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 110 E Chestnut St estimated to be worth?

Trulia's estimated value for 110 E Chestnut St in Saint Michaels, MD is $1,111,500 .

What is the price history for 110 E Chestnut St?

110 E Chestnut St in Saint Michaels, MD last sold for $190,000 in May 1995.

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 110 E Chestnut St?

The closest schools to 110 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).

How big is the lot at 110 E Chestnut St?

The lot at 110 E Chestnut St in Saint Michaels, MD is about 0.19 acres (8,400 sq ft).

110 E Chestnut St, Saint Michaels, MD 21663

OFF MARKET

$1,111,500

Trulia Estimate

Studio
3 Baths
3,270 sqft

110 E Chestnut St, Saint Michaels, MD 21663

Est. Refi. Payment $6,383/mo*

Refinance Your Home

Currently Off Market - Sold May 31, 1995 for $190,000

Home Value

Trulia Estimate

$1.11M

Since last month

$45K (-3.9%)

Since last year

$23K (-2.1%)

Since last sale

$905K (+476.5%)

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 +78% in the last 10 years

Month	Estimated value
2026
August 2026	$1.1M
July 2026	$1.14M
June 2026	$1.15M
May 2026	$1.15M
April 2026	$1.13M
March 2026	$1.14M
February 2026	$1.08M
January 2026	$1.11M
2025
December 2025	$1.11M
November 2025	$1.12M
October 2025	$1.12M
September 2025	$1.13M
August 2025	$1.12M
July 2025	$1.17M
June 2025	$1.13M
May 2025	$1.08M
April 2025	$1.04M
March 2025	$1.04M
February 2025	$992K
January 2025	$948K
2024
December 2024	$979K
November 2024	$1.02M
October 2024	$1.03M
September 2024	$1M
August 2024	$1.07M
July 2024	$1.02M
June 2024	$1.01M
May 2024	$1M
April 2024	$1.01M
March 2024	$981K
February 2024	$971K
January 2024	$983K
2023
December 2023	$972K
November 2023	$998K
October 2023	$1.01M
September 2023	$1.01M
August 2023	$978K
July 2023	$1.04M
June 2023	$1.05M
May 2023	$940K
April 2023	$904K
March 2023	$872K
February 2023	$841K
January 2023	$836K
2022
December 2022	$850K
November 2022	$878K
October 2022	$885K
September 2022	$884K
August 2022	$904K
July 2022	$921K
June 2022	$929K
May 2022	$917K
April 2022	$895K
March 2022	$863K
February 2022	$837K
January 2022	$842K
2021
December 2021	$852K
November 2021	$854K
October 2021	$851K
September 2021	$841K
August 2021	$842K
July 2021	$860K
June 2021	$869K
May 2021	$836K
April 2021	$807K
March 2021	$756K
February 2021	$770K
January 2021	$755K
2020
December 2020	$748K
November 2020	$722K
October 2020	$696K
September 2020	$686K
August 2020	$716K
July 2020	$710K
June 2020	$711K
May 2020	$711K
April 2020	$709K
March 2020	$714K
February 2020	$725K
January 2020	$734K
2019
December 2019	$735K
November 2019	$735K
October 2019	$725K
September 2019	$736K
August 2019	$743K
July 2019	$738K
June 2019	$740K
May 2019	$722K
April 2019	$699K
March 2019	$689K
February 2019	$700K
January 2019	$694K
2018
December 2018	$711K
November 2018	$717K
October 2018	$716K
September 2018	$714K
August 2018	$724K
July 2018	$724K
June 2018	$724K
May 2018	$712K
April 2018	$719K
March 2018	$716K
February 2018	$711K
January 2018	$719K
2017
December 2017	$682K
November 2017	$687K
October 2017	$682K
September 2017	$684K
August 2017	$676K
July 2017	$673K
June 2017	$622K
May 2017	$611K
April 2017	$605K
March 2017	$598K
February 2017	$597K
January 2017	$594K
2016
December 2016	$605K
November 2016	$591K
October 2016	$552K
September 2016	$610K
August 2016	$615K

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
807 Radcliff Ave, Saint Michaels, MD	0.33	Single-Family Home	$182,500	09/16/25	3	2.5	2,027
106 E Chestnut St, Saint Michaels, MD	0.03	Single-Family Home	$1,225,000	06/05/26	2	2.5	2,282
408 Water St, Saint Michaels, MD	0.07	Single-Family Home	$995,000	10/08/25	3	2.5	1,893
114 E Chew Ave, Saint Michaels, MD	0.06	Single-Family Home	$1,152,500	06/10/26	3	2.5	2,336
204 Mulberry St, Saint Michaels, MD	0.11	Single-Family Home	$1,350,000	10/27/25	3	2.5	2,320
121 W Chestnut St, St Michaels, MD	0.21	Single-Family Home	$1,395,000	06/22/26	3	2.5	2,540
222 E Chestnut St, Saint Michaels, MD	0.13	Single-Family Home	$1,825,000	08/10/26	3	2.5	2,284
100 Grace St, Saint Michaels, MD	0.14	Single-Family Home	$1,000,000	02/13/26	2	2.5	1,445
205 E Chew Ave, Saint Michaels, MD	0.06	Single-Family Home	$1,175,000	11/14/25	2	1.5	1,780
113 Thompson St, Saint Michaels, MD	0.18	Single-Family Home	$580,000	10/31/25	3	2	1,566

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	0.04	$1,250,000	3	3	2,052	For Sale
115 W Chew Ave, Saint Michaels, MD 21663	0.04	$1,011,300	4	2.5	1,781	Off Market
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	0.07	$1,823,700	3	3.5	2,579	Off Market
205 E Chew Ave, Saint Michaels, MD 21663	0.07	$1,175,000	2	1.5	1,780	Recently Sold
408 Water St, Saint Michaels, MD 21663	0.07	-	3	2.5	1,893	Off Market
106 E Chestnut St, Saint Michaels, MD 21663	0.03	$1,225,000	2	2.5	2,282	Recently Sold
114 E Chew Ave, Saint Michaels, MD 21663	0.06	$1,152,500	3	2.5	2,336	Recently Sold
107 E Chestnut St, Saint Michaels, MD 21663	0.05	$1,135,000	2	2	2,024	Recently Sold
218 E Chestnut St, Saint Michaels, MD 21663	0.11	$1,942,200	4	4	2,639	Off Market
201 E Marengo St, St Michaels, MD 21663	0.09	$846,700	3	2.5	2,294	Off Market
222 E Chestnut St, Saint Michaels, MD 21663	0.13	$1,825,000	3	2.5	2,284	Recently Sold

Local Information

Map ViewExplore the area around 110 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

1860

Living Area

3,270 sqft

Price/Sqft

$340

About this House

This single-family home is located at 110 E Chestnut St, Saint Michaels, MD. 110 E Chestnut St is in Saint Michaels, MD and in ZIP code 21663. This property has 3 bathrooms and approximately 3,270 sqft of floor space. This property has a lot size of 8400 sqft and was built in 1860.

110 E Chestnut St, Saint Michaels, MD 21663 is a studio, 3 bathroom, 3,270 sqft single-family home built in 1860. It last sold for $190,000 on May 31, 1995. This property is not currently displayed as for sale or rent on Trulia. The Trulia Estimate is $1,111,500, with a rent estimate of $2,993/month.

Home Details for 110 E Chestnut St

Interior Features
Heating & Cooling Heating: ElectricHeating Fuel: Electric
Levels, Entrance, & Accessibility Stories: 2
Fireplace & Spa Fireplace

Exterior Features
Exterior Home Features Roof: Shake ShingleExterior: Other

Property Information
Year Built Year Built: 1860
Property Type / Style Property Type: Single Family HomeArchitecture: Conventional

Community
Units in Building: 1

Lot Information
Lot Area: 8400 sqft

Price and Tax history

Date	Event	Price
May 31, 1995 Source: N/A	Sold	$190,000

Year	Property tax	Tax assessment
2025	$2,731	$641,700

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
Flag
Christopherbthomas24
Resident
7y ago
"Love this town, great spot for young families and retirees as well. Awesome spots to eat and hang out"
2
Flag
Kats0791
Resident
8y ago
"Different kinds of houses to chose from including single family, town homes & condos. New Pete Dye Golf Course. "
0
Flag
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
Flag
rctdesign
12y ago
"Wonderful town with lots to do and very walkable!"
0
Flag

LGBTQ Local Legal Protections

Frequently asked questions about 110 E Chestnut St

What is 110 E Chestnut St estimated to be worth?
Trulia's estimated value for 110 E Chestnut St in Saint Michaels, MD is $1,111,500.
What is the price history for 110 E Chestnut St?
110 E Chestnut St in Saint Michaels, MD last sold for $190,000 in May 1995.
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 110 E Chestnut St?
The closest schools to 110 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).
How big is the lot at 110 E Chestnut St?
The lot at 110 E Chestnut St in Saint Michaels, MD is about 0.19 acres (8,400 sq ft).

Explore by feature - Air Conditioning

6 rentals with air conditioning in Saint Michaels, MD

APPLY INSTANTLY
$1,800/mo
2 bd
1 ba
550 sqft
113 Fremont St #A,
Saint Michaels, MD 21663
APPLY INSTANTLY
PET FRIENDLY
$1,950/mo
3 bd
1 ba
1,128 sqft
104 Glory Ave,
Saint Michaels, MD 21663
APPLY INSTANTLY
PET FRIENDLY
$2,100/mo
2 bd
2 ba
1,296 sqft
24580 Deepwater Point Dr #3,
Saint Michaels, MD 21663
PET FRIENDLY
$2,800/mo
2 bd
2 ba
1,500 sqft
308 Cove View Dr,
St Michaels, MD 21663
APPLY INSTANTLY
PET FRIENDLY
$2,000/mo
3 bd
2 ba
1,232 sqft
105 Bush Ter,
Saint Michaels, MD 21663
$2,400/mo
4 bd
2 ba
1,680 sqft
103 Douglas Ln,
Saint Michaels, MD 21663

Apartments for Rent

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Contact for price
1-2 bd
1-2 ba
24700 Deepwater Point Dr #776f18ccb,
Saint Michaels, MD 21663
Contact for price
1-2 bd
1-2 ba
113 Mitchell St #f320a52c6,
Saint Michaels, MD 21663
Contact for price
1-2 bd
1-2 ba
111 Mitchell St #f320a52c6,
Saint Michaels, MD 21663
APPLY INSTANTLY
$1,800/mo
2 bd
1 ba
113 Fremont St #A,
Saint Michaels, MD 21663
APPLY INSTANTLY
PET FRIENDLY
$2,100/mo
2 bd
2 ba
24580 Deepwater Point Dr #3,
Saint Michaels, MD 21663
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Saint Michaels
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Off Market Homes Near 110 E Chestnut St

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SOLD
AUG 25, 2026
$1,187,500
3 bd
2.5 ba
1,836 sqft
344 Perry Cabin Dr,
Saint Michaels, MD 21663
Chesapeake Bay Real Estate Plus, LLC
SOLD
JUL 29, 2026
$620,000
3 bd
3 ba
2,144 sqft
24561 Deepwater Point Dr,
Saint Michaels, MD 21663
Chesapeake Bay Real Estate Plus, LLC
SOLD
JUL 27, 2026
$1,135,000
2 bd
2 ba
2,024 sqft
107 E Chestnut St,
Saint Michaels, MD 21663
TTR Sotheby's International Realty
SOLD
JUL 14, 2026
$1,100,000
Pea neck Rd,
Saint michaels, MD 21663
SOLD
JUL 8, 2026
$650,000
5 bd
3.5 ba
2,306 sqft
26698 Arcadia Shores Rd,
Easton, MD 21601
Coldwell Banker Realty
SOLD
JUN 30, 2026
$560,000
4 bd
3 ba
2,410 sqft
6980 Hopkins Neck Rd,
Royal Oak, MD 21662
Long & Foster Real Estate, Inc.
SOLD
JUN 30, 2026
$560,000
4 bd
3 ba
2,410 sqft
6980 Hopkins Neck Rd,
Easton, MD 21601
SOLD
JUN 22, 2026
$1,395,000
3 bd
2.5 ba
2,540 sqft
121 W Chestnut St,
St Michaels, MD 21663
Benson & Mangold, LLC
SOLD
JUN 18, 2026
$860,000
2 ba
1,822 sqft
503 Tilden St,
Saint Michaels, MD 21663
SOLD
JUN 15, 2026
$616,000
4 bd
2 ba
2,448 sqft
25714 Edgeview Rd,
Royal Oak, MD 21662
Benson & Mangold, LLC
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Saint Michaels
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Homes for sale near 110 E Chestnut St

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$1,470,000
3 bd
2.5 ba
1,938 sqft
104 Mulberry St,
Saint Michaels, MD 21663
RE/MAX One
$995,000
4 bd
3 ba
2,250 sqft
109 W Marengo St,
St Michaels, MD 21663
Benson & Mangold, LLC
OPEN SAT, 1:30-3:30PM
0.25 ACRES
$995,000
3 bd
2.5 ba
2,091 sqft
101 Seymour Ave,
Saint Michaels, MD 21663
Meredith Fine Properties
NEW - 2 DAYS AGO
$995,000
4 bd
3 ba
2,718 sqft
104 Cherry St,
Saint Michaels, MD 21663
Redfin Corp
$1,250,000
3 bd
3 ba
2,052 sqft
202 E Chestnut St,
Saint Michaels, MD 21663
Benson & Mangold, LLC
NEW CONSTRUCTION
0.41 ACRES
$1,985,000
3 bd
3 ba
2,622 sqft
303 Manor St,
Saint Michaels, MD 21663
TTR Sotheby's International Realty
$799,900
3 bd
2.5 ba
2,027 sqft
807 Radcliff Ave,
Saint Michaels, MD 21663
$799,900
3 bd
2.5 ba
2,027 sqft
807 Radcliff Ave,
Saint Michaels, MD 21663
Long & Foster Real Estate, Inc.
COMING SOON 9/10
$949,000
4 bd
2.5 ba
2,168 sqft
111 Chesapeake Ave,
Saint Michaels, MD 21663
Meredith Fine Properties
OPEN FRI, 11-1PM
$1,129,000
4 bd
2.5 ba
1,500 sqft
101 Mulberry St,
Saint Michaels, MD 21663
Meredith Fine Properties
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