# 105 HIGH Street, Chestertown, MD 21620

> **TL;DR:** 5bd/5ba single family, $1,245,500 ($384/sqft), built 1863, 3,243 sqft.
> Fireplace, A/C, 1-car garage. Est. $6,661/mo. Listed 320 days.

## Property at a Glance

| Attribute | Value |
|-----------|-------|
| Price | $1,245,500 |
| Price/sqft | $384 |
| 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 | 320 |

## Estimated Monthly Costs

| Category | Amount |
|----------|--------|
| Principal & Interest (20% down, 30-year at 6.5%) | $6,298 |
| Estimated Insurance | $363 |
| **Total** | **$6,661** |

## 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
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

## 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
- **Phone:** 4434804275
- **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-f348325756r.jpg)

![105 HIGH Street - Photo 2](http://lh.rdcpix.com/7ab19ee49a05e4d718c0c285543348e6l-f2342431689r.jpg)

![105 HIGH Street - Photo 3](http://lh.rdcpix.com/7ab19ee49a05e4d718c0c285543348e6l-f287187846r.jpg)

![105 HIGH Street - Photo 4](http://lh.rdcpix.com/7ab19ee49a05e4d718c0c285543348e6l-f3341368310r.jpg)

![105 HIGH Street - Photo 5](http://lh.rdcpix.com/7ab19ee49a05e4d718c0c285543348e6l-f2747181974r.jpg)

![105 HIGH Street - Photo 6](http://lh.rdcpix.com/7ab19ee49a05e4d718c0c285543348e6l-f2610825390r.jpg)

![105 HIGH Street - Photo 7](http://lh.rdcpix.com/7ab19ee49a05e4d718c0c285543348e6l-f3933193709r.jpg)

![105 HIGH Street - Photo 8](http://lh.rdcpix.com/7ab19ee49a05e4d718c0c285543348e6l-f2333301759r.jpg)

![105 HIGH Street - Photo 9](http://lh.rdcpix.com/7ab19ee49a05e4d718c0c285543348e6l-f3555032737r.jpg)

![105 HIGH Street - Photo 10](http://lh.rdcpix.com/7ab19ee49a05e4d718c0c285543348e6l-f1226294174r.jpg)

![105 HIGH Street - Photo 11](http://lh.rdcpix.com/7ab19ee49a05e4d718c0c285543348e6l-f3933032458r.jpg)

![105 HIGH Street - Photo 12](http://lh.rdcpix.com/7ab19ee49a05e4d718c0c285543348e6l-f613338489r.jpg)

![105 HIGH Street - Photo 13](http://lh.rdcpix.com/7ab19ee49a05e4d718c0c285543348e6l-f3214080155r.jpg)

![105 HIGH Street - Photo 14](http://lh.rdcpix.com/7ab19ee49a05e4d718c0c285543348e6l-f3184387820r.jpg)

![105 HIGH Street - Photo 15](http://lh.rdcpix.com/7ab19ee49a05e4d718c0c285543348e6l-f591570739r.jpg)

![105 HIGH Street - Photo 16](http://lh.rdcpix.com/7ab19ee49a05e4d718c0c285543348e6l-f860737356r.jpg)

![105 HIGH Street - Photo 17](http://lh.rdcpix.com/7ab19ee49a05e4d718c0c285543348e6l-f4231400018r.jpg)

![105 HIGH Street - Photo 18](http://lh.rdcpix.com/7ab19ee49a05e4d718c0c285543348e6l-f3671022481r.jpg)

![105 HIGH Street - Photo 19](http://lh.rdcpix.com/7ab19ee49a05e4d718c0c285543348e6l-f2973210994r.jpg)

![105 HIGH Street - Photo 20](http://lh.rdcpix.com/7ab19ee49a05e4d718c0c285543348e6l-f2302762894r.jpg)

![105 HIGH Street - Photo 21](http://lh.rdcpix.com/7ab19ee49a05e4d718c0c285543348e6l-f2129200949r.jpg)

![105 HIGH Street - Photo 22](http://lh.rdcpix.com/7ab19ee49a05e4d718c0c285543348e6l-f1825213972r.jpg)

![105 HIGH Street - Photo 23](http://lh.rdcpix.com/7ab19ee49a05e4d718c0c285543348e6l-f1825570707r.jpg)

![105 HIGH Street - Photo 24](http://lh.rdcpix.com/7ab19ee49a05e4d718c0c285543348e6l-f2788435675r.jpg)

![105 HIGH Street - Photo 25](http://lh.rdcpix.com/7ab19ee49a05e4d718c0c285543348e6l-f2540593454r.jpg)

![105 HIGH Street - Photo 26](http://lh.rdcpix.com/7ab19ee49a05e4d718c0c285543348e6l-f464057598r.jpg)

![105 HIGH Street - Photo 27](http://lh.rdcpix.com/7ab19ee49a05e4d718c0c285543348e6l-f3110199207r.jpg)

![105 HIGH Street - Photo 28](http://lh.rdcpix.com/7ab19ee49a05e4d718c0c285543348e6l-f2606003333r.jpg)

![105 HIGH Street - Photo 29](http://lh.rdcpix.com/7ab19ee49a05e4d718c0c285543348e6l-f862786188r.jpg)

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

![105 HIGH Street - Photo 31](http://lh.rdcpix.com/7ab19ee49a05e4d718c0c285543348e6l-f2755740257r.jpg)

![105 HIGH Street - Photo 32](http://lh.rdcpix.com/7ab19ee49a05e4d718c0c285543348e6l-f787480377r.jpg)

![105 HIGH Street - Photo 33](http://lh.rdcpix.com/7ab19ee49a05e4d718c0c285543348e6l-f843484690r.jpg)

![105 HIGH Street - Photo 34](http://lh.rdcpix.com/7ab19ee49a05e4d718c0c285543348e6l-f2084082424r.jpg)

![105 HIGH Street - Photo 35](http://lh.rdcpix.com/7ab19ee49a05e4d718c0c285543348e6l-f2964099821r.jpg)

![105 HIGH Street - Photo 36](http://lh.rdcpix.com/7ab19ee49a05e4d718c0c285543348e6l-f1613977386r.jpg)

![105 HIGH Street - Photo 37](http://lh.rdcpix.com/7ab19ee49a05e4d718c0c285543348e6l-f3189224429r.jpg)

![105 HIGH Street - Photo 38](http://lh.rdcpix.com/7ab19ee49a05e4d718c0c285543348e6l-f2822817397r.jpg)

![105 HIGH Street - Photo 39](http://lh.rdcpix.com/7ab19ee49a05e4d718c0c285543348e6l-f976943151r.jpg)

![105 HIGH Street - Photo 40](http://lh.rdcpix.com/7ab19ee49a05e4d718c0c285543348e6l-f1199170351r.jpg)

![105 HIGH Street - Photo 41](http://lh.rdcpix.com/7ab19ee49a05e4d718c0c285543348e6l-f1132783486r.jpg)

![105 HIGH Street - Photo 42](http://lh.rdcpix.com/7ab19ee49a05e4d718c0c285543348e6l-f1530712989r.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)

---

**MLS#:** MDKE2005890 | **Updated:** 2026-09-21
**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.ai/listing/105-high-street-chestertown-md-21620-e2005890)

---

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        "name": "Heating",
        "value": "Heat Pump (Heating)"
      },
      {
        "@type": "LocationFeatureSpecification",
        "name": "Cooling",
        "value": "Central Air"
      },
      {
        "@type": "LocationFeatureSpecification",
        "name": "Construction Materials",
        "value": "Frame"
      },
      {
        "@type": "LocationFeatureSpecification",
        "name": "Parking Features",
        "value": "Garage - Detached"
      },
      {
        "@type": "LocationFeatureSpecification",
        "name": "Fireplace",
        "value": true
      },
      {
        "@type": "LocationFeatureSpecification",
        "name": "Air Conditioning",
        "value": true
      }
    ],
    "additionalProperty": [
      {
        "@type": "PropertyValue",
        "name": "Lot Size",
        "value": "0.06 acres"
      },
      {
        "@type": "PropertyValue",
        "name": "Stories",
        "value": 4
      },
      {
        "@type": "PropertyValue",
        "name": "Parking Spaces",
        "value": 1
      },
      {
        "@type": "PropertyValue",
        "name": "Garage Spaces",
        "value": 1
      },
      {
        "@type": "PropertyValue",
        "name": "Property Subtype",
        "value": "Other"
      }
    ]
  },
  "offers": {
    "@type": "Offer",
    "@id": "https://www.propertysimple.ai/listing/105-high-street-chestertown-md-21620-e2005890#offer",
    "url": "https://www.propertysimple.ai/listing/105-high-street-chestertown-md-21620-e2005890",
    "price": 1245500,
    "priceCurrency": "USD",
    "businessFunction": "http://purl.org/goodrelations/v1#Sell",
    "availability": "https://schema.org/InStock",
    "seller": {
      "@id": "https://www.propertysimple.ai/listing/105-high-street-chestertown-md-21620-e2005890#agent"
    }
  },
  "provider": {
    "@type": "Person",
    "@id": "https://www.propertysimple.ai/listing/105-high-street-chestertown-md-21620-e2005890#agent",
    "name": "Michael ONeill",
    "telephone": "4434804275",
    "worksFor": {
      "@type": "Organization",
      "@id": "https://www.propertysimple.ai/listing/105-high-street-chestertown-md-21620-e2005890#brokerage",
      "name": "Coldwell Banker Chesapeake Real Estate Co, LLC",
      "telephone": "(410) 822-9000"
    }
  }
}
```