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
261
# of Listings
3
Avg # of Bedrooms
$271
Avg. $ / Sq.Ft.
$642,232
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

261 Properties Found. Page 14 of 18.

**This Novella Interior townhome is one of the selected homes eligible for the Blenheim Cornerstone Initiative in compliance with the New Castle County MPDU program. Visit our website or NCC’s website for more details on qualifications and income requirements. ** This home is under construction. Delivery time frame should be discussed with a sales representative. Located in The Overlook at Bayberry in Middletown, Delaware, The Novella blends contemporary comfort with everyday convenience in a way few homes can. Offering spacious rooms and open layouts with flexible living spaces, The Novella is thoughtfully crafted for all that want room to live, work, and unwind. From its inviting main level to its well-proportioned 4 bedrooms, every square foot is designed with livability in mind. Whether you’re hosting friends, setting up a home office, or simply enjoying a quiet evening in, this townhome adapts effortlessly to your lifestyle. What adds to The Novella’s appeal is its unmatched location. Situated just steps from Bayberry Town Center, homeowners can walk to life’s daily essentials like grocery store, pharmacy, dining, coffee, quick bites, and neighborhood services. The Overlook is thoughtfully planned to support a connected and walkable way of living. Imagine grabbing dinner, running errands, or meeting friends without ever needing to get in the car, then returning to your dream home! Families will also appreciate that The Novella sits only blocks from top-rated Appoquinimink schools, consistently recognized among the highest-rated in Delaware for academic excellence, innovative programs, and exceptional community engagement. Homeowners will also enjoy having their own clubhouse and playground in The Overlook in addition to being surrounded by miles of walking trails throughout Bayberry.
#DENC2097418

MIDDLETOWN

746 ROSLER WAY

4 Beds

3 Baths

1,980 Sq.Ft.

$386,500

MLS#: DENC2097418

**This Novella Interior townhome is one of the selected homes eligible for the Blenheim Cornerstone Initiative in compliance with the New Castle County MPDU program. Visit our website or NCC’s website for more details on qualifications and income requirements. ** This home is under construction. Delivery time frame should be discussed with a sales representative. Located in The Overlook at Bayberry in Middletown, Delaware, The Novella blends contemporary comfort with everyday convenience in a way few homes can. Offering spacious rooms and open layouts with flexible living spaces, The Novella is thoughtfully crafted for all that want room to live, work, and unwind. From its inviting main level to its well-proportioned 4 bedrooms, every square foot is designed with livability in mind. Whether you’re hosting friends, setting up a home office, or simply enjoying a quiet evening in, this townhome adapts effortlessly to your lifestyle. What adds to The Novella’s appeal is its unmatched location. Situated just steps from Bayberry Town Center, homeowners can walk to life’s daily essentials like grocery store, pharmacy, dining, coffee, quick bites, and neighborhood services. The Overlook is thoughtfully planned to support a connected and walkable way of living. Imagine grabbing dinner, running errands, or meeting friends without ever needing to get in the car, then returning to your dream home! Families will also appreciate that The Novella sits only blocks from top-rated Appoquinimink schools, consistently recognized among the highest-rated in Delaware for academic excellence, innovative programs, and exceptional community engagement. Homeowners will also enjoy having their own clubhouse and playground in The Overlook in addition to being surrounded by miles of walking trails throughout Bayberry.
#DENC2097430

MIDDLETOWN

754 ROSLER WAY

4 Beds

3 Baths

1,980 Sq.Ft.

$386,500

MLS#: DENC2097430

Welcome to 113 Crawford Street. Located in the heart of Middletown, Delaware. Enjoy close proximity to local shops, restaurants, parks and everyday conveniences with easy access to major routes for commuting. Middletown is known for its small town charm, strong sense of community and continued growth, making this an ideal place to call home. Whether you are taking a stroll around the neighborhood, heading out for dinner nearby, or enjoying the surrounding outdoor spaces, this location truly offers the best of comfort and convenience. This home is perched on an extra large home site with a newly installed privacy fence. A separate foyer leads to a spacious living room with decorative fireplace creating a warm and inviting atmosphere. Just off the dining room offers a powder room and laundry. While the kitchen provides ample room for additional dining and a sliding glass door accessing a deck and expansive backyard which offers space and seclusion. The second floor features an owner suite, two additional bedrooms, and a full bath. An unfinished attic offers potential for added living space. Two large backyard sheds in good condition complete the property providing ample storage solutions. This is a MUST SEE property. ALL the comforts of HOME and IN WALKING DISTANCE to town with amazing amenities!!! Come see this amazing property!
#DENC2096714

MIDDLETOWN

113 CRAWFORD STREET

3 Beds

1 Baths

1,875 Sq.Ft.

$385,000

MLS#: DENC2096714

** WORKFORCE HOUSING-BUYER MUST QUALIFY FOR THE NEW CASTLE COUNTY PROGRAM TO PURCHASE - MASSEY INTERIOR UNIT- 3 bedrooms, 2.5 baths, 1 car garage. Approx. 2001 SF! This home features a Finished den, 42" cabinets in kitchen, island, stainless range, dishwasher, microwave and recessed lighting in Kitchen. Tiled floor and Shower surround in master bath. 3 pc rough in walk out basement. Don't miss out on this spectacular floor plan! Builder Splits Transfer Tax
#DENC2080232

MIDDLETOWN

460 REDERICK LANE MASSEY LOT 61

3 Beds

2 Baths

2,300 Sq.Ft.

$384,900

MLS#: DENC2080232

Nestled at the quiet end of a cul-de-sac with sweeping countryside views, this impeccably maintained home offers a perfect blend of modern updates and serene living just minutes from the Hershey Medical Center. The bright, open-concept main floor features rich hardwood planks, a dedicated den, and a stylish white kitchen equipped with solid wood cabinetry and a double-oven gas range. Step outside to the expansive deck to enjoy the peaceful scenery, or retreat upstairs, including a primary suite with a massive walk-in closet and a dual-vanity ensuite. With a walk-out lower level ready for your custom finishing touches, a fully fenced backyard, and two-car garage, this move-in-ready residence provides the space and sophistication you’ve been searching for.
#PADA2056308

MIDDLETOWN

45 PAVERS COVE COURT

3 Beds

2 Baths

1,731 Sq.Ft.

$379,000

MLS#: PADA2056308

Welcome to 1500 Rosedale Ave where thoughtful design meets modern living. From the moment you walk in, you’ll feel the difference. Luxury vinyl plank flooring flows throughout the main living area and finished basement, creating a seamless, high-end feel that’s both beautiful and built to last. The kitchen has been elevated with stunning granite countertops and sleek stainless steel appliances, offering the perfect space to cook, gather, and entertain. Just off the main living area, the powder room has been completely refreshed with clean, modern finishes. Upstairs, comfort and luxury continue. Brand new carpeting adds warmth, while both bathrooms feature ceramic tile for a polished, timeless look. The primary suite has been completely transformed with the addition of a private full bathroom, creating the kind of personal retreat today’s buyers truly value. Step outside and you’ll find one of this home’s standout features a brand new deck overlooking the fully fenced yard. Whether it’s morning coffee, summer cookouts, or giving pets and loved ones space to roam freely, this outdoor space delivers both privacy and possibility.
#PADA2056698

MIDDLETOWN

1500 ROSEDALE AVENUE

3 Beds

2 Baths

2,004 Sq.Ft.

$374,900

MLS#: PADA2056698

Welcome to Venue at Winchelsea by Lennar — Middletown’s premier active adult (55+) community offering low-maintenance living, spacious designs, and exceptional value. This 2,669 sq. ft. two-story townhome is part of Lennar's Pathway to Ownership Program - application and income qualification are required for purchase. 3114 Pett Level Drive is move-in ready and thoughtfully designed for comfort and ease. The first floor features an inviting open-concept layout that blends the kitchen, dining, and living areas—perfect for both everyday living and entertaining. The luxurious first-floor owner’s suite is privately tucked away in the rear of the home and includes a spa-inspired en-suite bath and generous closet space. A secondary bedroom at the front of the home offers flexibility for guests or a home office. Upstairs, a central loft anchors three additional bedrooms, providing ample space for hobbies, visitors, or multigenerational living. About the community: Venue at Winchelsea is designed for an active, social lifestyle. Future amenities currently under construction include a 5,400 state-of-the-art clubhouse, outdoor pool, pickleball and bocce courts, community gardens, and more. *Pictures are artist renderings and for representational purposes only. Please see New Home Consultant for details. Taxes to be assessed after settlement. If using a Realtor: the agent's client must acknowledge on their first interaction with Lennar that they are being represented by a Realtor, and the Realtor must accompany their client on their first visit. Please contact the Lennar Sales Team directly for questions about qualifications and how to apply for the MPDU program. We are happy to walk you through the process.* For appointments and open houses, please visit the welcome home center at 2405 Greyfriar Loop.
#DENC2098062

MIDDLETOWN

3114 PETT LEVEL DRIVE

5 Beds

2 Baths

2,669 Sq.Ft.

$365,200

MLS#: DENC2098062

UNDER CONSTRUCTION. *$10,000 builder incentive; thru 3/31/26* This Swallow model is a 3 BD, 2.5 BA, 1,798 sq. feet, center-unit townhome. With its nine foot ceilings and lots of natural light, this home feels comfortably spacious. Included in this kitchen is an island, granite counters, stainless steel appliances, recessed lighting, an adjacent pantry and many more features. You will feel right at home in the owner’s suite with its ample space and lots of natural light which also features a private bath and walk-in closet. Also on the second floor are bedrooms two and three, a family bath and the laundry room, which is just steps from all bedrooms and bathrooms. This home has a full, unfinished, walkout lower level and a 2 car garage. A composite deck, as well as the patio below, affords additional outdoor living space. Interior selections may still be available. All taxes are estimated since this is new construction and has not yet been assessed. Interior photos are of a similar home.
#PADA2051546

MIDDLETOWN

132 MAGNOLIA DRIVE

3 Beds

2 Baths

1,798 Sq.Ft.

$360,581

MLS#: PADA2051546

Welcome to 868 Lissicasey Loop, a beautifully maintained home nestled in one of Middletown’s most sought-after communities and located within the prestigious Colonial School District. Built less than seven years ago, this property offers modern living, generous space, and a layout designed for today’s lifestyles. Step through the front door, and you are greeted by a bright foyer that sets the tone for the rest of the home. To your right is the attached one-car garage, and straight ahead is a hallway leading to the versatile lower level—perfect as a recreation room, home gym, office, or additional living space. This level offers incredible flexibility, whether you need extra room for guests, hobbies, or entertainment. This is a shortsale, home is being sold as is Head up to the second floor and discover a fully open, airy, and beautifully lit main living area. Large windows fill the floor with natural light, creating a warm and inviting atmosphere. The living room sits to the right, offering a comfortable gathering space. At the same time, the center of the home features a spacious kitchen with maple-brown cabinetry and a large breakfast island—ideal for meal prep, hosting, or casual dining. Adjacent to the kitchen is an eat-in area plus a dedicated dining space, giving you multiple options for family meals and entertaining. A sliding glass door on this level provides the opportunity to add a second-floor deck for outdoor enjoyment. The third floor features three well-sized bedrooms. The owner’s suite includes a private bathroom and ample closet space. Down the hall is a full guest bath and a conveniently located laundry area, keeping daily routines efficient and straightforward. This home offers the perfect balance of comfort, functionality, and room to grow. With multiple levels of living space, defined areas for privacy, and open spaces for connection, it fits the needs of families with young children, teens, or multigenerational households. Located minutes from major highways, shopping centers, restaurants, and everything Middletown has to offer, this property delivers both convenience and community. 868 Lissicasey Loop is truly an excellent opportunity to live in a thriving area.
#DENC2095734

MIDDLETOWN

868 LISSICASEY LOOP

3 Beds

2 Baths

2,100 Sq.Ft.

$359,000

MLS#: DENC2095734

Being "SOLD AS IS"- Rancher with two bedrooms and two full bath. Kitchen with granite and appliances. Spacious living area. Sunroom. Owners suite with full bath. Two car attached garage. Home is a guardianship sale. Appointed guardian has no knowledge of the home. Buyers and buyers agent should do their own due diligence. Neighborhood information is in the MLS.
#DENC2094084

MIDDLETOWN

561 WHISPERING TRAIL

2 Beds

2 Baths

1,650 Sq.Ft.

$351,900

MLS#: DENC2094084

What an opportunity to purchase a single family home under $375,000 in Middletown Delaware. This 4 bedroom home boast hardwoods through out. And what every buyer can appreciate, a newer roof and Hvac. These major updates can give you pease of mind for years to come. With a lot size of .81 there is potential room to expand. Location, location!! Just minutes from Rt 1 for all your commuting needs!! MORE PHOTOS COMING SOON!
#DENC2096262

MIDDLETOWN

2481 N DUPONT PARKWAY

4 Beds

1 Baths

1,400 Sq.Ft.

$350,000

MLS#: DENC2096262

Welcome to Venue at Winchelsea by Lennar — Middletown’s premier active adult (55+) community offering low-maintenance living, spacious designs, and exceptional value. This 2,669 sq. ft. two-story townhome is part of Lennar's Pathway to Ownership Program - application and income qualification are required for purchase. 3134 Pett Level Drive is move-in ready and thoughtfully designed for comfort and ease. The first floor features an inviting open-concept layout that blends the kitchen, dining, and living areas—perfect for both everyday living and entertaining. The luxurious first-floor owner’s suite is privately tucked away in the rear of the home and includes a spa-inspired en-suite bath and generous closet space. A secondary bedroom at the front of the home offers flexibility for guests or a home office. Upstairs, a central loft anchors three additional bedrooms, providing ample space for hobbies, visitors, or multigenerational living. About the community: Venue at Winchelsea is designed for an active, social lifestyle. Future amenities currently under construction include a 5,400 state-of-the-art clubhouse, outdoor pool, pickleball and bocce courts, community gardens, and more. *Pictures are artist renderings and for representational purposes only. Please see New Home Consultant for details. Taxes to be assessed after settlement. If using a Realtor: the agent's client must acknowledge on their first interaction with Lennar that they are being represented by a Realtor, and the Realtor must accompany their client on their first visit. Please contact the Lennar Sales Team directly for questions about qualifications and how to apply for the MPDU program. We are happy to walk you through the process.* For appointments and open houses, please visit the welcome home center at 2405 Greyfriar Loop.
#DENC2095688

MIDDLETOWN

3134 PETT LEVEL DRIVE

5 Beds

2 Baths

2,669 Sq.Ft.

$350,000

MLS#: DENC2095688

Welcome to this beautiful, modern, like-new duplex raised ranch townhome in the highly desirable Woodland Hills community of Middletown! Designed with today’s lifestyle in mind, this bright and open floor plan is centered around a stunning kitchen featuring granite countertops, a spacious island, pantry, and stainless steel appliances. The seamless flow makes entertaining effortless, while the private rear patio just off the kitchen provides the perfect spot to enjoy your morning coffee or unwind in the evening. The main level offers three generously sized bedrooms, including an impressive 19 x 17 primary suite complete with a walk-in closet and plenty of room to create your own relaxing retreat. Convenient laundry hookups are located on both the main and lower levels, adding everyday flexibility and ease. Downstairs, you’ll find a versatile room ideal for a fourth bedroom, home office, or guest space. In addition, the enormous 37 x 28 lower-level area offers incredible potential—ready to be finished into additional living space such as a family room, gym, media room, or whatever suits your needs. Located in a prime location near local schools, major highways, and the Pennsylvania Turnpike, this exceptional home offers the perfect blend of comfort, space, and convenience in one of the area’s most appealing and sought-after neighborhoods. Don’t miss your opportunity to own this move-in-ready gem in Woodland Hills!
#PADA2056934

MIDDLETOWN

125 SAGE BOULEVARD

4 Beds

2 Baths

1,970 Sq.Ft.

$349,900

MLS#: PADA2056934

Opportunity awaits in this end unit townhome offering great natural light, functional living space, and strong potential. This home presents a fantastic opportunity for a buyer looking to personalize their space or an investor seeking a valuable addition to their portfolio. The main level features a convenient powder room, first floor laundry, and inside access from the garage, providing additional storage and everyday ease. Upstairs, you will find two full bathrooms, including a spacious primary suite with a walk in closet and private bath featuring a stand up shower and soaking tub. A versatile loft area at the top of the stairs offers flexible space perfect for a home office, second living area, or entertainment space. Enjoy relaxing on the front porch during warmer days. As an end unit, the property benefits from added privacy and additional outdoor space. The two car driveway provides ample off street parking. Bring your vision and make this home your own, great value and potential in a desirable location.
#DENC2097244

MIDDLETOWN

187 GILLESPIE AVENUE

3 Beds

2 Baths

2,075 Sq.Ft.

$348,000

MLS#: DENC2097244

Welcome to 108 E Cochran Avenue in the heart of Middletown, Delaware. This cute house has it all - including location. The moment you arrive you will pull up in the driveway and feel like you belong here. The covered porch is wonderful and adds to the curb appeal and style of hte home. Inside, the kitchen is open and spacious. There are plenty of cabinets along with ample counter space. The living room is wide open with large windows and tons of natural light. The rear of the home has a enclosed three-season room where the windows are amazing. There are three ample bedrooms ensuring everyone has a place to call their own. Downstairs the full basement is perfect for extra storage space. The back yard is flat and perfect for spending time outdoors during those summer barbecues with family and friends. Come see this one today!.
#DENC2097978

MIDDLETOWN

108 E COCHRAN STREET

3 Beds

1 Baths

875 Sq.Ft.

$339,900

MLS#: DENC2097978

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