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

114 E Chestnut St
Saint Michaels, MD 21663

3 Beds
3 Baths
1,868 sqft

$856,100

Trulia Estimate

as of Jul 4, 2026

Est. Refi. Payment $4,790/mo*

Refinance Your Home

$856,100

Trulia Estimate

as of Jul 4, 2026

Est. Refi. Payment $4,790/mo*

Refinance Your Home

3 Beds

3 Baths

1,868 sqft

Local Information

Map ViewExplore the area around 114 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 114 E Chestnut St, Saint Michaels, MD. 114 E Chestnut St is in Saint Michaels, MD and in ZIP code 21663. This property has 3 bedrooms, 3 bathrooms and approximately 1,868 sqft of floor space. This property has a lot size of 2640 sqft and was built in 1851.

114 E Chestnut St, Saint Michaels, MD 21663 is a 3 bedroom, 3 bathroom, 1,868 sqft single-family home built in 1851. It last sold for $431,000 on Jul 21, 2004. It is currently off market. The Trulia Estimate is $856,100, with a rent estimate of $2,427/month.

Home Highlights

Parking

No Info

Outdoor

Patio

A/C

Heating & Cooling

HOA

None

Price/Sqft

No Info

Listed

Less than a day ago

Home Details for 114 E Chestnut St

Interior Features
Heating & Cooling Heating: Baseboard, OilCooling System: OtherHeating Fuel: Baseboard
Levels, Entrance, & Accessibility Stories: 2Floors: Tile, Carpet, Hardwood
Appliances & Utilities DishwasherDisposalDryerRefrigeratorWasher
Fireplace & Spa Fireplace

Exterior Features
Exterior Home Features Roof: Shake ShingleExterior: WoodPatio
Parking & Garage Parking: On Street

Property Information
Year Built Year Built: 1851Year Updated: 2003
Property Type / Style Property Type: Single Family HomeArchitecture: Conventional

Community
Units in Building: 1

Lot Information
Lot Area: 2640 sqft

Price History for 114 E Chestnut St

Date	Price	Event	Source
07/21/2004	$431,000	Sold	N/A
Recording Date 07/21/2004 County Transfer Tax N/A Total Transfer Tax N/A
06/06/2001	$251,000	Sold	N/A
Recording Date 06/06/2001 County Transfer Tax N/A Total Transfer Tax N/A
04/29/1996	$92,000	Sold	N/A
Recording Date 04/29/1996 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	$441,800

Home facts updated by county records

Comparable Sales for 114 E Chestnut St

Address	Distance	Property Type	Sold Price	Sold Date	Bed	Bath	Sqft
504 Talbot St, Saint Michaels, MD	0.10	Single-Family Home	$850,000	07/31/25	3	2.5	2,072
106 Grace St, Saint Michaels, MD	0.17	Single-Family Home	$775,000	12/02/25	3	1.5	2,068
204 W Chew Ave, Saint Michaels, MD	0.23	Single-Family Home	$660,000	09/16/25	3	2	1,500
114 E Chew Ave, Saint Michaels, MD	0.06	Single-Family Home	$1,152,500	06/10/26	3	2.5	2,336
408 Water St, Saint Michaels, MD	0.07	Single-Family Home	$995,000	10/08/25	3	2.5	1,893
109 W Chew Ave, Saint Michaels, MD	0.16	Single-Family Home	$662,500	07/18/25	3	2	1,824
204 Mulberry St, Saint Michaels, MD	0.11	Single-Family Home	$1,350,000	10/27/25	3	2.5	2,320
113 Thompson St, Saint Michaels, MD	0.19	Single-Family Home	$580,000	10/31/25	3	2	1,566
901 S Talbot St, St Michaels, MD	0.23	Single-Family Home	$600,000	08/08/25	3	2	1,660
304 N Talbot St, St Michaels, MD	0.47	Single-Family Home	$785,000	10/15/25	3	2.5	2,028

Nearby homes

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

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OFF MARKET
Est. $1,706,500
4 bd
2.5 ba
3,694 sqft
201 E Chew Ave,
Saint Michaels, MD 21663
Benson & Mangold, LLC
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
OFF MARKET
Est. $1,869,300
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
OFF MARKET
Est. $1,947,100
4 bd
4 ba
2,639 sqft
218 E Chestnut St,
Saint Michaels, MD 21663
Meredith Fine Properties
OFF MARKET
Est. $843,900
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.
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
Est. $1,174,700
4 bd
3 ba
2,703 sqft
202 Mulberry St,
Saint Michaels, MD 21663
TTR Sotheby's International Realty

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Additional Cost

Assigned Schools

These are the assigned schools for 114 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
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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
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
Contact for price
1-2 bd
1-2 ba
111 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
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Saint Michaels
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Homes for sale near 114 E Chestnut St

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OPEN SAT, 11-1PM
$1,179,000
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.
$1,049,000
4 bd
3 ba
2,250 sqft
109 W Marengo St,
St Michaels, MD 21663
Benson & Mangold, LLC
$799,900
3 bd
2.5 ba
2,027 sqft
807 Radcliff Ave,
Saint Michaels, MD 21663
Long & Foster Real Estate, Inc.
$799,900
3 bd
2.5 ba
2,027 sqft
807 Radcliff St,
Michaels, MD 21663
NEW
OPEN SAT, 12-3PM
$849,000
3 bd
2 ba
1,288 sqft
803 New Ln,
Saint Michaels, MD 21663
TTR Sotheby's International Realty
OPEN SUN, 1-4PM
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
$342,900
3 bd
2 ba
1,364 sqft
203 Canton St,
Saint Michaels, MD 21663
Coldwell Banker Chesapeake Real Estate Company
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
$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
Saint Michaels
Take a look

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Off Market Homes Near 114 E Chestnut St

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SOLD
JUN 30, 2026
$560,000
4 bd
3 ba
2,410 sqft
6980 Hopkins Neck Rd,
Royal Oak, MD 21662
Long & Foster Real Estate, Inc.
SOLD
JUN 30, 2026
$539,500
3 bd
2 ba
1,456 sqft
113 Gloria Ave,
Saint Michaels, MD 21663
Benson & Mangold, LLC
SOLD
JUN 30, 2026
$560,000
4 bd
3 ba
2,410 sqft
6980 Hopkins Neck Rd,
Easton, MD 21601
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
See more homes for sale in
Saint Michaels
Take a look

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114 E Chestnut St
Saint Michaels, MD 21663

$856,100

$856,100

Local Information