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
263
# of Listings
3
Avg # of Bedrooms
$271
Avg. $ / Sq.Ft.
$633,497
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

263 Properties Found. Page 7 of 18.

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.

$629,990

MLS#: DENC2091996

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

NEW PRICE! 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.

$625,000

MLS#: VAWR2012638

New on site today
Beautiful 4 bedroom, 3.5 bath single family home situated on a generous .53 acre flat corner lot with peaceful tree lined views in the desirable Foxfield community of Middletown. Inside, the home features an open kitchen that flows into the sunken family room with cathedral ceilings and brick wood burning fireplace, creating a comfortable and inviting space for everyday living and entertaining. The kitchen offers upgraded hickory cabinetry, quartzite countertops, tile backsplash, slide out drawers in the island, and corner lazy Susans, providing both style and functionality. The main level floor plan includes a first floor office/study, open living and dining rooms, LVP flooring and an updated powder room adding to the home's appeal. An added bonus of a discrete convenient laundry chute from the upper floor that opens directly into the main floor laundry room. Upstairs, you will find Bruce hardwood flooring throughout all bedrooms, closets, and the hallway, along with custom closet organizers in each bedroom for added storage and organization. This home offers a partially finished basement with a walk up, that includes a small room, full bathroom and plenty of storage opportunities as well. Step outside to a front covered porch or out back to a beautifully designed patio, perfect for relaxing or hosting family and friends with an incredible view of the annual Middletown Independence fireworks celebration. The spacious corner lot offers privacy and room to enjoy the outdoors. Recent updates include a new roof, gutters, and downspouts (July 2025), new water heater (February 2024), whole house water softening system (February 2024), expanded and newly installed driveway with gravel underlay and additional parking space (April 2024). Located in just minutes and an easy walk to Coblentz Park, the Middletown School Campus (grades 3-12), many walking trails, sports fields, skate park, open green space, playgrounds, and a peaceful pond. Enjoy the convenience of being able to walk to nearby restaurants, grocery store and coffee shops while living in a quiet, well maintained neighborhood with no HOA. This home offers a wonderful combination of space, thoughtful updates, outdoor living, and small town charm.
#MDFR2078098

MIDDLETOWN

118 MANDA DRIVE

4 Beds

3 Baths

2,892 Sq.Ft.

$625,000

MLS#: MDFR2078098

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

New on site 1 day ago
Tucked within the desirable Old Reliance Farms neighborhood, this exceptional home offers a rare chance to own in this peaceful community. Step inside to find bright hardwood flooring leading through the foyer to the formal dining room, highlighted by classic chair rail detailing and a lighted tray ceiling. The spacious eat-in kitchen features an island/breakfast bar and opens up to the bright sunroom, creating an inviting space for gatherings. The cozy family room showcases a stone gas fireplace, serving as the heart of the home. The main level also includes an additional living area, a versatile office or recreation room, a full bath, and a convenient laundry area. Upstairs, the primary suite is complete with a large walk-in closet and a private ensuite bath featuring a soaking tub and a walk-in shower. Two additional spacious bedrooms each offer walk-in closets and share a full bath. The finished basement expands your living space with a game room full bath, additional office, and ample storage—ideal for both entertaining and everyday functionality. Step outside to enjoy the beautifully designed back patio, perfect for relaxing or entertaining while taking in the peaceful surroundings of this quiet community.
#PADA2057588

MIDDLETOWN

1325 PHEASANT RUN ROAD

3 Beds

4 Baths

4,126 Sq.Ft.

$624,999

MLS#: PADA2057588

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

Build your dream home with Schaeffer Homes in Middletown with Schaeffer Homes! This home is to be built through their Build On Your Lot Program. Starting at 2,223 square feet, the Ellis is a sizable home, with 2 modern elevations options. This model includes 4 bedrooms, 2 1⁄2 baths, and a 2-car garage, providing ample space for families of all sizes. The home starts at 2-stories, with the option to add to a 3rd floor if you are in need of an extra bedroom and bath!! The great room is adequate enough to fit a large dining table, while still allowing extra space to spread out between the kitchen and family room. With its sleek design and thoughtful layout, the Ellis is the perfect blend of style and functionality. The homesite is listed for $230,000, the home is $271,900, and the estimate for land development cost is $120,000. Land development costs can be more or less than $120,000. Seller and Builder make no representation of the feasibility and cost for site development and will provide a due diligence period to the Buyer. Schaeffer Homes has the exclusive right to build on this lot and will assist the Buyer through the due diligence process. It is unknown if a basement foundation is available until soil testing is completed, which will be the responsibility of the Buyer. Seller and Builder make no representation of the feasibility and cost for site development and will provide a due diligence period to the Buyer. Schaeffer Homes has the exclusive right to build on this lot and will assist the Buyer through the due diligence process. ***NOTE: Home is to be built. Pictures and virtual tour are of the same base model with upgraded options shown. Other Schaeffer Floorplans are available to be built on this homesite.
#DENC2092334

MIDDLETOWN

1487 BUNKER HILL ROAD

4 Beds

2 Baths

2,223 Sq.Ft.

$621,900

MLS#: DENC2092334

Stunning 4-bed, 3.5-bath single-family home ideally located just minutes from Downtown Middletown. Set on a generous 15,000 sq. ft. corner lot with peaceful tree-lined views, this residence boasts numerous enhancements inside and out. Step inside to upgraded flooring and sophisticated finishes throughout. The inviting living room showcases custom built-ins with shelving and storage, while the dining area is adorned with classic wainscoting and elegant lighting. The kitchen is a chef’s dream, equipped with custom cabinetry, granite countertops, a stylish stone backsplash, recessed lighting, and stainless steel appliances—including a newer refrigerator, dishwasher, and microwave (2022–2024). Adjacent to the kitchen, the expansive family room is perfect for entertaining, featuring a cozy wood-burning fireplace and French doors that open to a stone patio overlooking the tranquil backyard. A convenient powder room completes the main level. Upstairs, retreat to the spacious owner’s suite with custom accent wall, walk-in closet, and a recently renovated luxurious en-suite bath (2024). This spa-like bathroom offers a dual-sink vanity and an oversized walk-in shower with a built-in bench, body jets, and three shower heads—including an overhead rainfall system—designed for ultimate relaxation. Three additional bedrooms share a modern full bath with tub/shower combo and updated wall and floor tiles. The lower level provides flexible living space, featuring a large rec room with a wet bar, a potential 5th bedroom, full bath with stand-up shower, and laundry area with ample storage—ideal for an in-law suite, home office, gym, or play area. Step outside and enjoy your private oasis, complete with a stone patio, hot tub, outdoor string lights, storage shed, and a flat, fully fenced yard for everyone to enjoy! The attached two-car garage and driveway offer off-street parking for up to four vehicles. Other recent improvements include newer HVAC (2023), water heater (2022), and roof (approx. 2019). No HOA fees! Ideally situated near Middletown Park with sports fields, trails, and pond, Middletown Library, and all the dining and shopping that Downtown Middletown and Frederick have to offer!
#MDFR2077776

MIDDLETOWN

4300 ZIRCON ROAD

4 Beds

3 Baths

2,912 Sq.Ft.

$619,900

MLS#: MDFR2077776

TO BE BUILT-The Greenspring -This beautiful 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! Self-Guided Tours available daily 7 am-8 pm. Download "NterNow" APP on smart phone. Enter property ID at front door of Model; scan drivers license and door will auto unlock. Please make sure door is closed and door will auto lock.
#DENC2079324

MIDDLETOWN

400 REDERICK LANE 1 GREENSPRING

4 Beds

2 Baths

3,021 Sq.Ft.

$619,000

MLS#: DENC2079324

Welcome to Baymont Farms — where resort-style living meets effortless luxury. Located in one of Middletown’s premier 55+ active adult communities, this stunning single-family home—just 2.5 years young—offers refined design, thoughtful upgrades, and the relaxed elegance you are looking for in your next home. Freshly painted and beautifully maintained, the home is completely move-in ready and radiates a bright, sophisticated feel throughout. Offering 3 bedrooms and 3 full baths, the versatile floor plan is designed for both everyday comfort and effortless entertaining. A private upper-level suite creates the perfect retreat for guests, grandkids, or hobbies, complete with its own bedroom, full bath, and sitting area. At the heart of the home is a beautifully appointed gourmet kitchen featuring crisp white cabinetry, quartz countertops, stainless steel appliances, and a spacious center island with bar seating—ideal for casual gatherings. The adjoining dining area is accented with charming farmhouse wainscoting, while the dramatic floor-to-ceiling stone gas fireplace anchors the great room and creates a warm, inviting focal point. A thoughtfully designed private office with custom built-in bookcase and rolling ladder offers both style and function—perfect for reading, working, or pursuing favorite hobbies. Designed with easy one-floor living in mind, the spacious owner’s suite provides a peaceful retreat with a luxurious en-suite bath and an oversized walk-in closet. Outdoor living is equally special. The Trex deck offers a perfect setting for entertaining or quiet evenings outdoors, while the sun-filled east-facing sunroom welcomes morning light and overlooks the beautifully landscaped backyard highlighted by merlot crepe myrtle trees. In the evening, unwind on the charming front porch and enjoy picturesque sunset views framed by apricot and berry-red miniature rose bushes. Additional highlights include professionally landscaped grounds, an irrigation system, a full unfinished basement already plumbed for future expansion, and a spacious two-car garage. Life at Baymont Farms feels like being on vacation year-round, with amenities including: • Resort-style pool with tiki bar • Pickleball and bocce courts • Scenic walking and biking trails • Kayak access to Drawyers Creek • Dog park • A stunning clubhouse hosting over 50 social clubs and activities, from mahjong and bourbon tastings to yoga, arts & crafts, book clubs, poker nights, and festive holiday gatherings. Experience the perfect blend of luxury, comfort, and vibrant community living. Schedule your private tour today and discover why Baymont Farms is one of Middletown’s most sought-after active adult communities
#DENC2098450

MIDDLETOWN

507 CHERRY BARK ROAD

3 Beds

3 Baths

2,700 Sq.Ft.

$615,000

MLS#: DENC2098450

Welcome to 3016 Barber Lane! This gorgeous, 55+ newly constructed detached home was built in 2024 and is located in Parks Edge, a part of the Village of Bayberry community in Middletown, Delaware! Situated on a premium corner lot, this beautifully upgraded Cooper II model with a two car garage offers great views with a pocket park in front and a meadow behind the home that cannot be built on! This thoughtfully designed home features 2 bedrooms, 2 full baths, and a versatile den/flex space that can serve as an office or easily convert to a third bedroom. From the moment you step inside, you’ll appreciate the luxury vinyl plank flooring that runs throughout the main living areas and bedrooms! The gourmet kitchen is a standout, featuring a huge level 3 quartz island, stainless steel appliances, a double wall oven, electric glass-top range, built-in microwave, and dishwasher. The cabinetry package was the highest upgrade offered (level 3), complete with soft-close doors and drawers and pull-out racks for maximum functionality, and the pantry has been enhanced with a custom Closet Factory system! The kitchen flows seamlessly into the living and dining areas with a nice open floor plan! Heading to the bedrooms you will find a spacious primary suite that includes a beautifully tiled bath with a walk-in shower and built-in seat. A large primary closet is also outfitted with a fully customized master closet system by Closet Factory. The second bedroom is also a great size with a large closet and a cozy nook in the room! Additional custom Closet Factory upgrades were added to the laundry room, providing exceptional organization and storage. The outdoor living is just as impressive, with a screened-in porch leading to a 16x20 maintenance-free vinyl deck with metal spindles—perfect for entertaining or simply enjoying the peaceful meadow views. The home also includes a two-car garage with a Liftmaster garage door open that connects to MyQ App- so convenient! There is also a huge unfinished basement which has been professionally water-sealed floor for added peace of mind. After move-in, the owner put in over $40,000 in additional upgrades to the home, including custom zebra blinds on nine windows, tinted privacy mirror polarized glass at the front door, patio sliders, and primary bath window, grab rails in the bathroom and five ceiling fans with remotes were installed. In addition- EVERY light fixture, faucet, and door handle was upgraded throughout the home, and three wall-mounted TV setups with electrical were installed. Front railings were also added to the front porch! The irrigation system includes a Wi-fi adaptor so it connects to your phone and can control each zone in the system! This exceptional property combines premium lot positioning, extensive upgrades, and move-in-ready condition in one of Middletown’s most desirable active adult communities! Book your tour today!
#DENC2098048

MIDDLETOWN

3016 BARBER LANE

2 Beds

2 Baths

1,866 Sq.Ft.

$615,000

MLS#: DENC2098048

Welcome to the Cottonwood Model, TO BE BUILT, in the highly sought-after 55+ community of Traditions at Whitehall. This 3-bedroom home features a generous Owner’s Suite at the front of the home, complete with double walk-in closets leading to a luxurious en-suite bath, offering a privacy water closet and a 5-foot tile shower. At the rear of the home, you will find the kitchen and dining area that opens to a bright and airy great room, perfect for relaxation or entertaining. Step outside to enjoy the peaceful surroundings on the optional deck off the breakfast area, where you can take in views of the trees and open space. With a variety of structural and decorative options available, this home can be customized to suit your style and needs. The Cottonwood Model offers the perfect blend of comfort, size, elegance, and low-maintenance living in a vibrant active adult community. As a resident you will enjoy access to amenities that include a clubhouse, fitness facilities, swimming pools, walking trails, and a full calendar of social events to keep you engaged and connected with neighbors.
#DENC2080210

MIDDLETOWN

204 BALDY LANE COTTONWOOD

3 Beds

2 Baths

2,477 Sq.Ft.

$614,000

MLS#: DENC2080210

TO BE BUILT-The Eden II is our largest four-bedroom model with a lot of versatility. It can easily accommodate a fifth bedroom if needed. The owner's suite has a separate sitting area, and two walk-in closets. All bedrooms are generously sized. The eat-in kitchen is well laid out with an open flow to the rest of the living space. This floor plan is outstanding. Standard features include stone water table, stainless steel appliances, granite counter tops, hardwood in foyer, kitchen & breakfast.
#DENC2079332

MIDDLETOWN

400 REDERICK LANE 5 EDEN II

4 Beds

2 Baths

3,195 Sq.Ft.

$614,000

MLS#: DENC2079332

Welcome Home! Located in the sought-after 55+ community of The Ponds at Bayberry, this exquisite 3-bedroom, 2-full-bath home offers comfort, style, and resort-style living. Residents enjoy fantastic amenities, including a clubhouse, pool, and a full calendar of activities. The home features a stunning stone front exterior and a spacious covered porch perfect for relaxing. Inside, you’ll find an open-concept layout with gleaming hardwood floors, large windows that fill the home with natural light, and a beautifully upgraded kitchen ideal for cooking and entertaining. Step outside to a gorgeous back deck with a retractable awning overlooking a private, tree-lined backyard—a peaceful retreat for morning coffee or evening gatherings. In the basement you will find a rough in for plumbing and a walk-out with sliding doors leading to the private back yard. This beautiful home in The Ponds at Bayberry has everything you’re looking for in a vibrant 55+ community. Don’t miss your chance to make it yours
#DENC2093966

MIDDLETOWN

624 VIVALDI DRIVE

3 Beds

2 Baths

2,050 Sq.Ft.

$609,999

MLS#: DENC2093966

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