Google street view image for 111 Bentons Pleasure Rd, Chester, MD 21619

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SOLD

$854,371

Est. refi paymentEst. refi $4,137/mo

—

•

3.5 ba

•

3,048

sq ft

111 Bentons Pleasure Rd, Chester, MD 21619

About this home

KENT ISLAND * FINISHED BASEMENT * 1 ACRE; 2-STORY FOYER W/ HARDWD FLRS; 2-STORY FAMILY RM W/ GAS FP; KITCHEN W/ OAK CABINETS, CENTER BAR-TOP ISLAND; GOURMET DESK; BREAKFAST AREA W/ SLIDERS TO REAR DECK; SPEAKER DISTRIBUTION SYS; SECURITY SYS; WATER FILTER/SOFTENER; WASHER/DRYER; X-TRA FREEZER; 2-CAR GAR W/ HIGH CEILING. HM WARRANTY; NO HOA

Single-familyProperty Type

2003Year Built

1 acresLot Size

$280Est. Price/Sq.Ft.

2 spacesParking

Source:Public Records

Redfin Estimate

$854,371

$209K since sold in June 2006$21K since August

Recently sold homes
Estimate history
Homes for sale

This home's estimate is 28% lower than the average sale price ($1.19M) of 5 comparable homes.

SOLD DEC 10, 2025
$795,000
A
5 beds3.5 baths3,065 sq ft
104 Woods Rd, Chester, MD 21619
SOLD FEB 26, 2026
$895,000
B
5 beds4 baths4,275 sq ft
115 Cedar Rd, Chester, MD 21619
SOLD JAN 9, 2026
$740,000
C
4 beds2.5 baths2,791 sq ft
123 Bentons Pleasure Rd, Chester, MD 21619
SOLD JUL 24, 2026
$2,200,000
D
5 beds4 baths3,250 sq ft
328 Bentons Pleasure Rd, Chester, MD 21619
SOLD JUL 17, 2026
$1,300,000
E
3 beds4 baths4,208 sq ft
1719 Harbor Dr, Chester, MD 21619

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Earn from this home

Sell

$803,245

Est. take-home

List your home with Redfin and save $8,544

Refinance

Est. cash available

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Rent

$4,015/mo

Redfin rental estimate

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Market trends in 21619, MD

Last updated August 2026

Buyer's Market

Seller's Market

Balanced market

Sale-to-List Price

97.9%

0.3% MoM

Median sale price

$606K

$98K MoM

Avg. days on market

54d

3 days MoM

Recently sold homes

1 MoM

New listings for sale

NEW 11 HRS AGO
$349,000
3 beds1.5 baths1,302 sq ft
6005 Bridgepointe Dr, Chester, MD 21619
(410) 758-0333
$459,000
3 beds2.5 baths2,008 sq ft
43-A Queen Neva Ct, Chester, MD 21619
(410) 224-3600
$550,000
5 beds3.5 baths3,552 sq ft
326 Castle Marina Rd, Chester, MD 21619
(410) 643-5005
$439,000
3 beds3 baths1,750 sq ft
41-D Queen Catherine Ct, Chester, MD 21619
(410) 465-1770
COMING SOON
$350,000
2 beds2 baths1,274 sq ft
200 Church St, Chester, MD 21619
(443) 274-1900
3D WALKTHROUGH
$944,900
3 beds3 baths2,761 sq ft
275 Warbler Way, Chester, MD 21619
(703) 378-8810
OPEN SUN, 12PM TO 1PM
$400,000
5 beds3.5 baths3,250 sq ft
1868 Roberta Dr, Chester, MD 21619
(410) 828-4838
COMING SOON
$1,250,000
3 beds2.5 baths2,742 sq ft
1717 Harbor Dr, Chester, MD 21619
(410) 476-2201
EARLY ACCESS
$450,000
3 beds4 baths2,100 sq ft
609 Blenny Ln, Chester, MD 21619
$868,000
4 beds2.5 baths3,168 sq ft
113 Bentons Pleasure Rd, Chester, MD 21619
(410) 823-0033
See all

Provided by Redfin

Sale history for 111 Bentons Pleasure Rd

** Price available after signing in.

Year

Property tax

Land + Additions

Assessment*

2025

$5,733 (+5.5%)

$189,600 + $514,000

$703,600

2024

$5,436 (+5.5%)

2023

$5,151

$175,800 + $371,000

$546,800

2022

$5,151 (−1.8%)

$175,800 + $371,000

$546,800

2021

$5,244 (−9.3%)

$175,800 + $371,000

$546,800

2020

$5,780 (+2.3%)

$175,800 + $371,000

$546,800

2019

$5,652 (+2.3%)

$175,800 + $426,800

$602,600

2018

$5,525 (+2.9%)

2017

$5,369 (+10.3%)

$149,900 + $412,900

$562,800

2016

$4,868 (+5.0%)

2015

$4,634

$149,900 + $333,300

$483,200

2014

$4,634 (+3.5%)

2013

$4,479 (+1.6%)

2012

$4,407 (+10.4%)

2011

$3,993 (+5.4%)

2010

$3,789 (+5.7%)

2009

$3,585

Tax history for 111 Bentons Pleasure Rd

Year

Property tax

Land + Additions

Assessment*

2025

$5,733 (+5.5%)

$189,600 + $514,000

$703,600

2024

$5,436 (+5.5%)

2023

$5,151

$175,800 + $371,000

$546,800

2022

$5,151 (−1.8%)

$175,800 + $371,000

$546,800

2021

$5,244 (−9.3%)

$175,800 + $371,000

$546,800

2020

$5,780 (+2.3%)

$175,800 + $371,000

$546,800

2019

$5,652 (+2.3%)

$175,800 + $426,800

$602,600

2018

$5,525 (+2.9%)

2017

$5,369 (+10.3%)

$149,900 + $412,900

$562,800

2016

$4,868 (+5.0%)

2015

$4,634

$149,900 + $333,300

$483,200

2014

$4,634 (+3.5%)

2013

$4,479 (+1.6%)

2012

$4,407 (+10.4%)

2011

$3,993 (+5.4%)

2010

$3,789 (+5.7%)

2009

$3,585

*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
Permits

Beds

—

Baths

3.5

Stories

Lot width

—

Lot depth

—

Lot size

1 Acre

Year renovated

—

Sq. Ft.

3,048

Year built

2003

Style

Single Family Residential

County

Queen Anne's County

APN

04 076745

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

Around this home

Schools

Kent Island Elementary School

Public PreK-2 • Assigned • 1.8mi

Matapeake Middle School

Public 6-8 • Assigned • 2.0mi

8/10

Kent Island High School

Public 9-12 • Assigned • 2.6mi

6/10

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 104° expected this year, 16 days in 30 years

6/10 Wind Factor

71% chance of strong winds in next 30 years

3/10 Air Factor

2 unhealthy days expected this year, 3 days in 30 years

Provided by First Street

Historical weather

Chester, MD • 21619

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 9.3 hours in June and 4.8 hours in December, which is comparable to the U.S. average for solar exposure.

9.3 hrs

4.8 hrs

JuneDecember

Provided by Shadowmap

Estimated sale price

$812,000 – $983,000

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Nearby similar homes

$19,500

2 beds1 bath764 sq ft

1405 Little Creek Rd, Chester, MD 21619

(302) 217-6692

NEW CONSTRUCTION

$1,200,000

3 beds3.5 baths2,930 sq ft

117 Flycatcher Way, Chester, MD 21619

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NEW CONSTRUCTION

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5 beds4.5 baths3,225 sq ft

111 Flycatcher Way, Chester, MD 21619

(410) 208-3500

NEW CONSTRUCTION

$1,100,000

3 beds3 baths2,789 sq ft

123 Flycatcher Way, Chester, MD 21619

(410) 208-3500

New listings for sale in 21619

NEW 11 HRS AGO

$349,000

3 beds1.5 baths1,302 sq ft

6005 Bridgepointe Dr, Chester, MD 21619

(410) 758-0333

$459,000

3 beds2.5 baths2,008 sq ft

43-A Queen Neva Ct, Chester, MD 21619

(410) 224-3600

$550,000

5 beds3.5 baths3,552 sq ft

326 Castle Marina Rd, Chester, MD 21619

(410) 643-5005

$439,000

3 beds3 baths1,750 sq ft

41-D Queen Catherine Ct, Chester, MD 21619

(410) 465-1770

COMING SOON

$350,000

2 beds2 baths1,274 sq ft

200 Church St, Chester, MD 21619

(443) 274-1900

3D WALKTHROUGH

$944,900

3 beds3 baths2,761 sq ft

275 Warbler Way, Chester, MD 21619

(703) 378-8810

OPEN SUN, 12PM TO 1PM

$400,000

5 beds3.5 baths3,250 sq ft

1868 Roberta Dr, Chester, MD 21619

(410) 828-4838

COMING SOON

$1,250,000

3 beds2.5 baths2,742 sq ft

1717 Harbor Dr, Chester, MD 21619

(410) 476-2201

EARLY ACCESS

$450,000

3 beds4 baths2,100 sq ft

609 Blenny Ln, Chester, MD 21619

Home values near 111 Bentons Pleasure Rd

Data from public records.

Address	Redfin Estimate
104 Bentons Pleasure Road, Chester, MD - Beds \| 2.5 Baths \| 2270 Sq. Ft.	$620,183
115 Bentons Pleasure Road, Chester, MD 4 Beds \| 2.5 Baths \| 2880 Sq. Ft.	$814,955

Address	Redfin Estimate
109 Bentons Pleasure Road, Chester, MD - Beds \| 3.5 Baths \| 3166 Sq. Ft.	$932,939
114 Bentons Pleasure Road, Chester, MD 3 Beds \| 2 Baths \| 1824 Sq. Ft.	$528,035

Address	Redfin Estimate
105 Bentons Pleasure Road, Chester, MD - Beds \| 2 Baths \| 1692 Sq. Ft.	$568,357
106 Bentons Pleasure Road, Chester, MD - Beds \| 2 Baths \| 1350 Sq. Ft.	$480,578

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GreatSchools Ratings provided by GreatSchools.org.

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111 Bentons Pleasure Rd, Chester, MD 21619

About this home

Redfin Estimate

Earn from this home

Market trends in 21619, MD

Sale history for 111 Bentons Pleasure Rd

Tax history for 111 Bentons Pleasure Rd

Public record

Property details

Public facts

Around this home

Schools

Lifestyle

Climate risks

Historical weather

Sun exposure

Nearby similar homes

New listings for sale in 21619

Home values near 111 Bentons Pleasure Rd

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