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 Middletown, MD real estate 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
97
# of Listings
3
Avg # of Bedrooms
$329
Avg. $ / Sq.Ft.
$502,882
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

47 Properties Found. Page 3 of 4.

Enjoy single level living in this ranch plan Three bedrooms and 2 full baths. The Master Suite has a large walk-in closet and a private bath. Laundry is situation near the master suite offering ultimate convenience. Large kitchen island, fireplace, deck off the great room and an unfinished basement with a 3-piece plumbing rough-in for future bathroom. This beautiful home is a must see! Call today to schedule your tour of our Onyx ranch style plan.
#VAFV2034546

MIDDLETOWN

104 MIDSUMMER LANE

3 Beds

2 Baths

1,610 Sq.Ft.

$464,999

MLS#: VAFV2034546

Welcome to your new home in the charming town of Middletown, VA! This spacious 4-bedroom, 2.5-bath single-family home offers the perfect blend of comfort, style, and convenience. Enjoy an open floor plan that’s ideal for both everyday living and entertaining, featuring a large kitchen island and plenty of room to gather. The generously sized bedrooms provide comfort and flexibility, while the large, useable backyard offers an inviting space for outdoor relaxation or play. Conveniently located near major commuter routes—including I-81, Route 11, I-66, Route 7, and Route 50—this home makes commuting simple and efficient. You’ll also be just minutes from Winchester and Stephens City, and close to Shenandoah National Park, the Shenandoah River, local restaurants, and shopping. With its prime location and inviting layout, this Middletown rental offers the best of comfort and convenience in a fantastic setting.
#VAFV2038238

MIDDLETOWN

129 BIRMINGHAM

4 Beds

2 Baths

2,880 Sq.Ft.

$460,000

MLS#: VAFV2038238

Renovated oversized farmhouse nestled in the heart of Middletown Valley, where timeless character meets modern comfort. This charming 3-bedroom, 2-full-bath home is truly move-in ready and filled with warmth and natural light. On the main floor you will find a spacious open concept living area with custom fireplace, while the updated kitchen showcases SS appliances/quartz countertops/white shaker cabinets/ a custom tiled backsplash and lots of countertop space for entertaining. On the 2nd floor there are 3 large bedrooms, a laundry room, a large full bath with custom tile work and owners suite with a access to a private rear balcony as well as access to the full walk up attic! Outside you can relax on the covered front porch and take in the peaceful surroundings, or entertain in the generous yard framed by scenic valley views. A standout feature is the two-story “man cave” with a workshop below and an upper-level living space—ideal for conversion into a private studio, home office, or creative retreat. On top of all this there is a brand new roof, new furnace and new AC!
#MDFR2074744

MIDDLETOWN

8109 OLD HAGERSTOWN ROAD

3 Beds

2 Baths

1,752 Sq.Ft.

$449,000

MLS#: MDFR2074744

HAPPY HOLIDAY'S!!! Are you Tired of the City Noise & Traffic, have you been longing for that small town feel, then come checkout this 4 Bedroom 2.5 Bath 4yr old Colonial Home in the Shenandoah Valley. It's Close to I-81 & I-66 and Rt/11. This home Boasts with an Open Concept on the Main Level. The Family room overlooks the Kitchen with a Large Island & Stainless-Steel Appliances & Dining Room; Powder Room & Office complete this level. There's Luxury Vinyl Plank Flooring & Carpet Throughout. Up to the 2nd level that has a Generous size Primary Bedroom with a walk-in Closet & Full Bathroom. There are 3 more Bedrooms, a Full Bath & a separate Laundry Room complete this level. Down to the Basement that has rough in plumbing for another Bathroom. You can Create in this Unfinished space Another Bedroom if needed, Or A Huge Family room. Plenty of room to grow. The Possibilities are Endless. Off the Dining room slip out to the large Private (10'x20') Deck Outback for Entertaining or Relaxing & with stairs to the yard. The home comes with Recessed lighting & 6 Ceiling fans, Attached 2 Car Garage. Home was built by Ryan Homes & sits on a Premium Lot. Short drive to the Blue Ridge Mountains & the Shenandoah River. Shopping & Drive-in Theater nearby. So, if you're starting out, relocating or just need more SPACE Come Checkout this Next Place to Call HOME!
#VAFV2038186

MIDDLETOWN

163 EMMET STREET

4 Beds

2 Baths

1,930 Sq.Ft.

$446,000

MLS#: VAFV2038186

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

Fully Renovated Rancher!! Beautiful Country Setting! Come check out this Incredibly SPACIOUS Home on just over an Acre. Over 2600+ finished sq feet, 3 bedrooms & 2 full baths. Extra bonus rooms could be bedrooms as well or however you choose. ALL BRAND NEW Flooring, Painting, Lighting, 3 Mini Splits, Architectural Roof, Septic System, Well pressure tank, Windows, and Kitchen! HVAC in Great Shape! Light and Bright and Ready for Move in!=
#VAFV2037978

MIDDLETOWN

6731 MIDDLE ROAD

3 Beds

2 Baths

2,630 Sq.Ft.

$430,000

MLS#: VAFV2037978

Nestled in the charming Middletown community, this delightful split foyer home offers a perfect blend of comfort and convenience. Located on a corner lot, there is ample space for guest parking and outdoor activities. The exterior of the home has been updated with beautiful new siding, gutters and downspouts in 2019. The well-maintained interior boasts 1,396 sq. ft. of living space, featuring three cozy bedrooms and a full bath. This home includes a spacious basement that contains 2 additional rooms for your convenience, a half bath and private office space. Enjoy evenings by the fireplace or host gatherings on the inviting patio overlooking a spacious 0.4-acre lot, complete with a personal above-ground pool and a play area for outdoor fun. The neighborhood is known for its friendly atmosphere and proximity to local parks, providing many opportunities for recreation and relaxation. With easy access to essential amenities and a welcoming spirit, this home is not just a place to live, but a place to thrive. Experience the warmth of Middletown and make this lovely residence your own!
#MDFR2073592

MIDDLETOWN

7129 LIMESTONE LANE

4 Beds

1 Baths

1,396 Sq.Ft.

$399,900

MLS#: MDFR2073592

Dream Homesite, Discover your perfect escape on this wooded, well installed and septic approved and engineered and ready to build, Nestled high above Middletown Valley the lot has a cleared homesite. views privacy and tranquility and minutes from town.
#MDFR2061288

MIDDLETOWN

8511 ROSEBUD COURT

None Beds

None Baths

8.2 acres

$339,000

MLS#: MDFR2061288

Beautiful three-level townhome in the Enfield Knolls community of charming Middletown, VA. The open floor plan is filled with natural light and features a modern kitchen with stainless steel appliances and a moveable island that conveys. Enjoy durable luxury vinyl plank flooring, a composite deck for outdoor relaxation, and the convenience of bedroom-level laundry. With 3 bedrooms, 2.5 baths, and a walk-out basement offering great storage space and access to the backyard, this home has it all. Ideally located near commuter routes to both I-66 and I-81, and with trash collection handled by the Town of Middletown, this is easy living in a great location.
#VAFV2037714

MIDDLETOWN

119 KENSINGTON CIRCLE

3 Beds

2 Baths

1,307 Sq.Ft.

$334,000

MLS#: VAFV2037714

Welcome to this delightful 3-bedroom, 1-bath single-family home nestled on Main St. in the heart of historic Middletown. Full of character and timeless appeal, this vintage gem is brimming with potential. Situated on a generous lot, the home boasts a spacious backyard—perfect for outdoor entertaining, gardening, or future expansion. Inside, you'll find original details that speak to the home's heritage, creating a warm and inviting atmosphere that’s ready to be reimagined. Whether you're looking to bring new life to a classic property or create your dream home in a sought-after location, this residence offers the perfect canvas. Attic is fully floored for extra storage, basement is unfinished & is another great storage space. With its unbeatable location in a charming community close to schools, shops, and parks, this is an opportunity you don’t want to miss.
#MDFR2069270

MIDDLETOWN

417 W MAIN STREET

3 Beds

1 Baths

1,392 Sq.Ft.

$279,990

MLS#: MDFR2069270

New on site 3 days ago
Welcome home to this charming Cape Cod located just outside the town limits of Middletown, VA, in Frederick County. Situated on two separate lots, this inviting property offers a rare combination of space, updates, and flexibility at an incredible value. The home features three bedrooms and two bathrooms, including a versatile upper-level bedroom that can serve as a private retreat, office, or guest space. Numerous updates have been completed, including replacement windows, a newer heat pump, water heater, and well pump, providing comfort and peace of mind for the next owner. Enjoy a peaceful setting while still being just minutes from downtown Middletown, schools, shopping, and commuter routes. Whether you’re a first-time buyer, downsizer, or investor, this property presents an excellent opportunity in a highly desirable area.
#VAFV2036748

MIDDLETOWN

2085 CHAPEL ROAD

3 Beds

2 Baths

1,053 Sq.Ft.

$199,900

MLS#: VAFV2036748

If you are in search of the perfect building lot that provides seclusion, yet has easy access to state maintained roads nearby. You've found it! Tremendous views of the Signal Knob Mountain from various lots! Perfect Dream Home Lot for the commuter looking to escape from the hustle of the city! Whether you want a House-on-the-Hillside Lot surrounded by seclusion, or a lot located close to the Private Common Use area for Lake Access, we have exactly what you're looking for. Only 3 lots remain out of 41!
#1000074677

MIDDLETOWN

COMFORTER LANE LOT 31

None Beds

None Baths

2.0 acres

$110,000

MLS#: 1000074677

3 bedroom perk
#VAFV2038332

MIDDLETOWN

HUTTLE

None Beds

None Baths

2.83 acres

$74,000

MLS#: VAFV2038332

Welcome to your new rental home in the charming town of Middletown, VA! This spacious 4-bedroom, 2.5-bath single-family home offers the perfect blend of comfort, style, and convenience. Enjoy an open floor plan that’s ideal for both everyday living and entertaining, featuring a large kitchen island and plenty of room to gather. The generously sized bedrooms provide comfort and flexibility, while the large, useable backyard offers an inviting space for outdoor relaxation or play. Need an office? A first floor office or playroom provides additional convenience. Conveniently located near major commuter routes—including I-81, Route 11, I-66, Route 7, and Route 50—this home makes commuting simple and efficient. You’ll also be just minutes from Winchester and Stephens City, and close to Shenandoah National Park, the Shenandoah River, local restaurants, and shopping. With its prime location and inviting layout, this Middletown rental offers the best of comfort and convenience in a fantastic setting.
#VAFV2037730

MIDDLETOWN

129 BIRMINGHAM

4 Beds

2 Baths

N/A

$2,850

MLS#: VAFV2037730

Escape to country living in this charming 4-bedroom, 3 full baths all brick ranch-style home set on 1.5 beautiful acre with mountain views. This well-maintained property offers plenty of space, comfort, and privacy. Animals considered on case by case basis. Apply with NVAR or VAR rental application or may apply online thru listers website. $50 app fee per person.
#VAFV2037856

MIDDLETOWN

1308 MINEBANK ROAD

4 Beds

3 Baths

2,679 Sq.Ft.

$2,500

MLS#: VAFV2037856

1 2 3 4

properties found. properties found. Page of .

- property

Send a message

Message successfully sent.

Your message

What is 3 + 4 ?

Reason for contacting?

Update Your Temporary Password

Personalize your search

Enter your email and we'll notify you immediately when new listings match what you're looking for.

or enter email address

Already have an account ? Login here

Continue your home search

Already have an account ? Login here

We use cookies

We use cookies primarily for analytics to enhance your experience. By accepting, you agree to our use of these cookies. You can manage your preferences or learn more about our cookies policy.

Privacy Policy Terms of Service