
106 Woods Rd Chester, MD 21619
Highlights
- View of Trees or Woods
- 0.56 Acre Lot
- Colonial Architecture
- Bayside Elementary School Rated A-
- Open Floorplan
- Deck
About This Home
As of June 2025This 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.
Last Buyer's Agent
Ari Musliu
Redfin Corp License #674452

Home Details
Home Type
- Single Family
Est. Annual Taxes
- $4,343
Year Built
- Built in 2000
Lot Details
- 0.56 Acre Lot
- Split Rail Fence
- Landscaped
- Back Yard Fenced, Front and Side Yard
- Property is in excellent condition
- Property is zoned NC-20
Parking
- 2 Car Direct Access Garage
- Front Facing Garage
- Garage Door Opener
- Driveway
Property Views
- Woods
- Garden
Home Design
- Colonial Architecture
- Vinyl Siding
Interior Spaces
- 2,551 Sq Ft Home
- Property has 2 Levels
- Open Floorplan
- Chair Railings
- Crown Molding
- Cathedral Ceiling
- Ceiling Fan
- Recessed Lighting
- Fireplace Mantel
- Gas Fireplace
- Double Pane Windows
- Vinyl Clad Windows
- Casement Windows
- Window Screens
- Atrium Doors
- Six Panel Doors
- Entrance Foyer
- Living Room
- Dining Room
- Sun or Florida Room
- Crawl Space
- Fire and Smoke Detector
- Attic
Kitchen
- Breakfast Area or Nook
- Eat-In Kitchen
- Electric Oven or Range
- Built-In Microwave
- Ice Maker
- Dishwasher
- Stainless Steel Appliances
- Upgraded Countertops
- Disposal
Flooring
- Wood
- Carpet
- Laminate
- Ceramic Tile
- Luxury Vinyl Plank Tile
Bedrooms and Bathrooms
- En-Suite Primary Bedroom
- En-Suite Bathroom
- Walk-In Closet
- Soaking Tub
- Bathtub with Shower
Laundry
- Laundry Room
- Laundry on main level
- Dryer
- Washer
Outdoor Features
- Deck
- Storage Shed
- Porch
Schools
- Matapeake Middle School
- Kent Island High School
Utilities
- Central Air
- Heat Pump System
- Well
- Electric Water Heater
Community Details
- No Home Owners Association
- Bentons Pleasure Subdivision, Colonial Floorplan
Listing and Financial Details
- Tax Lot 94B
- Assessor Parcel Number 1804112911
Ownership History
Purchase Details
Home Financials for this Owner
Home Financials are based on the most recent Mortgage that was taken out on this home.Purchase Details
Home Financials for this Owner
Home Financials are based on the most recent Mortgage that was taken out on this home.Purchase Details
Home Financials for this Owner
Home Financials are based on the most recent Mortgage that was taken out on this home.Purchase Details
Home Financials for this Owner
Home Financials are based on the most recent Mortgage that was taken out on this home.Purchase Details
Home Financials for this Owner
Home Financials are based on the most recent Mortgage that was taken out on this home.Purchase Details
Similar Homes in Chester, MD
Home Values in the Area
Average Home Value in this Area
Purchase History
Date | Type | Sale Price | Title Company |
---|---|---|---|
Deed | $650,000 | First American Title | |
Deed | $575,000 | Rextar Title | |
Deed | $440,000 | Liberty T&E Of Md Llc | |
Deed | $457,500 | -- | |
Deed | $457,500 | -- | |
Deed | $234,926 | -- |
Mortgage History
Date | Status | Loan Amount | Loan Type |
---|---|---|---|
Open | $487,500 | New Conventional | |
Previous Owner | $380,000 | New Conventional | |
Previous Owner | $374,000 | New Conventional | |
Previous Owner | $354,808 | Stand Alone Second | |
Previous Owner | $368,000 | Stand Alone Refi Refinance Of Original Loan | |
Previous Owner | $91,500 | Purchase Money Mortgage | |
Previous Owner | $366,000 | Purchase Money Mortgage | |
Previous Owner | $366,000 | Purchase Money Mortgage | |
Closed | -- | No Value Available |
Property History
Date | Event | Price | Change | Sq Ft Price |
---|---|---|---|---|
06/26/2025 06/26/25 | Sold | $650,000 | -1.5% | $255 / Sq Ft |
05/20/2025 05/20/25 | Price Changed | $659,900 | -1.5% | $259 / Sq Ft |
05/08/2025 05/08/25 | For Sale | $670,000 | +16.5% | $263 / Sq Ft |
08/31/2022 08/31/22 | Sold | $575,000 | -1.7% | $221 / Sq Ft |
08/11/2022 08/11/22 | Pending | -- | -- | -- |
08/08/2022 08/08/22 | Price Changed | $585,000 | -1.7% | $225 / Sq Ft |
07/22/2022 07/22/22 | Price Changed | $595,000 | -0.8% | $229 / Sq Ft |
06/09/2022 06/09/22 | For Sale | $600,000 | +36.4% | $231 / Sq Ft |
03/26/2019 03/26/19 | Sold | $440,000 | -2.2% | $169 / Sq Ft |
02/09/2019 02/09/19 | Pending | -- | -- | -- |
01/22/2019 01/22/19 | Price Changed | $450,000 | -5.3% | $173 / Sq Ft |
10/22/2018 10/22/18 | For Sale | $475,000 | -- | $183 / Sq Ft |
Tax History Compared to Growth
Tax History
Year | Tax Paid | Tax Assessment Tax Assessment Total Assessment is a certain percentage of the fair market value that is determined by local assessors to be the total taxable value of land and additions on the property. | Land | Improvement |
---|---|---|---|---|
2025 | $4,343 | $506,567 | $0 | $0 |
2024 | $4,343 | $461,033 | $0 | $0 |
2023 | $3,914 | $415,500 | $173,900 | $241,600 |
2022 | $3,914 | $415,500 | $173,900 | $241,600 |
2021 | $3,985 | $415,500 | $173,900 | $241,600 |
2020 | $4,064 | $437,800 | $173,900 | $263,900 |
2019 | $3,853 | $401,767 | $0 | $0 |
2018 | $3,508 | $365,733 | $0 | $0 |
2017 | $3,152 | $329,700 | $0 | $0 |
2016 | -- | $328,667 | $0 | $0 |
2015 | $1,780 | $327,633 | $0 | $0 |
2014 | $1,780 | $326,600 | $0 | $0 |
Agents Affiliated with this Home
-
Seller's Agent in 2025
Jackie Ball Daley
Creig Northrop Team of Long & Foster
(443) 622-3022
10 in this area
157 Total Sales
-
A
Buyer's Agent in 2025
Ari Musliu
Redfin Corp
-
Seller's Agent in 2022
Kathleen Higginbotham
Keller Williams Flagship
(301) 370-5696
46 in this area
180 Total Sales
-
F
Buyer's Agent in 2022
Frances Middleton
Douglas Realty, LLC
(443) 310-9000
3 in this area
7 Total Sales
-
Seller's Agent in 2019
Linda Austin
Long & Foster
(410) 604-6330
12 in this area
98 Total Sales
-
Buyer's Agent in 2019
Rick Parreco
RE/MAX
(410) 703-4315
12 in this area
81 Total Sales
Map
Source: Bright MLS
MLS Number: MDQA2013010

APN: 04-112911
- 104 Woods Rd
- Lot 53 Woods Rd
- 0 Parks Rd
- 203 Riverside Dr
- 0 Bentons Pleasure Rd Unit MDQA2010470
- 203 Barren Ridge Rd
- 1757 Harbor Dr
- 1771 Harbor Dr
- 1405 Little Creek Rd
- 1773 Harbor Dr
- 2653 Cox Neck Rd
- 2008 Palm Dr
- 1872 Harbor Dr
- 720 Thompson Creek Rd
- 1906 Harbor Dr
- 602 Dominion Rd
- 455 Creeks End Ln
- 18 Mariners Way Unit 4
- 7B Mariners Way
- 2723 Cox Neck Rd