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

$859,100

Trulia Estimate
  • 3 Beds
  • 3 Baths
  • 1,649 sqft

208 E Chestnut St, Saint Michaels, MD 21663

Est. Refi. Payment $4,969/mo*
Refinance Your Home
Currently Off Market - Sold Aug 18, 2022 for $650,000

Home Value

Trulia Estimate
$859K
Since last month
Increased$13K (+1.5%)
Since last year
Increased$42K (+5.1%)
Since last sale
Increased$206K (+31.6%)
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 +129% in the last 10 years
MonthEstimated value
2026
August 2026$856K
July 2026$843K
June 2026$847K
May 2026$843K
April 2026$836K
March 2026$835K
February 2026$818K
January 2026$800K
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
204 W Chew Ave, Saint Michaels, MD
0.28
Single-Family Home
$660,000
09/16/25
3
2
1,500
106 Grace St, Saint Michaels, MD
0.22
Single-Family Home
$775,000
12/02/25
3
1.5
2,068
114 E Chew Ave, Saint Michaels, MD
0.07
Single-Family Home
$1,152,500
06/10/26
3
2.5
2,336
408 Water St, Saint Michaels, MD
0.07
Single-Family Home
$995,000
10/08/25
3
2.5
1,893
107 E Chestnut St, Saint Michaels, MD
0.11
Single-Family Home
$1,135,000
07/27/26
2
2
2,024
204 Mulberry St, Saint Michaels, MD
0.12
Single-Family Home
$1,350,000
10/27/25
3
2.5
2,320
304 N Talbot St, St Michaels, MD
0.48
Single-Family Home
$785,000
10/15/25
3
2.5
2,028
113 Thompson St, Saint Michaels, MD
0.24
Single-Family Home
$580,000
10/31/25
3
2
1,566
207 Seymour Ave, Saint Michaels, MD
0.18
Single-Family Home
$800,000
11/17/25
4
3.5
1,983
205 E Chew Ave, Saint Michaels, MD
0.03
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
0.03
$1,175,000
2
1.5
1,780
Recently Sold
203 E Chew Ave, Saint Michaels, MD 21663
0.03
$2,125,000
5
5.5
4,673
Recently Sold
218 E Chestnut St, Saint Michaels, MD 21663
0.04
$1,942,200
4
4
2,639
Off Market
202 E Chestnut St, Saint Michaels, MD 21663
0.02
$1,250,000
3
3
2,052
For Sale
417 Water St, Saint Michaels, MD 21663
0.03
$1,844,800
3
3.5
2,579
Off Market
222 E Chestnut St, Saint Michaels, MD 21663
0.07
$1,825,000
3
2.5
2,284
Recently Sold
115 W Chew Ave, Saint Michaels, MD 21663
0.05
$1,011,300
4
2.5
1,781
Off Market
114 E Chew Ave, Saint Michaels, MD 21663
0.07
$1,152,500
3
2.5
2,336
Recently Sold
201 E Marengo St, St Michaels, MD 21663
0.08
$846,700
3
2.5
2,294
Off Market
204 E Marengo St, Saint Michaels, MD 21663
0.11
$549,999
2
1
1,200
For Sale
408 Water St, Saint Michaels, MD 21663
0.07
$975,300
3
2.5
1,893
Off Market
303 Manor St, Saint Michaels, MD 21663
0.13
$1,985,000
3
3
2,622
For Sale

Local Information

  • Map ViewExplore the area around 208 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
1853
Living Area
1,649 sqft
Price/Sqft
$521
Parking
Garage

About this House

What a find! Historical home in the heart of St. Michaels. House has two front porches, first floor bedroom and lovely rear brick private patio. Also has a rear detached workshop could be office. Charm of yesteryear galore in this property Come take a look today!
208 E Chestnut St, Saint Michaels, MD 21663 is a 3 bedroom, 3 bathroom, 1,649 sqft single-family home built in 1853. It last sold for $650,000 on Aug 18, 2022. This property is not currently displayed as for sale or rent on Trulia. The Trulia Estimate is $859,100, with a rent estimate of $2,468/month.

Home Details for 208 E Chestnut St

Interior Features

Heating & Cooling
Heating: Heat Pump, OilAir ConditioningHeating Fuel: Heat Pump
Levels, Entrance, & Accessibility
Stories: 2Floors: Other
Appliances & Utilities
DishwasherDryerMicrowaveRefrigeratorWasher
Fireplace & Spa
Fireplace

Exterior Features

Exterior Home Features
Roof: Other, Shake ShingleDeckExterior: Other, Wood
Parking & Garage
GarageParking: Carport, Garage Attached

Property Information

Year Built
Year Built: 1853
Property Type / Style
Property Type: Single Family HomeArchitecture: Conventional

Community

Units in Building: 1

Lot Information

Lot Area: 3600 sqft

Price and Tax history

DateEventPrice
Aug 18, 2022
Source: Bright MLS #MDTA2002656
Sold
$650,000
Jul 18, 2022
Source: Bright MLS #MDTA2002656
Pending
$717,000
Jul 4, 2022
Source: Bright MLS #MDTA2002656
ListingRemoved
$717,000
Jul 2, 2022
Source: Bright MLS #MDTA2002656
Listed For Sale
$717,000
Jun 6, 2022
Source: Bright MLS #MDTA2002656
ListingRemoved
$717,000

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 208 E Chestnut St

  • What is 208 E Chestnut St estimated to be worth?
    Trulia's estimated value for 208 E Chestnut St in Saint Michaels, MD is $859,100.
  • What is the price history for 208 E Chestnut St?
    208 E Chestnut St in Saint Michaels, MD last sold for $650,000 in August 2022.
  • 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 208 E Chestnut St?
    The closest schools to 208 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 208 E Chestnut St have laundry facilities?
    Yes, 208 E Chestnut St in Saint Michaels, MD has in-unit laundry.
  • How big is the lot at 208 E Chestnut St?
    The lot at 208 E Chestnut St in Saint Michaels, MD is about 0.08 acres (3,600 sq ft).

Explore by feature - Air Conditioning

6 rentals with air conditioning in Saint Michaels, MD

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