in pantry, and designer Looks interior selections that elevate the space. A covered front porch and rear deck invite you to welcome guests or unwind outdoors, while the impressive great room with a vaulted ceiling creates a bright, open atmosphere inside. The luxurious primary suite is a true retreat, highlighted by triple windows and an elegant tray ceiling. The primary bath offers a spa-like experience with dual sinks, a walk-in closet, and the option for a freestanding tub. Downstairs, the finished basement expands your living space with a recreation room, bedroom, and full bath—ideal for guests, hobbies, or flexible living needs. This listing is for a to be built home and photos are of a model home for display purposes only. Please see sales consultant for details.
#DENC2096240

MIDDLETOWN

1930 DIXON WAY

4 Beds

3 Baths

2,833 Sq.Ft.

$554,990

MLS#: DENC2096240

1 ... 7 8 9 10 11 ... 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