OFF MARKET

Off Market Aug 2017 for $517K

$779,428

Est. refi paymentEst. refi $4,036/mo

•

3,389

sq ft

311 Bentons Pleasure Rd, Chester, MD 21619

About this home

Welcome to your Dream Home in Bentons Pleasure! Every inch of this 3515 SQFT Beauty has been Renovated w/ complete Quality Construction! Nestled on a Spacious 1.89 Acre w/ Mature Landscaping & Inground Pool offers pure serenity across Cox Creek. Truly Immaculate 4 BR, 2.5 BA Sprawling Tri-Level complete w/ Porch, Patio, FP, Wood Flrs, Crown Molding, Ceramic Tile & FINISHED BASEMENT! Public Sewer too!

Single-familyProperty Type

1969Year Built

1.89 acresLot Size

$230Est. Price/Sq.Ft.

2 car garageParking

Listed by Pam Doll Ackermann • RE/MAX Executive

•443-274-1900 (broker)

Bought with Marilyn Hendley • Better Homes & Gardens Real Estate The J. Melvin

•410-280-1646 (broker)

Redfin checked: 2 minutes ago

•Source:BRIGHT MLS #1001036223

Redfin Estimate

$779,428

$262K since sold in August 2017$13K since August

Recently sold homes
Estimate history
Homes for sale

This home's estimate is 22.7% lower than the average sale price ($1.01M) of 6 comparable homes.

SOLD AUG 25, 2026
$491,023
A
3 beds2 baths3,128 sq ft
114 Cedar Rd, Chester, MD 21619
SOLD JAN 9, 2026
$740,000
B
4 beds2.5 baths2,791 sq ft
123 Bentons Pleasure Rd, Chester, MD 21619
SOLD AUG 3, 2026
$1,125,000
C
4 beds3 baths3,017 sq ft
2812 Harvest Ct, 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 MAR 10, 2026
$853,000
E
4 beds2.5 baths2,404 sq ft
162 Kirwans Landing Ln, Chester, MD 21619
SOLD AUG 14, 2026
$640,000
F
4 beds2.5 baths2,570 sq ft
479 Creeks End Ln, Stevensville, MD 21666

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Earn from this home

Sell

$397,604

Est. take-home

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Refinance

Est. cash available

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Rent

$3,241/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

98.3%

+0.4% MoM

Median sale price

$640K

$27K MoM

Avg. days on market

66d

12 days MoM

Recently sold homes

3 MoM

New listings for sale

COMING SOON
$379,900
1 bed1.5 baths1,260 sq ft
12 Queen Anne Way Unit J, Chester, MD 21619
(410) 643-4663
$350,000
2 beds2 baths1,274 sq ft
200 Church St, Chester, MD 21619
(443) 274-1900
$469,989
4 beds2.5 baths1,350 sq ft
9 Ackerman, Stevensville, MD 21666
(443) 249-7653
COMING SOON
$789,000
3 beds2.5 baths2,787 sq ft
402 Macum Creek Dr, Chester, MD 21619
(703) 378-8810
OPEN THU, 5PM TO 7PM
$1,250,000
3 beds2.5 baths2,742 sq ft
1717 Harbor Dr, Chester, MD 21619
(410) 476-2201
$349,000
3 beds2.5 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
3D WALKTHROUGH
$944,900
3 beds3 baths2,761 sq ft
275 Warbler Way, Chester, MD 21619
(703) 378-8810
See all

Provided by Redfin

Sale history for 311 Bentons Pleasure Rd

** Price available after signing in.

Year

Property tax

Land + Additions

Assessment*

2025

$5,221 (+5.1%)

$193,900 + $405,300

$599,200

2024

$4,966 (+5.2%)

2023

$4,721

$193,800 + $307,400

$501,200

2022

$4,721 (−1.8%)

$193,800 + $307,400

$501,200

2021

$4,807 (−0.3%)

$193,800 + $307,400

$501,200

2020

$4,822 (+11.4%)

$193,800 + $307,400

$501,200

2019

$4,329 (+14.6%)

$193,800 + $309,000

$502,800

2018

$3,776 (+17.2%)

2017

$3,223

$167,800 + $162,000

$329,800

2016

$3,223 (−0.7%)

$167,800 + $162,000

$329,800

2015

$3,246

$167,800 + $164,400

$332,200

2014

$3,246

2013

$3,246 (+0.9%)

2012

$3,218 (+10.3%)

2011

$2,919 (+5.4%)

2010

$2,771 (+6.9%)

2009

$2,592

Tax history for 311 Bentons Pleasure Rd

Year

Property tax

Land + Additions

Assessment*

2025

$5,221 (+5.1%)

$193,900 + $405,300

$599,200

2024

$4,966 (+5.2%)

2023

$4,721

$193,800 + $307,400

$501,200

2022

$4,721 (−1.8%)

$193,800 + $307,400

$501,200

2021

$4,807 (−0.3%)

$193,800 + $307,400

$501,200

2020

$4,822 (+11.4%)

$193,800 + $307,400

$501,200

2019

$4,329 (+14.6%)

$193,800 + $309,000

$502,800

2018

$3,776 (+17.2%)

2017

$3,223

$167,800 + $162,000

$329,800

2016

$3,223 (−0.7%)

$167,800 + $162,000

$329,800

2015

$3,246

$167,800 + $164,400

$332,200

2014

$3,246

2013

$3,246 (+0.9%)

2012

$3,218 (+10.3%)

2011

$2,919 (+5.4%)

2010

$2,771 (+6.9%)

2009

$2,592

*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

2.5

Stories

Lot width

—

Lot depth

—

Lot size

1.89 Acres

Year renovated

—

Sq. Ft.

3,389

Year built

1969

Style

Single Family Residential

County

Queen Anne's County

APN

04 057465

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 Attached Garage Spaces: 2
Garage Features: Garage Door Opener, Garage - Side Entry
# of Total Garage and Parking Spaces: 2
Has Garage
# of Garage Spaces: 2
Parking Space # Assigned: 6
Garage
Off Street, Attached Garage

Interior

Virtual Tour

Bedroom Information
# of Bedrooms On 1st Upper Level: 3
# of Bedrooms On Main Level: 1

Bathroom Information
# of Bathrooms (Full) On 1st Upper Level: 2
# of Bathrooms (Half) On Main Level: 1
# of Bathrooms (Half): 1
# of Bathrooms (Full): 2

Interior Information
Appliances: Washer/Dryer Hookups Only, Dishwasher, Dryer - Front Loading, Exhaust Fan, Extra Refrigerator/Freezer, Refrigerator, Washer - Front Loading, Water Heater, Microwave, Oven/Range - Gas
Door Features: French, Six Panel, Sliding Glass
Entry Location: Foyer
Interior Features: Family Room Off Kitchen, Kitchen - Table Space, Dining Area, Kitchen - Eat-In, Master Bath(s), Entry Level Bedroom, Crown Moldings, Wood Floors, Recessed Lighting, Floor Plan - Traditional, Other
Living Area Sq.Ft. Source: Estimated
Wall & Ceiling Types: 9'+ Ceilings

Room Information
Living Room, Dining Room, Master Bedroom, Bedroom 2, Bedroom 3, Kitchen, Game Room, Family Room, Foyer, Laundry, Storage Room, Utility Room, Workshop, Bedroom 6

Fireplace Information
Has Fireplace
# of Fireplaces: 1
Mantel(s), Screen

Basement Information
Basement: Yes
Outside Entrance, Connecting Stairway, Fully Finished, Daylight, Full, Improved

Exterior

Property Information
Improvement Assessed Value: $162,000
Ownership Interest: Fee Simple
Property Condition: Very Good
Year Built Source: Estimated
Year Major Reno/Remodel: 2004

Building Information
Construction Materials: Vinyl Siding, Combination, Brick
Other Structures: Above Grade
Outdoor Living Structures: Patio(s), Porch(es)
Roof: Shingle, Fiberglass
Structure Type: Detached
Window Features: Screens
Other Structures: Shed

Exterior Information
Flood Lights, Sidewalks
Fencing: Partially, Vinyl

Pool Information
Personal Pool
Private Pool
In Ground

Lot Information
Lot Features: Backs to Trees, Corner, Landscaping, Poolside
Tidal Water: No

Land Information
Land Assessed Value: $167,800

Above Grade Information
Finished Sq.Ft.: 3,389
Finished Sq.Ft. Source: Estimated

Financial

Tax Information
County Tax: $3,163.11
Tax Assessed Value: $329,800
Tax Year: 2016
Tax Annual Amount: $3,223.11

Assessments Information
Special Assessment Payment: Annually
Year Assessed: 2017

Utilities

Utilities Information
Central Air
Cooling Type: Ceiling Fan(s), Central A/C
Cooling Fuel: Electric
Hot Water, Forced Air
Heating Fuel: Oil
Hot Water: Oil
Sewer Septic: Public Sewer
Cable TV Available, DSL Available
Water Source: Well

Location

School Information
Elementary School: BAYSIDE
Middle Or Junior School: CALL SCHOOL BOARD
High School: KENT ISLAND
School District Name: QUEEN ANNE'S COUNTY PUBLIC SCHOOLS

Location Information
Directions: Route 50 East to Cox Neck Rd. Exit, turn Right onto Bentons Pleasure Road and follow around to #311 the sprawling property across from the Water!
Road Surface Type: Black Top

Public facts

Beds: —
Baths: 2.5
Sq. Ft.: 3,389
Stories: 2.0
Lot Size: 1.89 acres
Style: Single Family Residential
Year Built: 1969
Year Renovated: —
County: Queen Anne's County
APN: 04 057465

Home facts updated by county records on Jul 17, 2026

Around this home

Schools

Kent Island Elementary School

Public PreK-2 • Assigned • 2.0mi

Matapeake Middle School

Public 6-8 • Assigned • 1.8mi

8/10

Kent Island High School

Public 9-12 • Assigned • 2.8mi

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

78% 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

$741,000 – $897,000

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New listings for sale in 21619

COMING SOON

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12 Queen Anne Way Unit J, Chester, MD 21619

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$350,000

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200 Church St, Chester, MD 21619

(443) 274-1900

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COMING SOON

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OPEN THU, 5PM TO 7PM

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3 beds2.5 baths2,742 sq ft

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3 beds2.5 baths1,302 sq ft

6005 Bridgepointe Dr, Chester, MD 21619

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Home values near 311 Bentons Pleasure Rd

Data from public records.

Address	Redfin Estimate
309 Bentons Pleasure Rd, Chester, MD 3 Beds \| 2 Baths \| 1878 Sq. Ft.	$617,176
325 Bentons Pleasure Rd, Chester, MD - Beds \| 3.5 Baths \| 2939 Sq. Ft.	—

Address	Redfin Estimate
315 Bentons Pleasure Rd, Chester, MD 3 Beds \| 2 Baths \| 1688 Sq. Ft.	—
243 Bentons Pleasure Rd, Chester, MD - Beds \| 2 Baths \| 2033 Sq. Ft.	$676,869

Address	Redfin Estimate
328 Bentons Pleasure Rd, Chester, MD 5 Beds \| 4 Baths \| 3250 Sq. Ft.	$1,973,533
306 Bentons Pleasure Rd, Chester, MD 4 Beds \| 2.5 Baths \| 2793 Sq. Ft.	$1,037,317

Property information provided by BRIGHT MLS when last listed in 2017. 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 21619, MD

Sale history for 311 Bentons Pleasure Rd

Tax history for 311 Bentons Pleasure Rd

Public record

Property details

Around this home

Schools

Lifestyle

Climate risks

Historical weather

Sun exposure

Nearby similar homes

New listings for sale in 21619

Home values near 311 Bentons Pleasure Rd

More real estate resources