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
256
# of Listings
3
Avg # of Bedrooms
$266
Avg. $ / Sq.Ft.
$652,024
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

256 Properties Found. Page 11 of 18.

Welcome to the popular Bloomfield Model in the 55+ community of Traditions at Whitehall. This floor plan has 2-Bedrooms with a standard loft and a generously sized great room open to the kitchen and dining area. You will have plenty of space if you like to entertain. A rear Owner's Suite gives maximum privacy and includes a large walk-in closet and en-suite with a double bowl vanity and 5-foot tile shower. The second floor features a large loft and walk-in closet for additional storage or overnight guests. With many structural options available, another bedroom and another bathroom can easily be added. Customize your interior and exterior finishes and make this house your home! As a resident you will enjoy access to amenities that include a clubhouse, fitness facilities, swimming pools, walking trails, and a full calendar of social events to keep you engaged and connected with neighbors.
#DENC2080216

MIDDLETOWN

120 BURLINA BLVD BLOOMFIELD MODEL

2 Beds

2 Baths

2,053 Sq.Ft.

$527,000

MLS#: DENC2080216

Welcome to the Belville Model in the 55+community of Traditions at Whitehall. TO BE BUILT. This inviting 2-Bedroom home has a welcoming foyer which leads you down the hall towards the main living area! An open kitchen and breakfast area which flows into the large great room and is perfect for entertaining! The owner’s suite in the front features a large walk-in closet and owner’s bath with a double bowl vanity and 5-foot tile shower. The second floor offers a standard loft with the option to add an additional bedroom and/or bathroom. Customize your interior and exterior finishes and make this home yours! As a resident you will enjoy access to amenities that include a clubhouse, fitness facilities, swimming pools, walking trails, and a full calendar of social events to keep you engaged and connected with neighbors.
#DENC2080214

MIDDLETOWN

204 BALDY LANE BELVILLE

2 Beds

2 Baths

2,059 Sq.Ft.

$521,500

MLS#: DENC2080214

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.

$509,900

MLS#: DENC2096586

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

1,966 Sq.Ft.

$509,900

MLS#: PADA2045388

New on site today
Welcome to this beautifully updated 3-bedroom, 1.5-bath home in sought-after Middletown. Thoughtfully renovated throughout, this home features a brand-new kitchen, updated flooring, and refinished hardwoods that blend modern updates with classic charm. Major improvements include new double-hung windows, a new heat pump, new 200-amp electrical service, new gutters, and a roof replaced in 2024—offering peace of mind for years to come. Enjoy a spacious backyard perfect for relaxing, entertaining, or everyday living. Convenient location for commuters but also within walking distance to local schools, shops and other towns amenities. Tucked away into a desirable community, this move-in-ready home is a rare find! PROFESSIONAL PHOTOS COMING SOON!
#MDFR2077570

MIDDLETOWN

10 LINDEN BOULEVARD

None Beds

None Baths

2,104 Sq.Ft.

$509,000

MLS#: MDFR2077570

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

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

1930 DIXON WAY

4 Beds

3 Baths

2,833 Sq.Ft.

$499,990

MLS#: DENC2096240

**Move-in ready** Discover the perfect blend of comfort and sophistication at 2228 Winchelsea Parkway, a 3 bedroom, 2.5 bath Carson floorplan. A gourmet kitchen overlooking the great room with a fireplace creates a warm and inviting centerpiece for both daily living, and entertaining. Boasting sleek pure white quartz countertops, modern pewter maple cabinetry, stainless steel appliances, 3X6 fawn gloss backsplash, and a gas cooktop and wall oven, this kitchen is a chef’s dream! The first floor owners suite provides privacy and convenience, while upstairs, a versatile lost connects two secondary bedrooms with a jack and jill bath, ideal for family or guests. Thoughtful design continues outdoors with a composite deck offering a seamless extension of your living space. Every detail of this home is crafted to enhance both style and function. About Venue at Winchelsea: Future amenities include a 5,400 sq. ft. clubhouse offering a BYOB sports bar, fitness center, multi-purpose room, kitchen, library, billiards, and more. Outdoor amenities include tennis, pickleball, community gardens, a pool, pavilion, dog park, and additional recreational options. *Pictures of a similar home and for representational purposes only. Please see New Home Consultant for details. Taxes to be assessed after settlement. If using a Realtor: the agent's client must acknowledge on their first interaction with Lennar that they are being represented by a Realtor, and the Realtor must accompany their client on their first visit. * For appointments and open houses, please visit the welcome home center located at 2405 Greyfriar Loop.
#DENC2096366

MIDDLETOWN

2228 WINCHELSEA PARKWAY

3 Beds

2 Baths

3,397 Sq.Ft.

$499,900

MLS#: DENC2096366

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

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.

$490,000

MLS#: DENC2096388

New on site 1 day ago
**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.

$484,509

MLS#: DENC2097802

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

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

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.

$475,000

MLS#: DENC2094428

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.

$464,999

MLS#: VAFV2035268

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