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 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
25
# of Listings
3
Avg # of Bedrooms
$240
Avg. $ / Sq.Ft.
$957,671
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

25 Properties Found. Page 2 of 2.

New on site 3 days ago
Welcome to Foxfields at Middletown, one of the area’s most sought-after 55+ communities. This beautifully maintained Admar-built Radford II offers the ease of main-level living paired with exceptional space for guests, entertaining, and everyday comfort. With 3 bedrooms, 4 full bathrooms, and the potential for a 4th bedroom in the finished lower level, this home is thoughtfully designed for both function and flexibility. Filled with natural light, the open floor plan features hardwood flooring, plantation shutters, and a spacious family room centered around a gas fireplace. The kitchen is both stylish and practical with espresso cabinetry, granite countertops, stainless steel appliances, abundant counter space, a large island, and generous table space perfect for gatherings. A convenient laundry room is located just off the kitchen. The main-level primary suite offers a walk-in closet and private bath, while a second main-level bedroom and full bath provide the ideal setup for guests or a home office. Upstairs, you’ll find a private third bedroom with its own full bathroom. The fully finished walk-up lower level expands the living space even further with a large recreation area, full bar, additional full bathroom, potential 4th bedroom, and extensive storage space. Step outside to enjoy the beautiful covered and screened porch overlooking the backyard with stunning sunset views — the perfect place to relax and unwind at the end of the day. Additional highlights include a 2-car garage and major system updates already completed: hot water heater (2022), HVAC (2024), and roof and gutters (May 2025). The HOA handles snow removal, allowing for truly low-maintenance living. Move right in and start enjoying everything Foxfields has to offer.
#MDFR2082252

MIDDLETOWN

11 CRONE LANE

3 Beds

4 Baths

2,649 Sq.Ft.

$625,000

MLS#: MDFR2082252

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 has 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.

$624,900

MLS#: MDFR2078904

Charming Victorian Home offers the perfect blend of historic character and modern upgrades in the heart of Middletown. Vehicle access from both Beautiful Main Street and Convenient Broad Street, this home provides excellent accessibility and curb appeal. Beautiful Hard Wood Floors, Wainscoting, Crown Molding throughout. Main Level Features Separate Living Room, Dining Room w/Pocket Doors, Family Room, Kitchen, Updated Full Bath. Kitchen includes Center Island w/Seating, Gas Cook-top, and Pantry. (2024: New Refrigerator, New Gas Cooktop, New Kitchen Disposal). Upper Level Features 3 Nice Size Bedrooms. Updated Full Bath with Heated Floor, Large Glass Front Shower, Custom Cabinets, Makeup Vanity, and Jetted Claw Foot Tub. An Oversized 2nd Floor Laundry Room with a Pocket Door features a second kitchenette area including upper and lower cabinets and countertop space. New Washer and Dryer in 2022. Access to Attic and a Small room with view overlooking back yard. Property also includes a Large/Tall Detached 2 Car Garage w/Tesla EV Charger. Attached to the Garage is a Large Shop/General Use Space. Home includes a Large Rear Deck off the Kitchen. A Whole-House Backup Power Generator w/New Battery in 2026. 2 Whole-House Surge Protectors, 2 Outdoor A/C unit Surge Protectors installed 2025. 4 Propane Tanks. This Listing also includes an Attached Additional Lot of Record w/Temp Restrictions. Conveniently located near schools, shopping, dining, parks, and easy access to major highways. This well-cared-for Victorian on Main Street is truly special.
#MDFR2081222

MIDDLETOWN

124 E MAIN STREET

3 Beds

2 Baths

2,474 Sq.Ft.

$599,900

MLS#: MDFR2081222

New on site today
Scenic views, top-rated schools, and no HOA—this beautifully updated Quad-level home in sought-after Middletown offers the perfect blend of comfort, efficiency, and lifestyle. Situated on a quiet street and backing to open farmland adjacent Summers Farm, this 4–5 bedroom, 2.5 bath home provides 2,200 square feet of versatile living space. Inside, you’ll find hardwood floors throughout, fresh paint, updated bathrooms, crown molding and a bright, functional layout designed for both everyday living and entertaining. The kitchen features new granite countertops, stainless steel appliances, and a spacious island, creating a central gathering space that flows seamlessly into the main living areas. The flexible lower level offers the option for a family room, home office, or guest suite. Recent upgrades include a high-efficiency 4-ton centrally ducted HVAC system and a 6kW OWNED (not leased) solar system—delivering comfort and long-term energy savings. Located just minutes from downtown Frederick—consistently ranked among the best places to live in the U.S.—this home offers small-town charm with convenient access to shopping, dining, and commuter routes. Move-in ready, thoughtfully updated, and set in one of Frederick County’s most desirable communities—this is a home you won’t want to miss.
#MDFR2081576

MIDDLETOWN

4510 WILLOW TREE DRIVE

4 Beds

2 Baths

2,200 Sq.Ft.

$529,000

MLS#: MDFR2081576

New on site 2 days ago
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! All new Siding, New Gutters, New Roof, Freshly painted interior of Garage, New Well Pump and SO MUCH MORE!!
#MDFR2082600

MIDDLETOWN

8209 OLD HAGERSTOWN ROAD

5 Beds

3 Baths

2,312 Sq.Ft.

$514,900

MLS#: MDFR2082600

Don't miss out on this very well maintained all-brick rancher situated on a level, half acre lot! This charming home features many updates and newer features -- including roof, water treatment system, well pump and much more. The kitchen boasts of solid surface countertops, tile backsplash and stainless steel appliances. Entering the living room, you will find a brick hearth fireplace and bright space thanks to plenty of windows. Just down the hallway is a convenient full bath and three bedrooms, including a primary bedroom with adjacent half bath. Hardwood and ceramic tile floors are featured throughout the main level bedrooms and baths. On the lower level, you will find an additional full bath, craft/sewing room, large workshop, two storage areas, laundry and areaway leading up to the fully fenced back yard. Enjoy the outdoors on the brick-paver patio with permanently attached gazebo-type structure which provides comfort & shade in the summer months. There is also a shed in the rear yard for storage of gardening tools, lawn mower, etc. Opportunities like this don't come along often so act fast!
#MDFR2079538

MIDDLETOWN

4432 VALLEY VIEW ROAD

3 Beds

2 Baths

1,232 Sq.Ft.

$479,900

MLS#: MDFR2079538

New on site 1 day ago
Your Private Oasis in Middletown Valley The Wait is Over! Welcome to the perfect blend of classic Maryland charm and modern peace of mind. Nestled on a quiet cul-de-sac, this stunning all-brick rancher offers the lifestyle you’ve been searching for in beautiful Middletown. Step through the front door and feel instantly at home. The hardwood floors gleam under the natural light pouring through the windows. Imagine cozy winter evenings gathered around the wood-burning fireplace in the spacious living room, or hosting casual brunches in the bright, cheerful eat-in kitchen. With three comfortable bedrooms on the main level this home is a clean canvas waiting for your personal touch. The walk-out basement is where your imagination can truly take flight. Partially finished with durable tile flooring and bathed in natural light, this space is far from your typical basement. With an extra unfinished room featuring a bathroom rough-in, the opportunities are endless:Create a private guest suite or multi-generational living space.Design the ultimate home office or gym. Build out a dream media room or hobby workshop. Step outside to a backyard that feels like an extension of nature. Unlike most neighborhood lots, this property does not back to other houses. Instead, you have direct access to a serene walking path, perfect for morning strolls or evening jogs in the fresh valley air. The exterior is virtually maintenance-free, allowing you to spend your weekends enjoying the view rather than keeping up with chores. Modern Updates for Peace of Mind Don’t let the 1965 charm fool you; the heavy lifting has already been done: Roof & Gutters: Only 1.5 years young. Electrical upgraded panel. Driveway: Re-paved approximately 6 years ago. Garage: Spacious attached 2-car garage for vehicles and storage. If you are looking for a home that offers privacy, stability, and the chance to build equity by finishing the lower level exactly how you want it, this is the one. Schedule your tour today—this Middletown gem won’t last!
#MDFR2082092

MIDDLETOWN

112 LOCUST COURT

3 Beds

1 Baths

1,680 Sq.Ft.

$439,900

MLS#: MDFR2082092

Beautifully updated townhome in sought after Glenbrook community backing to the Richland Golf club offering serene golf course views and an exceptional setting. Recent improvements include a brand-new architectural shingle roof, fresh paint, new carpet, and a stamped concrete patio. Gleaming solid oak hardwood floors and elegant accent molding highlight the main level, where a designated living room flows into an open-concept layout. The chef’s kitchen features a center island, granite countertops, and stainless steel appliances, seamlessly connecting to the dining area and inviting family room with a gas-burning fireplace and patio access. A convenient half bath completes this level. Upstairs, the spacious primary suite boasts a vaulted ceiling, large walk-in closet, and a luxurious bath with soaking tub, separate shower, and dual vanity. Two additional bedrooms and a hall full bath complete the upper level. The finished lower level offers a versatile fourth bedroom, full bathroom, large recreation room, and ample storage space. Enjoy the lifestyle offered in Glenbrook, surrounded by beautiful scenery and located close to top-rated schools, parks, shopping, dining, and major commuter routes, all within the highly desirable Middletown Valley has to offer..
#MDFR2081514

MIDDLETOWN

110 STONE SPRINGS LANE

4 Beds

3 Baths

2,652 Sq.Ft.

$435,000

MLS#: MDFR2081514

Welcome to this inviting rancher tucked into the heart of Middletown where you can enjoy scenic views and walk for ice cream all in a few steps. This one screams for ice cream. Just kidding. It screams LOCATION, LOCATION, LOCATION! No HOA and under $400K. That should be a headline! Inside, you'll find three bedrooms, three baths and an easy, open layout designed for everyday living. Neutral paint, LVP flooring and stainless appliances make the upper level shine bright-like a diamond. A newly built breezeway that connects the oversized single car garage is charming and will keep you dry! A cute little backyard to get creative with. Bring the chickens or a play set. It's open space, waiting for you. The lower level is finished and screams movie room and let's hang out! Flex space and plenty of storage. Did I mention Middletown schools? This district is known for its school spirit and community. GO Knights! Views, Updates, space, NO HOA and BRAND NEW HVAC!!! THIS one checks all the boxes. YOU ARE HOME!!
#MDFR2082096

MIDDLETOWN

98 SUMMERS DRIVE

3 Beds

2 Baths

2,152 Sq.Ft.

$399,999

MLS#: MDFR2082096

Completely remodeled and beautifully restored, this charming Main Street Middletown home combines timeless character with modern comfort and custom high-end finishes throughout. Every inch of the home has been thoughtfully redesigned and updated, creating a warm, inviting space that feels both stylish and functional. Major renovations include a brand-new roof with new sheathing, new electrical and plumbing systems, new HVAC throughout the entire home, new water heater, new recessed lighting with dimmer switches, new fixtures and all-new Frigidaire stainless steel appliances including range, refrigerator, microwave, dishwasher, washer, and dryer. The home has been professionally renovated and cleaned for immediate move-in readiness. The newly redesigned main level features a spacious primary suite with a beautifully finished full bath, plus a newly added half bath for guests. Original hardwood floors on both the main and upper levels have been professionally cleaned and sealed, blending classic charm with the home’s modern updates. Brand new matching Tile floors in the kitchen and bathrooms create continuity throughout the home. At the heart of the home is a stunning gourmet kitchen designed with custom cabinetry, quartzite countertops, white tile backsplash, gold hardware and fixtures, built-in pantry storage and a custom buffet area with extra electrical outlets for small appliances. The oversized center island with seating for four creates the perfect gathering space for everyday living and entertaining. Upstairs offers three additional spacious bedrooms with hardwood floors all with ample closet space and another beautifully updated full bath. Warm tones, natural finishes, and abundant light throughout the home create a cozy and welcoming atmosphere in every room. Outside, enjoy a private backyard ideal for relaxing, gardening, or entertaining. Convenient free parking is available nearby, including walkable public lots with EV charging stations. Located in the heart of historic Middletown, this home offers the unique charm of Main Street living with easy access to local shops, restaurants, community events, farmers markets, wineries, breweries, parks, and the Appalachian Trail. Just minutes from Frederick, Brunswick, Boonsboro, and nearby state parks. This fully remodeled home offers the perfect blend of historic charm, thoughtful design, and modern upgrades with custom finishes throughout. Schedule your private showing today.
#MDFR2080400

MIDDLETOWN

208 MAIN STREET

4 Beds

2 Baths

1,616 Sq.Ft.

$374,900

MLS#: MDFR2080400

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