# 114 W CHESTNUT Street, Saint Michaels, MD 21663

> **TL;DR:** 4bd/5ba single family, $1,285,000 ($364/sqft), built 1850, 3,528 sqft.
> Fireplace. Est. $5,568/mo. Listed 76 days.

## Property at a Glance

| Attribute | Value |
|-----------|-------|
| Price | $1,285,000 |
| Price/sqft | $364 |
| Bedrooms | 4 |
| Bathrooms | 4 full, 1 half |
| Square Feet | 3,528 |
| Year Built | 1850 |
| Lot Size | 7,200 sqft (0.17 acres) |
| Stories | 3 |
| Property Type | Single Family (Other) |
| Status | For Sale |
| Days on Market | 76 |

## Estimated Monthly Costs

| Category | Amount |
|----------|--------|
| Mortgage (20% down, 6.5%) | $5,568 |
| **Total** | **$5,568** |

## Key Amenities

- Fireplace

## Property Highlights

- Built in 1850
- 0.17 acre lot
- 3 stories
- Fireplace

## Description

### Agent Description
Enjoy historic in-town living in the heart of St. Michaels, where this beautifully maintained residence offers a rare combination of timeless architecture, a sought-after waterfront-adjacent location, and convenient access to the harbor, parks, trails, shops, and restaurants. Ideally located near the waterfront, scenic trails, park, kayak launch, and the town's many amenities, the home provides easy access to the best of Eastern Shore living. Inside, warm and inviting interiors feature hardwood floors throughout, multiple living areas, and four wood-burning fireplaces that enhance the home's historic character. The flexible floor plan includes four bedrooms, four and one-half baths, a dedicated office, custom built-ins, and generous storage, well-suited for a variety of living arrangements and lifestyle needs. Thoughtfully designed spaces offer both comfortable everyday living and additional room for guests, creative pursuits, work-from-home flexibility, or future customization. Outdoor features include a landscaped fenced yard designed for privacy and low-maintenance enjoyment, along with a spacious patio ideal for outdoor entertaining and relaxation. A detached cottage provides added versatility for use as a studio, workshop, or storage space. Off-street parking is an added convenience within the Historic District. Blending historic charm, adaptable living spaces, and an exceptional in-town location, this distinctive residence offers a unique opportunity to experience life in one of Maryland's most desirable waterfront communities.

## Location

- **Address:** 114 W CHESTNUT Street, Saint Michaels, MD 21663
- **County:** TALBOT
- **Neighborhood:** NONE AVAILABLE
- **Coordinates:** 38.78167295, -76.22489381
- **Google Maps:** https://www.google.com/maps?q=38.78167295,-76.22489381

## Listing Agent

- **Name:** Winifred C Cowee
- **Brokerage:** Benson & Mangold, LLC
- **Phone:** 4103100208
- **Email:** winkcowee@gmail.com

## Primary Photo

![114 W CHESTNUT Street - Primary Photo](http://lh.rdcpix.com/32390308a945e8e5a98606d582751ae7l-f3589449792r.jpg)

*75 total photos available on [listing page](https://www.propertysimple.com/listing/114-w-chestnut-street-saint-michaels-md-21663-a2013116)*

---

**MLS#:** MDTA2013116 | **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/114-w-chestnut-street-saint-michaels-md-21663-a2013116)

---

## Structured Data

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{
  "@context": "https://schema.org",
  "@type": "RealEstateListing",
  "name": "114 W CHESTNUT Street, Saint Michaels, MD 21663",
  "description": "Enjoy historic in-town living in the heart of St. Michaels, where this beautifully maintained residence offers a rare combination of timeless architecture, a sought-after waterfront-adjacent location, and convenient access to the harbor, parks, trails, shops, and restaurants. Ideally located near the waterfront, scenic trails, park, kayak launch, and the town's many amenities, the home provides easy access to the best of Eastern Shore living. Inside, warm and inviting interiors feature hardwood ",
  "url": "https://www.propertysimple.com/listing/114-w-chestnut-street-saint-michaels-md-21663-a2013116",
  "image": "http://lh.rdcpix.com/32390308a945e8e5a98606d582751ae7l-f3589449792r.jpg",
  "datePosted": "2026-06-18",
  "price": 1285000,
  "priceCurrency": "USD",
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  "numberOfBedrooms": 4,
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  "numberOfPartialBathrooms": 1,
  "floorSize": {
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```