205 Cherry St

St. Michaels, MD 21663

$2,575,000
Price
5
Beds
4,394 Sq. Ft.
$586 / Sq. Ft.
4,394
Sq. Ft.
$586
per Sq. Ft.
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Active Under Contract
Active Under Contract
a front view of a house with a yard
a front view of a house with a yard
a view of swimming pool with wooden deck and furniture
a view of swimming pool with a garden and plants
a view of a house with a yard from a balcony
Back Porch Looking Towards the Harbor
Relaxing on the Back Porch
Honeymoon Bridge and Harbor
St. Michaels Harbor
a view of a house with a big yard and potted plants
a view of outdoor space and yard
a front view of a house with a yard
a balcony with chairs and wooden floor
Hallway and Staircase
a view of water heater room
a living room with furniture a chandelier and a rug
a living room with furniture and a fireplace
a dining room with furniture and a fireplace
a view of a dining room with furniture large windows and wooden floor
a bedroom with bed and a fireplace
a living room with furniture and a mirror
a close view of a room with gym equipment
a bathroom with a double vanity sink mirror and bathtub
Upper Bedroom One
a bedroom with a large bed and a lamp on dresser
a bathroom with a granite countertop sink toilet and mirror
a bedroom with a bed a couch and dresser
a bed sitting in a bedroom next to a lamp
a living room with furniture fireplace and flat screen tv
a bathroom with a stove and a mirror
a bedroom with a bed and a television
Upper Bedroom Three
a living room with furniture and wooden floor
a bathroom with a sink and a toilet
Upper Bedroom Four
a bedroom with a bed and a dresser
a bedroom with a bed and dresser
a bedroom with furniture and a window
Bedroomn View of Harbor
a view of a chairs and table in the balcony
a view of balcony with wooden floor and outdoor seating
a front view of a house with garden
Guest Cottage Stairs to Second Floor Bedroom
a living room with furniture a window and wooden floor
a bedroom with a bed and a window
a bedroom with a bed and a chandelier
Guest Cottage Primary Bathroom
Guest Cottage Primary Bathroom
a bathroom with a sink and a mirror
a kitchen with a sink cabinets and window
a kitchen with a table chairs a sink and dishwasher
a view of a dining room with furniture window and wooden floor
a living room with furniture and a large window
a living room with furniture and a large window
a bedroom with a bed and a table in it
Guest Cottage Second Bedroom Area
a bathroom with a sink vanity and a mirror
a view of a patio with couches under an umbrella
a view of a patio with couches under an umbrella
a patio with patio a table and chairs under an umbrella
a view of a patio with couches and a umbrella
a picture of a wall with a white wall and a painting
Guest Cottage Floor Plan - Upper
a picture of a black and white photo

Description

205 Cherry Street is one of the most prestigious addresses in historic St. Michaels. Originally built as a single-family residence, it currently operates as an Inn. It is being marketed both as a 7 bedroom inn and also as a single family residence, offering 5 bedrooms (including the first floor primary bedroom suite). The original living room/office with fireplaces on the first floor are currently being used as bedrooms for the inn but can easily be converted back to living areas. (see virtual images...205 Cherry Street is one of the most prestigious addresses in historic St. Michaels. Originally built as a single-family residence, it currently operates as an Inn. It is being marketed both as a 7 bedroom inn and also as a single family residence, offering 5 bedrooms (including the first floor primary bedroom suite). The original living room/office with fireplaces on the first floor are currently being used as bedrooms for the inn but can easily be converted back to living areas. (see virtual images in photos). The beautiful front lawn provides a park-like setting with one-of-a-kind water-views overlooking St. Michaels Harbor. There is also a 2 bedroom, 2 bath guest cottage on the property. The property directly across the street (FKA The Hambeleton Inn) was purchased as a private residence and serves as a second home to its owner. This is a wonderful opportunity to own a landmark historic inn or primary or second home in the heart of St. Michaels.
  1. Listed by Robert D Lacaze • TTR Sotheby's International Realty
    P: (410)-310-7835 rlacaze@ttrsir.com

Property Details for 205 Cherry Street

Tax ID Number
2102065207
Ownership
Fee Simple
Condo Coop Association
No
HOA
No
Entry Floor Number
1
Structure Type
Detached
Style
Victorian, Colonial, Traditional
Levels/Stories
3
LISTING UPDATED: 05/03/2026 11:24 AM

Property Details for 205 Cherry Street

StatusActive Under Contract
MLS #MDTA2012738
Days on Market66
Taxes$23,653 / year
HOA Fees-
Condo/Co-op Fees-
Property TypeSingle Family
MLS TypeResidential / Fee Simple
Year Built1875
Lot Size0.73 AC / 31,801 SF
CountyTalbot County
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Location

Listing Courtesy of TTR Sotheby's International Realty
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Building Information for 205 Cherry Street

Stories3Year Built1875Building Size-Lot Size0.73 AC / 31,801 SF

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$14,803 per month

30 year fixed, 6.36% Interest

Principal and Interest

$12,832

Property Taxes

$1,971

HOA Dues

$0

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Property Information for 205 Cherry Street

Location
Location
  • In City Limits: Yes
  • School District Name: TALBOT COUNTY PUBLIC SCHOOLS
  • School District County ID: 121138072466
  • SchoolDistrictSource: Listing Agent
  • Elementary School: ST. MICHAELS (TALBOT MD)
  • ElementarySchoolSource: Listing Agent
  • Middle Or Junior School: ST. MICHAELS (TALBOT MD)
  • MiddleSchoolSource: Listing Agent
  • High School: ST. MICHAELS (TALBOT MD)
  • County: TALBOT
Waterfront / Water Access
Waterfront / Water Access
  • Water View: No
  • Water Access: Yes
  • Water Access Features: Canoe/Kayak, Public Access
  • Water Oriented: Yes
  • Navigable Water: No
  • Tidal Water: Yes
  • Water Body Type: River
  • Water Frontage In Feet: 200.0
  • Riparian Rights Y/N: Yes
  • Docks Count: 0
Association / Community Info
Association / Community Info
  • Property Manager Y/N: No
  • Senior Community: No
  • Association Recreation Fee Y/N: No
Taxes and Assessment
Taxes and Assessment
  • Tax Year: 2021
  • Tax Assessed Value: $1,891,767
  • Year Assessed: 2026
  • County Tax: $14,817
  • Improvement Assessed Value: $405,400
  • City Town Tax: $8,835
  • Land Assessed Value: $1,169,800
  • Clean Green Assessed: No
  • Land Use Code: 104
  • Loss Mitigation Fee: No
  • Agricultural Tax Due: No
  • Historic: Yes
  • Zoning: R2
  • Tax Lot: 31
  • Tax Page Number: 350
  • Automatically Update Tax Values Y/N: No
Lease Information
Lease Information
  • Pets Allowed: Yes
  • Pet Restrictions: No Pet Restrictions
Rooms
Main
  • # Bedrooms Count Main Level: 1
  • # Bathrooms Count Main Level: 4
  • # Bathrooms Full Main Level: 3
  • # Bathrooms Half Main Level: 1
All Upper Levels
  • # Bedrooms Count All Upper Levels: 4
  • # Bathrooms Count All Upper Levels: 4
  • # Bathrooms Full All Upper Levels: 4
Upper Level 1
  • # Bedrooms Count Upper Level: 4
  • # Bathrooms Count Upper Level: 4
  • # Bathrooms Full Upper Level: 4
All Lower Levels
  • # Bathrooms All Lower Levels: 1
  • # Bathrooms Full All Lower Levels: 1
Lower Level 1
  • # Bathrooms Lower Level: 1
  • # Bathrooms Full Lower Level: 1
Rooms
  • Room List: Living Room, Dining Room, Primary Bedroom, Bedroom 2, Bedroom 3, Bedroom 4, Kitchen, Family Room, Bedroom 1, Office, Bathroom 1, Bathroom 2, Bathroom 3, Full Bath
  • Stories: Lower 1, Main, Upper 1
Rooms Information
Room 1
  • Room Type: Bathroom 1
  • Room Level: Upper 1
  • Room Exists: Yes
Room 2
  • Room Type: Bathroom 2
  • Room Level: Upper 1
  • Room Exists: Yes
Room 3
  • Room Type: Bedroom 3
  • Room Level: Upper 1
  • Room Exists: Yes
Room 4
  • Room Type: Primary Bedroom
  • Room Level: Main
  • Room Exists: Yes
  • Room Features: Flooring - HardWood
Room 5
  • Room Type: Bedroom 1
  • Room Level: Upper 1
  • Room Exists: Yes
Room 6
  • Room Type: Bedroom 2
  • Room Level: Upper 1
  • Room Exists: Yes
Room 7
  • Room Type: Living Room
  • Room Level: Main
  • Room Exists: Yes
Room 8
  • Room Type: Office
  • Room Level: Main
  • Room Exists: Yes
Room 9
  • Room Type: Kitchen
  • Room Level: Main
  • Room Exists: Yes
Room 10
  • Room Type: Family Room
  • Room Level: Main
  • Room Exists: Yes
Room 11
  • Room Type: Dining Room
  • Room Level: Main
  • Room Exists: Yes
Room 12
  • Room Type: Bedroom 4
  • Room Level: Upper 1
  • Room Exists: Yes
Room 13
  • Room Type: Bathroom 3
  • Room Level: Upper 1
  • Room Exists: Yes
Room 14
  • Room Type: Full Bath
  • Room Level: Upper 1
  • Room Exists: Yes
Building Info
Building Info
  • Builder Name: Henry Clay Dodson
  • Year Major Reno Remodel: 1987
  • Building Level Count: 2
  • Total Finished SQFT: 4,394.00
  • Total Finished SQFT Source: Estimated
  • Total SQFT: 4,394.00
  • Total SQFT Source: Estimated
  • Elevators Count: 0
  • Main Entrance Orientation: Southwest
  • Construction Materials: Other, Wood Siding, Vinyl Siding
  • Roof: Slate, Architectural Shingle
  • Ext Main Mid-res: http://bright-media01.prd.brightmls.com/bright/images/0000/8044/7168/5224/804471685224_512_384_WM_CDD2uLd1i3iK1Gly.jpg
  • Wall and Ceiling Types: 9'+ Ceilings, High
  • Flooring Type: Hardwood
  • Basement Type: Other, Full
  • Foundation Details: Brick/Mortar, Concrete Perimeter
  • Room and Floor: Bedrooms-Main Level-1, Bathrooms Full-Main Level-1, Bathrooms Full-Main Level-2, Bathrooms Full-Main Level-3, Bathrooms Half-Main Level-1, Bedrooms-Upper Level 1-1, Bedrooms-Upper Level 1-2, Bedrooms-Upper Level 1-3, Bedrooms-Upper Level 1-4, Bathrooms Full-Upper Level 1-1, Bathrooms Full-Upper Level 1-2, Bathrooms Full-Upper Level 1-3, Bathrooms Full-Upper Level 1-4, Bathrooms Full-Lower Level 1-1
  • # Bathrooms Full: 8
  • # Bathrooms Half: 1
  • Other Structure: 2nd House
Lot / Land Information
Lot / Land Information
  • Lot Size Source: Estimated
  • Fencing: Partially
  • Additional Parcels: No
  • Ground Rent Exists: No
Parking
Parking
  • Type Of Parking: Driveway, Parking Lot
Interior Features
Interior Features
  • Interior Features: Built-Ins, Ceiling Fan(s), Kitchen - Eat-In, Kitchen - Table Space, Pantry, Sprinkler System, Wood Floors, Formal/Separate Dining Room, Primary Bedroom - Bay Front, Recessed Lighting, Stain/Lead Glass, Window Treatments
  • Fireplace: Yes
  • Fireplaces Count: 3
  • Fireplace Features: Gas/Propane, Wood
  • Appliances: Dishwasher, Disposal, Dryer, Oven - Self Cleaning, Oven/Range - Gas, Range Hood, Refrigerator, Stainless Steel Appliances, Washer, Water Heater, Extra Refrigerator/Freezer, Icemaker, Microwave
  • Accessibility Features: None
  • Laundry Type: Basement
Exterior Features
Exterior Features
  • Spa: No
  • Exterior Features: Flood Lights, Sidewalks
  • Outdoor Living Structures: Deck(s), Porch(es)
  • Pool: No Pool
Utilities
Utilities
  • Heating: Yes
  • Cooling Type: Heat Pump(s)
  • Cooling Fuel: Electric
  • Heating Type: Radiator
  • Heating Fuel: Oil
  • Hot Water: Multi-tank
  • Water Source: Public
  • Sewer Septic: Public Sewer
Confidential Data
Listing Office
  • List Agent AOR: Mid-Shore Board of REALTORS
  • List Agent URL: www.RobLacaze.com

Property History for 205 Cherry Street

DateEvent & SourcePriceAppreciation
May 2, 2026

Active Under Contract

BRIGHT #MDTA2012738

—
Feb 27, 2026

Listed (Active)

BRIGHT #MDTA2012738

$2,575,000—
Apr 22, 2022

Closed (Public Record)

Public Record #1488630257

$2,100,000—
DateEvent & SourcePrice
05/02/2026

Active Under Contract

BRIGHT #MDTA2012738

—
02/27/2026

Listed (Active)

BRIGHT #MDTA2012738

$2,575,000
04/22/2022

Closed (Public Record)

Public Record #1488630257

$2,100,000

For completeness, we often displays two records for one sale: the MLS record and the public record.

Public Records for 205 Cherry Street

Taxable ValueLand$1,169,800Additions$710,100Total$1,879,900
Tax Record2023$16,750 ($1,396 / month)
Home Facts
Baths8.5Total Finished SqFt3,200 SqFtAbove Grade Finished SqFt3,200 SqFtStories2Lot Size31,801 SqFtStyleOffice BuildingYear Built1875CountyTALBOTAPN02-065207Fireplace TypeHas Fireplace

Schools near 205 Cherry Street

This home is within Talbot County Public Schools.
Rating
School
Type
Grades
Distance
St. Michaels Elementary School
Public - PK to 5
St. Michaels Middle/High School
Public - 6 to 12
Easton High School
Public - 9 to 12
Rating
School
Distance
St. Michaels Elementary School
PublicPK to 5

St. Michaels Middle/High School
Public6 to 12

Easton High School
Public9 to 12

School ratings and boundaries are provided by GreatSchools.org and Pitney Bowes. This information should only be used as a reference. Proximity or boundaries shown here are not a guarantee of enrollment. Please reach out to schools directly to verify all information and enrollment eligibility.

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No guarantee, warranty or representation of any kind is made regarding the completeness or accuracy of descriptions or measurements (including square footage measurements and property condition), such should be independently verified, and Compass, Inc., its subsidiaries, affiliates and their agents and associated third parties expressly disclaims any liability in connection therewith. Photos may be virtually staged or digitally enhanced and may not reflect actual property conditions. Offers of compensation are subject to change at the discretion of the seller. No financial or legal advice provided. Equal Housing Opportunity. Subject to change at any time. Compass, Inc., its subsidiaries, affiliates and their agents and associated third parties make no guarantee, warranty or representation regarding the accuracy of any waterfront feature, water view or waterfront view.

Listing Courtesy of TTR Sotheby's International Realty

© 2026 Bright MLS. All rights reserved. All information is deemed reliable, but accuracy is not guaranteed. Listing information is from various brokers who participate in IDX and not all listings may be visible on the site. The property information being provided is for the consumer’s personal, non-commercial use and may not be used for any purpose other than to identify prospective properties consumers may be interested in purchasing. Data last updated on 05/03/2026 11:24 AM