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 Middletown, MD real estate 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
232
# of Listings
3
Avg # of Bedrooms
$273
Avg. $ / Sq.Ft.
$647,221
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

232 Properties Found. Page 6 of 16.

To be built - New Construction! Monarch offers resort-style living featuring high-end finishes and flexible floor plans. At the heart of the community, residents will enjoy an amenity-rich clubhouse complete with a resort-style pool, pickleball and sports courts, and inviting indoor lounge spaces perfect for relaxation or connection. Combining the sophistication of luxury homes with the laid-back charm of Delaware living, Monarch delivers the perfect balance of comfort, style, and convenience—all just minutes from Middletown’s shopping, dining, and entertainment. The Cassidy is a ranch home starting at 2,528 sq. ft., featuring 4 bedrooms, 3.5 baths, and an unfinished bonus room. Open kitchen with walk-in pantry flows to great room and dining. Options available for extra bedrooms, baths, and outdoor living.
#DENC2093486

MIDDLETOWN

2205 EARLY COURT

4 Beds

3 Baths

2,528 Sq.Ft.

$674,900

MLS#: DENC2093486

Price Reduced! 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.

$665,000

MLS#: DENC2094672

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 amazing home feels and smells like brand-new construction! Don’t miss this rare opportunity to own a home 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 — complete with a game room and wet bar, media room, workshop or exercise area, full bathroom, and ample storage space. The main level showcases an inviting foyer with a coat closet, leading to a bright and open living and dining area filled with natural light. The kitchen includes birch cabinetry, granite countertops, stainless steel appliances, a pantry, and a large island with seating, opening to both the breakfast area and family room featuring a cozy fireplace. A convenient powder room completes the first floor. Upstairs, the owner’s suite features a spacious bedroom, two walk-in closets, and a large ensuite bathroom. Additional well-sized bedrooms and a hall bathroom offer comfort for family or guests. Additional highlights include a first-floor laundry room adjacent to the garage entry, an oversized deck perfect for outdoor entertaining, and a two-car garage. This home combines thoughtful design, functionality, and quality finishes—ready for you to move right in!
#DENC2092178

MIDDLETOWN

1236 PIMPERNELL PATH

5 Beds

3 Baths

2,550 Sq.Ft.

$662,000

MLS#: DENC2092178

Brand New 55+ Community in Middletown, DE The Morse home design blends a spacious open floorplan with classic architectural details, creating a timeless yet modern living experience. With 3 bedrooms (including one in the finished basement), 3.5 baths, and a 2.5-car garage, this home offers both functionality and refined style. Highlights include a fireplace with shiplap surround, feature walls in the foyer and owner’s suite, and a screened porch that overlooks beautiful community open space—perfect for relaxing or entertaining. The finished basement adds extra versatility, complete with a full bedroom and bath ideal for guests or extended family. The kitchen is designed for convenience and style, featuring smart appliance upgrades and quartz countertops for a sleek, modern finish. Laminate flooring throughout the first floor enhances the flow of the open-concept layout while offering easy maintenance. In the owner’s bath, a tiled shower enclosure with a rain shower head brings a spa-like touch to everyday living. For a full list of included features, please contact our sales representatives. Photos are for illustrative purposes only and may not represent the exact home or finishes available.
#DENC2091996

MIDDLETOWN

1602 JAYMES CIRCLE

3 Beds

2 Baths

2,349 Sq.Ft.

$659,900

MLS#: DENC2091996

New construction without the wait. This 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 with partially finished 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

Welcome to 734 Wood Duck Ct – A Stunning Blend of Comfort and Style in Middletown! Nestled on a quiet cul-de-sac in one of Middletown’s most desirable neighborhoods, this beautifully maintained 4-bedroom, 3-full-bath home is the perfect combination of space, function, and modern updates. Step inside to find an inviting layout featuring a dedicated home office, ideal for remote work or study. The heart of the home is the newly updated kitchen, equipped with sleek brand-new appliances, ample cabinetry, and a layout that opens seamlessly into the main living areas—perfect for everyday living and entertaining alike. Retreat to the spacious primary suite with its own private bath, while three additional bedrooms offer flexibility for family, guests, or hobbies. The home features three full bathrooms, ensuring convenience for everyone. Step outside to your personal oasis—an expansive stone and brick back patio that’s perfect for summer barbecues, cozy evenings, or morning coffee in a peaceful setting. Located just minutes from top-rated Appoquinimink schools, parks, shopping, and major commuter routes, this home checks all the boxes.
#DENC2083782

MIDDLETOWN

734 WOOD DUCK COURT

4 Beds

3 Baths

3,025 Sq.Ft.

$655,000

MLS#: DENC2083782

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

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.

$649,900

MLS#: VAWR2012638

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.
#DENC2093526

MIDDLETOWN

2206 EARLY COURT

3 Beds

2 Baths

2,254 Sq.Ft.

$644,900

MLS#: DENC2093526

The Fayetteville offers an open-concept layout paired with timeless classic design, creating a home that feels both inviting and refined. Scheduled for settlement in April 2026, this thoughtfully designed residence includes 3 bedrooms, 3 baths, and a 2-car garage, with flexible spaces ideal for everyday living and entertaining. Standout features include a finished basement that expands your living area, a cozy fireplace that anchors the main living space, and laminate wood flooring throughout the first floor for a warm, cohesive feel. A dramatic backsplash extending to the ceiling adds a designer touch in the kitchen. The kitchen is styled with light grey cabinetry and white quartz countertops, blending clean lines with modern elegance. Upstairs, carpeted bedrooms provide comfort and privacy, while the bathrooms feature upgraded showers with eye-catching diamond backsplash details. For a full list of included features, please contact our sales representatives. Photos are for illustrative purposes only and may not represent the exact home or finishes available.
#DENC2094616

MIDDLETOWN

851 MERLIN DRIVE

3 Beds

3 Baths

2,307 Sq.Ft.

$639,900

MLS#: DENC2094616

This is a builder model home sale. This beautiful Calloway Queen Anne offers 2,657 square feet of living space. The abundance of windows floods the family room and kitchen with natural light. Upgraded luxury vinyl plank runs throughout the first floor, the upstairs hall, and primary bedroom. The kitchen boasts an oversized island, quartz countertops, and a tiled backsplash. Both bathrooms offer quartz vanity tops.
#DENC2088810

MIDDLETOWN

5605 S BAYBERRY PKY

4 Beds

2 Baths

N/A

$639,000

MLS#: DENC2088810

Rothwell Estates from Benchmark Builders. The CLAYTON (to be built) is our starter 4 bedroom 2.5 bath 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
#DENC2079880

MIDDLETOWN

126 GREEN FOREST DRIVE 2 CLAYTON

4 Beds

2 Baths

2,586 Sq.Ft.

$638,000

MLS#: DENC2079880

Rothwell Estates from Benchmark Builders. The ARMSTRONG (to be built) is the smaller 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
#DENC2079868

MIDDLETOWN

126 GREEN FOREST DRIVE 1 ARMSTRONG

3 Beds

2 Baths

2,225 Sq.Ft.

$638,000

MLS#: DENC2079868

New on site 4 days ago
Welcome to this stunning home located in sought-after Middletown, DE. This gorgeous property boasts 3 bedrooms, 3.1 bathrooms, and a 2-car garage, offering plenty of space for comfortable living. As you step inside, you are greeted by luxury vinyl plank flooring that runs throughout the first floor. The main level features an office/flex room, perfect for those who work from home or need a versatile space. The open kitchen is a chef's dream, complete with granite countertops, tile backsplash, a large island, and stainless steel appliances. The kitchen seamlessly flows into the dining area and family room, where you can cozy up by the gas fireplace. Step outside to the rear yard, where you will find a composite deck and a fully fenced yard, perfect for outdoor entertaining. Upstairs, you will find a large loft area that offers additional flex space. The primary bedroom is generously sized and features a huge walk-in closet and an en suite bathroom with double sinks, a water closet, and a glass shower. There are two additional bedrooms, a hall bathroom, and a convenient laundry room. The lower level of the home is finished and offers a full bathroom, providing endless possibilities for use. Currently set up as a theater room and gym, this space could easily be converted into a 4th bedroom if desired. The Preserve at Deep Creek community amenities include a pool and lawn care, making this home low maintenance and perfect for those seeking a relaxed lifestyle. Conveniently located near downtown Middletown, routes 299, and 301, this home is move-in ready and meticulously maintained. Don't miss out on the opportunity to make this beautiful property your next home!
#DENC2095996

MIDDLETOWN

772 WALLASEY DRIVE

3 Beds

3 Baths

3,243 Sq.Ft.

$630,000

MLS#: DENC2095996

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.

$628,898

MLS#: DENC2095376

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Buyers resources
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Selling Your Home for More $$

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