# 105 HIGH Street, Chestertown, MD 21620

> **TL;DR:** 5bd/5ba single family, $1,295,500 ($399/sqft), built 1863, 3,243 sqft.
> Fireplace, A/C. Est. $5,614/mo. Listed 206 days.

## Property at a Glance

| Attribute | Value |
|-----------|-------|
| Price | $1,295,500 |
| Price/sqft | $399 |
| Bedrooms | 5 |
| Bathrooms | 4 full, 1 half |
| Square Feet | 3,243 |
| Year Built | 1863 |
| Lot Size | 2,688 sqft (0.06 acres) |
| Stories | 4 |
| Property Type | Single Family (Other) |
| Status | For Sale |
| Days on Market | 206 |

## Estimated Monthly Costs

| Category | Amount |
|----------|--------|
| Mortgage (20% down, 6.5%) | $5,614 |
| **Total** | **$5,614** |

## Key Amenities

- Fireplace
- A/C

## Property Highlights

- Built in 1863
- 0.06 acre lot
- 4 stories
- 1 parking spaces
- Fireplace

## Description

### Agent Description
Rebuilt in 1863, the Tilley Residence showcases classic Second Empire architecture on one of Chestertown's most prominent historic corners across from the Custom House, one of the first British Royal Ports of Entry to the Americas. Completely restored in 2025 by one of the Eastern Shore's iconic builders, the home blends historic character with modern comfort through thoughtful updates, new systems, and refined living spaces. Just one block to the waterfront promenade or to morning coffee at Evergrain, the location captures the rhythm of Chestertown living-laid back yet polished, historic yet vibrant. This is more than a home; it is an irreplaceable asset and a true legacy property within one of Maryland's most beloved waterfront towns.

## Location

- **Address:** 105 HIGH Street, Chestertown, MD 21620
- **County:** KENT
- **Neighborhood:** CHESTERTOWN HISTORIC DISTRICT
- **Coordinates:** 39.20731, -76.06417
- **Google Maps:** https://www.google.com/maps?q=39.20731,-76.06417

## Listing Agent

- **Name:** Michael ONeill
- **Brokerage:** Coldwell Banker Chesapeake Real Estate Company
- **Phone:** 4434804275
- **Email:** murphy@cbchesapeake.com

## Primary Photo

![105 HIGH Street - Primary Photo](http://lh.rdcpix.com/7ab19ee49a05e4d718c0c285543348e6l-f2822817397r.jpg)

*48 total photos available on [listing page](https://www.propertysimple.com/listing/105-high-street-chestertown-md-21620-e2005890)*

---

**MLS#:** MDKE2005890 | **Updated:** 2026-06-18
**Source:** listhub

*Copyright © 2026 Bright MLS. All rights reserved. All information provided by the listing agent/broker is deemed reliable but is not guaranteed and should be independently verified.*

[View on PropertySimple](https://www.propertysimple.com/listing/105-high-street-chestertown-md-21620-e2005890)

---

## Structured Data

```json
{
  "@context": "https://schema.org",
  "@type": "RealEstateListing",
  "name": "105 HIGH Street, Chestertown, MD 21620",
  "description": "Rebuilt in 1863, the Tilley Residence showcases classic Second Empire architecture on one of Chestertown's most prominent historic corners across from the Custom House, one of the first British Royal Ports of Entry to the Americas. Completely restored in 2025 by one of the Eastern Shore's iconic builders, the home blends historic character with modern comfort through thoughtful updates, new systems, and refined living spaces. Just one block to the waterfront promenade or to morning coffee at Eve",
  "url": "https://www.propertysimple.com/listing/105-high-street-chestertown-md-21620-e2005890",
  "image": "http://lh.rdcpix.com/7ab19ee49a05e4d718c0c285543348e6l-f2822817397r.jpg",
  "datePosted": "2026-06-18",
  "price": 1295500,
  "priceCurrency": "USD",
  "address": {
    "@type": "PostalAddress",
    "streetAddress": "105 HIGH Street",
    "addressLocality": "Chestertown",
    "addressRegion": "MD",
    "postalCode": "21620",
    "addressCountry": "US"
  },
  "geo": {
    "@type": "GeoCoordinates",
    "latitude": 39.20731,
    "longitude": -76.06417
  },
  "numberOfBedrooms": 5,
  "numberOfBathroomsTotal": 5,
  "numberOfFullBathrooms": 4,
  "numberOfPartialBathrooms": 1,
  "floorSize": {
    "@type": "QuantitativeValue",
    "value": 3243,
    "unitCode": "FTK"
  },
  "yearBuilt": 1863
}
```