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
245
# of Listings
3
Avg # of Bedrooms
$275
Avg. $ / Sq.Ft.
$649,565
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

66 Properties Found. Page 1 of 5.

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

Price Improvement!!!!!!!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.

$499,900

MLS#: DENC2096586

Welcome to 79 Lattice Lane, a beautifully maintained detached ranch home in the highly desirable 55+ community of Spring Arbor in Middletown. Offering the ease of one-level living with the added bonus of an expansive finished basement, this home combines comfort, functionality, and low-maintenance living in one of the area’s most sought-after active adult communities. Inside, you’ll find a bright and inviting open floor plan filled with abundant natural light, beautiful hardwood flooring, and spacious living areas designed for both everyday enjoyment and entertaining. The kitchen opens seamlessly into the main living space, creating a warm and connected feel, while the sunroom offers the perfect place to relax with morning coffee, enjoy a good book, or host guests year-round. Step outside to the low-maintenance Trex deck, an ideal outdoor retreat for enjoying fresh air without the upkeep. Whether you are entertaining friends or simply enjoying a quiet evening at home, this property offers easy living both inside and out. The home features 2 generously sized bedrooms and 2 full baths, including a spacious primary suite with a walk-in closet and private bath. Both full bathrooms include linen closets for extra storage, and the home also offers a refreshed laundry area with additional cabinetry and folding space, making everyday tasks more convenient and organized. One of the most unique features of this home is the rare massive basement—a standout amenity in Spring Arbor. With 9-foot ceilings, a finished area, abundant storage, and workshop space, this lower level provides incredible flexibility for a home office, theater room, craft area, fitness space, hobby room, guest overflow, or additional living area. The possibilities are truly endless. Thoughtful updates add value and peace of mind, including kitchen appliances, sink, and garbage disposal approximately 2 years old, a Lennox natural gas heat system installed in 2020, and a 50-gallon electric Bradford White water heater. Additional features include a PEX manifold system, an extra electric panel in the basement, and ceiling fans in the bedrooms, living room, and sunroom, with some recently updated. Spring Arbor residents enjoy an exceptional lifestyle with outstanding community amenities, including a clubhouse, pool, fitness center, walking paths, and a variety of social and recreational activities. The HOA provides true low-maintenance living by covering grass cutting, mulching, tree pruning, snow removal, and common area maintenance. Even more impressive, the HOA also includes exterior maintenance for the roof, siding, and driveway—a rare and valuable benefit for a detached home. The roof was replaced approximately 6 years ago, offering even more confidence for the next owner. Move-in ready and filled with hard-to-find features, 79 Lattice Lane is a rare opportunity to enjoy spacious living, extensive storage, and a vibrant active adult lifestyle in a premier Middletown location (restaurants, shopping, and entertainment just minutes away). If you have been searching for a home that offers comfort, convenience, and room to spread out, this one is a must-see.
#DENC2099100

MIDDLETOWN

79 LATTICE LANE

2 Beds

2 Baths

2,275 Sq.Ft.

$499,000

MLS#: DENC2099100

MASSEY ELITE END UNIT- Late Spring Move-In! 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

New on site today
Your Next Chapter Begins in Springmill This isn’t just another home for sale in Springmill—it’s where your next chapter unfolds. Imagine waking up in the heart of Springmill, one of the most sought-after 55+ active adult communities near you, where every day feels like a retreat and every neighbor feels like a friend. As you arrive home, the beautifully manicured surroundings welcome you. The quiet charm of the neighborhood instantly sets the tone—this is more than a place to live; it’s a lifestyle designed for comfort, connection, and ease. Where Light, Space, and Comfort Meet. (side note, the square footage listed, does not include the finished basement) Step inside, and the home opens up before you—an airy, flowing layout that naturally draws your gaze toward peaceful, tree-lined views. At the center of it all is a chef-inspired kitchen, featuring timeless white cabinetry and generous counter space. Whether you're hosting Sunday dinner or enjoying a quiet morning coffee, everything feels connected. The kitchen flows effortlessly into the living area, where a warm gas fireplace creates the perfect setting for cozy evenings. Just beyond, your private retreat awaits: Sunroom – A light-filled sanctuary for reading, relaxing, and recharging year-round Screened Porch – Fresh air, no bugs, and tranquil views of a rare wooded backdrop This is indoor-outdoor living at its best—ideal for both quiet mornings and effortless entertaining. A Home Designed for Living—and Hosting While the main level offers two spacious bedrooms and 2.5 baths, the finished basement transforms this home into something truly special. This isn’t just extra space—it’s your entertainment hub, your guest retreat, your everything room: A third full bedroom for guests or a private home office A stylish wet bar ready for happy hour or celebrations A convenient half bath, keeping everything within reach Whether you're hosting overnight visitors or game night gatherings, this space adapts to your lifestyle. The Lifestyle You’ve Been Searching For Living in Springmill means more than owning a beautiful home—it means being part of a vibrant, active community. Enjoy access to: A welcoming clubhouse Fitness center and pool A full calendar of social events Beautifully maintained grounds and friendly neighbors If you’ve been searching for active adult communities near me, this is where comfort meets connection. Why This Home Stands Out If you're looking for: Homes for sale in Springmill 3-bedroom homes with finished basements 55+ communities with private wooded backyards This property checks every box—and then some. It offers a rare blend of privacy and community, elegance and functionality, relaxation and opportunity. The Story Starts Here This home isn’t just a place—it’s the setting for your next memories. Morning coffee in the sunroom. Evenings by the fire. Laughter echoing from the basement during gatherings. All that’s missing is you.
#DENC2100642

MIDDLETOWN

88 SPRINGMILL DRIVE

3 Beds

3 Baths

3,150 Sq.Ft.

$495,000

MLS#: DENC2100642

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 2,380 square feet of living space. This home includes a 2-car garage and a 12x10 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.
#DENC2090408

MIDDLETOWN

452 REDERICK LANE MASSEY ELITE LOT 65

3 Beds

2 Baths

2,380 Sq.Ft.

$489,900

MLS#: DENC2090408

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

Welcome to 365 Andrew Ct! This beautifully maintained, like-new home offers all the advantages of new construction without the wait. Nestled within the highly acclaimed Appoquinimink School District, this stunning end-unit townhome combines luxury with convenience. Featuring an expansive open-concept floor plan, this home is tailored for modern living. With 3 bedrooms, 2 full baths, 2 half baths, and a 2-car garage, there’s ample space for everyday life and entertaining. The chef’s kitchen is a standout with upgraded cabinetry, Quartz countertops, a stylish tile backsplash, and GE stainless steel appliances, seamlessly flowing into the dining area and great room. The lower level, currently used as a bedroom, offers versatile options for your needs. It could easily serve as a home office, gym, playroom, or guest suite. Luxury finishes throughout include LVP flooring on the main level, upgraded tile, and elegant details that enhance the home’s appeal. No need to wait for construction; this home is move-in ready in a community where opportunities like this are truly rare!
#DENC2092040

MIDDLETOWN

365 ANDREW COURT

3 Beds

2 Baths

N/A

$477,000

MLS#: DENC2092040

Welcome to the desirable community of Ponds of Odessa, where you’ll find this beautifully maintained and spacious carriage home. This property offers 3 bedrooms, 2 full bathrooms, and 1 half bathroom, with additional potential for a fourth bedroom or private office on the main level perfect for flexible living. As you enter, you’re greeted by a welcoming foyer that leads to a spacious eat-in kitchen, ideal for entertaining. The home features an open-concept dining and living area complete with an electric fireplace, creating a warm and inviting atmosphere. Just off the kitchen, enjoy a generous 16x12 deck overlooking a private backyard perfect for outdoor gatherings. The partially finished basement provides additional living space with endless possibilities, including a recreation area, home gym, or office. It also includes rough-ins for a future full bathroom, offering even more potential for customization. Upstairs, the primary suite boasts two separate walk-in closets, dual vanities, a walk-in shower, and a private water closet. The upper level also includes two additional spacious bedrooms, a full hall bathroom, and a conveniently located laundry room. Freshly painted with recently cleaned carpets, this home is move-in ready and waiting for its new owners. Schedule your private tour today!
#DENC2098026

MIDDLETOWN

1325 CARRICK COURT

3 Beds

2 Baths

2,575 Sq.Ft.

$475,000

MLS#: DENC2098026

**Move-in ready new construction townhome in idyllic 55+ community** Now is the perfect time to buy your new 3BR/2.5BA 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.
#DENC2099004

MIDDLETOWN

2243 WINCHELSEA PARKWAY

3 Beds

2 Baths

2,443 Sq.Ft.

$474,809

MLS#: DENC2099004

*More photos will be added soon* Welcome to this stunning, fully remodeled gem in the heart of Middletown! The house is near the 500 acres of Reserved State land. Thus there is no more place to build a new house in this area and it will never be crowded. If you wish to live in a serine scenic beauty and walk along the beach every afternoon then this house is the best for you. This house is a quick one minute walk away from the great Augustine beach. Also the Augustine Tavern is one minute walking distance from the house. No detail has been overlooked in this top-to-bottom transformation, offering the luxury of new construction with modern, high-end finishes throughout. The open-concept interior boasts all-new flooring, contemporary lighting, and a fresh, neutral palette. The living room is equipped with an electric fireplace is the centerpiece. Kitchen is featuring brand-new stainless steel appliances.. Step outside to your private, fully fenced backyard, providing the perfect space for entertaining, gardening, or pets. Location is everything! This home puts you minutes from the scenic C&D Canal and the natural beauty of the Woodland Beach and Augustine Beach areas. Enjoy easy access to the local ferry, vibrant downtown Middletown shops, and all area attractions. With all-new finishes and an unbeatable location near the water, this move-in-ready home is the perfect retreat. Schedule your tour today—this one won't last!
#DENC2098750

MIDDLETOWN

4 FARM LANE

4 Beds

2 Baths

1,900 Sq.Ft.

$465,000

MLS#: DENC2098750

Rare Opportunity – Fully Renovated 4-Bedroom Ranch in Middletown Don’t miss this rare opportunity to own a beautifully updated 4-bedroom, 2-bathroom ranch home in a peaceful setting in Middletown, DE, conveniently located just minutes from Route 13 and Route 1. You’ll fall in love with the elegant design and modern upgrades throughout, The modern kitchen is a true highlight, offering white cabinetry, black granite countertops, and high-end stainless steel appliances, along with new doors and windows, new flooring, and fresh paint throughout. Recent improvements include a new roof (2023) and siding, new concrete driveway, new HVAC, fresh paint, new light fixtures and new appliances throughout. The STUNNING fully finished basement adds approximately 1,000 sq. ft. of additional living space, complete with a recreation area and walkout access, providing excellent flexibility for entertainment, storage, or future use. Step outside to your private backyard retreat, featuring a spacious patio and Gazebo —perfect for family BBQs, summer gatherings, or relaxing evenings. This move-in ready home offers exceptional value, modern comfort, and long-term savings. Schedule your showing today!
#DENC2099828

MIDDLETOWN

2 GINA DRIVE

4 Beds

2 Baths

2,175 Sq.Ft.

$465,000

MLS#: DENC2099828

**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.

$463,409

MLS#: DENC2097802

Located in the highly sought after community Ponds Of Odessa this pristine end-unit townhouse offers the perfect balance of convenience as well as comfort. Upon entering you are greeted by natural light and a spacious open floor plan complete with a flex room that can double as an office. Upon exploring more of the home you have a vaulted ceiling and open living room and beautiful kitchen complete with upgraded countertops and cabinets. Downstairs you have an unfinished basement with a plethora of options gym, theater, or additional bedrooms and complete with rough plumbing for a future bathroom. Upstairs you'll find the spacious primary suite fully equipped with walk-in closet as well as an en-suite bathroom with dual vanities. The additional bedrooms are very comfortable sized with their own walk-in closets. Outside you'll find a concrete patio perfect for any outdoor activity. This property is located minutes from many amenities, shopping and local businesses. Also just minutes from major highways great for commuting. Schedule your showing today.
#DENC2094428

MIDDLETOWN

1341 CARRICK COURT

3 Beds

2 Baths

2,325 Sq.Ft.

$460,000

MLS#: DENC2094428

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