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

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
108
# of Listings
3
Avg # of Bedrooms
$329
Avg. $ / Sq.Ft.
$549,088
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

298 Properties Found. Page 18 of 20.

Brand new, never-lived-in home available for rent! This beautiful house features 4 bedrooms, 2 full baths, and 1 half bath. It is located in a very convenient area, close to shopping and major amenities. We require applicants to have a minimum credit score of 625 and have a monthly gross income of 2X rent or more. If you’re looking for a comfortable and modern home in a great location, please come and see it!
#DENC2093866

MIDDLETOWN

309 S THALES DRIVE

4 Beds

2 Baths

2,300 Sq.Ft.

$3,800

MLS#: DENC2093866

This gorgeous four bedrooms, two & a half bathrooms and two car garage estate in the heart of the Estates at St. Anne's in stunning Middletown is the rental of your dreams! With a gorgeous open plan layout where the two story foyer gives way to the formal living and dining room which wraps around to the great room with plentiful windows and a towering vaulted ceiling! The kitchen boasts all updated appliances, a giant island, a breakfast nook and an attached breakfast room with windows & natural light everywhere. The upper level shows off a giant master suite complete with sitting room and four huge closets, an en-suite bath with separate tub and shower, dual vanities. The backyard is large & spacious with so much room to spread out, and this grand estate is set in the heart of the highly coveted Appoquinimink School District!! Apply today- this rental will not be available long!
#DENC2093490

MIDDLETOWN

304 GALLOWAY STREET

4 Beds

2 Baths

2,975 Sq.Ft.

$3,200

MLS#: DENC2093490

Limited time offer... TWO MONTHS FREE (must take possession before the end of 2025 & sign a 14 month lease). END UNIT. BRAND NEW. NEVER BEEN LIVED IN. Pet friendly townhome from Benchmark Builders at The Town of Whitehall. Unfurnished. This sawt after community has loads to offer. Christiana Care's medical offices, Lorewood Grove Elementary, playgrounds, summer bear garden, dog park, fire pits, walking trails and much more. These 3 bedroom, 2.5 bath homes feature 2 car garages with opener, private driveways, LVP flooring on all floors, NO CARPET, tile baths, a large composite deck, granite countertops in the kitchen & stainless steel kitchen appliances. Located within the coveted Appoquinimink School District. EV CHARGER AVAILABLE FOR AN ADDITIONAL FEE. General liability Renters Insurance Required. Pets allowed at landlord's digression. Dogs: $500 deposit & an extra $50/month; Cats: $800 deposit & an extra $25/month. Tenant pays: electric, gas, water, & communication/cable, internet if desired. Landlord pays: trash, community assessments, sewer, property taxes & exterior landscaping/grass cutting. No smoking permitted. Please go to Zillow to fill out the online application. We require applicants to have a minimum credit score of 600 (If under 680 you need at least an 85% on time payment history) and have a monthly gross income of 2.5X rent or more.
#DENC2093100

MIDDLETOWN

862 MAPLETON AVENUE

3 Beds

2 Baths

2,067 Sq.Ft.

$3,199

MLS#: DENC2093100

Limited time offer... TWO MONTHS FREE (must take possession before the end of 2025 & sign a 14 month lease). END UNIT WITH LARGE PORCH. BRAND NEW. NEVER BEEN LIVED IN. Pet friendly townhome from Benchmark Builders at The Town of Whitehall. Unfurnished. This sawt after community has loads to offer. Christiana Care's medical offices, Lorewood Grove Elementary, playgrounds, summer bear garden, dog park, fire pits, walking trails and much more. These 3 bedroom, 2.5 bath homes feature 2 car garages with opener, private driveways, LVP flooring on all floors, NO CARPET, tile baths, a large composite deck, granite countertops in the kitchen & stainless steel kitchen appliances. Located within the coveted Appoquinimink School District. EV CHARGER AVAILABLE FOR AN ADDITIONAL FEE. General liability Renters Insurance Required. Pets allowed at landlord's digression. Dogs: $500 deposit & an extra $50/month; Cats: $800 deposit & an extra $25/month. Tenant pays: electric, gas, water, & communication/cable, internet if desired. Landlord pays: trash, community assessments, sewer, property taxes & exterior landscaping/grass cutting. No smoking permitted. Please go to Zillow to fill out the online application. We require applicants to have a minimum credit score of 600 (If under 680 you need at least an 85% on time payment history) and have a monthly gross income of 2.5X rent or more.
#DENC2093116

MIDDLETOWN

872 MAPLETON AVENUE

3 Beds

2 Baths

2,067 Sq.Ft.

$3,199

MLS#: DENC2093116

Welcome to 319 E Cochran St, a beautifully upgraded almost new townhouse offering 2,125 square feet of comfortable living space on a 2,178 square foot lot. This spacious home features 4 bedrooms and 3.5 bathrooms, thoughtfully designed to accommodate both functionality and style. Among the highlights are two owner’s suites, perfect for multi-generational living or added privacy—one of which is conveniently located on the first floor and includes a full ensuite bath. The interior boasts elegant hardwood and luxury vinyl flooring and stairs, adding warmth and character throughout. The kitchen is a chef’s dream with sleek granite countertops and ample space for cooking and entertaining. Step outside to the enclosed porch, complete with a cozy gas fireplace, creating a perfect year-round retreat for relaxation or gatherings. This home is move-in ready and blends comfort, versatility, and upgraded features in a desirable location. SPECIAL CLAUSES: 1) No smoking permitted 2) No pets permitted 3) Renters insurance required 4) Tenant pays all utilities including water, sewer, trash, oil, propane 5) Property is currently wired for security system, monitoring available at tenant expense 6) No alterations to home or grounds without written permission from Landlord 7) Use of area rugs or floor protectors required under all furniture resting on hardwood flooring 8) Tenant responsible for replacement of any batteries, bulbs, or filters in the property during tenancy 9) The property has a gas fireplace and tenant is prohibited from burning any additional materials 10) Clogged drains resulting from tenants’ actions will be repaired at the tenants’ expense 11) Tenant pays all utilities not provided by HOA/Condo Association. If you are currently working with an agent, please contact them to schedule a tour. If you do not have an agent, we can connect you with one who can assist you.
#DENC2086304

MIDDLETOWN

319 E COCHRAN STREET

4 Beds

3 Baths

2,125 Sq.Ft.

$3,000

MLS#: DENC2086304

Limited time offer... TWO MONTHS FREE (must take possession before the end of 2025 & sign a 14 month lease). BRAND NEW. NEVER BEEN LIVED IN. Pet friendly townhome from Benchmark Builders at The Town of Whitehall. Unfurnished. This sawt after community has loads to offer. Christiana Care's medical offices, Lorewood Grove Elementary, playgrounds, summer bear garden, dog park, fire pits, walking trails and much more. These 3 bedroom, 2.5 bath homes feature 2 car garages with opener, private driveways, LVP flooring on all floors, NO CARPET, tile baths, a large composite deck, granite countertops in the kitchen & stainless steel kitchen appliances. Located within the coveted Appoquinimink School District. EV CHARGER AVAILABLE FOR AN ADDITIONAL FEE. General liability Renters Insurance Required. Pets allowed at landlord's digression. Dogs: $500 deposit & an extra $50/month; Cats: $800 deposit & an extra $25/month. Tenant pays: electric, gas, water, & communication/cable, internet if desired. Landlord pays: trash, community assessments, sewer, property taxes & exterior landscaping/grass cutting. No smoking permitted. Please go to Zillow to fill out the online application. We require applicants to have a minimum credit score of 600 (If under 680 you need at least an 85% on time payment history) and have a monthly gross income of 2.5X rent or more.
#DENC2093106

MIDDLETOWN

866 MAPLETON AVENUE

3 Beds

2 Baths

2,067 Sq.Ft.

$2,999

MLS#: DENC2093106

Limited time offer... TWO MONTHS FREE (must take possession before the end of 2025 & sign a 14 month lease). BRAND NEW. NEVER BEEN LIVED IN. Pet friendly townhome from Benchmark Builders at The Town of Whitehall. Unfurnished. This sawt after community has loads to offer. Christiana Care's medical offices, Lorewood Grove Elementary, playgrounds, summer bear garden, dog park, fire pits, walking trails and much more. These 3 bedroom, 2.5 bath homes feature 2 car garages with opener, private driveways, LVP flooring on all floors, NO CARPET, tile baths, a large composite deck, granite countertops in the kitchen & stainless steel kitchen appliances. Located within the coveted Appoquinimink School District. EV CHARGER AVAILABLE FOR AN ADDITIONAL FEE. General liability Renters Insurance Required. Pets allowed at landlord's digression. Dogs: $500 deposit & an extra $50/month; Cats: $800 deposit & an extra $25/month. Tenant pays: electric, gas, water, & communication/cable, internet if desired. Landlord pays: trash, community assessments, sewer, property taxes & exterior landscaping/grass cutting. No smoking permitted. Please go to Zillow to fill out the online application. We require applicants to have a minimum credit score of 600 (If under 680 you need at least an 85% on time payment history) and have a monthly gross income of 2.5X rent or more.
#DENC2093114

MIDDLETOWN

870 MAPLETON AVENUE

3 Beds

2 Baths

2,067 Sq.Ft.

$2,949

MLS#: DENC2093114

Gorgeous 3 bedroom 2.5 Bath Town-home is available in the heart of Middletown DE. The home is spotless. Entertain on the ground floor lounge area with a Refreshment Bar. 2nd floor has a Huge Living-room with Electric fireplace, recessed lights, and plenty of windows flooding the space with light. Kitchen and dining room is on the same floor. Kitchen has Granite counters including an island. Sliding door to large Deck is off the dining room for ultimate relaxation or dining al fresco. The third floor boasts a large Main bedroom with ensuite and walk in closet. The other two bedroom are a good size with good closet space. The Washer and Dryer is conveniently located on the third floor. The garage fits two cars and there is enough space for you to park two cars in the off-street parking space. Enjoy the fenced in yard. Easy walk to Walmart, Marshall's, Koh'ls, and eateries. Great Landlord. ACT NOW
#DENC2092962

MIDDLETOWN

114 RIDGEMONT DRIVE

3 Beds

2 Baths

2,200 Sq.Ft.

$2,900

MLS#: DENC2092962

Limited time offer... TWO MONTHS FREE (must take possession before the end of 2025 & sign a 14 month lease). BRAND NEW. NEVER BEEN LIVED IN. Pet friendly townhome from Benchmark Builders at The Town of Whitehall. Unfurnished. This sawt after community has loads to offer. Christiana Care's medical offices, Lorewood Grove Elementary, playgrounds, summer bear garden, dog park, fire pits, walking trails and much more. These 3 bedroom, 2.5 bath homes feature 2 car garages with opener, private driveways, LVP flooring on all floors, NO CARPET, tile baths, a large composite deck, granite countertops in the kitchen & stainless steel kitchen appliances. Located within the coveted Appoquinimink School District. EV CHARGER AVAILABLE FOR AN ADDITIONAL FEE. General liability Renters Insurance Required. Pets allowed at landlord's digression. Dogs: $500 deposit & an extra $50/month; Cats: $800 deposit & an extra $25/month. Tenant pays: electric, gas, water, & communication/cable, internet if desired. Landlord pays: trash, community assessments, sewer, property taxes & exterior landscaping/grass cutting. No smoking permitted. Please go to Zillow to fill out the online application. We require applicants to have a minimum credit score of 600 (If under 680 you need at least an 85% on time payment history) and have a monthly gross income of 2.5X rent or more.
#DENC2093104

MIDDLETOWN

864 MAPLETON AVENUE

3 Beds

2 Baths

2,067 Sq.Ft.

$2,899

MLS#: DENC2093104

Brand new, never been lived in rental in Appo school district. Fence coming soon. Pet friendly townhome from Benchmark Builders at The Town of Whitehall. Unfurnished. This sawt after community has loads to offer. Christiana Care's medical offices, Lorewood Grove Elementary, playgrounds, summer bear garden, dog park, fire pits, walking trails and much more. These 3 bedroom, 2.5 bath homes feature a private driveway with 2 parking spots, LVP flooring on all floors, NO CARPET, tile baths, FINISHED BASEMENT, granite countertops in the kitchen & stainless steel kitchen appliances. Located within the coveted Appoquinimink School District. EV CHARGER AVAILABLE FOR AN ADDITIONAL FEE. General liability Renters Insurance Required. Pets allowed at landlord's digression. Dogs: $500 deposit & an extra $50/month; Cats: $800 deposit & an extra $25/month. Tenant pays: electric, gas, water, & communication/cable, internet if desired. Landlord pays: trash, community assessments, sewer, property taxes & exterior landscaping/grass cutting. No smoking permitted. Please go to Zillow to fill out the online application. We require applicants to have a minimum credit score of 600 (If under 680 you need at least an 85% on time payment history) and have a monthly gross income of 2.5X rent or more.
#DENC2089214

MIDDLETOWN

851 MAPLETON AVENUE

3 Beds

2 Baths

1,922 Sq.Ft.

$2,899

MLS#: DENC2089214

Welcome to your new rental home in the charming town of Middletown, VA! This spacious 4-bedroom, 2.5-bath single-family home offers the perfect blend of comfort, style, and convenience. Enjoy an open floor plan that’s ideal for both everyday living and entertaining, featuring a large kitchen island and plenty of room to gather. The generously sized bedrooms provide comfort and flexibility, while the large, useable backyard offers an inviting space for outdoor relaxation or play. Need an office? A first floor office or playroom provides additional convenience. Conveniently located near major commuter routes—including I-81, Route 11, I-66, Route 7, and Route 50—this home makes commuting simple and efficient. You’ll also be just minutes from Winchester and Stephens City, and close to Shenandoah National Park, the Shenandoah River, local restaurants, and shopping. With its prime location and inviting layout, this Middletown rental offers the best of comfort and convenience in a fantastic setting.
#VAFV2037730

MIDDLETOWN

129 BIRMINGHAM

4 Beds

2 Baths

N/A

$2,850

MLS#: VAFV2037730

Brand New, Pet friendly townhome is ready for lease in Appoquinimink School District. 3-bedroom, 2 full, 2 half bath home features a 2-car garage, private driveway. The HOA fee is included in the rent. The HOA fee covers the following: snow removal from common areas (not porch or driveway), and lawn mowing/lawn care. General Liability Renters Insurance required. Tenant pays electric, gas, water, trash & communication/cable, internet if desired. Property pays community assessments, sewer, property taxes & exterior landscaping/grass cutting. No smoking permitted. Pets allowed at landlord's digression. Dogs: $500 deposit & an extra $50/month; Cats: $800 deposit & an extra $25/month.
#DENC2090742

MIDDLETOWN

549 LEWES LANDING ROAD

3 Beds

2 Baths

1,972 Sq.Ft.

$2,849

MLS#: DENC2090742

Welcome to 830 Woodline Drive in Middletown. This home sits on a large lot in a quiet setting and offers a practical layout with comfortable living space. The main level includes a living area, dining space, and a functional kitchen. The bedrooms are well-sized and allow for flexible use, including an office or guest room. The property provides ample outdoor space for everyday use, recreation, or future plans. Located close to local amenities, schools, and major routes, this home offers convenience and privacy. We look forward to having you as one of our valued tenants! Our company provides a property manager for you to contact at all times as well as a software system for reporting maintenance situations 24/7. Your customized move-in packet holds all the information you need to make your tenancy successful. No application is required before viewing the home. Any licensed realtor in the State of Delaware can show you the property. The property owner requires the following: 1) A credit score of 625 or higher, 2) They do a national eviction and criminal record check on anyone 18 and older. 3)The application fee is $50 per applicant. ONCE YOU SEE THE PROPERTY, we will need: 1) 2 months' worth of pay stubs or a job offer letter, or proof of any verifiable income such as child support, social security, pension, etc., 2)Photo ID, 3) A signed application which can be found on our 1stClassProperties website. Utilities will be put in your name, and to move in, you need one month's rent for the security deposit and the first month's rent
#DENC2092846

MIDDLETOWN

830 WOODLINE DRIVE

4 Beds

3 Baths

1,975 Sq.Ft.

$2,800

MLS#: DENC2092846

This building is divided into 3 rental units. Unit A (1) 1170 SF offices over full basement Unit B (2) 270 office with PR and kitchenette Unit C (3) 576 Two Car Garage with Two overhead garage doors with openers
#DENC2090664

MIDDLETOWN

5193 SUMMIT BRIDGE ROAD

None Beds

None Baths

N/A

$2,750

MLS#: DENC2090664

Welcome to your dream townhome nestled in a serene neighborhood in highly acclaimed Appo School District. This sunning 3-bedroom end unit with fenced yard boasts a wealth of amenities. PLEASE CALL FOR APPLICATION DETAILS AND TOUR SCHEDULING. Minimum 12 month lease, tenant to pay all utilities except lawn care. Call for details. NO SMOKING--NO EXEPTIONS.
#DENC2093848

MIDDLETOWN

1611 W MATISSE DRIVE

3 Beds

2 Baths

1,800 Sq.Ft.

$2,700

MLS#: DENC2093848

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