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 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
227
# of Listings
3
Avg # of Bedrooms
$271
Avg. $ / Sq.Ft.
$659,066
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

227 Properties Found. Page 4 of 16.

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.
#DENC2093550

MIDDLETOWN

1139 MAJESTY LANE

4 Beds

2 Baths

3,018 Sq.Ft.

$759,900

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

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

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

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

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.
#DENC2093592

MIDDLETOWN

1141 MAJESTY LANE

3 Beds

2 Baths

3,020 Sq.Ft.

$749,900

MLS#: DENC2093592

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

New on site 4 days ago
Welcome to 29 W. Kilts Ln, an exceptional residence offering 5,950 square feet of finished living space designed for both everyday comfort and elevated entertaining. This stunning home features two staircases, 4 spacious bedrooms, and 4.5 bathrooms, with hardwood flooring throughout the main level and upstairs hallway. The heart of the home is the dramatic sunken family room with soaring 10’ ceilings, shiplap accents, coffered ceiling, and a cozy gas fireplace, seamlessly flowing into a huge sunroom off the kitchen filled with natural light. Upstairs, the expansive primary suite boasts two walk-in closets and a spa-like en suite bath with a soaking tub. Bedrooms two and three share a Jack-and-Jill bathroom, while bedroom four enjoys its own private en suite bath, ideal for guests or multigenerational living. The professionally finished lower level offers over 1,000 square feet of purpose-built entertainment space, designed as a high-end sports bar and media retreat. Featuring seven pre-wired TV locations with matrix control, multiple audio zones including outdoor sound, and a fully equipped custom bar with kegerators, refrigerators, ice machine, wine fridge, and dishwasher, this space is ideal for hosting and everyday enjoyment. Built with 27 dedicated 20-amp circuits, heavy-duty electrical capacity, and acoustical ceiling insulation, the basement also includes an arcade-style gaming area and delivers a true, resort-level entertainment experience rarely found in residential homes. There is also a full bathroom and a full 6’ staircase with walk-out access to the backyard. Out back, enjoy a fully fenced yard with a paver patio, perfect for outdoor gatherings. This home delivers space, style, and functionality in every detail—an impressive offering within the Town of Middletown.
#DENC2096132

MIDDLETOWN

29 W KILTS LANE

4 Beds

4 Baths

5,950 Sq.Ft.

$735,000

MLS#: DENC2096132

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.
#DENC2093484

MIDDLETOWN

1143 MAJESTY LANE

3 Beds

2 Baths

2,705 Sq.Ft.

$729,900

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.
#DENC2093362

MIDDLETOWN

1145 MAJESTY LANE

3 Beds

2 Baths

2,566 Sq.Ft.

$719,900

MLS#: DENC2093362

The Omaha home offers a spacious open-concept layout infused with farmhouse-inspired design and is projected to settle in April, making it an ideal option for buyers planning ahead. With 5 bedrooms, 4.5 baths, and a 2-car garage, this home is thoughtfully designed to accommodate both everyday living and entertaining. Notable features include a private home office, a striking stone fireplace, soaring ceilings, and a screened-in deck that extends your living space outdoors. These design elements create a warm yet elevated atmosphere throughout the home. The farmhouse-style kitchen serves as the heart of the home, featuring gas cooking, dual ovens, and elegant Quartz Calacatta Abezzo countertops—perfect for hosting or daily meal prep with style. Flooring selections are both practical and polished, with laminate throughout the first floor (excluding the home office), carpet in the home office and upstairs living areas, and tile in all full baths. The owner’s bath offers a true retreat, highlighted by a freestanding tub for a spa-like experience. 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.
#DENC2095366

MIDDLETOWN

847 MERLIN DRIVE

4 Beds

3 Baths

2,772 Sq.Ft.

$709,900

MLS#: DENC2095366

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.
#DENC2093486

MIDDLETOWN

2205 EARLY COURT

4 Beds

3 Baths

2,528 Sq.Ft.

$709,900

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

Welcome home Joanna Gaines! YOU will love this 5 bedroom, over an acre of land and NO HOA farmhouse....in the middle of it all. I know that was a lot in the opening sentence so, shocker, there's more. An in ground pool. I know. It's all true and I had to wake you up! This beauty is the real deal, old meets new and affordable enough for you, BOO. Warning....I will rhyme more. In ground pool and you can walk to school. Don't be a fool and overlook this one. You can even bring your mule. Well, ok, you can't but it works so well on an acre plus of land. Just bring your dogs, kids and friends. Don't forget to invite me, I make killer deviled eggs. This home has survived world wars and it will probably outlast you too. It's big, has class and sass. Here I go again! That was all for the rhyming. I will dial it back. Renovations are abundant and beautiful, just like your Mom. New roof and windows circa 2022. Detached garage, fenced in yard and charm. Not Lucky charms, just pure charm and beauty. Original woodwork and trim. Also, pocket doors. Pocket doors should truly be in every home. They are so cool and efficient. A one of a kind original on Main Street; the GREAT street.
#MDFR2075782

MIDDLETOWN

706 E MAIN STREET

5 Beds

3 Baths

2,202 Sq.Ft.

$699,999

MLS#: MDFR2075782

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.

$699,999

MLS#: DENC2092878

1 2 3 4 5 6 ... 16

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