Middletown Real Estate & Homes for Sale

3 bed 1.5 bath split foyer with garage, walkout basement with den, office, and storage at the end of cul de sac. Replaced within the last 5 years: roof, hvac, sewer main,...

Foxfield at its Finest! Beautiful home on one of the best lots Foxfield has to offer. With just over 3100 finished SF, and just shy of a half acre...this home has it al...

Nestled in the charming community of Middletown, this delightful bungalow offers a perfect blend of comfort and convenience. Built in 1945, this home exudes character wit...

A little bit of country feel, a lot of usable space, and a location that is increasingly hard to find. Tucked at the end of a cul-de-sac on more than half an acre, this c...

Welcome to 1 Wagon Shed Lane, a stunning five-bedroom, five-full- and one-half-bath Colonial offering nearly 7,000 square feet of luxurious living space in the sought-aft...

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Welcome to this former model home on a spacious corner lot offering comfort, flexibility and inviting indoor and outdoor living. The main level features refinished hardwo...

Welcome to 5 Bankbarn Circle, a stunning three-story townhouse offering 2,416 square feet of beautifully designed living space in Middletown’s highly desirable Glenbrook ...

Carefully reimagined between 2018 and 2021 with over $1.5M in updates, this historic Main Street home now lives like a luxury boutique retreat hidden in the heart of Midd...

Welcome to 4492 Jade Court, where a complete interior and exterior renovation meets an exceptional private backyard retreat. Situated on a generous .55-acre lot, this tru...

Welcome to 7008 Mountain Church Road, a beautifully renovated and move-in-ready home offering the best of country living with stunning mountain views. This charming two...

OPEN HOUSE SATURDAY 8/29 11AM-1PM Welcome to this charming 3-bedroom home right across the street from Memorial Park in the heart of Middletown. offering classic charact...

Welcome to 411 Glenbrook Drive in the desirable Glenbrook community of Middletown. This home offers over 4,600 finished square feet of living space with a great layout, b...

Escape the ordinary with this one-of-a-kind mountain-inspired retreat set on more than 5 secluded acres of mature woodland. Designed to embrace its natural surroundings, ...

To-be-Built. Set against the stunning backdrop of scenic Middletown Valley, Heritage Oak Estates is Middletown’s premier 12 lot luxury home community presented by local ...

To-be-Built. Set against the stunning backdrop of scenic Middletown Valley, Heritage Oak Estates is a premier 12 lot luxury estate home community presented by local buil...

To-be-Built. Set against the stunning backdrop of scenic Middletown Valley, Heritage Oak Estates is Middletown’s premier 12 lot luxury home community presented by local ...

Welcome to 7 Derr Lane in the sought-after Villages at Foxfield—Middletown’s premier 55+ community—where Original Owners have meticulously maintained and thoughtfully upg...

This home is an absolute MUST SEE. This home has been immaculately maintained and features all of it's original charm. You will fall in love with the beautiful hardwood f...

Welcome to this beautiful colonial in the heart of Middletown, MD, where small-town charm, community character, and a prime Main Street address come together on a generou...

Welcome to this charming 4-bedroom, 2-bathroom home ideally situated on Main Street in the heart of Middletown, offering the perfect blend of character, comfort, and conv...

*One or more photos in this listing have been virtually staged using AI* Completely Renovated & Move-In Ready! Welcome to this beautifully updated ranch-style home situat...

Welcome to 5 Dean Lane, a stunning 4-bedroom, 4.5-bath home in the sought-after Middletown Glen community. Ideally located within walking distance of schools, parks, and ...

Welcome to your own private retreat! This 3-bedroom, 3 full bath home offers nearly 2,500 square feet of finished living space and comes with not one, but two parcels tot...

Charming 1/4 acre buildable on E. Green Street. The buyer of 19 E. Main Street will have the right of first refusal on the sale. Additional photos available on the 19 ...

Experience the flow of space and harmony a private 5-acre sanctuary where mid-century soul meets meticulous architectural restoration. Set among park-like grounds and hun...

Experience the flow of space and harmony a private 5-acre sanctuary where mid-century soul meets meticulous architectural restoration. Set among park-like grounds and hun...

HOME TO BE BUILT - Don't miss the final opportunity to build your custom home! Experience the breathtaking mountain views and modern luxury in this stunning new construct...

HOME TO BE BUILT. Nestled on a beautiful, wooded 2.25-acre lot, this to-be-built home by Grossnickle Construction offers the perfect blend of luxury and comfort. The hom...

LOCATION! LOCATION! LOCATION!!! Prime Commercial Property Zoned GC with endless possiblilities, easy access to highways & walkability to downtown/residential development ...

Escape the subdivision life for a residence defined by scale, privacy, and rugged utility. Set on 32.39+/- acres, this cabin-style estate is built for those who want thei...