Middletown MD Homes for Sale

Middletown, MD is located in the western portion of Frederick County, with a population of about 4,000. This small mountain town is a tight-knit community with a quaint town center. There is plenty to do, especially if you enjoy outdoor activities. This area is perfect for those that want a home with lots of space and lots of land. There are tons of options for single family homes, including single story ranchers, neo-traditional homes within subdivisions, new-build and custom homes, or more established homes that have been a part of the community for a while. 

Browse current Middletown MD real estate listings below.
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3219 Middle Ridge Way Middletown MD 21769

Middletown, MD3219 Middle Ridge Way

Price$555,000

Est. Mortgage: $/month

MLS Number MDFR2026396

  • Single Family
  • Bedrooms 4
  • Bathroom 3
  • Square Feet 2,191
  • Acreage 1.36

OPPORTUNITY KNOCKS! Hurry to this 4 bedroom, solid brick Ausherman-built home on 1.3 acre in Brookridge North! When quality construction is coupled with original owners who have lovingly maintained their home, it's a WIN-WIN situation for any buyer! You'll find almost 2,200 finished sq ft on the main level with another 1,950 sq ft of unfinished space in the full lower level with double door walk-out. The main level includes formal living and dining rooms, an upgraded kitchen with granite countertops, full height backsplash and eating peninsula, stainless steel appliances including a full wall oven and built-in microwave/convection oven, wood cabinets, LVP flooring and pantry. The family room off the kitchen with vaulted ceiling and skylights offers a cozy propane fireplace with wooden mantle and raised brick hearth. The primary bedroom with renovated en-suite bath (2021) includes a walk-in shower and skylight with separate vanity area and walk-in closet. The main level laundry/mud room with front loader washer/dryer and built-in cabinetry opens to the powder room and 2 car garage with utility sink and extra storage above. Enjoy both indoor and outdoor living in the 4 season Florida Room overlooking the large, tree-lined backyard, or relax on the oversized front porch, rear Trex deck or gazebo! Pocket doors, central vac, original wood floors and trim, extra wide driveway, top-rated schools, parks, the works! 2016 UPDATES: Roof, Florida Room Addition, Anderson Windows, HVAC, Water Heater, Well Pump

Listed by Michelle Hodos of Long & Foster Real Estate,Inc.

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$/month over payments
Federal 30-year interest rate: 6.7% last updated on Sep 29, 2022
* All Figures are estimates. Check with your bank or proposed mortgage company for actual interest rates.
This product uses the FRED® API but is not endorsed or certified by the Federal Reserve Bank of St. Louis.

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31 Wagon Shed Lane Middletown MD 21769

Middletown, MD31 Wagon Shed Lane

Price$774,900

Est. Mortgage: $/month

Open House

MLS Number MDFR2026320

  • Single Family
  • Next Open House: Sat 10/1 12:00 pm. to 4:00 pm.
  • Bedrooms 5
  • Bathroom 5
  • Square Feet 4,716

This elegant, 5 bedroom, 4.5 bath brick-front home, previously featured in Frederick Lifestyle Magazine, backs to golf course with glorious mountain views & sunsets! Walk in to gleaming hardwood floors throughout dining room with butler's pantry, and living room. Formal office with french doors gives a great work-from-home space or playroom. Two-story family room with floor to ceiling windows and fireplace. Gorgeous kitchen with huge kitchen island, large corner pantry, all stainless steel appliances, desk area, and morning room lined with light-filled windows! Main-floor laundry off the kitchen. Dual staircases lead to the upper floor. Luxury primary suite complete with sitting room and walk-in closet. Primary bath boasts beautiful vanity area, shower, and large soaking tub. Huge walk-out basement with partially finished space including an "apartment" area with 5th bedroom with walk-in closet complete with 2nd washer/dryer hookup, a study, and full bathroom. Unfinished part of basement has kitchenette with 2nd dishwasher (2nd fridge does not convey). Several additional storage rooms and closet in basement area.

Listed by Kenneth A Grant of RE/MAX Plus

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$
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$/month over payments
Federal 30-year interest rate: 6.7% last updated on Sep 29, 2022
* All Figures are estimates. Check with your bank or proposed mortgage company for actual interest rates.
This product uses the FRED® API but is not endorsed or certified by the Federal Reserve Bank of St. Louis.

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3111 Bennies Hill Road Middletown MD 21769

MLS Number MDFR2026456

  • Single Family
  • Bedrooms 4
  • Bathroom 4
  • Square Feet 2,984
  • Acreage 5

A stunning home in Middletown on 5 acres elevates sophistication and detail. Wide pine planked floors, neutral color pallet, and design-inspired features in every room! From the open floor plan to the spectacular outdoor living space, this gorgeous home hits the perfect balance of privacy and every entertainer's dream; Gourmet eat-in kitchen with sleek stainless steel appliances, Wolf professional 6 burner range, range hood, custom cabinetry, decorative backsplash, marble countertops, island, breakfast bar, and easy access to the outdoor oasis; Spectacular family room adorned with a wood burning fireplace, lofty windows, hints of shiplap, and amazing backyard views. The upper level proudly features the enormous exquisite primary quarters with spa-like elements including an oversized shower, double vanities, a soaking tub, and a Juliet balcony with calming views. A secondary bedroom with a private full bath, laundry room, and loft area complete the second level. The SPECIAL FEATURE of this property is the private suite showcasing its own family room, full bath, wet bar, laundry, HVAC, loft, and secluded entrance. Travel downstairs to find the expansive open area just waiting to be completed, with walkup stairs and full bath rough in. The exterior features beautifully landscaped grounds, some extensive hardscape, an outside TV and entertainment area on the wrap-around porch, a fenced backyard, a 24x24 barn with running water and electricity, a private lot, backs to trees, trails, and panoramic views! This exquisite property aims to please and is truly the embodiment of peaceful living! Recent Upgrades: resurfaced fireplace, painted foundation, resurfaced flagstone & patio, replaced all bath & kit faucets, 24kw house generator, paved driveway, refinished flooring, new carpet, new life proof vinyl, radon system, counter & cabinets. This is simply A MUST-SEE Property.

Listed by Sean C Brink of Coldwell Banker Realty

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$
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$/month over payments
Federal 30-year interest rate: 6.7% last updated on Sep 29, 2022
* All Figures are estimates. Check with your bank or proposed mortgage company for actual interest rates.
This product uses the FRED® API but is not endorsed or certified by the Federal Reserve Bank of St. Louis.

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2509 Milt Summers Road Middletown MD 21769
Active With Contract

MLS Number MDFR2025940

  • Single Family
  • Bedrooms 3
  • Bathroom 2
  • Square Feet 1,600
  • Acreage 1.22

Lovely brick 3 bedroom, 1.5 bathroom rancher on 1.22 scenic acres with an incredible 2021 kitchen renovation has what you are looking for and more in Middletown! Country living with easy access to Rt 70 and 40! The Pinterest-inspired kitchen update has new two-toned cabinets, granite countertops, double sink, black appliances including a double-oven range, glass subway tile backsplash and LVP!! Beautiful hardwood flooring in the living room and bedrooms. Simonton replacement windows including a gorgeous bay window in the living room to look out over the mountain vistas in the distance while enjoying your wood-burning brick fireplace. Updated tub/shower main bathroom with new vanity and beadboard. Approximately 360 sq ft finished family room on the lower level with another brick fireplace and LVP flooring! Attached one-car garage, detached brick storage building with concrete slab/electric/heat, concrete patio with pergola in addition to a fenced backyard area. This property has it all and with newer architectural shingle roof (2019), hot water heater (2021), heat pump compressor (2017), well pump (2016) and new LVP flooring in the mudroom. No HOA! You have top rated schools, a library, golf courses & Greenbrier State Park with beach area all nearby!

Listed by Leigh Ann Fangmeyer of RE/MAX Plus

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$
%
$/month over payments
Federal 30-year interest rate: 6.7% last updated on Sep 29, 2022
* All Figures are estimates. Check with your bank or proposed mortgage company for actual interest rates.
This product uses the FRED® API but is not endorsed or certified by the Federal Reserve Bank of St. Louis.

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9316 Mount Tabor Road Middletown MD 21769

Middletown, MD9316 Mount Tabor Road

Price$625,000

Est. Mortgage: $/month

Active With Contract

MLS Number MDFR2025100

  • Single Family
  • Bedrooms 6
  • Bathroom 3
  • Square Feet 1,974
  • Acreage 13.54

Enjoy 13.5 acres, privacy and many recent updates! Great for entertaining, this 6 bed, 2.5 bath split foyer offers an open floor plan, new carpet and luxury vinyl plank flooring, brand new granite counters and fresh paint. A charming picket fence and front porch welcome you and make a great first impression. Once inside, the upper level hosts the open concept living room, kitchen and dining area. The spacious living room features a brick surround wood burning fireplace and French doors that lead to the rear deck, while the kitchen offers stainless steel appliances, a pantry and gorgeous granite counters. Just down the hall, your primary suite includes a walk-in closet and en suite with dual sinks, a soaking tub and walk-in shower. Two additional bedrooms and a full hall bath round out the top floor. In the partially finished lower level you will find 3 more bedrooms, a half bath, laundry area and ample storage space. When the weather allows, open up all the windows and doors and let the fresh country air inside! Exterior highlights include an oversized detached garage, a loafing shed and an additional storage shed. Enjoy the serenity and gorgeous valley views this property has to offer, while being just minutes from the highway and local amenities, parks, wineries and campgrounds.

Listed by Jay A Day and Christina L Day of Real Estate Teams,LLC

$
$
%
$/month over payments
Federal 30-year interest rate: 6.7% last updated on Sep 29, 2022
* All Figures are estimates. Check with your bank or proposed mortgage company for actual interest rates.
This product uses the FRED® API but is not endorsed or certified by the Federal Reserve Bank of St. Louis.

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119 Manda Drive Middletown MD 21769

Middletown, MD119 Manda Drive

Price$595,000

Est. Mortgage: $/month

MLS Number MDFR2025876

  • Single Family
  • Bedrooms 4
  • Bathroom 3
  • Square Feet 2,768
  • Acreage 0.47

This beautiful colonial is lovingly maintained and will make a wonderful home. It sits on a quiet street, with mature trees to welcome you. Upon entry, you'll find lovely hardwood flooring that flows into the private home office, living and dining rooms, complete with crown molding. The eat-in kitchen has brand new granite countertops a center island, SS appliances, ceramic tile flooring and a slider to the large rear deck. The family room has cathedral ceilings and a wood burning fireplace with brick surround. There is a main level laundry with access to the large two car garage. Upstairs is the large master bedroom with walk-in closet and en-suite bathroom with dual vanity, large soaking tub and separate shower. There are three more bedrooms and a full bath. The basement has a large rec room and a huge unfinished space where there is a lot of room for exercising, storage or expansion. Walk up to the huge level yard, almost half an acre in total, that is great for recreation or sports practice. There is a deck and a patio in the back. Enjoy the beautiful mountain views and nature while relaxing in your Adirondack chairs around the fire pit on the patio. Extremely well maintained, featuring many updates such as a recently replaced 50 year roof, an HVAC system and a water heater that was replaced last summer and some recently replaced appliances and carpets. VERY desirable location in the community of Foxfield at Middletown within walking distance to all of the excellent Middletown schools, the grocery store, the county park and the local athletic fields. No HOA! Don't wait, see it today!

Listed by Kevin M Coyne of Redfin Corp

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$
%
$/month over payments
Federal 30-year interest rate: 6.7% last updated on Sep 29, 2022
* All Figures are estimates. Check with your bank or proposed mortgage company for actual interest rates.
This product uses the FRED® API but is not endorsed or certified by the Federal Reserve Bank of St. Louis.

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7418 Mason Drive Middletown MD 21769

Middletown, MD7418 Mason Drive

Price$535,000

Est. Mortgage: $/month

Active With Contract

MLS Number MDFR2025818

  • Single Family
  • Bedrooms 4
  • Bathroom 3
  • Square Feet 2,256
  • Acreage 1.2

This spacious well-maintained 4 bedroom, 3 full bathroom corner lot home on 1.2 acres in the sought after Middletown South neighborhood is ready for you! The large living room and kitchen greet you with neutral painted walls on the main level as you make your way to the entertainment-sized screened-in porch and deck overlooking your beautiful backyard! Your primary bedroom sanctuary with updated ensuite (2021) modern shower, new vanity and LVP awaits you upstairs along with 2 other generous bedrooms and another updated full bathroom (tub/shower). On the lower level an HGTV-worthy brick accent wall with built-ins and gas fireplace will warm your heart along with the 4th bedroom, 3rd updated full bathroom & practical craft/utility room. In 2018 the HVAC, hot water heater and water softener were updated. Replacement double-hung windows , roof & 5" gutters (2008), oversized side loading 2-car garage & driveway, large shed, no HOA, leased energy-saving solar panels are all a part of this ideal Middletown property.

Listed by Leigh Ann Fangmeyer of RE/MAX Plus

$
$
%
$/month over payments
Federal 30-year interest rate: 6.7% last updated on Sep 29, 2022
* All Figures are estimates. Check with your bank or proposed mortgage company for actual interest rates.
This product uses the FRED® API but is not endorsed or certified by the Federal Reserve Bank of St. Louis.

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3394 Red Oak Court Middletown MD 21769

Middletown, MD3394 Red Oak Court

Price$589,900

Est. Mortgage: $/month

Pending

MLS Number MDFR2025582

  • Single Family
  • Bedrooms 3
  • Bathroom 3
  • Square Feet 2,944
  • Acreage 4.95

Bring your horses! Enjoy quiet country living, yet minutes to the center of town. Wonderful updated rancher on on 4.95 acres in a neighborhood, with a stream! Rear of lot is adjacent to Catoctin Creek. Original owners. Impeccably maintained. Oversized garage (27x27). Front (27x10) and rear (19x14) covered porches. Beautiful views. Updated kitchen and baths with spacious family room addition (19x15) with mudroom & 1st floor laundry off kitchen. Heated floor in the kitchen. Walk out level basement with fenced area around house. Basement includes large rec room (30x26) with den/bdrm, 1/2 bath & spacious storage area with its own exterior entrance. 45 yr architectural shingles on roof (2008). Partially fenced pasture with barn as well. Nature lovers paradise. Nothing to do but move right in and add your finishing touches!

Listed by Bobbi Prescott of RE/MAX Results

$
$
%
$/month over payments
Federal 30-year interest rate: 6.7% last updated on Sep 29, 2022
* All Figures are estimates. Check with your bank or proposed mortgage company for actual interest rates.
This product uses the FRED® API but is not endorsed or certified by the Federal Reserve Bank of St. Louis.

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706 E Main Street Middletown MD 21769

Middletown, MD706 E Main Street

Price$699,900

Est. Mortgage: $/month

MLS Number MDFR2025412

  • Single Family
  • Bedrooms 5
  • Bathroom 4
  • Square Feet 2,690
  • Acreage 1.5

Small Town, USA! Location! Location! Location! 706 E Main St was built in 1915 . Renovations throughout entire home has brought it to today's standards, leaving the original 1900 Charm! All handled with care by a local, trusted builder! Featuring ALL NEW 2022- Roof, Windows, HVAC/Ductless Splits, Hot Water Heater, Asphalt Driveway, Pool Liner, Drains, Equipment, Pool house and so much more! Inside the home you will be met with ALL NEW Flooring, Baths, Paint, Kitchen with Island, Granite countertops, Stainless Steel appliances. The Main level features Kitchen, Half Bath, Formal Dining, Formal Living, Family Room, Laundry & Office! Original Trim, Woodwork, and Lovely Pocket doors in the Perfect Places! Upper Level 1 Boasts 4 Bedrooms, Hall Tub Bath, and En-Suite. Upper Level 2 is ALL NEW Primary Suite with it's own Full Bath, Walk in Closet, Egress Windows and Storage! It's not easy to sum up ALL this home has to OFFER, it is a MUST SEE! Schedule your showing today!!

Listed by Hilery M Leatherman of Charis Realty Group

$
$
%
$/month over payments
Federal 30-year interest rate: 6.7% last updated on Sep 29, 2022
* All Figures are estimates. Check with your bank or proposed mortgage company for actual interest rates.
This product uses the FRED® API but is not endorsed or certified by the Federal Reserve Bank of St. Louis.

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3601 Westchester Court Middletown MD 21769
Pending

MLS Number MDFR2024740

  • Single Family
  • Bedrooms 3
  • Bathroom 3
  • Square Feet 1,772
  • Acreage 1.04

Wonderful custom built colonial with panoramic sunset views off Pete Wiles Road in Middletown. Original owner meticulously cared for this charming home. Front and back porches. Large spacious flat yard. Big family room with hearth & fireplace. NO HOA. New HVAC '19, Roof '12 and Septic pumped '20. Some new vinyl windows. Original decor in great shape. Ready for your personal touches. Come enjoy nature's art work every evening....

Listed by Bobbi Prescott of RE/MAX Results

$
$
%
$/month over payments
Federal 30-year interest rate: 6.7% last updated on Sep 29, 2022
* All Figures are estimates. Check with your bank or proposed mortgage company for actual interest rates.
This product uses the FRED® API but is not endorsed or certified by the Federal Reserve Bank of St. Louis.

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1709 Dahlgren Road Middletown MD 21769

Middletown, MD1709 Dahlgren Road

Price$1,299,900

Est. Mortgage: $/month

MLS Number MDFR2025124

  • Single Family
  • Bedrooms 4
  • Bathroom 5
  • Square Feet 4,555
  • Acreage 29.06

Welcome to 1709 dahlgren road! Beautifully and well-maintained home that shows pride of ownership! Location! Location! Location! Expansive estate on 29.06 park-like acres with picturesque stone walls surrounding this gem! Exceptional views that overlook the valleys and rolling hills from an elevated view. Approximately 8-9 acres of manicured revenue generating pastures. Home boasts three finished levels and features natural stone exterior, wood floors, 4 large bedrooms, 4.5 bathrooms and a combination of wood, pellet and lp gas fireplaces/stoves sprinkled throughout. Large finished basement and a separate hobby room with direct access to a two car garage. Massive 2 story barn with concrete floor and four 10' x 10' garage doors. Conveniently located close to major commuter routes and downtown middletown.

Listed by William A Haag Jr and Kimberly Haag of Long & Foster Real Estate,Inc.

$
$
%
$/month over payments
Federal 30-year interest rate: 6.7% last updated on Sep 29, 2022
* All Figures are estimates. Check with your bank or proposed mortgage company for actual interest rates.
This product uses the FRED® API but is not endorsed or certified by the Federal Reserve Bank of St. Louis.

Save FavoriteSchedule TourAsk A QuestionMore Details

321 S Church Street Middletown MD 21769

Middletown, MD321 S Church Street

Price$375,000

Est. Mortgage: $/month

Pending

MLS Number MDFR2025000

  • Single Family
  • Bedrooms 2
  • Bathroom 1
  • Square Feet 1,125
  • Acreage 0.29

Priced below appraised value!! Welcome home! This adorable all brick, 2 bedroom, 1 full bath rancher home, in the sought after Middletown School District won't last long! Featuring gorgeous hardwood floors throughout, a cozy wood-burning fireplace in the living room, separate kitchen and dining room and a light filled sunroom, perfect to sit and enjoy your morning coffee or could be a great home office! The attic has some nice options for additional living space and there is plenty of storage in the unfinished basement, as well as the shed out back! This is your opportunity.....Schedule your showing today, before it is gone! Property is being sold "As-Is"

Listed by Julie M Byrd of Long & Foster Real Estate,Inc.

$
$
%
$/month over payments
Federal 30-year interest rate: 6.7% last updated on Sep 29, 2022
* All Figures are estimates. Check with your bank or proposed mortgage company for actual interest rates.
This product uses the FRED® API but is not endorsed or certified by the Federal Reserve Bank of St. Louis.

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Copyright 2022 BRIGHT, All Rights Reserved.  Information Deemed Reliable But Not Guaranteed. The data relating to real estate for sale on this website appears in part through the BRIGHT Internet Data Exchange program, a voluntary cooperative exchange of property listing data between licensed real estate brokerage firms in which Premier Group | Long & Foster Real Estate, Inc. participates, and is provided by BRIGHT through a licensing agreement. The information provided by this website is for the personal, non-commercial use of consumers and may not be used for any purpose other than to identify prospective properties consumers may be interested in purchasing.Data last updated October 1, 2022. Some properties which appear for sale on this website may no longer be available because they are under contract, have Closed or are no longer being offered for sale.