Chester Real Estate, Homes and Condos for sale

All Chester homes currently listed for sale in Chester as of 12/08/2019 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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$1,399,999
2838 COX NECK RD, Chester MD 21619
4
BEDS
4
BATHS
4,248
SQFT
$330
$/SQFT
1.20
ACRES
1994
BUILT
"New Price! 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. Perfect for summer! Motivated sellers."
* PRICE LOWERED - $1,499,000 TO $1,399,999 
$1,199,990
202 WINCHESTER STREET, Chester MD 21619
4
BEDS
4
BATHS
3,624
SQFT
$331
$/SQFT
0.15
ACRES
2018
BUILT
"Our gorgeous Craftsman-style Kingston Model is a must see today. This home won't last long! Located on a corner home site by the community pavillion and fishing pier, this home offers 4 bedrooms, 4 baths,10 foot ceilings on the first floor, 9 on the 2nd and 3rd floor. Patio with kitchen & fire pit and so much more. For those who love to entertain, this is the home for you! Do not miss out on this opportunity to own this beautiful Koch Homes Kingston model home. Home not available for immediate occupancy."
$1,195,000
2813 COX NECK RD, Chester MD 21619
5
BEDS
4
BATHS
3,694
SQFT
$323
$/SQFT
1.00
ACRES
1996
BUILT
"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 steps to a multi level very large gorgeous paver patio and fire pit. Upstairs now offers 5~ wide hand scraped hardwoods 3/4~, not engineered. You will be amazed at how well built this custom home is, from the Anderson windows to the two Trane HVAC systems. Did I mention the brand new architectural roof installed in 2019, the list goes on and on. You will never have to worry about any drafts in this house, it is well built. Be sure to take a look at both attics upstairs, one of them can be finished as a large bonus room for those kids or grand kids to enjoy. Room for a pool and only 5 min to the Bay Bridge."
* NEW LISTING 
$939,000
2839 COX NECK RD, Chester MD 21619
3
BEDS
3
BATHS
2,664
SQFT
$352
$/SQFT
1.10
ACRES
1994
BUILT
"Move right in to this 1 level waterfront home in Southwinds. Lovely brick home w/ 2664' of living space. Elegant foyer. Spacious family room. First floor master suite. Main level laundry room. Perfect for entertaining or relaxing. 2 car garage and driveway. Broad water views and perfect sunrises across Crab Alley Bay."
* PRICE LOWERED - $949,000 TO $939,000 
$749,900
152 WATERMANS COVE LN, Chester MD 21619
4
BEDS
3
BATHS
2,400
SQFT
$312
$/SQFT
0.31
ACRES
2019
BUILT
"Kent Island's newest exclusive private waterfront community, peacefully located on Cox Creek. Enjoy a deep water private pier, beautiful sunset views across the creek, and easy access by boat to Eastern Bay. 4 bedrooms with a spacious master suite, huge open kitchen/dining/family room, sunroom, home office, and mud room off garage. Large rear composite deck for outdoor entertaining. Concrete driveway and 2 car garage. Just over 1 mile from Rt. 50 for easy commute and shopping access. Take a deep breath and delight in the serenity of the Eastern Shore. HOA handles lawn care and trash removal. HOME IS READY FOR DELIVERY!"
$719,000
2816 HARVEST CT, Chester MD 21619
3
BEDS
3
BATHS
2,788
SQFT
$258
$/SQFT
3.28
ACRES
1988
BUILT
"* Views of Cox Neck Creek and Crab Alley, its all about the views. Waterfront without the tax, One of 3 premium lots with direct access to shoreline. Water views from almost every room. There is even a Golf practice area with 2 greens on this property. Beautiful and meticulously maintained by the original owners. There is fixed stairs to a large area over the garage that could possibly be finished off for more living space or another bedroom and bath also off the master bedroom are fixed stairs to a floored attic area. Upscale community with private clubhouse, tennis, beach, boat ramp and playground. Easy 1 hour commute to D.C. 30 Min. to Annapolis.* *Great eateries & AAMC health facilities * You will not want to miss this home * Seller Offering a 1 year Home Warranty Service Agreement*"
$714,900
1610 MIDWAY RD, Chester MD 21619
5
BEDS
3
BATHS
3,861
SQFT
$185
$/SQFT
0.88
ACRES
2018
BUILT
"***MOTIVATED SELLERS READY TO TURN THE KEYS OVER TO YOU!***The perfect blend of island living and custom built elegance. This stunning colonial features over 3800 sq ft of finished living space, 5 bedrooms and 3 full bath complete with a gourmet kitchen--built in table with seating, stainless appliances, pot filler, ice maker, lots of soft close cabinets, endless countertops and separate pantry Coretech scratch resistant hardwood flooring is on trend and makes a stunning first impression. Large propane fireplace anchors the huge family room just off the kitchen. Large covered porch off the kitchen is wired for sound and is the perfect spot to entertain or relax after a long day. Sitting on one of the largest single lots in the community, the back yard is fenced and space for a pool is already designated on the plat with the county. First floor bedroom and full bath provides lots of flexibility. Upper level features master bedroom with tray ceilings, large walk in closet and master bath suite that feels like a spa and features heated flooring, oversized shower, 2 separate vanities and huge tub. Three additional bedrooms, full bath and off the 4th bedroom is an unfinished bonus room above the garage that offers an additional 800 sq ft of space. Upper level laundry too! The unfinished basement was designed to be the entertaining spot of the house and has rough ins for a full bath and wet bar and space to create your own theatre room--an additional 1500 sq ft of endless possibilities. High efficient HVAC and insulation means low utility bills. PLUS you are steps away from 2 of the 4 beaches in Marling Farms. You'll enjoy crabbing and fishing from the community pier and boat ramp where there is also a covered pavilion and tot lot at water's edge. Centrally located on Kent Island and only 10 minutes from the bridge. Don't miss YOUR DREAM HOUSE!"
* PRICE LOWERED - $724,900 TO $714,900 
$699,900
132 WATERMANS COVE LN, Chester MD 21619
3
BEDS
3
BATHS
0.41
ACRES
2019
BUILT
"Beautiful waterfront home to be built. Enjoy the serenity of Cox Creek in the new community of Waterman's Cove. This enclave of nine private home sites is nestled on a quiet dead end street. Private pier. 3 bedrooms. 2.5 baths. Kitchen with granite counter tops and stainless steel appliances. Hardwood floors. First floor master bedroom with attached bath. Large 2nd story waterfront office or media room. Rear composite deck for outdoor entertaining overlooks water. Concrete driveway and nice attached garage. Located just a short mile off Rt. 50. HOA includes lawn care and trash removal."
$675,000
208 THOMAS WHITE BLVD, Chester MD 21619
5
BEDS
5
BATHS
3,984
SQFT
$169
$/SQFT
0.13
ACRES
2011
BUILT
"Must see this spacious home offering approx 4,000' of living space. One of the larger KOCH home floor plans. Many upgrades here include: Lovely hardwoods throughout main level. Coiffured ceilings in dining room. Stone fireplace in large family room. Kitchen loaded with cabinets, island, breakfast bar and granite counters. Master with sitting room, fabulous walk thru closet and huge master bath. Master bedroom has access to 2nd level porch where you can enjoy sunrises and sunsets. Very private 3rd level bedroom, play area with full bath. Bonus room above garage finished and could be in-law/aupair space. Several rooms with flexible uses. 2 Car Garage. Lovely water oriented community, centrally located and steps away from clubhouse and pool. Low HOA fees, 1-2 miles from Bay Bridge. Much to love here. More photos coming but don't wait...this home is a must see!"
* NEW LISTING 
$659,990
0000 EVELYNE STREET, Chester MD 21619
4
BEDS
4
BATHS
3,516
SQFT
$188
$/SQFT
0.14
ACRES
2020
BUILT
"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. 3 rd floor studio. Do not miss out living in Gibson Grant with Community center, swimming pool. fitness center, kayak racks. Fishing and crabbing pier. This home is to be built base price. Pictures from a past Kingston 2 story home & 3 story model home."
$650,000
137 JOHN DABB CT, Chester MD 21619
3
BEDS
3
BATHS
3,000
SQFT
$217
$/SQFT
0.13
ACRES
2017
BUILT
"Enjoy the Gibson's Grant lifestyle. You will love relaxing on the front porch, enjoying the river and pond views and breeze. This is a modified Ashford model with a main level master suite and finished bonus room over the garage. Triple-pane dormers grace the two upper level bedrooms, rendering them much more functional, spacious, and comfortable than the standard floor plan. The finished bonus room over garage and office on main level have potential to serve as 4th & 5th bedrooms. Professionally designed landscaping and hardscape, including a fire pit. Plantation shutters, California Closets, stained glass, granite, marble, stainless, wood floors, built-in bookcases, custom glass shower doors... Over $140,000 in upgrades and options!"
* NEW LISTING 
$649,900
1771 HARBOR DR, Chester MD 21619
5
BEDS
3
BATHS
1,836
SQFT
$354
$/SQFT
0.58
ACRES
1986
BUILT
"Kent Island Waterfront, start your life of leisure here where peaceful waters flow..Approx 2300 sq ft, solid construction and well-maintained. Charming, relaxed craftsman style home with a laid back vibe, spanning 1.5 levels - spacious eat-in kitchen w/ corian counter tops, breakfast bar, double oven and tons of natural light, formal living, cozy family room leading to huge florida room, 3 bedrooms on main level, master bedroom with a view, 2nd floor boast 4th bedroom, office/study (could be 5th bedroom), loft area and massive storage area. Large backyard, deck and pier."
* PRICE LOWERED - $695,000 TO $649,900 
$634,900
151 JOHN GIBSON DR, Chester MD 21619
5
BEDS
4
BATHS
3,856
SQFT
$165
$/SQFT
0.14
ACRES
2010
BUILT
"New LOWER PRICE on this spectacular home with all the bells and whistles in a community with top notch amenities. The home was custom built just nine short years ago and no option was overlooked. Room extensions & bump-outs, oversized & detailed moldings, three zone heating & cooling, premium hardwood flooring, ceramic tile, recessed & pendant lighting, smart wiring, gas heat, fireplace & cooking, double wall oven, three car garage (with 700 sq ft living space above including a full bath), fluted columns, trex decking, paver walks & patio, and much more! Be sure to see the attention to detail on the crown molding, picture framing, and tile accents. And the waterfront community of Gibson's Grant is just as stellar! Clubhouse, beautiful pool, playground, bocce ball court, jogging/walking trail, kayak area, exercise room and pier. Go to https://www.youtube.com/watch?v=sDFd_56_t28 (copy and paste the link in your browser) to see more about the community. You can relax on your front wrap around porch as the landscaping is all included as well! Enjoy all that Kent Island has to offer with restaurants, tiki bars, public boat ramps and marinas. Close to route 50 and a short drive to the beaches and Annapolis - this home is a must see!"
* PRICE LOWERED - $639,900 TO $634,900 
$629,999
1868 ROBERTA DR, Chester MD 21619
5
BEDS
4
BATHS
3,250
SQFT
$194
$/SQFT
0.43
ACRES
2007
BUILT
"Custom built home with many upgrades, and water views. A few upgrades are, 12 ceilings and windows are 6 on first floor. Custom window treatments throughout. Custom hardwoods and tile throughout. Dedicated laundry room with washer and dryer and a laundry sink. Eat in kitchen with granite counter tops and a large center island with pantry. Sun room off of kitchen. Finished garage.800 sq. ft. wrap around maintenance free deck. Room to build inground pool.Master bath with custom tile shower and 36 in. double sink vanity. 2 additional Jack & Jill bathrooms with double sink vanities.1820 sq. ft crawl space. 4 ft high finished concrete with indoor access perfect for storage."
* PRICE LOWERED - $630,000 TO $629,999 
$611,990
140 JOHN DABB CT, Chester MD 21619
4
BEDS
3
BATHS
2,907
SQFT
$211
$/SQFT
0.13
ACRES
"Featured homesite 51. Build a Langley, Hartley 2 or Kingston 2 or 3 story.Beautiful views to the Chester River and Gibson's Grant ponds. This home is for a new be built Kingston base price. The pictures are of a Kingston 2 story past home."
$601,990
0000 EVELYNE STREET, Chester MD 21619
4
BEDS
3
BATHS
2,907
SQFT
$207
$/SQFT
0.14
ACRES
2020
BUILT
"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 miss out living in Gibson Grant with Community center, swimming pool. fitness center, kayak racks. Fishing and crabbing pier. This home is to be built base price. Pictures from a past Kingston 2 story home."
$600,000
214 BARREN RIDGE RD, Chester MD 21619
4
BEDS
3
BATHS
2,204
SQFT
$272
$/SQFT
0.22
ACRES
2002
BUILT
"Want waterfront at an affordable price??? Look NO further! This home is IT! This is the home you have worked so hard for!!! The views from this home are STUNNING!! Sunsets like you have NEVER seen before. This home boasts 4 LARGE bedrooms, with 2 of them being waterfront. The entire home has been freshly painted and new carpet has been installed. The Living Room is open with a gas fireplace and sliders across the back of the home so your views are not obstructed!!! The Dining Room is open to the Living Room and the Kitchen and also has the stunning water views. The Gorgeous and Spacious master suite is directly on the water with it's own balcony. Enjoy your time relaxing on the balcony soaking up these views! Bedroom #2 is also water front with it's own balcony. The bonus room over the garage is MASSIVE and can be used as a bedroom, family room, man cave, toy room, etc. So many possibilities!!! Moving back outside, the 2 tiered deck is an amazing space to soak in all the water views and the perfect the entertainers backyard. The lower deck features extra support for a hot tub or swim spa. Moving to the water, the LONG pier with 2 jet ski lifts and boat lifts, is ideal for all those water toys, fishing, crabbing, and just soaking it all in!!! Added bonus, irrigation system installed!!! You won't find this anywhere else!!!"
* NEW LISTING 
$599,990
0000 WINCHESTER STREET, Chester MD 21619
4
BEDS
3
BATHS
2,963
SQFT
$202
$/SQFT
0.13
ACRES
2020
BUILT
"Grand and Elegant! Koch Homes Chatham floor plan. 4 bedrooms, First Floor Study 2.5 baths, 2 car garage. Finished garage studio available. # floor loft/bathroom available. Do not miss out on living in Gibson Grant with community center, swimming pool. kayak racks.Fishing and crabbing pier. This home is to be built. Pictures are from past Chatham floorplan."
$599,000
1604 BAYSIDE DR, Chester MD 21619
3
BEDS
3
BATHS
2,844
SQFT
$211
$/SQFT
0.50
ACRES
1973
BUILT
"Marling Farms Waterfront - The views and sunsets are everything you want and more from this property. The home has a new kitchen, hardwood flooring, pier and boat lifts. Three Bedrooms and Three Bath, need an inlaw apartment, downstairs features a separate kitchen as well. Nice size lot of .50 of an acre, with rip rap water front and 110' pier. Seller in the process of installing NEW SEPTIC and WELL! NEW Roof is already installed!"
$595,854
224 SALTWORKS DRIVE, Chester MD 21619
2
BEDS
2
BATHS
2,597
SQFT
$229
$/SQFT
0.22
ACRES
2019
BUILT
"AVAILABLE NOW!!! The San Sebastian features an inviting foyer, 2 bedrooms, 2 baths, home office and gourmet kitchen with quartz and shaker style cabinets. Beautiful luxury vinyl floors throughout common areas, 42'' modern fireplace and dry bar are some of the designer finishes in this home. Photos are from our model and shows additional upgrades."
$595,000
112 FRANCIS BRIGHT WAY, Chester MD 21619
3
BEDS
3
BATHS
2,785
SQFT
$214
$/SQFT
0.18
ACRES
2013
BUILT
"Southern/Coastal-inspired design in Gibson~s Grant. Open floor plan, this 3 Bedroom/2.5 Bath home is impeccably maintained, featuring Granite tops, Hardwoods & SS appl. Family room with stacked stone fireplace, finished Bonus Room above garage, built-in cabinets, Finished courtyard pavers in private patio, 2 car garage. Premium lot across from the community amenities ~ pool, pavilion, workout facility, community water access, kayak launch, walking trails. Ideal location close to the Bridge."
$594,990
0000 WINCHESTER STREET, Chester MD 21619
3
BEDS
2
BATHS
2,184
SQFT
$272
$/SQFT
0.13
ACRES
2020
BUILT
"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 Gibson Grant with community center, swimming pool. kayak racks. Fishing and crabbing pier.This home is to be built. Pictures from a past Stanford home."
$559,990
0000 WINCHESTER STREET, Chester MD 21619
3
BEDS
3
BATHS
2,275
SQFT
$246
$/SQFT
0.13
ACRES
2020
BUILT
"First Floor Master suite featured in Koch Homes Ashford floor plan. 3 bedrooms, 2nd floor sitting area, 2.5 baths, 2 car garage. Finished garage studio available. Do not miss out on living in Gibson Grant with community center, swimming pool. kayak racks.Fishing and crabbing pier.This home is to be built base price. Pictures from a past Ashford home."
$554,865
1131 HERON'S NEST, Chester MD 21619
3
BEDS
3
BATHS
2,602
SQFT
$213
$/SQFT
2019
BUILT
"Low maintenance living at its best! Luxury Condominiums now selling! Building has elevator access, 1 car garage per unit and secure storage rooms. The Severn floor plan has tons of windows and it features 3 bedrooms, 2.5 baths and a balcony. Home includes a Gourmet Kitchen with 30'' cooktop and canopy hood, quartz counter tops and many other designer upgrades. Home will be ready Spring 2020. Photos are a virtual representation of our future models and show additional upgrades."
 
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