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
284
# of Listings
3
Avg # of Bedrooms
$268
Avg. $ / Sq.Ft.
$636,911
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

28 Properties Found. Page 2 of 2.

A Truly Rare Opportunity! For the first time ever on the public market, the iconic 1937 Brick Tudor Revival residence and the former Rudy’s Cold Beer & Welding commercial building next door are being offered together. These two separately deeded parcels share a well and septic system and present an exceptional opportunity for a flexible live-work setup or investment. The Tudor Revival home has been freshly painted and offers timeless character blended with thoughtful updates. The kitchen features stainless steel appliances, a new cooktop, custom cabinetry, and granite countertops. The formal dining room boasts built-in china closets and an oversized bay window, while the living room centers around a classic wood-burning fireplace. The primary suite includes custom wood-paneled walls, an oversized bay window, a walk-in closet plus two additional closets, and a private ensuite bath. A new hot water heater, and a new roof on the home and pool house provides added peace of mind. The finished basement expands the living area with a recreation room, partial kitchen, office, laundry area with shower, and a half bath. Outside, the oversized fully fenced backyard features an in-ground pool with a new liner installed in 2022, a brick pool house, and a storage shed—perfect for entertaining or relaxing in your own private retreat! The adjacent commercial building adds remarkable versatility. It includes three-phase 400-amp electrical service, a 4,000-pound jib crane, and an interior build-out previously used for beer and wine retail, complete with refrigeration and dedicated storage areas. While currently zoned R3, it had been operating under a non-conforming commercial use. It is our understanding this use may be eligible to continue under applicable zoning regulations. However, it is the buyer’s responsibility to verify all zoning, permitted uses, and continuation of non-conforming status with the appropriate authorities, as the Seller cannot guarantee approval. Commercial listing can also be found at MLS #MDFR2076716
#MDFR2076696

MIDDLETOWN

3213 OLD NATIONAL PIKE

3 Beds

2 Baths

1,782 Sq.Ft.

$750,000

MLS#: MDFR2076696

New on site 2 days ago
OPEN HOUSE SATURDAY 4/25 - 1:00-3:00! Welcome to 7 Derr Lane in the sought-after Villages at Foxfield—Middletown’s premier 55+ community—where Original Owners have meticulously maintained and thoughtfully upgraded this beautiful home, showcasing true pride of ownership everywhere you look. Perfectly positioned within walking distance to Middletown Park and its many amenities, this home also backs to serene woods, walking/jogging paths, and open green space—offering both convenience and some privacy. Enjoy peaceful mornings on the covered front porch or unwind in the backyard retreat featuring a walkout patio, koi pond, and a hidden “secret garden” be sure not to miss. Inside, the home blends comfort and modern updates. The kitchen is a standout with a Corian island, mosaic tile backsplash, stainless steel appliances (replaced 2019), induction downdraft cooktop, double oven, and ceramic flooring—ideal for both everyday living and entertaining. The main level boasts hardwood flooring (2018) and a warm, inviting family room with a propane fireplace and direct access to the newer, enlarged Trex deck (2022, with updated door in 2025). The spacious layout includes vaulted ceilings, a tray ceiling in the primary suite, and a dramatic two-story overlook with loft above. The primary bath was beautifully renovated in 2017, and the upper level features new carpet (2019). Additional updates include leased solar panels for energy efficiency (2018), washer and dryer (2021), vinyl fencing (2022), new roof and ventilation (2024), HVAC (2015), and water heater (2018). The unfinished lower level offers a walkout to the backyard, rough-in for a full bath, and a wide-open layout ready to be customized to your needs. Garage is equipped with a 200 amp 240 volt EV charging circuit and a newer garage door opener (2021). This is a rare opportunity to own a truly move-in-ready home in Middletown’s most desirable active adult communities—combining thoughtful upgrades, natural beauty, and a vibrant lifestyle.
#MDFR2080220

MIDDLETOWN

7 DERR LANE

3 Beds

2 Baths

2,208 Sq.Ft.

$675,000

MLS#: MDFR2080220

Tucked away on over 5 private acres, this chalet-style home is not your typical property – and that’s exactly the point. With soaring ceilings, expansive windows, and skylights throughout, the home has a great balance of natural light and surrounded by wooded views that give it a true treehouse-like feel. A cozy fireplace anchors the main living space, while hardwood floors and warm finishes add to its character. The wraparound deck extends the living space outdoors, offering a peaceful setting for morning coffee or unwinding at the end of the day. An oversized detached two-car garage provides ample space for storage, hobbies, or projects. The kitchen has been refreshed with granite countertops and stainless steel appliances, blending modern convenience with the home’s unique style. This is a home for someone who appreciates privacy, architecture, and a setting that feels removed from it all - while still being just 15 minutes to Middletown’s shops, dining, and Middletown Schools. Updates include: Roof (2020), Skylights (2020), Stove & Microwave (2021), Refrigerator (2023), and Water Softener/Neutralizer (2022).
#MDFR2078904

MIDDLETOWN

6838 MOUNTAIN CHURCH ROAD

4 Beds

3 Baths

2,488 Sq.Ft.

$639,900

MLS#: MDFR2078904

Welcome Home to 8209 Old Hagerstown a beautifully updated and spacious 5-bedroom, 3-bathroom home located in the highly sought-after Middletown, MD. This move-in ready property features modern upgrades throughout, offering the perfect blend of style, comfort, and functionality. Enjoy generous living spaces, an updated kitchen featuring SS Appliances, white shaker cabinets, quartz counters and MORE! Well-appointed bedrooms ideal for both everyday living and entertaining. Fully finished basement offers so much space for entertaining. Large deck great for relaxation! Private off street parking in driveway and SO MUCH MORE! Situated in a desirable location close to commuter routes and many attractions —this is a home you won’t want to miss!
#MDFR2077940

MIDDLETOWN

8209 OLD HAGERSTOWN ROAD

5 Beds

3 Baths

2,312 Sq.Ft.

$524,900

MLS#: MDFR2077940

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

NEW PRICE! OPEN HOUSE SUNDAY 4/26 - 1:00-3:00! Welcome to 9233 Baltimore National Pike in Middletown—where country charm meets everyday convenience. This well-maintained 3 bed, 2 full bath home offers over 2,100 finished square feet, including a mostly finished lower level that provides flexible space for a family room, home office, and bonus room. Upstairs, you’ll find a blend of hardwood and luxury vinyl plank flooring, creating a warm and durable living environment. The home is equipped for year-round comfort with a 2016 forced air heat pump, baseboard backup oil heat, and a cozy wood stove—giving you multiple climate control options to suit your needs. Step outside and enjoy the peaceful setting from the screened-in front porch, or entertain in the spacious backyard featuring a patio and storage shed. The oversized 732 sq ft detached garage easily accommodates a vehicle with additional room for storage or a workshop, while the large driveway offers ample parking for guests. RECENT UPDATES: include a 2020 tin roof on both the main house and garage, a 2022 water heater, plus a UV filtration system and water softener for added peace of mind. Appliances have been updated between 2025–2026, making this home move-in ready, budget-friendly to get into Middletown! Located in the desirable Middletown school district, this property offers the best of both worlds—quiet country living with easy access to commuter routes and all the conveniences of nearby town amenities. Don’t miss your opportunity to enjoy space, versatility, and comfort in a beautiful Frederick County setting.
#MDFR2078968

MIDDLETOWN

9233 BALTIMORE NATIONAL PIKE

3 Beds

2 Baths

2,117 Sq.Ft.

$429,000

MLS#: MDFR2078968

New on site 1 day ago
Discover the charm of this inviting townhouse nestled in the desirable Glenbrook community, where comfort meets convenience. Built in 2004, this traditional-style home boasts 2,652 sq. ft. of thoughtfully designed living space, perfect for creating lasting memories. Step inside to find a warm and welcoming interior featuring a cozy gas fireplace and tons of natural light. The heart of the home is the spacious eat-in kitchen, complete with upgraded countertops, a convenient island, and stainless steel appliances, making meal prep a delight. With four bedrooms and three and a half bathrooms, there's ample space for everyone. The daylight basement offers additional versatility, whether for a playroom, home office, or guest suite. Enjoy the serene views of the adjoining golf course and South Mountain, from your maintenance free deck, perfect for morning coffee or evening relaxation. The Glenbrook community enhances your lifestyle with amenities like tot lots and playgrounds, while the association takes care of the lawn care, allowing you more time to enjoy your home. Nearby parks provide ample opportunities for outdoor activities, while local schools are known for their commitment to excellence. With convenient access to public services and a welcoming community spirit, this home is not just a place to live, but a place to thrive. Experience the perfect blend of comfort, community, and convenience in this lovely Glenbrook townhouse.
#MDFR2080900

MIDDLETOWN

502 STONE SPRINGS LANE

4 Beds

3 Baths

2,652 Sq.Ft.

$425,000

MLS#: MDFR2080900

Welcome to 304 Washington Street, a charming Cape Cod nestled in the heart of Middletown, Maryland—where natural light, character, and walkability take center stage. Built by Lancaster Homes, this residence is tucked on a quiet cul-de-sac and set on approximately 0.18 acres, offering 1,229 square feet above grade with a thoughtful and inviting layout. The main level features a first-floor primary bedroom with a full bath, along with a light-filled family room, kitchen, and convenient half bath designed for everyday living. Recent updates create a fresh, move-in-ready feel, including new luxury vinyl plank flooring throughout the main level, brand-new carpet upstairs, and a freshly painted exterior that enhances curb appeal. All three bedrooms offer walk-in closets, with the upstairs bedrooms featuring separate sinks within the shared Jack and Jill full bath for added functionality. The unfinished basement provides excellent storage with built-in shelving, while additional storage continues in the attached one-car garage, complete with a rear door for easy access to both the patio and front of the home. From the front porch, a bird’s-eye perspective reveals a more level setting, leading to a flatter, walkable backyard that adds to the home’s everyday ease. The yard is thoughtfully maintained with trees and plantings and offers beautiful sunset views stretching toward the mountains—a truly special feature. A small rear patio creates the perfect spot to relax and enjoy the outdoor space. Located in a quiet, friendly neighborhood just moments from Middletown’s Historic Main Street, shops, dining, parks, schools, and library, this home offers the charm of in-town living with the ease of a truly walkable lifestyle.
#MDFR2079976

MIDDLETOWN

304 WASHINGTON STREET

3 Beds

2 Baths

1,229 Sq.Ft.

$419,900

MLS#: MDFR2079976

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.

$399,000

MLS#: MDFR2073722

New on site 1 day ago
Here is your chance to own a COMPLETELY RENOVATED and beautifully re-designed home in highly sought after Middletown MD! All new inside and out with impeccable details added throughout the home presenting a warm and inviting space with a total of 4 bedrooms, 2 full baths and 1 half bath! A MAIN LEVEL PRIMARY SUITE has been added with three more spacious bedrooms upstairs all with hardwood floors and closets. The dream kitchen features extensive custom cabinetry with a built-in buffet including extra electrical outlets for small appliances, Quartzite countertops, Gold pulls and faucet, White tile backsplash, Brand new FRIGIDAIRE appliances including Refrigerator, Electric Stove/Oven, Microwave, Dishwasher and a built in pantry for additional storage. A huge center island with seating for four and new light fixtures complete the gorgeous finishes and makes a great space for gathering with friends and family for all of the great Middletown events! Many other new features include: recessed lighting with dimmer switches, light fixtures, extra electrical outlets, washer and dryer, 1/2 bath added to main level, two closets in primary suite, White tile in bath, Electric, Plumbing, Roof and HVAC to all of the rooms! Vintage touches remain and add to the appeal and authentic period details. Hard wood floors on the main and second floor have been professionally cleaned and sealed. The roof replacement included structural soundness and added columns to structure and authenticated structurally sound by a structural engineer. Warm tones and matching floors and surfaces through-out the home create continuity and a comfortable feel for easy living. A great back yard offers outdoor space for relaxing, gardening and more. Walkable to everywhere downtown Middletown and lots of extra parking nearby for guests. Enjoy all the events and markets that living on a small town main street offers. This property has been professionally renovated, professionally cleaned and professionally staged and is ready for it new owners to settle immediately.
#MDFR2080400

MIDDLETOWN

208 MAIN STREET

4 Beds

2 Baths

1,616 Sq.Ft.

$387,000

MLS#: MDFR2080400

Welcome to 25 Boileau Court in Middletown. This three-level townhome is located in a small neighborhood with no HOA and is conveniently situated near downtown Middletown. The main level features a living room, dining room, kitchen, and half bathroom. The spacious primary suite is located on the upper level and includes an en suite bathroom. Two additional bedrooms and a full hallway bathroom complete the second level. The lower level provides additional living space with a family room that has walkout access to the backyard, along with a half bathroom for added convenience. Recent updates include a roof that is just 2 years old, fresh paint throughout, and new carpet in the lower level. This home has been well maintained, thoughtfully updated, and is truly move-in ready. Plenty of parking available. This property offers easy access to the local shops, dining, parks, and everyday amenities of downtown Middletown. It is so close you may not even need to take your car. Don't miss your chance to see this home. Schedule your tour today!
#MDFR2080102

MIDDLETOWN

25 BOILEAU COURT

3 Beds

2 Baths

1,870 Sq.Ft.

$359,000

MLS#: MDFR2080102

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

New on site 3 days ago
Wow! How often do you see a reasonably priced parcel with close access and water privileges? Ever wish you had a place to recreate close to home? Have you ever wanted to escape from your home and still have a place to go? This could be it!! No HOA, you don't even have to mow it! Just show up and enjoy. The sound of the water going over the weir is so peaceful and relaxing. It diminishes the sound of the road traffic on Hwy 17. There is easy access from the road which provides plenty of parking. There are stairs down to the water which could use a handrail repair. But I'm sure you'll have plenty of time for that this summer while you're there enjoying the stream. Please call the agent, Debbie Hugo, for a personal tour. It doesn't have an address but it's between and across the street from addresses 7102A and 7020 Burkittsville Road.
#MDFR2080876

MIDDLETOWN

BURKITTSVILLE ROAD

None Beds

None Baths

1.36 acres

$35,000

MLS#: MDFR2080876

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