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
25
# of Listings
4
Avg # of Bedrooms
$235
Avg. $ / Sq.Ft.
$994,576
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

25 Properties Found. Page 2 of 2.

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! 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

*PRICE TO SELL* 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.

$625,000

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.

$585,000

MLS#: MDFR2081222

New on site 1 day ago
Welcome to 2 Derr Lane, a beautifully maintained home in the highly sought-after Foxfield 55+ Community in Middletown. Offering 2,279 square feet of living space on a desirable corner lot, this home combines comfort, convenience, and thoughtful upgrades throughout. Proudly offered by the original owners, this meticulously maintained residence showcases true pride of ownership at every turn. Recent improvements include new roof, new carpet, fresh paint in select rooms, and all new stainless steel appliances, making the home move-in ready for its next owner. The spacious floor plan features three generously sized bedrooms and three full bathrooms, including a main-level primary suite and a second main-floor bedroom, providing the ease and convenience of main-level living. Soaring vaulted ceilings create an open and airy feel, while the dramatic two-story overlook and loft above add architectural character and flexible living space. The bright living room opens directly to a beautiful covered patio complete with a ceiling fan, creating a seamless indoor-outdoor flow and an ideal space for relaxing or entertaining. Beyond the patio, you'll find a private backyard retreat with a secluded area that offers the perfect setting for gardening, enjoying nature, or simply unwinding in your own peaceful outdoor oasis. Ideally located within walking distance of Middletown Park and its many amenities, this home offers the perfect balance of accessibility and privacy. Enjoy peaceful mornings on the covered front porch, entertain guests on the patio, or simply appreciate the care and attention that has gone into maintaining this exceptional property. A rare opportunity to own a thoughtfully upgraded home in one of Middletown's most desirable active adult communities.
#MDFR2083076

MIDDLETOWN

2 DERR LANE

3 Beds

3 Baths

2,279 Sq.Ft.

$555,000

MLS#: MDFR2083076

Welcome Home to 8209 Old Hagerstown a beautifully updated and spacious 5-bedroom, 3-bathroom home located in the highly sought-after Middletown, MD. This move-in ready property features modern upgrades throughout, offering the perfect blend of style, comfort, and functionality. Enjoy generous living spaces, an updated kitchen featuring SS Appliances, white shaker cabinets, quartz counters and MORE! Well-appointed bedrooms ideal for both everyday living and entertaining. Fully finished basement offers so much space for entertaining. Large deck great for relaxation! Private off street parking in driveway and SO MUCH MORE! Situated in a desirable location close to commuter routes and many attractions —this is a home you won’t want to miss! All new Siding, New Gutters, New Roof, Freshly painted interior of Garage, New Well Pump and SO MUCH MORE!!
#MDFR2082600

MIDDLETOWN

8209 OLD HAGERSTOWN ROAD

5 Beds

3 Baths

2,312 Sq.Ft.

$499,900

MLS#: MDFR2082600

Adorable well-kept and maintained one level living in this ranch located between Middletown and Myersville with fully finished basement. As you enter through the front door you are greeted with an open living room, kitchen and dining area. The doors from the kitchen lead out to a screened in porch that is adjacent to a grilling area for lots of entertaining space. The main level has been freshly painted and has 3 bedrooms and 1 full bath that has been recently updated. The basement is bright with a large family room and efficiency kitchen, full bath, office/den/game room/guest room and separate laundry area. In cold months enjoy cozy nights near the basement pellet stove. The lush flat backyard has plenty of room for activities and gatherings. Plenty of storage in the storage shed. The attached carport is great for parking and also a family entertaining area. Minutes to Middletown with shopping, grocery stores, library, numerous restaurant choices and local schools. Close to commuter routes. This one won't last long!
#MDFR2083354

MIDDLETOWN

8914 GLORIA AVENUE

3 Beds

2 Baths

2,040 Sq.Ft.

$489,900

MLS#: MDFR2083354

New on site 3 days ago
Welcome to 213 W Main Street in the heart of historic Middletown! This charming home blends historic character with everyday functionality. Inside, you’ll find original Southern yellow heart pine flooring, 9-foot ceilings on the main level, and beautiful architectural details throughout. The main level features a spacious living room, dining room, kitchen, full bath with shower, and convenient laundry area. Upstairs offers three bedrooms, one full bath, and one-half bath, including a bedroom with exposed brick that adds warmth and character. The top floor features a large fourth bedroom with exposed beams and skylights, creating a bright and inviting retreat. Outdoor living is just as appealing with a fenced backyard and new deck, perfect for relaxing or entertaining. Adding even more versatility, the property is zoned Town Commercial with numerous approved commercial uses. Enjoy a walkable lifestyle close to local restaurants, shops, parks, schools, and the brand-new library. Nearby favorites include Fratelli's Italian & Seafood, The Main Cup, and Dempsey's Grille, along with other popular local spots just minutes away. Grocery stores, golf courses, additional dining, and shopping along the Middletown Parkway corridor are also conveniently nearby. Throughout the year, the town hosts community events that further enhance the appeal of this charming historic community. Don’t miss your opportunity to own a piece of Middletown history offering space, character, versatility, and an unbeatable location. Schedule your tour today!
#MDFR2081090

MIDDLETOWN

213 W MAIN STREET

4 Beds

2 Baths

2,518 Sq.Ft.

$435,000

MLS#: MDFR2081090

Charming 1/4 acre buildable on E. Green Street. The buyer of 19 E. Main Street will have the right of first refusal on the sale. Additional photos available on the 19 E. Main Street listing MDFR2082574.
#MDFR2082686

MIDDLETOWN

Lot 1 E GREEN STREET

None Beds

None Baths

0.24 acres

$150,000

MLS#: MDFR2082686

1 2

properties found. properties found. Page of .

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