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
259
# of Listings
3
Avg # of Bedrooms
$274
Avg. $ / Sq.Ft.
$648,255
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

259 Properties Found. Page 6 of 18.

New on site today
Welcome to 546 Buck Tavern Drive, a like-new, impeccably upgraded luxury residence in the prestigious community of Rothwell Estates in Middletown. Built in 2022 and set on a beautifully landscaped 0.28-acre homesite, this exceptional property offers over 3,300 square feet of thoughtfully designed living space where sophistication meets everyday comfort. From the moment you arrive, you’re welcomed by a grand two-story foyer with soaring ceilings and sightlines that lead effortlessly into the breathtaking main living area. Here, dramatic cathedral ceilings, expansive windows, and a striking fireplace create a light-filled statement space that feels both elevated and inviting. Designed with both entertaining and daily living in mind, the home features elegant formal living and dining rooms, complemented by a stunning gourmet kitchen outfitted with quartz countertops, stainless steel appliances, abundant cabinetry, and a spacious eat-in area perfect for gathering. The main level offers exceptional versatility, featuring a private bedroom with a beautifully appointed en suite bath, ideal for guests or multi-generational living. A well-designed mudroom enhances everyday convenience with a dedicated washer and dryer, blending functionality seamlessly into the home’s elevated design. The entire home has been freshly painted, offering a crisp, move-in-ready feel. Upstairs, a dramatic catwalk overlooks the main living space, adding architectural interest and an open, airy ambiance. Four generously sized bedrooms complete the upper level, including a luxurious primary suite featuring a spa-inspired bath with a soaking tub, creating the perfect retreat at the end of the day. There is also a full laundry room on the second floor for added convenience. The expansive lower level offers incredible flexibility, with a partially finished area ideal for additional living or recreation space, along with a large unfinished section ready for storage or future customization. The home is thoughtfully equipped for modern, energy-efficient living, featuring a newly installed 20-panel solar system designed to reduce utility costs and environmental impact. An electric vehicle charging station in the garage adds everyday convenience, making this home as functional as it is forward-thinking. With five bedrooms, three full bathrooms, one half bath, upgrades and access to the highly sought-after Appoquinimink School District, this home delivers an exceptional combination of style, space, and location. This is more than a home, it’s a statement of modern luxury living. Schedule your private tour today.
#DENC2100736

MIDDLETOWN

546 BUCK TAVERN DRIVE

5 Beds

3 Baths

3,750 Sq.Ft.

$700,000

MLS#: DENC2100736

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

New on site today
For Sale in Middletown on 5.21 Gorgeous Acres! Spacious Custom home with a fully finished lower-level apartment, perfect for multi-generational living. Tucked along a private gravel lane in the Shenandoah Valley, this property offers a peaceful, semi-secluded setting with a blend of open yard and wooded privacy. The main level features a split-level design with the primary suite privately situated on one side of the home, while the kitchen and main living areas sit at the heart of the layout. You’ll also find three additional bedrooms, including one currently staged as an office, along with a full bath and half bath. The home offers high ceilings, quality finishes, and a comfortable, functional flow. The primary suite includes an en-suite bath with new shower glass coming soon. The finished lower level lives like its own private apartment with a separate entrance, making it ideal for in-law living or extended guest space. This level includes a full kitchen with laminate countertops and full appliance package, a spacious living area, a bar/entertaining space with tile flooring, a second laundry area, and a full bathroom. One bedroom is considered a true bedroom, while an additional finished room (without a window or closet) offers great flexibility as an office, hobby room, or bonus space. A screened porch adds even more usable living area to the lower level. Additional highlights include a walk-out basement, a mix of carpet, tile, and LVP flooring, and thoughtfully designed spaces throughout. Situated on 5.21 acres with no HOA or restrictive covenants, the property offers ample room for outdoor activities, gardening, or hobby farming—all while still being conveniently located near commuter routes and local amenities. Out of respect for the occupants, please do not drive by the property.
#VAFV2040064

MIDDLETOWN

201 LIBERTY LANE

4 Beds

1 Baths

3,540 Sq.Ft.

$699,900

MLS#: VAFV2040064

Welcome to Dove Run – Luxury Living in Middletown! Located within the highly sought-after Appoquinimink School District, this exquisite traditional residence offers the perfect blend of elegance, space, and modern upgrades—all within Middletown city limits. Built in 2004, this impressive home spans approximately 4,175 square feet and features 4 spacious bedrooms and 3.5 bathrooms, designed for both comfortable living and effortless entertaining. Enjoy an oversized family room and a luxury kitchen complete with 42-inch cabinets, granite countertops, and a stylish backsplash. A whole-house central vacuum system adds convenience across all levels. The thoughtfully designed layout creates a warm and inviting atmosphere throughout. Recent upgrades include brand new carpet on the main and upper levels, extending into all bedrooms and closets, along with a new roof and hot water heater installed within the last 6 months—providing peace of mind for years to come. Additional enhancements include new window screens that complement the home’s updated exterior and roof design. The fully finished basement offers incredible versatility, featuring a dedicated movie room with surround sound, a game area, or the perfect private retreat tailored to your lifestyle. Step outside to a backyard designed for both entertaining and relaxation, showcasing over 800+ square feet of concrete patio space and a 10x12 gazebo—ideal for gatherings or quiet evenings at home. The full-yard irrigation system with 32 sprinkler heads ensures a lush, well-maintained lawn all season long. Parking is a breeze with an oversized 2-car garage, a spacious driveway, and additional on-street parking for guests. This home truly offers the luxury of space, timeless design, and modern convenience. Don’t miss the opportunity to own a remarkable property where comfort meets lifestyle. Your dream home awaits in Dove Run. One owner is a Delaware Real Estate Broker.
#DENC2100692

MIDDLETOWN

917 BENALLI DRIVE

4 Beds

3 Baths

4,581 Sq.Ft.

$695,000

MLS#: DENC2100692

New Construction with semi-custom builder, Benchmark Builders. LAST LOT AVAILABLE in the sought after community of Rothwell Estates. This lot backs to trees and faces West. The Grandview floor plan is a gorgeously large ranch with expansive kitchen and cathedral ceilings. This proposed home has an option for a 2nd floor with loft and additional bed and bath. Make an appointment with the site sales manager to talk over all the details. Pictures are of similar homes we have done. The Benchmark Builders website has more information like the site map, standard features, and virtual tours. The Grandview is one of 6 floor plans available to build.
#DENC2100356

MIDDLETOWN

619 MCCRACKEN DRIVE 2 GRANDVIEW

5 Beds

3 Baths

3,560 Sq.Ft.

$694,000

MLS#: DENC2100356

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

New Construction with semi-custom builder, Benchmark Builders. LAST LOT AVAILABLE in the sought after community of Rothwell Estates. This lot backs to trees and faces West. The Houston floor plan has been our most popular and is the same as the model home on Green Forest Dr. The 2 story foyer & great room, & catwalk gives this home the WOW FACTOR you have been looking for. This proposed home has an option for a morning room or sunroom & 1st floor in-law suit complete with full bath. Make an appointment with the site sales manager to talk over all the details and tour the model. Pictures are of similar homes we have done. The Benchmark Builders website has more information like the site map, standard features, and virtual tours. The Houston is one of 6 floor plans available to build.
#DENC2100346

MIDDLETOWN

619 MCCRACKEN DRIVE 1 HOUSTON

5 Beds

3 Baths

3,560 Sq.Ft.

$685,000

MLS#: DENC2100346

New on site 2 days ago
Welcome to Shannon Cove, where space, convenience, and comfort come together in this beautifully maintained single-family home situated on a generous half-acre lot. With public water and sewer and a prime location offering easy access to the beaches as well as Wilmington and Philadelphia, this home delivers both tranquility and connectivity. Inside, you’ll find five spacious bedrooms and two-and-a-half baths, providing plenty of room for family, guests, or a home office setup. The kitchen is designed for both everyday living and entertaining, featuring granite countertops, a breakfast bar, and gas cooking. A dual HVAC system ensures efficient comfort year-round. The exterior is just as impressive, with a well-landscaped lot and a fully fenced backyard. Enjoy outdoor living on the large deck, complemented by a shed for additional storage and privacy plantings that are well on their way to creating a secluded backyard retreat. Additional highlights include an attached two-car garage and a full unfinished basement, offering endless potential to expand your living space and truly make this home your own. Affordable, spacious, and ideally located—this home has everything you need and more. Schedule your appointment today!
#DENC2100188

MIDDLETOWN

1105 CARDIGAN ROAD

6 Beds

2 Baths

3,275 Sq.Ft.

$679,900

MLS#: DENC2100188

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

3 Beds

1 Baths

4,936 Sq.Ft.

$679,900

MLS#: DENC2096684

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.

$679,000

MLS#: VAWR2013346

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

None Beds

None Baths

3,250 Sq.Ft.

$675,000

MLS#: DENC2098226

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 Whimbrel is a ranch home starting at 1,971 sq. ft., with 3 bedrooms, 2 baths, and a flex space ideal for a home office. Open kitchen with island flows to dining and great room. Options available for extra bedrooms, baths, loft, 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.
#DENC2093528

MIDDLETOWN

2204 EARLY COURT

3 Beds

2 Baths

1,971 Sq.Ft.

$669,900

MLS#: DENC2093528

Welcome to 42 Watson Lane—offering the space, layout, and setting you’ve been searching for. With over 3,000 square feet and a prime location backing to the golf course, this well-maintained home is ready for its next owner to make it their own. Step inside to a spacious foyer with a striking double staircase leading to the second level. The main floor features a formal dining room to the left and a living room to the right, along with a convenient half bath and a dedicated office—perfect for working from home. The expansive family room is ideal for everyday living and entertaining, featuring a wood fireplace and large windows that bring in abundant natural light. The open-concept kitchen offers generous counter space, stainless steel appliances, recessed lighting, and a full pantry. Just off the kitchen, you’ll find access to the laundry room, garage, and side yard. Sliding doors from the kitchen lead to an enclosed porch—perfect for relaxing or hosting guests—while the outdoor deck overlooks the golf course, creating a peaceful backdrop for gatherings. The backyard offers plenty of space for outdoor enjoyment. Upstairs, accessible from both the foyer and kitchen staircases, you’ll find a spacious owner’s suite complete with a sitting area, dual closets, and a private bath featuring a jetted tub, double vanity, and a large glass-enclosed shower. Three additional bedrooms with ample closet space and a full hallway bath complete the upper level. The unfinished basement provides endless potential, featuring a three-piece rough-in for a future bathroom and walk-up access to the backyard—ready for your vision and customization. Freshly painted throughout, this home offers a clean slate with incredible space and flexibility. Ideally situated along the golf course at Frog Hollow, you’ll enjoy close proximity to shopping, dining, and everyday conveniences, with easy access to major routes connecting you to Wilmington, Philadelphia, Baltimore, and Delaware beaches. Schedule your private tour today and discover all this home has to offer!
#DENC2099846

MIDDLETOWN

42 WATSON LANE

4 Beds

2 Baths

3,475 Sq.Ft.

$669,000

MLS#: DENC2099846

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Buyers resources
7 Reasons to Work with a Realtor
7 Principles For Home Buying Success
Getting a Mortgage To Buy a Home
Home Hazards Awareness
Key Items For Home Inspection
Questions When Buying a Condo
Questions When Choosing a Realtor
Sellers resources
8 reasons to work with a realtor
Calculating Capital Gains
Checklist for Better Showing
Cleaning Home For Sale
Improving Odds Of an Offer
Preparing Home for photoshoot
Selling Your Home for More $$

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