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 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

129 Properties Found. Page 6 of 9.

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.

$619,000

MLS#: DENC2079324

Welcome to Baymont Farms — where resort-style living meets effortless luxury. Located in one of Middletown’s premier 55+ active adult communities, this stunning single-family home—just 2.5 years young—offers refined design, thoughtful upgrades, and the relaxed elegance you are looking for in your next home. Freshly painted and beautifully maintained, the home is completely move-in ready and radiates a bright, sophisticated feel throughout. Offering 3 bedrooms and 3 full baths, the versatile floor plan is designed for both everyday comfort and effortless entertaining. A private upper-level suite creates the perfect retreat for guests, grandkids, or hobbies, complete with its own bedroom, full bath, and sitting area. At the heart of the home is a beautifully appointed gourmet kitchen featuring crisp white cabinetry, quartz countertops, stainless steel appliances, and a spacious center island with bar seating—ideal for casual gatherings. The adjoining dining area is accented with charming farmhouse wainscoting, while the dramatic floor-to-ceiling stone gas fireplace anchors the great room and creates a warm, inviting focal point. A thoughtfully designed private office with custom built-in bookcase and rolling ladder offers both style and function—perfect for reading, working, or pursuing favorite hobbies. Designed with easy one-floor living in mind, the spacious owner’s suite provides a peaceful retreat with a luxurious en-suite bath and an oversized walk-in closet. Outdoor living is equally special. The Trex deck offers a perfect setting for entertaining or quiet evenings outdoors, while the sun-filled east-facing sunroom welcomes morning light and overlooks the beautifully landscaped backyard highlighted by merlot crepe myrtle trees. In the evening, unwind on the charming front porch and enjoy picturesque sunset views framed by apricot and berry-red miniature rose bushes. Additional highlights include professionally landscaped grounds, an irrigation system, a full unfinished basement already plumbed for future expansion, and a spacious two-car garage. Life at Baymont Farms feels like being on vacation year-round, with amenities including: • Resort-style pool with tiki bar • Pickleball and bocce courts • Scenic walking and biking trails • Kayak access to Drawyers Creek • Dog park • A stunning clubhouse hosting over 50 social clubs and activities, from mahjong and bourbon tastings to yoga, arts & crafts, book clubs, poker nights, and festive holiday gatherings. Experience the perfect blend of luxury, comfort, and vibrant community living. Schedule your private tour today and discover why Baymont Farms is one of Middletown’s most sought-after active adult communities
#DENC2098450

MIDDLETOWN

507 CHERRY BARK ROAD

3 Beds

3 Baths

2,700 Sq.Ft.

$615,000

MLS#: DENC2098450

Welcome to 3016 Barber Lane! This gorgeous, 55+ newly constructed detached home was built in 2024 and is located in Parks Edge, a part of the Village of Bayberry community in Middletown, Delaware! Situated on a premium corner lot, this beautifully upgraded Cooper II model with a two car garage offers great views with a pocket park in front and a meadow behind the home that cannot be built on! This thoughtfully designed home features 2 bedrooms, 2 full baths, and a versatile den/flex space that can serve as an office or easily convert to a third bedroom. From the moment you step inside, you’ll appreciate the luxury vinyl plank flooring that runs throughout the main living areas and bedrooms! The gourmet kitchen is a standout, featuring a huge level 3 quartz island, stainless steel appliances, a double wall oven, electric glass-top range, built-in microwave, and dishwasher. The cabinetry package was the highest upgrade offered (level 3), complete with soft-close doors and drawers and pull-out racks for maximum functionality, and the pantry has been enhanced with a custom Closet Factory system! The kitchen flows seamlessly into the living and dining areas with a nice open floor plan! Heading to the bedrooms you will find a spacious primary suite that includes a beautifully tiled bath with a walk-in shower and built-in seat. A large primary closet is also outfitted with a fully customized master closet system by Closet Factory. The second bedroom is also a great size with a large closet and a cozy nook in the room! Additional custom Closet Factory upgrades were added to the laundry room, providing exceptional organization and storage. The outdoor living is just as impressive, with a screened-in porch leading to a 16x20 maintenance-free vinyl deck with metal spindles—perfect for entertaining or simply enjoying the peaceful meadow views. The home also includes a two-car garage with a Liftmaster garage door open that connects to MyQ App- so convenient! There is also a huge unfinished basement which has been professionally water-sealed floor for added peace of mind. After move-in, the owner put in over $40,000 in additional upgrades to the home, including custom zebra blinds on nine windows, tinted privacy mirror polarized glass at the front door, patio sliders, and primary bath window, grab rails in the bathroom and five ceiling fans with remotes were installed. In addition- EVERY light fixture, faucet, and door handle was upgraded throughout the home, and three wall-mounted TV setups with electrical were installed. Front railings were also added to the front porch! The irrigation system includes a Wi-fi adaptor so it connects to your phone and can control each zone in the system! This exceptional property combines premium lot positioning, extensive upgrades, and move-in-ready condition in one of Middletown’s most desirable active adult communities! Book your tour today!
#DENC2098048

MIDDLETOWN

3016 BARBER LANE

2 Beds

2 Baths

1,866 Sq.Ft.

$615,000

MLS#: DENC2098048

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 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.

$614,000

MLS#: DENC2079332

Welcome Home! Located in the sought-after 55+ community of The Ponds at Bayberry, this exquisite 3-bedroom, 2-full-bath home offers comfort, style, and resort-style living. Residents enjoy fantastic amenities, including a clubhouse, pool, and a full calendar of activities. The home features a stunning stone front exterior and a spacious covered porch perfect for relaxing. Inside, you’ll find an open-concept layout with gleaming hardwood floors, large windows that fill the home with natural light, and a beautifully upgraded kitchen ideal for cooking and entertaining. Step outside to a gorgeous back deck with a retractable awning overlooking a private, tree-lined backyard—a peaceful retreat for morning coffee or evening gatherings. In the basement you will find a rough in for plumbing and a walk-out with sliding doors leading to the private back yard. This beautiful home in The Ponds at Bayberry has everything you’re looking for in a vibrant 55+ community. Don’t miss your chance to make it yours
#DENC2093966

MIDDLETOWN

624 VIVALDI DRIVE

3 Beds

2 Baths

2,050 Sq.Ft.

$609,999

MLS#: DENC2093966

The Fayetteville offers an open-concept layout paired with timeless classic design, creating a home that feels both inviting and refined. Scheduled for settlement in April 2026, this thoughtfully designed residence includes 3 bedrooms, 3 baths, and a 2-car garage, with flexible spaces ideal for everyday living and entertaining. Standout features include a finished basement that expands your living area, a cozy fireplace that anchors the main living space, and laminate wood flooring throughout the first floor for a warm, cohesive feel. A dramatic backsplash extending to the ceiling adds a designer touch in the kitchen. The kitchen is styled with light grey cabinetry and white quartz countertops, blending clean lines with modern elegance. Upstairs, carpeted bedrooms provide comfort and privacy, while the bathrooms feature upgraded showers with eye-catching diamond backsplash details. For a full list of included features, please contact our sales representatives. Photos are for illustrative purposes only and may not represent the exact home or finishes available.
#DENC2094616

MIDDLETOWN

851 MERLIN DRIVE

3 Beds

3 Baths

2,307 Sq.Ft.

$609,990

MLS#: DENC2094616

This home is a To-Be- Built. The Fayetteville offers a private home office just off the foyer, perfect for working from home in comfort. The striking modern kitchen features Looks interior options and opens to a spacious great room filled with natural light from abundant windows. The luxurious primary suite includes a generous walk-in closet and a relaxing primary bath with dual sinks. Upstairs, a versatile loft provides flexible space ideal for a game room, playroom, home theater, or additional living area. 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.
#DENC2095730

MIDDLETOWN

883 MERLIN DRIVE

3 Beds

3 Baths

2,307 Sq.Ft.

$602,990

MLS#: DENC2095730

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

Discover the charm of this stunning traditional home nestled in the desirable subdivision of The Legends. This beautifully maintained residence, built in 2001, boasts a generous 2,700 sq. ft. of finished living space, perfect for creating lasting memories. Situated on a spacious corner lot, this property offers both privacy and a welcoming atmosphere. Step inside to find a harmonious blend of comfort and style, featuring elegant hardwood, ceramic tile flooring and carpet throughout. The heart of the home is the inviting kitchen, equipped with modern stainless steel appliances and a double oven, ideal for culinary enthusiasts and entertaining guests. The open layout seamlessly connects the kitchen to the cozy living area, complete with a charming fireplace that sets the perfect ambiance for gatherings. With four well-appointed bedrooms and 2.5 bathrooms, this home provides ample space for relaxation and rejuvenation. The convenience of a main floor laundry adds to the ease of daily living. The full basement, with rough bath plumbing, offers endless possibilities for customization—think home gym, playroom, or additional living space. Enjoy the convenience of an attached front-entry garage with space for two vehicles, along with additional driveway parking. The outdoor space is perfect for enjoying sunny days and evening strolls in the neighborhood. This property is not just a house; it’s a place to call home. ALSO a New Furnace was just installed. Experience the perfect blend of comfort, style, and location—schedule your private tour today!
#DENC2092438

MIDDLETOWN

1 HOGAN CIRCLE

4 Beds

2 Baths

2,700 Sq.Ft.

$599,900

MLS#: DENC2092438

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

Back on the market due to buyer’s home sale contingency not being satisfied. No fault of the seller or property. Inspections have been done and repairs completed so this home is ready for your buyers! Pride of ownership shines throughout this beautifully maintained home in the desirable Chesapeake Meadows community, located within the Appoquinimink School District. Set on just over an acre of meticulously landscaped grounds, this 3-bedroom, 2.5-bath residence offers privacy, space, and timeless comfort. As you enter, you’re welcomed by a stunning two-story foyer featuring a graceful turned staircase, complete with a chairlift for added accessibility. Formal living and dining rooms offer elegant spaces for entertaining, while the open-concept family room provides a comfortable retreat with the warmth of a natural gas fireplace. At the heart of the home, the gourmet kitchen features granite countertops, a center island, stainless steele appliances, and a sliding glass door that opens to a sprawling, level backyard—your own private outdoor oasis, perfect for gatherings, play, or peaceful evenings at home. The main level also offers a versatile fourth flex room/bedroom or home office, ideal for today’s flexible lifestyles. Laundry is located in a closet on the main floor in the flex room. Upstairs, the oversized primary suite is a true retreat, complete with a sitting area and a spa-like primary bath designed for relaxation. Additional bedrooms are generously sized and thoughtfully laid out. Major updates have already been completed, including a newer roof, HVAC system, radon remediation system, windows, front door, and patio door, allowing the next owner to focus on cosmetic updates and personal touches. Home has been freshly painted. Additional highlights include an electric fence for pets and a home that has been lovingly cared for inside and out. Inspections and recommended repairs have already been made. Septic Inspection completed and passed. Home has a chairlift attached to stairwell. Seller will remove chairlift if buyer does not want it.
#DENC2094560

MIDDLETOWN

54 MEADOW DRIVE

3 Beds

2 Baths

2,879 Sq.Ft.

$599,900

MLS#: DENC2094560

Introducing the CHELSEA Model, to be built in the highly desirable 55+ community of Traditions at Whitehall. This thoughtfully designed 3-bedroom, 2-bath home features an open-concept floor plan, with a spacious foyer, formal dining area, and a large great room that flows into the kitchen perfect for entertaining. The Owner’s Suite includes a walk-in closet and an en-suite bath with a double vanity and standard tile shower. The home also offers flexible options to add a 4th bedroom, loft, and third bathroom on the second floor. The gourmet kitchen is a highlight, with stainless steel appliances, granite countertops, and a large island. The community offers a clubhouse, fitness center, swimming pool, walking trails, and plenty of social activities. With a 2-car garage and low-maintenance living, the Chelsea Model offers a perfect combination of comfort and style.
#DENC2080208

MIDDLETOWN

204 BALDY LANE CHELSEA

3 Beds

2 Baths

2,296 Sq.Ft.

$599,000

MLS#: DENC2080208

24 Hours Notice Required for ALL Showings. Even though this property is in good shape and habitable the property is being sold As-Is, Where-Is. Information regarding the stucco condition, including documentation and a contractor quote outlining the estimated cost to remediate, has been uploaded to the Bright MLS document section. The list price reflects the property’s current condition and presents an opportunity compared to recent neighborhood sales, with comparable homes selling from the mid-upper $600,000s to over $700,000. Some sweat equity can go a long way, offering the potential to build value with updates and improvements. Enter at the grand 2-sty Foyer w/ HW fls, neutral decor, a large arched window over the door adding loads of natural light & a turned HW staircase that also offers convenient "butterfly" entry from the Kitchen & features 2nd fl bridge views of both the Family Rm/Foyer entry! To the right & left as you enter the Foyer are the spacious Living & Dining Rms each featuring neutral carpet & paint, crown moldings, 9ft ceilings, 6ft windows for great natural light & an arched bump-out in the DR adding space as well as lovely design to your formal occasion or celebratory meals! The HW fls flow straight back to the entry of the 2-sty Family Rm, full sized Office w/ ceiling fan & double door access (could also be used as a play room, exercise room, guest room, etc!), a spacious Powder Rm w/ HW fls & pedestal sink next to the Office & a double closet! The rear main floor plan of the large Kitchen w/ expanded Morning Rm addition are open to the Family Rm creating a great flow for both day-to-day or when entertaining! The gourmet Kitchen features recessed lighting, tile fls, granite counters, 42" cherry cabinets w/ upper/lower moldings & nickel pulls, subway tile backsplash, a center island w/ pendant lighting & seating for at least 2, double wall ovens, a gas cooktop, SS appls, an oversized pantry closet & a pass-thru opening at the sink into the Morning Rm addition featuring cathedral ceilings, ceiling fan, loads of windows for natural light & sliders out to the large brick rear patio w/ decorative brick knee wall accents & tranquil views of the private backyard w/ plenty of mature trees, bushes & evergreens! The 2sty Fam Rm provides a cozy yet spacious room to relax featuring a gas FP, neutral carpet, ceiling fan & loads of natural light. A convenient main floor Laundry Rm w/ vinyl flooring, window & shelving, another double closet for daily coat/etc storage & a convenient inside garage access round off the amenities on the first fl. Upstairs, the Primary Owner Suite is impressively sized & features a tray ceiling in the separate Br, a private 11x10 Sitting Rm & full bath featuring tile fls, dual single sink vanities, recessed lights, a jetted tub w/ separate tiled shower stall & an 11x8 walk-in closet! All 3 addl Brs on this level are spacious and feature double closets, neutral carpeting, lighted ceiling fans & great natural light. There's still way more living space for family & entertaining in the finished basement where you will find not 1, not 2, but THREE large finished rooms that can be a Media Rm, Game Rm, Exercise Rm, Hobby/Music Rm, Guest Rm, etc! These areas all have neutral decor throughout including long-lasting Berber carpet, multiple lighted wall sconces & a safety egress window! There's also a 3rd full bath in the lower level for convenience of visiting family/guests featuring tile fls, vanity sink, linen closet & tub/shower! No need to worry about losing basic storage space w/ all of these finished rooms, there are still 2 unfinished rooms in the Bsmnt housing the utilities & plenty of extra space for storage & shelving! This community is conveniently located just off Levels Rd in Middletown so its very close to loads of shopping, dining & entertainment. See it Love it! Buy it!
#DENC2098270

MIDDLETOWN

20 W KILTS LANE

4 Beds

3 Baths

3,425 Sq.Ft.

$597,000

MLS#: DENC2098270

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.

$596,000

MLS#: DENC2091784

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