This beautifully updated Kent Island retreat in the Benton’s Pleasure community offers space, style, and serenity, with over 2,500 square feet of thoughtfully designed living on more than half an acre. Surrounded by mature landscaping and blooming flowers, the home sits in a peaceful, private setting with no houses directly across the street, just a tranquil view of the woods. Step onto the charming covered front porch, where the home's position offers a sense of seclusion rarely found in a neighborhood setting. Inside, a dramatic two-story foyer welcomes you with light and openness. To the left, the expansive living room features refinished hardwood flooring, crown molding, chair railing, and a cozy fireplace, creating a warm and inviting atmosphere. The living space flows seamlessly into the dining area and kitchen. The kitchen is outfitted with granite countertops, a custom wood breakfast bar, and recently replaced stainless steel appliances. At the back of the home, a stunning sunroom serves as a true showpiece. With its cathedral ceiling and casement windows on three sides, it floods the space with natural light and offers uninterrupted views of the backyard. This space also provides direct access to the composite deck, where indoor-outdoor living comes to life. The backyard is a private, park-like escape. Fully fenced and thoughtfully landscaped, it features a lush lawn, mature trees, and a beautiful apple tree. There are two gates, one recently added, for easy access from either side of the property. A powered storage shed provides additional space for tools, gardening supplies, or hobby gear. The main-level primary bedroom is a peaceful retreat tucked away for privacy. It features a walk-in closet and an en-suite bath with a soaking tub, a separate shower, and recently updated tile. A convenient powder room and laundry room, both with new tile flooring, complete the main level. Vinyl plank stairs lead to three additional bedrooms on the upper level, each with new carpeting. A full bath on this level provides plenty of room for family or guests. The home also includes a spacious two-car garage, a recently replaced well pump, and an encapsulated crawl space for comfort and peace of mind. Beyond the property, Kent Island offers endless opportunities for recreation and relaxation. Take a scenic walk or bike ride on the Cross Island Trail, spend the day at nearby Matapeake State Park with its beach, fishing pier, and dog-friendly area, or launch your boat from one of the many public piers and ramps. Marinas and waterfront dining options are just minutes away, along with a variety of local shops and restaurants that give Chester its small-town charm. From its spacious interior to its peaceful outdoor oasis and unbeatable location, this home truly offers the best of Kent Island living.
$15k Price Improvement Welcome to 106 Woods Drive located in the Benton's Pleasure community of Chester on beautiful Kent Island. You will fall in love with the space - inside and out! Inside, there is 2500+ sq ft of living space and it will be hard to pick a favorite room. Will it be the grand family room with hard wood floors, crown moldings and propane fireplace? The sun room with walls of windows? Or the main floor primary with walk in closet and en suite with walk-in shower plus a soaking tub? There are 3 additional guest rooms plus full bath on the 2nd floor as well. Like the outdoors? Enjoy the sunshine on your new trek deck perfect for grilling and chilling. This home is perfectly situated on over a 1/2 acre that is fully fenced and offers a storage shed. This home is on public sewer and NO HOA. This is a the home you have been waiting for. It's time to make THE SHORE HOME! Call to schedule your showing TODAY!
*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
2
Lot width
—
Lot depth
—
Lot size
0.56 Acres
Year renovated
—
Sq. Ft.
2,551
Year built
2000
Style
Single Family Residential
County
Queen Anne's County
APN
04 112911
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, Garage Door Opener, Inside Access
# of Total Garage and Parking Spaces: 2
Has Garage
# of Garage Spaces: 2
Asphalt Driveway
Attached Garage, Driveway
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: 1
# of Bathrooms (Half) On Main Level: 1
# of Bathrooms (Full) On Main Level: 1
# of Bathrooms (Full) On All Upper Levels: 1
# of Bathrooms (Half): 1
# of Bathrooms (Full): 2
Interior Information
Appliances: Built-In Microwave, Dishwasher, Dryer, Icemaker, Oven - Single, Oven/Range - Electric, Refrigerator, Stainless Steel Appliances, Washer, Water Heater, Disposal