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
107
# of Listings
3
Avg # of Bedrooms
$329
Avg. $ / Sq.Ft.
$549,729
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

124 Properties Found. Page 8 of 9.

Welcome to the Ponds at Bayberry, a 55+ community in Middletown Delaware. Offering a 3-year young Kelly Americana with 3 beds and 2 baths, this home has an open floor plan which features LVP throughout the main living areas, 9’ ceilings, a great room with a high-efficiency gas fireplace, dining area and a designer kitchen that boasts 42" cabinets, quartz countertops, combo in-wall microwave and oven, gas cooktop, stainless steel appliances, and large island. The primary suite offers an en suite bath and 2 walk-in closets. The 2-bedroom guest suite offers privacy from the main area of the home. Head out to the screened-in rear porch with a spacious backyard ready for designing additional entertainment space. The basement is the full footprint of the home offering plenty of possibilities for its use. The Ponds at Bayberry is resort-style living in a country-like setting. Located in the thriving Bayberry Community, natural parks and miles of walking and biking trails lay before you, with 450 acres of beautifully landscaped open spaces, a 70-acre Central Park with an 11-acre kayaking and fishing lake and two dog parks. The Ponds amenities include numerous clubs and activities, pickleball courts, a beautiful pool, a 10,000 sq. ft. clubhouse w/ fitness center, billiards, ballroom, community lounge, meeting/card rooms and outdoor fire pit that overlooks one of the many private ponds. The Ponds is located minutes from local golf courses, county parks, shops, restaurants and medical facilities. The Bayberry Town Center now offers a newly opened Weiss grocery store and soon to come gas station, walkable shopping and dining options. Close to I-95 and Rt 1, the Wilmington train station, and the Wilmington, Philadelphia and Baltimore Washington International Airports. The Delaware Beaches are only an hour away! HOA fees include clubhouse amenities, trash and snow removal as well as lawn care. This home and community are a must see!
#DENC2085152

MIDDLETOWN

4602 BOGART LANE

3 Beds

2 Baths

1,875 Sq.Ft.

$569,900

MLS#: DENC2085152

Beautifully maintained 5 bedroom 3.5 bathroom home! Huge yard at the end of a cul-de-sac Fully finished basement with Bedroom and full bath Close to parks and playgrounds Large fenced in backyard features a koi pond, gardens, multiple fruit trees, blueberry bushes and honeysuckle New professionally installed fence with warranty HVAC and water heater regularly serviced by professional Plenty of parking with a 2 car garage and 6 car driveway Only 8 years old Don't miss out on this incredible home at this incredible price! Schedule your tour today!! Open house this weekend Saturday and Monday!! Home inspection available via request!
#DENC2094468

MIDDLETOWN

510 CILANTRO COURT

5 Beds

3 Baths

4,275 Sq.Ft.

$569,900

MLS#: DENC2094468

New on site 3 days ago
**Move-in ready** Welcome to the Carson—an elegant and versatile 3-bed, 3.5-bath home spanning 2,389 square feet of above ground living space. The main level features a welcoming foyer that opens into a spacious great room, a bright breakfast nook, and a thoughtfully planned kitchen, creating the perfect hub for gatherings. Homeowners will appreciate the convenience of a first-floor owner’s suite with a walk-in closet, along with a mudroom, powder room, and an attached 2-car garage for everyday functionality. Upstairs, two comfortable secondary bedrooms, a full bath, and a generous loft, offer flexible space for a media room, crafting space, office, or lounge. A partially finished basement with its own full bath makes the perfect hangout spot for you or your guests! This home’s elevated finishes and upgrades add both luxury and practicality—from white kitchen and vanity cabinetry, quartz countertops, and fawn subway tile backsplash to Toasted Taupe LVP flooring, open railing, stained oak stair treads, and included stainless-steel refrigerator and front-load washer and dryer. A composite covered deck and gas fireplace further enhance comfort of your home. To top it off, this community offers a stunning 5,400 square foot clubhouse, pickleball courts, tennis courts, bocce, a swimming pool, fitness center, and so much more! Relax and enjoy the peace of mind that your lawncare, snow removal, and trash/recycle are all taken care of for you. *Pictures of a similar home and for representational purposes only. 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 welcome home center located at 2405 Greyfriar Loop.
#DENC2094634

MIDDLETOWN

3506 PIPEWELL LANE

3 Beds

2 Baths

3,397 Sq.Ft.

$565,825

MLS#: DENC2094634

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 3 bedrooms and 2 full baths on the main level—with one currently used as a home office—plus a bonus second level that includes an additional bedroom, full bath, and a spacious loft living area. 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

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

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

BACK ON THE MARKET! Don't miss your second chance to call this incredible house your home before the holidays. Welcome to this stunning 4-bedroom, 3.5-bath home in High Hook Farms, where location and luxury make for an opportunity you don't want to miss. Beautifully updated and in an ideal location just off of Vance Neck Rd, this home is just minutes from the hustle and bustle of a growing Middletown, while being nestled off quiet back roads for privacy and comfort. The exterior is accented by beautiful stone, and the rear yard is fenced and private, the perfect place to enjoy the custom paver patio. Inside, luxury vinyl plank flooring leads you through the entry to a formal dining room, just before the turned staircase. The family room with natural gas fireplace is expansive and open to the beautifully renovated kitchen. Quartz countertops, sleek gold hardware, upgraded appliances, center island, these are just SOME of the incredible features of this beautiful modern kitchen. Sliding glass doors provide access to the rear yard, providing the perfect flow for indoor outdoor entertaining. Upstairs, second floor laundry adds to the convenience, and a sprawling primary suite with a large walk-in closet and primary bath with double vanity, tile shower, and soaking tub. Three more incredible bedrooms share a full hall bath on the second floor, but the living space doesn't stop there. The finished basement offers additional living space and a full bathroom. Don't miss the chance to call this house your home - it won't last long!
#DENC2094348

MIDDLETOWN

834 WHITEBIRD DRIVE

4 Beds

3 Baths

2,925 Sq.Ft.

$544,900

MLS#: DENC2094348

Middleton Elite -TO BE BUILT new construction. This 3 bedroom open innovative floor plan welcomes homeowners and visitors alike in a space that flows effortlessly from one room to the next. Spacious kitchen with hardwood floors, along with 42" maple cabinets, granite countertops, and so much more. The picture shows this home with the largest optional porch, but there are 3 front elevations to chose from. If you are looking for a community with planned amenities, retail, school and everything else you can imagine, visit the first new urbanism concept community in Delaware, The Town of Whitehall. Agent must accompany client on first visit or pre-register on builder's website prior to first visit.
#DENC2079222

MIDDLETOWN

530 WHEELMEN STREET #2 MIDDLETON ELITE

3 Beds

2 Baths

2,052 Sq.Ft.

$540,000

MLS#: DENC2079222

Welcome to Parks Edge! This exceptional 55+ community in Delaware offers an array of amenities that are truly hard to beat, designed to enhance your active lifestyle. We are pleased to present the Cooper II model, a two-bedroom, two-bath home built by Blenheim Homes. This particular residence features a flexible room that offers the versatility to be easily converted into a third bedroom, an office, or a hobby room, catering to your specific needs. There is also a rough-in for a third bathroom in the basement for the potential need to add another bathroom. The home was constructed with numerous high-quality and energy-efficient features, a detailed list of which can be found in the attached documents for your review. Furthermore, the balance of the 10-year structural warranty is transferable to the new owner(s), providing additional peace of mind. Parks Edge residents enjoy unparalleled access to both the Bayberry South Lakehouse and their own exclusive luxury clubhouse. The clubhouse includes a state-of-the-art fitness center, a refreshing outdoor pool, and various athletic courts for your enjoyment. Beyond these facilities, the community boasts an 11-acre boating and fishing lake and a sprawling 70-acre park, offering ample opportunities for recreation and relaxation. To further enhance your living experience, these features come with the added convenience of included lawn maintenance, snow removal, and irrigated lawns. We invite you to schedule your showing today to experience all that this remarkable home and community have to offer.
#DENC2089864

MIDDLETOWN

3037 BARBER LANE

2 Beds

2 Baths

1,800 Sq.Ft.

$539,000

MLS#: DENC2089864

Welcome to the popular Bloomfield Model in the 55+ community of Traditions at Whitehall. This floor plan has 2-Bedrooms with a standard loft and a generously sized great room open to the kitchen and dining area. You will have plenty of space if you like to entertain. A rear Owner's Suite gives maximum privacy and includes a large walk-in closet and en-suite with a double bowl vanity and 5-foot tile shower. The second floor features a large loft and walk-in closet for additional storage or overnight guests. With many structural options available, another bedroom and another bathroom can easily be added. Customize your interior and exterior finishes and make this house your home! 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.
#DENC2080216

MIDDLETOWN

120 BURLINA BLVD BLOOMFIELD MODEL

2 Beds

2 Baths

2,053 Sq.Ft.

$527,000

MLS#: DENC2080216

Welcome to the Belville Model in the 55+community of Traditions at Whitehall. TO BE BUILT. This inviting 2-Bedroom home has a welcoming foyer which leads you down the hall towards the main living area! An open kitchen and breakfast area which flows into the large great room and is perfect for entertaining! The owner’s suite in the front features a large walk-in closet and owner’s bath with a double bowl vanity and 5-foot tile shower. The second floor offers a standard loft with the option to add an additional bedroom and/or bathroom. 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.
#DENC2080214

MIDDLETOWN

204 BALDY LANE BELVILLE

2 Beds

2 Baths

2,059 Sq.Ft.

$521,500

MLS#: DENC2080214

**Move-in ready** Discover the perfect blend of comfort and sophistication at 3502 Pipewell Lane, a 3 bedroom, 2.5 bath Carson floorplan. A gourmet kitchen overlooking the great room with a fireplace creates a warm and inviting centerpiece for both daily living, and entertaining. Boasting sleek quartz countertops, modern pewter maple cabinetry, stainless steel appliances, and a gas cooktop and wall oven, this kitchen is a chef’s dream! The first floor owners suite provides privacy and convenience, while upstairs, a versatile lost connects two secondary bedrooms with a jack and jill bath, ideal for family or guests. Thoughtful design continues outdoors with a covered porch, offering a seamless extension of your living space, and the corner homesite offers great views and privacy. Every detail of this home is crafted to enhance both style and function. About Venue at Winchelsea: Future amenities include a 5,400 sq. ft. clubhouse offering a BYOB sports bar, fitness center, multi-purpose room, kitchen, library, billiards, and more. Outdoor amenities include tennis, pickleball, community gardens, a pool, pavilion, dog park, and additional recreational options. *Pictures of a similar home and for representational purposes only. 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 welcome home center located at 2405 Greyfriar Loop.
#DENC2092064

MIDDLETOWN

3502 PIPEWELL LANE

3 Beds

2 Baths

3,397 Sq.Ft.

$519,750

MLS#: DENC2092064

Beautifully Updated Home with Inground Pool in Middletown! Welcome to this stunning, fully updated home offering 4 spacious bedrooms with the potential for up to 6 bedrooms, 2 full bathrooms, and 1 half bath — perfect for anyone looking for extra space. Step inside to find a brand-new kitchen featuring quartz countertops, stainless steel appliances, and modern cabinetry, creating the ideal setting for cooking and entertaining. The home boasts fresh updates throughout, including contemporary flooring, stylish fixtures, and much more. Outside, enjoy your own private oasis with a beautiful inground swimming pool, perfect for relaxing or hosting summer gatherings. The backyard offers plenty of space for outdoor living including a trex style deck . With a New roof and paid off solar panels . Located in desirable Middletown, Delaware, this home is close to top-rated schools, shopping, dining, and major routes — combining convenience with comfort.
#DENC2092298

MIDDLETOWN

10 OSPREY LANE

4 Beds

2 Baths

2,075 Sq.Ft.

$513,000

MLS#: DENC2092298

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