CHARIS REALTY GROUP
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MIDDLETOWN

One of the most popular communities provided by Charis Realty Group - Christine Issler, Broker

MIDDLETOWN

About MIDDLETOWN

Middletown, MD Real Estate and Community

Welcome to Middletown, Maryland, a charming town that combines small-town charm with modern amenities. Known for its scenic views and rich history, Middletown is an ideal place to call home.

Why Choose Middletown for Your Next Home?

Middletown is more than just a place to live; it’s a community brimming with potential. Here are some reasons to consider:

  • Excellent School System: Experience quality education in top-rated schools.
  • Beautiful Parks: Enjoy outdoor activities in our well-maintained parks.
  • Rich History: Explore historical sites that reflect our community’s heritage.
  • Convenient Location: Easy access to major highways and nearby cities like Frederick and Hagerstown.

Real Estate Opportunities

Middletown offers a diverse range of real estate options for families, retirees, and professionals alike. Whether you’re searching for a cozy single-family home, a spacious townhome, or an elegant estate, Middletown has it all.

Current Market Overview

  • Average Home Price: $XXX,XXX
  • Market Trend: Link to local market trends
  • New Listings: Check out the latest properties available in Middletown.

Popular Neighborhoods

  1. Downtown Middletown: Known for its historic homes and vibrant downtown area.
  2. Catoctin Estates: Spacious lots and modern amenities, perfect for families.
  3. Rolling Hills: A serene, upscale neighborhood with beautiful views.

Community Highlights

Local Amenities

  • Shopping: Enjoy various local boutiques and major retailers.
  • Dining: Savor delicious meals at community-favorite restaurants.
  • Recreation: Engage in sports and outdoor activities at local parks.

Annual Events

  • Middletown Heritage Festival: Celebrate our history with food, music, and fun.
  • Summer Concert Series: Enjoy live music in the park every summer.

Engage with the Community

Join local groups and organizations to become an active part of Middletown. Here are some ways to connect:

  • Community Center Events: Participate in workshops and classes.
  • Social Media Groups: Stay updated through Facebook Community Page.

Get Started on Your Real Estate Journey

Are you ready to find your dream home in Middletown, MD? Whether you’re a first-time buyer or looking to upgrade, our team is here to help you every step of the way.

Contact Us Today!

To learn more about available properties or to schedule a consultation, reach out to us:

Discover why Middletown, MD is the perfect place for you and your family!

One of the most popular communities provided by Charis Realty Group - Christine Issler, Broker
34
# of Listings
3
Avg # of Bedrooms
$212
Avg. $ / Sq.Ft.
$877,131
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

13 Properties Found. Page 1 of 1.

Escape the subdivision life for a residence defined by scale, privacy, and rugged utility. Set on 32.39+/- acres, this cabin-style estate is built for those who want their permanent home to feel like a fortress of solitude without sacrificing modern comforts. The interior features a recently updated kitchen equipped with new appliances and granite countertops. While there is a propane furnace, there is also a classic woodstove that provides a high-efficiency heating source and a focal point for the entertainment area in the basement. The home’s footprint is anchored by an expansive rear deck designed for four-season use; whether you’re hosting or decompressing, the integrated hot tub offers total privacy, screened by a dense canopy of mature timber to create an outdoor living room that feels completely removed from the outside world. This isn't just a woodlot; it's a gateway. The property borders Gambrill State Park, providing exploration and recreational opportunities right out your back door. For the serious outdoorsman or the family seeking an active lifestyle, the land offers endless utility for hiking, scouting, and wildlife management. The long, wooded approach ensures a level of seclusion and security that is increasingly rare, making this an ideal primary residence for those seeking a quiet, secure environment. Practicality meets potential inside and out, with a walkout basement that provides the ideal entertainment area or can be converted into a home office, gym, or additional bedrooms to grow with your needs. An existing shed provides organized storage for ATVs and maintenance equipment, keeping your primary living spaces clutter-free. Shown by appointment only, this is more than a getaway—it is a rare opportunity to own a significant piece of acreage with your ideal mountain retreat on your own recreational land in the Catocin Mountains.
#MDFR2074476

MIDDLETOWN

8939 HAWBOTTOM ROAD

3 Beds

3 Baths

3,236 Sq.Ft.

$949,000

MLS#: MDFR2074476

HOME TO BE BUILT. Nestled on a beautiful, wooded 2.25-acre lot, this to-be-built home by Grossnickle Construction offers the perfect blend of luxury and comfort. The home features 3 spacious bedrooms, including a private primary suite, 2 full bathrooms, and a convenient powder room. This plan also includes 400 sqft rec room in the basement and the option for an upstairs bonus room. Enjoy the peaceful, natural setting with mature trees and scenic surroundings while still having the opportunity to personalize your new home. This featured plan can be built as-is, tweaked to your preferences, or you can choose a completely different custom plan to fit this homesite. Don’t miss this chance to build your dream home in a truly serene location.
#MDFR2080886

MIDDLETOWN

MOUNTAIN CHURCH ROAD

3 Beds

2 Baths

3,000 Sq.Ft.

$924,500

MLS#: MDFR2080886

Welcome to 5 Dean Lane, a stunning 4-bedroom, 4.5-bath home in the sought-after Middletown Glen community. Ideally located within walking distance of schools, parks, and the library, this home also enjoys a beautiful view of the neighborhood’s open common area directly across the street, creating a spacious and inviting setting . Also this exceptional home is also just minutes from the nature center, local restaurants, golf courses, and major commuter routes. Step inside to a welcoming foyer featuring a private home office, then continue past the elegant formal dining room into the spacious living room that seamlessly opens to the bright, eat-in kitchen—perfect for everyday living and entertaining. Entering through the attached 2-car garage, you'll appreciate the thoughtfully designed mudroom with built-in storage, along with an oversized pantry and convenient powder room on the main level. Upstairs offers an ideal layout with an additional loft-style lounge that provides flexible living space. The luxurious primary suite occupies its own private wing and features a sitting area, two walk-in closets, and a spa-like ensuite bath. Two additional bedrooms share a full hall bath, while the opposite wing includes a fourth bedroom with its own ensuite bath and a conveniently located laundry room. The finished walkout basement is an entertainer's dream, featuring a large recreation area, wet bar, full bathroom, and ample storage space. Outside, the beautifully hardscaped backyard offers a low-maintenance setting that's perfect for relaxing or hosting gatherings. Meticulously maintained and truly move-in ready, this thoughtfully upgraded home combines generous living spaces, quality finishes, and an unbeatable location. 5 Dean Lane has everything you've been looking for.
#MDFR2084684

MIDDLETOWN

5 DEAN LANE

4 Beds

4 Baths

4,497 Sq.Ft.

$834,000

MLS#: MDFR2084684

Welcome to 411 Glenbrook Drive in the desirable Glenbrook community of Middletown. This home offers over 4,600 finished square feet of living space with a great layout, beautiful golf course views, and several recent updates. The main level features a two-story foyer, formal living and dining rooms, and a spacious kitchen with upgraded cabinetry, a large center island, and a bright morning room overlooking the surrounding landscape. The open living area features soaring ceilings, abundant natural light, and a welcoming space that is ideal for relaxing or entertaining. The main level primary suite offers convenience with an ensuite bathroom and generous closet space. The upper level includes additional bedrooms and flexible living areas to fit a variety of needs. The finished walk-out lower level provides additional space for recreation, a home office, or additional living areas. Outside, enjoy the patio and peaceful golf course setting that Glenbrook has to offer. Recent improvements include a brand new roof, new gutters, and an owned photovoltaic solar system that conveys with the property, providing energy efficiency and added value for the next homeowner. Conveniently located in Middletown with easy access to shopping, dining, commuter routes, and Frederick County schools. This wonderful home offers a combination of space, updates, and a desirable location - don't miss your opportunity to call this house, home!
#MDFR2086740

MIDDLETOWN

411 GLENBROOK DRIVE

4 Beds

3 Baths

4,603 Sq.Ft.

$774,900

MLS#: MDFR2086740

This home is an absolute MUST SEE. This home has been immaculately maintained and features all of it's original charm. You will fall in love with the beautiful hardwood floors throughout this spacious 5 bedroom, 3 full bath colonial that features 3,200 square feet of living space along with a large 832 square foot basement, with outside entrance. This classic beauty is situated on a large, beautifully landscaped and manicured, corner lot of .64 acres in Middletown's Historic District. You will fall in love with all of the historic charm and craftsmanship that blends seamlessly with modern upgrades such as vinyl siding and replacement windows. There are several bonus areas that provide added charm to this already captivating home. There is a family room that was crafted from a former garage, a second floor sunroom area for relaxing, a bonus room that could be a home office and a sitting area off of the formal dining room. This is a true gem and you will be amazed at the incredible condition.
#MDFR2085770

MIDDLETOWN

200 PROSPECT STREET

5 Beds

3 Baths

3,206 Sq.Ft.

$699,000

MLS#: MDFR2085770

Step into a world of timeless elegance with this stunning Victorian home, a true masterpiece of craftsmanship and design. Built in 1900, this residence boasts and shows a life of owners who loved it and those who appreciated its unique architectural features. Beautiful hardwood floors throughout the entire home, including in the updated and modernized kitchen! Upgraded countertops and stainless steel appliances, including a dishwasher, 40" dual-fuel range and refrigerator. An extra refrigerator/freezer in the basement provide ample storage for all your culinary needs. The main floor laundry acts as a separator and tie between the rest of the house and the "in-law" suite which was once the summer kitchen. Retreat to one of the five generously sized bedrooms, each offering a peaceful haven for rest and relaxation. The home boasts 3 fireplaces, one fully flued for log burning, and though the other two are sealed off, the one in the kitchen has a wood-style, ventless propane stove installed. The bathrooms are thoughtfully designed, featuring walk-in showers, glass doors and electric, radiant-heat tile floors. One bathroom has even had accessibility in mind making it a "wet room" for those with mobility issues. Outside you will find no detail missed, as even the exterior shingles were hand scalloped to properly match the original victorian look and design. The front porch is inviting and relaxing to watch traffic drive by on their way through Middletown, and the sleeper porch allows you to have some peace and quiet while enjoying nature. With nearly a third acre lot, there's plenty of room for outdoor activities or gardening. This Victorian gem is not just a house; it's a place where memories are made, and stories are shared. Experience the perfect blend of classic elegance and contemporary comfort-your dream home awaits!
#MDFR2089044

MIDDLETOWN

21 E MAIN STREET

5 Beds

3 Baths

2,820 Sq.Ft.

$680,000

MLS#: MDFR2089044

WHERE HOME MEETS HOMETOWN! Beautifully built in 2019 and ideally located on a premium corner homesite, this exceptional Colonial offers the rare combination of a beautifully appointed, move-in-ready home and the welcoming lifestyle of Historic Middletown, one of Maryland's most desirable small towns. With 3 finished levels, new carpeting, a freshly painted interior, four bedrooms, 3 full and 1 half baths, a covered front porch, a covered rear maintenance-free deck, and a location where schools, restaurants, the recently built library, community parks, and Historic Main Street are all within easy reach, this is a home designed to be lived in, enjoyed, and remembered. From the moment you arrive, the covered front porch invites you to slow down and enjoy the neighborhood and serene mountain views. Inside, the light-filled open floor plan creates an effortless flow for both everyday living and entertaining. Beautiful, engineered wood flooring throughout the main level, high ceilings, and an abundance of windows give the main level a bright, welcoming feel. The private office with French doors offers the perfect place to work from home, while the heart of the home is undoubtedly the spacious kitchen, breakfast/dining area, and family room. Gather around the oversized island in the gorgeous kitchen featuring timeless white cabinetry, quartz countertops, stainless steel appliances, gas range, wall oven, built-in microwave, dishwasher, refrigerator, and plenty of workspace for preparing everything from weekday meals to holiday dinners. The kitchen opens to the breakfast/dining area and family room, making it easy to stay connected with family and guests. A gas fireplace adds warmth and ambiance, while the extra windows bring the outdoors in. Just beyond the kitchen, the covered maintenance-free deck creates another inviting place to relax, dine al fresco, or gather with friends. A convenient rear hallway includes a pantry closet, powder room, coat closet, and access to the two-car garage. Upstairs, the spacious primary suite feels like a private retreat, complete with room for a sitting area, massive walk-in closet, and beautifully appointed ensuite bath with walk-in shower, dual-sink vanity, and private toilet room. Three additional bedrooms provide space for family, guests, hobbies, or a second home office. One bedroom features a large picture window that fills the room with natural light. The convenient upper-level laundry room with built-in shelving and full hall bath add to the thoughtful functionality of this level. The finished lower level adds an entirely new dimension to the home with a generous recreation room and walkout to a paver pad and the rear yard, along with a full bath, storage room, and utility room. Whether envisioned as a game room, movie night destination, guest space, exercise area, or simply a place to spread out, this flexible level adapts beautifully to your lifestyle. Freshly painted interiors, newly installed carpeting, a tankless water heater, natural gas heat, and an exceptionally well-designed floor plan make this home truly move-in ready. But perhaps what makes this property most special is the life you can live here. Step outside, and you're part of a community where neighbors gather, traditions matter, and there is always something to look forward to. Walk to Historic Main Street for restaurants and local events, enjoy Friday night football, stroll to the library, hear the church bells ring, or spend an afternoon at nearby Middletown Community Park with its trails, playgrounds, soccer and football fields, fishing pond, picnic areas, sand volleyball, disc golf, bandstand, and more. Middletown has a way of taking you back to a simpler time with holiday celebrations, parades down Main Street, outdoor movies, concerts in the park, and the familiar rhythm of a community that comes together. This is more than a beautiful house. It is a place to put down roots, make memories, and truly enjoy coming home.
#MDFR2088792

MIDDLETOWN

12 DEAN LANE

4 Beds

3 Baths

3,142 Sq.Ft.

$675,000

MLS#: MDFR2088792

Welcome to this former model home on a spacious corner lot offering comfort, flexibility and inviting indoor and outdoor living. The main level features refinished hardwood floors, a dedicated office, a bright kitchen with granite counters and large island, and a family room with a wood-burning fireplace framed by a dramatic floor-to-ceiling brick surround. Just off the kitchen, the skylit three-season sunroom offers a peaceful retreat with electric heat. Upstairs, four bedrooms include a spacious primary suite with walk-in closet and renovated bath featuring a tub and separate shower. The fully finished and renovated basement adds a large recreation room with propane stove plus a separate flex room for guests, an office, workout space or hobbies. Outside, enjoy a fenced yard, maintenance-free deck with built-in bar counter, adjoining patio and fire pit, plus a side-load two-car garage. All this just a short distance to Middletown Park, downtown shops, restaurants, grocery shopping and the many amenities of this charming Main Street community.
#MDFR2088234

MIDDLETOWN

301 CONE BRANCH DRIVE

4 Beds

3 Baths

3,822 Sq.Ft.

$665,000

MLS#: MDFR2088234

New on site 3 days ago
Welcome to 7312 Countryside Circle, set on 2.54 acres in Middletown. This 4-bedroom, 3.5-bath home offers approximately 2,116 square feet above grade plus a finished lower level, creating plenty of flexibility for everyday living. The main level features comfortable gathering areas, while four bedrooms provide room for family, guests, or a home office. Downstairs, the finished lower level offers even more possibilities for a family room, gym, playroom, hobbies, or entertaining. Outside, the yard gives you room to garden, play, entertain, or simply enjoy the property and its peaceful surroundings. Served by well and septic, this home offers a more private setting while still being convenient to everyday necessities. Enjoy all that Middletown has to offer, including local restaurants, shops, parks, and schools, with Downtown Frederick just a short drive away. Easy access to Route 40A, Route 17, I-70, I-270, and Route 15 makes getting around Frederick County and commuting toward Montgomery County and the D.C. area convenient. If you’re looking for acreage, a versatile floor plan, and a Middletown location that keeps you connected without sacrificing breathing room, this one is worth a look.
#MDFR2089606

MIDDLETOWN

7312 COUNTRYSIDE CIRCLE

4 Beds

3 Baths

2,866 Sq.Ft.

$649,000

MLS#: MDFR2089606

***OPEN HOUSE SUNDAY 10/4 - 11:00-1:00***PRICE DROP $25K! SELLER SAYS GET IT SOLD! Welcome to 7 Derr Lane in the sought-after Villages at Foxfield—Middletown’s premier 55+ community—where Original Owners have meticulously maintained and thoughtfully upgraded this beautiful home, showcasing true pride of ownership everywhere you look. Perfectly positioned within walking distance to Middletown Park and its many amenities, this home also backs to serene woods, walking/jogging paths, and open green space—offering both convenience and some privacy. Enjoy peaceful mornings on the covered front porch or unwind in the backyard retreat featuring a walkout patio, koi pond, and a hidden “secret garden” be sure not to miss. Inside, the home blends comfort and modern updates. The kitchen is a standout with a Corian island, mosaic tile backsplash, stainless steel appliances (replaced 2019), induction downdraft cooktop, double oven, and ceramic flooring—ideal for both everyday living and entertaining. The main level boasts hardwood flooring (2018) and a warm, inviting family room with a propane fireplace and direct access to the newer, enlarged Trex deck (2022, with updated door in 2025). The spacious layout includes vaulted ceilings, a tray ceiling in the primary suite, and a dramatic two-story overlook with loft above. The primary bath was beautifully renovated in 2017, and the upper level features new carpet (2019). Additional updates include leased solar panels for energy efficiency (2018), washer and dryer (2021), vinyl fencing (2022), new roof and ventilation (2024), HVAC (2015), and water heater (2018). The unfinished lower level offers a walkout to the backyard, rough-in for a full bath, and a wide-open layout ready to be customized to your needs. Garage is equipped with a 200 amp 240 volt EV charging circuit and a newer garage door opener (2021). This is a rare opportunity to own a truly move-in-ready home in Middletown’s most desirable active adult communities—combining thoughtful upgrades, natural beauty, and a vibrant lifestyle.
#MDFR2086228

MIDDLETOWN

7 DERR LANE

3 Beds

2 Baths

2,208 Sq.Ft.

$600,000

MLS#: MDFR2086228

Escape the ordinary with this one-of-a-kind mountain-inspired retreat set on more than 5 secluded acres of mature woodland. Designed to embrace its natural surroundings, this distinctive chalet welcomes the outdoors in with dramatic vaulted ceilings, walls of windows, and multiple skylights that fill the home with sunlight while showcasing peaceful forest views from nearly every room. The inviting great room is centered around a beautiful fireplace, creating the perfect gathering place, while rich hardwood flooring and natural finishes enhance the home's warm, rustic charm. Step outside onto the expansive wraparound deck, where you can enjoy the sights and sounds of nature, entertain guests, or simply relax in complete privacy. The updated kitchen features granite countertops and stainless-steel appliances including gas cooking, offering modern functionality without sacrificing the home's unique character. An oversized detached two-car garage provides exceptional space for vehicles, a workshop, outdoor equipment, or additional storage. Offering the rare combination of privacy, distinctive architecture, and everyday convenience, this exceptional property feels like a secluded woodland retreat while remaining only about 15 minutes from Middletown's restaurants, shopping, and Middletown schools. Recent improvements include a new roof and skylights (2020), stove and microwave (2021), water softener and neutralizer (2022), and refrigerator (2025). Better see it soon before someone else gets to call it home!
#MDFR2086608

MIDDLETOWN

6838 MOUNTAIN CHURCH ROAD

3 Beds

3 Baths

2,488 Sq.Ft.

$584,900

MLS#: MDFR2086608

New on site 3 days ago
Start your mornings with coffee on the deck, surrounded by peaceful, pasture-like views and a gentle breeze. This well-built all-brick 3-bedroom rancher sits on a beautiful 2.08-acre lot and offers easy one-level living, an attached two-car garage, and exceptional storage throughout. Wood floors on the main level, gas fireplace in living room and wood fireplace in lower level, French doors with built in shades in dining room allows for generous natural sunlight to filter through. The owners have thoughtfully completed numerous upgrades over the years while fully enjoying everything this special property has to offer. The full bathroom offers a double vanity with generous counter space, a deep linen closet with shelving and a laundry chute that drops next to the laundry area in the lower-level making that task a bit easier. The lower level provides additional flexibility, currently arranged with a comfortable living area featuring a wood stove, along with a separate storage area with auto-fan for ventilation. 2 mini split units to heat and cool the space .With its generous layout and exterior access through a French door with built-in shades and extra-wide steps to the backyard, this space can be easily reimagined to suit your needs. Outside, the setting truly shines. Meander through the lovely garden, where seasonal color, beautiful plantings, a charming potting shed, and a stepping-stone path create a serene place to relax and explore. Continue a bit farther to discover the 56x36 pole barn with electricity and water, once used for horses, offering even more possibilities for hobbies, plenty of storage for your tractor, lawn equipment, etc) or whatever suits your needs.
#MDFR2089736

MIDDLETOWN

8922 MOUNT TABOR ROAD

3 Beds

1 Baths

1,380 Sq.Ft.

$535,000

MLS#: MDFR2089736

***Room to Breathe, Space to Grow, and Mountain Views to Come Home To*** Set on 3.72 acres just minutes from the heart of Middletown, this 3-bedroom, 2.5-bath ranch offers the kind of space and versatility that's increasingly hard to find. Here, you can enjoy a peaceful country setting and mountain views while keeping shopping, dining, schools, and everyday conveniences within easy reach. Inside, the home offers comfortable main-level living complemented by a finished lower level that expands the possibilities for recreation, hobbies, working from home, or simply having more room to spread out. The kitchen features granite countertops and two sinks, while the rear deck creates a natural extension of the living space and a place to take in the surrounding landscape. Outside is where this property really begins to set itself apart. An above-ground pool adds another way to enjoy the warmer months, while the expansive acreage offers room to garden, play, entertain, or simply enjoy having more space between you and the everyday hustle. The oversized detached shop adds flexibility, featuring a 10' x 10' door clearance and its own HVAC system. Whether you need space for vehicles, equipment, storage, a workshop, or your favorite hobby, it's a valuable extension of the property. Recent improvements to the main house include a roof and siding that are less than one year old. The owners have also installed a new well-water filtration system and completed repairs to the septic system. All of this comes without an HOA or city taxes and with the convenience of Middletown just minutes away. The property is also located in a USDA-eligible area, offering an additional financing option for qualified buyers. If you've been looking for more land, more flexibility, and a little more breathing room without giving up access to town, 7820 Myersville Road is ready for its next chapter. Property is being sold as-is and is subject to third-party approval as a short sale.
#MDFR2087120

MIDDLETOWN

7820 MYERSVILLE ROAD

3 Beds

2 Baths

2,496 Sq.Ft.

$534,999

MLS#: MDFR2087120

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