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 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 Group
232
# of Listings
3
Avg # of Bedrooms
$273
Avg. $ / Sq.Ft.
$647,221
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

232 Properties Found. Page 12 of 16.

None
#DENC2094038

MIDDLETOWN

40 S CUMMINGS DRIVE

3 Beds

2 Baths

2,200 Sq.Ft.

$429,500

MLS#: DENC2094038

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 153 Crystal Run Dr! This ranch home is located on an amazing one acre lot in a cul de sac as well as being in the Appoquinimink School District! One floor living is made easy with a floor plan that flows from one room to another. The kitchen is the center of the home and offers ample cabinet space and storage. There are two living areas that have vaulted ceilings and great natural lighting. A sunroom is also ideal for the warmer months. Three large bedrooms and two full bathrooms complete the first floor. The basement spans the entire home and can be finished for additional living space and recreation. Outside, the large deck showcases the private yard. This home is centrally located close to 896, 301 and more. Schedule your tour today!
#DENC2094658

MIDDLETOWN

153 CRYSTAL RUN DRIVE

4 Beds

2 Baths

1,975 Sq.Ft.

$425,000

MLS#: DENC2094658

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

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

3 Beds

2 Baths

1,378 Sq.Ft.

$425,000

MLS#: VAFV2039012

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

New on site 3 days ago
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 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. 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.

$420,000

MLS#: DENC2096092

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

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.

$399,998

MLS#: DENC2086978

Nestled in the charming Middletown community, this delightful split foyer home offers a perfect blend of comfort and convenience. Located on a corner lot, there is ample space for guest parking and outdoor activities. The exterior of the home has been updated with beautiful new siding, gutters and downspouts in 2019. The well-maintained interior boasts 1,396 sq. ft. of living space, featuring three cozy bedrooms and a full bath. This home includes a spacious basement that contains 2 additional rooms for your convenience, a half bath and private office space. Enjoy evenings by the fireplace or host gatherings on the inviting patio overlooking a spacious 0.4-acre lot, complete with a personal above-ground pool and a play area for outdoor fun. The neighborhood is known for its friendly atmosphere and proximity to local parks, providing many opportunities for recreation and relaxation. With easy access to essential amenities and a welcoming spirit, this home is not just a place to live, but a place to thrive. Experience the warmth of Middletown and make this lovely residence your own!
#MDFR2073592

MIDDLETOWN

7129 LIMESTONE LANE

4 Beds

1 Baths

1,396 Sq.Ft.

$399,900

MLS#: MDFR2073592

Welcome to 827 Lissicasey Loop, a beautifully maintained home that offers the feel of new construction without the additional costs or waiting on a building timeline. Located in one of Middletown’s sought-after communities, this move-in-ready property allows you to enjoy modern finishes and thoughtful upgrades from day one. Inside, you'll find a welcoming entryway that leads to a newly renovated bonus room with fresh paint and LVP flooring, perfect for an office, playroom, or additional entertaining space. On the second floor, you’ll find hardwood floors, granite countertops, and upgraded cabinetry with soft-close drawers that create a refined yet comfortable living environment. The open layout is ideal for both everyday living and entertaining, with natural light flowing throughout the space. On the third level, the primary suite is a true retreat, featuring a walk-in closet and ensuite bathroom with a double sink vanity, offering both style and functionality. Located in one of the neighborhood's best lots, you'll enjoy nature views and watching sunsets every evening from your western facing windows. Conveniently located near Route 1, US-301, Route 13, shopping, dining, and Bayberry Town Center amenities, this home provides easy access to essentials while still offering a peaceful neighborhood feel. Every detail has been carefully selected and gently lived in, making this home feel fresh, current, and ready for its next owner. Schedule your tour today to fall in love with your next home!
#DENC2095946

MIDDLETOWN

827 LISSICASEY LOOP

3 Beds

2 Baths

2,100 Sq.Ft.

$399,900

MLS#: DENC2095946

Investor Alert! High Cash Flow + Strong ROI - Welcome to 219 South Union Street in Middletown - a fully improved mixed-use, multi-unit property offering impressive income and strong long-term upside! Featuring 1 commercial unit and 3 residential apartments, all separately metered and recently updated, this is a turn-key investment opportunity in a desirable downtown location. Income Breakdown: Commercial Unit: $1,195/mo, 1BR/1BA Apartment: $1,070/mo (currently leased month to month - higher market rent potential), (2) 2BR/1BA Apartments: $1,495/mo each. - Total Monthly Gross Rent: $5,255 Annual Gross Income: $63,060 WOW!! CAP Rate of 11.56%, and Cash on Cash Return of 19.91%, 5-Year Investment Rate of Return (5% Appreciation) - 31.72%!! MASSIVE Depreciation Benefit!! This property combines commercial stability with residential demand and future appreciation off the charts. Tenants pay their own electric, minimizing owner expenses. The building features high ceilings, exposed brick, ornate details, and private rear balconies for each apartment. Don’t miss this rare, high-yield investment opportunity in thriving downtown Middletown!
#PADA2049614

MIDDLETOWN

219 S UNION STREET

None Beds

None Baths

3,186 Sq.Ft.

$399,000

MLS#: PADA2049614

Investor Alert! High Cash Flow + Strong ROI - Welcome to 219 South Union Street in Middletown - a fully improved mixed-use, multi-unit property offering impressive income and strong long-term upside! Featuring 1 commercial unit and 3 residential apartments, all separately metered and recently updated, this is a turn-key investment opportunity in a desirable downtown location. Income Breakdown: Commercial Unit: $1,195/mo, 1BR/1BA Apartment: $1,070/mo (currently leased month to month - higher market rent potential), (2) 2BR/1BA Apartments: $1,495/mo each. - Total Monthly Gross Rent: $5,255 Annual Gross Income: $63,060 WOW!! CAP Rate of 11.56%, and Cash on Cash Return of 19.91%, 5-Year Investment Rate of Return (5% Appreciation) - 31.72%!! MASSIVE Depreciation Benefit!! This property combines commercial stability with residential demand and future appreciation off the charts. Tenants pay their own electric, minimizing owner expenses. The building features high ceilings, exposed brick, ornate details, and private rear balconies for each apartment. Don’t miss this rare, high-yield investment opportunity in thriving downtown Middletown!
#PADA2048820

MIDDLETOWN

219 S UNION STREET

5 Beds

None Baths

3,186 Sq.Ft.

$399,000

MLS#: PADA2048820

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

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