Are yards well-kept in Saint Michaels, MD?

As of early 2026, 100% of users say yards are well-kept

Are the streets well-lit in Saint Michaels, MD?

As of early 2026, 100% of users say streets are well-lit

Is Saint Michaels, MD dog-friendly?

As of early 2026, 92% of users say it's dog friendly

Is Saint Michaels, MD quiet?

As of early 2026, 92% of users say it's quiet

Is a car needed in Saint Michaels, MD?

As of early 2026, 90% of users say car is needed

Is parking easy in Saint Michaels, MD?

As of early 2026, 82% of users say parking is easy

Is there wildlife in Saint Michaels, MD?

As of early 2026, 79% of users say there's wildlife

Does Saint Michaels, MD show holiday spirit?

As of early 2026, 75% of users say there's holiday spirit

Do kids play outside in Saint Michaels, MD?

As of early 2026, 73% of users say kids play outside

Would people walk alone at night in Saint Michaels, MD?

As of early 2026, 67% of users say people would walk alone at night

Is Saint Michaels, MD walkable to restaurants?

As of early 2026, 64% of users say it's walkable to restaurants

Are there community events in Saint Michaels, MD?

As of early 2026, 63% of users say there are community events

Are neighbors friendly in Saint Michaels, MD?

As of early 2026, 58% of users say neighbors are friendly

Is Saint Michaels, MD walkable to grocery stores?

As of early 2026, 50% of users say it's walkable to grocery stores

Does Saint Michaels, MD have sidewalks?

As of early 2026, 45% of users say there are sidewalks

Do residents of Saint Michaels, MD plan to stay at least 5 years?

As of early 2026, 40% of users say they plan to stay for at least 5 years

FOR SALE

202 E Chestnut St
Saint Michaels, MD 21663

3 Beds
3 Baths
2,052 sqft

$1,275,000

Est. Mortgage $7,103/mo*

Get Pre-Qualified

$1,275,000

Est. Mortgage $7,103/mo*

Get Pre-Qualified

3 Beds

3 Baths

2,052 sqft

Local Information

-- mins to

Commute Destination

Description

Known as the William J. Wrightson House, this distinguished circa 1897 residence in the heart of St. Michaels beautifully blends timeless elegance and refined architectural detail with the comforts and conveniences of modern living. Lovingly restored from top to bottom, the home has undergone extensive renovations and improvements, including all new HVAC systems, tankless hot water system, updated wiring, crawlspace encapsulation, new roof and gutters, recessed lighting, high-end appliances, three fully renovated baths, a custom butler’s pantry, complete interior and exterior painting, and new patio grading and drainage, among many others. A full list of improvements is available. Ideally situated just steps from the waterfront, marinas, boutique shops, waterfront dining, and renowned local restaurants, the property offers an exceptional in-town lifestyle in one of the Eastern Shore’s most beloved waterfront communities. Filled with natural light throughout, the beautiful 3BR/3BA residence showcases heart pine and yellow pine flooring, custom millwork, and thoughtfully renovated living spaces designed for both everyday comfort and effortless entertaining. The welcoming living room, anchored by a new gas fireplace/stove, flows seamlessly into a gracious formal dining room ideal for gatherings with family and friends. The gourmet kitchen features quartz countertops, top-tier appliances, abundant cabinetry, and custom built-ins, effortlessly combining style and functionality. At the rear of the home, a stunning sunroom addition serves as a true focal point, featuring vaulted ceilings, a shiplap accent wall, wet bar and custom butler’s pantry with beverage chiller and bar sink, custom built-ins, a renovated full bath, and French doors opening to the picturesque gardens and brick patio beyond. Upstairs, the comfortable primary suite offers a peaceful retreat, complemented by a luxurious bath with a clawfoot soaking tub, Carrara Bella marble flooring (in shower as well), custom antique vanity, and glass-enclosed walk-in shower. Two additional guest bedrooms and a beautifully renovated bath with marble tile flooring, granite-topped vanity, and Perrin & Rowe fixtures provide inviting accommodations for family and guests. The outdoor spaces are equally enchanting, highlighted by a stunning English garden filled with roses, crepe myrtles, and hydrangeas, all enclosed by a charming French Gothic lattice shadowbox fence, creating a private and storybook setting.

Home Highlights

Parking

Open Parking

Outdoor

Porch, Patio

A/C

Heating & Cooling

HOA

None

Price/Sqft

$621

Listed

26 days ago

Home Details for 202 E Chestnut St

Interior Features
Interior Details Number of Rooms: 12Types of Rooms: Primary Bedroom, Bedroom 2, Bedroom 3, Primary Bathroom, Dining Room, Foyer, Full Bath, Kitchen, Laundry, Living Room, Sun Florida Room
Beds & Baths Number of Bedrooms: 3Number of Bathrooms: 3Number of Bathrooms (full): 3Number of Bathrooms (main level): 1
Dimensions and Layout Living Area: 2052 Square Feet
Appliances & Utilities Utilities: PropaneAppliances: Dishwasher, Disposal, Refrigerator, Oven/Range - Gas, Dryer, Freezer, Oven, Range Hood, Washer, Washer/Dryer Stacked, Tankless Water Heater, Water HeaterDishwasherDisposalDryerLaundry: Main Level,Laundry RoomRefrigeratorWasher
Heating & Cooling Heating: Heat Pump,ElectricHas CoolingAir Conditioning: Ductless,Heat Pump,ElectricHas HeatingHeating Fuel: Heat Pump
Fireplace & Spa Number of Fireplaces: 1Fireplace: Free Standing, Gas/PropaneHas a FireplaceNo Spa
Gas & Electric Electric: 120/240V
Windows, Doors, Floors & Walls Window: Palladian, Transom, Screens, Window Treatments, Stain/Lead GlassDoor: Storm Door(s), French DoorsFlooring: Hardwood, Marble, Wood
Levels, Entrance, & Accessibility Stories: 2Levels: TwoAccessibility: NoneFloors: Hardwood, Marble, Wood
View Has a ViewView: Garden, Courtyard, Scenic Vista, Trees/Woods

Exterior Features
Exterior Home Features Roof: ShinglePatio / Porch: Porch, Patio, Brick, RoofFencing: Back Yard, Decorative, PrivacyOther Structures: Above Grade, Below Grade, OutbuildingExterior: Extensive HardscapeFoundation: Crawl SpaceNo Private Pool
Parking & Garage No CarportNo GarageNo Attached GarageHas Open ParkingParking: Public,On Street
Pool Pool: None
Frontage Responsible for Road Maintenance: City/CountyRoad Surface Type: PavedNot on Waterfront
Water & Sewer Sewer: Public Sewer
Finished Area Finished Area (above surface): 2052 Square Feet

Days on Market
Days on Market: 26

Property Information
Year Built Year Built: 1897Year Renovated: 2024
Property Type / Style Property Type: ResidentialProperty Subtype: Single Family ResidenceStructure Type: DetachedArchitecture: Traditional,Victorian
Building Construction Materials: Frame, Stick Built, Wood SidingNot a New Construction
Property Information Condition: ExcellentParcel Number: 2102066831

Price & Status
Price List Price: $1,275,000Price Per Sqft: $621
Status Change & Dates Possession Timing: Close Of Escrow

Active Status
MLS Status: ACTIVE

Location
Direction & Address City: SAINT MICHAELSCommunity: None Available
School Information Elementary School District: Talbot County Public SchoolsJr High / Middle School District: Talbot County Public SchoolsHigh School District: Talbot County Public Schools

Agent Information
Listing Agent Listing ID: MDTA2013714

Building
Building Area Building Area: 2052 Square Feet

Community
Not Senior Community

HOA
No HOA

Lot Information
Lot Area: 3567 sqft

Listing Info
Special Conditions: Standard

Offer
Listing Agreement Type: Exclusive Right To Sell

Business
Business Information Ownership: Fee Simple

Miscellaneous
Mls Number: MDTA2013714Municipality: Saint MichaelsAbove Grade Unfinished Area: 2052

Additional Information
Source Internet Entire Listing Display: Y

Last check for updates: about 22 hours ago

Listing courtesy of Laura Carney, (410) 310-3307

TTR Sotheby's International Realty, (410) 673-3344

Source: Bright MLS, MLS#MDTA2013714

Also Listed on Bright MLS.

Price History for 202 E Chestnut St

Date	Price	Event	Source
05/07/2026	$1,275,000	Listed For Sale	Bright MLS #MDTA2013714

08/12/2021	$710,000	Sold	Bright MLS #MDTA141450
Recording Date 08/12/2021 County Transfer Tax N/A Total Transfer Tax N/A
07/28/2021	$645,000	Pending	Bright MLS #MDTA141450

06/15/2021	$645,000	Contingent	Bright MLS #MDTA141450

06/12/2021	$645,000	Listed For Sale	Bright MLS #MDTA141450

11/30/2020	$589,000	ListingRemoved	Agent Provided

08/15/2020	$589,000	Listed For Sale	Agent Provided

12/21/2019	$610,000	ListingRemoved	Agent Provided

04/07/2019	$610,000	Listed For Sale	Agent Provided

10/02/2018	$645,000	ListingRemoved	Agent Provided

10/10/2017	$645,000	Listed For Sale	Agent Provided

05/07/1996	$206,000	Sold	N/A
Recording Date 05/07/1996 County Transfer Tax N/A Total Transfer Tax N/A

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Property Tax and Assessment

Year	2025
Tax
Assessment	$558,200

Home facts updated by county records

Comparable Sales for 202 E Chestnut St

Address	Distance	Property Type	Sold Price	Sold Date	Bed	Bath	Sqft
106 Grace St, Saint Michaels, MD	0.20	Single-Family Home	$775,000	12/02/25	3	1.5	2,068
504 Talbot St, Saint Michaels, MD	0.13	Single-Family Home	$850,000	07/31/25	3	2.5	2,072
408 Water St, Saint Michaels, MD	0.06	Single-Family Home	$995,000	10/08/25	3	2.5	1,893
204 W Chew Ave, Saint Michaels, MD	0.26	Single-Family Home	$660,000	09/16/25	3	2	1,500
204 Mulberry St, Saint Michaels, MD	0.11	Single-Family Home	$1,350,000	10/27/25	3	2.5	2,320
304 N Talbot St, St Michaels, MD	0.47	Single-Family Home	$785,000	10/15/25	3	2.5	2,028
207 Seymour Ave, Saint Michaels, MD	0.19	Single-Family Home	$800,000	11/17/25	4	3.5	1,983
109 W Chew Ave, Saint Michaels, MD	0.19	Single-Family Home	$662,500	07/18/25	3	2	1,824
205 E Chew Ave, Saint Michaels, MD	0.03	Single-Family Home	$1,175,000	11/14/25	2	1.5	1,780
901 S Talbot St, St Michaels, MD	0.24	Single-Family Home	$600,000	08/08/25	3	2	1,660

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Get a sense of prices in the area by checking nearby homes.

Skip to last item

OFF MARKET
Est. $1,696,600
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OCT 27, 2025
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Skip to first item

Additional Cost

Assigned Schools

These are the assigned schools for 202 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
Resident
5y ago
"There are many dog friendly places and lost of nice outdoor spaces for walks. People are very comfortable around dogs here. "
0
Flag
Christopherbthomas24
Resident
7y ago
"Love this town, great spot for young families and retirees as well. Awesome spots to eat and hang out"
2
Flag
Kats0791
Resident
7y ago
"Different kinds of houses to chose from including single family, town homes & condos. New Pete Dye Golf Course. "
0
Flag
Janet S.
11y ago
"Work and live here. Fantastic area - beautiful, with great sailing. The town has constantly improved since I moved here in 1993."
0
Flag
rctdesign
11y ago
"Wonderful town with lots to do and very walkable!"
0
Flag

LGBTQ Local Legal Protections

Laura Carney, TTR Sotheby's International Realty, (410) 673-3344

Agent Phone: (410) 310-3307

The data relating to real estate for sale on this website appears in part through the BRIGHT Internet Data Exchange program, a voluntary cooperative exchange of property listing data between licensed real estate brokerage firms, and is provided by BRIGHT through a licensing agreement. Listing information is from various brokers who participate in the Bright MLS IDX program and not all listings may be visible on the site. The property information being provided on or through the website is for the personal, non-commercial use of consumers and such information may not be used for any purpose other than to identify prospective properties consumers may be interested in purchasing. Some properties which appear for sale on the website may no longer be available because they are for instance, under contract, sold or are no longer being offered for sale. Property information displayed is deemed reliable but is not guaranteed. Copyright 2026 Bright MLS, Inc. Click here for more information

202 E Chestnut St, Saint Michaels, MD 21663 is a 3 bedroom, 3 bathroom, 2,052 sqft single-family home built in 1897. This property is currently available for sale and was listed by Bright MLS on May 7, 2026. The MLS # for this home is MLS# MDTA2013714.

202 E Chestnut St Saint Michaels, MD 21663

$1,275,000

$1,275,000

Local Information

Description

Home Highlights

Home Details for 202 E Chestnut St

Interior Features

Exterior Features

Days on Market

Property Information

Price & Status

Active Status

Location

Agent Information

Building

Community

HOA

Lot Information

Listing Info

Offer

Business

Miscellaneous

Additional Information

Price History for 202 E Chestnut St

Similar Homes You May Like

New Listings near 202 E Chestnut St

Property Tax and Assessment

Comparable Sales for 202 E Chestnut St

Nearby homes

Additional Cost

Assigned Schools

What Locals Say about Saint Michaels

LGBTQ Local Legal Protections

Housing

Employment

Public accommodations

202 E Chestnut St
Saint Michaels, MD 21663