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
254
# of Listings
3
Avg # of Bedrooms
$267
Avg. $ / Sq.Ft.
$648,044
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

84 Properties Found. Page 3 of 6.

This charming brick rancher is located at the end of a cul-de-sac in sought after Middletown and sits on a peaceful 1.72 acre level lot. The first floor features an open floor plan complete with hardwood floors throughout, formal living room, formal dining room, family room with brick fireplace, breakfast nook leads to a relaxing Trex deck and patio overlooking the large backyard. 1st floor laundry room leads to a oversized 2 car garage. 3 bedrooms and 2 full baths. The fully finished walkout lower level features another full bathroom and large storage room. Some recent upgrades include 20 SEER heat pump (2023), new septic field (2023), electric fireplace (2024), well pump (2020), Ecobee smart thermostat (2023).
#MDFR2073664

MIDDLETOWN

6527 MORNINGSIDE COURT

3 Beds

3 Baths

2,275 Sq.Ft.

$549,900

MLS#: MDFR2073664

New on site 2 days ago
Rare opportunity in the heart of Middletown! This beautiful 8-acre parcel offers the perfect blend of small-town charm, open space, and future potential. Currently used for cattle and hay production, the property is partially fenced and includes a shed, making it ideal for continued agricultural use or your own private farmette — bring your animals! With town water and sewer hookup available, you’ll enjoy the convenience of municipal services while embracing the peaceful rural setting. Zoned RA, this property offers exciting possibilities, including potential subdivision for up to four homes (buyer to verify). Whether you envision a family compound, custom home sites, or investment opportunity, the options are plentiful. Enjoy sweeping views of pastureland and the surrounding mountains, all while being just a short walk to Main Street to experience local dining, shops, and community festivities. Conveniently located just minutes from I-81 for easy commuting. Property is being sold as-is. Buyer to verify all information. Property is in land use - buyer assumes rollback taxes if it is removed from land use! Please note: Livestock are currently on the property; showings are by appointment only and an agent must accompany for showings.
#VAFV2039608

MIDDLETOWN

VETERANS - LOT 12 ROAD

None Beds

None Baths

8.0 acres

$549,000

MLS#: VAFV2039608

New on site 3 days ago
Welcome to 1 Walnut Pond Ct in the heart of Middletown! Nestled on a desirable corner lot in a small, quiet neighborhood, this beautifully updated 4-bedroom, 2.5-bath home offers comfort, style, and peace of mind with major upgrades already completed. Enjoy brand new windows, a new HVAC system, new hot water heater, and new stainless steel appliances. The home features new flooring throughout, including laminate flooring and carpet, along with fresh paint that gives the entire space a clean, modern feel. Step outside to a 5-year-old Trex deck overlooking your private backyard retreat complete with a screened-in porch and a pool with a 2-year-old liner — perfect for entertaining or relaxing all summer long. Additional highlights include a 2-car garage and a prime corner lot location in one of Middletown’s most desirable areas. Move-in ready and loaded with upgrades — this one won’t last!
#MDFR2076532

MIDDLETOWN

1 WALNUT POND COURT

4 Beds

2 Baths

1,620 Sq.Ft.

$530,000

MLS#: MDFR2076532

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

Rare opportunity to own a beautiful parcel on River Ridge Drive offering privacy, potential, and long-term value. This undeveloped lot provides the perfect canvas for a custom home, recreational retreat, or investment hold in an area experiencing steady land demand. Surrounded by natural beauty and located within close proximity to local amenities, this property offers both tranquility and convenience. Strategically priced based on current land market trends and buyer activity, this property is being marketed to attract qualified end users and investors alike. Ideal for out-of-state buyers, builders, or those seeking to secure land for future use. Don’t miss the chance to own land with flexibility, upside potential, and location appeal. Come build your dream home on this stunning 20-acre parcel tucked within a private community. Ideally located just minutes from Front Royal, Winchester, I-66, and I-81, this property offers the perfect balance of peaceful seclusion and easy access to nearby towns and amenities. Enjoy mountain views and direct frontage on the beautiful Shenandoah River — ideal for fishing, kayaking, and embracing nature’s serenity. With gently rolling terrain and potential building sites, the possibilities are endless for creating your full-time residence, weekend escape, or legacy property. Approximately 400 feet of frontage on the North Fork of the Shenandoah River. Don’t miss this rare opportunity to own a private piece of the Shenandoah Valley.
#VAWR2011208

MIDDLETOWN

0 RIVER RIDGE DRIVE

None Beds

None Baths

20.0 acres

$480,000

MLS#: VAWR2011208

Enjoy single-floor living in this inspired ranch home! At the front of the home, you'll find two bedrooms flanking a full bath. Toward the back, there's a well-appointed kitchen nestled between an elegant dining room and generous great room. The laundry is located near the primary bedroom, which has a large walk-in closet and a private bath. You'll love the professionally curated finishes! Situated on a corner lot and backing to open common area.
#VAFV2035268

MIDDLETOWN

100 MIDSUMMER LANE

3 Beds

2 Baths

1,610 Sq.Ft.

$464,999

MLS#: VAFV2035268

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

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.

$444,999

MLS#: VAFV2034546

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

The main floor of this Coral home offers a large, uninterrupted space for relaxing and entertaining. The kitchen features a spacious center island and opens to the dining and great rooms. Upstairs, you'll find a convenient laundry, a full bath tucked between two generous bedrooms, and an inviting primary suite with a walk-in closet and private bath. This home is built a loft. To round out this home a basement is included and this beautiful home backs to common area.
#VAFV2035270

MIDDLETOWN

102 MIDSUMMER LANE

3 Beds

2 Baths

1,840 Sq.Ft.

$439,999

MLS#: VAFV2035270

* $15,000 builder incentive; thru 2/28/26 * 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

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

One-level living in the sought-after Village at Middletown! This move-in-ready home welcomes new owners with an open floor plan designed for comfortable living and easy entertaining. The living room flows seamlessly into the kitchen, creating a bright and inviting main living space. The spacious kitchen features a breakfast bar, ample table space, and access to a large, low-maintenance Trex deck—perfect for cookouts or relaxing outdoors. Main-level laundry adds everyday convenience. The primary suite offers a walk-in closet with generous storage and a private bath with shower. Two additional well-sized bedrooms and a full hall bath complete the main level. The full unfinished basement includes egress for a future bedroom, a rough-in for a full bath, and the potential to nearly double your living space. A two-car garage with additional storage and a concrete driveway provide plenty of off-street parking. Ideally located for commuters, just minutes to I-81 and I-66, with easy access to local shops, schools, and amenities.
#VAFV2039012

MIDDLETOWN

151 COUGILL

3 Beds

2 Baths

1,378 Sq.Ft.

$425,000

MLS#: VAFV2039012

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