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
254
# of Listings
3
Avg # of Bedrooms
$268
Avg. $ / Sq.Ft.
$655,181
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

134 Properties Found. Page 4 of 9.

Stunning new construction by Rachuba Homes in the heart of historic downtown Middletown. This is a rare opportunity to enjoy walkable small-town living in a brand new, move-in ready home, with no HOA! Situated on nearly half an acre, this thoughtfully designed 4 bedroom, 2.5 bath residence offers comfortable, practical living with an open layout ideal for everyday life and entertaining. The kitchen features stainless steel appliances, quality cabinetry, premium countertops, and a stylish backsplash. The main level includes 7-inch luxury plank flooring, black hardware accents, and a welcoming covered front porch. Upstairs, the spacious owner’s suite includes a walk-in closet and a private bath with a 6x7 shower and dual sinks. Three additional bedrooms, a full bath, and a conveniently located upper-level laundry complete the second floor. The finished lower level provides a large recreation space for additional living or entertaining, plus a rough-in for a full bath and space for a fifth bedroom with egress already in place. Located just steps from Middletown’s shops, restaurants, parks, and community events, and within the highly regarded Middletown school district, this home offers the convenience of an established downtown setting with the efficiency and peace of mind of new construction.
#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

New on site 1 day ago
Spacious ranch living on 6 fenced in acres! This well-maintained ranch home offers 3 acres with a 2-stall horse barn plus an additional 3 fenced in acres—perfect for horses, hobby farming, or room to roam. Enjoy the bonus of 21 fully paid solar panels, delivering energy efficiency and long-term savings. 2025 New Hot Water Heater, 2025 New Septic Pump, 2024 Peat Moss Drain Field was redone, 2022 New HVAC, 2019 Twenty One Solar Panels installed which are all paid for, 2016 Architectural Shingle Roof.
#VAWR2013462

MIDDLETOWN

5670 LONG MEADOW ROAD

3 Beds

2 Baths

2,975 Sq.Ft.

$695,000

MLS#: VAWR2013462

New on site 4 days ago
Semi-Custom Builder, so talk to the sales manager for additional design options. Last lot left in Rothwell Estates from Benchmark Builders. All 6 of our floor plans fit. We have a 7 month build time and rentals available for our buyers if you need a place to stay during the build. See the sales manager, Lindsay, for all the details. The GRANDVIEW (to be built) is the larger of our 2 ranch floor plans. It has an optional 2nd floor loft/bedroom area, but is spacious without it. The large kitchen & vaulted ceiling in the great room are some of the stand out features in this home. We encourage you to take the virtual tour to see this floor plan. Rothwell Estates is endowed with a rich variety of two-story and ranch models, which include basements and an abundance of standard features such as a stone water table, hardwood standard in the foyer, kitchen and breakfast area,& powder room. Granite counter tops in the kitchen, stainless steel appliances, an island, 42" maple cabinets, gas fireplace, recessed lights, tile baths, fully sodded yard and much, much more! With an emphasis on open and versatile floor plans, you are certain to find the home of your dreams. Residences are situated on perfectly sized home sites, most of which back up to open space. And, you'll love the comfort and peace of mind these energy-efficient homes provide. Located in the highly regarded Appoquinimink School District, families will find much to appreciate. Whether you're looking for a home that offers first-floor living or a grand two-story design, Rothwell Estates has something for everyone! Please visit the model home at 126 Green Forest Drive, Middletown, DE 19709. Agent must accompany buyer on first visit or pre-register prior to first visit on builder website
#DENC2097538

MIDDLETOWN

619 MCCRACKEN DRIVE 3 GRANDVIEW

3 Beds

2 Baths

2,822 Sq.Ft.

$694,000

MLS#: DENC2097538

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

Beautiful 6 bedroom, 3 1/2 bathroom colonial offering a covered front porch, 2 car garage, partially finished basement 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.

$689,900

MLS#: DENC2097264

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.

$689,575

MLS#: DENC2081304

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 on site 4 days ago
Semi-Custom Builder, so talk to the sales manager for additional design options. Last lot left in Rothwell Estates from Benchmark Builders. All 6 of our floor plans fit. We have a 7 month build time and rentals available for our buyers if you need a place to stay during the build. See the sales manager, Lindsay, for all the details. The HOUSTON (to be built) is our main decorated model. The 2 story foyer & great room, and a 2nd floor bridge are some of the stand out features in this home. We encourage you to take the virtual tour to see this floor plan. Rothwell Estates is endowed with a rich variety of two-story and ranch models, which include basements and an abundance of standard features such as a stone water table, hardwood standard in the foyer, kitchen and breakfast area,& powder room. Granite counter tops in the kitchen, stainless steel appliances, an island, 42" maple cabinets, gas fireplace, recessed lights, tile baths, fully sodded yard and much, much more! With an emphasis on open and versatile floor plans, you are certain to find the home of your dreams. Residences are situated on perfectly sized home sites, most of which back up to open space. And, you'll love the comfort and peace of mind these energy-efficient homes provide. Located in the highly regarded Appoquinimink School District, families will find much to appreciate. Whether you're looking for a home that offers first-floor living or a grand two-story design, Rothwell Estates has something for everyone! Please visit the model home at 126 Green Forest Drive, Middletown, DE 19709. Agent must accompany buyer on first visit or pre-register prior to first visit on builder website
#DENC2097540

MIDDLETOWN

619 MCCRACKEN DRIVE 5 HOUSTON

4 Beds

2 Baths

3,368 Sq.Ft.

$685,000

MLS#: DENC2097540

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.

$684,900

MLS#: DENC2093526

Discover the ideal blend of comfort, convenience, and refined charm in this spacious Middletown home featuring 4 bedrooms and 2.5 baths. Thoughtfully designed for everyday living and effortless entertaining, the property offers an inviting front porch and sits just steps from the community clubhouse, pool, and tennis courts. Inside, an eat-in kitchen with a butler’s pantry opens to bright living spaces enhanced by hardwood flooring, recessed lighting, and desirable modern features. A private first-floor office provides a quiet work-from-home solution, while a separate sitting room off the primary suite creates a relaxing retreat. Outdoor living is equally impressive with a private paver patio, ideal for dining al fresco or hosting friends and family. Additional highlights include an irrigation system, alarm system, and a walk-out basement with walls and a bathroom already roughed in, offering endless potential for future finishing. With its coveted location, thoughtful floor plan, and access to sought-after community amenities, this home is a Middletown gem ready for its next owner. Home is being sold AS-IS.
#DENC2095970

MIDDLETOWN

308 ELLENWOOD DRIVE

4 Beds

2 Baths

4,624 Sq.Ft.

$680,000

MLS#: DENC2095970

New on site 2 days ago
Enjoy easy one-level living on 4.25 scenic acres in beautiful Middletown, complete with two exceptional outbuildings and stunning rural mountain views. This well-maintained, updated home offers hardwood floors throughout the main level (tile in baths), an updated primary suite with walk-in shower and mini-split system, and a spacious, well-equipped kitchen with abundant cabinetry and counter space. The living room is perfect for cozy nights in, featuring pellet stove inserts and a motorized, ceiling-mounted retractable projector screen. The fully finished lower level adds valuable living space with an additional bedroom, office or craft area, exercise room, and half bath—ideal for guests or working from home. Outside is where this property truly shines. A 24’ x 40’ heated and air-conditioned outbuilding provides ample space for vehicles, equipment, and a wood workshop, and is supported by a quiet 30KW whole-property generator capable of powering the home and both outbuildings. The second outbuilding, 42’ x 30’, features propane heat and two motor-operated 12’ x 14’ insulated doors—perfect for an RV, boat, or large equipment. Relax on the front porch or enclosed rear deck, entertain with ease thanks to expanded parking, and enjoy peace of mind with tall chain-link fencing—great for pets. Offering space, power, and flexibility rarely found in today’s market, this property is one you won’t want to miss. Best of all... the sellers elected to list this home $45,000 below the current market value for a quick sale! Better hurry!
#MDFR2076638

MIDDLETOWN

1676 MONUMENT ROAD

5 Beds

2 Baths

3,688 Sq.Ft.

$675,000

MLS#: MDFR2076638

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Selling Your Home for More $$

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