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
246
# of Listings
3
Avg # of Bedrooms
$275
Avg. $ / Sq.Ft.
$637,544
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

246 Properties Found. Page 11 of 17.

PRICE IMPROVEMENT! Enjoy breathtaking sunsets and peaceful privacy from this bright and sunny 3-bedroom, 2-bath ranch set on 2.2 acres with state-owned land directly behind the property. This inviting home offers easy one-floor living, a 2-car garage, and an unfinished basement (which also offers a pellet stove) providing excellent storage and future potential. Inside, you'll find hardwood floors and tile throughout the main living areas and an abundance of natural light that fills the home. The living and dining rooms feature soaring cathedral ceilings, creating an open and spacious feel, and lead to sliding glass doors that open to a sun porch and concrete patio, perfect for relaxing or entertaining while enjoying the surrounding landscape and evening sunsets. The primary suite features cathedral ceilings and sliding doors leading directly outside, offering a private retreat with beautiful views of the backyard and the preserved land beyond. Two additional bedrooms and a second full bath complete the main level. The home also includes a convenient laundry area located near the kitchen and a layout designed for comfortable everyday living. While the property needs work, it presents an exceptional opportunity to update and make it your own in a truly special setting. With peaceful surroundings, stunning sunsets, and protected land just beyond the backyard, this property is a rare find for buyers seeking privacy, nature, and potential. Perfect for investors. Home needs work. Property is being sold as-is. No unrepresented Buyers. No offers accepted via text message. Seller will consider all offers.
#DENC2098160

MIDDLETOWN

847 SILVER RUN ROAD

3 Beds

2 Baths

1,375 Sq.Ft.

$475,000

MLS#: DENC2098160

**Move-in ready new construction townhome in idyllic 55+ community** Now is the perfect time to buy your new 3BR/2.5BA 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.
#DENC2099004

MIDDLETOWN

2243 WINCHELSEA PARKWAY

3 Beds

2 Baths

2,443 Sq.Ft.

$474,809

MLS#: DENC2099004

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.

$470,000

MLS#: DENC2094428

*More photos will be added soon* Welcome to this stunning, fully remodeled gem in the heart of Middletown! The house is near the 500 acres of Reserved State land. Thus there is no more place to build a new house in this area and it will never be crowded. If you wish to live in a serine scenic beauty and walk along the beach every afternoon then this house is the best for you. This house is a quick one minute walk away from the great Augustine beach. Also the Augustine Tavern is one minute walking distance from the house. No detail has been overlooked in this top-to-bottom transformation, offering the luxury of new construction with modern, high-end finishes throughout. The open-concept interior boasts all-new flooring, contemporary lighting, and a fresh, neutral palette. The living room is equipped with an electric fireplace is the centerpiece. Kitchen is featuring brand-new stainless steel appliances.. Step outside to your private, fully fenced backyard, providing the perfect space for entertaining, gardening, or pets. Location is everything! This home puts you minutes from the scenic C&D Canal and the natural beauty of the Woodland Beach and Augustine Beach areas. Enjoy easy access to the local ferry, vibrant downtown Middletown shops, and all area attractions. With all-new finishes and an unbeatable location near the water, this move-in-ready home is the perfect retreat. Schedule your tour today—this one won't last!
#DENC2098750

MIDDLETOWN

4 FARM LANE

4 Beds

2 Baths

1,900 Sq.Ft.

$465,000

MLS#: DENC2098750

New on site 1 day ago
Rare Opportunity – Fully Renovated 4-Bedroom Ranch in Middletown Don’t miss this rare opportunity to own a beautifully updated 4-bedroom, 2-bathroom ranch home in a peaceful setting in Middletown, DE, conveniently located just minutes from Route 13 and Route 1. You’ll fall in love with the elegant design and modern upgrades throughout, The modern kitchen is a true highlight, offering white cabinetry, black granite countertops, and high-end stainless steel appliances, along with new doors and windows, new flooring, and fresh paint throughout. Recent improvements include a new roof (2023) and siding, new concrete driveway, new HVAC, fresh paint, new light fixtures and new appliances throughout. The STUNNING fully finished basement adds approximately 1,000 sq. ft. of additional living space, complete with a recreation area and walkout access, providing excellent flexibility for entertainment, storage, or future use. Step outside to your private backyard retreat, featuring a spacious patio and Gazebo —perfect for family BBQs, summer gatherings, or relaxing evenings. This move-in ready home offers exceptional value, modern comfort, and long-term savings. Schedule your showing today!
#DENC2099828

MIDDLETOWN

2 GINA DRIVE

4 Beds

2 Baths

2,175 Sq.Ft.

$465,000

MLS#: DENC2099828

**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

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

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

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.

$449,900

MLS#: VAFV2040048

Welcome to 301 White Pine Dr in charming Middletown, DE! Nestled on an expansive corner lot, this property offers the perfect blend of space, freedom, and potential. With no HOA restrictions, you’re free to let your imagination run wild—whether you envision a lush garden oasis, a backyard entertainment haven, this property has two garages for storage for your hobbies and toys. The home itself is bursting with possibilities to make it truly your own. Located in a desirable area of Middletown, you’ll enjoy the peace of suburban living while staying close to local shops, dining, and top-rated schools. Don’t miss this rare opportunity to create the home you’ve always wanted, with no limitations holding you back! Schedule a showing today and discover all the potential waiting for you at 301 White Pine Dr
#DENC2096792

MIDDLETOWN

301 WHITE PINE DRIVE

4 Beds

3 Baths

2,578 Sq.Ft.

$445,000

MLS#: DENC2096792

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

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

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

New on site 3 days ago
Enjoy easy main-level living in this beautifully designed home featuring 2 bedrooms, 2 bathrooms, and a 2-car garage in the sought-after Springmill 55+ resort-style community. The inviting layout offers a living room with a gas fireplace, plus a sitting room and dining room at the front of the home for added flexibility and charm. The spacious kitchen is well-equipped with a center island, abundant prep space, generous storage, and a sunny breakfast room. The primary bedroom offers plush carpeting for comfort, while the laundry room includes a utility sink and extra storage space for everyday convenience. Upstairs, a versatile flex room provides the perfect space for guests, a home office, or hobbies. Step outside to the rear patio and enjoy the peaceful setting backing to walking paths and trees. Springmill delivers the vibrant lifestyle you’ve been looking for, with a sparkling outdoor pool, tennis and pickleball courts, a clubhouse filled with social activities, scenic walking paths, and low-maintenance living that includes lawn care, exterior upkeep, and snow removal. All of this is just minutes from shopping, dining, and medical services in Middletown.
#DENC2099804

MIDDLETOWN

27 SPRINGMILL DRIVE

2 Beds

2 Baths

2,275 Sq.Ft.

$435,000

MLS#: DENC2099804

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

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