CHARIS REALTY GROUP
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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
245
# of Listings
3
Avg # of Bedrooms
$277
Avg. $ / Sq.Ft.
$645,106
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

245 Properties Found. Page 6 of 17.

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

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.

$684,900

MLS#: DENC2096684

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

New construction without the wait. This brand new gorgeous estate home has everything you could want and more! With four bedrooms and 2.5 baths, it ensures enough space for the whole family - and that includes a modern Study/Laundry Upgrade. Additional features include an upgraded kitchen with island, gas range & granite counters; a 1st-floor powder room; a 3-piece basement rough-in at basement, and a roomy two-car garage. Make an appointment to tour it now.
#DENC2091264

MIDDLETOWN

642 GORDON HOUSE WAY

4 Beds

2 Baths

2,889 Sq.Ft.

$657,712

MLS#: DENC2091264

Beautiful 6 bedroom, 3 1/2 bathroom colonial offering a covered front porch, 2 car garage, and a backyard paradise. The main floor offers a guest/in-law suite with full bathroom, formal living room/office, dining room, family room with gas fireplace featuring exquisite word working including ship lap and coffered ceiling, Kitchen with center island, granite counter tops, stainless steel appliances, and a pantry, as well as a morning room with access to the backyard deck. The upper level offers 5 bedrooms and features an owner suite, a large bedroom over the garage, laundry and 3 other generously sized bedrooms. The basement has a finished room, bathroom and offers a double well walk up exit to the backyard. The fenced backyard features an in ground salt water swimming pool with remote controlled underwater lighting, 3 deck jets, pennsylvania jump boulders/waterfall, deck, patio and a lounge area covered by a pergola with privacy trees. The home also features hardwood flooring, central vacuum system, bonus dedicated mini splits in most upper bedrooms, and plenty of storage space in the garage. Community amenities include walking trails, gazebo, park with playground, sand volley ball court, basketball court and wall ball. There is also a 18 hole golf course with clubhouse, Lore Woodfyre and Highlands Whiskey Bar. Don't miss the opportunity to make this impressive property your new home!
#DENC2097264

MIDDLETOWN

303 BRAEMAR STREET

6 Beds

3 Baths

3,716 Sq.Ft.

$650,000

MLS#: DENC2097264

Welcome to 321 Ellenwood Drive, located in the sought out neighborhood of PARKSIDE. What an unique home!!!! a semi custom home built by Lifestyle by the original owners. This inviting 4 bedroom, 3.1 bathroom home is very special....first floor very large primary suite...Beautiful kitchen with all new appliances including a double oven, great counter space and eat in area with sliding doors out to a lovely paver patio with real wrought iron railing. The family room just had their hardwoods refinished and WOW ... did they come out beautiful, a gas fireplace a 4 windows pouring in with natural sunlight. 2nd floor has a large loft, 2 bedrooms and 1 full bathroom and then a large office/playroom/flex room that has an opening to the the family room below....and a cute balcony to sit our on and stare out the stunning tree lined street..... then a third floor with another loft, large bedroom and full bathroom....wait, so much more.... a 3 season room that has 3 points of exits... one to side yard, one to the other side yard that is fenced and one off the back of the house connecting to the 2 car garage. Now, if that is not enough, there is a large unfinished basement waiting for you to finish if you wish with a rough in and 9 foot ceilings... also a walkup bilco door... radon remediation added... a generator...beautiful landscaping...upgraded and maintained so well.... Now for the best news...brand new roof and the solar panels are being put back up 12/1 and will be owned up until March of 2036....Sellers bought out the lease for your savings!!!! Parkside has so much to offer... the community pool, where you can soak up the sun and enjoy a refreshing swim during warm summer days. The gym..... the club house.... and all our beautiful pocket parks. Don't miss your chance to call this charming home in a sought-after neighborhood yours. Schedule a viewing today to experience the comfort and convenience this property has to offer in person.
#DENC2092224

MIDDLETOWN

321 ELLENWOOD DRIVE

4 Beds

3 Baths

3,175 Sq.Ft.

$649,999

MLS#: DENC2092224

Tucked away on over 5 private acres, this chalet-style home is not your typical property – and that’s exactly the point. With soaring ceilings, expansive windows, and skylights throughout, the home a great balance of natural light and surrounded by wooded views that give it a true treehouse-like feel. A cozy fireplace anchors the main living space, while hardwood floors and warm finishes add to its character. The wraparound deck extends the living space outdoors, offering a peaceful setting for morning coffee or unwinding at the end of the day. An oversized detached two-car garage provides ample space for storage, hobbies, or projects. The kitchen has been refreshed with granite countertops and stainless steel appliances, blending modern convenience with the home’s unique style. This is a home for someone who appreciates privacy, architecture, and a setting that feels removed from it all - while still being just 15 minutes to Middletown’s shops, dining, and Middletown Schools. Updates include: Roof (2020), Skylights (2020), Stove & Microwave (2021), Refrigerator (2023), and Water Softener/Neutralizer (2022).
#MDFR2078904

MIDDLETOWN

6838 MOUNTAIN CHURCH ROAD

4 Beds

3 Baths

2,488 Sq.Ft.

$649,900

MLS#: MDFR2078904

Have you been looking for the perfect sophisticated and elegant historic home? Do you want everything; a gracious home, amazing space, acreage, a place for chickens, but also walkable and close to town? It sounds impossible, but you've found it! Welcome to historic Maplewood, circa 1872, know colloquially as The Tower. With no HOA and business B-1 zoning, this property presents endless possibilities, allowing dozens of potential uses! With stunning Italianate architecture and over an acre of land, this property is one in a million. This landmark home located in the heart of lovely downtown Middletown is a piece of history with all the modern conveniences. Rich with history, this amazing property was once the home and studio of John Chumley, a famous local artist. (The current owners have tons of photos and information about the history of the home that they'd love to share with you!) Too many amazing features to list; gorgeous high ceilings, original hardwood floors, wrap around built ins, huge windows, original millwork throughout, a generous kitchen and huge walk in pantry, fabulous mudroom, several outbuildings for storage and work space, an amazing chicken coop; the list goes on and on! Featuring four large bedrooms and two and half bathrooms, this home is spacious, beautiful, and elegant. The panoramic mountain views will take your breath away, especially from the tower studio room. And the home sits on a fantastic level lot behind public memorial land! All of this, located right in the center of town, so shopping and restaurants are just steps away. Middletown is an ideal location for commuters, with Rt 37, I-66 and I-81 within just a few minutes drive, not to mention all the natural beauty, activities, and amenities of the Shenandoah Valley. This is the one!!!
#VAFV2038812

MIDDLETOWN

2239 SIXTH STREET

4 Beds

2 Baths

2,944 Sq.Ft.

$649,900

MLS#: VAFV2038812

The Carver - with 4,000 finished sq. ft. - is a thoughtfully designed home that blends open living with private retreats. A welcoming foyer with a detailed ceiling treatment sets the tone as you enter. Just off the entry, a private home office with stylish barn doors offers the perfect space for telecommuting or quiet focus. The spacious great room and dining area come together beneath a vaulted ceiling, creating an open, airy feel ideal for both everyday living and entertaining. The striking kitchen features abundant counter space and a large pantry, making meal prep and storage effortless. Tucked away for privacy, the primary suite showcases an elegant ceiling treatment, a generous walk-in closet, and a luxurious primary bath with freestanding vanities and a large walk-in shower. The finished basement expands the living space with a recreation room, additional bedroom, and full bath—perfect for guests, hobbies, or multi-generational living. This listing is for a to be built home and photos are of a model home for display purposes only. Please see sales consultant for details.
#DENC2096234

MIDDLETOWN

1932 DIXON WAY

3 Beds

3 Baths

4,147 Sq.Ft.

$639,990

MLS#: DENC2096234

Major Price Reduction Move-in ready and offering over 4,000 square feet of beautifully finished living space, this expansive 4-bedroom home is set within the sought-after golf course community of The Estates at St. Anne’s, located in the highly regarded Appoquinimink School District. Designed for both everyday comfort and elegant entertaining, the main level features formal living and dining rooms, a spacious Great Room with a cozy fireplace, and an upgraded kitchen with a center island that opens to a sun-filled morning/breakfast room with access to the large Trex deck and pergola overlooking the expansive wrought-iron fenced yard. A dedicated home office, convenient laundry room, and half bath complete the first floor. Upstairs, you’ll find four generously sized bedrooms and two full baths, highlighted by the oversized Owner’s Suite with a sitting room, two large walk-in closets, and a spa-like bath with dual vanities, a corner soaking tub, and separate shower. Additional living space awaits in the full finished basement, while a two-car garage adds everyday convenience. Residents of The Estates at St. Anne’s enjoy access to a semi-private 18-hole golf course, the acclaimed Lore Modern Woodfyre restaurant, Highlands Whiskey Bar, and an on-site banquet facility. Ideally located with easy access to major highways, tax-free shopping at Christiana Mall, nearby parks, fine dining, and entertainment, and close to Middletown’s charming downtown—plus just about an hour from the Delaware beaches—this home truly offers the best of space, style, lifestyle, and location. Mortgage savings may be available for buyers of this listing.
#DENC2094672

MIDDLETOWN

312 GALLOWAY STREET

4 Beds

2 Baths

4,475 Sq.Ft.

$635,000

MLS#: DENC2094672

Freshly Painted Interior & Refinished Hardwood Floors-Upper-Level Hallway & Stairs! Beautiful Stone Front Colonial in Sought-After Pineland Park 3,887 total finished square feet offering 6 bedrooms and 3.5 baths on a 1-acre lot. Located in the desirable Pineland Park neighborhood of Warren County, ideal for commuting via I-66 and I-81. Minutes to golf, wineries, hiking, shopping, and downtown Front Royal. The Jefferson III model by H & H Builders features a stone front exterior, wide trim, interior columns, and 9-ft ceilings. Main level includes newly refinished hardwood floors throughout, a formal living room, and a formal dining room with chair rail and box ceiling detail. Spacious family room with corner gas fireplace opens to the kitchen with abundant cabinetry, countertop space, and breakfast area. Covered wrap-around front porch and rear covered porch provide great outdoor living spaces. Upper level offers hardwood hallway floors and new carpet in bedrooms. Newly remodeled primary suite includes vinyl plank flooring, tiled bath with soaking tub, separate shower, and walk-in closet. Newly remodeled upper-level bath. Three additional bedrooms and upper-level laundry for added convenience. Fully finished walk-out basement features tile flooring, kitchenette/wet bar, family room, two bedrooms, full bath, and ample storage—perfect in-law or guest suite. New AC units; furnace less than 5 years old. 2-car front-load garage with concrete driveway and plenty of off-street parking. Over 1 acre of open yard to enjoy.
#VAWR2012638

MIDDLETOWN

76 KATIE LANE

6 Beds

3 Baths

3,888 Sq.Ft.

$635,000

MLS#: VAWR2012638

Do Not Miss Your Opportunity to Check Out This Beautiful 5-Bedroom, 4.5-Bathroom Home in the Desirable Woodland Hills Community! Built in 2022, this Custom Designed Residence offers Modern Finishes and A Family Friendly Layout Throughout. Welcoming Main Level Features an Open-Concept Kitchen Featuring Custom Countertops, Luxury Vinyl Flooring, and Spacious Living Areas Perfect for Everyday Living and Entertaining. Main Floor Also Features a Versatile In-Law Suite or Primary Bedroom with an Attached Full Bath for Added Convenience. Enjoy the Abundance of Natural Light in the Sunroom, Surrounded by Large Windows that Create a Warm and Inviting Atmosphere. Upstairs,4 Generously Sized Bedrooms with Ceiling Fans and 3 Well-Appointed Bathrooms provide Comfort and Privacy for Family or Guests. A Large Unfinished Walkout Basement with 9ft Ceiling and Bathroom Already Roughed - In is Waiting for Your Ideas, Plenty of Space for a Super Man Cave , Hobby, Play Area and Work-Out Room. Outside, a Charming Brick Patio offers the Ideal Spot for Relaxing or Entertaining in the Peaceful Environment of this Quiet Neighborhood. Economical Gas Heat, Split System for Heat and Cooling , Instant ON Hot Water System , Water Conditioning , Softening and Filtering Unit Provide Cost Effective Services . This Home Has So Much To Offer , Do Not Miss Your Opportunity to Check This Upscale Property Out !!
#PADA2057844

MIDDLETOWN

182 MAGNOLIA DRIVE

5 Beds

4 Baths

3,576 Sq.Ft.

$629,900

MLS#: PADA2057844

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 Newport – Single-level ranch home with 1,662+ sq. ft., 3 bedrooms, and 2 baths. Features a spacious kitchen with island seating open to the dining area and great room. Options include an added second-floor bedroom and bath, unfinished storage, 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.
#DENC2093608

MIDDLETOWN

2202 EARLY COURT

3 Beds

2 Baths

1,662 Sq.Ft.

$629,900

MLS#: DENC2093608

Welcome to 2 Susie Court, located in the lovely community of The Legends at Frog Hollow Golf Club. This lovely corner lot home with amazing curb appeal, plush green grass and stunning landscaping shouts Pride of ownership. A two story colonial home located in a cul-de-sac.... where do I begin, the hardwoods, throughout, the crown moldings, the large rooms, the sun room... the list is endless. This home has 4 bedrooms and 2.1 bathrooms that have been renovated, a large living room and dining room, a large office, a stunning Kitchen open to the family room with Catedral ceilings and a stone gas fireplace, but my favorite is sunroom with its beautiful wooden ceiling. There is more than just beauty, young roof, young HVAC, young hot water heater, new hardwoods, newer rugs, newer crown moldings, newer appliances, refinished kitchen cabinets, freshly painted, workshop in the basement, central vacuum and a spacious unfinished basement with 9 ft ceilings and a rough in for a bathroom just waiting to be finished. This home is located in the Appoquinimink School District.
#DENC2099456

MIDDLETOWN

2 SUSIE COURT

4 Beds

2 Baths

2,850 Sq.Ft.

$625,000

MLS#: DENC2099456

Quick Delivery 5 bedroom home in Appoquinimink school district. READY TO GO! This lovely home offers a 1st floor full bath with bedroom/office space, and the remaining 4 beds and 2 baths upstairs. The Charleston floor plan offers a well crafted layout with walk-in pantry, butler's pantry, switchback staircase, and much more. Quality products like Hardie Plank Siding, Timbertech front porch, and Anderson windows add to the fine construction by this local, semi-custom builder (Benchmark Builders). Check in at the model home during business hours for a tour and more information. This home can be seen 7am-8pm via the NTerNow app. Simply show up, scan the QR code, and follow the instructions.
#DENC2095376

MIDDLETOWN

1011 STUYVESANT STREET

5 Beds

3 Baths

2,716 Sq.Ft.

$624,999

MLS#: DENC2095376

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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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