102 Skipper Ln, Chester, MD 21619
Property image
Property image
OFF MARKET

$576,500

Trulia Estimate
  • 3 Beds
  • 2.5 Baths
  • 1,810 sqft (on 0.50 acres)

102 Skipper Ln, Chester, MD 21619

Est. Refi. Payment $3,370/mo*
Refinance Your Home
Currently Off Market - Sold Oct 2, 2023 for $525,000

Home Value

Trulia Estimate
$577K
Since last month
Increased$1K (+0.2%)
Since last year
$100 (0%)
Since last sale
Increased$52K (+9.8%)
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 +69% in the last 10 years
MonthEstimated value
2026
August 2026$577K
August 2026$576K
July 2026$576K
June 2026$582K
May 2026$582K
April 2026$581K
March 2026$580K
February 2026$572K
January 2026$575K
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
206 Anchor Ln, Chester, MD
0.11
Single-Family Home
$555,000
07/17/26
3
2
1,944
307 Skipper Ln, Chester, MD
0.18
Single-Family Home
$490,000
10/30/25
3
2
2,180
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
0.10
Single-Family Home
$630,000
10/30/25
6
3
3,760
224 Bayberry Dr, Chester, MD
0.21
Single-Family Home
$550,000
01/23/26
2
2
1,913
129 Sailcloth Way, Chester, MD
0.23
Single-Family Home
$764,900
05/22/26
3
2
2,303
135 Nauset Ln, Chester, MD
0.27
Single-Family Home
$787,500
08/07/26
3
3
2,795
219 Broadwater Dr, Chester, MD
0.25
Single-Family Home
$643,000
04/08/26
2
2
1,913
124 Nauset Ln, Chester, MD
0.26
Single-Family Home
$825,000
12/09/25
3
3
2,583
223 Broadwater Dr, Chester, MD
0.25
Single-Family Home
$837,000
09/30/25
3
3
2,745

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
203 Anchor Ln, Chester, MD 21619
0.08
$524,400
3
2
1,890
Off Market
205 Anchor Ln, Chester, MD 21619
0.10
$525,000
5
3
3,000
For Sale
206 Anchor Ln, Chester, MD 21619
0.11
$555,000
3
2
1,944
Recently Sold
326 Castle Marina Rd, Chester, MD 21619
0.06
$550,000
5
3.5
3,552
For Sale
105 Pilot Ct, Chester, MD 21619
0.07
$596,200
5
3
2,726
Off Market
204 Skipper Ln, Chester, MD 21619
0.10
$658,000
6
3
3,760
Off Market
511 Skipper Ct, Chester, MD 21619
0.15
$613,000
3
2
1,754
Off Market
119 Marshgrass Way #1243, Chester, MD 21619
0.14
$669,400
2
2.5
1,900
Off Market
106 Warbler Way, Chester, MD 21619
0.14
$770,200
3
3
2,750
Off Market
136 Nighthawk Dr, Chester, MD 21619
0.14
$877,400
3
2
2,657
Off Market
307 Skipper Ln, Chester, MD 21619
0.18
$511,800
3
2
2,180
Off Market

Local Information

  • Map ViewExplore the area around 102 Skipper Ln.
  • Schools1 Preschool School2 Elementary Schools1 Middle School1 High School
  • Shop & Eat
-- mins to
Commute Destination

Home Highlights

Single-Family Home
Built in 2006
0.5 acre lot
1,810 sqft
$319/sqft
2 Car Garage

About this House

Here is your opportunity to purchase in Castle Marina!! This beautiful home was custom built in 2006! This 3 bedroom, 2 1/2 bath home sits on 1/2 an acre. Enjoy the large porches on both front and back of the home. The rear porch was screened in 2022. It makes for enjoyable summer evenings overlooking the brick patio. You will feel as if you have been transplanted to Charleston! The private primary suite boasts sliding glass doors to the porch, walk in closet, walk in shower, custom cabinetry and the most relaxing air tub. The solar panels and hot water heater, will keep your energy bills low all year long! Park your cars in the 2 car oversized garage with storage and access to the back yard! There are so many upgrades to this home, you will need to take a look at it yourself! Freshly painted this spring, this home is ready for you to make your own!!!
102 Skipper Ln, Chester, MD 21619 is a 3 bedroom, 3 bathroom, 1,810 sqft single-family home built in 2006. It last sold for the $525,000 asking price on Oct 2, 2023. This property is not currently displayed as for sale or rent on Trulia. The Trulia Estimate is $576,500, with a rent estimate of $2,758/month.
Last check for updates: about 20 hours ago
Listed by SALLY KERCHNER, (410) 903-5960
Benson & Mangold, LLC
Bought with: Cat Marucci, (443) 883-1609, Coldwell Banker Realty
Source: Bright MLS, MLS#MDQA2007448

Home Details for 102 Skipper Ln

Interior Features

Interior Details
Number of Rooms: 1Types of Rooms: Basement
Beds & Baths
Number of Bedrooms: 3Main Level Bedrooms: 3Number of Bathrooms: 3Number of Bathrooms (full): 2Number of Bathrooms (half): 1Number of Bathrooms (main level): 3
Dimensions and Layout
Living Area: 1810 Square Feet
Appliances & Utilities
Appliances: Microwave, Central Vacuum, Down Draft, Dishwasher, Disposal, Dryer, ENERGY STAR Qualified Refrigerator, Extra Refrigerator/Freezer, Oven, Washer, Water Conditioner - Owned, Solar Hot Water, Water Treat System, Electric Water HeaterDishwasherDisposalDryerLaundry: Main LevelMicrowaveWasher
Heating & Cooling
Heating: Heat Pump,ElectricHas CoolingAir Conditioning: Central Air,Heat Pump,Programmable Thermostat,ElectricHas HeatingHeating Fuel: Heat Pump
Fireplace & Spa
No FireplaceNo Spa
Windows, Doors, Floors & Walls
Window: Window TreatmentsFlooring: Carpet, Bamboo, Ceramic Tile, Hardwood, Wood
Levels, Entrance, & Accessibility
Stories: 1Levels: OneAccessibility: Accessible Hallway(s)Floors: Carpet, Bamboo, Ceramic Tile, Hardwood, Wood
View
No View

Exterior Features

Exterior Home Features
Roof: Architectural ShinglePatio / Porch: Patio, Screened, PorchOther Structures: Above Grade, Below GradeExterior: LightingFoundation: Brick/Mortar, Crawl SpaceNo 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,Oversized,Driveway,Attached,Off Street
Pool
Pool: None
Frontage
Not on Waterfront
Water & Sewer
Sewer: Public Sewer
Farm & Range
Not Allowed to Raise Horses
Finished Area
Finished Area (above surface): 1810 Square Feet

Property Information

Year Built
Year Built: 2006
Property Type / Style
Property Type: ResidentialProperty Subtype: Single Family ResidenceStructure Type: DetachedArchitecture: Cape Cod,Coastal,Craftsman,Traditional
Building
Construction Materials: Frame, Stick Built, Vinyl SidingNot a New Construction
Property Information
Condition: ExcellentParcel Number: 1804004124

Price & Status

Price
List Price: $525,000
Status Change & Dates
Off Market Date: Mon Oct 02 2023Possession Timing: 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: 1810 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 SellListing Terms: Cash, Conventional, FHA, USDA Loan, VA Loan

Business

Business Information
Ownership: Fee Simple

Miscellaneous

Mls Number: MDQA2007448Above Grade Unfinished Area: 1810

Price and Tax history

DateEventPrice
Oct 2, 2023
Source: Bright MLS #MDQA2007448
Sold
$525,000
Aug 30, 2023
Source: Bright MLS #MDQA2007448
Pending
$525,000
Aug 24, 2023
Source: Bright MLS #MDQA2007448
Listed For Sale
$525,000

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

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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 102 Skipper Ln

  • What is 102 Skipper Ln estimated to be worth?
    Trulia's estimated value for 102 Skipper Ln in Chester, MD is $576,500.
  • What is the price history for 102 Skipper Ln?
    102 Skipper Ln in Chester, MD last sold for $525,000 in October 2023.
  • 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 102 Skipper Ln have air conditioning?
    Yes, 102 Skipper Ln in Chester, MD has air conditioning.
  • Does 102 Skipper Ln have laundry facilities?
    Yes, 102 Skipper Ln in Chester, MD has in-unit laundry.

Explore by feature - Air Conditioning

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Off Market Homes Near 102 Skipper Ln

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