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 Charis Realty Group 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
259
# of Listings
3
Avg # of Bedrooms
$274
Avg. $ / Sq.Ft.
$647,646
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

259 Properties Found. Page 12 of 18.

**Move-in ready new construction townhome in idyllic 55+ community** 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. Enter 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 unwinding during the upcoming spring and summer months. 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. Schedule your private tour today!! 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.
#DENC2097802

MIDDLETOWN

2311 WINCHELSEA PARKWAY

3 Beds

2 Baths

2,443 Sq.Ft.

$463,409

MLS#: DENC2097802

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.

$460,000

MLS#: DENC2094428

WOW! Simply Gorgeous! This popular Kipling model offers open floor plan, foyer with 11 FT ceiling, wainscoting and gleaming hardwoods extending from foyer thru living room, dining room and kitchen. Well appointed kitchen has granite counters including island with seating for 3, stainless steel appliances, recessed & upgraded lighting. Dining area has sliders to upgraded & enlarged paver patio, upgraded landscaping with paver edging, wonderful front porch & irrigation system. Primary bedroom has plush carpeting, tray ceiling, walk-in closets and full bath with raised height vanity, walk-in tiled shower and beautiful ceramic tiled floor. 2nd bedroom is close to the entry door and another full bath. Main floor laundry room has tiled floor, cabinets, wash tub and washer & dryer included. Additional 2nd floor 12 X 15 Storage Room and storage in the crawl space.This sensational home is located in the premier 55+ Community of Spring Arbor offering a clubhouse, heated salt water pool, bocci ball courts, picnic area, fitness room, immense gathering room with kitchen facilities, library and game rooms including billiards. Great location close to major roads, walking distance to restaurants and shopping..
#DENC2096388

MIDDLETOWN

148 GAZEBO LANE

3 Beds

2 Baths

1,650 Sq.Ft.

$459,900

MLS#: DENC2096388

Welcome to the 55+ community of Traditions at Whitehall - Ashton Carriage Town Home. This home is an end unit has a first-floor owner's bedroom w/ full ensuite bath and walk-in closets, second floor has the 2nd bedroom, loft and an additional full bath. Standard 2-car garage, and additional finished upgrades can be purchased to your taste and budget. Community offers in ground pool w/lounge areas, clubhouse featuring exercise & billiards room, gathering/lounge space, full kitchen and a large outdoor patio/grilling area! Builder Splits Transfer Tax (***Photos are of a similar home and may contain options & upgrades not included in listing price shown.***)
#DENC2095106

MIDDLETOWN

314 CHAROLAIS STREET ASHTON

2 Beds

2 Baths

1,794 Sq.Ft.

$456,000

MLS#: DENC2095106

Priced to Sell! Move right in to this beautifully maintained 3-bedroom, 2.5-bath carriage home in the highly sought-after Village of Bayberry! Step inside to a bright, open floor plan with 9-foot ceilings and gleaming hardwood floors throughout the entire main level. The layout offers a warm, welcoming flow that’s perfect for both everyday living and entertaining. The kitchen, upgraded to include a natural gas line for gourmet cooking, features stainless steel appliances, 42” cabinets, ceramic tile backsplash and under-cabinet lighting. LED flush-mount lighting and custom Levelor window treatments add a clean, modern touch throughout. Upstairs, all three sizable bedrooms include ceiling fans and generous closet space, and the conveniently located second-floor laundry makes daily living easy. The spacious primary suite offers a walk-in closet and private bath. The finished basement provides incredible flexibility—ideal for a large recreation room, home office, gym, or media space with a 92" TV—and is already prepped for an additional half bath. The thoughtfully designed fenced outdoor living space includes a newer gas grill, paver patio and walkway, a cedar pergola with Edison string lighting, and raised garden beds—all complemented by an underground drainage system. With soft ambient lighting and included patio set, this turnkey retreat offers an inviting atmosphere and perfect vibe for days or evenings. Additional features include a smart garage door opener, storm door, upgraded powder room vanity, and a charming park just out front. Located in the vibrant Bayberry community, residents enjoy access to walking trails, playgrounds, gathering spaces, a clubhouse and lake. Situated in the award-winning Appoquinimink school district, this home offers both comfort and active lifestyle. The nearby, newly built Bayberry Town Center features a Weis grocery store, restaurants, and everyday conveniences, all while providing easy access to major routes and downtown Middletown. Welcome home!
#DENC2099566

MIDDLETOWN

2212 S OKEEFFE LANE

3 Beds

2 Baths

2,584 Sq.Ft.

$450,000

MLS#: DENC2099566

New on site 4 days ago
Welcome to 409 Galway Court in the Popular Community of Hyetts Crossing. Conveniently located with quick access to Rt's 1 & 301. This Home is the Spacious Chesterfield Model Carriage House with a Main Level Owners Suite. Designed for Open Concept Living the Main Level has a Great Room with a Break Away Ceiling (2 Story High) with 2 Walls of Windows allowing in ample sunlight. There is a Gourmet Kitchen with Enamel White Cabinets, Large Center Island, Granite Counter Tops, Tile Backsplash, 2 Wall Ovens, B/I Micro Wave Oven & a Side-by-Side Refrigerator. All Appliances are Stainless Steel. There is also a Dining Room just offer the Kitchen. A conveniently located center hall just off the Entry Area leads to the 2nd Floor Turned Staircase, Access Door to the Garage, the Laundry Closet & The Owner's Suite which is spacious with a picture window and a Walk-in Closet. The Full Bath has a Double Sink with ample storage in the Vanity and Glass Enclosed Tile Shower with seat. The Main Level and Upper Level have recently installed LVP Flooring, Neutral Stain. There is also has a Powder Room on this level. The Upper Level has a Loft Area perfect for a Home Office, Exercise Area or TV Room. There are 2 Guess Bedrooms. The Front Bedroom has its own Full Bath and Walk-in Closet. There is also a 3rd Full Bath and a 2nd Bedroom just off the Loft. The Lower Level is a Full Basement with Poured Foundation/Insulated & a Egress Window. Perfect Area for future living space. There is a Deck just off the Kitchen that over looks Fenced rear yard.
#DENC2100606

MIDDLETOWN

409 GALWAY COURT

3 Beds

3 Baths

1,700 Sq.Ft.

$450,000

MLS#: DENC2100606

Brand new to the market and just recorded, complete with well, 4 BR conventional perc, electric at edge of lot, and spectacular view of South Mountain historic area and Middletown Valley. Middletown Middle and High schools and Myersville ES for top education. Farm animals allowed accept for swine. Bring your own builder or listing agent will introduce you to top builders in the area. There is no sign on the property, please call LA to set up showing. This lot and the one next to it are the "cream of the crop" and will be gone before Spring build! Hurry today to inspect.
#MDFR2075328

MIDDLETOWN

9702 MOUNT TABOR - LOT 11 ROAD

None Beds

None Baths

10.26 acres

$450,000

MLS#: MDFR2075328

OPEN HOUSE SUNDAY 4/12 - 12:00-2:00! Welcome to 9233 Baltimore National Pike in Middletown—where country charm meets everyday convenience. This well-maintained 3 bed, 2 full bath home offers over 2,100 finished square feet, including a mostly finished lower level that provides flexible space for a family room, home office, and bonus room. Upstairs, you’ll find a blend of hardwood and luxury vinyl plank flooring, creating a warm and durable living environment. The home is equipped for year-round comfort with a 2016 forced air heat pump, baseboard backup oil heat, and a cozy wood stove—giving you multiple climate control options to suit your needs. Step outside and enjoy the peaceful setting from the screened-in front porch, or entertain in the spacious backyard featuring a patio and storage shed. The oversized 732 sq ft detached garage easily accommodates a vehicle with additional room for storage or a workshop, while the large driveway offers ample parking for guests. RECENT UPDATES: include a 2020 tin roof on both the main house and garage, a 2022 water heater, plus a UV filtration system and water softener for added peace of mind. Appliances have been updated between 2025–2026, making this home move-in ready, budget-friendly to get into Middletown! Located in the desirable Middletown school district, this property offers the best of both worlds—quiet country living with easy access to commuter routes and all the conveniences of nearby town amenities. Don’t miss your opportunity to enjoy space, versatility, and comfort in a beautiful Frederick County setting.
#MDFR2078968

MIDDLETOWN

9233 BALTIMORE NATIONAL PIKE

3 Beds

2 Baths

2,117 Sq.Ft.

$449,000

MLS#: MDFR2078968

Welcome to 398 Goodwick Dr in Middletown, DE — where space, style, and location come together effortlessly. This impressive 3-bedroom, 3.5-bathroom townhome offers over 2,500 square feet of thoughtfully designed living space, ideal for modern living and entertaining alike. Step inside to a warm and inviting interior featuring a blend of hardwood-style flooring, plush carpeting, and recessed lighting, creating a bright and comfortable atmosphere throughout. The heart of the home is the chef-inspired kitchen, complete with stone countertops, stainless steel appliances, a spacious island, and an open-concept layout that flows seamlessly into the dining and living areas—perfect for hosting or everyday life. Upstairs, retreat to the spacious primary suite, featuring a private ensuite bath designed for comfort and relaxation. Additional bedrooms are generously sized, each with access to well-appointed bathrooms, offering flexibility for guests, family, or a home office. This home truly stands out with its attached garage and full basement, providing exceptional storage, parking, and endless potential for additional living space, a home gym, or recreation area. Enjoy low-maintenance living with access to a community pool and shared outdoor spaces, adding a touch of convenience and lifestyle to your everyday routine. Location is everything—and this home delivers. Ideally situated in the heart of Middletown, you’re just minutes from top-rated Appoquinimink schools, popular shopping and dining, parks, and major routes for easy commuting to Wilmington, Newark, and beyond. This vibrant and growing community offers the perfect balance of suburban comfort and everyday convenience.
#DENC2099328

MIDDLETOWN

398 GOODWICK DRIVE

3 Beds

3 Baths

3,201 Sq.Ft.

$445,000

MLS#: DENC2099328

The one many buyers wait for—but rarely find. Welcome to this beautifully maintained 3-bedroom, 2.1-bath home in the desirable Village of Bayberry active adult community, thoughtfully designed for the lifestyle today’s buyers want: main-level living, open entertaining spaces, and comfortable guest accommodations. Step inside and you’ll immediately notice the bright, open layout and gleaming hardwood floors that create a warm and welcoming atmosphere. The heart of the home is the gourmet kitchen, featuring quartz countertops, stainless steel appliances, wall oven, custom cabinetry, pull-out pantry shelving, and designer tile backsplash—perfect for everyday living or entertaining. The first-floor primary suite offers the convenience many buyers are searching for, complete with a walk-in closet with Elfa organizer and private en-suite bath, allowing for true single-floor living. Just beyond the living area, the screened porch overlooking dedicated open space provides a peaceful retreat—ideal for morning coffee or relaxing evenings while enjoying the tranquil setting. Upstairs, you’ll find two additional bedrooms, a full bath, and a versatile loft, providing flexible space for guests, hobbies, or a home office. The full basement with egress window and rough-in for a future bathroom offers exceptional potential for additional living space, recreation, or abundant storage. Situated on a premium lot facing open space, this home offers both privacy and connection to a vibrant community atmosphere. Residents of the Village of Bayberry active adult section enjoy amenities including a clubhouse, pool, walking paths, and community activities. For those considering new construction, this home offers something even better—upgrades already completed, a premium location, and move-in ready convenience without the construction timeline. Opportunities like this—featuring a first-floor primary suite, screened porch, and expansion potential—do not come along often in this community. Schedule your showing today.
#DENC2098640

MIDDLETOWN

2510 CHOPIN DRIVE

3 Beds

2 Baths

1,900 Sq.Ft.

$439,900

MLS#: DENC2098640

A rare townhome in Middletown—where comfort, style, and location come together—at 118 Fletcher Circle, Middletown, DE 19709. Welcome to this modern, move-in-ready end-unit townhome that backs to open space and offers effortless access to Routes 1, 13, and 301, making it an exceptional choice for commuters and those seeking a connected lifestyle. Located within the Appoquinimink School District. This home blends thoughtful design, quality finishes, and a prime location. The exterior showcases timeless stone accents and an inviting covered portico, creating striking curb appeal. An attached garage is complemented by an expanded driveway accommodating up to three additional vehicles—a rare and practical feature. Inside, the entry level welcomes you with a spacious foyer, convenient powder room, and interior garage access. A versatile family room with carpet offers endless possibilities as a media room, home office, or playroom, with sliding doors leading to the backyard and open space beyond. The main living level is bright and inviting, highlighted by 9-foot ceilings, luxury vinyl plank flooring, and neutral modern décor throughout. The open-concept layout seamlessly connects the living room, dining area, and kitchen—perfect for both everyday living and entertaining. Recessed lighting enhances the home’s modern look while offering adjustable settings that allow you to customize the brightness to suit your needs. At the heart of the home, the chef-inspired kitchen features a large center island with seating, granite countertops, stainless steel appliances, and a spacious pantry. Upstairs, the owner’s suite offers a relaxing retreat with a tray ceiling, elegant board-and-batten accent wall, generous walk-in closet, and a luxurious en-suite bath complete with a dual-sink vanity and walk-in tiled shower with bench seating. Two additional sun-filled bedrooms with recessed lighting share a beautifully appointed full bath, while the bedroom-level laundry adds everyday convenience. Combining modern style, low-maintenance living, and an exceptional Middletown location, this home delivers the appeal of new construction without the wait. Conveniently located near shopping, dining and parks, it presents an outstanding opportunity for buyers seeking comfort, style, and long-term value. Schedule your private tour today and discover why this beautifully upgraded home stands out as a premier choice for modern living. All room sizes and square footage are approximate and should be verified by the buyer.
#DENC2098284

MIDDLETOWN

118 FLETCHER CIRCLE

3 Beds

2 Baths

1,975 Sq.Ft.

$435,000

MLS#: DENC2098284

** $10,000 Builder Incentive offered on all homes!; thru 4/30/26. ** UNDER CONSTRUCTION! This Swift model is a 3 BD, 2.5 BA, semi-detached home. Come discover the value that is packed into this 1,980 sq. ft. home. Nine foot first floor walls enhance the spacious feeling of this open floor plan. A self-cleaning electric range, granite counters and soft-close cabinet doors/drawers are featured in this kitchen. The luxury vinyl plank flooring flows throughout the main living area. The first floor study is the perfect space for a home office or den. The owner’s suite is sure to please with large walk-in closet and private bath. Bedrooms 2 and 3 have their own full bath. The laundry room is just steps from all bedrooms and bathrooms. This home also boasts a walk-out lower level, 10×12 composite deck, and a 2 car garage. This home is situated on a perimeter homesite that borders woodland so you will continually be delighted with the wonders of the natural beauty around you. Total taxes are estimated.
#PADA2057886

MIDDLETOWN

251 SAGE BOULEVARD

3 Beds

2 Baths

1,980 Sq.Ft.

$434,976

MLS#: PADA2057886

WOW - What a price! Motivated sellers. Priced well below market value. Built in 2020, this well-maintained 4-bedroom, 2.5-bath home in Middletown, VA offers modern comfort with thoughtful design and room to grow. The main level with open plan flows from entry, to living room, to kitchen, to dining area, and also features a dedicated office with beautiful custom built-ins—perfect for working from home or creating an organized study space. The spacious primary suite on the upper level includes a private full bath and walk-in closet, while two additional bedrooms also feature walk-in closets, providing plenty of storage throughout the home. A convenient walk-in laundry room adds to the home’s functional layout and space. The full unfinished basement offers excellent potential and is already plumbed for a third full bath—ready for your future expansion and storage needs. Outside, enjoy a fully fenced rear yard ideal for pets, play, or outdoor entertaining. A great opportunity for a newer home with space, flexibility, and modern features in a convenient and charming Middletown location. Minutes from I-81 and across from Laurel Ridge Community College.
#VAFV2040048

MIDDLETOWN

471 COVILLE STREET

4 Beds

2 Baths

1,920 Sq.Ft.

$434,900

MLS#: VAFV2040048

** $10,000 Builder Incentive offered on all homes!; thru 4/30/26. ** UNDER CONSTRUCTION! This Swift model is a 3 BD, 2.5 BA, right-side unit, semi-detached home. Come discover the value that is packed into this 1,980 sq. ft. home. Nine foot first floor walls enhance the spacious feeling of this open floor plan. A self-cleaning electric range, granite counters and soft-close cabinet doors/drawers are featured in this kitchen. The first floor study is the perfect space for a home office or den. The owner’s suite is sure to please with large walk-in closet and private bath. Bedrooms 2 and 3 have their own full bath. The laundry room is just steps from all bedrooms and bathrooms. This home also boasts a walk-out lower level, 10×12 composite deck, and a 2 car garage. This home is situated on a perimeter homesite that borders woodland so you will continually be delighted with the wonders of the natural beauty around you. Total taxes are estimated.
#PADA2057890

MIDDLETOWN

253 SAGE BOULEVARD

3 Beds

2 Baths

1,980 Sq.Ft.

$434,267

MLS#: PADA2057890

Motivated seller with a new price!!! Property sold as-is, offering upside potential in a great location. Well suited for cash buyers. 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.

$429,000

MLS#: MDFR2073722

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Buyers resources
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Getting a Mortgage To Buy a Home
Home Hazards Awareness
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Sellers resources
8 reasons to work with a realtor
Calculating Capital Gains
Checklist for Better Showing
Cleaning Home For Sale
Improving Odds Of an Offer
Preparing Home for photoshoot
Selling Your Home for More $$

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