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
257
# of Listings
3
Avg # of Bedrooms
$274
Avg. $ / Sq.Ft.
$639,186
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

48 Properties Found. Page 3 of 4.

New on site today
Backing to trees with a fully fenced backyard, Trex deck, hot tub, built-in fire pit, and storage shed, this beautiful craftsman-style home offers the outdoor setting buyers are looking for along with a warm, functional interior designed for everyday living. Inside, you will find 4 spacious upper-level bedrooms, a main-level office, and a bright layout that blends comfort and flexibility. The kitchen serves as the heart of the home with marble backsplash, recessed lighting, upgraded lighting over the island and dining area, and updated fixtures that add a fresh modern feel throughout. An updated hall closet adds both style and additional practicality. Upstairs, the laundry room is thoughtfully positioned for convenience and includes added cabinetry for storage and organization. The unfinished basement with interior access and fire exit window offers excellent potential for future finished living space, recreation, gym, or storage. The 2-car garage features an epoxy-finished floor for a clean polished look that elevates the space. Located in a welcoming HOA community with trash and snow removal included, this neighborhood is known for cookouts, football watch parties, and year-round connection. Conveniently located near historic Middletown, local dining, commuter routes, and approximately 15 minutes to Skyline Drive, offering easy access to both daily conveniences and outdoor adventure. Open House this Sunday, March 29th 11am - 1pm.
#VAFV2040404

MIDDLETOWN

135 BIRMINGHAM

4 Beds

2 Baths

1,900 Sq.Ft.

$484,900

MLS#: VAFV2040404

Rare opportunity to own a private homesite in the desirable River Ridge on the Shenandoah community in Middletown, VA. This undeveloped parcel offers the perfect setting for a custom-built home, weekend retreat, or long-term investment. Enjoy natural surroundings, peaceful privacy, and the flexibility to design and build to your vision (subject to county approvals). Located just minutes from historic Middletown, local dining, wineries, and commuter routes, this property offers a unique balance of seclusion and convenience. Land opportunities in this area are limited, secure your future homesite today. 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

Built in 2020, this well-maintained 4-bedroom, 2.5-bath home in Middletown, VA offers modern comfort with thoughtful design and room to grow. The main level with open plan flows from entry, to living room, to kitchen, to dining area, and also features a dedicated office with beautiful custom built-ins—perfect for working from home or creating an organized study space. The spacious primary suite on the upper level includes a private full bath and walk-in closet, while two additional bedrooms also feature walk-in closets, providing plenty of storage throughout the home. A convenient walk-in laundry room adds to the home’s functional layout and space. The full unfinished basement offers excellent potential and is already plumbed for a third full bath—ready for your future expansion and storage needs. Outside, enjoy a fully fenced rear yard ideal for pets, play, or outdoor entertaining. A great opportunity for a newer home with space, flexibility, and modern features in a convenient and charming Middletown location. Minutes from I-81 and across from Laurel Ridge Community College.
#VAFV2040048

MIDDLETOWN

471 COVILLE STREET

4 Beds

2 Baths

1,920 Sq.Ft.

$459,900

MLS#: VAFV2040048

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

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

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

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

New on site 2 days ago
Well-maintained single-family home built in 1974 featuring a classic split foyer design. The main level showcases beautiful hardwood floors and newer carpet in the bedrooms, along with custom window blinds in the living room and front bedroom. The kitchen is equipped with a recently replaced range/oven (Jan 2026). Enjoy year round relaxation in the rear solarium, which opens to a deck and spacious backyard perfect for entertaining or quiet outdoor living. Major updates include a newer HVAC system (2024) and roof replacement (2015), offering added peace of mind. The partially finished lower level features a cozy wood-burning fireplace, half bath, separate laundry area, and a utility/storage room with exterior access leading to the side of the home and garage. As an added bonus, the seller is offering a transferable First American Home Warranty for the new owner.
#MDFR2078668

MIDDLETOWN

4614 PINEWOOD TRAIL

3 Beds

2 Baths

1,684 Sq.Ft.

$440,000

MLS#: MDFR2078668

Welcome to 107 Jefferson Street. This Charming Colonial was recently rehabbed in (2019) to include a new roof, new dual zone HVAC and new wiring and plumbing throughout. Blending classic character with thoughtful modern updates, this home is truly move-in ready and is located in the heart of Middletown. Step inside to find a bright and inviting interior featuring refreshed finishes, open floorplan and cozy propane fireplace, updated flooring, and a neutral color palette that complements any style. The renovated kitchen offers modern cabinetry, updated countertops, and appliances, making it both functional and stylish. Updated bathrooms showcase contemporary fixtures while maintaining the home’s timeless appeal. Upstairs, 3 comfortable bedrooms provide peaceful retreats, while the flexible layout offers space for everyday living, entertaining, or working from home. Recent renovations enhance both comfort and peace of mind, allowing you to simply unpack and enjoy. Outside, the property offers a detached garage, a shed, a fenced rear yard, and a stone patio for entertaining. The front and back yards are thoughtfully landscaped with several mature trees that provide shade during hot summer months and an abundance of colorful butterfly-attracting perennials and bushes that provide a serene setting throughout the Spring to Fall. This yard wlll provide tranquility year round. Just a short walk to Middletown’s charming downtown shops, restaurants, schools, parks, the new public library and town events. Just 4 miles to commuter route70...this home delivers small-town charm with everyday convenience. A wonderful opportunity to own a fully rehabbed Colonial in one of Middletown’s most desirable locations - USDA Eligible —don’t miss it!
#MDFR2077730

MIDDLETOWN

107 S JEFFERSON STREET

3 Beds

2 Baths

1,584 Sq.Ft.

$429,900

MLS#: MDFR2077730

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

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.

$424,900

MLS#: VAFV2037978

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 ROAD

3 Beds

2 Baths

1,378 Sq.Ft.

$399,900

MLS#: VAFV2039012

Charming brick rancher set on 4.64 acres with stunning views and exceptional potential. This 3-bedroom, 1-bath home offers classic construction and “good bones,” making it a fantastic opportunity for buyers looking to add their own updates or build sweat equity. The home features a functional layout with an unfinished basement that provides additional space for storage, hobbies, or future finishing. This property consists of 2 tax parcels, offering added privacy, flexibility, and potential uses. The property also features a small stall barn, making it especially appealing for hobby farming, animals, or additional storage. Surrounded by trees and scenic countryside, the setting provides peaceful views and a sense of privacy while still being conveniently located near local commuter routes. Outdoor enthusiasts will appreciate the close proximity to Civil War historical sites, nearby battlefields, and the Appalachian Trail. Whether you’re looking for a primary residence, investment opportunity, or a property with room to grow, this home offers a rare combination of location, land, and opportunity.
#MDFR2078078

MIDDLETOWN

1629 DAHLGREN ROAD

3 Beds

1 Baths

1,056 Sq.Ft.

$335,000

MLS#: MDFR2078078

Looking for a million-dollar view in Middletown Valley- school district minutes from Frederick City limits and commuter routes? Look no further! Lot offers 3 possible home sites to choose from. Power is run to site, approved well with 15 GPM, driveway is in ready for building. Forest stewardship in place also- so no dealing with FRO easement applications and costs. Sediment plan has been completed by Fox & Assoc. Storm water plan has been completed. VA construction loans with no money down possible, 10% down construction loans available. Rear corners are marked.
#MDFR2077606

MIDDLETOWN

8511 ROSEBUD COURT

None Beds

None Baths

8.2 acres

$275,000

MLS#: MDFR2077606

Price Improved and ready for you to make this your new home in 2026 !! 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.

$254,000

MLS#: MDFR2069270

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