533 Round Top Road

Coming Soon
Coming Soon
Gallery Image 1
Coming Soon
$225,000
4 beds1,800 sqft$125/sqft
533 Round Top Rd, Chestertown, MD 21620
Est: $1,322/moGet pre-approved
Single FamilyProperty Type
0.55 acresLot Size
1962Year Built
$125/sq ftPrice per sq ft
1 carParking Spaces

Description

Introducing this spacious 4-bedroom, 1.5-bath ranch on an extra-wide fenced lot in the Chester Harbor community, just minutes from historic Chestertown. Offering comfortable single-level living, the home features a large family room, an expansive kitchen with abundant cabinet and counter space, and a functional floor plan ready for your personal updates and vision. Whether you’re looking for your next home, an investment opportunity, or a property to renovate and build equity, this home offers exceptional...Introducing this spacious 4-bedroom, 1.5-bath ranch on an extra-wide fenced lot in the Chester Harbor community, just minutes from historic Chestertown. Offering comfortable single-level living, the home features a large family room, an expansive kitchen with abundant cabinet and counter space, and a functional floor plan ready for your personal updates and vision. Whether you’re looking for your next home, an investment opportunity, or a property to renovate and build equity, this home offers exceptional potential. The generous layout includes four bedrooms, one full bath, one half bath, and flexible space for guests, a home office, or hobbies. Outside, the oversized iron-fenced yard provides plenty of room for gardening, entertaining, pets, or future expansion. Enjoy your morning coffee or evening unwind on the side porch, while the attached one-car garage adds convenient storage. As part of the Chester Harbor community, you’ll enjoy access to the community boat ramp and the Chester River, making it easy to spend your days boating, fishing, kayaking, or simply enjoying life on the water. Ideally located near marinas, parks, and the shops, restaurants, and waterfront charm of historic downtown Chestertown, this property offers the perfect blend of space, convenience, recreation, and opportunity. Priced to reflect its condition, this is a chance to create a home that’s uniquely your own while building equity in a sought-after location.
  • Listed by: Christopher Craddock 703.688.2635 offers@thereduxgroup.com • EXP Realty, LLC
  • Listed by: Alex Justin McCracken 202.506.0202 alex.mccracken@exprealty.com • EXP Realty, LLC
Last updated: 08/21/2026 04:37 PM • Source: BRIGHT, MLS#: MDQA2018038

Location

Listing Courtesy of EXP Realty, LLC
Add your commute

Payment Calculator

Get preapproved with
OriginPoint Mortgage or Rocket Mortgage1

$1,322 per month

30 year fixed, 6.55% Interest

Principal and Interest

$1,144

Property Taxes

$179

HOA Dues

$0

The Payment Calculator is for illustrative purposes only.

Know your buying power with a preapproval and custom rate in minutes

Rocket Mortgage1

Property Information for 533 Round Top Road

Property Details
  • Taxes: $2,144 / year
  • MLS Type: Residential / Fee Simple
  • County: Queen Anne's County
  • Tax ID Number: 1802008408
  • Ownership: Fee Simple
  • Condo Coop Association: No
  • HOA: No
  • Structure Type: Detached
  • Style: Ranch/Rambler
  • Levels/Stories: 1
  • Waterfront: No
  • Garage: Yes
  • Expected On Market Date: 09-01-2026
  • Subdivision: CHESTER HARBOR
  • Subdivision: CHESTER HARBOR (QUEEN ANNES MD)
  • Legal Subdivision: CHESTER HARBOR
  • Total Parking Spaces: 1
  • Central Air: No
  • Basement: No
  • Above Grade Finished SQFT: 1,800.00
  • Above Grade Fin SQFT Source: Assessor
  • Below Grade Finished SQFT: .00
  • Below Grade Fin SQFT Source: Assessor
  • Below Grade Unfinished SQFT: .00
  • Below Grade Unfin SQFT Source: Assessor
  • Total Below Grade SQFT: .00
  • Total Below Grade SQFT Source: Assessor
  • New Construction: No
Building Information
  • Stories: 1
  • Year Built: 1962
  • Lot Size: 0.55 AC / 24,000 SF
Location
Location
  • In City Limits: No
  • School District Name: QUEEN ANNE'S COUNTY PUBLIC SCHOOLS
  • School District County ID: 121137777627
  • SchoolDistrictSource: Listing Agent
  • County: QUEEN ANNES
Waterfront / Water Access
Waterfront / Water Access
  • Water View: No
  • Water Access: Yes
  • Water Oriented: Yes
  • Navigable Water: Yes
  • Tidal Water: No
  • Water Body Name: ROSIN CREEK
  • Water Body Type: Creek
  • Docks Count: 0
  • Mean Low Water Feet: 2.00
  • Distance To Body Of Water: 1.00
  • Distance To Body Of Water Units: Blocks
Association / Community Info
Association / Community Info
  • Senior Community: No
Taxes and Assessment
Taxes and Assessment
  • Tax Year: 2025
  • Tax Assessed Value: $243,233
  • Year Assessed: 2026
  • County Tax: $2,144
  • Improvement Assessed Value: $144,800
  • Land Assessed Value: $129,700
  • Clean Green Assessed: No
  • Land Use Code: R
  • Section: 1
  • Zoning: NC-20
  • Tax Lot: 341
  • School Tax: $0
  • Automatically Update Tax Values Y/N: Yes
Rooms
Main
  • # Bedrooms Count Main Level: 4
  • # Bathrooms Count Main Level: 2
  • # Bathrooms Full Main Level: 1
  • # Bathrooms Half Main Level: 1
Rooms
  • Room List: Living Room, Primary Bedroom, Bedroom 2, Bedroom 3, Bedroom 4, Kitchen, Family Room
  • Stories: Main
Rooms Information
Room 1
  • Room Type: Living Room
  • Room Length: 19.0
  • Room Width: 12.0
  • Room Level: Main
  • Room Exists: Yes
  • Room Dimensions: 19 X 12
  • Room Features: Flooring - Carpet
Room 2
  • Room Type: Bedroom 4
  • Room Length: 10.0
  • Room Width: 8.0
  • Room Level: Main
  • Room Exists: Yes
  • Room Dimensions: 10 X 8
  • Room Features: Flooring - Vinyl
Room 3
  • Room Type: Bedroom 3
  • Room Length: 8.0
  • Room Width: 8.0
  • Room Level: Main
  • Room Exists: Yes
  • Room Dimensions: 8 X 8
  • Room Features: Flooring - HardWood
Room 4
  • Room Type: Bedroom 2
  • Room Length: 10.0
  • Room Width: 11.0
  • Room Level: Main
  • Room Exists: Yes
  • Room Dimensions: 10 X 11
  • Room Features: Flooring - HardWood
Room 5
  • Room Type: Kitchen
  • Room Length: 17.0
  • Room Width: 16.0
  • Room Level: Main
  • Room Exists: Yes
  • Room Dimensions: 17 X 16
  • Room Features: Flooring - Vinyl
Room 6
  • Room Type: Family Room
  • Room Length: 16.0
  • Room Width: 12.0
  • Room Level: Main
  • Room Exists: Yes
  • Room Dimensions: 16 X 12
  • Room Features: Flooring - Carpet
Room 7
  • Room Type: Primary Bedroom
  • Room Length: 11.0
  • Room Width: 11.0
  • Room Level: Main
  • Room Exists: Yes
  • Room Dimensions: 11 X 11
  • Room Features: Flooring - HardWood
Building Info
Building Info
  • Total Finished SQFT: 1,800.00
  • Total Finished SQFT Source: Assessor
Lot / Land Information
Lot / Land Information
  • Lot Size Source: Assessor
  • Location Type: Creek/Stream
  • Parcel ID: 4513339
Parking
Parking
  • Type Of Parking: Attached Garage
  • Num of Attached Garage Spaces: 1
  • Total Garage Spaces: 1
  • Garage Features: Garage - Front Entry
Interior Features
Interior Features
  • Interior Features: Attic, Kitchen - Eat-In, Family Room Off Kitchen
  • Fireplace: No
  • Appliances: Dishwasher, Stove, Refrigerator, Washer, Dryer
  • Accessibility Features: None
Exterior Features
Exterior Features
  • Pool: No Pool
Utilities
Utilities
  • Heating: Yes
  • Cooling Type: None
  • Cooling Fuel: Electric
  • Heating Type: Forced Air
  • Heating Fuel: Electric, Oil
  • Hot Water: Electric
  • Water Source: Well
  • Sewer Septic: Septic Exists
Confidential Data
Listing Office
  • List Agent AOR: Northern Virginia Association of REALTORS
  • List Agent URL: www.reduxrealty.com

Property History for 533 Round Top Road

DateEvent & SourcePriceAppreciation
May 12, 2017

Closed (Public Record)

Public Record #601118478

$175,000

-0.2% / yr

Nov 3, 2016

Withdrawn

BRIGHT #1008130314

$159,000—
Nov 3, 2016

Withdrawn

BRIGHT #1008130314

—
DateEvent & SourcePrice
05/12/2017

Closed (Public Record)

Public Record #601118478

$175,000

-0.2% / yr

11/03/2016

Withdrawn

BRIGHT #1008130314

$159,000
11/03/2016

Withdrawn

BRIGHT #1008130314

—

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

Public Records for 533 Round Top Road

Taxable ValueLand-Additions-Total-
Tax Record2025$2,204 ($184 / month)
Home Facts
Beds0Baths1.5Total Finished SqFt1,800 SqFtAbove Grade Finished SqFt1,800 SqFtStories1Lot Size24,000 SqFtStyleSingle Family ResidenceYear Built1962Year Renovated1962ZoningNC-20CountyQUEEN ANNE'SAPN02-008408

Schools near 533 Round Top Road

This home is within Queen Anne's County Public Schools.
Rating
School
Type
Grades
Distance
Church Hill Elementary School
Public - PK to 4
Sudlersville Middle School
Public - 5 to 8
Queen Anne's County High School
Public - 9 to 12
Chestertown Christian Academy
Private - PK to 12
Rating
School
Distance
Church Hill Elementary School
PublicPK to 4

Sudlersville Middle School
Public5 to 8

Queen Anne's County High School
Public9 to 12

Chestertown Christian Academy
PrivatePK 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.

Similar Homes

New listings in 21620

$1,195,000 | 302 South Mill Street, Chestertown, MD 21620
1/17
New

$1,195,000

2
Bedrooms
806
Square Feet
0.99
Acres

302 South Mill Street, Chestertown, MD 21620

$295,000 | 240 Round Top Road, Chestertown, MD 21620
1/30
Active Under Contract

$295,000

3
Bedrooms
1,132
Square Feet
1
Acres

240 Round Top Road, Chestertown, MD 21620

$369,000 | 101 South College Avenue, Chestertown, MD 21620
1/35

$369,000

2
Bedrooms
1,036
Square Feet
0.03
Acres

101 South College Avenue, Chestertown, MD 21620

$345,000 | 217 Edmore Road, Chestertown, MD 21620
Coming Soon

$345,000

3
Bedrooms
1,398
Square Feet
0.34
Acres

217 Edmore Road, Chestertown, MD 21620

$649,000 | 22400 Great Oak Landing Road, Chestertown, MD 21620
1/61

$649,000

4
Bedrooms
2,864
Square Feet
1.03
Acres

22400 Great Oak Landing Road, Chestertown, MD 21620

$524,900 | 1003 Twin Court, Chestertown, MD 21620
1/43

$524,900

3
Bedrooms
2,076
Square Feet
0.70
Acres

1003 Twin Court, Chestertown, MD 21620

a living room with furniture and kitchen with furniture
1/18

$295,000

1
Bedrooms
Unavailable
Square Feet

117 North Water Street, Unit 3B, Chestertown, MD 21620

a front view of a house with a yard
1/34
Active Under Contract

$440,000

2
Bedrooms
1,058
Square Feet
0.04
Acres

104 Church Alley, Chestertown, MD 21620

$750,000 | 216 Birch Run Road, Chestertown, MD 21620
1/52

$750,000

3
Bedrooms
2,176
Square Feet
0.63
Acres

216 Birch Run Road, Chestertown, MD 21620

Explore Nearby Homes

More information about 533 Round Top Road, Chestertown, MD 21620

533 Round Top Road is a single family home Coming Soon in Chestertown, MD 21620. This property is currently priced at $225,000. This listing's school district is Queen Anne's County Public Schools. Nearby schools include Church Hill Elementary School, Sudlersville Middle School and Queen Anne's County High School. 533 Round Top Road is a 4-bed, 2-bath, 1,800 sqft single family home built in 1962.

No guarantee, warranty or representation of any kind is made regarding the completeness or accuracy of any information, descriptions or measurements (including square footage measurements and property condition), such should be independently verified through appropriate means, including, but not limited to, in person inspection and public records, and Compass International Holdings, its subsidiaries, affiliates and independently owned and operated franchisees, and their affiliated agents and associated third parties expressly disclaim 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 seller's discretion. 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 EXP Realty, LLC

© 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 08/21/2026 04:37 PM