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

101 Bufflehead Ct
Chester, MD 21619

2 Beds
2 Baths
1,030 sqft

$279,500

Trulia Estimate

as of Jul 10, 2026

Est. Refi. Payment $1,653/mo*

Refinance Your Home

$279,500

Trulia Estimate

as of Jul 10, 2026

Est. Refi. Payment $1,653/mo*

Refinance Your Home

2 Beds

2 Baths

1,030 sqft

Local Information

Map ViewExplore the area around 101 Bufflehead Ct.
Schools1 Preschool School2 Elementary Schools1 Middle School1 High School
Shop & Eat

-- mins to

Commute Destination

Description

BEAUTIFUL! 2 bdrm 2 full bath, ground level condo on Kent island in the community of Bayside. Features upgraded appliances, fireplace, and hardwood floors. Located a few steps from the amenities and restaurants. Community offers pool w/ clubhouse, gym, tennis avail for tenants use. Only 1 miles from the Bay Bridge makes for an easy commute to Annapolis, Baltimore and Washington D.C. Available now! Dogs allowed. No cats.

101 Bufflehead Ct, Chester, MD 21619 is a 2 bedroom, 2 bathroom, 1,030 sqft townhouse built in 1992. It last sold for $210,000 on Oct 7, 2009. More recently, it was listed as a rental in January 2019 with an asking price of $1,600 per month. That rental listing was removed on February 3, 2019. It is currently off market. The Trulia Estimate is $279,500, with a rent estimate of $2,118/month.

Home Highlights

Parking

No Info

Outdoor

Deck, Pool

A/C

Heating & Cooling

HOA

None

Price/Sqft

No Info

Listed

Less than a day ago

Home Details for 101 Bufflehead Ct

Interior Features
Interior Details BasementAdditional StorageStorage
Heating & Cooling Heating: Heat PumpAir ConditioningHeating Fuel: Heat Pump
Fireplace & Spa Fireplace

Property Information
Year Built Year Built: 1992
Property Type / Style Property Type: Townhouse

Exterior Features
Exterior Home Features Deck
Pool Pool

Community
Units in Building: 1

Lot Information
Lot Area: 954 sqft

Building
Community rooms Fitness Center
Fitness & Sports Tennis Court

Price History for 101 Bufflehead Ct

Date	Price	Event	Source
02/03/2019	$1,600	ListingRemoved	Agent Provided

01/04/2019	$1,600	Listed For Rent	Agent Provided

10/07/2009	$210,000	Sold	N/A
Recording Date 10/07/2009 Contract Date 10/05/2009 County Transfer Tax N/A Total Transfer Tax N/A
05/09/2002	$128,574	Sold	N/A
Recording Date 05/09/2002 County Transfer Tax N/A Total Transfer Tax N/A

Market trends in Chester

Last updated May 2026

Avg. sale price

—

Sale-to-List Price

—

Price per sq ft

—

Available listings

6MoM

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Property Tax and Assessment

Year	2025
Tax	$2,120
Assessment	$225,000

Home facts updated by county records

Comparable Sales for 101 Bufflehead Ct

Address	Distance	Property Type	Sold Price	Sold Date	Bed	Bath	Sqft
202 Ringneck Ct, Chester, MD	0.04	Townhouse	$335,000	09/05/25	2	2.5	1,956
3A Queen Victoria Way, Chester, MD	0.33	Townhouse	$394,000	07/16/25	2	2	1,380
9B Queen Victoria Way, Chester, MD	0.35	Townhouse	$360,000	03/31/26	2	2	1,680
206 Ringneck Ct, Chester, MD	0.05	Townhouse	$335,000	05/05/26	2	2.5	1,747
35F Queen Anne Way, Chester, MD	0.44	Townhouse	$355,000	10/31/25	2	2.5	1,440
208 Ringneck Ct, Chester, MD	0.05	Townhouse	$330,000	09/16/25	2	2.5	1,747
34B Queen Anne Way, Chester, MD	0.44	Townhouse	$320,000	08/12/25	1	1	724
31 Queen Anne Way, Chester, MD	0.41	Townhouse	$322,500	09/04/25	2	1.5	1,104
23 Queen Victoria Way, Chester, MD	0.35	Townhouse	$445,000	05/14/26	2	2	1,104
206 Ringneck Ct #78, Chester, MD	0.05	Townhouse	$335,000	01/02/26	3	2.5	1,747

Nearby homes

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

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OFF MARKET
Est. $347,400
2 bd
2.5 ba
1,956 sqft
202 Ringneck Ct,
Chester, MD 21619
Benson & Mangold, LLC
SOLD
MAY 5, 2026
$326,000
3 bd
3.5 ba
1,747 sqft
204 Ringneck Ct,
Chester, MD 21619
Cummings & Co. Realtors
SOLD
SEP 16, 2025
$330,000
2 bd
2.5 ba
1,747 sqft
208 Ringneck Ct,
Chester, MD 21619
Long & Foster Real Estate, Inc.
SOLD
JAN 2, 2026
$335,000
3 bd
2.5 ba
1,747 sqft
206 Ringneck Ct #78,
Chester, MD 21619
RE/MAX Executive
OFF MARKET
Est. $402,600
3 bd
2.5 ba
1,747 sqft
212 Ringneck Ct,
Chester, MD 21619
Rosendale Realty
OFF MARKET
Est. $394,300
3 bd
2.5 ba
1,747 sqft
102 Ringneck Ct,
Chester, MD 21619
RE/MAX Executive
OFF MARKET
Est. $288,300
2 bd
2 ba
1,050 sqft
216 Teal Ct,
Chester, MD 21619
RE/MAX Executive
OFF MARKET
Est. $272,800
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
OFF MARKET
Est. $306,200
2 bd
2 ba
1,073 sqft
204 Teal Ct #B,
Chester, MD 21619
NetRealtyNow.com, LLC
SOLD
APR 1, 2026
$265,000
2 bd
2 ba
1,073 sqft
306 Teal Ct #C,
Chester, MD 21619
Kelly and Co Realty, LLC
OFF MARKET
Est. $372,100
3 bd
2.5 ba
1,788 sqft
305 Schooner Way #43,
Chester, MD 21619
Coldwell Banker Realty

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Additional Cost

Assigned Schools

These are the assigned schools for 101 Bufflehead Ct.

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
7y ago
"I've lived here for three years and the neighbors are very friendly mostly. They look out for each other..."
0
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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
NEW - 2 DAYS AGO
$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 101 Bufflehead Ct

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OPEN SAT, 11-2PM
$435,000
3 bd
2.5 ba
1,595 sqft
106 Bodys Neck Rd,
Chester, MD 21619
Realty Navigator
$559,900
2 bd
2.5 ba
1,425 sqft
29A Queen Mary Ct,
Chester, MD 21619
Jorge A. Zea
$349,500
2 bd
2.5 ba
1,312 sqft
45 Queen Neva Ct,
Chester, MD 21619
Coldwell Banker Realty
$329,000
2 bd
2.5 ba
1,280 sqft
54 Queen Caroline Ct,
Chester, MD 21619
Long & Foster Real Estate, Inc.
$414,900
3 bd
3 ba
1,899 sqft
208 Blenny Ln,
Chester, MD 21619
RE/MAX Executive
$249,000
1 bd
1 ba
724 sqft
3 Queen Victoria Way,
Chester, MD 21619
Coldwell Banker Realty
$425,500
3 bd
3.5 ba
2,100 sqft
807 Auckland Way,
Chester, MD 21619
Real Broker, LLC
$329,900
3 bd
2.5 ba
1,440 sqft
54D Queen Caroline Ct,
Chester, MD 21619
Island Realty, LLC
$359,900
3 bd
2.5 ba
1,440 sqft
54F Queen Caroline Ct,
Chester, MD 21619
Long & Foster Real Estate, Inc.
$240,000
1 bd
1 ba
724 sqft
8 Queen Victoria Way,
Chester, MD 21619
Long & Foster Real Estate, Inc.
See more homes for sale in
Chester
Take a look

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Off Market Homes Near 101 Bufflehead Ct

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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
JUN 26, 2026
$400,000
3 bd
2 ba
1,260 sqft
607 Kimberly Way,
Stevensville, MD 21666
Samson Properties
SOLD
JUN 25, 2026
$390,000
3 bd
2 ba
1,248 sqft
117 Dundee Ave,
Chester, MD 21619
Coldwell Banker Realty
SOLD
JUN 18, 2026
$379,000
3 bd
2 ba
1,204 sqft
1838 Sherman Dr,
Chester, MD 21619
Keller Williams Realty Centre
SOLD
JUN 18, 2026
$338,000
1 bd
1 ba
724 sqft
34 Queen Anne Way #F,
Chester, MD 21619
Cross Street Realtors LLC
SOLD
JUN 9, 2026
$289,000
600 Old Point Rd,
Chester, MD 21619
SOLD
JUN 8, 2026
$299,900
3 bd
2 ba
1,800 sqft
1914 Anchorage Dr,
Chester, MD 21619
Century 21 Downtown
SOLD
JUN 5, 2026
$410,000
1 ba
1,064 sqft
416 Love Point Rd,
Stevensville, MD 21666
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 2, 2026
$255,000
2 ba
968 sqft
7A Mariners Way,
Stevensville, MD 21666
See more homes for sale in
Chester
Take a look

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101 Bufflehead Ct
Chester, MD 21619

$279,500

$279,500

Local Information