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

$877,200

Trulia Estimate

as of Jun 30, 2026

Est. Refi. Payment $4,860/mo*

Refinance Your Home

$877,200

Trulia Estimate

as of Jun 30, 2026

Est. Refi. Payment $4,860/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

Description

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

This property is off market, which means it's not currently listed for sale or rent on Trulia. This may be different from what's available on other websites or public sources.

Home Highlights

Parking

Garage

Outdoor

No Info

A/C

Heating & Cooling

HOA

None

Price/Sqft

No Info

Listed

Less than a day ago

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 May 2026

Avg. sale price

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Sale-to-List Price

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Price per sq ft

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Available listings

8MoM

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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
400 Railroad Ave, Saint Michaels, MD	0.20	Single-Family Home	$505,000	07/09/25	3	2	1,674
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
109 W Chew Ave, Saint Michaels, MD	0.35	Single-Family Home	$662,500	07/18/25	3	2	1,824
203 Mulberry St, Saint Michaels, MD	0.15	Single-Family Home	$926,000	01/15/26	3	2	1,740

Nearby homes

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

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OFF MARKET
Est. $808,100
2 bd
2 ba
1,228 sqft
107 Carpenter St,
Saint Michaels, MD 21663
Coldwell Banker Chesapeake Real Estate Company
OFF MARKET
Est. $2,813,300
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. $786,100
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
4 bd
3 ba
2,703 sqft
202 Mulberry St,
Saint Michaels, MD 21663
TTR Sotheby's International Realty
OFF MARKET
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. $391,900
3 bd
1 ba
1,080 sqft
106 Conner St #C,
Saint Michaels, MD 21663
Benson & Mangold, LLC
FOR SALE
$342,900
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
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
111 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
113 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
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Homes for sale near 106 Cherry St

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$342,900
3 bd
2 ba
1,364 sqft
203 Canton St,
Saint Michaels, MD 21663
Coldwell Banker Chesapeake Real Estate Company
$1,885,000
3 bd
2.5 ba
2,284 sqft
222 E Chestnut St,
Saint Michaels, MD 21663
Long & Foster Real Estate, Inc.
$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
$1,165,000
2 bd
2 ba
2,024 sqft
107 E Chestnut St,
Saint Michaels, MD 21663
TTR Sotheby's International Realty
$425,000
3 bd
2 ba
1,120 sqft
101 Brooks Ln,
Saint Michaels, MD 21663
Benson & Mangold, LLC
$825,000
3 bd
2.5 ba
2,027 sqft
807 Radcliff St,
Michaels, MD 21663
$1,195,000
4 bd
4.5 ba
3,528 sqft
114 W Chestnut St,
St Michaels, MD 21663
Benson & Mangold, LLC
$825,000
3 bd
2.5 ba
2,027 sqft
807 Radcliff Ave,
Saint Michaels, MD 21663
Long & Foster Real Estate, Inc.
OPEN SAT, 11-1PM
$1,049,000
3 bd
2.5 ba
2,200 sqft
504 Seymour Ave,
Saint Michaels, MD 21663
Benson & Mangold, LLC
See more homes for sale in
Saint Michaels
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Off Market Homes Near 106 Cherry St

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SOLD
JUN 15, 2026
$616,000
4 bd
2 ba
2,448 sqft
25714 Edgeview Rd,
Royal Oak, MD 21662
Benson & Mangold, LLC
SOLD
JUN 12, 2026
$465,000
3 bd
2 ba
1,540 sqft
314 Cove View Dr #5B,
Saint Michaels, MD 21663
Meredith Fine Properties
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
SOLD
JUN 10, 2026
$685,000
4 bd
3.5 ba
3,010 sqft
24977 Back Creek Dr,
Saint Michaels, MD 21663
Benson & Mangold, LLC
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
JUN 3, 2026
$514,000
3 bd
2 ba
1,744 sqft
23266 Mallard Point Rd,
McDaniel, MD 21647
Benson & Mangold, LLC
SOLD
JUN 3, 2026
$765,000
3 bd
2.5 ba
3,166 sqft
24912 Back Creek Dr,
Saint Michaels, MD 21663
Benson & Mangold, LLC
SOLD
MAY 27, 2026
$1,055,000
3 bd
2.5 ba
2,840 sqft
7605 Pendleton Farm Ln,
Easton, MD 21601
Benson & Mangold, LLC
SOLD
MAY 21, 2026
$675,000
4 bd
2.5 ba
1,957 sqft
408 Spinnaker Ln,
Saint Michaels, MD 21663
Northrop Realty
SOLD
MAY 15, 2026
$600,000
3 bd
2.5 ba
2,080 sqft
23201 Stewart Way,
McDaniel, MD 21647
Benson & Mangold, LLC
See more homes for sale in
Saint Michaels
Take a look

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106 Cherry St, Saint Michaels, MD 21663 is a 4 bedroom, 2 bathroom, 2,277 sqft unknown built in 1860. This property is not currently available for sale. 106 Cherry St was last sold on May 24, 2012 for $401,108. The current Trulia Estimate for 106 Cherry St is $877,200.

106 Cherry St
Saint Michaels, MD 21663

$877,200

$877,200

Local Information