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

106 Cherry St
Saint Michaels, MD 21663

4 Beds
2 Baths
2,277 sqft

$869,900

Trulia Estimate

as of Jul 26, 2026

Est. Refi. Payment $4,938/mo*

Refinance Your Home

$869,900

Trulia Estimate

as of Jul 26, 2026

Est. Refi. Payment $4,938/mo*

Refinance Your Home

4 Beds

2 Baths

2,277 sqft

Local Information

Map ViewExplore the area around 106 Cherry St.
Schools1 Preschool School1 Elementary School1 Middle School1 High School
Shop & Eat

-- mins to

Commute Destination

Home Highlights

Year Built

1860

Living Area

2,277 sqft

Price/Sqft

$382

Parking

Garage

About this House

Charming c. 1860's historic St. Michaels home featuring upper & lower porches on lovely corner lot with picket fence. Very livable home features original historic detail, all wood floors, living room with fireplace, separate dining room, 1-car garage, & parking pad. Very desirable location at the corner of Cherry & Locust St, just steps to harbor, shops, restaurants, Honeymoon Bridge, & Navy Point

106 Cherry St, Saint Michaels, MD 21663 is a 4 bedroom, 2 bathroom, 2,277 sqft unknown built in 1860. It last sold for $401,108 on May 24, 2012. It is currently off market. The Trulia Estimate is $869,900, with a rent estimate of $2,272/month.

Home Details for 106 Cherry St

Interior Features
Heating & Cooling Heating: OtherAir ConditioningHeating Fuel: Other
Levels, Entrance, & Accessibility Stories: 2
Fireplace & Spa Fireplace

Exterior Features
Exterior Home Features Roof: OtherExterior: Other
Parking & Garage GarageParking: Garage Detached

Property Information
Year Built Year Built: 1860
Property Type / Style Property Type: UnknownArchitecture: Conventional

Community
Units in Building: 1

Lot Information
Lot Area: 5999 sqft

Price History for 106 Cherry St

Date	Price	Event	Source
05/24/2012	$401,108	Sold	N/A
Recording Date 05/24/2012 Contract Date 05/23/2012 County Transfer Tax $3,511 Total Transfer Tax $4,514
01/15/2012	$425,000	PriceChange	Agent Provided
Price Change $69,500 (-14%)
09/13/2011	$494,500	PriceChange	Agent Provided
Price Change $39,500 (-7%)
07/13/2011	$534,000	Listed For Sale	Agent Provided

Market trends in Saint Michaels

Last updated June 2026

Avg. sale price

—

Sale-to-List Price

—

Price per sq ft

—

Available listings

2MoM

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Property Tax and Assessment

Year	2025
Tax
Assessment	$551,100

Home facts updated by county records

Comparable Sales for 106 Cherry St

Address	Distance	Property Type	Sold Price	Sold Date	Bed	Bath	Sqft
103 Mulberry St, Saint Michaels, MD	0.15	Single-Family Home	$800,000	08/15/25	4	1.5	1,596
113 Gloria Ave, Saint Michaels, MD	0.23	Single-Family Home	$539,500	06/30/26	3	2	1,456
113 Thompson St, Saint Michaels, MD	0.29	Single-Family Home	$580,000	10/31/25	3	2	1,566
111 Gloria Ave, Saint Michaels, MD	0.21	Single-Family Home	$425,000	05/18/26	2	1.5	1,125
109 Chesapeake Ave, Saint Michaels, MD	0.24	Single-Family Home	$865,000	08/12/25	4	2.5	2,168
106 Grace St, Saint Michaels, MD	0.24	Single-Family Home	$775,000	12/02/25	3	1.5	2,068
602 S Talbot St, St Michaels, MD	0.30	Single-Family Home	$740,000	10/02/25	4	2.5	2,433
204 Mulberry St, Saint Michaels, MD	0.17	Single-Family Home	$1,350,000	10/27/25	3	2.5	2,320
203 Mulberry St, Saint Michaels, MD	0.15	Single-Family Home	$926,000	01/15/26	3	2	1,740
110 Lee St, Saint Michaels, MD	0.38	Single-Family Home	$475,000	09/18/25	3	2	1,500

Nearby homes

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

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OFF MARKET
Est. $811,200
2 bd
2 ba
1,228 sqft
107 Carpenter St,
Saint Michaels, MD 21663
Coldwell Banker Chesapeake Real Estate Company
OFF MARKET
Est. $2,786,800
8 bd
8.5 ba
3,640 sqft
202 Cherry St,
Saint Michaels, MD 21663
TTR Sotheby's International Realty
SOLD
JAN 15, 2026
$926,000
3 bd
2 ba
1,740 sqft
203 Mulberry St,
Saint Michaels, MD 21663
Benson & Mangold, LLC
OFF MARKET
Est. $783,300
4 bd
1.5 ba
1,596 sqft
103 Mulberry St,
Saint Michaels, MD 21663
Benson & Mangold, LLC
FOR SALE
$1,179,000
4 bd
2.5 ba
1,500 sqft
101 Mulberry St,
Saint Michaels, MD 21663
Meredith Fine Properties
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
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
124 Fremont St,
Saint Michaels, MD 21663
TTR Sotheby's International Realty
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. $390,400
3 bd
1 ba
1,080 sqft
106 Conner St #C,
Saint Michaels, MD 21663
Benson & Mangold, LLC
FOR SALE
$309,000
3 bd
2 ba
1,364 sqft
203 Canton St,
Saint Michaels, MD 21663
Coldwell Banker Chesapeake Real Estate Company

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Additional Cost

Assigned Schools

These are the assigned schools for 106 Cherry 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
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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
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
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rctdesign
12y ago
"Wonderful town with lots to do and very walkable!"
0
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LGBTQ Local Legal Protections

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
See more homes for rent in
Saint Michaels
Take a look

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Homes for sale near 106 Cherry St

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$309,000
3 bd
2 ba
1,364 sqft
203 Canton St,
Saint Michaels, MD 21663
Coldwell Banker Chesapeake Real Estate Company
$1,179,000
4 bd
2.5 ba
1,500 sqft
101 Mulberry St,
Saint Michaels, MD 21663
Meredith Fine Properties
$1,049,000
4 bd
3 ba
2,250 sqft
109 W Marengo St,
St Michaels, MD 21663
Benson & Mangold, LLC
$425,000
3 bd
2 ba
1,120 sqft
101 Brooks Ln,
Saint Michaels, MD 21663
Benson & Mangold, LLC
$799,900
3 bd
2.5 ba
2,027 sqft
807 Radcliff St,
Michaels, MD 21663
$849,000
3 bd
2 ba
1,288 sqft
803 New Ln,
Saint Michaels, MD 21663
TTR Sotheby's International Realty
$1,195,000
4 bd
4.5 ba
3,528 sqft
114 W Chestnut St,
St Michaels, MD 21663
Benson & Mangold, LLC
$799,900
3 bd
2.5 ba
2,027 sqft
807 Radcliff Ave,
Saint Michaels, MD 21663
Long & Foster Real Estate, Inc.
$1,049,000
3 bd
2.5 ba
2,200 sqft
504 Seymour Ave,
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