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
239
# of Listings
3
Avg # of Bedrooms
$270
Avg. $ / Sq.Ft.
$653,388
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

239 Properties Found. Page 5 of 16.

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

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

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

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.

$699,900

MLS#: DENC2089908

FINAL HOME AT COPPERLEAF AVAILABLE IN 2026!!!! 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.

$699,515

MLS#: DENC2081304

New on site 2 days ago
Stunning new construction by Rachuba Homes in historic downtown Middletown. This beautifully designed 4 bedroom, 2.5 bath family home sits on nearly half an acre and offers comfort and practicality throughout. The open floor plan kitchen features stainless steel appliances, high-end cabinetry, premium counters, and a stylish backsplash. The main level includes 7' luxury plank flooring, black hardware accents, and an inviting covered front porch. An attached 2-car garage provides convenient access and storage. Upstairs, the deluxe owner’s suite includes a spacious walk-in closet and a spa-inspired bath with a 6x7 shower and dual sinks. Three additional bedrooms, a second full bath, and a conveniently located upper-level laundry complete the second floor. The lower level offers a large finished recreation room for additional living or entertaining space, and a rough-in to complete a full bathroom and 5th bedroom with egress already in place. Located in the highly regarded Middletown school district and walkable to shops, parks, and restaurants, this home combines modern comfort with small-town charm. Home is complete and ready to be your own!
#MDFR2074184

MIDDLETOWN

26 WALNUT STREET

4 Beds

2 Baths

2,712 Sq.Ft.

$699,000

MLS#: MDFR2074184

EXTREME PRICE IMPROVEMENT! Motivated Sellers! Be the lucky one to OWN this previous MODEL HOME and move in before Holiday season. Welcome to 712 Wallasey Drive! This beautiful 3 years young home by Ryan Homes is located in Middletown, Delaware, in the popular Preserve at Deep Creek. 712 Wallasey Dr is in the sought out Appoquinimink School District, conveniently located off of 301. You can enjoy this spacious new construction, with all the bells and whistles of a model home. This Seneca model offers 4450 square feet of living space with three gorgeous levels, boasting a finished basement with a full bathroom on a great lot. As you drive to the house, you are greeted with a beautiful upgraded front elevation, lovely landscaping, and a full size porch. As you enter the foyer, you will find a spacious study/office on your right and a powder room. As you continue your tour, you'll find that the home opens up to a big open family entertainment space – complete with a comfortable dining room, a warm family room, an expansive kitchen with a huge island, and another beautiful dining area. The entire first level has upgraded LVP flooring. You will love the white on white modern kitchen featuring quartz countertops, plentiful 42” crown cabinetry, updated hardware, new light fixtures, stainless appliances, gas cooking, vented out hood, a large island, an eat-in dining area, and a walk-in pantry. From the kitchen, you can walk out to a large, accessible, no maintenance deck and leveled lot, perfect for entertaining and for outdoor gatherings. The huge family room has a gas fireplace to keep you warm and cozy in all seasons. By the side of the family room, you'll find a convenient garage entrance which has an arrival center for all your accessories. From the family room, take the stairs to the second level where you'll find the enormous primary bedroom with a luxurious en-suite, featuring a large tile shower and two walk-in closets. You will have plenty of room for your family with three additional bedrooms, two of which share a Jack and Jill bath and a third, potentially a guest bedroom, that offers an en-suite bath. All bedrooms have walk-in closets, all bathrooms have easily maintained and aesthetically pleasing tiled floors. There is also a spacious center loft in this level for upper level entertainment. Upper level laundry completes the tour of second level. The finished lower level has three different entertaining areas for family to enjoy different activities. This gorgeous basement also has a full bath with finishes similar to the stylish bathrooms upstairs. There is a good size unfinished section in the basement for all your storage needs. All three levels have ample recess lighting and plenty windows to keep your home bright yet cozy. Other special features unique to this house are side entrance door for the garage, irrigation system for your lawn. Carrier HVAC system with two zone thermostat and tankless water heater are features that are done with functional convenience in mind. Schedule your tour today. House comes with no furniture. Pictures give idea of the size and furniture option visualization. Any questions contact listing agent.
#DENC2089228

MIDDLETOWN

712 WALLASEY DRIVE

4 Beds

4 Baths

4,450 Sq.Ft.

$699,000

MLS#: DENC2089228

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.

$698,999

MLS#: MDFR2075782

This stunning executive home located in sought-after Westside Hunt and the Appoquinimink School District offers casual elegance, almost 5000 square feet of living space, and fine craftsmanship by Desabatino Construction. This home features a beautiful stone facade, gracious covered porch for morning coffee or relaxing afternoons, gleaming hardwood floors, 9' first floor ceilings, an ample family room with cozy gas fireplace adjoining the generous kitchen with center island, great pantry, newer stainless steel appliances, and a sunlit breakfast alcove overlooking the large deck and the expansive, fully fenced back yard. The two story foyer with handsome oak staircase takes you to the second floor where you'll find four comfortable bedrooms, three full baths, and a spacious 20 x 24 bonus room or 5th bedroom . The primary retreat offers a luxurious en-suite bath with huge soaking tub, walk-in shower and double vanity. The fourth bedroom/guest suite is complete with a private full bath and jetted tub. The massive finished lower level with built-in bar is the perfect entertainment, media/game room, work or hobby space. The two car garage is equipped with a plug for your EV charger and leads to a handy mudroom/drop zone for shoes and gear. Other features include a new water heater, new carpet, newer A/C unit and a radon mitigation system. Nestled on .8 acres and conveniently located in peaceful and picturesque West Middletown this home offers easy access to restaurants, shopping, schools, marinas, YMCA, parks and outdoor recreation as well as the Rt. 301 bypass and Rt. 1 for a quick commute to points North and South.
#DENC2096684

MIDDLETOWN

103 WESTSIDE LANE

4 Beds

3 Baths

4,936 Sq.Ft.

$695,000

MLS#: DENC2096684

Welcome to this beautiful 5 bedroom home located in the highly desirable Estates of St. Annes. This home has been impeccably maintained by its original owners. As you enter the home you have a formal dining area to your right, and a living room or office space to your right. Continuing down the hall you will enter the open kitchen and living room area with a gorgeous fireplace. There is also a morning room that leads out to the lovely patio with no homes behind you! Upstairs you have all 5 bedrooms, including the massive primary suite with vaulted ceilings, a spa like bathroom, and walk in closets! Downstairs you have an amazing wet bar and tons of finished space for entertaining. We can't wait for you to see this home!
#DENC2086432

MIDDLETOWN

50 HAGGIS ROAD

5 Beds

2 Baths

4,700 Sq.Ft.

$689,999

MLS#: DENC2086432

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