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
21
# of Listings
3
Avg # of Bedrooms
$240
Avg. $ / Sq.Ft.
$1,015,376
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

10 Properties Found. Page 1 of 1.

Escape the subdivision life for a residence defined by scale, privacy, and rugged utility. Set on 32.39+/- acres, this cabin-style estate is built for those who want their permanent home to feel like a fortress of solitude without sacrificing modern comforts. The interior features a recently updated kitchen equipped with new appliances and granite countertops. While there is a propane furnace, there is also a classic woodstove that provides a high-efficiency heating source and a focal point for the entertainment area in the basement. The home’s footprint is anchored by an expansive rear deck designed for four-season use; whether you’re hosting or decompressing, the integrated hot tub offers total privacy, screened by a dense canopy of mature timber to create an outdoor living room that feels completely removed from the outside world. This isn't just a woodlot; it's a gateway. The property borders Gambrill State Park, providing exploration and recreational opportunities right out your back door. For the serious outdoorsman or the family seeking an active lifestyle, the land offers endless utility for hiking, scouting, and wildlife management. The long, wooded approach ensures a level of seclusion and security that is increasingly rare, making this an ideal primary residence for those seeking a quiet, secure environment. Practicality meets potential inside and out, with a walkout basement that provides the ideal entertainment area or can be converted into a home office, gym, or additional bedrooms to grow with your needs. An existing shed provides organized storage for ATVs and maintenance equipment, keeping your primary living spaces clutter-free. Shown by appointment only, this is more than a getaway—it is a rare opportunity to own a significant piece of acreage with your ideal mountain retreat on your own recreational land in the Catocin Mountains.
#MDFR2074476

MIDDLETOWN

8939 HAWBOTTOM ROAD

3 Beds

3 Baths

3,236 Sq.Ft.

$989,000

MLS#: MDFR2074476

HOME TO BE BUILT. Nestled on a beautiful, wooded 2.25-acre lot, this to-be-built home by Grossnickle Construction offers the perfect blend of luxury and comfort. The home features 3 spacious bedrooms, including a private primary suite, 2 full bathrooms, and a convenient powder room. This plan also includes 400 sqft rec room in the basement and the option for an upstairs bonus room. Enjoy the peaceful, natural setting with mature trees and scenic surroundings while still having the opportunity to personalize your new home. This featured plan can be built as-is, tweaked to your preferences, or you can choose a completely different custom plan to fit this homesite. Don’t miss this chance to build your dream home in a truly serene location.
#MDFR2080886

MIDDLETOWN

MOUNTAIN CHURCH ROAD

3 Beds

2 Baths

3,000 Sq.Ft.

$924,500

MLS#: MDFR2080886

Welcome to this beautifully upgraded colonial nestled in the sought after Glenbrook golf community- backing to the 15th fairway. Relax, entertain and unwind in your resort style backyard with a stunning inground salt water pool, beautifully landscaped private back yard and new paver walkways. This light filled beauty is loaded with desirable features and upgrades offering nearly 5400 square feet of exceptional living space designed for both everyday comfort and elegant entertaining. This stunning home features brand new luxury vinyl flooring across two levels, creating a modern and cohesive feel from the moment you enter. The spacious gourmet kitchen is the heart of the home complete with granite counter tops and abundant cabinetry, and an inviting morning room filled with natural light and overlooking the private pool and yard- the perfect setting for morning coffee or evening gatherings. The impressive family room showcases a cozy fireplace and soaring ceilings for an open and airy layout, while the dual staircases add timeless architectural charm and functionality. Upstairs the expansive primary suite offers a peaceful retreat with a separate sitting room and a spa-like primary bathroom designed for relaxation. The finished walk up basement provides incredible versatility with an extensive built-in storage space making it ideal for recreation, hobbies, a home gym or additional entertaining space. There is also a EV charger in the garage and the roof and gutters have both been replaced! This home combines elegant updates, generous living spaces and exceptional outdoor living which lends itself to the perfect blend of luxury, warmth and lifestyle all while located in a desirable school district, nearby dining, shopping, parks and convenient commuter routes! Welcome home!
#MDFR2080926

MIDDLETOWN

503 GLENBROOK DRIVE

4 Beds

3 Baths

4,892 Sq.Ft.

$885,000

MLS#: MDFR2080926

Price Improvement! This iconic 1937 Brick Tudor Revival residence and adjacent additional structure are being sold together, situated on two separately deeded parcels that share a well and septic system. The Tudor Revival home has been freshly painted and offers timeless character blended with thoughtful updates throughout. 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 inviting 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, along with new roofs on both the home and pool house, provides added peace of mind. The finished basement expands the living space with a recreation room, partial kitchen, office, laundry area with shower, and a half bath—ideal for a variety of residential needs. Outside, the oversized fully fenced backyard creates a private retreat, featuring an in-ground pool with a new liner installed in 2022, a brick pool house, and a storage shed—perfect for entertaining or relaxing. The adjacent structure offers substantial additional space and includes notable features such as three-phase 400-amp electrical service, a 4,000-pound jib crane, and existing interior infrastructure. The property is currently zoned R3 and is being sold strictly for residential use. Any future use of the additional structure is subject to zoning regulations, and buyers are encouraged to conduct their own due diligence with the appropriate local authorities.
#MDFR2076696

MIDDLETOWN

3213 OLD NATIONAL PIKE

3 Beds

2 Baths

1,782 Sq.Ft.

$699,900

MLS#: MDFR2076696

NEW PRICE! OPEN HOUSE SUNDAY 5/17 - 10:00-12:00! 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.

$650,000

MLS#: MDFR2080220

Now on market! This picturesque single-family home sits in the heart of beautiful historic Middletown. Meticulously cared for from top to bottom, this exceptional property is perfectly positioned on a premium lot with stunning views of Middletown’s historic steeples, the breathtaking South Mountain range, and the charm of a white-picket-fence community. Tucked within a small clustered neighborhood with no HOA, this home offers the feel of a close-knit community without the added monthly dues. Inside, you’ll find five distinct bedrooms, including a convenient main-level bedroom and full bathroom. Step outside to the expansive rear deck, the perfect place to enjoy your morning coffee or unwind with evening cocktails while taking in the mountain views. The beautiful kitchen is ideal for intimate entertaining and is complemented by a well-appointed butler’s pantry. Downstairs, the fully finished basement is an entertainer’s dream, featuring a full wet bar, high-tech theater system with surround sound and projector, and additional gathering space with a walkout to the backyard.
#MDFR2079846

MIDDLETOWN

307 WASHINGTON STREET

5 Beds

3 Baths

3,288 Sq.Ft.

$645,000

MLS#: MDFR2079846

New on site 2 days ago
Welcome to Foxfields at Middletown, one of the area’s most sought-after 55+ communities. This beautifully maintained Admar-built Radford II offers the ease of main-level living paired with exceptional space for guests, entertaining, and everyday comfort. With 3 bedrooms, 4 full bathrooms, and the potential for a 4th bedroom in the finished lower level, this home is thoughtfully designed for both function and flexibility. Filled with natural light, the open floor plan features hardwood flooring, plantation shutters, and a spacious family room centered around a gas fireplace. The kitchen is both stylish and practical with espresso cabinetry, granite countertops, stainless steel appliances, abundant counter space, a large island, and generous table space perfect for gatherings. A convenient laundry room is located just off the kitchen. The main-level primary suite offers a walk-in closet and private bath, while a second main-level bedroom and full bath provide the ideal setup for guests or a home office. Upstairs, you’ll find a private third bedroom with its own full bathroom. The fully finished walk-up lower level expands the living space even further with a large recreation area, full bar, additional full bathroom, potential 4th bedroom, and extensive storage space. Step outside to enjoy the beautiful covered and screened porch overlooking the backyard with stunning sunset views — the perfect place to relax and unwind at the end of the day. Additional highlights include a 2-car garage and major system updates already completed: hot water heater (2022), HVAC (2024), and roof and gutters (May 2025). The HOA handles snow removal, allowing for truly low-maintenance living. Move right in and start enjoying everything Foxfields has to offer.
#MDFR2082252

MIDDLETOWN

11 CRONE LANE

3 Beds

4 Baths

2,649 Sq.Ft.

$625,000

MLS#: MDFR2082252

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.

$624,900

MLS#: MDFR2078904

Charming Victorian Home offers the perfect blend of historic character and modern upgrades in the heart of Middletown. Vehicle access from both Beautiful Main Street and Convenient Broad Street, this home provides excellent accessibility and curb appeal. Beautiful Hard Wood Floors, Wainscoting, Crown Molding throughout. Main Level Features Separate Living Room, Dining Room w/Pocket Doors, Family Room, Kitchen, Updated Full Bath. Kitchen includes Center Island w/Seating, Gas Cook-top, and Pantry. (2024: New Refrigerator, New Gas Cooktop, New Kitchen Disposal). Upper Level Features 3 Nice Size Bedrooms. Updated Full Bath with Heated Floor, Large Glass Front Shower, Custom Cabinets, Makeup Vanity, and Jetted Claw Foot Tub. An Oversized 2nd Floor Laundry Room with a Pocket Door features a second kitchenette area including upper and lower cabinets and countertop space. New Washer and Dryer in 2022. Access to Attic and a Small room with view overlooking back yard. Property also includes a Large/Tall Detached 2 Car Garage w/Tesla EV Charger. Attached to the Garage is a Large Shop/General Use Space. Home includes a Large Rear Deck off the Kitchen. A Whole-House Backup Power Generator w/New Battery in 2026. 2 Whole-House Surge Protectors, 2 Outdoor A/C unit Surge Protectors installed 2025. 4 Propane Tanks. This Listing also includes an Attached Additional Lot of Record w/Temp Restrictions. Conveniently located near schools, shopping, dining, parks, and easy access to major highways. This well-cared-for Victorian on Main Street is truly special.
#MDFR2081222

MIDDLETOWN

124 E MAIN STREET

3 Beds

2 Baths

2,474 Sq.Ft.

$599,900

MLS#: MDFR2081222

New on site 1 day ago
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! All new Siding, New Gutters, New Roof, Freshly painted interior of Garage, New Well Pump and SO MUCH MORE!!
#MDFR2082600

MIDDLETOWN

8209 OLD HAGERSTOWN ROAD

5 Beds

3 Baths

2,312 Sq.Ft.

$514,900

MLS#: MDFR2082600

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