Kentislandlifestyle.com
  • Home
  • Property Search
  • Selling
  • Buying
  • About
  • Blog
  • Contact Us
Login
410-490-8556

Sign in to your account

Need to reset your phone number?

Don't have an account with us?

Click here to sign up.

Chester Real Estate Search

TO
Advanced Search

Address Search

Chester Homes For Sale

Chester Homes for Sale

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. 

Chester Homes Map Search

Latest Listings In Chester

413 Hanna   Court, Chester image
413 Hanna Court, Chester $400,000

***ALL OFFERS WILL BE PRESENTED 1/24/21 at 10AM***Welcome to this stunning, 4 BR 2.5 Bath showpiece in turn-key condition, on a cul-de-sac street backing to the woods, in...

  • 4 Beds
  • 3 Baths
  • MDQA146486 MLS
227 Claiborne   Street, Chester image
227 Claiborne Street, Chester $649,000

Stunning home in amenity rich community of Gibsons Grant! Hardwood floors throughout both floors accented by designer light fixtures welcome you to this perfectly design...

  • 5 Beds
  • 3 Baths
  • MDQA146524 MLS
515 Teal   Court Unit #H, Chester image
515 Teal Court Unit #H, Chester $260,000

Bayside - End Upper Unit with one level living overlooking the pond. Open floor plan for entertaining and enjoying the views of the pond. The gas fireplace is a nice f...

  • 2 Beds
  • 2 Baths
  • MDQA146482 MLS
2907 Cox Neck  E Road E, Chester image
2907 Cox Neck E Road E, Chester $1,195,000

Waterfront in the desirable Southwind community minutes to the Bay Bridge. Four bedrooms and six bathrooms. Waterfront - elevated- lot with open views. Large FIRST FLO...

  • 4 Beds
  • 6 Baths
  • MDQA146446 MLS
214 Blenny   Lane, Chester image
214 Blenny Lane, Chester $335,000

Renovations completed in 2020. Enjoy the Great Room and Kitchen with new Hardwood Flooring & FP leading to a deck with power awing overlooking the Pond. Kitchen with ne...

  • 3 Beds
  • 4 Baths
  • MDQA146290 MLS
131 Claiborne   Street, Chester image
131 Claiborne Street, Chester $759,000

Welcome to this Charming 4 bedroom, 3 1/2 bath Coastal Colonial situated in the Water Privileged community of Gibson's Grant!! You are immediately Welcomed with a Gorgeou...

  • 4 Beds
  • 4 Baths
  • MDQA146350 MLS
208 Teal   Court Unit #D, Chester image
208 Teal Court Unit #D, Chester $225,900

Wonderful first floor entry level, single level living in sought after Bayside. A stones throw from the Pool and and Clubhouse/ Exercise area. This wonderful unit offe...

  • 2 Beds
  • 2 Baths
  • MDQA146376 MLS
Chester image
Chester $210,000

WATERFRONT ACCESS - INVESTMENT or Occupy. Current tenant has been here 13 yrs, $1400 /month would like to stay, Minimum 60 days notice for tenant to move. C...

  • 3 Beds
  • 3 Baths
  • MDQA146314 MLS
1915 Stevens   Drive, Chester image
1915 Stevens Drive, Chester $355,000 ▼

Kent Island BEST VALUE ALERT!! You won't find another home this size & condition on Kent Island near this price!! Updated 3 GENEROUS sized Bedrooms 2 Full Bath One Level ...

  • 3 Beds
  • 2 Baths
  • MDQA146282 MLS
1908 Harbor   Drive, Chester image
1908 Harbor Drive, Chester $315,000

Exceptionally cozy and well-maintained one-level living home, with lots of upgrades, awaits its lucky new owners! Crown molding, tilt-in easy-clean windows, the newest lo...

  • 2 Beds
  • 2 Baths
  • MDQA146226 MLS
908 Auckland   Way, Chester image
908 Auckland Way, Chester $450,000

Bayside - Luxury Bayside Villa directly overlooking Castle Marina Harbor and views of the Chester River. This unit is the first time on the market and shows pride of own...

  • 3 Beds
  • 4 Baths
  • MDQA146280 MLS
102 Cavalier   Court, Chester image
102 Cavalier Court, Chester $579,900

This home is a rare quick delivery opportunity in Four Seasons at Kent Island. Available in Spring 2021 the San Sebastian will feature over 2500 square feet, elegant firs...

  • 2 Beds
  • 2 Baths
  • MDQA146246 MLS
2000 Heron's Nest   Way Unit #32, Chester image
2000 Heron's Nest Way Unit #32, Chester $449,900

Welcome to a new active adult 55+ community on Maryland's Chesapeake Bay, offering island-living with new single-family homes and condominiums. Discover an amenity-filled...

  • 2 Beds
  • 3 Baths
  • MDQA146234 MLS
3000 Heron's Nest   Way Unit #24, Chester image
3000 Heron's Nest Way Unit #24, Chester $539,900 ▼

* Home is availble to move in March 2021. Call today to find out the details and start living the life you want. Welcome to a new active adult 55+ community on Maryland'...

  • 3 Beds
  • 3 Baths
  • MDQA146232 MLS
2902 Cox Neck  E Road E, Chester image
2902 Cox Neck E Road E, Chester $1,149,000

Casual elegance in the water privileged community of Southwind. Water views of both Eastern Bay and Crab Alley Bay from almost every room in the house. Two story foyer, ...

  • 5 Beds
  • 5 Baths
  • MDQA146170 MLS
101 Swan Cove   Lane Unit #101, Chester image
101 Swan Cove Lane Unit #101, Chester $799,000 ▼

BIG PRICE DROP 25k . GREAT TIME TO OWN THIS WATER FRONT CONDO ! WATERFRONT LIVING IN LUXURY ! Absolutely the best location !!!! This 4 bedroom 3.5 bath 3300 + square fee...

  • 4 Beds
  • 4 Baths
  • MDQA146100 MLS
917 Auckland   Way, Chester image
917 Auckland Way, Chester $439,900

Nature abounds in this end unit townhome with views of the marsh and Chester River. Such peaceful surrounds and serene picturesque setting, you will be relaxed forever! E...

  • 3 Beds
  • 4 Baths
  • MDQA144464 MLS
1405 Little Creek   Road, Chester image
1405 Little Creek Road, Chester $39,900 ▼

2 bed, 1 bath home located in Chester MD. The home is in need of updates and repairs before move in ready.

  • 2 Beds
  • 1 Baths
  • MDQA145928 MLS
4004 Bridgepointe   Drive, Chester image
4004 Bridgepointe Drive, Chester $318,900 ▼

One of the most desirable location on KI. Easy commute to Bay Bridge, shopping, fine dining, island cross trail and more. This one is a "Showstopper". Vaulted ceilings...

  • 3 Beds
  • 3 Baths
  • MDQA145748 MLS
107 Chester Station   Lane, Chester image
107 Chester Station Lane, Chester $1,200,000 ▼

66,000 cars go by this building every day. Sits right on RT 50, your sign will be your best advertisement, saving money on your advertising budget. This building will i...

  • MDQA145740 MLS
53 Queen Caroline   Court, Chester image
53 Queen Caroline Court, Chester $259,900 ▼

Reduced! Beautifully Updated 2 Bedroom, 2.5 Bath Townhome in the Popular Water Oriented Community of Queen's Landing. Features Newer White Kitchen with Granite Counters a...

  • 2 Beds
  • 3 Baths
  • MDQA145522 MLS
2510 Roberta   Drive, Chester image
2510 Roberta Drive, Chester $179,000

*BUILDABLE .42 acre corner lot with PUBLIC SEWER and peek at the water across the street. HARBOR VIEW* Close to the Bay Bridge and convenient to Annapolis and Easton.* B...

  • MDQA145548 MLS
3000 Heron's Nest   Way Unit #11, Chester image
3000 Heron's Nest Way Unit #11, Chester $443,900 ▲

Call today to find out the details and start living the life you want. Welcome to a new active adult 55+ community on Maryland's Chesapeake Bay, offering island-living w...

  • 2 Beds
  • 3 Baths
  • MDQA145482 MLS
3000 Heron's Nest   Way Unit #42, Chester image
3000 Heron's Nest Way Unit #42, Chester $499,900 ▼

Welcome to a new active adult 55+ community on Maryland's Chesapeake Bay, offering island-living with new single-family homes and condominiums. Discover an amenity-filled...

  • 2 Beds
  • 3 Baths
  • MDQA145472 MLS
3000 Heron's Nest   Way Unit #23, Chester image
3000 Heron's Nest Way Unit #23, Chester $457,900

Welcome to a new active adult 55+ community on Maryland's Chesapeake Bay, offering island-living with new single-family homes and condominiums. Discover an amenity-filled...

  • 2 Beds
  • 3 Baths
  • MDQA145478 MLS
107 Chester Station   Lane, Chester image
107 Chester Station Lane, Chester $1,800,000 ▼

66,000 cars a day go by with easy on and off access. No need to spend money on advertising with this location. There are 2 buildings on this parcel. An Upscale, class ...

  • MDQA145434 MLS
2012 Chester   Road, Chester image
2012 Chester Road, Chester $3,400,000

Gorgeous water views, stunning wetlands and farmland! Easy commute to Washington DC, Baltimore, MD, Philadelphia PA. and other major cities on the East Coast! This par...

  • MDQA145218 MLS
226 Bentons Pleasure   Road, Chester image
226 Bentons Pleasure Road, Chester $895,000

FORGET DAYS ON MARKET THIS HOME IS READY TO GO-- NOW VACANT -- FRESHLY PAINTED THE PLEASING GRAY TONE -- NEW CARPET-- BEAUTIFUL! PLEASE CHECK OUT NEW PHOTOS AND VIRTUAL ...

  • 4 Beds
  • 3 Baths
  • MDQA145366 MLS
5009 Bridgepointe   Drive, Chester image
5009 Bridgepointe Drive, Chester $343,000

Kent Island, Maryland --- Turn Key -- MOVE IN READY! 3 or 4 Bedrooms LOW HoA ($160/mo.) INSPECTED. PRIVATE! HOME WARRANTY. Move in Quickly. 3 or 4 bedrooms - 4th can...

  • 4 Beds
  • 2 Baths
  • MDQA145238 MLS
107 Chester Station   Lane, Chester image
107 Chester Station Lane, Chester $650,000

None

  • MDQA145210 MLS
Like or Share
Loading likes...

Address Search

Check Current Mortgage Rates

 

Rates provided by Ability Mortgage Group, LLC

 

------------------------------------------------

 

Stevensville

  • Bay City
  • Bloody Point Farm
  • Claibornes Landing
  • Cloverfields
  • Goose Point Estates
  • Kent Island Estates
  • Kentmorr
  • Kent Point Farm
  • Long Creek Farm
  • Love Point
  • Matapeake Estates
  • Queen Anne's Colony
  • Romancoke
  • Sunny Isle of Kent
  • Tower Gardens

Chester

  • Bayside
  • Benton's Pleasure
  • Castle Marina
  • Clayborne Woods
  • Gibson's Grant
  • Harbor View
  • Kirwan's Landing
  • Marling Farms
  • Queens Landing
  • Southwind

Grasonville

  • Greenwood
  • Narrows Pointe
  • Prospect Plantation
  • Prospect Bay
  • The Woods

Queenstown

  • Bennett's Point
  • Belle Point
  • Governor Grason Manor
  • Hickory Ridge
  • Overlook at Carmichael
  • Queen Anne Acres
  • Queen Anne Woods
  • Sayers Forest
  • Sportsman Hall
  • Wye Acres
  • Wye Harbor
  • Wye Knot Farm
  • Wyoming on the Wye

Centreville

  • Bridgetown Estates
  • Claiborne Fields
  • Corsica River Estates
  • Earles Branch
  • Hunters Ridge
  • McKenney Forest
  • Northbrook
  • Recovery
  • Three Creeks

Popular Areas to Live

  • Wye River Waterfront
  • Eastern Shore

Maryland Counties

  • Allegany County
  • Anne Arundel County
  • Baltimore City
  • Baltimore County
  • Calvert County
  • Caroline County
  • Carroll County
  • Cecil County
  • Charles County
  • Dorchester County
  • Frederick County
  • Garrett County
  • Harford County
  • Howard County
  • Kent County
  • Montgomery County
  • Prince George's County
  • Queen Anne's County
  • Saint Mary's County
  • Somerset County
  • Talbot County
  • Washington County
  • Wicomico County
  • Worcester County
  • Home
  • Property Search
  • Sell Smart
  • Buying
  • About Us
  • Blog
  • Contact Us

Laurie Dellane
Realtor
Chesapeake Real Estate Associates
Office:  410-643-4663 |
Cell:  410-490-8556
www.kentislandlifestyle.com


© 2017 - All Rights Reserved

Optin Architect

  • Stevensville
  • Chester
  • Grasonville
  • Queenstown
  • Centreville
IDX Real Estate Websites by
• Accessibility