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

MIDDLETOWN

About MIDDLETOWN

Middletown, MD Real Estate: Your Ultimate Guide

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
106
# of Listings
3
Avg # of Bedrooms
$335
Avg. $ / Sq.Ft.
$553,986
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

106 Properties Found. Page 3 of 8.

Charming Secluded Cabin Retreat This stunning 3 bedroom, 1.5 bath log cabin is the perfect getaway, nestled on a private lot with ample space and amenities. Featuring exposed wood throughout, the home boasts a cozy and rustic ambiance that will make you feel right at home. The main level offers an open-concept living area with a fully equipped kitchen, complete with granite countertops and new appliances. Step outside to the wraparound deck and enjoy the beautiful wooded views, or take a dip in the above-ground pool and relax in the hot tub. Upstairs, the loft area provides additional living space, while the main floor bedrooms offer comfortable sleeping quarters. An attached one-car garage and a separate two-car detached garage provide ample storage and parking. Ideal for short-term rentals, this cabin is currently a successful vacation property and can be sold fully furnished, making it a turnkey investment opportunity. Gather around the fire pit in the evenings, or explore the nearby hiking trails - this private oasis has it all. Don't miss your chance to own this one-of-a-kind retreat! Schedule a showing today.
#PADA2040594

MIDDLETOWN

1250 HIGHSPIRE ROAD

3 Beds

1 Baths

2,691 Sq.Ft.

$583,700

MLS#: PADA2040594

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

3,137 Sq.Ft.

$574,900

MLS#: MDFR2073664

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

3,229 Sq.Ft.

$564,900

MLS#: MDFR2071176

Welcome to the beautifully crafted Lexington model—brand new and READY NOW in the desirable Greenwood Hills community! This energy-efficient home offers nearly 2,000 sq. ft. of thoughtfully designed living space, with 4 spacious bedrooms and 3 full bathrooms, including a main-level bedroom and full bath w/ walk-in shower, perfect for guests, multi-generational living, or a home office. The kitchen features 36” painted cabinets w/ crown molding, elegant quartz countertops, floating shelves, stainless steel appliances with gas cooking, and a walk-in pantry with solid shelving. The kitchen flows seamlessly into the dining area and open family room, creating a welcoming space for both everyday living and entertaining. Upstairs, the primary suite provides a peaceful retreat, complete with a walk-in closet and private en-suite bath with tile shower. Two additional bedrooms and a hall bath complete the upper level. Additional highlights include a two-car garage, walk-out lower level ready to finish, and a 10 year home warranty for added peace of mind. Enjoy life in Greenwood Hills—a thoughtfully planned neighborhood with sidewalks, community benches, a modern park, and a scenic pond with an observation deck. Conveniently located with easy access to Route 283 and the PA Turnpike.
#PADA2045388

MIDDLETOWN

160 HARTFORD DRIVE

4 Beds

3 Baths

3,114 Sq.Ft.

$509,900

MLS#: PADA2045388

Enjoy single-floor living in this inspired ranch home! At the front of the home, you'll find two bedrooms flanking a full bath. Toward the back, there's a well-appointed kitchen nestled between an elegant dining room and generous great room. The laundry is located near the primary bedroom, which has a large walk-in closet and a private bath. You'll love the professionally curated finishes! Situated on a corner lot and backing to open common area.
#VAFV2035268

MIDDLETOWN

100 MIDSUMMER LANE

3 Beds

2 Baths

1,610 Sq.Ft.

$484,999

MLS#: VAFV2035268

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

Discover this exceptional Citrine home. Included features: a charming, covered entry, a large great room with an electric fireplace, an open dining area, an inviting kitchen offering a roomy pantry and a center island, a stunning primary suite showcasing a spacious walk-in closet and a private bath, a convenient laundry, an unfinished basement, a deck landing and a 2-car garage. This could be your dream home!
#VAFV2033310

MIDDLETOWN

106 MIDSUMMER LANE

3 Beds

2 Baths

1,980 Sq.Ft.

$479,999

MLS#: VAFV2033310

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

New on site 3 days ago
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.

$465,000

MLS#: VAFV2038238

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

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 and 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 office or den. 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

2,628 Sq.Ft.

$459,000

MLS#: MDFR2070724

Fully Renovated Rancher!! Beautiful Country Setting! Come check out this Incredibly SPACIOUS Home on just over an Acre. Over 2600+ finished sq feet, 3 bedrooms & 2 full baths. Extra bonus rooms could be bedrooms as well or however you choose. ALL BRAND NEW Flooring, Painting, Lighting, 3 Mini Splits, Architectural Roof, Septic System, Well pressure tank, Windows, and Kitchen! HVAC in Great Shape! Light and Bright and Ready for Move in!=
#VAFV2037978

MIDDLETOWN

6731 MIDDLE ROAD

3 Beds

2 Baths

2,630 Sq.Ft.

$450,000

MLS#: VAFV2037978

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

$449,900

MLS#: MDFR2071442

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

3,092 Sq.Ft.

$449,000

MLS#: VAFV2037906

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

2,726 Sq.Ft.

$446,000

MLS#: VAFV2038186

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