Spy Price Points: What $100,000 to $400,000 Buys You in  Chestertown 


This week’s feature is a property listed for $399,900 in Chestertown.

The massing, exterior color palette and wooded setting gives this Cape Cod style house great curb appeal. I liked how the massing was broken down by a breezeway with a porch and separate entry that connected the garage wing to the house. The main part of the house with its pitched roof is set slightly forward from the garage wing with its inset front gable for additional architectural interest. I am not fond of front loading garages but the craftsman detailing of the garage doors with their windows won me over.  

The breezeway opens to the pantry, mudroom and laundry for a very functional service area between the kitchen and the garage which so many floor plans lack. A secondary stair leads to the large airy bonus room above the garage. The kitchen and family room have stained wood beams that break up the expanse of the ceiling. The angled fireplace and direct access to the screened porch make this a great family space with views to the private back yard with lush low maintenance plantings.

The large master suite on the main floor also has a fireplace flanked by double windows and the pitched ceiling has exposed stained beams. I have one closet in my small house so I was envious of the dressing room with built-in storage and a window for daylight. The living room has built-in bookcases ready for the next family’s books and photographs.   

My favorite room was the bonus room over the garage.  I loved the wide dormers with double windows and the transoms over the front gable window.  The pitched ceiling, wood floors, recessed lighting and the white walls to reflect the light made this a special room for myriad uses.  


For more information about this property, contact  Peter Heller with Coldwell Banker Chesapeake Real Estate Company at 410-778-0330 (o), 410-708-3301 (c) or pheller@cbchesapeake.com, “Equal Housing Opportunity”.

Spy House of the Week is an ongoing series that selects a different home each week. The Spy’s Habitat editor Jennifer Martella makes these selections based exclusively on her experience as a architect.

Jennifer Martella has pursued her dual careers in architecture and real estate since she moved to the Eastern Shore in 2004. Her award winning work has ranged from revitalization projects to a collaboration with the Maya Lin Studio for the Children’s Defense Fund’s corporate retreat in her home state of Tennessee. Her passion for Italian food, wine and culture led her to Piazza Italian Market where she is the Director of Special Events, including weekly wine tastings and quarterly wine dinners.


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