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
108
# of Listings
3
Avg # of Bedrooms
$329
Avg. $ / Sq.Ft.
$549,088
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

77 Properties Found. Page 2 of 6.

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

*** Seller Offering 4.875% FHA Financing For Those Who Quality *** Beautifully renovated oversized farmhouse in the heart of Middletown Valley. Blending timeless character with modern updates, this 3-bedroom, 2-full bath home is move-in ready & full of charm. Step inside to find spacious living areas filled with natural light, a thoughtfully updated kitchen with quality finishes and two full bathrooms that have been tastefully remodeled. Original farmhouse details are complemented by contemporary upgrades, creating the perfect balance of old and new. Enjoy the peaceful setting from the covered porch or entertain in the generous yard surrounded by scenic views as well as the 2 story mancave with workshop below and a living space above that can be updated to make a private studio or office. With its ideal location close to Middletown’s shops, restaurants and commuter routes this home offers both convenience and countryside tranquility.
#MDFR2070724

MIDDLETOWN

8109 OLD HAGERSTOWN ROAD

3 Beds

2 Baths

1,752 Sq.Ft.

$458,000

MLS#: MDFR2070724

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

IMMEDIATE AVAILABILITY! Welcome to the 55+ community of Traditions at Whitehall - Annandale Carriage Town Home. This interior first floor owner suite comes w/a 2nd bedroom, loft, 2.5 baths, 2 car rear load attached garage, front porch, and additional finished upgrades. Community offers trails, in ground pool w/lounge areas, open clubhouse featuring exercise room, billiards, gathering space, full kitchen and a large outdoor patio area! Builder Splits Transfer Tax
#DENC2084904

MIDDLETOWN

1104 HIGHLAND STREET 138 ANNANDALE

2 Beds

2 Baths

1,794 Sq.Ft.

$449,500

MLS#: DENC2084904

Welcome home! Spacious craftsman style home in Villages at Middletown. The main level with large kitchen, dining and living room area is open and light-filled, making it perfect for entertaining. Walk out onto the back deck to enjoy the views with your morning coffee (or dine outside, there's plenty of room!)The upper level of this home boasts 5 bedrooms (or potentially use one as an office space), 2.5 baths, and large laundry room. Need more space? The basement is ready for your vision! Finish your way , it already has a rough in for a full bath! Walk out basement leads to beautiful patio space and large fully fenced backyard (corner lot backs to green space and tree line). ***ASK ABOUT THE VA assumable mortgage under 3%***
#VAFV2037906

MIDDLETOWN

100 COVILLE STREET

5 Beds

2 Baths

2,198 Sq.Ft.

$449,000

MLS#: VAFV2037906

New on site 1 day ago
Beautifully renovated oversized farmhouse nestled in the heart of Middletown Valley, where timeless character meets modern comfort. This charming 3-bedroom, 2-full-bath home is truly move-in ready and filled with warmth and natural light. On the main floor you will find a spacious open concept living area with custom fireplace, while the updated kitchen showcases SS appliances/quartz countertops/white shaker cabinets/ a custom tiled backsplash and lots of countertop space for entertaining. On the 2nd floor there are 3 large bedrooms, a laundry room, a large full bath with custom tile work and owners suite with a access to a private rear balcony as well as access to the full walk up attic! Outside you can relax on the covered front porch and take in the peaceful surroundings, or entertain in the generous yard framed by scenic valley views. A standout feature is the two-story “man cave” with a workshop below and an upper-level living space—ideal for conversion into a private studio, home office, or creative retreat. On top of all this there is a brand new roof, new furnace and new AC!
#MDFR2074744

MIDDLETOWN

8109 OLD HAGERSTOWN ROAD

3 Beds

2 Baths

1,752 Sq.Ft.

$449,000

MLS#: MDFR2074744

MASSEY INTERIOR UNIT- 3 bedrooms, 3.5 baths, 1 car garage. Approx. 2232 SF! This home features a Finished den, 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
#DENC2092586

MIDDLETOWN

444 REDERICK LANE MASSEY LOT 69

3 Beds

2 Baths

N/A

$446,291

MLS#: DENC2092586

HAPPY HOLIDAY'S!!! Are you Tired of the City Noise & Traffic, have you been longing for that small town feel, then come checkout this 4 Bedroom 2.5 Bath 4yr old Colonial Home in the Shenandoah Valley. It's Close to I-81 & I-66 and Rt/11. This home Boasts with an Open Concept on the Main Level. The Family room overlooks the Kitchen with a Large Island & Stainless-Steel Appliances & Dining Room; Powder Room & Office complete this level. There's Luxury Vinyl Plank Flooring & Carpet Throughout. Up to the 2nd level that has a Generous size Primary Bedroom with a walk-in Closet & Full Bathroom. There are 3 more Bedrooms, a Full Bath & a separate Laundry Room complete this level. Down to the Basement that has rough in plumbing for another Bathroom. You can Create in this Unfinished space Another Bedroom if needed, Or A Huge Family room. Plenty of room to grow. The Possibilities are Endless. Off the Dining room slip out to the large Private (10'x20') Deck Outback for Entertaining or Relaxing & with stairs to the yard. The home comes with Recessed lighting & 6 Ceiling fans, Attached 2 Car Garage. Home was built by Ryan Homes & sits on a Premium Lot. Short drive to the Blue Ridge Mountains & the Shenandoah River. Shopping & Drive-in Theater nearby. So, if you're starting out, relocating or just need more SPACE Come Checkout this Next Place to Call HOME!
#VAFV2038186

MIDDLETOWN

163 EMMET STREET

4 Beds

2 Baths

1,930 Sq.Ft.

$446,000

MLS#: VAFV2038186

Welcome to 25 Chester Court in Middletown, MD, a stunning end unit townhome. This spacious home offers 2472 square feet of modern living across three floors, featuring 3 bedrooms and 3.5 bathrooms. The main level boasts a contemporary kitchen with white quartz countertops, stainless steel appliances, and a large deck perfect for entertaining. The expansive open walkout basement includes a full bathroom, providing ample space for recreation or an additional living area. The home also features luxury vinyl plank (LVP) flooring on all three floors, and an upstairs laundry room for convenience. The oversized primary bedroom is a true retreat, complete with two walk-in closets and an en-suite bathroom with dual vanities and a large shower. Two additional guest rooms and a full hall bathroom complete the upper level. The property includes a one-car garage and plenty of parking in a quiet community. Enjoy the tranquility of this neighborhood while being close to local attractions, shopping, dining, and outdoor activities. This beautiful home is perfect for those seeking modern amenities and a peaceful living environment. Don't miss the opportunity to make 25 Chester Court your new home.
#MDFR2071442

MIDDLETOWN

25 CHESTER COURT

3 Beds

3 Baths

N/A

$444,900

MLS#: MDFR2071442

MASSEY INTERIOR UNIT- 3 bedrooms, 2.5 baths, 1 car garage. Approx. 2232 SF! This home features a Finished den, 42" cabinets in kitchen, island, stainless steel appliances, gas range, dishwasher, microwave and recessed lighting in Kitchen. LVP flooring upgrades and Breakfast Bar in kitchen. 3 pc rough in walk out basement. Don't miss out on this spectacular floor plan! Builder Splits Transfer Tax
#DENC2092556

MIDDLETOWN

448 REDERICK LANE MASSEY LOT 67

3 Beds

2 Baths

2,232 Sq.Ft.

$439,311

MLS#: DENC2092556

* $5,000 Builder Incentive offered on all homes! Call for details. * NOW UNDER CONSTRUCTION! There are so many things to like about this three bedroom, two bath, raised rancher plan. Enjoy the openness of the main living area as your family and guests gather around the action. The kitchen includes a 5′ island, granite countertops and pantry cabinet. The primary bedroom features a private bath and walk-in closet. Bedrooms 2 and 3 are just steps from the hall bath and laundry. The lower level has a large, unfinished area in addition to the two car garage and a finished flex room. Who doesn’t enjoy relaxing on a front porch or the back patio? Enjoy the view as you watch the changing seasons from this hilltop location. This home will be completed and ready for an early February settlement.
#PADA2051442

MIDDLETOWN

168 MAGNOLIA DRIVE

3 Beds

2 Baths

1,806 Sq.Ft.

$436,825

MLS#: PADA2051442

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