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

409 Skipper Ln
Chester, MD 21619

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

$485,500

Trulia Estimate

as of Jun 8, 2026

Est. Refi. Payment $2,822/mo*

Refinance Your Home

$485,500

Trulia Estimate

as of Jun 8, 2026

Est. Refi. Payment $2,822/mo*

Refinance Your Home

4 Beds

3 Baths

1,094 sqft

(on 0.47 acres)

Local Information

-- mins to

Commute Destination

Description

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!

This property is off market, which means it's not currently listed for sale or rent on Trulia. This may be different from what's available on other websites or public sources.

Home Highlights

Parking

No Info

Outdoor

Deck

A/C

Heating & Cooling

HOA

None

Price/Sqft

No Info

Listed

Less than a day ago

Home Details for 409 Skipper Ln

Interior Features
Interior Details Basement
Heating & Cooling Heating: OtherAir ConditioningHeating Fuel: Other
Levels, Entrance, & Accessibility Stories: 1
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 History for 409 Skipper Ln

Date	Price	Event	Source
02/09/2010	$270,000	Sold	N/A
Recording Date 02/09/2010 Contract Date 02/03/2010 County Transfer Tax N/A Total Transfer Tax N/A
10/16/2009	$280,000	Listed For Sale	Agent Provided

03/29/2004	$255,000	Sold	N/A
Recording Date 03/29/2004 County Transfer Tax N/A Total Transfer Tax N/A

Market trends in Chester

Last updated April 2026

Avg. sale price

—

Sale-to-List Price

—

Price per sq ft

—

Available listings

11MoM

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Property Tax and Assessment

Year	2025
Tax	$3,262
Assessment	$346,300

Home facts updated by county records

Comparable Sales for 409 Skipper Ln

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
203 Anchor Ln, Chester, MD	0.24	Single-Family Home	$499,000	08/06/25	3	2	1,890
204 Skipper Ln, Chester, MD	0.25	Single-Family Home	$630,000	10/30/25	6	3	3,760
2723 Cox Neck Rd, Chester, MD	0.92	Single-Family Home	$447,500	10/17/25	4	2.5	1,600
124 Nauset Ln, Chester, MD	0.29	Single-Family Home	$825,000	12/09/25	3	3	2,583
412 Hanna Ct, Chester, MD	0.76	Single-Family Home	$485,000	07/31/25	4	2.5	1,840
2747 Cecil Dr, Chester, MD	0.82	Single-Family Home	$350,000	06/13/25	3	2	1,560
223 Broadwater Dr, Chester, MD	0.37	Single-Family Home	$837,000	09/30/25	3	3	2,745
326 Hanna Ct, Chester, MD	0.81	Single-Family Home	$400,000	12/01/25	4	2.5	1,840

Nearby homes

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

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SOLD
APR 30, 2026
$405,000
2 bd
2 ba
1,380 sqft
27 Queen Mary Ct #F,
Chester, MD 21619
Long & Foster Real Estate, Inc.
FOR SALE
$584,900
2 bd
2.5 ba
1,425 sqft
29 Queen Mary Ct,
Chester, MD 21619
Jorge A. Zea
FOR SALE
$269,000
1 bd
1 ba
724 sqft
3 Queen Victoria Way,
Chester, MD 21619
Coldwell Banker Realty
OFF MARKET
Est. $361,900
2 bd
2.5 ba
1,660 sqft
28 Queen Mary Ct,
Chester, MD 21619
Realty Navigator
OFF MARKET
Est. $382,200
3 bd
2 ba
1,763 sqft
2 Queen Victoria Ct,
Chester, MD 21619
Northrop Realty
SOLD
JAN 14, 2026
$339,900
2 bd
2.5 ba
1,440 sqft
30 Queen Mary Ct,
Chester, MD 21619
Douglas Realty, LLC
OFF MARKET
Est. $384,800
2 bd
2 ba
1,260 sqft
1 Queen Victoria Ct,
Chester, MD 21619
Cummings & Co. Realtors
OFF MARKET
Est. $284,400
1 bd
1 ba
640 sqft
26 Queen Anne Way #26K,
Chester, MD 21619
Rosendale Realty
SOLD
APR 30, 2026
$275,000
1 bd
1 ba
724 sqft
6 Queen Victoria Way,
Chester, MD 21619
Realty Navigator
OFF MARKET
Est. $235,000
1 bd
1 ba
724 sqft
8F Queen Victoria Way,
Chester, MD 21619
Star Realty
FOR SALE
$240,000
1 bd
1 ba
724 sqft
8 Queen Victoria Way,
Chester, MD 21619
Long & Foster Real Estate, Inc.
OFF MARKET
Est. $616,700
3 bd
2 ba
1,754 sqft
511 Skipper Ct,
Chester, MD 21619
Sellers Choice Real Estate, LLC.

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Additional Cost

Assigned Schools

These are the assigned schools for 409 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
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kara
Resident
6y 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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APPLY INSTANTLY
PET FRIENDLY
$1,850 - $2,995/mo
Total price
Studio-2 bd
1-2 ba
Bay Manor Shops and Apartments | 214 Pier 1 Rd #225,
Stevensville, MD 21666
PET FRIENDLY
INCOME RESTRICTED
$1,083/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
PET FRIENDLY
$3,250/mo
3 bd
3 ba
906 Moorings Cir #9,
Stevensville, MD 21666
APPLY INSTANTLY
$2,000/mo
2 bd
2 ba
205 Golden Eye Ct #205,
Chester, MD 21619
APPLY INSTANTLY
$2,090/mo
2 bd
2 ba
115 Bufflehead Ct #H,
Chester, MD 21619
APPLY INSTANTLY
PET FRIENDLY
$2,700/mo
3 bd
1 ba
440 Main St #1000-C,
Stevensville, MD 21666
APPLY INSTANTLY
PET FRIENDLY
$2,200/mo
2 bd
1 ba
480 Main St #1000-B,
Stevensville, MD 21666
APPLY INSTANTLY
PET FRIENDLY
$2,100/mo
2 bd
1 ba
460 Main St #1000-B,
Stevensville, MD 21666
APPLY INSTANTLY
$2,200/mo
3 bd
2 ba
1508 Marion Quimby Dr #8,
Stevensville, MD 21666
See more homes for rent in
Chester
Take a look

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Explore by feature

PET FRIENDLY
INCOME RESTRICTED
$1,083/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
APPLY INSTANTLY
$1,650/mo
1 bd
1 ba
700 sqft
1910 Churchhill Ln,
Chester, MD 21619
NEW - 2 DAYS AGO
APPLY INSTANTLY
PET FRIENDLY
$2,300/mo
2 bd
2 ba
1,069 sqft
316 Merganser Ct,
Chester, MD 21619
APPLY INSTANTLY
$2,000/mo
2 bd
2 ba
1,075 sqft
205 Golden Eye Ct #205,
Chester, MD 21619
APPLY INSTANTLY
$2,090/mo
2 bd
2 ba
1,069 sqft
115 Bufflehead Ct #H,
Chester, MD 21619
APPLY INSTANTLY
PET FRIENDLY
$2,950/mo
4 bd
2.5 ba
1,852 sqft
2605 Harrington Rd,
Chester, MD 21619
PET FRIENDLY
$1,950/mo
2 bd
1.5 ba
1,200 sqft
2201 Main St #105,
Chester, MD 21619
8 rentals with air conditioning in Chester, MD

Homes for sale near 409 Skipper Ln

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NEW
COMING SOON 6/12
0.5 ACRES
$569,000
3 bd
2 ba
1,944 sqft
206 Anchor Ln,
Chester, MD 21619
Coldwell Banker Waterman Realty
$594,500
3 bd
2.5 ba
1,839 sqft
134 McHenny Ct,
Chester, MD 21619
Coldwell Banker Realty
$1,350,000
5 bd
3.5 ba
4,334 sqft
108 Carriage Heath,
Chester, MD 21619
Coldwell Banker Realty
$775,000
3 bd
2.5 ba
2,276 sqft
126 Claiborne St,
Chester, MD 21619
Samson Properties
$780,000
4 bd
3.5 ba
2,185 sqft
134 Richard Ingle Way,
Chester, MD 21619
Keller Williams Realty Central-Delaware
$945,000
4 bd
3.5 ba
3,634 sqft
132 Kestrel Ln,
Chester, MD 21619
TTR Sotheby's International Realty
$865,000
4 bd
3.5 ba
3,312 sqft
232 Evelyne St,
Chester, MD 21619
TTR Sotheby's International Realty
$707,000
4 bd
3 ba
2,870 sqft
266 Peregrine Dr,
Chester, MD 21619
RE/MAX Executive
$640,000
3 bd
2.5 ba
2,119 sqft
265 Evelyne St,
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
See more homes for sale in
Chester
Take a look

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Off Market Homes Near 409 Skipper Ln

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SOLD
JUN 5, 2026
$529,000
3 bd
2.5 ba
1,752 sqft
308 Wallman Way,
Stevensville, MD 21666
Chaney Homes, LLC
SOLD
JUN 3, 2026
$375,000
3 bd
1.5 ba
2,200 sqft
1150 Little Creek Rd,
Chester, MD 21619
Coldwell Banker Realty
SOLD
JUN 1, 2026
$440,000
3 bd
2 ba
1,736 sqft
711 Shi Ln,
Stevensville, MD 21666
Long & Foster Real Estate, Inc.
SOLD
MAY 29, 2026
$599,900
2 bd
2.5 ba
1,900 sqft
630 Warbler Way #2233,
Chester, MD 21619
KOVO Realty
SOLD
MAY 28, 2026
$612,500
2 bd
2.5 ba
1,900 sqft
630 Warbler Way #2232,
Chester, MD 21619
KOVO Realty
SOLD
MAY 27, 2026
$714,280
5 bd
2.5 ba
3,864 sqft
1000 Chesapeake Dr,
Stevensville, MD 21666
Coldwell Banker Realty
SOLD
MAY 27, 2026
$559,900
2 bd
2.5 ba
1,900 sqft
630 Warbler Way #2223,
Chester, MD 21619
KOVO Realty
SOLD
MAY 22, 2026
$417,500
3 bd
2 ba
1,312 sqft
635 Davol Rd,
Stevensville, MD 21666
Blackwell Real Estate, LLC
SOLD
MAY 21, 2026
$470,000
4 bd
3 ba
2,640 sqft
620 Old Love Point Rd,
Stevensville, MD 21666
Berkshire Hathaway HomeServices PenFed Realty
SOLD
MAY 21, 2026
$519,900
3 bd
2.5 ba
2,000 sqft
1921 Harbor Dr,
Chester, MD 21619
Coldwell Banker Waterman Realty
See more homes for sale in
Chester
Take a look

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Homes for rent near 409 Skipper Ln

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APPLY INSTANTLY
$1,650/mo
1 bd
1 ba
700 sqft
1910 Churchhill Ln,
Chester, MD 21619
APPLY INSTANTLY
PET FRIENDLY
$3,600/mo
4 bd
3 ba
2,730 sqft
314 John Patrick Dr,
Stevensville, MD 21666
APPLY INSTANTLY
FURNISHED
$2,950/mo
3 bd
2 ba
2,073 sqft
410 Main St,
Stevensville, MD 21666
APPLY INSTANTLY
PET FRIENDLY
$2,950/mo
4 bd
2.5 ba
1,852 sqft
2605 Harrington Rd,
Chester, MD 21619
PET FRIENDLY
$2,550/mo
2 bd
2.5 ba
1,232 sqft
341 Creekside Commons Ct,
Stevensville, MD 21666
See more homes for rent in
Chester
Take a look

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409 Skipper Ln, Chester, MD 21619 is a 4 bedroom, 3 bathroom, 1,094 sqft single-family home built in 1987. This property is not currently available for sale. 409 Skipper Ln was last sold on Feb 9, 2010 for $270,000. The current Trulia Estimate for 409 Skipper Ln is $485,500.

409 Skipper Ln
Chester, MD 21619

$485,500

$485,500

Local Information