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

102 E Chestnut St
St Michaels, MD 21663

Studio
1 Bath
830 sqft

$640,100

Trulia Estimate

as of Jun 12, 2026

Est. Refi. Payment $3,607/mo*

Refinance Your Home

$640,100

Trulia Estimate

as of Jun 12, 2026

Est. Refi. Payment $3,607/mo*

Refinance Your Home

Studio

1 Bath

830 sqft

Local Information

-- mins to

Commute Destination

Description

This single-family home is located at 102 E Chestnut St, St Michaels, MD. 102 E Chestnut St is in St Michaels, MD and in ZIP code 21663. This property has 1 bathroom and approximately 830 sqft of floor space. This property has a lot size of 6358 sqft and was built in 1948.

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

No Info

Outdoor

No Info

A/C

Heating & Cooling

HOA

None

Price/Sqft

No Info

Listed

Less than a day ago

Home Details for 102 E Chestnut St

Interior Features
Heating & Cooling Heating: Heat PumpAir ConditioningHeating Fuel: Heat Pump
Levels, Entrance, & Accessibility Stories: 1
Fireplace & Spa Fireplace

Exterior Features
Exterior Home Features Roof: Shake ShingleExterior: Other

Property Information
Year Built Year Built: 1948
Property Type / Style Property Type: Single Family HomeArchitecture: Conventional

Community
Units in Building: 1

Lot Information
Lot Area: 6358 sqft

Price History for 102 E Chestnut St

Date	Price	Event	Source
06/02/1997	$110,000	Sold	N/A
Recording Date 06/02/1997 County Transfer Tax N/A Total Transfer Tax N/A
11/01/1996	$100,000	Sold	N/A
Recording Date 11/01/1996 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

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Price per sq ft

—

Available listings

8MoM

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Property Tax and Assessment

Year	2025
Tax
Assessment	$432,900

Home facts updated by county records

Homeowner tools

Estimated monthly rent$2,056/mo

List your home for rent

Homes for rent near 102 E Chestnut St

See what comparable homes in the neighborhood are renting for.

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PET FRIENDLY
$2,650/mo
4 bd
2.5 ba
1,700 sqft
921 S Talbot St #C,
Easton, MD 21663
2 bd
2 ba
111 Mitchell St #f320a52c6,
Saint Michaels, MD 21663
2 bd
2 ba
113 Mitchell St #f320a52c6,
Saint Michaels, MD 21663
1 bd
1 ba
24700 Deepwater Point Dr #776f18ccb,
Saint Michaels, MD 21663
See more homes for rent in
St Michaels
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Comparable Sales for 102 E Chestnut St

Address	Distance	Property Type	Sold Price	Sold Date	Bed	Bath	Sqft
115 Thompson St, Saint Michaels, MD	0.15	Single-Family Home	$290,000	01/21/26		1	972
103 W Marengo St, St Michaels, MD	0.10	Single-Family Home	$545,000	07/11/25	2	1.5	1,209
106 Conner St #C, Saint Michaels, MD	0.31	Single-Family Home	$399,000	07/18/25	3	1	1,080
111 Gloria Ave, Saint Michaels, MD	0.27	Single-Family Home	$425,000	05/18/26	2	1.5	1,125
113 Thompson St, Saint Michaels, MD	0.13	Single-Family Home	$580,000	10/31/25	3	2	1,566
109 W Chew Ave, Saint Michaels, MD	0.09	Single-Family Home	$662,500	07/18/25	3	2	1,824
112 Mitchell St, Saint Michaels, MD	0.59	Single-Family Home	$275,000	07/31/25	3	1	1,368
113 Glory Ave, Saint Michaels, MD	0.26	Single-Family Home	$400,000	01/22/26		2	1,456
103 Mulberry St, Saint Michaels, MD	0.14	Single-Family Home	$800,000	08/15/25	4	1.5	1,596
106C Conner St, Saint Michaels, MD	0.31	Single-Family Home	$399,000	09/15/25		2	1,080

Nearby homes

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

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OFF MARKET
Est. $461,300
1 bd
1 ba
494 sqft
507 Talbot St #1,
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
JUN 5, 2026
$1,225,000
2 bd
2.5 ba
2,282 sqft
106 E Chestnut St,
Saint Michaels, MD 21663
Taylor Properties
FOR SALE
$1,165,000
2 bd
2 ba
2,024 sqft
107 E Chestnut St,
Saint Michaels, MD 21663
TTR Sotheby's International Realty
OFF MARKET
Est. $994,400
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
OFF MARKET
Est. $1,688,100
4 bd
2.5 ba
3,694 sqft
201 E Chew Ave,
Saint Michaels, MD 21663
Benson & Mangold, LLC
OFF MARKET
Est. $535,200
2 bd
1.5 ba
1,209 sqft
103 W Marengo St,
St Michaels, MD 21663
TTR Sotheby's International Realty
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
OFF MARKET
Est. $1,286,200
2 bd
2 ba
2,654 sqft
104 Chew West Ave,
Saint Michaels, MD 21663
Non Subscribing Office
OFF MARKET
Est. $831,100
3 bd
2.5 ba
2,294 sqft
201 E Marengo St,
St Michaels, MD 21663
Benson & Mangold, LLC
OFF MARKET
Est. $650,600
3 bd
2 ba
1,824 sqft
109 W Chew Ave,
Saint Michaels, MD 21663
Benson & Mangold, LLC

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Additional Cost

Assigned Schools

These are the assigned schools for 102 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
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
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
St Michaels
Take a look

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Homes for sale near 102 E Chestnut St

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NEW - 7 HRS AGO
0.28 ACRES
$574,999
2 bd
1 ba
1,200 sqft
204 E Marengo St,
Saint Michaels, MD 21663
Compass
$342,900
3 bd
2 ba
1,364 sqft
203 Canton St,
Saint Michaels, MD 21663
Coldwell Banker Chesapeake Real Estate Company
$1,165,000
2 bd
2 ba
2,024 sqft
107 E Chestnut St,
Saint Michaels, MD 21663
TTR Sotheby's International Realty
$1,049,000
4 bd
3 ba
2,250 sqft
109 W Marengo St,
St Michaels, MD 21663
Benson & Mangold, LLC
OPEN FRI, 12-2PM
$1,194,000
4 bd
2.5 ba
1,500 sqft
101 Mulberry St,
Saint Michaels, MD 21663
Meredith Fine Properties
$1,885,000
3 bd
2.5 ba
2,284 sqft
222 E Chestnut St,
Saint Michaels, MD 21663
Long & Foster Real Estate, Inc.
$1,275,000
3 bd
3 ba
2,052 sqft
202 E Chestnut St,
Saint Michaels, MD 21663
TTR Sotheby's International Realty
$825,000
3 bd
2.5 ba
2,027 sqft
807 Radcliff St,
Michaels, MD 21663
$425,000
3 bd
2 ba
1,120 sqft
101 Brooks Ln,
Saint Michaels, MD 21663
Benson & Mangold, LLC
$1,195,000
4 bd
4.5 ba
3,528 sqft
114 W Chestnut St,
St Michaels, MD 21663
Benson & Mangold, LLC
See more homes for sale in
St Michaels
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Off Market Homes Near 102 E Chestnut St

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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 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 29, 2026
$345,000
2 bd
2.5 ba
1,800 sqft
24354 Widgeon Pl #20,
St Michaels, MD 21663
TTR Sotheby's International Realty
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 18, 2026
$425,000
2 bd
1.5 ba
1,125 sqft
111 Gloria Ave,
Saint Michaels, MD 21663
Benson & Mangold, LLC
SOLD
MAY 15, 2026
$600,000
3 bd
2.5 ba
2,080 sqft
23201 Stewart Way,
McDaniel, MD 21647
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.
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
See more homes for sale in
St Michaels
Take a look

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102 E Chestnut St, St Michaels, MD 21663 is a studio, 1 bathroom, 830 sqft single-family home built in 1948. This property is not currently available for sale. 102 E Chestnut St was last sold on Jun 2, 1997 for $110,000. The current Trulia Estimate for 102 E Chestnut St is $640,100.

102 E Chestnut St
St Michaels, MD 21663

$640,100

$640,100

Local Information