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.
Sold for $650,000
$650,000
106 Woods Rd, Chester, MD 21619
4beds
2,551sqft
Single Family Residence
Built in 2000
0.56 Acres Lot
$681,100 Zestimate®
$255/sqft
$3,774 Estimated rent
Home value
$681,100
$572,000 - $811,000
$3,774/mo
Zestimate® history
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$3,901/mo
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Est. payment
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List your homeWhat's special
Cozy fireplaceLush lawnBlooming flowersWalk-in closetPeaceful private settingMature landscapingDramatic two-story foyer
Zillow last checked:
Listing updated:
Listed by:
Jackie Daley 443-622-3022,
Northrop Realty
Bought with:
Ari Musliu, 674452
Redfin Corp
Source: Bright MLS,MLS#: MDQA2013010
Facts & features
Interior
Bedrooms & bathrooms
- Bedrooms: 4
- Bathrooms: 3
- Full bathrooms: 2
- 1/2 bathrooms: 1
- Main level bathrooms: 2
- Main level bedrooms: 1
Rooms
- Room types: Living Room, Dining Room, Primary Bedroom, Bedroom 2, Bedroom 3, Bedroom 4, Kitchen, Foyer, Sun/Florida Room, Laundry
Primary bedroom
- Features: Flooring - Laminate Plank, Attached Bathroom, Ceiling Fan(s), Walk-In Closet(s)
- Level: Main
- Area: 225 Square Feet
- Dimensions: 15 x 15
Bedroom 2
- Features: Flooring - Carpet, Ceiling Fan(s)
- Level: Upper
- Area: 120 Square Feet
- Dimensions: 16 X 12
Bedroom 3
- Features: Flooring - Carpet, Ceiling Fan(s)
- Level: Upper
- Area: 120 Square Feet
- Dimensions: 11 X 10
Bedroom 4
- Features: Flooring - Carpet
- Level: Upper
- Area: 208 Square Feet
- Dimensions: 11 X 10
Dining room
- Features: Flooring - Luxury Vinyl Plank, Chair Rail, Crown Molding
- Level: Main
- Area: 144 Square Feet
- Dimensions: 12 x 12
Foyer
- Features: Flooring - HardWood, Crown Molding
- Level: Main
- Area: 91 Square Feet
- Dimensions: 13 x 7
Kitchen
- Features: Flooring - Luxury Vinyl Plank, Granite Counters, Breakfast Bar
- Level: Main
- Area: 165 Square Feet
- Dimensions: 15 x 11
Laundry
- Features: Flooring - Ceramic Tile
- Level: Main
- Area: 42 Square Feet
- Dimensions: 7 x 6
Living room
- Features: Flooring - HardWood, Ceiling Fan(s), Chair Rail, Crown Molding, Fireplace - Gas
- Level: Main
- Area: 352 Square Feet
- Dimensions: 22 x 16
Other
- Features: Flooring - Luxury Vinyl Plank, Cathedral/Vaulted Ceiling
- Level: Main
- Area: 322 Square Feet
- Dimensions: 23 x 14
Heating
- Heat Pump, Electric
Cooling
- Central Air, Electric
Appliances
- Included: Microwave, Dishwasher, Dryer, Ice Maker, Oven, Oven/Range - Electric, Refrigerator, Stainless Steel Appliance(s), Washer, Water Heater, Disposal, Electric Water Heater
- Laundry: Has Laundry, Main Level, Laundry Room
Features
- Attic, Soaking Tub, Bathroom - Tub Shower, Ceiling Fan(s), Chair Railings, Combination Kitchen/Dining, Combination Dining/Living, Crown Molding, Dining Area, Entry Level Bedroom, Open Floorplan, Eat-in Kitchen, Kitchen - Table Space, Primary Bath(s), Recessed Lighting, Upgraded Countertops, Walk-In Closet(s), Breakfast Area, 9'+ Ceilings, 2 Story Ceilings, Cathedral Ceiling(s), Dry Wall, High Ceilings
- Flooring: Carpet, Ceramic Tile, Laminate, Luxury Vinyl, Wood
- Doors: Atrium, Six Panel
- Windows: Casement, Double Pane Windows, Screens, Vinyl Clad
- Has basement: No
- Number of fireplaces: 1
- Fireplace features: Mantel(s), Gas/Propane
Interior area
- Total structure area: 2,551
- Total interior livable area: 2,551 sqft
- Finished area above ground: 2,551
- Finished area below ground: 0
Property
Parking
- Total spaces: 2
- Parking features: Garage Faces Front, Garage Door Opener, Inside Entrance, Asphalt, Attached, Driveway
- Attached garage spaces: 2
- Has uncovered spaces: Yes
Accessibility
- Accessibility features: Other
Features
- Levels: Two
- Stories: 2
- Patio & porch: Deck, Porch
- Pool features: None
- Fencing: Back Yard,Split Rail
- Has view: Yes
- View description: Garden, Trees/Woods
Lot
- Size: 0.56 Acres
- Features: Front Yard, Landscaped, Rear Yard, SideYard(s)
Details
- Additional structures: Above Grade, Below Grade
- Parcel number: 1804112911
- Zoning: NC-20
- Special conditions: Standard
Construction
Type & style
- Home type: SingleFamily
- Architectural style: Colonial
- Property subtype: Single Family Residence
Materials
- Vinyl Siding
- Foundation: Other, Crawl Space
Condition
- Excellent
- New construction: No
- Year built: 2000
Details
- Builder model: COLONIAL
Utilities & green energy
- Sewer: Public Sewer
- Water: Well
Community & HOA
Community
- Security: Main Entrance Lock, Smoke Detector(s)
- Subdivision: Bentons Pleasure
HOA
- Has HOA: No
Location
- Region: Chester
Financial & listing details
- Price per square foot: $255/sqft
- Tax assessed value: $506,567
- Annual tax amount: $4,343
- Date on market: 5/8/2025
- Listing agreement: Exclusive Right To Sell
- Ownership: Fee Simple
Price history
| Date | Event | Price |
|---|---|---|
| 6/26/2025 | Sold | $650,000-1.5%$255/sqft |
Source:  Bright MLS #MDQA2013010 Report a problem | ||
| 5/30/2025 | Contingent | $659,900$259/sqft |
Source: Bright MLS #MDQA2013010 Report a problem | ||
| 5/20/2025 | Price change | $659,900-1.5%$259/sqft |
Source: Bright MLS #MDQA2013010 Report a problem | ||
| 5/8/2025 | Listed for sale | $670,000+16.5%$263/sqft |
Source: Bright MLS #MDQA2013010 Report a problem | ||
| 8/31/2022 | Sold | $575,000-1.7%$225/sqft |
Source: Bright MLS #MDQA2003772 Report a problem | ||
| 8/29/2022 | Pending sale | $585,000$229/sqft |
Source: Bright MLS #MDQA2003772 Report a problem | ||
| 8/11/2022 | Contingent | $585,000$229/sqft |
Source: Bright MLS #MDQA2003772 Report a problem | ||
| 8/8/2022 | Price change | $585,000-1.7%$229/sqft |
Source: Bright MLS #MDQA2003772 Report a problem | ||
| 7/22/2022 | Price change | $595,000-0.8%$233/sqft |
Source: Bright MLS #MDQA2003772 Report a problem | ||
| 6/9/2022 | Listed for sale | $600,000+36.4%$235/sqft |
Source: Bright MLS #MDQA2003772 Report a problem | ||
| 4/5/2019 | Sold | $440,000-2.2%$172/sqft |
Source: Public Record Report a problem | ||
| 2/10/2019 | Pending sale | $450,000$176/sqft |
Source: Long & Foster Real Estate, Inc. #1009972750 Report a problem | ||
| 1/23/2019 | Price change | $450,000-5.3%$176/sqft |
Source: Long & Foster Real Estate, Inc. #1009972750 Report a problem | ||
| 10/24/2018 | Price change | $475,000+1.1%$186/sqft |
Source: Long & Foster Real Estate, Inc. #1009972750 Report a problem | ||
| 10/9/2018 | Price change | $469,900-1.1%$184/sqft |
Source: Glen Burnie - WEICHERT, REALTORS - Platinum Service #1002278600 Report a problem | ||
| 9/19/2018 | Price change | $474,900-3.1%$186/sqft |
Source: Glen Burnie - WEICHERT, REALTORS - Platinum Service #1002278600 Report a problem | ||
| 8/29/2018 | Listed for sale | $489,900+7.1%$192/sqft |
Source: Weichert, Realtors Platinum Service #1002278600 Report a problem | ||
| 4/30/2007 | Sold | $457,500+94.7%$179/sqft |
Source: Public Record Report a problem | ||
| 7/2/2001 | Sold | $234,926$92/sqft |
Source: Public Record Report a problem | ||
Public tax history
| Year | Property taxes | Tax assessment |
|---|---|---|
| 2025 | $4,772 +9.9% | $506,567 +9.9% |
| 2024 | $4,343 +11% | $461,033 +11% |
| 2023 | $3,914 | $415,500 |
| 2022 | $3,914 -1.8% | $415,500 |
| 2021 | $3,985 -5.1% | $415,500 -5.1% |
| 2020 | $4,199 +9% | $437,800 |
| 2019 | $3,853 +9.9% | $437,800 +19.7% |
| 2018 | $3,508 +8.9% | $365,733 +10.9% |
| 2017 | $3,222 +81% | $329,700 +0.3% |
| 2016 | $1,780 | $328,667 +0.3% |
| 2015 | $1,780 | $327,633 +0.3% |
| 2014 | $1,780 | $326,600 |
| 2013 | -- | $326,600 +0.1% |
| 2012 | -- | $326,300 -15.8% |
| 2011 | -- | $387,390 +2.5% |
| 2010 | -- | $377,856 +2.6% |
| 2009 | -- | $368,323 +2.7% |
| 2008 | -- | $358,790 +12.7% |
| 2007 | -- | $318,416 +14.5% |
| 2006 | -- | $278,043 +17% |
| 2005 | -- | $237,670 |
| 2004 | -- | $237,670 |
| 2003 | -- | $237,670 -1% |
| 2002 | -- | $240,020 +1.2% |
| 2001 | -- | $237,166 |
Find assessor info on the county website
Neighborhood: 21619
Nearby homes
- $795,0005 bd4 ba3k sqft104 Woods Rd, Chester, MD 21619Sold
- $787,6004 bd3 ba3.4k sqft107 Bentons Pleasure Rd, Chester, MD 21619Off Market
- $353,9000.918 Acres105 Bentons Pleasure Rd, Chester, MD 21619Off Market
- $893,100-- bd3 ba3.1k sqft109 Bentons Pleasure Rd, Chester, MD 21619Off Market
- $632,000-- bd2 ba2.7k sqft102 Woods Rd, Chester, MD 21619Off Market
- $499,5003 bd2 ba1.8k sqft110 Woods Rd, Chester, MD 21619Off Market
- $825,7005 bd5 ba3.1k sqft111 Bentons Pleasure Rd, Chester, MD 21619Off Market
- $516,2003 bd3 ba1.7k sqft101 Bentons Pleasure Rd, Chester, MD 21619Off Market
Nearby schools
GreatSchools rating
- NAKent Island Elementary SchoolGrades: PK-2Distance: 1.9 mi
- 7/10Matapeake Middle SchoolGrades: 6-8Distance: 2.1 mi
- 5/10Kent Island High SchoolGrades: 9-12Distance: 2.7 mi
Schools provided by the listing agent
- Middle: Matapeake
- High: Kent Island
- District: Queen Anne's County Public Schools
Source: Bright MLS. This data may not be complete. We recommend contacting the local school district to confirm school assignments for this home.
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Estimated market value
$681,100
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Find out how much your home could sell for in as little as 3 minutes with a no-obligation cash offer.
Estimated market value
$681,100
- Maryland
- Queen Annes County
- Chester
- 21619
- 106 Woods Rd
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