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

1900 Roberta Dr
Chester, MD 21619

4 Beds
4 Baths
3,250 sqft (on 0.42 acres)

$742,100

Trulia Estimate

as of Jun 29, 2026

$742,100

Trulia Estimate

as of Jun 29, 2026

4 Beds

4 Baths

3,250 sqft

(on 0.42 acres)

Local Information

Map ViewExplore the area around 1900 Roberta Dr.
Schools1 Preschool School2 Elementary Schools1 Middle School1 High School
Shop & Eat

-- mins to

Commute Destination

Description

Gorgeous home priced to move! This beautiful, spacious house has been meticulously taken care of. Save on cost of utilities, 75% of electricity is generated by solar panels. Hardwood flooring, stainless steel appliances, 2 car garage and numerous upgrades throughout the house you'll be hard pressed to find any property remotely comparable at this price. Be sure to get in and see this house before someone else snatches it up! Beautiful water view of Cox Creek.

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

Garage

Outdoor

Patio, Deck

A/C

Heating & Cooling

HOA

None

Price/Sqft

No Info

Listed

Less than a day ago

Home Details for 1900 Roberta Dr

Interior Features
Heating & Cooling Heating: Heat Pump, Other, Electric, Gas, SolarAir ConditioningCooling System: Central, SolarHeating Fuel: Heat Pump
Levels, Entrance, & Accessibility Stories: 2Floors: Tile, Carpet, Hardwood
Interior Details AtticNumber of Rooms: 9Types of Rooms: Walk In Closet, Breakfast Nook, Dining Room, Family Room, Laundry Room, Master Bath, Mud Room, Pantry, Sun RoomCeiling Fan
Appliances & Utilities Cable ReadyDishwasherDisposalDryerMicrowaveRefrigerator
Fireplace & Spa FireplaceJetted Bath Tub
Windows, Doors, Floors & Walls Double Paned Windows
Security Security System

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

Property Information
Year Built Year Built: 2007
Property Type / Style Property Type: Single Family HomeArchitecture: Conventional

Community
Units in Building: 1

Lot Information
Lot Area: 0.42 acres

Price History for 1900 Roberta Dr

Date	Price	Event	Source
05/13/2022	$675,000	Sold	Bright MLS #MDQA2003120
Recording Date 05/13/2022 County Transfer Tax N/A Total Transfer Tax N/A
04/10/2022	$665,000	Pending	Bright MLS #MDQA2003120

04/09/2022	$665,000	Contingent	Bright MLS #MDQA2003120

04/08/2022	$665,000	Listed For Sale	Bright MLS #MDQA2003120

02/20/2013	$360,000	Sold	N/A
Recording Date 02/20/2013 Contract Date 02/07/2013 County Transfer Tax $1,800 Total Transfer Tax $3,600
09/07/2012	$375,000	PriceChange	Agent Provided
Price Change $40,000 (-10%)
06/29/2012	$415,000	PriceChange	Agent Provided
Price Change $10,000 (-2%)
03/13/2012	$425,000	PriceChange	Agent Provided
Price Change $25,000 (-6%)
09/10/2011	$450,000	Listed For Sale	Agent Provided

02/07/2008	$505,000	Sold	N/A
Recording Date 02/07/2008 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

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Price per sq ft

—

Available listings

6MoM

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Property Tax and Assessment

Year	2025
Tax	$5,354
Assessment	$568,367

Home facts updated by county records

Comparable Sales for 1900 Roberta Dr

Address	Distance	Property Type	Sold Price	Sold Date	Bed	Bath	Sqft
2613 Cecil Dr, Chester, MD	0.21	Single-Family Home	$900,000	05/13/26	5	2.5	2,496
203 Barren Ridge Rd, Chester, MD	0.12	Single-Family Home	$475,000	09/29/25	3	1.5	2,072
1771 Harbor Dr, Chester, MD	0.48	Single-Family Home	$735,000	09/05/25	5	2.5	2,564
104 Woods Rd, Chester, MD	0.63	Single-Family Home	$795,000	12/10/25	5	3.5	3,065
1773 Harbor Dr, Chester, MD	0.49	Single-Family Home	$610,000	08/29/25	3	2.5	2,142
1809 Stevens Dr, Chester, MD	0.48	Single-Family Home	$445,000	08/14/25	4	2.5	1,896
123 Bentons Pleasure Rd, Chester, MD	0.63	Single-Family Home	$740,000	01/09/26	4	2.5	2,791
1803 Chester Dr, Chester, MD	0.39	Single-Family Home	$385,000	05/09/26	4	2	1,636
1903 Churchhill Ln, Chester, MD	0.59	Single-Family Home	$405,000	11/14/25	4	3	1,682
2008 Palm Dr, Chester, MD	0.56	Single-Family Home	$500,000	08/22/25	3	2.5	2,283

Nearby homes

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

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FOR SALE
0.43 ACRES
$724,500
5 bd
3.5 ba
3,250 sqft
1868 Roberta Dr,
Chester, MD 21619
Coldwell Banker Realty
OFF MARKET
Est. $469,400
4 bd
2 ba
2,055 sqft
104 Barren Ridge Rd,
Chester, MD 21619
Long & Foster Real Estate, Inc.
OFF MARKET
Est. $522,900
4 bd
3 ba
2,560 sqft
1903 Roberta Dr,
Chester, MD 21619
Long & Foster Real Estate, Inc.
OFF MARKET
Est. $611,200
3 bd
2.5 ba
2,100 sqft
1905 Roberta Dr,
Chester, MD 21619
Clark & Co Realty, LLC
OFF MARKET
Est. $684,200
4 bd
4.5 ba
3,016 sqft
105 Barren Ridge Rd,
Chester, MD 21619
Coldwell Banker Waterman Realty
FOR SALE
1.65 ACRES
$1,350,000
5 bd
2 ba
2,700 sqft
2513 Cecil Dr,
Chester, MD 21619
Real Broker, LLC
SOLD
SEP 29, 2025
$475,000
3 bd
1.5 ba
2,072 sqft
203 Barren Ridge Rd,
Chester, MD 21619
Keller Williams Gateway LLC
SOLD
DEC 26, 2025
$205,000
3 bd
1 ba
1,600 sqft
1905-1907 Keister Dr,
Chester, MD 21619
VYBE Realty
OFF MARKET
Est. $698,700
3 bd
2.5 ba
2,336 sqft
2608 Cecil Dr,
Chester, MD 21619
Long & Foster Real Estate, Inc.
OFF MARKET
Est. $491,500
4 bd
2 ba
2,000 sqft
1911 Keister Dr,
Chester, MD 21619
Coldwell Banker Realty
OFF MARKET
Est. $601,800
4 bd
2.5 ba
2,392 sqft
2612 Cecil Dr,
Chester, MD 21619
Rosendale Realty
SOLD
MAY 13, 2026
$900,000
5 bd
2.5 ba
2,496 sqft
2613 Cecil Dr,
Chester, MD 21619
Benson & Mangold, LLC

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Additional Cost

Assigned Schools

These are the assigned schools for 1900 Roberta Dr.

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 | 214 Pier 1 Rd #225,
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
$2,000/mo
2 bd
1.5 ba
16 Mariners Way #A-4,
Stevensville, MD 21666
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
$1,200/mo
1 bd
1 ba
101 Chester Vlg #203,
Chester, MD 21619
PET FRIENDLY
$1,650/mo
1 bd
1 ba
1910 Churchhill Ln #A,
Chester, MD 21619
$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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Explore by feature - Air Conditioning

6 rentals with air conditioning in Chester, MD

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
APPLY INSTANTLY
PET FRIENDLY
$2,100/mo
2 bd
2 ba
1,069 sqft
316 Merganser Ct,
Chester, MD 21619
$1,200/mo
1 bd
1 ba
450 sqft
101 Chester Vlg #203,
Chester, MD 21619
PET FRIENDLY
$1,650/mo
1 bd
1 ba
370 sqft
1910 Churchhill Ln #A,
Chester, MD 21619
$2,300/mo
2 bd
2.5 ba
1,312 sqft
45 Queen Neva Ct #B,
Chester, MD 21619

Homes for sale near 1900 Roberta Dr

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0.43 ACRES
$724,500
5 bd
3.5 ba
3,250 sqft
1868 Roberta Dr,
Chester, MD 21619
Coldwell Banker Realty
1.65 ACRES
$1,350,000
5 bd
2 ba
2,700 sqft
2513 Cecil Dr,
Chester, MD 21619
Real Broker, LLC
$559,000
3 bd
3 ba
1,536 sqft
126 Watermans Cove Ln,
Chester, MD 21619
Coldwell Banker Realty
0.35 ACRES
$475,000
3 bd
2.5 ba
1,728 sqft
1916 Stevens Dr,
Chester, MD 21619
Coldwell Banker Realty
0.34 ACRES
$399,500
3 bd
1.5 ba
1,192 sqft
2645 Cox Neck Rd,
Chester, MD 21619
Compass
$545,000
4 bd
2.5 ba
1,979 sqft
124 Riverside Dr,
Chester, MD 21619
Douglas Realty LLC
0.28 ACRES
$449,900
4 bd
2 ba
1,750 sqft
1906 Harbor Dr,
Chester, MD 21619
Five Star Real Estate
0.41 ACRES
$749,000
3 bd
2 ba
1,524 sqft
205 Riverside Dr,
Chester, MD 21619
Engel & Volkers Annapolis
$665,000
4 bd
2.5 ba
2,564 sqft
303 Creeks End Ln,
Stevensville, MD 21666
Paul Wesley Real Estate
0.28 ACRES
$420,000
3 bd
2.5 ba
1,296 sqft
200 Newtown Rd,
Chester, MD 21619
Samson Properties
See more homes for sale in
Chester
Take a look

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Off Market Homes Near 1900 Roberta Dr

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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 24, 2026
$480,000
3 bd
2 ba
1,804 sqft
1848 Harbor Dr,
Chester, MD 21619
EXP Realty, LLC
SOLD
JUN 19, 2026
$570,000
2 bd
2.5 ba
1,900 sqft
1000 Herons Nest Way #402,
Chester, MD 21619
RE/MAX United Real Estate
SOLD
JUN 18, 2026
$569,000
4 bd
2.5 ba
2,200 sqft
107 Chestnut Rd,
Stevensville, MD 21666
Taylor Properties
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
$430,000
3 bd
2 ba
1,412 sqft
1029 Romancoke Rd,
Stevensville, MD 21666
RE/MAX Executive
SOLD
JUN 18, 2026
$600,000
4 bd
3 ba
2,092 sqft
115 Bay Meadows Ln,
Stevensville, MD 21666
RE/Max Experience
SOLD
JUN 18, 2026
$546,000
5 bd
2.5 ba
2,184 sqft
515 Bayside Dr,
Stevensville, MD 21666
Douglas Realty, LLC
SOLD
JUN 17, 2026
$584,000
4 bd
2.5 ba
2,016 sqft
421 Victoria Way,
Stevensville, MD 21666
Samson Properties
See more homes for sale in
Chester
Take a look

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1900 Roberta Dr, Chester, MD 21619 is a 4 bedroom, 4 bathroom, 3,250 sqft single-family home built in 2007. This property is not currently available for sale. 1900 Roberta Dr was last sold on May 13, 2022 for $675,000. The current Trulia Estimate for 1900 Roberta Dr is $742,100.

1900 Roberta Dr
Chester, MD 21619

$742,100

$742,100

Local Information