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

76 Properties Found. Page 3 of 6.

Rare opportunity to own a double lot in town at an affordable price. This spacious home offers a ton of possibilities. The current owner has done a lot of upgrades over the last few years by updating the kitchen, the flooring, vanities, interior doors and paint. The metal roof was installed in 2021 and the A/C is only 3 years old. The double lot adds to this property in many ways, build a pole barn, build a separate rental or just leave it empty and let the kids play. Schedule your tour today.
#DENC2092074

MIDDLETOWN

908 S CASS STREET

4 Beds

1 Baths

2,200 Sq.Ft.

$430,000

MLS#: DENC2092074

None
#DENC2094038

MIDDLETOWN

40 S CUMMINGS DRIVE

3 Beds

2 Baths

2,200 Sq.Ft.

$429,500

MLS#: DENC2094038

Welcome to your next chapter in the vibrant, caring haven of Whispering Woods — an active adult community where life is anything but boring. This beautifully maintained, just 5 years young home greets you with an open concept layout, two full baths, two bedrooms and a truly spacious walk‑in closet that feels almost like a private room. Spectacularly clean, neutral finishes, adult friendly 1 story home and walk in tub, 2 sink kitchen and spacious cooking area! Step outside your door and into a world of daily fun: pickleball, bocce, swimming, social clubs, themed events all year round, and a dining hall with a bar and billiards area tailor‑made for neighbors to become friends. All of this is just minutes shopping and restaurants, with easy access to Routes 1, 301, and 896. The remaining balance of the builder's warranty are transferable to the new owner making this home a smart choice in today’s market. Landscape and exterior care are handled by the community.
#DENC2090658

MIDDLETOWN

1428 WHISPERING WOODS ROAD

2 Beds

2 Baths

1,275 Sq.Ft.

$428,000

MLS#: DENC2090658

** WORKFORCE HOUSING-BUYER MUST QUALIFY FOR THE NEW CASTLE COUNTY PROGRAM TO PURCHASE -MASSEY INTERIOR UNIT- 3 bedrooms, 2.5 baths, 1 car garage. Approx. 2001 SF! This home features a Finished den, 12x10 DECK, 42" cabinets in kitchen, island, stainless steel appliances, gas range, dishwasher, microwave and recessed lighting in Kitchen. LVP flooring upgrades. 3 pc rough in walk out basement. Don't miss out on this spectacular floor plan! Builder Splits Transfer Tax
#DENC2092584

MIDDLETOWN

446 REDERICK LANE MASSEY LOT 68

3 Beds

2 Baths

2,001 Sq.Ft.

$427,056

MLS#: DENC2092584

Superb. newer carriage style home located in the ever popular active adult community of Whispering Woods!! Oversized great room with recessed lighting, gas fireplace and luxury vinyl plank flooring, gourmet kitchen w/granite countertops, stainless steel appliances, island and separate eating area, owners suite with coffered ceiling, ceiling fans, sitting area and oversized walk-in closet and more!! Outside enjoy the private screened porch with ceiling fan and paver patio!! Two car garage!!! Community amenities are countless with the pool, clubhouse, pickleball, themed events and more!! Don't miss this gem!!
#DENC2093778

MIDDLETOWN

1415 WHISPERING WOODS ROAD

2 Beds

2 Baths

1,875 Sq.Ft.

$424,900

MLS#: DENC2093778

Nestled in the charming Middletown community, this delightful split foyer home offers a perfect blend of comfort and convenience. Located on a corner lot, there is ample space for guest parking and outdoor activities. The exterior of the home has been updated with beautiful new siding, gutters and downspouts in 2019. The well-maintained interior boasts 1,396 sq. ft. of living space, featuring three cozy bedrooms and a full bath. This home includes a spacious basement that contains 2 additional rooms for your convenience, a half bath and private office space. Enjoy evenings by the fireplace or host gatherings on the inviting patio overlooking a spacious 0.4-acre lot, complete with a personal above-ground pool and a play area for outdoor fun. The neighborhood is known for its friendly atmosphere and proximity to local parks, providing many opportunities for recreation and relaxation. With easy access to essential amenities and a welcoming spirit, this home is not just a place to live, but a place to thrive. Experience the warmth of Middletown and make this lovely residence your own!
#MDFR2073592

MIDDLETOWN

7129 LIMESTONE LANE

4 Beds

1 Baths

1,396 Sq.Ft.

$420,000

MLS#: MDFR2073592

Experience elevated living at 306 E Harvest Lane—an impeccably renovated two-story home in the desirable Appoquinimink school district. Step into an inviting foyer with an updated half bath and new luxury vinyl plank flooring, setting the tone for contemporary style throughout the residence. The newly refreshed eat-in kitchen dazzles with shaker white cabinets, granite countertops, striking glass tile backsplash, high-end stainless steel appliances (including a French Door refrigerator with ice maker), recessed lighting, and a remote-controlled ceiling fan. From here, a sliding door opens to a spacious rear deck and ample backyard, perfect for gatherings and play. Retreat upstairs to three comfortable bedrooms, including a king-sized master suite featuring vaulted ceilings, recessed lighting, and a private bath with a walk-in shower and sleek floating vanity. Both full bathrooms are fully updated, adorned with matte black finishes and modern vanities. The home’s theme of sophisticated matte black details carries throughout every space. The versatile partially finished basement offers flexible extra space—ideal for a playroom, home gym, office, or a secluded man cave. The basement also contains a generous laundry room with brand new washer and dryer appliances for convenience and comfort. Sitting on a large 151 x 136 lot, the property boasts an attached two-car garage with an electric door opener, further enhancing everyday ease. With recent upgrades in paint, flooring, kitchen, lighting, and appliances, this home is move-in ready and embodies exceptional value for anyone seeking top-tier amenities and extra space in a sought-after community. Schedule your private tour today to take advantage of this rare opportunity—homes in this condition and location don’t last long!
#DENC2094422

MIDDLETOWN

306 E HARVEST LANE

3 Beds

2 Baths

1,250 Sq.Ft.

$419,999

MLS#: DENC2094422

BASE PRICE LISTING - MODEL HOME IS NOT FOR SALE. Welcome to a stylish and spacious 3-story townhome that offers 1 or 2 garages, square footage ranging from 2,001-2,333 & contemporary living at its finest. With 3 bedrooms, 2.5 baths, and a finished den on the first level with rough in plumbing for a future bathroom, this home is designed to provide both comfort and versatility. As you step inside, you're greeted by a modern floor plan that seamlessly connects the living, dining, and kitchen areas. The first level features a beautifully finished den, perfect for use as a home office, entertainment room, or guest space. Sliding glass doors lead to a private outdoor area where you can enjoy your private space and create a tranquil retreat. The builder is currently offering this optional finished space as part of their incentive. The second floor is the heart of the home, boasting a spacious great room flooded with natural light. It's an ideal space for relaxation, with enough room to accommodate your favorite furniture and decor. The nearby dining area is perfect for hosting meals and gatherings, and it flows effortlessly into the well-appointed kitchen. The kitchen features modern appliances & ample cabinet space. Whether you're preparing a quick weekday dinner or hosting a special occasion, this kitchen has everything you need. On the third level, you'll discover three generously sized bedrooms, each with its own character and charm. The primary bedroom is a luxurious retreat, complete with an en-suite bathroom featuring double vanities, and a separate shower. The other bedrooms share a well-appointed full bathroom, ensuring convenience for family and guests. These 3-story townhome offer the perfect blend of modern living and functionality. It provides plenty of space for relaxation and entertainment, and the finished den on the first level adds extra versatility to suit your lifestyle. With its contemporary design & ample storage, these townhomes are a welcoming place to call home. Massey Elite Model Home - 3 bedrooms, 2.5 baths, 2 car garage. Approx. 2333+ SF! This home features a laundry list of upgrades! *Price does not reflect all upgrades and designer features shown in model home. Base Price Only. For self-guided tours 7am-8pm daily; Download "NterNow" on your smart phone. Complete registration while standing in front of homes door. Have driver's license handy as the app will ask you to scan. Enter property ID located on front door. Door will automatically unlock. Please secure door when leaving as the door will lock itself within 30 seconds of leaving property.
#DENC2080226

MIDDLETOWN

1300 CARRICK COURT MASSEY ELITE MODEL

3 Beds

2 Baths

2,001 Sq.Ft.

$416,000

MLS#: DENC2080226

Welcome to Venue at Winchelsea by Lennar — Middletown’s premier 𝐚𝐜𝐭𝐢𝐯𝐞 𝐚𝐝𝐮𝐥𝐭 (𝟓𝟓+) 𝐜𝐨𝐦𝐦𝐮𝐧𝐢𝐭𝐲 offering low-maintenance living, spacious designs, and exceptional value. This 2,669 sq. ft. two-story townhome is part of 𝐋𝐞𝐧𝐧𝐚𝐫’𝐬 𝐏𝐚𝐭𝐡𝐰𝐚𝐲 𝐭𝐨 𝐎𝐰𝐧𝐞𝐫𝐬𝐡𝐢𝐩 𝐏𝐫𝐨𝐠𝐫𝐚𝐦 -𝐚𝐩𝐩𝐥𝐢𝐜𝐚𝐭𝐢𝐨𝐧 𝐚𝐧𝐝 𝐢𝐧𝐜𝐨𝐦𝐞 𝐪𝐮𝐚𝐥𝐢𝐟𝐢𝐜𝐚𝐭𝐢𝐨𝐧 𝐚𝐫𝐞 𝐫𝐞𝐪𝐮𝐢𝐫𝐞𝐝 𝐟𝐨𝐫 𝐩𝐮𝐫𝐜𝐡𝐚𝐬𝐞. 3108 Pett Level Drive is a move-in ready home thoughtfully designed for comfort and ease. The first floor features an inviting open-concept layout that blends the kitchen, dining, and living areas—perfect for both everyday living and entertaining. The luxurious first-floor owner’s suite is privately tucked away in the rear of the home and includes a spa-inspired en-suite bath and generous closet space. A secondary bedroom at the front of the home offers flexibility for guests or a home office. Upstairs, a central loft anchors three additional bedrooms, providing ample space for hobbies, visitors, or multigenerational living. About the community: Venue at Winchelsea is designed for an active, social lifestyle. Come tour the amenities which include a 5,400 state-of-the-art clubhouse, outdoor pool, pickleball and bocce courts, community gardens, and more. *Pictures are artist renderings and for representational purposes only. Please see New Home Consultant for details. Taxes to be assessed after settlement. If using a Realtor: the agent's client must acknowledge on their first interaction with Lennar that they are being represented by a Realtor, and the Realtor must accompany their client on their first visit. Please contact the Lennar Sales Team directly for questions about qualifications and how to apply for the MPDU program. We are happy to walk you through the process.* For appointments and open houses, please visit the welcome home center at 2405 Greyfriar Loop.
#DENC2093754

MIDDLETOWN

3108 PETT LEVEL DRIVE

5 Beds

2 Baths

2,669 Sq.Ft.

$412,800

MLS#: DENC2093754

Welcome to 149 Gazebo Lane, a charming, well-appointed, end unit carriage home in the highly sought after Spring Arbor community! You'll love the welcoming 2-story foyer that flows seamlessly into the expansive living & dining areas, complete with gleaming hardwoods & timeless style! The spacious, bright eat-in kitchen features newer appliances & maple cabinetry- perfect for casual meals or culinary creativity. There's a sunroom retreat that boasts vaulted ceilings & direct access to the screened porch, an inviting space for relaxation or entertaining. The main level also offers a comfortable guest bedroom, conveniently located adjacent to a full bath, ideal for visitors. The primary bedroom features tray ceiling, walk-in closet, and full ensuite for comfort & style. There's a FULLY FINISHED bonus room/ loft, perfect for an office, hobby room, & more! Practical conveniences with this property include a full laundry room, storage area, as well as inside access to the garage, helping to make everyday living effortless! Energy Efficient Comfort: This home features dual-zone heating & cooling- a definite money saver during seasonal changes and a great way to keep both floors comfortable year 'round! There's also walking & biking trails, tennis courts, a large clubhouse with library, hobby/game room, fitness center, billiards & more, with outside pool- great for events and connecting with neighbors. This is a prime location, SO close to shopping, restaurants, entertainment, Urgent Care/hospitals, and more- everything you need just steps away! This home has the perfect blend of style, functionality and community living! Don't miss your chance- schedule a tour and make an offer TODAY!
#DENC2093004

MIDDLETOWN

149 GAZEBO LANE

2 Beds

2 Baths

1,825 Sq.Ft.

$410,000

MLS#: DENC2093004

OPEN HOUSE; SATURDAY & SUNDAY ;DECEMBER 6th & 7th; NOON-2pm. Welcome Home to Spring Arbor! This beautifully maintained end-unit carriage-style home nestled in the quiet, highly desirable active adult community of Spring Arbor. The open floor-plan offers comfort, convenience, and elegant one-floor living—perfectly designed with your lifestyle in mind. Step inside to discover a bright and airy layout featuring two generously sized bedrooms, two full bathrooms, and luxury vinyl plank (LVP) flooring throughout—no carpet! The primary suite is a true retreat, offering space for a cozy sitting area, an expansive walk-in closet, and a private en-suite bath with a walk-in shower. The heart of the home features a large living room that flows seamlessly into the dining area, ideal for entertaining family and friends. The sun-room provides a tranquil sitting area with access to the backyard patio, creating the perfect indoor-outdoor living experience. The kitchen offers abundant counter space, plenty of cabinetry, and a pantry—providing plenty of storage and workspace for any home chef. As an end unit, you’ll appreciate the added privacy, extra windows for natural light, and a serene setting within this vibrant 55+ community known for its welcoming neighbors and active lifestyle. Recent updates include: High-efficiency heat pump water heater (1 year old), HVAC system (3 years old) and Whole-house professional painting (completed before listing). For added peace of mind, the seller is including a comprehensive 2-10 One-Year Home Warranty. Don’t miss this opportunity to make this exceptional home your own in one of the area’s most sought-after communities—Spring Arbor, where comfort, convenience, and community come together beautifully.
#DENC2092132

MIDDLETOWN

107 GAZEBO LANE

2 Beds

2 Baths

1,675 Sq.Ft.

$409,900

MLS#: DENC2092132

Beautifully updated 4-bedroom, 2-bath Cape Cod situated on a spacious 0.36-acre corner lot in the heart of Middletown. Perfectly located within walking distance to Appoquinimink schools, Main Street shopping, and all that downtown Middletown has to offer, this home blends timeless charm with modern updates. The stately brick exterior, lush landscaping, and split sidewalks set the tone as you approach, with two covered entrances providing convenient protection from the elements. Nearly every aspect of this home has been updated over the past decade, including a modern open-concept kitchen, renovated bathrooms, architectural shingle roof, newer windows, furnace, and interior paint throughout. Inside, gleaming hardwood floors flow through the living room, dining area, hallways, and bedrooms. The stunning kitchen boasts 42” shaker-style cabinetry with crown molding, granite countertops, stainless steel appliances, tiled floors and backsplash, and a peninsula with bar seating. The kitchen opens to a bright living area anchored by a brick fireplace. The main level features two spacious bedrooms and an updated full bath, while the upper level offers two additional bedrooms, a renovated full bath, and a versatile flex space. The walk-out basement expands your options for future finishing potential. Outdoor living shines here—step from the kitchen into a large screened breezeway with epoxy-coated floors, ceiling fan, updated lighting, and a built-in brick grill for bug-free summer evenings. Prefer the sun? Relax on the newer Trex deck overlooking a landscaped backyard bordered by Rose of Sharon and Crepe Myrtle trees. The property also includes a two-car enclosed carport that can easily be converted into a garage, along with driveway parking for up to four additional vehicles. With its prime location, thoughtful updates, and charming outdoor spaces, this Middletown gem is a must-see!
#DENC2089002

MIDDLETOWN

701 S BROAD STREET

4 Beds

2 Baths

2,125 Sq.Ft.

$409,000

MLS#: DENC2089002

Welcome to 810 Lisicassey Loop in Middletown! This well-maintained 3 bedroom, 2.5 bath home offers comfortable living in the quiet picturesque community of Hyatt's Crossing. The main level features an open, functional layout with a bright living area, dining space, and a well-equipped kitchen designed for everyday convenience. Upstairs, the spacious primary suite includes a private bath, accompanied by two additional bedrooms suited for guests, family, or home office use. The finished basement provides valuable extra living space — ideal for recreation, fitness, or media. The home is in close proximity to shopping, dining, schools, and major routes, blending privacy with accessibility. A great opportunity for buyers looking for space, comfort, and a welcoming community.
#DENC2093128

MIDDLETOWN

810 LISSICASEY LOOP

3 Beds

2 Baths

2,425 Sq.Ft.

$400,000

MLS#: DENC2093128

Vintage charm with modern amenities. This home built in the 1800s is on just about 1 acre. It has 2 bedrooms and 2 full baths and 1 powder room. There is also an extra room in the back that could be a third bedroom . The exposed beams and brickwork are amazing. The kitchen has been updated with a quartz countertop, tile backsplash and a new stainless appliance package. You have to see this in person so add this to your tour today.
#DENC2086978

MIDDLETOWN

467 HYETTS CORNER ROAD

3 Beds

2 Baths

1,900 Sq.Ft.

$399,999

MLS#: DENC2086978

Investor Alert! High Cash Flow + Strong ROI - Welcome to 219 South Union Street in Middletown - a fully improved mixed-use, multi-unit property offering impressive income and strong long-term upside! Featuring 1 commercial unit and 3 residential apartments, all separately metered and recently updated, this is a turn-key investment opportunity in a desirable downtown location. Income Breakdown: Commercial Unit: $1,195/mo, 1BR/1BA Apartment: $1,070/mo (currently leased month to month - higher market rent potential), (2) 2BR/1BA Apartments: $1,495/mo each. - Total Monthly Gross Rent: $5,255 Annual Gross Income: $63,060 WOW!! CAP Rate of 11.56%, and Cash on Cash Return of 19.91%, 5-Year Investment Rate of Return (5% Appreciation) - 31.72%!! MASSIVE Depreciation Benefit!! This property combines commercial stability with residential demand and future appreciation off the charts. Tenants pay their own electric, minimizing owner expenses. The building features high ceilings, exposed brick, ornate details, and private rear balconies for each apartment. Don’t miss this rare, high-yield investment opportunity in thriving downtown Middletown!
#PADA2049614

MIDDLETOWN

219 S UNION STREET

None Beds

None Baths

3,186 Sq.Ft.

$399,000

MLS#: PADA2049614

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