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

$1,072,900

Trulia Estimate
  • 3 Beds
  • 4 Baths
  • 2,926 sqft

209 E Chestnut St, Saint Michaels, MD 21663

Est. Refi. Payment $6,107/mo*
Refinance Your Home
Currently Off Market - Sold Aug 15, 2011 for $590,000

Home Value

Trulia Estimate
$1.07M
Since last month
Decreased$26K (-2.4%)
Since last year
Decreased$41K (-3.7%)
Since last sale
Increased$484K (+82%)
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 +55% in the last 10 years
MonthEstimated value
2026
August 2026$1.07M
August 2026$1.07M
July 2026$1.1M
June 2026$1.12M
May 2026$1.11M
April 2026$1.11M
March 2026$1.11M
February 2026$1.1M
January 2026$1.09M
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
114 E Chew Ave, Saint Michaels, MD
0.09
Single-Family Home
$1,152,500
06/10/26
3
2.5
2,336
204 Mulberry St, Saint Michaels, MD
0.09
Single-Family Home
$1,350,000
10/27/25
3
2.5
2,320
207 Seymour Ave, Saint Michaels, MD
0.21
Single-Family Home
$800,000
11/17/25
4
3.5
1,983
408 Water St, Saint Michaels, MD
0.04
Single-Family Home
$995,000
10/08/25
3
2.5
1,893
106 Grace St, Saint Michaels, MD
0.19
Single-Family Home
$775,000
12/02/25
3
1.5
2,068
222 E Chestnut St, Saint Michaels, MD
0.09
Single-Family Home
$1,825,000
08/10/26
3
2.5
2,284
113 Thompson St, Saint Michaels, MD
0.22
Single-Family Home
$580,000
10/31/25
3
2
1,566
204 W Chew Ave, Saint Michaels, MD
0.26
Single-Family Home
$660,000
09/16/25
3
2
1,500
121 W Chestnut St, St Michaels, MD
0.25
Single-Family Home
$1,395,000
06/22/26
3
2.5
2,540
107 E Chestnut St, Saint Michaels, MD
0.08
Single-Family Home
$1,135,000
07/27/26
2
2
2,024

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
202 E Chestnut St, Saint Michaels, MD 21663
0.02
$1,250,000
3
3
2,052
For Sale
203 E Chew Ave, Saint Michaels, MD 21663
0.06
$2,125,000
5
5.5
4,673
Recently Sold
417 Water St, Saint Michaels, MD 21663
0.02
$1,811,800
3
3.5
2,579
Off Market
205 E Chew Ave, Saint Michaels, MD 21663
0.06
$1,175,000
2
1.5
1,780
Recently Sold
408 Water St, Saint Michaels, MD 21663
0.04
$971,000
3
2.5
1,893
Off Market
106 E Chestnut St, Saint Michaels, MD 21663
0.08
$1,225,000
2
2.5
2,282
Recently Sold
114 E Chew Ave, Saint Michaels, MD 21663
0.09
$1,152,500
3
2.5
2,336
Recently Sold
107 E Chestnut St, Saint Michaels, MD 21663
0.08
$1,135,000
2
2
2,024
Recently Sold
218 E Chestnut St, Saint Michaels, MD 21663
0.07
$1,925,400
4
4
2,639
Off Market
201 E Marengo St, St Michaels, MD 21663
0.11
$835,900
3
2.5
2,294
Off Market
222 E Chestnut St, Saint Michaels, MD 21663
0.09
$1,825,000
3
2.5
2,284
Recently Sold
204 Mulberry St, Saint Michaels, MD 21663
0.09
$1,318,700
3
2.5
2,320
Off Market

Local Information

  • Map ViewExplore the area around 209 E Chestnut St.
  • Schools1 Preschool School1 Elementary School1 Middle School1 High School
  • Shop & Eat
-- mins to
Commute Destination

Home Highlights

Single-Family Home
Built in 1970
2,926 sqft
$367/sqft

About this House

Wow! a great place to "Call Home" ready to move in and enjoy the ambiance of St Michaels and the land of pleasant living. Walk to shops, restaurants, farmers market, waterfront parks and the harbor with water access is one block away.

Neighborhood Description

Very walkable, locally owned grocery store 1 block away, great meats, flowers, & local produce. Waterfront park 1 block away,harbor 1 block away, post office 2 blocks away, and very convenient to other amenities.
209 E Chestnut St, Saint Michaels, MD 21663 is a 3 bedroom, 4 bathroom, 2,926 sqft single-family home built in 1970. It last sold for $590,000 on Aug 15, 2011. This property is not currently displayed as for sale or rent on Trulia. The Trulia Estimate is $1,072,900, with a rent estimate of $2,938/month.

Home Details for 209 E Chestnut St

Interior Features

Heating & Cooling
Heating: Heat Pump, ElectricAir ConditioningCooling System: CentralHeating Fuel: Heat Pump
Levels, Entrance, & Accessibility
Stories: 2Floors: Tile, Hardwood
Interior Details
Types of Rooms: Walk In Closet, Breakfast Nook, Dining Room, Laundry Room, Master BathCeiling Fan
Appliances & Utilities
DishwasherDisposalDryerRefrigeratorWasher
Fireplace & Spa
FireplaceJetted Bath Tub
Windows, Doors, Floors & Walls
Double Paned Windows

Exterior Features

Exterior Home Features
Roof: Shake ShingleExterior: OtherGardenPatioPorchSprinkler System
Parking & Garage
Parking: Off Street

Property Information

Year Built
Year Built: 1970Year Updated: 2009
Property Type / Style
Property Type: Single Family HomeArchitecture: Conventional

Community

Units in Building: 1

Lot Information

Lot Area: 4560 sqft

Price and Tax history

DateEventPrice
Aug 15, 2011
Source: N/A
Sold
$590,000
Jun 26, 2008
Source: N/A
Sold
$450,000
Feb 19, 1997
Source: N/A
Sold
$160,000

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

Frequently asked questions about 209 E Chestnut St

  • What is 209 E Chestnut St estimated to be worth?
    Trulia's estimated value for 209 E Chestnut St in Saint Michaels, MD is $1,072,900.
  • What is the price history for 209 E Chestnut St?
    209 E Chestnut St in Saint Michaels, MD last sold for $590,000 in August 2011.
  • 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 209 E Chestnut St?
    The closest schools to 209 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 209 E Chestnut St have air conditioning?
    Yes, 209 E Chestnut St in Saint Michaels, MD has air conditioning.
  • Does 209 E Chestnut St have laundry facilities?
    Yes, 209 E Chestnut St in Saint Michaels, MD has in-unit laundry.

Explore by feature - Pet Friendly

Explore by feature - Air Conditioning

9 rentals with air conditioning in Saint Michaels, MD

Explore by feature - Washer/dryer

7 rentals with a washer/dryer in Saint Michaels, MD

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Off Market Homes Near 209 E Chestnut St

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