306 Skipper Ln, Chester, MD 21619
Property image
Property image
SOLD
DEC 3, 2025

$589,600

Trulia Estimate
  • 4 Beds
  • 2.5 Baths
  • 2,610 sqft (on 0.51 acres)

306 Skipper Ln, Chester, MD 21619

Est. Refi. Payment $3,601/mo*
Refinance Your Home
Currently Off Market - Sold Dec 3, 2025 for $569,000

Home Value

Trulia Estimate
$590K
Since last month
Increased$4K (+0.6%)
Since last year
Decreased$29K (-4.7%)
Since last sale
Increased$21K (+3.7%)
Learn more about this home's value by checking out its Trulia Estimate, the value of nearby homes, and how much similar homes have sold for.

Trulia Estimate

The of this home's value increased by +54% in the last 10 years
MonthEstimated value
2026
September 2026$590K
August 2026$592K
July 2026$587K
June 2026$583K
May 2026$580K
April 2026$579K
March 2026$571K
February 2026$566K
January 2026$570K
2025
2024
2023
2022
2021
2020
2019
2018
2017
2016

Comparable sales

These are recently sold homes that have a similar location or other similar features to this home, like bedrooms, bathrooms, and square footage. Get a sense of the expected prices in the area by viewing these homes.
Address
Distance
Property Type
Sold Price
Sold Date
Bed
Bath
Sqft
307 Skipper Ln, Chester, MD
0.05
Single-Family Home
$490,000
10/30/25
3
2
2,180
206 Anchor Ln, Chester, MD
0.18
Single-Family Home
$555,000
07/17/26
3
2
1,944
204 Skipper Ln, Chester, MD
0.10
Single-Family Home
$630,000
10/30/25
6
3
3,760
135 Nauset Ln, Chester, MD
0.10
Single-Family Home
$787,500
08/07/26
3
3
2,795
136 Nauset Ln, Chester, MD
0.12
Single-Family Home
$799,000
09/15/26
3
3
2,986
124 Nauset Ln, Chester, MD
0.11
Single-Family Home
$825,000
12/09/25
3
3
2,583
154 Bluebell Ct, Chester, MD
0.06
Single-Family Home
$965,000
08/24/26
3
3
3,434
558 Cross Creek Ct, Chester, MD
0.62
Single-Family Home
$542,500
11/13/25
4
2.5
2,558
235 Bayberry Dr, Chester, MD
0.18
Single-Family Home
$910,000
10/03/25
3
3.5
3,514

Nearby home prices

Get a sense of expected prices in the area by checking the value of nearby homes.
Address
Distance
Price
Bed
Bath
Sqft
Status
307 Skipper Ln, Chester, MD 21619
0.05
$509,500
3
2
2,180
Off Market
154 Bluebell Ct, Chester, MD 21619
0.06
$965,000
3
3
3,434
Recently Sold
135 Nauset Ln, Chester, MD 21619
0.10
$787,500
3
3
2,795
Recently Sold
30 Queen Mary Ct, Chester, MD 21619
0.13
$339,900
2
2.5
1,440
Recently Sold
119 Marshgrass Way #1243, Chester, MD 21619
0.09
$665,100
2
2.5
1,900
Off Market
106 Warbler Way, Chester, MD 21619
0.09
$770,200
3
3
2,750
Off Market
204 Skipper Ln, Chester, MD 21619
0.10
$655,100
6
3
3,760
Off Market
511 Skipper Ct, Chester, MD 21619
0.13
$613,000
3
2
1,754
Off Market
124 Nauset Ln, Chester, MD 21619
0.11
$825,000
3
3
2,583
Recently Sold
136 Nauset Ln, Chester, MD 21619
0.12
$799,000
3
3
2,986
Recently Sold
111 Bluebell Ct, Chester, MD 21619
0.12
$532,600
2
2
1,693
Off Market

Local Information

  • Map ViewExplore the area around 306 Skipper Ln.
  • Schools1 Preschool School2 Elementary Schools1 Middle School1 High School
  • Shop & Eat
-- mins to
Commute Destination

Home Highlights

Single-Family Home
Built in 1974
0.51 acre lot
2,610 sqft
$218/sqft
2 Car Garage

About this House

Move-in ready and full of upgrades, this thoughtfully designed home offers a bright, open layout perfect for everyday living and entertaining. The renovated kitchen features quartz counters, a coastal tile backsplash, and opens to the dining and living areas with soaring ceilings and access to the deck and fenced yard. The fire pit and mature landscaping makes for a private, serene setting. A private path through the backyard connects directly to Four Seasons and the Cross Island Trail—ideal for walking, biking, or enjoying the outdoors. The main level includes a bedroom and bonus room/office, while upstairs offers three additional bedrooms including a spacious primary suite with attached bath. Additional highlights include a two-car garage with extra storage, side gardens, tankless water heater, paved driveway with bonus parking, and no HOA. All this in a prime Kent Island location, just minutes to local shopping, dining, trails, and Rt. 50 for easy commuting to Annapolis, St. Michaels, Washington, D.C., Baltimore, and beyond. Don’t miss this opportunity to own a conveniently located, beautifully updated home in Castle Marina! Schedule your tour today - you won't want to miss this conveniently located and move in ready gem on Kent Island.
306 Skipper Ln, Chester, MD 21619 is a 4 bedroom, 3 bathroom, 2,610 sqft single-family home built in 1974. It last sold for the $569,000 asking price on Dec 3, 2025. This property is not currently displayed as for sale or rent on Trulia. The Trulia Estimate is $589,600, with a rent estimate of $3,083/month.
Last check for updates: about 9 hours ago
Listed by Elizabeth Arentz, (443) 988-3495
Coldwell Banker Realty
Bought with: Jennifer Thomas, (410) 598-8343, RE/MAX Executive
Source: Bright MLS, MLS#MDQA2015066

Home Details for 306 Skipper Ln

Interior Features

Interior Details
Number of Rooms: 7Types of Rooms: Bedroom 1, Bedroom 2, Bedroom 3, Bathroom 1, Bathroom 2, Half Bath
Beds & Baths
Number of Bedrooms: 4Main Level Bedrooms: 1Number of Bathrooms: 3Number of Bathrooms (full): 2Number of Bathrooms (half): 1Number of Bathrooms (main level): 1
Dimensions and Layout
Living Area: 2610 Square Feet
Appliances & Utilities
Appliances: Tankless Water Heater, Water Heater
Heating & Cooling
Heating: Heat Pump,ElectricHas CoolingAir Conditioning: Other,Central Air,Programmable Thermostat,ElectricHas HeatingHeating Fuel: Heat Pump
Fireplace & Spa
Number of Fireplaces: 2Fireplace: BrickHas a Fireplace
Levels, Entrance, & Accessibility
Stories: 2Levels: TwoAccessibility: Accessible Entrance, Low Pile Carpeting
View
No View

Exterior Features

Exterior Home Features
Other Structures: Above GradeFoundation: Crawl Space, SlabNo Private Pool
Parking & Garage
Number of Garage Spaces: 2Number of Covered Spaces: 2No CarportHas a GarageHas an Attached GarageHas Open ParkingParking Spaces: 2Parking: Storage,Garage Faces Front,Garage Door Opener,Inside Entrance,Attached,Driveway
Pool
Pool: None
Frontage
Not on Waterfront
Water & Sewer
Sewer: Public Sewer
Finished Area
Finished Area (above surface): 2610 Square Feet

Property Information

Year Built
Year Built: 1974
Property Type / Style
Property Type: ResidentialProperty Subtype: Single Family ResidenceStructure Type: DetachedArchitecture: Colonial,Mid-Century Modern
Building
Construction Materials: Brick, Vinyl SidingNot a New Construction
Property Information
Condition: ExcellentParcel Number: 1804062205

Price & Status

Price
List Price: $569,000Price Per Sqft: $218/sqft
Status Change & Dates
Off Market Date: Wed Dec 03 2025Possession Timing: 0-30 Days CD, Negotiable

Active Status

MLS Status: CLOSED

Location

Direction & Address
City: CHESTERCommunity: Castle Marina
School Information
Elementary School District: Queen Anne's County Public SchoolsJr High / Middle School District: Queen Anne's County Public SchoolsHigh School District: Queen Anne's County Public Schools

Building

Building Area
Building Area: 2610 Square Feet

Community

Not Senior Community

HOA

No HOA

Lot Information

Lot Area: 0.51 acres

Listing Info

Special Conditions: Standard

Offer

Listing Agreement Type: Exclusive Right To Sell

Business

Business Information
Ownership: Fee Simple

Miscellaneous

Mls Number: MDQA2015066Above Grade Unfinished Area: 2610

Price and Tax history

DateEventPrice
Dec 3, 2025
Source: Bright MLS #MDQA2015066
Sold
$569,000
Oct 26, 2025
Source: Bright MLS #MDQA2015066
Contingent
$569,000
Oct 17, 2025
Source: Bright MLS #MDQA2015066
Listed For Sale
$569,000
Dec 9, 2005
Source: N/A
Sold
$417,000

Market trends in Chester

Last updated August 2026
Buyer'sMarketSeller'sMarket
Avg. sale price
—
Sale-to-List Price
—
Price per sq ft
—
Available listings
69
1MoM

Around this home

What Locals Say about Chester

At least 36 Trulia users voted on each feature.

  • 88 % Say parking is easy

  • 88 % Say car is needed

  • 86 % Say people would walk alone at night

  • 83 % Say it's dog friendly

  • 83 % Say it's quiet

  • 80 % Say there's holiday spirit

  • 65 % Say neighbors are friendly

  • 64 % Say kids play outside

  • 64 % Say there's wildlife

  • 57 % Say yards are well-kept

  • 53 % Say there are sidewalks

  • 49 % Say they plan to stay for at least 5 years

  • 48 % Say there are community events

  • 44 % Say streets are well-lit

  • 41 % Say it's walkable to restaurants

  • 17 % Say it's walkable to grocery stores

Sourced by Trulia users. Learn more about our methodology.
  • Dlmaheux
    "I’ve been here 20 years and don’t even lock my doors the majority of the time. Super safe. Wonderful sense of community all around "
    0
    Flag
  • Colinjgallagher525
    "Tucked away million dollar homes with great down-to-earth people living in them. It’s a warm community and bay living at its finest. "
    0
    Flag
  • Peggy Young
    "Board meetings, water aerobics, pickle ball, tennis, a gym, kayaking, paddle boarding. Mah jongg, bingo, games day, social committee,walking club "
    0
    Flag
  • Trulia User
    "Water aerobics, happy hours, cardboard boat races, kayaking, mah jongg, game day dog walking. Boating "
    0
    Flag
  • Peggy.young
    "Lots of spaces to walk dogs, lots of people who love dogs. Great way to meet neighbors. Just about everyone on the shore has a dog. Also a number of good kennels for when you travel. "
    3
    Flag
  • Taylor T.
    "Lots of dogs everyone walks them all hours of the night and their is little stops with bags to pick up Feeses "
    0
    Flag
  • kara
    "I've lived here for three years and the neighbors are very friendly mostly. They look out for each other..."
    0
    Flag
  • Robert M Heyn
    "Its always so pleasant here in Chester. Its like Everyone says HI and knows one another. The school systems are great and Chester is central located to all surrounding areas of shopping, dining, water, Annapolis and Easton. Some of tue most beautiful views in the MD pertaining to water and nature."
    1
    Flag
  • J0J0s4X4
    "They are required to clean up after them. The HOA used to pay a pooper scooper company which provided pooper containers, scoops, and bags after used to be deposited in the container. The Board decided that the dog owners should pick up the cost of picking up after their dogs and quit paying the $26,000 per year for the company."
    0
    Flag
  • Wilson
    "Not very many families, but within a great school district. Good community for people who don’t really have children. "
    0
    Flag
  • J0J0s4X4
    "it is a child friendly development and very safe. also, most homeowners have video security systems."
    0
    Flag
  • Peggy y.
    "Chester is a real community, where you know just about everyone. I live in a condo, so life is as easy as it gets. There are lots of walking trails, and you are always a stone’s throw from the Chesapeake Bay or the Chester River."
    3
    Flag
  • Eric D.
    "I live in this area. Great place to raise a family. Access to beaches, parks, cross island trail."
    0
    Flag

LGBTQ Local Legal Protections

The data relating to real estate for sale on this website appears in part through the BRIGHT Internet Data Exchange program, a voluntary cooperative exchange of property listing data between licensed real estate brokerage firms, and is provided by BRIGHT through a licensing agreement. Listing information is from various brokers who participate in the Bright MLS IDX program and not all listings may be visible on the site. The property information being provided on or through the website is for the personal, non-commercial use of consumers and such information may not be used for any purpose other than to identify prospective properties consumers may be interested in purchasing. Some properties which appear for sale on the website may no longer be available because they are for instance, under contract, sold or are no longer being offered for sale. Property information displayed is deemed reliable but is not guaranteed. Copyright 2026 Bright MLS, Inc. Click here for more information

Frequently asked questions about 306 Skipper Ln

  • What is 306 Skipper Ln estimated to be worth?
    Trulia's estimated value for 306 Skipper Ln in Chester, MD is $589,600.
  • What is the price history for 306 Skipper Ln?
    306 Skipper Ln in Chester, MD last sold for $569,000 in December 2025.
  • Is Chester a buyer's or seller's market?
    Chester is currently a balanced market, based on recent for-sale activity.
  • What do residents say about Chester?
    Residents describe Chester, MD as easy to park in, dog-friendly, and quiet. Most residents say you need a car. See recently sold homes in Chester, MD.
  • Does 306 Skipper Ln have air conditioning?
    Yes, 306 Skipper Ln in Chester, MD has air conditioning.
  • How big is the lot at 306 Skipper Ln?
    The lot at 306 Skipper Ln in Chester, MD is about 0.51 acres (22,216 sq ft).

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