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
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 7 of 18.

Brand New 55+ Community in Middletown, DE Welcome to the Aberdeen II, a beautifully designed home that blends an open-concept layout with charming Farmhouse-inspired elements. Offering 3 bedrooms, 3 baths, and a 2-car garage, this home delivers the perfect balance of comfort, style, and functionality. The main living area features a stunning stone fireplace and stained ceiling beams in the great room, creating a warm and inviting space filled with character. A finished basement provides additional living space ideal for entertaining, guests, or a private retreat, while the screened deck extends your living area outdoors for relaxing and enjoying the surroundings. The kitchen is equipped with a smart cooking suite of appliances and quartz countertops, combining modern convenience with timeless design. Laminate flooring flows throughout the first floor for a cohesive and low-maintenance finish. The baths include a walk-in shower with a rain shower head, offering 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.
#DENC2100330

MIDDLETOWN

1618 JAYMES CIRCLE

3 Beds

3 Baths

2,148 Sq.Ft.

$659,990

MLS#: DENC2100330

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

BACK ON THE MARKET THROUGH NO FAULT OF THE SELLERS AND AT A NEW LOW PRICE - SHOWINGS RESTART 4/12. MOTIVATED SELLERS! BRING YOUR OFFERS! Nestled in the Brighton subdivision, this exquisite Colonial-style residence, built by Toll Brothers in 2023 on a corner lot, embodies the pinnacle of modern luxury living. Spanning approximately 2,650 square feet, this detached home offers a harmonious blend of elegance and functionality, perfect for those who appreciate high-end finishes and thoughtful design. Step inside the front door from the covered porch to discover an open floor plan that seamlessly integrates living spaces, accentuated by luxury vinyl plank flooring and strategically placed recessed lighting that enhances the ambiance of the 9' ceilings. The heart of the home is the gourmet kitchen, featuring granite countertops and a spacious island that invites culinary creativity. Equipped with top-of-the-line appliances, including a smart refrigerator, smart double oven, built-in microwave, and sleek induction cooktop, this kitchen is a chef's dream. The adjoining flex space serves perfectly as a dining area providing an ideal setting for entertaining naturally extending between the kitchen, dining, and great room areas. The large pantry ensures ample storage for all your culinary essentials coupled with a second closet space off the kitchen which can feature as an additional pantry or kitchen appliance storage to keep those granite countertops clear of clutter! The great room is a natural gathering space lit by abundant natural light. The far wall features sound absorbing slated Sonolok by Artika paneling making movie night an experience! Around the corner on the main level the home office is easily accessible without feeling overly pronounced striking the perfect balance for those who want to separate work in the office from living in the home. The main level powder room includes the PEX plumbing ran to convert to a full bath should you wish to do so in the future. Upstairs the primary suite ties together the same luxury vinyl plank from the main level. The suite includes a generous walk-in closet with extensive built-in shelving offering a dream wardrobe organization system. The en-suite tile floored bathroom is a haven showcasing a walk-in shower compatible with voice control through Anthem by Kohler and enriched by green porcelain tile and gold colored fixtures that promises relaxation and rejuvenation. A designated electrical outlet provides the opportunity for smart toilet or electronic bidet options should the future owners wish to continue adding to the modern oasis. Three additional spacious bedrooms adorn the upper level each featuring soft carpet flooring and ceiling fans. These bedrooms are complemented by a stylish full bathroom. The upper-floor laundry room adds a touch of practicality, making everyday chores a breeze and easily keeping laundry out of view when entertaining. Security is paramount, with a Ring camera as well as an advanced Reolink system of exterior cameras ensuring peace of mind. Outside, the fenced-in corner lot enhances privacy and curb appeal, while the rear-entry detached two car garage continues to elevate with an electric vehicle charger and additional storage space. Additionally, the asphalt driveway accommodates multiple vehicles. A charming small greenhouse easily accessed from the basement walkout adds a unique touch, perfect for gardening enthusiasts. When finished gardening, the gorgeous backyard patio provides space to relax and unwind enjoying fresh air. In addition to the walkout stairs the basement includes storage shelving, an active radon mitigation system, and rough-in plumbing. This property is not just a home; it's a lifestyle featuring intentional upgrades and boundless potential. Experience the luxury of modern living where every detail has been meticulously crafted for comfort, style and functionality -and all in the renowned Appoquinimink School District.
#DENC2092354

MIDDLETOWN

141 S LORES LANDING ROAD

4 Beds

2 Baths

2,650 Sq.Ft.

$649,999

MLS#: DENC2092354

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

WELCOME TO 1236 PIMPERNELL PATH! THIS BEAUTIFULLY MAINTAINED, MOVE-IN READY, 4-YEAR-OLD D.R. HORTON HOME OFFERS EXCEPTIONAL SPACE AND MODERN DESIGN THROUGHOUT. THIS STUNNING HOME FEELS AND SMELLS LIKE BRAND-NEW CONSTRUCTION! DON’T MISS THIS RARE OPPORTUNITY TO OWN IN ONE OF THE MOST DESIRABLE COMMUNITIES. THIS SPACIOUS TWO-STORY RESIDENCE OFFERS NEARLY 2,600 SQ. FT. OF LIVING SPACE, FEATURING 5 BEDROOMS AND 3 BATHROOMS. THE CLEAN, READY-TO-FINISH BASEMENT PROVIDES INCREDIBLE POTENTIAL—IDEAL FOR A GAME ROOM WITH WET BAR, MEDIA ROOM, WORKSHOP OR EXERCISE AREA, FULL BATHROOM, AND AMPLE STORAGE. THE MAIN LEVEL FEATURES AN INVITING FOYER WITH A COAT CLOSET, LEADING TO A BRIGHT, OPEN-CONCEPT LIVING AND DINING AREA FILLED WITH NATURAL LIGHT. THE KITCHEN IS EQUIPPED WITH BIRCH CABINETRY, GRANITE COUNTERTOPS, STAINLESS STEEL APPLIANCES, A PANTRY, AND A LARGE ISLAND WITH SEATING. IT FLOWS SEAMLESSLY INTO THE BREAKFAST AREA AND FAMILY ROOM, COMPLETE WITH A COZY FIREPLACE. A CONVENIENT POWDER ROOM COMPLETES THE FIRST FLOOR. UPSTAIRS, THE OWNER’S SUITE OFFERS A SPACIOUS BEDROOM, TWO WALK-IN CLOSETS, AND A LARGE ENSUITE BATHROOM. ADDITIONAL WELL-SIZED BEDROOMS AND A HALL BATHROOM PROVIDE COMFORT FOR FAMILY OR GUESTS. ADDITIONAL HIGHLIGHTS INCLUDE A FIRST-FLOOR LAUNDRY ROOM LOCATED NEAR THE GARAGE ENTRY, AN OVERSIZED DECK PERFECT FOR OUTDOOR ENTERTAINING, AND A TWO-CAR GARAGE. THIS HOME PERFECTLY COMBINES THOUGHTFUL DESIGN, FUNCTIONALITY, AND QUALITY FINISHES—READY FOR YOU TO MOVE RIGHT IN!
#DENC2100206

MIDDLETOWN

1236 PIMPERNELL PATH

5 Beds

3 Baths

2,550 Sq.Ft.

$649,000

MLS#: DENC2100206

QUICK DELIVERY!!! Welcome to the popular Bloomfield Model in the 55+ community of Traditions at Whitehall. This floor plan has 2-Bedrooms with a standard 2 car attached garage. Vaulted ceiling great room open to the kitchen and dining area and sunroom. You will have plenty of space if you like to entertain. A rear Owner's Suite gives maximum privacy and includes a large walk-in closet and en-suite with a double bowl vanity and tile shower. The second floor features a large loft, walk-in closet for additional storage or overnight guests, as well as a full bathroom. Community offers in ground pool w/lounge areas, clubhouse featuring exercise & billiards room, gathering/lounge space, full kitchen and a large outdoor patio/grilling area! Builder Splits Transfer Tax (***Photos are of a similar home and may contain options & upgrades not included in listing price shown.***). Come by the model home during business hours for more details and to take a tour.
#DENC2100364

MIDDLETOWN

264 BALDY LN

2 Beds

3 Baths

2,053 Sq.Ft.

$639,999

MLS#: DENC2100364

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

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 has 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.

$639,900

MLS#: MDFR2078904

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 Armstrong floor plan is the smaller of our two ranch floor plans. It has a large kitchen and vaulted 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 Armstrong is one of 6 floor plans available to build, and we have one to see in person until May 2026.
#DENC2100368

MIDDLETOWN

619 MCCRACKEN DRIVE 3 ARMSTRONG

5 Beds

3 Baths

3,560 Sq.Ft.

$638,000

MLS#: DENC2100368

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

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 Traditions @ Whitehall, a 55+ Active Community just south of the C&D Canal in Middletown, DE. This better than new home built in 2022 is ready for you to move right into. No need to wait months on end for a house to be built AND $125K less expensive than building this home new. The owners of this lovely home welcome you to unpack your bags and enjoy the fruits of their labor with additional upgrades they have made along the way: like a patio, LVP flooring and more. This Cottonwood model, the largest offered in this community, boasts 3 bedrooms, 2 full baths and an enormous full footprint basement awaiting your vision to be finished. This house has too many upgrades to mention but rest assured all the bells and whistles have been appropriately added. Ask agent for complete list and floor plans. Come make this house your home.
#DENC2097830

MIDDLETOWN

240 BALDY LANE

3 Beds

2 Baths

2,725 Sq.Ft.

$625,000

MLS#: DENC2097830

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

TO BE BUILT - The Bennett This beautiful 2 story home features 4 bedrooms, 2.5 baths, 2 car garage. Standard features include a partially finished basement, Granite kitchen countertops, 42" maple cabinets, stainless steel appliances, hardwood floors in foyer, kitchen & breakfast area & a stone water table on the exterior. Appoquinimink School district!
#DENC2079328

MIDDLETOWN

400 REDERICK LANE 3 BENNETT

4 Beds

2 Baths

3,000 Sq.Ft.

$624,000

MLS#: DENC2079328

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