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
254
# of Listings
3
Avg # of Bedrooms
$268
Avg. $ / Sq.Ft.
$655,181
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

66 Properties Found. Page 1 of 5.

**Move-in ready** Discover the perfect blend of comfort and sophistication at 2228 Winchelsea Parkway, a 3 bedroom, 2.5 bath Carson floorplan. A gourmet kitchen overlooking the great room with a fireplace creates a warm and inviting centerpiece for both daily living, and entertaining. Boasting sleek pure white quartz countertops, modern pewter maple cabinetry, stainless steel appliances, 3X6 fawn gloss backsplash, and a gas cooktop and wall oven, this kitchen is a chef’s dream! The first floor owners suite provides privacy and convenience, while upstairs, a versatile lost connects two secondary bedrooms with a jack and jill bath, ideal for family or guests. Thoughtful design continues outdoors with a composite deck offering a seamless extension of your living space. Every detail of this home is crafted to enhance both style and function. About Venue at Winchelsea: Future amenities include a 5,400 sq. ft. clubhouse offering a BYOB sports bar, fitness center, multi-purpose room, kitchen, library, billiards, and more. Outdoor amenities include tennis, pickleball, community gardens, a pool, pavilion, dog park, and additional recreational options. *Pictures of a similar home 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. * For appointments and open houses, please visit the welcome home center located at 2405 Greyfriar Loop.
#DENC2096366

MIDDLETOWN

2228 WINCHELSEA PARKWAY

3 Beds

2 Baths

3,397 Sq.Ft.

$499,900

MLS#: DENC2096366

MASSEY ELITE END UNIT- 3 bedrooms, 2.5 baths, 2 car garage. Approx. 2380 SF! 12x10 Deck. This home features a Finished den, 42" cabinets in kitchen, island, stainless gas range, dishwasher, microwave, LVP flooring and recessed lighting in Kitchen. LVP floor and Tile 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. Beautifully appointed end unit townhome featuring 3 bedrooms, 2.5 baths, and approximately 2,333 square feet of living space. This home includes a 2-car garage and a 12x16 deck overlooking open farmland. Interior features include upgraded luxury vinyl plank flooring throughout the main level, a gourmet kitchen with granite countertops, Level 3 cabinetry, a large center island, and a gas range. The primary suite offers a spacious layout with a walk-in closet and private bath. Located in one of the community’s most desirable settings with no building in front, open space surrounding, and ample parking.
#DENC2092162

MIDDLETOWN

442 REDERICK LANE MASSEY ELITE LOT 70

3 Beds

2 Baths

2,333 Sq.Ft.

$498,053

MLS#: DENC2092162

WOW! Simply Gorgeous! This popular Kipling model offers open floor plan, foyer with 11 FT ceiling, wainscoting and gleaming hardwoods extending from foyer thru living room, dining room and kitchen. Well appointed kitchen has granite counters including island with seating for 3, stainless steel appliances, recessed & upgraded lighting. Dining area has sliders to upgraded & enlarged paver patio, upgraded landscaping with paver edging, wonderful front porch & irrigation system. Primary bedroom has plush carpeting, tray ceiling, walk-in closets and full bath with raised height vanity, walk-in tiled shower and beautiful ceramic tiled floor. 2nd bedroom is close to the entry door and another full bath. Main floor laundry room has tiled floor, cabinets, wash tub and washer & dryer included. Additional 2nd floor 12 X 15 Storage Room and storage in the crawl space.This sensational home is located in the premier 55+ Community of Spring Arbor offering a clubhouse, heated salt water pool, bocci ball courts, picnic area, fitness room, immense gathering room with kitchen facilities, library and game rooms including billiards. Great location close to major roads, walking distance to restaurants and shopping..
#DENC2096388

MIDDLETOWN

148 GAZEBO LANE

3 Beds

2 Baths

1,650 Sq.Ft.

$490,000

MLS#: DENC2096388

Rare opportunity to own a private homesite in the desirable River Ridge on the Shenandoah community in Middletown, VA. This undeveloped parcel offers the perfect setting for a custom-built home, weekend retreat, or long-term investment. Enjoy natural surroundings, peaceful privacy, and the flexibility to design and build to your vision (subject to county approvals). Located just minutes from historic Middletown, local dining, wineries, and commuter routes, this property offers a unique balance of seclusion and convenience. Land opportunities in this area are limited, secure your future homesite today. Strategically priced based on current land market trends and buyer activity, this property is being marketed to attract qualified end users and investors alike. Ideal for out-of-state buyers, builders, or those seeking to secure land for future use. Don’t miss the chance to own land with flexibility, upside potential, and location appeal. Come build your dream home on this stunning 20-acre parcel tucked within a private community. Ideally located just minutes from Front Royal, Winchester, I-66, and I-81, this property offers the perfect balance of peaceful seclusion and easy access to nearby towns and amenities. Enjoy mountain views and direct frontage on the beautiful Shenandoah River — ideal for fishing, kayaking, and embracing nature’s serenity. With gently rolling terrain and potential building sites, the possibilities are endless for creating your full-time residence, weekend escape, or legacy property. Approximately 400 feet of frontage on the North Fork of the Shenandoah River. Don’t miss this rare opportunity to own a private piece of the Shenandoah Valley.
#VAWR2011208

MIDDLETOWN

0 RIVER RIDGE DRIVE

None Beds

None Baths

20.0 acres

$480,000

MLS#: VAWR2011208

Welcome to 365 Andrew Ct! This beautifully maintained, like-new home offers all the advantages of new construction without the wait. Nestled within the highly acclaimed Appoquinimink School District, this stunning end-unit townhome combines luxury with convenience. Featuring an expansive open-concept floor plan, this home is tailored for modern living. With 3 bedrooms, 2 full baths, 2 half baths, and a 2-car garage, there’s ample space for everyday life and entertaining. The chef’s kitchen is a standout with upgraded cabinetry, Quartz countertops, a stylish tile backsplash, and GE stainless steel appliances, seamlessly flowing into the dining area and great room. The lower level, currently used as a bedroom, offers versatile options for your needs. It could easily serve as a home office, gym, playroom, or guest suite. Luxury finishes throughout include LVP flooring on the main level, upgraded tile, and elegant details that enhance the home’s appeal. No need to wait for construction; this home is move-in ready in a community where opportunities like this are truly rare!
#DENC2092040

MIDDLETOWN

365 ANDREW COURT

3 Beds

2 Baths

N/A

$477,000

MLS#: DENC2092040

Located in the highly sought after community Ponds Of Odessa this pristine end-unit townhouse offers the perfect balance of convenience as well as comfort. Upon entering you are greeted by natural light and a spacious open floor plan complete with a flex room that can double as an office. Upon exploring more of the home you have a vaulted ceiling and open living room and beautiful kitchen complete with upgraded countertops and cabinets. Downstairs you have an unfinished basement with a plethora of options gym, theater, or additional bedrooms and complete with rough plumbing for a future bathroom. Upstairs you'll find the spacious primary suite fully equipped with walk-in closet as well as an en-suite bathroom with dual vanities. The additional bedrooms are very comfortable sized with their own walk-in closets. Outside you'll find a concrete patio perfect for any outdoor activity. This property is located minutes from many amenities, shopping and local businesses. Also just minutes from major highways great for commuting. Schedule your showing today.
#DENC2094428

MIDDLETOWN

1341 CARRICK COURT

3 Beds

2 Baths

2,325 Sq.Ft.

$475,000

MLS#: DENC2094428

Enjoy single-floor living in this inspired ranch home! At the front of the home, you'll find two bedrooms flanking a full bath. Toward the back, there's a well-appointed kitchen nestled between an elegant dining room and generous great room. The laundry is located near the primary bedroom, which has a large walk-in closet and a private bath. You'll love the professionally curated finishes! Situated on a corner lot and backing to open common area.
#VAFV2035268

MIDDLETOWN

100 MIDSUMMER LANE

3 Beds

2 Baths

1,610 Sq.Ft.

$464,999

MLS#: VAFV2035268

Welcome to the 55+ community of Traditions at Whitehall - Ashton Carriage Town Home. This home is an end unit has a first-floor owner's bedroom w/ full ensuite bath and walk-in closets, second floor has the 2nd bedroom, loft and an additional full bath. Standard 2-car garage, and additional finished upgrades can be purchased to your taste and budget. Community offers in ground pool w/lounge areas, clubhouse featuring exercise & billiards room, gathering/lounge space, full kitchen and a large outdoor patio/grilling area! Builder Splits Transfer Tax (***Photos are of a similar home and may contain options & upgrades not included in listing price shown.***)
#DENC2095106

MIDDLETOWN

314 CHAROLAIS STREET ASHTON

2 Beds

2 Baths

1,794 Sq.Ft.

$456,000

MLS#: DENC2095106

Classic R.C. Peoples-built 2 Story in rarely available Great Oak Farms. This home has fantastic curb appeal starting with the brick siding, but not forgetting the long driveway that is complimented by two decorative brick pillars. Moving inside, there is a living room with a cozy fireplace; just a few steps away from the formal dining room. The kitchen its own dining area, no shortage of cabinet space, and has access to the basement and family room featuring another fireplace! The second story has a full bathroom, and four spacious bedrooms which includes the primary suite that boasts its own full bathroom and plenty of closet space! Additional features include: a mud/laundry area off of the family room with access to the powder room, a total of 4 garage spaces (2 sets of 2 car garages), a brand new septic system, all resting on a large 1 acre lot. While tucked away in the tranquil community, this home is still located just minutes from major routes making your commute an absolute breeze. An excellent home that is ready for your personal touch!
#DENC2072634

MIDDLETOWN

325 GREAT OAK DRIVE

4 Beds

2 Baths

2,150 Sq.Ft.

$455,900

MLS#: DENC2072634

Brand new to the market and just recorded, complete with well, 4 BR conventional perc, electric at edge of lot, and spectacular view of South Mountain historic area and Middletown Valley. Middletown Middle and High schools and Myersville ES for top education. Farm animals allowed accept for swine. Bring your own builder or listing agent will introduce you to top builders in the area. There is no sign on the property, please call LA to set up showing. This lot and the one next to it are the "cream of the crop" and will be gone before Spring build! Hurry today to inspect. Please do not drive on the property without accompaniment of the listing agent.
#MDFR2075330

MIDDLETOWN

9702 MOUNT TABOR - LOT 12 ROAD

None Beds

None Baths

10.2 acres

$450,000

MLS#: MDFR2075330

Brand new to the market and just recorded, complete with well, 4 BR conventional perc, electric at edge of lot, and spectacular view of South Mountain historic area and Middletown Valley. Middletown Middle and High schools and Myersville ES for top education. Farm animals allowed accept for swine. Bring your own builder or listing agent will introduce you to top builders in the area. There is no sign on the property, please call LA to set up showing. This lot and the one next to it are the "cream of the crop" and will be gone before Spring build! Hurry today to inspect.
#MDFR2075328

MIDDLETOWN

9702 MOUNT TABOR - LOT 11 ROAD

None Beds

None Baths

10.26 acres

$450,000

MLS#: MDFR2075328

*Major Price Drop* Welcome to 2804 Mondrian Lane! The moment you step inside, you’re welcomed by a bright and spacious foyer filled with abundant natural light, setting the tone for this beautifully maintained, eight-year-young carriage home featuring the popular Bainbridge model design. This residence offers three bedrooms and two-and-a-half bathrooms, with all bedrooms, two full baths, and a conveniently located laundry area upstairs for everyday ease. The open and functional main level showcases vinyl flooring throughout the foyer, kitchen, breakfast area, powder room, creating a cohesive and stylish flow. The kitchen is thoughtfully appointed with stainless steel appliances, 42-inch cabinets with hardware and crown molding, granite countertops, recessed lighting, and an open concept ideal for daily living and entertaining. Upstairs, the primary bedroom includes an upgraded five-foot stall shower with semi-frameless glass doors, adding a modern and refined touch. The finished basement expands the living space with a comfortable recreation room, brand-new carpet, and a three-piece plumbing rough-in ready for a future full bath. Additional highlights include a one-car garage and a home that presents like new construction—truly move-in ready. Located within the highly sought-after Village of Bayberry community, this home offers access to tree-lined walking trails, well-maintained parks, and the New Town Center featuring a Weis grocery store, along with convenient proximity to Route 1, Route 301, and Route 13, making everyday travel simple and efficient.
#DENC2095880

MIDDLETOWN

2804 MONDRIAN LANE

3 Beds

2 Baths

1,900 Sq.Ft.

$449,900

MLS#: DENC2095880

Great Opportunity in sought after Bayberry North Awaits. Enjoy the flowing floorplan and generous sized rooms in this expanded 2450 sq.ft unit w awesome new EVP flooring in the second floor family room and an in- home office enclave conveniently situated in the bump out off the kitchen. Plenty of natural light and thoughtful lay-out add to the feeling of roominess. Relax on the wonderful rear deck overlooking the neighborhood protected space with tree lined back drop. Truly one of the best lots in the back of the community...quiet and serene. The first floor entryway provides inside access to the 1-car garage, the laundry and utility area (washer and dryer included!!!), a spacious family / recreation room with a rear slider that leads to the fenced in yard. The third floor features an owners suite w private bath and walk in closet, two additional bedrooms and a hall bath. Come take advantage of the community walking trails and playgrounds, or the lake side club house for any specially planned activity you may want to schedule. Convenient and close to all major arteries and the new Bayberry Town Center that features a Weis Market grocery store. This great house that falls within the award winning Appoquinimick School District also includes all appliances, window treatments, ceiling fans (7), and a motivated Seller. Please come take a look today and experience all that Bayberry North has to offer... It's sure to please and will not last long!!!
#DENC2096904

MIDDLETOWN

2189 AUDUBON TRAIL

3 Beds

2 Baths

2,450 Sq.Ft.

$449,900

MLS#: DENC2096904

Welcome to 301 White Pine Dr in charming Middletown, DE! Nestled on an expansive corner lot, this property offers the perfect blend of space, freedom, and potential. With no HOA restrictions, you’re free to let your imagination run wild—whether you envision a lush garden oasis, a backyard entertainment haven, this property has two garages for storage for your hobbies and toys. The home itself is bursting with possibilities to make it truly your own. Located in a desirable area of Middletown, you’ll enjoy the peace of suburban living while staying close to local shops, dining, and top-rated schools. Don’t miss this rare opportunity to create the home you’ve always wanted, with no limitations holding you back! Schedule a showing today and discover all the potential waiting for you at 301 White Pine Dr
#DENC2096792

MIDDLETOWN

301 WHITE PINE DRIVE

4 Beds

3 Baths

2,578 Sq.Ft.

$445,000

MLS#: DENC2096792

Enjoy single level living in this ranch plan Three bedrooms and 2 full baths. The Master Suite has a large walk-in closet and a private bath. Laundry is situation near the master suite offering ultimate convenience. Large kitchen island, fireplace, deck off the great room and an unfinished basement with a 3-piece plumbing rough-in for future bathroom. This beautiful home is a must see! Call today to schedule your tour of our Onyx ranch style plan.
#VAFV2034546

MIDDLETOWN

104 MIDSUMMER LANE

3 Beds

2 Baths

1,610 Sq.Ft.

$444,999

MLS#: VAFV2034546

1 2 3 ... 5
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 $$

properties found. properties found. Page of .

- property

Send a message

Message successfully sent.

Your message

What is 3 + 4 ?

Reason for contacting?

Update Your Temporary Password

Personalize your search

Enter your email and we'll notify you immediately when new listings match what you're looking for.

or enter email address

Already have an account ? Login here

Continue your home search

Already have an account ? Login here

We use cookies

We use cookies primarily for analytics to enhance your experience. By accepting, you agree to our use of these cookies. You can manage your preferences or learn more about our cookies policy.

Privacy Policy Terms of Service