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
259
# of Listings
3
Avg # of Bedrooms
$274
Avg. $ / Sq.Ft.
$648,255
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

259 Properties Found. Page 9 of 18.

CHARLESTON -TO BE BUILT. This 4 bedroom (OPTIONAL 1ST FLOOR 5TH 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

**MOVE-IN READY!!** 2212 Winchelsea Parkway, featuring the 3-bedroom, 2.5-bath Carson floorplan. A gourmet kitchen overlooking the great room with a fireplace creates a warm and inviting centerpiece for daily living and entertaining. Boasting sleek Carrara White quartz countertops, modern white cabinetry on the perimeter and pewter maple island, stainless steel appliances, a 3x6 white gloss backsplash, and a gas cooktop with wall oven, this kitchen is a chef’s dream! The first-floor owner’s suite offers privacy and convenience, while upstairs, a versatile loft connects two secondary bedrooms with a Jack and Jill bath—ideal for family or guests. Thoughtful design continues outdoors with a composite deck, providing a seamless extension of your living space. Every detail of this home is crafted to enhance both style and function. Schedule your private tour today! About Venue at Winchelsea: Amenities include a 5,400 sq. ft. clubhouse offering a BYOB sports bar, fitness center, multi-purpose room, kitchen, library, billiards, and more. Outdoor amenities include tennis, pickleball, community gardens, a pool, pavilion, dog park, and additional recreational options. *Pictures of a similar model home and for representational purposes only. 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 welcome home center located at 2405 Greyfriar Loop.
#DENC2100434

MIDDLETOWN

2212 WINCHELSEA PARKWAY

3 Beds

2 Baths

3,397 Sq.Ft.

$582,775

MLS#: DENC2100434

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.

$582,500

MLS#: DENC2079330

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.

$582,500

MLS#: DENC2079326

This is a To-Be-Built Home. The Rockford is a beautifully designed one-story floorplan offering 3 bedrooms, 2.5 bathrooms, and a 2-car garage, thoughtfully crafted for comfort, convenience, and modern living. The open-concept layout features a gorgeous kitchen with an oversized island and spacious pantry, flowing seamlessly into an oversized great room that is ideal for entertaining or everyday relaxation. The spacious primary suite serves as a private retreat, complete with a luxurious bath designed for comfort and style. A private home office provides the perfect space for telecommuting, while secondary bedrooms are thoughtfully positioned away from the primary suite for added privacy. Optional outdoor living spaces, including a deck or screened porch, allow you to extend your living area and enjoy the outdoors. 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. For a full list of features please contact our sales consultants. Welcome to Four Seasons at Baymont Farms, a new active adult 55+ community in Middletown, DE, offering low-maintenance, resort-style living. With spacious home designs and access to countless amenities, come enjoy the best that active living has to offer. Residents can take advantage of the community's 6,000 sq. ft. clubhouse, a pool with tiki hut, a state-of-the-art fitness center, a kayak launch, and multiple bocce and pickleball courts. With a full-time lifestyle director on site, Baymont Farms also features a well-maintained calendar of activities such as Zumba classes, yoga sessions, billiards and more. At Four Seasons at Baymont Farms, the focus is on community. Make friends and enjoy the company of people who have worked hard and now want to enjoy all that a luxury 55+ active adult community has to offer. Just minutes from downtown Middletown, DE with access to Delaware Rt. 1, Baymont Farms offers great convenience while preserving the serenity of its picturesque landscape. At this beautiful active lifestyle community, the relationships that you make and the people you spend time with will create memories that last a lifetime.
#DENC2099176

MIDDLETOWN

19 GOLDEN RAINTREE COURT

3 Beds

2 Baths

2,378 Sq.Ft.

$580,400

MLS#: DENC2099176

Welcome to 541 Diamond Dr - where your future home awaits. Located in the desirable Lakeside community, this beautifully updated Colonial offers the perfect blend of comfort, space, and style. Featuring 4 bedrooms and 2.5 bathrooms, this move-in ready home has been completely refreshed with brand new carpets, fresh paint throughout, new countertops, and updated kitchen appliances. Step inside to an inviting open floor plan designed for both everyday living and entertaining. Beautiful new luxury vinyl plank flooring spans the foyer and formal living and dining spaces on the left, that lead into your beautifully polished kitchen that has been completely refreshed. Gorgeous quartz countertops, crisp white cabinetry, stainless steel appliances, a center island, eat-in area and pantry are just some of the incredible features of this jaw-dropping kitchen. Sliding glass doors lead you outside, where a large deck overlooks a beautiful in-ground pool. This private fenced yard has mature trees for privacy and shade, keeping you cool and covered for summer pool parties. The cozy family room glows with natural light from large windows and features a natural gas fireplace. Upstairs, the second floor laundry space brings added convenience, and the primary bedroom has stunning vaulted ceilings, double walk-in closets, and a primary bath with a double vanity, shower, and separate bath. Three more incredible bedrooms and a full bathroom round out the second floor, but the fun really begins in the finished basement, with even more room to spread out. This home is located in a prime location in the town limits of Middletown, within walking distance to Silver Lake Park, Middletown YMCA, and Middletown Library. This combination of elegance, convenience, and functionality is a rarity 0- don't miss your chance to call 541 Diamond Dr your home!
#DENC2098996

MIDDLETOWN

541 DIAMOND DRIVE

4 Beds

2 Baths

2,100 Sq.Ft.

$580,000

MLS#: DENC2098996

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

*$10,000 builder incentive; thru 3/31/26* The home you have been admiring is now available! There are so many beautiful features in this Woodland Hills model home and they can be yours without the wait time of a new home build. The Osprey model has 2,898 sq ft with 4 bedrooms and two and a half bathrooms. With ample storage and counter space, the kitchen will be where the family and guests will want to gather. The beautiful granite counters, oversized island and under-cabinet lighting are a few of the custom features that you will enjoy. Soak up the sun all year round in the 12x14 sunroom that is situated just off the great room area. A gas fireplace and built-in bookshelves are the natural focal point of the living room area. Also on the 1st floor is the flex room, study, laundry room, powder room and a mudroom area with a bench seat, coat hooks and lockers. The second floor has 4 larger bedrooms and 2 bathrooms. The master bath, with it's ceramic tile floor, tiled shower and soaking tub, will be your place to retreat and pamper yourself at the end of the day. The hall bath has a tub/shower. The unfinished basement features 9' poured concrete walls. You also have the convenience of a central vac system. This home is situated on a corner homesite and has easy access to Vine Street and I-283. Although loaded with custom features, this home is priced well below replacement cost.
#PADA2048296

MIDDLETOWN

195 MAGNOLIA DRIVE

4 Beds

2 Baths

2,898 Sq.Ft.

$579,000

MLS#: PADA2048296

Welcome to a home that truly has it all—style, space, and an unbeatable lifestyle—now even more enticing with the seller offering $10,000 in settlement assistance or as an allowance for brand-new carpet, giving you the flexibility to make it perfectly your own. Step inside to a main level designed for both everyday living and unforgettable entertaining. A spacious, light-filled living room and elegant formal dining room set the tone, while the beautifully appointed kitchen shines with stunning granite countertops and sleek stainless steel appliances. The inviting eat-in area flows seamlessly into the warm and welcoming family room, where custom built-in bookcases and a cozy fireplace create the perfect backdrop for relaxing evenings and lively gatherings. Upstairs, you’ll find four generously sized bedrooms, along with the ease and convenience of second-floor laundry. The primary suite is a true retreat—your own private escape—featuring a luxurious soaking tub and separate shower designed for ultimate relaxation. The partially finished basement offers incredible potential, highlighted by a large 30x30 egress window and a full rough-in for a future bath—ideal for expanding your living space, creating a guest suite, home gym, or entertainment area. Peace of mind comes standard with major updates already completed, including a one-year-old HVAC system and a two-year-old roof. Step outside and fall in love with your own backyard oasis. The stunning paver patio, complete with a built-in fire pit and knee wall, is the perfect setting for entertaining under the stars or enjoying quiet evenings at home. A spacious two-car garage adds even more convenience. Located in the highly sought-after Bayberry community, you’ll enjoy an exceptional lifestyle with access to a beautiful clubhouse, scenic lake, walking paths, sidewalks, open green spaces, and a children’s play park—offering endless opportunities to connect, unwind, and make lasting memories. This isn’t just a home—it’s the lifestyle you’ve been waiting for.
#DENC2099108

MIDDLETOWN

1537 E MATISSE DRIVE

4 Beds

2 Baths

2,950 Sq.Ft.

$574,900

MLS#: DENC2099108

PRICE IMPROVEMENT!! - Get it while it's hot!! This spacious 3-bedroom home with a VERSATILE BONUS ROOM offers a thoughtfully designed layout and numerous updates throughout. The inviting family room with fireplace opens seamlessly to the center-island kitchen with a bar area at the island , now updated with a new stove, microwave, dishwasher, refreshed countertops, and a stylish backsplash, making it perfect for both everyday living and entertaining. Just off the kitchen you’ll find a convenient mudroom, pantry closet, half bath, and garage entry. Upstairs, the spacious primary suite boasts a tray ceiling, double vanities, his and her walk-in closets, and a beautifully tiled shower. Two additional bedrooms are generously sized, and the bonus room can be used as a den, home office, or playroom. The laundry room is conveniently located on this level. The full basement provides exceptional additional living space with a second family room, a large storage area, and a utility room. Plumbing is already roughed in for a future bathroom, and the water heater was replaced in 2019. Location Location Location!! Minutes from Routes 1, 13, and 301 with no tolls to go north and a grocery store 5 minutes away! Best of all—no grass to cut. The HOA handles lawn care, allowing you to enjoy your weekends relaxing by the community pool. HOA fees also include common area maintenance and snow removal.
#DENC2095628

MIDDLETOWN

336 ACASTA DRIVE

3 Beds

2 Baths

3,100 Sq.Ft.

$572,000

MLS#: DENC2095628

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

Alluring Appoquinimink Abode!! Beautifully nestled at the end of Silverhill Crossing, having only one side neighbor, and backing to trees, this home offers a bit of seclusion and lovely views! This grand colonial is a delightful mix of modern upgrades and some fun and warmth! A sweeping two story foyer with a captivating curved staircase greets you upon entering! To the right there is a charming living room, and to the left, there is a useful office with french doors! Beyond those, the back of the house has a splendid layout featuring a massive kitchen with a large island and roomy pantry! Entertaining is a dream since the kitchen adjoins a large dining room and a spacious sunroom that can also be used for dining! A sunken living room with a two story vaulted ceiling and a fireplace is a crowd pleaser! The lower level takes entertaining to a new level! Enjoy a movie in the theater that features a popcorn machine and six comfy seats! But, have some cocktails before the movie at the bar! Work off the movie goodies in the workout room! Once the entertaining has concluded for the night, head upstairs and enjoy some slumber in one of the 4 bedrooms! The primary suite is simply delicious, boasting a massive main bedroom with a lighted tray ceiling, a sizable sitting room, two walk in closets, a soaking tub with room for candles or wine, a separate shower, a doored commode, and 2 vanities! There are three more nicely sized bedrooms. Two of the three have walk in closets! Betwixt those, there is handsome full bathroom with plenty of cabinet space! New carpet was just added to the top two floors! Solar panels were just serviced. The garage is another spacious spot for it includes an additional bump out for a tool bench! The laundry/mud room connects the garage to the main floor and comes with a large coat closet and a utility sink. This Cantwell Cutie offers a lot to like!! Make it yours today!!
#DENC2100650

MIDDLETOWN

528 SILVERHILL CROSSING

4 Beds

2 Baths

4,900 Sq.Ft.

$570,000

MLS#: DENC2100650

New on site 1 day ago
Welcome to this spacious 5-bedroom, 3-bath ranch, perfectly situated on a cleared 1-acre lot with no HOA restrictions. This home offers the ideal blend of comfort, functionality, and freedom. Step inside to find stunning hardwood floors flowing throughout the main living areas, creating a warm and inviting atmosphere. The home features a formal dining room for gatherings and a generous family room perfect for relaxing or entertaining. A convenient first-floor laundry room adds to the ease of everyday living. The full basement expands your living and working space even further, featuring a bonus workshop, a separate office or gym, and plenty of storage to keep everything organized. Outside, the property truly shines. Enjoy plenty of parking with a 6-car driveway, and take full advantage of the expansive yard—complete with an above-ground pool, a chicken coop, and ample open space for gardening, recreation, or future additions. Energy efficiency is a major bonus with owned solar panels, helping reduce utility costs while adding long-term value. If you’re looking for space, flexibility, and a property with no restrictions, this one checks all the boxes.
#DENC2100926

MIDDLETOWN

160 PINE VALLEY DRIVE

5 Beds

3 Baths

2,900 Sq.Ft.

$565,000

MLS#: DENC2100926

Below market value & PRICED TO SELL!!!!! This meticulously maintained home reflects true pride of ownership, both inside and out. Thoughtfully priced and offering exceptional value, this home is ideally situated in the prestigious community of The Legends in Middletown, enjoying convenient access to shopping, dining, and everyday amenities while offering a peaceful, scenic setting overlooking the golf course. Upon entry, a grand two-story foyer welcomes you with soaring ceilings and an elegant turned staircase, immediately setting a tone of sophistication. The thoughtfully designed, flowing floor plan leads to a stunning two-story family room, highlighted by a gas fireplace that creates a warm and inviting focal point—perfect for cozy evenings or refined entertaining. The spacious kitchen is designed for both function and style, featuring abundant cabinetry and counter space, a center island for added storage, and sliding glass doors that open to the deck—seamlessly blending indoor and outdoor living. The rear fenced yard offers privacy and generous space for entertaining, gardening, or simply unwinding while enjoying tranquil golf course views. Enhancing the home’s functionality, the main level also features a private office, ideal for today’s work-from-home lifestyle, as well as a convenient main-level laundry room with direct access to the garage, adding everyday ease and practicality. The primary suite serves as a private retreat, complete with a walk-in closet, linen closet, and a beautifully appointed en-suite bath. Three additional generously sized bedrooms and a well-appointed hall bath complete the upper level, offering comfort and flexibility for family, guests, or home office needs. A true highlight of this home is the fully finished basement, providing exceptional bonus space. It features two additional rooms with closets, a full bath, a counter and cabinet area ideal for entertaining, a dedicated theater area, and a large unfinished space for ample storage—perfect for multi-generational living, recreation, or extended guest accommodations. This home is a MUST SEE!!!
#DENC2093134

MIDDLETOWN

241 PORKY OLIVER DRIVE

4 Beds

2 Baths

2,650 Sq.Ft.

$564,900

MLS#: DENC2093134

Welcome home to 1220 N Olmsted Pkwy located in the sought-after Village of Bayberry North. Upon arrival, you’ll immediately notice the beautiful stone veneer exterior, offering timeless curb appeal and setting the tone for this well-maintained, 5-year-old ranch home. An inviting covered front porch welcomes you in, perfect for morning coffee, evening relaxation, or connecting with neighbors. Step inside to an OPEN -CONCEPT LAYOUT filled with natural light and hardwood flooring. The entire home has just been FRESHLY PAINTED , giving it a clean and modern feel -making it truly move-in ready. The spacious living room flows seamlessly into the dining area and continues into the kitchen, creating an ideal space for everyday living and entertaining.The kitchen features a CENTER ISLAND, GRANITE COUNTERTOPS, STAINLESS STEEL APPLIANCES, A DOUBLE OVEN, and a sunny BUMP- OUT BREAKFAST area that fills the home with natural light. Step outside to the fully fenced backyard, offering endless possibilities for entertaining, relaxing, or outdoor activities. Back inside, the home offers a convenient laundry room with access to the two-car garage. You’ll find 2 generously sized bedrooms, along with a versatile additional room that can be used as a third bedroom, home office, or playroom. The primary suite boasts a spacious walk-in closet and a private bath with double vanity and a glass stand-up shower. An additional full bathroom serves family and guests. The spacious unfinished basement offers exceptional ceiling height and a blank canvas for future customization, ideal for creating additional luxury living space, a home theater, fitness area, or private retreat. A two-car garage and ample driveway parking complete the home. With new shopping centers, grocery stores, dining, and major commuter routes just minutes away, this home offers the perfect balance of suburban charm and modern convenience. This move-in-ready home is ideal for families ready to connect and enjoy everything Bayberry North has to offer. Schedule your tour today and imagine the possibilities.
#DENC2096488

MIDDLETOWN

1220 N OLMSTED PARKWAY

3 Beds

2 Baths

1,850 Sq.Ft.

$564,900

MLS#: DENC2096488

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Buyers resources
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Selling Your Home for More $$

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