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
107
# of Listings
3
Avg # of Bedrooms
$329
Avg. $ / Sq.Ft.
$549,729
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

124 Properties Found. Page 7 of 9.

Edmonston -TO BE BUILT. Come tour our decorated model during business hours. This 4 bedroom open floor plan welcomes homeowners and visitors alike in a space that flows effortlessly from one room to the next. This plan offers 2 version, the standard offering a first floor owner's suite, and the alternate offering a larger great room and secondary bedroom on the first floor. There is a spacious kitchen with hardwood floors, along with 42" maple cabinets, granite countertops, and so much more! The picture shown is of our largest porch option, but there are several sizes to choose from. If you are looking for a community with planned amenities, retail, school and everything else you can imagine, visit the first new urbanism concept community in Delaware, The Town of Whitehall. Agents must accompany buyer on first visit or pre-register on builder's website prior to first visit.
#DENC2079210

MIDDLETOWN

530 WHEELMEN STREET 1 EDMONSTON

4 Beds

2 Baths

2,716 Sq.Ft.

$591,000

MLS#: DENC2079210

NEW FLOOR PLAN - CHARLESTON -TO BE BUILT. This 4 bedroom open floor plan welcomes homeowners and visitors alike in a space that flows effortlessly from one room to the next. There is a spacious kitchen with hardwood floors, along with 42" maple cabinets, granite countertops, and so much more! Be the first to build this floor plan and get a special incentive off any upgrades. Ask the sales manager for details. If you are looking for a community with planned amenities, retail, school and everything else you can imagine, visit the first new urbanism concept community in Delaware, The Town of Whitehall. Agents must accompany buyer on first visit or pre-register on builder's website prior to first visit.
#DENC2079248

MIDDLETOWN

530 WHEELMEN STREET 6 CHARLESTON

4 Beds

2 Baths

2,730 Sq.Ft.

$590,000

MLS#: DENC2079248

Welcome to 3151 Schuman Drive, a stunning Cooper Model home situated on a premier lot in the Village of Bayberry South, Middletown. This elegant residence, one of the few backing to serene woodlands, offers an expansive backyard with unobstructed views, providing unparalleled privacy. Encompassing 2,050 square feet of sophisticated living space, this home boasts three spacious bedrooms and two well-appointed bathrooms. The primary bedroom features a luxurious two-foot extension for additional comfort. Notably, the third bedroom, currently styled as an office, is graced with charming bay windows. Culinary enthusiasts will delight in the kitchen, complete with upgraded granite countertops and a state-of-the-art induction cooktop. The adjacent four-season sunroom seamlessly connects to the back deck, equipped with an electric retractable awning. This home is further enhanced by modern conveniences and upgrades such as hardwood flooring, remote-controlled blinds across three zones, recessed lighting, and a top-tier Bosch electric heat pump. A full unfinished basement with an egress window and sump pump offers endless possibilities for additional living and entertainment spaces. Energy efficiency is prioritized with owned solar panels rated at an impressive 10,000 kW, often nullifying electricity costs outside of the coldest winter months. The property also includes a WiFi-controlled irrigation system, a paving pad with discreet trash storage, and three ceiling fans for added comfort. Experience the perfect blend of elegance, modernity, and privacy in this exquisite home.
#DENC2093704

MIDDLETOWN

3151 SCHUMAN DRIVE

3 Beds

2 Baths

2,050 Sq.Ft.

$589,900

MLS#: DENC2093704

Welcome to 30 Cantwell Drive in the sought after community of Cantwell Ridge. You are invited in by a two story foyer with high ceilings and tons of natural light. Just off the entry there is a home office to the left, with glass doors, perfect for a private meeting or working from home. To the right of the entry is a dining room. As you continue down the hall you will find a generously sized powder room. The kitchen is open concept, overlooking the family room, which has a fireplace, so you don't miss out on the action when you have guests over. There is a large sunroom lined with floor to ceiling windows that overlooks the backyard. On the second floor you will find a huge owner's suite with a private sitting room, two walk-in closets that will not disappoint! And wait, the owner's bathroom is a retreat, with two vanities, a walk-in shower, and the soaking tub is a dream! Down the hall is three additional bedrooms and one full hall bathroom. There is a full basement, unfinished, waiting for your ideas to come to life. This home is in the Award Winning school district of Appoquinimink School District. Be in your new home before the holidays.
#DENC2088128

MIDDLETOWN

30 CANTWELL DRIVE

4 Beds

2 Baths

3,342 Sq.Ft.

$585,000

MLS#: DENC2088128

New on site 4 days ago
Middletown’s fastest-selling active adult community is selling quickly—and opportunities like this don’t come around often. Venue at Winchelsea is in its final stretch of Phase One single-family homes, so now is the time to secure an incredible home at an exceptional value before it’s gone. Welcome to 2918 Cordwainers Lane, featuring the highly sought-after Mendocino Luxe floorplan. This beautifully designed home offers 2 bedrooms, 3 bathrooms, and a finished basement, checking every box for comfort, style, and flexibility. The inviting foyer opens to a rare and valuable flex space, ideal for a home office or hobby room, along with a formal dining room perfect for entertaining. The bright white, open-concept kitchen shines with a large center island, abundant cabinetry, a wall oven, and gas cooktop—making hosting effortless. Sunlight fills the family room, which flows seamlessly to a spacious covered patio, the perfect place to unwind and enjoy sunset views. The owner’s suite is a true retreat with two walk-in closets and a spa-like en-suite bath featuring a double vanity and walk-in shower. Upstairs, a finished loft offers endless possibilities—crafting, hobbies, or a cozy getaway for visiting grandchildren. The finished basement with a full bath adds even more space for guests, entertaining, or relaxation. About the Community: This vibrant 55+ active adult community is designed for living your best life. Residents will enjoy a 5,400-square-foot clubhouse, pickleball and tennis courts, bocce, a resort-style pool, a state-of-the-art fitness center, and a full calendar of activities—so there’s always something to look forward to. Best of all, lawn care, snow removal, and trash and recycling are included, giving you the freedom to spend your time exactly how you choose. Homes are selling quickly, and Phase One is almost gone—don’t wait to claim your place at Venue at Winchelsea. This is your chance to get in before it’s too late. *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 model home located at 2405 Greyfriar Loop.
#DENC2094580

MIDDLETOWN

2918 CORDWAINERS LANE

2 Beds

3 Baths

3,422 Sq.Ft.

$584,990

MLS#: DENC2094580

Welcome to the Cayot Model, in the desirable 55+ community of Traditions at Whitehall. This charming 3-bedroom home has a great open concept floor plan which offers all one floor living and a welcoming dining room and great room upon entry. At the rear of the home, you will find the luxurious owner's suite complete with walk-in closet and an en-suite bath, including a 5-foot tile shower. With a variety of structural and decorative options available, this home can be customized to perfectly fit your style and needs. Make this your dream home today! As a resident of this vibrant active adult community, you'll enjoy access to a wealth of amenities, including a state-of-the-art clubhouse, fitness facilities, sparkling swimming pools, walking trails, and a full calendar of social events to keep you engaged and connected with neighbors.
#DENC2080204

MIDDLETOWN

204 BALDY LANE CAYOT

3 Beds

2 Baths

2,004 Sq.Ft.

$579,000

MLS#: DENC2080204

Welcome to the Village of Bayberry South — an exceptional 55+ community where resort-style amenities and low-maintenance living come together to create a truly elevated lifestyle. This impeccably maintained home is move-in ready and positioned on one of the largest lots in the neighborhood, peacefully tucked away on a quiet, tree-lined street. Designed for effortless single-level living, the open-concept layout blends sophistication, comfort, and everyday practicality. Step inside to a warm and inviting foyer that flows into a bright and flexible living space, easily adaptable to multiple seating or dining configurations. The living room is filled with natural light from twin sets of double windows, creating a cheerful, airy atmosphere that sets the tone for the rest of the home. At the heart of the residence is the beautifully appointed chef’s kitchen, featuring granite countertops, upgraded cabinetry, and a generous center island perfect for both casual meals and stylish entertaining. A charming breakfast nook sits just beyond, with sliding glass doors that open to a private TREX deck overlooking the beautifully manicured backyard — the ideal spot for morning coffee, alfresco dining, or a quiet evening unwind. This thoughtfully designed home offers three spacious bedrooms, 2.5 bathrooms, and an additional flex room that can serve as an office, den, or even a fourth bedroom. Two of the bedrooms offer private en-suite bathrooms, providing comfort and convenience for both owners and guests. The third bedroom offers excellent versatility, whether used for visitors or a dedicated workspace. The full basement, complete with an egress window, provides exceptional storage and offers the potential to create additional living space tailored to your needs. For added peace of mind, the home is equipped with a whole-house generator, ensuring comfort and security in any weather. Life at Bayberry South is truly maintenance-free — lawn care, landscaping, and snow removal are all handled for you, allowing more time to enjoy the community’s impressive amenities. The clubhouse serves as the vibrant social hub of the neighborhood, offering a resort-style pool with tranquil pond views, a state-of-the-art fitness center, game and billiards rooms, and tennis/pickleball courts. With a robust calendar of clubs, activities, and events, you’ll find endless opportunities to stay active, engaged, and connected.
#DENC2091776

MIDDLETOWN

4116 LAUGHTON LANE

4 Beds

2 Baths

2,650 Sq.Ft.

$579,000

MLS#: DENC2091776

TO BE BUILT - The Oxford - Whether you're looking for a detached homes home large enough to raise a growing family, an intelligently designed attached carriage home, or a modern townhome with tons of living space, it's all here at the Reserve at Ponds of Odessa. Our homes feature 2-4 bedrooms with optional first floor owner's bedroom, 2 car garage, 2/2.5 baths, 42" cabinets, wall to wall carpeting, spacious open- concept main level, public sewer and water, underground utilities, blacktop driveway, streetlights, sidewalks and curb lined streets. Located in Appoquinimink School district. This beautiful home features 4 bedrooms, 2.5 full baths, 2 car garage. Standard features include a partially finished basement, Granite kitchen countertops, 42" maple cabinets, stainless steel appliances, hardwood floors in foyer, kitchen & breakfast area & a stone water table on the exterior. Builder Splits Transfer Tax
#DENC2079326

MIDDLETOWN

400 REDERICK LANE 2 OXFORD

4 Beds

2 Baths

2,357 Sq.Ft.

$576,500

MLS#: DENC2079326

TO BE BUILT - The Sassafras II- This beautiful ranch home features 3 bedrooms, 2 full baths, 2 car garage. Standard features include a full unfinished basement, Granite kitchen countertops, 42" maple cabinets, stainless steel appliances, hardwood floors in foyer, kitchen & breakfast area & a stone water table on the exterior. Appoquinimink School district! *Photos shown are of similar home, not listed property. Agent must accompany buyer on first visit or preregister prior to first visit on builder website.
#DENC2079330

MIDDLETOWN

400 REDERICK LANE 4 SASSAFRAS II

3 Beds

2 Baths

2,200 Sq.Ft.

$576,000

MLS#: DENC2079330

Looking for a beautiful place to call home that offers a country feel with a 3/4 acre corner lot, fenced in backyard and an inground pool? Then Misty Vale Farms is calling your name with this beautifully updated home featuring acacia hardwood floors throughout with tile bathrooms, an upgraded kitchen with stainless steel appliances, butcher block counters, wood burning fireplace, formal dining room and and a sunken family room right off the kitchen that leads to a deck and bridge to your incredible backyard with patio, raised garden beds, perennial flowers and large grasses to complete the landscaping. Warmth and openness make this a perfect home for relaxing, entertaining or game night! Sellers installed a NEW vinyl white privacy fence around the pool area, with grassy patches, a fire pit section and concrete decking with plenty of room to entertain and enjoy the outdoor serenity of your very own inground pool - with NEW HEATER! They also upgraded the second floor with all NEW HARDWOOD floors to match the main level. The main level also features a great bonus room with glass framed french doors - perfect for home office, library, playroom - you decide! Upstairs, the primary suite impresses with vaulted ceilings, stunning tile in the en suite bath, and an 11-ft walk in closet. Two additional upstairs bedrooms, a stylish hall bath, and convenient upstairs laundry complete the second floor. The finished basement adds even more flexibility with a media/playroom and an additional bedroom for guests. But the real showstopper is outside where your summer paradise awaits! Enjoy a sparkling in-ground pool with diving board. And the roof is only 8 years young! All this home needs is you and homes like this don’t come along often—don’t miss your chance to make it yours!
#DENC2093922

MIDDLETOWN

102 NEWBURY COURT

4 Beds

2 Baths

2,292 Sq.Ft.

$575,000

MLS#: DENC2093922

This charming brick rancher is located at the end of a cul-de-sac in sought after Middletown and sits on a peaceful 1.72 acre level lot. The first floor features an open floor plan complete with hardwood floors throughout, formal living room, formal dining room, family room with brick fireplace, breakfast nook leads to a relaxing Trex deck and patio overlooking the large backyard. 1st floor laundry room leads to a oversized 2 car garage. 3 bedrooms and 2 full baths. The fully finished walkout lower level features another full bathroom and large storage room. Some recent upgrades include 20 SEER heat pump (2023), new septic field (2023), electric fireplace (2024), well pump (2020), Ecobee smart thermostat (2023).
#MDFR2073664

MIDDLETOWN

6527 MORNINGSIDE COURT

3 Beds

3 Baths

2,275 Sq.Ft.

$574,900

MLS#: MDFR2073664

Benchmark Builders at The Town of Whitehall, Chadwick Floor Plan. TO BE BUILT. The hometown is finally getting its come back. It's the first town to be founded in Delaware in over a century, and it's planned for all homes, businesses and community traditions that make real towns real places. Whitehall has it all! Chadwick floor plan feature 4bedrooms, 2.5 baths, 2nd floor laundry, 2 car attached rear entry garage, an open floor plan for entertainment with a huge great room! **Optional Chadwick front porch shown in photo**.Agent must accompany client on first visit or pre-register client on builder website prior to first visit
#DENC2079246

MIDDLETOWN

530 WHEELMEN STREET 5 CHADWICK

4 Beds

2 Baths

2,456 Sq.Ft.

$570,500

MLS#: DENC2079246

New on site 4 days ago
This well built, all brick rancher sits on a corner lot and is in excellent condition. It has 4 generous sized bedrooms and 3 full bathrooms (every bedroom has direct access to a full bath) and an in-law suite with 2 separate entrances. Gas fireplace on main level and wood burning fireplace in finished basement. Beautiful hardwood floors in the foyer, hallway, dining room, living room and 3 bedrooms. Huge finished walk-out basement with large storage area. Floors in basement (rec room and basement bedroom) were recently replaced. Circular driveway and 2 car garage.
#MDFR2074538

MIDDLETOWN

215 BROAD STREET

4 Beds

3 Baths

2,580 Sq.Ft.

$570,000

MLS#: MDFR2074538

Sitting in the heart of Middletown, this fully renovated colonial is located in the desirable community of Middletown Crossing and Appo school district. Tastefully remodeled top to bottom with spacious rooms and a basement that's ready to be finished. Features include New Roof, New HVAC, Updated Kitchen, New Appliances, Updated Bathrooms, Vinyl flooring through out the first floor just to name a few. Make your appointment today, you won't be disappointed. Seller is a licensed real estate agent and has financial interest.
#DENC2094216

MIDDLETOWN

40 BROWNING CIRCLE

4 Beds

2 Baths

2,425 Sq.Ft.

$569,900

MLS#: DENC2094216

To be built - New Construction! Monarch offers resort-style living featuring high-end finishes and flexible floor plans. At the heart of the community, residents will enjoy an amenity-rich clubhouse complete with a resort-style pool, pickleball and sports courts, and inviting indoor lounge spaces perfect for relaxation or connection. Combining the sophistication of luxury homes with the laid-back charm of Delaware living, Monarch delivers the perfect balance of comfort, style, and convenience—all just minutes from Middletown’s shopping, dining, and entertainment. The Newport – Single-level ranch home with 1,662+ sq. ft., 3 bedrooms, and 2 baths. Features a spacious kitchen with island seating open to the dining area and great room. Options include an added second-floor bedroom and bath, unfinished storage, and outdoor living spaces.
#DENC2093608

MIDDLETOWN

2202 EARLY COURT

3 Beds

2 Baths

1,662 Sq.Ft.

$569,900

MLS#: DENC2093608

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