111 E Chestnut St, Saint Michaels, MD 21663
Kitchen leading out to the courtyard, easy access for BBQ parties.
Upstairsl bedroom #2 - corner bedroom with large windows, views of the front street and St. Michaels Museum.
OFF MARKET

$914,000

Trulia Estimate
as of Aug 29, 2026
  • 4 Beds
  • 2.5 Baths
  • 1,852 sqft
  • 4 Beds
  • 2.5 Baths
  • 1,852 sqft

111 E Chestnut St, Saint Michaels, MD 21663

Home Highlights

Property Type
Single-Family Home
Living Area
1,852 sqft
Price/Sqft
$494
Parking
Attached Garage

Local Information

  • Map ViewExplore the area around 111 E Chestnut St.
  • Schools1 Preschool School1 Elementary School1 Middle School1 High School
  • Shop & Eat
-- mins to
Commute Destination

About this House

Historic Home for Long-Term Lease in Vibrant St. Michaels - 111 E. Chestnut St, St. Michaels, MD 21663

Discover a charming, historic home on the corner of East Chestnut Street and St. Mary's Square, perfect for a single person, young couple, or family seeking a year-round retreat in St. Michaels. Carefully preserved and updated, this residence blends timeless character with practical comforts, offering a serene base in the heart of a lively waterfront town.

This house is an ideal home for you:

Walkable Lifestyle: Steps from St. Michaels Harbor, world-class restaurants, boutique shops, and cultural treasures like the Chesapeake Bay Maritime Museum and St. Michaels Museum (across the street). Enjoy quiet privacy despite the central location.
Outdoor Adventures: Enjoy sailing summer camps, yacht racing, or log canoe racing at the Chesapeake Bay Maritime Museum, Miles River Yacht Club, or Tred Avon Yacht Club. Bike or jog the St. Michaels Nature Trail, or tee off at premier golf courses like Links at Perry Cabin (a Pete Dye design), Hog Neck Golf Course, or Blue Heron Golf Course.

Community Gems: Unwind at Muskrat Park's harbor gazebo (0.5 acres), explore Hollis Park's pirate ship playground (1.9 acres), or reflect at Frederick Douglass Park's historic kiosk (0.1 acres). Clint S. Bradley Park (2 acres) offers play structures, while Canton Farm Nature Preserve (40 acres) beckons nature lovers.

Work & Play: High-speed Wi-Fi and cable make remote work seamless ideal for museum staff, freelancers, or nearby employers. Celebrate your special events at the five-star Inn at Perry Cabin or nearby four-star hotels and restaurants with your friends and family.

Seasonal Delights: St. Michaels offers year-round activities. Summer buzzes with sailing and festivals; winter events are full of joy and happiness. Or just wrap yourself in cozy charm with tree-lined streets glowing under old-fashioned lamp posts, visible from every upstairs bedroom.

Home Features:

Rare Private Garage: A St. Michaels rarity, with pantry access for easy grocery unloading.

Inviting Kitchen: Granite countertops of the highest grade, stainless steel appliances, propane range, and ample cabinets for cozy meals.

Private Fenced Courtyard: Relax by the BBQ grill or fire pit, or grow a small garden a tranquil haven.

Flexible Layout: Four bedrooms, including a first-floor master suite tied to the family room. Three upstairs rooms, each framing the picturesque street, double as offices or a gym.

Lease Details:

Perfect for year-round living in a high-demand area.

Dog-friendly! St. Michaels welcomes pups with water bowls at shops, restaurants, and ample dog-walking paths along parks, trails, brick sidewalks, and quiet streets.

This home is your gateway to St. Michaels' tight-knit community, rich history, and endless activities from sailing to golfing to savoring local flavors. Whether you're working remotely or raising a family, settle into a space where every season shines.

Contact Us to Secure Your Lease Today!

Tenant pays utilities: electricity, water, sewer, propane, and optional cable.

Tenant takes care of the landscaping of the front, side, and courtyard.

We suggest that you obtain renters insurance.
111 E Chestnut St, Saint Michaels, MD 21663 is a 4 bedroom, 3 bathroom, 1,852 sqft single-family home. It last sold for $350,000 on Aug 13, 2009 (8,672% above the $3,990 asking price). More recently, it was listed as a rental in March 2026 with an asking price of $3,990 per month. That rental listing was removed on April 12, 2026. This property is not currently displayed as for sale or rent on Trulia. The Trulia Estimate is $914,000, with a rent estimate of $2,900/month.

Home Details for 111 E Chestnut St

Interior Features

Heating & Cooling
Heating: Baseboard, Forced Air, Heat Pump, Wall FurnaceAir ConditioningCooling System: Central AirHeating Fuel: Baseboard
Appliances & Utilities
DishwasherDryerMicrowaveRefrigeratorWasher
Levels, Entrance, & Accessibility
Floors: Hardwood, Tile

Property Information

Property Type / Style
Property Type: Single Family Home

Rental Terms, Policies & Fees

Lease Term: 1 YearAvailable: now

Exterior Features

Parking & Garage
GarageParking: Attached Garage Off Street, On Site

Comparable Sales for 111 E Chestnut St

Address
Distance
Property Type
Sold Price
Sold Date
Bed
Bath
Sqft
408 Water St, Saint Michaels, MD
0.06
Single-Family Home
$995,000
10/08/25
3
2.5
1,893 sqft
113 Thompson St, Saint Michaels, MD
0.15
Single-Family Home
$580,000
10/31/25
3
2
1,566 sqft
106 Grace St, Saint Michaels, MD
0.13
Single-Family Home
$775,000
12/02/25
3
1.5
2,068 sqft
203 Mulberry St, Saint Michaels, MD
0.11
Single-Family Home
$926,000
01/15/26
3
2
1,740 sqft
204 W Chew Ave, Saint Michaels, MD
0.21
Single-Family Home
$660,000
09/16/25
3
2
1,500 sqft
113 Gloria Ave, Saint Michaels, MD
0.26
Single-Family Home
$539,500
06/30/26
3
2
1,456 sqft
207 Seymour Ave, Saint Michaels, MD
0.23
Single-Family Home
$800,000
11/17/25
4
3.5
1,983 sqft
114 E Chew Ave, Saint Michaels, MD
0.10
Single-Family Home
$1,152,500
06/10/26
3
2.5
2,336 sqft
107 E Chestnut St, Saint Michaels, MD
0.02
Single-Family Home
$1,135,000
07/27/26
2
2
2,024 sqft
204 Mulberry St, Saint Michaels, MD
0.09
Single-Family Home
$1,350,000
10/27/25
3
2.5
2,320 sqft

Nearby homes

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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

Price and Tax history

DateEventPrice
Apr 12, 2026
Source: Zillow Rentals
ListingRemoved
$3,990
Mar 22, 2026
Source: Zillow Rentals
Listed For Rent
$3,990
Oct 15, 2025
Source: Zillow Rentals
ListingRemoved
$2,990
Sep 3, 2025
Source: Zillow Rentals
PriceChange
$2,990
Price decreased by 14%
Aug 4, 2025
Source: Zillow Rentals
PriceChange
$3,490
Price decreased by 11%

Frequently asked questions about 111 E Chestnut St

  • What is 111 E Chestnut St estimated to be worth?
    Trulia's estimated value for 111 E Chestnut St in Saint Michaels, MD is $914,000.
  • What is the price history for 111 E Chestnut St?
    111 E Chestnut St in Saint Michaels, MD last sold for $350,000 in August 2009.
  • 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 111 E Chestnut St?
    The closest schools to 111 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 111 E Chestnut St have air conditioning?
    Yes, 111 E Chestnut St in Saint Michaels, MD has air conditioning.
  • Does 111 E Chestnut St have laundry facilities?
    Yes, 111 E Chestnut St in Saint Michaels, MD has in-unit laundry.

Homes for rent near 111 E Chestnut St

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Affordability

TIP:Try to keep your rent within a third of your gross household income. Learn why in our Renter's Guide.
For this property
PER YEAR
is the suggested income
Win over prospective landlords with your smart budgeting. As a good rule of thumb, ideally you would have at least three times your monthly rent in combined household income.
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