# 105 HIGH Street, Chestertown, MD 21620

> **TL;DR:** 5bd/5ba single family, $1,195,000 ($368/sqft), built 1863, 3,243 sqft.
> Fireplace, A/C, 1-car garage. Est. $6,392/mo. Listed 355 days.

## Property at a Glance

| Attribute | Value |
|-----------|-------|
| Price | $1,195,000 |
| Price/sqft | $368 |
| Bedrooms | 5 |
| Bathrooms | 4 full, 1 half |
| Square Feet | 3,243 |
| Year Built | 1863 |
| Lot Size | 2,688 sqft (0.06 acres) |
| Stories | 4 |
| Garage | 1-car |
| Property Type | Single Family (Other) |
| Status | Active |
| Days on Market | 355 |

## Estimated Monthly Costs

| Category | Amount |
|----------|--------|
| Principal & Interest (20% down, 30-year at 6.5%) | $6,043 |
| Estimated Insurance | $349 |
| **Total** | **$6,392** |

## Key Amenities

- Fireplace
- A/C
- 1-car garage

## Property Highlights

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

## Description

### Agent Description
Morning light pours through restored original windows. The river shimmers a block away, and a mansard roof that has watched over High Street since 1863 frames it all. Rebuilt after the fire of its day, the Tilley Residence has been brought back since 2022 by a top builder and his designer sister. A grand staircase, refinished by hand over many months, rises past glimpses of the water. The new custom kitchen is made for gathering. Upstairs, the primary suite has its own fireplace, and there are 4.5 brand-new baths. Below, a bright lower level holds a wine cellar. Everything unseen is new, too: HVAC, electrical, plumbing, roof and insulation. Outside, there's a private fenced yard, a remodeled garage, and the historic Custom House next door. Shops, galleries, dining and the marina are all a short stroll away. There is no better chance to drop your keys and create your legacy in Chestertown's Historic District.

## 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

## Virtual Tour & Media

- **Video Tour:** https://www.youtube.com/watch?v=bOoR9Fi5cM8&t=1s

## Listing Agent

- **Name:** Michael ONeill · **License:** 5010912
- **Brokerage:** Coldwell Banker Chesapeake Real Estate Co, LLC
- **Broker Phone:** (410) 822-9000
- **Listing URL:** [View original listing](https://www.realtor.com/realestateandhomes-detail/105-High-St_Chestertown_MD_21620_M53559-04553?f=listhub&s=TRENDPA&m=MDKE2005890&c=propsimple)

## Photos

![105 HIGH Street - Photo 1](http://lh.rdcpix.com/7ab19ee49a05e4d718c0c285543348e6l-f3899406779r.jpg)

![105 HIGH Street - Photo 2](http://lh.rdcpix.com/7ab19ee49a05e4d718c0c285543348e6l-f3990517990r.jpg)

![105 HIGH Street - Photo 3](http://lh.rdcpix.com/7ab19ee49a05e4d718c0c285543348e6l-f590894853r.jpg)

![105 HIGH Street - Photo 4](http://lh.rdcpix.com/7ab19ee49a05e4d718c0c285543348e6l-f2282072870r.jpg)

![105 HIGH Street - Photo 5](http://lh.rdcpix.com/7ab19ee49a05e4d718c0c285543348e6l-f976130753r.jpg)

![105 HIGH Street - Photo 6](http://lh.rdcpix.com/7ab19ee49a05e4d718c0c285543348e6l-f3418505794r.jpg)

![105 HIGH Street - Photo 7](http://lh.rdcpix.com/7ab19ee49a05e4d718c0c285543348e6l-f906502597r.jpg)

![105 HIGH Street - Photo 8](http://lh.rdcpix.com/7ab19ee49a05e4d718c0c285543348e6l-f3555032737r.jpg)

![105 HIGH Street - Photo 9](http://lh.rdcpix.com/7ab19ee49a05e4d718c0c285543348e6l-f2715786267r.jpg)

![105 HIGH Street - Photo 10](http://lh.rdcpix.com/7ab19ee49a05e4d718c0c285543348e6l-f3613918047r.jpg)

![105 HIGH Street - Photo 11](http://lh.rdcpix.com/7ab19ee49a05e4d718c0c285543348e6l-f1917916525r.jpg)

![105 HIGH Street - Photo 12](http://lh.rdcpix.com/7ab19ee49a05e4d718c0c285543348e6l-f2392108188r.jpg)

![105 HIGH Street - Photo 13](http://lh.rdcpix.com/7ab19ee49a05e4d718c0c285543348e6l-f2461233770r.jpg)

![105 HIGH Street - Photo 14](http://lh.rdcpix.com/7ab19ee49a05e4d718c0c285543348e6l-f860737356r.jpg)

![105 HIGH Street - Photo 15](http://lh.rdcpix.com/7ab19ee49a05e4d718c0c285543348e6l-f4231400018r.jpg)

![105 HIGH Street - Photo 16](http://lh.rdcpix.com/7ab19ee49a05e4d718c0c285543348e6l-f2550429063r.jpg)

![105 HIGH Street - Photo 17](http://lh.rdcpix.com/7ab19ee49a05e4d718c0c285543348e6l-f3184387820r.jpg)

![105 HIGH Street - Photo 18](http://lh.rdcpix.com/7ab19ee49a05e4d718c0c285543348e6l-f2431363580r.jpg)

![105 HIGH Street - Photo 19](http://lh.rdcpix.com/7ab19ee49a05e4d718c0c285543348e6l-f4052266522r.jpg)

![105 HIGH Street - Photo 20](http://lh.rdcpix.com/7ab19ee49a05e4d718c0c285543348e6l-f252171822r.jpg)

![105 HIGH Street - Photo 21](http://lh.rdcpix.com/7ab19ee49a05e4d718c0c285543348e6l-f2798469853r.jpg)

![105 HIGH Street - Photo 22](http://lh.rdcpix.com/7ab19ee49a05e4d718c0c285543348e6l-f1675770228r.jpg)

![105 HIGH Street - Photo 23](http://lh.rdcpix.com/7ab19ee49a05e4d718c0c285543348e6l-f3963792342r.jpg)

![105 HIGH Street - Photo 24](http://lh.rdcpix.com/7ab19ee49a05e4d718c0c285543348e6l-f1915377047r.jpg)

![105 HIGH Street - Photo 25](http://lh.rdcpix.com/7ab19ee49a05e4d718c0c285543348e6l-f464057598r.jpg)

![105 HIGH Street - Photo 26](http://lh.rdcpix.com/7ab19ee49a05e4d718c0c285543348e6l-f3110199207r.jpg)

![105 HIGH Street - Photo 27](http://lh.rdcpix.com/7ab19ee49a05e4d718c0c285543348e6l-f3011242457r.jpg)

![105 HIGH Street - Photo 28](http://lh.rdcpix.com/7ab19ee49a05e4d718c0c285543348e6l-f2935771918r.jpg)

![105 HIGH Street - Photo 29](http://lh.rdcpix.com/7ab19ee49a05e4d718c0c285543348e6l-f2606003333r.jpg)

![105 HIGH Street - Photo 30](http://lh.rdcpix.com/7ab19ee49a05e4d718c0c285543348e6l-f178506607r.jpg)

![105 HIGH Street - Photo 31](http://lh.rdcpix.com/7ab19ee49a05e4d718c0c285543348e6l-f1252485286r.jpg)

![105 HIGH Street - Photo 32](http://lh.rdcpix.com/7ab19ee49a05e4d718c0c285543348e6l-f2755740257r.jpg)

![105 HIGH Street - Photo 33](http://lh.rdcpix.com/7ab19ee49a05e4d718c0c285543348e6l-f2588275319r.jpg)

![105 HIGH Street - Photo 34](http://lh.rdcpix.com/7ab19ee49a05e4d718c0c285543348e6l-f150398473r.jpg)

![105 HIGH Street - Photo 35](http://lh.rdcpix.com/7ab19ee49a05e4d718c0c285543348e6l-f2705865412r.jpg)

![105 HIGH Street - Photo 36](http://lh.rdcpix.com/7ab19ee49a05e4d718c0c285543348e6l-f2680297293r.jpg)

![105 HIGH Street - Photo 37](http://lh.rdcpix.com/7ab19ee49a05e4d718c0c285543348e6l-f173520157r.jpg)

![105 HIGH Street - Photo 38](http://lh.rdcpix.com/7ab19ee49a05e4d718c0c285543348e6l-f115000677r.jpg)

![105 HIGH Street - Photo 39](http://lh.rdcpix.com/7ab19ee49a05e4d718c0c285543348e6l-f3736798886r.jpg)

![105 HIGH Street - Photo 40](http://lh.rdcpix.com/7ab19ee49a05e4d718c0c285543348e6l-f2822817397r.jpg)

![105 HIGH Street - Photo 41](http://lh.rdcpix.com/7ab19ee49a05e4d718c0c285543348e6l-f976943151r.jpg)

![105 HIGH Street - Photo 42](http://lh.rdcpix.com/7ab19ee49a05e4d718c0c285543348e6l-f1199170351r.jpg)

![105 HIGH Street - Photo 43](http://lh.rdcpix.com/7ab19ee49a05e4d718c0c285543348e6l-f897091675r.jpg)

![105 HIGH Street - Photo 44](http://lh.rdcpix.com/7ab19ee49a05e4d718c0c285543348e6l-f4225050101r.jpg)

![105 HIGH Street - Photo 45](http://lh.rdcpix.com/7ab19ee49a05e4d718c0c285543348e6l-f1377784652r.jpg)

![105 HIGH Street - Photo 46](http://lh.rdcpix.com/7ab19ee49a05e4d718c0c285543348e6l-f2747181974r.jpg)

---

**MLS#:** MDKE2005890 | **Updated:** 2026-10-26
**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://staging.propertysimple.ai/listing/105-high-street-chestertown-md-21620-ea8fa6b760b841bcac4a07c42c6502fb)

---

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