208 E Chestnut St
Saint Michaels, MD 21663
3 Beds
2 Baths
1,649 sqft
3 Beds
2 Baths
1,649 sqft
Local Information
© Google
-- mins to
Description
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!
This property is off market, which means it's not currently listed for sale or rent on Trulia. This may be different from what's available on other websites or public sources.
Home Highlights
Parking
Garage
Outdoor
Deck
A/C
Heating & Cooling
HOA
None
Price/Sqft
No Info
Listed
No Info
Home Details for 208 E Chestnut St
|
|---|
Heating & Cooling Heating: Heat Pump, OilAir ConditioningHeating Fuel: Heat Pump |
Levels, Entrance, & Accessibility Stories: 3Floors: Other |
Appliances & Utilities DishwasherDryerMicrowaveRefrigeratorWasher |
Fireplace & Spa Fireplace |
|
|---|
Exterior Home Features Roof: OtherDeckExterior: Wood |
Parking & Garage GarageParking: Carport, Garage Attached |
|
|---|
Year Built Year Built: 1853 |
Property Type / Style Property Type: Single Family HomeArchitecture: Conventional |
|
|---|
Units in Building: 1 |
|
|---|
Lot Area: 3598 sqft |
Price History for 208 E Chestnut St
| Date | Price | Event | Source |
|---|---|---|---|
| 08/18/2022 | $650,000 | Sold | Bright MLS #MDTA2002656 |
| 07/18/2022 | $717,000 | Pending | Bright MLS #MDTA2002656 |
| 07/04/2022 | $717,000 | ListingRemoved | Bright MLS #MDTA2002656 |
| 07/02/2022 | $717,000 | Listed For Sale | Bright MLS #MDTA2002656 |
| 06/06/2022 | $717,000 | ListingRemoved | Bright MLS #MDTA2002656 |
| 05/29/2022 | $717,000 | Pending | Bright MLS #MDTA2002656 |
| 05/22/2022 | $717,000 | Listed For Sale | Bright MLS #MDTA2002656 |
| 11/28/2017 | $350,000 | Sold | N/A |
| 10/13/2017 | $303,000 | Pending | Agent Provided |
| 09/25/2017 | $303,000 | Listed For Sale | Agent Provided |
| 06/29/2017 | $358,254 | Sold | N/A |
| 12/31/2016 | $399,000 | ListingRemoved | Agent Provided |
| 12/12/2016 | $399,000 | Listed For Sale | Agent Provided |
| 10/30/2016 | $399,000 | ListingRemoved | Agent Provided |
| 07/15/2016 | $399,000 | PriceChange | Agent Provided |
| 05/09/2016 | $425,000 | PriceChange | Agent Provided |
| 12/20/2015 | $455,000 | PriceChange | Agent Provided |
| 11/20/2015 | $485,000 | Pending | Agent Provided |
| 09/10/2015 | $485,000 | Listed For Sale | Agent Provided |
- Results are loading
Property Tax and Assessment
| Year | 2025 |
|---|---|
| Tax | |
| Assessment | $494,500 |
Home facts updated by county records
Comparable Sales for 208 E Chestnut St
Address | Distance | Property Type | Sold Price | Sold Date | Bed | Bath | Sqft |
|---|---|---|---|---|---|---|---|
0.28 | Single-Family Home | $660,000 | 09/16/25 | 3 | 2 | 1,500 | |
0.22 | Single-Family Home | $775,000 | 12/02/25 | 3 | 1.5 | 2,068 | |
0.21 | Single-Family Home | $662,500 | 07/18/25 | 3 | 2 | 1,824 | |
0.24 | Single-Family Home | $600,000 | 08/08/25 | 3 | 2 | 1,660 | |
0.24 | Single-Family Home | $580,000 | 10/31/25 | 3 | 2 | 1,566 | |
0.16 | Single-Family Home | $800,000 | 08/15/25 | 4 | 1.5 | 1,596 | |
0.03 | Single-Family Home | $1,175,000 | 11/14/25 | 2 | 1.5 | 1,780 | |
0.14 | Single-Family Home | $926,000 | 01/15/26 | 3 | 2 | 1,740 | |
0.20 | Single-Family Home | $525,000 | 06/03/25 | 3 | 2 | 1,560 | |
0.15 | Single-Family Home | $850,000 | 07/31/25 | 3 | 2.5 | 2,072 |
Nearby homes
Get a sense of prices in the area by checking nearby homes.
FOR SALEColdwell Banker Chesapeake Real Estate Company
FOR SALETTR Sotheby's International Realty
FOR SALEOPEN SAT, 11-1PM1.51 ACRESTTR Sotheby's International Realty
FOR SALE
3D VIEW0.7 ACRESBenson & Mangold, LLC
SOLDMAY 13, 2026Long & Foster Real Estate, Inc.
FOR SALE
FOR SALELong & Foster Real Estate, Inc.
SOLDMAY 22, 2026Long & Foster Real Estate, Inc.
FOR SALE0.34 ACRESLong & Foster Real Estate, Inc.
FOR SALEBenson & Mangold, LLC
FOR SALE1.03 ACRESChesapeake Bay Real Estate Plus, LLC
Assigned Schools
These are the assigned schools for 208 E Chestnut St.
- St. Michaels Elementary School
- PK-5
- Public
- 333 Students
5/10GreatSchools RatingParent Rating AverageThis USED to be a good school. I have had 3 children at this school and now they are in private school. We moved here so I could be a stay at home mom. Because of the lack of accountability at this school I had to go back to work to pay for private school. The dream of living in a small town with a small school and being able to get my kids off the bus in the afternoon is gone. Teachers that have had children in this school are sending their own kids to private school. This should tell you enough right there. Also, this school only goes up to 5th grade and the student to teacher ratio is not accurate. They have eliminated teachers/classes so they have larger class sizes.Parent Review8y ago - St. Michaels Middle/High School
- 6-12
- Public
- 443 Students
5/10GreatSchools RatingParent Rating AverageN/ATeacher Review18y ago 
Check out schools near 208 E Chestnut St.
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.
LGBTQ Local Legal Protections
LGBTQ Local Legal Protections
Apartments for Rent
APPLY INSTANTLY
PET FRIENDLYFURNISHED
PET FRIENDLY
See more homes for rent inSaint Michaels
Homes for sale near 208 E Chestnut St
- TTR Sotheby's International Realty
OPEN FRI, 11-1PMMeredith Fine Properties
Long & Foster Real Estate, Inc.- Coldwell Banker Chesapeake Real Estate Company
- Long & Foster Real Estate, Inc.
NEW CONSTRUCTION0.41 ACRESTTR Sotheby's International Realty
See more homes for sale inSaint Michaels
Off Market Homes Near 208 E Chestnut St
- SOLDMAY 21, 2026Northrop Realty
SOLDMAY 18, 2026Benson & Mangold, LLC
SOLDMAY 15, 2026Benson & Mangold, LLC- SOLDMAY 13, 2026Long & Foster Real Estate, Inc.
SOLDMAY 4, 2026
SOLDMAY 1, 2026Benson & Mangold, LLC
SOLDAPR 30, 2026Benson & Mangold, LLC- SOLDAPR 29, 2026
- SOLDAPR 23, 2026
- See more homes for sale inSaint Michaels
Homes for rent near 208 E Chestnut St
- APPLY INSTANTLY
- PET FRIENDLYFURNISHED
- PET FRIENDLY
- See more homes for rent inSaint Michaels
208 E Chestnut St, Saint Michaels, MD 21663 is a 3 bedroom, 2 bathroom, 1,649 sqft single-family home built in 1853. This property is not currently available for sale. 208 E Chestnut St was last sold on Aug 18, 2022 for $650,000. The current Trulia Estimate for 208 E Chestnut St is $840,500.