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

OFF MARKET

109 E Chestnut St
Saint Michaels, MD 21663

3 Beds
1.5 Baths
1,488 sqft

$824,500

Trulia Estimate

as of Jul 6, 2026

Est. Refi. Payment $4,615/mo*

Refinance Your Home

$824,500

Trulia Estimate

as of Jul 6, 2026

Est. Refi. Payment $4,615/mo*

Refinance Your Home

3 Beds

1.5 Baths

1,488 sqft

Local Information

Map ViewExplore the area around 109 E Chestnut St.
Schools1 Preschool School1 Elementary School1 Middle School1 High School
Shop & Eat

-- mins to

Commute Destination

Description

This c. 1875 Victorian charmer in the heart of St. Michaels historic district is close to shops, restaurants and the harbor. Nicely maintained with central air, pine floors, screened porch and fenced yard. Great curb appeal.

109 E Chestnut St, Saint Michaels, MD 21663 is a 3 bedroom, 2 bathroom, 1,488 sqft single-family home built in 1873. It last sold for $450,000 on Apr 24, 2017. It is currently off market. The Trulia Estimate is $824,500, with a rent estimate of $2,141/month.

Home Highlights

Parking

No Info

Outdoor

No Info

A/C

Heating only

HOA

None

Price/Sqft

No Info

Listed

Less than a day ago

Home Details for 109 E Chestnut St

Interior Features
Heating & Cooling Heating: Heat PumpHeating Fuel: Heat Pump
Levels, Entrance, & Accessibility Stories: 2
Appliances & Utilities DishwasherDryerRefrigeratorWasher
Fireplace & Spa Fireplace

Exterior Features
Exterior Home Features Roof: Shake ShingleExterior: Other

Property Information
Year Built Year Built: 1873
Property Type / Style Property Type: Single Family HomeArchitecture: Conventional

Community
Units in Building: 1

Lot Information
Lot Area: 3598 sqft

Price History for 109 E Chestnut St

Date	Price	Event	Source
04/24/2017	$450,000	Sold	N/A
Recording Date 04/24/2017 Contract Date 04/21/2017 County Transfer Tax $4,500 Total Transfer Tax $6,750
03/16/2017	$479,000	Pending	Agent Provided

02/16/2017	$479,000	Listed For Sale	Agent Provided

03/30/2012	$475,000	Sold	N/A
Recording Date 03/30/2012 Contract Date 12/13/2011 County Transfer Tax $4,750 Total Transfer Tax $7,125
07/16/2002	$339,900	Sold	N/A
Recording Date 07/16/2002 County Transfer Tax N/A Total Transfer Tax N/A
03/14/1997	$150,000	Sold	N/A
Recording Date 03/14/1997 County Transfer Tax N/A Total Transfer Tax N/A

Market trends in Saint Michaels

Last updated May 2026

Avg. sale price

—

Sale-to-List Price

—

Price per sq ft

—

Available listings

8MoM

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Property Tax and Assessment

Year	2025
Tax
Assessment	$491,600

Home facts updated by county records

Comparable Sales for 109 E Chestnut St

Address	Distance	Property Type	Sold Price	Sold Date	Bed	Bath	Sqft
204 W Chew Ave, Saint Michaels, MD	0.20	Single-Family Home	$660,000	09/16/25	3	2	1,500
106 Grace St, Saint Michaels, MD	0.12	Single-Family Home	$775,000	12/02/25	3	1.5	2,068
113 Thompson St, Saint Michaels, MD	0.14	Single-Family Home	$580,000	10/31/25	3	2	1,566
106 Conner St #C, Saint Michaels, MD	0.29	Single-Family Home	$399,000	07/18/25	3	1	1,080
109 W Chew Ave, Saint Michaels, MD	0.13	Single-Family Home	$662,500	07/18/25	3	2	1,824
113 Gloria Ave, Saint Michaels, MD	0.25	Single-Family Home	$539,500	06/30/26	3	2	1,456
901 S Talbot St, St Michaels, MD	0.26	Single-Family Home	$600,000	08/08/25	3	2	1,660
103 Mulberry St, Saint Michaels, MD	0.10	Single-Family Home	$800,000	08/15/25	4	1.5	1,596
103 W Marengo St, St Michaels, MD	0.15	Single-Family Home	$545,000	07/11/25	2	1.5	1,209
400 Railroad Ave, Saint Michaels, MD	0.35	Single-Family Home	$505,000	07/09/25	3	2	1,674

Nearby homes

Get a sense of prices in the area by checking nearby homes.

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SOLD
JUN 5, 2026
$1,225,000
2 bd
2.5 ba
2,282 sqft
106 E Chestnut St,
Saint Michaels, MD 21663
Taylor Properties
SOLD
OCT 8, 2025
$995,000
3 bd
2.5 ba
1,893 sqft
408 Water St,
Saint Michaels, MD 21663
TTR Sotheby's International Realty
OFF MARKET
Est. $1,006,600
4 bd
2.5 ba
1,781 sqft
115 W Chew Ave,
Saint Michaels, MD 21663
Meredith Fine Properties
OFF MARKET
Est. $1,869,300
3 bd
3.5 ba
2,579 sqft
417 Water St,
Saint Michaels, MD 21663
Meredith Fine Properties
OFF MARKET
Est. $1,706,500
4 bd
2.5 ba
3,694 sqft
201 E Chew Ave,
Saint Michaels, MD 21663
Benson & Mangold, LLC
OFF MARKET
Est. $1,174,700
4 bd
3 ba
2,703 sqft
202 Mulberry St,
Saint Michaels, MD 21663
TTR Sotheby's International Realty
OFF MARKET
Est. $1,270,600
3 bd
2.5 ba
1,938 sqft
104 Mulberry St,
Saint Michaels, MD 21663
Benson & Mangold, LLC
OFF MARKET
Est. $834,900
3 bd
2.5 ba
2,072 sqft
504 Talbot St,
Saint Michaels, MD 21663
Benson & Mangold, LLC
SOLD
OCT 27, 2025
$1,350,000
3 bd
2.5 ba
2,320 sqft
204 Mulberry St,
Saint Michaels, MD 21663
TTR Sotheby's International Realty
OFF MARKET
2 bd
1 ba
1,608 sqft
402 S Talbot St,
St Michaels, MD 21663
Benson & Mangold, LLC
SOLD
NOV 14, 2025
$1,175,000
2 bd
1.5 ba
1,780 sqft
205 E Chew Ave,
Saint Michaels, MD 21663
Benson & Mangold, LLC
SOLD
JUN 10, 2026
$1,152,500
3 bd
2.5 ba
2,336 sqft
114 E Chew Ave,
Saint Michaels, MD 21663
Benson & Mangold, LLC

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Additional Cost

Assigned Schools

These are the assigned schools for 109 E Chestnut St.

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
11y ago
"Wonderful town with lots to do and very walkable!"
0
Flag

LGBTQ Local Legal Protections

Apartments for Rent

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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
24700 Deepwater Point Dr #776f18ccb,
Saint Michaels, MD 21663
Contact for price
1-2 bd
1-2 ba
111 Mitchell St #f320a52c6,
Saint Michaels, MD 21663
PET FRIENDLY
$2,650/mo
4 bd
2.5 ba
921 S Talbot St #C,
Easton, MD 21663
See more homes for rent in
Saint Michaels
Take a look

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Homes for sale near 109 E Chestnut St

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$1,179,000
4 bd
2.5 ba
1,500 sqft
101 Mulberry St,
Saint Michaels, MD 21663
Meredith Fine Properties
$342,900
3 bd
2 ba
1,364 sqft
203 Canton St,
Saint Michaels, MD 21663
Coldwell Banker Chesapeake Real Estate Company
NEW - 2 DAYS AGO
$849,000
3 bd
2 ba
1,288 sqft
803 New Ln,
Saint Michaels, MD 21663
TTR Sotheby's International Realty
$1,885,000
3 bd
2.5 ba
2,284 sqft
222 E Chestnut St,
Saint Michaels, MD 21663
Long & Foster Real Estate, Inc.
OPEN SAT, 11-1PM
$1,049,000
4 bd
3 ba
2,250 sqft
109 W Marengo St,
St Michaels, MD 21663
Benson & Mangold, LLC
0.28 ACRES
$574,999
2 bd
1 ba
1,200 sqft
204 E Marengo St,
Saint Michaels, MD 21663
Compass
$799,900
3 bd
2.5 ba
2,027 sqft
807 Radcliff St,
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.
$425,000
3 bd
2 ba
1,120 sqft
101 Brooks Ln,
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
See more homes for sale in
Saint Michaels
Take a look