309 Skipper Ln, Chester, MD 21619
OFF MARKET

$414,600

Trulia Estimate
  • 4 Beds
  • 2 Baths
  • 1,092 sqft (on 0.49 acres)

309 Skipper Ln, Chester, MD 21619

Est. Refi. Payment $2,460/mo*
Refinance Your Home
Currently Off Market - Sold Apr 25, 2016 for $215,000

Home Value

Trulia Estimate
$415K
Since last month
Decreased$9K (-2.1%)
Since last year
Increased$2K (+0.4%)
Since last sale
Increased$200K (+92.8%)
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 +88% in the last 10 years
MonthEstimated value
2026
August 2026$415K
August 2026$415K
July 2026$423K
June 2026$428K
May 2026$430K
April 2026$427K
March 2026$420K
February 2026$412K
January 2026$400K
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
0.01
Single-Family Home
$490,000
10/30/25
3
2
2,180
206 Anchor Ln, Chester, MD
0.16
Single-Family Home
$555,000
07/17/26
3
2
1,944
306 Skipper Ln, Chester, MD
0.05
Single-Family Home
$569,000
12/03/25
4
2.5
2,610
204 Skipper Ln, Chester, MD
0.13
Single-Family Home
$630,000
10/30/25
6
3
3,760
1914 Anchorage Dr, Chester, MD
0.81
Single-Family Home
$299,900
06/08/26
3
2
1,800
29D Queen Mary Ct, Chester, MD
0.13
Single-Family Home
$363,000
08/12/26
3
2.5
1,440
135 Nauset Ln, Chester, MD
0.14
Single-Family Home
$787,500
08/07/26
3
3
2,795
224 Bayberry Dr, Chester, MD
0.27
Single-Family Home
$550,000
01/23/26
2
2
1,913
154 Bluebell Ct, Chester, MD
0.10
Single-Family Home
$965,000
08/24/26
3
3
3,434
124 Nauset Ln, Chester, MD
0.15
Single-Family Home
$825,000
12/09/25
3
3
2,583

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
306 Skipper Ln, Chester, MD 21619
0.05
$569,000
4
2.5
2,610
Recently Sold
307 Skipper Ln, Chester, MD 21619
0.01
$511,800
3
2
2,180
Off Market
154 Bluebell Ct, Chester, MD 21619
0.10
$965,000
3
3
3,434
Recently Sold
41 Queen Catherine Ct, Chester, MD 21619
0.08
$439,000
3
3
1,750
For Sale
135 Nauset Ln, Chester, MD 21619
0.14
$787,500
3
3
2,795
Recently Sold
30 Queen Mary Ct, Chester, MD 21619
0.09
$339,900
2
2.5
1,440
Recently Sold
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
204 Skipper Ln, Chester, MD 21619
0.14
$658,000
6
3
3,760
Off Market
511 Skipper Ct, Chester, MD 21619
0.10
$613,000
3
2
1,754
Off Market
124 Nauset Ln, Chester, MD 21619
0.15
$825,000
3
3
2,583
Recently Sold
111 Bluebell Ct, Chester, MD 21619
0.17
$530,100
2
2
1,693
Off Market

Local Information

  • Map ViewExplore the area around 309 Skipper Ln.
  • Schools1 Preschool School2 Elementary Schools1 Middle School1 High School
  • Shop & Eat
-- mins to
Commute Destination

Home Highlights

Single-Family Home
Built in 1975
0.49 acre lot
1,092 sqft
$380/sqft

About this House

This single-family home is located at 309 Skipper Ln, Chester, MD. 309 Skipper Ln is in Chester, MD and in ZIP code 21619. This property has 4 bedrooms, 2 bathrooms and approximately 1,092 sqft of floor space. This property has a lot size of 0.49 acres and was built in 1975.
309 Skipper Ln, Chester, MD 21619 is a 4 bedroom, 2 bathroom, 1,092 sqft single-family home built in 1975. It last sold for $215,000 on Apr 25, 2016. This property is not currently displayed as for sale or rent on Trulia. The Trulia Estimate is $414,600, with a rent estimate of $2,364/month.

Home Details for 309 Skipper Ln

Interior Features

Interior Details
Basement
Heating & Cooling
Heating: Forced AirAir ConditioningCooling System: CentralHeating Fuel: Forced Air
Appliances & Utilities
Dishwasher
Fireplace & Spa
Fireplace

Exterior Features

Exterior Home Features
Roof: Shake ShingleDeckExterior: VinylPatio

Property Information

Year Built
Year Built: 1975
Property Type / Style
Property Type: Single Family HomeArchitecture: split entry

Community

Units in Building: 1

Lot Information

Lot Area: 0.49 acres

Price and Tax history

DateEventPrice
Apr 25, 2016
Source: N/A
Sold
$215,000
Jan 9, 2016
Source: Agent Provided
Pending
$224,900
Nov 19, 2015
Source: Agent Provided
PriceChange
$224,900
Price decreased by 4%
Sep 29, 2015
Source: Agent Provided
PriceChange
$234,900
Price decreased by 4%
Aug 10, 2015
Source: Agent Provided
Listed For Sale
$244,900

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 309 Skipper Ln

  • What is 309 Skipper Ln estimated to be worth?
    Trulia's estimated value for 309 Skipper Ln in Chester, MD is $414,600.
  • What is the price history for 309 Skipper Ln?
    309 Skipper Ln in Chester, MD last sold for $215,000 in April 2016.
  • 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 309 Skipper Ln have air conditioning?
    Yes, 309 Skipper Ln in Chester, MD has air conditioning.
  • How big is the lot at 309 Skipper Ln?
    The lot at 309 Skipper Ln in Chester, MD is about 0.49 acres (21,522 sq ft).

Explore by feature - Air Conditioning

7 rentals with air conditioning in Chester, MD

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