CHARIS REALTY GROUP
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MIDDLETOWN

One of the most popular communities provided by Charis Realty Group

MIDDLETOWN

About MIDDLETOWN

Discover Middletown, MD Real Estate

Welcome to Middletown, Maryland! Nestled in the heart of Frederick County, Middletown offers a charming blend of small-town atmosphere and modern amenities. If you’re searching for a place where community, convenience, and natural beauty meet, Middletown, MD real estate is the perfect choice.

Why Choose Middletown, MD?

Located just minutes west of Frederick, Middletown boasts picturesque landscapes, historic landmarks, and a warm, welcoming community. Here’s why so many homebuyers are looking for houses for sale in Middletown, MD:

  • Stunning Mountain Views: Surrounded by the scenic Catoctin Mountains and rolling farmland, this area provides breathtaking vistas year-round.
  • Top-Rated Schools: Middletown is renowned for its excellent public schools, including Middletown High School.
  • Charming Downtown: Explore locally-owned shops, cafes, and eateries along Main Street for a classic small-town experience.
  • Nearby Recreation: Enjoy outdoor activities at Middletown Park, South Mountain State Park, and local golf courses.
  • Easy Access: Quick commutes to Frederick, Hagerstown, and even Washington, DC make Middletown ideal for professionals and families alike.

Middletown, MD Housing Market Overview

The Middletown, MD real estate market features a wide variety of properties, from historic Victorian homes to modern new constructions. Whether you’re a first-time buyer, looking to upgrade, or seeking a peaceful place to retire, Middletown offers:

  • Single-family homes
  • Townhouses
  • New builds and developments
  • Spacious lots and acreage

Interested in recent listings? Check current homes for sale in Middletown, MD for up-to-date market trends and pricing.

Live in the Heart of Frederick County

Relocating to Middletown, MD means you’ll experience:

  • A strong sense of community and friendly neighbors
  • Highly walkable streets with beautiful historic architecture
  • Year-round events, including the popular Middletown Heritage Festival
  • An unbeatable blend of rural charm and convenient suburban living

Ready to Find Your Dream Home in Middletown?

From stately colonials to custom-built estates, Middletown, Maryland real estate delivers exceptional value and quality of life. If you’re considering a move, now is the perfect time to contact a trusted 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.
$549,611
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

296 Properties Found. Page 7 of 20.

Welcome to this beautiful ranch home in the highly sought‐after 55+ community of Four Seasons at Baymont Farms in Middletown—where maintenance-free living meets upscale comfort! This single‐level home offers a spacious, yet seamless layout, perfect for easy living including 3 bedrooms and 3 full bathrooms, along with a professionally finished lower level (approx 1800 additional sq ft) — giving you the extra space you desire: Ideal for hosting family, guests, or setting up a home office / hobby space. The layout flows from a welcoming entry into the living room and dining areas — perfect for relaxed entertaining or quiet evenings. The upgraded kitchen is a chef’s dream. The finishing details offer clean lines, modern soft-close cabinetry, beautiful Quartz counter tops and stainless-steel appliances making everyday living a pleasure. The Spacious Primary Bedroom with luxurious En-suite Bath invites relaxation with its spa-like finishes. A beautifully designed, extra large walk-in closet provides abundant storage and organization, making this primary suite both functional and indulgent... the perfect place to unwind at the end of the day. The Baymont community offers resort‐style living — clubhouse, pool, and social opportunities built into your lifestyle. Situated in New Castle County and right in the heart of Middletown’s growing landscape, this home offers convenience to local shopping, dining, and major commuter routes while still preserving a peaceful neighborhood feel. Easy access to nearby amenities makes day‐to‐day living a breeze. If you’re looking to downsize or transition to a low-maintenance lifestyle without compromising on space or style, this home checks all the boxes. With everything you need on one level, a desirable newer construction home in move-in ready condition, you’re free to focus on enjoying life — not home upkeep! The practical, yet elegant layout allows flexibility for guests, a craft room, or a comfortable office. Homes in this neighborhood show strong value and demand making this a smart place to make your next move. Imagine having a morning coffee on your patio, or screened porch, an afternoon swim, or clubhouse time just steps from your door. Whether you’re aiming for relaxed retirement living or simply want a well‐designed home with minimal maintenance, this is the perfect home for you! Please contact me to schedule your private tour and see how seamless your next chapter can be.
#DENC2092652

MIDDLETOWN

798 HONEY LOCUST ROAD

3 Beds

3 Baths

1,875 Sq.Ft.

$620,000

MLS#: DENC2092652

This is a great opportunity to live at the beautiful Parks Edge at Bayberry 55 + community. The Hudson Quick Delivery! Come experience the active adult lifestyle that homeowners are raving about: a vibrant social scene, luxury amenities, stunning outdoor spaces and a place that will make you feel welcome and at home from the day you move in. Enjoy low maintenance living with lawn care & snow removal all taken care of for you leaving you more time to enjoy events & activities at your luxury clubhouse with resort style pool overlooking a pretty lake, fitness center, games/billiard room, pickleball & more. Visit our decorated model homes open daily: Monday 1-5, Tuesday -Sunday 10-5.
#DENC2092406

MIDDLETOWN

5735 E CENTRAL PARK DRIVE

3 Beds

2 Baths

2,156 Sq.Ft.

$619,723

MLS#: DENC2092406

TO BE BUILT - The Bennett This beautiful 2 story home features 4 bedrooms, 2.5 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. Appoquinimink School district!
#DENC2079328

MIDDLETOWN

400 REDERICK LANE 3 BENNETT

4 Beds

2 Baths

3,000 Sq.Ft.

$618,000

MLS#: DENC2079328

Welcome to the Cottonwood Model, TO BE BUILT, in the highly sought-after 55+ community of Traditions at Whitehall. This 3-bedroom home features a generous Owner’s Suite at the front of the home, complete with double walk-in closets leading to a luxurious en-suite bath, offering a privacy water closet and a 5-foot tile shower. At the rear of the home, you will find the kitchen and dining area that opens to a bright and airy great room, perfect for relaxation or entertaining. Step outside to enjoy the peaceful surroundings on the optional deck off the breakfast area, where you can take in views of the trees and open space. With a variety of structural and decorative options available, this home can be customized to suit your style and needs. The Cottonwood Model offers the perfect blend of comfort, size, elegance, and low-maintenance living in a vibrant active adult community. As a resident you will enjoy access to amenities that include a clubhouse, fitness facilities, swimming pools, walking trails, and a full calendar of social events to keep you engaged and connected with neighbors.
#DENC2080210

MIDDLETOWN

204 BALDY LANE COTTONWOOD

3 Beds

2 Baths

2,477 Sq.Ft.

$614,000

MLS#: DENC2080210

TO BE BUILT-The Greenspring -This beautiful home features 4 bedrooms, 2.5 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. Appoquinimink School district! Self-Guided Tours available daily 7 am-8 pm. Download "NterNow" APP on smart phone. Enter property ID at front door of Model; scan drivers license and door will auto unlock. Please make sure door is closed and door will auto lock.
#DENC2079324

MIDDLETOWN

400 REDERICK LANE 1 GREENSPRING

4 Beds

2 Baths

3,021 Sq.Ft.

$613,000

MLS#: DENC2079324

Built in 2023 and just two years young, this beautiful 3 bedroom, 3.5 bath home offers over 3,000 square feet of stylish, modern living in the highly sought-after Appoquinimink School District. Perfectly east-facing and set on a desirable end-lot location, it combines open-concept design with high-end touches that make everyday living both comfortable and elegant. The gourmet kitchen is a true showstopper, featuring stainless steel appliances, an oversized island with stunning pendant lighting, and plenty of space for cooking and entertaining. Just off the main living areas, you will find thoughtful upgrades like a custom accent wall in the office and a dramatic accent wall in the two-story stairwell, perfectly framed by the home’s soaring ceilings adding character and architectural interest to the space. Upstairs, a spacious loft offers a versatile flex space perfect for a home office, reading nook, or play area. The owner’s suite is a private retreat highlighted by elegant tray ceilings, an en-suite bath with double sinks and a walk-in shower, and a massive closet with its own window for natural light making it easier to find what you need and keeping the space bright and inviting. Two additional bedrooms and another full bath complete the second level, along with a laundry room featuring shelving, a convenient and organized space that makes household tasks easier and more efficient. The partially finished basement provides even more living space including a full bath and a huge unfinished storage area that is ready for your personal touch. It features a large walkout with double doors. This space is ideal for a home gym, media room, or future expansion. As a bonus, the HOA covers lawn mowing, adding convenience and ease to your homeownership experience. Located just minutes from Route 1, local shops, dining, and parks, this home offers the perfect blend of convenience and community living. Don’t miss your chance to own this beautifully maintained, move-in-ready property in one of Middletown’s most desirable neighborhoods. 300 Jasper Way – Your next chapter starts here.
#DENC2087620

MIDDLETOWN

300 JASPER WAY

3 Beds

3 Baths

3,025 Sq.Ft.

$612,000

MLS#: DENC2087620

Step into the past and own a piece of Delaware's history with the Dilworth House, one of the earliest homes built in the state by Olla Jansen, a Swedish colonist from the 1600-1700 Native American Period. Situated on 12.25 acres of pristine land that backs up to the Augustine Wildlife Preserve, this property is a rare find, offering both a home and a rich connection to the past. The Dilworth House is a true gem, showcasing some of the finest early masonry craftsmanship in Delaware. The distinctive "diapering" pattern, glazed brick in diagonal lines, adorns the gable ends, while stepped belt courses and intricate framework add to its historic charm. Inside, you'll find beautifully exposed beams and brick fireplaces, which once served as the heart of the home’s heating system, with the house originally built in two sections and warmed by a single chimney. This three-story home offers 6 bedrooms, 3 full bathrooms, and 2 half bathrooms, with a fully finished attic on the third floor providing additional living space. The partial basement remains unfinished. Updates over the years have enhanced the home’s functionality, while carefully preserving its historic features. Most of the home remains in it's original state which will require work. For those with a passion for farming, mechanics, or automobiles, this property offers everything you could need. A silo, milk house, dairy barn, cow shed, and storage shed are all included, with the barn having been converted into a workshop—though it could be easily repurposed for a variety of uses. The expansive grounds also offer the possibility of subdivision, providing ample opportunity for future development. This is a once-in-a-lifetime chance to own a truly historic property in a prime location. Don't miss out, schedule your tour today!
#DENC2078246

MIDDLETOWN

875 PORT PENN ROAD

6 Beds

3 Baths

2,900 Sq.Ft.

$611,500

MLS#: DENC2078246

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 Whimbrel is a ranch home starting at 1,971 sq. ft., with 3 bedrooms, 2 baths, and a flex space ideal for a home office. Open kitchen with island flows to dining and great room. Options available for extra bedrooms, baths, loft, and outdoor living.
#DENC2093528

MIDDLETOWN

2204 EARLY COURT

3 Beds

2 Baths

1,971 Sq.Ft.

$609,900

MLS#: DENC2093528

TO BE BUILT-The Eden II is our largest four-bedroom model with a lot of versatility. It can easily accommodate a fifth bedroom if needed. The owner's suite has a separate sitting area, and two walk-in closets. All bedrooms are generously sized. The eat-in kitchen is well laid out with an open flow to the rest of the living space. This floor plan is outstanding. Standard features include stone water table, stainless steel appliances, granite counter tops, hardwood in foyer, kitchen & breakfast.
#DENC2079332

MIDDLETOWN

400 REDERICK LANE 5 EDEN II

4 Beds

2 Baths

3,195 Sq.Ft.

$608,000

MLS#: DENC2079332

This Santa-approved home now offers a new holiday price! What would make the best present this year - keys to your beautiful new home!!!! This meticulously maintained property boasts pride of ownership both inside & out! Situated in the prestigious community of The Legends in Middletown, conveniently located moments from shopping, dining and everyday conveniences. This spacious residence offers an unparalleled blend of comfort and scenic beauty, set against a tranquil backdrop that overlooks the golf course. As you enter the grand entryway greets you with a soaring ceiling and impressive turned staircase that sets a sophisticated tone from the moment you arrive. The flowing floor plan features a striking two-story family room that showcases a gas fireplace for those chilly evenings. This floor plan creates an inviting atmosphere for both intimate gatherings and elegant entertaining. The spacious kitchen offers abundant cabinet/counter space, center island for additional storage & convenient access to the deck through sliding glass doors—perfect for effortless indoor-outdoor living. The spacious rear fenced yard provides both privacy and space, ideal for entertaining, gardening, or simply relaxing while enjoying serene golf course views. The primary suite serves as a private sanctuary, complete with a spacious walk-in closet, linen closet and beautifully designed en-suite bath. Three additional generously sized bedrooms & tastefully appointed hall bath complete the upper level, offering comfort and versatility for guests, family or friends. THE BONUS TO THIS HOME IS THE FINISHED BASEMENT ------ The finished basement features two additional rooms with closets, full bath, counter/cabinet area ideal for entertaining, theater area & large unfinished area for additional storage.
#DENC2093134

MIDDLETOWN

241 PORKY OLIVER DRIVE

4 Beds

2 Baths

2,650 Sq.Ft.

$605,000

MLS#: DENC2093134

Very unusual historic home in the heart of Middletown. Just blocks from new YMCA. Home was assembled in 1944-1948 from parts of multiple historic homes being demolished to make room for post war housing. The front facade and much of the brick exterior were transported and re-assembled on site, proudly boasting 1736 construction. Add various plank floors, beamed ceiling, fireplaces with Mable surround or beautiful delft tiles, decorative moldings, beautiful wood doors.... You may think you can visualize how beautiful this house is, but it will still surprise you, now add recent kitchen, a first floor primary suite with spacious en-suite, large closets and room for washer and dryer. Wait there's more!! Recent HVAC (2 zone) a large Amish built workshop shed , a carriage house/pool house with full bathroom. Ornate gardens and landscaping, a koi pond, brick walkways encased with privacy fencing , yet walking distance to schools, stores , dining and entertainment. A Must see to imagine. Book your private tour as soon as possible.
#DENC2091784

MIDDLETOWN

12 E COCHRAN STREET

4 Beds

2 Baths

2,275 Sq.Ft.

$605,000

MLS#: DENC2091784

This home is a To-Be- Built. The Amadora offers a private home office off the foyer, a beautiful kitchen with a large island overlooking the dining area, and a spacious great room. In addition, a luxurious primary suite with triple windows and a relaxing primary bath with dual sinks and walk-in closet. This community includes a tot lot, walking trails and a dog park and is located in the Appoquinimink School District. Choose from 7 distinct floorplans including a mix of ranch, 1st floor bedrooms and up to 5 bedroom homes. To schedule a tour please and to receive a full brochure of all features in this home please contact our sales representatives.
#DENC2053844

MIDDLETOWN

125 PATTERSON COURT

3 Beds

2 Baths

2,167 Sq.Ft.

$603,990

MLS#: DENC2053844

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.
#DENC2079252

MIDDLETOWN

530 WHEELMEN STREET 8 WENTWORTH

4 Beds

2 Baths

2,680 Sq.Ft.

$602,000

MLS#: DENC2079252

Brand New 55+ Community in Middletown, DE - Four Seasons at Pennfield. Coming This November: Aberdeen II Home Design Blending classic charm with open-concept living, this Aberdeen II home offers 3 bedrooms, 2 baths, and a 2-car garage on a spacious ¼-acre lot. From the welcoming screened porch to the finished basement, there’s room to relax, entertain, and grow. The main living area showcases stylish laminate flooring throughout, anchored by a fireplace with custom paneling trim. In the kitchen, Profile appliances pair with quartz countertops to create a beautiful and functional culinary space. The primary bath features a large walk-in shower with multiple shower heads—your own private retreat. For a full list of features, please contact our sales representatives. Photos are for illustrative purposes only and may show optional features and upgrades.
#DENC2086764

MIDDLETOWN

1521 LESTERFIELD WAY

4 Beds

2 Baths

2,148 Sq.Ft.

$599,990

MLS#: DENC2086764

This ranch home located in a quiet Middletown neighborhood is a gem hidden in plain sight and full of surprises. First, it has 4,000 resplendent finished square feet, and second, it offers two levels of independent living. The floorplan flows seamlessly, providing the kind of breathing room you’ll appreciate, enhanced with an elegant color palette, natural light, and stunning hardwood floors that pull it all together. The living room easily provides the space for various seating configurations and offers a fireplace along the main wall to center around. It opens to the renovated kitchen, inviting with its pristine white cabinetry, backsplash, and eat-in island—and where you’ll find ample workspace and storage plus high-end stainless appliances and fixtures. The dining room sits adjacent with space for extras such as china cupboards or buffets. A bonus room affords decent space for an office, playroom, crafts or hobbies, etc. Conveniently located next to the kitchen, a mudroom combines with the laundry area with storage cabinets and a utility sink. This level boasts four bedrooms and three full baths. The primary suite shines with the addition of a sliding barn door to separate the appealing attached bath plus a walk-in closet. The other bedrooms and baths are all lovely, matching the theme. The downstairs is a complete floor designed as an in-law suite or rental. It boasts a full kitchen, comfortable living/dining area, bedroom, bath, and dedicated laundry room. The aesthetic matches the upstairs to a backdrop of LVP plank-style flooring. It contains a private separate entrance, and even its own parking. The home rests on .31 acres with a view of the mountains, along with plenty of trees and landscaped shrubs to enjoy. A screened-in porch adds another tranquil respite, as does a covered porch stretching along the front of the home. A two-car attached garage provides space for vehicles or storage. This home has been updated, renovated, and carefully maintained—and presents a unique opportunity. But also, this residence is the ticket to enjoy Middletown’s quaint, historic downtown, well-rated schools, and peaceful atmosphere plus proximity to Winchester, Shenandoah Valley, and all the area has to offer.
#VAFV2037492

MIDDLETOWN

2140 SIXTH STREET

5 Beds

4 Baths

4,006 Sq.Ft.

$599,900

MLS#: VAFV2037492

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