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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 Middletown, MD real estate 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

238

# of Listings

Avg # of Bedrooms

$269

Avg. $ / Sq.Ft.

$653,613

Med. List Price

Browse MIDDLETOWN Real Estate Listings

$500,000 - $1M

125 Properties Found. Page 2 of 9.

MIDDLETOWN

870 SWEET BIRCH DRIVE

5 Beds

3 Baths

5,100 Sq.Ft.

$799,900

MLS#: DENC2094674

To be built - New Construction! Monarch offers resort-style living featuring high-end finishes and flexible floor plans. At the heart of the community, residents will enjoy an amenity-rich clubhouse complete with a resort-style pool, pickleball and sports courts, and inviting indoor lounge spaces perfect for relaxation or connection. Combining the sophistication of luxury homes with the laid-back charm of Delaware living, Monarch delivers the perfect balance of comfort, style, and convenience—all just minutes from Middletown’s shopping, dining, and entertainment. The Waterford – Two-story home with a first-floor owner’s suite and 3,642+ sq. ft. Includes 4 bedrooms and 3.5 baths. Features an open kitchen with island seating, breakfast nook, spacious great room, and flex room. A first-floor guest bedroom with full bath adds convenience. Upstairs offers 2 bedrooms, a loft, full bath, and unfinished bonus room. Options include additional bedrooms, baths, and outdoor living spaces. Monarch’s HOA fee includes grass cutting on your property, curbside garbage and recycling services, common area maintenance including walking paths, landscaping, streetlights, entrance monuments, and all community amenities.

MIDDLETOWN

2200 EARLY COURT

4 Beds

3 Baths

3,642 Sq.Ft.

$799,900

MLS#: DENC2093610

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

MIDDLETOWN

3213 OLD NATIONAL PIKE

3 Beds

2 Baths

1,782 Sq.Ft.

$799,000

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 or adaptation to a new concept. 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

MIDDLETOWN

OLD NATIONAL

None Beds

None Baths

1,750 Sq.Ft.

$799,000

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.

MIDDLETOWN

0 RELIANCE

None Beds

None Baths

3.84 acres

$799,000

MLS#: VAFV2039508

MIDDLETOWN

1135 MAJESTY LANE

4 Beds

3 Baths

3,500 Sq.Ft.

$784,900

MLS#: DENC2093606

#DENC2086934

MIDDLETOWN

844 MERLIN DRIVE

6 Beds

4 Baths

3,707 Sq.Ft.

$779,900

MLS#: DENC2086934

Welcome to Highlands at Back Creek, a small community of only 42 lots. Most lots back to open space, and they're all at least 3/4 acre. S Homes has always been ahead of its time with stunning, well-designed, large homes. The Brandywine Grand is proof of that. It has 3,700 square feet of living space on the first and second floors (excluding the unfinished basement). The living room and dining room flank the large foyer.
A bay window complements the dining room. Double doors lead to the study, located next to the Family Room. Custom-boxed, trimmed columns are throughout the first floor, adding to the home's ambiance. The large two-story family room features a fireplace and a wall of windows, and it's next to the kitchen, making it perfect for entertaining. In the kitchen is a massive island and a breakfast area with plenty of standard windows for extra light. You can access the second floor by the butterfly staircase. You'll find the laundry room with double doors nd a laundry tub. The hall bath has a double vanity. Two of the secondary bedrooms have double closets. Double doors lead into the Owner's Suite, and what a suite it is! The sitting room is as large as a bedroom! The Owner's bedroom has two large walk-in closets. The Owner's bath has a double vanity with a make-up area, a large shower, and a soaking tub. The basement can be finished to your liking. When looking at this floor plan, note the room sizes. No one else builds a house like this except JS Homes. Looking to make custom changes? No problem. We can do that!
Tired of massive developments with no sense of community? This is the place for you. ;) Check out some of the many standard features- 9' first and second floors, crown molding in the living room, dining room, and foyer. Shaw hardwood flooring in the foyer, kitchen, dining room, and powder room. 6'x6' ceramic tile in the hall and Owner's bath. Gourmet kitchen with granite countertops, stainless steel appliances, double wall oven, microwave, separate cooktop, and dishwasher. Side entry garage with a garage door opener. Energy-efficient HVAC- LENNOX furnace, LENNOX 14 SEER central air conditioning, wifi-thermostat, and Low E Argon windows. Everyone loves an open floor plan, and this house doesn't disappoint. Give Nancy a call- let her help you pick a lot and design your stunning new home. Use 129 Ayshire Dr., Middletown, for GPS. The pictures shown are not of the actual home. Photos are for marketing purposes only and are not of the actual house. County, city, school taxes, assessment value, and square footage are approximate. If you are working with a realtor, the agent's client must acknowledge that a realtor is representing them during their first interaction with JS Homes, and the realtor must accompany their client on the first visit.
If you are working with a realtor, the agent's client must acknowledge that a realtor is representing them during their first interaction with JS Homes, and the realtor must accompany their client on the first visit.

MIDDLETOWN

129 AYSHIRE DRIVE BRANDYWINE GRAND

4 Beds

2 Baths

3,700 Sq.Ft.

$774,990

MLS#: DENC2039486

MIDDLETOWN

1137 MAJESTY LANE

4 Beds

3 Baths

3,383 Sq.Ft.

$774,900

MLS#: DENC2093596

The search is over! You will be amazed from the moment you walk inside. A stunning 2 story 4725 sq foot colonial home PLUS finished basement with 4th full bathroom offers the new buyers a turnkey option on an amazing private lot backing to woods that has been professional landscaped with a low maintenance salt water inground pool! Enter into an open foyer with Cathedral ceilings, catwalk above the open staircase. The Formal living room and dining room will also greet you in the entry while the gourmet kitchen enhanced with marble, granite and tea stain mocha glazed maple cabinets, stainless steel appliance and breakfast room is a chef dream. Exit off the kitchen pass the Triple French doors open to the large deck with a pergola that overlook the low maintenance salt water in ground pool great for outdoor entertaining. The rest of the yard backs to a wooded area for extra privacy. Come back inside and relax in the sunken family room with a gas fireplace. Office/study/den, laundry room with built ins round out the main floor. Upstairs you will find a magnificent owner suite with a sitting room, (2) walk in closets and a custom (4) piece bathroom with a jetted tub, open shower, double vanities and water closet is an owner respite. Preferred Princess suite with private bathroom and Jack and Jill bedrooms with their own bathroom round up the upstairs. This home also has back staircase that leads to family room, finished basement with a full bathroom and (2) storage rooms. This home has it all with room to spread out and then some. This home is also in the desirable Appoquinimink School District. Don't miss out and don't wait too long. Schedule a showing today.
This home is being sold as-is.

MIDDLETOWN

624 NESTING LANE

4 Beds

4 Baths

4,725 Sq.Ft.

$770,000

MLS#: DENC2094112

New on site 2 days ago

About to break ground on this beautiful Houston spec home. Anticipated delivery is around July of 2026. Benchmark Builders has rentals townhomes available if you need a place in the interim. We have planned for this home to have a 1st floor bedroom with private full bath, an added powder room on the 1st floor, 2nd floor laundry, 2nd floor primary bedroom with 3 other secondary bedroom, morning room with extended kitchen layout, and 9' basement walls with a rough in for a future full bath. Talk to the site manager for full details and to schedule a tour of a similar home. There is still time to personalize finishes.

MIDDLETOWN

617 MCCRACKEN DRIVE

5 Beds

3 Baths

3,560 Sq.Ft.

$769,999

MLS#: DENC2097222

Welcome to Highlands at Back Creek- a small community of only 42 lots. Most lots back to open space, and they're all a minimum of 3/4 acre. Tired of massive developments with no sense of a community? This is the place for you;) One of the front doors leads to a 2-story foyer, and the other brings you into the mudroom. The mudroom, located off the garage, is a perfect place to add additional built-ins for coats, shoes, book bags, etc. The living room is at the front of the house, which could be used as a library, office, or playroom. The kitchen has an island, plenty of cabinets, and a flex area that could be a massive walk-in pantry. Everyone loves an open floor plan, and this house doesn't disappoint. The family room is next to the kitchen with a beautiful fireplace, mantel, and marble surround. On the second floor are three nice-sized secondary bedrooms and a laundry room with a handy laundry tub. The Owner's suite ( 15'x20') has 2 WALK-IN closets, and the Owner's bath has a double vanity and a large shower. Check out some of the standard features- 9' first and second floors and crown molding in the living room, dining room, and foyer. Shaw hardwood flooring in the foyer, kitchen, dining room, and powder room. 6'x6' ceramic tile in the hall and owner's bath. Gourmet kitchen with granite countertops, stainless steel appliances, double wall oven, microwave, separate cooktop, and dishwasher. Side entry garage with a garage door opener.
Energy-efficient HVAC- LENNOX furnace, LENNOX 14 SEER central air conditioning, wifi-thermostat, and Low-E Argon windows. The SOMERSET has a well-designed floor plan. This is a to-be-built home. Visit the model for information -129 Ayshire Dr. The photos are of a similar home and are for marketing purposes only. THIS IS A TO-BE-BUILT HOME. County, city, and school taxes, assessment value, and square footage are approximate. If you are working with a realtor, the agent's client must acknowledge that a realtor is representing them during their first interaction with JS Homes, and the realtor must accompany their client on the first visit.

MIDDLETOWN

129 AYSHIRE DRIVE SOMERSET FLOORPLAN

4 Beds

2 Baths

3,116 Sq.Ft.

$769,990

MLS#: DENC495462

MIDDLETOWN

1036 APPLECROSS DRIVE

5 Beds

4 Baths

5,400 Sq.Ft.

$765,000

MLS#: DENC2096686

MIDDLETOWN

1139 MAJESTY LANE

4 Beds

2 Baths

3,018 Sq.Ft.

$764,900

MLS#: DENC2093550

Absolutely stunning home in The Estates at St Annes! Built in 2020 this home backs up to the golf course with breathtaking views of the fairways, tees and ponds. The exterior features a covered front porch perfect for enjoying your favorite book or beverage, an architectural roof shingle, stone water table, beaded vinyl siding and a soded yard with lawn irrigation. As you enter through the front door you are welcomed by a voluminous 2 story foyer with sprawling hand scrapped hardwood engineered flooring, private study/office to the left, living room to the right, and a hardwood staircase with iron balusters leading to the upper level. The main floor features a gourmet kitchen with custom slate flooring, extended island, exceptional counter surface, tile backsplash, and 42-inch cabinets with crown, stainless steel appliances including cooktop range, double wall over, microwave, refrigerator and dishwasher. The dining room with bay window is just off the kitchen, the expanded family room offers tremendous space, vaulted ceiling, transom windows, motorized blinds and gas fireplace. The morning room offers an abundance of windows with motorized blinds, provides the extra space near the kitchen perfect for entertaining guests and offers access to the rear deck and patio. The upper floor offers 4 bedrooms, and 2 baths features a private owner’s bedroom with trey ceiling, retreat/sitting room and a luxury bath with tile flooring, soaking tub, tiled stall shower and 2 separate vanities. The lower level is finished with a legit tiki bar, billiard room, recreation room and a full bathroom offers convenient access to the rear yard via the double English well exit stairs. The rear yard is fenced and offers an expansive paver patio with a fire pit, area for hot tub and golf cart parking and a large low maintenance deck, all perfect for outdoor barbeques or spectacular sunset happy hours! Community amenities include walking trails, gazebo, park with playground, sand volleyball court, basketball court and wall ball. There is also an 18-hole golf course with clubhouse featuring, Lore Woodfyre and Highlands Whiskey Bar. The St Annes Club Pool offers memberships for your enjoyment as well. Superbly maintained and move-in ready!

MIDDLETOWN

205 CLYDIA COURT

4 Beds

3 Baths

4,175 Sq.Ft.

$764,500

MLS#: DENC2095328

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properties found. properties found. Page of .

MIDDLETOWN

MIDDLETOWN

Why Choose Middletown, MD?

Middletown, MD Housing Market Overview

Live in the Heart of Frederick County

Ready to Find Your Dream Home in Middletown?

Browse MIDDLETOWN Real Estate Listings

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