Skip to content
Photo 1 of 93
Photo 1 of 93 — 106 PROSPECT STREET, MIDDLETOWN, MD 21769
View all 93 photos

106 PROSPECT STREET, MIDDLETOWN, MD 21769

MIDDLETOWN · FREDERICK County

Key Facts

3Beds
2Baths
2,574Sq Ft
1920Year Built
0.41Lot (acres)
1Garage

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

Kitchen IslandOpen Floorplan

Appliances

CooktopGas Water HeaterRefrigeratorDishwasher

Cooling

Central AirElectric

Heating

PropaneRadiant

Flooring

Wood

Fireplace

Gas

Basement

DaylightPartial

Pool

None

Parking

GarageDrivewayDetached

Laundry

Upper Level

Patio

PatioPorch

Lot Features

Back Yard

Construction

Stucco

Foundation

Slab

Roof

Shingle

Windows

Storm Window(s)

Sewer

Public Sewer

Water Source

Public

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.

Commute Calculator

Travel mode

Nearby Homes

Similar Homes Nearby

Similar Home Values

Comparable nearby listings and their asking prices.

Moving Cost Estimate

EXIT Agents in MIDDLETOWN

Listing Courtesy: RE/MAX Results - 3016985005

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 EXIT Realty 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. 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. Information Deemed Reliable But Not Guaranteed. Copyright ©2026 Bright MLS. All rights reserved.

The data relating to real estate for sale on this web site comes in part from the Internet Data Exchange (IDX) program of one or more Multiple Listing Services (MLS). Listing information is deemed reliable but is not guaranteed accurate. Copyright © EXIT Realty® and respective MLS providers.

Data provided by BRIGHT. MLS® Listing#MDFR2084304. © 2026EXIT Realty®. All rights reserved.