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

216 E Chestnut St
Saint Michaels, MD 21663

Studio
3 Baths
2,913 sqft

$1,403,100

Trulia Estimate

as of May 27, 2026

Est. Refi. Payment $7,949/mo*

Refinance Your Home

$1,403,100

Trulia Estimate

as of May 27, 2026

Est. Refi. Payment $7,949/mo*

Refinance Your Home

Studio

3 Baths

2,913 sqft

Local Information

-- mins to

Commute Destination

Description

This single-family home is located at 216 E Chestnut St, Saint Michaels, MD. 216 E Chestnut St is in Saint Michaels, MD and in ZIP code 21663. This property has 3 bathrooms and approximately 2,913 sqft of floor space. This property has a lot size of 4800 sqft and was built in 1850.

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

Patio

A/C

Heating & Cooling

HOA

None

Price/Sqft

No Info

Listed

No Info

Home Details for 216 E Chestnut St

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

Exterior Features
Exterior Home Features Roof: Shake ShingleExterior: OtherPatio
Parking & Garage GarageParking: Garage Attached

Property Information
Year Built Year Built: 1850
Property Type / Style Property Type: Single Family HomeArchitecture: Conventional

Community
Units in Building: 2

Lot Information
Lot Area: 4800 sqft

Price History for 216 E Chestnut St

Date	Price	Event	Source
09/12/2012	$675,000	Sold	N/A
Recording Date 09/12/2012 Contract Date 08/30/2012 County Transfer Tax $6,750 Total Transfer Tax $10,125
09/28/2005	$975,000	Sold	N/A
Recording Date 09/28/2005 County Transfer Tax N/A Total Transfer Tax N/A
06/11/2002	$505,000	Sold	N/A
Recording Date 06/11/2002 County Transfer Tax N/A Total Transfer Tax N/A
10/17/1997	$364,750	Sold	N/A
Recording Date 10/17/1997 County Transfer Tax N/A Total Transfer Tax N/A

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Property Tax and Assessment

Year	2025
Tax
Assessment	$816,600

Home facts updated by county records

Comparable Sales for 216 E Chestnut St

Address	Distance	Property Type	Sold Price	Sold Date	Bed	Bath	Sqft
204 Mulberry St, Saint Michaels, MD	0.14	Single-Family Home	$1,350,000	10/27/25	3	2.5	2,320
504 Talbot St, Saint Michaels, MD	0.19	Single-Family Home	$850,000	07/31/25	3	2.5	2,072
207 Seymour Ave, Saint Michaels, MD	0.19	Single-Family Home	$800,000	11/17/25	4	3.5	1,983
408 Water St, Saint Michaels, MD	0.09	Single-Family Home	$995,000	10/08/25	3	2.5	1,893
701A New Ln, Saint Michaels, MD	0.19	Single-Family Home	$900,000	06/24/25		2	2,592
106 Grace St, Saint Michaels, MD	0.25	Single-Family Home	$775,000	12/02/25	3	1.5	2,068
205 E Chew Ave, Saint Michaels, MD	0.05	Single-Family Home	$1,175,000	11/14/25	2	1.5	1,780
109 W Chew Ave, Saint Michaels, MD	0.24	Single-Family Home	$662,500	07/18/25	3	2	1,824
103 Mulberry St, Saint Michaels, MD	0.18	Single-Family Home	$800,000	08/15/25	4	1.5	1,596
100 Grace St, Saint Michaels, MD	0.22	Single-Family Home	$1,000,000	02/13/26	2	2.5	1,445

Nearby homes

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

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FOR SALE
$350,000
3 bd
2 ba
1,364 sqft
203 Canton St,
Saint Michaels, MD 21663
Coldwell Banker Chesapeake Real Estate Company
FOR SALE
$1,275,000
3 bd
3 ba
2,052 sqft
202 E Chestnut St,
Saint Michaels, MD 21663
TTR Sotheby's International Realty
FOR SALE
OPEN SAT, 11-1PM
1.51 ACRES
$2,449,000
4 bd
4.5 ba
3,300 sqft
962 San Domingo Ct,
Saint Michaels, MD 21663
TTR Sotheby's International Realty
FOR SALE
3D VIEW
0.7 ACRES
$1,725,000
3 bd
2.5 ba
3,078 sqft
602 Landing Rd,
Saint Michaels, MD 21663
Benson & Mangold, LLC
SOLD
MAY 13, 2026
$947,000
3 bd
2.5 ba
1,836 sqft
360 Perry Cabin Dr,
Saint Michaels, MD 21663
Long & Foster Real Estate, Inc.
FOR SALE
$849,900
3 bd
2.5 ba
2,027 sqft
807 Radcliff St,
Michaels, MD 21663
FOR SALE
$849,900
3 bd
2.5 ba
2,027 sqft
807 Radcliff Ave,
Saint Michaels, MD 21663
Long & Foster Real Estate, Inc.
SOLD
MAY 22, 2026
$2,435,000
3 bd
2.5 ba
2,875 sqft
24830 Deepwater Point Dr,
Saint Michaels, MD 21663
Long & Foster Real Estate, Inc.
FOR SALE
0.34 ACRES
$598,000
3 bd
2 ba
2,348 sqft
204 Lincoln Ave,
Saint Michaels, MD 21663
Long & Foster Real Estate, Inc.
FOR SALE
$1,200,000
3 bd
2.5 ba
2,200 sqft
504 Seymour Ave,
Saint Michaels, MD 21663
Benson & Mangold, LLC
FOR SALE
1.03 ACRES
$699,000
4 bd
2.5 ba
2,841 sqft
9206 Martingham Dr,
Saint Michaels, MD 21663
Chesapeake Bay Real Estate Plus, LLC
FOR SALE
$2,538,000
5 bd
5.5 ba
4,673 sqft
203 E Chew Ave,
Saint Michaels, MD 21663
Benson & Mangold, LLC

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Additional Cost

Assigned Schools

These are the assigned schools for 216 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
7y 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
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
APPLY INSTANTLY
$2,200/mo
2 bd
2.5 ba
24345 Widgeon Pl #29,
St Michaels, MD 21663
PET FRIENDLY
FURNISHED
$2,300/mo
2 bd
2.5 ba
24362 Widgeon Pl #2,
St 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 216 E Chestnut St

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$1,275,000
3 bd
3 ba
2,052 sqft
202 E Chestnut St,
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 FRI, 11-1PM
$1,194,000
4 bd
2.5 ba
1,500 sqft
101 Mulberry St,
Saint Michaels, MD 21663
Meredith Fine Properties
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
$2,538,000
5 bd
5.5 ba
4,673 sqft
203 E Chew Ave,
Saint Michaels, MD 21663
Benson & Mangold, LLC
0.34 ACRES
$1,795,000
4 bd
3.5 ba
3,575 sqft
216 E Chew Ave,
Saint Michaels, MD 21663
Coldwell Banker Chesapeake Real Estate Company
$849,900
3 bd
2.5 ba
2,027 sqft
807 Radcliff Ave,
Saint Michaels, MD 21663
Long & Foster Real Estate, Inc.
$1,350,000
4 bd
4.5 ba
3,528 sqft
114 W Chestnut St,
St Michaels, MD 21663
Benson & Mangold, LLC
$1,200,000
3 bd
2.5 ba
2,200 sqft
504 Seymour Ave,
Saint Michaels, MD 21663
Benson & Mangold, LLC
$849,900
3 bd
2.5 ba
2,027 sqft
807 Radcliff St,
Michaels, MD 21663
See more homes for sale in
Saint Michaels
Take a look

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Off Market Homes Near 216 E Chestnut St

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SOLD
MAY 13, 2026
$947,000
3 bd
2.5 ba
1,836 sqft
360 Perry Cabin Dr,
Saint Michaels, MD 21663
Long & Foster Real Estate, Inc.
SOLD
MAY 4, 2026
$775,000
4 bd
4 ba
4,000 sqft
8453 Ingleton Rd,
Easton, MD 21601
SOLD
MAY 1, 2026
$740,000
3 bd
2 ba
1,518 sqft
23869 Mount Misery Rd,
Saint Michaels, MD 21663
Benson & Mangold, LLC
SOLD
APR 30, 2026
$785,000
3 bd
3 ba
2,439 sqft
24822 Swan Rd,
Saint Michaels, MD 21663
Benson & Mangold, LLC
SOLD
MAR 13, 2026
$1,118,892
2 bd
2.5 ba
1,557 sqft
320 Perry Cabin Dr,
Saint Michaels, MD 21663
TTR Sotheby's International Realty
SOLD
FEB 27, 2026
$1,600,000
3 ba
3,562 sqft
7369 Drum Point Rd,
Saint Michaels, MD 21663
SOLD
FEB 19, 2026
$1,202,000
3 bd
2 ba
2,012 sqft
7361 Solitude Rd,
Saint Michaels, MD 21663
Benson & Mangold, LLC
SOLD
FEB 13, 2026
$1,000,000
2 bd
2.5 ba
1,445 sqft
100 Grace St,
Saint Michaels, MD 21663
Benson & Mangold, LLC
SOLD
FEB 6, 2026
$1,130,000
3 bd
3 ba
2,085 sqft
24318 Oakwood Park Rd,
Saint Michaels, MD 21663
Compass
SOLD
FEB 5, 2026
$990,000
3 ba
2,916 sqft
7343 Drum Point Rd,
Saint Michaels, MD 21663
See more homes for sale in
Saint Michaels
Take a look

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Homes for rent near 216 E Chestnut St

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APPLY INSTANTLY
$2,200/mo
2 bd
2.5 ba
1,800 sqft
24345 Widgeon Pl #29,
St Michaels, MD 21663
PET FRIENDLY
FURNISHED
$2,300/mo
2 bd
2.5 ba
1,800 sqft
24362 Widgeon Pl #2,
St Michaels, MD 21663
PET FRIENDLY
$2,650/mo
4 bd
2.5 ba
1,700 sqft
921 S Talbot St #C,
Easton, MD 21663
See more homes for rent in
Saint Michaels
Take a look

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216 E Chestnut St, Saint Michaels, MD 21663 is a studio, 3 bathroom, 2,913 sqft single-family home built in 1850. This property is not currently available for sale. 216 E Chestnut St was last sold on Sep 12, 2012 for $675,000. The current Trulia Estimate for 216 E Chestnut St is $1,403,100.

216 E Chestnut St
Saint Michaels, MD 21663

$1,403,100

$1,403,100

Local Information