Chester Real Estate, Homes and Condos for sale

All Chester homes currently listed for sale in Chester as of 12/18/2018 are shown below.  You can change the search criteria at any time by pressing the 'Change Search' button below.

If you have any questions or you would like more information about any Chester homes for sale or other Chester real estate, please contact us and one of our knowledgeable Chester REALTORS® would be pleased to assist you.


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$1,850,000
2923 COX NECK RD E, Chester MD 21619
5
BEDS
5
BATHS
1.20
ACRES
2017
BUILT
"Gorgeous to-be-built Zero Energy waterfront home on Crab Alley Bay! Green aspects include geothermal energy, solar panels, energy star appl, air purification system, low VOC materials, home automation, superior framing and insulation! This open floor plan features 2 master bdrm suites w/ water views, great room and 3 additional bedrooms. Enjoy one level living and entertaining for years to come!"
* LISTED OVER 120 DAYS 
$1,645,000
2886 COX NECK RD, Chester MD 21619
4
BEDS
6
BATHS
5,789
SQFT
$284
$/SQFT
4.10
ACRES
1990
BUILT
"SUPERB QUALITY AND DETAIL IN THIS CUSTOM HOME ON AN EXCEPTIONAL PREMIER WATERFRONT POINT WITH ENDLESS VIEWS, A PRIVATE PIER AND YOUR OWN PRIVATE BEACH! You will find extraordinary appointments at every turn, and Nature abounds all around you. BREATHTAKING VIEWS & SUNSETS entertain you every day, and you will enjoy the lovely inground pool with abundant sitting areas. A huge two-story Great Room features soaring volume walls of windows looking out to gorgeous broad water views. The open floorplan brings you into a fabulous kitchen offering a very large pantry and built-ins that include a desk with hutch/bookshelves and charming curved custom tufted upholstered kitchen nook seating. Both the oversized Game and Billiard Room and the Kitchen provide access to a generous enclosed Florida Room that goes out to the extensive vast terracing and a parklike setting ensconced in a very special, secluded site. The separate dining room features pocket doors and a walk-in linen closet to house your dining accessories. All BRs are ensuite and have walk-in closets. Most even have private WF balconies! The incomparable two story Owner's Suite has a WF terrace, a WF deck, a super-sized luxury Master Bath with separate vanities and enormous multi-customized organized Master Closets. An Office, a Den, a three-car garage, multiple outdoor storage units, Dual staircases and a partially fenced yard couple with a Butler Service Wet Bar and extensive lush landscaping and hardscapes for a superb year-round getaway! There is a Community Clubhouse for ongoing neighborhood gatherings, a Community Dock, Boat Ramp, tot lot tennis court and WF walking trails to complete the best Eastern Shore lifestyle has to offer!"
* LISTED OVER 120 DAYS  * PRICE LOWERED - $1,797,000 TO $1,645,000 
$1,595,000
2838 COX NECK RD, Chester MD 21619
4
BEDS
4
BATHS
4,248
SQFT
$375
$/SQFT
1.20
ACRES
1994
BUILT
"Stunning Southwind home w/living area of 4,248 sq. ft. Gourmet kitchen off great room with soaring windows to enjoy the Eastern Bay views. First floor bedroom with 3 additional bedrooms up. Office wing could be add'l bedroom. Huge master with sitting room.Radiant heat. Commercially constructed pier and boat lifts and waterside adirondeck. Community club house, tennis, beach, scenic trails."
* LISTED OVER 120 DAYS 
$1,225,000
228 BENTONS PLEASURE RD, Chester MD 21619
4
BEDS
4
BATHS
3,519
SQFT
$348
$/SQFT
0.61
ACRES
2005
BUILT
"The pinnacle of waterfront living on Kent Island! This artfully designed 4 bedroom, 3.5 bathroom residence boasts over 3,500 square feet with open living and entertainment spaces throughout. An elevated and screened in deck yields to sweeping water views. A private dock with boat and jet ski lifts complete the picture on Bentons Pleasure Road!"
$1,149,000
200 DRAKE LN, Chester MD 21619
4
BEDS
4
BATHS
3,839
SQFT
$299
$/SQFT
11.00
ACRES
1993
BUILT
"PRICE adjustment! A waterfront with 11+ acres on Crab Alley Creek, where you can have your own very private retreat. The house is a unique contemporary Victorian style, perfect for entertaining with a huge game room off the kitchen and lots of windows creekside. An adjacent craft room, two master suites and 2 new gas furnaces...making the utility bills extremely low...are just some of the many upgrades and features! For summer fun there's a gorgeous pool and patio! The huge 25' x 50' 2-story barn, with electricity, is just the place for a home business, the car collector, winter boat storage and/or the hobbyist! This is one of the few properties in Q.A. Co. with a boat house! Home warranty being given. Within minutes of the Bay Bridge, the property is an easy commute to Annapolis, Baltimore, D.C., as well as major and commuter airports. Please allow 24 hrs. to arrange an appointment. Thank you."
* LISTED OVER 120 DAYS  * PRICE LOWERED - $1,195,000 TO $1,149,000 
$824,900
203 MCHENNY COURT CT, Chester MD 21619
5
BEDS
5
BATHS
3,314
SQFT
$249
$/SQFT
0.21
ACRES
2014
BUILT
"Click on video icon for virtual tour for interior and aerial overview --- 5 Bedroom 4.5 Bath Koch Builders Home, Including Guest Apartment w Full Bath, Kitchen Area and Separate Entrance. Main Level and Second Level Master Suites with Sunset View Balconies. Incredible Water Views from Sunrise on the Chester River to Sunset on Macum Creek. Front and Rear Covered Porches. Gourmet Kitchen w granite, SS and Hardwoods.Great Room w Stone Fireplace, Whirlpool Jetted Tub + More. Direct access to Cross Island Nature Trail, 10 -minute drive to Annapolis, Community Center featuring pool, fitness center, Chester Riverside Pavilion and Fishing Pier."
* PRICE LOWERED - $849,900 TO $824,900 
$779,989
114 PARKS RD, Chester MD 21619
6
BEDS
6
BATHS
4,400
SQFT
$177
$/SQFT
1.55
ACRES
1991
BUILT
"WATER FRONT!*1.5 acres*Conveniently located 3 miles of the bridge, 15 mins to Annapolis* 2 Homes on this Wonderful Property...Main house offers 4 beds 2.5 baths hardwood floors, 2 fireplaces while the guest house/possible rental/In-Law house has 2 bedrooms, 2 baths.*Gourmet Kitchen*fully updated!*Gather Everyone around the Fire-pit outback in the Evenings (in between the 2 Homes)Kent Island Living w Amazing VIEWs Go crabbing, kayaking, paddle boarding from your large PRIVATE PIER W 10,000# BOAT LIFT."
* LISTED OVER 120 DAYS  * PRICE LOWERED - $799,999 TO $779,989 
$649,999
228 CLAIBORNE ST, Chester MD 21619
4
BEDS
3
BATHS
3,144
SQFT
$207
$/SQFT
0.19
ACRES
2010
BUILT
"BACK ON MARKET! Buyers home sale contingency expired and sellers are motivated to sell this again! We are reintroducing one of Gibsons Grant's premiere properties built by NV Homes in 2009. With 4 bedrooms, 4 baths, and over 3000sf its ideal for all situations. Other features include gas fireplace, formal study, gourmet kitchen w big island, second floor laundry, huge front porch- a must see! Comes with a 3 car detached garage with a separately heated and cooled bonus room above (w full bath)!"
* LISTED OVER 120 DAYS  * PRICE LOWERED - $675,000 TO $649,999 
$639,999
126 MCHENNY CT, Chester MD 21619
3
BEDS
3
BATHS
2,394
SQFT
$267
$/SQFT
0.13
ACRES
2010
BUILT
"Most charming home in wonderful Gibson's Grant! Open floor plan w/tons of sunlight & rare soaring 2-story ceilings in great room, dining rm & gourmet kitchen w/island. Main level owner's suite, powder room & laundry room ~ French door leads to screened-in porch leading to deck and fenced yard. Upper level has cozy loft, 2 large bedrms & full bath! Community pool/gym/pier+!!"
* LISTED OVER 120 DAYS 
$594,900
212 EVELYNE ST, Chester MD 21619
4
BEDS
3
BATHS
"Koch Homes newest design the Kingston! 10 ceilings on the first floor, beautiful gourmet kitchen, gas fireplace, fenced courtyard, and porch off of the master bedroom. This home has so many features. Come visit to"
$549,999
101 HENRY STOUPE WAY, Chester MD 21619
4
BEDS
3
BATHS
2,620
SQFT
$210
$/SQFT
0.19
ACRES
2011
BUILT
"Gibsons Grant*Ready to Move in Now *Brand New Carpet & Paint Throughout*Eat in Gourmet Kitchen w Breakfast Bar*Gas Fireplace*Formal Dining Room*Corner Lot location*Detached 2 Car Garage*Community Offers Pool, Kayaking, Just off The Cross Island Trail*Clubhouse/Pier/Playground/Fitness Center & Open Play Areas*This Home is a Must See!"
* PRICE LOWERED - $559,789 TO $549,999 
$549,000
2608 CECIL DR, Chester MD 21619
3
BEDS
3
BATHS
2,336
SQFT
$235
$/SQFT
0.46
ACRES
1976
BUILT
"Entertainer's Delight! Renovated inside & out. Not a square inch left untouched. Home offers granite counters, wet bar, SS appliances, luxury vinyl tile, ceramic, built in entertainment center, 16x32 gunite heated pool with tiki bar and 2 waterfalls, 2 garages for 3 cars, den that could be 4th bedroom, huge sunroom, pellet stove, generator, and more. Sellers have added over 100K in upgrades!"
$539,900
RICHARD INGLE, Chester MD 21619
4
BEDS
3
BATHS
2,454
SQFT
$220
$/SQFT
0.09
ACRES
2017
BUILT
"Eastern Shore's popular location for a wonderfully planned community. Craftsman styled Hartley floor plan with many included features. Hardwood floors, gourmet kitchen with upgraded appliances and granite countertops are only a few of the many features. Plan a visit and see what is waiting for you!"
* LISTED OVER 120 DAYS  * PRICE INCREASED - $532,900 TO $539,900 
$525,000
1803 HARBOR DR, Chester MD 21619
3
BEDS
3
BATHS
1,833
SQFT
$286
$/SQFT
0.34
ACRES
1963
BUILT
"BACK ON THE MARKET. Buyer unable to fulfill home sale contingency. Their loss is your gain! New lowered price. WAKE UP TO WATER VIEWS in your private, upstairs master suite w/waterview deck, HUGE walkin closet & spa bath. Downstairs find 2 more bedrooms & 1.5 baths. Kitchen has corian, gas cooking, breakfast bar. More water views from family room or step out into your ample screened in patio w/jacuzzi tub & privacy screens. Large grassy yard leads to newly replaced 190 ft pier w/3 boat lifts. 2 car garage!"
* PRICE LOWERED - $550,000 TO $525,000 
$520,000
121 HENRY STOUPE WAY, Chester MD 21619
3
BEDS
3
BATHS
2,320
SQFT
$224
$/SQFT
0.15
ACRES
2012
BUILT
"Seeking Gibson's Grant without the high price tag? Welcome Home! Nearly 2400 sq ft, Spacious, Open Floor-Plan, Impeccably Kept & Move-in-Ready- Walk to Community Pool/Clubhouse/Pier/Playground/Fitness Center & Open Play Areas- 5 mins from Bay Bridge- TOP-RATED SCHOOLS- Fenced Yard w/ Large Patio ready to entertain- Break into Coveted Gibsons Grant with this one- Priced UNDER tax assessment- HURRY"
* LISTED OVER 120 DAYS 
$499,000
122 CEDAR RD, Chester MD 21619
4
BEDS
3
BATHS
2,804
SQFT
$178
$/SQFT
1.00
ACRES
2001
BUILT
"Check out this new price!! Largest house on largest lot under 510K in Chester!! Fantastic, spacious and well kept colonial in Benton's Pleasure. 4 BR/2.5BA w/ an over-sized master bedroom with private master bath. Enjoy the Sunroom, Covered Patio and the over-sized 2 car garage which has a bonus room above. Well maintained 2800 sq/ft of living space and sits on a flat 1 acre lot on a quiet street!"
* LISTED OVER 120 DAYS  * PRICE LOWERED - $509,000 TO $499,000 
$475,000
106 WOODS RD, Chester MD 21619
4
BEDS
3
BATHS
2,600
SQFT
$183
$/SQFT
0.56
ACRES
2000
BUILT
$471,900
RICHARD INGLE, Chester MD 21619
3
BEDS
3
BATHS
1,851
SQFT
$255
$/SQFT
0.09
ACRES
2017
BUILT
"Eastern Shore's popular location for a wonderfully planned community. Craftsman styled Langley floor plan with many included features. Hardwood floors, gourmet kitchen with upgraded appliances and granite countertops are only a few of the many features. Plan a visit and see what is waiting for you!"
* LISTED OVER 120 DAYS  * PRICE INCREASED - $469,900 TO $471,900 
$450,000
1703 BAYSIDE DR, Chester MD 21619
3
BEDS
2
BATHS
2,000
SQFT
$225
$/SQFT
0.33
ACRES
1995
BUILT
"Waterfront views without the waterfront tax bill!!This unique home offers lots of space!Second family room/office with separate entrance off of first floor master.SS appliances including 6 burner viking stove, corian counters, wood floors, gas fireplace, water conditioner, large bedrooms, & more.Room on third level would make great office with 360 degree views.Unfinished room above garage.Love it!"
* LISTED OVER 120 DAYS  * PRICE LOWERED - $475,000 TO $450,000 
$435,000
400 CASTLE MARINA RD, Chester MD 21619
4
BEDS
3
BATHS
1,785
SQFT
$244
$/SQFT
0.40
ACRES
1973
BUILT
"One level living at it's best! This beautifully updated home boasts 4 bedrooms, 2 1/2 baths, 2 car garage, and an in-ground pool with a cabana/bath house. Enjoy views of the pool and backyard paradise from every room in the house! One bedroom is fully equipped to be a hair salon! Brand new floors through kitchen and living room. This home is turn key and ready for it's next owner!"
$400,000
102 BROWN RD, Chester MD 21619
4
BEDS
3
BATHS
2,160
SQFT
$185
$/SQFT
0.94
ACRES
1995
BUILT
"OPEN SAT, Dec 1, 11-1 PM! Almost an acre on KI! What a RARE find!! Amazing colonial with large deck overlooking fenced yard, BUT THE LOT DOESN'T STOP THERE..includes dense woods behind and beside for optimum privacy. Oversized 2-car garage completes this 4Br, 2.5 bath home. A bargain price, but hurry before other buyers claim this one!"
$369,926
201 BARREN RIDGE RD, Chester MD 21619
4
BEDS
3
BATHS
2,008
SQFT
$184
$/SQFT
0.63
ACRES
1991
BUILT
"OPEN HOUSE Sun, 12/2, 12-2 pm*WATERVIEWS & SUNSETS! Vaulted ceilings, Light Bright Kitchen, Open Floorplan, Spacious Family RM W/FIREPLACE, 4 LARGE bedrooms (BR over garage), HUGE DECK & Sited on a rare OVER 1/2 acre lot makes thisVERY DESIRABLE HOME w/water priv. HURRY!"
* LISTED OVER 120 DAYS  * PRICE LOWERED - $371,926 TO $369,926 
$360,000
301 SKIPPER LN, Chester MD 21619
5
BEDS
3
BATHS
2,726
SQFT
$132
$/SQFT
0.50
ACRES
1968
BUILT
"Luxuriate in 2700 Sq. Ft. 5 Bedroom Castle Marina Home. You'll Be awed by the wide open Floor plan, and renovations. The gracious rooms are great for entertaining, and comfortable living. The walk out lower level, leads to landscaped patio and detached workshop with finished office. Short stroll to area restaurants, marinas and boat landings."
* LISTED OVER 120 DAYS  * PRICE LOWERED - $375,000 TO $360,000 
$339,000
114 HARBOUR SOUND, Chester MD 21619
3
BEDS
4
BATHS
2,200
SQFT
$154
$/SQFT
1989
BUILT
"Large end unit with marina views and easy walk to Bayside amenities! 4 stories with multiple decks and patio. Large master suite with loft office. Open design for entertaining, eat in kitchen...come take a look!"
 
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