Is parking easy in Chester, MD?

As of early 2026, 88% of users say parking is easy

Is a car needed in Chester, MD?

As of early 2026, 88% of users say car is needed

Would people walk alone at night in Chester, MD?

As of early 2026, 86% of users say people would walk alone at night

Is Chester, MD dog-friendly?

As of early 2026, 83% of users say it's dog friendly

Is Chester, MD quiet?

As of early 2026, 83% of users say it's quiet

Does Chester, MD show holiday spirit?

As of early 2026, 80% of users say there's holiday spirit

Are neighbors friendly in Chester, MD?

As of early 2026, 65% of users say neighbors are friendly

Do kids play outside in Chester, MD?

As of early 2026, 64% of users say kids play outside

Is there wildlife in Chester, MD?

As of early 2026, 64% of users say there's wildlife

Are yards well-kept in Chester, MD?

As of early 2026, 57% of users say yards are well-kept

Does Chester, MD have sidewalks?

As of early 2026, 53% of users say there are sidewalks

Do residents of Chester, MD plan to stay at least 5 years?

As of early 2026, 49% of users say they plan to stay for at least 5 years

Are there community events in Chester, MD?

As of early 2026, 48% of users say there are community events

Are the streets well-lit in Chester, MD?

As of early 2026, 44% of users say streets are well-lit

Is Chester, MD walkable to restaurants?

As of early 2026, 41% of users say it's walkable to restaurants

Is Chester, MD walkable to grocery stores?

As of early 2026, 17% of users say it's walkable to grocery stores

OFF MARKET

104 Skipper Ln
Chester, MD 21619

4 Beds
2 Baths
2,200 sqft (on 0.42 acres)

$470,300

Trulia Estimate

as of Jul 12, 2026

Est. Refi. Payment $2,743/mo*

Refinance Your Home

$470,300

Trulia Estimate

as of Jul 12, 2026

Est. Refi. Payment $2,743/mo*

Refinance Your Home

4 Beds

2 Baths

2,200 sqft

(on 0.42 acres)

Local Information

Map ViewExplore the area around 104 Skipper Ln.
Schools1 Preschool School2 Elementary Schools1 Middle School1 High School
Shop & Eat

-- mins to

Commute Destination

Description

This single-family home is located at 104 Skipper Ln, Chester, MD. 104 Skipper Ln is in Chester, MD and in ZIP code 21619. This property has 4 bedrooms, 2 bathrooms and approximately 2,200 sqft of floor space. This property has a lot size of 0.42 acres and was built in 1962.

104 Skipper Ln, Chester, MD 21619 is a 4 bedroom, 2 bathroom, 2,200 sqft single-family home built in 1962. It is currently off market. The Trulia Estimate is $470,300, with a rent estimate of $3,071/month.

Home Highlights

Parking

Garage

Outdoor

Patio, Deck

A/C

Heating & Cooling

HOA

None

Price/Sqft

No Info

Listed

Less than a day ago

Home Details for 104 Skipper Ln

Interior Features
Interior Details BasementAtticIn-law unitNumber of Rooms: 11Types of Rooms: Dining Room, Family Room, Laundry Room, Mud Room, Office, Recreation Room, Solarium Atrium, Sun RoomWet BarCeiling Fan
Heating & Cooling Heating: Other, ElectricAir ConditioningCooling System: CentralHeating Fuel: Other
Levels, Entrance, & Accessibility Stories: 3Floors: Tile, Hardwood
Appliances & Utilities Cable ReadyDishwasherDryerMicrowaveRefrigeratorWasher
Fireplace & Spa FireplaceHot Tub or Spa
Windows, Doors, Floors & Walls Double Paned Windows
Security Security System

Exterior Features
Exterior Home Features Roof: Shake ShingleDeckExterior: Other, BrickGardenLawnPatio
Parking & Garage GarageParking Spaces: 4Parking: Garage Attached

Property Information
Year Built Year Built: 1962Year Updated: 2015
Property Type / Style Property Type: Single Family HomeArchitecture: Split-level

Community
Units in Building: 1

Lot Information
Lot Area: 0.42 acres

Market trends in Chester

Last updated June 2026

Avg. sale price

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Sale-to-List Price

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Price per sq ft

—

Available listings

1MoM

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Property Tax and Assessment

Year	2025
Tax	$3,349
Assessment	$355,467

Home facts updated by county records

Comparable Sales for 104 Skipper Ln

Address	Distance	Property Type	Sold Price	Sold Date	Bed	Bath	Sqft
203 Anchor Ln, Chester, MD	0.06	Single-Family Home	$499,000	08/06/25	3	2	1,890
307 Skipper Ln, Chester, MD	0.20	Single-Family Home	$490,000	10/30/25	3	2	2,180
306 Skipper Ln, Chester, MD	0.20	Single-Family Home	$569,000	12/03/25	4	2.5	2,610
129 Sailcloth Way, Chester, MD	0.22	Single-Family Home	$764,900	05/22/26	3	2	2,303
204 Skipper Ln, Chester, MD	0.12	Single-Family Home	$630,000	10/30/25	6	3	3,760
320 Bayberry Dr, Chester, MD	0.29	Single-Family Home	$775,000	07/28/25	3	2	2,331
255 Sailcloth Way, Chester, MD	0.18	Single-Family Home	$898,000	10/01/25	4	4	3,450
224 Bayberry Dr, Chester, MD	0.23	Single-Family Home	$550,000	01/23/26	2	2	1,913
223 Broadwater Dr, Chester, MD	0.22	Single-Family Home	$837,000	09/30/25	3	3	2,745
219 Broadwater Dr, Chester, MD	0.23	Single-Family Home	$643,000	04/08/26	2	2	1,913

Nearby homes

Get a sense of prices in the area by checking nearby homes.

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OFF MARKET
Est. $585,100
3 bd
2.5 ba
1,810 sqft
102 Skipper Ln,
Chester, MD 21619
Benson & Mangold, LLC
OFF MARKET
Est. $518,900
3 bd
2 ba
1,890 sqft
203 Anchor Ln,
Chester, MD 21619
Wilson Realty & Staging LLC
COMING SOON 7/14
3D VIEW
0.5 ACRES
$535,000
5 bd
3 ba
3,000 sqft
205 Anchor Ln,
Chester, MD 21619
Samson Properties
OFF MARKET
Est. $603,800
5 bd
3 ba
2,726 sqft
105 Pilot Ct,
Chester, MD 21619
Redfin Corp
SOLD
OCT 30, 2025
$630,000
6 bd
3 ba
3,760 sqft
204 Skipper Ln,
Chester, MD 21619
Douglas Realty, LLC
OFF MARKET
Est. $882,600
3 bd
4 ba
3,299 sqft
103 Spinnaker Way,
Chester, MD 21619
RE/MAX Executive
OFF MARKET
Est. $625,100
2 bd
2 ba
1,913 sqft
124 Spinnaker Way,
Chester, MD 21619
Samson Properties
OFF MARKET
Est. $617,400
3 bd
2 ba
1,754 sqft
511 Skipper Ct,
Chester, MD 21619
Sellers Choice Real Estate, LLC.
OFF MARKET
Est. $284,100
2 bd
2 ba
1,030 sqft
109 Bufflehead Ct #E,
Chester, MD 21619
OFF MARKET
Est. $278,100
2 bd
2 ba
1,069 sqft
115 Bufflehead Ct #H,
Chester, MD 21619
Coldwell Banker Waterman Realty
SOLD
OCT 1, 2025
$898,000
4 bd
4 ba
3,450 sqft
255 Sailcloth Way,
Chester, MD 21619
Keller Williams Flagship
OFF MARKET
Est. $843,200
3 bd
3 ba
2,480 sqft
171 Spinnaker Way,
Chester, MD 21619
Long & Foster Real Estate, Inc.

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Additional Cost

Assigned Schools

These are the assigned schools for 104 Skipper Ln.

View nearby schools on GreatSchools

The GreatSchools Rating compares schools on a variety of school quality indicators including test scores, college readiness, equity and more. Learn more.

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
Resident
2y ago
"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
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Colinjgallagher525
Resident
2y ago
"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
Resident
2y ago
"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
Resident
2y ago
"Water aerobics, happy hours, cardboard boat races, kayaking, mah jongg, game day dog walking. Boating "
0
Flag
Peggy.young
Resident
6y ago
"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.
Resident
6y ago
"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
Resident
7y ago
"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
Resident
7y ago
"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
Resident
7y ago
"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
Resident
7y ago
"Not very many families, but within a great school district. Good community for people who don’t really have children. "
0
Flag
J0J0s4X4
Resident
7y ago
"it is a child friendly development and very safe. also, most homeowners have video security systems."
0
Flag
Peggy y.
Resident
8y ago
"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.
11y ago
"I live in this area. Great place to raise a family. Access to beaches, parks, cross island trail."
0
Flag

LGBTQ Local Legal Protections

Apartments for Rent

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PET FRIENDLY
$1,850 - $2,995/mo
Total price
Studio-2 bd
1-2 ba
Bay Manor Shops and Apartments | Pier 1 Rd,
Stevensville, MD 21666
PET FRIENDLY
INCOME RESTRICTED
$1,158/mo
1 bd
1 ba
101 Ellicott Dr #1B-1Ba-552Sqft,
Chester, MD 21619
PET FRIENDLY
INCOME RESTRICTED
$1,091/mo
2 bd
1 ba
39 Sherman Way #a656b564b,
Chester, MD 21619
Contact for price
1-2 bd
1-2 ba
800 Abruzzi Dr #f320a52c6,
Chester, MD 21619
APPLY INSTANTLY
PET FRIENDLY
$2,600/mo
3 bd
1 ba
440 Main St #1000-C,
Stevensville, MD 21666
APPLY INSTANTLY
PET FRIENDLY
$2,200/mo
2 bd
1 ba
460 Main St #1000-B,
Stevensville, MD 21666
APPLY INSTANTLY
PET FRIENDLY
$2,200/mo
2 bd
1 ba
480 Main St #1000-B,
Stevensville, MD 21666
$2,300/mo
2 bd
2.5 ba
45 Queen Neva Ct #B,
Chester, MD 21619
See more homes for rent in
Chester
Take a look

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Homes for sale near 104 Skipper Ln

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COMING SOON 7/14
0.5 ACRES
$535,000
5 bd
3 ba
3,000 sqft
205 Anchor Ln,
Chester, MD 21619
Samson Properties
0.28 ACRES
$449,900
4 bd
2 ba
1,750 sqft
1906 Harbor Dr,
Chester, MD 21619
Five Star Real Estate
NEW
OPEN SUN, 12-3PM
COMING SOON 7/15
$719,900
2 bd
2 ba
2,118 sqft
121 Merlin Dr,
Chester, MD 21619
Coldwell Banker Realty
$749,900
4 bd
3 ba
3,151 sqft
233 Peregrine Dr,
Chester, MD 21619
Rosendale Realty
0.35 ACRES
$475,000
3 bd
2.5 ba
1,728 sqft
1916 Stevens Dr,
Chester, MD 21619
Coldwell Banker Realty
$619,900
4 bd
2.5 ba
2,208 sqft
324 Web Foot Ln,
Stevensville, MD 21666
Rosendale Realty
0.34 ACRES
$399,500
3 bd
1.5 ba
1,192 sqft
2645 Cox Neck Rd,
Chester, MD 21619
Compass
0.36 ACRES
$499,900
4 bd
2.5 ba
1,704 sqft
606 Kimberly Way,
Stevensville, MD 21666
Long & Foster Real Estate, Inc.
See more homes for sale in
Chester
Take a look

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Off Market Homes Near 104 Skipper Ln

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SOLD
JUL 10, 2026
$551,000
4 bd
3 ba
2,216 sqft
412 Bay City Rd,
Stevensville, MD 21666
Samson Properties
SOLD
JUL 9, 2026
$280,000
2 bd
1 ba
1,120 sqft
4003 Main St,
Grasonville, MD 21638
Long & Foster Real Estate, Inc.
SOLD
JUL 7, 2026
$450,000
4 bd
3 ba
1,800 sqft
708 Dixon Dr,
Stevensville, MD 21666
Long & Foster Real Estate, Inc.
SOLD
JUL 6, 2026
$258,000
2 bd
1.5 ba
968 sqft
1 Compass Cir #2,
Stevensville, MD 21666
Berkshire Hathaway Homeservice Homesale Realty
SOLD
JUL 1, 2026
$665,000
4 bd
3.5 ba
2,437 sqft
1033 Avalon Ct,
Stevensville, MD 21666
Chesapeake Real Estate Associates, LLC
SOLD
JUL 1, 2026
$489,000
4 bd
2 ba
1,596 sqft
756 Kimberly Way,
Stevensville, MD 21666
Samson Properties
SOLD
JUL 1, 2026
$699,990
2 bd
2.5 ba
2,602 sqft
630 Warbler Way #2224,
Chester, MD 21619
KOVO Realty
SOLD
JUN 30, 2026
$471,500
3 bd
2 ba
2,016 sqft
1906 Stevens Dr,
Chester, MD 21619
RE/MAX Executive
SOLD
JUN 30, 2026
$480,000
3 bd
3 ba
2,256 sqft
118 Sophie Ln,
Stevensville, MD 21666
Wilson Realty & Staging LLC
SOLD
JUN 26, 2026
$400,000
3 bd
2 ba
1,260 sqft
607 Kimberly Way,
Stevensville, MD 21666
Samson Properties
See more homes for sale in
Chester
Take a look

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104 Skipper Ln
Chester, MD 21619

$470,300

$470,300

Local Information