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
248
# of Listings
3
Avg # of Bedrooms
$269
Avg. $ / Sq.Ft.
$656,503
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

248 Properties Found. Page 5 of 17.

Its a new year and your new home awaits you!!! Welcome to this stunning, nearly new home located in the highly desirable Preserves of Deep Creek community in Middletown, Delaware. Built just three years ago, this beautifully maintained property offers 4550 sq ft of thoughtfully designed living space with 4 bedrooms, 4.5 bathrooms, and a finished basement complete with a full bath—ideal for entertaining, guests, or a recreation space. Key Features: Open-concept main level with abundant natural light and neutral decor throughout Gourmet kitchen with large center island, walk-in pantry, and seamless flow to dining and living areas Cozy living room fireplace perfect for cooler evenings Dedicated home office—ideal for remote work or a quiet study space Second-floor loft area for added flexibility—media room, play area, or second office Convenient second-floor laundry room Step outside to a beautifully designed patio featuring a built-in fire pit and permanent seating, creating a perfect space for relaxing or entertaining under the stars. Community Amenities: HOA includes lawn care for low-maintenance living Outdoor pool with splash pad, basketball courts, clubhouse with a fitness center, playground, and more Enjoy being just minutes from golf courses, county parks, and Middletown’s expanding shopping and dining scene. Plus, just minutes from your front door is easy access to the 301 bypass. If you desire to spend time at the beaches you're only a short, convenient drive to the Delaware shore, making for doable day trips.
#DENC2095778

MIDDLETOWN

911 CADMAN DRIVE

4 Beds

4 Baths

4,450 Sq.Ft.

$750,000

MLS#: DENC2095778

New on site 3 days ago
Welcome to an extraordinary residence in the prestigious community of Saint Anne’s, nestled within the highly acclaimed Appoquinimink School District. Perfectly positioned on a premier corner lot, this exceptional property offers a private backyard sanctuary designed for refined living and unforgettable entertaining. Step outside and experience true resort-style luxury — a brand-new in-ground pool sparkles as the centerpiece, surrounded by an expansive deck, elegant patio, and fully fenced grounds that create both privacy and presence. Whether hosting summer soirées or enjoying peaceful evenings under the stars, this outdoor oasis is simply breathtaking. Inside, timeless architectural elegance meets modern openness. A grand two-story foyer makes an unforgettable first impression, framed by sophisticated formal living and dining rooms and a private executive office ideal for working from home in style. The dramatic two-story family room, anchored by a striking fireplace and bathed in natural light, offers a stunning yet inviting space to gather. The gourmet kitchen is thoughtfully appointed with granite countertops, stainless steel appliances, dual wall ovens, a sleek glass cooktop, upgraded cabinetry, and a generous walk-in pantry. A sunlit breakfast area and adjoining sunroom enhance the home’s airy flow, while sliding doors seamlessly connect indoor and outdoor living. Upstairs, retreat to the magnificent primary suite — a serene escape designed for indulgence. Featuring a tray ceiling, spacious sitting area, and dual walk-in closets, this sanctuary offers both comfort and sophistication. The spa-inspired ensuite bath boasts a dual vanity, soaking tub, separate glass-enclosed shower, and private water closet. Three additional well-appointed bedrooms and a full bath complete the upper level. The fully finished lower level transforms the home into an entertainer’s dream, offering a spacious media lounge, game area, sitting space, expansive fitness room, an additional bedroom, and a half bath — ideal for guests, extended stays, or elevated multi-generational living. This is not just a home — it is a statement of lifestyle, comfort, and distinction.
#DENC2097746

MIDDLETOWN

301 BRAEMAR STREET

5 Beds

2 Baths

5,179 Sq.Ft.

$749,900

MLS#: DENC2097746

Semi-Custom Builder, so talk to the sales manager for additional design options. Last lot left in Rothwell Estates from Benchmark Builders. All 6 of our floor plans fit. We have a 7 month build time and rentals available for our buyers if you need a place to stay during the build. See the sales manager, Lindsay, for all the details. The COCHRAN (to be built) is the largest of out floor plans. The large kitchen, 2 story great room, & 2 stair cases are some of the stand out features in this home. We encourage you to take the virtual tour to see this floor plan. Rothwell Estates is endowed with a rich variety of two-story and ranch models, which include basements and an abundance of standard features such as a stone water table, hardwood standard in the foyer, kitchen and breakfast area,& powder room. Granite counter tops in the kitchen, stainless steel appliances, an island, 42" maple cabinets, gas fireplace, recessed lights, tile baths, fully sodded yard and much, much more! With an emphasis on open and versatile floor plans, you are certain to find the home of your dreams. Residences are situated on perfectly sized home sites, most of which back up to open space. And, you'll love the comfort and peace of mind these energy-efficient homes provide. Located in the highly regarded Appoquinimink School District, families will find much to appreciate. Whether you're looking for a home that offers first-floor living or a grand two-story design, Rothwell Estates has something for everyone! Please visit the model home at 126 Green Forest Drive, Middletown, DE 19709. Agent must accompany buyer on first visit or pre-register prior to first visit on builder website
#DENC2097536

MIDDLETOWN

619 MCCRACKEN DRIVE 6 COCHRAN

4 Beds

2 Baths

3,700 Sq.Ft.

$740,000

MLS#: DENC2097536

Welcome to 234 Baldy Ln - the epitome of the term "dream home" combined with luxury, low-maintenance living in the sought-after 55+ community of Traditions at Whitehall in Middletown. Here, you'll find resort-style amenities that meet a beautifully upgraded, move-in-ready home. Enjoy an active lifestyle with the community clubhouse and fitness center, sparkling pool, plus pickleball, bocce ball, and shuffleboard—along with close proximity to area trails, parks, shopping, and everyday conveniences. From the moment you arrive, this home makes a statement with a two-car garage, charming stone skirting, and a welcoming front porch. Out back, unwind on the expansive Trex deck overlooking a private tree-lined yard with garden boxes, the perfect view for morning coffee, weekend entertaining, or a little homegrown harvest. Inside, every detail feels elevated: luxury vinyl plank flooring, custom woodworking, tall ceilings, and a gracious foyer complemented by custom shutters throughout. The spacious family room centers around a natural gas fireplace, accented with board and batten trim and flows seamlessly into an entertainer’s dream setup—an added dry bar with built-in beverage fridge and vintage glass cabinet doors. The adjacent dining area shines with custom built-in china cabinetry and lighting, and opens to a bright, beautiful kitchen featuring a Nancy Meyers-inspired pot rack, striking two-tone cabinetry, granite counters, and a classic tile backsplash. The sunroom extension provides access to the incredible rear deck and yard. The layout offers three bedrooms including a serene primary suite with tray ceiling and a spa-style primary bath with walk-in closet. A full hall bath stands out with a stunning, custom painted mural. Downstairs, the finished basement expands your living options with multiple functional spaces and incredible modern "open" ceiling feature adding to the luxurious feel. The additional square footage adds a workout area, additional living space with custom built-ins, and a full bathroom, plus an additional workshop, perfect for woodworking, tinkering, or hobbies, and a generous storage space. Why wait on new construction when you can have the finished product, already upgraded, thoughtfully customized, and ready to enjoy now—within a community designed for connection, comfort, and active adult living. Don't miss the opportunity to view this beautiful one of a kind property - it won't last long.
#DENC2096354

MIDDLETOWN

234 BALDY LANE

3 Beds

3 Baths

2,725 Sq.Ft.

$735,000

MLS#: DENC2096354

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 Jameson, a two-story home with a first-floor owner’s suite and 2,568+ sq. ft. Includes 3 bedrooms and 2.5 baths. Features a tandem 3-car garage, open kitchen with island seating, breakfast nook, spacious great room, flex room, and walk-in pantry. Upstairs offers 2 bedrooms, loft, full bath, and two unfinished bonus rooms. Options include additional bedrooms, baths, a second owner’s suite, and outdoor living spaces. Monarch’s HOA fee includes grass cutting on your property, curbside garbage and recycling services, common area maintenance including walking paths, landscaping, streetlights, entrance monuments, and all community amenities.
#DENC2093484

MIDDLETOWN

1143 MAJESTY LANE

3 Beds

2 Baths

2,705 Sq.Ft.

$734,900

MLS#: DENC2093484

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 Kingfisher, a two-story home with a first-floor owner’s suite and 2,566+ sq. ft. Includes 3 bedrooms and 2.5 baths. Features an open kitchen with island seating, breakfast nook, spacious great room, and flex room. Upstairs offers 2 bedrooms, a loft, full bath, and unfinished bonus room. Options include additional bedrooms, baths, and outdoor living spaces. Schedule your appointment today for details and incentives. Monarch’s HOA fee includes grass cutting on your property, curbside garbage and recycling services, common area maintenance including walking paths, landscaping, streetlights, entrance monuments, and all community amenities.
#DENC2093362

MIDDLETOWN

1145 MAJESTY LANE

3 Beds

2 Baths

2,566 Sq.Ft.

$724,900

MLS#: DENC2093362

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 Cassidy is a ranch home starting at 2,528 sq. ft., featuring 4 bedrooms, 3.5 baths, and an unfinished bonus room. Open kitchen with walk-in pantry flows to great room and dining. Options available for extra bedrooms, baths, and outdoor living. Monarch’s HOA fee includes grass cutting on your property, curbside garbage and recycling services, common area maintenance including walking paths, landscaping, streetlights, entrance monuments, and all community amenities.
#DENC2093486

MIDDLETOWN

2205 EARLY COURT

4 Beds

3 Baths

2,528 Sq.Ft.

$714,900

MLS#: DENC2093486

Build Your Dream Home in Middletown with Schaeffer Homes! Home is to be built. Photos and virtual tours show the same base model with optional upgrades. Discover our most quintessential rancher with the Weatherby! This generously-sized home starts at 2,498 square feet of living space. The Weatherby includes 3 bedrooms, 2 ½ bathrooms, 2-car garage, as well as a study! With one of our most sizable footprints, this remarkable abode gives plenty of room to spread out in this one-story home. This model also includes the option to upgrade to a larger front porch, perfect for relaxing out front with a warm cup of coffee. The Weatherby is ideal for those seeking ample space to expand and live comfortably. Pricing Overview Land Asking Price: $230,000 Home (The Ravello): $355,900 Estimated land development: $120,000* *Land development costs may be higher or lower. Seller and Builder make no representation of feasibility or final costs. The buyer should request a due diligence period to investigate. Schaeffer Homes will assist you throughout the due diligence process. Additional Details: It is unknown whether a basement foundation can be built on this property at this time. Other Schaeffer floorplans are available to be built here. Note: Home is to be built. Photos and virtual tours show the same base model with optional upgrades.
#DENC2089760

MIDDLETOWN

1487 BUNKER HILL ROAD

3 Beds

2 Baths

2,498 Sq.Ft.

$705,900

MLS#: DENC2089760

New on site 2 days ago
Experience the rare opportunity to own a truly move‑in‑ready, “better‑than‑new” home—without the wait or hassle of new construction. Completed in May 2025, this impeccably maintained residence has been thoughtfully enhanced with high‑end upgrades throughout, offering modern comfort and elevated style from the moment you step inside. The first floor features upgraded flooring, 9‑foot ceilings, and a desirable main‑level bedroom with full bath access, perfect for guests or multi‑generational living. Upstairs, you’ll find four additional spacious bedrooms with generous closets, a beautifully upgraded hall bath, and a versatile sitting/family room ideal for relaxation or play. The luxurious primary suite boasts a tray ceiling, two walk‑in closets, and a stunning en‑suite bathroom complete with a walk‑in shower and dual sinks. The finished basement extends your living space even further and includes an additional full bath—ideal for recreation, a home office, or private guest quarters. Enjoy outdoor living on the inviting front porch, and take advantage of the oversized garage, recess lighting, high‑efficiency HVAC system, and tankless water heater. The home is perfectly situated on a level lot within the desirable Baker Farm community. With immediate access to major routes and close proximity to shopping, entertainment, and recreation, this location offers both convenience and lifestyle. Don’t miss your chance to make this nearly new, impeccably upgraded home your next address!
#DENC2097712

MIDDLETOWN

434 BAKER FARM DRIVE

5 Beds

4 Baths

4,830 Sq.Ft.

$700,000

MLS#: DENC2097712

Step into modern comfort in this beautifully renovated Colonial-style home in sought-after Valley Overlook in Frederick. Offering 4 bedrooms, 3 full baths, and 1 half bath, this spacious residence blends classic charm with fresh, contemporary updates throughout. The main level welcomes you with a bright, open layout featuring a fresh kitchen, inviting living and dining spaces, and a convenient half bath. Upstairs, you’ll find a serene primary suite with en-suite bath. Three more generous bedrooms and a hall bath complete the upper level. The fully finished lower level adds even more versatility with a large recreation space, full bath, and walk-up access to the backyard—perfect for guests, hobbies, or movie nights. Located in a well-established community close to parks, shopping, dining, and commuter routes, this home offers the best of Frederick living with nothing left to do but move in and enjoy!
#MDFR2072474

MIDDLETOWN

2431 QUEBEC SCHOOL ROAD

4 Beds

3 Baths

2,917 Sq.Ft.

$699,999

MLS#: MDFR2072474

The Carver offers a thoughtfully designed open floorplan with classic design touches, with a projected settlement of June 2026. This spacious home includes 3 bedrooms and 3.5 baths, featuring a finished basement complete with a private bedroom and full bath—perfect for guests, extended family, or a flexible retreat. A shiplap-accented fireplace anchors the main living space, while feature walls in the foyer and primary bedroom add character and charm. The screened porch overlooks community open space, and the large homesite tucked at the end of a cul-de-sac provides added privacy and curb appeal. The kitchen shines with a smart appliance upgrade, quartz countertops, and flows seamlessly into the main living areas finished with laminate flooring throughout the first floor. The primary bath is a relaxing escape with a tiled shower enclosure and rain shower head. A 2.5-car garage offers extra room for storage or hobbies. For a full list of features for this home, please contact our sales representatives. Photos are for illustrative purposes only and may not represent the exact home or finishes available.
#DENC2096346

MIDDLETOWN

1525 LESTERFIELD WAY

3 Beds

3 Baths

2,493 Sq.Ft.

$699,990

MLS#: DENC2096346

Stunning new construction by Rachuba Homes in the heart of historic downtown Middletown. This is a rare opportunity to enjoy walkable small-town living in a brand new, move-in ready home, with no HOA! Situated on nearly half an acre, this thoughtfully designed 4 bedroom, 2.5 bath residence offers comfortable, practical living with an open layout ideal for everyday life and entertaining. The kitchen features stainless steel appliances, quality cabinetry, premium countertops, and a stylish backsplash. The main level includes 7-inch luxury plank flooring, black hardware accents, and a welcoming covered front porch. Upstairs, the spacious owner’s suite includes a walk-in closet and a private bath with a 6x7 shower and dual sinks. Three additional bedrooms, a full bath, and a conveniently located upper-level laundry complete the second floor. The finished lower level provides a large recreation space for additional living or entertaining, plus a rough-in for a full bath and space for a fifth bedroom with egress already in place. Located just steps from Middletown’s shops, restaurants, parks, and community events, and within the highly regarded Middletown school district, this home offers the convenience of an established downtown setting with the efficiency and peace of mind of new construction.
#MDFR2074184

MIDDLETOWN

26 WALNUT STREET

4 Beds

2 Baths

2,712 Sq.Ft.

$699,000

MLS#: MDFR2074184

WELCOME to 712 Wallasey Dr, the HUGE previously SENECA MODEL HOME by Ryan Homes. It is located in the sought out Appoquinimink School District, conveniently located off of 301 in the popular Preserve at Deep Creek community. Be the PROUD OWNER to enjoy this model home with many upgrades at a DEAL PRICE. This Seneca model offers 4450 square feet of living space with three gorgeous levels, boasting a finished basement with a full bathroom on a great lot. As you drive to the house, you are greeted with a beautiful upgraded front elevation, lovely landscaping, and a full size porch. As you enter the foyer, you will find a spacious study/office on your right and a powder room. As you continue your tour, you'll find a gorgeous dining room and then the home opens up to a big open family entertainment space – a warm living room, an expansive kitchen with a huge island, and beautiful eat-in kitchen area. The entire first level has upgraded LVP flooring. You will love the white on white modern kitchen featuring quartz countertops, plentiful 42” crown cabinetry, updated hardware, new light fixtures, stainless appliances, gas cooking, vented out hood, a large island, an eat-in dining area, and a walk-in pantry. From the kitchen, you can walk out to a large, accessible, no maintenance deck and leveled lot, perfect for entertaining and for outdoor gatherings. The huge family room has a gas fireplace to keep you warm and cozy in all seasons. By the side of the family room, you'll find a convenient garage entrance which has an arrival center for all your accessories. From the living room, take the stairs to the second level where you'll find the enormous primary bedroom with a luxurious en-suite, featuring a large tile shower and two walk-in closets. You will have plenty of room for your family with three additional bedrooms, two of which share a Jack and Jill bath and a third, potentially a guest bedroom, that offers an en-suite bath. All bedrooms have walk-in closets, all bathrooms have easily maintained and aesthetically pleasing tiled floors. There is also a spacious center loft in this level for upper level entertainment. Upper level laundry completes the tour of second level. The finished lower level has three different entertaining areas to enjoy different activities. You can easily convert a section into 5th bedroom. This gorgeous basement also has a full bath with finishes similar to the stylish bathrooms upstairs. There is a good size unfinished section in the basement for all your storage needs. All three levels have ample recess lighting and plenty windows to keep your home bright yet cozy. Other special features unique to this house are side entrance door for the garage, irrigation system for your lawn. Carrier HVAC system with two zone thermostat and tankless water heater are features that are done with functional convenience in mind. Schedule your tour today. House comes with no furniture. Pictures give idea of the size and furniture option visualization. Any questions contact listing agent. One of the owners is DE licensed real estate agent and listing agent.
#DENC2089228

MIDDLETOWN

712 WALLASEY DRIVE

4 Beds

4 Baths

4,450 Sq.Ft.

$699,000

MLS#: DENC2089228

Welcome home Joanna Gaines! YOU will love this 5 bedroom, over an acre of land and NO HOA farmhouse....in the middle of it all. I know that was a lot in the opening sentence so, shocker, there's more. An in ground pool. I know. It's all true and I had to wake you up! This beauty is the real deal, old meets new and affordable enough for you, BOO. Warning....I will rhyme more. In ground pool and you can walk to school. Don't be a fool and overlook this one. You can even bring your mule. Well, ok, you can't but it works so well on an acre plus of land. Just bring your dogs, kids and friends. Don't forget to invite me, I make killer deviled eggs. This home has survived world wars and it will probably outlast you too. It's big, has class and sass. Here I go again! That was all for the rhyming. I will dial it back. Renovations are abundant and beautiful, just like your Mom. New roof and windows circa 2022. Detached garage, fenced in yard and charm. Not Lucky charms, just pure charm and beauty. Original woodwork and trim. Also, pocket doors. Pocket doors should truly be in every home. They are so cool and efficient. A one of a kind original on Main Street; the GREAT street.
#MDFR2075782

MIDDLETOWN

706 E MAIN STREET

5 Beds

3 Baths

2,202 Sq.Ft.

$698,999

MLS#: MDFR2075782

This stunning executive home located in sought-after Westside Hunt and the Appoquinimink School District offers casual elegance, almost 5000 square feet of living space, and fine craftsmanship by Desabatino Construction. This home features a beautiful stone facade, gracious covered porch for morning coffee or relaxing afternoons, gleaming hardwood floors, 9' first floor ceilings, an ample family room with cozy gas fireplace adjoining the generous kitchen with center island, great pantry, newer stainless steel appliances, and a sunlit breakfast alcove overlooking the large deck and the expansive, fully fenced back yard. The two story foyer with handsome oak staircase takes you to the second floor where you'll find four comfortable bedrooms, three full baths, and a spacious 20 x 24 bonus room or 5th bedroom . The primary retreat offers a luxurious en-suite bath with huge soaking tub, walk-in shower and double vanity. The fourth bedroom/guest suite is complete with a private full bath and jetted tub. The massive finished lower level with built-in bar is the perfect entertainment, media/game room, work or hobby space. The two car garage is equipped with a plug for your EV charger and leads to a handy mudroom/drop zone for shoes and gear. Other features include a new water heater, new carpet, newer A/C unit and a radon mitigation system. Nestled on .8 acres and conveniently located in peaceful and picturesque West Middletown this home offers easy access to restaurants, shopping, schools, marinas, YMCA, parks and outdoor recreation as well as the Rt. 301 bypass and Rt. 1 for a quick commute to points North and South.
#DENC2096684

MIDDLETOWN

103 WESTSIDE LANE

4 Beds

3 Baths

4,936 Sq.Ft.

$695,000

MLS#: DENC2096684

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