108 E Chestnut St, Saint Michaels, MD 21663
OFF MARKET

$1,513,900

Trulia Estimate
  • 4 Beds
  • 4 Baths
  • 3,064 sqft

108 E Chestnut St, Saint Michaels, MD 21663

Est. Refi. Payment $8,667/mo*
Refinance Your Home
Currently Off Market - Sold Dec 14, 2012 for $767,000

Home Value

Trulia Estimate
$1.51M
Since last month
Decreased$45K (-2.9%)
Since last year
Decreased$51K (-3.3%)
Since last sale
Increased$744K (+97%)
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 +82% in the last 10 years
MonthEstimated value
2026
August 2026$1.51M
July 2026$1.56M
June 2026$1.56M
May 2026$1.56M
April 2026$1.55M
March 2026$1.56M
February 2026$1.51M
January 2026$1.52M
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
408 Water St, Saint Michaels, MD
0.08
Single-Family Home
$995,000
10/08/25
3
2.5
1,893
207 Seymour Ave, Saint Michaels, MD
0.21
Single-Family Home
$800,000
11/17/25
4
3.5
1,983
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
0.07
Single-Family Home
$1,152,500
06/10/26
3
2.5
2,336
203 Mulberry St, Saint Michaels, MD
0.13
Single-Family Home
$926,000
01/15/26
3
2
1,740
204 Mulberry St, Saint Michaels, MD
0.11
Single-Family Home
$1,350,000
10/27/25
3
2.5
2,320
121 W Chestnut St, St Michaels, MD
0.19
Single-Family Home
$1,395,000
06/22/26
3
2.5
2,540
203 W Chew Ave, Saint Michaels, MD
0.19
Single-Family Home
$1,382,500
09/29/25
4
5
2,048
222 E Chestnut St, Saint Michaels, MD
0.15
Single-Family Home
$1,825,000
08/10/26
3
2.5
2,284
100 Grace St, Saint Michaels, MD
0.12
Single-Family Home
$1,000,000
02/13/26
2
2.5
1,445

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
107 E Chestnut St, Saint Michaels, MD 21663
0.04
$1,135,000
2
2
2,024
Recently Sold
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
-
3
2.5
1,893
Off Market
202 E Chestnut St, Saint Michaels, MD 21663
0.06
$1,250,000
3
3
2,052
For Sale
115 W Chew Ave, Saint Michaels, MD 21663
0.05
$1,011,300
4
2.5
1,781
Off Market
417 Water St, Saint Michaels, MD 21663
0.08
$1,823,700
3
3.5
2,579
Off Market
104 Mulberry St, Saint Michaels, MD 21663
0.11
$1,470,000
3
2.5
1,938
For Sale
202 Mulberry St, Saint Michaels, MD 21663
0.11
-
4
3
2,703
Off Market
504 Talbot St, Saint Michaels, MD 21663
0.07
-
3
2.5
2,072
Off Market
204 Mulberry St, Saint Michaels, MD 21663
0.11
-
3
2.5
2,320
Off Market
402 S Talbot St, St Michaels, MD 21663
0.11
-
2
1
1,608
Off Market
203 E Chew Ave, Saint Michaels, MD 21663
0.07
$2,125,000
5
5.5
4,673
Recently Sold

Local Information

  • Map ViewExplore the area around 108 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
1840
Living Area
3,064 sqft
Price/Sqft
$494

About this House

This single-family home is located at 108 E Chestnut St, Saint Michaels, MD. 108 E Chestnut St is in Saint Michaels, MD and in ZIP code 21663. This property has 4 bedrooms, 4 bathrooms and approximately 3,064 sqft of floor space. This property has a lot size of 9720 sqft and was built in 1840.
108 E Chestnut St, Saint Michaels, MD 21663 is a 4 bedroom, 4 bathroom, 3,064 sqft single-family home built in 1840. It last sold for $767,000 on Dec 14, 2012. This property is not currently displayed as for sale or rent on Trulia. The Trulia Estimate is $1,513,900, with a rent estimate of $3,384/month.

Home Details for 108 E Chestnut St

Interior Features

Heating & Cooling
Heating: Heat Pump, Electric, GasAir ConditioningCooling System: CentralHeating Fuel: Heat Pump
Levels, Entrance, & Accessibility
Stories: 2Floors: Hardwood
Interior Details
AtticNumber of Rooms: 10Types of Rooms: Walk In Closet, Dining Room, Family Room, Laundry Room, Master Bath, Mud Room
Appliances & Utilities
Cable ReadyDishwasherDryerMicrowaveRefrigeratorWasher
Fireplace & Spa
FireplaceHot Tub or Spa

Exterior Features

Exterior Home Features
Roof: Shake ShingleExterior: OtherLawnPatioPorch
Pool
Pool

Property Information

Year Built
Year Built: 1840Year Updated: 2004
Property Type / Style
Property Type: Single Family HomeArchitecture: Conventional

Community

Units in Building: 1

Lot Information

Lot Area: 9720 sqft

Price and Tax history

DateEventPrice
Dec 14, 2012
Source: N/A
Sold
$767,000
Aug 30, 2007
Source: N/A
Sold
$845,000
Oct 29, 2004
Source: N/A
Sold
$850,000
Oct 4, 2001
Source: N/A
Sold
$400,000

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

Frequently asked questions about 108 E Chestnut St

  • What is 108 E Chestnut St estimated to be worth?
    Trulia's estimated value for 108 E Chestnut St in Saint Michaels, MD is $1,513,900.
  • What is the price history for 108 E Chestnut St?
    108 E Chestnut St in Saint Michaels, MD last sold for $767,000 in December 2012.
  • 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 108 E Chestnut St?
    The closest schools to 108 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 108 E Chestnut St have air conditioning?
    Yes, 108 E Chestnut St in Saint Michaels, MD has air conditioning.
  • Does 108 E Chestnut St have a pool?
    Yes, 108 E Chestnut St in Saint Michaels, MD has a pool.

Explore by feature - Air Conditioning

6 rentals with air conditioning in Saint Michaels, MD

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Off Market Homes Near 108 E Chestnut St

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