107 E Chestnut St, Saint Michaels, MD 21663
Property image
Property image
SOLD
JUL 27, 2026

$1,134,600

Trulia Estimate
  • 2 Beds
  • 2 Baths
  • 2,024 sqft

107 E Chestnut St, Saint Michaels, MD 21663

Est. Refi. Payment $6,454/mo*
Refinance Your Home
Currently Off Market - Sold Jul 27, 2026 for $1,135,000 (3% below list price)

Home Value

Trulia Estimate
$1.14M
Since last month
Decreased$3K (-0.3%)
Since last year
Increased$190K (+20.2%)
Since last sale
Decreased$3K (-0.3%)
Learn more about this home's value by checking out its Trulia Estimate, the value of nearby homes, and how much similar homes have sold for.

Trulia Estimate

The of this home's value increased by +159% in the last 10 years
MonthEstimated value
2026
August 2026$1.13M
August 2026$1.13M
July 2026$1.13M
June 2026$1.12M
May 2026$953K
April 2026$1.14M
March 2026$1.13M
February 2026$1.13M
January 2026$1.13M
2025
2024
2023
2022
2021
2020
2019
2018
2017
2016

Comparable sales

These are recently sold homes that have a similar location or other similar features to this home, like bedrooms, bathrooms, and square footage. Get a sense of the expected prices in the area by viewing these homes.
Address
Distance
Property Type
Sold Price
Sold Date
Bed
Bath
Sqft
205 E Chew Ave, Saint Michaels, MD
0.11
Single-Family Home
$1,175,000
11/14/25
2
1.5
1,780
106 Grace St, Saint Michaels, MD
0.12
Single-Family Home
$775,000
12/02/25
3
1.5
2,068
106 E Chestnut St, Saint Michaels, MD
0.02
Single-Family Home
$1,225,000
06/05/26
2
2.5
2,282
114 E Chew Ave, Saint Michaels, MD
0.11
Single-Family Home
$1,152,500
06/10/26
3
2.5
2,336
204 W Chew Ave, Saint Michaels, MD
0.19
Single-Family Home
$660,000
09/16/25
3
2
1,500
100 Grace St, Saint Michaels, MD
0.09
Single-Family Home
$1,000,000
02/13/26
2
2.5
1,445
204 Mulberry St, Saint Michaels, MD
0.09
Single-Family Home
$1,350,000
10/27/25
3
2.5
2,320
203 Mulberry St, Saint Michaels, MD
0.11
Single-Family Home
$926,000
01/15/26
3
2
1,740
408 Water St, Saint Michaels, MD
0.08
Single-Family Home
$995,000
10/08/25
3
2.5
1,893

Nearby home prices

Get a sense of expected prices in the area by checking the value of nearby homes.
Address
Distance
Price
Bed
Bath
Sqft
Status
106 E Chestnut St, Saint Michaels, MD 21663
0.02
$1,225,000
2
2.5
2,282
Recently Sold
408 Water St, Saint Michaels, MD 21663
0.08
$971,000
3
2.5
1,893
Off Market
202 E Chestnut St, Saint Michaels, MD 21663
0.08
$1,250,000
3
3
2,052
For Sale
417 Water St, Saint Michaels, MD 21663
0.10
$1,811,800
3
3.5
2,579
Off Market
104 Mulberry St, Saint Michaels, MD 21663
0.08
$1,470,000
3
2.5
1,938
For Sale
202 Mulberry St, Saint Michaels, MD 21663
0.09
$1,240,500
4
3
2,703
Off Market
504 Talbot St, Saint Michaels, MD 21663
0.07
$827,000
3
2.5
2,072
Off Market
204 Mulberry St, Saint Michaels, MD 21663
0.09
$1,318,700
3
2.5
2,320
Off Market
402 S Talbot St, St Michaels, MD 21663
0.07
-
2
1
1,608
Off Market
203 E Chew Ave, Saint Michaels, MD 21663
0.11
$2,125,000
5
5.5
4,673
Recently Sold
205 E Chew Ave, Saint Michaels, MD 21663
0.11
$1,175,000
2
1.5
1,780
Recently Sold

Local Information

  • Map ViewExplore the area around 107 E Chestnut St.
  • Schools1 Preschool School1 Elementary School1 Middle School1 High School
  • Shop & Eat
-- mins to
Commute Destination

Home Highlights

Property Type
Single-Family Home
Year Built
1880
Living Area
2,024 sqft
Price/Sqft
$561/sqft
Parking
Open Parking

About this House

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.
107 E Chestnut St, Saint Michaels, MD 21663 is a 2 bedroom, 2 bathroom, 2,024 sqft single-family home built in 1880. It last sold for $1,135,000 on Jul 27, 2026 (3% below the $1,165,000 asking price). This property is not currently displayed as for sale or rent on Trulia. The Trulia Estimate is $1,134,600, with a rent estimate of $2,371/month.
Last check for updates: about 9 hours ago
Listed by Monica Penwell, (410) 310-0225
TTR Sotheby's International Realty
Bought with: Pam Doll Ackermann, (410) 320-0366, RE/MAX Executive
Source: Bright MLS, MLS#MDTA2013968

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

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: $561/sqft
Status Change & Dates
Off Market Date: Mon Jul 27 2026Possession Timing: Close Of Escrow

Active Status

MLS Status: CLOSED

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

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 Automated Valuation Display: YSource Internet Consumer Comment: YSource Internet Entire Listing Display: YSource Internet Address Display: Y

Price and Tax history

DateEventPrice
Jul 27, 2026
Source: Bright MLS #MDTA2013968
Sold
$1,135,000
Jul 20, 2026
Source: Bright MLS #MDTA2013968
Pending
$1,165,000
Jun 30, 2026
Source: Bright MLS #MDTA2013968
Contingent
$1,165,000
Jun 11, 2026
Source: Bright MLS #MDTA2013968
Listed For Sale
$1,165,000
Jan 2, 2026
Source: Bright MLS #MDTA2011802
ListingRemoved
$1,195,000

Market trends in Saint Michaels

Last updated July 2026
Buyer'sMarketSeller'sMarket
Avg. sale price
—
Sale-to-List Price
—
Price per sq ft
—
Available listings
50
3MoM

Around this home

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
    "There are many dog friendly places and lost of nice outdoor spaces for walks. People are very comfortable around dogs here. "
    0
    Flag
  • Christopherbthomas24
    "Love this town, great spot for young families and retirees as well. Awesome spots to eat and hang out"
    2
    Flag
  • Kats0791
    "Different kinds of houses to chose from including single family, town homes & condos. New Pete Dye Golf Course. "
    0
    Flag
  • Janet S.
    "Work and live here. Fantastic area - beautiful, with great sailing. The town has constantly improved since I moved here in 1993."
    0
    Flag
  • rctdesign
    "Wonderful town with lots to do and very walkable!"
    0
    Flag

LGBTQ Local Legal Protections

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

Frequently asked questions about 107 E Chestnut St

  • What is 107 E Chestnut St estimated to be worth?
    Trulia's estimated value for 107 E Chestnut St in Saint Michaels, MD is $1,134,600.
  • What is the price history for 107 E Chestnut St?
    107 E Chestnut St in Saint Michaels, MD last sold for $1,135,000 in July 2026.
  • Is Saint Michaels a buyer's or seller's market?
    Saint Michaels is currently a buyer's market, based on recent for-sale activity.
  • What are the closest schools to 107 E Chestnut St?
    The closest schools to 107 E Chestnut St in Saint Michaels, MD are St. Michaels Elementary School (Pre-K, rated 8/10), St. Michaels Middle/High School (rated 6/10).
  • Does 107 E Chestnut St have air conditioning?
    Yes, 107 E Chestnut St in Saint Michaels, MD has air conditioning.
  • How big is the lot at 107 E Chestnut St?
    The lot at 107 E Chestnut St in Saint Michaels, MD is about 0.08 acres (3,600 sq ft).

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