
106 PROSPECT STREET, MIDDLETOWN, MD 21769
MIDDLETOWN · FREDERICK County
Key Facts
Description
Some homes simply have a soul—and this beautifully preserved 1920's 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, 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. Showings to begin August 1st, not before.
Property Information
Property Type
Residential
Sub-Type
Single Family Residence
Structure Type
House
Year Built
1920
Living Area
2,574 sq ft
Lot Size
0.41 acres
Garage Spaces
1
Parking Spaces
5
Zoning
R
MLS® Listing#
MDFR2084304
Property Features
Interior
Appliances
Cooling
Heating
Flooring
Fireplace
Basement
Pool
Parking
Laundry
Patio
Lot Features
Construction
Foundation
Roof
Windows
Sewer
Water Source
Schools
- Elementary:
- MIDDLETOWN
- Middle:
- MIDDLETOWN
- High:
- MIDDLETOWN
- District:
- FREDERICK COUNTY PUBLIC SCHOOLS
Financial Details
HOA
None
Annual Taxes
$5,352
Tax year 2025
Assessed Value
$409,800
Parcel Number
1103148238
Directions
Main Street to Prospect. Home on the LEFT.
Affordability Calculator
$99,000
Estimated monthly payment
$2,635/mo
Principal $396,000 · Est. interest $552,455 over 30 yrs
Neighborhood Market Statistics
How this home compares to active listings in MIDDLETOWN, MD
- $733,333
- Median Listing Price
- 60
- Median Days on Market
- 2,820
- Median Sq Ft
- $300
- Median Price / Sq Ft
- 14
- Active Listings
- This home’s price is 32% below the area median.
- Its price per sq ft is 36% below the area median.
Market statistics compiled from active EXIT Realty® and MLS listings in MIDDLETOWN, MD.
Location
Map is currently unavailable for this location.
Points of Interest in MIDDLETOWN, MD
Showing the MIDDLETOWN area map.
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Nearby Homes
Similar Homes Nearby
Similar Home Values
Comparable nearby listings and their asking prices.
| Address | Price | Beds | Baths | Sq Ft |
|---|---|---|---|---|
| 400 STONE SPRINGS LANE, MIDDLETOWN, MD | $439,900 | 4 | 4 | 2,640 |
| 4 LAMAR LANE, MIDDLETOWN, MD | $489,900 | 2 | 2 | 1,359 |
| 708 E MAIN STREET, MIDDLETOWN, MD | $499,000 | 4 | 2 | 2,036 |
| 2 DERR LANE, MIDDLETOWN, MD | $555,000 | 3 | 3 | 2,279 |
| 2748 BENNIES HILL ROAD, MIDDLETOWN, MD | $599,000 | 3 | 3 | 2,451 |
Moving Cost Estimate
EXIT Agents in MIDDLETOWN
Listing Courtesy: RE/MAX Results - 3016985005
















