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
261
# of Listings
3
Avg # of Bedrooms
$271
Avg. $ / Sq.Ft.
$642,232
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

135 Properties Found. Page 5 of 9.

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. 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.
#DENC2093526

MIDDLETOWN

2206 EARLY COURT

3 Beds

2 Baths

2,254 Sq.Ft.

$684,900

MLS#: DENC2093526

Beautiful 6 bedroom, 3 1/2 bathroom colonial offering a covered front porch, 2 car garage, and a backyard paradise. The main floor offers a guest/in-law suite with full bathroom, formal living room/office, dining room, family room with gas fireplace featuring exquisite word working including ship lap and coffered ceiling, Kitchen with center island, granite counter tops, stainless steel appliances, and a pantry, as well as a morning room with access to the backyard deck. The upper level offers 5 bedrooms and features an owner suite, a large bedroom over the garage, laundry and 3 other generously sized bedrooms. The basement has a finished room, bathroom and offers a double well walk up exit to the backyard. The fenced backyard features an in ground salt water swimming pool with remote controlled underwater lighting, 3 deck jets, pennsylvania jump boulders/waterfall, deck, patio and a lounge area covered by a pergola with privacy trees. The home also features hardwood flooring, central vacuum system, bonus dedicated mini splits in most upper bedrooms, and plenty of storage space in the garage. Community amenities include walking trails, gazebo, park with playground, sand volley ball court, basketball court and wall ball. There is also a 18 hole golf course with clubhouse, Lore Woodfyre and Highlands Whiskey Bar. Don't miss the opportunity to make this impressive property your new home!
#DENC2097264

MIDDLETOWN

303 BRAEMAR STREET

6 Beds

3 Baths

3,716 Sq.Ft.

$674,900

MLS#: DENC2097264

FINAL HOME AT COPPERLEAF AVAILABLE IN 2026!!!! 411 Crownleaf Dr., the beautiful Montgomery Farmhouse! Off your front porch, you are greeted by a grand double story entry way with your formal dining room off to the side. Moving inward, an open layout seamlessly connects the family room with cozy fireplace, gourmet kitchen (complete w/ quartz counters, tile backsplash, and upgraded cabinetry), and included sunroom, creating an ideal setting for gatherings. Additionally, on the first level you will find your very own home office, as well as a spacious mudroom and walk-in pantry. The upper-level features 3 guest bedrooms, a hall bath, laundry room, and luxurious owner's suite. The owner’s suite offers a tranquil retreat area, perfect for relaxation. On the lower level, a large unfinished basement equipped with walk-up steps is ready for your personal touch—whether it’s a home theater, gym, additional living space, or storage. Enjoy luxurious living with convenient access to top-rated schools, shopping, dining, and recreation. This is more than just a home—it's a lifestyle. Contact us today to schedule a private tour. Prices, dimensions, and features may vary and are subject to change. Photos are for illustrative purposes only. Please see sales team for final details and finishes. 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.*
#DENC2081304

MIDDLETOWN

411 CROWNLEAF DRIVE

4 Beds

2 Baths

2,955 Sq.Ft.

$669,989

MLS#: DENC2081304

Semi-Custom Builder, so talk to the sales manager for additional design options. Last lot left in Rothwell Estates from Benchmark Builders. All 6 of our floor plans fit. We have a 7 month build time and rentals available for our buyers if you need a place to stay during the build. See the sales manager, Lindsay, for all the details. The JAMISON (to be built). The large kitchen, great room, and Extra Large Primary Suite 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
#DENC2097542

MIDDLETOWN

619 MCCRACKEN DRIVE 4 JAMISON

3 Beds

2 Baths

2,225 Sq.Ft.

$669,000

MLS#: DENC2097542

Nestled in the Brighton subdivision, this exquisite Colonial-style residence, built by Toll Brothers in 2023 on a corner lot, embodies the pinnacle of modern luxury living. Spanning approximately 2,650 square feet, this detached home offers a harmonious blend of elegance and functionality, perfect for those who appreciate high-end finishes and thoughtful design. Step inside the front door from the covered porch to discover an open floor plan that seamlessly integrates living spaces, accentuated by luxury vinyl plank flooring and strategically placed recessed lighting that enhances the ambiance of the 9' ceilings. The heart of the home is the gourmet kitchen, featuring granite countertops and a spacious island that invites culinary creativity. Equipped with top-of-the-line appliances, including a smart refrigerator, smart double oven, built-in microwave, and sleek induction cooktop, this kitchen is a chef's dream. The adjoining flex space serves perfectly as a dining area providing an ideal setting for entertaining naturally extending between the kitchen, dining, and great room areas. The large pantry ensures ample storage for all your culinary essentials coupled with a second closet space off the kitchen which can feature as an additional pantry or kitchen appliance storage to keep those granite countertops clear of clutter! The great room is a natural gathering space lit by abundant natural light. The far wall features sound absorbing slated Sonolok by Artika paneling making movie night an experience! Around the corner on the main level the home office is easily accessible without feeling overly pronounced striking the perfect balance for those who want to separate work in the office from living in the home. The main level powder room includes the PEX plumbing ran to convert to a full bath should you wish to do so in the future. Upstairs the primary suite ties together the same luxury vinyl plank from the main level. The suite includes a generous walk-in closet with extensive built-in shelving offering a dream wardrobe organization system. The en-suite tile floored bathroom is a haven showcasing a walk-in shower compatible with voice control through Anthem by Kohler and enriched by green porcelain tile and gold colored fixtures that promises relaxation and rejuvenation. A designated electrical outlet provides the opportunity for smart toilet or electronic bidet options should the future owners wish to continue adding to the modern oasis. Three additional spacious bedrooms adorn the upper level each featuring soft carpet flooring and ceiling fans. These bedrooms are complemented by a stylish full bathroom. The upper-floor laundry room adds a touch of practicality, making everyday chores a breeze and easily keeping laundry out of view when entertaining. Security is paramount, with a Ring camera as well as an advanced Reolink security system of exterior cameras ensuring peace of mind. Outside, the fenced-in corner lot enhances privacy and curb appeal, while the rear-entry detached two car garage continues to elevate with an electric vehicle charger and additional storage space. Additionally, the asphalt driveway accommodates multiple vehicles. A charming small greenhouse easily accessed from the basement walkout adds a unique touch, perfect for gardening enthusiasts. When finished gardening, the gorgeous backyard patio provides space to relax and unwind enjoying fresh air. In addition to the walkout stairs the basement includes storage shelving, an active radon mitigation system, and rough-in plumbing. This property is not just a home; it's a lifestyle featuring intentional upgrades and boundless potential. Experience the luxury of modern living where every detail has been meticulously crafted for comfort, style and functionality. This is more than a residence; it's an invitation to elevate your everyday life allowing you to focus on what truly matters - and all in the renowned Appoquinimink School District.
#DENC2092354

MIDDLETOWN

141 S LORES LANDING ROAD

4 Beds

2 Baths

2,650 Sq.Ft.

$664,999

MLS#: DENC2092354

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 Whimbrel is a ranch home starting at 1,971 sq. ft., with 3 bedrooms, 2 baths, and a flex space ideal for a home office. Open kitchen with island flows to dining and great room. Options available for extra bedrooms, baths, loft, and outdoor living. 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.
#DENC2093528

MIDDLETOWN

2204 EARLY COURT

3 Beds

2 Baths

1,971 Sq.Ft.

$664,900

MLS#: DENC2093528

Welcome to 1236 Pimpernell Path! This beautifully maintained, move-in ready 4-year-old D.R. Horton home offers exceptional space and modern design throughout. This amazing home feels and smells like brand-new construction! Don’t miss this rare opportunity to own a home in one of the most desirable communities. This spacious two-story residence offers nearly 2,600 sq. ft. of living space featuring 5 bedrooms and 3 bathrooms. The clean, ready-to-finish basement provides incredible potential — complete with a game room and wet bar, media room, workshop or exercise area, full bathroom, and ample storage space. The main level showcases an inviting foyer with a coat closet, leading to a bright and open living and dining area filled with natural light. The kitchen includes birch cabinetry, granite countertops, stainless steel appliances, a pantry, and a large island with seating, opening to both the breakfast area and family room featuring a cozy fireplace. A convenient powder room completes the first floor. Upstairs, the owner’s suite features a spacious bedroom, two walk-in closets, and a large ensuite bathroom. Additional well-sized bedrooms and a hall bathroom offer comfort for family or guests. Additional highlights include a first-floor laundry room adjacent to the garage entry, an oversized deck perfect for outdoor entertaining, and a two-car garage. This home combines thoughtful design, functionality, and quality finishes—ready for you to move right in!
#DENC2092178

MIDDLETOWN

1236 PIMPERNELL PATH

5 Beds

3 Baths

2,550 Sq.Ft.

$662,000

MLS#: DENC2092178

New construction without the wait. This gorgeous estate home has everything you could want and more! With four bedrooms and 2.5 baths, it ensures enough space for the whole family - and that includes a modern Study/Laundry Upgrade. Additional features include an upgraded kitchen with island, gas range & granite counters; a 1st-floor powder room; a 3-piece basement rough-in with partially finished basement, and a roomy two-car garage. Make an appointment to tour it now.
#DENC2091264

MIDDLETOWN

642 GORDON HOUSE WAY

4 Beds

2 Baths

2,889 Sq.Ft.

$657,712

MLS#: DENC2091264

Price Reduced! 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.

$650,000

MLS#: DENC2094672

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

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.

$649,990

MLS#: DENC2091996

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.

$649,990

MLS#: DENC2094616

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

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