218 E Chestnut St, Saint Michaels, MD 21663
Property image
Property image
OFF MARKET

$1,942,200

Trulia Estimate
  • 4 Beds
  • 4 Baths
  • 2,639 sqft

218 E Chestnut St, Saint Michaels, MD 21663

Est. Refi. Payment $11,097/mo*
Refinance Your Home
Currently Off Market - Sold Apr 30, 2024 for $1,775,000

Home Value

Trulia Estimate
$1.94M
Since last month
Decreased$13K (-0.7%)
Since last year
Increased$59K (+3.1%)
Since last sale
Increased$163K (+9.2%)
Learn more about this home's value by checking out its Trulia Estimate, the value of nearby homes, and how much similar homes have sold for.

Trulia Estimate

The of this home's value increased by +158% in the last 10 years
MonthEstimated value
2026
August 2026$1.94M
July 2026$1.95M
June 2026$1.95M
May 2026$1.94M
April 2026$1.92M
March 2026$1.93M
February 2026$1.89M
January 2026$1.85M
2025
2024
2023
2022
2021
2020
2019
2018
2017
2016

Comparable sales

These are recently sold homes that have a similar location or other similar features to this home, like bedrooms, bathrooms, and square footage. Get a sense of the expected prices in the area by viewing these homes.
Address
Distance
Property Type
Sold Price
Sold Date
Bed
Bath
Sqft
222 E Chestnut St, Saint Michaels, MD
0.02
Single-Family Home
$1,825,000
08/10/26
3
2.5
2,284
204 Mulberry St, Saint Michaels, MD
0.14
Single-Family Home
$1,350,000
10/27/25
3
2.5
2,320
203 E Chew Ave, Saint Michaels, MD
0.07
Single-Family Home
$2,125,000
08/05/26
5
5.5
4,673
114 E Chew Ave, Saint Michaels, MD
0.11
Single-Family Home
$1,152,500
06/10/26
3
2.5
2,336
121 W Chestnut St, St Michaels, MD
0.32
Single-Family Home
$1,395,000
06/22/26
3
2.5
2,540
207 Seymour Ave, Saint Michaels, MD
0.19
Single-Family Home
$800,000
11/17/25
4
3.5
1,983
408 Water St, Saint Michaels, MD
0.10
Single-Family Home
$995,000
10/08/25
3
2.5
1,893
106 E Chestnut St, Saint Michaels, MD
0.14
Single-Family Home
$1,225,000
06/05/26
2
2.5
2,282
205 E Chew Ave, Saint Michaels, MD
0.06
Single-Family Home
$1,175,000
11/14/25
2
1.5
1,780

Nearby home prices

Get a sense of expected prices in the area by checking the value of nearby homes.
Address
Distance
Price
Bed
Bath
Sqft
Status
205 E Chew Ave, Saint Michaels, MD 21663
0.06
$1,175,000
2
1.5
1,780
Recently Sold
203 E Chew Ave, Saint Michaels, MD 21663
0.07
$2,125,000
5
5.5
4,673
Recently Sold
202 E Chestnut St, Saint Michaels, MD 21663
0.07
$1,250,000
3
3
2,052
For Sale
417 Water St, Saint Michaels, MD 21663
0.05
$1,823,700
3
3.5
2,579
Off Market
222 E Chestnut St, Saint Michaels, MD 21663
0.03
$1,825,000
3
2.5
2,284
Recently Sold
115 W Chew Ave, Saint Michaels, MD 21663
0.09
$1,011,300
4
2.5
1,781
Off Market
114 E Chew Ave, Saint Michaels, MD 21663
0.11
$1,152,500
3
2.5
2,336
Recently Sold
201 E Marengo St, St Michaels, MD 21663
0.11
$846,700
3
2.5
2,294
Off Market
204 E Marengo St, Saint Michaels, MD 21663
0.12
$549,999
2
1
1,200
For Sale
408 Water St, Saint Michaels, MD 21663
0.10
-
3
2.5
1,893
Off Market
303 Manor St, Saint Michaels, MD 21663
0.11
$1,985,000
3
3
2,622
For Sale

Local Information

  • Map ViewExplore the area around 218 E Chestnut St.
  • Schools1 Preschool School1 Elementary School1 Middle School1 High School
  • Shop & Eat
-- mins to
Commute Destination

Home Highlights

Property Type
Single-Family Home
Year Built
1870
Living Area
2,639 sqft
Price/Sqft
$736
Parking
Open Parking

About this House

This home is everything that is Historic St. Michaels! Water views from almost every room with the harbor across the street. Magnificent addition of a first floor primary suite which offers tall ceilings and doors leading to a private patio. This beautiful homes brings the perfect balance between historical charm, and updated modern features with a vibrant, coastal decor and flow! Classic tree lined street with no through traffic brings calm surroundings. Enjoy first floor living, but don't miss out on the second floor additional primary suite, cozy study/bonus room and additional bedrooms with beautiful water views! Private outdoor entertainment area with a detached workshop equipped with electric and heat. Off street parking with additional options with access to the alley in the back. Walk to your favorite restaurants and shops and enjoy the charm of everything St. Michaels has to offer! Call today to schedule your private tour.
218 E Chestnut St, Saint Michaels, MD 21663 is a 4 bedroom, 4 bathroom, 2,639 sqft single-family home built in 1870. It last sold for $1,775,000 on Apr 30, 2024 (5% below the $1,875,000 asking price). This property is not currently displayed as for sale or rent on Trulia. The Trulia Estimate is $1,942,200, with a rent estimate of $3,065/month.
Last check for updates: about 4 hours ago
Listed by Keith Hensley, (410) 739-2526
Meredith Fine Properties
Bought with: Cliff Meredith, (410) 822-6272, Meredith Fine Properties
Source: Bright MLS, MLS#MDTA2007312

Home Details for 218 E Chestnut St

Interior Features

Interior Details
Number of Rooms: 1Types of Rooms: Basement
Beds & Baths
Number of Bedrooms: 4Main Level Bedrooms: 1Number of Bathrooms: 4Number of Bathrooms (full): 4Number of Bathrooms (main level): 2
Dimensions and Layout
Living Area: 2639 Square Feet
Appliances & Utilities
Appliances: Electric Water Heater
Heating & Cooling
Heating: Heat Pump,ElectricHas CoolingAir Conditioning: Central Air,Heat Pump,ElectricHas HeatingHeating Fuel: Heat Pump
Fireplace & Spa
Number of Fireplaces: 1Has a Fireplace
Levels, Entrance, & Accessibility
Stories: 2Levels: TwoAccessibility: Doors - Swing In
View
Has a ViewView: Water

Exterior Features

Exterior Home Features
Other Structures: Above Grade, Below GradeFoundation: Crawl SpaceNo Private Pool
Parking & Garage
No CarportNo GarageNo Attached GarageHas Open ParkingParking: Driveway,Off Street
Pool
Pool: None
Frontage
Waterfront: RiverNot on Waterfront
Water & Sewer
Sewer: Public Sewer
Finished Area
Finished Area (above surface): 2639 Square Feet

Property Information

Year Built
Year Built: 1870
Property Type / Style
Property Type: ResidentialProperty Subtype: Single Family ResidenceStructure Type: DetachedArchitecture: Colonial
Building
Construction Materials: FrameNot a New Construction
Property Information
Parcel Number: 2102109697

Price & Status

Price
List Price: $1,875,000
Status Change & Dates
Off Market Date: Tue Apr 30 2024Possession Timing: Close Of Escrow

Active Status

MLS Status: CLOSED

Location

Direction & Address
City: SAINT MICHAELSCommunity: Historic St Michaels
School Information
Elementary School District: Talbot County Public SchoolsJr High / Middle School District: Talbot County Public SchoolsHigh School District: Talbot County Public Schools

Building

Building Area
Building Area: 2639 Square Feet

Community

Not Senior Community

HOA

No HOA

Lot Information

Lot Area: 7687 sqft

Listing Info

Special Conditions: Standard

Offer

Listing Agreement Type: Exclusive Right To Sell

Business

Business Information
Ownership: Fee Simple

Miscellaneous

Mls Number: MDTA2007312Municipality: Saint MichaelsWater ViewWater View: WaterAbove Grade Unfinished Area: 2639

Price and Tax history

DateEventPrice
Apr 30, 2024
Source: Bright MLS #MDTA2007312
Sold
$1,775,000
Mar 29, 2024
Source: Bright MLS #MDTA2007312
Pending
$1,875,000
Mar 8, 2024
Source: Bright MLS #MDTA2007312
Contingent
$1,875,000
Mar 2, 2024
Source: Bright MLS #MDTA2007312
Listed For Sale
$1,875,000
Jan 29, 2019
Source: N/A
Sold
$880,000

Market trends in Saint Michaels

Last updated July 2026
Buyer'sMarketSeller'sMarket
Avg. sale price
—
Sale-to-List Price
—
Price per sq ft
—
Available listings
50
3MoM

Around this home

What Locals Say about Saint Michaels

At least 2 Trulia users voted on each feature.

  • 100 % Say yards are well-kept

  • 100 % Say streets are well-lit

  • 92 % Say it's dog friendly

  • 92 % Say it's quiet

  • 90 % Say car is needed

  • 82 % Say parking is easy

  • 79 % Say there's wildlife

  • 75 % Say there's holiday spirit

  • 73 % Say kids play outside

  • 67 % Say people would walk alone at night

  • 64 % Say it's walkable to restaurants

  • 63 % Say there are community events

  • 58 % Say neighbors are friendly

  • 50 % Say it's walkable to grocery stores

  • 45 % Say there are sidewalks

  • 40 % Say they plan to stay for at least 5 years

Sourced by Trulia users. Learn more about our methodology.
  • Kgialo
    "There are many dog friendly places and lost of nice outdoor spaces for walks. People are very comfortable around dogs here. "
    0
    Flag
  • Christopherbthomas24
    "Love this town, great spot for young families and retirees as well. Awesome spots to eat and hang out"
    2
    Flag
  • Kats0791
    "Different kinds of houses to chose from including single family, town homes & condos. New Pete Dye Golf Course. "
    0
    Flag
  • Janet S.
    "Work and live here. Fantastic area - beautiful, with great sailing. The town has constantly improved since I moved here in 1993."
    0
    Flag
  • rctdesign
    "Wonderful town with lots to do and very walkable!"
    0
    Flag

LGBTQ Local Legal Protections

The data relating to real estate for sale on this website appears in part through the BRIGHT Internet Data Exchange program, a voluntary cooperative exchange of property listing data between licensed real estate brokerage firms, and is provided by BRIGHT through a licensing agreement. Listing information is from various brokers who participate in the Bright MLS IDX program and not all listings may be visible on the site. The property information being provided on or through the website is for the personal, non-commercial use of consumers and such information may not be used for any purpose other than to identify prospective properties consumers may be interested in purchasing. Some properties which appear for sale on the website may no longer be available because they are for instance, under contract, sold or are no longer being offered for sale. Property information displayed is deemed reliable but is not guaranteed. Copyright 2026 Bright MLS, Inc. Click here for more information

Frequently asked questions about 218 E Chestnut St

  • What is 218 E Chestnut St estimated to be worth?
    Trulia's estimated value for 218 E Chestnut St in Saint Michaels, MD is $1,942,200.
  • What is the price history for 218 E Chestnut St?
    218 E Chestnut St in Saint Michaels, MD last sold for $1,775,000 in April 2024.
  • Is Saint Michaels a buyer's or seller's market?
    Saint Michaels is currently a buyer's market, based on recent for-sale activity.
  • What are the closest schools to 218 E Chestnut St?
    The closest schools to 218 E Chestnut St in Saint Michaels, MD are St. Michaels Elementary School (Pre-K, rated 8/10), St. Michaels Middle/High School (rated 6/10).
  • Does 218 E Chestnut St have air conditioning?
    Yes, 218 E Chestnut St in Saint Michaels, MD has air conditioning.
  • How big is the lot at 218 E Chestnut St?
    The lot at 218 E Chestnut St in Saint Michaels, MD is about 0.18 acres (7,687 sq ft).

Explore by feature - Air Conditioning

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