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 Middletown, MD real estate agent to start your search.

Start living the life you’ve always dreamed of in Middletown, Maryland—where homes are more than houses; they’re part of a vibrant, enduring community.

One of the most popular communities provided by Charis Realty Group
243
# of Listings
3
Avg # of Bedrooms
$266
Avg. $ / Sq.Ft.
$640,253
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

243 Properties Found. Page 10 of 17.

New on site today
Welcome to 377 Northampton Drive—a beautifully renovated, move-in-ready home in Willow Grove Mill, perfectly positioned in the heart of Middletown where everyday convenience truly shines. Enjoy being minutes from shopping, grocery stores, restaurants, schools, and major commuter routes—close to everything, yet tucked into an established neighborhood setting. From the moment you step inside, the home makes an impression with a striking entry staircase and thoughtful updates throughout. Hardwood flooring flows through the formal living and dining rooms, creating warm, timeless spaces for entertaining and everyday life. At the center of it all is the newly renovated kitchen, finished with sleek tile flooring, crisp cabinetry, high-end stainless steel appliances, quartz countertops, and a classic subway tile backsplash elevated by complementary gray grout for a clean, modern edge. Just off the kitchen, the family room is a dream with natural gas fireplace, shiplap accent, and built-in floating shelves for added elegance. A dedicated main-level office adds the flexible space today’s lifestyle demands. Upstairs, retreat to a generously sized primary suite featuring two massive closets and a spa-inspired renovated bath—complete with a tiled shower and glass enclosure, a freestanding luxury soaking tub, double vanity, and a private water closet. Three additional large bedrooms share a fully renovated hall bath, and you’ll love the ease of a second-floor laundry room. Downstairs, the finished basement expands your living space with a full bathroom, a large entertaining area, and additional unfinished storage. This house checks every box, with updates in all the right places - a true move-in ready dream waiting for you to call it home!
#DENC2096678

MIDDLETOWN

377 NORTHHAMPTON WAY

4 Beds

3 Baths

3,175 Sq.Ft.

$550,000

MLS#: DENC2096678

New on site today
Welcome to 4311 Zircon, a well-maintained split-level home with a spacious addition, offering 6 bedrooms, 4.5 baths, and 3,072 square feet on a 0.34-acre lot. The home blends original character with thoughtful updates, including a new roof and an beautifully updated kitchen with stainless steel appliances. The addition provides flexibility for a variety of living needs, including guest accommodations, work-from-home options, or extended living arrangements. The backyard offers privacy and a peaceful setting, ideal for enjoying a morning cup of coffee from the main-level bedroom or hosting relaxed dinners in the gazebo. Additional outdoor features include extensive landscaping , deck and porch, creating inviting areas to unwind or gather. Located in a sought-after Middletown community, this property allows you to enjoy the Middletown lifestyle without paying town taxes and No HOA. Conveniently located minutes from I-70, I-270, Route 340, and approximately 15 minutes from downtown Frederick. **Some photos have been virtually staged to help illustrate the home’s potential and possible furniture placement. The property is currently vacant, and all furnishings shown are digital enhancements only.
#MDFR2075506

MIDDLETOWN

4311 ZIRCON ROAD

6 Beds

4 Baths

3,072 Sq.Ft.

$549,900

MLS#: MDFR2075506

The Alton Model. TO BE BUILT. Cape Cod style home offering 2 bedrooms, 2 baths, open floor plan, loft included. Visit The Town of Whitehall for a home town living experience! *Photo shown is not actual home for sale. This community features an abundance of standard features! Hardie board siding, Andersen 200 series windows on all homes. Please stop in for all details. 530 Wheelmen Street, Middletown, DE 19709. Agent must accompany client on first visit or pre-register client on builder website prior to first visit.
#DENC2079242

MIDDLETOWN

530 WHEELMEN STREET 4 ALTON

3 Beds

3 Baths

1,850 Sq.Ft.

$549,000

MLS#: DENC2079242

The Bristol Model is a thoughtfully designed 3-bedroom home that is TO BE BUILT in the highly sought-after 55+ community of Traditions at Whitehall. This home features an open floor plan with a spacious dining area, kitchen, great room, and perfect for modern living and entertaining. The large Owner’s Suite offers two walk-in closets, an en-suite bath with a double vanity, and a luxurious 5-foot tile shower. A versatile loft on the second floor provides additional space and the option to add another bedroom and bathroom for expanded living. 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.
#DENC2080218

MIDDLETOWN

204 BALDY LANE BRISTOLE

3 Beds

2 Baths

2,441 Sq.Ft.

$548,500

MLS#: DENC2080218

Priced to Sell and Move-in Ready!! Sellers are ready for a new owner to enjoy all the amenities right in your own backyard. Looking for a fantastic place to call home that offers a country feel with a 3/4 acre corner lot, fenced in backyard and a HEATED inground pool? Then Misty Vale Farms is calling your name with this beautifully updated home featuring acacia hardwood floors throughout with tile bathrooms, an upgraded kitchen with stainless steel appliances, butcher block counters, wood burning fireplace, formal dining room and and a sunken family room right off the kitchen that leads to a deck and bridge to your incredible backyard with patio, raised garden beds, perennial flowers and large grasses to complete the landscaping. Warmth and openness make this a perfect home for relaxing, entertaining or game night! Sellers installed a NEW vinyl white privacy fence around the pool area, with grassy patches, a fire pit section and concrete decking with plenty of room to entertain and enjoy the outdoor serenity of your very own inground pool - with NEW HEATER! They also upgraded the second floor with all NEW HARDWOOD floors to match the main level. The main level also features a great bonus room with glass framed french doors - perfect for home office, library, playroom - you decide! Upstairs, the primary suite impresses with vaulted ceilings, stunning tile in the en suite bath, and an 11-ft walk in closet. Two additional upstairs bedrooms, a stylish hall bath, and convenient upstairs laundry complete the second floor. The finished basement adds even more flexibility with a media/playroom and an additional bedroom for guests. But the real showstopper is outside where your summer paradise awaits! Enjoy a sparkling in-ground pool with diving board. And the roof is only 8 years young! All this home needs is you and homes like this don’t come along often—don’t miss your chance to make it yours!
#DENC2093922

MIDDLETOWN

102 NEWBURY COURT

3 Beds

2 Baths

2,292 Sq.Ft.

$545,000

MLS#: DENC2093922

Middleton Elite -TO BE BUILT new construction. This 3 bedroom open innovative floor plan welcomes homeowners and visitors alike in a space that flows effortlessly from one room to the next. Spacious kitchen with hardwood floors, along with 42" maple cabinets, granite countertops, and so much more. The picture shows this home with the largest optional porch, but there are 3 front elevations to chose from. If you are looking for a community with planned amenities, retail, school and everything else you can imagine, visit the first new urbanism concept community in Delaware, The Town of Whitehall. Agent must accompany client on first visit or pre-register on builder's website prior to first visit.
#DENC2079222

MIDDLETOWN

530 WHEELMEN STREET 2 MIDDLETON ELITE

3 Beds

2 Baths

2,052 Sq.Ft.

$540,000

MLS#: DENC2079222

This stunning 3BR, 2BA Sonoma home is now available! Move-in ready! With a spacious single-level floorplan, it truly stands out in the neighborhood. Featuring three bedrooms and two bathrooms, the primary suite offers generous closet space with two walk-in closets and an en suite bath. The added sunroom extension extends the home, creating the perfect space for entertaining guests. The kitchen is equipped with stainless steel appliances, sleek quartz countertops, 42’’ cabinetry with hardware, oven, and gas cooktop for all your culinary needs! Plus, the unfinished basement provides ample storage potential. Step outside to enjoy the deck off the sunroom, ideal for relaxing or hosting gatherings. About the Community: This vibrant 55+ active adult community is designed for living your best life. Residents will enjoy a 5,400-square-foot clubhouse, pickleball and tennis courts, bocce, a resort-style pool, a state-of-the-art fitness center, and a full calendar of activities—so there’s always something to look forward to. Best of all, lawn care, snow removal, and trash and recycling are included, giving you the freedom to spend your time exactly how you choose. Homes are selling quickly, and Phase One is almost gone—don’t wait to claim your place at Venue at Winchelsea. This is your chance to get in before it’s too late. *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 model home located at 2405 Greyfriar Loop.
#DENC2095728

MIDDLETOWN

3029 IVYHOUSE LANE

3 Beds

2 Baths

2,065 Sq.Ft.

$538,793

MLS#: DENC2095728

UPDATE!!! PRICE REDUCTION!!! Welcome to Parks Edge! This exceptional 55+ community in Delaware offers an array of amenities that are truly hard to beat, designed to enhance your active lifestyle. We are pleased to present the Cooper II model, a two-bedroom, two-bath home built by Blenheim Homes. This particular residence features a flexible room that offers the versatility to be easily converted into a third bedroom, an office, or a hobby room, catering to your specific needs. There is also a rough-in for a third bathroom in the basement for the potential need to add another bathroom. The home was constructed with numerous high-quality and energy-efficient features, a detailed list of which can be found in the attached documents for your review. Furthermore, the balance of the 10-year structural warranty is transferable to the new owner(s), providing additional peace of mind. Parks Edge residents enjoy unparalleled access to both the Bayberry South Lakehouse and their own exclusive luxury clubhouse. The clubhouse includes a state-of-the-art fitness center, a refreshing outdoor pool, and various athletic courts for your enjoyment. Beyond these facilities, the community boasts an 11-acre boating and fishing lake and a sprawling 70-acre park, offering ample opportunities for recreation and relaxation. To further enhance your living experience, these features come with the added convenience of included lawn maintenance, snow removal, and irrigated lawns. We invite you to schedule your showing today to experience all that this remarkable home and community have to offer.
#DENC2089864

MIDDLETOWN

3037 BARBER LANE

2 Beds

2 Baths

1,800 Sq.Ft.

$528,900

MLS#: DENC2089864

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

BACK ON THE MARKET at no fault of the seller, don't miss your second chance to call 318 Northhampton Way home! This meticulously maintained 4-bedroom, 2.5-bath home offering 2,825 square feet of comfortable living space in one of Middletown’s most sought-after neighborhoods. From the moment you arrive, pride of ownership is evident throughout every detail. The stunning curb appeal draws you in with beautiful exterior, landscaping, and forward facing two-car garage. Step inside to find a bright and open floor plan with spacious living and dining areas that flow seamlessly into a well-appointed kitchen—perfect for both entertaining and everyday living. Large windows throughout the main floor offer beautiful natural light making the space feel bright and crisp. Upstairs, the expansive primary suite provides a relaxing retreat with generous closet space and a private ensuite bath with his and hers vanities, large corner tub, and a separate shower, while three additional bedrooms offer plenty of room for family, guests, or a home office. The second floor laundry room adds an element of convenience you will never want to live without! The finished basement adds valuable bonus space ideal for recreation, a home gym, or media room. Outside, enjoy the fully fenced backyard complete with a beautiful composite deck, creating the perfect spot for outdoor dining and entertaining. Ideally located in Willow Grove Mill, this home offers easy access to local parks, award-winning Appoquinimink schools, shopping, dining, and major roadways. With its thoughtful updates and turn-key condition, this home is ready for you to move right in and enjoy everything Middletown living has to offer. Don't miss your opportunity to call it home!
#DENC2095562

MIDDLETOWN

318 NORTHHAMPTON WAY

4 Beds

2 Baths

2,825 Sq.Ft.

$515,000

MLS#: DENC2095562

**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.

$509,900

MLS#: DENC2096366

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

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

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

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