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

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
108
# of Listings
3
Avg # of Bedrooms
$329
Avg. $ / Sq.Ft.
$549,088
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

298 Properties Found. Page 4 of 20.

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.
#DENC495462

MIDDLETOWN

129 AYSHIRE DRIVE SOMERSET FLOORPLAN

4 Beds

2 Baths

3,116 Sq.Ft.

$769,990

MLS#: DENC495462

This is a builder model home sale. This ever-popular Duke floorplan with it's stunning 2-story family room offers 2,795 square feet of living space. The finished basement adds another 456 square feet, as well as a full bath. Hardwood flooring runs throughout the first floor, the upstairs hall, the primary bedroom and the basement recreation room. The kitchen offers quartz countertops, an oversized island, tiled backsplash, and a huge walk-in pantry. Upstairs you'll find quartz vanity tops and tiled flooring in both bathrooms and a luxurious spa shower in the primary bathroom.
#DENC2088814

MIDDLETOWN

5607 S BAYBERRY PKY

4 Beds

3 Baths

3,251 Sq.Ft.

$765,300

MLS#: DENC2088814

Proposed new build. LAST LOT AVAILABLE in the sought after Rothwell Estates community by Benchmark Builders. This lot backs to trees and faces West. The price includes the lot, a set of standard features, and optional items that have been the most popular for our customers. We can customize and change the options to fit your needs and budget. The Houston floor plan has been our most popular and is the same as the model home on Green Forest Dr. The 2 story foyer & great room, & catwalk gives this home the WOW FACTOR you have been looking for. This proposed home has the optional morning room & 1st floor in-law suit complete with full bath. It is planned to have the Craftsman elevation with brick water table, but there is time to change what you wish. Make an appointment with the site sales manager to talk over all the details and tour the model. Pictures are of similar homes we have done. The Benchmark Builders website has more information like the site map, standard features, and virtual tours.
#DENC2092292

MIDDLETOWN

619 MCCRACKEN DRIVE

5 Beds

3 Baths

3,560 Sq.Ft.

$764,999

MLS#: DENC2092292

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

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.
#DENC2090446

MIDDLETOWN

911 CADMAN DRIVE

4 Beds

4 Baths

4,450 Sq.Ft.

$750,000

MLS#: DENC2090446

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

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.
#DENC2093610

MIDDLETOWN

2200 EARLY COURT

4 Beds

3 Baths

3,642 Sq.Ft.

$744,900

MLS#: DENC2093610

Rothwell Estates from Benchmark Builders. 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
#DENC2079896

MIDDLETOWN

126 GREEN FOREST DRIVE 6 COCHRAN

4 Beds

2 Baths

3,700 Sq.Ft.

$740,000

MLS#: DENC2079896

Don’t miss this opportunity to own a brand-new custom home on a 1-acre established neighborhood in Middletown, (you will not have to live through construction surrounding your home!) Offering 3,428 sq. ft. of thoughtfully designed living space. This home blends luxury, functionality, and space for the modern lifestyle. Enter through the double front doors into an impressive two-story foyer, & stained oak stairs that sets the tone for the rest of the home. To the right, a formal dining room provides ample space for large gatherings and includes a butler’s pantry for added convenience. The main living area features a bright and open-concept kitchen and family room, complete with a propane fireplace and picturesque views of the surrounding land. The kitchen boasts a hidden walk-in pantry designed to impress and accommodate all your storage needs. Granite countertops, stainless steel appliances and a gorgeous island make this kitchen perfect. A first-floor bedroom or home office with a full bath adds flexibility for guests or remote work. Upstairs, the primary suite is a true retreat with a spacious layout, stand-up shower, soaking tub, double bowl vanity, and an 8’ x 8’ walk-in closet. Two additional generously sized bedrooms (with walk in closets), and a full hall bath complete the second level. The finished basement includes a half bath, walk-out access, and the option to customize a large family or recreation room while still offering ample storage space. Propane gas and a 2 zone heating/Cooling system make for a comfortable home. A rear-facing 2-car garage adds both privacy and curb appeal. Located only 6 minutes from the St Georges Bridge gives you the luxury to take RT 1 wherever you need to go. This home combines high-end features with peaceful surroundings—perfect for those looking for new construction with room to grow.
#DENC2089908

MIDDLETOWN

704 BULLEN

4 Beds

3 Baths

3,428 Sq.Ft.

$739,900

MLS#: DENC2089908

Gorgeous Lot -Backs to open space! Great opportunity to buy at the new 55+ Parks Edge at Bayberry- The Tracy II Quick Delivery! Come experience the active adult lifestyle that home owners are raving about: a vibrant social scene, luxury amenities, stunning outdoor spaces and a place that will make you feel welcome and at home form the day you move in. Enjoy maintenance-free living with grass cutting and snow plowing taken care of, so you can enjoy events and activities at your luxury clubhouse with resort-style pool overlooking a pond, fitness center, games/billiards room, Tennis/pickleball court and more. Open House Saturday & Sunday 11am-4pm
#DENC2086766

MIDDLETOWN

3227 S CENTRAL PARK DRIVE

3 Beds

2 Baths

2,757 Sq.Ft.

$734,500

MLS#: DENC2086766

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 Bridgeport is a two-story home starting at 3,500 sq. ft., featuring a first-floor secondary owner’s suite, 4 bedrooms, and 3.5 baths. Open kitchen with island, breakfast nook, walk-in pantry, and flex room. Upstairs includes the Owner’s suite, 2 bedrooms, loft, 2 baths, and laundry. Optional layouts available for additional bedrooms, baths, and outdoor living.
#DENC2093606

MIDDLETOWN

1135 MAJESTY LANE

4 Beds

3 Baths

3,500 Sq.Ft.

$729,900

MLS#: DENC2093606

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!
#DENC2062974

MIDDLETOWN

1481 BUNKER HILL ROAD

None Beds

None Baths

3.85 acres

$725,000

MLS#: DENC2062974

Stunning 4BR/3.5BA Duncaneshire Colonial Model by L.C. Homes in the sought-after Estates at St. Anne’s! Located in the Appoquinimink School District, this spacious home offers over 4,475 sq. ft. of living space on a premium .51-acre corner lot with a two-car side-entry garage. Enter the home through the grand two-story foyer featuring hardwood floors and a beautiful turned staircase. The formal living room offers an eye-catching bay window and crown molding, while the formal dining room features crown molding and an open box bay window. French doors off the foyer lead to a private home office or guest room. The two-story family room with a double-sided gas fireplace opens to the eat-in kitchen, complete with a spacious island, recessed lighting, and a walk-in pantry. A bonus sunroom/solarium provides flexible use as a playroom, gym, or game room and opens directly to the backyard. A powder room and convenient first-floor laundry complete the main level. The full unfinished basement is framed for a workshop and includes plumbing rough-in for a fourth full bathroom, offering endless customization potential total below grade 2,304 sq.ft. Upstairs, a loft overlooks the family room below. The expansive primary suite features two walk-in closets, a sitting area, and a luxurious 5-piece bath with dual vanities, large soaking tub, walk-in shower, private water closet, and space ideal for lounging, reading, quiet work, or workouts. Three additional bedrooms, including one with its own private full bath, plus a full hall bath complete the upper level. The Estates at St. Anne’s offers resort-style amenities, including walking trails, playgrounds, basketball and volleyball courts, a gazebo, community pool, clubhouse, banquet facilities, and a semi-private 18-hole links-style golf course with Highlands Whiskey Bar and Lore Modern Woodfyre restaurant. Conveniently located minutes from tax-free shopping, recreation, dining, and major highways. Walking distance to MOT Charter and just minutes from Routes 1, 13, and 301 for easy access to beaches and the city.
#DENC2092878

MIDDLETOWN

14 HAGGIS ROAD

4 Beds

3 Baths

4,475 Sq.Ft.

$725,000

MLS#: DENC2092878

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.

$725,000

MLS#: MDFR2072474

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 Chesapeake, a two-story home with a first-floor owner’s suite and 3,383+ sq. ft. Includes 4 bedrooms, 3 baths, flex room, and loft. The first floor features a spacious kitchen open to the dining area and two-story great room, owner’s suite, additional bedroom, and flex room/office. Upstairs offers 2 bedrooms, loft, full bath, and unfinished bonus room. Options include extra bedrooms/baths and outdoor living spaces such as a courtyard or screened porch.
#DENC2093596

MIDDLETOWN

1137 MAJESTY LANE

4 Beds

3 Baths

3,383 Sq.Ft.

$719,900

MLS#: DENC2093596

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