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

296 Properties Found. Page 11 of 20.

Located in the highly sought after community Ponds Of Odessa this pristine end-unit townhouse offers the perfect balance of convenience as well as comfort. Upon entering you are greeted by natural light and a spacious open floor plan complete with a flex room that can double as an office. Upon exploring more of the home you have a vaulted ceiling and open living room and beautiful kitchen complete with upgraded countertops and cabinets. Downstairs you have an unfinished basement with a plethora of options gym, theater, or additional bedrooms and complete with rough plumbing for a future bathroom. Upstairs you'll find the spacious primary suite fully equipped with walk-in closet as well as an en-suite bathroom with dual vanities. The additional bedrooms are very comfortable sized with their own walk-in closets. Outside you'll find a concrete patio perfect for any outdoor activity. This property is located minutes from many amenities, shopping and local businesses. Also just minutes from major highways great for commuting. Schedule your showing today.
#DENC2094428

MIDDLETOWN

1341 CARRICK COURT

3 Beds

2 Baths

2,325 Sq.Ft.

$480,000

MLS#: DENC2094428

20 Acres with River Frontage & Mountain Views 0 River Ridge Road, Middletown, VA Come build your dream home on this stunning 20-acre parcel tucked within a private community. Ideally located just minutes from Front Royal, Winchester, I-66, and I-81, this property offers the perfect balance of peaceful seclusion and easy access to nearby towns and amenities. Enjoy mountain views and direct frontage on the beautiful Shenandoah River — ideal for fishing, kayaking, and embracing nature’s serenity. With gently rolling terrain and potential building sites, the possibilities are endless for creating your full-time residence, weekend escape, or legacy property. Approximately 400 feet of frontage on the North Fork of the Shenandoah River. Don’t miss this rare opportunity to own a private piece of the Shenandoah Valley.
#VAWR2011208

MIDDLETOWN

0 RIVER RIDGE DRIVE

None Beds

None Baths

20.0 acres

$480,000

MLS#: VAWR2011208

Welcome to 365 Andrew Ct! This beautifully maintained, like-new home offers all the advantages of new construction without the wait. Nestled within the highly acclaimed Appoquinimink School District, this stunning end-unit townhome combines luxury with convenience. Featuring an expansive open-concept floor plan, this home is tailored for modern living. With 3 bedrooms, 2 full baths, 2 half baths, and a 2-car garage, there’s ample space for everyday life and entertaining. The chef’s kitchen is a standout with upgraded cabinetry, Quartz countertops, a stylish tile backsplash, and GE stainless steel appliances, seamlessly flowing into the dining area and great room. The lower level, currently used as a bedroom, offers versatile options for your needs. It could easily serve as a home office, gym, playroom, or guest suite. Luxury finishes throughout include LVP flooring on the main level, upgraded tile, and elegant details that enhance the home’s appeal. No need to wait for construction; this home is move-in ready in a community where opportunities like this are truly rare!
#DENC2092040

MIDDLETOWN

365 ANDREW COURT

3 Beds

2 Baths

N/A

$477,000

MLS#: DENC2092040

The main floor of this Coral home offers a large, uninterrupted space for relaxing and entertaining. The kitchen features a spacious center island and opens to the dining and great rooms. Upstairs, you'll find a convenient laundry, a full bath tucked between two generous bedrooms, and an inviting primary suite with a walk-in closet and private bath. This home is built a loft. To round out this home a basement is included and this beautiful home backs to common area.
#VAFV2035270

MIDDLETOWN

102 MIDSUMMER LANE

3 Beds

2 Baths

1,840 Sq.Ft.

$469,999

MLS#: VAFV2035270

Move In Before the New Year! Now is the perfect time to buy your new home at The Venue at Winchelsea, Middletown, DE's premiere active adult community. This move-in ready two-story townhome offers low-maintenance living with sophisticated style and thoughtful design. Step inside to find a dedicated study—perfect for a home office—and a convenient first-floor laundry. The gourmet kitchen shines with modern stainless steel appliances, sleek quartz countertops, 42” cabinetry, a wall oven, and gas cooktop. The open layout flows seamlessly into the dining and living areas, with an included patio to enjoy serene views of Middletown’s farmland. The first-floor owner’s suite is a peaceful retreat with a private bath and spacious walk-in closet. Upstairs, two additional bedrooms, a full bath, and a versatile loft provide comfort and privacy for guests. Best of all, 3104 Pett Level Dr. is just a short walk to the clubhouse, so you’re always close to community activities. Community Highlights: This 55+ Active Adult neighborhood features a 5,400 sq. ft. clubhouse, pickleball, tennis, bocce, swimming pool, fitness center, and more. Lawn care, snow removal, trash, and recycling are all included—leaving you free to enjoy the lifestyle you’ve been waiting for. Pictures are artist renderings for representational purposes only. Please see New Home Consultant for details. Taxes to be assessed after settlement. Realtor representation must be acknowledged on the first interaction with Lennar, and the agent must accompany their client on the first visit. For tours and open houses, visit the model home at 2405 Greyfriar Loop.
#DENC2093758

MIDDLETOWN

3104 PETT LEVEL DRIVE

3 Beds

2 Baths

2,443 Sq.Ft.

$469,509

MLS#: DENC2093758

A Rare Opportunity Awaits! Private Tree-Lined Lot & Rare Basement in Springmill! Discover the perfect blend of comfort, convenience, and community at 102 Springmill Drive, nestled in the sought-after Springmill 55+ resort-style neighborhood. This isn’t just a home — it’s a lifestyle. Set on a premium private lot backing to serene trees, this well-maintained Dunbar model offers easy single-level living with an incredible bonus: one of only 28 homes in the community with a full basement — a truly rare find! The expansive unfinished basement opens the door to endless possibilities: create a home gym, craft room, game room, or additional living space tailored to your dreams. Enjoy peaceful mornings or lively evenings on your back deck with wooded views, or entertain friends in the bright, open layout designed for both comfort and connection. Springmill delivers the vibrant lifestyle you’ve been looking for, with: Sparkling outdoor pool, Tennis and pickleball courts, Clubhouse with countless social activities, Scenic walking paths, Worry-free, low-maintenance living with lawn care, exterior upkeep, and snow removal included, All this just minutes from shopping, dining, and medical services in vibrant Middletown. Homes on premium lots with basements are rarely available — don’t miss your chance! Schedule your private tour today.
#DENC2087760

MIDDLETOWN

102 SPRINGMILL DRIVE

2 Beds

2 Baths

2,100 Sq.Ft.

$467,000

MLS#: DENC2087760

This is a unique one! Beautiful 1+ Acre Corner Lot! Car enthusiast? Perfect for the Garage Hobbyist! 2 oversized 2 Car Garages - attached/rear access garages AND a detached garage too! New roof in 2024! This home has a unique floor plan & a great use of space. This home is eligible for a VA Assumption for a VA Buyer who wants to take advantage of a low interest rate. Schedule today!
#DENC2085744

MIDDLETOWN

301 WHITE PINE DRIVE

3 Beds

3 Baths

2,175 Sq.Ft.

$465,000

MLS#: DENC2085744

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.

$465,000

MLS#: MDFR2073722

25K PREMIUM LOT.....Yes this is the one! Welcome to this charming 3-bedroom home with 3.1 bathrooms in The Preserve at Deep Creek located in Middletown, DE just minutes from plenty of dining, shopping, the 301 highway to connect you to all major roads and a great park across the way with walking trails, fishing, 2 large dog parks, an amazing tot lot, gazebo with bbq grills to host a fun day out and so much more ..... This traditional town home is a corner unit backed to open space..... so not only is it one of the best lots because of its large side yard, open space behind you and additional parking across the street .... I can promise you its the best lawn (my clients pride themselves in their maintenance of it ) to top it off they added a large 16x14 treks deck to enjoy all the views of this lovely property. As you enter this home you will notice the updated and well kept freshly painted home with great living space. As you head back to the heart of this home you are greeted by a spacious living area perfect for relaxation and entertaining. The kitchen is equipped with a very large island, all modern appliances, tons of counter tops, beautiful white cabinets with white quartz and tons of natural light. Heading upstairs you will find three c bedrooms, 2 full bathrooms, upstairs laundry, great closet space. The finished basement is one of my favorites .....what great space, large egress window giving off nice natural light, tons of space to entertain and a full bathroom.....This is the one....Last but not least residents will have access to the community pool, a gym and an area to go play basketball and other activities .... so much to offer - LAWN CARE INCLUDED
#DENC2091008

MIDDLETOWN

527 SWANSEA DRIVE

3 Beds

3 Baths

2,550 Sq.Ft.

$465,000

MLS#: DENC2091008

Enjoy single level living in this ranch plan Three bedrooms and 2 full baths. The Master Suite has a large walk-in closet and a private bath. Laundry is situation near the master suite offering ultimate convenience. Large kitchen island, fireplace, deck off the great room and an unfinished basement with a 3-piece plumbing rough-in for future bathroom. This beautiful home is a must see! Call today to schedule your tour of our Onyx ranch style plan.
#VAFV2034546

MIDDLETOWN

104 MIDSUMMER LANE

3 Beds

2 Baths

1,610 Sq.Ft.

$464,999

MLS#: VAFV2034546

Welcome to your new home in the charming town of Middletown, VA! This spacious 4-bedroom, 2.5-bath single-family home offers the perfect blend of comfort, style, and convenience. Enjoy an open floor plan that’s ideal for both everyday living and entertaining, featuring a large kitchen island and plenty of room to gather. The generously sized bedrooms provide comfort and flexibility, while the large, useable backyard offers an inviting space for outdoor relaxation or play. Conveniently located near major commuter routes—including I-81, Route 11, I-66, Route 7, and Route 50—this home makes commuting simple and efficient. You’ll also be just minutes from Winchester and Stephens City, and close to Shenandoah National Park, the Shenandoah River, local restaurants, and shopping. With its prime location and inviting layout, this Middletown rental offers the best of comfort and convenience in a fantastic setting.
#VAFV2038238

MIDDLETOWN

129 BIRMINGHAM

4 Beds

2 Baths

2,880 Sq.Ft.

$460,000

MLS#: VAFV2038238

Why not add a new home to your Christmas Shopping List?? Schedule your tour and make an offer today!! TV wall mounts are included and installed if Santa Claus brings you a brand-new TV this year. This beautiful, 4-year-old 3 bedroom 2.5-bathroom townhome is located in the Community of Preserve at Deep Creek in Middletown, DE close to shopping, dining and entertainment in the countryside of Middletown, DE. The Preserve at Deep Creek is directly across the street from the Charles Price Memorial Park (Middletown’s dog park) off Levels Road. Featuring: stainless steel appliances, granite countertops, double wall ovens, recessed lighting, tiled backsplash, tankless water heater and whole house humidifier. Luxury vinyl plank flooring is throughout the main floor, carpeting on the 2nd floor, 2nd floor walk-in laundry room and a fully finished basement with recessed lighting that includes a pool table for entertaining. The owner has put some personal touches on the walls such as a kitchen backsplash, neutral paint colors, upgraded ceiling fans and shiplap on walls in rooms and bathrooms creating a warm, cozy environment. The Primary bathroom includes a double shower and double sinks. While outside, enjoy a custom hardscaped patio to a peaceful open space. This property has a spacious 1 car garage with 2 additional parking spots in the driveway. The Community of Preserve at Deep Creek offers an in-ground pool, gym, club house for entertaining and basketball court with low monthly HOA fee. ALL Appliances are included.
#DENC2091972

MIDDLETOWN

1404 FLINTSHIRE DRIVE

3 Beds

2 Baths

2,550 Sq.Ft.

$457,000

MLS#: DENC2091972

New on site 3 days ago
*Move-in ready townhome! Start 2026 off right!* Now is the perfect time to buy your new home at The Venue at Winchelsea, Middletown, DE's premiere active adult community. This move-in ready 3BR, 2.5BA two-story townhome offers low-maintenance living with sophisticated style and thoughtful design. Step inside to find a dedicated study—perfect for a home office—and a convenient first-floor laundry. The gourmet kitchen shines with modern stainless steel appliances, sleek quartz countertops, 42” cabinetry, a wall oven, and gas cooktop. The open layout flows seamlessly into the dining and living areas, with an included patio to enjoy serene views of Middletown’s surroundings. The first-floor owner’s suite is a peaceful retreat with a private bath and spacious walk-in closet. Upstairs, two additional bedrooms, a full bath, and a versatile loft provide comfort and privacy for guests. Best of all, 3104 Pett Level Dr. is just a short walk to the clubhouse, so you’re always close to community activities. Community Highlights: This 55+ Active Adult neighborhood features a 5,400 sq. ft. clubhouse, pickleball, tennis, bocce, swimming pool, fitness center, and more. Lawn care, snow removal, trash, and recycling are all included—leaving you free to enjoy the lifestyle you’ve been waiting for. Pictures are of model home and for representational purposes only. Please see New Home Consultant for details. Taxes to be assessed after settlement. Realtor representation must be acknowledged on the first interaction with Lennar, and the agent must accompany their client on the first visit. For tours and open houses, visit the model home at 2405 Greyfriar Loop.
#DENC2094632

MIDDLETOWN

3110 PETT LEVEL DRIVE

3 Beds

2 Baths

2,443 Sq.Ft.

$457,000

MLS#: DENC2094632

Classic R.C. Peoples-built 2 Story in rarely available Great Oak Farms. This home has fantastic curb appeal starting with the brick siding, but not forgetting the long driveway that is complimented by two decorative brick pillars. Moving inside, there is a living room with a cozy fireplace; just a few steps away from the formal dining room. The kitchen its own dining area, no shortage of cabinet space, and has access to the basement and family room featuring another fireplace! The second story has a full bathroom, and four spacious bedrooms which includes the primary suite that boasts its own full bathroom and plenty of closet space! Additional features include: a mud/laundry area off of the family room with access to the powder room, a total of 4 garage spaces (2 sets of 2 car garages), a brand new septic system, all resting on a large 1 acre lot. While tucked away in the tranquil community, this home is still located just minutes from major routes making your commute an absolute breeze. An excellent home that is ready for your personal touch!
#DENC2072634

MIDDLETOWN

325 GREAT OAK DRIVE

4 Beds

2 Baths

2,150 Sq.Ft.

$455,900

MLS#: DENC2072634

Welcome to your new home in Bayberry! This 55+ retirement community offers lots of activities and amenities to its residents, including clubhouse, gym, and pool! The home was built in 2021 and has been well kept by its owner so you can essentially buy new construction without the wait! As you enter, you'll be greeted by an open living space with room for a seating area and dining table. The bright kitchen includes plentiful white cabinetry, granite counters, island with storage and breakfast counter, and stainless appliances including gas cooktop and double wall ovens. This level also includes the laundry room, powder room, and owner's suite with ensuite bathroom featuring dual sink vanity and walk-in shower. On the second level there's an additional 2 bedrooms and hall bath, plus the landing area that provides versatile space for additional seating, office space, your choice! The home also includes a full unfinished basement for plentiful storage or possibility to make it more usable space. Additional features include recessed lighting throughout, 1-car garage and driveway parking, and screened porch and yard space to enjoy outside! This is the place to see if you're looking for no frills retirement community living at its finest! Schedule a showing today and make it your new home!
#DENC2080318

MIDDLETOWN

5924 RAVEL LANE

3 Beds

2 Baths

2,175 Sq.Ft.

$450,000

MLS#: DENC2080318

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