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
107
# of Listings
3
Avg # of Bedrooms
$329
Avg. $ / Sq.Ft.
$549,611
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

296 Properties Found. Page 12 of 20.

IMMEDIATE AVAILABILITY! Welcome to the 55+ community of Traditions at Whitehall - Annandale Carriage Town Home. This interior first floor owner suite comes w/a 2nd bedroom, loft, 2.5 baths, 2 car rear load attached garage, front porch, and additional finished upgrades. Community offers trails, in ground pool w/lounge areas, open clubhouse featuring exercise room, billiards, gathering space, full kitchen and a large outdoor patio area! Builder Splits Transfer Tax
#DENC2084904

MIDDLETOWN

1104 HIGHLAND STREET 138 ANNANDALE

2 Beds

2 Baths

1,794 Sq.Ft.

$449,500

MLS#: DENC2084904

Welcome home! Spacious craftsman style home in Villages at Middletown. The main level with large kitchen, dining and living room area is open and light-filled, making it perfect for entertaining. Walk out onto the back deck to enjoy the views with your morning coffee (or dine outside, there's plenty of room!)The upper level of this home boasts 5 bedrooms (or potentially use one as an office space), 2.5 baths, and large laundry room. Need more space? The basement is ready for your vision! Finish your way , it already has a rough in for a full bath! Walk out basement leads to beautiful patio space and large fully fenced backyard (corner lot backs to green space and tree line). ***ASK ABOUT THE VA assumable mortgage under 3%***
#VAFV2037906

MIDDLETOWN

100 COVILLE STREET

5 Beds

2 Baths

2,198 Sq.Ft.

$449,000

MLS#: VAFV2037906

New on site 1 day ago
Beautifully 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

MASSEY INTERIOR UNIT- 3 bedrooms, 3.5 baths, 1 car garage. Approx. 2232 SF! This home features a Finished den, 42" cabinets in kitchen, island, stainless steel appliances, gas range, dishwasher, microwave and recessed lighting in Kitchen. LVP flooring upgrades. 3 pc rough in walk out basement. Don't miss out on this spectacular floor plan! Builder Splits Transfer Tax
#DENC2092586

MIDDLETOWN

444 REDERICK LANE MASSEY LOT 69

3 Beds

2 Baths

N/A

$446,291

MLS#: DENC2092586

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

MASSEY INTERIOR UNIT- 3 bedrooms, 2.5 baths, 1 car garage. Approx. 2232 SF! This home features a Finished den, 42" cabinets in kitchen, island, stainless steel appliances, gas range, dishwasher, microwave and recessed lighting in Kitchen. LVP flooring upgrades and Breakfast Bar in kitchen. 3 pc rough in walk out basement. Don't miss out on this spectacular floor plan! Builder Splits Transfer Tax
#DENC2092556

MIDDLETOWN

448 REDERICK LANE MASSEY LOT 67

3 Beds

2 Baths

2,232 Sq.Ft.

$439,311

MLS#: DENC2092556

* $5,000 Builder Incentive offered on all homes! Call for details. * NOW UNDER CONSTRUCTION! There are so many things to like about this three bedroom, two bath, raised rancher plan. Enjoy the openness of the main living area as your family and guests gather around the action. The kitchen includes a 5′ island, granite countertops and pantry cabinet. The primary bedroom features a private bath and walk-in closet. Bedrooms 2 and 3 are just steps from the hall bath and laundry. The lower level has a large, unfinished area in addition to the two car garage and a finished flex room. Who doesn’t enjoy relaxing on a front porch or the back patio? Enjoy the view as you watch the changing seasons from this hilltop location. This home will be completed and ready for an early February settlement.
#PADA2051442

MIDDLETOWN

168 MAGNOLIA DRIVE

3 Beds

2 Baths

1,806 Sq.Ft.

$436,825

MLS#: PADA2051442

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.

$435,000

MLS#: VAFV2037978

Rare opportunity to own a double lot in town at an affordable price. This spacious home offers a ton of possibilities. The current owner has done a lot of upgrades over the last few years by updating the kitchen, the flooring, vanities, interior doors and paint. The metal roof was installed in 2021 and the A/C is only 3 years old. The double lot adds to this property in many ways, build a pole barn, build a separate rental or just leave it empty and let the kids play. Schedule your tour today.
#DENC2092074

MIDDLETOWN

908 S CASS STREET

4 Beds

1 Baths

2,200 Sq.Ft.

$430,000

MLS#: DENC2092074

None
#DENC2094038

MIDDLETOWN

40 S CUMMINGS DRIVE

3 Beds

2 Baths

2,200 Sq.Ft.

$429,500

MLS#: DENC2094038

Welcome to your next chapter in the vibrant, caring haven of Whispering Woods — an active adult community where life is anything but boring. This beautifully maintained, just 5 years young home greets you with an open concept layout, two full baths, two bedrooms and a truly spacious walk‑in closet that feels almost like a private room. Spectacularly clean, neutral finishes, adult friendly 1 story home and walk in tub, 2 sink kitchen and spacious cooking area! Step outside your door and into a world of daily fun: pickleball, bocce, swimming, social clubs, themed events all year round, and a dining hall with a bar and billiards area tailor‑made for neighbors to become friends. All of this is just minutes shopping and restaurants, with easy access to Routes 1, 301, and 896. The remaining balance of the builder's warranty are transferable to the new owner making this home a smart choice in today’s market. Landscape and exterior care are handled by the community.
#DENC2090658

MIDDLETOWN

1428 WHISPERING WOODS ROAD

2 Beds

2 Baths

1,275 Sq.Ft.

$428,000

MLS#: DENC2090658

** 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, 12x10 DECK, 42" cabinets in kitchen, island, stainless steel appliances, gas range, dishwasher, microwave and recessed lighting in Kitchen. LVP flooring upgrades. 3 pc rough in walk out basement. Don't miss out on this spectacular floor plan! Builder Splits Transfer Tax
#DENC2092584

MIDDLETOWN

446 REDERICK LANE MASSEY LOT 68

3 Beds

2 Baths

2,001 Sq.Ft.

$427,056

MLS#: DENC2092584

Superb. newer carriage style home located in the ever popular active adult community of Whispering Woods!! Oversized great room with recessed lighting, gas fireplace and luxury vinyl plank flooring, gourmet kitchen w/granite countertops, stainless steel appliances, island and separate eating area, owners suite with coffered ceiling, ceiling fans, sitting area and oversized walk-in closet and more!! Outside enjoy the private screened porch with ceiling fan and paver patio!! Two car garage!!! Community amenities are countless with the pool, clubhouse, pickleball, themed events and more!! Don't miss this gem!!
#DENC2093778

MIDDLETOWN

1415 WHISPERING WOODS ROAD

2 Beds

2 Baths

1,875 Sq.Ft.

$424,900

MLS#: DENC2093778

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.

$420,000

MLS#: MDFR2073592

1 ... 10 11 12 13 14 ... 20

properties found. properties found. Page of .

- property

Send a message

Message successfully sent.

Your message

What is 3 + 4 ?

Reason for contacting?

Sign Out

Virtual Assistant

Would you like to take the next step with this property? We can help you schedule a showing or virtual tour, or send you more details.

Yes, I would like more information.

Thank You for Your Reply, One of Our Agents will contact you as soon as possible

No, maybe later.

Thank you, you can always contact me via email, phone number or through the contact form.

Realhub AI

Lucy - Your AI-Powered Realtor

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