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

$899,500

Trulia Estimate
  • Studio
  • 3 Baths
  • 2,067 sqft

116 E Chestnut St, Saint Michaels, MD 21663

Est. Refi. Payment $5,314/mo*
Refinance Your Home
Currently Off Market - Sold Sep 8, 1998 for $230,000

Home Value

Trulia Estimate
$900K
Since last month
Decreased$45K (-4.8%)
Since last year
Decreased$99K (-10%)
Since last sale
Increased$666K (+289.5%)
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 +89% in the last 10 years
MonthEstimated value
2026
November 2026$896K
October 2026$925K
September 2026$941K
August 2026$978K
July 2026$1.01M
June 2026$1.02M
May 2026$1.03M
April 2026$1M
March 2026$1.01M
February 2026$945K
January 2026$982K
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
206 E Chestnut St, Saint Michaels, MD
0.07
Single-Family Home
$1,000,000
09/16/26
3
2,032
114 E Chew Ave, Saint Michaels, MD
0.07
Single-Family Home
$1,152,500
06/10/26
3
2.5
2,336
107 E Chestnut St, Saint Michaels, MD
0.04
Single-Family Home
$1,135,000
10/07/26
2
2
2,024
106 Grace St, Saint Michaels, MD
0.15
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
203 Canton St, Saint Michaels, MD
0.24
Single-Family Home
$285,000
09/10/26
3
2
1,364
104 Cherry St, Saint Michaels, MD
0.28
Single-Family Home
$650,000
10/08/26
4
3
2,718
207 Seymour Ave, Saint Michaels, MD
0.21
Single-Family Home
$800,000
11/17/25
4
3.5
1,983
100 Grace St, Saint Michaels, MD
0.12
Single-Family Home
$1,000,000
02/13/26
2
2.5
1,445
205 E Chew Ave, Saint Michaels, MD
0.08
Single-Family Home
$1,175,000
11/14/25
2
1.5
1,780

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
108 E Chestnut St, Saint Michaels, MD 21663
0.01
$1,443,100
4
4
3,064
Off Market
110 E Chestnut St, Saint Michaels, MD 21663
0.01
$1,012,100
Studio
3
3,270
Off Market
106 E Chestnut St, Saint Michaels, MD 21663
0.02
$1,225,000
2
2.5
2,282
Recently Sold
111 Chestnut St W, Saint Michaels, MD 21663
0.02
$950,900
3
2.5
1,890
Off Market
111 E Chestnut St, Saint Michaels, MD 21663
0.02
$860,300
4
2.5
1,852
Off Market
114 E Chestnut St, Saint Michaels, MD 21663
0.02
$779,900
3
3
1,868
Off Market
112 E Chestnut St, Saint Michaels, MD 21663
0.02
$1,429,500
3
4
2,587
Off Market
109 E Chestnut St, Saint Michaels, MD 21663
0.03
$772,900
3
1.5
1,488
Off Market
109 E Chew Ave, Saint Michaels, MD 21663
0.03
$741,500
3
3
1,456
Off Market
107 E Chew Ave, Saint Michaels, MD 21663
0.03
$523,100
-
-
992
Off Market
410 Saint Marys Sq, Saint Michaels, MD 21663
0.03
$761,500
3
2.5
2,092
Off Market
104 E Chestnut St, St Michaels, MD 21663
0.03
$958,900
Studio
1
1,460
Off Market
107 E Chestnut St, Saint Michaels, MD 21663
0.04
$1,135,000
2
2
2,024
Recently Sold
105 E Chew Ave, Saint Michaels, MD 21663
0.04
$901,900
Studio
2
1,703
Off Market
105 E Chestnut St, Saint Michaels, MD 21663
0.04
$1,292,400
Studio
3
2,576
Off Market
103 E Chew Ave, Saint Michaels, MD 21663
0.04
$999,100
3
2.5
2,126
Off Market
410 Water St, Saint Michaels, MD 21663
0.04
$1,040,100
4
2
2,265
Off Market
205 E Chestnut St, Saint Michaels, MD 21663
0.04
$461,400
Studio
1
640
Off Market
201 E Chestnut St, St Michaels, MD 21663
0.04
$1,107,300
Studio
1
2,227
Off Market
115 E Chew Ave, Saint Michaels, MD 21663
0.04
$2,131,300
4
3.5
3,845
Off Market

Local Information

  • Map ViewExplore the area around 116 E Chestnut St.
  • Schools1 Preschool School1 Elementary School1 Middle School1 High School
  • Shop & Eat
-- mins to
Commute Destination

Home Highlights

Single-Family Home
Built in 1825
2,067 sqft
$435/sqft
Garage

About this House

This single-family home is located at 116 E Chestnut St, Saint Michaels, MD. 116 E Chestnut St is in Saint Michaels, MD and in ZIP code 21663. This property has 3 bathrooms and approximately 2,067 sqft of floor space. This property has a lot size of 4320 sqft and was built in 1825.
116 E Chestnut St, Saint Michaels, MD 21663 is a studio, 3 bathroom, 2,067 sqft single-family home built in 1825. It last sold for $230,000 on Sep 8, 1998. This property is not currently displayed as for sale or rent on Trulia. The Trulia Estimate is $899,500, with a rent estimate of $2,561/month.

Home Details for 116 E Chestnut St

Interior Features

Heating & Cooling
Heating: ElectricAir ConditioningHeating Fuel: Electric
Levels, Entrance, & Accessibility
Stories: 1.5
Fireplace & Spa
Fireplace

Exterior Features

Exterior Home Features
Roof: Shake ShingleExterior: OtherPatio
Parking & Garage
GarageParking: Garage

Property Information

Year Built
Year Built: 1825
Property Type / Style
Property Type: Single Family HomeArchitecture: Conventional

Community

Units in Building: 1

Lot Information

Lot Area: 4320 sqft

Price and Tax history

DateEventPrice
Sep 8, 1998
Source: N/A
Sold
$230,000

Market trends in Saint Michaels

Last updated October 2026
Buyer'sMarketSeller'sMarket
Avg. sale price
—
Sale-to-List Price
—
Price per sq ft
—
Available listings
44
2MoM
Sourced by Trulia Market Trends

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 116 E Chestnut St

  • What is 116 E Chestnut St estimated to be worth?
    Trulia's estimated value for 116 E Chestnut St in Saint Michaels, MD is $899,500.
  • What is the price history for 116 E Chestnut St?
    116 E Chestnut St in Saint Michaels, MD last sold for $230,000 in September 1998.
  • Is Saint Michaels a buyer's or seller's market?
    Saint Michaels is currently a balanced market, based on recent for-sale activity.
  • What are the closest schools to 116 E Chestnut St?
    The closest schools to 116 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).
  • How big is the lot at 116 E Chestnut St?
    The lot at 116 E Chestnut St in Saint Michaels, MD is about 0.10 acres (4,320 sq ft).
  • Does 116 E Chestnut St have a garage?
    Yes, 116 E Chestnut St in Saint Michaels, MD has a garage.

Explore by feature - Pet Friendly

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Off Market Homes Near 116 E Chestnut St

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