Homes for sale under $500k in Middletown, MD

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COMING SOON

ABOUT THIS HOME
Homes for sale under $500k in Middletown, MD
Historic elegance meets expansive acreage in this one-of-a-kind property at 1936 Old National Pike, Middletown, MD. Spanning nearly 4 acres, this brick home exudes old-world charm while offering a blank canvas for personalization and modern living. Discover a rare find: a historic, brick-constructed home built around the turn of the last century, situated on nearly 4 acres along Old National Pike in Middletown, MD. This property offers generous interior space, a durable metal roof, and beautifully mature grounds that present tremendous opportunity for landscaping, expansion, or outdoor living. Positioned on a historic artery — Maryland’s original National Road — this home

$465,000

4 beds2 baths2,824 sq ft

1936 Old National Pike, Middletown, MD 21769

3.87 acre lot • Built 1900 • Listed 5 days

(301) 662-0155

ABOUT THIS HOME
Homes for sale under $500k in Middletown, MD
Beautifully renovated oversized farmhouse in the heart of Middletown Valley. Blending timeless character with modern updates, this 3-bedroom, 2-full bath home is move-in ready and full of charm. Step inside to find spacious living areas filled with natural light, a thoughtfully updated kitchen with quality finishes, and two full bathrooms that have been tastefully remodeled. Original farmhouse details are complemented by contemporary upgrades, creating the perfect balance of old and new. Enjoy the peaceful setting from the covered porch or entertain in the generous yard surrounded by scenic views as well as the 2 story mancave with workshop below and a living space above that can be updated

$459,000

3 beds2 baths1,752 sq ft

8109 Old Hagerstown Rd, Middletown, MD 21769

Renovated farmhouse • Covered porch • Generous yard

(410) 705-6296

ABOUT THIS HOME
Homes for sale under $500k in Middletown, MD
Welcome to 25 Chester Court in Middletown, MD, a stunning end unit townhome. This spacious home offers 2472 square feet of modern living across three floors, featuring 3 bedrooms and 3.5 bathrooms. The main level boasts a contemporary kitchen with white quartz countertops, stainless steel appliances, and a large deck perfect for entertaining. The expansive open walkout basement includes a full bathroom, providing ample space for recreation or an additional living area. The home also features luxury vinyl plank (LVP) flooring on all three floors, and an upstairs laundry room for convenience. The oversized primary bedroom is a true retreat, complete with two walk-in closets and an en-suite ba

$449,900

3 beds3.5 baths— sq ft

25 Chester Ct, Middletown, MD 21769

Large deck • Contemporary kitchen • $200 HOA

(703) 679-1700

COMING SOON

ABOUT THIS HOME
Homes for sale under $500k in Middletown, MD
Stunning End-Unit Townhouse Backing to Golf Course – A Rare Find! Welcome to this beautifully maintained end-unit townhouse, perfectly situated on a gorgeous lot backing to the golf course. Offering peaceful views, exceptional privacy, and wonderful natural light throughout, this home is a true standout. Step inside to discover thoughtful upgrades and modern comforts, including: New hot water heater (2022), Brand-new HVAC system—furnace and AC (2024), New garbage disposal (2025), Upgraded hardwood flooring on the upstairs hall and stairs (2021). The main level features an inviting layout ideal for both everyday living and entertaining. Upstairs, the upgraded hardwoods lead you

$425,000

3 beds2.5 baths2,640 sq ft

600 Stone Springs Ln, Middletown, MD 21769

$85 HOA • Community pool • Built 2009

(240) 815-9040

COMING SOON

ABOUT THIS HOME
Homes for sale under $500k in Middletown, MD
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

$420,000

4 beds1.5 baths1,396 sq ft

7129 Limestone Ln, Middletown, MD 21769

0.4 acre lot • 6 parking spots • Pool

(240) 309-6000

Property at 10 Linden Blvd, Middletown, MD 21769, 3 beds, 1.5 baths

$349,000

3 beds1.5 baths2,104 sq ft

10 Linden Blvd, Middletown, MD 21769

(717) 597-9100

Property at 417 W Main St, Middletown, MD 21769, 3 beds, 1 bath

$299,990

3 beds1 bath1,392 sq ft

417 W Main St, Middletown, MD 21769

(301) 591-3920

Property at 1246 Mountain Church Rd, Middletown, MD 21769, 2 beds, 1 bath

$224,900

2 beds1 bath900 sq ft

1246 Mountain Church Rd, Middletown, MD 21769

(443) 627-2900

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ABOUT THIS HOME
Homes for sale under $500k in Middletown, MD
Welcome to this beautifully maintained raised rancher nestled in the heart of Myersville, offering spectacular mountain views and peaceful privacy on over two acres of land. This unique property includes a second adjoining lot, giving you plenty of room to relax, garden, or simply take in the stunning scenery. Step inside through the lower-level entryway to find a spacious family room with a cozy gas fireplace — the perfect place to unwind. This level also features a renovated and stylish full bath and laundry room, an office/den that could easily serve as a fourth bedroom or guest space, and an entry from the attached one car garage. Upstairs, the main level is bright and inviting, w

$499,900

3 beds2 baths1,524 sq ft

10215 Harmony Rd, Myersville, MD 21773

Cozy gas fireplace • Laundry room • Renovated full bath

(410) 312-0000

$499,000

4 beds3 baths2,208 sq ft

421 Main St, Myersville, MD 21773

0.29 acre lot • Parking • Built 1910

(301) 271-3487

NEW CONSTRUCTION

ABOUT THIS HOME
Homes for sale under $500k in Middletown, MD
* * Fantastic financing!! 5.5% 30-yr fixed rate with zero points on this home for qualified buyers!! * * November update. .. .. .construction is coming down the home stretch! Move into this unique property in less than 30 days! * * Don't miss out on this "Tiny House" built by master builder Lenak Company! A true rare find! Thought it was impossible to purchase a brand new home on nearly three quarters of an acre that includes woods and a stream for less than 500k? Well. .. .here it is! Yes, it's a very small house. .. .that's for sure, but no HOA, no condo association, no attached neighbors, everything is brand new, extremely low utility costs, and you get to enjoy your

$495,000

2 beds1 bath650 sq ft

7125 Edgemont Rd, Frederick, MD 21702

0.73 acre lot • Built 2025 • Listed 183 days

(301) 424-0900

ABOUT THIS HOME
Homes for sale under $500k in Middletown, MD
NEW PRICE! Come take a look at the all the updates. A great opportunity to own a home in Meadowridge at an incredible value. This 4 bedroom, 2.5 bath colonial home offers the features you've been looking for. Located on a quiet cul-de-sac with sidewalks throughout the neighborhood enabling those safe strolls and exercise. Inside you'll find gleaming wood floors, lots of natural light and spacious rooms throughout. The kitchen opens to the cozy family room which offers a sunken floor and wood burning fireplace for those chilly nights. The separate dining and living rooms provide space for those holiday meals and larger gatherings. From the kitchen you'll exit onto the covered and open decks

$489,900

4 beds2.5 baths2,438 sq ft

2703 Meadowridge Ct, Myersville, MD 21773

Storage shed • Cul-de-sac • Mature trees

(240) 815-9040

$479,000

5 beds2 baths1,628 sq ft

1510 Havilland Pl, Frederick, MD 21702

5,665 sq ft lot • Built 1981 • Listed 25 days

(301) 445-1395

ABOUT THIS HOME
Homes for sale under $500k in Middletown, MD
This quaint rancher in the Wye Creek area, just outside Frederick, offers 1,800 sq ft of living space with 3 bedrooms and 1 bathroom. The fully remodeled interior features a newly finished basement that provides versatile multipurpose space and a convenient walkout to the backyard. The kitchen boasts stainless steel appliances, quartz countertops, and a stylish tile backsplash. Refinished hardwood floors enhance the main level's charm, while the dining room opens to a covered back deck overlooking the serene woodland on nearly an acre lot. Additionally, this property includes a large detached garage and is situated in a convenient commuting location that balances rural tranquility with acce

$475,000

3 beds1 bath1,800 sq ft

4814 Teen Barnes Rd, Frederick, MD 21703

Remodeled interior • Quartz countertops • Tile backsplash

(240) 309-6000

Property at 10255 Rollingridge Ct, Myersville, MD 21773, 3 beds, 3 baths

$450,000

3 beds3 baths1,608 sq ft

10255 Rollingridge Ct, Myersville, MD 21773

(301) 882-8710

Property at 3805 Bedford Dr, Jefferson, MD 21755, 3 beds, 2.5 baths

$449,000

3 beds2.5 baths2,037 sq ft

3805 Bedford Dr, Jefferson, MD 21755

(301) 439-9500

Property at 2802 Monument Rd, Myersville, MD 21773, 3 beds, 2 baths

$444,900

3 beds2 baths1,225 sq ft

2802 Monument Rd, Myersville, MD 21773

(301) 831-5099

Property at 4810 Old Swimming Pool Rd, Frederick, MD 21703, 3 beds, 2 baths

$435,000

3 beds2 baths1,470 sq ft

4810 Old Swimming Pool Rd, Frederick, MD 21703

(410) 705-6296

Property at 106 E Main St, Burkittsville, MD 21718, 3 beds, 2 baths

$420,000

3 beds2 baths1,597 sq ft

106 E Main St, Burkittsville, MD 21718

(443) 542-2251

Property at 5719 Shookstown Rd, Frederick, MD 21702, 3 beds, 1 bath

$419,900

3 beds1 bath1,420 sq ft

5719 Shookstown Rd, Frederick, MD 21702

(301) 698-5005

Property at 114 Potomac St, Boonsboro, MD 21713, 3 beds, 2.5 baths

$415,000

3 beds2.5 baths2,016 sq ft

114 Potomac St, Boonsboro, MD 21713

(877) 366-2213

Property at 7625 Mountain Laurel Rd, Boonsboro, MD 21713, 3 beds, 2 baths

$399,900

3 beds2 baths1,800 sq ft

7625 Mountain Laurel Rd, Boonsboro, MD 21713

(301) 882-7567

Property at 123 Potomac St, Boonsboro, MD 21713, 3 beds, 3 baths

$395,000

3 beds3 baths2,192 sq ft

123 Potomac St, Boonsboro, MD 21713

(301) 695-3020

Property at 3412 Jefferson Pike, Jefferson, MD 21755, 3 beds, 1 bath

$390,000

3 beds1 bath1,282 sq ft

3412 Jefferson Pike, Jefferson, MD 21755

(443) 353-5281

Property at 3830 Jefferson Pike, Jefferson, MD 21755, 4 beds, 2 baths

$389,900

4 beds2 baths1,638 sq ft

3830 Jefferson Pike, Jefferson, MD 21755

(877) 366-2213

Property at 211 Della Ln, Boonsboro, MD 21713, 3 beds, 2 baths

$384,999

3 beds2 baths1,540 sq ft

211 Della Ln, Boonsboro, MD 21713

(877) 366-2213

Property at 5922 Clevelandtown Rd, Boonsboro, MD 21713, 3 beds, 1.5 baths

$375,000

3 beds1.5 baths1,534 sq ft

5922 Clevelandtown Rd, Boonsboro, MD 21713

(301) 694-8000

Property at 126 Lakin Ave, Boonsboro, MD 21713, 2 beds, 1 bath

$369,900

2 beds1 bath1,200 sq ft

126 Lakin Ave, Boonsboro, MD 21713

(301) 662-0155

Homes for sale under $500k in Middletown

There are currently 8 homes for sale under $500k in Middletown. Some of these homes are "Hot Homes," meaning they're likely to sell quickly. Most homes for sale in Middletown stay on the market for 29 days and receive 1 offers. This map is refreshed with the newest listings in Middletown every 15 minutes.

In the past month, 12 homes have been sold in Middletown. In addition to houses in Middletown, there were also 0 condos, 4 townhouses, and 0 multi-family units for sale in Middletown last month. Find your dream home in Middletown using the tools above. Use filters to narrow your search by price, square feet, beds, and baths to find homes that fit your criteria. Our top-rated real estate agents in Middletown are local experts and are ready to answer your questions about properties, neighborhoods, schools, and the newest listings for sale in Middletown. Our Middletown real estate stats and trends will give you more information about home buying and selling trends in Middletown. If you're looking to sell your home in the Middletown area, our listing agents can help you get the best price. Redfin is redefining real estate and the home buying process in Middletown with industry-leading technology, full-service agents, and lower fees that provide a better value for Redfin buyers and sellers.

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