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 youā€™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. Hereā€™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 youā€™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 youā€™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 youā€™re considering a move, now is the perfect time to contact a trusted Charis Realty Group agent to start your search.

Start living the life youā€™ve always dreamed of in Middletown, Marylandā€”where homes are more than houses; theyā€™re part of a vibrant, enduring community.

One of the most popular communities provided by Charis Realty Group
259
# of Listings
3
Avg # of Bedrooms
$274
Avg. $ / Sq.Ft.
$648,255
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

259 Properties Found. Page 14 of 18.

If youā€™ve been searching for a move-in ready home that blends style, comfort, and convenience ā€” this is the one. Located in the highly desirable Appoquinimink School District, this beautiful ranch-style home has been designed with todayā€™s lifestyle in mind. Step inside and youā€™ll immediately notice the open layout, natural light, and thoughtful details throughout. The kitchen is truly the heart of the home ā€” featuring sleek countertops, elegant cabinetry, stainless steel appliances, recessed lighting, and a spacious pantry. Whether youā€™re cooking dinner or entertaining guests, this space was made to enjoy. From the kitchen, step right out onto your back deck ā€” perfect for relaxing after a long day or hosting weekend get-togethers. This home offers three comfortable bedrooms, two full bathrooms, and a flex room that can easily be used as an office, reading nook, or playroom. The large laundry room adds plenty of storage and practicality, while every room feels fresh, bright, and ready to move in. The finished lower level adds even more space to spread out ā€” ideal for a media room, gym, or guest suite. Outside, the fenced-in backyard, paver patio, and private deck create an inviting setting for everyday living or entertaining. āœØ With its modern touches, flexible layout, and prime Middletown location, this home truly has it all ā€” and itā€™s offered at under $400,000! Donā€™t wait ā€” schedule your private showing today and see why 8 Redding Circle feels like home the moment you walk through the door.
#DENC2091860

MIDDLETOWN

8 REDDING CIRCLE

3 Beds

2 Baths

1,800 Sq.Ft.

$379,000

MLS#: DENC2091860

Welcome home to this beautifully maintained move-in ready 3-bedroom, 2.1-bath home in the highly sought-after community of Willow Grove Mill, located within the highly desirable Appoquinimink School District. From the moment you step inside, youā€™ll appreciate the warm and inviting layout designed for both comfortable everyday living and easy entertaining. The spacious family room offers the perfect place to relax, gather with friends, or enjoy cozy evenings at home, and it flows effortlessly into the large eat-in kitchen featuring upgraded 42-inch cabinets, abundant storage, and plenty of room for casual dining. Upstairs, the generously sized primary suite provides a peaceful private retreat with a walk-in closet and its own full bath. Two additional spacious bedrooms offer flexibility for family, guests, or a home office and are served by a well-appointed full hall bath. The convenient second-floor laundry makes daily living even easier. It even has a brand new roof! Step outside to enjoy the fenced backyard, ideal for pets, play, gardening, or summer barbecues, along with the added convenience of a 1-car garage. Perfectly located just minutes from shopping, dining, and major commuting routes including Route 1, this home combines neighborhood charm, convenience, and top-tier school district appeal. Homes in Willow Grove Mill and Appo schools are always in demandā€”schedule your private showing today before this one is gone.
#DENC2100224

MIDDLETOWN

417 WILMORE DRIVE

3 Beds

2 Baths

1,650 Sq.Ft.

$375,000

MLS#: DENC2100224

**This Novella Interior townhome is one of the selected homes eligible for the Blenheim Cornerstone Initiative in compliance with the New Castle County MPDU program. Visit our website or NCCā€™s website for more details on qualifications and income requirements. ** This home is under construction. Delivery time frame should be discussed with a sales representative. Located in The Overlook at Bayberry in Middletown, Delaware, The Novella blends contemporary comfort with everyday convenience in a way few homes can. Offering spacious rooms and open layouts with flexible living spaces, The Novella is thoughtfully crafted for all that want room to live, work, and unwind. From its inviting main level to its well-proportioned 4 bedrooms, every square foot is designed with livability in mind. Whether youā€™re hosting friends, setting up a home office, or simply enjoying a quiet evening in, this townhome adapts effortlessly to your lifestyle. What adds to The Novellaā€™s appeal is its unmatched location. Situated just steps from Bayberry Town Center, homeowners can walk to lifeā€™s daily essentials like grocery store, pharmacy, dining, coffee, quick bites, and neighborhood services. The Overlook is thoughtfully planned to support a connected and walkable way of living. Imagine grabbing dinner, running errands, or meeting friends without ever needing to get in the car, then returning to your dream home! Families will also appreciate that The Novella sits only blocks from top-rated Appoquinimink schools, consistently recognized among the highest-rated in Delaware for academic excellence, innovative programs, and exceptional community engagement. Homeowners will also enjoy having their own clubhouse and playground in The Overlook in addition to being surrounded by miles of walking trails throughout Bayberry.
#DENC2097434

MIDDLETOWN

758 ROSLER WAY

4 Beds

3 Baths

1,980 Sq.Ft.

$369,900

MLS#: DENC2097434

**This Novella Interior townhome is one of the selected homes eligible for the Blenheim Cornerstone Initiative in compliance with the New Castle County MPDU program. Visit our website or NCCā€™s website for more details on qualifications and income requirements. ** This home is under construction. Delivery time frame should be discussed with a sales representative. Located in The Overlook at Bayberry in Middletown, Delaware, The Novella blends contemporary comfort with everyday convenience in a way few homes can. Offering spacious rooms and open layouts with flexible living spaces, The Novella is thoughtfully crafted for all that want room to live, work, and unwind. From its inviting main level to its well-proportioned 4 bedrooms, every square foot is designed with livability in mind. Whether youā€™re hosting friends, setting up a home office, or simply enjoying a quiet evening in, this townhome adapts effortlessly to your lifestyle. What adds to The Novellaā€™s appeal is its unmatched location. Situated just steps from Bayberry Town Center, homeowners can walk to lifeā€™s daily essentials like grocery store, pharmacy, dining, coffee, quick bites, and neighborhood services. The Overlook is thoughtfully planned to support a connected and walkable way of living. Imagine grabbing dinner, running errands, or meeting friends without ever needing to get in the car, then returning to your dream home! Families will also appreciate that The Novella sits only blocks from top-rated Appoquinimink schools, consistently recognized among the highest-rated in Delaware for academic excellence, innovative programs, and exceptional community engagement. Homeowners will also enjoy having their own clubhouse and playground in The Overlook in addition to being surrounded by miles of walking trails throughout Bayberry.
#DENC2097430

MIDDLETOWN

754 ROSLER WAY

4 Beds

3 Baths

1,980 Sq.Ft.

$369,900

MLS#: DENC2097430

**This Novella Interior townhome is one of the selected homes eligible for the Blenheim Cornerstone Initiative in compliance with the New Castle County MPDU program. Visit our website or NCCā€™s website for more details on qualifications and income requirements. ** This home is under construction. Delivery time frame should be discussed with a sales representative. Please contact the sales office for more information. Located in The Overlook at Bayberry in Middletown, Delaware, The Novella blends contemporary comfort with everyday convenience in a way few homes can. Offering spacious rooms and open layouts with flexible living spaces, The Novella is thoughtfully crafted for all that want room to live, work, and unwind. From its inviting main level to its well-proportioned 4 bedrooms, every square foot is designed with livability in mind. Whether youā€™re hosting friends, setting up a home office, or simply enjoying a quiet evening in, this townhome adapts effortlessly to your lifestyle. What adds to The Novellaā€™s appeal is its unmatched location. Situated just steps from Bayberry Town Center, homeowners can walk to lifeā€™s daily essentials like grocery store, pharmacy, dining, coffee, quick bites, and neighborhood services. The Overlook is thoughtfully planned to support a connected and walkable way of living. Imagine grabbing dinner, running errands, or meeting friends without ever needing to get in the car, then returning to your dream home! Families will also appreciate that The Novella sits only blocks from top-rated Appoquinimink schools, consistently recognized among the highest-rated in Delaware for academic excellence, innovative programs, and exceptional community engagement. Homeowners will also enjoy having their own clubhouse and playground in The Overlook in addition to being surrounded by miles of walking trails throughout Bayberry.
#DENC2097418

MIDDLETOWN

746 ROSLER WAY

4 Beds

3 Baths

1,980 Sq.Ft.

$369,900

MLS#: DENC2097418

Welcome to 113 Crawford Street. Located in the heart of Middletown, Delaware. Enjoy close proximity to local shops, restaurants, parks and everyday conveniences with easy access to major routes for commuting. Middletown is known for its small town charm, strong sense of community and continued growth, making this an ideal place to call home. Whether you are taking a stroll around the neighborhood, heading out for dinner nearby, or enjoying the surrounding outdoor spaces, this location truly offers the best of comfort and convenience. This home is perched on an extra large home site with a newly installed privacy fence. A separate foyer leads to a spacious living room with decorative fireplace creating a warm and inviting atmosphere. Just off the dining room offers a powder room and laundry. While the kitchen provides ample room for additional dining and a sliding glass door accessing a deck and expansive backyard which offers space and seclusion. The second floor features an owner suite, two additional bedrooms, and a full bath. An unfinished attic offers potential for added living space. Two large backyard sheds in good condition complete the property providing ample storage solutions. This is a MUST SEE property. ALL the comforts of HOME and IN WALKING DISTANCE to town with amazing amenities!!! Come see this amazing property!
#DENC2096714

MIDDLETOWN

113 CRAWFORD STREET

3 Beds

1 Baths

1,875 Sq.Ft.

$365,000

MLS#: DENC2096714

UNDER CONSTRUCTION. *$10,000 builder incentive; thru 4/30/26* This Swallow model is a 3 BD, 2.5 BA, 1,798 sq. feet, center-unit townhome. With its nine foot ceilings and lots of natural light, this home feels comfortably spacious. Included in this kitchen is an island, granite counters, stainless steel appliances, recessed lighting, an adjacent pantry and many more features. You will feel right at home in the ownerā€™s suite with its ample space and lots of natural light which also features a private bath and walk-in closet. Also on the second floor are bedrooms two and three, a family bath and the laundry room, which is just steps from all bedrooms and bathrooms. This home has a full, unfinished, walkout lower level and a 2 car garage. A composite deck, as well as the patio below, affords additional outdoor living space. Interior selections may still be available. All taxes are estimated since this is new construction and has not yet been assessed. Interior photos are of a similar home.
#PADA2051546

MIDDLETOWN

132 MAGNOLIA DRIVE

3 Beds

2 Baths

1,798 Sq.Ft.

$360,581

MLS#: PADA2051546

New on site today
Spring has sprung and so has this move in ready townhome in the much sought after community of Willow Grove Mill. This home sets inside the town limits of Middletown Delaware. The growth of Middletown offers not only the essential needs of todays home buyers but the extras that make this home even more appealing. From desired retail shopping and eateries to the newer YMCA and so much more. And just outside of the community is access to Rt 1 and 13 for all your commuting needs. Want to go to the beach? The Delaware shore is day trip drivable. The seller has updated the HVAC unit. With 3 bedroom and 2.5 bath all to be done here is bring your moving truck and unpack!!
#DENC2100732

MIDDLETOWN

304 NORWALK WAY

3 Beds

2 Baths

1,650 Sq.Ft.

$360,000

MLS#: DENC2100732

Welcome to 868 Lissicasey Loop, a beautifully maintained home nestled in one of Middletownā€™s most sought-after communities and located within the prestigious Colonial School District. Built less than seven years ago, this property offers modern living, generous space, and a layout designed for todayā€™s lifestyles. Step through the front door, and you are greeted by a bright foyer that sets the tone for the rest of the home. To your right is the attached one-car garage, and straight ahead is a hallway leading to the versatile lower levelā€”perfect as a recreation room, home gym, office, or additional living space. This level offers incredible flexibility, whether you need extra room for guests, hobbies, or entertainment. This is a shortsale, home is being sold as is Head up to the second floor and discover a fully open, airy, and beautifully lit main living area. Large windows fill the floor with natural light, creating a warm and inviting atmosphere. The living room sits to the right, offering a comfortable gathering space. At the same time, the center of the home features a spacious kitchen with maple-brown cabinetry and a large breakfast islandā€”ideal for meal prep, hosting, or casual dining. Adjacent to the kitchen is an eat-in area plus a dedicated dining space, giving you multiple options for family meals and entertaining. A sliding glass door on this level provides the opportunity to add a second-floor deck for outdoor enjoyment. The third floor features three well-sized bedrooms. The ownerā€™s suite includes a private bathroom and ample closet space. Down the hall is a full guest bath and a conveniently located laundry area, keeping daily routines efficient and straightforward. This home offers the perfect balance of comfort, functionality, and room to grow. With multiple levels of living space, defined areas for privacy, and open spaces for connection, it fits the needs of families with young children, teens, or multigenerational households. Located minutes from major highways, shopping centers, restaurants, and everything Middletown has to offer, this property delivers both convenience and community. 868 Lissicasey Loop is truly an excellent opportunity to live in a thriving area.
#DENC2095734

MIDDLETOWN

868 LISSICASEY LOOP

3 Beds

2 Baths

2,100 Sq.Ft.

$359,000

MLS#: DENC2095734

New on site today
Welcome to 25 Boileau Court in Middletown. This three-level townhome is located in a small neighborhood with no HOA and is conveniently situated near downtown Middletown. The main level features a living room, dining room, kitchen, and half bathroom. The spacious primary suite is located on the upper level and includes an en suite bathroom. Two additional bedrooms and a full hallway bathroom complete the second level. The lower level provides additional living space with a family room that has walkout access to the backyard, along with a half bathroom for added convenience. Recent updates include a roof that is just 2 years old, fresh paint throughout, and new carpet in the lower level. This home has been well maintained, thoughtfully updated, and is truly move-in ready. Plenty of parking available. This property offers easy access to the local shops, dining, parks, and everyday amenities of downtown Middletown. It is so close you may not even need to take your car. Don't miss your chance to see this home. Schedule your tour today!
#MDFR2080102

MIDDLETOWN

25 BOILEAU COURT

3 Beds

2 Baths

1,870 Sq.Ft.

$359,000

MLS#: MDFR2080102

Welcome to this beautifully maintained 3 bed, 2.5 bath townhome with some upgrades including granite counters, offering the perfect blend of comfort, convenience, and lifestyle. In excellent condition, this home features an open floor plan with spacious living areas, abundant natural light, and modern finishes throughout. Located just minutes from I81 and I66, this home provides easy access for commuters while still offering a peaceful residential setting. Enjoy weekends exploring nearby wineries and the scenic countryside or stay home and have a cookout on the deck with family and friends. Owner/Agent Related
#VAFV2040714

MIDDLETOWN

139 KENSINGTON CIR

3 Beds

2 Baths

1,220 Sq.Ft.

$347,499

MLS#: VAFV2040714

UNDER CONSTRUCTION. *$10,000 builder incentive; thru 4/30/26* This Bluebird model is a 3 BD, 2.5 BA, center unit townhome. Youā€™ll soon discover the value of the many included features that are packed into this home. The open first floor plan will make entertaining family and friends a pleasure. Nine foot first floor walls make this home feel even more spacious. A self-cleaning electric range, granite counters and soft-close cabinet doors/drawers are featured in this kitchen. You will love all the storage available in the walk-in pantry. The entire first floor has luxury vinyl plank flooring. Check out the size of these bedrooms! The ownerā€™s suite is sure to please with large spaces and lots of natural light. Bedrooms 2 and 3 have their own full bath. The laundry room is just steps from all bedrooms and bathrooms. This home also boasts a walk-out lower level, 10Ɨ12 composite deck, and a 2 car garage. - Interior photos are of a similar model. - All taxes are estimated since this is new construction and has not yet been assessed.
#PADA2051548

MIDDLETOWN

128 MAGNOLIA DRIVE

3 Beds

2 Baths

1,539 Sq.Ft.

$339,375

MLS#: PADA2051548

*$10,000 builder incentive; thru 4/30/26* UNDER CONSTRUCTION. This Bluebird model is a 3 BD, 2.5 BA, center unit townhome. Youā€™ll soon discover the value of the many included features that are packed into this home. The open first floor plan will make entertaining family and friends a pleasure. Nine foot first floor walls make this home feel even more spacious. A self-cleaning electric range, granite counters and soft-close cabinet doors/drawers are featured in this kitchen. You will love all the storage available in the walk-in pantry. The entire first floor has luxury vinyl plank flooring. Check out the size of these bedrooms! The ownerā€™s suite is sure to please with large spaces and lots of natural light. Bedrooms 2 and 3 have their own full bath. The laundry room is just steps from all bedrooms and bathrooms. This home also boasts a walk-out lower level, 10Ɨ12 composite deck, and a 2 car garage. - Interior photos are of a similar model. - All taxes are estimated since this is new construction and has not yet been assessed.
#PADA2051576

MIDDLETOWN

130 MAGNOLIA DRIVE

3 Beds

2 Baths

1,539 Sq.Ft.

$339,375

MLS#: PADA2051576

Charming brick rancher set on 4.64 acres with stunning views and exceptional potential. This 3-bedroom, 1-bath home offers classic construction and ā€œgood bones,ā€ making it a fantastic opportunity for buyers looking to add their own updates or build sweat equity. The home features a functional layout with an unfinished basement that provides additional space for storage, hobbies, or future finishing. This property consists of 2 tax parcels, offering added privacy, flexibility, and potential uses. The property also features a small stall barn, making it especially appealing for hobby farming, animals, or additional storage. Surrounded by trees and scenic countryside, the setting provides peaceful views and a sense of privacy while still being conveniently located near local commuter routes. Outdoor enthusiasts will appreciate the close proximity to Civil War historical sites, nearby battlefields, and the Appalachian Trail. Whether youā€™re looking for a primary residence, investment opportunity, or a property with room to grow, this home offers a rare combination of location, land, and opportunity.
#MDFR2078078

MIDDLETOWN

1629 DAHLGREN ROAD

3 Beds

1 Baths

1,056 Sq.Ft.

$335,000

MLS#: MDFR2078078

Rare opportunity to own approximately 14 acres of raw land in the sought-after Middletown, Delaware area. This expansive parcel is currently farmed and also used for hunting, offering a beautiful natural setting with wide open space and incredible potential. Whether you're looking for recreational land, agricultural use, a long-term investment, or exploring future possibilities, this property offers the space and flexibility to bring your vision to life. Large tracts like this are becoming increasingly difficult to find in this growing area, making this a unique opportunity for buyers seeking land with versatility and value. Buyers are responsible for conducting their own due diligence regarding zoning, permitted uses, and any potential development opportunities with the appropriate local authorities. There are wetlands on the property, which will need approval from Army Core of Engineers and DNREC to put in a lane or driveway to access the back area where you can build. IMPORTANT: The property is actively used for hunting. Do not enter the property without a confirmed appointment. Access without authorization will be considered trespassing. All showings must be scheduled in advance through the listing agent. Thank you
#DENC2098214

MIDDLETOWN

866 OLD SCHOOL HOUSE ROAD

None Beds

None Baths

14.91 acres

$330,000

MLS#: DENC2098214

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Buyers resources
7 Reasons to Work with a Realtor
7 Principles For Home Buying Success
Getting a Mortgage To Buy a Home
Home Hazards Awareness
Key Items For Home Inspection
Questions When Buying a Condo
Questions When Choosing a Realtor
Sellers resources
8 reasons to work with a realtor
Calculating Capital Gains
Checklist for Better Showing
Cleaning Home For Sale
Improving Odds Of an Offer
Preparing Home for photoshoot
Selling Your Home for More $$

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