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

111 E Chestnut St
Saint Michaels, MD 21663

  • 4 Beds
  • 2.5 Baths
  • 1,852 sqft

$947,600

Trulia Estimate
as of Jun 2, 2026
Est. Refi. Payment $5,298/mo*
Refinance Your Home

$947,600

Trulia Estimate
as of Jun 2, 2026
Est. Refi. Payment $5,298/mo*
Refinance Your Home
4 Beds
2.5 Baths
1,852 sqft

Local Information

Map showing home location
© Google
-- mins to
Commute Destination

Description

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.
This property is off market, which means it's not currently listed for sale or rent on Trulia. This may be different from what's available on other websites or public sources. This description is from March 22, 2026

Home Highlights

Parking
Attached Garage
Outdoor
No Info
A/C
Heating & Cooling
HOA
None
Price/Sqft
No Info
Listed
72 days ago

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

Price History for 111 E Chestnut St

DatePriceEventSource
04/12/2026$3,990ListingRemovedZillow Rentals
03/22/2026$3,990Listed For RentZillow Rentals
10/15/2025$2,990ListingRemovedZillow Rentals
09/03/2025$2,990PriceChange
Zillow Rentals
08/04/2025$3,490PriceChange
Zillow Rentals
06/23/2025$3,900PriceChange
Zillow Rentals
04/15/2025$4,490Listed For RentZillow Rentals
10/14/2024$3,950ListingRemovedZillow Rentals
07/29/2024ListingRemovedZillow Rentals
07/04/2024$3,950PriceChange
Zillow Rentals
05/08/2024$4,500PriceChange
Zillow Rentals
05/02/2024$4,800Listed For RentZillow Rentals
04/17/2024ListingRemovedZillow Rentals
03/22/2024$4,800Listed For RentZillow Rentals
06/05/2022ListingRemovedZillow Rental Manager
05/05/2022$4,950Listed For RentZillow Rental Manager
08/17/2020$549,900ListingRemovedAgent Provided
07/08/2020$549,900PriceChange
Agent Provided
07/08/2020$2,800ListingRemovedN/A
06/30/2020$2,800Listed For RentN/A
06/09/2020$589,000Listed For SaleAgent Provided
06/28/2019$2,200ListingRemovedAgent Provided
06/20/2019$2,200Listed For RentAgent Provided
06/20/2019$535,000ListingRemovedAgent Provided
08/13/2009$350,000Sold
N/A
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Property Tax and Assessment

Year2025
Tax
Assessment$499,100
Home facts updated by county records

Comparable Sales for 111 E Chestnut St

Address
Distance
Property Type
Sold Price
Sold Date
Bed
Bath
Sqft
103 Mulberry St, Saint Michaels, MD
0.10
Single-Family Home
$800,000
08/15/25
4
1.5
1,596
109 W Chew Ave, Saint Michaels, MD
0.14
Single-Family Home
$662,500
07/18/25
3
2
1,824
408 Water St, Saint Michaels, MD
0.06
Single-Family Home
$995,000
10/08/25
3
2.5
1,893
113 Thompson St, Saint Michaels, MD
0.15
Single-Family Home
$580,000
10/31/25
3
2
1,566
504 Talbot St, Saint Michaels, MD
0.08
Single-Family Home
$850,000
07/31/25
3
2.5
2,072
106 Grace St, Saint Michaels, MD
0.13
Single-Family Home
$775,000
12/02/25
3
1.5
2,068
203 Mulberry St, Saint Michaels, MD
0.11
Single-Family Home
$926,000
01/15/26
3
2
1,740
901 S Talbot St, St Michaels, MD
0.25
Single-Family Home
$600,000
08/08/25
3
2
1,660
204 W Chew Ave, Saint Michaels, MD
0.21
Single-Family Home
$660,000
09/16/25
3
2
1,500
702 Radcliff Ave, Saint Michaels, MD
0.29
Single-Family Home
$525,000
06/03/25
3
2
1,560

Nearby homes

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Assigned Schools

These are the assigned schools for 111 E Chestnut St.
View nearby schools on GreatSchools
The GreatSchools Rating compares schools on a variety of school quality indicators including test scores, college readiness, equity and more. Learn more.

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

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Apartments for Rent

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Homes for sale near 111 E Chestnut St

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Off Market Homes Near 111 E Chestnut St

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Homes for rent near 111 E Chestnut St

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111 E Chestnut St, Saint Michaels, MD 21663 is a 4 bedroom, 3 bathroom, 1,852 sqft single-family home. This property is not currently available for sale. 111 E Chestnut St was last sold on Aug 13, 2009 for $350,000 (8,672% higher than the asking price of $3,990). The current Trulia Estimate for 111 E Chestnut St is $947,600.