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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

261

# of Listings

Avg # of Bedrooms

$272

Avg. $ / Sq.Ft.

$637,643

Med. List Price

Browse MIDDLETOWN Real Estate Listings

$500,000 - $1M

129 Properties Found. Page 8 of 9.

#DENC2098486

MIDDLETOWN

505 CHERRY BARK ROAD

3 Beds

3 Baths

2,650 Sq.Ft.

$565,000

MLS#: DENC2098486

Back on the market at no fault of the sellers - You don't want to miss this beautifully maintained single-family home set on 1.39 acres. Offering 3 bedrooms, 2.5 baths, and 2,175 square feet of finished living space above grade plus a full unfinished basement of equal size this home provides comfort today and flexibility for the future. Inside, the layout is ideal for everyday living and entertaining. Hardwood floors and architectural details create a warm, inviting atmosphere throughout. The eat-in kitchen connects seamlessly to the main living areas, while the sunroom offers a peaceful space to relax year-round. The spacious primary suite features a large ensuite bath with both a walk-in shower and a tub/shower combination, creating a private retreat designed for comfort and convenience. The outdoor space is equally impressive. The in-ground pool is enclosed by a white vinyl picket fence and complemented by hardscape features, making it perfect for summer gatherings or quiet evenings at home. The expansive lot offers privacy, room to play, and endless possibilities. A two-car garage adds everyday convenience. The full unfinished basement, complete with a Bilco door, offers excellent storage and future finishing potential. Built in 1993, this move-in-ready home has been well cared for and is being sold AS IS, providing an excellent opportunity for buyers to personalize the space. Conveniently located near Route 1 for easy commuting and situated in a desirable school district, this property offers a strong combination of space, functionality, and location. Buyers who choose our preferred lender, Ed Rexroth with Lower Mortgage, will receive a minimum of $2,500 in lender credits toward closing costs.

MIDDLETOWN

656 VANCE NECK ROAD

3 Beds

2 Baths

2,175 Sq.Ft.

$565,000

MLS#: DENC2096726

REFRESHED, REVAMPED AND MOVE-IN READY. YOU SPOKE AND WE LISTENED. CHECK IT OUT AGAIN! This beautifully updated Dulaney model by ADMAR Custom Homes is nestled in the highly sought-after 55+ section of Foxfield in picturesque Middletown and has been lovingly maintained by its original owner. Recent updates make this home truly turnkey, including new quartz countertops, new stainless steel appliances, new luxury vinyl plank flooring in the kitchen, updated lighting, and refreshed hardware—allowing you to simply move in and enjoy. A welcoming ceramic-tiled foyer offers convenient access to the attached two-car garage and a perfectly placed powder room. The kitchen features abundant cabinetry and opens seamlessly to the living room, creating a comfortable and connected space for everyday living. Sunlight pours into the breakfast nook through two large corner windows, making it an inviting spot for morning coffee. The main level showcases beautiful hardwood flooring, a spacious primary bedroom, and a bright living room with sliding glass doors leading to a private patio—ideal for relaxing outdoors or entertaining friends. You’ll also appreciate the main-level washer and dryer, providing the ease of single-level living. Upstairs, two additional bedrooms and a full bath offer flexible space for guests, hobbies, or a home office—perfect for today’s active lifestyle. The fully finished walk-out basement expands your living space with wall-to-wall wood flooring, recessed lighting, and a warm, open feel ideal for entertaining, game nights, or gatherings. A large utility room with ceramic tile, utility sink, and deep-freezer outlet adds everyday practicality, while the nearly completed roughed-in bathroom awaits your finishing touch. Step outside to a lush, green backyard that offers both privacy and tranquility—your own peaceful retreat. Enjoy low-maintenance living, thoughtful updates, and a welcoming community designed for active adults. This exceptional home is ready for your next chapter—don’t miss it.

MIDDLETOWN

1 KELLER LANE

3 Beds

2 Baths

3,161 Sq.Ft.

$564,900

MLS#: MDFR2076674

Below market value & PRICED TO SELL!!!!! This meticulously maintained home reflects true pride of ownership, both inside and out. Thoughtfully priced and offering exceptional value, this home is ideally situated in the prestigious community of The Legends in Middletown, enjoying convenient access to shopping, dining, and everyday amenities while offering a peaceful, scenic setting overlooking the golf course. Upon entry, a grand two-story foyer welcomes you with soaring ceilings and an elegant turned staircase, immediately setting a tone of sophistication. The thoughtfully designed, flowing floor plan leads to a stunning two-story family room, highlighted by a gas fireplace that creates a warm and inviting focal point—perfect for cozy evenings or refined entertaining. The spacious kitchen is designed for both function and style, featuring abundant cabinetry and counter space, a center island for added storage, and sliding glass doors that open to the deck—seamlessly blending indoor and outdoor living. The rear fenced yard offers privacy and generous space for entertaining, gardening, or simply unwinding while enjoying tranquil golf course views. Enhancing the home’s functionality, the main level also features a private office, ideal for today’s work-from-home lifestyle, as well as a convenient main-level laundry room with direct access to the garage, adding everyday ease and practicality.
The primary suite serves as a private retreat, complete with a walk-in closet, linen closet, and a beautifully appointed en-suite bath. Three additional generously sized bedrooms and a well-appointed hall bath complete the upper level, offering comfort and flexibility for family, guests, or home office needs. A true highlight of this home is the fully finished basement, providing exceptional bonus space. It features two additional rooms with closets, a full bath, a counter and cabinet area ideal for entertaining, a dedicated theater area, and a large unfinished space for ample storage—perfect for multi-generational living, recreation, or extended guest accommodations. This home is a MUST SEE!!!

MIDDLETOWN

241 PORKY OLIVER DRIVE

4 Beds

2 Baths

2,650 Sq.Ft.

$564,900

MLS#: DENC2093134

*Move-in ready home! New construction without the typical wait* This beautifully designed 3BR/3BA home is ready for immediate occupancy and offers both comfort and style. Enter into a bright and airy office, perfect for work-from-home or hobby space. Just beyond, a formal dining room sets the stage for holiday gatherings and meals. The heart of the home is truly stunning — the kitchen features quartz countertops, 42" cabinetry, and a refrigerator included, all seamlessly flowing into a casual dining area and a spacious great room with a cozy fireplace. A sunroom with glass doors brings in abundant natural light and leads to a private deck, ideal for indoor-outdoor living. The first-floor primary suite boasts a large walk-in closet and a luxurious en suite bath. Upstairs, guests can enjoy their own space with a comfortable loft, an additional bedroom, and a full bathroom — perfect for media, visitors, or multi-use living. This home also has an unfinished basement, offering endless possibilities for future living space, storage, or your favorite hobbies. Don’t miss your chance to live in one of the area’s most desirable communities — schedule your tour today!

About the Community: This vibrant 55+ 𝐚𝐜𝐭𝐢𝐯𝐞 𝐚𝐝𝐮𝐥𝐭 neighborhood is designed for your best life, offering everything you need to stay active, connected, and relaxed. The community will have a 5,400-square-foot clubhouse, pickleball and tennis courts, bocce, a sparkling swimming pool, a state-of-the-art fitness center, and more, there will be no shortage of activities to enjoy. Plus, with lawn care, snow removal, and trash and recycling included, you can spend your time doing what you love instead of worrying about upkeep!

*Pictures of the model home - actual options and finishes vary per homesite. 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.

MIDDLETOWN

3027 IVYHOUSE LANE

3 Beds

3 Baths

2,356 Sq.Ft.

$564,495

MLS#: DENC2096310

#DENC2096390

MIDDLETOWN

1909 GLADYS STREET

4 Beds

2 Baths

2,775 Sq.Ft.

$560,000

MLS#: DENC2096390

New on site 4 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.

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.

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.***

MIDDLETOWN

3225 RYE HARBOUR WAY

2 Beds

2 Baths

1,873 Sq.Ft.

$551,567

MLS#: DENC2098586

New on site 1 day ago

Step back in time and own a remarkable piece of Delaware history with the Dilworth House, believed to be one of the earliest homes built in the state. Set on 12.25 scenic acres backing to the Augustine Wildlife Preserve, this extraordinary property offers a rare blend of historic significance, timeless character, and endless potential.
The Dilworth House is a true architectural treasure, showcasing exceptional early masonry craftsmanship. Distinctive glazed brick “diapering” in diagonal patterns decorates the gable ends, while stepped belt courses and detailed framework further highlight the home’s historic charm. Inside, original character abounds with exposed beams, impressive brick fireplaces, and period details that reflect the home’s early construction, when it was built in two sections and heated by a single chimney.
This three-story residence features 6 bedrooms, 3 full bathrooms, and 2 half bathrooms, with a finished third-floor attic offering additional living space. The partial basement remains unfinished. While updates have been made over time including the plumbing and electrical, much of the home remains in its original condition and will require major restoration,.
Beyond the home, the property is well suited for those interested in farming, mechanical work, or automotive pursuits. Existing improvements include a silo, milk house, dairy barn, cow shed, and storage shed. The barn has been converted into a workshop but could easily be adapted for a variety of uses. The expansive acreage may also offer subdivision potential, adding even more value and opportunity.
This is a rare chance to own an iconic and historically significant property in a breathtaking setting. Schedule your private tour today.

MIDDLETOWN

875 PORT PENN ROAD

6 Beds

3 Baths

2,900 Sq.Ft.

$550,000

MLS#: DENC2099244

New on site 2 days ago

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.

MIDDLETOWN

530 WHEELMEN STREET 4 ALTON

3 Beds

3 Baths

1,850 Sq.Ft.

$549,000

MLS#: DENC2079242

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.

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.

MIDDLETOWN

13 GOLDEN RAINTREE COURT

2 Beds

2 Baths

1,859 Sq.Ft.

$541,400

MLS#: DENC2075684

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MIDDLETOWN

MIDDLETOWN

Why Choose Middletown, MD?

Middletown, MD Housing Market Overview

Live in the Heart of Frederick County

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