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

$3,950,800

Trulia Estimate
  • 5 Beds
  • 4 Baths
  • 3,953 sqft (on 0.31 acres)

217 E Chestnut St, Saint Michaels, MD 21663

Est. Refi. Payment $22,288/mo*
Refinance Your Home
Currently Off Market - Sold Jan 12, 2007 for $2,600,000

Home Value

Trulia Estimate
$3.95M
Since last month
Decreased$31K (-0.8%)
Since last year
Decreased$72K (-1.8%)
Since last sale
Increased$1M (+51.9%)
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 +44% in the last 10 years
MonthEstimated value
2026
August 2026$3.95M
August 2026$3.95M
July 2026$3.98M
June 2026$4.04M
May 2026$3.94M
April 2026$3.92M
March 2026$3.97M
February 2026$3.94M
January 2026$3.96M
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
216 E Chew Ave, Saint Michaels, MD
0.08
Single-Family Home
$1,522,000
08/28/26
4
3.5
3,575
203 E Chew Ave, Saint Michaels, MD
0.08
Single-Family Home
$2,125,000
08/05/26
5
5.5
4,673
703 Riverview Ter, Saint Michaels, MD
0.26
Single-Family Home
$3,200,000
08/28/26
4
5
3,100
222 E Chestnut St, Saint Michaels, MD
0.03
Single-Family Home
$1,825,000
08/10/26
3
2.5
2,284
205 Cherry St, Saint Michaels, MD
0.29
Single-Family Home
$2,500,000
08/20/26
5
8.5
4,394
408 Water St, Saint Michaels, MD
0.09
Single-Family Home
$995,000
10/08/25
3
2.5
1,893
204 Mulberry St, Saint Michaels, MD
0.13
Single-Family Home
$1,350,000
10/27/25
3
2.5
2,320
106 E Chestnut St, Saint Michaels, MD
0.14
Single-Family Home
$1,225,000
06/05/26
2
2.5
2,282
114 E Chew Ave, Saint Michaels, MD
0.12
Single-Family Home
$1,152,500
06/10/26
3
2.5
2,336
121 W Chestnut St, St Michaels, MD
0.32
Single-Family Home
$1,395,000
06/22/26
3
2.5
2,540

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
218 E Chestnut St, Saint Michaels, MD 21663
0.02
$1,925,400
4
4
2,639
Off Market
222 E Chestnut St, Saint Michaels, MD 21663
0.03
$1,825,000
3
2.5
2,284
Recently Sold
417 Water St, Saint Michaels, MD 21663
0.05
$1,811,800
3
3.5
2,579
Off Market
202 E Chestnut St, Saint Michaels, MD 21663
0.07
$1,250,000
3
3
2,052
For Sale
408 Water St, Saint Michaels, MD 21663
0.09
$971,000
3
2.5
1,893
Off Market
205 E Chew Ave, Saint Michaels, MD 21663
0.08
$1,175,000
2
1.5
1,780
Recently Sold
203 E Chew Ave, Saint Michaels, MD 21663
0.08
$2,125,000
5
5.5
4,673
Recently Sold
216 E Chew Ave, Saint Michaels, MD 21663
0.08
$1,522,000
4
3.5
3,575
Recently Sold
103 N Harbor Rd, St Michaels, MD 21663
0.12
$2,259,400
4
4.5
3,732
Off Market
204 Mulberry St, Saint Michaels, MD 21663
0.13
$1,318,700
3
2.5
2,320
Off Market
202 Mulberry St, Saint Michaels, MD 21663
0.13
$1,240,500
4
3
2,703
Off Market
203 Mulberry St, Saint Michaels, MD 21663
0.14
$926,000
3
2
1,740
Recently Sold

Local Information

  • Map ViewExplore the area around 217 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
1800
Lot Size
0.31 acres
Living Area
3,953 sqft
Price/Sqft
$999
Parking
Garage

About this House

This single-family home is located at 217 E Chestnut St, Saint Michaels, MD. 217 E Chestnut St is in Saint Michaels, MD and in ZIP code 21663. This property has 5 bedrooms, 4 bathrooms and approximately 3,953 sqft of floor space. This property has a lot size of 0.31 acres and was built in 1800.
217 E Chestnut St, Saint Michaels, MD 21663 is a 5 bedroom, 4 bathroom, 3,953 sqft single-family home built in 1800. It last sold for $2,600,000 on Jan 12, 2007. This property is not currently displayed as for sale or rent on Trulia. The Trulia Estimate is $3,950,800, with a rent estimate of $4,050/month.

Home Details for 217 E Chestnut St

Interior Features

Heating & Cooling
Heating: BaseboardAir ConditioningCooling System: CentralHeating Fuel: Baseboard
Levels, Entrance, & Accessibility
Stories: 3Floors: Hardwood
Interior Details
Types of Rooms: Dining Room
Appliances & Utilities
DishwasherDryerRefrigeratorWasher
Fireplace & Spa
Fireplace

Exterior Features

Exterior Home Features
Roof: Shake ShingleDeckExterior: OtherFoundation Type: PiersPatio
Pool
Pool
Parking & Garage
GarageParking: Garage

Property Information

Year Built
Year Built: 1800
Property Type / Style
Property Type: Single Family HomeArchitecture: Conventional

Community

Units in Building: 1

Lot Information

Lot Area: 0.31 acres

Price and Tax history

DateEventPrice
Oct 31, 2018
Source: Agent Provided
ListingRemoved
$2,995,000
Mar 1, 2018
Source: Agent Provided
Listed For Sale
$2,995,000
Dec 2, 2016
Source: Agent Provided
ListingRemoved
$2,995,000
Mar 30, 2016
Source: Agent Provided
Listed For Sale
$2,995,000
Jan 12, 2007
Source: N/A
Sold
$2,600,000

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 217 E Chestnut St

  • What is 217 E Chestnut St estimated to be worth?
    Trulia's estimated value for 217 E Chestnut St in Saint Michaels, MD is $3,950,800.
  • What is the price history for 217 E Chestnut St?
    217 E Chestnut St in Saint Michaels, MD last sold for $2,600,000 in January 2007.
  • 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 217 E Chestnut St?
    The closest schools to 217 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 217 E Chestnut St have air conditioning?
    Yes, 217 E Chestnut St in Saint Michaels, MD has air conditioning.
  • Does 217 E Chestnut St have a pool?
    Yes, 217 E Chestnut St in Saint Michaels, MD has a pool.

Explore by feature - Pet Friendly

Explore by feature - Air Conditioning

8 rentals with air conditioning in Saint Michaels, MD

Explore by feature - Washer/dryer

6 rentals with a washer/dryer in Saint Michaels, MD

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