328 Bentons Pleasure Road Chester, MD $ 2,049,000
328 Bentons Pleasure Road
$ 2,049,000
Share Save

328 Bentons Pleasure Road

Chester, MD, 21619
$ 2,049,000
Bedrooms5 Baths4.0 Sq 3,250

Monthly Estimate*

$ 12,938

328 Bentons Pleasure Road, Chester, MD 21619 - Image 1
328 Bentons Pleasure Road, Chester, MD 21619 - Image 2
328 Bentons Pleasure Road, Chester, MD 21619 - Image 3
328 Bentons Pleasure Road, Chester, MD 21619 - Image 4
328 Bentons Pleasure Road, Chester, MD 21619 - Image 5
328 Bentons Pleasure Road, Chester, MD 21619 - Image 6
328 Bentons Pleasure Road, Chester, MD 21619 - Image 7
328 Bentons Pleasure Road, Chester, MD 21619 - Image 8
328 Bentons Pleasure Road, Chester, MD 21619 - Image 9
328 Bentons Pleasure Road, Chester, MD 21619 - Image 10
328 Bentons Pleasure Road, Chester, MD 21619 - Image 11
328 Bentons Pleasure Road, Chester, MD 21619 - Image 12
328 Bentons Pleasure Road, Chester, MD 21619 - Image 13
328 Bentons Pleasure Road, Chester, MD 21619 - Image 14
328 Bentons Pleasure Road, Chester, MD 21619 - Image 15
328 Bentons Pleasure Road, Chester, MD 21619 - Image 16
328 Bentons Pleasure Road, Chester, MD 21619 - Image 17
328 Bentons Pleasure Road, Chester, MD 21619 - Image 18
328 Bentons Pleasure Road, Chester, MD 21619 - Image 19
328 Bentons Pleasure Road, Chester, MD 21619 - Image 20
328 Bentons Pleasure Road, Chester, MD 21619 - Image 21
328 Bentons Pleasure Road, Chester, MD 21619 - Image 22
328 Bentons Pleasure Road, Chester, MD 21619 - Image 23
328 Bentons Pleasure Road, Chester, MD 21619 - Image 24
328 Bentons Pleasure Road, Chester, MD 21619 - Image 25
328 Bentons Pleasure Road, Chester, MD 21619 - Image 26
328 Bentons Pleasure Road, Chester, MD 21619 - Image 27
328 Bentons Pleasure Road, Chester, MD 21619 - Image 28
328 Bentons Pleasure Road, Chester, MD 21619 - Image 29
328 Bentons Pleasure Road, Chester, MD 21619 - Image 30
328 Bentons Pleasure Road, Chester, MD 21619 - Image 31
328 Bentons Pleasure Road, Chester, MD 21619 - Image 32
328 Bentons Pleasure Road, Chester, MD 21619 - Image 33
328 Bentons Pleasure Road, Chester, MD 21619 - Image 34
328 Bentons Pleasure Road, Chester, MD 21619 - Image 35
328 Bentons Pleasure Road, Chester, MD 21619 - Image 36
328 Bentons Pleasure Road, Chester, MD 21619 - Image 37
328 Bentons Pleasure Road, Chester, MD 21619 - Image 38
328 Bentons Pleasure Road, Chester, MD 21619 - Image 39
328 Bentons Pleasure Road, Chester, MD 21619 - Image 40
328 Bentons Pleasure Road, Chester, MD 21619 - Image 41
328 Bentons Pleasure Road, Chester, MD 21619 - Image 42
328 Bentons Pleasure Road, Chester, MD 21619 - Image 43
328 Bentons Pleasure Road, Chester, MD 21619 - Image 44
328 Bentons Pleasure Road, Chester, MD 21619 - Image 45
328 Bentons Pleasure Road, Chester, MD 21619 - Image 46
328 Bentons Pleasure Road, Chester, MD 21619 - Image 47
328 Bentons Pleasure Road, Chester, MD 21619 - Image 48
328 Bentons Pleasure Road, Chester, MD 21619 - Image 49
328 Bentons Pleasure Road, Chester, MD 21619 - Image 50
328 Bentons Pleasure Road, Chester, MD 21619 - Image 51
328 Bentons Pleasure Road, Chester, MD 21619 - Image 52
328 Bentons Pleasure Road, Chester, MD 21619 - Image 53
328 Bentons Pleasure Road, Chester, MD 21619 - Image 54
328 Bentons Pleasure Road, Chester, MD 21619 - Image 55
328 Bentons Pleasure Road, Chester, MD 21619 - Image 56
328 Bentons Pleasure Road, Chester, MD 21619 - Image 57
328 Bentons Pleasure Road, Chester, MD 21619 - Image 58
328 Bentons Pleasure Road, Chester, MD 21619 - Image 59
328 Bentons Pleasure Road, Chester, MD 21619 - Image 60
328 Bentons Pleasure Road, Chester, MD 21619 - Image 61
328 Bentons Pleasure Road, Chester, MD 21619 - Image 62
328 Bentons Pleasure Road, Chester, MD 21619 - Image 63
328 Bentons Pleasure Road, Chester, MD 21619 - Image 64
328 Bentons Pleasure Road, Chester, MD 21619 - Image 65
328 Bentons Pleasure Road, Chester, MD 21619 - Image 66
328 Bentons Pleasure Road, Chester, MD 21619 - Image 67
328 Bentons Pleasure Road, Chester, MD 21619 - Image 68
328 Bentons Pleasure Road, Chester, MD 21619 - Image 69
328 Bentons Pleasure Road, Chester, MD 21619 - Image 70
328 Bentons Pleasure Road, Chester, MD 21619 - Image 71
328 Bentons Pleasure Road, Chester, MD 21619 - Image 72
328 Bentons Pleasure Road, Chester, MD 21619 - Image 73
328 Bentons Pleasure Road, Chester, MD 21619 - Image 74
328 Bentons Pleasure Road, Chester, MD 21619 - Image 75
328 Bentons Pleasure Road, Chester, MD 21619 - Image 76
328 Bentons Pleasure Road, Chester, MD 21619 - Image 77
328 Bentons Pleasure Road, Chester, MD 21619 - Image 78
328 Bentons Pleasure Road, Chester, MD 21619 - Image 79
328 Bentons Pleasure Road, Chester, MD 21619 - Image 80
328 Bentons Pleasure Road, Chester, MD 21619 - Image 81
328 Bentons Pleasure Road, Chester, MD 21619 - Image 82
328 Bentons Pleasure Road, Chester, MD 21619 - Image 83
328 Bentons Pleasure Road, Chester, MD 21619 - Image 84
View a Virtual Tour

Single Family Home for sale in Chester, MD

for $2,049,000 with 5 bedrooms and 4 full baths. This 3,250 square foot home was built in 1953 on a lot size of 1.55.

Gorgeous Waterfront property on Cox Creek with stunning sunset views. Open house Friday June 19, 7:00-8:30 PM for sunset viewing This cottage-style retreat on Cox Creek offers the perfect blend of cozy charm and luxury living. Featuring a refreshing pool (grandfathered in the 100 foot buffer) with 180 degree views, fully equipped gym, 4 garage spaces, dock with 2 boat lifts and jet-ski lift, a versatile guesthouse with full kitchen that sleeps 8, and an outdoor kitchen with Italian pizza oven and Evo grill! The property provides panoramic breathtaking sunset views over the water which makes it the perfect Home for those looking for the ultimate Eastern shore lifestyle! The charming main house, renovated in 2022, with its huge wrap around porch and cozy screened in porch, boasts 3 bedrooms and 3 full baths, expansive windows, high end finishes, custom moldings, and unobstructed water views. The guesthouse, built in 2021 with Full kitchen, living room, and 2 bedrooms and bath, blends character and luxury offering an inviting space with beautiful water views. It comfortably sleeps 8 with king bedroom, and bunk-bedroom with built in bunks. Reclaimed wood floors provide character, blending with the crisp white board-and-batten walls, wood ceilings, and elegant wainscoting molding. Included is a fitness gym featuring top-tier equipment built for rigorous training, and the water views inspire every workout. Guest house was used as a short term rental, generating extra income. The oversized in-ground pool has been extensively renovated to create a true resort-style outdoor experience. Major improvements completed in 2021 included new pool equipment, new plumbing and electric, new tile, a premium pool deck, and sun shelf. Newly resurfaced in 2026 provides years of beauty and enjoyment. Designed for both relaxation and recreation, the pool features an in-water sun shelf with integrated mounts for umbrellas, tables, and seating. Perfectly positioned to capture panoramic Cox Creek views and spectacular sunsets, this exceptional pool setting serves as the focal point of the propertys outdoor living and entertaining spaces, delivering a waterfront resort experience. The guest house is enhanced by a three-car garage configuration consisting of an attached two-car garage and single-car garage, providing exceptional space for vehicles, recreational equipment, and storage. Built-in shelving and storage racks accommodate kayaks, bicycles, and other outdoor gear, making the space ideally suited for an active waterfront lifestyle. In addition, the property includes a separate detached single-car garage offering outstanding flexibility for vehicle storage, a workshop, hobby area, or storage of landscaping and maintenance equipment. The detached garage is equipped with dual 30-amp, 240-volt camper receptacles with weather-protected in-use covers, providing convenient power access for recreational vehicles, trailers, or specialty equipment. Together, these garage facilities provide four enclosed garage bays and abundant storage capacity for vehicles, boats, water toys, outdoor equipment, and workshop needs. The Outdoor kitchen is positioned to capture unobstructed panoramic sunset views of the water, featuring a gas fired Alfa Pizza Oven and a flat top circular EVO cooktop. Its teppanyaki style flattop allows you to sear scallops, stir fry vegetables, or smash burgers facing the water. The private dock with a large over-water entertainment platform, electric, water, decorative lighting, two Magnum boat lifts with remote control, personal watercraft lift, and spectacular western-facing sunset views over Cox Creek. This *must see* home is more than just a house, it's a lifestyle. This property is custom built for family gatherings, entertaining, and endless outdoor recreation: Swimming, Boating, Jet-skiing, Kayaking, Paddle boarding, Yard games, Crabbing and Fishing off the dock, Biking and Pickle ball!

See more

Single Family Pending

Price

$ 2,049,000

Bedrooms

5

Full Bath

4

Property Type

Single Family

Taxes

$ 10,435

Style

Cape Cod

Lot Size

1.55

Year Built

1953

Town/City

Chester

County/Region

Queen Annes

MLS | Web ID

MDQA2017668

Features
General
Living Area 3250
Sewer Public Sewer
Heating Heat Pump - Gas BackUp Heat Pump - Electric BackUp
Cooling Ceiling Fan(s) Central A/C Programmable Thermostat
Utilities Electric Available Sewer Available Water Available
Possession 61-90 Days CD
Roof Architectural Shingle
Appliances Built-In Microwave Dishwasher Disposal Dryer - Front Loading ENERGY STAR Clothes Washer Oven - Double Water Heater - Tankless Energy Efficient Appliances Six Burner Stove Washer - Front Loading Water
Zoning NC-20
Garage Spaces 4.00
Patio/Porch Features Balcony Breezeway Patio(s) Porch(es) Wrap Around Screened Deck(s)
Architectural Style Cape Cod
Pool Features In Ground Permits
Construction Materials Stick Built Vinyl Siding
School District QUEEN ANNE'S COUNTY PUBLIC SCHOOLS
Year Built 1953
View Water
Levels 1.5
Tax Year 2025
Ownership Fee Simple
Cool Fuel Electric
Accessibility None
County QUEEN ANNES
New Construction N
Property Type Residential
HOA N
Subdivision Name NONE AVAILABLE
Facing Direction East
Garage Y/N Y
Water Access Y/N N
Other Structures Above Grade Below Grade
Full Baths 4
Status PENDING
Directions Cox neck take a right on Woods la. house on left
City CHESTER
Senior Community Y/N N
Lot Size Units Square Feet
Lot Size Square Feet 67518.00
Tax Annual Amount 10435.0
Home Warranty Y/N N
Property Condition Excellent
Structure Type Detached
Condo/Coop Association fee Y/N N
Bathrooms Full Main Level 2
Bathrooms Count Main Level 2.00
Price Per Sq Ft Total AG 630.46
Acceptable Financing Cash Conventional
Lease Considered Y/N N
Vacation Rental Y/N N
Virtual Tour https://virtualtours.katseyevirtualtours.com/s/idx/326733
Standard Status Pending
Year Built Source Assessor
Legal Subdivision BENTONS PLEASURE
Tax Lot 1R
See more
Interior
Interior Amenities Carpet Ceiling Fan(s) Combination Dining/Living Crown Moldings Entry Level Bedroom Floor Plan - Open Kitchen - Gourmet Primary Bedroom - Bay Front Recessed Lighting Sprinkler System Upgraded Countert
Heating Fuel Propane - Owned Electric
Basement Daylight Partial Drainage System Outside Entrance Sump Pump
Flooring Carpet Hardwood
Total Fireplaces 3
Fireplace Features Gas/Propane
Hot Water Instant Hot Water Oil
Basement (Y/N) Y
Heating Y/N Y
Fireplace Y/N Y
Above Grade Finished Area 3250
Central Air Y/N Y
Total Bedrooms 5
Below Grade Finished Area 0
Main Level Bedrooms 2
Below Grade Finished Area Unit Type Square Feet
Laundry Type Basement Main Floor
Below Grade Finished Area Source Assessor
Above Grade Finished Area Source Estimated
Above Grade Finished Area Unit Type Square Feet
Total Baths 4
See more
Exterior
Exterior Amenities BBQ Grill Boat Storage Exterior Lighting Outbuilding(s) Secure Storage Other
Pool Yes - Personal
Fencing Partially
Water Source Well
Inclusions Gym equipment other than several sets of dumbells and 2 mats All blinds Matching quilts for the bunk bed room
Garage Features Garage Door Opener
Type of Parking Attached Garage Detached Garage
Foundation Details Block Slab
Water View Y/N Y
Lot Size Acres 1.55
Road Surface Type Paved
Lot Size Source Assessor
Waterfront Y/N N
Land Assessed Value 513700.00
Navigable Water Y/N N
Water Oriented Y/N N
See more
Internal Only
Street Number 1 328
See more
* Excluded Features
List By
Homezu By Simple Choice

Broker

support@simplechoicerealty.com

Email

Affordability Calculator

$13,807
Per Month
94%
6%
0%
Monthly Principal & Interest
$12,938
Monthly Property Taxes
$870
Monthly Home Insurance
--
Default based on a 30-year fixed rate of 6.49% with 20% down. The estimated payment is offered for convenience and is not an offer of credit. Due to market fluctuations, interest rates are subject to change at any time and without notice. Your individual rate may vary. Rates may differ for FHA, VA or jumbo loans.
Learn more about how to save

Discover how much house you can afford

Your dream home may be within reach.

Learn More about how to save

The time to sell is now
THE TIME TO SELL IS NOW! What's my home worth?
Nearby
3536296 Elementary School
3535811 Middle School
Kent Island High School High School
Pricing History
DatePricePrice ChangeDescription
6/15/2026$2,049,000 Listed Price

Map


See all

328 Bentons Pleasure Road, Chester, MD, 21619 is a Single Family Home for sale at $2,049,000 with 3,250 sqft and a lot size of 1.55. 328 Bentons Pleasure Road has 5 bedrooms, 4.0 baths, and was built in 1953. The property's zip code is 21619 which is in Chester, MD