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

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Under $250,000

$250,000 - $500,000

$500,000 - $1M

$1M - $3M

$3M - $5M

Over $5M

123 Properties Found. Page 5 of 9.

Welcome to 321 Ellenwood Drive, located in the sought out neighborhood of PARKSIDE. What an unique home!!!! a semi custom home built by Lifestyle by the original owners. This inviting 4 bedroom, 3.1 bathroom home is very special....first floor very large primary suite...Beautiful kitchen with all new appliances including a double oven, great counter space and eat in area with sliding doors out to a lovely paver patio with real wrought iron railing. The family room just had their hardwoods refinished and WOW ... did they come out beautiful, a gas fireplace a 4 windows pouring in with natural sunlight. 2nd floor has a large loft, 2 bedrooms and 1 full bathroom and then a large office/playroom/flex room that has an opening to the the family room below....and a cute balcony to sit our on and stare out the stunning tree lined street..... then a third floor with another loft, large bedroom and full bathroom....wait, so much more.... a 3 season room that has 3 points of exits... one to side yard, one to the other side yard that is fenced and one off the back of the house connecting to the 2 car garage. Now, if that is not enough, there is a large unfinished basement waiting for you to finish if you wish with a rough in and 9 foot ceilings... also a walkup bilco door... radon remediation added... a generator...beautiful landscaping...upgraded and maintained so well.... Now for the best news...brand new roof and the solar panels are being put back up 12/1 and will be owned up until March of 2036....Sellers bought out the lease for your savings!!!! Parkside has so much to offer... the community pool, where you can soak up the sun and enjoy a refreshing swim during warm summer days. The gym..... the club house.... and all our beautiful pocket parks. Don't miss your chance to call this charming home in a sought-after neighborhood yours. Schedule a viewing today to experience the comfort and convenience this property has to offer in person.
#DENC2092224

MIDDLETOWN

321 ELLENWOOD DRIVE

4 Beds

3 Baths

3,175 Sq.Ft.

$649,999

MLS#: DENC2092224

Stunning home, located on a culdesac, and beautifully situated on the golf course of the Frog Hollow Golf Club located in the popular community of The Legends in Middletown. Great Location, down the street from Club House (pool, golf, pickle ball, tennis, pub, banquet hall). This beautiful home has been well maintained, updated and improved, smoke/pet free. Active Security System (audio and visual). Some noteworthy details: High Efficiency HVAC Replaced July 2020 with Honeywell Humidifier; RainSoft Water System with Reverse Osmosis in 2015; Kitchen Renovation 2015; Air Duct Clean 2023; Roof 2014; Electric SolarWorld Sunfix Plus(R) in 2016; Garbage Disposal 2025; Front Door and Storm Door in 2017; Invisible Fence 2014. Privacy on culdesac, short distance to Pool, Club House, etc. Located on the golf course with view and privacy of trees. As you enter this home you will feel the elegant and welcoming ambiance onto a Cathedral Foyer with hardwood floor, curved steps; flanked by the Office with double doors with and a living room, each with front view. A spacious Dining Room with back view and sconce lighting that opens into the kitchen. The kitchen is a beautiful wow factor with lots of windows, large sink, tile floor, multiple granite counters and tile backsplash, recessed and pendant lighting, pantry and a Eat-In Kitchen dining area with sliding door to the multi-level back deck. Nicely transitioning from the Kitchen, an area to the garage and closet, and walk into the Family Room, surrounded by large windows with beautiful backyard view and direct access to the back stairs leading, cozy gas fireplace, recessed lighting and ceiling fan with light. The private quarters on the upper floor with a large primary bed suite with sitting area hosting additional storage (would be great for additional office area or relaxing area), ceiling fan, dual closets, private bath with tile flooring, dual sinks, large jetted tub with multiple windows above, glass door shower and recessed and over the sink lighting. Completing the upper floor are 3 additional bedrooms (total 4) with recessed lights (and ceiling fan in Bed 2 and 3; Bed 4 wired for fan), a Full Bath with linen closet, double sink and tub/shower and window with back view and a Laundry Room with linen closet, laundry sink and side by side large washer, dryer and window with back view. Wait, there’s more….a large Full Size basement, great for storage, craft/workshop, or finish for additional living space, includes Bilco doors for quick outdoor access and convenient for patio/deck furniture storage, and if you decide to finish the basement you already meet the current Building Code for having an egress in the basement (saves you money if the basement doesn’t have egress). If you’re looking for a great entertaining style backyard, this is for you… a great deck (multi-level) with pergola and steps down to a large concrete patio. Beautiful landscaping around the home (plant sketch with pics to be provide to buyer) and some large trees around back provide privacy while open to the view of the golf course. The double door garage offers storage, direct access to the home into area near the kitchen (convenient for carrying in groceries). Quick settlement possible. Home Warranty included and Membership to the Pool. The Community Name is The Legends. The Golf Course is The Frog Hollow Golf Club and hosts The Pub and Golf Pro Shop. TheEdge18 manages the Banquet Hall, Swimming Club and Pickle Ball and Tennis. Property Size and Tax Info provide by MLS, NCC parcel view website, and Town of Middletown web site is presumed accurate. Listing Agent/Brokerage not responsible if any inaccuracies.
#DENC2097798

MIDDLETOWN

6 BRADLEY CIRCLE

4 Beds

2 Baths

3,233 Sq.Ft.

$640,000

MLS#: DENC2097798

The Carver - with 4,000 finished sq. ft. - is a thoughtfully designed home that blends open living with private retreats. A welcoming foyer with a detailed ceiling treatment sets the tone as you enter. Just off the entry, a private home office with stylish barn doors offers the perfect space for telecommuting or quiet focus. The spacious great room and dining area come together beneath a vaulted ceiling, creating an open, airy feel ideal for both everyday living and entertaining. The striking kitchen features abundant counter space and a large pantry, making meal prep and storage effortless. Tucked away for privacy, the primary suite showcases an elegant ceiling treatment, a generous walk-in closet, and a luxurious primary bath with freestanding vanities and a large walk-in shower. The finished basement expands the living space with a recreation room, additional bedroom, and full bath—perfect for guests, hobbies, or multi-generational living. This listing is for a to be built home and photos are of a model home for display purposes only. Please see sales consultant for details.
#DENC2096234

MIDDLETOWN

1932 DIXON WAY

3 Beds

3 Baths

4,147 Sq.Ft.

$639,990

MLS#: DENC2096234

This is a builder model home sale. This beautiful Calloway Queen Anne offers 2,657 square feet of living space. The abundance of windows floods the family room and kitchen with natural light. Upgraded luxury vinyl plank runs throughout the first floor, the upstairs hall, and primary bedroom. The kitchen boasts an oversized island, quartz countertops, and a tiled backsplash. Both bathrooms offer quartz vanity tops.
#DENC2088810

MIDDLETOWN

5605 S BAYBERRY PKY

4 Beds

2 Baths

N/A

$639,000

MLS#: DENC2088810

Major Price Reduction Move-in ready and offering over 4,000 square feet of beautifully finished living space, this expansive 4-bedroom home is set within the sought-after golf course community of The Estates at St. Anne’s, located in the highly regarded Appoquinimink School District. Designed for both everyday comfort and elegant entertaining, the main level features formal living and dining rooms, a spacious Great Room with a cozy fireplace, and an upgraded kitchen with a center island that opens to a sun-filled morning/breakfast room with access to the large Trex deck and pergola overlooking the expansive wrought-iron fenced yard. A dedicated home office, convenient laundry room, and half bath complete the first floor. Upstairs, you’ll find four generously sized bedrooms and two full baths, highlighted by the oversized Owner’s Suite with a sitting room, two large walk-in closets, and a spa-like bath with dual vanities, a corner soaking tub, and separate shower. Additional living space awaits in the full finished basement, while a two-car garage adds everyday convenience. Residents of The Estates at St. Anne’s enjoy access to a semi-private 18-hole golf course, the acclaimed Lore Modern Woodfyre restaurant, Highlands Whiskey Bar, and an on-site banquet facility. Ideally located with easy access to major highways, tax-free shopping at Christiana Mall, nearby parks, fine dining, and entertainment, and close to Middletown’s charming downtown—plus just about an hour from the Delaware beaches—this home truly offers the best of space, style, lifestyle, and location. Mortgage savings may be available for buyers of this listing.
#DENC2094672

MIDDLETOWN

312 GALLOWAY STREET

4 Beds

2 Baths

4,475 Sq.Ft.

$635,000

MLS#: DENC2094672

Brand New 55+ Community in Middletown, DE The Morse home design blends a spacious open floorplan with classic architectural details, creating a timeless yet modern living experience. With 3 bedrooms (including one in the finished basement), 3.5 baths, and a 2.5-car garage, this home offers both functionality and refined style. Highlights include a fireplace with shiplap surround, feature walls in the foyer and owner’s suite, and a screened porch that overlooks beautiful community open space—perfect for relaxing or entertaining. The finished basement adds extra versatility, complete with a full bedroom and bath ideal for guests or extended family. The kitchen is designed for convenience and style, featuring smart appliance upgrades and quartz countertops for a sleek, modern finish. Laminate flooring throughout the first floor enhances the flow of the open-concept layout while offering easy maintenance. In the owner’s bath, a tiled shower enclosure with a rain shower head brings a spa-like touch to everyday living. 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.
#DENC2091996

MIDDLETOWN

1602 JAYMES CIRCLE

3 Beds

2 Baths

2,349 Sq.Ft.

$629,990

MLS#: DENC2091996

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 Newport – Single-level ranch home with 1,662+ sq. ft., 3 bedrooms, and 2 baths. Features a spacious kitchen with island seating open to the dining area and great room. Options include an added second-floor bedroom and bath, unfinished storage, and outdoor living spaces. Monarch’s HOA fee includes grass cutting on your property, curbside garbage and recycling services, common area maintenance including walking paths, landscaping, streetlights, entrance monuments, and all community amenities.
#DENC2093608

MIDDLETOWN

2202 EARLY COURT

3 Beds

2 Baths

1,662 Sq.Ft.

$629,900

MLS#: DENC2093608

New on site 4 days ago
Welcome to this beautiful Schell Brothers Ranch style home situated in the sought-after community of PARKSIDE in Middletown, DE. This delightful property offers 3 bedrooms and 2 full bathrooms, providing a cozy and inviting space for comfortable living. The home features a single level/stories layout, perfect for easy accessibility and convenience. Step inside to discover a spacious living area with a charming fireplace, creating a warm and welcoming atmosphere for both relaxing evenings and entertaining guests. The kitchen is equipped with modern appliances, 2 islands ....one working island and one that sits 4..... all stainless steel appliances ... so many counters .....and opens up to a dining area, and family room..... ideal for family meals and gatherings. Outside, the property boasts extensive hardscaping, exterior lighting, and a well-maintained lawn with a sprinkler system, adding to the charm and appeal of the outdoor space. Relax and unwind on the paver patio with beautiful landscaped yard... did you notice the 3 car garage.... wait!!!! the unfinished basement over 2000 sq ft..... to do whatever your heart desires.... Parkside offers a wonderful club house with a pool, tennis, pickleball, gym and great open space
#DENC2098416

MIDDLETOWN

677 SPRING HOLLOW DRIVE

3 Beds

2 Baths

2,450 Sq.Ft.

$629,000

MLS#: DENC2098416

NEW PRICE! 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. Newly remodeled upper-level bath. 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.

$625,000

MLS#: VAWR2012638

Quick Delivery 5 bedroom home in Appoquinimink school district. READY TO GO! This lovely home offers a 1st floor full bath with bedroom/office space, and the remaining 4 beds and 2 baths upstairs. The Charleston floor plan offers a well crafted layout with walk-in pantry, butler's pantry, switchback staircase, and much more. Quality products like Hardie Plank Siding, Timbertech front porch, and Anderson windows add to the fine construction by this local, semi-custom builder (Benchmark Builders). Check in at the model home during business hours for a tour and more information. This home can be seen 7am-8pm via the NTerNow app. Simply show up, scan the QR code, and follow the instructions.
#DENC2095376

MIDDLETOWN

1011 STUYVESANT STREET

5 Beds

3 Baths

2,716 Sq.Ft.

$624,999

MLS#: DENC2095376

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.

$624,000

MLS#: DENC2079328

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

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.

$619,000

MLS#: DENC2079324

Welcome to Baymont Farms — where resort-style living meets effortless luxury. Located in one of Middletown’s premier 55+ active adult communities, this stunning single-family home—just 2.5 years young—offers refined design, thoughtful upgrades, and the relaxed elegance you are looking for in your next home. Freshly painted and beautifully maintained, the home is completely move-in ready and radiates a bright, sophisticated feel throughout. Offering 3 bedrooms and 3 full baths, the versatile floor plan is designed for both everyday comfort and effortless entertaining. A private upper-level suite creates the perfect retreat for guests, grandkids, or hobbies, complete with its own bedroom, full bath, and sitting area. At the heart of the home is a beautifully appointed gourmet kitchen featuring crisp white cabinetry, quartz countertops, stainless steel appliances, and a spacious center island with bar seating—ideal for casual gatherings. The adjoining dining area is accented with charming farmhouse wainscoting, while the dramatic floor-to-ceiling stone gas fireplace anchors the great room and creates a warm, inviting focal point. A thoughtfully designed private office with custom built-in bookcase and rolling ladder offers both style and function—perfect for reading, working, or pursuing favorite hobbies. Designed with easy one-floor living in mind, the spacious owner’s suite provides a peaceful retreat with a luxurious en-suite bath and an oversized walk-in closet. Outdoor living is equally special. The Trex deck offers a perfect setting for entertaining or quiet evenings outdoors, while the sun-filled east-facing sunroom welcomes morning light and overlooks the beautifully landscaped backyard highlighted by merlot crepe myrtle trees. In the evening, unwind on the charming front porch and enjoy picturesque sunset views framed by apricot and berry-red miniature rose bushes. Additional highlights include professionally landscaped grounds, an irrigation system, a full unfinished basement already plumbed for future expansion, and a spacious two-car garage. Life at Baymont Farms feels like being on vacation year-round, with amenities including: • Resort-style pool with tiki bar • Pickleball and bocce courts • Scenic walking and biking trails • Kayak access to Drawyers Creek • Dog park • A stunning clubhouse hosting over 50 social clubs and activities, from mahjong and bourbon tastings to yoga, arts & crafts, book clubs, poker nights, and festive holiday gatherings. Experience the perfect blend of luxury, comfort, and vibrant community living. Schedule your private tour today and discover why Baymont Farms is one of Middletown’s most sought-after active adult communities
#DENC2098450

MIDDLETOWN

507 CHERRY BARK ROAD

3 Beds

3 Baths

2,700 Sq.Ft.

$615,000

MLS#: DENC2098450

Welcome to 3016 Barber Lane! This gorgeous, 55+ newly constructed detached home was built in 2024 and is located in Parks Edge, a part of the Village of Bayberry community in Middletown, Delaware! Situated on a premium corner lot, this beautifully upgraded Cooper II model with a two car garage offers great views with a pocket park in front and a meadow behind the home that cannot be built on! This thoughtfully designed home features 2 bedrooms, 2 full baths, and a versatile den/flex space that can serve as an office or easily convert to a third bedroom. From the moment you step inside, you’ll appreciate the luxury vinyl plank flooring that runs throughout the main living areas and bedrooms! The gourmet kitchen is a standout, featuring a huge level 3 quartz island, stainless steel appliances, a double wall oven, electric glass-top range, built-in microwave, and dishwasher. The cabinetry package was the highest upgrade offered (level 3), complete with soft-close doors and drawers and pull-out racks for maximum functionality, and the pantry has been enhanced with a custom Closet Factory system! The kitchen flows seamlessly into the living and dining areas with a nice open floor plan! Heading to the bedrooms you will find a spacious primary suite that includes a beautifully tiled bath with a walk-in shower and built-in seat. A large primary closet is also outfitted with a fully customized master closet system by Closet Factory. The second bedroom is also a great size with a large closet and a cozy nook in the room! Additional custom Closet Factory upgrades were added to the laundry room, providing exceptional organization and storage. The outdoor living is just as impressive, with a screened-in porch leading to a 16x20 maintenance-free vinyl deck with metal spindles—perfect for entertaining or simply enjoying the peaceful meadow views. The home also includes a two-car garage with a Liftmaster garage door open that connects to MyQ App- so convenient! There is also a huge unfinished basement which has been professionally water-sealed floor for added peace of mind. After move-in, the owner put in over $40,000 in additional upgrades to the home, including custom zebra blinds on nine windows, tinted privacy mirror polarized glass at the front door, patio sliders, and primary bath window, grab rails in the bathroom and five ceiling fans with remotes were installed. In addition- EVERY light fixture, faucet, and door handle was upgraded throughout the home, and three wall-mounted TV setups with electrical were installed. Front railings were also added to the front porch! The irrigation system includes a Wi-fi adaptor so it connects to your phone and can control each zone in the system! This exceptional property combines premium lot positioning, extensive upgrades, and move-in-ready condition in one of Middletown’s most desirable active adult communities! Book your tour today!
#DENC2098048

MIDDLETOWN

3016 BARBER LANE

2 Beds

2 Baths

1,866 Sq.Ft.

$615,000

MLS#: DENC2098048

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