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
262
# of Listings
3
Avg # of Bedrooms
$271
Avg. $ / Sq.Ft.
$635,705
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

262 Properties Found. Page 11 of 18.

IMMEDIATE AVAILABILITY! Welcome to the 55+ community of Traditions at Whitehall - Ashton Carriage Town Home. This end unit first floor master comes w/a 2nd bedroom & loft, 2.5 baths, 2 car rear load attached garage, front porch, and additional finished upgrades. Community also 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 (***Photos are of a similar home and may contain options & upgrades not included in listing price shown.***)
#DENC2081004

MIDDLETOWN

1102 HIGHLAND STREET 137 ASHTON

2 Beds

2 Baths

1,794 Sq.Ft.

$504,900

MLS#: DENC2081004

This is a To-Be-Built Home. The Eastwood is a beautifully designed one-story floorplan offering 2 bedrooms, 2 bathrooms, and a 2-car garage, thoughtfully created for comfortable and convenient living. An elegant foyer entry welcomes friends and family into the home and leads into a bright, open living space. Generous ceiling heights throughout enhance the sense of openness and allow for an abundance of natural light. The single-story layout centers around a dream kitchen with a spacious island, flowing seamlessly into the great room—perfect for both everyday living and entertaining. An optional fireplace in the great room creates a warm and relaxing atmosphere. The secluded owner’s suite offers a private retreat, complete with an oversized closet and a well-appointed private bath. For a full list of features for this home please contact our sales representatives. Photos are for illustrative purposes only and may not represent the exact home or finishes available. For a full list of features please contact our sales consultants. Welcome to Four Seasons at Baymont Farms, a new active adult 55+ community in Middletown, DE, offering low-maintenance, resort-style living. With spacious home designs and access to countless amenities, come enjoy the best that active living has to offer. Residents can take advantage of the community's 6,000 sq. ft. clubhouse, a pool with tiki hut, a state-of-the-art fitness center, a kayak launch, and multiple bocce and pickleball courts. With a full-time lifestyle director on site, Baymont Farms also features a well-maintained calendar of activities such as Zumba classes, yoga sessions, billiards and more. At Four Seasons at Baymont Farms, the focus is on community. Make friends and enjoy the company of people who have worked hard and now want to enjoy all that a luxury 55+ active adult community has to offer. Just minutes from downtown Middletown, DE with access to Delaware Rt. 1, Baymont Farms offers great convenience while preserving the serenity of its picturesque landscape. At this beautiful active lifestyle community, the relationships that you make and the people you spend time with will create memories that last a lifetime.
#DENC2098894

MIDDLETOWN

15 GOLDEN RAINTREE COURT

2 Beds

2 Baths

1,780 Sq.Ft.

$504,400

MLS#: DENC2098894

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 a little TLC, 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. Property is being sold as-is. No unrepresented Buyers. No offers accepted via text message.
#DENC2098160

MIDDLETOWN

847 SILVER RUN ROAD

3 Beds

2 Baths

1,375 Sq.Ft.

$500,000

MLS#: DENC2098160

The Asheville - with over 2,800 finished sq. ft. - delivers modern design and comfortable living with spaces made for both entertaining and everyday relaxation. The contemporary kitchen is the heart of the home, featuring a large island, walk-in pantry, and designer Looks interior selections that elevate the space. A covered front porch and rear deck invite you to welcome guests or unwind outdoors, while the impressive great room with a vaulted ceiling creates a bright, open atmosphere inside. The luxurious primary suite is a true retreat, highlighted by triple windows and an elegant tray ceiling. The primary bath offers a spa-like experience with dual sinks, a walk-in closet, and the option for a freestanding tub. Downstairs, the finished basement expands your living space with a recreation room, bedroom, and full bath—ideal for guests, hobbies, or flexible living needs. This listing is for a to be built home and photos are of a model home for display purposes only. Please see sales consultant for details.
#DENC2096240

MIDDLETOWN

1511 LESTERFIELD WAY

3 Beds

2 Baths

1,811 Sq.Ft.

$499,990

MLS#: DENC2096240

Price Improvement!!!!!!!Welcome to 248 Ann Drive in the heart of Middletown at the Crossland at the Canal! This beautifully maintained 15 year old 4 bedroom 2.2 bathrooms home offers the perfect blend of comfort, space, and convenience. Step inside to find a bright and inviting layout with generous living areas, ideal for both everyday living and entertaining. The kitchen features ample cabinetry and workspace, flowing seamlessly into the dining area for easy gatherings. Upstairs, you’ll find 4 spacious bedrooms with great natural light, including a primary suite designed for relaxation at the end of a long day. The home also features a finished basement that provides additional living space — perfect for a home office, gym, or recreation area. Basement improvements were completed without permits and are being sold as-is; buyer to perform their own due diligence. Enjoy outdoor living with an unfenced private yard, ideal for summer barbecues and quiet evenings. Conveniently located near shopping, dining and major routes. Don’t miss your opportunity to own a home in one of Middletown’s most desirable communities — schedule your tour today!
#DENC2096586

MIDDLETOWN

248 ANN DRIVE

4 Beds

2 Baths

1,900 Sq.Ft.

$499,900

MLS#: DENC2096586

MASSEY ELITE END UNIT- 3 bedrooms, 2.5 baths, 2 car garage. Approx. 2380 SF! 12x10 Deck. This home features a Finished den, 42" cabinets in kitchen, island, stainless gas range, dishwasher, microwave, LVP flooring and recessed lighting in Kitchen. LVP floor and Tile Shower surround in master bath. 3 pc rough in walk out basement. Don't miss out on this spectacular floor plan! Builder Splits Transfer Tax. Beautifully appointed end unit townhome featuring 3 bedrooms, 2.5 baths, and approximately 2,333 square feet of living space. This home includes a 2-car garage and a 12x16 deck overlooking open farmland. Interior features include upgraded luxury vinyl plank flooring throughout the main level, a gourmet kitchen with granite countertops, Level 3 cabinetry, a large center island, and a gas range. The primary suite offers a spacious layout with a walk-in closet and private bath. Located in one of the community’s most desirable settings with no building in front, open space surrounding, and ample parking.
#DENC2092162

MIDDLETOWN

442 REDERICK LANE MASSEY ELITE LOT 70

3 Beds

2 Baths

2,333 Sq.Ft.

$498,053

MLS#: DENC2092162

New on site 2 days ago
Welcome to this charming Cape Cod nestled in a beautiful rural setting and located within the Middletown school district. This well-cared-for three bedroom, two bath home offers the perfect blend of character and modern updates, featuring an upstairs loft/den that provides flexible living space and a partially finished basement for additional room to spread out. A spacious sunroom filled with natural light creates the ideal spot for relaxing or entertaining year-round, while the large fenced-in backyard offers plenty of space for outdoor enjoyment. The homeowners have thoughtfully renovated and improved many aspects of the property, creating a move-in ready experience while preserving its timeless character. Enjoy the added efficiency and comfort of geothermal heating and take in the peaceful surroundings that make this property truly special. Please note, the tax record square footage is believed to be inaccurate and does not reflect approximately 300 additional square feet of finished living space.
#MDFR2078640

MIDDLETOWN

7201 MOUNTAIN CHURCH ROAD

3 Beds

2 Baths

1,970 Sq.Ft.

$494,500

MLS#: MDFR2078640

Rare opportunity to own a private homesite in the desirable River Ridge on the Shenandoah community in Middletown, VA. This undeveloped parcel offers the perfect setting for a custom-built home, weekend retreat, or long-term investment. Enjoy natural surroundings, peaceful privacy, and the flexibility to design and build to your vision (subject to county approvals). Located just minutes from historic Middletown, local dining, wineries, and commuter routes, this property offers a unique balance of seclusion and convenience. Land opportunities in this area are limited, secure your future homesite today. Strategically priced based on current land market trends and buyer activity, this property is being marketed to attract qualified end users and investors alike. Ideal for out-of-state buyers, builders, or those seeking to secure land for future use. Don’t miss the chance to own land with flexibility, upside potential, and location appeal. 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

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.

$479,900

MLS#: DENC2096388

**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.

$479,890

MLS#: DENC2097802

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

New on site 4 days ago
**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

Where original character remains and modern updates prevail. This gem has the potential to be converted back to a single family home by opening up the interior staircase or investors are sure to appreciate the two separate updated apartments in this turn of the century home with off-street parking. Owner can live in one unit and rent out the other. Each apartment features its own separate entrance, living room, dining room, two bedrooms, full kitchen, laundry room, ample closet and storage space. Enjoy outdoor living with a large back yard. Be in the heart of in-town living with amenities - restaurants, churches, convenience stores, schools, and parks.
#MDFR2078348

MIDDLETOWN

507 MAIN STREET

4 Beds

2 Baths

2,698 Sq.Ft.

$460,000

MLS#: MDFR2078348

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