Off Market1330d on marketHistoric · 173 yrs

208 E Chestnut St

Saint Michaels, MD, 21663 • 21663 • Talbot County

$834,800

$506/sqft

3Beds

2Baths

1,649Sqft

0.08 acLot

1853Built

Property DNA

1 highlights

Conventional Style

Built 1853 · 173 years of history

Market activity

Demand and pricing signals for this listing

2 views

People checking out this listing

1330 days on market

Established listing

$506/sqft

Price per square foot

About this home

Single Family · Built 1853 · Historic

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!

Estimated monthly payment

Based on current rates

$5,161/month

Principal & Interest$4,048

Property Tax$835

Insurance$278

Down payment20% ($166,960)

3%50%

Est. 6.10% rate · 30yr fixed · $667,840 loan

Full calculator →

At a glance

Key facts and listing details

TypeSingleFamily

Year Built1853

HeatingHeat pump, Oil

ParkingCarport, Garage - Attached

Lot3,598 sqft

Property

Home typeSingle Family

StyleConventional

Year built1853

Systems

HeatingHeat pump, Oil

RoofOther

ConstructionFrame

Parking & Outdoor

ParkingCarport, Garage - Attached

Lot3,598 sqft

Location & Tax

Neighborhood21663

Parcel02063565

Bathrooms & Fees

Full baths2

Features & details

6 categories of property features

Interior Features

Appliances

Dishwasher

Dryer

Microwave

Refrigerator

Washer

Flooring

Other

Heating

Heat pump

Oil

Exterior Features

Exterior

Wood

Parking

Carport

Garage - Attached

Construction

Frame

Listing insights

Market data and value estimates

StatusOff Market

Days on market1330

Est. value$834,800

Est. rent$2,368/mo

Tax rate0.66%

Price/sqft$506

Last sold$650,000

Tour days6

How are the schools in Saint Michaels?

2 schools rated nearby

St. Michaels Elementary School

Primary • Public • PK-5

0.3 mi

St. Michaels Middle/High School

Middle • Public • 6-12

0.3 mi

Location

Saint Michaels, MD, 21663

Expand map

Price history

19 events

DateEventPrice$/sqftSource

Aug 18, 2022Sold$650,000$394Bright MLS

Jul 18, 2022Pending Sale$717,000$435Bright MLS

Jul 4, 2022Listing Removed$717,000$435Bright MLS

Jul 2, 2022Listed For Sale$717,000$435Bright MLS

Jun 6, 2022Listing Removed$717,000$435Bright MLS

May 29, 2022Pending Sale$717,000$435Bright MLS

May 22, 2022Listed For Sale$717,000$435Bright MLS

Nov 28, 2017Sold$350,000$212Public Record

Oct 13, 2017Pending Sale$303,000$184Champion Realty, Inc.

Sep 25, 2017Listed For Sale$303,000$184Champion Realty, Inc.

Jun 29, 2017Sold$358,254$217Public Record

Dec 31, 2016Listing Removed$399,000$242Benson & Mangold LLC

Dec 12, 2016Listed For Sale$399,000$242Benson & Mangold LLC

Oct 30, 2016Listing Removed$399,000$242Benson & Mangold LLC

Jul 15, 2016Price Change$399,000$242Benson & Mangold LLC

May 9, 2016Price Change$425,000$258Benson & Mangold LLC

Dec 20, 2015Price Change$455,000$276Benson & Mangold LLC

Nov 20, 2015Pending Sale$485,000$294Benson & Mangold LLC

Sep 10, 2015Listed For Sale$485,000$294Benson & Mangold LLC

Sold$650,000

Aug 18, 2022•$394/sqft•Bright MLS

Pending Sale$717,000

Jul 18, 2022•$435/sqft•Bright MLS

Listing Removed$717,000

Jul 4, 2022•$435/sqft•Bright MLS

Listed For Sale$717,000

Jul 2, 2022•$435/sqft•Bright MLS

Listing Removed$717,000

Jun 6, 2022•$435/sqft•Bright MLS

Pending Sale$717,000

May 29, 2022•$435/sqft•Bright MLS

Listed For Sale$717,000

May 22, 2022•$435/sqft•Bright MLS

Sold$350,000

Nov 28, 2017•$212/sqft•Public Record

Pending Sale$303,000

Oct 13, 2017•$184/sqft•Champion Realty, Inc.

Listed For Sale$303,000

Sep 25, 2017•$184/sqft•Champion Realty, Inc.

Sold$358,254

Jun 29, 2017•$217/sqft•Public Record

Listing Removed$399,000

Dec 31, 2016•$242/sqft•Benson & Mangold LLC

Listed For Sale$399,000

Dec 12, 2016•$242/sqft•Benson & Mangold LLC

Listing Removed$399,000

Oct 30, 2016•$242/sqft•Benson & Mangold LLC

Price Change$399,000

Jul 15, 2016•$242/sqft•Benson & Mangold LLC

Price Change$425,000

May 9, 2016•$258/sqft•Benson & Mangold LLC

Price Change$455,000

Dec 20, 2015•$276/sqft•Benson & Mangold LLC

Pending Sale$485,000

Nov 20, 2015•$294/sqft•Benson & Mangold LLC

Listed For Sale$485,000

Sep 10, 2015•$294/sqft•Benson & Mangold LLC

Tax history

25 years of records

YearTax paidAssessed value

Apr 10, 2025—$494,500

Apr 10, 2024$6,040$484,767

Apr 10, 2023$5,693$475,033

Apr 10, 2022$5,384$465,300

Apr 10, 2021$5,333$465,300

Apr 10, 2020$5,333$465,300

Apr 10, 2019$5,399$471,000

Apr 10, 2018$5,023$450,467

Apr 10, 2017$4,642$429,933

Apr 10, 2016$1,669$409,400

Apr 10, 2015$1,669$409,400

Apr 10, 2014$1,857$409,400

Apr 10, 2013—$518,900

Apr 10, 2012—$518,900

Apr 10, 2011—$518,900

Apr 10, 2010—$621,250

Apr 10, 2009—$559,042

Apr 10, 2008—$496,836

Apr 10, 2007—$434,630

Apr 10, 2006—$387,930

Apr 10, 2005—$341,230

Apr 10, 2004—$294,530

Apr 10, 2003—$271,262

Apr 10, 2002—$247,996

Apr 10, 2001—$224,730

Nearby homes

Off Market

$1,020,200

4 bd3 ba2,168 sqft

210 E Chestnut St, Saint Michaels, MD

Off Market

$1,343,300

3 ba2,032 sqft

206 E Chestnut St, Saint Michaels, MD

Off Market

$1,099,500

3 bd3 ba2,515 sqft

212 E Chestnut St, Saint Michaels, MD

Off Market

$828,000

1.5 ba1,732 sqft

204 E Chestnut St, Saint Michaels, MD

Off Market

$1,876,900

3 bd4 ba2,249 sqft

401 Water St, Saint Michaels, MD

Off Market

$1,012,100

3 bd2 ba2,052 sqft

202 E Chestnut St, Saint Michaels, MD

Off Market

$942,700

2.5 ba2,533 sqft

400 Water St, Saint Michaels, MD

Off Market

$1,262,500

3.5 ba2,823 sqft

214 E Chestnut St, Saint Michaels, MD

Neighborhood details

Local context around this listing

Saint Michaels, MD • Talbot County

Nearby cities

BozmanCordovaEastonOxfordQueen AnneRoyal OakSaint MichaelsTrappe

Nearby zip codes

2162421663

Similar homes

For Sale

$599,000

2 bd1 ba1,200 sqft

204 E Marengo St, Saint Michaels, MD

For Sale

$615,000

3 bd2 ba1,456 sqft

113 Gloria Ave, Saint Michaels, MD

For Sale

$1,194,000

4 bd3 ba1,500 sqft

101 Mulberry St, Saint Michaels, MD

For Sale

$699,000

4 bd3 ba1,957 sqft

408 Spinnaker Ln, Saint Michaels, MD

For Sale

$425,000

3 bd2 ba1,120 sqft

101 Brooks Ln, Saint Michaels, MD

For Sale

$525,000

4 bd4 ba2,420 sqft

1211 Washington Dr, Saint Michaels, MD

For Sale

$450,000

2 bd2 ba1,125 sqft

111 Gloria Ave, Saint Michaels, MD

For Sale

$480,000

3 bd2 ba1,232 sqft

100 Bush Ter, Saint Michaels, MD

For Sale

$525,000

4 bd4 ba2,420 sqft

1215 Washington Dr, Saint Michaels, MD

For Sale

$474,000

2 bd1 ba1,080 sqft

105 Seymour Ave, Saint Michaels, MD

For Sale

$724,900

4 bd2 ba2,208 sqft

10118 Hiners Ln, Easton, MD

For Sale

$724,900

4 bd3 ba2,400 sqft

201 Beachside Dr, Stevensville, MD

For Sale

$549,000

3 bd2 ba1,761 sqft

8000 Bozman Neavitt Rd, Bozman, MD

For Sale

$749,000

3 bd2 ba1,500 sqft

28567 Holden Rd, Easton, MD

For Sale

$875,000

3 bd3 ba2,240 sqft

122 N Lake Dr, Stevensville, MD

9518 Quail Hollow Dr APT 702, Saint Michaels, MD

For Sale

$480,000

3 bd3 ba1,800 sqft

9518 Quail Hollow Dr APT 702, Saint Michaels, MD

For Sale

$895,000

3 bd2 ba1,314 sqft

21560 Chicken Point Rd, Tilghman, MD

For Sale

$700,000

5 bd4 ba2,306 sqft

26698 Arcadia Shores Rd, Easton, MD

For Sale

$575,000

3 bd2 ba1,680 sqft

21869 Albie Rd, Sherwood, MD

For Sale

$719,000

3 bd2 ba1,538 sqft

102 Golf Ct, Stevensville, MD

Tour This Home

Pick a date

Preferred time

Apr 10, 2026

No obligation · Same-day confirmation · Takes 30 seconds

Need a different time? Request custom scheduling

Have a Question?

Get details on this property, the neighborhood, or the buying process.

Ask About This Property

We typically respond within a few hours

Download property brochure

Photos, details & neighborhood info in one PDF

Get brochure

Free · No sign-up required

Get pre-approved

Know your budget & strengthen your offer

Check eligibility

Value estimates

Live

Est. value$834,800

Est. rent$2,368/mo

30yr rate est.6.10%

Affordability$4,737/mo

Own a home nearby?

See what it's worth in today's market

Get estimate

Schedule Tour Ask

No obligation · Same-day response