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$395,000

349 High St Chestertown, MD 21620

7 beds
3 full, 1 partial
3,664 sqft
0.1 acres
$108 / sqft
Townhouse

Property details

About 349 High St

A Rare Opportunity in the Heart of Historic Chestertown Discover a truly special offering in the vibrant core of Chestertown’s Historic and Arts & Entertainment Districts. Owned by the same family for over 50 years, this multi-family property sits on a generous double lot known historically as the Laurence Lots—featured on original town maps and steeped in local heritage. Brimming with character and potential, the property currently features a townhouse on one side and two apartments on the other, offering a flexible layout ideal for renovation, income generation, or a creative reimagining. Whether you're envisioning a stately single-family residence, a dynamic live/work space, or a thoughtfully restored multi-unit investment, the possibilities are as expansive as the lot itself. That said, this is not a turnkey property. Significant settling has occurred over the years, and a substantial renovation will be required to bring it back to life. Offered strictly as-is, this is a true fixer-upper for the visionary buyer ready to take on a transformative project. Situated within both the Arts & Entertainment District and Enterprise Zone, this location supports both residential and commercial uses—making it an ideal candidate for those looking to merge lifestyle, business, and history. Bring your vision, creativity, and tools—and seize the chance to breathe new life into a piece of Chestertown’s storied past. Opportunities like this don’t come along often. Schedule your showing today and imagine the future you can build here.

Highlights

Home typeTownhouse
HeatingRadiant
StatusActive
(ACTIVE)
CoolingWindow Unit(s)
Size3,664 sqft
Lot size0.13 Acres
Year built1900
ParkingOn Street
MLS #MDKE2004076

Summary

  • Partial Bathrooms: 1
  • Full Bathrooms: 3
  • Basement: No
  • Total Bedroom Count: 7
  • Parking: On Street
  • Architectural Style: Victorian
  • Heating: Radiant
  • Cooling: Window Unit(s)
  • List Price: $395,000
  • Price/SqFt: $107
  • Annual Tax Amount: $5,442
  • Tax Year: 2024
  • Directions: Rt 213N - L on Spring, R on High St, property on L
  • Year Built: 1900
  • Stories: 3
  • Living Area: 3,664 SqFt
  • Municipality: Chestertown
  • Lot Size: 0.13 Acres
  • MLS Number: MDKE2004076
  • MLS Name: BRIGHT
  • Office Name: Coldwell Banker Chesapeake Real Estate Company
  • Office Phone: (410) 778-0330
  • Listing Agent: Cheryl Hurt
  • Agent Phone: (619) 755-7730
  • Agent Email: cherylh@cbchesapeake.com

IDX Information Deemed Reliable But Not Guaranteed. 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 in which participates, and is provided by BRIGHT through a licensing agreement.

The information provided by this website is for the personal, non-commercial use of consumers and 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 this website may no longer be available because they are under contract, have sold or are no longer being offered for sale. Some real estate firms do not participate in IDX and their listings do not appear on this website. Some properties listed with participating firms do not appear on this website at the request of the seller. This home sale information is not to be construed as an appraisal and may not be used as such for any purpose.

BRIGHT MLS is the (or a) provider of this home sale information and has compiled content from various sources. Some properties represented may not have actually sold due to reporting errors. ©2025 BrightMLS. All rights reserved.
Data displayed may be a portion of, and not a complete set of all listings published in the MLS.
Last updated on: 7/23/2025, 4:45:28 AM Eastern. If you have any questions regarding the accuracy of this data, please contact us at help@rockethomes.com.

Price information

Property sales

We're sorry, we currently don't have property sales data for this listing.

Tax history

YearAssessmentProperty Tax
2024$347,267$5,442
2023$336,133$5,060
2022$325,000$5,060
2021$324,167$5,067
2020$323,333$5,067
2019$322,500$5,043
2018$322,500$5,011
2017$322,500$4,850

History based on county public records data.

Nearby schools

4

Henry Highland Garnet Elementary School

Public District PK-5

0.2 mi

320 Calvert St

7

Church Hill Elementary School

Public District PK-4

6.4 mi

631 Main St

7

Rock Hall Elementary School

Public District PK-5

10.4 mi

21203 W Sharp St

School ratings are a score out of 10, where 10 is the highest and 1 is the lowest.

All data from GreatSchools

Neighborhood

The neighbors living near this home have an average income of $41,287. The majority of Chestertown, MD residents have income less than $<35k annually. The most common type of family is single, no kids. The most common level of education of people living in this area is post secondary degree.

How much money do the neighbors make?

44%
<35k
32%
35k-100k
13%
100k-200k
11%
200k+

What level of education do the neighbors have?

High School Diploma
Post Secondary Degree
Masters Degree
Doctorate

What types of families live nearby?

64%
Single, No Kids
8%
Single, with Kids
24%
Married, No Kids
4%
Married, with Kids

Are the neighbors home owners or renters?

Home Owners
Renters

How old are people in this area?

7%
<11 yrs old
4%
12-17 yrs old
30%
18-34 yrs old
37%
35-64 yrs old
22%
65+ yrs old

What do the neighbors do for fun?

  • Pro WrestlingPro Wrestling
  • PGA/LPGAPGA/LPGA
  • College FootballCollege Football

Where do the neighbors shop?

  • Family DollarFamily Dollar
  • Stein MartStein Mart
  • Express/Express For MenExpress/Express For Men

Where do the neighbors go to eat?

  • Dominos PizzaDominos Pizza
  • Bob EvansBob Evans
  • SonicSonic

What do the neighbors drive?

  • FordFord
  • LincolnLincoln
  • KiaKia

What do the neighbors listen to?

  • New CountryNew Country
  • News/Talk/InformationNews/Talk/Information
  • OldiesOldies
All data provided by Home Junction and Claritas

Frequently asked questions

About 349 High St

The listing price of 349 High St property is $395,000.

The property 349 High St is a townhouse located in Chestertown, Maryland, 21620.

Active Listing: 349 High St is For Sale (Active/New) which means the seller is accepting offers.

The nearby schools for 349 High St are: Henry Highland Garnet Elementary School (GreatSchools Rating 4/10), Church Hill Elementary School (GreatSchools Rating 7/10), Rock Hall Elementary School (GreatSchools Rating 7/10), Kent County Middle School (GreatSchools Rating 3/10), Sudlersville Middle School (GreatSchools Rating 5/10), Centreville Middle School (GreatSchools Rating 7/10), Kent County High School (GreatSchools Rating 5/10), Queen Anne's County High School (GreatSchools Rating 8/10), Edgewood High School (GreatSchools Rating 4/10).

According to the records, the last property tax for 2024 is $5,442 (source: MLS/based on county public records data).

The property at 349 High St has 7 bedrooms and 3 full and 1 half bathrooms.

The property 349 High St is 3,664 SqFt (source: MLS/tax record).

The year of construction for 349 High St is 1900.

This home is located at 349 High St in Chestertown, MD and zip code 21620. This 3,664 square foot home, which was built in 1900, sits on a 0.13 acre lot. Features: 7 bedrooms, 4 bathrooms. It has been listed on Rocket Homes since June 3, 2024 and is currently priced at $395,000.

The number of homes for sale in Chestertown, MD increased by 44.2% between May and June 2025. While the average time on the market in June 2025 was 109 days, the median list price was $419,000.

From Rocket Homes Real Estate and based on county public records data.

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