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 youā€™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. Hereā€™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 youā€™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 youā€™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 youā€™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 youā€™ve always dreamed of in Middletown, Marylandā€”where homes are more than houses; theyā€™re part of a vibrant, enduring community.

One of the most popular communities provided by Charis Realty Group
256
# of Listings
3
Avg # of Bedrooms
$266
Avg. $ / Sq.Ft.
$652,024
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

256 Properties Found. Page 14 of 18.

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.

$395,000

MLS#: DENC2096714

UNDER CONSTRUCTION. *$15,000 builder incentive; thru 2/28/26* This Pheasant model is a 3 BD, 2.5 BA, 1,895 sq. foot, end unit townhome. With its nine foot ceilings and open foyer, well-lit, spacious and open first floor, this home exudes elegance. Included in this kitchen is an island, granite countertops, stainless steel appliances, recessed lighting, an adjacent pantry and many more features. You will feel right at home in the ownerā€™s suite with its large spaces and lots of natural light. The ownerā€™s bath and walk-in closet are exceptionally spacious. Also on the second floor are a loft, bedrooms two and three, a family bath and the laundry room, which is just steps from all bedrooms and bathrooms. This home features a full lower level, a 10'x12' concrete patio, and a 2 car garage. A side porch affords additional outdoor living space. - Interior photos are of a similar home. - All taxes are estimated as this is new construction and has not been assessed.
#PADA2051536

MIDDLETOWN

134 MAGNOLIA DRIVE

3 Beds

2 Baths

1,895 Sq.Ft.

$392,581

MLS#: PADA2051536

If youā€™ve been searching for a move-in ready home that blends style, comfort, and convenience ā€” this is the one. Located in the highly desirable Appoquinimink School District, this beautiful ranch-style home has been designed with todayā€™s lifestyle in mind. Step inside and youā€™ll immediately notice the open layout, natural light, and thoughtful details throughout. The kitchen is truly the heart of the home ā€” featuring sleek countertops, elegant cabinetry, stainless steel appliances, recessed lighting, and a spacious pantry. Whether youā€™re cooking dinner or entertaining guests, this space was made to enjoy. From the kitchen, step right out onto your back deck ā€” perfect for relaxing after a long day or hosting weekend get-togethers. This home offers three comfortable bedrooms, two full bathrooms, and a flex room that can easily be used as an office, reading nook, or playroom. The large laundry room adds plenty of storage and practicality, while every room feels fresh, bright, and ready to move in. The finished lower level adds even more space to spread out ā€” ideal for a media room, gym, or guest suite. Outside, the fenced-in backyard, paver patio, and private deck create an inviting setting for everyday living or entertaining. āœØ With its modern touches, flexible layout, and prime Middletown location, this home truly has it all ā€” and itā€™s offered at under $400,000! Donā€™t wait ā€” schedule your private showing today and see why 8 Redding Circle feels like home the moment you walk through the door.
#DENC2091860

MIDDLETOWN

8 REDDING CIRCLE

3 Beds

2 Baths

1,800 Sq.Ft.

$386,900

MLS#: DENC2091860

**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 NCCā€™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 youā€™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 Novellaā€™s appeal is its unmatched location. Situated just steps from Bayberry Town Center, homeowners can walk to lifeā€™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.
#DENC2097434

MIDDLETOWN

758 ROSLER WAY

4 Beds

3 Baths

1,980 Sq.Ft.

$386,500

MLS#: DENC2097434

**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 NCCā€™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 youā€™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 Novellaā€™s appeal is its unmatched location. Situated just steps from Bayberry Town Center, homeowners can walk to lifeā€™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

**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 NCCā€™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 youā€™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 Novellaā€™s appeal is its unmatched location. Situated just steps from Bayberry Town Center, homeowners can walk to lifeā€™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

** 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

This solidly-built 3BR/2.1BA luxury garage townhome is situated in the Appoquinimink School District and features an impressive main floor with gleaming hardwood floors, a giant living room/dining room combo, and a gourmet kitchen with sliding door leading out to a fenced yard. Head upstairs to three spacious bedrooms, including a primary bedroom with en suite, sitting area, and balcony. On the third floor, you'll find a massive loft that would be perfect as a guest room, game room, office, or craft room. All of this in one of the most convenient locations in Middletown - close to all kinds of shopping, restaurants, and medical facilities. With Route 1 right around the corner, you can be at Christiana Mall/I-95 or the beautiful Delaware beaches in no time! Schedule your tour today!
#DENC2097132

MIDDLETOWN

408 QUINCY AVENUE

3 Beds

2 Baths

2,125 Sq.Ft.

$375,000

MLS#: DENC2097132

New on site today
Welcome to 1500 Rosedale Ave where thoughtful design meets modern living. From the moment you walk in, youā€™ll feel the difference. Luxury vinyl plank flooring flows throughout the main living area and finished basement, creating a seamless, high-end feel thatā€™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 todayā€™s buyers truly value. Step outside and youā€™ll find one of this homeā€™s standout features a brand new deck overlooking the fully fenced yard. Whether itā€™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 home to this beautifully maintained 2-bedroom, 2.5-bath, three-level townhome featuring a versatile third-floor loftā€”perfect for a potential third bedroom, playroom, home office, or recreation space. The main level showcases gorgeous hardwood floors and a bright, open layout ideal for everyday living and entertaining. The kitchen is equipped with newer appliances, including a refrigerator, dishwasher, and microwave. Recent upgrades provide peace of mind, with a brand-new roof, a gas furnace just one month old, and central air only three years old. The home has also been freshly painted throughout and very well maintained, making it truly move-in ready. With its flexible living space and major mechanical updates already completed, this home is an outstanding value. Donā€™t let this one slip through your fingersā€”schedule your showing today!
#DENC2096648

MIDDLETOWN

167 SPRINGFIELD CIRCLE

3 Beds

2 Baths

2,125 Sq.Ft.

$365,000

MLS#: DENC2096648

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.

$361,900

MLS#: DENC2094084

UNDER CONSTRUCTION. *$15,000 builder incentive; thru 2/28/26* 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 ownerā€™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

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 2691 Dupont Pkwy, Middletown, DEā€”4 acres nestled in a location that balances serene surroundings with convenient access to nearby amenities. This property features generous acreage that provides ample space for a variety of uses. The level terrain and open landscape make it an ideal setting for those seeking to create a custom home or explore investment potential. With easy access to major routes, this property ensures connectivity to surrounding areas while offering a sense of seclusion and privacy.
#DENC2078196

MIDDLETOWN

2691 N DUPONT PARKWAY

None Beds

None Baths

3.99 acres

$350,000

MLS#: DENC2078196

New on site today
Welcome to this beautiful, modern, like-new duplex raised ranch townhome in the highly desirable Woodland Hills community of Middletown! Designed with todayā€™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, youā€™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 potentialā€”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 areaā€™s most appealing and sought-after neighborhoods. Donā€™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

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