CHARIS REALTY GROUP
One of the most popular communities provided by {{page_data.agentName}}

MIDDLETOWN

One of the most popular communities provided by Charis Realty Group

MIDDLETOWN

About MIDDLETOWN

Discover Middletown, MD Real Estate 

Welcome to Middletown, Maryland! Nestled in the heart of Frederick County, Middletown offers a charming blend of small-town atmosphere and modern amenities. If you’re searching for a place where community, convenience, and natural beauty meet, Middletown, MD real estate is the perfect choice.

Why Choose Middletown, MD?

Located just minutes west of Frederick, Middletown boasts picturesque landscapes, historic landmarks, and a warm, welcoming community. Here’s why so many homebuyers are looking for houses for sale in Middletown, MD:

  • Stunning Mountain Views: Surrounded by the scenic Catoctin Mountains and rolling farmland, this area provides breathtaking vistas year-round.
  • Top-Rated Schools: Middletown is renowned for its excellent public schools, including Middletown High School.
  • Charming Downtown: Explore locally-owned shops, cafes, and eateries along Main Street for a classic small-town experience.
  • Nearby Recreation: Enjoy outdoor activities at Middletown Park, South Mountain State Park, and local golf courses.
  • Easy Access: Quick commutes to Frederick, Hagerstown, and even Washington, DC make Middletown ideal for professionals and families alike.

Middletown, MD Housing Market Overview

The Middletown, MD real estate market features a wide variety of properties, from historic Victorian homes to modern new constructions. Whether you’re a first-time buyer, looking to upgrade, or seeking a peaceful place to retire, Middletown offers:

  • Single-family homes
  • Townhouses
  • New builds and developments
  • Spacious lots and acreage

Interested in recent listings? Check current homes for sale in Middletown, MD for up-to-date market trends and pricing.

Live in the Heart of Frederick County

Relocating to Middletown, MD means you’ll experience:

  • A strong sense of community and friendly neighbors
  • Highly walkable streets with beautiful historic architecture
  • Year-round events, including the popular Middletown Heritage Festival
  • An unbeatable blend of rural charm and convenient suburban living

Ready to Find Your Dream Home in Middletown?

From stately colonials to custom-built estates, Middletown, Maryland real estate delivers exceptional value and quality of life. If you’re considering a move, now is the perfect time to contact a trusted Charis Realty Group agent to start your search.

Start living the life you’ve always dreamed of in Middletown, Maryland—where homes are more than houses; they’re part of a vibrant, enduring community.

One of the most popular communities provided by Charis Realty Group
244
# of Listings
3
Avg # of Bedrooms
$273
Avg. $ / Sq.Ft.
$639,184
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

244 Properties Found. Page 5 of 17.

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.

$729,900

MLS#: DENC2093362

Welcome to this beautifully maintained 3-year-old Colonial-style home, offering the perfect blend of modern comfort and timeless design. This spacious 4-bedroom, 2.5-bath residence is ideal for both everyday living and entertaining. Step inside to find a bright and inviting layout with generous living spaces, complemented by thoughtful upgrades throughout. The home features a partially finished basement, complete with a full bathroom rough-in—ready for your personal touch to create additional living space, a home gym, or entertainment area. Enjoy outdoor living at its best with a 12x16 Trex deck overlooking a patio—perfect for gatherings, grilling, or relaxing evenings. The fully fenced yard provides privacy and security, while the 8x10 shed offers convenient extra storage. This property is equipped with a 6-zone underground Rain Bird sprinkler system to keep your lawn lush and well-maintained with ease. For added peace of mind, the home also includes an Arlo security system. Additional highlights include a 2-car garage and modern construction that ensures efficiency and low maintenance for years to come. Don’t miss the opportunity to own this move-in ready home that truly checks all the boxes!
#DENC2098944

MIDDLETOWN

663 GORDON HOUSE WAY

4 Beds

2 Baths

3,375 Sq.Ft.

$725,000

MLS#: DENC2098944

Options galore! Purchase or ground lease with potential seller financing for a qualified purchaser. I-81 Exit #302 is the Gateway entrance into the Historic Town of Middletown, Virginia. This is the last remaining lot at the corner of Reliance Road and Valley Ave (Rt #11). We have 3.84 acres zoned B2 highway commercial. You are surrounded by The Village at Middletown by Ryan Homes. Richmond American Homes are building 90 additional single family homes on the south end of town. Middletown is home to Historic Wayside Inn, circa 1797, Laurel Ridge Community College with 3,500 students and staff. Immediate neighbors include; Comfort Inn, McDonalds, Dollar General, 7-11, Liberty C-store with fuel depot, Sheetz C-store with fuel depot has recently opened on the east side of the interstate. Locate your successful business venture where the growth is happening.
#VAFV2039508

MIDDLETOWN

0 RELIANCE

None Beds

None Baths

3.84 acres

$725,000

MLS#: VAFV2039508

Brand New 55+ Community in Middletown, DE Welcome to the Carver, a beautifully designed home that blends an open-concept layout with timeless Classic-inspired elements. Scheduled for settlement in July 2026, this home offers 3 bedrooms (including one in the finished basement), 3.5 baths, and a 2.5-car garage, providing both flexibility and comfort. The main living area features a stunning fireplace with shiplap, creating a warm and inviting focal point. A finished basement with a full bathroom and bedroom offers additional living space ideal for guests, entertaining, or a private retreat. Feature walls in the foyer and primary bedroom add character and style throughout the home. Enjoy outdoor living on the screened porch overlooking community open space, perfect for relaxing and taking in the surroundings. The kitchen is enhanced with a smart appliance upgrade and quartz countertops, combining modern convenience with elegant design. Laminate flooring flows throughout the first floor, creating a seamless and cohesive look. The baths include a tiled shower enclosure with a rain shower head, adding a spa-like touch to your daily routine. 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.
#DENC2099418

MIDDLETOWN

1606 JAYMES CIRCLE

2 Beds

2 Baths

2,493 Sq.Ft.

$719,990

MLS#: DENC2099418

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.

$719,900

MLS#: DENC2093486

Looking for that perfect place to call home? Look no further! Not only is this gorgeous home on a quiet cul-de-sac in the peaceful yet conveniently located luxury 55+ active adult community of Four Seasons at Baymont Farms but it is also practically new at less than 2 years old. The home, itself, offers a true one level living and boasts an open floor plan, open kitchen with soft close cabinets and drawers, stainless steel appliances, quartz counters, gas cooking, tile backsplash, a pantry and large center island, a designated dining area, a living room with a cozy gas fireplace with blower, main floor primary bedroom suite with tray ceiling, a large walk-in closet and full bathroom with dual sinks, a separate thrown room, and walk-in tile shower, 1 additional bedroom and full bathroom on the main level along with a sunroom, flex room (which would make a great office, den, or formal dining room), and mud/laundry room, a 2nd floor with large loft, a 3rd bedroom and full bathroom as well as a storge closet, a full mostly finished light and bright basement with recreation room and a 4th bedroom and full bathroom as well as 2 unfinished utility/storage areas, lots of natural light, neutral colors, and window treatments throughout, 9ft ceilings, 2 car garage with keyless entry, a serene front porch, screened in back porch overlooking your peaceful back yard, and much more. And if the home itself isn't enough to make you want to pack your bags and move right in, the fact that you will no longer have to mow your own grass or shovel your own snow surely will. Low maintenance living at its best! In addition to individual lawn/yard maintenance and snow removal, community and Homeowners Association fee includes many community amenities such as an outdoor pool with tiki hut , multiple bocce and pickleball courts, tennis court, dog park, a kayak launch, fishing, walking path, and a 6,000 sq. ft. clubhouse complete with library, billiard room, a state-of-the-art fitness center (so home owners can say good bye to expensive gym membership fees), card room, yoga room, lounge, bar and dining room. Baymont Farms also boasts a full-time on-site lifestyle director to help ensure residents have a well-maintained calendar of activities available to them to help keep the mind, body, and spirit happy.
#DENC2095542

MIDDLETOWN

114 AUSTRIAN PINE COURT

4 Beds

4 Baths

2,595 Sq.Ft.

$715,000

MLS#: DENC2095542

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

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

This is the home you have been waiting for! A rare opportunity in Villages at Fairview Farm, set on nearly an acre backing to wooded views and the C&D Canal. The updated kitchen features white cabinetry, granite countertops, a peninsula and center island, eat-in space, a large pantry, and abundant storage. Adjacent to the kitchen, a bright sunroom with skylights and sliding glass doors opens to the rear patio with an awning, perfect for seamless indoor-outdoor living. The spacious family room offers vaulted ceilings, expansive windows for natural light, a gas fireplace, and a rear staircase. The main level also includes a dining room, separate living room, office, powder room, and convenient first-floor laundry and garage access. Upstairs, you’ll find four generously sized bedrooms, including a spacious primary suite. The additional three bedrooms offer ample closet space and share a full hall bath. The primary suite features a double-door entry, a comfortable sitting area, with dual closets, and a private en-suite bath with a separate shower and Jacuzzi tub. The lower level features a spacious, partially finished basement complete with a gaming area along with additional pantry space and two large unfinished areas ideal for storage. Bilco doors provide convenient walk-out access directly to the backyard. Step outside to enjoy a large stone and concrete patio with a removable awning, an expansive yard with endless possibilities, and a charming brick walkway that leads to your private oasis featuring an in-ground pool and plenty of space for lounging and entertaining. An oversized shed provides ample outdoor storage. A separate firepit area near the shed offers the perfect spot to relax and gather on cool evenings. The extended driveway offers generous parking, and the two-car garage adds additional convenience and space. Recent updates include the roof, hot water heater, sump pump, and HVAC system. Don’t miss this rare opportunity. Schedule your tour today!
#DENC2098226

MIDDLETOWN

32 CHANCELLORSVILLE CIRCLE

4 Beds

2 Baths

3,250 Sq.Ft.

$699,000

MLS#: DENC2098226

WELCOME to 712 Wallasey Dr, the HUGE previously SENECA MODEL HOME by Ryan Homes. It is located in the sought out Appoquinimink School District, conveniently located off of 301 in the popular Preserve at Deep Creek community. Be the PROUD OWNER to enjoy this model home with many upgrades at a DEAL PRICE. 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 a gorgeous dining room and then the home opens up to a big open family entertainment space – a warm living room, an expansive kitchen with a huge island, and beautiful eat-in kitchen 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 living 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 to enjoy different activities. You can easily convert a section into 5th bedroom. 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. One of the owners is DE licensed real estate agent and listing agent.
#DENC2089228

MIDDLETOWN

712 WALLASEY DRIVE

4 Beds

4 Baths

4,450 Sq.Ft.

$699,000

MLS#: DENC2089228

Welcome to the perfect blend of modern style and peaceful country living. This brand-new modern farmhouse with craftsman influence is privately nestled on 6.6 wooded acres, offering the seclusion you crave while remaining just minutes from Routes 66 and 81 for an easy commute. Thoughtfully designed with meticulous attention to detail, this 3-bedroom home offers 2,000 square feet of beautifully finished living space. The heart of the home features a stunning stone gas fireplace that anchors the living room, creating a warm and inviting gathering space. The kitchen showcases gorgeous custom cabinetry, quality finishes, and a layout ideal for both everyday living and entertaining. A durable metal roof adds both character and long-term peace of mind. Downstairs, the walk-out basement includes 1,000 square feet of unfinished space ready for your vision, whether it’s a home gym, media room, guest suite, or additional living area. Surrounded by woods, this property offers privacy and serenity, yet remains part of a community with HOA access to a private lake, perfect for fishing and relaxing weekends outdoors. If you’ve been searching for new construction, acreage, and convenience all in one… this is it. See attached notes for Builder Upgrades.
#VAWR2013346

MIDDLETOWN

220 LAKELAND CIRCLE

3 Beds

2 Baths

2,000 Sq.Ft.

$695,000

MLS#: VAWR2013346

New on site 1 day ago
Welcome home to this timeless late 19th-century Victorian, gracefully set in the heart of Middletown’s historic district. Framed by a classic white picket fence, this enchanting property welcomes you from the moment you arrive. The distinctive front door—with its red stained glass and charming doorbell—offers a memorable first impression and sets the tone for the character found throughout. Inside, the original home showcases rich hardwood floors, beautifully preserved woodwork, and the kind of craftsmanship rarely found today. Generous living spaces include a formal living room, inviting family room, cozy den, and a thoughtfully updated kitchen remodeled in 2012—blending modern convenience with historic charm. A later addition provides a private apartment suite—ideal for guests, rental income, or a potential Airbnb opportunity. Complete with its own kitchenette (refrigerator, hot plate, microwave, and sink) as well as a private washer and dryer, this flexible space expands the home’s possibilities. Outdoors, stone pavers lead from the back porch to a welcoming firepit area—perfect for gathering on cool evenings—while a slate patio near the driveway offers additional space for relaxing or entertaining. Located just steps from local shops, parks, and dining, this remarkable property offers more than generous living space—it offers a lifestyle where history, character, and comfort come together in one of Middletown’s most treasured settings. Don’t miss your opportunity to experience this historic beauty for yourself. *Sold as-is. inspections for informational purposes only.*
#MDFR2076970

MIDDLETOWN

200 E MAIN STREET

6 Beds

2 Baths

3,441 Sq.Ft.

$694,900

MLS#: MDFR2076970

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 Mayberry is a ranch home starting at 2,254 sq. ft., with 3 bedrooms, 2 baths, and a flex space. Split-bedroom design offers privacy; open kitchen with walk-in pantry flows to great room and dining. Options available for extra bedrooms, baths, and outdoor 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.
#DENC2093526

MIDDLETOWN

2206 EARLY COURT

3 Beds

2 Baths

2,254 Sq.Ft.

$689,900

MLS#: DENC2093526

This move-in ready, 3-year-old D.R. Horton home is a spacious two-story with five bedrooms, three and a half bathrooms. It also includes a game room with a wet bar, a media room, a workshop or exercise room, a full bathroom, and plenty of storage space in the basement, as well as a two-car garage and an oversized deck. The foyer features a coat closet and creates a welcoming flow for greeting guests. The front room is filled with natural light and is large enough to accommodate both a living and dining area. The spacious kitchen boasts beautiful birch cabinetry, granite countertops, stainless steel appliances, a pantry, and an island with seating. It opens to both the breakfast area and a sizable family room. A convenient powder room is located on the first floor, and the stairs to the second floor are tucked away in the family room, which also includes a cozy fireplace. Upstairs, the owner’s suite offers a large bedroom, two walk-in closets, and an oversized ensuite bathroom. The four additional generously sized bedrooms and a hall bathroom provide ample space for everyone. The first-floor laundry room is conveniently located near the garage, along with an additional coat closet. The property is vacant and ready to move in for the holiday.
#DENC2089762

MIDDLETOWN

1245 PIMPERNELL PATH

5 Beds

3 Baths

3,175 Sq.Ft.

$689,000

MLS#: DENC2089762

IMMEDIATE AVAILABILITY!!! Introducing the CHELSEA model in the highly desirable 55+ community of Traditions at Whitehall. This thoughtfully designed 3-bedroom, 2-bath home features an open-concept floor plan with a spacious foyer, 9 ft ceilings, formal dining area, great room w/fireplace & an additional sunroom that flows into the kitchen perfect for entertaining. The Owner’s Suite includes a large walk-in closet and en-suite bath with a double vanity and standard tile shower. The gourmet kitchen comes w/stainless steel appliances, granite countertops, a large island, 1st floor laundry, and butlers pantry. In addition to your true one floor living this home also has a 2-car attached garage and unfinished full basement. The Chelsea Model offers the perfect combination of comfort and style. As a resident of this vibrant active adult community, you'll enjoy access to a wealth of amenities, including a state-of-the-art clubhouse, fitness facilities, sparkling swimming pools, and a full calendar of social events to keep you engaged and connected with neighbors.
#DENC2088952

MIDDLETOWN

548 LONGHORN LOOP LOT 33 CHELSEA

3 Beds

2 Baths

2,296 Sq.Ft.

$688,893

MLS#: DENC2088952

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Buyers resources
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