Back 106 Woods Rd
Off Market

106 Woods Rd

Chester MD 21619

4
3
2
2551 sq. ft.
24354 sq. ft.
Single-Family
Last sold for $650,000
Jackie DaleyJackie Daley, last sold this property on 26 June 2025 after 48 days on market.

Overview

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.

Features

4 bedrooms
3 bathrooms
2 carspaces
2 garage spaces
2551 sq. ft. floor area
24354 sq. ft. lot size
Single-Family

Estimated Value

Based on this property and similar 4 bedroom single-family properties sold in Chester over the last 12 months, the estimated median property value of 106 Woods Rd is $717.45k.

Median value
$717.45k
Estimated value range
$350k - $2.35m
Median days on market
28
Estimated value trend
7%
increase over the last 12 months
Average days on market is based on recent, comparable sales in Chester. It is only an indication of the time a property is actively listed and should not be relied upon as an accurate representation of how soon a property will be sold.

Property history for 106 Woods Rd

2025
Sold
$650,000
26 Jun 2025 by Jackie Daley, of Northrop Realty
2022
Sold
$575,000
31 Aug 2022 by Kathleen Higginbotham, of Keller Williams Flagship of Maryland
2019
Sold
$440,000
04 Apr 2019 by Douglas Milburn, of Weichert, Realtors Platinum Service

Happy sellers in Chester

92%
92% of sellers in Chester reported that their sale price either exceeded or met their price expectations.

Chester stands out for consistently delivering exceptional satisfaction and strong market results for homeowners.

This is based on voluntary sentiment collected from 12 reviews in Chester over the last 12 months.

Local market activity for 4 bedroom single-family properties in Chester

In the last 12 months, 41 four-bedroom single-family properties similar to 106 Woods Rd, have been sold.

This represents a 8% increase in four-bedroom single-family properties sales when compared to the previous 12 months.

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