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

209 E Chestnut St
Saint Michaels, MD 21663

3 Beds
4 Baths
2,926 sqft

$1,151,000

Trulia Estimate

as of Jun 24, 2026

Est. Refi. Payment $6,408/mo*

Refinance Your Home

$1,151,000

Trulia Estimate

as of Jun 24, 2026

Est. Refi. Payment $6,408/mo*

Refinance Your Home

3 Beds

4 Baths

2,926 sqft

Local Information

Map ViewExplore the area around 209 E Chestnut St.
Schools1 Preschool School1 Elementary School1 Middle School1 High School
Shop & Eat

-- mins to

Commute Destination

Description

Wow! a great place to "Call Home" ready to move in and enjoy the ambiance of St Michaels and the land of pleasant living. Walk to shops, restaurants, farmers market, waterfront parks and the harbor with water access is one block away.

Neighborhood Description

Very walkable, locally owned grocery store 1 block away, great meats, flowers, & local produce. Waterfront park 1 block away,harbor 1 block away, post office 2 blocks away, and very convenient to other amenities.

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

Porch, Patio

A/C

Heating & Cooling

HOA

None

Price/Sqft

No Info

Listed

Less than a day ago

Home Details for 209 E Chestnut St

Interior Features
Heating & Cooling Heating: Heat Pump, ElectricAir ConditioningCooling System: CentralHeating Fuel: Heat Pump
Levels, Entrance, & Accessibility Stories: 2Floors: Tile, Hardwood
Interior Details Types of Rooms: Walk In Closet, Breakfast Nook, Dining Room, Laundry Room, Master BathCeiling Fan
Appliances & Utilities DishwasherDisposalDryerRefrigeratorWasher
Fireplace & Spa FireplaceJetted Bath Tub
Windows, Doors, Floors & Walls Double Paned Windows

Exterior Features
Exterior Home Features Roof: Shake ShingleExterior: OtherGardenPatioPorchSprinkler System
Parking & Garage Parking: Off Street

Property Information
Year Built Year Built: 1970Year Updated: 2009
Property Type / Style Property Type: Single Family HomeArchitecture: Conventional

Community
Units in Building: 1

Lot Information
Lot Area: 4560 sqft

Price History for 209 E Chestnut St

Date	Price	Event	Source
08/15/2011	$590,000	Sold	N/A
Recording Date 08/15/2011 County Transfer Tax N/A Total Transfer Tax N/A
06/26/2008	$450,000	Sold	N/A
Recording Date 06/26/2008 County Transfer Tax N/A Total Transfer Tax N/A
02/19/1997	$160,000	Sold	N/A
Recording Date 02/19/1997 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	$698,700

Home facts updated by county records

Comparable Sales for 209 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
204 Mulberry St, Saint Michaels, MD	0.09	Single-Family Home	$1,350,000	10/27/25	3	2.5	2,320
504 Talbot St, Saint Michaels, MD	0.14	Single-Family Home	$850,000	07/31/25	3	2.5	2,072
207 Seymour Ave, Saint Michaels, MD	0.21	Single-Family Home	$800,000	11/17/25	4	3.5	1,983
408 Water St, Saint Michaels, MD	0.04	Single-Family Home	$995,000	10/08/25	3	2.5	1,893
106 Grace St, Saint Michaels, MD	0.19	Single-Family Home	$775,000	12/02/25	3	1.5	2,068
109 W Chew Ave, Saint Michaels, MD	0.20	Single-Family Home	$662,500	07/18/25	3	2	1,824
113 Thompson St, Saint Michaels, MD	0.22	Single-Family Home	$580,000	10/31/25	3	2	1,566
901 S Talbot St, St Michaels, MD	0.26	Single-Family Home	$600,000	08/08/25	3	2	1,660
204 W Chew Ave, Saint Michaels, MD	0.26	Single-Family Home	$660,000	09/16/25	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. $1,708,500
4 bd
2.5 ba
3,694 sqft
201 E Chew Ave,
Saint Michaels, MD 21663
Benson & Mangold, LLC
OFF MARKET
Est. $1,011,200
4 bd
2.5 ba
1,781 sqft
115 W Chew Ave,
Saint Michaels, MD 21663
Meredith Fine Properties
FOR SALE
3D VIEW
$2,195,000
5 bd
5.5 ba
4,673 sqft
203 E Chew Ave,
Saint Michaels, MD 21663
Benson & Mangold, LLC
OFF MARKET
Est. $1,891,500
3 bd
3.5 ba
2,579 sqft
417 Water St,
Saint Michaels, MD 21663
Meredith Fine Properties
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
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
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 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
$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. $1,974,500
4 bd
4 ba
2,639 sqft
218 E Chestnut St,
Saint Michaels, MD 21663
Meredith Fine Properties
OFF MARKET
Est. $835,400
3 bd
2.5 ba
2,294 sqft
201 E Marengo St,
St Michaels, MD 21663
Benson & Mangold, LLC
FOR SALE
3D VIEW
$1,885,000
3 bd
2.5 ba
2,284 sqft
222 E Chestnut St,
Saint Michaels, MD 21663
Long & Foster Real Estate, Inc.

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Additional Cost

Assigned Schools

These are the assigned schools for 209 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
Saint Michaels
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Homes for sale near 209 E Chestnut St

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$1,885,000
3 bd
2.5 ba
2,284 sqft
222 E Chestnut St,
Saint Michaels, MD 21663
Long & Foster Real Estate, Inc.
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
$1,165,000
2 bd
2 ba
2,024 sqft
107 E Chestnut St,
Saint Michaels, MD 21663
TTR Sotheby's International Realty
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
$1,195,000
4 bd
4.5 ba
3,528 sqft
114 W Chestnut St,
St Michaels, MD 21663
Benson & Mangold, LLC
$2,195,000
5 bd
5.5 ba
4,673 sqft
203 E Chew Ave,
Saint Michaels, MD 21663
Benson & Mangold, LLC
$1,049,000
4 bd
3 ba
2,250 sqft
109 W Marengo St,
St 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
$825,000
3 bd
2.5 ba
2,027 sqft
807 Radcliff Ave,
Saint Michaels, MD 21663
Long & Foster Real Estate, Inc.
$825,000
3 bd
2.5 ba
2,027 sqft
807 Radcliff St,
Michaels, MD 21663
See more homes for sale in
Saint Michaels
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Off Market Homes Near 209 E Chestnut St

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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 15, 2026
$616,000
4 bd
2 ba
2,448 sqft
25714 Edgeview Rd,
Royal Oak, MD 21662
Benson & Mangold, LLC
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 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
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.
See more homes for sale in
Saint Michaels
Take a look

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209 E Chestnut St, Saint Michaels, MD 21663 is a 3 bedroom, 4 bathroom, 2,926 sqft single-family home built in 1970. This property is not currently available for sale. 209 E Chestnut St was last sold on Aug 15, 2011 for $590,000. The current Trulia Estimate for 209 E Chestnut St is $1,151,000.

209 E Chestnut St
Saint Michaels, MD 21663

$1,151,000

$1,151,000

Local Information