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

FOR SALE

107 E Chestnut St
Saint Michaels, MD 21663

2 Beds
2 Baths
2,024 sqft

$1,165,000

Est. Mortgage $6,497/mo*

Get Pre-Qualified

$1,165,000

Est. Mortgage $6,497/mo*

Get Pre-Qualified

2 Beds

2 Baths

2,024 sqft

Local Information

-- mins to

Commute Destination

Description

Welcome to 107 E. Chestnut, a beautifully restored circa-1870 residence nestled in the heart of St. Michaels. From the moment you step inside, you are greeted by the perfect blend of timeless character and modern sophistication, where original architectural details have been thoughtfully preserved and seamlessly integrated with extensive renovations. The spacious entry combines an elegant living and dining area, featuring wood floors, a gas fireplace flanked by custom built-ins, and custom shutters have been added to each window. Throughout this home you will find historic charm and craftsmanship are evident at every turn. At the rear of the home is a full bath and designer kitchen that opens to the family room highlighted by soaring ceilings and an abundance of windows that fill the space with natural light year round. This inviting area flows to the screened-in porch and brick patio, creating the perfect setting for indoor-outdoor living. Beyond the patio lies a garden oasis featuring lush landscaping, colorful perennials, pond and large detached shed/storage building. The current owner has worked with the Town of St. Michaels to obtain approvals for converting this structure into a separate guest suite, and architectural plans are available for the next owner. The second level offers two generously sized bedrooms and a beautifully redesigned full bath. The rear bedroom includes an overlook of the family room, which offers additional space that could easily be transformed into a private sitting area, dressing room or walk-in closet. The front bedroom features a dedicated dressing room and oversized closet, providing the potential to create an en-suite bath. Both rooms offer cathedral ceilings with exposed rafters adding to the rooms architectural interest and charm. This is a true gem in historic St. Michaels that includes off street parking. Don't miss this exceptional opportunity to own a home in the one of the most popular towns on the Eastern Shore.

Home Highlights

Parking

Open Parking

Outdoor

No Info

A/C

Heating & Cooling

HOA

None

Price/Sqft

$576

Listed

4 days ago

Home Details for 107 E Chestnut St

Interior Features
Interior Details Number of Rooms: 1Types of Rooms: Basement
Beds & Baths Number of Bedrooms: 2Number of Bathrooms: 2Number of Bathrooms (full): 2Number of Bathrooms (main level): 1
Dimensions and Layout Living Area: 2024 Square Feet
Appliances & Utilities Appliances: Water Heater
Heating & Cooling Heating: Heat Pump,ElectricHas CoolingAir Conditioning: Central Air,ElectricHas HeatingHeating Fuel: Heat Pump
Fireplace & Spa Number of Fireplaces: 1Has a Fireplace
Windows, Doors, Floors & Walls Flooring: Hardwood
Levels, Entrance, & Accessibility Stories: 2Levels: TwoAccessibility: NoneFloors: Hardwood
View No View

Exterior Features
Exterior Home Features Other Structures: Above Grade, Below GradeFoundation: Crawl SpaceNo Private Pool
Parking & Garage No CarportNo GarageNo Attached GarageHas Open ParkingParking: Driveway
Pool Pool: None
Frontage Not on Waterfront
Water & Sewer Sewer: Public Sewer
Finished Area Finished Area (above surface): 2024 Square Feet

Days on Market
Days on Market: 4

Property Information
Year Built Year Built: 1880
Property Type / Style Property Type: ResidentialProperty Subtype: Single Family ResidenceStructure Type: DetachedArchitecture: Victorian
Building Construction Materials: Aluminum Siding, Wood SidingNot a New Construction
Property Information Condition: ExcellentParcel Number: 2102063735

Price & Status
Price List Price: $1,165,000Price Per Sqft: $576
Status Change & Dates Possession Timing: Close Of Escrow

Active Status
MLS Status: ACTIVE

Location
Direction & Address City: SAINT MICHAELSCommunity: St. Michaels
School Information Elementary School District: Talbot County Public SchoolsJr High / Middle School District: Talbot County Public SchoolsHigh School District: Talbot County Public Schools

Agent Information
Listing Agent Listing ID: MDTA2013968

Building
Building Area Building Area: 2024 Square Feet

Community
Not Senior Community

HOA
No HOA

Lot Information
Lot Area: 3600 sqft

Listing Info
Special Conditions: Standard

Offer
Listing Agreement Type: Exclusive Right To SellListing Terms: Cash, Conventional

Business
Business Information Ownership: Fee Simple

Miscellaneous
Mls Number: MDTA2013968Municipality: Saint MichaelsAbove Grade Unfinished Area: 2024

Additional Information
Source Internet Entire Listing Display: Y

Last check for updates: about 6 hours ago

Listing courtesy of Monica Penwell, (410) 310-0225

TTR Sotheby's International Realty, (410) 745-2596

Source: Bright MLS, MLS#MDTA2013968

Also Listed on Bright MLS.

Market trends in Saint Michaels

Last updated May 2026

Avg. sale price

—

Sale-to-List Price

—

Price per sq ft

—

Available listings

8MoM

Price History for 107 E Chestnut St

Date	Price	Event	Source
06/11/2026	$1,165,000	Listed For Sale	Bright MLS #MDTA2013968

01/02/2026	$1,195,000	ListingRemoved	Bright MLS #MDTA2011802

10/28/2025	$1,195,000	PriceChange	Bright MLS #MDTA2011802
Price Change $100,000 (-8%)
09/13/2025	$1,295,000	Listed For Sale	Bright MLS #MDTA2011802

07/15/2022	$815,000	Sold	Bright MLS #MDTA2002896
Recording Date 07/15/2022 County Transfer Tax N/A Total Transfer Tax N/A
05/25/2022	$719,000	Pending	Bright MLS #MDTA2002896

05/06/2022	$719,000	Contingent	Bright MLS #MDTA2002896

05/04/2022	$719,000	Listed For Sale	Long & Foster Broker Feed #MDTA2002896_100

11/23/2010	$410,000	Sold	N/A
Recording Date 11/23/2010 Contract Date 11/23/2010 County Transfer Tax N/A Total Transfer Tax N/A
05/31/2001	$205,000	Sold	N/A
Recording Date 05/31/2001 County Transfer Tax N/A Total Transfer Tax N/A

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Property Tax and Assessment

Year	2025
Tax
Assessment	$531,300

Home facts updated by county records

Comparable Sales for 107 E Chestnut St

Address	Distance	Property Type	Sold Price	Sold Date	Bed	Bath	Sqft
106 Grace St, Saint Michaels, MD	0.12	Single-Family Home	$775,000	12/02/25	3	1.5	2,068
205 E Chew Ave, Saint Michaels, MD	0.11	Single-Family Home	$1,175,000	11/14/25	2	1.5	1,780
204 W Chew Ave, Saint Michaels, MD	0.19	Single-Family Home	$660,000	09/16/25	3	2	1,500
504 Talbot St, Saint Michaels, MD	0.07	Single-Family Home	$850,000	07/31/25	3	2.5	2,072
109 W Chew Ave, Saint Michaels, MD	0.12	Single-Family Home	$662,500	07/18/25	3	2	1,824
106 E Chestnut St, Saint Michaels, MD	0.02	Single-Family Home	$1,225,000	06/05/26	2	2.5	2,282
100 Grace St, Saint Michaels, MD	0.09	Single-Family Home	$1,000,000	02/13/26	2	2.5	1,445
103 Mulberry St, Saint Michaels, MD	0.10	Single-Family Home	$800,000	08/15/25	4	1.5	1,596
203 Mulberry St, Saint Michaels, MD	0.11	Single-Family Home	$926,000	01/15/26	3	2	1,740
103 W Marengo St, St Michaels, MD	0.14	Single-Family Home	$545,000	07/11/25	2	1.5	1,209

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JUN 5, 2026
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Skip to first item

Additional Cost

Assigned Schools

These are the assigned schools for 107 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

Monica Penwell, TTR Sotheby's International Realty, (410) 745-2596

Agent Phone: (410) 310-0225

The data relating to real estate for sale on this website appears in part through the BRIGHT Internet Data Exchange program, a voluntary cooperative exchange of property listing data between licensed real estate brokerage firms, and is provided by BRIGHT through a licensing agreement. Listing information is from various brokers who participate in the Bright MLS IDX program and not all listings may be visible on the site. The property information being provided on or through the website is for the personal, non-commercial use of consumers and such information may not be used for any purpose other than to identify prospective properties consumers may be interested in purchasing. Some properties which appear for sale on the website may no longer be available because they are for instance, under contract, sold or are no longer being offered for sale. Property information displayed is deemed reliable but is not guaranteed. Copyright 2026 Bright MLS, Inc. Click here for more information

107 E Chestnut St, Saint Michaels, MD 21663 is a 2 bedroom, 2 bathroom, 2,024 sqft single-family home built in 1880. This property is currently available for sale and was listed by Bright MLS on May 29, 2026. The MLS # for this home is MLS# MDTA2013968.

107 E Chestnut St Saint Michaels, MD 21663

$1,165,000

$1,165,000

Local Information

Description

Home Highlights

Home Details for 107 E Chestnut St

Interior Features

Exterior Features

Days on Market

Property Information

Price & Status

Active Status

Location

Agent Information

Building

Community

HOA

Lot Information

Listing Info

Offer

Business

Miscellaneous

Additional Information

Market trends in Saint Michaels

Price History for 107 E Chestnut St

Similar Homes You May Like

New Listings near 107 E Chestnut St

Property Tax and Assessment

Comparable Sales for 107 E Chestnut St

Nearby homes

Additional Cost

Assigned Schools

What Locals Say about Saint Michaels

LGBTQ Local Legal Protections

Housing

Employment

Public accommodations

107 E Chestnut St
Saint Michaels, MD 21663