OFF MARKET

Off Market Jun 2024 for $1.3M

$1,510,490

Est. refi paymentEst. refi $8,668/mo

•

3,571

sq ft

228 Bentons Pleasure Rd, Chester, MD 21619

About this home

WOAH!! Just in time for waterfront season, this stunning custom-built home features a private pier with BOAT LIFT & JET SKI LIFT ready for emdless adventures. Featuring primary suites on both levels, this 3200 SF home is exactly what you've been searching for to enjoy life on Maryland's Eastern Shore. Views of Cox Creek greet you from the minute you step through the front door! The great room features a wall of French Doors to maximize the view, vauled ceilings and a gorgeous stone fireplace--one of 4 fire places in the house. Large eat in kitchen has lots of seating at the sprawling island and table space that soaks in the view. Seperate den offers another cozy space to relax. Main level primary suite is creek side and has slider access to waterside patio, fire place and large walk in closet. Upstairs the catwalk overlooks the great room. One side side is the second primary suite also with fire place and features a charming screened porch balcony. On the other side of the upper level there are two bedrooms connected by a Jack N Jill bathroom. If you need storage, there is a huge unfinished room above the garage for all your treasures. Oversized attached 2 car garage, too and for your best buddy, an invisible fence. GEMS like this one don't come around very often. Get in and start enjoying your best shore life!

Single-familyProperty Type

2005Year Built

0.61 acresLot Size

$423Est. Price/Sq.Ft.

2 car garageParking

Listed by Tricia Z Wilson • Chaney Homes, LLC

•443-249-7653 (broker)

•jchaney@chaneyhomes.com (broker)

Bought with Jimmy White • Long & Foster Real Estate, Inc.

•410-643-2244 (broker)

Redfin checked: 2 minutes ago

•Source:BRIGHT MLS #MDQA2009608

Redfin Estimate

$1,510,490

$155K since sold in June 2024$20K since August

Recently sold homes
Estimate history
Homes for sale

This home's estimate is 78.8% higher than the average sale price ($845K) of 6 comparable homes.

SOLD NOV 7, 2025
$700,000
A
4 beds3 baths2,868 sq ft
419 Creeks End Ln, Stevensville, MD 21666
SOLD JUL 17, 2026
$1,300,000
B
3 beds4 baths4,208 sq ft
1719 Harbor Dr, Chester, MD 21619
SOLD DEC 10, 2025
$795,000
C
5 beds3.5 baths3,065 sq ft
104 Woods Rd, Chester, MD 21619
SOLD FEB 26, 2026
$895,000
D
5 beds4 baths4,275 sq ft
115 Cedar Rd, Chester, MD 21619
SOLD JAN 9, 2026
$740,000
E
4 beds2.5 baths2,791 sq ft
123 Bentons Pleasure Rd, 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

$380,703

Est. take-home

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Refinance

Est. cash available

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Rent

$4,247/mo

Redfin rental estimate

List your home for rent

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

COMING SOON
$550,000
5 beds3.5 baths3,552 sq ft
326 Castle Marina Rd, Chester, MD 21619
(410) 643-5005
COMING SOON
$350,000
2 beds2 baths1,274 sq ft
200 Church St, Chester, MD 21619
(443) 274-1900
OPEN SAT, 11AM TO 1PM
$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
COMING SOON
$439,000
3 beds3 baths1,750 sq ft
41-D Queen Catherine Ct, Chester, MD 21619
(410) 465-1770
$569,900
4 beds2.5 baths2,332 sq ft
233 Cross Creek Ct, Chester, MD 21619
(301) 340-8700
$1,290,000
5 beds2 baths2,700 sq ft
2513 Cecil Dr, Chester, MD 21619
(855) 450-0442
See all

Provided by Redfin

Sale history for 228 Bentons Pleasure Rd

Date

Event

Price

BRIGHT MLS #MDQA2009608

Jun 17, 2024

Sold

$1,355,000

$379/sq ft

May 5, 2024

Pending

—

May 3, 2024

Listed

$1,250,000

$350/sq ft

Apr 26, 2024

Coming Soon

$1,250,000

$350/sq ft

BRIGHT MLS #MDQA143022

Oct 9, 2020

Sold

$1,070,000

$300/sq ft

Sep 28, 2020

Pending

—

Aug 28, 2020

Contingent

—

Aug 17, 2020

Relisted

—

Aug 16, 2020

Pending

—

Apr 10, 2020

Relisted

—

Mar 30, 2020

Listing Removed

—

Feb 21, 2020

Listed

$1,075,000

$301/sq ft

+79

Summer Is HERE!! . .. Better Hurry to This GORGEOUS Custom-Built Kent Island WATERFRONT! It's what 'Island Living' is All About! Private Pier, w/ Boat Lift & Jet Ski Lift Just Begging For Playtime! Boating, Jet Ski, Crabbing, Fishing- all from your back door! Your Private Island Oasis! Million-Dollar Sunsets & SPACE! Boasting Over 3200 sq ft of Exquisite Craftsmanship, Millwork & Style- the Open, Generously Sized Floor-Plan Affords Something for All! Inviting, 2-Story Foyer Greets Guests, Leading to Spacious Family Room w/ Wall of French Doors to Stunning Waterfront Views! Stacked Stone Gas Fireplace is one of FOUR for Cozy Nights! Gourmet Kitchen w/ Gleaming Granite, Custom Cabinetry & Large Breakfast Bar Opens to Morning Room w/ Table Space for Waterfront Dining! Main-Level Master Suite w/ Fireplace & Sliders to Private Waterfront Patio! Spa-Like Master Bath & Huge Walk-in-Closet! Main-Level Den w/ Fireplace & Built-Ins Makes Perfect Office or Tucked-in Sanctuary! 3 Upper-Level Bedrooms Each Attached to Full Bath are accessed over Catwalk w/ Inescapable Water-Views! Private Waterfront Balcony off 2nd Bedroom will have Guests Never Wanting to Leave! Large Private Bath & Fireplace. Jack-and-Jill shared Full Bath for Large 3rd/4th Bedrooms. Ample Storage! Over-Sized 2-Car Garage, Walk-in-Storage Room Above & Generously-Sized Closets Throughout! 10 Mins from Bay Bridge- 1-Hr DC. 20 Mins by Boat to St Michaels! Claim this Stylish Beauty Soon. .. Before your competition is living YOUR Waterfront Dream!

BRIGHT MLS #MDQA137238

Nov 25, 2019

Listing Removed

—

Oct 23, 2019

Price Changed

$1,089,000

$305/sq ft

Sep 5, 2019

Price Changed

$1,139,000

$319/sq ft

Apr 1, 2019

Listed

$1,199,000

$336/sq ft

BRIGHT MLS #1009914480

Dec 22, 2018

Listing Removed

—

Oct 11, 2018

Listed

$1,225,000

$343/sq ft

Public Records

Sep 20, 2012

Sold

$1,120,000

$314/sq ft

MRIS #QA7859032

Aug 30, 2012

Delisted

—

Aug 30, 2012

Sold

$1,120,000

$314/sq ft

Jul 31, 2012

Pending

—

Jun 7, 2012

Listed

$361/sq ft

BRIGHT MLS #1004022908

Aug 30, 2012

Sold

$1,120,000

$314/sq ft

Jul 30, 2012

Listing Removed

—

Jun 7, 2012

Listed

$1,290,000

$361/sq ft

BRIGHT MLS #1009306044

Jan 5, 2012

Listing Removed

—

Jan 25, 2011

Listed

$1,290,000

$361/sq ft

MRIS #QA7518965

Jan 5, 2012

Delisted

—

May 16, 2011

Price Changed

Jan 25, 2011

Relisted

—

Jan 25, 2011

Listed

Jan 25, 2011

Delisted

—

MRIS #QA7427772

Jan 7, 2011

Delisted

—

Dec 1, 2010

Price Changed

Sep 21, 2010

Price Changed

Sep 3, 2010

Relisted

—

Sep 3, 2010

Delisted

—

Sep 2, 2010

Listed

MRIS #QA7119373

Nov 23, 2009

Delisted

—

Jul 27, 2009

Listed

BRIGHT MLS #1008894920

Nov 23, 2009

Listing Removed

—

Jul 27, 2009

Listed

$1,629,000

$456/sq ft

Public Records

Jul 27, 2004

Sold

$280,000

$78/sq ft

** Price available after signing in.

Year

Property tax

Land + Additions

Assessment*

2025

$11,794 (+9.4%)

$463,800 + $895,300

$1,359,100

2024

$10,786 (+10.3%)

2023

$9,777

$347,800 + $690,100

$1,037,900

2022

$9,777 (−1.8%)

$347,800 + $690,100

$1,037,900

2021

$9,955 (−2.9%)

$347,800 + $690,100

$1,037,900

2020

$10,255

$347,800 + $690,100

$1,037,900

2019

$10,255

$376,100 + $693,100

$1,069,200

2018

$10,255 (−4.6%)

$376,100 + $693,100

$1,069,200

2017

$10,745

$372,100 + $748,200

$1,120,300

2016

$10,744 (−2.2%)

$372,100 + $748,200

$1,120,300

2015

$10,985

$378,900 + $766,500

$1,145,400

2014

$10,986 (+1.3%)

2013

$10,841 (+1.9%)

2012

$10,638 (+10.1%)

2011

$9,665 (+5.2%)

2010

$9,189 (+5.6%)

2009

$8,700

Tax history for 228 Bentons Pleasure Rd

Year

Property tax

Land + Additions

Assessment*

2025

$11,794 (+9.4%)

$463,800 + $895,300

$1,359,100

2024

$10,786 (+10.3%)

2023

$9,777

$347,800 + $690,100

$1,037,900

2022

$9,777 (−1.8%)

$347,800 + $690,100

$1,037,900

2021

$9,955 (−2.9%)

$347,800 + $690,100

$1,037,900

2020

$10,255

$347,800 + $690,100

$1,037,900

2019

$10,255

$376,100 + $693,100

$1,069,200

2018

$10,255 (−4.6%)

$376,100 + $693,100

$1,069,200

2017

$10,745

$372,100 + $748,200

$1,120,300

2016

$10,744 (−2.2%)

$372,100 + $748,200

$1,120,300

2015

$10,985

$378,900 + $766,500

$1,145,400

2014

$10,986 (+1.3%)

2013

$10,841 (+1.9%)

2012

$10,638 (+10.1%)

2011

$9,665 (+5.2%)

2010

$9,189 (+5.6%)

2009

$8,700

*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

3.5

Stories

Lot width

—

Lot depth

—

Lot size

0.61 Acres

Year renovated

—

Sq. Ft.

3,571

Year built

2005

Style

Single Family Residential

County

Queen Anne's County

APN

04 075870

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 - Front Entry
# of Total Garage and Parking Spaces: 2
Has Garage
# of Garage Spaces: 2
Attached Garage

Interior

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 (Full) On Main Level: 1
# of Bathrooms (Full) On All Upper Levels: 2
# of Bathrooms (Half): 1
# of Bathrooms (Full): 3

Interior Information
Appliances: Built-In Microwave, Cooktop, Dishwasher, Dryer, Oven - Wall, Refrigerator, Washer, Water Heater
Interior Features: Breakfast Area, CeilngFan(s), Kitchen - Eat-In, Kitchen - Island, Master Bath(s), Master Bedroom - Bay Front
Living Area Sq.Ft. Source: Assessor

Room Information
Living Room, Master Bedroom, Bedroom 2, Bedroom 3, Kitchen, Den, Foyer, Breakfast Room, Laundry, Bathroom 2, Bathroom 3, Master Bathroom, Half Bath

Fireplace Information
Has Fireplace
# of Fireplaces: 4
Gas/Propane

Basement Information
Basement: No

Exterior

Property Information
Total Below Grade Sq. Ft.: 0
Accessibility Features: Entry Slope <1'
Improvement Assessed Value: $690,100
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: Asphalt, Shingle
Structure Type: Detached

Lot Information
Navigable Water
Water Frontage In Feet: 97
Tidal Water: Yes

Land Information
Land Assessed Value: $347,800

Dock Information
Dock Type and Features: Private, Hoist/Lift Electric
Dock/Slip Conveyance: Deeded
# of Docks: 1
Dock/Slip Conveys: Yes

Above Grade Information
Finished Sq.Ft.: 3,571
Finished Sq.Ft. Source: Assessor

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

Financial

Tax Information
County Tax: $9,777
Tax Assessed Value: $1,037,900
Tax Year: 2023
Tax Annual Amount: $9,777

Assessments Information
Year Assessed: 2023

Utilities

Utilities Information
Central Air
Cooling Type: Central A/C, Heat Pump(s)
Cooling Fuel: Electric
Heat Pump - Gas BackUp
Heating Fuel: Electric, Propane - Leased
Hot Water: Electric
Sewer Septic: Public Sewer
Water Source: Public

Location

School Information
Elementary School: KENT ISLAND
Middle Or Junior School: STEVENSVILLE
High School: KENT ISLAND
School District Name: QUEEN ANNE'S COUNTY PUBLIC SCHOOLS
Elementary School Source: Listing Agent
Middle School Source: Listing Agent
High School Source: Listing Agent
School District Source: Listing Agent

Location Information
Outside City Limits
Directions: From Rt 50 East, Take Exit 39 A Cox Creek South, make a RIGHT on Bentons Pleasure. Property will be on your RIGHT.
Mean Low Water Feet: 3

Waterfrontage Information
Water Access Features: Boat - Powered, Canoe/Kayak, Personal Watercraft (PWC), Waterski/Wakeboard
Water Access
Private Dock Site
On Waterfront
Water Oriented
Water Body Type: Creek
Water Body Name: Cox Creek

Public facts

Beds: —
Baths: 3.5
Sq. Ft.: 3,571
Stories: 2.0
Lot Size: 0.61 acres
Style: Single Family Residential
Year Built: 2005
Year Renovated: —
County: Queen Anne's County
APN: 04 075870

Home facts updated by county records on Jul 17, 2026

Around this home

Schools

Kent Island Elementary School

Public PreK-2 • Assigned • 1.7mi

Matapeake Middle School

Public 6-8 • Assigned • 1.7mi

8/10

Kent Island High School

Public 9-12 • Assigned • 2.5mi

6/10

Provided by GreatSchools

Lifestyle

Provided by Walk Score and Local Logic

Climate risks

5/10 Flood Factor

Estimated 17-25% chance 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

7/10 Wind Factor

79% 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

$1.44M – $1.74M

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New listings for sale in 21619

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5 beds3.5 baths3,250 sq ft

1868 Roberta Dr, Chester, MD 21619

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COMING SOON

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3 beds2.5 baths2,742 sq ft

1717 Harbor Dr, Chester, MD 21619

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EARLY ACCESSCOMPASS COMING SOON

$450,000

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COMING SOON

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3 beds3 baths1,750 sq ft

41-D Queen Catherine Ct, Chester, MD 21619

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Home values near 228 Bentons Pleasure Rd

Data from public records.

Address	Redfin Estimate
230 Bentons Pleasure Rd, Chester, MD 5 Beds \| 4 Baths \| 3802 Sq. Ft.	$2,017,684
237 Bentons Pleasure Rd, Chester, MD 5 Beds \| 3 Baths \| 2184 Sq. Ft.	$603,344

Address	Redfin Estimate
213 Bentons Pleasure Rd, Chester, MD - Beds \| 2 Baths \| 1880 Sq. Ft.	$688,315
222 Bentons Pleasure Rd, Chester, MD - Beds \| 2 Baths \| 2272 Sq. Ft.	$748,057

Address	Redfin Estimate
219 Bentons Pleasure Rd, Chester, MD 4 Beds \| 2 Baths \| 2084 Sq. Ft.	$649,815
236 Bentons Pleasure Rd, Chester, MD - Beds \| 2 Baths \| 2030 Sq. Ft.	$978,948

Property information provided by BRIGHT MLS when last listed in 2024. 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 228 Bentons Pleasure Rd

Tax history for 228 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 228 Bentons Pleasure Rd

More real estate resources