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
225
# of Listings
3
Avg # of Bedrooms
$274
Avg. $ / Sq.Ft.
$649,480
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

225 Properties Found. Page 11 of 15.

Ten acres in horse country. Build your dream home and or possible subdivide this 10-acre parcel of land. Bring your horses to this tranquil area that is so close but seems so far away from the hustle and bustle. The lot backs up directly to the 3,100 acre Augustine Wildlife area. Close to all major routes and only one hour to the Delaware beaches and 45 minutes to Philly International airport. This is a must-see property.
#DENC2093234

MIDDLETOWN

343 THORNTOWN ROAD

None Beds

None Baths

10.0 acres

$450,000

MLS#: DENC2093234

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

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

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.

$444,900

MLS#: MDFR2074744

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

"PRICE REDUCED, Motivated Owner." Are you Tired of all that 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.

$439,000

MLS#: VAFV2038186

* $5,000 Builder Incentive offered on all homes! Call for details. * Quick move-in! 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 is ready now.
#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.

$430,000

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

Motivated seller with a new price!!! Property sold as-is, offering upside potential in a great location. Well suited for cash buyers. Welcome to 1936 Old National Pike, a historic, brick-constructed home built around the turn of the last century, situated on nearly 4 acres along Old National Pike in Middletown, MD. Investors, flippers, and restoration experts, attention! A rare opportunity in Middletown, this turn-of-the-century brick home sits on almost four acres along Maryland’s historic Old National Pike. The property offers substantial upside for buyers prepared to take on a full-scale renovation, with large interior spaces, classic brick construction, a metal roof, and mature surrounding acreage. The home, built circa the turn of the last century, is listed strictly "as-is" and is currently not move-in ready. It offers a durable metal roof and generous interior space, but it needs a comprehensive overhaul. The Land & Outbuilding is nearly four acres, feature mature acreage and include a spacious outbuilding/barn structure with existing electric service. This asset can be used as a workshop, studio, storage, or for conversion. Historic Significance: This is a true piece of local history, positioned directly on Maryland’s original National Pike Road. This home is for the buyer dedicated to preservation; it provides the opportunity to bring a landmark property back to its former glory. Conservation Easement: The Maryland Environmental Trust (MET) Conservation Easement covers the property. This is an optimal acquisition for an experienced house flipper or investor looking for a major value-add project with significant potential ROI after full restoration. Ideal for buyers who value privacy, history, and the potential to make this property their own.
#MDFR2073722

MIDDLETOWN

1936 OLD NATIONAL PIKE

4 Beds

2 Baths

2,824 Sq.Ft.

$429,000

MLS#: MDFR2073722

** 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

Welcome to 153 Crystal Run Dr! This ranch home is located on an amazing one acre lot in a cul de sac as well as being in the Appoquinimink School District! One floor living is made easy with a floor plan that flows from one room to another. The kitchen is the center of the home and offers ample cabinet space and storage. There are two living areas that have vaulted ceilings and great natural lighting. A sunroom is also ideal for the warmer months. Three large bedrooms and two full bathrooms complete the first floor. The basement spans the entire home and can be finished for additional living space and recreation. Outside, the large deck showcases the private yard. This home is centrally located close to 896, 301 and more. Schedule your tour today!
#DENC2094658

MIDDLETOWN

153 CRYSTAL RUN DRIVE

4 Beds

2 Baths

1,975 Sq.Ft.

$425,000

MLS#: DENC2094658

Welcome to the 55+ community of Traditions at Whitehall - Alrich Carriage Town Home. This home is available as an interior or end unit & has a first-floor owner's bedroom w/ensuite bath and walk-in closets, second floor has a 2nd bedroom, loft and an additional full bath. Standard 1-car rear load attached garage but can be upgraded for a 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.***)
#DENC2095112

MIDDLETOWN

204 BALDY LN ALRICH

2 Beds

2 Baths

1,794 Sq.Ft.

$425,000

MLS#: DENC2095112

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