1868 Roberta Dr, Chester, MD 21619
Property image
Property image
AUCTION
0.43 ACRES

$400,000

  • 5 Beds
  • 3.5 Baths
  • 3,250 sqft (on 0.43 acres)

1868 Roberta Dr, Chester, MD 21619

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Home Highlights

Single-Family Home
Built in 2007
0.43 acre lot
$123/sqft
2 Car Garage

Local Information

  • Map ViewExplore the area around 1868 Roberta Dr.
  • Schools1 Preschool School2 Elementary Schools1 Middle School1 High School
  • Shop & Eat
-- mins to
Commute Destination

About this House

List price is Opening Bid at the Online auction to be conducted on Auctioneers website. - Auction ends Tuesday, September 29, 2026 at 11:00 AM. Discover the space and versatility of 1868 Roberta Drive in Chester, Maryland, a custom-built home offering 5 bedrooms, 3.5 bathrooms, multiple living areas, abundant storage, and no HOA. Conveniently located just minutes from Route 50 and the Chesapeake Bay Bridge, this property combines generous proportions with a layout designed for comfortable everyday living and entertaining. The main level makes an immediate impression with 12-foot ceilings and oversized 6-foot windows, creating bright, open living spaces throughout. The floor plan includes a spacious family room, vaulted morning room, sunroom, and an eat-in kitchen that serves as the heart of the home. The kitchen is equipped with granite countertops, a large center island, pantry, and ample cabinet and workspace. The home’s 5-bedroom, 3.5-bath configuration provides plenty of flexibility. The primary suite features a tray ceiling and private bath with a custom-tiled shower and double vanity. Four additional bedrooms are complemented by two Jack-and-Jill-style bathrooms, offering a functional arrangement for family, guests, home offices, or additional flex space. Outdoor living is another highlight, with an impressive 800± square-foot wraparound deck providing plenty of room for grilling, dining, entertaining, and relaxing. Additional features include: • Hardwood and tile flooring • Roman blinds and wood shutters • New HVAC system • Finished garage • Dedicated laundry room with New washer and dryer • Approximately 4-foot crawl-space ceiling height • Numerous custom builder upgrades • No HOA With its impressive bedroom count, expansive living areas, oversized deck, substantial storage, and convenient Chester location, 1868 Roberta Drive offers bidders a unique opportunity to purchase a custom Eastern Shore home and make it their own. Don’t miss your opportunity to bid!
Last check for updates: about 9 hours ago
Listing courtesy of Carley Cooper, (443) 470-1447
Alex Cooper Auctioneers, Inc.
Source: Bright MLS, MLS#MDQA2018570
Also Listed on Bright MLS.

Open House

Wednesday, September 16
5:30 PM to 6:30 PM
Saturday, September 26
12:00 PM to 1:00 PM

Home Details for 1868 Roberta Dr

Interior Features

Interior Details
Number of Rooms: 1Types of Rooms: Basement
Beds & Baths
Number of Bedrooms: 5Number of Bathrooms: 4Number of Bathrooms (full): 3Number of Bathrooms (half): 1Number of Bathrooms (main level): 1
Dimensions and Layout
Living Area: 3250 Square Feet
Appliances & Utilities
Utilities: Cable Connected, Phone, PropaneAppliances: Microwave, Dishwasher, Disposal, Dryer, ENERGY STAR Qualified Washer, Exhaust Fan, Oven/Range - Electric, Cooktop, Washer, Water Conditioner - Owned, Water Heater, Electric Water HeaterDishwasherDisposalDryerLaundry: Main LevelMicrowaveWasher
Heating & Cooling
Heating: Forced Air,Heat Pump,Programmable Thermostat,ElectricHas CoolingAir Conditioning: Ceiling Fan(s),Central Air,Heat Pump,Programmable Thermostat,ElectricHas HeatingHeating Fuel: Forced Air
Fireplace & Spa
Number of Fireplaces: 1Fireplace: Gas/PropaneHas a Fireplace
Windows, Doors, Floors & Walls
Flooring: Carpet, Ceramic Tile, Engineered Wood, Hardwood
Levels, Entrance, & Accessibility
Stories: 2Levels: TwoAccessibility: NoneFloors: Carpet, Ceramic Tile, Engineered Wood, Hardwood
View
Has a ViewView: Trees/Woods, Water

Exterior Features

Exterior Home Features
Roof: Architectural ShinglePatio / Porch: Deck, PorchOther Structures: Above Grade, Below GradeExterior: Bump-outs, Flood LightsFoundation: Crawl SpaceNo Private Pool
Parking & Garage
Number of Garage Spaces: 2Number of Covered Spaces: 2No CarportHas a GarageHas an Attached GarageHas Open ParkingParking Spaces: 2Parking: Garage Faces Front,Garage Door Opener,Inside Entrance,Oversized,Driveway,Attached,Off Street
Pool
Pool: None
Frontage
Not on Waterfront
Water & Sewer
Sewer: Public SewerWater Body: Cox Creek
Finished Area
Finished Area (above surface): 3250 Square Feet

Days on Market

Days on Market: 7

Property Information

Year Built
Year Built: 2007
Property Type / Style
Property Type: ResidentialProperty Subtype: Single Family ResidenceStructure Type: DetachedArchitecture: Coastal,Colonial
Building
Construction Materials: Stone, Vinyl SidingNot a New Construction
Property Information
Condition: Very GoodParcel Number: 1804117964

Price & Status

Price
List Price: $400,000Price Per Sqft: $123
Status Change & Dates
Possession Timing: Close Of Escrow

Active Status

MLS Status: ACTIVE

Location

Direction & Address
City: CHESTERCommunity: None Available
School Information
Elementary School District: Queen Anne's County Public SchoolsJr High / Middle School District: Queen Anne's County Public SchoolsHigh School District: Queen Anne's County Public Schools

Agent Information

Listing Agent
Listing ID: MDQA2018570

Building

Building Details
Builder Name: Lacrosse
Building Area
Building Area: 3250 Square Feet

Community

Not Senior Community

HOA

No HOA

Lot Information

Lot Area: 0.43 acres

Listing Info

Special Conditions: Auction

Offer

Listing Agreement Type: Exclusive Right To Sell

Business

Business Information
Ownership: Fee Simple

Miscellaneous

Mls Number: MDQA2018570Water ViewWater View: WaterAbove Grade Unfinished Area: 3250

Additional Information

Source Internet Automated Valuation Display: NSource Internet Consumer Comment: NSource Internet Entire Listing Display: YSource Internet Address Display: Y

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

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

Home Value

Trulia Estimate
$710K
Since last month
Decreased$3K (-0.4%)
Since last year
Decreased$49K (-6.5%)
Since last sale
Increased$61K (+9.4%)
Learn more about this home's value by checking out its Trulia Estimate and the value of nearby homes.

Trulia Estimate

The of this home's value increased by +5% in the last 10 years
MonthEstimated value
2026
August 2026$709K
August 2026$708K
July 2026$711K
June 2026$712K
May 2026$714K
April 2026$736K
March 2026$738K
February 2026$772K
January 2026$775K
2025
2024
2023
2022
2021
2020
2019
2018
2017
2016

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
104 Barren Ridge Rd, Chester, MD 21619
0.07
$461,900
4
2
2,055
Off Market
1905 Roberta Dr, Chester, MD 21619
0.06
$604,100
3
2.5
2,100
Off Market
105 Barren Ridge Rd, Chester, MD 21619
0.10
$671,300
4
4.5
3,016
Off Market
2513 Cecil Dr, Chester, MD 21619
0.09
$1,290,000
5
2
2,700
For Sale
203 Barren Ridge Rd, Chester, MD 21619
0.13
$496,700
3
1.5
2,072
Off Market
1905-1907 Keister Dr, Chester, MD 21619
0.12
$205,000
3
1
1,600
Recently Sold
2608 Cecil Dr, Chester, MD 21619
0.12
$697,500
3
2.5
2,336
Off Market
2612 Cecil Dr, Chester, MD 21619
0.17
$612,400
4
2.5
2,392
Off Market
2613 Cecil Dr, Chester, MD 21619
0.20
$900,000
5
2.5
2,496
Recently Sold
2616 B Cecil Dr, Chester, MD 21619
0.21
$485,800
4
3
-
Off Market
300 Skyler Ave, Chester, MD 21619
0.26
$535,200
3
2.5
2,250
Off Market

Price and Tax history

DateEventPrice
Aug 4, 2026
Source: Bright MLS #MDQA2016194
ListingRemoved
$724,500
Jun 26, 2026
Source: Bright MLS #MDQA2016194
PriceChange
$724,500
Price decreased by 0%
May 20, 2026
Source: Bright MLS #MDQA2016194
PriceChange
$725,000
Price decreased by 3%
May 1, 2026
Source: Bright MLS #MDQA2016194
PriceChange
$744,500
Price decreased by 1%
Mar 25, 2026
Source: Bright MLS #MDQA2016194
PriceChange
$749,500
Price decreased by 3%

LGBTQ Local Legal Protections

Carley Cooper, Alex Cooper Auctioneers, Inc.
Agent Phone: (443) 470-1447
The data relating to real estate for sale on this website appears in part through the BRIGHT Internet Data Exchange program, a voluntary cooperative exchange of property listing data between licensed real estate brokerage firms, and is provided by BRIGHT through a licensing agreement. Listing information is from various brokers who participate in the Bright MLS IDX program and not all listings may be visible on the site. The property information being provided on or through the website is for the personal, non-commercial use of consumers and such information may not be used for any purpose other than to identify prospective properties consumers may be interested in purchasing. Some properties which appear for sale on the website may no longer be available because they are for instance, under contract, sold or are no longer being offered for sale. Property information displayed is deemed reliable but is not guaranteed. Copyright 2026 Bright MLS, Inc. Click here for more information

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Frequently asked questions about 1868 Roberta Dr

  • What is the estimated monthly payment for 1868 Roberta Dr?
    Based on a $400,000 list price with 20% down at today's rates, the estimated monthly payment for 1868 Roberta Dr in Chester, MD is approximately $2,440 (about $2,102 principal & interest, $263 property taxes, and $75 homeowner's insurance). This is an estimate. Actual payment depends on your loan terms.
  • 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 homes for sale in Chester, MD.
  • What are the closest schools to 1868 Roberta Dr?
    The closest schools to 1868 Roberta Dr in Chester, MD are Bayside Elementary School (rated 8/10), Kent Island Elementary School (Pre-K), Kent Island High School (rated 6/10).
  • What is 1868 Roberta Dr estimated to be worth?
    Trulia's estimated value for 1868 Roberta Dr in Chester, MD is $709,500.
  • Does 1868 Roberta Dr have air conditioning?
    Yes, 1868 Roberta Dr in Chester, MD has air conditioning.
  • Does 1868 Roberta Dr have laundry facilities?
    Yes, 1868 Roberta Dr in Chester, MD has in-unit laundry.
1868 Roberta Dr, Chester, MD 21619 is a 5 bedroom, 4 bathroom, 3,250 sqft single-family home built in 2007. This property is currently available for sale and was listed by Bright MLS on Aug 31, 2026. The MLS # for this home is MLS# MDQA2018570.