CHARIS REALTY GROUP
One of the most popular communities provided by {{page_data.agentName}}

MIDDLETOWN

One of the most popular communities provided by Charis Realty Group

MIDDLETOWN

About MIDDLETOWN

Discover Middletown, MD Real Estate

Welcome to Middletown, Maryland! Nestled in the heart of Frederick County, Middletown offers a charming blend of small-town atmosphere and modern amenities. If you’re searching for a place where community, convenience, and natural beauty meet, Middletown, MD real estate is the perfect choice.

Why Choose Middletown, MD?

Located just minutes west of Frederick, Middletown boasts picturesque landscapes, historic landmarks, and a warm, welcoming community. Here’s why so many homebuyers are looking for houses for sale in Middletown, MD:

  • Stunning Mountain Views: Surrounded by the scenic Catoctin Mountains and rolling farmland, this area provides breathtaking vistas year-round.
  • Top-Rated Schools: Middletown is renowned for its excellent public schools, including Middletown High School.
  • Charming Downtown: Explore locally-owned shops, cafes, and eateries along Main Street for a classic small-town experience.
  • Nearby Recreation: Enjoy outdoor activities at Middletown Park, South Mountain State Park, and local golf courses.
  • Easy Access: Quick commutes to Frederick, Hagerstown, and even Washington, DC make Middletown ideal for professionals and families alike.

Middletown, MD Housing Market Overview

The Middletown, MD real estate market features a wide variety of properties, from historic Victorian homes to modern new constructions. Whether you’re a first-time buyer, looking to upgrade, or seeking a peaceful place to retire, Middletown offers:

  • Single-family homes
  • Townhouses
  • New builds and developments
  • Spacious lots and acreage

Interested in recent listings? Check current homes for sale in Middletown, MD for up-to-date market trends and pricing.

Live in the Heart of Frederick County

Relocating to Middletown, MD means you’ll experience:

  • A strong sense of community and friendly neighbors
  • Highly walkable streets with beautiful historic architecture
  • Year-round events, including the popular Middletown Heritage Festival
  • An unbeatable blend of rural charm and convenient suburban living

Ready to Find Your Dream Home in Middletown?

From stately colonials to custom-built estates, Middletown, Maryland real estate delivers exceptional value and quality of life. If you’re considering a move, now is the perfect time to contact a trusted Middletown, MD real estate agent to start your search.

Start living the life you’ve always dreamed of in Middletown, Maryland—where homes are more than houses; they’re part of a vibrant, enduring community.

One of the most popular communities provided by Charis Realty Group
227
# of Listings
3
Avg # of Bedrooms
$271
Avg. $ / Sq.Ft.
$658,983
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

227 Properties Found. Page 13 of 16.

Investor Alert! High Cash Flow + Strong ROI - Welcome to 219 South Union Street in Middletown - a fully improved mixed-use, multi-unit property offering impressive income and strong long-term upside! Featuring 1 commercial unit and 3 residential apartments, all separately metered and recently updated, this is a turn-key investment opportunity in a desirable downtown location. Income Breakdown: Commercial Unit: $1,195/mo, 1BR/1BA Apartment: $1,070/mo (currently leased month to month - higher market rent potential), (2) 2BR/1BA Apartments: $1,495/mo each. - Total Monthly Gross Rent: $5,255 Annual Gross Income: $63,060 WOW!! CAP Rate of 11.56%, and Cash on Cash Return of 19.91%, 5-Year Investment Rate of Return (5% Appreciation) - 31.72%!! MASSIVE Depreciation Benefit!! This property combines commercial stability with residential demand and future appreciation off the charts. Tenants pay their own electric, minimizing owner expenses. The building features high ceilings, exposed brick, ornate details, and private rear balconies for each apartment. Don’t miss this rare, high-yield investment opportunity in thriving downtown Middletown!
#PADA2049614

MIDDLETOWN

219 S UNION STREET

None Beds

None Baths

3,186 Sq.Ft.

$399,000

MLS#: PADA2049614

Attention developers... this 8 acres is currently being subdivided into 3 buildable lots. All 3 lots currently have passing perc tests. 1.19 acres, which you can see in the first photo of the cornfield. The other 2 lots are tucked in the woods with a private setting and are 3.29 acres, and 3.63 acres. All dry utilities are available out in the street. Another option for someone looking to build their dream home is to keep the last 2 larger lots (almost 7 acres combined) to build on, then sell the 1.19 acre separately. The remaining acreage kept to build on is right off the private road coming from Oberlin Rd., (see 2nd photo). Beautiful country setting, but close to shopping and restaurants.
#PADA2046770

MIDDLETOWN

675 OBERLIN ROAD

None Beds

None Baths

8.0 acres

$395,000

MLS#: PADA2046770

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 owner’s suite with its large spaces and lots of natural light. The owner’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 you’ve been searching for a move-in ready home that blends style, comfort, and convenience — this is the one. Located in the highly desirable Appoquinimink School District, this beautiful ranch-style home has been designed with today’s lifestyle in mind. Step inside and you’ll immediately notice the open layout, natural light, and thoughtful details throughout. The kitchen is truly the heart of the home — featuring sleek countertops, elegant cabinetry, stainless steel appliances, recessed lighting, and a spacious pantry. Whether you’re cooking dinner or entertaining guests, this space was made to enjoy. From the kitchen, step right out onto your back deck — 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 — 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. ✨ With its modern touches, flexible layout, and prime Middletown location, this home truly has it all — and it’s offered at under $400,000! Don’t wait — 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

Welcome to 810 Lisicassey Loop in Middletown! This well-maintained 3 bedroom, 2.5 bath home offers comfortable living in the quiet picturesque community of Hyatt's Crossing. The main level features an open, functional layout with a bright living area, dining space, and a well-equipped kitchen designed for everyday convenience. Upstairs, the spacious primary suite includes a private bath, accompanied by two additional bedrooms suited for guests, family, or home office use. The finished basement provides valuable extra living space — ideal for recreation, fitness, or media. The home is in close proximity to shopping, dining, schools, and major routes, blending privacy with accessibility. A great opportunity for buyers looking for space, comfort, and a welcoming community.
#DENC2093128

MIDDLETOWN

810 LISSICASEY LOOP

3 Beds

2 Baths

2,425 Sq.Ft.

$375,000

MLS#: DENC2093128

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.

$364,800

MLS#: DENC2095688

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 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. - All taxes are estimated since this is new construction and has not yet been assessed.
#PADA2051538

MIDDLETOWN

126 MAGNOLIA DRIVE

3 Beds

2 Baths

1,798 Sq.Ft.

$360,581

MLS#: PADA2051538

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 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

New on site 3 days ago
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

UNDER CONSTRUCTION. *$15,000 builder incentive; thru 2/28/26* This Bluebird model is a 3 BD, 2.5 BA, center unit townhome. You’ll soon discover the value of the many included features that are packed into this home. The open first floor plan will make entertaining family and friends a pleasure. Nine foot first floor walls make this home feel even more spacious. A self-cleaning electric range, granite counters and soft-close cabinet doors/drawers are featured in this kitchen. You will love all the storage available in the walk-in pantry. The entire first floor has luxury vinyl plank flooring. Check out the size of these bedrooms! The owner’s suite is sure to please with large spaces and lots of natural light. Bedrooms 2 and 3 have their own full bath. The laundry room is just steps from all bedrooms and bathrooms. This home also boasts a walk-out lower level, 10×12 composite deck, and a 2 car garage. - Interior photos are of a similar model. - All taxes are estimated since this is new construction and has not yet been assessed.
#PADA2051548

MIDDLETOWN

128 MAGNOLIA DRIVE

3 Beds

2 Baths

1,539 Sq.Ft.

$339,375

MLS#: PADA2051548

*$15,000 builder incentive; thru 2/28/26* UNDER CONSTRUCTION. This Bluebird model is a 3 BD, 2.5 BA, center unit townhome. You’ll soon discover the value of the many included features that are packed into this home. The open first floor plan will make entertaining family and friends a pleasure. Nine foot first floor walls make this home feel even more spacious. A self-cleaning electric range, granite counters and soft-close cabinet doors/drawers are featured in this kitchen. You will love all the storage available in the walk-in pantry. The entire first floor has luxury vinyl plank flooring. Check out the size of these bedrooms! The owner’s suite is sure to please with large spaces and lots of natural light. Bedrooms 2 and 3 have their own full bath. The laundry room is just steps from all bedrooms and bathrooms. This home also boasts a walk-out lower level, 10×12 composite deck, and a 2 car garage. - Interior photos are of a similar model. - All taxes are estimated since this is new construction and has not yet been assessed.
#PADA2051576

MIDDLETOWN

130 MAGNOLIA DRIVE

3 Beds

2 Baths

1,539 Sq.Ft.

$339,375

MLS#: PADA2051576

This beautifully kept 3-bedroom, 2.5-bath townhome in Woodland Hills is move-in ready and waiting for you! Inside, you'll find an open layout filled with natural light on the main floor, complete with stainless steel appliances (high end refrigerator stays) and a convenient second-floor laundry area. Washer and Dryer already installed. Other great features include: walk-out basement with plenty of potential to finish for extra living space, deck overlooking private woods, attached 2 car garage with another 2 car driveway, no homes or neighbors directly behind you. Location is super convenient—close to Route 283, shopping, dining, Hershey, Harrisburg, and Penn State Harrisburg. You're also just a short 3 minute walk to the Middletown Swim Club. The current owner has barely lived here, so the home feels almost new. Economical gas heat to help keep utility bills low. Don't miss out—schedule your showing today!
#PADA2056216

MIDDLETOWN

158 SAGE BOULEVARD

3 Beds

2 Baths

1,524 Sq.Ft.

$327,700

MLS#: PADA2056216

Dream Homesite, Discover your perfect escape on this wooded, well installed and septic approved and engineered and ready to build, Nestled high above Middletown Valley the lot has a cleared homesite. views privacy and tranquility and minutes from town.
#MDFR2061288

MIDDLETOWN

8511 ROSEBUD COURT

None Beds

None Baths

8.2 acres

$325,000

MLS#: MDFR2061288

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