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
232
# of Listings
3
Avg # of Bedrooms
$273
Avg. $ / Sq.Ft.
$647,221
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

232 Properties Found. Page 4 of 16.

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

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 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.

$744,900

MLS#: DENC2093606

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

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.

$734,900

MLS#: DENC2093596

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 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.

$724,900

MLS#: DENC2093550

WOW!!!! SELLER JUST MADE A $25,000 PRICE DROP!! OPEN HOUSE SAT, JAN 17TH 11am-1pm...............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.

$715,000

MLS#: DENC2089908

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.

$714,900

MLS#: DENC2093592

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

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

New on site 1 day ago
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

411 Crownleaf Dr., the beautiful Montgomery Farmhouse! Off your front porch, you are greeted by a grand double story entry way with your formal dining room off to the side. Moving inward, an open layout seamlessly connects the family room with cozy fireplace, gourmet kitchen (complete w/ quartz counters, tile backsplash, and upgraded cabinetry), and included sunroom, creating an ideal setting for gatherings. Additionally, on the first level you will find your very own home office, as well as a spacious mudroom and walk-in pantry. The upper-level features 3 guest bedrooms, a hall bath, laundry room, and luxurious owner's suite. The owner’s suite offers a tranquil retreat area, perfect for relaxation. On the lower level, a large unfinished basement equipped with walk-up steps is ready for your personal touch—whether it’s a home theater, gym, additional living space, or storage. Enjoy luxurious living with convenient access to top-rated schools, shopping, dining, and recreation. This is more than just a home—it's a lifestyle. Contact us today to schedule a private tour. Prices, dimensions, and features may vary and are subject to change. Photos are for illustrative purposes only. Please see sales team for final details and finishes. Taxes to be assessed after settlement. If using a Realtor, the agent's client must acknowledge on their first interaction with Lennar that they are being represented by a Realtor, and the Realtor must accompany their client on their first visit.*
#DENC2081304

MIDDLETOWN

411 CROWNLEAF DRIVE

4 Beds

2 Baths

2,955 Sq.Ft.

$699,990

MLS#: DENC2081304

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Buyers resources
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Selling Your Home for More $$

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