100 Prospect Street

Chestertown MD 21620

1373 sq. ft.

3475 sq. ft.

Single-Family

Last sold for $215,000

David Moore, last sold this property on 21 July 2026 after 47 days on market.

Overview

Fully Renovated Rancher in the Heart of Chestertown — Walk to Everything. Most homes in this price range make you choose: updated systems or a great location. This one delivers both. Tucked on a quiet corner lot just steps from Washington College, the Chester River marina, weekend Farmers Market, and Chestertown's thriving restaurant and shop scene, 100 Prospect Ave puts the best of the Eastern Shore's most walkable town right outside your front door — without the noise or traffic. The home has been completely overhauled from the outside in. New metal roof, gutters, downspouts, vinyl siding, and windows protect your investment from the elements before you ever step inside. Inside, a new HVAC system, updated 200-amp electrical panel, new hot water heater, and fully replaced water main and plumbing mean zero deferred maintenance — just move in and live. Refinished hardwood floors and new vinyl flooring run throughout open, light-filled spaces. The updated bathroom features a new vanity, and the laundry room comes equipped with a brand-new washer and dryer. The kitchen opens directly into the dining area and flows into the family room — a layout that makes everyday living easy and entertaining effortless. Start your mornings on the enclosed porch. Host friends on a generous corner lot with room to breathe. Park conveniently on the private gravel pad with direct kitchen access. This is what move-in ready actually looks like. Schedule your tour today.

Features

3 bedrooms

1 bathroom

1373 sq. ft. floor area

3475 sq. ft. lot size

Single-Family

Estimated Value

Based on this property and similar 3 bedroom single-family properties sold in Chestertown over the last 12 months, the estimated median property value of 100 Prospect Street is $350k.

Median value

$350k

Estimated value range

$80k - $1.65m

Median days on market

Estimated value trend

-1%

decrease over the last 12 months

Average days on market is based on recent, comparable sales in Chestertown. It is only an indication of the time a property is actively listed and should not be relied upon as an accurate representation of how soon a property will be sold.

Property history for 100 Prospect Street

2026

Sold

$215,000

21 Jul 2026 by David Moore, of Real Broker, LLC

2021

Sold

$182,400

30 Sep 2021 by Jeff Guthrie, of Cross Street Realtors LLC

2021

Sold

$45,000

02 Apr 2021

Happy sellers in Chestertown

We have insufficient information to provide an overview of customer satisfaction for Chestertown. Viewing the agent profiles, reviews and sales for Chestertown can provide insights for this location.