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

MIDDLETOWN

One of the most popular communities provided by Charis Realty Group

MIDDLETOWN

About MIDDLETOWN

Discover Middletown, MD Real Estate 

Welcome to Middletown, Maryland! Nestled in the heart of Frederick County, Middletown offers a charming blend of small-town atmosphere and modern amenities. If you’re searching for a place where community, convenience, and natural beauty meet, Middletown, MD real estate is the perfect choice.

Why Choose Middletown, MD?

Located just minutes west of Frederick, Middletown boasts picturesque landscapes, historic landmarks, and a warm, welcoming community. Here’s why so many homebuyers are looking for houses for sale in Middletown, MD:

  • Stunning Mountain Views: Surrounded by the scenic Catoctin Mountains and rolling farmland, this area provides breathtaking vistas year-round.
  • Top-Rated Schools: Middletown is renowned for its excellent public schools, including Middletown High School.
  • Charming Downtown: Explore locally-owned shops, cafes, and eateries along Main Street for a classic small-town experience.
  • Nearby Recreation: Enjoy outdoor activities at Middletown Park, South Mountain State Park, and local golf courses.
  • Easy Access: Quick commutes to Frederick, Hagerstown, and even Washington, DC make Middletown ideal for professionals and families alike.

Middletown, MD Housing Market Overview

The Middletown, MD real estate market features a wide variety of properties, from historic Victorian homes to modern new constructions. Whether you’re a first-time buyer, looking to upgrade, or seeking a peaceful place to retire, Middletown offers:

  • Single-family homes
  • Townhouses
  • New builds and developments
  • Spacious lots and acreage

Interested in recent listings? Check current homes for sale in Middletown, MD for up-to-date market trends and pricing.

Live in the Heart of Frederick County

Relocating to Middletown, MD means you’ll experience:

  • A strong sense of community and friendly neighbors
  • Highly walkable streets with beautiful historic architecture
  • Year-round events, including the popular Middletown Heritage Festival
  • An unbeatable blend of rural charm and convenient suburban living

Ready to Find Your Dream Home in Middletown?

From stately colonials to custom-built estates, Middletown, Maryland real estate delivers exceptional value and quality of life. If you’re considering a move, now is the perfect time to contact a trusted Charis Realty Group agent to start your search.

Start living the life you’ve always dreamed of in Middletown, Maryland—where homes are more than houses; they’re part of a vibrant, enduring community.

One of the most popular communities provided by Charis Realty Group
244
# of Listings
3
Avg # of Bedrooms
$273
Avg. $ / Sq.Ft.
$639,184
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

73 Properties Found. Page 3 of 5.

Motivated seller with a new price!!! Property sold as-is, offering upside potential in a great location. Well suited for cash buyers. Welcome to 1936 Old National Pike, a historic, brick-constructed home built around the turn of the last century, situated on nearly 4 acres along Old National Pike in Middletown, MD. Investors, flippers, and restoration experts, attention! A rare opportunity in Middletown, this turn-of-the-century brick home sits on almost four acres along Maryland’s historic Old National Pike. The property offers substantial upside for buyers prepared to take on a full-scale renovation, with large interior spaces, classic brick construction, a metal roof, and mature surrounding acreage. The home, built circa the turn of the last century, is listed strictly "as-is" and is currently not move-in ready. It offers a durable metal roof and generous interior space, but it needs a comprehensive overhaul. The Land & Outbuilding is nearly four acres, feature mature acreage and include a spacious outbuilding/barn structure with existing electric service. This asset can be used as a workshop, studio, storage, or for conversion. Historic Significance: This is a true piece of local history, positioned directly on Maryland’s original National Pike Road. This home is for the buyer dedicated to preservation; it provides the opportunity to bring a landmark property back to its former glory. Conservation Easement: The Maryland Environmental Trust (MET) Conservation Easement covers the property. This is an optimal acquisition for an experienced house flipper or investor looking for a major value-add project with significant potential ROI after full restoration. Ideal for buyers who value privacy, history, and the potential to make this property their own.
#MDFR2073722

MIDDLETOWN

1936 OLD NATIONAL PIKE

4 Beds

2 Baths

2,824 Sq.Ft.

$429,000

MLS#: MDFR2073722

** WORKFORCE HOUSING-BUYER MUST QUALIFY FOR THE NEW CASTLE COUNTY PROGRAM TO PURCHASE -MASSEY INTERIOR UNIT- 3 bedrooms, 2.5 baths, 1 car garage. Approx. 2001 SF! This home features a Finished den, 12x10 DECK, 42" cabinets in kitchen, island, stainless steel appliances, gas range, dishwasher, microwave and recessed lighting in Kitchen. LVP flooring upgrades. 3 pc rough in walk out basement. Don't miss out on this spectacular floor plan! Builder Splits Transfer Tax
#DENC2092584

MIDDLETOWN

446 REDERICK LANE MASSEY LOT 68

3 Beds

2 Baths

2,001 Sq.Ft.

$427,056

MLS#: DENC2092584

Welcome to the 55+ community of Traditions at Whitehall - Annandale Carriage Town Home. This home can be an interior or end unit. The first floor has an owner's bedroom w/ full ensuite bath and walk-in closets, second floor has the 2nd bedroom, loft overlooking the great room and another full bath. 1 car rear load attached garage standard but can be upgraded for a 2-car garage, additional finished upgrades can be purchased to your taste and budget. Community offers in ground pool w/lounge areas, clubhouse featuring exercise & billiards room, gathering/lounge space, full kitchen and a large outdoor patio/grilling area! Builder Splits Transfer Tax (***Photos are of a similar home and may contain options & upgrades not included in listing price shown***)
#DENC2095104

MIDDLETOWN

204 BALDY LN ANNANDALE

2 Beds

2 Baths

1,794 Sq.Ft.

$425,000

MLS#: DENC2095104

Welcome to the 55+ community of Traditions at Whitehall - Alrich Carriage Town Home. This home is available as an interior or end unit & has a first-floor owner's bedroom w/ensuite bath and walk-in closets, second floor has a 2nd bedroom, loft and an additional full bath. Standard 1-car rear load attached garage but can be upgraded for a 2-car garage, and additional finished upgrades can be purchased to your taste and budget. Community offers in ground pool w/lounge areas, clubhouse featuring exercise & billiards room, gathering/lounge space, full kitchen and a large outdoor patio/grilling area! Builder Splits Transfer Tax (***Photos are of a similar home and may contain options & upgrades not included in listing price shown.***)
#DENC2095112

MIDDLETOWN

204 BALDY LN ALRICH

2 Beds

2 Baths

1,794 Sq.Ft.

$425,000

MLS#: DENC2095112

Fantastic Clean, Cozy Townhome in THE 55+ Community of the Middletown area, SPRING ARBOR. Location, Location, Location! Nestled in the charming Spring Arbor community, conveniently close to all Middletown has to offer, this delightful twin/semi-detached residence offers a serene retreat designed for those seeking a vibrant yet peaceful lifestyle. Built in 2007, this home boasts a spacious 1,800 square feet of living space, providing ample room for relaxation and entertaining. As you step inside, you'll be greeted by an inviting atmosphere enhanced by a cozy gas fireplace, perfect for those cooler evenings. The layout allows for personal touches, making it easy to create a space that feels like home. With a new roof, new furnace and upgraded countertops, you can move in and rest easy. The home's attached garage and driveway provide convenient parking options, ensuring that you always have a place for your vehicle and can come inside without exposure to rainy or snowy weather. Lightly touched, almost-new furnishings are negotiable upon request. The excellent condition of the property ensures that you can move in with ease and quickly start enjoying all that this community has to offer. Spring Arbor is more than just a place to live; it's a lifestyle. The home's convenient location close to the Spring Arbor Clubhouse allows quick, easy access in mere minutes via a short walk without getting into and out of the car. The community is thoughtfully designed with a variety of amenities that cater to an active and engaging lifestyle. Residents can enjoy the heated outdoor swimming pool, perfect for a refreshing dip on sunny days, or gather with friends in the clubhouse for games and social events. The fitness center's exercise room provides opportunities to stay active, while the library and game rooms offer quiet spaces for relaxation and leisure. For those who love the outdoors, the community features scenic jog/walk paths and a picnic area, ideal for enjoying the beautiful surroundings. The shuffleboard and bocce courts, horseshoe pits and billiard room add a touch of fun and friendly competition to your days. With a strong sense of community, there are plenty of opportunities to connect with neighbors and make lasting friendships. The association fee includes comprehensive services such as lawn care, snow removal, and common area maintenance, allowing you to spend more time enjoying your home and less time on upkeep. The management office is staffed five days per week. Spring Arbor is the 55-or-better community in the location closest of all to local shops, dining, and entertainment options, making it easy to enjoy the best of what the area has to offer. With a welcoming atmosphere and a focus on community, this residence is perfect for those looking to embrace a fulfilling lifestyle in a beautiful setting. Experience the warmth and comfort of Spring Arbor, where every day feels like a getaway. New Guaranteed Roof was installed in Fall of 2025 and New Furnace was installed in late-January 2026. Close to Middletown shops and restaurants. Close to the Community Clubhouse. DON'T MISS OUT ON THIS HOME! Its in-town and in-community location cannot be beat!
#DENC2098306

MIDDLETOWN

264 TRELLIS LANE

2 Beds

2 Baths

1,800 Sq.Ft.

$425,000

MLS#: DENC2098306

None
#DENC2094038

MIDDLETOWN

40 S CUMMINGS DRIVE

3 Beds

2 Baths

2,200 Sq.Ft.

$424,500

MLS#: DENC2094038

Welcome to your next chapter in the vibrant, caring haven of Whispering Woods — an active adult community where life is anything but boring. This pristine and beautiful, just 5 years young home greets you with an open concept layout, two full baths, two bedrooms and a truly spacious Master's bedroom, tray ceiling and walk‑in closet . Spectacularly clean, neutral finishes, 1 story home and walk in shower and spacious cooking area with plenty of storage! Step outside your door and into a world of daily fun: pickleball, bocce, swimming, social clubs, themed events all year round, and a dining hall with a bar and billiards area tailor‑made for neighbors to become friends. All of these, just minutes from shopping centers and restaurants, with easy access to Routes 1, 301, and 896. The remaining balance of the builder's warranty are transferable to the new owner making this home a smart choice in today’s market. Landscape and exterior care are handled by the HOA.
#DENC2098814

MIDDLETOWN

1428 WHISPERING WOODS ROAD

2 Beds

2 Baths

1,275 Sq.Ft.

$423,000

MLS#: DENC2098814

BASE PRICE LISTING - MODEL HOME IS NOT FOR SALE. Welcome to a stylish and spacious 3-story townhome that offers 1 or 2 garages, square footage ranging from 2,001-2,333 & contemporary living at its finest. With 3 bedrooms, 2.5 baths, and a finished den on the first level with rough in plumbing for a future bathroom, this home is designed to provide both comfort and versatility. As you step inside, you're greeted by a modern floor plan that seamlessly connects the living, dining, and kitchen areas. The first level features a beautifully finished den, perfect for use as a home office, entertainment room, or guest space. Sliding glass doors lead to a private outdoor area where you can enjoy your private space and create a tranquil retreat. The builder is currently offering this optional finished space as part of their incentive. The second floor is the heart of the home, boasting a spacious great room flooded with natural light. It's an ideal space for relaxation, with enough room to accommodate your favorite furniture and decor. The nearby dining area is perfect for hosting meals and gatherings, and it flows effortlessly into the well-appointed kitchen. The kitchen features modern appliances & ample cabinet space. Whether you're preparing a quick weekday dinner or hosting a special occasion, this kitchen has everything you need. On the third level, you'll discover three generously sized bedrooms, each with its own character and charm. The primary bedroom is a luxurious retreat, complete with an en-suite bathroom featuring double vanities, and a separate shower. The other bedrooms share a well-appointed full bathroom, ensuring convenience for family and guests. These 3-story townhome offer the perfect blend of modern living and functionality. It provides plenty of space for relaxation and entertainment, and the finished den on the first level adds extra versatility to suit your lifestyle. With its contemporary design & ample storage, these townhomes are a welcoming place to call home. Massey Elite Model Home - 3 bedrooms, 2.5 baths, 2 car garage. Approx. 2333+ SF! This home features a laundry list of upgrades! *Price does not reflect all upgrades and designer features shown in model home. Base Price Only. For self-guided tours 7am-8pm daily; Download "NterNow" on your smart phone. Complete registration while standing in front of homes door. Have driver's license handy as the app will ask you to scan. Enter property ID located on front door. Door will automatically unlock. Please secure door when leaving as the door will lock itself within 30 seconds of leaving property.
#DENC2080226

MIDDLETOWN

1300 CARRICK COURT MASSEY ELITE MODEL

3 Beds

2 Baths

2,001 Sq.Ft.

$416,000

MLS#: DENC2080226

Excellent opportunity to own in the desirable 55+ community of Springmill. Well maintained, first floor living with everything you need. 2 spacious bedrooms, 2 full baths, a beautiful kitchen with BRAND NEW stainless steel appliances and dining space, and a spacious 2-car garage. The back porch area is perfect for garden enthusiasts or a nice, relaxing area to entertain guests. This freshly painted home is completely move in ready. Just minutes from the MANY popular shops, restaurants, and golf courses that Middletown has to offer. Come tour this wonderful home today!
#DENC2096092

MIDDLETOWN

304 DAY LILLY WAY

2 Beds

2 Baths

1,500 Sq.Ft.

$410,000

MLS#: DENC2096092

One of a Kind Rare Victorian located in the heart of Middletown that needs TOTAL RENOVATION. This expansive property offers over 3,700 square feet of living space and sits on a generous 0.29 acre lot, combining historic charm with endless potential. Featuring Five (5) Bedrooms and Three (3) Full Baths, this home is filled with character throughout, including hardwood floors, Two Fireplaces, and classic architectural details that make this property truly stand out. Currently set up as a mixed use property that can be used as a residential and an office. Situated on a busy main road, the location offers outstanding visibility and steady traffic flow—ideal for a home-based business or anyone seeking maximum exposure and convenience. Just minutes from shopping, dining, and local amenities, this property blends charm, space, and opportunity in one prime location. This home can easily be converted back into a large single-family residence—creating a stunning showpiece with room to grow. Come in, renovate, and make it your own! Whether you’re looking to restore its original grandeur or design a modern masterpiece, the possibilities here are endless.
#DENC2099260

MIDDLETOWN

102 S BROAD STREET

5 Beds

3 Baths

2,816 Sq.Ft.

$399,999

MLS#: DENC2099260

One-level living in the sought-after Village at Middletown! This move-in-ready home welcomes new owners with an open floor plan designed for comfortable living and easy entertaining. The living room flows seamlessly into the kitchen, creating a bright and inviting main living space. The spacious kitchen features a breakfast bar, ample table space, and access to a large, low-maintenance Trex deck—perfect for cookouts or relaxing outdoors. Main-level laundry adds everyday convenience. The primary suite offers a walk-in closet with generous storage and a private bath with shower. Two additional well-sized bedrooms and a full hall bath complete the main level. The full unfinished basement includes egress for a future bedroom, a rough-in for a full bath, and the potential to nearly double your living space. A two-car garage with additional storage and a concrete driveway provide plenty of off-street parking. Ideally located for commuters, just minutes to I-81 and I-66, with easy access to local shops, schools, and amenities.
#VAFV2039012

MIDDLETOWN

151 COUGILL ROAD

3 Beds

2 Baths

1,378 Sq.Ft.

$399,900

MLS#: VAFV2039012

Vintage charm with modern amenities. This home built in the 1800s is on just about 1 acre. It has 2 bedrooms and 2 full baths and 1 powder room. There is also an extra room in the back that could be a third bedroom . The exposed beams and brickwork are amazing. The kitchen has been updated with a quartz countertop, tile backsplash and a new stainless appliance package. You have to see this in person so add this to your tour today.
#DENC2086978

MIDDLETOWN

467 HYETTS CORNER ROAD

3 Beds

2 Baths

1,900 Sq.Ft.

$399,777

MLS#: DENC2086978

Attention developers... this 8 acres is currently being subdivided into 3 buildable lots. All 3 lots currently have passing perc tests. 1.19 acres, which you can see in the first photo of the cornfield. The other 2 lots are tucked in the woods with a private setting and are 3.29 acres, and 3.63 acres. All dry utilities are available out in the street. Another option for someone looking to build their dream home is to keep the last 2 larger lots (almost 7 acres combined) to build on, then sell the 1.19 acre separately. The remaining acreage kept to build on is right off the private road coming from Oberlin Rd., (see 2nd photo). Beautiful country setting, but close to shopping and restaurants.
#PADA2046770

MIDDLETOWN

675 OBERLIN ROAD

None Beds

None Baths

8.0 acres

$395,000

MLS#: PADA2046770

UNDER CONSTRUCTION. *$10,000 builder incentive; thru 4/30/26* This Pheasant model is a 3 BD, 2.5 BA, 1,895 sq. foot, end unit townhome. With its nine foot ceilings and open foyer, well-lit, spacious and open first floor, this home exudes elegance. Included in this kitchen is an island, granite countertops, stainless steel appliances, recessed lighting, an adjacent pantry and many more features. You will feel right at home in the owner’s suite with its large spaces and lots of natural light. The owner’s bath and walk-in closet are exceptionally spacious. Also on the second floor are a loft, bedrooms two and three, a family bath and the laundry room, which is just steps from all bedrooms and bathrooms. This home features a full lower level, a 10'x12' concrete patio, and a 2 car garage. A side porch affords additional outdoor living space. - Interior photos are of a similar home. - All taxes are estimated as this is new construction and has not been assessed.
#PADA2051536

MIDDLETOWN

134 MAGNOLIA DRIVE

3 Beds

2 Baths

1,895 Sq.Ft.

$392,581

MLS#: PADA2051536

New on site 1 day ago
This meticulously maintained home boasts pride of ownership both inside & out! The exterior features mature landscaping & ornate lighting for an added touch of curb appeal. This lovely home is nestled in the desirable community of Ponds of Odessa, where comfort, style, and convenience come together in this sought after community. This beautiful home features 4 spacious bedrooms and 3.1 baths, thoughtfully designed with a flowing, open-concept floor plan perfect for both everyday living and entertaining. As you enter this property, you’re greeted by neutral paint tones and a warm, inviting atmosphere that seamlessly carries throughout the home. The lower level features a generously sized bedroom, private full bath & convenient slider access to the fenced rear yard. This space offers flexibility for guests, a home office, or multi-generational living. The heart of the home is the expansive kitchen, offering ample cabinetry and counter space to inspire the chef in you. The main living areas provide an effortless flow, leading to a rear deck that overlooks a tranquil setting—an ideal spot for morning coffee or unwinding at the end of the day. Retire for the evening to the primary bedroom complete with spacious closet & tastefully appointed private bath. In addition, you’ll find two additional generously sized bedrooms, additional full bath & convenient upper level laundry that adds to the home’s practical design. Perfectly positioned near local amenities, including nearby parks, this home offers the ideal blend of peaceful surroundings and everyday convenience. A rare opportunity to own a well-appointed home in one of the area’s most desirable communities—schedule your tour today!
#DENC2099874

MIDDLETOWN

1302 CARRICK COURT

4 Beds

3 Baths

2,175 Sq.Ft.

$389,900

MLS#: DENC2099874

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Buyers resources
7 Reasons to Work with a Realtor
7 Principles For Home Buying Success
Getting a Mortgage To Buy a Home
Home Hazards Awareness
Key Items For Home Inspection
Questions When Buying a Condo
Questions When Choosing a Realtor
Sellers resources
8 reasons to work with a realtor
Calculating Capital Gains
Checklist for Better Showing
Cleaning Home For Sale
Improving Odds Of an Offer
Preparing Home for photoshoot
Selling Your Home for More $$

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