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
260
# of Listings
3
Avg # of Bedrooms
$273
Avg. $ / Sq.Ft.
$645,993
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

44 Properties Found. Page 2 of 3.

Lot 1 East at Heritage Oak Estates | To-Be-Built Custom Home Opportunity. Don’t miss this rare opportunity to build your dream home in Heritage Oak Estates, an exclusive twelve-lot community by Atlantic Homes, nestled in the heart of the scenic Middletown Valley. Located less than a mile from charming Main Street in Middletown, MD this enclave offers panoramic views of pastoral landscapes and surrounding mountains—all with no HOA restrictions. Lot 1 East spans a generous 4.6-acre homesite and has already been approved for a four-bedroom septic system, with a private well already in place—ready for your dream home. Choose from a range of fully customizable floor plans or bring your own design. Each home will feature elevated standard finishes throughout, including: Masonry board exterior siding with stone water table; 10’ to 12' ceilings on the main level. Lot sizes in the community range from 2 to 7 acres, each offering its own unique views and privacy. Protective covenants ensure architectural integrity and long-term value—vinyl siding is not permitted, and minimum build standards apply. Lot 1 East offers the perfect blend of rural tranquility, upscale living, and accessibility—all in one of Frederick County’s most desirable areas. Photos and renderings are representative and for illustrative purposes only. All builder plans can be customized to fit your preferences. Contact listing agent for available plans, site details, and to explore available homesite options and start designing your future dream home today at Heritage Oak Estates!
#MDFR2069796

MIDDLETOWN

3130 BIDLE RD

4 Beds

3 Baths

2,500 Sq.Ft.

$1,186,202

MLS#: MDFR2069796

Lot 1 West at Heritage Oak Estates | To-Be-Built Custom Home Opportunity. Don’t miss this rare opportunity to build your dream home in Heritage Oak Estates, an exclusive twelve-lot community by Atlantic Homes, nestled in the heart of the scenic Middletown Valley. Located less than a mile from charming Main Street in Middletown, MD this enclave offers panoramic views of pastoral landscapes and surrounding mountains—all with no HOA restrictions. Lot 1 West spans a generous 2-acre homesite and has already been approved for a four-bedroom septic system, with a private well already in place—ready for your dream home. Choose from a range of fully customizable floor plans or bring your own design. Each home will feature elevated standard finishes throughout, including: Masonry board exterior siding with stone water table; 10’ to 12' ceilings on the main level. Lot sizes in the community range from 2 to 7 acres, each offering its own unique views and privacy. Protective covenants ensure architectural integrity and long-term value—vinyl siding is not permitted, and minimum build standards apply. Lot 1 West offers the perfect blend of rural tranquility, upscale living, and accessibility—all in one of Frederick County’s most desirable areas. Photos and renderings are representative and for illustrative purposes only. All builder plans can be customized to fit your preferences. Contact listing agent for available plans, site details, and to explore available homesite options and start designing your future dream home today at Heritage Oak Estates!
#MDFR2069522

MIDDLETOWN

7452 HERITAGE OAK TERRACE

4 Beds

3 Baths

2,618 Sq.Ft.

$1,180,000

MLS#: MDFR2069522

Lot 203 is the last remaining lot in the Estates of Old Middletown, Section 2—an exclusive five-lot subdivision located on Sumantown Road within the Middletown School District. This 1.348-acre homesite is ideally situated at the end of a private common driveway and offers sweeping views of the Appalachian Mountains. Home packages are available through Grossnickle Construction, or you may bring your own plans to build the custom home of your dreams. The lot is approved for a 4-bedroom home, perc-tested, and permit-ready. Opportunities like this are rare—don’t miss your chance to own the final lot in this premier Middletown community.
#MDFR2072962

MIDDLETOWN

5916 CLOUDBERRY COURT

4 Beds

3 Baths

3,149 Sq.Ft.

$1,100,000

MLS#: MDFR2072962

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

New on site 1 day ago
Nestled in the heart of rural Middletown, this immaculate custom-built rancher sits on 6.9 picturesque acres, offering breathtaking mountain views in the front and serene private woods in the back. A portion of the property is protected under Frederick County Forest Resource Conservation, preserving the natural beauty and tranquility of the setting. Inside, you’ll find a bright and open floor plan filled with thoughtful upgrades. The main level features rich hardwood flooring, elegant crown molding throughout, and a stunning great room with a vaulted ceiling and cozy gas fireplace. The gourmet kitchen is a chef’s dream, complete with cherry cabinetry, granite countertops, newer stainless steel appliances, and a spacious breakfast area that opens to a screened porch—perfect for enjoying peaceful mornings or evening entertaining. The home also offers a formal dining room adorned with chair rail and crown molding. The spacious primary suite boasts a tray ceiling, two large closets with custom organizers, and a beautifully updated en-suite bath featuring an oversized shower, double vanity, and modern finishes. Two additional bedrooms, a full hallway bath, a powder room, and a versatile office/den complete the main level. The lower level expands your living space with a large family room, a fourth bedroom with LVP flooring, and a full bath—ideal for guests or extended living. There’s also an expansive unfinished area, offering endless possibilities for storage or future customization. Additional highlights include an oversized side-load two-car garage with drywall finish and automatic openers, a dual heat system (heat pump with gas backup), and a convenient generator for added peace of mind. Located in the highly sought-after Middletown school district and just minutes from local nature attractions, this exceptional property combines comfort, privacy, and scenic beauty. Schedule your private showing today—this one won’t last long!
#MDFR2079508

MIDDLETOWN

3156 SUMANTOWN ROAD

4 Beds

3 Baths

3,329 Sq.Ft.

$824,900

MLS#: MDFR2079508

New on site 3 days ago
Enjoy peaceful one-level living in this beautifully designed 3-bedroom, 2 bath home set on 20 private wooded acres with stunning mountain views. Although not on the river owners have easy access to the Shenandoah River. Featuring 10-foot ceilings and an open, airy layout, this home offers an inviting eat-in kitchen with granite countertops and stainless-steel appliances. The living room features a handcrafted built-in cabinet, perfect to display your keepsakes. Relax and take in the natural surrounding from the expansive wraparound porch, perfect for entertaining or quiet mornings. The wooded setting provides privacy and endless opportunities to enjoy nature, all while offering comfortable, modern conveniences in a serene environment. Home is located close to I-81 and I-66 for easy commuting to Winchester or Northern Virginia.
#VAWR2014040

MIDDLETOWN

155 TURKEY

3 Beds

2 Baths

1,748 Sq.Ft.

$765,000

MLS#: VAWR2014040

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

A Truly Rare Opportunity! For the first time ever on the public market, the former Rudy’s Cold Beer & Welding commercial building and the adjacent 1937 Brick Tudor Revival residence are being offered together. These two separately deeded parcels share a well and septic system and present exceptional potential for an investor, business owner, or buyer seeking a flexible live-work opportunity. The commercial building offers significant functional value with three-phase 400-amp electrical service, a 4,000-pound jib crane, and an existing interior build-out designed for beer and wine retail, including refrigeration and storage areas ready for continued use. While the property is currently zoned R3, it previously operated under a non-conforming commercial use. It is our understanding that 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. The charming Tudor Revival residence enhances the offering with fresh updates and original character. The home has been freshly painted throughout and features an updated kitchen with stainless steel appliances, a new cooktop, custom cabinetry, and granite countertops. The formal dining room includes built-in china closets and an oversized bay window, while the living room showcases a classic wood-burning fireplace. The primary suite offers 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. Outdoors, the oversized fully fenced backyard includes an in-ground pool with a new liner installed in 2022, a brick pool house, and a storage shed—ideal for entertaining or unwinding in your own private retreat. The residential listing can also be found at MLS # MDFR2076696
#MDFR2076716

MIDDLETOWN

OLD NATIONAL

None Beds

None Baths

1,750 Sq.Ft.

$750,000

MLS#: MDFR2076716

Options galore! Purchase or ground lease with potential seller financing for a qualified purchaser. I-81 Exit #302 is the Gateway entrance into the Historic Town of Middletown, Virginia. This is the last remaining lot at the corner of Reliance Road and Valley Ave (Rt #11). We have 3.84 acres zoned B2 highway commercial. You are surrounded by The Village at Middletown by Ryan Homes. Richmond American Homes are building 90 additional single family homes on the south end of town. Middletown is home to Historic Wayside Inn, circa 1797, Laurel Ridge Community College with 3,500 students and staff. Immediate neighbors include; Comfort Inn, McDonalds, Dollar General, 7-11, Liberty C-store with fuel depot, Sheetz C-store with fuel depot has recently opened on the east side of the interstate. Locate your successful business venture where the growth is happening.
#VAFV2039508

MIDDLETOWN

0 RELIANCE

None Beds

None Baths

3.84 acres

$725,000

MLS#: VAFV2039508

New on site today
Coming Soon in Middletown on 5.21 acres — custom home with a fully finished lower-level apartment, perfect for multi-generational living. Tucked along a private gravel lane in the Shenandoah Valley, this property offers a peaceful, semi-secluded setting with a blend of open yard and wooded privacy. The main level features a split-level design with the primary suite privately situated on one side of the home, while the kitchen and main living areas sit at the heart of the layout. You’ll also find three additional bedrooms, including one currently staged as an office, along with a full bath and half bath. The home offers high ceilings, quality finishes, and a comfortable, functional flow. The primary suite includes an en-suite bath with new shower glass coming soon. The finished lower level lives like its own private apartment with a separate entrance, making it ideal for in-law living or extended guest space. This level includes a full kitchen with laminate countertops and full appliance package, a spacious living area, a bar/entertaining space with tile flooring, a second laundry area, and a full bathroom. One bedroom is considered a true bedroom, while an additional finished room (without a window or closet) offers great flexibility as an office, hobby room, or bonus space. A screened porch adds even more usable living area to the lower level. Additional highlights include a walk-out basement, a mix of carpet, tile, and LVP flooring, and thoughtfully designed spaces throughout. Situated on 5.21 acres with no HOA or restrictive covenants, the property offers ample room for outdoor activities, gardening, or hobby farming—all while still being conveniently located near commuter routes and local amenities. Out of respect for the occupants, please do not drive by the property.
#VAFV2040064

MIDDLETOWN

201 LIBERTY LANE

4 Beds

3 Baths

3,540 Sq.Ft.

$699,900

MLS#: VAFV2040064

Welcome to the perfect blend of modern style and peaceful country living. This brand-new modern farmhouse with craftsman influence is privately nestled on 6.6 wooded acres, offering the seclusion you crave while remaining just minutes from Routes 66 and 81 for an easy commute. Thoughtfully designed with meticulous attention to detail, this 3-bedroom home offers 2,000 square feet of beautifully finished living space. The heart of the home features a stunning stone gas fireplace that anchors the living room, creating a warm and inviting gathering space. The kitchen showcases gorgeous custom cabinetry, quality finishes, and a layout ideal for both everyday living and entertaining. A durable metal roof adds both character and long-term peace of mind. Downstairs, the walk-out basement includes 1,000 square feet of unfinished space ready for your vision, whether it’s a home gym, media room, guest suite, or additional living area. Surrounded by woods, this property offers privacy and serenity, yet remains part of a community with HOA access to a private lake, perfect for fishing and relaxing weekends outdoors. If you’ve been searching for new construction, acreage, and convenience all in one… this is it. See attached notes for Builder Upgrades.
#VAWR2013346

MIDDLETOWN

220 LAKELAND CIRCLE

3 Beds

2 Baths

2,000 Sq.Ft.

$679,000

MLS#: VAWR2013346

Have you been looking for the perfect sophisticated and elegant historic home? Do you want everything; a gracious home, amazing space, acreage, a place for chickens, but also walkable and close to town? It sounds impossible, but you've found it! Welcome to historic Maplewood, circa 1872, know colloquially as The Tower. With no HOA and business B-1 zoning, this property presents endless possibilities, allowing dozens of potential uses! With stunning Italianate architecture and over an acre of land, this property is one in a million. This landmark home located in the heart of lovely downtown Middletown is a piece of history with all the modern conveniences. Rich with history, this amazing property was once the home and studio of John Chumley, a famous local artist. (The current owners have tons of photos and information about the history of the home that they'd love to share with you!) Too many amazing features to list; gorgeous high ceilings, original hardwood floors, wrap around built ins, huge windows, original millwork throughout, a generous kitchen and huge walk in pantry, fabulous mudroom, several outbuildings for storage and work space, an amazing chicken coop; the list goes on and on! Featuring four large bedrooms and two and half bathrooms, this home is spacious, beautiful, and elegant. The panoramic mountain views will take your breath away, especially from the tower studio room. And the home sits on a fantastic level lot behind public memorial land! All of this, located right in the center of town, so shopping and restaurants are just steps away. Middletown is an ideal location for commuters, with Rt 37, I-66 and I-81 within just a few minutes drive, not to mention all the natural beauty, activities, and amenities of the Shenandoah Valley. This is the one!!!
#VAFV2038812

MIDDLETOWN

2239 SIXTH STREET

4 Beds

2 Baths

2,944 Sq.Ft.

$649,900

MLS#: VAFV2038812

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

Prime commercial site. This 1.54-acre property boasts a coveted B-2 zoning, making it an ideal location for business ventures. Conveniently positioned just off Interstate 81 and a short drive from Interstate 66, this site offers excellent visibility, ensuring maximum exposure for any enterprise. Situated between two well-known establishments, McDonald's and Econo Lodge, it benefits from high traffic and customer flow. With public utilities readily available, the infrastructure is in place to support a wide range of commercial activities. Moreover, the surrounding area is experiencing substantial residential growth, indicating a thriving market and potential customer base. This commercial site's strategic location, zoning, excellent visibility, proximity to major highways, and supportive infrastructure make it an enticing prospect for entrepreneurs looking to establish or expand their businesses in a rapidly developing area.
#VAFV2013246

MIDDLETOWN

RELIANCE ROAD

None Beds

None Baths

1.38 acres

$595,000

MLS#: VAFV2013246

Rare opportunity in the heart of Middletown! Discover the perfect blend of small-town charm, open space, and future potential on this beautiful 8-acre property surrounded by scenic pastureland and mountain views. Currently used for cattle and hay production, the land is partially fenced and includes a shed, making it ready for agricultural use or the ideal setting for your own private farmette—bring your animals and start living the country lifestyle. Imagine building your dream home while enjoying the peace and wide-open space this property provides. With town water and sewer hookups available or you could do well & septic - depending on costs . you’ll have the convenience of municipal services while still enjoying the feel of rural living. Zoned RA, the parcel may offer up to three homesites (buyer to verify)—perfect for a family compound, custom home sites, or a long-term investment opportunity. Located just a short walk to historic Main Street, you can easily enjoy local restaurants, shops, and community events. Plus, I-81 is only minutes away, making commuting simple while you return home each day to your peaceful countryside retreat. Opportunities like this are hard to find in Middletown. Schedule your showing today and explore the possibilities this special property offers. Property sold as-is. Buyer to verify subdivision potential, utilities, and zoning. Property is currently in land use; rollback taxes may apply if removed. Livestock on property—showings by appointment with agent accompaniment only. The purchaser could choose to do well & septic instead of hooking up to the public utilities Q: Where is Middletown, Virginia located? A: Middletown is located in the scenic Shenandoah Valley of Virginia, just south of Winchester and minutes from Interstate 81. Q: What makes Middletown a desirable place to live? A: Middletown offers small-town charm, historic character, and beautiful mountain views while still being close to shopping, dining, and commuter routes. Q: What outdoor activities are nearby? A: Residents enjoy easy access to hiking, fishing, and exploring the Shenandoah Valley, as well as nearby parks, rivers, and scenic mountain drives. Q: Is Middletown convenient for commuters? A: Yes. With quick access to I-81 and nearby Route 11, Middletown provides a convenient commute to Winchester and surrounding Shenandoah Valley communities. Q: What is the lifestyle like in Middletown? A: The town is known for its welcoming community, historic Main Street, seasonal events, and peaceful rural surroundings that make it a great place to enjoy the Shenandoah Valley lifestyle.
#VAFV2039608

MIDDLETOWN

VETERANS - LOT 12 ROAD

None Beds

None Baths

8.0 acres

$549,000

MLS#: VAFV2039608

1 2 3

properties found. properties found. Page of .

- property

Send a message

Message successfully sent.

Your message

What is 3 + 4 ?

Reason for contacting?

Sign Out

Virtual Assistant

Would you like to take the next step with this property? We can help you schedule a showing or virtual tour, or send you more details.

Yes, I would like more information.

Thank You for Your Reply, One of Our Agents will contact you as soon as possible

No, maybe later.

Thank you, you can always contact me via email, phone number or through the contact form.

Realhub AI

Lucy - Your AI-Powered Realtor

Update Your Temporary Password

Personalize your search

Enter your email and we'll notify you immediately when new listings match what you're looking for.

or enter email address

Already have an account ? Login here

Continue your home search

Already have an account ? Login here

We use cookies

We use cookies primarily for analytics to enhance your experience. By accepting, you agree to our use of these cookies. You can manage your preferences or learn more about our cookies policy.

Privacy Policy Terms of Service