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
251
# of Listings
3
Avg # of Bedrooms
$276
Avg. $ / Sq.Ft.
$641,520
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

73 Properties Found. Page 4 of 5.

** 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

**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.
#DENC2097434

MIDDLETOWN

758 ROSLER WAY

4 Beds

3 Baths

1,980 Sq.Ft.

$369,900

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 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.

$369,900

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.

$369,900

MLS#: DENC2097430

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.

$365,000

MLS#: PADA2056698

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

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 one additional bedrooms, a den and office 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. *Please read: This community is designated as an active adult community. Owners must be 55 years of age or older. Any additional occupants must be over 18 years of age. 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

3 Beds

2 Baths

2,669 Sq.Ft.

$349,642

MLS#: DENC2098062

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

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.

$339,900

MLS#: DENC2096262

UNDER CONSTRUCTION. *$10,000 builder incentive; thru 3/31/26* 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

*$10,000 builder incentive; thru 3/31/26* 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

**PRICE REDUCTION** Discover comfort, space, and convenience in this move in ready Colonial townhome located in the Millbranch at Greenlawn community and within the sought after Appoquinimink School District. Built in 1998 and fully updated in 2018, this well maintained home blends modern updates with a layout designed for comfortable daily living. Step inside to an open open floor plan where the living room, dining area, and kitchen flow together with ease. The spacious living room fills with natural light and creates a welcoming place to relax or gather with friends and family. Recessed lighting and ceiling fans add comfort and warmth throughout the space. The eat in kitchen features granite countertops and energy efficient appliances, including a built in range, self cleaning oven, dishwasher, and built in microwave. Just off the kitchen is a large dining area which makes everyday meals and hosting guests simple and convenient. Upstairs you will find three generously sized bedrooms, including a primary bedroom with a walk in closet. The layout offers both comfort and privacy. The home includes a full bathroom along with a convenient half bath for guests. The finished lower level adds valuable living space and includes a laundry area. This level works well as a family room, home office, recreation area, workout space, or guest area. It also has a door leading to the backyard. Step outside through the sliding glass door to a second story deck overlooking the fenced backyard. This outdoor space creates a great spot for morning coffee, evening dinners, or relaxing after a long day. The neighborhood features sidewalks and street lighting which make the community welcoming and easy to enjoy. The home also includes off street parking for two vehicles. The location places you minutes from Middletown shopping, restaurants, parks, and major commuter routes. Homes in this condition within the Appoquinimink School District draw strong interest. Schedule your showing and see the home for yourself. You will be glad you did! Some photos have been enhanced by AI.
#DENC2096608

MIDDLETOWN

25 FRANKLIN DRIVE

3 Beds

1 Baths

1,325 Sq.Ft.

$335,000

MLS#: DENC2096608

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Buyers resources
7 Reasons to Work with a Realtor
7 Principles For Home Buying Success
Getting a Mortgage To Buy a Home
Home Hazards Awareness
Key Items For Home Inspection
Questions When Buying a Condo
Questions When Choosing a Realtor
Sellers resources
8 reasons to work with a realtor
Calculating Capital Gains
Checklist for Better Showing
Cleaning Home For Sale
Improving Odds Of an Offer
Preparing Home for photoshoot
Selling Your Home for More $$

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