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 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
232
# of Listings
3
Avg # of Bedrooms
$273
Avg. $ / Sq.Ft.
$647,221
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

232 Properties Found. Page 2 of 16.

Welcome home! Just 6 years young, this home has been meticulously maintained. A true blend of craftsman style and casual coastal charm, it offers endless possibilities with its thoughtful layout and multiple living spaces. Outside enjoy crisp fall evenings on the paved patio with fire-pit. Or take advantage of the 3 bay detached garage, perfect for extra vehicles, hobbies and all of your extra “toys” Step inside the home to an open concept main level with plenty of natural light with walls of windows overlooking the wooded 2.11 acre lot.. The kitchen boasts a large island ideal for gatherings and entertaining. The main level owner’s suite offers beautiful tray ceilings, large soaking tub, and a custom walk-in closet. Upstairs you’ll find 3 spacious bedrooms and a versatile media room perfect for movie nights, or relaxing retreats. The finished basement is a showstopper with its kitchenette, full bar, full bath, home office, and bonus flex room with walk-in closet. This space was designed for both work and play. This home balances modern functionality with timeless design. It offers abundant space for everyday living and entertaining. Don’t miss the opportunity to see it, schedule your tour today.
#DENC2088290

MIDDLETOWN

1215 BUNKER HILL ROAD

4 Beds

4 Baths

4,300 Sq.Ft.

$1,249,000

MLS#: DENC2088290

A lovely brick federal style home with some Georgian characteristics. This home is placed on the national historic register. The property itself is 14.6 acres improved by mature trees, magnificent boxwoods, and lots of privacy. The home and numerous outbuildings were originally built during the local peach era, making Monterey one of Middletown's peach plantation homes. The outbuildings have just as much history as the main house. Additionally featured are several barns, a second 3 bedroom home, 4 car garage, and a 3 hole privy which is also on the historic register along with the unique ice and smoke houses. This country estate home is a great opportunity to add your restoration touches and make this your farmette in which to raise your kids, horses, and animals. No homesale contingencies
#DENC2089970

MIDDLETOWN

692 BAYVIEW ROAD

None Beds

None Baths

7,026 Sq.Ft.

$1,200,000

MLS#: DENC2089970

Welcome to this stunning ranch-style home that redefines spacious living! With an impressive 5,000 square feet, this property features 7 generous bedrooms and 4.5 bathrooms, ensuring ample space for family and guests. Step inside to discover soaring 9-foot ceilings that enhance the open, airy feel throughout. The heart of the home is the modern kitchen, perfect for culinary enthusiasts and gatherings alike, with the open floorplan to the family room with a floor to ceiling stone hearth gas fireplace and sun room. Venture downstairs to find your personal retreat accommodating a stylish bar area with marble countertops and built in wine cooler and a second family room with full bathroom. Upstairs is a bedroom with sitting area. This loft area includes a full bath creating the perfect guest suite. As for parking, there is a two-car attached garage with opener and a one car detached garage with ½ bath accessible for the pool area. And a driveway that can accommodate 6 cars. Set on a beautiful fenced half-acre lot with in ground irrigation system, this outdoor oasis includes a gazebo, providing the perfect venue for gatherings and leisure activities. An addition to the oasis feel is the salt water in-ground pool, (that the seller will pay to have opened in the spring) ideal for relaxation and entertaining. Don't miss your chance to own this exceptional property that harmonizes luxury, comfort, and a lifestyle of elegance!
#DENC2095326

MIDDLETOWN

836 SWEET BIRCH DRIVE

7 Beds

4 Baths

5,650 Sq.Ft.

$1,200,000

MLS#: DENC2095326

A lovely brick federal style home with some Georgian characteristics. This home is placed on the national historic register. The property itself is 14.6 acres improved by mature trees, magnificent boxwoods, and lots of privacy. The home and numerous outbuildings were originally built during the local peach era, making Monterey one of Middletown's peach plantation homes. The outbuildings have just as much history as the main house. Additionally featured are several barns, a second 3 bedroom home, 4 car garage, and a 3 hole privy which is also on the historic register along with the unique ice and smoke houses. This country estate home is a great opportunity to add your restoration touches and make this your farmette in which to raise your kids, horses, and animals. No homesale contingencies
#DENC2089142

MIDDLETOWN

692 BAYVIEW ROAD

None Beds

None Baths

7,026 Sq.Ft.

$1,200,000

MLS#: DENC2089142

New on site 1 day ago
Mixed-Use Investment Opportunity! Well-maintained 10-unit on a prime corner location with high visibility in Middletown. The building includes 7 apartments (1 vacant) plus 3 commercial units, and a parking lot in the rear. Please be respectful as the first floor commercial businesses are active.
#PADA2052928

MIDDLETOWN

2 S UNION STREET

None Beds

None Baths

N/A

$1,199,900

MLS#: PADA2052928

Lot 1 East at Heritage Oak Estates | To-Be-Built Custom Home Opportunity. Don’t miss this rare opportunity to build your dream home in Heritage Oak Estates, an exclusive twelve-lot community by Atlantic Homes, nestled in the heart of the scenic Middletown Valley. Located less than a mile from charming Main Street in Middletown, MD this enclave offers panoramic views of pastoral landscapes and surrounding mountains—all with no HOA restrictions. Lot 1 East spans a generous 4.6-acre homesite and has already been approved for a four-bedroom septic system, with a private well already in place—ready for your dream home. Choose from a range of fully customizable floor plans or bring your own design. Each home will feature elevated standard finishes throughout, including: Masonry board exterior siding with stone water table; 10’ to 12' ceilings on the main level. Lot sizes in the community range from 2 to 7 acres, each offering its own unique views and privacy. Protective covenants ensure architectural integrity and long-term value—vinyl siding is not permitted, and minimum build standards apply. Lot 1 East offers the perfect blend of rural tranquility, upscale living, and accessibility—all in one of Frederick County’s most desirable areas. Photos and renderings are representative and for illustrative purposes only. All builder plans can be customized to fit your preferences. Contact listing agent for available plans, site details, and to explore available homesite options and start designing your future dream home today at Heritage Oak Estates!
#MDFR2069796

MIDDLETOWN

3130 BIDLE RD

4 Beds

3 Baths

2,500 Sq.Ft.

$1,186,202

MLS#: MDFR2069796

Lot 1 West at Heritage Oak Estates | To-Be-Built Custom Home Opportunity. Don’t miss this rare opportunity to build your dream home in Heritage Oak Estates, an exclusive twelve-lot community by Atlantic Homes, nestled in the heart of the scenic Middletown Valley. Located less than a mile from charming Main Street in Middletown, MD this enclave offers panoramic views of pastoral landscapes and surrounding mountains—all with no HOA restrictions. Lot 1 West spans a generous 2-acre homesite and has already been approved for a four-bedroom septic system, with a private well already in place—ready for your dream home. Choose from a range of fully customizable floor plans or bring your own design. Each home will feature elevated standard finishes throughout, including: Masonry board exterior siding with stone water table; 10’ to 12' ceilings on the main level. Lot sizes in the community range from 2 to 7 acres, each offering its own unique views and privacy. Protective covenants ensure architectural integrity and long-term value—vinyl siding is not permitted, and minimum build standards apply. Lot 1 West offers the perfect blend of rural tranquility, upscale living, and accessibility—all in one of Frederick County’s most desirable areas. Photos and renderings are representative and for illustrative purposes only. All builder plans can be customized to fit your preferences. Contact listing agent for available plans, site details, and to explore available homesite options and start designing your future dream home today at Heritage Oak Estates!
#MDFR2069522

MIDDLETOWN

7452 HERITAGE OAK TERRACE

4 Beds

3 Baths

2,618 Sq.Ft.

$1,180,000

MLS#: MDFR2069522

Modern Luxury Meets Timeless Craftsmanship on a Private 1-Acre Estate Welcome to this stunning custom-built luxury residence, meticulously designed to combine modern elegance, high-end finishes, and thoughtful functionality. Situated on a perfectly flat 1- acre lot, this exceptional home offers over 3,000 square feet of living space, every detail curated for comfort and sophistication. The exterior features bold black windows, James Hardie board & batten siding, premium vinyl siding, and metal roofing and architectural shingles. Car enthusiasts and hobbyists will appreciate the 800 square feet of garage space, including a 2-car turned garage and a separate 1- car front-facing garage, both featuring high ceilings and recessed lighting—perfect for storage, a workshop, or a car lift setup. The oversized, concrete front porch has beautiful rough-cut cedar posts, while a beautifully designed hardscape walkway guides you to the entrance featuring an 8-foot craftsman front door. Once inside you’ll notice the architecturally pleasing open floor plan, the 9-foot ceilings, the wide-board white oak hardwood flooring that flows throughout the main level, and the white oak railings with sleek black horizontal metal balusters that adds a modern architectural touch to the grand staircase. The main floor also boasts 8-foot craftsman-style interior doors, custom trim work, modern custom floor vents, and full recessed lighting throughout. Chef’s Dream Kitchen The heart of the home is a gourmet kitchen that redefines luxury and function. Features include 42-inch custom cabinetry with detailed crown molding and under-cabinet lighting, a hidden walk-in pantry seamlessly integrated into the cabinetry, Additional pantry cabinets with rollout drawers for effortless organization , a Custom vent hood flanked by built-in spice cabinets and a 36-inch gas range, Full quartz countertops and backsplash plus a massive quartz slab island with a farmhouse sink, Integrated microwave drawer for clean a modern convenience. Enjoy cozy evenings in the spacious living room featuring vaulted ceilings and a gas fireplace with a custom barn beam mantle. The main level features the primary bedroom as well as a second bedroom/in-law suite with access to another full bathroom and laundry room. The primary suite features a large walk-in closet and barn doors that leads into the spa-inspired bathroom. This beautiful custom bathroom features large format tiles floors, a freestanding soaking tub, a floating double vanity, and a custom tiled walk-in shower with a frameless glass door. Upstairs, discover two additional bedrooms, a full bathroom with custom tile and shower, a second laundry area, and a spacious lounge area with a half bath—perfect for a media room, playroom, or home office. Additionally, the basement is over 2000 square feet and features 9-foot ceilings, offering unlimited potential for customization. This home is the perfect blend of luxury, practicality, and custom craftsmanship—an ideal sanctuary for modern living. Whether you're entertaining, working from home, or simply relaxing, every inch of this home has been designed with lifestyle in mind.
#DENC2091082

MIDDLETOWN

415 MARCUS ROAD

4 Beds

3 Baths

3,178 Sq.Ft.

$1,150,000

MLS#: DENC2091082

Nestled in the prestigious Summit Pointe community, this exquisite Colonial-style residence, built in 2023, offers a harmonious blend of luxury and comfort. Spanning an impressive 4,175 square feet, this home is designed for those who appreciate high-end living and thoughtful details. As you step inside, you are greeted by a grand staircase that sets the tone for the elegance found throughout the home. The spacious family room, conveniently located off the gourmet kitchen, invites gatherings and cherished moments. The kitchen is a culinary enthusiast's dream, featuring a large island, stainless steel appliances, and a generous pantry, ensuring that every meal is a delight to prepare and enjoy. The formal dining room provides an ideal setting for entertaining guests, while the cozy gas fireplace in the living area creates a warm ambiance for intimate evenings at home. The luxurious primary suite is a true retreat, featuring a large sitting room perfect for relaxing or a private home office. The luxurious primary suite is a true retreat, featuring a large sitting room, a walk-in closet, and a spacious en-suite bath with a soaking tub and separate shower stall. The upper level also includes three additional bedrooms—one with its own private en-suite and two that share a convenient Jack and Jill bathroom—offering comfort and flexibility for family or guests. The main floor laundry adds everyday convenience, while the unfinished full basement with a rough-in for a future bathroom and walkout stairs offers endless possibilities. Whether you envision a home theater, fitness area, or additional living space, this lower level is ready to be customized to suit your lifestyle. Set on a beautifully landscaped 0.51-acre lot, the property features a level rear yard and a charming front yard, perfect for outdoor activities or simply enjoying the serene surroundings. The side-entry oversized garage, with space for two vehicles, along with additional driveway parking ensures that you and your guests will always have ample space. With its excellent condition and modern amenities, it promises a life of comfort and luxury in a sought-after neighborhood. Experience the perfect blend of elegance and functionality in this stunning property, where every detail has been meticulously crafted to create a true sanctuary.
#DENC2088926

MIDDLETOWN

258 DILLON CIRCLE

4 Beds

3 Baths

4,175 Sq.Ft.

$995,000

MLS#: DENC2088926

The Kennedy Model Home by Blenheim Homes, located at 1203 N. Olmsted Parkway in the prestigious Bayberry North community, offers a masterclass in modern luxury and functional design. This expansive residence boasts 5 bedrooms and 5.5 bathrooms, including a convenient main-level in-law suite and a spacious 3-car garage. The home greets visitors with a grand two-story foyer and an elegant butterfly staircase that leads to an open-concept main level featuring a gourmet chef’s kitchen and a soaring two-story family room. The living space extends into a fully finished basement designed for entertaining, complete with durable tile flooring and 6' sliding glass egress doors that provide ample natural light and easy outdoor access. Situated within the award-winning Appoquinimink School District, this home is surrounded by Bayberry’s premier amenities, including a 70-acre park and an 11-acre lake. Please note that all viewings of this model home are by appointment only; interested parties must call the sales center to schedule a visit.
#DENC2095914

MIDDLETOWN

1203 N OLMSTED PARKWAY

5 Beds

5 Baths

4,600 Sq.Ft.

$989,000

MLS#: DENC2095914

MOVE-IN READY! This newly built home offers a rare opportunity to enjoy modern living on a 3-acre homesite in the highly regarded Middletown School District. Thoughtfully designed with both comfort and style in mind, it makes a striking first impression with its wide covered front porch and scenic wooded surroundings. Inside, the main level features an inviting, open layout filled with natural light and clean, modern finishes. A private office provides a quiet workspace, while the bright living and dining areas offer flexible spaces for gathering and entertaining. At the heart of the home is the showstopping gourmet kitchen, designed for both everyday living and hosting. It features white shaker cabinetry with warm wood accents, soft-close drawers, quartz countertops, double wall oven, Cafe stainless steel appliances, striking pendant lighting, and a spacious walk-in pantry. The expansive center island with seating creates a natural place to gather. Upstairs, you’ll find four spacious bedrooms, three well-appointed baths, and a convenient second-level laundry room. The primary suite offers a relaxing retreat with abundant natural light, a generous walk-in closet, and a spa-like bath with quartz countertops and an oversized shower wrapped in floor-to-ceiling porcelain tile. Situated on a beautiful 3-acre lot with mature trees, this home brings together modern design, quality craftsmanship, and the comfort of new construction—all in a desirable Middletown setting. NO HOA, No City Taxes. Builder Incentives Available!
#MDFR2074988

MIDDLETOWN

3105 SUMANTOWN ROAD

4 Beds

3 Baths

3,544 Sq.Ft.

$949,900

MLS#: MDFR2074988

PDR Homes is offering house packages at Americus Manor, a private subdivision featuring three lots within the Middletown school district. The subdivision is adjacent to over 135 acres of parkland, ensuring serenity and seclusion. The pricing shown is for the Lexington model, elevation 4 on Lot 2, a 2.37-acre partially wooded lot with an approved septic and existing well. PDR Homes is the exclusive builder at Americus Manor. The photos showcase some of the house designs offered, which can be customized to fit your preferences.
#MDFR2071116

MIDDLETOWN

Lot 2 SUMANTOWN ROAD

3 Beds

2 Baths

3,200 Sq.Ft.

$940,865

MLS#: MDFR2071116

810 Ashby Drive is a resort-style luxury estate in Middletown’s coveted Ashby’s Place community, offering the perfect blend of high-end finishes, thoughtful updates and true indoor–outdoor living. Built in 2015 by K. Hovnanian, this expansive Aspen II model offers approximately 5,225 sq ft of finished living space with 5 bedrooms, 4 full baths and 1 half bath on a beautifully hardscaped. A dramatic two-story foyer with sweeping hardwood staircase sets the tone the moment you enter, opening to elegant formal living and dining rooms ideal for entertaining. The gourmet kitchen is the heart of the home, featuring granite countertops, an oversized prep island, double wall ovens, stainless steel appliances, walk-in pantry and a bright morning room that flows seamlessly into the family room with a cozy gas fireplace. A private main-level office, stylish powder room and a well-appointed laundry room with 2 washer/dryer setup to add everyday convenience. Upstairs, the luxury continues with a serene owner’s suite offering dual walk-in closets and a spa-inspired bath. Secondary bedrooms are generously sized, including one with an en-suite bath—perfect for family, guests or multigenerational living. The fully finished basement is designed for entertaining and extended stays, showcasing a granite wet bar with wine fridge, expansive recreation space, a fifth bedroom, full bathroom and multiple egress windows for natural light. Step outside to your private resort: an L-shaped in-ground pool, Trex deck, custom paver patio, fire pit, and an outdoor kitchen with bar seating create an unforgettable backdrop for summer gatherings. A climate-controlled pool house with full bath and cabana-style amenities completes this incredible outdoor oasis. Additional highlights include a three-car front-entry garage, extensive exterior lighting and hardscaping, public utilities, natural gas heat and central air, all within a low-fee HOA community convenient to top-rated Appoquinimink schools, walking trail, commuter routes, shopping and dining.
#DENC2093464

MIDDLETOWN

810 ASHBY DRIVE

5 Beds

4 Baths

5,225 Sq.Ft.

$919,900

MLS#: DENC2093464

Welcome to 448 Spring Hollow Drive. This well-maintained freshy painted colonial home sits on a lovely corner lot located in the desirable community of Parkside, with an additional 1/2 acre of non-buildable open space behind the property. Being a former model home, this 5 bedroom, 5 1/2 bath home features many well-executed upgrades, 4 fireplaces, stunning trim and lighting upgrades throughout. The first floor offers an elegant living room with a two-sided fireplace, large dining room that comfortably seats 14, a unique curved conservatory/music room featuring a lovely marble floor and a two-sided fireplace, a large eat-in kitchen as the heart of the home that opens to a sunroom, large family room with a natural stone fireplace. There is also a library, 1/2 bath and first floor laundry. On the second floor you will find a spacious primary bedroom with fireplace, sitting area, 2 walk-in closets (one large enough to be a dressing room), and a large bright bathroom with a private toilet room, and features a get-away jetted tub to unwind and relax. The other 3 large bedrooms and 2 baths round out that floor. On the third floor you are welcomed to a private space with a sitting area, full bath and large bedroom. The highly finished 1367 sq ft lower level has the 4th fireplace and lots of open space for entertaining, watching movies, and game playing. There is a spacious granite wet bar with a full-size refrigerator and dishwasher. There is also a full bath and an additional bonus room to use as a playroom, office, exercise room or anything you need. The large walk-out basement door with sidelights provides lots of natural light into the lower level. The unfinished portion is spacious with tons of storage space. Because this was the model home for the builder, the garage was transformed into a large office with glass divider, french doors and windows for natural light. It is a perfect, quiet, private space for the professional who works from home. The garage can be returned to a 2-car garage easily if that is better for your family’s needs. This garage space is not included in the 5475 square footage of the home. The additional space in the garage area is a mud/exercise room and provides lots of additional storage for kitchen overflow, etc. The clubhouse and pool are easily walkable. Cool off in the pool on hot summer days or maybe make working out in the gym a part of your daily routine all year round.
#DENC2086894

MIDDLETOWN

448 SPRING HOLLOW DRIVE

5 Beds

5 Baths

6,840 Sq.Ft.

$899,000

MLS#: DENC2086894

Welcome to 434 Spring Hollow Drive, a beautiful residence nestled in Middletown's most sought-after community. This home is ideally situated on one of the finest lots, offering tranquil views as it backs onto lush woods. Located on a charming tree-lined street, it's just a short walk to the community clubhouse, which boasts a large pool and fitness center. As you approach the home, the inviting front porch welcomes you. Step inside to be greeted by stunning hardwood floors that extend throughout the first floor and up to the second level. The first floor features a versatile office, a cozy living room, an elegant dining room, and a gourmet kitchen that overlooks the family room, complete with a striking stone gas fireplace. Adjacent to the kitchen is a spacious sunroom that offers lovely views of the expansive backyard. The home also includes a walk-out basement, making it an entertainer's paradise, perfect for hosting gatherings with family and friends. Whether you're enjoying the serene surroundings or crafting delicious meals, this property provides all the amenities needed for a luxurious and comfortable lifestyle. Seize the opportunity to own this exceptional home in a premier location. Schedule your tour today and make this dream home yours!
#DENC2090088

MIDDLETOWN

434 SPRING HOLLOW DRIVE

5 Beds

3 Baths

5,092 Sq.Ft.

$899,000

MLS#: DENC2090088

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