Historic Charm, Thoughtful Updates & Gardens to Fall in Love With

Some homes simply have a soul—and this beautifully preserved 1920s Craftsman bungalow is one of them. Situated on a rare lot and a half in the heart of historic Middletown, this contributing home to both the National and Frederick Historic Registers has been lovingly cared for by just two families throughout its history.

From the moment you arrive, you’ll notice the timeless character that sets this home apart. Tall original windows frame mature trees, gardens, and changing seasonal views from nearly every room, filling the home with natural light and creating a peaceful connection to the outdoors. Original wood floors, handcrafted trim work, pocket doors, custom storm windows, and historic architectural details blend seamlessly with thoughtful modern updates. The sellers have always appreciated the home’s solid clay block construction, which provides a remarkably quiet, comfortable feel and exceptional insulation rarely found in homes of this era.

At the heart of the home is a beautifully renovated kitchen that has served as the gathering place for everything from weeknight dinners to holiday celebrations. A spacious island welcomes family and friends, while the thoughtful layout offers the perfect balance of openness and functionality. Upstairs, generously sized bedrooms, second-floor laundry, and an updated bath provide modern convenience while honoring the home’s historic roots.

Outside, the property unfolds into a collection of extraordinary outdoor living spaces. Enjoy sunrise views from the backyard, summer sunsets from the welcoming front porch, abundant gardens, mature trees, a kitchen garden, and a private backyard retreat complete with a pergola and gas firepit. Every outdoor space offers its own unique experience, creating a rare sense of privacy and connection to nature in the heart of town.

Major improvements include a renovated kitchen and baths, HVAC system, NTI combi-boiler, roof, insulation, updated electrical, propane installation, custom storm windows, and asbestos remediation.

Perhaps most special of all are the home’s original handcrafted windows and custom-built storm windows—an increasingly rare treasure that has been lovingly maintained and thoughtfully restored. Throughout their stewardship, the sellers viewed themselves less as owners and more as caretakers of something truly special, dedicated to preserving the integrity and craftsmanship the original builders intended. The result is a home that honors its past while offering the comfort, beauty, and functionality today’s buyers desire.

A rare opportunity to own a piece of Middletown history—where historic craftsmanship, thoughtful updates, beautiful gardens, and small-town charm come together to create something truly exceptional.

For Sale: $500,000

Seller offering 2.5% Commission to Buyer's Agent

3 Beds
1 ½ Baths
Detached
Bungalow
2,574 sq ft
Lot 0.41 acres
Driveway, Garage
Basement, Garage
Year Built: 1920
MLS: MDFR2084304
Property Tax: $5,477.01/year

Amenities

Air Conditioning
Bungalow
Covered Patio
Family Room
Fenced Yard
Fireplace
Patio
Remodeled
Recessed Lighting
Stainless Appliances
Stone Countertops

Map & Nearby Places

106 Prospect Street
Middletown, MD 21769
3 Bed | 1 ½ Baths

Video

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Open House

Tue, June 30, 2026 Tue, Jun 30, 2026
11:00 AM - 4:00 PM
In-Person
Open House
Thu, July 9, 2026 Thu, Jul 9, 2026
11:00 AM - 4:00 PM
In-Person
Open House
Mon, July 13, 2026 Mon, Jul 13, 2026
11:00 AM - 4:00 PM
In-Person
Open House

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