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
251
# of Listings
3
Avg # of Bedrooms
$276
Avg. $ / Sq.Ft.
$641,480
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

123 Properties Found. Page 8 of 9.

Huge price drop and ready to sell!! Welcome to 1909 Gladys Street in the highly sought-after Town of Whitehall! Whitehall is a community that offers fantastic amenities, quality craftsmanship, and a warm welcome. This home's wow factor is abundant, from the curb appeal outside to the model home vibes inside. You will notice the beautiful landscaping and striking deep blue hardi-plank siding as you approach the home. Get ready to decorate the charming front porch for every season! Upon entering the front door, you will be greeted with a large living room to your right and a den to your left, which can be used for various purposes. The foyer, bathrooms, and kitchen have hardwood flooring, which gives the home a warm and welcoming feel. Moving forward, you will pass a hall closet and powder room and enter the main living space with an open floor concept. The kitchen is equipped with a large island, stainless appliances, beautiful 42" white cabinetry, and granite countertops. The family room and dining room are just off the kitchen. This model features a first-floor primary bedroom with double closets and en-suite bathroom, which includes a double sink vanity and a stand-up shower with glass doors. The laundry room is also on the main level, with tile flooring and access to the backyard and the garage. The massive garage can easily accommodate two large vehicles and provide ample storage space (including overhead storage). Upstairs, (iron balusters on the staircase) you will find an extra large loft perfect for various purposes, three spacious bedrooms, and a full bathroom! The unfinished basement is a vast space with an egress window, providing endless customization possibilities. The backyard has a brand-new vinyl fence, and the light fixtures and ceiling fans were just installed throughout the home. 1909 Gladys St. has a tree-lined view in the backyard and is tucked away in the neighborhood for extra privacy. A couple of NEW updates include new carpet in the lower level and fresh paint in several rooms and bathrooms. This home is conveniently located near the recreation center, where you can enjoy various activities such as Zumba, yoga, and self-defense classes. Additionally, the chiropractor, Christiana Care, and Wellness Center are located on-site. Lorewood Grove Elementary is within walking distance, and many shops have just opened and are coming soon! Convenience is just outside your door.
#DENC2096390

MIDDLETOWN

1909 GLADYS STREET

4 Beds

2 Baths

2,775 Sq.Ft.

$560,000

MLS#: DENC2096390

New on site 2 days ago
**FINAL CARSON HOME! Move-in ready!** Introducing Winchelsea's very last Carson! An elegant and versatile 3-bed, 3.5-bath home spanning 2,389 square feet above ground. Designed for modern living, the main level features a welcoming foyer that opens into a spacious great room, a bright breakfast nook, and a thoughtfully planned kitchen, creating the perfect hub for gatherings. Homeowners will appreciate the convenience of a first-floor owner’s suite, along with a mudroom, powder room, and an attached 2-car garage for everyday functionality. Upstairs, two comfortable secondary bedrooms are joined by a full bath and a generous loft, offering flexible space for a media room, crafting space, office, or lounge. A partially finished basement with its own full bath provides endless possibilities for both you and your guests. This home’s elevated finishes and upgrades add both luxury and practicality—from pewter maple kitchen and vanity cabinetry, quartz countertops, and subway tile backsplash to LVP flooring, open railing, stained oak stair treads, and included stainless-steel refrigerator and front-load washer and dryer. A composite covered deck and gas fireplace further enhance comfort and livability. To top it off, this community offers a stunning 5,400 square foot clubhouse, pickleball courts, tennis courts, bocce, a swimming pool, fitness center, and so much more! Relax and enjoy the peace of mind that your lawncare, snow removal, and trash/recycle are all taken care of for you! *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.
#DENC2099006

MIDDLETOWN

2220 WINCHELSEA PARKWAY

3 Beds

2 Baths

3,397 Sq.Ft.

$559,775

MLS#: DENC2099006

Middleton Reserve -To be built new construction. Photos of similar home shown with optional front porch. Benchmark Builders at The Town of Whitehall. Welcome to your new hometown. At Whitehall, the hometown is finally getting its comeback. It's the first town to be founded in Delaware in over a century, and it's planned for all homes, businesses and community traditions that make real towns real places.
#DENC2079238

MIDDLETOWN

530 WHEELMEN STREET 3 MIDDLETON RESERVE

4 Beds

2 Baths

2,280 Sq.Ft.

$554,000

MLS#: DENC2079238

**MOVE-IN READY, SINGLE STORY LIVING!** 2BR, 2BA w/ included sun room home is now available! With a spacious single-level floorplan, it truly stands out in the neighborhood. Featuring two 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 carrara breve 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—don’t wait to claim your place at Venue at Winchelsea. This is your chance to get in before it’s too late. ***Photos for illustrative purposes only. See sales team for final options and colors. 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.***
#DENC2098586

MIDDLETOWN

3225 RYE HARBOUR WAY

2 Beds

2 Baths

1,873 Sq.Ft.

$551,567

MLS#: DENC2098586

New on site today
Welcome Home to 8209 Old Hagerstown a beautifully updated and spacious 5-bedroom, 3-bathroom home located in the highly sought-after Middletown, MD. This move-in ready property features modern upgrades throughout, offering the perfect blend of style, comfort, and functionality. Enjoy generous living spaces, an updated kitchen featuring SS Appliances, white shaker cabinets, quartz counters and MORE! Well-appointed bedrooms ideal for both everyday living and entertaining. Fully finished basement offers so much space for entertaining. Large deck great for relaxation! Private off street parking in driveway and SO MUCH MORE! Situated in a desirable location close to commuter routes and many attractions —this is a home you won’t want to miss!
#MDFR2077940

MIDDLETOWN

8209 OLD HAGERSTOWN ROAD

5 Beds

3 Baths

2,312 Sq.Ft.

$549,900

MLS#: MDFR2077940

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

Rare opportunity in the heart of Middletown! Discover the perfect blend of small-town charm, open space, and future potential on this beautiful 8-acre property surrounded by scenic pastureland and mountain views. Currently used for cattle and hay production, the land is partially fenced and includes a shed, making it ready for agricultural use or the ideal setting for your own private farmette—bring your animals and start living the country lifestyle. Imagine building your dream home while enjoying the peace and wide-open space this property provides. With town water and sewer hookups available, you’ll have the convenience of municipal services while still enjoying the feel of rural living. Zoned RA, the parcel may offer the potential for up to three homesites (buyer to verify)—perfect for a family compound, custom home sites, or a long-term investment opportunity. Located just a short walk to historic Main Street, you can easily enjoy local restaurants, shops, and community events. Plus, I-81 is only minutes away, making commuting simple while you return home each day to your peaceful countryside retreat. Opportunities like this are hard to find in Middletown. Schedule your showing today and explore the possibilities this special property offers. Property sold as-is. Buyer to verify subdivision potential, utilities, and zoning. Property is currently in land use; rollback taxes may apply if removed. Livestock on property—showings by appointment with agent accompaniment only. Q: Where is Middletown, Virginia located? A: Middletown is located in the scenic Shenandoah Valley of Virginia, just south of Winchester and minutes from Interstate 81. Q: What makes Middletown a desirable place to live? A: Middletown offers small-town charm, historic character, and beautiful mountain views while still being close to shopping, dining, and commuter routes. Q: What outdoor activities are nearby? A: Residents enjoy easy access to hiking, fishing, and exploring the Shenandoah Valley, as well as nearby parks, rivers, and scenic mountain drives. Q: Is Middletown convenient for commuters? A: Yes. With quick access to I-81 and nearby Route 11, Middletown provides a convenient commute to Winchester and surrounding Shenandoah Valley communities. Q: What is the lifestyle like in Middletown? A: The town is known for its welcoming community, historic Main Street, seasonal events, and peaceful rural surroundings that make it a great place to enjoy the Shenandoah Valley lifestyle.
#VAFV2039608

MIDDLETOWN

VETERANS - LOT 12 ROAD

None Beds

None Baths

8.0 acres

$549,000

MLS#: VAFV2039608

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

This is a To-Be-Built Home. The Dorchester is a thoughtfully designed one-story floorplan offering 2 bedrooms, 2.5 bathrooms, and a 2-car garage, providing the perfect blend of comfort, convenience, and style. An elegant foyer welcomes guests into the home and sets the tone for the open and inviting layout. Designed for convenient single-story living, the spacious great room and dining area flow seamlessly into the kitchen, creating an ideal space for both everyday living and entertaining. The kitchen features an oversized island and a spacious corner pantry, offering both functionality and storage. A private owner’s suite serves as a relaxing retreat with a large walk-in closet and a spa-inspired bath. Additional highlights include a laundry room with plenty of space to fold and iron, adding extra convenience to daily living. 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.
#DENC2075684

MIDDLETOWN

13 GOLDEN RAINTREE COURT

2 Beds

2 Baths

1,859 Sq.Ft.

$541,400

MLS#: DENC2075684

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

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

This is your opportunity to move into Silver Maple, one of the area’s most desirable 55+ communities, known for its exceptional amenities and active lifestyle. From the moment you enter this 3BR, 2BA, 2-car garage home, you’ll notice the beautiful hardwood floors that flow from the foyer through the main living areas. The open-concept floor plan seamlessly connects the living room, featuring recessed lighting, to the gourmet kitchen with upgraded cabinetry, stainless steel appliances, granite countertops and nice breakfast bar area. The spacious primary suite includes a large walk-in closet and a private bath. Just off the living room, the sunroom addition provides the perfect spot to relax, while the upgraded Trex deck with retractable awning is ideal for enjoying your morning coffee or entertaining outdoors. The full basement with egress window presents endless possibilities for additional living space and includes plumbing hook-ups for future expansion. Additional updates include fresh paint throughout, new roof with 50-year warranty (2026), updated light fixtures, new porch railing, and more. Four Seasons at Silver Maple, built by K. Hovnanian, offers resort-style living with a clubhouse, meeting rooms, outdoor pool, pickleball and bocce courts, horseshoes, fire pit, walking trails, and community garden. Don’t miss the chance to enjoy low-maintenance living in one of Delaware’s premier active adult communities.
#DENC2098642

MIDDLETOWN

137 SILVER MAPLE ROAD

3 Beds

2 Baths

1,625 Sq.Ft.

$519,900

MLS#: DENC2098642

Step into comfort and style in this stunning Florence model located in the highly desirable High Hook Farms community. With its charming stone exterior and inviting front porch, this home offers the perfect blend of curb appeal and modern living. Inside, you’ll find 3 bedrooms and 3.5 bathrooms with a bright, open layout designed for both everyday living and entertaining. Beautiful hardwood floors flow from the foyer through the main level, leading to a spacious living area, an eat-in kitchen with a large island, and a generous family room complete with surround sound speakers and a ceiling fan. If you’ve been considering new construction, this home delivers many of the upgrades builders typically charge extra for: granite countertops, a fully finished basement with a full bath, and a versatile upper-level loft already in place. Step outside to enjoy the maintenance-free deck overlooking a beautifully manicured lawn, creating the perfect space for relaxing or hosting guests. This move-in ready home offers the modern features you want without the wait of building — all in one of the area’s most sought-after neighborhoods.
#DENC2098228

MIDDLETOWN

338 TIGER LILY DRIVE

3 Beds

3 Baths

2,800 Sq.Ft.

$509,900

MLS#: DENC2098228

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

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