537 High St
Chestertown, MD 21620
3 Beds
2.5 Baths
1,584 sqft
3 Beds
2.5 Baths
1,584 sqft
Homes for sale near 537 High St
Long & Foster Real Estate, Inc.- Chesapeake Real Estate Associates, LLC
- Coldwell Banker Chesapeake Real Estate Company
- 0.41 ACRESColdwell Banker Chesapeake Real Estate Company
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Apartments for Rent
- NEW - 9 HRS AGOPET FRIENDLY
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Local Information
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Description
This single-family home is located at 537 High St, Chestertown, MD. 537 High St is in Chestertown, MD and in ZIP code 21620. This property has 3 bedrooms, 3 bathrooms and approximately 1,584 sqft of floor space. This property has a lot size of 3249 sqft and was built in 1900.
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.
Home Highlights
Parking
No Info
Outdoor
Deck
A/C
Heating & Cooling
HOA
None
Price/Sqft
No Info
Listed
No Info
Home Details for 537 High St
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Interior Details BasementTypes of Rooms: Dining RoomCeiling Fan |
Heating & Cooling Heating: Heat PumpAir ConditioningCooling System: CentralHeating Fuel: Heat Pump |
Levels, Entrance, & Accessibility Stories: 3Floors: Hardwood |
Appliances & Utilities DishwasherMicrowaveRefrigerator |
Fireplace & Spa Fireplace |
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Exterior Home Features Roof: MetalDeckExterior: Other |
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Year Built Year Built: 1900 |
Property Type / Style Property Type: Single Family HomeArchitecture: Conventional |
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Units in Building: 1 |
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Lot Area: 3249 sqft |
Price History for 537 High St
| Date | Price | Event | Source |
|---|---|---|---|
| 07/21/2020 | $300,000 | Sold | N/A |
| 06/15/2020 | $310,000 | Pending | Agent Provided |
| 02/27/2020 | $310,000 | PriceChange | Agent Provided |
| 12/10/2019 | $325,000 | Listed For Sale | Agent Provided |
| 07/31/2018 | $65,000 | Sold | N/A |
| 06/14/2018 | $25,000 | PriceChange | Agent Provided |
| 04/30/2018 | $50,000 | PriceChange | Agent Provided |
| 03/01/2018 | $119,900 | PriceChange | Agent Provided |
| 01/06/2018 | $124,000 | Listed For Sale | Agent Provided |
| 10/24/2017 | $64,378 | Sold | N/A |
| 07/02/1998 | $104,500 | Sold | N/A |
| 03/09/1998 | $37,000 | Sold | N/A |
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Property Tax and Assessment
| Year | 2025 |
|---|---|
| Tax | $9,027 |
| Assessment | $288,000 |
Home facts updated by county records
Comparable Sales for 537 High St
Address | Distance | Property Type | Sold Price | Sold Date | Bed | Bath | Sqft |
|---|---|---|---|---|---|---|---|
0.22 | Single-Family Home | $490,000 | 05/21/25 | 2 | 2.5 | 1,476 | |
0.16 | Single-Family Home | $350,000 | 07/18/25 | 2 | 2 | 1,080 | |
0.26 | Single-Family Home | $410,000 | 07/08/25 | 4 | 2 | 1,656 | |
0.09 | Single-Family Home | $150,000 | 06/06/25 | 3 | 3 | 2,240 | |
0.08 | Single-Family Home | $230,000 | 02/02/26 | 2 | 1 | 928 | |
0.47 | Single-Family Home | $575,000 | 06/06/25 | 3 | 2.5 | 2,296 | |
0.48 | Single-Family Home | $240,000 | 08/26/25 | 2 | 2 | 1,218 | |
0.20 | Single-Family Home | $120,000 | 02/27/26 | 4 | 1.5 | 1,156 | |
0.19 | Single-Family Home | $695,000 | 11/05/25 | 3 | 3.5 | 2,492 | |
0.44 | Single-Family Home | $600,000 | 05/16/25 | 5 | 2.5 | 2,536 |
Assigned Schools
These are the assigned schools for 537 High St.
- H. H. Garnett Elementary School
- PK-5
- Public
- 347 Students
7/10GreatSchools RatingParent Rating AverageA great school with dedicated teachers and staff and a warm, friendly feel. Principal Rose is engaged and knows all of her students, and Miss Kiki at the front desk is great for answering questions and getting things done. I've had three older kids go through the school and they still reminisce about it, and my youngest is in first grade and loves going to school every day. He is sometimes even disappointed when school is closed for holidays! I could not ask for more in a positive and engaging early experience with learning. This is a great little school that gets a bad rap for test scores, but the truth is our student population has a high level of need that our teachers and staff have to go above and beyond to meet. My only complaint is that they don't get paid enough for all they do for their kids and there aren't enough of them to keep them from being completely overworked all the time. They are real heroes.Parent Review2y ago - Kent County Middle School
- 6-8
- Public
- 399 Students
2/10GreatSchools RatingParent Rating Average
No reviews available for this school. - Kent County High School
- 9-12
- Public
- 531 Students
5/10GreatSchools RatingParent Rating AverageThe school offers STEM academy, Dual enrollment & Career Pathways. It’s a great school, you just have to do a bit of research for the programs offered.Parent Review1y ago 
Check out schools near 537 High St.
What Locals Say about Chestertown
At least 34 Trulia users voted on each feature.
85 % Say car is needed
84 % Say there's holiday spirit
83 % Say it's dog friendly
77 % Say people would walk alone at night
77 % Say parking is easy
76 % Say yards are well-kept
74 % Say it's quiet
61 % Say neighbors are friendly
57 % Say there's wildlife
56 % Say it's walkable to restaurants
54 % Say there are sidewalks
49 % Say kids play outside
46 % Say it's walkable to grocery stores
44 % Say streets are well-lit
41 % Say there are community events
38 % Say they plan to stay for at least 5 years
Learn more about our methodology.
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Homes for rent near 537 High St
- APPLY INSTANTLYPET FRIENDLY
- NEW - 9 HRS AGOPET FRIENDLY
- PET FRIENDLY
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Off Market Homes Near 537 High St
- SOLDAPR 17, 2026Cross Street Realtors LLC
- SOLDAPR 17, 2026Cross Street Realtors LLC
- SOLDAPR 17, 2026Doug Ashley Realtors, LLC
- SOLDAPR 17, 2026Chesapeake Real Estate Associates, LLC
- SOLDAPR 14, 2026Cummings & Co. Realtors
- SOLDAPR 13, 2026Chesapeake Real Estate Associates, LLC
- SOLDAPR 8, 2026Integrity Real Estate
- SOLDMAR 31, 2026Chesapeake Real Estate Associates, LLC
- SOLDMAR 31, 2026Coldwell Banker Chesapeake Real Estate Company
- See more homes for sale inChestertown
537 High St, Chestertown, MD 21620 is a 3 bedroom, 3 bathroom, 1,584 sqft single-family home built in 1900. This property is not currently available for sale. 537 High St was last sold on Jul 21, 2020 for $300,000. The current Trulia Estimate for 537 High St is $385,200.