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
107
# of Listings
3
Avg # of Bedrooms
$329
Avg. $ / Sq.Ft.
$549,729
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

124 Properties Found. Page 5 of 9.

Tucked away on over 5 private acres, this chalet-style retreat feels like living in your own treehouse. Soaring ceilings, expansive windows, and skylights bathe the open interior in natural light, highlighting the warmth of hardwood floors and a striking fireplace centerpiece. The wraparound deck is perfect for morning coffee or evening sunsets, surrounded by nature. The oversized, detached two-car garage offers endless possibilities for storage, projects, or tinkering. Inside, you’ll find eclectic charm blended with modern updates: a beautifully refreshed kitchen featuring stainless steel appliances and granite countertops. Whether you’re seeking a private escape or a home with character, this property delivers both. Enjoy rustic serenity without sacrificing convenience—just 15 minutes to Middletown’s shops and dining, and within the desirable Middletown school district. A rare opportunity to own a one-of-a-kind home that truly captures the best of mountain-style living. Roof - 2020, Skylights - 2020, Stove/Microwave - 2021, Fridge 2023+, Water Softener/Neutralizer - 2022.
#MDFR2070626

MIDDLETOWN

6838 MOUNTAIN CHURCH ROAD

4 Beds

3 Baths

2,488 Sq.Ft.

$649,900

MLS#: MDFR2070626

Beautiful Stone Front Colonial in Sought-After Pineland Park 3,887 total finished square feet offering 6 bedrooms and 3.5 baths on a 1-acre lot. Located in the desirable Pineland Park neighborhood of Warren County, ideal for commuting via I-66 and I-81. Minutes to golf, wineries, hiking, shopping, and downtown Front Royal. The Jefferson III model by H & H Builders features a stone front exterior, wide trim, interior columns, and 9-ft ceilings. Main level includes newly refinished hardwood floors throughout, a formal living room, and a formal dining room with chair rail and box ceiling detail. Spacious family room with corner gas fireplace opens to the kitchen with abundant cabinetry, countertop space, and breakfast area. Covered wrap-around front porch and rear covered porch provide great outdoor living spaces. Upper level offers hardwood hallway floors and new carpet in bedrooms. Newly remodeled primary suite includes vinyl plank flooring, tiled bath with soaking tub, separate shower, and walk-in closet. Three additional bedrooms and upper-level laundry for added convenience. Fully finished walk-out basement features tile flooring, kitchenette/wet bar, family room, two bedrooms, full bath, and ample storage—perfect in-law or guest suite. New AC units; furnace less than 5 years old. 2-car front-load garage with concrete driveway and plenty of off-street parking. Over 1 acre of open yard to enjoy.
#VAWR2012638

MIDDLETOWN

76 KATIE LANE

6 Beds

3 Baths

3,888 Sq.Ft.

$649,900

MLS#: VAWR2012638

New on site 4 days ago
The Fayetteville offers an open-concept layout paired with timeless classic design, creating a home that feels both inviting and refined. Scheduled for settlement in April 2026, this thoughtfully designed residence includes 3 bedrooms, 3 baths, and a 2-car garage, with flexible spaces ideal for everyday living and entertaining. Standout features include a finished basement that expands your living area, a cozy fireplace that anchors the main living space, and laminate wood flooring throughout the first floor for a warm, cohesive feel. A dramatic backsplash extending to the ceiling adds a designer touch in the kitchen. The kitchen is styled with light grey cabinetry and white quartz countertops, blending clean lines with modern elegance. Upstairs, carpeted bedrooms provide comfort and privacy, while the bathrooms feature upgraded showers with eye-catching diamond backsplash details. For a full list of included features, please contact our sales representatives. Photos are for illustrative purposes only and may not represent the exact home or finishes available.
#DENC2094616

MIDDLETOWN

851 MERLIN DRIVE

3 Beds

3 Baths

2,307 Sq.Ft.

$639,900

MLS#: DENC2094616

Welcome Home to the Ponds at Bayberry, Middletown’s premier 55plus community! Trade in the lawnmower for your pickleball racket and prepare to retire in style! The tree-lined streets with sidewalks at The Ponds of Bayberry lead you through a stunning community with resort-style living. Natural parks, miles of trails, a glamorous clubhouse with fitness room, library, game room and heated outdoor pool with courts and bocci ball are just a walk away! Bayberry is at the epicenter of shopping, dining, and more - a country setting with easy access to major routes North or South for you to get away or friends and family to visit. Situated on a premium lot with under ground sprinkler system and a nature filled view of woods behind you, this turnkey 3 bedroom, 2 full bath home features gleaming wood floor, 9’ ceilings, gourmet kitchen, sunroom, designer upgrades everywhere you look, a new maintenance free large deck, 2 car garage. Perfect for entertaining and hosting gatherings with the showcase kitchen featuring the gas cooktop, stainless steel appliances, combination microwave and oven, oversized island with counter and double sink. The bedrooms are large and spacious with lighted ceiling fans and dimmers. This home has all the upgrades and you’ll feel at home the moment you walk up to the front porch and through the front door. Need more storage or living space? The full unfinished basement is huge and includes the rough-in for a full bath. Come see this one in person.
#DENC2093398

MIDDLETOWN

5338 NEWMAN LANE

3 Beds

2 Baths

1,925 Sq.Ft.

$639,000

MLS#: DENC2093398

Rothwell Estates from Benchmark Builders. The CLAYTON (to be built) is our starter 4 bedroom 2.5 bath home. We encourage you to take the virtual tour to see this floor plan. Rothwell Estates is endowed with a rich variety of two-story and ranch models, which include basements and an abundance of standard features such as a stone water table, hardwood standard in the foyer, kitchen and breakfast area,& powder room. Granite counter tops in the kitchen, stainless steel appliances, an island, 42" maple cabinets, gas fireplace, recessed lights, tile baths, fully sodded yard and much, much more! With an emphasis on open and versatile floor plans, you are certain to find the home of your dreams. Residences are situated on perfectly sized home sites, most of which back up to open space. And, you'll love the comfort and peace of mind these energy-efficient homes provide. Located in the highly regarded Appoquinimink School District, families will find much to appreciate. Whether you're looking for a home that offers first-floor living or a grand two-story design, Rothwell Estates has something for everyone! Please visit the model home at 126 Green Forest Drive, Middletown, DE 19709. Agent must accompany buyer on first visit or pre-register prior to first visit on builder website
#DENC2079880

MIDDLETOWN

126 GREEN FOREST DRIVE 2 CLAYTON

4 Beds

2 Baths

2,586 Sq.Ft.

$638,000

MLS#: DENC2079880

Rothwell Estates from Benchmark Builders. The ARMSTRONG (to be built) is the smaller of our 2 ranch floor plans. It has an optional 2nd floor loft/bedroom area, but is spacious without it. The large kitchen & vaulted ceiling in the great room are some of the stand out features in this home. We encourage you to take the virtual tour to see this floor plan. Rothwell Estates is endowed with a rich variety of two-story and ranch models, which include basements and an abundance of standard features such as a stone water table, hardwood standard in the foyer, kitchen and breakfast area,& powder room. Granite counter tops in the kitchen, stainless steel appliances, an island, 42" maple cabinets, gas fireplace, recessed lights, tile baths, fully sodded yard and much, much more! With an emphasis on open and versatile floor plans, you are certain to find the home of your dreams. Residences are situated on perfectly sized home sites, most of which back up to open space. And, you'll love the comfort and peace of mind these energy-efficient homes provide. Located in the highly regarded Appoquinimink School District, families will find much to appreciate. Whether you're looking for a home that offers first-floor living or a grand two-story design, Rothwell Estates has something for everyone! Please visit the model home at 126 Green Forest Drive, Middletown, DE 19709. Agent must accompany buyer on first visit or pre-register prior to first visit on builder website
#DENC2079868

MIDDLETOWN

126 GREEN FOREST DRIVE 1 ARMSTRONG

3 Beds

2 Baths

2,225 Sq.Ft.

$638,000

MLS#: DENC2079868

To be built - New Construction! Monarch offers resort-style living featuring high-end finishes and flexible floor plans. At the heart of the community, residents will enjoy an amenity-rich clubhouse complete with a resort-style pool, pickleball and sports courts, and inviting indoor lounge spaces perfect for relaxation or connection. Combining the sophistication of luxury homes with the laid-back charm of Delaware living, Monarch delivers the perfect balance of comfort, style, and convenience—all just minutes from Middletown’s shopping, dining, and entertainment. The Mayberry is a ranch home starting at 2,254 sq. ft., with 3 bedrooms, 2 baths, and a flex space. Split-bedroom design offers privacy; open kitchen with walk-in pantry flows to great room and dining. Options available for extra bedrooms, baths, and outdoor spaces.
#DENC2093526

MIDDLETOWN

2206 EARLY COURT

3 Beds

2 Baths

2,254 Sq.Ft.

$629,900

MLS#: DENC2093526

Build your dream home with Schaeffer Homes in Middletown with Schaeffer Homes! This home is to be built through their Build On Your Lot Program. Starting at 2,223 square feet, the Ellis is a sizable home, with 2 modern elevations options. This model includes 4 bedrooms, 2 1⁄2 baths, and a 2-car garage, providing ample space for families of all sizes. The home starts at 2-stories, with the option to add to a 3rd floor if you are in need of an extra bedroom and bath!! The great room is adequate enough to fit a large dining table, while still allowing extra space to spread out between the kitchen and family room. With its sleek design and thoughtful layout, the Ellis is the perfect blend of style and functionality. The homesite is listed for $230,000, the home is $271,900, and the estimate for land development cost is $120,000. Land development costs can be more or less than $120,000. Seller and Builder make no representation of the feasibility and cost for site development and will provide a due diligence period to the Buyer. Schaeffer Homes has the exclusive right to build on this lot and will assist the Buyer through the due diligence process. It is unknown if a basement foundation is available until soil testing is completed, which will be the responsibility of the Buyer. Seller and Builder make no representation of the feasibility and cost for site development and will provide a due diligence period to the Buyer. Schaeffer Homes has the exclusive right to build on this lot and will assist the Buyer through the due diligence process. ***NOTE: Home is to be built. Pictures and virtual tour are of the same base model with upgraded options shown. Other Schaeffer Floorplans are available to be built on this homesite.
#DENC2092334

MIDDLETOWN

1487 BUNKER HILL ROAD

4 Beds

2 Baths

2,223 Sq.Ft.

$621,900

MLS#: DENC2092334

Welcome to this beautiful ranch home in the highly sought‐after 55+ community of Four Seasons at Baymont Farms in Middletown—where maintenance-free living meets upscale comfort! This single‐level home offers a spacious, yet seamless layout, perfect for easy living including 3 bedrooms and 3 full bathrooms, along with a professionally finished lower level (approx 1800 additional sq ft) — giving you the extra space you desire: Ideal for hosting family, guests, or setting up a home office / hobby space. The layout flows from a welcoming entry into the living room and dining areas — perfect for relaxed entertaining or quiet evenings. The upgraded kitchen is a chef’s dream. The finishing details offer clean lines, modern soft-close cabinetry, beautiful Quartz counter tops and stainless-steel appliances making everyday living a pleasure. The Spacious Primary Bedroom with luxurious En-suite Bath invites relaxation with its spa-like finishes. A beautifully designed, extra large walk-in closet provides abundant storage and organization, making this primary suite both functional and indulgent... the perfect place to unwind at the end of the day. The Baymont community offers resort‐style living — clubhouse, pool, and social opportunities built into your lifestyle. Situated in New Castle County and right in the heart of Middletown’s growing landscape, this home offers convenience to local shopping, dining, and major commuter routes while still preserving a peaceful neighborhood feel. Easy access to nearby amenities makes day‐to‐day living a breeze. If you’re looking to downsize or transition to a low-maintenance lifestyle without compromising on space or style, this home checks all the boxes. With everything you need on one level, a desirable newer construction home in move-in ready condition, you’re free to focus on enjoying life — not home upkeep! The practical, yet elegant layout allows flexibility for guests, a craft room, or a comfortable office. Homes in this neighborhood show strong value and demand making this a smart place to make your next move. Imagine having a morning coffee on your patio, or screened porch, an afternoon swim, or clubhouse time just steps from your door. Whether you’re aiming for relaxed retirement living or simply want a well‐designed home with minimal maintenance, this is the perfect home for you! Please contact me to schedule your private tour and see how seamless your next chapter can be.
#DENC2092652

MIDDLETOWN

798 HONEY LOCUST ROAD

3 Beds

3 Baths

1,875 Sq.Ft.

$620,000

MLS#: DENC2092652

This is a great opportunity to live at the beautiful Parks Edge at Bayberry 55 + community. The Hudson Quick Delivery! Come experience the active adult lifestyle that homeowners are raving about: a vibrant social scene, luxury amenities, stunning outdoor spaces and a place that will make you feel welcome and at home from the day you move in. Enjoy low maintenance living with lawn care & snow removal all taken care of for you leaving you more time to enjoy events & activities at your luxury clubhouse with resort style pool overlooking a pretty lake, fitness center, games/billiard room, pickleball & more. Visit our decorated model homes open daily: Monday 1-5, Tuesday -Sunday 10-5.
#DENC2092406

MIDDLETOWN

5735 E CENTRAL PARK DRIVE

3 Beds

2 Baths

2,156 Sq.Ft.

$619,723

MLS#: DENC2092406

TO BE BUILT - The Bennett This beautiful 2 story home features 4 bedrooms, 2.5 baths, 2 car garage. Standard features include a partially finished basement, Granite kitchen countertops, 42" maple cabinets, stainless steel appliances, hardwood floors in foyer, kitchen & breakfast area & a stone water table on the exterior. Appoquinimink School district!
#DENC2079328

MIDDLETOWN

400 REDERICK LANE 3 BENNETT

4 Beds

2 Baths

3,000 Sq.Ft.

$618,000

MLS#: DENC2079328

Welcome to the Cottonwood Model, TO BE BUILT, in the highly sought-after 55+ community of Traditions at Whitehall. This 3-bedroom home features a generous Owner’s Suite at the front of the home, complete with double walk-in closets leading to a luxurious en-suite bath, offering a privacy water closet and a 5-foot tile shower. At the rear of the home, you will find the kitchen and dining area that opens to a bright and airy great room, perfect for relaxation or entertaining. Step outside to enjoy the peaceful surroundings on the optional deck off the breakfast area, where you can take in views of the trees and open space. With a variety of structural and decorative options available, this home can be customized to suit your style and needs. The Cottonwood Model offers the perfect blend of comfort, size, elegance, and low-maintenance living in a vibrant active adult community. 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.
#DENC2080210

MIDDLETOWN

204 BALDY LANE COTTONWOOD

3 Beds

2 Baths

2,477 Sq.Ft.

$614,000

MLS#: DENC2080210

TO BE BUILT-The Greenspring -This beautiful home features 4 bedrooms, 2.5 baths, 2 car garage. Standard features include a partially finished basement, Granite kitchen countertops, 42" maple cabinets, stainless steel appliances, hardwood floors in foyer, kitchen & breakfast area & a stone water table on the exterior. Appoquinimink School district! Self-Guided Tours available daily 7 am-8 pm. Download "NterNow" APP on smart phone. Enter property ID at front door of Model; scan drivers license and door will auto unlock. Please make sure door is closed and door will auto lock.
#DENC2079324

MIDDLETOWN

400 REDERICK LANE 1 GREENSPRING

4 Beds

2 Baths

3,021 Sq.Ft.

$613,000

MLS#: DENC2079324

Built in 2023 and just two years young, this beautiful 3 bedroom, 3.5 bath home offers over 3,000 square feet of stylish, modern living in the highly sought-after Appoquinimink School District. Perfectly east-facing and set on a desirable end-lot location, it combines open-concept design with high-end touches that make everyday living both comfortable and elegant. The gourmet kitchen is a true showstopper, featuring stainless steel appliances, an oversized island with stunning pendant lighting, and plenty of space for cooking and entertaining. Just off the main living areas, you will find thoughtful upgrades like a custom accent wall in the office and a dramatic accent wall in the two-story stairwell, perfectly framed by the home’s soaring ceilings adding character and architectural interest to the space. Upstairs, a spacious loft offers a versatile flex space perfect for a home office, reading nook, or play area. The owner’s suite is a private retreat highlighted by elegant tray ceilings, an en-suite bath with double sinks and a walk-in shower, and a massive closet with its own window for natural light making it easier to find what you need and keeping the space bright and inviting. Two additional bedrooms and another full bath complete the second level, along with a laundry room featuring shelving, a convenient and organized space that makes household tasks easier and more efficient. The partially finished basement provides even more living space including a full bath and a huge unfinished storage area that is ready for your personal touch. It features a large walkout with double doors. This space is ideal for a home gym, media room, or future expansion. As a bonus, the HOA covers lawn mowing, adding convenience and ease to your homeownership experience. Located just minutes from Route 1, local shops, dining, and parks, this home offers the perfect blend of convenience and community living. Don’t miss your chance to own this beautifully maintained, move-in-ready property in one of Middletown’s most desirable neighborhoods. 300 Jasper Way – Your next chapter starts here.
#DENC2087620

MIDDLETOWN

300 JASPER WAY

3 Beds

3 Baths

3,025 Sq.Ft.

$612,000

MLS#: DENC2087620

Step into the past and own a piece of Delaware's history with the Dilworth House, one of the earliest homes built in the state by Olla Jansen, a Swedish colonist from the 1600-1700 Native American Period. Situated on 12.25 acres of pristine land that backs up to the Augustine Wildlife Preserve, this property is a rare find, offering both a home and a rich connection to the past. The Dilworth House is a true gem, showcasing some of the finest early masonry craftsmanship in Delaware. The distinctive "diapering" pattern, glazed brick in diagonal lines, adorns the gable ends, while stepped belt courses and intricate framework add to its historic charm. Inside, you'll find beautifully exposed beams and brick fireplaces, which once served as the heart of the home’s heating system, with the house originally built in two sections and warmed by a single chimney. This three-story home offers 6 bedrooms, 3 full bathrooms, and 2 half bathrooms, with a fully finished attic on the third floor providing additional living space. The partial basement remains unfinished. Updates over the years have enhanced the home’s functionality, while carefully preserving its historic features. Most of the home remains in it's original state which will require work. For those with a passion for farming, mechanics, or automobiles, this property offers everything you could need. A silo, milk house, dairy barn, cow shed, and storage shed are all included, with the barn having been converted into a workshop—though it could be easily repurposed for a variety of uses. The expansive grounds also offer the possibility of subdivision, providing ample opportunity for future development. This is a once-in-a-lifetime chance to own a truly historic property in a prime location. Don't miss out, schedule your tour today!
#DENC2078246

MIDDLETOWN

875 PORT PENN ROAD

6 Beds

3 Baths

2,900 Sq.Ft.

$611,500

MLS#: DENC2078246

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