OFF MARKET

Off Market Aug 2025 for $315K

$329,992

Est. refi paymentEst. refi $1,571/mo

•

1,056

sq ft

106 Wilton Rd, Chestertown, MD 21620

About this home

Charming Updated and Well Maintained Rancher in the Chester Harbor Community of Queen Anne's County Chestertown! This house is the definition of "move-in ready" as the owner has taken tremendous pride in keeping the property updated. Over the years, they've installed new windows, new HVAC unit, new hot water heater, remodeled the kitchen, installed new appliances, painted the interior, added new flooring , and given the bathroom a refresh. The fully fenced backyard includes an oversized detached shed, upgraded BAT septic system, concrete patio and mature trees for additional privacy and shade. Plus, a brand new roof!! Conveniently located close to Church Hill, Centreville, Wye Mills and Kent Island. Or head across the Chester River (moments away) into Kent County Chestertown, Worton, Galena or Kennedyville!! Community of Chester Harbor also features a neighborhood playground, basketball hoop, pier and small boat launch with voluntary fee.

Single-familyProperty Type

1975Year Built

0.34 acresLot Size

$312Est. Price/Sq.Ft.

2 spacesParking

Listed by Crystal Smith • RE/MAX Executive

•443-274-1900 (broker)

Bought with Peter Heller • Coldwell Banker Chesapeake Real Estate Company

•410-778-0330 (broker)

Redfin checked: a minute ago

•Source:BRIGHT MLS #MDQA2013930

Redfin Estimate

$329,992

$15K since sold in August 2025$0 since August

Recently sold homes
Estimate history
Homes for sale

This home's estimate is 10.2% higher than the average sale price ($300K) of 5 comparable homes.

SOLD MAY 14, 2026
$278,500
A
3 beds1 bath— sq ft
107 Longfellow Dr, Chestertown, MD 21620
SOLD AUG 21, 2026
$289,000
B
3 beds1 bath1,248 sq ft
517 Round Top Rd, Chestertown, MD 21620
SOLD MAY 27, 2026
$300,000
C
3 beds1 bath1,408 sq ft
154 Longfellow Dr, Chestertown, MD 21620
SOLD SEP 26, 2025
$300,000
D
3 beds1 bath1,056 sq ft
925 Round Top Rd, Chestertown, MD 21620
SOLD MAR 31, 2026
$330,000
E
3 beds2 baths1,170 sq ft
129 Parma Rd, Chestertown, MD 21620

Claim this home to receive a free report every month with insights on the changing estimate.

Earn from this home

Refinance

Est. cash available

Get cash now or lower your monthly rate

Rent

$1,977/mo

Redfin rental estimate

List your home for rent

Market trends in 21620, MD

Last updated August 2026

Buyer's Market

Seller's Market

Seller's market

Sale-to-List Price

98.0%

+0.0% MoM

Median sale price

$347K

$15K MoM

Avg. days on market

48d

2 days MoM

Recently sold homes

1 MoM

New listings for sale

$263,000
3 beds2 baths1,140 sq ft
115 Chester Arms Dr, Chestertown, MD 21620
(703) 378-8810
$229,000
3 beds1 bath936 sq ft
7415 Wilkins Ln, Chestertown, MD 21620
(410) 810-0010
COMING SOON
$275,000
3 beds1 bath975 sq ft
7482 Poplar Ave, Chestertown, MD 21620
(301) 970-2447
COMING SOON
$315,000
3 beds1 bath1,008 sq ft
24775 Langford Rd, Chestertown, MD 21620
(410) 398-9200
COMING SOON
$300,000
3 beds1 bath960 sq ft
104 Lincoln Dr, Chestertown, MD 21620
(443) 274-1900
$315,000
3 beds2 baths1,288 sq ft
109 Parma Rd, Chestertown, MD 21620
(410) 778-0330
$225,000
4 beds1.5 baths1,800 sq ft
533 Round Top Rd, Chestertown, MD 21620
(833) 335-7433
$304,000
3 beds2 baths1,232 sq ft
7464 Shortall St, Chestertown, MD 21620
(410) 476-2201
COMING SOON
$675,000
5 beds3 baths2,838 sq ft
212 Washington Ave, Chestertown, MD 21620
(410) 778-0330
$38,200,000
4 beds2 baths2,330 sq ft
8184 Rock Hall Rd, Chestertown, MD 21620
(410) 778-3779
See all

Provided by Redfin

Sale history for 106 Wilton Rd

Date

Event

Price

BRIGHT MLS #MDQA2013930

Aug 29, 2025

Sold

$315,000

$298/sq ft

Jul 28, 2025

Relisted

—

Jul 22, 2025

Listing Removed

—

Jul 10, 2025

Listed

$299,500

$284/sq ft

Jul 1, 2025

Coming Soon

$299,500

$284/sq ft

MRIS #QA7720997

Jan 30, 2012

Sold

$130,000

$123/sq ft

Dec 23, 2011

Pending

—

Dec 15, 2011

Price Changed

$131/sq ft

Nov 3, 2011

Listed

$137/sq ft

BRIGHT MLS #1004631980

Jan 30, 2012

Sold

$130,000

$123/sq ft

Dec 22, 2011

Listing Removed

—

Nov 3, 2011

Listed

$138,000

$131/sq ft

MRIS #QA6309895

Mar 21, 2007

Delisted

—

Feb 9, 2007

Listed

Public Records

Mar 31, 2004

Sold

$117,000

$111/sq ft

Public Records

Jul 5, 2000

Sold

$88,000

$83/sq ft

MRIS #QA3016298

Mar 1, 2000

Delisted

—

Jul 29, 1999

Listed

$84/sq ft

MRIS #QA2655003

Jul 7, 1999

Delisted

—

Jan 9, 1999

Listed

MRIS #QA2009216

Aug 20, 1996

Delisted

—

Jun 17, 1996

Listed

** Price available after signing in.

Year

Property tax

Land + Additions

Assessment*

2025

$1,759 (+9.0%)

2024

$1,614 (+9.9%)

$76,000 + $104,400

$180,400

2023

$1,468 (+11.0%)

2022

$1,322 (+3.2%)

2021

$1,282 (+5.2%)

$56,000 + $78,000

$134,000

2020

$1,219 (+5.5%)

2019

$1,155

2018

$1,155

$56,000 + $58,200

$114,200

2017

$1,155 (−11.5%)

$56,000 + $58,200

$114,200

2016

$1,306

$47,200 + $82,800

$130,000

2015

$1,306 (−3.0%)

$47,200 + $82,800

$130,000

2014

$1,346

$82,100 + $52,000

$134,100

2013

$1,346 (+2.3%)

2012

$1,316 (−7.4%)

2011

$1,422 (+9.2%)

2010

$1,303 (+10.7%)

2009

$1,177

Tax history for 106 Wilton Rd

Year

Property tax

Land + Additions

Assessment*

2025

$1,759 (+9.0%)

2024

$1,614 (+9.9%)

$76,000 + $104,400

$180,400

2023

$1,468 (+11.0%)

2022

$1,322 (+3.2%)

2021

$1,282 (+5.2%)

$56,000 + $78,000

$134,000

2020

$1,219 (+5.5%)

2019

$1,155

2018

$1,155

$56,000 + $58,200

$114,200

2017

$1,155 (−11.5%)

$56,000 + $58,200

$114,200

2016

$1,306

$47,200 + $82,800

$130,000

2015

$1,306 (−3.0%)

$47,200 + $82,800

$130,000

2014

$1,346

$82,100 + $52,000

$134,100

2013

$1,346 (+2.3%)

2012

$1,316 (−7.4%)

2011

$1,422 (+9.2%)

2010

$1,303 (+10.7%)

2009

$1,177

*Taxable value of land and structures on it ("additions") is determined regularly by local assessors and does not affect market price.

Public record

Public record
Zoning

Beds

—

Baths

Stories

Lot width

—

Lot depth

—

Lot size

0.34 Acres

Year renovated

—

Sq. Ft.

1,056

Year built

1975

Style

Single Family Residential

County

Queen Anne's County

APN

02 011530

Parking Spaces

—

Basement

—

Accessible

—

HOA Dues

—

Garage

—

Features

—

Last updated by owner on Jul 18, 2026.

NC-20

Neighborhood Conservation-20 District

There are several varieties of NC Districts. The NC Districts are intended to preserve the character, density, and scale of existing residential neighborhoods. The NC Districts allow existing neighborhoods to conform to this Chapter 18:1, and they allow for in-fill development to be compatible with the surrounding area. NC Districts are designated for existing residential developments as follows: NC-20: 20,000 sq ft average lot size.; All NC District regulations apply to NC Districts with a T designation on the Zoning Maps; except that single-wide manufactured homes are a permitted use within NC-T Districts.

Permitted uses

Include but are not limited to:

Equestrian facility
Housing-Single unit
Housing-Multiple units
Public service
Recreation
Housing-Mobile home park

Property details

Parking

Parking Information
# of Total Garage and Parking Spaces: 2
Driveway - # of Spaces: 2
Driveway

Interior

Virtual Tour

Bedroom Information
# of Bedrooms On Main Level: 3

Bathroom Information
# of Bathrooms (Full) On Main Level: 1
# of Bathrooms (Full): 1

Interior Information
Flooring Type: Hardwood
Living Area Sq.Ft. Source: Assessor
Wall & Ceiling Types: Dry Wall

Basement Information
Basement: No

Exterior

Property Information
Total Below Grade Sq. Ft.: 0
Improvement Assessed Value: $104,400
Ownership Interest: Fee Simple
Year Built Source: Assessor

Building Information
Construction Materials: Vinyl Siding
Foundation Details: Crawl Space
Other Structures: Above Grade, Below Grade
Roof: Architectural Shingle
Structure Type: Detached

Lot Information
Tidal Water: No

Land Information
Land Assessed Value: $76,000

Above Grade Information
Finished Sq.Ft.: 1,056
Finished Sq.Ft. Source: Assessor

Below Grade Information
Unfinished Sq.Ft. Source: Assessor
Finished Sq.Ft. Source: Assessor

Financial

Tax Information
County Tax: $1,554
Tax Assessed Value: $180,400
Tax Year: 2024
Tax Annual Amount: $1,554

Assessments Information
Year Assessed: 2025

Utilities

Utilities Information
Central Air
Cooling Type: Central A/C
Cooling Fuel: Electric
Heat Pump(s)
Heating Fuel: Electric
Hot Water: Electric
Sewer Septic: On Site Septic
Water Source: Well

Location

School Information
School District Name: QUEEN ANNE'S COUNTY PUBLIC SCHOOLS
School District Source: Listing Agent

Location Information
Outside City Limits
Directions: Round Top Road to Rosin Drive or Farwell Road. Turn on Wilton Road. Sign on Property.

Public facts

Beds: —
Baths: 1.0
Sq. Ft.: 1,056
Stories: 1.0
Lot Size: 0.34 acres
Style: Single Family Residential
Year Built: 1975
Year Renovated: —
County: Queen Anne's County
APN: 02 011530

Home facts updated by county records on Jul 17, 2026

Around this home

Schools

Church Hill Elementary School

Public PreK-4 • Assigned • 5.1mi

5/10

Sudlersville Middle School

Public 5-8 • Assigned • 9.4mi

5/10

Queen Anne's County High School

Public 9-12 • Assigned • 12.2mi

7/10

Provided by GreatSchools

Lifestyle

Provided by Walk Score and Local Logic

Climate risks

1/10 Flood Factor

Minimal risk of a flood reaching the building in the next 30 years

1/10 Fire Factor

Unlikely to be in a wildfire in next 30 years

8/10 Heat Factor

7 days above 105° expected this year, 15 days in 30 years

6/10 Wind Factor

27% chance of strong winds in next 30 years

3/10 Air Factor

2 unhealthy days expected this year, 4 days in 30 years

Provided by First Street

Historical weather

Chestertown, MD • 21620

Average low and high temperatures (°F)

Jan

Feb

Mar

Apr

May

Jun

Jul

Aug

Sep

Oct

Nov

Dec

Sun exposure

In this area, properties receive around 9.2 hours in June and 4.7 hours in December, which is comparable to the U.S. average for solar exposure.

9.2 hrs

4.7 hrs

JuneDecember

Provided by Shadowmap

Estimated sale price

$314,000 – $380,000

Sell confidently with a local market expert in Chestertown. 3 minutes to get started.

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Home values near 106 Wilton Rd

Data from public records.

Address	Redfin Estimate
118 Wilton Road, Chestertown, MD - Beds \| 2 Baths \| 1808 Sq. Ft.	$342,023
103 Wilton Road, Chestertown, MD - Beds \| 1.5 Baths \| 1536 Sq. Ft.	$310,527

Address	Redfin Estimate
113 Wilton Road, Chestertown, MD 4 Beds \| 2 Baths \| 2034 Sq. Ft.	$358,827
114 Wilton Road, Chestertown, MD 3 Beds \| 2 Baths \| 1152 Sq. Ft.	$335,216

Address	Redfin Estimate
110 Wilton Road, Chestertown, MD 3 Beds \| 2 Baths \| 1411 Sq. Ft.	$361,387
124 Wilton Road, Chestertown, MD 3 Beds \| 1 Baths \| 1056 Sq. Ft.	$300,467

Property information provided by BRIGHT MLS when last listed in 2025. This data may not match . Learn more.

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GreatSchools Ratings provided by GreatSchools.org.

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About this home

Redfin Estimate

Earn from this home

Market trends in 21620, MD

Sale history for 106 Wilton Rd

Tax history for 106 Wilton Rd

Public record

Property details

Around this home

Schools

Lifestyle

Climate risks

Historical weather

Sun exposure

Nearby similar homes

New listings for sale in 21620

Home values near 106 Wilton Rd

More real estate resources