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
261
# of Listings
3
Avg # of Bedrooms
$272
Avg. $ / Sq.Ft.
$637,643
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

76 Properties Found. Page 2 of 6.

The main floor of this Coral home offers a large, uninterrupted space for relaxing and entertaining. The kitchen features a spacious center island and opens to the dining and great rooms. Upstairs, you'll find a convenient laundry, a full bath tucked between two generous bedrooms, and an inviting primary suite with a walk-in closet and private bath. This home is built a loft. To round out this home a basement is included and this beautiful home backs to common area.
#VAFV2035270

MIDDLETOWN

102 MIDSUMMER LANE

3 Beds

2 Baths

1,840 Sq.Ft.

$459,999

MLS#: VAFV2035270

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

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

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.

$449,999

MLS#: VAFV2035268

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.

$449,900

MLS#: DENC2072634

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

Welcome to 25 Chester Court in Middletown, MD, a stunning end unit townhome. This spacious home offers 2472 square feet of modern living across three floors, featuring 3 bedrooms and 3.5 bathrooms. The main level boasts a contemporary kitchen with white quartz countertops, stainless steel appliances, and a large deck perfect for entertaining. The expansive open walkout basement includes a full bathroom, providing ample space for recreation or an additional living area. The home also features luxury vinyl plank (LVP) flooring on all three floors, and an upstairs laundry room for convenience. The oversized primary bedroom is a true retreat, complete with two walk-in closets and an en-suite bathroom with dual vanities and a large shower. Two additional guest rooms and a full hall bathroom complete the upper level. The property includes a one-car garage and plenty of parking in a quiet community. Enjoy the tranquility of this neighborhood while being close to local attractions, shopping, dining, and outdoor activities. This beautiful home is perfect for those seeking modern amenities and a peaceful living environment. Don't miss the opportunity to make 25 Chester Court your new home.
#MDFR2071442

MIDDLETOWN

25 CHESTER COURT

3 Beds

3 Baths

N/A

$444,900

MLS#: MDFR2071442

Welcome to 60 S Cummings Dr, a refined and beautifully updated residence in the desirable community of Middletown Crossin. This elegant 4-bedroom, 2.5-bath home offers a sophisticated blend of scale, comfort, and modern design, with thoughtfully upgraded finishes and a layout that feels both impressive and inviting. From the moment you enter, the home opens into a spacious interior designed to make a lasting impression. The dramatic two-story family room creates a grand focal point, filled with natural light and anchored by a fireplace that adds warmth and style. A second-floor gallery overlook enhances the home's architectural character and gives the main living space a striking open feel. The interior has been enhanced with new vinyl and wood flooring, beautiful light fixtures, and details that elevate everyday living. The main level flows with ease, offering generous space for entertaining, relaxing, and hosting in style. Upstairs, the owner’s suite provides a peaceful private retreat, while the additional bedrooms offer ample space and flexibility. The second-floor landing adds another layer of comfort and can serve as a sitting area, reading space, or bonus functional zone. The fully finished basement further enhances the home’s appeal, featuring a fourth bedroom and a bathroom rough-in that offers future potential for an additional bath. This level is ideal for guest accommodations, extended living, a private office suite, or a recreation space tailored to your lifestyle. Outside, the fully fenced yard offers privacy and room to enjoy outdoor living, while the one-car garage and driveway provide convenient parking. A central vacuum system adds another practical touch to this well-appointed home. Set in one of Middletown’s attractive neighborhoods, this residence offers the space, features, and polished presentation today’s buyers are seeking. 60 S Cummings Dr is where comfort meets presence, and where everyday living feels elevated.
#DENC2098278

MIDDLETOWN

60 S CUMMINGS DRIVE

4 Beds

2 Baths

3,300 Sq.Ft.

$440,000

MLS#: DENC2098278

New on site today
The one many buyers wait for—but rarely find. Welcome to this beautifully maintained 3-bedroom, 2.1-bath home in the desirable Village of Bayberry active adult community, thoughtfully designed for the lifestyle today’s buyers want: main-level living, open entertaining spaces, and comfortable guest accommodations. Step inside and you’ll immediately notice the bright, open layout and gleaming hardwood floors that create a warm and welcoming atmosphere. The heart of the home is the gourmet kitchen, featuring quartz countertops, stainless steel appliances, wall oven, custom cabinetry, pull-out pantry shelving, and designer tile backsplash—perfect for everyday living or entertaining. The first-floor primary suite offers the convenience many buyers are searching for, complete with a walk-in closet with Elfa organizer and private en-suite bath, allowing for true single-floor living. Just beyond the living area, the screened porch overlooking dedicated open space provides a peaceful retreat—ideal for morning coffee or relaxing evenings while enjoying the tranquil setting. Upstairs, you’ll find two additional bedrooms, a full bath, and a versatile loft, providing flexible space for guests, hobbies, or a home office. The full basement with egress window and rough-in for a future bathroom offers exceptional potential for additional living space, recreation, or abundant storage. Situated on a premium lot facing open space, this home offers both privacy and connection to a vibrant community atmosphere. Residents of the Village of Bayberry active adult section enjoy amenities including a clubhouse, pool, walking paths, and community activities. For those considering new construction, this home offers something even better—upgrades already completed, a premium location, and move-in ready convenience without the construction timeline. Opportunities like this—featuring a first-floor primary suite, screened porch, and expansion potential—do not come along often in this community. Schedule your showing today.
#DENC2098640

MIDDLETOWN

2510 CHOPIN DRIVE

3 Beds

2 Baths

1,900 Sq.Ft.

$439,900

MLS#: DENC2098640

New on site 2 days ago
A rare townhome in Middletown—where comfort, style, and location come together—at 118 Fletcher Circle, Middletown, DE 19709. Welcome to this modern, move-in-ready end-unit townhome that backs to open space and offers effortless access to Routes 1, 13, and 301, making it an exceptional choice for commuters and those seeking a connected lifestyle. Located within the Appoquinimink School District. This home blends thoughtful design, quality finishes, and a prime location. The exterior showcases timeless stone accents and an inviting covered portico, creating striking curb appeal. An attached garage is complemented by an expanded driveway accommodating up to three additional vehicles—a rare and practical feature. Inside, the entry level welcomes you with a spacious foyer, convenient powder room, and interior garage access. A versatile family room with carpet offers endless possibilities as a media room, home office, or playroom, with sliding doors leading to the backyard and open space beyond. The main living level is bright and inviting, highlighted by 9-foot ceilings, luxury vinyl plank flooring, and neutral modern décor throughout. The open-concept layout seamlessly connects the living room, dining area, and kitchen—perfect for both everyday living and entertaining. Recessed lighting enhances the home’s modern look while offering adjustable settings that allow you to customize the brightness to suit your needs. At the heart of the home, the chef-inspired kitchen features a large center island with seating, granite countertops, stainless steel appliances, and a spacious pantry. Upstairs, the owner’s suite offers a relaxing retreat with a tray ceiling, elegant board-and-batten accent wall, generous walk-in closet, and a luxurious en-suite bath complete with a dual-sink vanity and walk-in tiled shower with bench seating. Two additional sun-filled bedrooms with recessed lighting share a beautifully appointed full bath, while the bedroom-level laundry adds everyday convenience. Combining modern style, low-maintenance living, and an exceptional Middletown location, this home delivers the appeal of new construction without the wait. Conveniently located near shopping, dining and parks, it presents an outstanding opportunity for buyers seeking comfort, style, and long-term value. Schedule your private tour today and discover why this beautifully upgraded home stands out as a premier choice for modern living. All room sizes and square footage are approximate and should be verified by the buyer.
#DENC2098284

MIDDLETOWN

118 FLETCHER CIRCLE

3 Beds

2 Baths

1,975 Sq.Ft.

$435,000

MLS#: DENC2098284

New on site 2 days ago
Welcome to 107 Jefferson Street. This Charming Colonial was recently rehabbed in (2019) to include a new roof, new dual zone HVAC and new wiring and plumbing throughout. Blending classic character with thoughtful modern updates, this home is truly move-in ready and is located in the heart of Middletown. Step inside to find a bright and inviting interior featuring refreshed finishes, open floorplan and cozy propane fireplace, updated flooring, and a neutral color palette that complements any style. The renovated kitchen offers modern cabinetry, updated countertops, and appliances, making it both functional and stylish. Updated bathrooms showcase contemporary fixtures while maintaining the home’s timeless appeal. Upstairs, 3 comfortable bedrooms provide peaceful retreats, while the flexible layout offers space for everyday living, entertaining, or working from home. Recent renovations enhance both comfort and peace of mind, allowing you to simply unpack and enjoy. Outside, the property offers a detached garage, a shed, a fenced rear yard, and a stone patio for entertaining. The front and back yards are thoughtfully landscaped with several mature trees that provide shade during hot summer months and an abundance of colorful butterfly-attracting perennials and bushes that provide a serene setting throughout the Spring to Fall. This yard wlll provide tranquility year round. Just a short walk to Middletown’s charming downtown shops, restaurants, schools, parks, the new public library and town events. Just 4 miles to commuter route70...this home delivers small-town charm with everyday convenience. A wonderful opportunity to own a fully rehabbed Colonial in one of Middletown’s most desirable locations - USDA Eligible —don’t miss it!
#MDFR2077730

MIDDLETOWN

107 S JEFFERSON STREET

3 Beds

2 Baths

1,584 Sq.Ft.

$429,900

MLS#: MDFR2077730

Motivated seller with a new price!!! Property sold as-is, offering upside potential in a great location. Well suited for cash buyers. Welcome to 1936 Old National Pike, a historic, brick-constructed home built around the turn of the last century, situated on nearly 4 acres along Old National Pike in Middletown, MD. Investors, flippers, and restoration experts, attention! A rare opportunity in Middletown, this turn-of-the-century brick home sits on almost four acres along Maryland’s historic Old National Pike. The property offers substantial upside for buyers prepared to take on a full-scale renovation, with large interior spaces, classic brick construction, a metal roof, and mature surrounding acreage. The home, built circa the turn of the last century, is listed strictly "as-is" and is currently not move-in ready. It offers a durable metal roof and generous interior space, but it needs a comprehensive overhaul. The Land & Outbuilding is nearly four acres, feature mature acreage and include a spacious outbuilding/barn structure with existing electric service. This asset can be used as a workshop, studio, storage, or for conversion. Historic Significance: This is a true piece of local history, positioned directly on Maryland’s original National Pike Road. This home is for the buyer dedicated to preservation; it provides the opportunity to bring a landmark property back to its former glory. Conservation Easement: The Maryland Environmental Trust (MET) Conservation Easement covers the property. This is an optimal acquisition for an experienced house flipper or investor looking for a major value-add project with significant potential ROI after full restoration. Ideal for buyers who value privacy, history, and the potential to make this property their own.
#MDFR2073722

MIDDLETOWN

1936 OLD NATIONAL PIKE

4 Beds

2 Baths

2,824 Sq.Ft.

$429,000

MLS#: MDFR2073722

** 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, 12x10 DECK, 42" cabinets in kitchen, island, stainless steel appliances, gas range, dishwasher, microwave and recessed lighting in Kitchen. LVP flooring upgrades. 3 pc rough in walk out basement. Don't miss out on this spectacular floor plan! Builder Splits Transfer Tax
#DENC2092584

MIDDLETOWN

446 REDERICK LANE MASSEY LOT 68

3 Beds

2 Baths

2,001 Sq.Ft.

$427,056

MLS#: DENC2092584

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