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 Charis Realty Group 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
261
# of Listings
3
Avg # of Bedrooms
$273
Avg. $ / Sq.Ft.
$646,169
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

261 Properties Found. Page 12 of 18.

**Move-in ready new construction townhome in idyllic 55+ community** Now is the perfect time to buy your new home at The Venue at Winchelsea, Middletown, DE's premiere active adult community. This move-in ready two-story townhome offers low-maintenance living with sophisticated style and thoughtful design. Enter to find a dedicated study—perfect for a home office—and a convenient first-floor laundry. The gourmet kitchen shines with modern stainless steel appliances, sleek quartz countertops, 42” cabinetry, a wall oven, and gas cooktop. The open layout flows seamlessly into the dining and living areas, with an included patio to enjoy unwinding during the upcoming spring and summer months. The first-floor owner’s suite is a peaceful retreat with a private bath and spacious walk-in closet. Upstairs, two additional bedrooms, a full bath, and a versatile loft provide comfort and privacy for guests. Schedule your private tour today!! Community Highlights: This 55+ Active Adult neighborhood features a 5,400 sq. ft. clubhouse, pickleball, tennis, bocce, swimming pool, fitness center, and more. Lawn care, snow removal, trash, and recycling are all included—leaving you free to enjoy the lifestyle you’ve been waiting for. Pictures are of model home and for representational purposes only. Please see New Home Consultant for details. Taxes to be assessed after settlement. Realtor representation must be acknowledged on the first interaction with Lennar, and the agent must accompany their client on the first visit. For tours and open houses, visit the model home at 2405 Greyfriar Loop.
#DENC2097802

MIDDLETOWN

2311 WINCHELSEA PARKWAY

3 Beds

2 Baths

2,443 Sq.Ft.

$479,890

MLS#: DENC2097802

Welcome to 365 Andrew Ct! This beautifully maintained, like-new home offers all the advantages of new construction without the wait. Nestled within the highly acclaimed Appoquinimink School District, this stunning end-unit townhome combines luxury with convenience. Featuring an expansive open-concept floor plan, this home is tailored for modern living. With 3 bedrooms, 2 full baths, 2 half baths, and a 2-car garage, there’s ample space for everyday life and entertaining. The chef’s kitchen is a standout with upgraded cabinetry, Quartz countertops, a stylish tile backsplash, and GE stainless steel appliances, seamlessly flowing into the dining area and great room. The lower level, currently used as a bedroom, offers versatile options for your needs. It could easily serve as a home office, gym, playroom, or guest suite. Luxury finishes throughout include LVP flooring on the main level, upgraded tile, and elegant details that enhance the home’s appeal. No need to wait for construction; this home is move-in ready in a community where opportunities like this are truly rare!
#DENC2092040

MIDDLETOWN

365 ANDREW COURT

3 Beds

2 Baths

N/A

$477,000

MLS#: DENC2092040

Located in the highly sought after community Ponds Of Odessa this pristine end-unit townhouse offers the perfect balance of convenience as well as comfort. Upon entering you are greeted by natural light and a spacious open floor plan complete with a flex room that can double as an office. Upon exploring more of the home you have a vaulted ceiling and open living room and beautiful kitchen complete with upgraded countertops and cabinets. Downstairs you have an unfinished basement with a plethora of options gym, theater, or additional bedrooms and complete with rough plumbing for a future bathroom. Upstairs you'll find the spacious primary suite fully equipped with walk-in closet as well as an en-suite bathroom with dual vanities. The additional bedrooms are very comfortable sized with their own walk-in closets. Outside you'll find a concrete patio perfect for any outdoor activity. This property is located minutes from many amenities, shopping and local businesses. Also just minutes from major highways great for commuting. Schedule your showing today.
#DENC2094428

MIDDLETOWN

1341 CARRICK COURT

3 Beds

2 Baths

2,325 Sq.Ft.

$470,000

MLS#: DENC2094428

New on site 3 days ago
*More photos will be added soon* Welcome to this stunning, fully remodeled gem in the heart of Middletown! The house is near the 500 acres of Reserved State land. Thus there is no more place to build a new house in this area and it will never be crowded. If you wish to live in a serine scenic beauty and walk along the beach every afternoon then this house is the best for you. This house is a quick one minute walk away from the great Augustine beach. Also the Augustine Tavern is one minute walking distance from the house. No detail has been overlooked in this top-to-bottom transformation, offering the luxury of new construction with modern, high-end finishes throughout. The open-concept interior boasts all-new flooring, contemporary lighting, and a fresh, neutral palette. The living room is equipped with an electric fireplace is the centerpiece. Kitchen is featuring brand-new stainless steel appliances.. Step outside to your private, fully fenced backyard, providing the perfect space for entertaining, gardening, or pets. Location is everything! This home puts you minutes from the scenic C&D Canal and the natural beauty of the Woodland Beach and Augustine Beach areas. Enjoy easy access to the local ferry, vibrant downtown Middletown shops, and all area attractions. With all-new finishes and an unbeatable location near the water, this move-in-ready home is the perfect retreat. Schedule your tour today—this one won't last!
#DENC2098750

MIDDLETOWN

4 FARM LANE

4 Beds

2 Baths

1,900 Sq.Ft.

$465,000

MLS#: DENC2098750

New on site 3 days ago
Where original character remains and modern updates prevail. This gem has the potential to be converted back to a single family home by opening up the interior staircase or investors are sure to appreciate the two separate updated apartments in this turn of the century home with off-street parking. Owner can live in one unit and rent out the other. Each apartment features its own separate entrance, living room, dining room, two bedrooms, full kitchen, laundry room, ample closet and storage space. Enjoy outdoor living with a large back yard. Be in the heart of in-town living with amenities - restaurants, churches, convenience stores, schools, and parks.
#MDFR2078348

MIDDLETOWN

507 MAIN STREET

4 Beds

2 Baths

2,698 Sq.Ft.

$460,000

MLS#: MDFR2078348

Where original character remains and modern updates prevail. Investors are sure to appreciate the two separate updated apartments in this turn of the century home with off-street parking. Owner can live in one unit and rent out the other. Each apartment features its own separate entrance, living room, dining room, two bedrooms, full kitchen, laundry room, ample closet and storage space. Enjoy outdoor living with a large back yard. Be in the heart of in-town living with amenities - restaurants, churches, convenience stores, schools, and parks.
#MDFR2078050

MIDDLETOWN

507 MAIN STREET

4 Beds

None Baths

2,698 Sq.Ft.

$460,000

MLS#: MDFR2078050

The main floor of this Coral home offers a large, uninterrupted space for relaxing and entertaining. The kitchen features a spacious center island and opens to the dining and great rooms. Upstairs, you'll find a convenient laundry, a full bath tucked between two generous bedrooms, and an inviting primary suite with a walk-in closet and private bath. This home is built a loft. To round out this home a basement is included and this beautiful home backs to common area.
#VAFV2035270

MIDDLETOWN

102 MIDSUMMER LANE

3 Beds

2 Baths

1,840 Sq.Ft.

$459,999

MLS#: VAFV2035270

Welcome to the 55+ community of Traditions at Whitehall - Ashton Carriage Town Home. This home is an end unit has a first-floor owner's bedroom w/ full ensuite bath and walk-in closets, second floor has the 2nd bedroom, loft and an additional full bath. Standard 2-car garage, and additional finished upgrades can be purchased to your taste and budget. Community offers in ground pool w/lounge areas, clubhouse featuring exercise & billiards room, gathering/lounge space, full kitchen and a large outdoor patio/grilling area! Builder Splits Transfer Tax (***Photos are of a similar home and may contain options & upgrades not included in listing price shown.***)
#DENC2095106

MIDDLETOWN

314 CHAROLAIS STREET ASHTON

2 Beds

2 Baths

1,794 Sq.Ft.

$456,000

MLS#: DENC2095106

Brand new to the market and just recorded, complete with well, 4 BR conventional perc, electric at edge of lot, and spectacular view of South Mountain historic area and Middletown Valley. Middletown Middle and High schools and Myersville ES for top education. Farm animals allowed accept for swine. Bring your own builder or listing agent will introduce you to top builders in the area. There is no sign on the property, please call LA to set up showing. This lot and the one next to it are the "cream of the crop" and will be gone before Spring build! Hurry today to inspect. Please do not drive on the property without accompaniment of the listing agent.
#MDFR2075330

MIDDLETOWN

9702 MOUNT TABOR - LOT 12 ROAD

None Beds

None Baths

10.2 acres

$450,000

MLS#: MDFR2075330

Welcome to 1823 N Pollock Way, a beautifully maintained townhome located in the sought-after Village of Bayberry, one of the most vibrant and fast-growing communities in the Middletown area. From the moment you arrive, the home’s classic brick exterior, charming covered front porch with beautiful views of the park, and picturesque streetscape create immediate curb appeal and set the tone for the warmth found inside. Tucked along a quiet street, the property also offers the convenience and privacy of a rear-access garage with alley entry, keeping the front of the home welcoming and uncluttered. Step inside to find an airy and light-filled main level with 9ft ceilings where hardwood flooring spans the entry level, complemented by fresh paint and abundant natural sunlight pouring in through multiple windows with custom shades. The open layout creates a comfortable flow for everyday living and entertaining. The well-appointed kitchen is both stylish and functional, featuring upgraded cabinetry, granite countertops, stainless steel appliances, and a versatile center island perfect for meal prep or casual seating. An eat-in dining area offers a cozy spot for everyday meals while also providing convenient access to the garage. Sliding glass doors lead to the rear fenced yard, creating a great space for outdoor relaxation, grilling, or pets. Upstairs, the primary suite offers a peaceful retreat with a walk-in closet with custom organization and a beautifully upgraded en-suite bath featuring a double vanity, soaking tub, and separate tile shower with recently upgraded glass surround. Two additional generously sized bedrooms share a full hall bath, and the laundry room is thoughtfully located on the bedroom level, making daily routines easy and efficient. The finished basement expands the home’s living space, offering endless flexibility for a recreation room, home office, gym, or media area, and it includes the added convenience of a half bath. Living in Bayberry means more than just owning a home—it means being part of a thriving community known for its beautiful green spaces, playgrounds, walking trails, and neighborhood gathering spots that encourage an active and connected lifestyle. Residents enjoy quick access to the growing Bayberry Town Center, where new shops, restaurants, and everyday conveniences continue to make the area even more desirable. The home is also located close to local schools, major commuting routes, and the dining and shopping destinations of Middletown, making daily errands and travel simple. If you’re looking for a home that combines style, comfort, community, and convenience, 1823 N Pollock Way offers the perfect opportunity to enjoy everything that makes Bayberry living so special.
#DENC2097964

MIDDLETOWN

1823 N POLLOCK WAY

3 Beds

2 Baths

2,400 Sq.Ft.

$450,000

MLS#: DENC2097964

Brand new to the market and just recorded, complete with well, 4 BR conventional perc, electric at edge of lot, and spectacular view of South Mountain historic area and Middletown Valley. Middletown Middle and High schools and Myersville ES for top education. Farm animals allowed accept for swine. Bring your own builder or listing agent will introduce you to top builders in the area. There is no sign on the property, please call LA to set up showing. This lot and the one next to it are the "cream of the crop" and will be gone before Spring build! Hurry today to inspect.
#MDFR2075328

MIDDLETOWN

9702 MOUNT TABOR - LOT 11 ROAD

None Beds

None Baths

10.26 acres

$450,000

MLS#: MDFR2075328

Enjoy single-floor living in this inspired ranch home! At the front of the home, you'll find two bedrooms flanking a full bath. Toward the back, there's a well-appointed kitchen nestled between an elegant dining room and generous great room. The laundry is located near the primary bedroom, which has a large walk-in closet and a private bath. You'll love the professionally curated finishes! Situated on a corner lot and backing to open common area.
#VAFV2035268

MIDDLETOWN

100 MIDSUMMER LANE

3 Beds

2 Baths

1,610 Sq.Ft.

$449,999

MLS#: VAFV2035268

Classic R.C. Peoples-built 2 Story in rarely available Great Oak Farms. This home has fantastic curb appeal starting with the brick siding, but not forgetting the long driveway that is complimented by two decorative brick pillars. Moving inside, there is a living room with a cozy fireplace; just a few steps away from the formal dining room. The kitchen its own dining area, no shortage of cabinet space, and has access to the basement and family room featuring another fireplace! The second story has a full bathroom, and four spacious bedrooms which includes the primary suite that boasts its own full bathroom and plenty of closet space! Additional features include: a mud/laundry area off of the family room with access to the powder room, a total of 4 garage spaces (2 sets of 2 car garages), a brand new septic system, all resting on a large 1 acre lot. While tucked away in the tranquil community, this home is still located just minutes from major routes making your commute an absolute breeze. An excellent home that is ready for your personal touch!
#DENC2072634

MIDDLETOWN

325 GREAT OAK DRIVE

4 Beds

2 Baths

2,150 Sq.Ft.

$449,900

MLS#: DENC2072634

Welcome to 301 White Pine Dr in charming Middletown, DE! Nestled on an expansive corner lot, this property offers the perfect blend of space, freedom, and potential. With no HOA restrictions, you’re free to let your imagination run wild—whether you envision a lush garden oasis, a backyard entertainment haven, this property has two garages for storage for your hobbies and toys. The home itself is bursting with possibilities to make it truly your own. Located in a desirable area of Middletown, you’ll enjoy the peace of suburban living while staying close to local shops, dining, and top-rated schools. Don’t miss this rare opportunity to create the home you’ve always wanted, with no limitations holding you back! Schedule a showing today and discover all the potential waiting for you at 301 White Pine Dr
#DENC2096792

MIDDLETOWN

301 WHITE PINE DRIVE

4 Beds

3 Baths

2,578 Sq.Ft.

$445,000

MLS#: DENC2096792

Welcome to 25 Chester Court in Middletown, MD, a stunning end unit townhome. This spacious home offers 2472 square feet of modern living across three floors, featuring 3 bedrooms and 3.5 bathrooms. The main level boasts a contemporary kitchen with white quartz countertops, stainless steel appliances, and a large deck perfect for entertaining. The expansive open walkout basement includes a full bathroom, providing ample space for recreation or an additional living area. The home also features luxury vinyl plank (LVP) flooring on all three floors, and an upstairs laundry room for convenience. The oversized primary bedroom is a true retreat, complete with two walk-in closets and an en-suite bathroom with dual vanities and a large shower. Two additional guest rooms and a full hall bathroom complete the upper level. The property includes a one-car garage and plenty of parking in a quiet community. Enjoy the tranquility of this neighborhood while being close to local attractions, shopping, dining, and outdoor activities. This beautiful home is perfect for those seeking modern amenities and a peaceful living environment. Don't miss the opportunity to make 25 Chester Court your new home.
#MDFR2071442

MIDDLETOWN

25 CHESTER COURT

3 Beds

3 Baths

N/A

$444,900

MLS#: MDFR2071442

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