One of the most popular communities provided by {{page_data.agentName}}

MIDDLETOWN

One of the most popular communities provided by Charis Realty

MIDDLETOWN

About MIDDLETOWN

Middletown, MD Real Estate: Your Ultimate Guide

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
103
# of Listings
3
Avg # of Bedrooms
$320
Avg. $ / Sq.Ft.
$564,040
Med. List Price

Browse MIDDLETOWN Real Estate Listings

20 Properties Found. Page 1 of 2.

*DO NOT DRIVE DOWN THE DRIVEWAY AT ANYTIME WITHOUT AN APPROVED SHOWING APPT W/YOUR REALTOR*
Welcome to your own private sanctuary—an extraordinary craftsman-style home nestled deep in the woods on a secluded half-mile shared driveway. Tucked away from the world, this one-of-a-kind residence is a rare blend of natural beauty, unique architectural charm, & refined comfort.

From the moment you arrive, the stone & cedar exterior sets the tone for what’s to come—unparalleled character, warmth, & craftsmanship. The driveway winds through the trees and opens up to a perfectly manicured landscape with a harmonious mix of open lawn & wooded serenity.

Step into the home through the oversized two-car garage, then ascend the striking split-level open staircase—just one of the many architectural highlights that make this home unforgettable. From here, choose to step down into the sunlit lower-level family room, where windows bring the outdoors in. This space also features one of two pellet stoves, creating cozy comfort during the winter months. A half bath & a separate garage bay—ideal for storing your ATV or outdoor gear—complete this level.

Upstairs, the main level is nothing short of breathtaking. An open-concept layout & lots of windows showcase the surrounding woods, offering peace & privacy at every turn. The chef’s kitchen boasts beautiful cabinetry, granite & natural stone countertops, a large island, stainless steel appliances, a gas range, & rustic barnwood floors. A charming butler’s pantry is perfectly tucked away, creating the ideal coffee nook or prep station.

At the heart of the home sits a stunning two-sided gas fireplace, anchoring the kitchen & adjacent sunken living room. Here, Juliet balconies, lots of windows for added natural light, & French doors offer enchanting views & access to the outdoors. Step into the screened-in porch built around a tree—a truly magical space where you can sip your morning coffee & enjoy the wildlife that shares your peaceful retreat.

Follow the open staircase to the upper level, where the home continues to impress. One side features a luxurious primary suite with a walk-in closet, dual sinks, and On the opposite side, two additional bedrooms with skylights & another full bath offer space for guests or family. This level is also warmed by its own pellet stove, perfect for chilly nights.

Outside, the property transforms into a woodland oasis. A massive hardscaped patio with a beautiful stone retaining wall, outdoor fireplace, & built-in shed with cabinetry & mini-fridge creates an entertainer’s dream. Unwind in the hot tub, or enjoy dinner under the stars with room for all your guests. Stone steps lead down both sides of the patio to your private hillside, which rolls gently into the trees.

Just beyond the patio is one of the most exceptional features of all—a 10x40 heated lap pool with an automatic cover & a nearby fire pit—the perfect place to relax & take in views of Middletown Valley in the fall & winter months.

A massive detached 3-bay garage provides more than enough room for all your hobbies & toys. One bay, previously used as a showroom, features a wood stove & plumbed for a full bath & could easily convert back into a standard garage. The other side offers 2-car parking, with a covered equipment area in the rear. Upstairs, a fully finished 1,200 sq ft studio awaits—not currently approved as living space but ideal for a possible in-law suite, guest quarters, or a creative retreat. Complete with a kitchen, fireplace, & up to 3 possible bedrooms, this space offers incredible flexibility. 

And yes—there’s even a chicken coop with resident hens ready to stay, should you wish to keep them.

This is not just a home—it’s a lifestyle. A nature lover’s dream, an entertainer’s paradise, & a true escape from the everyday. There is nothing else like it on the market. Don’t miss the opportunity to make this extraordinary property your forever home!
#MDFR2070966

MIDDLETOWN

8935 HAWBOTTOM ROAD

3 Beds

2 Baths

4,440 Sq.Ft.

$999,000

MLS#: MDFR2070966

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

DOWNTOWN...MIDDLETOWN, ..........VINTAGE FIVE UNIT APARTMENT BUILDING......COMMERCIAL ON ,MAIN LEVEL...........FOUR ROOMY TWO BEDROOM ONE BATH APARTMENT..............NEWER ROOF.........LEASES ON ALL COMMERCIAL/RESIDENTIAL APARTMENTS..........CENTRAL AIR CONDITION, EXCEPT 8A UNIT............ALL SEPERATE UTILITIES, OWNER PAYS WATER & SEWER.
#MDFR2067992

MIDDLETOWN

4-8 SOUTH CHURCH 6

None Beds

None Baths

5,000 Sq.Ft.

$829,900

MLS#: MDFR2067992

Options galore! Purchase or ground lease with potential seller financing for a qualified purchaser. I-81 Exit #302 is the Gateway entrance into the Historic Town of Middletown, Virginia. This is the last remaining lot at the corner of Reliance Road and Valley Ave (Rt #11). We have 3.84 acres zoned B2 highway commercial. You are surrounded by The Village at Middletown by Ryan Homes. Richmond American Homes are building 90 additional single family homes on the south end of town. Middletown is home to Historic Wayside Inn, circa 1797, Laurel Ridge Community College with 3,500 students and staff. Immediate neighbors include; Comfort Inn, McDonalds, Dollar General, 7-11, Liberty C-store with fuel depot, Sheetz C-store with fuel depot has recently opened on the east side of the interstate. Locate your successful business venture where the growth is happening.
#VAFV2024656

MIDDLETOWN

0 RELIANCE

None Beds

None Baths

3.84 acres

$799,000

MLS#: VAFV2024656

New on site 2 days ago
Welcome home to 107 Mina Drive — where comfort, style, and location come together beautifully in the heart of Middletown. Lovingly maintained and thoughtfully updated, this Admar custom-built 4-bedroom, 3.5-bath residence in the sought-after Foxfield neighborhood sits on a beautifully level lot measuring just under a half acre. Enjoy being just steps from Middletown Park and walking distance to the highly rated Middletown schools, the public library, and Main Street’s shops, restaurants, and community events.

Inside, warmth and style unfold in every detail. The open-concept design features wood floors, neutral paint, custom plantation shutters, and expansive windows that fill the home with natural light and frame serene views of the backyard. The family room’s vaulted ceiling and custom built-ins surrounding a stunning floor-to-ceiling stone gas fireplace create the perfect gathering spot—cozy in winter, bright and welcoming year-round. The updated kitchen showcases new cherry cabinetry, quartz countertops, a glass tile backsplash, and stainless-steel appliances, blending beauty and function for everyday living and effortless entertaining. A first-floor office provides the perfect space for remote work or quiet study, and a main-level laundry room adds everyday convenience.

Upstairs, the spacious primary suite offers a private retreat with an updated shower and generous closet space, while custom closet organizers throughout add style and efficiency to every room. Three additional bedrooms provide flexibility for family, guests, or creative use. The finished basement expands your living area with a large recreation room, separate game room, full bath, ample storage, and a convenient walk-out exit—ideal for guests, hobbies, or movie nights.

Outdoors, unwind on the comfortable front porch or enjoy your park-like backyard oasis, complete with a 25,000-gallon heated pool, expansive deck, and soft mountain views in the distance. The fenced rear yard also includes a spacious deck and storage shed, offering both beauty and function for everyday enjoyment. From pool parties to peaceful sunsets, every season feels special here. A two-car garage provides ample parking and additional storage for today’s lifestyle.

Major system updates include an HVAC system with an indoor unit from 2014 and an outdoor unit from 2018, a 2022 water heater, and an architectural shingle roof installed in 2019. Offering 2,580 finished square feet above grade and 1,100 finished square feet below grade (1,440 total basement), this home perfectly balances comfort, craftsmanship, and convenience.

This is the kind of home where mornings start with coffee on the porch and evenings end with sunsets by the pool. Designed for connection and comfort, every space invites you to slow down and savor life in Middletown.
#MDFR2072806

MIDDLETOWN

107 MINA DRIVE

4 Beds

3 Baths

4,020 Sq.Ft.

$775,000

MLS#: MDFR2072806

This exceptional home offers the perfect blend of privacy and convenience, nestled on a beautifully treed lot with serene views from every window—including breathtaking vistas of Skyline Drive from the two rear patios and the upper-level deck off the master bedroom. Despite its tranquil, sanctuary-like setting, the property is less than five minutes from Target, Walmart, Starbucks, and Lowe’s, and Restaurants. Designed for both comfortable living and effortless entertaining, the home features a spacious open-concept kitchen, family room, and dining area, complemented by two outdoor patios. Two refrigerators offer ample space for food storage—ideal for hosting gatherings or separating family groceries. With two laundry rooms (one on each level), a private office with high-speed Xfinity internet, and thoughtful upgrades such as gutter leaf guards, a paved asphalt driveway, front paver walkway with landscaping, and a tankless water heater, this home is as functional as it is inviting. More Info- Aerobic Septic system was pumped in August 2024, and has a maintenance  agreement. Exterior lawn maintenance is paid for the remainder of this season. The last mow is usually in October – so the purchasers will not have the lawn to worry about this year, allowing them to spend time getting settled. The propane tank which is leased runs the gas fireplace, kitchen stove, and tankless water heater. Electric Dual Zone central A/C with 2 heat pumps. Water Treatment system is Culligan.  Comcast is the internet and cable provider. The TV and mount above the mantle can convey.  The HOA  takes care of snow removal, and road maintenance, and is paid once a year. There are 4 Bedrooms and  2 Full baths upstairs, and 1 full bath on the first level, with room for an extra bedroom. This well maintained home is a must see!
#VAWR2011312

MIDDLETOWN

115 RELIANCE WOODS DRIVE

4 Beds

3 Baths

4,810 Sq.Ft.

$769,900

MLS#: VAWR2011312

None
#MDFR2072474

MIDDLETOWN

2431 QUEBEC SCHOOL ROAD

4 Beds

3 Baths

3,013 Sq.Ft.

$750,000

MLS#: MDFR2072474

Motivated Seller!! Welcome to the sought-after Jackson’s Meadow subdivision with no HOA! This spacious Quaker-built home was completely remodeled down to the studs in 2021, with everything new inside and out. Offering over 4,000 finished square feet across three levels and backing to the Sly Fox Golf Course, this property has room for everyone. On the upper level, you’ll find 4 bedrooms, including the oversized primary suite with a jetted tub, porcelain shower with glass roller door, and a large walk-in closet with built-ins. Convenient upstairs laundry includes washer and dryer. The main level is warm and inviting with hardwood floors, 9’ ceilings, crown and chair rail molding, and recessed lighting. The gourmet kitchen features granite countertops, a 7’ island with flat-top stove and hood, stainless steel appliances, and opens to a cozy family room with propane fireplace. A main level study with French glass doors makes a perfect office, while an additional bedroom and full bath provide main-level living flexibility. The finished walk-out basement adds even more possibilities. It includes a large recreation/living room, kitchenette, full bathroom, and a 6th bedroom. Plus, there’s an additional room that could serve as a potential 7th bedroom, office, playroom, or gym! Since purchase, the owners have added thoughtful upgrades, including a large deck, perfect for entertaining or relaxing while enjoying the established 1-acre lot. Other highlights include ample storage and an attached two-car garage. Just minutes to Front Royal and commuter routes, this home blends comfort, space, and modern convenience.
#VAWR2012424

MIDDLETOWN

43 LITTLE SORREL DRIVE

6 Beds

4 Baths

4,164 Sq.Ft.

$699,900

MLS#: VAWR2012424

Welcome to 95 E Green Street, a beautifully designed home  in  Middletown. The main level boasts an inviting open layout with bright, spacious living and dining areas that flow seamlessly into a modern kitchen—ideal for entertaining or everyday comfort. Upstairs, you'll find four generously sized bedrooms, including a serene primary suite with an ensuite bath and ample closet space. The lower level offers an unfinished, full-size basement with bathroom rough-ins and windows, ready for your personal touch—perfect for adding a recreation room, gym, or guest suite. Move-in ready with a fully paid 8.45 kW Tesla solar panel system. Step outside to enjoy the peaceful surroundings, from your front porch with mountain views, sunsets, and sunrises to your private backyard space. Just one street away, explore Middletown’s brand-new library, and enjoy quick access to Middletown High, Middle, and Elementary Schools, all within walking distance.

Located only 15 minutes from historic Downtown Frederick, you’ll have easy access to major employers, commuter routes like I-70 and US-40, and a wealth of shopping, dining, and entertainment options. Nearby, discover parks, local breweries, and scenic trails, making this home an ideal balance of comfort, convenience, and charm in one of Maryland’s most sought-after communities.
#MDFR2072286

MIDDLETOWN

95 E GREEN STREET

4 Beds

3 Baths

4,106 Sq.Ft.

$669,000

MLS#: MDFR2072286

Welcome to 149 Foxglove Drive, a spacious and well-maintained Red Cedar model located in a desirable neighborhood of Middletown. This thoughtfully designed home features a bright and open main living area filled with natural light and large windows. The first-floor in-law suite includes its own bedroom and full bath—perfect for extended family or guests.

The kitchen is a true centerpiece with granite countertops, stainless steel appliances, and ample cabinet space. Upstairs, you'll find four generously sized bedrooms and three full bathrooms, offering plenty of space for everyone. The walk-out basement provides easy access to the backyard and offers great potential for future finishing or extra storage.

Situated on a private perimeter lot, this home offers comfort, flexibility, and room to grow—all in a convenient location close to schools, shopping, and major highways. Don’t miss your chance to make this beautiful home yours!
#PADA2047838

MIDDLETOWN

149 FOXGLOVE DRIVE

5 Beds

3 Baths

3,092 Sq.Ft.

$649,900

MLS#: PADA2047838

Tucked away on over 5 private acres, this chalet-style retreat feels like living in your own treehouse. Soaring ceilings, expansive windows, and skylights bathe the open interior in natural light, highlighting the warmth of hardwood floors and a striking fireplace centerpiece. The wraparound deck is perfect for morning coffee or evening sunsets, surrounded by nature. The oversized, detached two-car garage offers endless possibilities for storage, projects, or tinkering. Inside, you’ll find eclectic charm blended with modern updates: a beautifully refreshed kitchen featuring stainless steel appliances and granite countertops. Whether you’re seeking a private escape or a home with character, this property delivers both. Enjoy rustic serenity without sacrificing convenience—just 15 minutes to Middletown’s shops and dining, and within the desirable Middletown school district. A rare opportunity to own a one-of-a-kind home that truly captures the best of mountain-style living.  Roof - 2020, Skylights - 2020, Stove/Microwave - 2021,  Fridge 2023+, Water Softener/Neutralizer - 2022.
#MDFR2070626

MIDDLETOWN

6838 MOUNTAIN CHURCH ROAD

4 Beds

3 Baths

2,586 Sq.Ft.

$649,900

MLS#: MDFR2070626

Imagine relaxing on an refinished deck, listening to the birds, and watching wildlife as you take in the serene rolling hills and distant mountains of the Middletown Valley. Despite the peaceful surroundings, you’re only minutes from Main Street Middletown’s restaurants, schools, shops, and all the charm of small-town USA!

This beautiful ranch home sits on 3.59 acres and offers 3 bedrooms (with the potential for a 4th bedroom on the main level or additional bedrooms to be finished in the basement), 3 full baths, and 1,820 sq ft of finished living space on the main level—plus another 1,820 sq ft of unfinished space ready for you to build out and customize to your liking.

The outdoor space truly shines with a large 1,320 sq ft pavilion—perfect for family BBQs, reunions, and events—or for cracking crabs on a summer evening! Enjoy the above-ground private pool to cool off on sunny days, or relax on the shaded deck overlooking your private oasis as you sip your morning coffee or evening drink of choice to unwind. The property backs to woods, offering privacy, seclusion and room to explore your 3.59 acre retreat.

Car and workshop enthusiasts will love the detached 3-car, 1,124 sq ft garage with 10-foot bays and 12-foot ceilings, as well as the 2-car, 751 sq ft attached carport. All buildings, including the house, carport, garage, pavilion & shed, have new lifetime architectural roofs with transferrable warranty to new Owner!

This is country-style living at its best with all the modern amenities you expect—and even a few you don’t. Make it your own before someone else does!
#MDFR2072484

MIDDLETOWN

3226 BIDLE ROAD

3 Beds

3 Baths

3,640 Sq.Ft.

$649,000

MLS#: MDFR2072484

This ranch home located in a quiet Middletown neighborhood is a gem hidden in plain sight and full of surprises. First, it has 4,000 resplendent finished square feet, and second, it offers two levels of independent living. The floorplan flows seamlessly, providing the kind of breathing room you’ll appreciate, enhanced with an elegant color palette, natural light, and stunning hardwood floors that pull it all together. The living room easily provides the space for various seating configurations and offers a fireplace along the main wall to center around. It opens to the renovated kitchen, inviting with its pristine white cabinetry, backsplash, and eat-in island—and where you’ll find ample workspace and storage plus high-end stainless appliances and fixtures. The dining room sits adjacent with space for extras such as china cupboards or buffets. A bonus room affords decent space for an office, playroom, crafts or hobbies, etc. Conveniently
located next to the kitchen, a mudroom combines with the laundry area with storage cabinets and a utility sink. This level boasts four bedrooms and three full baths. The primary suite shines with the addition of a sliding barn door to separate the appealing attached bath plus a walk-in closet. The other bedrooms and baths are all lovely, matching the theme. The downstairs is a complete floor designed as an in-law suite or
rental. It boasts a full kitchen, comfortable living/dining area, bedroom, bath, and dedicated laundry room. The aesthetic matches the upstairs to a backdrop of LVP plank-style flooring. It contains a private separate entrance, and even its own parking. The home rests on .31 acres with a view of the mountains, along with plenty of trees and landscaped shrubs to enjoy. A screened-in porch adds another tranquil respite, as
does a covered porch stretching along the front of the home. A two-car attached garage provides space for vehicles or storage. This home has been updated, renovated, and carefully maintained—and presents a unique opportunity. But also, this residence is the ticket to enjoy Middletown’s quaint, historic downtown, well-rated schools, and peaceful atmosphere plus proximity to Winchester, Shenandoah Valley, and all the area has to offer.
#VAFV2037492

MIDDLETOWN

2140 SIXTH STREET

5 Beds

4 Baths

4,006 Sq.Ft.

$635,000

MLS#: VAFV2037492

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.

$603,499

MLS#: PADA2048296

QUICK SETTLEMENT! Upgrades throughout, new roof, bathroom, kitchen, with all new stainless steel appliances. The renovated main bathroom has a beautiful new tub with ceramic tile and a spacious new vanity. In 2023 the driveway was paved, in 2021, the heat pumps were replaced.  Some of the features are over the top, like multiple master bedrooms, one on the first floor, one on the second floor, both with private bathrooms. The upstairs master suite has a jacuzzi tub along with a built-in vanity and, separate shower.  There are a total of 6 bedrooms and 4.5 baths, 2 family rooms.   Total of 3 walk-in closets and a storage room. The new wheelchair ramp gives one access to the first floor.  The outdoor living space is phenomenal, which includes multiple decks, a gazebo, and more! The landscaping is over-the-top beautiful, yet minimal maintenance with lots of perennials in place. The local outdoor parks are ideal for sports families. Local Fountaindale community park, and the well-known Middletown Park! This home has been maintained, upgraded and loved! A rare find! This could be the perfect multi-generational home, with a quick settlement! Just in time for the upcoming Holidays! If you want a car port or garage, that may be a possibility as well, reach out to the local zoning office for more specifics to confirm.
#MDFR2066902

MIDDLETOWN

4311 ZIRCON ROAD

6 Beds

4 Baths

3,072 Sq.Ft.

$599,000

MLS#: MDFR2066902

1 2

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