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
245
# of Listings
3
Avg # of Bedrooms
$277
Avg. $ / Sq.Ft.
$645,147
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

73 Properties Found. Page 4 of 5.

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.

$386,900

MLS#: DENC2091860

** WORKFORCE HOUSING-BUYER MUST QUALIFY FOR THE NEW CASTLE COUNTY PROGRAM TO PURCHASE - MASSEY INTERIOR UNIT- 3 bedrooms, 2.5 baths, 1 car garage. Approx. 2001 SF! This home features a Finished den, 42" cabinets in kitchen, island, stainless range, dishwasher, microwave and recessed lighting in Kitchen. Tiled floor and Shower surround in master bath. 3 pc rough in walk out basement. Don't miss out on this spectacular floor plan! Builder Splits Transfer Tax
#DENC2080232

MIDDLETOWN

460 REDERICK LANE MASSEY LOT 61

3 Beds

2 Baths

2,300 Sq.Ft.

$384,900

MLS#: DENC2080232

New on site 4 days ago
Discover this charming 3-bedroom, 2-bath ranch home on a spacious 0.63-acre lot in the desirable Middletown Valley (Fountaindale North neighborhood). This 1,651 sq ft single-family residence, built in 1957, features beautiful hardwood floors throughout the first floor and offers incredible potential for your personal touches to bring it to life. Enjoy breathtaking mountain sunsets right from your front porch! The peaceful setting provides stunning views while offering the perfect blend of privacy and convenience. Located in the heart of Middletown, youā€™ll love the benefits of: ā€¢ Top-rated Middletown schools ā€¢ Nearby shopping and dining ā€¢ Easy commuting in every direction ā€” east, west, north, or south Whether youā€™re looking for a starter home, investment opportunity, or peaceful retreat, this home delivers. Key Features: ā€¢ 3 bedrooms ā€¢ 2 full bathrooms ā€¢ Hardwood floors throughout the first floor ā€¢ 1-car garage ā€¢ Generous 0.63-acre lot ā€¢ Single-level living ā€¢ Wood-burning fireplaces (2) Donā€™t miss your chance to own a piece of Middletown Valley! Schedule your showing today and imagine the possibilities.
#MDFR2078768

MIDDLETOWN

7201 DOGWOOD LANE

3 Beds

2 Baths

1,651 Sq.Ft.

$371,000

MLS#: MDFR2078768

**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

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

Being "SOLD AS IS"- Rancher with two bedrooms and two full bath. Kitchen with granite and appliances. Spacious living area. Sunroom. Owners suite with full bath. Two car attached garage. Home is a guardianship sale. Appointed guardian has no knowledge of the home. Buyers and buyers agent should do their own due diligence. Neighborhood information is in the MLS.
#DENC2094084

MIDDLETOWN

561 WHISPERING TRAIL

2 Beds

2 Baths

1,650 Sq.Ft.

$351,900

MLS#: DENC2094084

***Professional photos 3/25/26*** Beautifully renovated and thoughtfully updated, this charming 3-bedroom, 2 full bathroom farmhouse at 1602 N Union Street blends classic character with modern comfort. Renovated from top to bottom just over a year ago, this home is truly move-in ready with high-quality finishes throughout. Step inside from the convenient off-street parking into a bright and inviting sunroom/dining area, perfect for everyday living or entertaining. This space flows seamlessly into the stunning kitchen, featuring rich hardwood soft-close cabinetry, sleek granite countertops, and a clean, modern design. Just beyond the kitchen, youā€™ll find a second sunroom filled with natural light ideal as a home office, reading nook, or study along with the added convenience of first-floor laundry. The main level also offers a spacious and comfortable living room, as well as a beautifully remodeled full bathroom. Durable and stylish Luxury Vinyl Plank flooring runs throughout the entire first floor, tying the space together with a warm, cohesive feel. Upstairs, youā€™ll find three generously sized bedrooms with plush carpeting, along with a second fully remodeled full bathroom designed with modern finishes and functionality in mind. The exterior has been extensively updated, featuring a durable new metal roof, new windows, new gutters, and fresh siding on both the home and detached garage offering peace of mind for years to come. Enjoy the added benefit of a fenced-in yard, perfect for outdoor gatherings, pets, or relaxing in your own private space. A rare opportunity to own a fully renovated home with character, space, and upgrades already complete.
#PADA2057798

MIDDLETOWN

1602 N UNION STREET

3 Beds

2 Baths

1,788 Sq.Ft.

$350,000

MLS#: PADA2057798

New on site 2 days ago
None
#PADA2057578

MIDDLETOWN

552 N SPRING STREET

3 Beds

3 Baths

2,133 Sq.Ft.

$349,999

MLS#: PADA2057578

Motivated seller offering seller credit, providing flexibility for buyers to help with closing costs or interest rate buy-downs. Even better, this home qualifies for the USDA 0% down financing program, making homeownership more accessible than ever. Welcome to 1500 Rosedale Ave, where thoughtful design meets modern living. Luxury vinyl plank flooring flows throughout the main level and finished basement. The updated kitchen features granite countertops and stainless steel appliances, perfect for everyday living and entertaining. A refreshed powder room adds a clean, modern touch. Upstairs, youā€™ll find brand new carpeting and beautifully finished bathrooms with ceramic tile. The primary suite now includes a private full bath, offering a true retreat. Enjoy the outdoors on your brand new deck overlooking a fully fenced yard ideal for relaxing or entertaining.
#PADA2056698

MIDDLETOWN

1500 ROSEDALE AVENUE

3 Beds

2 Baths

2,004 Sq.Ft.

$349,900

MLS#: PADA2056698

New on site 1 day ago
Welcome to Venue at Winchelsea by Lennar ā€” Middletownā€™s premier active adult (55+) community offering low-maintenance living, spacious designs, and exceptional value. This 2,669 sq. ft. two-story townhome is part of Lennar's Pathway to Ownership Program - application and income qualification are required for purchase. 3102 Pett Level Drive is move-in ready and thoughtfully designed for comfort and ease. The first floor features an inviting open-concept layout that blends the kitchen, dining, and living areasā€”perfect for both everyday living and entertaining. The luxurious first-floor ownerā€™s suite is privately tucked away in the rear of the home and includes a spa-inspired en-suite bath and generous closet space. A secondary bedroom at the front of the home offers flexibility for guests or a home office. Upstairs, a central loft anchors one additional bedrooms, a den and office providing ample space for hobbies, visitors, or multigenerational living. About the community: Venue at Winchelsea is designed for an active, social lifestyle. Future amenities currently under construction include a 5,400 state-of-the-art clubhouse, outdoor pool, pickleball and bocce courts, community gardens, and more. *Please read: This community is designated as an active adult community. Owners must be 55 years of age or older. Any additional occupants must be over 18 years of age. Pictures are artist renderings and for representational purposes only. 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. Please contact the Lennar Sales Team directly for questions about qualifications and how to apply for the MPDU program. We are happy to walk you through the process.* For appointments and open houses, please visit the welcome home center at 2405 Greyfriar Loop.
#DENC2099142

MIDDLETOWN

3102 PETT LEVEL DRIVE

3 Beds

2 Baths

2,669 Sq.Ft.

$345,000

MLS#: DENC2099142

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

1 2 3 4 5
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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