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
259
# of Listings
3
Avg # of Bedrooms
$272
Avg. $ / Sq.Ft.
$645,798
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

259 Properties Found. Page 11 of 18.

UPDATE!!! PRICE REDUCTION!!! Now being offered at below the base price for a new Cooper ll model!! Be sure to check the included features sheet and additional upgrades to see the overall value. Welcome to Parks Edge! This exceptional 55+ community in Delaware offers an array of amenities that are truly hard to beat, designed to enhance your active lifestyle. We are pleased to present the Cooper II model, a two-bedroom, two-bath home built by Blenheim Homes. This particular residence features a flexible room that offers the versatility to be easily converted into a third bedroom, an office, or a hobby room, catering to your specific needs. There is also a rough-in for a third bathroom in the basement for the potential need to add another bathroom. The home was constructed with numerous high-quality and energy-efficient features, a detailed list of which can be found in the attached documents for your review. Furthermore, the balance of the 10-year structural warranty is transferable to the new owner(s), providing additional peace of mind. Parks Edge residents enjoy unparalleled access to both the Bayberry South Lakehouse and their own exclusive luxury clubhouse. The clubhouse includes a state-of-the-art fitness center, a refreshing outdoor pool, and various athletic courts for your enjoyment. Beyond these facilities, the community boasts an 11-acre boating and fishing lake and a sprawling 70-acre park, offering ample opportunities for recreation and relaxation. To further enhance your living experience, these features come with the added convenience of included lawn maintenance, snow removal, and irrigated lawns. Close to everything Delaware and surrounding states have to offer, including the grand opening of the largest grocery-anchored retail center in Middletown. Weis Market and 280,000 sf retail center with all the shopping you need right outside your door. We invite you to schedule your showing today to experience all that this remarkable home, community, and area have to offer.
#DENC2089864

MIDDLETOWN

3037 BARBER LANE

2 Beds

2 Baths

1,800 Sq.Ft.

$528,000

MLS#: DENC2089864

Welcome to the popular Bloomfield Model in the 55+ community of Traditions at Whitehall. This floor plan has 2-Bedrooms with a standard loft and a generously sized great room open to the kitchen and dining area. You will have plenty of space if you like to entertain. A rear Owner's Suite gives maximum privacy and includes a large walk-in closet and en-suite with a double bowl vanity and 5-foot tile shower. The second floor features a large loft and walk-in closet for additional storage or overnight guests. With many structural options available, another bedroom and another bathroom can easily be added. Customize your interior and exterior finishes and make this house your home! As a resident you will enjoy access to amenities that include a clubhouse, fitness facilities, swimming pools, walking trails, and a full calendar of social events to keep you engaged and connected with neighbors.
#DENC2080216

MIDDLETOWN

120 BURLINA BLVD BLOOMFIELD MODEL

2 Beds

2 Baths

2,053 Sq.Ft.

$527,000

MLS#: DENC2080216

Welcome to the Belville Model in the 55+community of Traditions at Whitehall. TO BE BUILT. This inviting 2-Bedroom home has a welcoming foyer which leads you down the hall towards the main living area! An open kitchen and breakfast area which flows into the large great room and is perfect for entertaining! The owner’s suite in the front features a large walk-in closet and owner’s bath with a double bowl vanity and 5-foot tile shower. The second floor offers a standard loft with the option to add an additional bedroom and/or bathroom. Customize your interior and exterior finishes and make this home yours! As a resident you will enjoy access to amenities that include a clubhouse, fitness facilities, swimming pools, walking trails, and a full calendar of social events to keep you engaged and connected with neighbors.
#DENC2080214

MIDDLETOWN

204 BALDY LANE BELVILLE

2 Beds

2 Baths

2,059 Sq.Ft.

$521,500

MLS#: DENC2080214

Welcome to 1 Walnut Pond Ct in the heart of Middletown! Nestled on a desirable corner lot in a small, quiet neighborhood, this beautifully updated 4-bedroom, 2.5-bath home offers comfort, style, and peace of mind with major upgrades already completed. Enjoy brand new windows, a new HVAC system, new hot water heater, and new stainless steel appliances. The home features new flooring throughout, including laminate flooring and carpet, along with fresh paint that gives the entire space a clean, modern feel. Step outside to a 5-year-old Trex deck overlooking your private backyard retreat complete with a screened-in porch and a pool with a 2-year-old liner — perfect for entertaining or relaxing all summer long. Additional highlights include a 2-car garage and a prime corner lot location in one of Middletown’s most desirable areas. Move-in ready and loaded with upgrades — this one won’t last!
#MDFR2076532

MIDDLETOWN

1 WALNUT POND COURT

4 Beds

2 Baths

1,620 Sq.Ft.

$520,000

MLS#: MDFR2076532

New on site 1 day ago
This is your opportunity to move into Silver Maple, one of the area’s most desirable 55+ communities, known for its exceptional amenities and active lifestyle. From the moment you enter this 3BR, 2BA, 2-car garage home, you’ll notice the beautiful hardwood floors that flow from the foyer through the main living areas. The open-concept floor plan seamlessly connects the living room, featuring recessed lighting, to the gourmet kitchen with upgraded cabinetry, stainless steel appliances, granite countertops and nice breakfast bar area. The spacious primary suite includes a large walk-in closet and a private bath. Just off the living room, the sunroom addition provides the perfect spot to relax, while the upgraded Trex deck with retractable awning is ideal for enjoying your morning coffee or entertaining outdoors. The full basement with egress window presents endless possibilities for additional living space and includes plumbing hook-ups for future expansion. Additional updates include fresh paint throughout, new roof with 50-year warranty (2026), updated light fixtures, new porch railing, and more. Four Seasons at Silver Maple, built by K. Hovnanian, offers resort-style living with a clubhouse, meeting rooms, outdoor pool, pickleball and bocce courts, horseshoes, fire pit, walking trails, and community garden. Don’t miss the chance to enjoy low-maintenance living in one of Delaware’s premier active adult communities.
#DENC2098642

MIDDLETOWN

137 SILVER MAPLE ROAD

3 Beds

2 Baths

1,625 Sq.Ft.

$519,900

MLS#: DENC2098642

Welcome to 248 Ann Drive in the heart of Middletown at the Crossland at the Canal! This beautifully maintained 15 year old 4 bedroom 2.2 bathrooms home offers the perfect blend of comfort, space, and convenience. Step inside to find a bright and inviting layout with generous living areas, ideal for both everyday living and entertaining. The kitchen features ample cabinetry and workspace, flowing seamlessly into the dining area for easy gatherings. Upstairs, you’ll find 4 spacious bedrooms with great natural light, including a primary suite designed for relaxation at the end of a long day. The home also features a finished basement that provides additional living space — perfect for a home office, gym, or recreation area. Basement improvements were completed without permits and are being sold as-is; buyer to perform their own due diligence. Enjoy outdoor living with an unfenced private yard, ideal for summer barbecues and quiet evenings. Conveniently located near shopping, dining and major routes. Don’t miss your opportunity to own a home in one of Middletown’s most desirable communities — schedule your tour today!
#DENC2096586

MIDDLETOWN

248 ANN DRIVE

4 Beds

2 Baths

1,900 Sq.Ft.

$509,900

MLS#: DENC2096586

Welcome to the beautifully crafted Lexington model—brand new and READY NOW in the desirable Greenwood Hills community! This energy-efficient home offers nearly 2,000 sq. ft. of thoughtfully designed living space, with 4 spacious bedrooms and 3 full bathrooms, including a main-level bedroom and full bath w/ walk-in shower, perfect for guests, multi-generational living, or a home office. The kitchen features 36” painted cabinets w/ crown molding, elegant quartz countertops, floating shelves, stainless steel appliances with gas cooking, and a walk-in pantry with solid shelving. The kitchen flows seamlessly into the dining area and open family room, creating a welcoming space for both everyday living and entertaining. Upstairs, the primary suite provides a peaceful retreat, complete with a walk-in closet and private en-suite bath with tile shower. Two additional bedrooms and a hall bath complete the upper level. Additional highlights include a two-car garage, walk-out lower level ready to finish, and a 10 year home warranty for added peace of mind. Enjoy life in Greenwood Hills—a thoughtfully planned neighborhood with sidewalks, community benches, a modern park, and a scenic pond with an observation deck. Conveniently located with easy access to Route 283 and the PA Turnpike.
#PADA2045388

MIDDLETOWN

160 HARTFORD DRIVE

4 Beds

3 Baths

1,966 Sq.Ft.

$509,900

MLS#: PADA2045388

Welcome to a fully renovated, move-in ready home in the heart of Middletown — where the charm of a well-established neighborhood meets the confidence of major modern upgrades already completed. This beautifully updated 3-bedroom, 1.5-bath home features a brand-new kitchen, updated flooring, and refinished hardwoods that blend timeless character with today’s style. But what truly sets this home apart is what you won’t have to worry about: a new heat pump, new double-hung windows, new 200-amp electrical service, new gutters, and a roof replaced in 2024. The big-ticket items are done — offering peace of mind for years to come. Enjoy a spacious backyard ideal for entertaining, play, gardening, or simply relaxing after a long day. The location offers the best of both convenience and community — walk to local schools, shops, and town amenities, with easy access for commuters. Opportunities like this — fully updated with major systems already replaced — rarely come available in Middletown at this price point. Schedule your showing before it’s gone
#MDFR2077570

MIDDLETOWN

10 LINDEN BOULEVARD

3 Beds

1 Baths

2,104 Sq.Ft.

$509,000

MLS#: MDFR2077570

IMMEDIATE AVAILABILITY! Welcome to the 55+ community of Traditions at Whitehall - Ashton Carriage Town Home. This end unit first floor master comes w/a 2nd bedroom & loft, 2.5 baths, 2 car rear load attached garage, front porch, and additional finished upgrades. Community also offers trails, in ground pool w/lounge areas, open clubhouse featuring exercise room, billiards, gathering space, full kitchen and a large outdoor patio area! Builder Splits Transfer Tax (***Photos are of a similar home and may contain options & upgrades not included in listing price shown.***)
#DENC2081004

MIDDLETOWN

1102 HIGHLAND STREET 137 ASHTON

2 Beds

2 Baths

1,794 Sq.Ft.

$504,900

MLS#: DENC2081004

New on site 1 day ago
Enjoy breathtaking sunsets and peaceful privacy from this bright and sunny 3-bedroom, 2-bath ranch set on 2.2 acres with state-owned land directly behind the property. This inviting home offers easy one-floor living, a 2-car garage, and an unfinished basement (which also offers a pellet stove) providing excellent storage and future potential. Inside, you'll find hardwood floors and tile throughout the main living areas and an abundance of natural light that fills the home. The living and dining rooms feature soaring cathedral ceilings, creating an open and spacious feel, and lead to sliding glass doors that open to a sun porch and concrete patio, perfect for relaxing or entertaining while enjoying the surrounding landscape and evening sunsets. The primary suite features cathedral ceilings and sliding doors leading directly outside, offering a private retreat with beautiful views of the backyard and the preserved land beyond. Two additional bedrooms and a second full bath complete the main level. The home also includes a convenient laundry area located near the kitchen and a layout designed for comfortable everyday living. While the property needs a little TLC, it presents an exceptional opportunity to update and make it your own in a truly special setting. With peaceful surroundings, stunning sunsets, and protected land just beyond the backyard, this property is a rare find for buyers seeking privacy, nature, and potential. Property is being sold as-is. No unrepresented Buyers. No offers accepted via text message.
#DENC2098160

MIDDLETOWN

847 SILVER RUN ROAD

3 Beds

2 Baths

1,375 Sq.Ft.

$500,000

MLS#: DENC2098160

The Asheville - with over 2,800 finished sq. ft. - delivers modern design and comfortable living with spaces made for both entertaining and everyday relaxation. The contemporary kitchen is the heart of the home, featuring a large island, walk-in pantry, and designer Looks interior selections that elevate the space. A covered front porch and rear deck invite you to welcome guests or unwind outdoors, while the impressive great room with a vaulted ceiling creates a bright, open atmosphere inside. The luxurious primary suite is a true retreat, highlighted by triple windows and an elegant tray ceiling. The primary bath offers a spa-like experience with dual sinks, a walk-in closet, and the option for a freestanding tub. Downstairs, the finished basement expands your living space with a recreation room, bedroom, and full bath—ideal for guests, hobbies, or flexible living needs. 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.
#DENC2096240

MIDDLETOWN

1511 LESTERFIELD WAY

3 Beds

2 Baths

1,811 Sq.Ft.

$499,990

MLS#: DENC2096240

MASSEY ELITE END UNIT- 3 bedrooms, 2.5 baths, 2 car garage. Approx. 2380 SF! 12x10 Deck. This home features a Finished den, 42" cabinets in kitchen, island, stainless gas range, dishwasher, microwave, LVP flooring and recessed lighting in Kitchen. LVP floor and Tile Shower surround in master bath. 3 pc rough in walk out basement. Don't miss out on this spectacular floor plan! Builder Splits Transfer Tax. Beautifully appointed end unit townhome featuring 3 bedrooms, 2.5 baths, and approximately 2,333 square feet of living space. This home includes a 2-car garage and a 12x16 deck overlooking open farmland. Interior features include upgraded luxury vinyl plank flooring throughout the main level, a gourmet kitchen with granite countertops, Level 3 cabinetry, a large center island, and a gas range. The primary suite offers a spacious layout with a walk-in closet and private bath. Located in one of the community’s most desirable settings with no building in front, open space surrounding, and ample parking.
#DENC2092162

MIDDLETOWN

442 REDERICK LANE MASSEY ELITE LOT 70

3 Beds

2 Baths

2,333 Sq.Ft.

$498,053

MLS#: DENC2092162

Rare opportunity to own a private homesite in the desirable River Ridge on the Shenandoah community in Middletown, VA. This undeveloped parcel offers the perfect setting for a custom-built home, weekend retreat, or long-term investment. Enjoy natural surroundings, peaceful privacy, and the flexibility to design and build to your vision (subject to county approvals). Located just minutes from historic Middletown, local dining, wineries, and commuter routes, this property offers a unique balance of seclusion and convenience. Land opportunities in this area are limited, secure your future homesite today. Strategically priced based on current land market trends and buyer activity, this property is being marketed to attract qualified end users and investors alike. Ideal for out-of-state buyers, builders, or those seeking to secure land for future use. Don’t miss the chance to own land with flexibility, upside potential, and location appeal. Come build your dream home on this stunning 20-acre parcel tucked within a private community. Ideally located just minutes from Front Royal, Winchester, I-66, and I-81, this property offers the perfect balance of peaceful seclusion and easy access to nearby towns and amenities. Enjoy mountain views and direct frontage on the beautiful Shenandoah River — ideal for fishing, kayaking, and embracing nature’s serenity. With gently rolling terrain and potential building sites, the possibilities are endless for creating your full-time residence, weekend escape, or legacy property. Approximately 400 feet of frontage on the North Fork of the Shenandoah River. Don’t miss this rare opportunity to own a private piece of the Shenandoah Valley.
#VAWR2011208

MIDDLETOWN

0 RIVER RIDGE DRIVE

None Beds

None Baths

20.0 acres

$480,000

MLS#: VAWR2011208

WOW! Simply Gorgeous! This popular Kipling model offers open floor plan, foyer with 11 FT ceiling, wainscoting and gleaming hardwoods extending from foyer thru living room, dining room and kitchen. Well appointed kitchen has granite counters including island with seating for 3, stainless steel appliances, recessed & upgraded lighting. Dining area has sliders to upgraded & enlarged paver patio, upgraded landscaping with paver edging, wonderful front porch & irrigation system. Primary bedroom has plush carpeting, tray ceiling, walk-in closets and full bath with raised height vanity, walk-in tiled shower and beautiful ceramic tiled floor. 2nd bedroom is close to the entry door and another full bath. Main floor laundry room has tiled floor, cabinets, wash tub and washer & dryer included. Additional 2nd floor 12 X 15 Storage Room and storage in the crawl space.This sensational home is located in the premier 55+ Community of Spring Arbor offering a clubhouse, heated salt water pool, bocci ball courts, picnic area, fitness room, immense gathering room with kitchen facilities, library and game rooms including billiards. Great location close to major roads, walking distance to restaurants and shopping..
#DENC2096388

MIDDLETOWN

148 GAZEBO LANE

3 Beds

2 Baths

1,650 Sq.Ft.

$479,900

MLS#: DENC2096388

**Move-in ready new construction townhome in idyllic 55+ community** Now is the perfect time to buy your new home at The Venue at Winchelsea, Middletown, DE's premiere active adult community. This move-in ready two-story townhome offers low-maintenance living with sophisticated style and thoughtful design. Enter to find a dedicated study—perfect for a home office—and a convenient first-floor laundry. The gourmet kitchen shines with modern stainless steel appliances, sleek quartz countertops, 42” cabinetry, a wall oven, and gas cooktop. The open layout flows seamlessly into the dining and living areas, with an included patio to enjoy unwinding during the upcoming spring and summer months. The first-floor owner’s suite is a peaceful retreat with a private bath and spacious walk-in closet. Upstairs, two additional bedrooms, a full bath, and a versatile loft provide comfort and privacy for guests. Schedule your private tour today!! Community Highlights: This 55+ Active Adult neighborhood features a 5,400 sq. ft. clubhouse, pickleball, tennis, bocce, swimming pool, fitness center, and more. Lawn care, snow removal, trash, and recycling are all included—leaving you free to enjoy the lifestyle you’ve been waiting for. Pictures are of model home and for representational purposes only. Please see New Home Consultant for details. Taxes to be assessed after settlement. Realtor representation must be acknowledged on the first interaction with Lennar, and the agent must accompany their client on the first visit. For tours and open houses, visit the model home at 2405 Greyfriar Loop.
#DENC2097802

MIDDLETOWN

2311 WINCHELSEA PARKWAY

3 Beds

2 Baths

2,443 Sq.Ft.

$479,890

MLS#: DENC2097802

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