105 Pilot Ct, Chester, MD 21619
Property image
Property image
OFF MARKET

$596,200

Trulia Estimate
  • 5 Beds
  • 3 Baths
  • 2,726 sqft (on 0.50 acres)

105 Pilot Ct, Chester, MD 21619

Est. Refi. Payment $3,504/mo*
Refinance Your Home
Currently Off Market - Sold Oct 18, 2024 for $537,500

Home Value

Trulia Estimate
$596K
Since last month
Decreased$6K (-0.9%)
Since last year
Increased$44K (+8.1%)
Since last sale
Increased$57K (+10.7%)
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 +102% in the last 10 years
MonthEstimated value
2026
August 2026$595K
August 2026$594K
July 2026$600K
June 2026$596K
May 2026$588K
April 2026$574K
March 2026$552K
February 2026$535K
January 2026$538K
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
306 Skipper Ln, Chester, MD
0.18
Single-Family Home
$569,000
12/03/25
4
2.5
2,610
204 Skipper Ln, Chester, MD
0.07
Single-Family Home
$630,000
10/30/25
6
3
3,760
206 Anchor Ln, Chester, MD
0.17
Single-Family Home
$555,000
07/17/26
3
2
1,944
307 Skipper Ln, Chester, MD
0.20
Single-Family Home
$490,000
10/30/25
3
2
2,180
135 Nauset Ln, Chester, MD
0.24
Single-Family Home
$787,500
08/07/26
3
3
2,795
255 Sailcloth Way, Chester, MD
0.15
Single-Family Home
$898,000
10/01/25
4
4
3,450
124 Nauset Ln, Chester, MD
0.23
Single-Family Home
$825,000
12/09/25
3
3
2,583
235 Bayberry Dr, Chester, MD
0.13
Single-Family Home
$910,000
10/03/25
3
3.5
3,514
154 Bluebell Ct, Chester, MD
0.21
Single-Family Home
$965,000
08/24/26
3
3
3,434
558 Cross Creek Ct, Chester, MD
0.64
Single-Family Home
$542,500
11/13/25
4
2.5
2,558

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
102 Skipper Ln, Chester, MD 21619
0.07
$576,500
3
2.5
1,810
Off Market
326 Castle Marina Rd, Chester, MD 21619
0.10
$550,000
5
3.5
3,552
For Sale
204 Skipper Ln, Chester, MD 21619
0.07
$658,000
6
3
3,760
Off Market
203 Anchor Ln, Chester, MD 21619
0.15
$524,400
3
2
1,890
Off Market
136 Nighthawk Dr, Chester, MD 21619
0.09
$877,400
3
2
2,657
Off Market
255 Sailcloth Way, Chester, MD 21619
0.15
$940,900
4
4
3,450
Off Market
119 Marshgrass Way #1243, Chester, MD 21619
0.10
$669,400
2
2.5
1,900
Off Market
106 Warbler Way, Chester, MD 21619
0.10
$770,200
3
3
2,750
Off Market
205 Anchor Ln, Chester, MD 21619
0.17
$525,000
5
3
3,000
For Sale
171 Spinnaker Way, Chester, MD 21619
0.18
$824,400
3
3
2,480
Off Market
214 Bayberry Dr, Chester, MD 21619
0.12
$924,000
3
3
2,745
For Sale

Local Information

  • Map ViewExplore the area around 105 Pilot Ct.
  • Schools1 Preschool School2 Elementary Schools1 Middle School1 High School
  • Shop & Eat
-- mins to
Commute Destination

Home Highlights

Single-Family Home
Built in 1969
0.5 acre lot
2,726 sqft
$219/sqft
2 Car Garage

About this House

Welcome to 105 Pilot Ct. in Chester, MD! Located within the sought after community of Castle Marina, this wonderfully updated and renovated 5 bedroom, 3 full bath split level home features 5 bedrooms offers a blend of serene suburban living with easy access to both nature, parks and urban amenities. Traveling down the driveway, the new walkway and well-maintained lawn set a welcoming tone enhanced by the majestic Magnolia gracing the left side of the house. As you enter, you are greeted by a generous landing area, creating an inviting and spacious first impression. The landing guides you to wide stairs that lead up to the main level, that includes 4 bedrooms and 2 full baths, with high ceilings that enhance the sense of openness and an abundance of natural lighting. The expansive, open-concept layout boasts hardwood floors adding a touch of warmth and is perfect for both everyday living and entertaining. The updated eat-in kitchen features new appliances, hardwood flooring, beautiful honey maple cabinetry, and ample counter space making it the perfect spot for casual meals and everyday use. The separate, formal dining room is ideal for hosting gatherings and entertaining guests. The main level bedrooms are privately situated with generous space and deep closets. The primary suite includes renovated and private full bath. As you travel back towards the kitchen, you'll notice a second set of beautiful hardwood stairs that lead down to the beautifully renovated lower level of the home. This renovated space boasts a bump-out addition to the family room, creating an expansive and comfortable area perfect for relaxation and gatherings, ensuring everyone in the household has room to relax and enjoy. The lower level also includes a full bath and a spacious bedroom, offering a private retreat for guests or family members. The lower level also features ample storage space for your personal belongings and convenient access to a large, attached two-car garage designed to accommodate your vehicles while also offering built-in space for a workshop, making it perfect for hobbies, DIY projects, or additional storage needs. Love to entertain outdoors? This home includes a newer built, spacious composite deck with vinyl railing that is ready for your grill and outdoor furnishings, making it the perfect spot for summer barbecues, casual dining, and relaxing under the stars. The deck overlooks a large, level, and grassy private backyard, creating an ideal setting for outdoor activities and gatherings. At the heart of this inviting space is a beautiful tree that provides natural shade, making it a comfortable spot for relaxation and play. With ample room for kids and pets to roam and plenty of space for outdoor entertaining, this backyard is sure to be a favorite place for family and friends to gather. This turnkey home features recent renovations to the primary bath, side stairway to lower level, front walkway, and installation of maintenance free soffit and facia as well as new microwave, range and dishwasher (2024); Heat Pump Water Heater (2015); composite deck (2013); lower level renovation with bump out addition (2005); All windows and slider doors have been replaced with Anderson 400 series (2005); kitchen remodel with upgraded flooring and cabinets (1996). Close to Castle Marina, with members-only pool, provisions store, slip rentals, boat rentals, and two restaurants with marina views. Grab your bike or stroll down the Cross Island Trail, which is just moments from your home and leads to bay and river-front beaches and parks as well as waterfront dining and entertaining. Great location for commuting with easy access to the Bay Bridge and commuter buses. Live the island life! Welcome home!
105 Pilot Ct, Chester, MD 21619 is a 5 bedroom, 3 bathroom, 2,726 sqft single-family home built in 1969. It last sold for $537,500 on Oct 18, 2024 (1% below the $545,000 asking price). This property is not currently displayed as for sale or rent on Trulia. The Trulia Estimate is $596,200, with a rent estimate of $3,364/month.
Last check for updates: about 14 hours ago
Listed by Barbara McCaffrey, (443) 926-6075
Redfin Corp
Bought with: Colleen Kerrigan, (443) 694-3911, Redfin Corp
Source: Bright MLS, MLS#MDQA2010004

Home Details for 105 Pilot Ct

Interior Features

Interior Details
Basement: FinishedNumber of Rooms: 1Types of Rooms: Basement
Beds & Baths
Number of Bedrooms: 5Main Level Bedrooms: 4Number of Bathrooms: 3Number of Bathrooms (full): 3Number of Bathrooms (main level): 2
Dimensions and Layout
Living Area: 2726 Square Feet
Appliances & Utilities
Appliances: Microwave, Six Burner Stove, Dishwasher, Refrigerator, Electric Water HeaterDishwasherLaundry: Lower LevelMicrowaveRefrigerator
Heating & Cooling
Heating: Baseboard,ElectricHas CoolingAir Conditioning: Central Air,ElectricHas HeatingHeating Fuel: Baseboard
Fireplace & Spa
No Fireplace
Windows, Doors, Floors & Walls
Flooring: Wood, Carpet
Levels, Entrance, & Accessibility
Stories: 2Levels: Multi/Split, TwoAccessibility: NoneFloors: Wood, Carpet
View
No View

Exterior Features

Exterior Home Features
Patio / Porch: DeckOther Structures: Above Grade, Below GradeFoundation: OtherNo Private Pool
Parking & Garage
Number of Garage Spaces: 2Number of Covered Spaces: 2No CarportHas a GarageHas an Attached GarageHas Open ParkingParking Spaces: 2Parking: Garage Faces Front,Driveway,Attached
Pool
Pool: None
Frontage
Not on Waterfront
Water & Sewer
Sewer: Public Sewer
Finished Area
Finished Area (above surface): 1711 Square FeetFinished Area (below surface): 1015 Square Feet

Property Information

Year Built
Year Built: 1969
Property Type / Style
Property Type: ResidentialProperty Subtype: Single Family ResidenceStructure Type: DetachedArchitecture: Detached
Building
Construction Materials: BrickNot a New Construction
Property Information
Parcel Number: 1804004167

Price & Status

Price
List Price: $545,000
Status Change & Dates
Off Market Date: Fri Oct 18 2024Possession Timing: Negotiable, Close Of Escrow

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: 2726 Square Feet

Community

Not Senior Community

HOA

No HOA

Lot Information

Lot Area: 0.50 acres

Listing Info

Special Conditions: Standard

Offer

Listing Agreement Type: Exclusive Right To Sell

Business

Business Information
Ownership: Fee Simple

Miscellaneous

BasementMls Number: MDQA2010004Above Grade Unfinished Area: 1711

Price and Tax history

DateEventPrice
Oct 18, 2024
Source: Bright MLS #MDQA2010004
Sold
$537,500
Sep 9, 2024
Source: Bright MLS #MDQA2010004
Pending
$545,000
Aug 6, 2024
Source: Bright MLS #MDQA2010004
PriceChange
$545,000
Price decreased by 4%
Jun 18, 2024
Source: Bright MLS #MDQA2010004
Listed For Sale
$570,000

Market trends in Chester

Last updated July 2026
Buyer'sMarketSeller'sMarket
Avg. sale price
—
Sale-to-List Price
—
Price per sq ft
—
Available listings
70
5MoM

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 105 Pilot Ct

  • What is 105 Pilot Ct estimated to be worth?
    Trulia's estimated value for 105 Pilot Ct in Chester, MD is $596,200.
  • What is the price history for 105 Pilot Ct?
    105 Pilot Ct in Chester, MD last sold for $537,500 in October 2024.
  • Is Chester a buyer's or seller's market?
    Chester is currently a buyer's 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 105 Pilot Ct have air conditioning?
    Yes, 105 Pilot Ct in Chester, MD has air conditioning.
  • Does 105 Pilot Ct have laundry facilities?
    Yes, 105 Pilot Ct in Chester, MD has laundry facilities.

Explore by feature - Air Conditioning

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