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Chester, Maryland is the second town you will come to after crossing the Chesapeake Bay Bridge into Queen Anne’s County. This town is also a part of Kent Island and is a seven square mile area. The town of Chester has a wide variety of housing choices to meet any real estate need you may have. There are lovely waterfront condos, townhomes, single family homes and luxury waterfront estates. This area also has all of the conveniences to meet all of your shopping, dining, retail and entertainment needs. There are several public boat launches and marinas for the boating and water sport enthusiast.
Latest Listings In Chester
Come see the new look to this beautiful custom home on Crab Alley Bay. Gourmet chef's kit w/new quartz X large island and back-splash. Outside deck now offers waterfall ...
- 5 Beds
- 4 Baths
- MDQA143026 MLS
Hesitate and this RARE Opportunity will be GONE! One-Level Condo with WATERFRONT Views & Community Dock on Chester River is what ISLAND-Living is All About! Located at Ke...
- 2 Beds
- 2 Baths
- MDQA142940 MLS
The most charming bungalow on the Eastern Shore! A secluded oasis built for an owner who desires peace of mind and relaxation! Surrounded by tall trees and green grass, t...
- 2 Beds
- 2 Baths
- MDQA142838 MLS
Quality, custom construction with panoramic waterviews, large site, and state-of-the art systems. Features include...geothermal two-zone HVAC, 2x6 construction, 10' ceil...
- 4 Beds
- 3 Baths
- MDQA142948 MLS
BEST VIEWS OF CHESTER RIVER! End Unit with rear glassed Sunroom and grilling patio. Two Master Suites. Open Stairs, gas fireplace, and neutral paint palette. Many up...
- 2 Beds
- 3 Baths
- MDQA142844 MLS
Lovely 0.92 acre homesite with water views in Benton's Pleasure! PERMIT IN HAND for 2,600 + SF custom home! Bring your own builder or talk to mine! Ready to go! Public se...
- MDQA142998 MLS
Lovely 0.92 acre homesite with WATER VIEWS in Benton's Pleasure! Listing is for base price on a "to be built" DARTMOUTH by Caruso Homes - which can be customized! Other p...
- 4 Beds
- 3 Baths
- MDQA142986 MLS
This is the house you have been waiting to hit the market! Pride of ownership will be seen from the moment you pull up in the driveway. The nicely manicured yard with bea...
- 3 Beds
- 3 Baths
- MDQA142882 MLS
3600 square foot custom designed timber frame home with great water views. Architects Finelli & Gray designed a spacious and elegant wooden home with a cupola, expansive...
- 4 Beds
- 4 Baths
- MDQA142950 MLS
Do not miss this gorgeous, custom-built home in Benton's Pleasure that sits on a One Acre Lot. This stone-front home boasts a gourmet kitchen and open floor plan making ...
- 4 Beds
- 3 Baths
- MDQA142816 MLS
Broad water views and light fill this elegant contemporary located in the desirable community of Southwind. This custom built home has an outstanding floor plan offeri...
- 4 Beds
- 4 Baths
- MDQA142834 MLS
Charming 3 bedroom rancher in a great location. This home features freshly painted gray walls with white trim and new wall to wall carpet. The back deck and hardscaped pa...
- 3 Beds
- 1 Baths
- MDQA142766 MLS
This truly special waterfront home has been the joy of the Owners (and theirextended family) for more than 30 years. One visit and you will know why- It is what everyoneD...
- 3 Beds
- 3 Baths
- MDQA142874 MLS
Spectacular Custom Built Home - Bentons Pleasure Kent Island - Detailed upgrades and features on this truly amazing home - Here are just a few - Attached 3 car Garage, D...
- 5 Beds
- 4 Baths
- MDQA142700 MLS
Great home in Gibsons Grant has everything you are looking for plus more and it's Turnkey! Hardwoods run throughout most of the main level. High ceilings and tall windo...
- 4 Beds
- 3 Baths
- MDQA142836 MLS
This Gibson's Grant Langley model is pristine and picture perfect! Buy for less than brand new. This model is upgraded with the 2 car attached garage, fireplace stone hea...
- 3 Beds
- 3 Baths
- MDQA142762 MLS
Great, Custom Colonial on Crab Alley Bay, located in the community of Southwind. Home features large open spaces on first and third floor, custom kitchen, new master bath...
- 5 Beds
- 4 Baths
- MDQA142750 MLS
The one you've been waiting for! Awesome 3 to 4 Bedroom Contemporary in sought-after Clayborne Woods features dramatic 2 -story foyer~vaulted ceilings in light-filled spa...
- 3 Beds
- 3 Baths
- MDQA142752 MLS
OPEN HOUSE THIS SUNDAY 1-3PM ! One of the Largest & Most Exquisite Gibson Grant homes with HUGE corner lot fenced in. Boasting Double Balcony style with Elegant Charm. ...
- 4 Beds
- 4 Baths
- MDQA142712 MLS
LOWEST PRICE IN GIBSON'S GRANT! THIS STUNNING 3 BR KOCH LANGLEY MODEL OFFERS AFFORDABLE SINGLE FAMILY HOME LIVING IN THE POPULAR WATER PRIVILEGED COMMUNITY ON KENT ISLAND...
- 3 Beds
- 3 Baths
- MDQA142690 MLS
Do not miss out on One level living in our Stanford floorplan. 3 bedrooms, 2. full baths, 2 car garage. Finished garage studio available. Do not miss out on living in G...
- 3 Beds
- 2 Baths
- MDQA142290 MLS
Do not miss out on building a Kingston 3 story in Gibson's Grant . 4 bedrooms, 3. full 1 half baths, 10 foot first floor ceilings, 2 car garage. 2nd floor loft/tv area....
- 4 Beds
- 4 Baths
- MDQA142320 MLS
Do not miss out on building a Kingston 2 story in Gibson's Grant . 4 bedrooms, 3. full baths, 10 foot first floor ceilings, 2 car garage. 2nd floor loft/tv area. Do not...
- 4 Beds
- 3 Baths
- MDQA142318 MLS
Do not miss out on building a Hartley 2 in Gibson's Grant . 4 bedrooms, 2.5. full baths, first floor study, 2 car garage. Finished garage studio available. Do not miss ...
- 4 Beds
- 3 Baths
- MDQA142300 MLS
LOOKING FOR THAT AFFORDABLE LOT FOR YOUR NEW BUSINESS VENTURE--LOOK NO FURTHER! This Town Center lot has a multitude of uses and is ready for your vision. Ingress/egress ...
- MDQA142670 MLS
LOOKING FOR THAT AFFORDABLE LOT FOR YOUR NEW BUSINESS VENTURE--LOOK NO FURTHER! This Town Center lot has a multitude of uses and is ready for your vision. Ingress/egress ...
- MDQA142668 MLS
MOVE IN READY!!!! Come see this beautiful main living open floor plan home. The Ibiza features 2 bedrooms, 2 baths, home office and attic storage. Designer features incl...
- 2 Beds
- 2 Baths
- MDQA142660 MLS
Come see this Move In Ready Home! Main living open floor plan home on large corner lot. The Donegal features 2 bedrooms, 2 baths, home office, large kitchen, sunroom, scr...
- 2 Beds
- 2 Baths
- MDQA142658 MLS
$11k Price Improvement! Welcome Home! This one is a RARE find in Gibson's Grant - You will never have a neighbor across the street - just the peace of the protected pond ...
- 4 Beds
- 3 Baths
- MDQA142554 MLS
Ohhh MY!! DREAM HOMES Like THIS Don't Come to Market Often... Better Hurry! Custom-Built Craftsman Boasting Over 4400 SF Perfectly Perched Upon 3.1 Acres on Crab Alley Ba...
- 4 Beds
- 5 Baths
- MDQA142592 MLS