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

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
24
# of Listings
4
Avg # of Bedrooms
$234
Avg. $ / Sq.Ft.
$1,045,578
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

10 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.

$989,000

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 this beautifully upgraded colonial nestled in the sought after Glenbrook golf community- backing to the 15th fairway. Relax, entertain and unwind in your resort style backyard with a stunning inground salt water pool, beautifully landscaped private back yard and new paver walkways. This light filled beauty is loaded with desirable features and upgrades offering nearly 5400 square feet of exceptional living space designed for both everyday comfort and elegant entertaining. This stunning home features brand new luxury vinyl flooring across two levels, creating a modern and cohesive feel from the moment you enter. The spacious gourmet kitchen is the heart of the home complete with granite counter tops and abundant cabinetry, and an inviting morning room filled with natural light and overlooking the private pool and yard- the perfect setting for morning coffee or evening gatherings. The impressive family room showcases a cozy fireplace and soaring ceilings for an open and airy layout, while the dual staircases add timeless architectural charm and functionality. Upstairs the expansive primary suite offers a peaceful retreat with a separate sitting room and a spa-like primary bathroom designed for relaxation. The finished walk up basement provides incredible versatility with an extensive built-in storage space making it ideal for recreation, hobbies, a home gym or additional entertaining space. There is also a EV charger in the garage and the roof and gutters have both been replaced! This home combines elegant updates, generous living spaces and exceptional outdoor living which lends itself to the perfect blend of luxury, warmth and lifestyle all while located in a desirable school district, nearby dining, shopping, parks and convenient commuter routes! Welcome home!
#MDFR2080926

MIDDLETOWN

503 GLENBROOK DRIVE

4 Beds

3 Baths

4,892 Sq.Ft.

$885,000

MLS#: MDFR2080926

New on site 2 days ago
One of the largest and most sought-after models in the neighborhood, this beautifully updated home offers the perfect combination of space, style, and functionality, all set on a large lot backing to trees for added privacy and a more peaceful setting. From the moment you enter, the scale of the home stands out with hardwood flooring throughout the main level, a dramatic two-story family room filled with natural light and a gas fireplace, dual staircases, and spacious formal living and dining rooms that make the home feel both elegant and comfortable. A private main-level office, powder room, and laundry room add convenience and flexibility for today’s lifestyle needs. The fully renovated kitchen is truly the centerpiece of the home, designed with both everyday living and entertaining in mind. Features include granite countertops, updated cabinetry, stainless steel appliances, double wall ovens, and a cooktop built into the oversized island, along with a separate table space area overlooking the backyard. Upstairs, the oversized primary suite offers a true retreat with room for a sitting area, a huge walk-in closet, and a spacious bath featuring dual sinks, separate soaking tub and shower, and a private water closet. Three additional bedrooms offer generous room sizes and large closets, and the upper level also includes an additional full bath, providing a total of three full and one half baths throughout the home. The outdoor living spaces are just as impressive, with a screened porch and open deck overlooking the backyard and tree line, perfectly ideal for relaxing, entertaining, or enjoying the outdoors in every season. The finished walkout lower level provides incredible additional living space with a large recreation room, media room, full bath, and an oversized storage room, offering endless possibilities for entertaining, hobbies, fitness, guests, or flexible living arrangements. With its impressive size, updated finishes, versatile floorplan, and desirable Middletown location, this is the kind of home that rarely becomes available.
#MDFR2082766

MIDDLETOWN

8 N POINTE TERRACE

4 Beds

3 Baths

5,674 Sq.Ft.

$774,900

MLS#: MDFR2082766

Price Improvement! This iconic 1937 Brick Tudor Revival residence and adjacent additional structure are being sold together, situated on two separately deeded parcels that share a well and septic system. The Tudor Revival home has been freshly painted and offers timeless character blended with thoughtful updates throughout. The kitchen features stainless steel appliances, a new cooktop, custom cabinetry, and granite countertops. The formal dining room boasts built-in china closets and an oversized bay window, while the inviting living room centers around a classic wood-burning fireplace. The primary suite includes custom wood-paneled walls, an oversized bay window, a walk-in closet plus two additional closets, and a private ensuite bath. A new hot water heater, along with new roofs on both the home and pool house, provides added peace of mind. The finished basement expands the living space with a recreation room, partial kitchen, office, laundry area with shower, and a half bath—ideal for a variety of residential needs. Outside, the oversized fully fenced backyard creates a private retreat, featuring an in-ground pool with a new liner installed in 2022, a brick pool house, and a storage shed—perfect for entertaining or relaxing. The adjacent structure offers substantial additional space and includes notable features such as three-phase 400-amp electrical service, a 4,000-pound jib crane, and existing interior infrastructure. The property is currently zoned R3 and is being sold strictly for residential use. Any future use of the additional structure is subject to zoning regulations, and buyers are encouraged to conduct their own due diligence with the appropriate local authorities.
#MDFR2076696

MIDDLETOWN

3213 OLD NATIONAL PIKE

3 Beds

2 Baths

1,782 Sq.Ft.

$699,900

MLS#: MDFR2076696

New on site today
This home offers EVERYTHING you move to Middletown for; small-town feel, walkability to parks, restaurants, library and shopping, top-rated schools, easy access to commuter routes and THE VIEW! That’s right- one of the few homes in the neighborhood that backs to OPEN SPACE, owned by the town, with a view of South Mountain! With 3,696 sq ft of living space, you’ll find a welcoming open floor plan with hardwood floors, a sitting room to relax by the gas fireplace open to the family room which includes a second gas fireplace, both with wooden mantles with detailed Cornice molding and stone surrounds. This room includes a double door to the deck and is open to the eating area, complete with a second double door for maximum deck access. The kitchen offers 42-inch cabinetry, Corian countertops, an island with pendant lighting and seating for two. For ease of preparing meals you’ll have the double oven/range and recently renovated pantry with built-in drawers. The formal dining room includes custom boxed trim, chair rail and crown moldings that continue throughout the main level, completed by the full laundry room, powder room and access to the attached 2-car garage. With 5 true bedrooms upstairs, there is no lack of room for a growing family or guests! The primary bedroom includes its own en-suite bathroom with soaking tub, separate shower with Subway tile, dual sinks and a large walk-in closet. The 4 secondary bedrooms include lighted ceiling fans and access to the shared full bathroom in the hallway. The lower level game room with ample seating and entertaining area includes a pool/ping pong table, kitchenette with fridge/freezer combo, microwave and wet bar and a built-in desk with cabinets and access to the covered patio for afternoon shade. If that weren’t enough, you also get a 6th bedroom with a brand new egress window and huge walk-in closet, 3rd full bathroom and oversized storage room. The outdoor living space at 24 Young Branch Drive is unmatched with a vinyl, low-maintenance deck with 6 brand new support posts, lighted steps to the paver patio below and a comfortable screened porch where you can enjoy that peaceful view, even on a rainy day. Recessed lighting, custom window coverings and shutters, built-in shelving, central VAC… even a park that borders the neighborhood! Water heater (2026), gas fireplace log sets (2026), air purifier system and lower level egress window (2025), roof (2016), NO HOA! ONE YEAR HOME WARRANTY included!
#MDFR2082480

MIDDLETOWN

24 YOUNG BRANCH DRIVE

6 Beds

3 Baths

3,696 Sq.Ft.

$672,000

MLS#: MDFR2082480

NEW PRICE! OPEN HOUSE SUNDAY 5/17 - 10:00-12:00! 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.
#MDFR2080220

MIDDLETOWN

7 DERR LANE

3 Beds

2 Baths

2,208 Sq.Ft.

$650,000

MLS#: MDFR2080220

Now on market! This picturesque single-family home sits in the heart of beautiful historic Middletown. Meticulously cared for from top to bottom, this exceptional property is perfectly positioned on a premium lot with stunning views of Middletown’s historic steeples, the breathtaking South Mountain range, and the charm of a white-picket-fence community. Tucked within a small clustered neighborhood with no HOA, this home offers the feel of a close-knit community without the added monthly dues. Inside, you’ll find five distinct bedrooms, including a convenient main-level bedroom and full bathroom. Step outside to the expansive rear deck, the perfect place to enjoy your morning coffee or unwind with evening cocktails while taking in the mountain views. The beautiful kitchen is ideal for intimate entertaining and is complemented by a well-appointed butler’s pantry. Downstairs, the fully finished basement is an entertainer’s dream, featuring a full wet bar, high-tech theater system with surround sound and projector, and additional gathering space with a walkout to the backyard.
#MDFR2079846

MIDDLETOWN

307 WASHINGTON STREET

5 Beds

3 Baths

3,288 Sq.Ft.

$634,990

MLS#: MDFR2079846

Tucked away on over 5 private acres, this chalet-style home is not your typical property – and that’s exactly the point. With soaring ceilings, expansive windows, and skylights throughout, the home has a great balance of natural light and surrounded by wooded views that give it a true treehouse-like feel. A cozy fireplace anchors the main living space, while hardwood floors and warm finishes add to its character. The wraparound deck extends the living space outdoors, offering a peaceful setting for morning coffee or unwinding at the end of the day. An oversized detached two-car garage provides ample space for storage, hobbies, or projects. The kitchen has been refreshed with granite countertops and stainless steel appliances, blending modern convenience with the home’s unique style. This is a home for someone who appreciates privacy, architecture, and a setting that feels removed from it all - while still being just 15 minutes to Middletown’s shops, dining, and Middletown Schools. Updates include: Roof (2020), Skylights (2020), Stove & Microwave (2021), Refrigerator (2023), and Water Softener/Neutralizer (2022).
#MDFR2078904

MIDDLETOWN

6838 MOUNTAIN CHURCH ROAD

4 Beds

3 Baths

2,488 Sq.Ft.

$624,900

MLS#: MDFR2078904

Charming Victorian Home offers the perfect blend of historic character and modern upgrades in the heart of Middletown. Vehicle access from both Beautiful Main Street and Convenient Broad Street, this home provides excellent accessibility and curb appeal. Beautiful Hard Wood Floors, Wainscoting, Crown Molding throughout. Main Level Features Separate Living Room, Dining Room w/Pocket Doors, Family Room, Kitchen, Updated Full Bath. Kitchen includes Center Island w/Seating, Gas Cook-top, and Pantry. (2024: New Refrigerator, New Gas Cooktop, New Kitchen Disposal). Upper Level Features 3 Nice Size Bedrooms. Updated Full Bath with Heated Floor, Large Glass Front Shower, Custom Cabinets, Makeup Vanity, and Jetted Claw Foot Tub. An Oversized 2nd Floor Laundry Room with a Pocket Door features a second kitchenette area including upper and lower cabinets and countertop space. New Washer and Dryer in 2022. Access to Attic and a Small room with view overlooking back yard. Property also includes a Large/Tall Detached 2 Car Garage w/Tesla EV Charger. Attached to the Garage is a Large Shop/General Use Space. Home includes a Large Rear Deck off the Kitchen. A Whole-House Backup Power Generator w/New Battery in 2026. 2 Whole-House Surge Protectors, 2 Outdoor A/C unit Surge Protectors installed 2025. 4 Propane Tanks. This Listing also includes an Attached Additional Lot of Record w/Temp Restrictions. Conveniently located near schools, shopping, dining, parks, and easy access to major highways. This well-cared-for Victorian on Main Street is truly special.
#MDFR2081222

MIDDLETOWN

124 E MAIN STREET

3 Beds

2 Baths

2,474 Sq.Ft.

$599,900

MLS#: MDFR2081222

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