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
261
# of Listings
3
Avg # of Bedrooms
$272
Avg. $ / Sq.Ft.
$637,643
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

129 Properties Found. Page 7 of 9.

Prime commercial site. This 1.54-acre property boasts a coveted B-2 zoning, making it an ideal location for business ventures. Conveniently positioned just off Interstate 81 and a short drive from Interstate 66, this site offers excellent visibility, ensuring maximum exposure for any enterprise. Situated between two well-known establishments, McDonald's and Econo Lodge, it benefits from high traffic and customer flow. With public utilities readily available, the infrastructure is in place to support a wide range of commercial activities. Moreover, the surrounding area is experiencing substantial residential growth, indicating a thriving market and potential customer base. This commercial site's strategic location, zoning, excellent visibility, proximity to major highways, and supportive infrastructure make it an enticing prospect for entrepreneurs looking to establish or expand their businesses in a rapidly developing area.
#VAFV2013246

MIDDLETOWN

RELIANCE ROAD

None Beds

None Baths

1.38 acres

$595,000

MLS#: VAFV2013246

New on site 1 day ago
Welcome to 541 Diamond Dr - where your future home awaits. Located in the desirable Lakeside community, this beautifully updated Colonial offers the perfect blend of comfort, space, and style. Featuring 4 bedrooms and 2.5 bathrooms, this move-in ready home has been completely refreshed with brand new carpets, fresh paint throughout, new countertops, and updated kitchen appliances. Step inside to an inviting open floor plan designed for both everyday living and entertaining. Beautiful new luxury vinyl plank flooring spans the foyer and formal living and dining spaces on the left, that lead into your beautifully polished kitchen that has been completely refreshed. Gorgeous quartz countertops, crisp white cabinetry, stainless steel appliances, a center island, eat-in area and pantry are just some of the incredible features of this jaw-dropping kitchen. Sliding glass doors lead you outside, where a large deck overlooks a beautiful in-ground pool. This private fenced yard has mature trees for privacy and shade, keeping you cool and covered for summer pool parties. The cozy family room glows with natural light from large windows and features a natural gas fireplace. Upstairs, the second floor laundry space brings added convenience, and the primary bedroom has stunning vaulted ceilings, double walk-in closets, and a primary bath with a double vanity, shower, and separate bath. Three more incredible bedrooms and a full bathroom round out the second floor, but the fun really begins in the finished basement, with even more room to spread out. This home is located in a prime location in the town limits of Middletown, within walking distance to Silver Lake Park, Middletown YMCA, and Middletown Library. This combination of elegance, convenience, and functionality is a rarity 0- don't miss your chance to call 541 Diamond Dr your home!
#DENC2098996

MIDDLETOWN

541 DIAMOND DRIVE

4 Beds

2 Baths

2,100 Sq.Ft.

$595,000

MLS#: DENC2098996

Edmonston -TO BE BUILT. Come tour our decorated model during business hours. This 4 bedroom open floor plan welcomes homeowners and visitors alike in a space that flows effortlessly from one room to the next. This plan offers 2 version, the standard offering a first floor owner's suite, and the alternate offering a larger great room and secondary bedroom on the first floor. There is a spacious kitchen with hardwood floors, along with 42" maple cabinets, granite countertops, and so much more! The picture shown is of our largest porch option, but there are several sizes to choose from. If you are looking for a community with planned amenities, retail, school and everything else you can imagine, visit the first new urbanism concept community in Delaware, The Town of Whitehall. Agents must accompany buyer on first visit or pre-register on builder's website prior to first visit.
#DENC2079210

MIDDLETOWN

530 WHEELMEN STREET 1 EDMONSTON

4 Beds

2 Baths

2,716 Sq.Ft.

$591,000

MLS#: DENC2079210

Savannah -To be built. This floor plan feature 4 bedrooms, 2.5 baths, second floor laundry, 2 car attached or detached rear entry garage, and an open floor plan for entertainment with a huge great room. Welcome to your new hometown! At Whitehall, the hometown is finally getting its comeback. It's the first town to be founded in Delaware in over a century, and it's planned for all homes, businesses and community traditions that make real towns real places. Walk to the park, doctor's office, or to school. Whitehall will have it all! Agent must accompany client on first visit or pre-register client on builder website prior to first visit.
#DENC2079250

MIDDLETOWN

530 WHEELMEN STREET 7 SAVANNAH

4 Beds

2 Baths

2,854 Sq.Ft.

$591,000

MLS#: DENC2079250

CHARLESTON -TO BE BUILT. This 4 bedroom (OPTIONAL 1ST FLOOR 5TH BEDROOM) open floor plan welcomes homeowners and visitors alike in a space that flows effortlessly from one room to the next. There is a spacious kitchen with hardwood floors, along with 42" maple cabinets, granite countertops, and so much more! Be the first to build this floor plan and get a special incentive off any upgrades. Ask the sales manager for details. If you are looking for a community with planned amenities, retail, school and everything else you can imagine, visit the first new urbanism concept community in Delaware, The Town of Whitehall. Agents must accompany buyer on first visit or pre-register on builder's website prior to first visit.
#DENC2079248

MIDDLETOWN

530 WHEELMEN STREET 6 CHARLESTON

4 Beds

2 Baths

2,730 Sq.Ft.

$590,000

MLS#: DENC2079248

Welcome to 230 Anglesey Drive, a stunning home where luxury and thoughtful design meet everyday comfort. Step inside and be greeted by soaring 9-foot ceilings and rich 6-inch hardwood planks that flow throughout the main living areas, setting the tone for the elegance that awaits within. The open-concept floor plan creates a seamless transition between living, dining, and entertaining spaces, anchored by a warm gas fireplace and framed with timeless plantation shutters. At the heart of the home lies a chef-inspired kitchen, beautifully appointed with porcelain backsplash, quartzite countertops, and a striking 8.5-foot island perfect for gathering. GE stainless steel gas appliances – including an electric wall oven, built-in microwave, and full gas stove – ensure that both cooking and hosting are effortless. This home offers two spacious bedrooms along with a sophisticated office featuring designer grass cloth wallpaper, easily transformable into a third bedroom if desired. The primary suite is a true retreat with a dramatic trey ceiling and a spa-like bath showcasing a floating vanity, walk-in porcelain shower with mother-of-pearl accents, brushed gold fixtures, complemented by an anti-steam mirror with a mini heater above the shower. A custom-built linen closet adds both convenience and luxury. Two additional full bathrooms provide convenience and style for guests and family alike. A laundry room off the primary bedroom includes a Maytag washer and dryer (gas). The living space extends into the finished, wide-open basement, offering incredible flexibility with its own full bath and endless possibilities for recreation, hobbies, or guest accommodations. Storage is thoughtfully integrated throughout the home, complemented by modern recessed LED lighting and a tank-less Noritz water heater that ensures energy efficiency and endless comfort as well as a whole house water purifier and whole house blue light air filtration. Leading to the outside is a tinted sliding glass door, a fenced-in backyard invites relaxation and entertaining with a covered, composite deck – your private outdoor oasis with a whole yard irrigation system. An attached two-car garage completes this exceptional home and adds everyday practicality. Located in the 55+ section of the Preserve at Deep Creek known as Legacy, homeowners enjoy exclusive access to the 55+ pool, clubhouse, and fitness center, plus full use of community-wide amenities. While only two streets are age-restricted, all residents in Legacy enjoy shared benefits, with added exclusivity reserved for 55+ homeowners. Commuting and convenience are effortless thanks to the home’s central location – with quick access to I-95, Route 1, Delaware and New Jersey beaches, shopping, dining, and the bonus of tax-free retail in Delaware. With its blend of luxury finishes, modern comforts, and flexible living spaces, 230 Anglesey Drive offers the perfect home for your next chapter.
#DENC2095556

MIDDLETOWN

230 ANGLESEY DRIVE

2 Beds

3 Baths

2,475 Sq.Ft.

$584,900

MLS#: DENC2095556

TO BE BUILT - The Sassafras II- This beautiful ranch home features 3 bedrooms, 2 full baths, 2 car garage. Standard features include a full unfinished 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! *Photos shown are of similar home, not listed property. Agent must accompany buyer on first visit or preregister prior to first visit on builder website.
#DENC2079330

MIDDLETOWN

400 REDERICK LANE 4 SASSAFRAS II

3 Beds

2 Baths

2,200 Sq.Ft.

$582,500

MLS#: DENC2079330

TO BE BUILT - The Oxford - Whether you're looking for a detached homes home large enough to raise a growing family, an intelligently designed attached carriage home, or a modern townhome with tons of living space, it's all here at the Reserve at Ponds of Odessa. Our homes feature 2-4 bedrooms with optional first floor owner's bedroom, 2 car garage, 2/2.5 baths, 42" cabinets, wall to wall carpeting, spacious open- concept main level, public sewer and water, underground utilities, blacktop driveway, streetlights, sidewalks and curb lined streets. Located in Appoquinimink School district. This beautiful home features 4 bedrooms, 2.5 full 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. Builder Splits Transfer Tax
#DENC2079326

MIDDLETOWN

400 REDERICK LANE 2 OXFORD

4 Beds

2 Baths

2,357 Sq.Ft.

$582,500

MLS#: DENC2079326

New on site 2 days ago
This is a To-Be-Built Home. The Rockford is a beautifully designed one-story floorplan offering 3 bedrooms, 2.5 bathrooms, and a 2-car garage, thoughtfully crafted for comfort, convenience, and modern living. The open-concept layout features a gorgeous kitchen with an oversized island and spacious pantry, flowing seamlessly into an oversized great room that is ideal for entertaining or everyday relaxation. The spacious primary suite serves as a private retreat, complete with a luxurious bath designed for comfort and style. A private home office provides the perfect space for telecommuting, while secondary bedrooms are thoughtfully positioned away from the primary suite for added privacy. Optional outdoor living spaces, including a deck or screened porch, allow you to extend your living area and enjoy the outdoors. 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. For a full list of features please contact our sales consultants. Welcome to Four Seasons at Baymont Farms, a new active adult 55+ community in Middletown, DE, offering low-maintenance, resort-style living. With spacious home designs and access to countless amenities, come enjoy the best that active living has to offer. Residents can take advantage of the community's 6,000 sq. ft. clubhouse, a pool with tiki hut, a state-of-the-art fitness center, a kayak launch, and multiple bocce and pickleball courts. With a full-time lifestyle director on site, Baymont Farms also features a well-maintained calendar of activities such as Zumba classes, yoga sessions, billiards and more. At Four Seasons at Baymont Farms, the focus is on community. Make friends and enjoy the company of people who have worked hard and now want to enjoy all that a luxury 55+ active adult community has to offer. Just minutes from downtown Middletown, DE with access to Delaware Rt. 1, Baymont Farms offers great convenience while preserving the serenity of its picturesque landscape. At this beautiful active lifestyle community, the relationships that you make and the people you spend time with will create memories that last a lifetime.
#DENC2099176

MIDDLETOWN

19 GOLDEN RAINTREE COURT

3 Beds

2 Baths

2,378 Sq.Ft.

$580,400

MLS#: DENC2099176

This spacious 3-bedroom home with a VERSATILE BONUS ROOM offers a thoughtfully designed layout and numerous updates throughout. The inviting family room with fireplace opens seamlessly to the center-island kitchen with a bar area at the island , now updated with a new stove, microwave, dishwasher, refreshed countertops, and a stylish backsplash, making it perfect for both everyday living and entertaining. Just off the kitchen you’ll find a convenient mudroom, pantry closet, half bath, and garage entry. Upstairs, the spacious primary suite boasts a tray ceiling, double vanities, his and her walk-in closets, and a beautifully tiled shower. Two additional bedrooms are generously sized, and the bonus room can be used as a den, home office, or playroom. The laundry room is conveniently located on this level. The full basement provides exceptional additional living space with a second family room, a large storage area, and a utility room. Plumbing is already roughed in for a future bathroom, and the water heater was replaced in 2019. Location Location Location!! Minutes from Routes 1, 13, and 301 with no tolls to go north and a grocery store 5 minutes away! Best of all—no grass to cut. The HOA handles lawn care, allowing you to enjoy your weekends relaxing by the community pool. HOA fees also include common area maintenance and snow removal.
#DENC2095628

MIDDLETOWN

336 ACASTA DRIVE

3 Beds

2 Baths

3,100 Sq.Ft.

$580,000

MLS#: DENC2095628

New on site today
Welcome to this charming Colonial-style home located in Middletown, DE. This spacious property boasts 4 bedrooms and 2.1 bathrooms, perfect for a growing family. With a traditional two-level layout, this home offers ample space for both relaxation and entertaining. As you step inside, you are greeted by a bright and airy living space. The lovely floor plan creates a cozy atmosphere as the kitchen overlooks the family room which features a gas fireplace and open to the formal living room/ toy room/ office The kitchen has been updated with newer appliances, counter tops and plenty of cabinet space and an island. Upstairs, you'll find the four bedrooms, including a primary suite, primary bathroom, large walk in closet and an amazing bonus area. Each room offers ample closet space and natural light. Outside, the property features a well-maintained yard, perfect for enjoying the outdoors. The attached garage provides convenient parking and additional storage space. Located in the desirable area of Middletown, DE, this home is close to schools, parks, shopping, and dining options. Don't miss out on the opportunity to make this lovely property your own! Contact us today to schedule a showing.
#DENC2099196

MIDDLETOWN

163 MIDDESSA DRIVE

4 Beds

2 Baths

2,375 Sq.Ft.

$579,900

MLS#: DENC2099196

Welcome to the Cayot Model, in the desirable 55+ community of Traditions at Whitehall. This charming 3-bedroom home has a great open concept floor plan which offers all one floor living and a welcoming dining room and great room upon entry. At the rear of the home, you will find the luxurious owner's suite complete with walk-in closet and an en-suite bath, including a 5-foot tile shower. With a variety of structural and decorative options available, this home can be customized to perfectly fit your style and needs. Make this your dream home today! 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, walking trails, and a full calendar of social events to keep you engaged and connected with neighbors.
#DENC2080204

MIDDLETOWN

204 BALDY LANE CAYOT

3 Beds

2 Baths

2,004 Sq.Ft.

$579,000

MLS#: DENC2080204

*$10,000 builder incentive; thru 3/31/26* The home you have been admiring is now available! There are so many beautiful features in this Woodland Hills model home and they can be yours without the wait time of a new home build. The Osprey model has 2,898 sq ft with 4 bedrooms and two and a half bathrooms. With ample storage and counter space, the kitchen will be where the family and guests will want to gather. The beautiful granite counters, oversized island and under-cabinet lighting are a few of the custom features that you will enjoy. Soak up the sun all year round in the 12x14 sunroom that is situated just off the great room area. A gas fireplace and built-in bookshelves are the natural focal point of the living room area. Also on the 1st floor is the flex room, study, laundry room, powder room and a mudroom area with a bench seat, coat hooks and lockers. The second floor has 4 larger bedrooms and 2 bathrooms. The master bath, with it's ceramic tile floor, tiled shower and soaking tub, will be your place to retreat and pamper yourself at the end of the day. The hall bath has a tub/shower. The unfinished basement features 9' poured concrete walls. You also have the convenience of a central vac system. This home is situated on a corner homesite and has easy access to Vine Street and I-283. Although loaded with custom features, this home is priced well below replacement cost.
#PADA2048296

MIDDLETOWN

195 MAGNOLIA DRIVE

4 Beds

2 Baths

2,898 Sq.Ft.

$579,000

MLS#: PADA2048296

Benchmark Builders at The Town of Whitehall, Chadwick Floor Plan. TO BE BUILT. The hometown is finally getting its come back. It's the first town to be founded in Delaware in over a century, and it's planned for all homes, businesses and community traditions that make real towns real places. Whitehall has it all! Chadwick floor plan feature 4bedrooms, 2.5 baths, 2nd floor laundry, 2 car attached rear entry garage, an open floor plan for entertainment with a huge great room! **Optional Chadwick front porch shown in photo**.Agent must accompany client on first visit or pre-register client on builder website prior to first visit
#DENC2079246

MIDDLETOWN

530 WHEELMEN STREET 5 CHADWICK

4 Beds

2 Baths

2,456 Sq.Ft.

$570,500

MLS#: DENC2079246

Welcome home to 1220 N Olmsted Pkwy located in the sought-after Village of Bayberry North. Upon arrival, you’ll immediately notice the beautiful stone veneer exterior, offering timeless curb appeal and setting the tone for this well-maintained, 5-year-old ranch home. An inviting covered front porch welcomes you in, perfect for morning coffee, evening relaxation, or connecting with neighbors.. Step inside to an OPEN -CONCEPT LAYOUT filled with natural light and hardwood flooring . The spacious living room flows seamlessly into the dining area and continues into the kitchen, creating an ideal space for everyday living and entertaining.The kitchen features a CENTER ISLAND, GRANITE COUNTERTOPS, STAINLESS STEEL APPLIANCES, A DOUBLE OVEN, and a sunny BUMP- OUT BREAKFAST area that fills the home with natural light. Step outside to the fully fenced backyard, offering endless possibilities for entertaining, relaxing, or outdoor activities. Back inside, the home offers a convenient laundry room with access to the two-car garage. You’ll find generously sized bedrooms, along with a versatile additional room that can be used as a third bedroom, home office, or playroom. The primary suite boasts a spacious walk-in closet and a private bath with double vanity and a glass stand-up shower. An additional full bathroom serves family and guests. The spacious unfinished basement offers exceptional ceiling height and a blank canvas for future customization, ideal for creating additional luxury living space, a home theater, fitness area, or private retreat. A two-car garage and ample driveway parking complete the home. With new shopping centers, grocery stores, dining, and major commuter routes just minutes away, this home offers the perfect balance of suburban charm and modern convenience. This move-in-ready home is ideal for families ready to connect and enjoy everything Bayberry North has to offer. Schedule your tour today and imagine the possibilities.
#DENC2096488

MIDDLETOWN

1220 N OLMSTED PARKWAY

2 Beds

2 Baths

1,850 Sq.Ft.

$569,000

MLS#: DENC2096488

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