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
254
# of Listings
3
Avg # of Bedrooms
$268
Avg. $ / Sq.Ft.
$654,976
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

133 Properties Found. Page 3 of 9.

Absolutely stunning 4 bedroom, 4 1/2 bath colonial with a 3 car garage, finished basement all on 1.42 acres. Lovingly maintained and appropriately updated including the roof(2020), siding, most windows, HVAC(2025) and water heater(2019). The main floor offers a 2 story foyer; formal living room with crown molding; large dining room with crown molding and wainscoting; office/study with built-in cabinets and shelving, crown molding and recessed lighting; family room with built-in entertainment center and recessed lighting; kitchen with 42 inch raised panel cabinets with crown, center island, pendant lighting, recessed lighting, gas stove and newly installed luxury vinyl flooring; large morning room with gas fireplace featuring marble surround and decorative mantle and crown molding; convenient first floor laundry and mud room; and a powder room. The upper level features a owners suite with a luxury bath with 2 vanities and over sized tiled shower with frame less glass walls and walk in closet with custom organizers; a princess suite and 2 additional bedrooms with a shared full bathroom. The basement is finished with a recreation room, hobby/exercise room, kitchen and a den perfect for entertaining and offers a full bathroom and egress stairs to the back yard. Other exceptional features include sprawling hardwood flooring, spindle staircase, extensive crown moldings, exterior lighting, lawn irrigation, alarm system and recently sealed driveway. An exceptional home ready for you to move right in!
#DENC2097266

MIDDLETOWN

93 W DELAWARE CANAL COURT

4 Beds

4 Baths

5,390 Sq.Ft.

$765,000

MLS#: DENC2097266

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 Brady – Two-story home with 3,018+ sq. ft., 4 bedrooms, and 2.5 baths. Features an open kitchen with island seating, breakfast nook, flex room, and walk-in pantry. Upstairs offers an owner’s suite, three bedrooms, loft, two full baths, laundry room, 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.
#DENC2093550

MIDDLETOWN

1139 MAJESTY LANE

4 Beds

2 Baths

3,018 Sq.Ft.

$764,900

MLS#: DENC2093550

Welcome to the 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 community? This is the place for you. ;) Check out some of the standard features- 9' first and second-floor ceilings, 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 Hancock Grand is one of our most popular floorplans, and it's easy to see why. The sizeable two-story foyer has a unique turned staircase. The study, with a boxed bay window, is located at the front of the house. On the other side of the staircase is the living room that adjoins the dining room. If you like to entertain, this kitchen is for you! There's a walk-in pantry and an expanded island with an overhang for additional seating. The family room has a fireplace and a rear staircase. On the second floor are three nicely sized secondary bedrooms and a laundry room with a utility sink. The hall bath has a double vanity and a full-sized window. Double doors lead to the Owner's Suite. Bight and sunny with a triple-boxed bay window and a double window in the dressing area, this is a beautiful place to escape. The dressing area has a large mirror and a dressing table with two huge walk-in closets. A full basement can be finished during construction or after settlement. 3,260 square feet of living space on the first and second floors. This and a LONG list of standard features make this home your best choice. Use 129 Ayshire Dr for GPS. Visit the Philadelphian Grand model for information about the Hancock Grand—showings are by appointment only. The pictures shown are for marketing purposes only and are not of the actual house. THIS IS A TO-BE-BUILT HOME. County, city, and school taxes, assessments, 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.
#DENC2039458

MIDDLETOWN

129 AYSHIRE DRIVE HANCOCK GRAND

4 Beds

2 Baths

3,260 Sq.Ft.

$758,990

MLS#: DENC2039458

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 Shearwater – A two-story home with a first-floor owner’s suite and 3,020+ sq. ft. Features 3 bedrooms, 2.5 baths, and a flex room. The open layout offers a spacious kitchen, great room, and dining area. Upstairs includes a loft, two bedrooms, full bath, and unfinished bonus room. Personalize with optional extra bedrooms, baths, or outdoor living spaces like a courtyard or screened porch. 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.
#DENC2093592

MIDDLETOWN

1141 MAJESTY LANE

3 Beds

2 Baths

3,020 Sq.Ft.

$754,900

MLS#: DENC2093592

Last of the remaining lots!!!!! Unique and promising opportunity close to the Maryland Horse Farms, perfect for those seeking a picturesque and serene waterfront property to call home Lots #12 and #13 Great Bohemia Manor. Build your dream home today! No Builder Tie In. Lakefront property cleared flat land awaiting the perfect buyer, a total of 5 acres for both lots combined but lots can be purchased separately. Lot #12 - 221 ft. water frontage. The waterfront lot goes to the center of Great Bohemia Mill Pond. Lot #13 has a (5) ft. wide easement across Lot #12 to have water access. Enjoy boating and other water-related activities in the Great Bohemia Mill Pond which is over a mile long and stocked with many fish specifically wide-mouth bass. Both lots are close to the Bohemia River which is on the other side of Old Telegraph Rd. No Impact fee required, and property is perc approved. Lot #12 on water is 3 ¾ acres. Lot #13 with water access is 1 ¼ acres. Build your perfect home in APPOQUINIMINK SCHOOL DISTRICT. Contact listing agent for any questions! Schedule a showing today!
#DENC2095394

MIDDLETOWN

1481 BUNKER HILL ROAD

None Beds

None Baths

3.85 acres

$750,000

MLS#: DENC2095394

Home is back on market at NO FAULT to seller - the buyers financing fell apart. You don't get many second chances in life, so this is it - their loss can be your win! Your Dream Home Awaits! This stunning six-bedroom showcase beauty—including two with private ensuite baths—offers all the space, comfort, and elegance you’ve been searching for in your new home, with over 3,800sf plus an additional 1,100sf of grand living space in the private finished basement. There’s room for everyone in this beautiful home - especially if you're looking for multi-generational living - located in Shannon Cove, which has long been a sought-after neighborhood in the Appo School District, with it's miles of tree-lined, wide paved streets with sidewalks, grand entrance and a large in-ground community pool with tot lot and a baby pool. Situated on a serene lot next to bonus open space, this home delivers peaceful views from nearly every window. Whether you’re sipping your morning coffee in the primary suite’s sitting area, cozying up by the gas fireplace, or unwinding on the vaulted screened porch that flows onto an airy deck, every day here feels special. Step inside to a grand two-story foyer framed by gleaming hardwoods, crown molding, and a gracious formal dining room just perfect for hosting holidays or quiet evenings in. The impressive family room with a tray ceiling, built-ins book shelves, and a gas fireplace is an ideal backdrop for movie nights and gatherings. And it opens to the gourmet kitchen with large eat-in area so everyone can be part of the fun and enjoy the glow of the fireplace. Love to cook? You’ll fall in love with the gourmet kitchen featuring top-tier stainless appliances, upgraded cabinetry with molding and end panels, butlers pantry, granite countertops, double wall oven, an oversized island with gas range, and bright lighting throughout. The open floor plan keeps everyone connected, and just off the kitchen sits the first-floor in-law suite, complete with ensuite bath and peaceful backyard views. Up the turn staircase, you’ll find five spacious bedrooms, each with generous closets and ceiling fans. The primary suite is a true retreat with its vaulted ceiling, expansive sitting area, and spa-like bath with soaking tub and separate shower. And the surprises don’t stop there—head downstairs to a huge finished basement with laminate flooring, a workshop area, abundant storage, and a long counter space perfect for hobbies, crafts, or entertaining. A set of French doors leads you to a charming brick walkway surrounded by lush landscaping—your private garden oasis. This basement has full light and a separate entrance! Could easily be transformed into another in-law suite or whatever your heart desires. Beautiful, spacious, and filled with thoughtful upgrades, this home checks every box. Nothing was overlooked when designing each corner and cubby and its excellent condition is a testament to how meticulously this home was cared for and loved. Come see how perfect life can be! Floor plan is included in the photos.
#DENC2088978

MIDDLETOWN

530 MAIDEN COURT

6 Beds

3 Baths

3,950 Sq.Ft.

$750,000

MLS#: DENC2088978

Its a new year and your new home awaits you!!! Welcome to this stunning, nearly new home located in the highly desirable Preserves of Deep Creek community in Middletown, Delaware. Built just three years ago, this beautifully maintained property offers 4550 sq ft of thoughtfully designed living space with 4 bedrooms, 4.5 bathrooms, and a finished basement complete with a full bath—ideal for entertaining, guests, or a recreation space. Key Features: Open-concept main level with abundant natural light and neutral decor throughout Gourmet kitchen with large center island, walk-in pantry, and seamless flow to dining and living areas Cozy living room fireplace perfect for cooler evenings Dedicated home office—ideal for remote work or a quiet study space Second-floor loft area for added flexibility—media room, play area, or second office Convenient second-floor laundry room Step outside to a beautifully designed patio featuring a built-in fire pit and permanent seating, creating a perfect space for relaxing or entertaining under the stars. Community Amenities: HOA includes lawn care for low-maintenance living Outdoor pool with splash pad, basketball courts, clubhouse with a fitness center, playground, and more Enjoy being just minutes from golf courses, county parks, and Middletown’s expanding shopping and dining scene. Plus, just minutes from your front door is easy access to the 301 bypass. If you desire to spend time at the beaches you're only a short, convenient drive to the Delaware shore, making for doable day trips.
#DENC2095778

MIDDLETOWN

911 CADMAN DRIVE

4 Beds

4 Baths

4,450 Sq.Ft.

$750,000

MLS#: DENC2095778

New on site 4 days ago
Semi-Custom Builder, so talk to the sales manager for additional design options. Last lot left in Rothwell Estates from Benchmark Builders. All 6 of our floor plans fit. We have a 7 month build time and rentals available for our buyers if you need a place to stay during the build. See the sales manager, Lindsay, for all the details. The COCHRAN (to be built) is the largest of out floor plans. The large kitchen, 2 story great room, & 2 stair cases are some of the stand out features in this home. We encourage you to take the virtual tour to see this floor plan. Rothwell Estates is endowed with a rich variety of two-story and ranch models, which include basements and an abundance of standard features such as a stone water table, hardwood standard in the foyer, kitchen and breakfast area,& powder room. Granite counter tops in the kitchen, stainless steel appliances, an island, 42" maple cabinets, gas fireplace, recessed lights, tile baths, fully sodded yard and much, much more! With an emphasis on open and versatile floor plans, you are certain to find the home of your dreams. Residences are situated on perfectly sized home sites, most of which back up to open space. And, you'll love the comfort and peace of mind these energy-efficient homes provide. Located in the highly regarded Appoquinimink School District, families will find much to appreciate. Whether you're looking for a home that offers first-floor living or a grand two-story design, Rothwell Estates has something for everyone! Please visit the model home at 126 Green Forest Drive, Middletown, DE 19709. Agent must accompany buyer on first visit or pre-register prior to first visit on builder website
#DENC2097536

MIDDLETOWN

619 MCCRACKEN DRIVE 6 COCHRAN

4 Beds

2 Baths

3,700 Sq.Ft.

$740,000

MLS#: DENC2097536

Welcome to 234 Baldy Ln - the epitome of the term "dream home" combined with luxury, low-maintenance living in the sought-after 55+ community of Traditions at Whitehall in Middletown. Here, you'll find resort-style amenities that meet a beautifully upgraded, move-in-ready home. Enjoy an active lifestyle with the community clubhouse and fitness center, sparkling pool, plus pickleball, bocce ball, and shuffleboard—along with close proximity to area trails, parks, shopping, and everyday conveniences. From the moment you arrive, this home makes a statement with a two-car garage, charming stone skirting, and a welcoming front porch. Out back, unwind on the expansive Trex deck overlooking a private tree-lined yard with garden boxes, the perfect view for morning coffee, weekend entertaining, or a little homegrown harvest. Inside, every detail feels elevated: luxury vinyl plank flooring, custom woodworking, tall ceilings, and a gracious foyer complemented by custom shutters throughout. The spacious family room centers around a natural gas fireplace, accented with board and batten trim and flows seamlessly into an entertainer’s dream setup—an added dry bar with built-in beverage fridge and vintage glass cabinet doors. The adjacent dining area shines with custom built-in china cabinetry and lighting, and opens to a bright, beautiful kitchen featuring a Nancy Meyers-inspired pot rack, striking two-tone cabinetry, granite counters, and a classic tile backsplash. The sunroom extension provides access to the incredible rear deck and yard. The layout offers three bedrooms including a serene primary suite with tray ceiling and a spa-style primary bath with walk-in closet. A full hall bath stands out with a stunning, custom painted mural. Downstairs, the finished basement expands your living options with multiple functional spaces and incredible modern "open" ceiling feature adding to the luxurious feel. The additional square footage adds a workout area, additional living space with custom built-ins, and a full bathroom, plus an additional workshop, perfect for woodworking, tinkering, or hobbies, and a generous storage space. Why wait on new construction when you can have the finished product, already upgraded, thoughtfully customized, and ready to enjoy now—within a community designed for connection, comfort, and active adult living. Don't miss the opportunity to view this beautiful one of a kind property - it won't last long.
#DENC2096354

MIDDLETOWN

234 BALDY LANE

3 Beds

3 Baths

2,725 Sq.Ft.

$735,000

MLS#: DENC2096354

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 Jameson, a two-story home with a first-floor owner’s suite and 2,568+ sq. ft. Includes 3 bedrooms and 2.5 baths. Features a tandem 3-car garage, open kitchen with island seating, breakfast nook, spacious great room, flex room, and walk-in pantry. Upstairs offers 2 bedrooms, loft, full bath, and two unfinished bonus rooms. Options include additional bedrooms, baths, a second owner’s suite, 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.
#DENC2093484

MIDDLETOWN

1143 MAJESTY LANE

3 Beds

2 Baths

2,705 Sq.Ft.

$734,900

MLS#: DENC2093484

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 Kingfisher, a two-story home with a first-floor owner’s suite and 2,566+ sq. ft. Includes 3 bedrooms and 2.5 baths. Features an open kitchen with island seating, breakfast nook, spacious great room, and flex room. Upstairs offers 2 bedrooms, a loft, full bath, and unfinished bonus room. Options include additional bedrooms, baths, and outdoor living spaces. Schedule your appointment today for details and incentives. 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.
#DENC2093362

MIDDLETOWN

1145 MAJESTY LANE

3 Beds

2 Baths

2,566 Sq.Ft.

$724,900

MLS#: DENC2093362

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 Cassidy is a ranch home starting at 2,528 sq. ft., featuring 4 bedrooms, 3.5 baths, and an unfinished bonus room. Open kitchen with walk-in pantry flows to great room and dining. Options available for extra bedrooms, baths, and outdoor living. 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.
#DENC2093486

MIDDLETOWN

2205 EARLY COURT

4 Beds

3 Baths

2,528 Sq.Ft.

$714,900

MLS#: DENC2093486

Build Your Dream Home in Middletown with Schaeffer Homes! Home is to be built. Photos and virtual tours show the same base model with optional upgrades. Discover our most quintessential rancher with the Weatherby! This generously-sized home starts at 2,498 square feet of living space. The Weatherby includes 3 bedrooms, 2 ½ bathrooms, 2-car garage, as well as a study! With one of our most sizable footprints, this remarkable abode gives plenty of room to spread out in this one-story home. This model also includes the option to upgrade to a larger front porch, perfect for relaxing out front with a warm cup of coffee. The Weatherby is ideal for those seeking ample space to expand and live comfortably. Pricing Overview Land Asking Price: $230,000 Home (The Ravello): $355,900 Estimated land development: $120,000* *Land development costs may be higher or lower. Seller and Builder make no representation of feasibility or final costs. The buyer should request a due diligence period to investigate. Schaeffer Homes will assist you throughout the due diligence process. Additional Details: It is unknown whether a basement foundation can be built on this property at this time. Other Schaeffer floorplans are available to be built here. Note: Home is to be built. Photos and virtual tours show the same base model with optional upgrades.
#DENC2089760

MIDDLETOWN

1487 BUNKER HILL ROAD

3 Beds

2 Baths

2,498 Sq.Ft.

$705,900

MLS#: DENC2089760

Step into modern comfort in this beautifully renovated Colonial-style home in sought-after Valley Overlook in Frederick. Offering 4 bedrooms, 3 full baths, and 1 half bath, this spacious residence blends classic charm with fresh, contemporary updates throughout. The main level welcomes you with a bright, open layout featuring a fresh kitchen, inviting living and dining spaces, and a convenient half bath. Upstairs, you’ll find a serene primary suite with en-suite bath. Three more generous bedrooms and a hall bath complete the upper level. The fully finished lower level adds even more versatility with a large recreation space, full bath, and walk-up access to the backyard—perfect for guests, hobbies, or movie nights. Located in a well-established community close to parks, shopping, dining, and commuter routes, this home offers the best of Frederick living with nothing left to do but move in and enjoy!
#MDFR2072474

MIDDLETOWN

2431 QUEBEC SCHOOL ROAD

4 Beds

3 Baths

2,917 Sq.Ft.

$699,999

MLS#: MDFR2072474

The Carver offers a thoughtfully designed open floorplan with classic design touches, with a projected settlement of June 2026. This spacious home includes 3 bedrooms and 3.5 baths, featuring a finished basement complete with a private bedroom and full bath—perfect for guests, extended family, or a flexible retreat. A shiplap-accented fireplace anchors the main living space, while feature walls in the foyer and primary bedroom add character and charm. The screened porch overlooks community open space, and the large homesite tucked at the end of a cul-de-sac provides added privacy and curb appeal. The kitchen shines with a smart appliance upgrade, quartz countertops, and flows seamlessly into the main living areas finished with laminate flooring throughout the first floor. The primary bath is a relaxing escape with a tiled shower enclosure and rain shower head. A 2.5-car garage offers extra room for storage or hobbies. For a full list of features for this home, please contact our sales representatives. Photos are for illustrative purposes only and may not represent the exact home or finishes available.
#DENC2096346

MIDDLETOWN

1525 LESTERFIELD WAY

3 Beds

3 Baths

2,493 Sq.Ft.

$699,990

MLS#: DENC2096346

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