409 Skipper Ln, Chester, MD 21619
OFF MARKET

$465,300

Trulia Estimate
  • 4 Beds
  • 3 Baths
  • 1,094 sqft (on 0.47 acres)

409 Skipper Ln, Chester, MD 21619

Est. Refi. Payment $2,741/mo*
Refinance Your Home
Currently Off Market - Sold Feb 9, 2010 for $270,000

Home Value

Trulia Estimate
$465K
Since last month
Decreased$3K (-0.7%)
Since last year
Decreased$8K (-1.7%)
Since last sale
Increased$196K (+72.4%)
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 +88% in the last 10 years
MonthEstimated value
2026
August 2026$466K
August 2026$466K
July 2026$469K
June 2026$477K
May 2026$482K
April 2026$480K
March 2026$478K
February 2026$467K
January 2026$456K
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
0.19
Single-Family Home
$569,000
12/03/25
4
2.5
2,610
307 Skipper Ln, Chester, MD
0.14
Single-Family Home
$490,000
10/30/25
3
2
2,180
206 Anchor Ln, Chester, MD
0.17
Single-Family Home
$555,000
07/17/26
3
2
1,944
29D Queen Mary Ct, Chester, MD
0.08
Single-Family Home
$363,000
08/12/26
3
2.5
1,440
204 Skipper Ln, Chester, MD
0.25
Single-Family Home
$630,000
10/30/25
6
3
3,760
135 Nauset Ln, Chester, MD
0.26
Single-Family Home
$787,500
08/07/26
3
3
2,795
2723 Cox Neck Rd, Chester, MD
0.92
Single-Family Home
$447,500
10/17/25
4
2.5
1,600
154 Bluebell Ct, Chester, MD
0.24
Single-Family Home
$965,000
08/24/26
3
3
3,434
124 Nauset Ln, Chester, MD
0.29
Single-Family Home
$825,000
12/09/25
3
3
2,583
1914 Anchorage Dr, Chester, MD
0.94
Single-Family Home
$299,900
06/08/26
3
2
1,800

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
27 Queen Mary Ct #F, Chester, MD 21619
0.06
$405,000
2
2
1,380
Recently Sold
29-A Queen Mary Ct, Chester, MD 21619
0.08
$363,000
3
2.5
1,440
Recently Sold
3 Queen Victoria Way, Chester, MD 21619
0.04
$230,000
1
1
724
Recently Sold
28 Queen Mary Ct, Chester, MD 21619
0.07
$355,100
2
2.5
1,660
Off Market
2 Queen Victoria Ct, Chester, MD 21619
0.05
$391,300
3
2
1,763
Off Market
30 Queen Mary Ct, Chester, MD 21619
0.10
$339,900
2
2.5
1,440
Recently Sold
1 Queen Victoria Ct, Chester, MD 21619
0.06
$383,500
2
2
1,260
Off Market
41 Queen Catherine Ct, Chester, MD 21619
0.12
$439,000
3
3
1,750
For Sale
26 Queen Anne Way #26K, Chester, MD 21619
0.09
$251,800
1
1
640
Off Market
6 Queen Victoria Way, Chester, MD 21619
0.08
$275,000
1
1
724
Recently Sold
8F Queen Victoria Way, Chester, MD 21619
0.09
$235,600
1
1
724
Off Market
8 Queen Victoria Way, Chester, MD 21619
0.09
$240,000
1
1
724
For Sale

Local Information

  • Map ViewExplore the area around 409 Skipper Ln.
  • Schools1 Preschool School2 Elementary Schools1 Middle School1 High School
  • Shop & Eat
-- mins to
Commute Destination

Home Highlights

Property Type
Single-Family Home
Year Built
1987
Lot Size
0.47 acres
Living Area
1,094 sqft
Price/Sqft
$425

About this House

HUGE LOT! Almost 1/2Ac! Large rear & side yard to stop sign. 4Brs, 3 Ba, beautiful hardwood floors, AWESOME CLUBROOM W/WET BAR, FRIG. & TRACK LIGHTING w/custom ceiling & wainescotting for holiday gatherings or Super Bowl Parties! Lovely living room w/bow window, NEW stainless appl. in kit., newer HVAC, ceramic & corian, 16x12 Shed and very quiet comm. Walk to marina, dining & bike trail!
409 Skipper Ln, Chester, MD 21619 is a 4 bedroom, 3 bathroom, 1,094 sqft single-family home built in 1987. It last sold for $270,000 on Feb 9, 2010. This property is not currently displayed as for sale or rent on Trulia. The Trulia Estimate is $465,300, with a rent estimate of $2,466/month.

Home Details for 409 Skipper Ln

Interior Features

Interior Details
Basement
Levels, Entrance, & Accessibility
Stories: 1
Heating & Cooling
Air Conditioning
Fireplace & Spa
Fireplace

Exterior Features

Exterior Home Features
Roof: Shake ShingleDeckExterior: Other

Property Information

Year Built
Year Built: 1987
Property Type / Style
Property Type: Single Family HomeArchitecture: split entry

Community

Units in Building: 1

Lot Information

Lot Area: 0.47 acres

Price and Tax history

DateEventPrice
Feb 9, 2010
Source: N/A
Sold
$270,000
Oct 16, 2009
Source: Agent Provided
Listed For Sale
$280,000
Mar 29, 2004
Source: N/A
Sold
$255,000

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

Frequently asked questions about 409 Skipper Ln

  • What is 409 Skipper Ln estimated to be worth?
    Trulia's estimated value for 409 Skipper Ln in Chester, MD is $465,300.
  • What is the price history for 409 Skipper Ln?
    409 Skipper Ln in Chester, MD last sold for $270,000 in February 2010.
  • 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.
  • How big is the lot at 409 Skipper Ln?
    The lot at 409 Skipper Ln in Chester, MD is about 0.47 acres (20,452 sq ft).

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