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
238
# of Listings
3
Avg # of Bedrooms
$269
Avg. $ / Sq.Ft.
$653,613
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

125 Properties Found. Page 7 of 9.

Very unusual historic home in the heart of Middletown. Just blocks from new YMCA. Home was assembled in 1944-1948 from parts of multiple historic homes being demolished to make room for post war housing. The front facade and much of the brick exterior were transported and re-assembled on site, proudly boasting 1736 construction. Add various plank floors, beamed ceiling, fireplaces with Mable surround or beautiful delft tiles, decorative moldings, beautiful wood doors.... You may think you can visualize how beautiful this house is, but it will still surprise you, now add recent kitchen, a first floor primary suite with spacious en-suite, large closets and room for washer and dryer. Wait there's more!! Recent HVAC (2 zone) a large Amish built workshop shed , a carriage house/pool house with full bathroom. Ornate gardens and landscaping, a koi pond, brick walkways encased with privacy fencing , yet walking distance to schools, stores , dining and entertainment. A Must see to imagine. Book your private tour as soon as possible.
#DENC2091784

MIDDLETOWN

12 E COCHRAN STREET

4 Beds

2 Baths

2,275 Sq.Ft.

$596,000

MLS#: DENC2091784

Prime commercial site. This 1.54-acre property boasts a coveted B-2 zoning, making it an ideal location for business ventures. Conveniently positioned just off Interstate 81 and a short drive from Interstate 66, this site offers excellent visibility, ensuring maximum exposure for any enterprise. Situated between two well-known establishments, McDonald's and Econo Lodge, it benefits from high traffic and customer flow. With public utilities readily available, the infrastructure is in place to support a wide range of commercial activities. Moreover, the surrounding area is experiencing substantial residential growth, indicating a thriving market and potential customer base. This commercial site's strategic location, zoning, excellent visibility, proximity to major highways, and supportive infrastructure make it an enticing prospect for entrepreneurs looking to establish or expand their businesses in a rapidly developing area.
#VAFV2013246

MIDDLETOWN

RELIANCE ROAD

None Beds

None Baths

1.38 acres

$595,000

MLS#: VAFV2013246

Edmonston -TO BE BUILT. Come tour our decorated model during business hours. This 4 bedroom open floor plan welcomes homeowners and visitors alike in a space that flows effortlessly from one room to the next. This plan offers 2 version, the standard offering a first floor owner's suite, and the alternate offering a larger great room and secondary bedroom on the first floor. There is a spacious kitchen with hardwood floors, along with 42" maple cabinets, granite countertops, and so much more! The picture shown is of our largest porch option, but there are several sizes to choose from. If you are looking for a community with planned amenities, retail, school and everything else you can imagine, visit the first new urbanism concept community in Delaware, The Town of Whitehall. Agents must accompany buyer on first visit or pre-register on builder's website prior to first visit.
#DENC2079210

MIDDLETOWN

530 WHEELMEN STREET 1 EDMONSTON

4 Beds

2 Baths

2,716 Sq.Ft.

$591,000

MLS#: DENC2079210

Savannah -To be built. This floor plan feature 4 bedrooms, 2.5 baths, second floor laundry, 2 car attached or detached rear entry garage, and an open floor plan for entertainment with a huge great room. Welcome to your new hometown! At Whitehall, the hometown is finally getting its comeback. It's the first town to be founded in Delaware in over a century, and it's planned for all homes, businesses and community traditions that make real towns real places. Walk to the park, doctor's office, or to school. Whitehall will have it all! Agent must accompany client on first visit or pre-register client on builder website prior to first visit.
#DENC2079250

MIDDLETOWN

530 WHEELMEN STREET 7 SAVANNAH

4 Beds

2 Baths

2,854 Sq.Ft.

$591,000

MLS#: DENC2079250

CHARLESTON -TO BE BUILT. This 4 bedroom (OPTIONAL 1ST FLOOR 5TH BEDROOM) open floor plan welcomes homeowners and visitors alike in a space that flows effortlessly from one room to the next. There is a spacious kitchen with hardwood floors, along with 42" maple cabinets, granite countertops, and so much more! Be the first to build this floor plan and get a special incentive off any upgrades. Ask the sales manager for details. If you are looking for a community with planned amenities, retail, school and everything else you can imagine, visit the first new urbanism concept community in Delaware, The Town of Whitehall. Agents must accompany buyer on first visit or pre-register on builder's website prior to first visit.
#DENC2079248

MIDDLETOWN

530 WHEELMEN STREET 6 CHARLESTON

4 Beds

2 Baths

2,730 Sq.Ft.

$590,000

MLS#: DENC2079248

Welcome to 1909 Gladys Street in the highly sought-after Town of Whitehall! Whitehall is a community that offers fantastic amenities, quality craftsmanship, and a warm welcome. This home's wow factor is abundant, from the curb appeal outside to the model home vibes inside. You will notice the beautiful landscaping and striking deep blue hardi-plank siding as you approach the home. Get ready to decorate the charming front porch for every season! Upon entering the front door, you will be greeted with a large living room to your right and a den to your left, which can be used for various purposes. The foyer, bathrooms, and kitchen have hardwood flooring, which gives the home a warm and welcoming feel. Moving forward, you will pass a hall closet and powder room and enter the main living space with an open floor concept. The kitchen is equipped with a large island, stainless appliances, beautiful 42" white cabinetry, and granite countertops. The family room and dining room are just off the kitchen. This model features a first-floor primary bedroom with double closets and en-suite bathroom, which includes a double sink vanity and a stand-up shower with glass doors. The laundry room is also on the main level, with tile flooring and access to the backyard and the garage. The massive garage can easily accommodate two large vehicles and provide ample storage space (including overhead storage). Upstairs, (iron balusters on the staircase) you will find an extra large loft perfect for various purposes, three spacious bedrooms, and a full bathroom! The unfinished basement is a vast space with an egress window, providing endless customization possibilities. The backyard has a brand-new vinyl fence, and the light fixtures and ceiling fans were just installed throughout the home. 1909 Gladys St. has a tree-lined view in the backyard and is tucked away in the neighborhood for extra privacy. A couple of NEW updates include new carpet in the lower level and fresh paint in several rooms and bathrooms. This home is conveniently located near the recreation center, where you can enjoy various activities such as Zumba, yoga, and self-defense classes. Additionally, the chiropractor, Christiana Care, and Wellness Center are located on-site. Lorewood Grove Elementary is within walking distance, and many shops have just opened and are coming soon! Convenience is just outside your door.
#DENC2096390

MIDDLETOWN

1909 GLADYS STREET

4 Beds

2 Baths

2,775 Sq.Ft.

$585,000

MLS#: DENC2096390

Welcome to the Cayot Model, in the desirable 55+ community of Traditions at Whitehall. This charming 3-bedroom home has a great open concept floor plan which offers all one floor living and a welcoming dining room and great room upon entry. At the rear of the home, you will find the luxurious owner's suite complete with walk-in closet and an en-suite bath, including a 5-foot tile shower. With a variety of structural and decorative options available, this home can be customized to perfectly fit your style and needs. Make this your dream home today! As a resident of this vibrant active adult community, you'll enjoy access to a wealth of amenities, including a state-of-the-art clubhouse, fitness facilities, sparkling swimming pools, walking trails, and a full calendar of social events to keep you engaged and connected with neighbors.
#DENC2080204

MIDDLETOWN

204 BALDY LANE CAYOT

3 Beds

2 Baths

2,004 Sq.Ft.

$579,000

MLS#: DENC2080204

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

MIDDLETOWN

195 MAGNOLIA DRIVE

4 Beds

2 Baths

2,898 Sq.Ft.

$579,000

MLS#: PADA2048296

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

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

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