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
238
# of Listings
3
Avg # of Bedrooms
$269
Avg. $ / Sq.Ft.
$653,613
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

238 Properties Found. Page 7 of 16.

Welcome to 321 Ellenwood Drive, located in the sought out neighborhood of PARKSIDE. What an unique home!!!! a semi custom home built by Lifestyle by the original owners. This inviting 4 bedroom, 3.1 bathroom home is very special....first floor very large primary suite...Beautiful kitchen with all new appliances including a double oven, great counter space and eat in area with sliding doors out to a lovely paver patio with real wrought iron railing. The family room just had their hardwoods refinished and WOW ... did they come out beautiful, a gas fireplace a 4 windows pouring in with natural sunlight. 2nd floor has a large loft, 2 bedrooms and 1 full bathroom and then a large office/playroom/flex room that has an opening to the the family room below....and a cute balcony to sit our on and stare out the stunning tree lined street..... then a third floor with another loft, large bedroom and full bathroom....wait, so much more.... a 3 season room that has 3 points of exits... one to side yard, one to the other side yard that is fenced and one off the back of the house connecting to the 2 car garage. Now, if that is not enough, there is a large unfinished basement waiting for you to finish if you wish with a rough in and 9 foot ceilings... also a walkup bilco door... radon remediation added... a generator...beautiful landscaping...upgraded and maintained so well.... Now for the best news...brand new roof and the solar panels are being put back up 12/1 and will be owned up until March of 2036....Sellers bought out the lease for your savings!!!! Parkside has so much to offer... the community pool, where you can soak up the sun and enjoy a refreshing swim during warm summer days. The gym..... the club house.... and all our beautiful pocket parks. Don't miss your chance to call this charming home in a sought-after neighborhood yours. Schedule a viewing today to experience the comfort and convenience this property has to offer in person.
#DENC2092224

MIDDLETOWN

321 ELLENWOOD DRIVE

4 Beds

3 Baths

3,175 Sq.Ft.

$649,999

MLS#: DENC2092224

Have you been looking for the perfect sophisticated and elegant historic home? Do you want everything; a gracious home, amazing space, acreage, a place for chickens, but also walkable and close to town? It sounds impossible, but you've found it! Welcome to historic Maplewood, circa 1872, know colloquially as The Tower. With no HOA and business B-1 zoning, this property presents endless possibilities, allowing dozens of potential uses! With stunning Italianate architecture and over an acre of land, this property is one in a million. This landmark home located in the heart of lovely downtown Middletown is a piece of history with all the modern conveniences. Rich with history, this amazing property was once the home and studio of John Chumley, a famous local artist. (The current owners have tons of photos and information about the history of the home that they'd love to share with you!) Too many amazing features to list; gorgeous high ceilings, original hardwood floors, wrap around built ins, huge windows, original millwork throughout, a generous kitchen and huge walk in pantry, fabulous mudroom, several outbuildings for storage and work space, an amazing chicken coop; the list goes on and on! Featuring four large bedrooms and two and half bathrooms, this home is spacious, beautiful, and elegant. The panoramic mountain views will take your breath away, especially from the tower studio room. And the home sits on a fantastic level lot behind public memorial land! All of this, located right in the center of town, so shopping and restaurants are just steps away. Middletown is an ideal location for commuters, with Rt 37, I-66 and I-81 within just a few minutes drive, not to mention all the natural beauty, activities, and amenities of the Shenandoah Valley. This is the one!!!
#VAFV2038812

MIDDLETOWN

2239 SIXTH STREET

4 Beds

2 Baths

2,944 Sq.Ft.

$649,900

MLS#: VAFV2038812

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.

$649,900

MLS#: DENC2094616

This is a builder model home sale. This beautiful Calloway Queen Anne offers 2,657 square feet of living space. The abundance of windows floods the family room and kitchen with natural light. Upgraded luxury vinyl plank runs throughout the first floor, the upstairs hall, and primary bedroom. The kitchen boasts an oversized island, quartz countertops, and a tiled backsplash. Both bathrooms offer quartz vanity tops.
#DENC2088810

MIDDLETOWN

5605 S BAYBERRY PKY

4 Beds

2 Baths

N/A

$639,000

MLS#: DENC2088810

Quick Delivery 5 bedroom home in Appoquinimink school district. READY TO GO! This lovely home offers a 1st floor full bath with bedroom/office space, and the remaining 4 beds and 2 baths upstairs. The Charleston floor plan offers a well crafted layout with walk-in pantry, butler's pantry, switchback staircase, and much more. Quality products like Hardie Plank Siding, Timbertech front porch, and Anderson windows add to the fine construction by this local, semi-custom builder (Benchmark Builders). Check in at the model home during business hours for a tour and more information. This home can be seen 7am-8pm via the NTerNow app. Simply show up, scan the QR code, and follow the instructions.
#DENC2095376

MIDDLETOWN

1011 STUYVESANT STREET

5 Beds

3 Baths

2,716 Sq.Ft.

$628,898

MLS#: DENC2095376

The Carver - with 4,000 finished sq. ft. - is a thoughtfully designed home that blends open living with private retreats. A welcoming foyer with a detailed ceiling treatment sets the tone as you enter. Just off the entry, a private home office with stylish barn doors offers the perfect space for telecommuting or quiet focus. The spacious great room and dining area come together beneath a vaulted ceiling, creating an open, airy feel ideal for both everyday living and entertaining. The striking kitchen features abundant counter space and a large pantry, making meal prep and storage effortless. Tucked away for privacy, the primary suite showcases an elegant ceiling treatment, a generous walk-in closet, and a luxurious primary bath with freestanding vanities and a large walk-in shower. The finished basement expands the living space with a recreation room, additional bedroom, and full bath—perfect for guests, hobbies, or multi-generational living. This listing is for a to be built home and photos are of a model home for display purposes only. Please see sales consultant for details.
#DENC2096234

MIDDLETOWN

1932 DIXON WAY

3 Beds

3 Baths

4,147 Sq.Ft.

$626,990

MLS#: DENC2096234

Welcome to this stunning home located in sought-after Middletown, DE. This gorgeous property boasts 3 bedrooms, 3.1 bathrooms, and a 2-car garage, offering plenty of space for comfortable living. As you step inside, you are greeted by luxury vinyl plank flooring that runs throughout the first floor. The main level features an office/flex room, perfect for those who work from home or need a versatile space. The open kitchen is a chef's dream, complete with granite countertops, tile backsplash, a large island, and stainless steel appliances. The kitchen seamlessly flows into the dining area and family room, where you can cozy up by the gas fireplace. Step outside to the rear yard, where you will find a composite deck and a fully fenced yard, perfect for outdoor entertaining. Upstairs, you will find a large loft area that offers additional flex space. The primary bedroom is generously sized and features a huge walk-in closet and an en suite bathroom with double sinks, a water closet, and a glass shower. There are two additional bedrooms, a hall bathroom, and a convenient laundry room. Loft can be converted to the 4th bedroom. Based on offer, sellers will convert the space or credit buyer. The lower level of the home is finished and offers a full bathroom, providing endless possibilities for use. Currently set up as a theater room and gym, this space could easily be converted into an additional bedroom if desired. The Preserve at Deep Creek community amenities include a pool and lawn care, making this home low maintenance and perfect for those seeking a relaxed lifestyle. Conveniently located near downtown Middletown, routes 299, and 301, this home is move-in ready and meticulously maintained. Don't miss out on the opportunity to make this beautiful property your next home!
#DENC2095996

MIDDLETOWN

772 WALLASEY DRIVE

4 Beds

3 Baths

3,243 Sq.Ft.

$625,000

MLS#: DENC2095996

NEW PRICE! Owner has interior professionally painted! Beautiful Stone Front Colonial in Sought-After Pineland Park 3,887 total finished square feet offering 6 bedrooms and 3.5 baths on a 1-acre lot. Located in the desirable Pineland Park neighborhood of Warren County, ideal for commuting via I-66 and I-81. Minutes to golf, wineries, hiking, shopping, and downtown Front Royal. The Jefferson III model by H & H Builders features a stone front exterior, wide trim, interior columns, and 9-ft ceilings. Main level includes newly refinished hardwood floors throughout, a formal living room, and a formal dining room with chair rail and box ceiling detail. Spacious family room with corner gas fireplace opens to the kitchen with abundant cabinetry, countertop space, and breakfast area. Covered wrap-around front porch and rear covered porch provide great outdoor living spaces. Upper level offers hardwood hallway floors and new carpet in bedrooms. Newly remodeled primary suite includes vinyl plank flooring, tiled bath with soaking tub, separate shower, and walk-in closet. Newly remodeled upper-level bath. Three additional bedrooms and upper-level laundry for added convenience. Fully finished walk-out basement features tile flooring, kitchenette/wet bar, family room, two bedrooms, full bath, and ample storage—perfect in-law or guest suite. New AC units; furnace less than 5 years old. 2-car front-load garage with concrete driveway and plenty of off-street parking. Over 1 acre of open yard to enjoy.
#VAWR2012638

MIDDLETOWN

76 KATIE LANE

6 Beds

3 Baths

3,888 Sq.Ft.

$625,000

MLS#: VAWR2012638

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

MIDDLETOWN

2202 EARLY COURT

3 Beds

2 Baths

1,662 Sq.Ft.

$624,900

MLS#: DENC2093608

Build your dream home with Schaeffer Homes in Middletown with Schaeffer Homes! This home is to be built through their Build On Your Lot Program. Starting at 2,223 square feet, the Ellis is a sizable home, with 2 modern elevations options. This model includes 4 bedrooms, 2 1⁄2 baths, and a 2-car garage, providing ample space for families of all sizes. The home starts at 2-stories, with the option to add to a 3rd floor if you are in need of an extra bedroom and bath!! The great room is adequate enough to fit a large dining table, while still allowing extra space to spread out between the kitchen and family room. With its sleek design and thoughtful layout, the Ellis is the perfect blend of style and functionality. The homesite is listed for $230,000, the home is $271,900, and the estimate for land development cost is $120,000. Land development costs can be more or less than $120,000. Seller and Builder make no representation of the feasibility and cost for site development and will provide a due diligence period to the Buyer. Schaeffer Homes has the exclusive right to build on this lot and will assist the Buyer through the due diligence process. It is unknown if a basement foundation is available until soil testing is completed, which will be the responsibility of the Buyer. Seller and Builder make no representation of the feasibility and cost for site development and will provide a due diligence period to the Buyer. Schaeffer Homes has the exclusive right to build on this lot and will assist the Buyer through the due diligence process. ***NOTE: Home is to be built. Pictures and virtual tour are of the same base model with upgraded options shown. Other Schaeffer Floorplans are available to be built on this homesite.
#DENC2092334

MIDDLETOWN

1487 BUNKER HILL ROAD

4 Beds

2 Baths

2,223 Sq.Ft.

$621,900

MLS#: DENC2092334

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

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.

$610,000

MLS#: DENC2092652

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

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