Annapolis

With help from realtor Kirstin Whitaker, John and Christine visit the nautical town of Annapolis, Maryland’s capital. They tour and guess the listing prices of three homes, from historic to modern, all with water views. Also, follow along to learn about the famous naval history of the town, as well as the arts, culture and buildings that make the story of Annapolis come to life.

Long a center for sailing and oysters, Annapolis reached the height of its prominence in the 1770s - 1790s, when it was known as the "Athens of America." After decades as a crossroads for American political and cultural life, the city slipped into a century-long recession. The downturn served to stifle development and preserve much of the colonial architecture for which Annapolis is known today.

With original details around every corner, John and Christine love the flow and character of this 1940s home in Annapolis's Homewood neighborhood. Upstairs, large windows flood three bedrooms with light. Downstairs, a four season sun room looks out over a lush backyard built for entertaining. No wonder John calls it "the perfect starter home in Annapolis."

"Oh, what an outdoor space!", exclaims Christine as she steps out on the screened-in porch of this 5 Bedroom, 3.1 Bath home in Annapolis's Oyster Harbor neighborhood. It's one of many surprises that make guessing the list price of the property a challenge. Can you do better than John and Christine?

"This is the dream of Annapolis living," realtor Kirstin Whitaker tells John and Christine, and it's easy to see why. Situated on 3.5 acres overlooking the Severn River and built in 1910, this 7 bedroom, 4.2 bath home was once used as a retreat by Capuchin Monks. From the wrap around porch, to the interior renovations that meld with the home's original details, this home oozes character.