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
226
# of Listings
3
Avg # of Bedrooms
$269
Avg. $ / Sq.Ft.
$660,439
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

226 Properties Found. Page 9 of 16.

TO BE BUILT - The Oxford - Whether you're looking for a detached homes home large enough to raise a growing family, an intelligently designed attached carriage home, or a modern townhome with tons of living space, it's all here at the Reserve at Ponds of Odessa. Our homes feature 2-4 bedrooms with optional first floor owner's bedroom, 2 car garage, 2/2.5 baths, 42" cabinets, wall to wall carpeting, spacious open- concept main level, public sewer and water, underground utilities, blacktop driveway, streetlights, sidewalks and curb lined streets. Located in Appoquinimink School district. This beautiful home features 4 bedrooms, 2.5 full baths, 2 car garage. Standard features include a partially finished basement, Granite kitchen countertops, 42" maple cabinets, stainless steel appliances, hardwood floors in foyer, kitchen & breakfast area & a stone water table on the exterior. Builder Splits Transfer Tax
#DENC2079326

MIDDLETOWN

400 REDERICK LANE 2 OXFORD

4 Beds

2 Baths

2,357 Sq.Ft.

$576,500

MLS#: DENC2079326

TO BE BUILT - The Sassafras II- This beautiful ranch home features 3 bedrooms, 2 full baths, 2 car garage. Standard features include a full unfinished basement, Granite kitchen countertops, 42" maple cabinets, stainless steel appliances, hardwood floors in foyer, kitchen & breakfast area & a stone water table on the exterior. Appoquinimink School district! *Photos shown are of similar home, not listed property. Agent must accompany buyer on first visit or preregister prior to first visit on builder website.
#DENC2079330

MIDDLETOWN

400 REDERICK LANE 4 SASSAFRAS II

3 Beds

2 Baths

2,200 Sq.Ft.

$576,000

MLS#: DENC2079330

Welcome to 321 Jessica Drive, a spacious five bedroom, three and a half bathroom home offering a remarkable blend of generous living space and everyday convenience. Located in the highly sought after Appoquinimink School District, this residence sits on a 0.65 acre lot and provides plenty of room for outdoor enjoyment and personal expression. Inside you will find a thoughtful layout with large rooms that invite comfortable daily living and effortless entertaining. The open and connected living areas create a sense of flow while leaving plenty of room for privacy and separation. The property’s location gives you easy access to Route 1 for beach bound travel and Christiana Mall, as well as convenient connections to I-95 north toward the Philadelphia airport and south toward Baltimore and the Baltimore airport. Route 301 is nearby for travel toward Annapolis. Offered as a short sale, this home represents a rare opportunity to own a substantial residence in one of Middletown’s premier locations with long term potential.
#DENC2094594

MIDDLETOWN

321 JESSICA DRIVE

5 Beds

4 Baths

5,250 Sq.Ft.

$575,000

MLS#: DENC2094594

This charming brick rancher is located at the end of a cul-de-sac in sought after Middletown and sits on a peaceful 1.72 acre level lot. The first floor features an open floor plan complete with hardwood floors throughout, formal living room, formal dining room, family room with brick fireplace, breakfast nook leads to a relaxing Trex deck and patio overlooking the large backyard. 1st floor laundry room leads to a oversized 2 car garage. 3 bedrooms and 2 full baths. The fully finished walkout lower level features another full bathroom and large storage room. Some recent upgrades include 20 SEER heat pump (2023), new septic field (2023), electric fireplace (2024), well pump (2020), Ecobee smart thermostat (2023).
#MDFR2073664

MIDDLETOWN

6527 MORNINGSIDE COURT

3 Beds

3 Baths

2,275 Sq.Ft.

$574,900

MLS#: MDFR2073664

Benchmark Builders at The Town of Whitehall, Chadwick Floor Plan. TO BE BUILT. The hometown is finally getting its come back. It's the first town to be founded in Delaware in over a century, and it's planned for all homes, businesses and community traditions that make real towns real places. Whitehall has it all! Chadwick floor plan feature 4bedrooms, 2.5 baths, 2nd floor laundry, 2 car attached rear entry garage, an open floor plan for entertainment with a huge great room! **Optional Chadwick front porch shown in photo**.Agent must accompany client on first visit or pre-register client on builder website prior to first visit
#DENC2079246

MIDDLETOWN

530 WHEELMEN STREET 5 CHADWICK

4 Beds

2 Baths

2,456 Sq.Ft.

$570,500

MLS#: DENC2079246

This well built, all brick rancher sits on a corner lot and is in excellent condition. It has 4 generous sized bedrooms and 3 full bathrooms (every bedroom has direct access to a full bath) and an in-law suite with 2 separate entrances. Gas fireplace on main level and wood burning fireplace in finished basement. Beautiful hardwood floors in the foyer, hallway, dining room, living room and 3 bedrooms. Huge finished walk-out basement with large storage area. Floors in basement (rec room and basement bedroom) were recently replaced. Circular driveway and 2 car garage with a hot tub!
#MDFR2074538

MIDDLETOWN

215 BROAD STREET

4 Beds

3 Baths

2,580 Sq.Ft.

$570,000

MLS#: MDFR2074538

Welcome to 505 Cherry Bark Road in Four Seasons at Baymont Farms, a premier 55+ active adult community in Middletown, Delaware. This nearly new Eastwood Loft Floorplan, just 2 years young, offers low-maintenance, resort-style living with thoughtful design and modern upgrades throughout. Step inside to an open ranch-style floor plan featuring 2 bedrooms and 2 full baths on the main level—with an additional home office—plus a bonus second level with an additional bedroom, full bath, and a spacious loft living area, ideal for grandkids and guest. The home’s inviting exterior showcases a front porch with stone and shiplap accents. Inside, enjoy luxury vinyl plank flooring, a cozy gas fireplace, and a gourmet kitchen complete with soft-close cabinetry, GE Profile appliances, gas cooking, and a large quartz island and countertops. A sunroom bump-out fills the space with natural light, while the primary suite offers a private retreat with a large walk-in closet, dual vanities, and a spa-like walk-in shower. Additional highlights include a full basement with poured concrete foundation and egress window—partially started as a craft room, with rough-in for a future full bath—plus a sprinkler system for easy lawn care. Life at Four Seasons at Baymont Farms centers around connection and convenience. Residents enjoy a 6,000 sq. ft. clubhouse, resort-style pool with tiki hut, state-of-the-art fitness center, kayak launch, bocce and pickleball courts, and a vibrant calendar of events led by the community lifestyle director. From yoga and Zumba to billiards and social gatherings, there’s always something to enjoy. Located just minutes from downtown Middletown with quick access to Rt. 1, Baymont Farms offers the perfect blend of serenity and accessibility. With landscaping and community upkeep included through the HOA, you’ll have more time to focus on hobbies, friendships, and the lifestyle you deserve. Come see why 505 Cherry Bark Road is more than just a house—it’s the start of your next chapter in resort-style living.
#DENC2089330

MIDDLETOWN

505 CHERRY BARK ROAD

3 Beds

3 Baths

2,650 Sq.Ft.

$565,000

MLS#: DENC2089330

Welcome to this beautifully maintained Dulaney model by ADMAR Custom Homes, located in the sought-after 55+ section of the Foxfield subdivision in picturesque Middletown. Pride of ownership is evident throughout this home, lovingly cared for by its original owner. Step inside to a welcoming ceramic-tiled foyer, offering easy access to the attached two-car garage and a conveniently placed powder room. The kitchen features an abundance of cabinet space and overlooks the living room. Two large corner windows bathe the breakfast nook in natural light, making it a cozy space to start your day. The main level boasts gorgeous hardwood flooring throughout the spacious living room and primary bedroom. A set of sliding glass doors in the living room leads to a private outdoor patio — perfect for relaxing or entertaining guests. You'll also appreciate the main-level washer and dryer, offering convenient single-level living. Upstairs, you'll find two additional bedrooms and a full bath, ideal for guests, hobbies, or a home office. The fully finished basement adds even more living space, featuring wall-to-wall wood flooring, recessed lighting, and a warm, open atmosphere perfect for entertaining, game nights, or even dancing. A large utility room with ceramic tile, utility sink, and dedicated deep freezer outlet adds function, while a roughed-in bathroom is nearly complete — just waiting for your final touch. The walk-out basement stairs lead to a lush green yard. This backyard oasis offers both charm and seclusion — a perfect retreat. Don’t miss your chance to own this exceptional home — homes like this don’t stay on the market for long!
#MDFR2071176

MIDDLETOWN

1 KELLER LANE

3 Beds

2 Baths

3,161 Sq.Ft.

$564,900

MLS#: MDFR2071176

*Move-in ready home! New construction without the typical wait* This beautifully designed 3BR/3BA home is ready for immediate occupancy and offers both comfort and style. Enter into a bright and airy office, perfect for work-from-home or hobby space. Just beyond, a formal dining room sets the stage for holiday gatherings and meals. The heart of the home is truly stunning — the kitchen features quartz countertops, 42" cabinetry, and a refrigerator included, all seamlessly flowing into a casual dining area and a spacious great room with a cozy fireplace. A sunroom with glass doors brings in abundant natural light and leads to a private deck, ideal for indoor-outdoor living. The first-floor primary suite boasts a large walk-in closet and a luxurious en suite bath. Upstairs, guests can enjoy their own space with a comfortable loft, an additional bedroom, and a full bathroom — perfect for media, visitors, or multi-use living. This home also has an unfinished basement, offering endless possibilities for future living space, storage, or your favorite hobbies. Don’t miss your chance to live in one of the area’s most desirable communities — schedule your tour today! About the Community: This vibrant 55+ 𝐚𝐜𝐭𝐢𝐯𝐞 𝐚𝐝𝐮𝐥𝐭 neighborhood is designed for your best life, offering everything you need to stay active, connected, and relaxed. The community will have a 5,400-square-foot clubhouse, pickleball and tennis courts, bocce, a sparkling swimming pool, a state-of-the-art fitness center, and more, there will be no shortage of activities to enjoy. Plus, with lawn care, snow removal, and trash and recycling included, you can spend your time doing what you love instead of worrying about upkeep! *Pictures of the model home - actual options and finishes vary per homesite. Please see New Home Consultant for details. Taxes to be assessed after settlement. If using a Realtor: the agent's client must acknowledge on their first interaction with Lennar that they are being represented by a Realtor, and the Realtor must accompany their client on their first visit. For appointments and open houses, please visit the model home located at 2405 Greyfriar Loop.
#DENC2096310

MIDDLETOWN

3027 IVYHOUSE LANE

3 Beds

3 Baths

2,356 Sq.Ft.

$559,495

MLS#: DENC2096310

The Asheville - with over 2,800 finished sq. ft. - delivers modern design and comfortable living with spaces made for both entertaining and everyday relaxation. The contemporary kitchen is the heart of the home, featuring a large island, walk-in pantry, and designer Looks interior selections that elevate the space. A covered front porch and rear deck invite you to welcome guests or unwind outdoors, while the impressive great room with a vaulted ceiling creates a bright, open atmosphere inside. The luxurious primary suite is a true retreat, highlighted by triple windows and an elegant tray ceiling. The primary bath offers a spa-like experience with dual sinks, a walk-in closet, and the option for a freestanding tub. Downstairs, the finished basement expands your living space with a recreation room, bedroom, and full bath—ideal for guests, hobbies, or flexible living needs. This listing is for a to be built home and photos are of a model home for display purposes only. Please see sales consultant for details.
#DENC2096240

MIDDLETOWN

1930 DIXON WAY

4 Beds

3 Baths

2,833 Sq.Ft.

$554,990

MLS#: DENC2096240

Middleton Reserve -To be built new construction. Photos of similar home shown with optional front porch. Benchmark Builders at The Town of Whitehall. Welcome to your new hometown. At Whitehall, the hometown is finally getting its comeback. It's the first town to be founded in Delaware in over a century, and it's planned for all homes, businesses and community traditions that make real towns real places.
#DENC2079238

MIDDLETOWN

530 WHEELMEN STREET 3 MIDDLETON RESERVE

4 Beds

2 Baths

2,280 Sq.Ft.

$554,000

MLS#: DENC2079238

Welcome to 100 Lombardy Drive, a beautifully maintained all-brick rancher built by Morgan-Keller and lovingly cared for by its original owners. Offering 3 bedrooms and 2 full baths, this home features 1,537 square feet of finished living space above grade plus approximately 905 square feet below grade with a 426 square feet storage room, all situated on a generous .33-acre corner lot in the heart of Middletown—with no HOA. Classic charm meets solid construction with hardwood floors tucked beneath the carpet, custom built-ins, fresh interior paint, and two fireplaces, including one in the main living area and one in the partially finished walk-out basement. You can also enjoy beautiful sunsets from the bay window in the family room, adding a peaceful, everyday moment to the well-loved home. The kitchen has been remodeled and expanded, featuring custom-built cabinetry and a large kitchen and dining area, creating the true heart of the home and a natural gathering space. The partially finished walk-out basement adds valuable flexible living space and includes a recreation room with fireplace, craft area, laundry room, and ample storage, ideal for hobbies, entertaining, or future customization. Major systems have been thoughtfully updated, including a new roof in 2025, HVAC updates (outside unit 2017, inside unit 2012), and a boiler backup heat system with a new expansion tank installed in 2024. The boiler (1991) also provides hot water. Additional improvements include new garage doors (2012), sewer line repair and cleaning completed in 2019, and a new patio and sidewalks installed in 2021. Outdoor living is a standout feature and proudly noted as the seller’s favorite part of the home. Enjoy the covered back porch grilling area, perfect for entertaining, relaxing, and everyday enjoyment. An oversized 533 square foot side-load garage offers excellent functionality, while additional storage is available in the detached shed. Located within walking distance to schools, restaurants, grocery stores, parks, walking trails, and historic Main Street, this home offers the rare combination of timeless craftsmanship, meaningful updates, and a truly walkable small-town lifestyle. Solid, spacious, and full of heart—this is Middletown living at its best!
#MDFR2074850

MIDDLETOWN

100 LOMBARDY DRIVE

3 Beds

2 Baths

2,372 Sq.Ft.

$550,000

MLS#: MDFR2074850

The Alton Model. TO BE BUILT. Cape Cod style home offering 2 bedrooms, 2 baths, open floor plan, loft included. Visit The Town of Whitehall for a home town living experience! *Photo shown is not actual home for sale. This community features an abundance of standard features! Hardie board siding, Andersen 200 series windows on all homes. Please stop in for all details. 530 Wheelmen Street, Middletown, DE 19709. Agent must accompany client on first visit or pre-register client on builder website prior to first visit.
#DENC2079242

MIDDLETOWN

530 WHEELMEN STREET 4 ALTON

3 Beds

3 Baths

1,850 Sq.Ft.

$549,000

MLS#: DENC2079242

The Bristol Model is a thoughtfully designed 3-bedroom home that is TO BE BUILT in the highly sought-after 55+ community of Traditions at Whitehall. This home features an open floor plan with a spacious dining area, kitchen, great room, and perfect for modern living and entertaining. The large Owner’s Suite offers two walk-in closets, an en-suite bath with a double vanity, and a luxurious 5-foot tile shower. A versatile loft on the second floor provides additional space and the option to add another bedroom and bathroom for expanded living. Customize your interior and exterior finishes and make this home yours! As a resident you will enjoy access to amenities that include a clubhouse, fitness facilities, swimming pools, walking trails, and a full calendar of social events to keep you engaged and connected with neighbors.
#DENC2080218

MIDDLETOWN

204 BALDY LANE BRISTOLE

3 Beds

2 Baths

2,441 Sq.Ft.

$548,500

MLS#: DENC2080218

Priced to Sell and Move-in Ready!! Sellers are ready for a new owner to enjoy all the amenities right in your own backyard. Looking for a fantastic place to call home that offers a country feel with a 3/4 acre corner lot, fenced in backyard and a HEATED inground pool? Then Misty Vale Farms is calling your name with this beautifully updated home featuring acacia hardwood floors throughout with tile bathrooms, an upgraded kitchen with stainless steel appliances, butcher block counters, wood burning fireplace, formal dining room and and a sunken family room right off the kitchen that leads to a deck and bridge to your incredible backyard with patio, raised garden beds, perennial flowers and large grasses to complete the landscaping. Warmth and openness make this a perfect home for relaxing, entertaining or game night! Sellers installed a NEW vinyl white privacy fence around the pool area, with grassy patches, a fire pit section and concrete decking with plenty of room to entertain and enjoy the outdoor serenity of your very own inground pool - with NEW HEATER! They also upgraded the second floor with all NEW HARDWOOD floors to match the main level. The main level also features a great bonus room with glass framed french doors - perfect for home office, library, playroom - you decide! Upstairs, the primary suite impresses with vaulted ceilings, stunning tile in the en suite bath, and an 11-ft walk in closet. Two additional upstairs bedrooms, a stylish hall bath, and convenient upstairs laundry complete the second floor. The finished basement adds even more flexibility with a media/playroom and an additional bedroom for guests. But the real showstopper is outside where your summer paradise awaits! Enjoy a sparkling in-ground pool with diving board. And the roof is only 8 years young! All this home needs is you and homes like this don’t come along often—don’t miss your chance to make it yours!
#DENC2093922

MIDDLETOWN

102 NEWBURY COURT

3 Beds

2 Baths

2,292 Sq.Ft.

$545,000

MLS#: DENC2093922

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