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
261
# of Listings
3
Avg # of Bedrooms
$271
Avg. $ / Sq.Ft.
$642,232
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

135 Properties Found. Page 9 of 9.

Rare opportunity in the heart of Middletown! Discover the perfect blend of small-town charm, open space, and future potential on this beautiful 8-acre property surrounded by scenic pastureland and mountain views. Currently used for cattle and hay production, the land is partially fenced and includes a shed, making it ready for agricultural use or the ideal setting for your own private farmette—bring your animals and start living the country lifestyle. Imagine building your dream home while enjoying the peace and wide-open space this property provides. With town water and sewer hookups available, you’ll have the convenience of municipal services while still enjoying the feel of rural living. Zoned RA, the parcel may offer the potential for up to four homesites (buyer to verify)—perfect for a family compound, custom home sites, or a long-term investment opportunity. Located just a short walk to historic Main Street, you can easily enjoy local restaurants, shops, and community events. Plus, I-81 is only minutes away, making commuting simple while you return home each day to your peaceful countryside retreat. Opportunities like this are hard to find in Middletown. Schedule your showing today and explore the possibilities this special property offers. Property sold as-is. Buyer to verify subdivision potential, utilities, and zoning. Property is currently in land use; rollback taxes may apply if removed. Livestock on property—showings by appointment with agent accompaniment only. Q: Where is Middletown, Virginia located? A: Middletown is located in the scenic Shenandoah Valley of Virginia, just south of Winchester and minutes from Interstate 81. Q: What makes Middletown a desirable place to live? A: Middletown offers small-town charm, historic character, and beautiful mountain views while still being close to shopping, dining, and commuter routes. Q: What outdoor activities are nearby? A: Residents enjoy easy access to hiking, fishing, and exploring the Shenandoah Valley, as well as nearby parks, rivers, and scenic mountain drives. Q: Is Middletown convenient for commuters? A: Yes. With quick access to I-81 and nearby Route 11, Middletown provides a convenient commute to Winchester and surrounding Shenandoah Valley communities. Q: What is the lifestyle like in Middletown? A: The town is known for its welcoming community, historic Main Street, seasonal events, and peaceful rural surroundings that make it a great place to enjoy the Shenandoah Valley lifestyle.
#VAFV2039608

MIDDLETOWN

VETERANS - LOT 12 ROAD

None Beds

None Baths

8.0 acres

$549,000

MLS#: VAFV2039608

The Bristol Model is a thoughtfully designed 3-bedroom home that is TO BE BUILT in the highly sought-after 55+ community of Traditions at Whitehall. This home features an open floor plan with a spacious dining area, kitchen, great room, and perfect for modern living and entertaining. The large Owner’s Suite offers two walk-in closets, an en-suite bath with a double vanity, and a luxurious 5-foot tile shower. A versatile loft on the second floor provides additional space and the option to add another bedroom and bathroom for expanded living. Customize your interior and exterior finishes and make this home yours! 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.
#DENC2080218

MIDDLETOWN

204 BALDY LANE BRISTOLE

3 Beds

2 Baths

2,441 Sq.Ft.

$548,500

MLS#: DENC2080218

Middleton Elite -TO BE BUILT new construction. This 3 bedroom open innovative floor plan welcomes homeowners and visitors alike in a space that flows effortlessly from one room to the next. Spacious kitchen with hardwood floors, along with 42" maple cabinets, granite countertops, and so much more. The picture shows this home with the largest optional porch, but there are 3 front elevations to chose 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. Agent must accompany client on first visit or pre-register on builder's website prior to first visit.
#DENC2079222

MIDDLETOWN

530 WHEELMEN STREET 2 MIDDLETON ELITE

3 Beds

2 Baths

2,052 Sq.Ft.

$540,000

MLS#: DENC2079222

Come fall in love this Valentines Day - Sellers have Priced this move -in ready home to MOVE!! You can be the new owner to enjoy all the amenities right in your own backyard. Looking for a fantastic place to call home that offers a country feel with a 3/4 acre corner lot, fenced in backyard and a HEATED inground pool? Then Misty Vale Farms is calling your name with this beautifully updated home featuring acacia hardwood floors throughout with tile bathrooms, an upgraded kitchen with stainless steel appliances, butcher block counters, wood burning fireplace, formal dining room and and a sunken family room right off the kitchen that leads to a deck and bridge to your incredible backyard with patio, raised garden beds, perennial flowers and large grasses to complete the landscaping. Warmth and openness make this a perfect home for relaxing, entertaining or game night! Sellers installed a NEW vinyl white privacy fence around the pool area, with grassy patches, a fire pit section and concrete decking with plenty of room to entertain and enjoy the outdoor serenity of your very own inground pool - with NEW HEATER! They also upgraded the second floor with all NEW HARDWOOD floors to match the main level. The main level also features a great bonus room with glass framed french doors - perfect for home office, library, playroom - you decide! Upstairs, the primary suite impresses with vaulted ceilings, stunning tile in the en suite bath, and an 11-ft walk in closet. Two additional upstairs bedrooms, a stylish hall bath, and convenient upstairs laundry complete the second floor. The finished basement adds even more flexibility with a media/playroom and an additional bedroom for guests. But the real showstopper is outside where your summer paradise awaits! Enjoy a sparkling in-ground pool with diving board. And the roof is only 8 years young! All this home needs is you and homes like this don’t come along often—don’t miss your chance to make it yours!
#DENC2093922

MIDDLETOWN

102 NEWBURY COURT

3 Beds

2 Baths

2,292 Sq.Ft.

$530,000

MLS#: DENC2093922

New on site today
Welcome to 1818 S Pollock Way, where comfort, care and community come together beautifully in the heart of the highly sought-after Village of Bayberry neighborhood. This immaculately maintained 3-bedroom, 2 full and 2 half baths carriage home has been lovingly cared for and thoughtfully upgraded, offering the perfect blend of warmth, modern convenience, and inviting spaces designed for everyday living and memorable gatherings. From the moment you arrive, there is a sense that this home has been exceptionally well cared for. Inside, the atmosphere is bright, welcoming, and comfortable, with two gathering spaces that feel both elegant and easy to live in. Enhanced by beautiful ¾-inch solid oak hardwood flooring and recessed lighting that adds a soft and elegant glow throughout the home. The home also features a whole-home audio system controlled right from your mobile device—perfect for setting the mood whether you're entertaining guests or simply enjoying a quiet evening at home. The kitchen, which includes classic subway tile backsplash, blends style with smart functionality and has been recently enhanced with a Wi-Fi controlled Bosch dishwasher and GE Profile electric range. For those who prefer cooking with gas, a gas line is already in place for easy conversion. Under-cabinet LED lighting adds both efficiency and ambiance. Upstairs you will find the spacious owner’s suite offers a peaceful retreat at the end of the day. Designed with comfort and practicality in mind, it features a generous walk-in closet and a well-appointed ensuite bath complete with dual sinks, a walk-in shower, and plenty of room to start and end your day with ease. The additional bedrooms are equally welcoming and offer ample closet space, making them perfect for guests or choose one for a home office. The finished basement has new carpet, fresh paint, and durable luxury vinyl plank flooring with 9-foot ceiling. An entertainer’s dream, a fully equipped theater room awaits movie nights and game days, complete with an Epson 3D projector, impressive 107-inch screen, Denon receiver, full surround sound system, and all theater furnishings included—creating a true cinematic experience right at home. The adjacent home gym features a treadmill, workout bench, and equipment /cart, making it easy to stay active without ever leaving the comfort of home. Step outside and the inviting atmosphere continues. The deck/patio creates a beautiful outdoor retreat ideal for relaxing evenings or weekend gatherings. The sale includes all patio furniture, umbrella, Weber grill, and a rock speaker integrated with the home’s sound system. This home also offers peace of mind thanks to meticulous maintenance and proactive care. The garage door system and HVAC system were both recently professionally serviced. A Delaware Energy home inspection was completed and passed in August 2025. The lawn has already been cared for this year which included fertilization, grub control, aeration, and overseeding—ensuring the outdoor spaces remain lush and vibrant. Additional services will be available throughout 2026. Living in the Village of Bayberry means becoming part of a thriving and welcoming community. Enjoy mornings on scenic walking trails, afternoons in nearby playgrounds, and evenings gathering with neighbors in beautiful green spaces. Just minutes from the growing Bayberry Town Center, schools, major commuting routes, and Middletown’s shops and restaurants, this location offers both tranquility and convenience. Check out all the amenities this wonderful community provides. Homes that combine care, thoughtful upgrades, energy-efficient touches, and a true sense of pride in ownership rarely stay available for long. 1818 S Pollock Way offers an opportunity to move into a home that feels established, welcoming, and ready for its next chapter—one that a lucky new owner will be proud to call their own. Schedule your tour today!
#DENC2098578

MIDDLETOWN

1818 S POLLOCK WAY

3 Beds

2 Baths

2,550 Sq.Ft.

$530,000

MLS#: DENC2098578

UPDATE!!! PRICE REDUCTION!!! Now being offered at below the base price for a new Cooper ll model!! Be sure to check the included features sheet and additional upgrades to see the overall value. Welcome to Parks Edge! This exceptional 55+ community in Delaware offers an array of amenities that are truly hard to beat, designed to enhance your active lifestyle. We are pleased to present the Cooper II model, a two-bedroom, two-bath home built by Blenheim Homes. This particular residence features a flexible room that offers the versatility to be easily converted into a third bedroom, an office, or a hobby room, catering to your specific needs. There is also a rough-in for a third bathroom in the basement for the potential need to add another bathroom. The home was constructed with numerous high-quality and energy-efficient features, a detailed list of which can be found in the attached documents for your review. Furthermore, the balance of the 10-year structural warranty is transferable to the new owner(s), providing additional peace of mind. Parks Edge residents enjoy unparalleled access to both the Bayberry South Lakehouse and their own exclusive luxury clubhouse. The clubhouse includes a state-of-the-art fitness center, a refreshing outdoor pool, and various athletic courts for your enjoyment. Beyond these facilities, the community boasts an 11-acre boating and fishing lake and a sprawling 70-acre park, offering ample opportunities for recreation and relaxation. To further enhance your living experience, these features come with the added convenience of included lawn maintenance, snow removal, and irrigated lawns. Close to everything Delaware and surrounding states have to offer, including the grand opening of the largest grocery-anchored retail center in Middletown. Weis Market and 280,000 sf retail center with all the shopping you need right outside your door. We invite you to schedule your showing today to experience all that this remarkable home, community, and area have to offer.
#DENC2089864

MIDDLETOWN

3037 BARBER LANE

2 Beds

2 Baths

1,800 Sq.Ft.

$528,000

MLS#: DENC2089864

Welcome to the popular Bloomfield Model in the 55+ community of Traditions at Whitehall. This floor plan has 2-Bedrooms with a standard loft and a generously sized great room open to the kitchen and dining area. You will have plenty of space if you like to entertain. A rear Owner's Suite gives maximum privacy and includes a large walk-in closet and en-suite with a double bowl vanity and 5-foot tile shower. The second floor features a large loft and walk-in closet for additional storage or overnight guests. With many structural options available, another bedroom and another bathroom can easily be added. Customize your interior and exterior finishes and make this house your home! 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.
#DENC2080216

MIDDLETOWN

120 BURLINA BLVD BLOOMFIELD MODEL

2 Beds

2 Baths

2,053 Sq.Ft.

$527,000

MLS#: DENC2080216

Welcome to the Belville Model in the 55+community of Traditions at Whitehall. TO BE BUILT. This inviting 2-Bedroom home has a welcoming foyer which leads you down the hall towards the main living area! An open kitchen and breakfast area which flows into the large great room and is perfect for entertaining! The owner’s suite in the front features a large walk-in closet and owner’s bath with a double bowl vanity and 5-foot tile shower. The second floor offers a standard loft with the option to add an additional bedroom and/or bathroom. Customize your interior and exterior finishes and make this home yours! 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.
#DENC2080214

MIDDLETOWN

204 BALDY LANE BELVILLE

2 Beds

2 Baths

2,059 Sq.Ft.

$521,500

MLS#: DENC2080214

Welcome to 1 Walnut Pond Ct in the heart of Middletown! Nestled on a desirable corner lot in a small, quiet neighborhood, this beautifully updated 4-bedroom, 2.5-bath home offers comfort, style, and peace of mind with major upgrades already completed. Enjoy brand new windows, a new HVAC system, new hot water heater, and new stainless steel appliances. The home features new flooring throughout, including laminate flooring and carpet, along with fresh paint that gives the entire space a clean, modern feel. Step outside to a 5-year-old Trex deck overlooking your private backyard retreat complete with a screened-in porch and a pool with a 2-year-old liner — perfect for entertaining or relaxing all summer long. Additional highlights include a 2-car garage and a prime corner lot location in one of Middletown’s most desirable areas. Move-in ready and loaded with upgrades — this one won’t last!
#MDFR2076532

MIDDLETOWN

1 WALNUT POND COURT

4 Beds

2 Baths

1,620 Sq.Ft.

$520,000

MLS#: MDFR2076532

New on site today
This is your opportunity to move into Silver Maple, one of the area’s most desirable 55+ communities, known for its exceptional amenities and active lifestyle. From the moment you enter this 3BR, 2BA, 2-car garage home, you’ll notice the beautiful hardwood floors that flow from the foyer through the main living areas. The open-concept floor plan seamlessly connects the living room, featuring recessed lighting, to the gourmet kitchen with upgraded cabinetry, stainless steel appliances, granite countertops and nice breakfast bar area. The spacious primary suite includes a large walk-in closet and a private bath. Just off the living room, the sunroom addition provides the perfect spot to relax, while the upgraded Trex deck with retractable awning is ideal for enjoying your morning coffee or entertaining outdoors. The full basement with egress window presents endless possibilities for additional living space and includes plumbing hook-ups for future expansion. Additional updates include fresh paint throughout, new roof with 50-year warranty (2026), updated light fixtures, new porch railing, and more. Four Seasons at Silver Maple, built by K. Hovnanian, offers resort-style living with a clubhouse, meeting rooms, outdoor pool, pickleball and bocce courts, horseshoes, fire pit, walking trails, and community garden. Don’t miss the chance to enjoy low-maintenance living in one of Delaware’s premier active adult communities.
#DENC2098642

MIDDLETOWN

137 SILVER MAPLE ROAD

3 Beds

2 Baths

1,625 Sq.Ft.

$519,900

MLS#: DENC2098642

Welcome to 248 Ann Drive in the heart of Middletown at the Crossland at the Canal! This beautifully maintained 15 year old 4 bedroom 2.2 bathrooms home offers the perfect blend of comfort, space, and convenience. Step inside to find a bright and inviting layout with generous living areas, ideal for both everyday living and entertaining. The kitchen features ample cabinetry and workspace, flowing seamlessly into the dining area for easy gatherings. Upstairs, you’ll find 4 spacious bedrooms with great natural light, including a primary suite designed for relaxation at the end of a long day. The home also features a finished basement that provides additional living space — perfect for a home office, gym, or recreation area. Basement improvements were completed without permits and are being sold as-is; buyer to perform their own due diligence. Enjoy outdoor living with an unfenced private yard, ideal for summer barbecues and quiet evenings. Conveniently located near shopping, dining and major routes. Don’t miss your opportunity to own a home in one of Middletown’s most desirable communities — schedule your tour today!
#DENC2096586

MIDDLETOWN

248 ANN DRIVE

4 Beds

2 Baths

1,900 Sq.Ft.

$509,900

MLS#: DENC2096586

Welcome to the beautifully crafted Lexington model—brand new and READY NOW in the desirable Greenwood Hills community! This energy-efficient home offers nearly 2,000 sq. ft. of thoughtfully designed living space, with 4 spacious bedrooms and 3 full bathrooms, including a main-level bedroom and full bath w/ walk-in shower, perfect for guests, multi-generational living, or a home office. The kitchen features 36” painted cabinets w/ crown molding, elegant quartz countertops, floating shelves, stainless steel appliances with gas cooking, and a walk-in pantry with solid shelving. The kitchen flows seamlessly into the dining area and open family room, creating a welcoming space for both everyday living and entertaining. Upstairs, the primary suite provides a peaceful retreat, complete with a walk-in closet and private en-suite bath with tile shower. Two additional bedrooms and a hall bath complete the upper level. Additional highlights include a two-car garage, walk-out lower level ready to finish, and a 10 year home warranty for added peace of mind. Enjoy life in Greenwood Hills—a thoughtfully planned neighborhood with sidewalks, community benches, a modern park, and a scenic pond with an observation deck. Conveniently located with easy access to Route 283 and the PA Turnpike.
#PADA2045388

MIDDLETOWN

160 HARTFORD DRIVE

4 Beds

3 Baths

1,966 Sq.Ft.

$509,900

MLS#: PADA2045388

Welcome to a fully renovated, move-in ready home in the heart of Middletown — where the charm of a well-established neighborhood meets the confidence of major modern upgrades already completed. This beautifully updated 3-bedroom, 1.5-bath home features a brand-new kitchen, updated flooring, and refinished hardwoods that blend timeless character with today’s style. But what truly sets this home apart is what you won’t have to worry about: a new heat pump, new double-hung windows, new 200-amp electrical service, new gutters, and a roof replaced in 2024. The big-ticket items are done — offering peace of mind for years to come. Enjoy a spacious backyard ideal for entertaining, play, gardening, or simply relaxing after a long day. The location offers the best of both convenience and community — walk to local schools, shops, and town amenities, with easy access for commuters. Opportunities like this — fully updated with major systems already replaced — rarely come available in Middletown at this price point. Schedule your showing before it’s gone
#MDFR2077570

MIDDLETOWN

10 LINDEN BOULEVARD

3 Beds

1 Baths

2,104 Sq.Ft.

$509,000

MLS#: MDFR2077570

IMMEDIATE AVAILABILITY! Welcome to the 55+ community of Traditions at Whitehall - Ashton Carriage Town Home. This end unit first floor master comes w/a 2nd bedroom & loft, 2.5 baths, 2 car rear load attached garage, front porch, and additional finished upgrades. Community also offers trails, in ground pool w/lounge areas, open clubhouse featuring exercise room, billiards, gathering space, full kitchen and a large outdoor patio area! Builder Splits Transfer Tax (***Photos are of a similar home and may contain options & upgrades not included in listing price shown.***)
#DENC2081004

MIDDLETOWN

1102 HIGHLAND STREET 137 ASHTON

2 Beds

2 Baths

1,794 Sq.Ft.

$504,900

MLS#: DENC2081004

New on site today
Enjoy breathtaking sunsets and peaceful privacy from this bright and sunny 3-bedroom, 2-bath ranch set on 2.2 acres with state-owned land directly behind the property. This inviting home offers easy one-floor living, a 2-car garage, and an unfinished basement (which also offers a pellet stove) providing excellent storage and future potential. Inside, you'll find hardwood floors and tile throughout the main living areas and an abundance of natural light that fills the home. The living and dining rooms feature soaring cathedral ceilings, creating an open and spacious feel, and lead to sliding glass doors that open to a sun porch and concrete patio, perfect for relaxing or entertaining while enjoying the surrounding landscape and evening sunsets. The primary suite features cathedral ceilings and sliding doors leading directly outside, offering a private retreat with beautiful views of the backyard and the preserved land beyond. Two additional bedrooms and a second full bath complete the main level. The home also includes a convenient laundry area located near the kitchen and a layout designed for comfortable everyday living. While the property needs a little TLC, it presents an exceptional opportunity to update and make it your own in a truly special setting. With peaceful surroundings, stunning sunsets, and protected land just beyond the backyard, this property is a rare find for buyers seeking privacy, nature, and potential. Property is being sold as-is. No unrepresented Buyers. No offers accepted via text message.
#DENC2098160

MIDDLETOWN

847 SILVER RUN ROAD

3 Beds

2 Baths

1,375 Sq.Ft.

$500,000

MLS#: DENC2098160

1 ... 7 8 9

properties found. properties found. Page of .

- property

Send a message

Message successfully sent.

Your message

What is 3 + 4 ?

Reason for contacting?

Sign Out

Virtual Assistant

Would you like to take the next step with this property? We can help you schedule a showing or virtual tour, or send you more details.

Yes, I would like more information.

Thank You for Your Reply, One of Our Agents will contact you as soon as possible

No, maybe later.

Thank you, you can always contact me via email, phone number or through the contact form.

Realhub AI

Lucy - Your AI-Powered Realtor

Update Your Temporary Password

Personalize your search

Enter your email and we'll notify you immediately when new listings match what you're looking for.

or enter email address

Already have an account ? Login here

Continue your home search

Already have an account ? Login here

We use cookies

We use cookies primarily for analytics to enhance your experience. By accepting, you agree to our use of these cookies. You can manage your preferences or learn more about our cookies policy.

Privacy Policy Terms of Service