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
253
# of Listings
3
Avg # of Bedrooms
$274
Avg. $ / Sq.Ft.
$640,029
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

68 Properties Found. Page 2 of 5.

Stunning new construction by Rachuba Homes in the heart of historic downtown Middletown. Now offering a $15,000 incentive, with no lender tie-in! This is a rare opportunity to enjoy walkable small-town living in a brand new, move-in ready home, with no HOA. Situated on nearly half an acre, this thoughtfully designed 4 bedroom, 2.5 bath residence offers comfortable, practical living with an open layout ideal for everyday life and entertaining. The kitchen features stainless steel appliances, quality cabinetry, premium countertops, and a stylish backsplash. The main level includes 7-inch luxury plank flooring, black hardware accents, and a welcoming covered front porch. Upstairs, the spacious owner’s suite includes a walk-in closet and a private bath with a 6x7 shower and dual sinks. Three additional bedrooms, a full bath, and a conveniently located upper-level laundry complete the second floor. The finished lower level provides a large recreation space for additional living or entertaining, plus a rough-in for a full bath and space for a fifth bedroom with egress already in place. Located just steps from Middletown’s shops, restaurants, parks, and community events, and within the highly regarded Middletown school district, this home offers the convenience of an established downtown setting with the efficiency and peace of mind of new construction.
#MDFR2074184

MIDDLETOWN

26 WALNUT STREET

4 Beds

2 Baths

2,712 Sq.Ft.

$699,000

MLS#: MDFR2074184

New on site 2 days ago
Tucked away on over 5 private acres, this chalet-style home is not your typical property – and that’s exactly the point. With soaring ceilings, expansive windows, and skylights throughout, the home a great balance of natural light and surrounded by wooded views that give it a true treehouse-like feel. A cozy fireplace anchors the main living space, while hardwood floors and warm finishes add to its character. The wraparound deck extends the living space outdoors, offering a peaceful setting for morning coffee or unwinding at the end of the day. An oversized detached two-car garage provides ample space for storage, hobbies, or projects. The kitchen has been refreshed with granite countertops and stainless steel appliances, blending modern convenience with the home’s unique style. This is a home for someone who appreciates privacy, architecture, and a setting that feels removed from it all - while still being just 15 minutes to Middletown’s shops, dining, and Middletown Schools. Updates include: Roof (2020), Skylights (2020), Stove & Microwave (2021), Refrigerator (2023), and Water Softener/Neutralizer (2022).
#MDFR2078904

MIDDLETOWN

6838 MOUNTAIN CHURCH ROAD

4 Beds

3 Baths

2,488 Sq.Ft.

$649,900

MLS#: MDFR2078904

New on site 1 day ago
Do Not Miss Your Opportunity to Check Out This Beautiful 5-Bedroom, 4.5-Bathroom Home in the Desirable Woodland Hills Community! Built in 2022, this Custom Designed Residence offers Modern Finishes and A Family Friendly Layout Throughout. Welcoming Main Level Features an Open-Concept Kitchen Featuring Custom Countertops, Luxury Vinyl Flooring, and Spacious Living Areas Perfect for Everyday Living and Entertaining. Main Floor Also Features a Versatile In-Law Suite or Primary Bedroom with an Attached Full Bath for Added Convenience. Enjoy the Abundance of Natural Light in the Sunroom, Surrounded by Large Windows that Create a Warm and Inviting Atmosphere. Upstairs,4 Generously Sized Bedrooms and 3 Well-Appointed Bathrooms provide Comfort and Privacy for Family or Guests. A Large Unfinished Walkout Basement is Waiting for Your Ideas, Plenty of Space for a Super Man Cave , Hobby, Play Area and Work-Out Room. Outside, a Charming Brick Patio offers the Ideal Spot for Relaxing or Entertaining in the Peaceful Environment of this Quiet Neighborhood. Economical Gas Heat, Instant Hot Water System and Water Softening and Filtering Unit Provide Cost Effective Services . This Home Has So Much To Offer , Do Not Miss Your Opportunity to Check This Upscale Property Out !!
#PADA2057844

MIDDLETOWN

182 MAGNOLIA DRIVE

5 Beds

4 Baths

3,576 Sq.Ft.

$629,900

MLS#: PADA2057844

Tucked within the desirable Old Reliance Farms neighborhood, this exceptional home offers a rare chance to own in this peaceful community. Step inside to find bright hardwood flooring leading through the foyer to the formal dining room, highlighted by classic chair rail detailing and a lighted tray ceiling. The spacious eat-in kitchen features an island/breakfast bar and opens up to the bright sunroom, creating an inviting space for gatherings. The cozy family room showcases a stone gas fireplace, serving as the heart of the home. The main level also includes an additional living area, a versatile office or recreation room, a full bath, and a convenient laundry area. Upstairs, the primary suite is complete with a large walk-in closet and a private ensuite bath featuring a soaking tub and a walk-in shower. Two additional spacious bedrooms each offer walk-in closets and share a full bath. The finished basement expands your living space with a game room full bath, additional office, and ample storage—ideal for both entertaining and everyday functionality. Step outside to enjoy the beautifully designed back patio, perfect for relaxing or entertaining while taking in the peaceful surroundings of this quiet community.
#PADA2057588

MIDDLETOWN

1325 PHEASANT RUN ROAD

3 Beds

4 Baths

4,126 Sq.Ft.

$624,999

MLS#: PADA2057588

Stunning 4-bed, 3.5-bath single-family home ideally located just minutes from Downtown Middletown. Set on a generous 15,000 sq. ft. corner lot with peaceful tree-lined views, this residence boasts numerous enhancements inside and out. Step inside to upgraded flooring and sophisticated finishes throughout. The inviting living room showcases custom built-ins with shelving and storage, while the dining area is adorned with classic wainscoting and elegant lighting. The kitchen is a chef’s dream, equipped with custom cabinetry, granite countertops, a stylish stone backsplash, recessed lighting, and stainless steel appliances—including a newer refrigerator, dishwasher, and microwave (2022–2024). Adjacent to the kitchen, the expansive family room is perfect for entertaining, featuring a cozy wood-burning fireplace and French doors that open to a stone patio overlooking the tranquil backyard. A convenient powder room completes the main level. Upstairs, retreat to the spacious owner’s suite with custom accent wall, walk-in closet, and a recently renovated luxurious en-suite bath (2024). This spa-like bathroom offers a dual-sink vanity and an oversized walk-in shower with a built-in bench, body jets, and three shower heads—including an overhead rainfall system—designed for ultimate relaxation. Three additional bedrooms share a modern full bath with tub/shower combo and updated wall and floor tiles. The lower level provides flexible living space, featuring a large rec room with a wet bar, a potential 5th bedroom, full bath with stand-up shower, and laundry area with ample storage—ideal for an in-law suite, home office, gym, or play area. Step outside and enjoy your private oasis, complete with a stone patio, hot tub, outdoor string lights, storage shed, and a flat, fully fenced yard for everyone to enjoy! The attached two-car garage and driveway offer off-street parking for up to four vehicles. Other recent improvements include newer HVAC (2023), water heater (2022), and roof (approx. 2019). No HOA fees! Ideally situated near Middletown Park with sports fields, trails, and pond, Middletown Library, and all the dining and shopping that Downtown Middletown and Frederick have to offer!
#MDFR2077776

MIDDLETOWN

4300 ZIRCON ROAD

4 Beds

3 Baths

2,912 Sq.Ft.

$619,900

MLS#: MDFR2077776

*$10,000 builder incentive; thru 3/31/26* 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

REFRESHED, REVAMPED AND MOVE-IN READY. YOU SPOKE AND WE LISTENED. CHECK IT OUT AGAIN! This beautifully updated Dulaney model by ADMAR Custom Homes is nestled in the highly sought-after 55+ section of Foxfield in picturesque Middletown and has been lovingly maintained by its original owner. Recent updates make this home truly turnkey, including new quartz countertops, new stainless steel appliances, new luxury vinyl plank flooring in the kitchen, updated lighting, and refreshed hardware—allowing you to simply move in and enjoy. A welcoming ceramic-tiled foyer offers convenient access to the attached two-car garage and a perfectly placed powder room. The kitchen features abundant cabinetry and opens seamlessly to the living room, creating a comfortable and connected space for everyday living. Sunlight pours into the breakfast nook through two large corner windows, making it an inviting spot for morning coffee. The main level showcases beautiful hardwood flooring, a spacious primary bedroom, and a bright living room with sliding glass doors leading to a private patio—ideal for relaxing outdoors or entertaining friends. You’ll also appreciate the main-level washer and dryer, providing the ease of single-level living. Upstairs, two additional bedrooms and a full bath offer flexible space for guests, hobbies, or a home office—perfect for today’s active lifestyle. The fully finished walk-out basement expands your living space with wall-to-wall wood flooring, recessed lighting, and a warm, open feel ideal for entertaining, game nights, or gatherings. A large utility room with ceramic tile, utility sink, and deep-freezer outlet adds everyday practicality, while the nearly completed roughed-in bathroom awaits your finishing touch. Step outside to a lush, green backyard that offers both privacy and tranquility—your own peaceful retreat. Enjoy low-maintenance living, thoughtful updates, and a welcoming community designed for active adults. This exceptional home is ready for your next chapter—don’t miss it.
#MDFR2076674

MIDDLETOWN

1 KELLER LANE

3 Beds

2 Baths

3,161 Sq.Ft.

$564,900

MLS#: MDFR2076674

Welcome Home to 8209 Old Hagerstown a beautifully updated and spacious 5-bedroom, 3-bathroom home located in the highly sought-after Middletown, MD. This move-in ready property features modern upgrades throughout, offering the perfect blend of style, comfort, and functionality. Enjoy generous living spaces, an updated kitchen featuring SS Appliances, white shaker cabinets, quartz counters and MORE! Well-appointed bedrooms ideal for both everyday living and entertaining. Fully finished basement offers so much space for entertaining. Large deck great for relaxation! Private off street parking in driveway and SO MUCH MORE! Situated in a desirable location close to commuter routes and many attractions —this is a home you won’t want to miss!
#MDFR2077940

MIDDLETOWN

8209 OLD HAGERSTOWN ROAD

5 Beds

3 Baths

2,312 Sq.Ft.

$549,900

MLS#: MDFR2077940

Welcome to the beautifully crafted Lexington model—brand new and READY NOW in the desirable Greenwood Hills community! This energy-efficient home offers nearly 2,000 sq. ft. of thoughtfully designed living space, with 4 spacious bedrooms and 3 full bathrooms, including a main-level bedroom and full bath w/ walk-in shower, perfect for guests, multi-generational living, or a home office. The kitchen features 36” painted cabinets w/ crown molding, elegant quartz countertops, floating shelves, stainless steel appliances with gas cooking, and a walk-in pantry with solid shelving. The kitchen flows seamlessly into the dining area and open family room, creating a welcoming space for both everyday living and entertaining. Upstairs, the primary suite provides a peaceful retreat, complete with a walk-in closet and private en-suite bath with tile shower. Two additional bedrooms and a hall bath complete the upper level. Additional highlights include a two-car garage, walk-out lower level ready to finish, and a 10 year home warranty for added peace of mind. Enjoy life in Greenwood Hills—a thoughtfully planned neighborhood with sidewalks, community benches, a modern park, and a scenic pond with an observation deck. Conveniently located with easy access to Route 283 and the PA Turnpike.
#PADA2045388

MIDDLETOWN

160 HARTFORD DRIVE

4 Beds

3 Baths

1,966 Sq.Ft.

$509,900

MLS#: PADA2045388

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

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

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

New on site today
Well-maintained single-family home built in 1974 featuring a classic split foyer design. The main level showcases beautiful hardwood floors and newer carpet in the bedrooms, along with custom window blinds in the living room and front bedroom. The kitchen is equipped with a recently replaced range/oven (Jan 2026). Enjoy year round relaxation in the rear solarium, which opens to a deck and spacious backyard perfect for entertaining or quiet outdoor living. Major updates include a newer HVAC system (2024) and roof replacement (2015), offering added peace of mind. The partially finished lower level features a cozy wood-burning fireplace, half bath, separate laundry area, and a utility/storage room with exterior access leading to the side of the home and garage. As an added bonus, the seller is offering a transferable First American Home Warranty for the new owner.
#MDFR2078668

MIDDLETOWN

4614 PINEWOOD TRAIL

3 Beds

2 Baths

1,684 Sq.Ft.

$440,000

MLS#: MDFR2078668

New on site 3 days ago
UNDER CONSTRUCTION! This Swift model is a 3 BD, 2.5 BA, semi-detached home. Come discover the value that is packed into this 1,980 sq. ft. home. Nine foot first floor walls enhance the spacious feeling of this open floor plan. A self-cleaning electric range, granite counters and soft-close cabinet doors/drawers are featured in this kitchen. The luxury vinyl plank flooring flows throughout the main living area. The first floor study is the perfect space for a home office or den. The owner’s suite is sure to please with large walk-in closet and private bath. 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, 10×12 composite deck, and a 2 car garage. This home is situated on a perimeter homesite that borders woodland so you will continually be delighted with the wonders of the natural beauty around you. Total taxes are estimated.
#PADA2057886

MIDDLETOWN

251 SAGE BOULEVARD

3 Beds

2 Baths

1,980 Sq.Ft.

$434,976

MLS#: PADA2057886

New on site 3 days ago
UNDER CONSTRUCTION! This Swift model is a 3 BD, 2.5 BA, right-side unit, semi-detached home. Come discover the value that is packed into this 1,980 sq. ft. home. Nine foot first floor walls enhance the spacious feeling of this open floor plan. A self-cleaning electric range, granite counters and soft-close cabinet doors/drawers are featured in this kitchen. The first floor study is the perfect space for a home office or den. The owner’s suite is sure to please with large walk-in closet and private bath. 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, 10×12 composite deck, and a 2 car garage. This home is situated on a perimeter homesite that borders woodland so you will continually be delighted with the wonders of the natural beauty around you. Total taxes are estimated.
#PADA2057890

MIDDLETOWN

253 SAGE BOULEVARD

3 Beds

2 Baths

1,980 Sq.Ft.

$434,267

MLS#: PADA2057890

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