Are yards well-kept in Saint Michaels, MD?

As of early 2026, 100% of users say yards are well-kept

Are the streets well-lit in Saint Michaels, MD?

As of early 2026, 100% of users say streets are well-lit

Is Saint Michaels, MD dog-friendly?

As of early 2026, 92% of users say it's dog friendly

Is Saint Michaels, MD quiet?

As of early 2026, 92% of users say it's quiet

Is a car needed in Saint Michaels, MD?

As of early 2026, 90% of users say car is needed

Is parking easy in Saint Michaels, MD?

As of early 2026, 82% of users say parking is easy

Is there wildlife in Saint Michaels, MD?

As of early 2026, 79% of users say there's wildlife

Does Saint Michaels, MD show holiday spirit?

As of early 2026, 75% of users say there's holiday spirit

Do kids play outside in Saint Michaels, MD?

As of early 2026, 73% of users say kids play outside

Would people walk alone at night in Saint Michaels, MD?

As of early 2026, 67% of users say people would walk alone at night

Is Saint Michaels, MD walkable to restaurants?

As of early 2026, 64% of users say it's walkable to restaurants

Are there community events in Saint Michaels, MD?

As of early 2026, 63% of users say there are community events

Are neighbors friendly in Saint Michaels, MD?

As of early 2026, 58% of users say neighbors are friendly

Is Saint Michaels, MD walkable to grocery stores?

As of early 2026, 50% of users say it's walkable to grocery stores

Does Saint Michaels, MD have sidewalks?

As of early 2026, 45% of users say there are sidewalks

Do residents of Saint Michaels, MD plan to stay at least 5 years?

As of early 2026, 40% of users say they plan to stay for at least 5 years

What is 104 E Chestnut St estimated to be worth?

Trulia's estimated value for 104 E Chestnut St in St Michaels, MD is $1,018,800 .

What is the price history for 104 E Chestnut St?

104 E Chestnut St in St Michaels, MD last sold for $775,000 in April 2012.

Is St Michaels a buyer's or seller's market?

St Michaels is currently a buyer's market, based on recent for-sale activity.

What are the closest schools to 104 E Chestnut St?

The closest schools to 104 E Chestnut St in St Michaels, MD are St. Michaels Elementary School (Pre-K, rated 8/10), St. Michaels Middle/High School (rated 6/10).

How big is the lot at 104 E Chestnut St?

The lot at 104 E Chestnut St in St Michaels, MD is about 0.17 acres (7,200 sq ft).

OFF MARKET

104 E Chestnut St
St Michaels, MD 21663

Studio
1 Bath
1,460 sqft

$1,018,800

Trulia Estimate

as of Aug 24, 2026

Est. Refi. Payment $5,851/mo*

Refinance Your Home

$1,018,800

Trulia Estimate

as of Aug 24, 2026

Est. Refi. Payment $5,851/mo*

Refinance Your Home

Studio

1 Bath

1,460 sqft

Home Value

Trulia Estimate

$1.02M

Since last month

$5K (+0.5%)

Since last year

$22K (-2.1%)

Since last sale

$253K (+32.6%)

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 +134% in the last 10 years

Month	Estimated value
2026
August 2026	$1.03M
July 2026	$1.02M
June 2026	$1.04M
May 2026	$1.04M
April 2026	$1.01M
March 2026	$1.04M
February 2026	$1.02M
January 2026	$999K
2025
December 2025	$1.03M
November 2025	$1.05M
October 2025	$1.06M
September 2025	$1.05M
August 2025	$1.05M
July 2025	$1.08M
June 2025	$1.06M
May 2025	$1.05M
April 2025	$1.06M
March 2025	$1.02M
February 2025	$981K
January 2025	$956K
2024
December 2024	$978K
November 2024	$1.01M
October 2024	$1.05M
September 2024	$1.04M
August 2024	$1.08M
July 2024	$1.03M
June 2024	$1.04M
May 2024	$1.05M
April 2024	$1.03M
March 2024	$1.02M
February 2024	$993K
January 2024	$1.02M
2023
December 2023	$1.01M
November 2023	$1.04M
October 2023	$1.06M
September 2023	$1.1M
August 2023	$1.1M
July 2023	$1.1M
June 2023	$1.1M
May 2023	$1.09M
April 2023	$1.1M
March 2023	$1.1M
February 2023	$1.1M
January 2023	$1.11M
2022
December 2022	$1.12M
November 2022	$1.12M
October 2022	$1.11M
September 2022	$1.11M
August 2022	$1.1M
July 2022	$1.1M
June 2022	$1.08M
May 2022	$1.06M
April 2022	$1.07M
March 2022	$1.05M
February 2022	$1.04M
January 2022	$1.03M
2021
December 2021	$1.02M
November 2021	$1M
October 2021	$990K
September 2021	$904K
August 2021	$896K
July 2021	$884K
June 2021	$758K
May 2021	$509K
April 2021	$483K
March 2021	$469K
February 2021	$502K
January 2021	$484K
2020
December 2020	$493K
November 2020	$478K
October 2020	$446K
September 2020	$460K
August 2020	$436K
July 2020	$420K
June 2020	$434K
May 2020	$445K
April 2020	$438K
March 2020	$445K
February 2020	$446K
January 2020	$442K
2019
December 2019	$471K
November 2019	$484K
October 2019	$478K
September 2019	$499K
August 2019	$501K
July 2019	$493K
June 2019	$477K
May 2019	$473K
April 2019	$497K
March 2019	$467K
February 2019	$475K
January 2019	$478K
2018
December 2018	$486K
November 2018	$485K
October 2018	$500K
September 2018	$524K
August 2018	$535K
July 2018	$531K
June 2018	$538K
May 2018	$509K
April 2018	$509K
March 2018	$512K
February 2018	$490K
January 2018	$492K
2017
December 2017	$524K
November 2017	$510K
October 2017	$513K
September 2017	$495K
August 2017	$501K
July 2017	$505K
June 2017	$429K
May 2017	$405K
April 2017	$414K
March 2017	$426K
February 2017	$437K
January 2017	$433K
2016
December 2016	$433K
November 2016	$442K
October 2016	$452K
September 2016	$439K
August 2016	$439K

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
113 Thompson St, Saint Michaels, MD	0.14	Single-Family Home	$580,000	10/31/25	3	2	1,566
205 E Chew Ave, Saint Michaels, MD	0.11	Single-Family Home	$1,175,000	11/14/25	2	1.5	1,780
100 Grace St, Saint Michaels, MD	0.11	Single-Family Home	$1,000,000	02/13/26	2	2.5	1,445
503 Tilden St, Saint Michaels, MD	0.20	Single-Family Home	$860,000	06/18/26		2	1,822
203 Mulberry St, Saint Michaels, MD	0.14	Single-Family Home	$926,000	01/15/26	3	2	1,740
115 Thompson St, Saint Michaels, MD	0.16	Single-Family Home	$290,000	01/21/26		1	972
105 Seymour Ave, Saint Michaels, MD	0.20	Single-Family Home	$410,000	07/14/26	2	1	1,080
106 Grace St, Saint Michaels, MD	0.13	Single-Family Home	$775,000	12/02/25	3	1.5	2,068
113 Glory Ave, Saint Michaels, MD	0.26	Single-Family Home	$539,500	07/06/26		2	1,456
204 W Chew Ave, Saint Michaels, MD	0.17	Single-Family Home	$660,000	09/16/25	3	2	1,500

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
504 Talbot St, Saint Michaels, MD 21663	0.05	$831,000	3	2.5	2,072	Off Market
106 E Chestnut St, Saint Michaels, MD 21663	0.02	$1,225,000	2	2.5	2,282	Recently Sold
107 E Chestnut St, Saint Michaels, MD 21663	0.03	$1,135,000	2	2	2,024	Recently Sold
115 W Chew Ave, Saint Michaels, MD 21663	0.07	$1,015,600	4	2.5	1,781	Off Market
114 E Chew Ave, Saint Michaels, MD 21663	0.09	$1,152,500	3	2.5	2,336	Recently Sold
103 W Marengo St, St Michaels, MD 21663	0.11	$532,600	2	1.5	1,209	Off Market
202 E Chestnut St, Saint Michaels, MD 21663	0.09	$1,250,000	3	3	2,052	For Sale
104 Chew West Ave, Saint Michaels, MD 21663	0.11	$1,276,000	2	2	2,654	Off Market
201 E Marengo St, St Michaels, MD 21663	0.11	$846,700	3	2.5	2,294	Off Market
109 W Chew Ave, Saint Michaels, MD 21663	0.10	$647,500	3	2	1,824	Off Market
100 Marengo St, Saint Michaels, MD 21663	0.13	$760,400	3	2	1,680	Off Market
203 E Chew Ave, Saint Michaels, MD 21663	0.10	$2,125,000	5	5.5	4,673	Recently Sold

Local Information

Map ViewExplore the area around 104 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

1880

Living Area

1,460 sqft

Price/Sqft

$698

About this House

This single-family home is located at 104 E Chestnut St, St Michaels, MD. 104 E Chestnut St is in St Michaels, MD and in ZIP code 21663. This property has 1 bathroom and approximately 1,460 sqft of floor space. This property has a lot size of 7200 sqft and was built in 1880.

104 E Chestnut St, St Michaels, MD 21663 is a studio, 1 bathroom, 1,460 sqft single-family home built in 1880. It last sold for $775,000 on Apr 2, 2012. It is currently off market. The Trulia Estimate is $1,018,800, with a rent estimate of $2,115/month.

Home Details for 104 E Chestnut St

Interior Features
Heating & Cooling Heating: RadiantHeating Fuel: Radiant
Levels, Entrance, & Accessibility Stories: 2
Fireplace & Spa Fireplace

Exterior Features
Exterior Home Features Roof: Shake ShingleExterior: Other

Property Information
Year Built Year Built: 1880
Property Type / Style Property Type: Single Family HomeArchitecture: Conventional

Community
Units in Building: 1

Lot Information
Lot Area: 7200 sqft

Price and Tax history

Date	Event	Price
Apr 2, 2012 Source: N/A	Sold	$775,000

Year	Property tax	Tax assessment
2025	$3,316	$528,800

Additional Cost

Market trends in Saint Michaels

Last updated July 2026

Avg. sale price

—

Sale-to-List Price

—

Price per sq ft

—

Available listings

3MoM

Around this home

St. Michaels Elementary School
PK-5
Public
319 Students
Talbot County Public Schools
8/10
GreatSchools Rating
Parent Rating Average
This 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 Review
8y ago
7 Reviews

View nearby schools on GreatSchools

The GreatSchools Rating compares schools on a variety of school quality indicators including test scores, college readiness, equity and more. Learn more.

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
Resident
5y ago
"There are many dog friendly places and lost of nice outdoor spaces for walks. People are very comfortable around dogs here. "
0
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Christopherbthomas24
Resident
7y ago
"Love this town, great spot for young families and retirees as well. Awesome spots to eat and hang out"
2
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Kats0791
Resident
8y ago
"Different kinds of houses to chose from including single family, town homes & condos. New Pete Dye Golf Course. "
0
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Janet S.
11y ago
"Work and live here. Fantastic area - beautiful, with great sailing. The town has constantly improved since I moved here in 1993."
0
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rctdesign
12y ago
"Wonderful town with lots to do and very walkable!"
0
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Frequently asked questions about 104 E Chestnut St

What is 104 E Chestnut St estimated to be worth?
Trulia's estimated value for 104 E Chestnut St in St Michaels, MD is $1,018,800.
What is the price history for 104 E Chestnut St?
104 E Chestnut St in St Michaels, MD last sold for $775,000 in April 2012.
Is St Michaels a buyer's or seller's market?
St Michaels is currently a buyer's market, based on recent for-sale activity.
What are the closest schools to 104 E Chestnut St?
The closest schools to 104 E Chestnut St in St Michaels, MD are St. Michaels Elementary School (Pre-K, rated 8/10), St. Michaels Middle/High School (rated 6/10).
How big is the lot at 104 E Chestnut St?
The lot at 104 E Chestnut St in St Michaels, MD is about 0.17 acres (7,200 sq ft).