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

214 E Chestnut St
Saint Michaels, MD 21663

Studio
4 Baths
2,823 sqft

$1,263,300

Trulia Estimate

as of Jul 10, 2026

Est. Refi. Payment $7,085/mo*

Refinance Your Home

$1,263,300

Trulia Estimate

as of Jul 10, 2026

Est. Refi. Payment $7,085/mo*

Refinance Your Home

Studio

4 Baths

2,823 sqft

Local Information

Map ViewExplore the area around 214 E Chestnut St.
Schools1 Preschool School1 Elementary School1 Middle School1 High School
Shop & Eat

-- mins to

Commute Destination

Description

This single-family home is located at 214 E Chestnut St, Saint Michaels, MD. 214 E Chestnut St is in Saint Michaels, MD and in ZIP code 21663. This property has 4 bathrooms and approximately 2,823 sqft of floor space. This property has a lot size of 6000 sqft and was built in 1850.

214 E Chestnut St, Saint Michaels, MD 21663 is a studio, 4 bathroom, 2,823 sqft single-family home built in 1850. It last sold for $975,000 on Dec 9, 2022. It is currently off market. The Trulia Estimate is $1,263,300, with a rent estimate of $3,121/month.

Home Highlights

Parking

Garage

Outdoor

Patio, Deck

A/C

Heating & Cooling

HOA

None

Price/Sqft

No Info

Listed

Less than a day ago

Home Details for 214 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 ShingleDeckExterior: 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: 1

Lot Information
Lot Area: 6000 sqft

Price History for 214 E Chestnut St

Date	Price	Event	Source
12/09/2022	$975,000	Sold	Bright MLS #MDTA2004204
Recording Date 12/09/2022 County Transfer Tax N/A Total Transfer Tax N/A
11/05/2022	$995,000	Pending	Bright MLS #MDTA2004204

10/28/2022	$995,000	PriceChange	Bright MLS #MDTA2004204
Price Change $200,000 (-17%)
10/14/2022	$1,195,000	Listed For Sale	Bright MLS #MDTA2004204

09/17/2018	$750,000	Sold	N/A
Recording Date 09/17/2018 Contract Date 09/17/2018 County Transfer Tax $75 Total Transfer Tax $113
06/22/2016	$750,000	Sold	N/A
Recording Date 06/22/2016 County Transfer Tax N/A Total Transfer Tax N/A
09/03/2002	$449,900	Sold	N/A
Recording Date 09/03/2002 County Transfer Tax N/A Total Transfer Tax N/A
02/26/1998	$315,000	Sold	N/A
Recording Date 02/26/1998 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	$809,700

Home facts updated by county records

Comparable Sales for 214 E Chestnut St

Address	Distance	Property Type	Sold Price	Sold Date	Bed	Bath	Sqft
114 E Chew Ave, Saint Michaels, MD	0.09	Single-Family Home	$1,152,500	06/10/26	3	2.5	2,336
207 Seymour Ave, Saint Michaels, MD	0.19	Single-Family Home	$800,000	11/17/25	4	3.5	1,983
204 Mulberry St, Saint Michaels, MD	0.13	Single-Family Home	$1,350,000	10/27/25	3	2.5	2,320
408 Water St, Saint Michaels, MD	0.09	Single-Family Home	$995,000	10/08/25	3	2.5	1,893
504 Talbot St, Saint Michaels, MD	0.18	Single-Family Home	$850,000	07/31/25	3	2.5	2,072
106 E Chestnut St, Saint Michaels, MD	0.12	Single-Family Home	$1,225,000	06/05/26	2	2.5	2,282
205 E Chew Ave, Saint Michaels, MD	0.04	Single-Family Home	$1,175,000	11/14/25	2	1.5	1,780
100 Grace St, Saint Michaels, MD	0.21	Single-Family Home	$1,000,000	02/13/26	2	2.5	1,445
121 W Chestnut St, St Michaels, MD	0.30	Single-Family Home	$1,395,000	06/22/26	3	2.5	2,540
103 Mulberry St, Saint Michaels, MD	0.18	Single-Family Home	$800,000	08/15/25	4	1.5	1,596

Nearby homes

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

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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
OFF MARKET
Est. $1,936,300
4 bd
4 ba
2,639 sqft
218 E Chestnut St,
Saint Michaels, MD 21663
Meredith Fine Properties
OFF MARKET
Est. $1,677,200
4 bd
2.5 ba
3,694 sqft
201 E Chew Ave,
Saint Michaels, MD 21663
Benson & Mangold, LLC
OFF MARKET
Est. $1,815,600
3 bd
3.5 ba
2,579 sqft
417 Water St,
Saint Michaels, MD 21663
Meredith Fine Properties
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
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
FOR SALE
OPEN SAT, 12-2PM
0.34 ACRES
$1,595,000
4 bd
3.5 ba
3,575 sqft
216 E Chew Ave,
Saint Michaels, MD 21663
Coldwell Banker Chesapeake Real Estate Company
OFF MARKET
Est. $835,600
3 bd
2.5 ba
2,294 sqft
201 E Marengo St,
St Michaels, MD 21663
Benson & Mangold, LLC
FOR SALE
3D VIEW
0.28 ACRES
$574,999
2 bd
1 ba
1,200 sqft
204 E Marengo St,
Saint Michaels, MD 21663
Compass
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
FOR SALE
OPEN SAT, 1-3PM
NEW CONSTRUCTION
3D VIEW
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
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

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Additional Cost

Assigned Schools

These are the assigned schools for 214 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
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
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 214 E Chestnut St

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OPEN SAT, 12-2PM
0.34 ACRES
$1,595,000
4 bd
3.5 ba
3,575 sqft
216 E Chew Ave,
Saint Michaels, MD 21663
Coldwell Banker Chesapeake Real Estate Company
$1,195,000
4 bd
4.5 ba
3,528 sqft
114 W Chestnut St,
St Michaels, MD 21663
Benson & Mangold, LLC
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
OPEN SAT, 1-3PM
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
Long & Foster Real Estate, Inc.
OPEN SAT, 12-2PM
$1,179,000
4 bd
2.5 ba
1,500 sqft
101 Mulberry St,
Saint Michaels, MD 21663
Meredith Fine Properties
$1,049,000
3 bd
2.5 ba
2,200 sqft
504 Seymour Ave,
Saint Michaels, MD 21663
Benson & Mangold, LLC
$849,000
3 bd
2 ba
1,288 sqft
803 New Ln,
Saint Michaels, MD 21663
TTR Sotheby's International Realty
$799,900
3 bd
2.5 ba
2,027 sqft
807 Radcliff St,
Michaels, MD 21663
$342,900
3 bd
2 ba
1,364 sqft
203 Canton St,
Saint Michaels, MD 21663
Coldwell Banker Chesapeake Real Estate Company
See more homes for sale in
Saint Michaels
Take a look

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Off Market Homes Near 214 E Chestnut St

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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
JUL 6, 2026
$1,500,000
4 bd
4 ba
4,819 sqft
8466 Aveley Farm Rd,
Easton, MD 21601
Benson & Mangold, LLC
SOLD
JUN 26, 2026
$1,700,000
5 bd
3.5 ba
4,310 sqft
22707 Marshall Ln,
Wittman, MD 21676
TTR Sotheby's International Realty
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 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
$765,000
3 bd
2.5 ba
3,166 sqft
24912 Back Creek Dr,
Saint Michaels, MD 21663
Benson & Mangold, LLC
SOLD
MAY 28, 2026
$1,780,000
4 bd
3.5 ba
2,250 sqft
23857 Ebb Point Rd,
Bozman, MD 21612
Meredith Fine Properties
See more homes for sale in
Saint Michaels
Take a look

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214 E Chestnut St
Saint Michaels, MD 21663

$1,263,300

$1,263,300

Local Information