Chester Real Estate, Homes and Condos for sale

All Chester homes currently listed for sale in Chester as of 06/20/2019 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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$1,700,000
1605 CALVERT RD, Chester MD 21619
5
BEDS
4
BATHS
4,271
SQFT
$398
$/SQFT
4.17
ACRES
1965
BUILT
"Simply Spectacular!! THIS is the ONE You've Waited For!! A True' Estate' Home Ready for a Lifetime of Memories!! Boasting Over 4200 sq ft on Over 4 Acres with Expansive Panoramic Waterfront Views of Prospect Bay- Over 1/2 Mile of Shoreline! Brick Carriage House with Every Upgrade you Can Imagine- Inside & Out! Private Boat Basin w/ Lift to keep your vessel safe- 5 Bedrooms, 3.5 Baths, Main-Level Master Suite off Private Den/Office Rivals a Hotel Suite! Gourmet Kitchen will make your jaw drop!! WOW On Every Level! Vaulted Wooden Ceilings make Crisp White Cabinetry, Gleaming Granite & Brick Fireplace Pop! FOUR Fireplaces for chilly nights! In-Ground Gunite Pool Surrounded by Spacious Paver Patio w/ Built-in-Grill just Begging to Entertain! Detached 3-Car Garage w/ Ample Storage! Possible Additional Lot/Perc! A Stand-Out on Every Level! 10 Mins from Bay Bridge! Treat Yourself to This Stately Property- Rare Find!"
$1,499,000
2838 COX NECK RD, Chester MD 21619
4
BEDS
4
BATHS
4,248
SQFT
$353
$/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. Just in time for summer! Motivated sellers."
* LISTED OVER 120 DAYS  * PRICE LOWERED - $1,595,000 TO $1,499,000 
$1,199,000
228 BENTONS PLEASURE RD, Chester MD 21619
4
BEDS
4
BATHS
3,519
SQFT
$341
$/SQFT
0.61
ACRES
2005
BUILT
"This artfully designed 4 bedroom, 3.5 bathroom residence boasts over 3,500 sqft with open living and entertainment spaces both inside and out. An elevated deck yields to sweeping water views. Private dock with electric boat and jet ski lifts complete the picture on Bentons Pleasure Road!"
$1,195,000
2813 COX NECK RD, Chester MD 21619
5
BEDS
4
BATHS
3,694
SQFT
$323
$/SQFT
1.00
ACRES
1996
BUILT
"Everything you will ever need or want in a home is located in this upscale community of Southwind. This quality-built home is pristine and with over $ 100K in recent improvements inside and out - it is surely a WINNER. The gourmet kitchen now offers two islands with more than enough space to cook, entertain and take in the expansive water views. The first-floor master bedroom is exquisite and offers the most amazing waterfront view from the comfort of your own bed with direct access to the deck and patio area, where you can relax and enjoy quiet evenings under the stars. The 2nd floor offers 4 more spacious rooms that could easily be used for additional bedrooms, office space or at home gym ~ the possibilities are endless. One of the larger 2nd floor bedrooms is a private mini suite with enough room for a king size bed, and offers a small kitchenette as well as en suite bathroom ~ Caution!!! - your guests may never leave. There are also two more full bathrooms on the 2nd floor. The outdoor space is equally impressive with a brand new Trex deck(15'X20') and 2 beautiful custom paver patio areas (1-8'X10' and 2nd 22'X23') with fire-pit ~ completed Sept 2018. Expansive one-acre level lot with over 155 +/- Shoreline that is fully rip rapped and has a private pier for easy boating access to Crab Alley Bay and Eastern Bay. A few other items worth noting, Architectural roof installed Feb 2019, Anderson windows, Dual Zone Trane Heat/AC, 2 car attached garage, superior construction with 2X4 interior walls and 4X6 thick exterior walls, room for a pool (Verify with County). Far away but yet so close to everything you need - just minutes to the Bay Bridge and quick drive to Annapolis, easy commute to Baltimore or DC."
$1,150,000
2867 COX NECK RD, Chester MD 21619
3
BEDS
4
BATHS
6,068
SQFT
$190
$/SQFT
2.40
ACRES
1999
BUILT
"TRUSTEE SALE ! MUST SELL! One level living at it's finest. Breathtaking water views of Eastern Bay. large open living concept. Screened porch over looks private in ground pool, and flat yard leading to your own private dock. Located in Southwinds, this home will not disappoint!"
$1,050,000
200 DRAKE LN, Chester MD 21619
4
BEDS
4
BATHS
3,839
SQFT
$274
$/SQFT
11.31
ACRES
1993
BUILT
"A waterfront Retreat with 11+ acres on Crab Alley Creek. This 4 Bedroom/3.5 Bathroom house is a unique contemporary Victorian style, perfect for entertaining with a huge game room off the kitchen and lots of windows. The home features two master suites and 2 new gas furnaces! The dining room, next to a full bathroom, could be an office, den or bedroom. For summer fun there's a gorgeous pool, patio and screened porch! The huge 25' x 50' barn, with electricity, is just the place for a home business, the car collector, and/or storage. This is one of the few properties in Q.A. Co. with a boat house, and a rooftop deck! Incredible SUNSETS. The location makes it a great spot for the boating enthusiast, with many rivers off the Chesapeake Bay to explore and for fishing and crabbing! Within minutes of the Bay Bridge, the property is an easy commute to Annapolis, Baltimore, D.C., as well as major and commuter airports."
* NEW LISTING 
$989,000
328 BENTON PLEASURE RD, Chester MD 21619
3
BEDS
3
BATHS
1,725
SQFT
$573
$/SQFT
1.55
ACRES
1953
BUILT
"This truly special waterfront home has been the joy of the Owners (and their extended family) for more than 30 years. One visit and you will know why- It is what everyone DREAMS about when they imagine their perfect Shore Home. Placed with a commanding view of Cox Creek (and truly spectacular sunsets), this 3 Bedroom, 2-1/2 bath gem was designed to celebrate the outdoors. The Entry Foyer opens into the Living Room with a large brick fireplace. The two large bedrooms have their own beautifully detailed bathrooms. The third smaller, upstairs bedroom would also make a terrific home office, nursery or craft room.There is an enormous screened porch that connects to the wonderful gourmet kitchen. It opens onto a covered porch that has steps to a slate tile patio (partially heated along with the steps and front sidewalk!). The expansive yard sits well above the flood plain and has some mature trees that shade the second floor balcony. The concrete pool is a shady oasis that has outstanding, panoramic water views. The dock has TWO boat lifts and 4'+ MLW. Great crabbing, fishing and watersports await! There is truly nothing quite like it!"
$839,000
2914 COX NECK RD E, Chester MD 21619
4
BEDS
5
BATHS
4,750
SQFT
$177
$/SQFT
1.43
ACRES
1994
BUILT
"The Allure of Southwind... Waterviews Await from Front & Back in This Custom-Built, Stately Home Boasts Nearly 4800 sq ft, with ANOTHER 2500 sq ft+ in Unfinished Basement! Space & Style in One! Traditional Floor-Plan. Relax & Watch the Boats go by on your brick front porch! Step Inside to an Inviting 3-Story Foyer Opening to Dining Room Spacious Enough to Seat 12! Holidays & Gatherings Just Got Sweeter! Vaulted Family Room Ceiling Cascades Upon Stacked Stone Fireplace in Dramatic Family Room! Large Eat-In-Kitchen Opens to Large Brick, Covered Back Patio off Gourmet, Eat-in-Kitchen, Main-Level Master Suite w/ New Designer Master Bath! 4 Bedrooms, 2 Full Baths, 2 Half Baths! Attached, Side-Load 2-Car Oversized Garage! Walk to Community Boat Ramp, Tennis Courts, Clubhouse! Stately Homes in This Impressive Community Just 10 Mins from Bay Bridge... Hurry to this Exceptional Value!"
$799,000
1900 BAYSIDE DR, Chester MD 21619
3
BEDS
3
BATHS
2,588
SQFT
$309
$/SQFT
0.72
ACRES
1976
BUILT
"YOU HAVEN'T SEEN A VIEW LIKE THIS BEFORE! WOW, is only the start! Nature lovers and kayakers/paddleboarders will delight in this one of a kind property at the southern tip of Marling Farms. PLUS: FRESH APPRAISAL IN HAND for $801K means you start our with instant equity! Property is sold with adjacent 1+ acre lot ensuring a lifetime of panoramic views. Boasting total square footage of over 2600 sq ft, this rare find also features a large studio over the garage that connects to the main house via a deck that runs through the tree tops adding to the allure. Three decks in total and a waterfront screened porch gives multiple vantage points to soak it all in. Private pier and new rip-rap with living shoreline are the exclamation point on this amazing property. With a total of 3 bedrooms,3 full baths, 2 living spaces and an office in the main house alone, you'll appreciate the space almost as much as the incredible views throughout the home. The above garage studio features more than 700 additional sq ft of living space, a half bath, new gas stove and a all of window complete with a large deck again capitalizing on the unbeatable view. YOU TRULY HAVE TO SEE IT AND EXPERIENCE IT FOR YOURSELF! Schedule a showing today! FRESH APPRAISAL IN HAND FOR $801K! Instant equity--buy with confidence!"
$775,000
203 MCHENNY COURT CT, Chester MD 21619
5
BEDS
5
BATHS
3,314
SQFT
$234
$/SQFT
0.21
ACRES
2014
BUILT
"Main Level and Second Level Master Suites with Sunset View Balconies. Click on movie projector for VIMEO.COM virtual tour for interior and aerial overview https://vimeo.com/139273901 . --- 5 Bedroom 4.5 Bath Koch Builders Home, Including Guest Apartment w Full Bath, Kitchen Area and Separate Entrance. 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."
* LISTED OVER 120 DAYS  * PRICE LOWERED - $798,900 TO $775,000 
$749,900
114 PARKS RD, Chester MD 21619
6
BEDS
6
BATHS
3,294
SQFT
$228
$/SQFT
1.55
ACRES
1991
BUILT
"Amazing opportunity to own this waterfront property offering 2 upgraded homes on 1.5 acres with pier and 10k lb lift.Great water views from both homes. Spacious main house provides 4 bedrooms, 2.5 baths, hardwood floors & 2 fireplaces while cottage has 2 bedrooms (1 currently used as office) 2.5 baths,fabulous kitchen and gas fire place. Lovely decks on both houses with gorgeous water views. Did I mention the outdoor Firepit and Game Room? Rent one live in the other or live and entertain in both. The possibilities are endless. No HOA. Less than 5 minutes to Bay Bridge but this property feels like a sanctuary."
$739,000
2816 HARVEST CT, Chester MD 21619
3
BEDS
3
BATHS
2,788
SQFT
$265
$/SQFT
3.28
ACRES
1988
BUILT
"** Its all about the views of Cox Neck Creek and Crab Alley. 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*"
$729,000
1610 MIDWAY RD, Chester MD 21619
5
BEDS
3
BATHS
3,861
SQFT
$189
$/SQFT
0.88
ACRES
2018
BUILT
"Stunning contemporary in one of the most family friendly communities on the Eastern Shore... Marling Farms. This home is virtually brand new with tons of custom features. The Chefs kitchen comes complete with gas stove, pot filler, huge kitchen island with prep sink and built in banquet, stainless steel appliances, farm sink, walk in pantry and soft close cabinets. The Kitchen overlooks your massive family room with stone fireplace. The main floor bedroom has a connecting full bath that can serve as a play room or in-law suite. Retreat to your master bedroom with fireplace, spa like bathroom complete with heated floors and enormous walk-in closet. Additional bedrooms upstairs are large and the 4th bedroom has an unfinished room over the garage for whatever your dreams can envision. The basement is 1500 sqft that's roughed in to be an entertainer's dream. Rough ins include bathroom, wet bar and media room. Enjoy your porch off the kitchen that's ready for speakers and TV, the large flat yard is fully fenced and a pool is already on the plat with the county. Your new home is a few steps from the water in a family friendly community complete with multiple access points to the water, boat ramps and picnic areas. Escape the city madness just 10 miles from the Bay Bridge-this is the resort style life you've been looking for."
* PRICE LOWERED - $742,000 TO $729,000 
$725,000
1741 HARBOR DR., Chester MD 21619
4
BEDS
2
BATHS
2,040
SQFT
$355
$/SQFT
0.47
ACRES
1956
BUILT
"REDUCED $25K! This is what you have been waiting for! Elegant one level waterfront on peaceful Cox Creek! Stunning 4 BR, 2 full BA Rancher with 200' of prime shoreline, thoughtfully designed and offering superb layout, great entertaining spaces all while enjoying water views from most rooms. Recent upgrades include fresh paint in warm neutral tones, roof, siding, kitchen and baths, HVAC, windows and custom plantation shutters. Oversized garage easily fits 2 cars along with tons of storage and workspace options. Extra large driveway can easily accommodate several more cars. Lushly landscaped front and rear yards while you enjoy magnificent sunsets from the 30' raised patio. Seller added custom dog fence that can be removed. Pier sold as is. This home is a beauty and won't last long!"
* PRICE LOWERED - $750,000 TO $725,000 
$689,900
151 JOHN GIBSON DR, Chester MD 21619
5
BEDS
4
BATHS
3,856
SQFT
$179
$/SQFT
0.14
ACRES
2010
BUILT
"It just doesn't get better than this - a 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!"
$675,000
114 ELINOR ST, Chester MD 21619
5
BEDS
4
BATHS
3,966
SQFT
$170
$/SQFT
0.13
ACRES
2018
BUILT
"Koch home in Gibson's Grant with 5 bedrooms and 3.5 baths, including possible bedroom above the garage, with a full bath. Main second level master suite with a sunset view balcony. Water views of the Chester River. Two front covered porches. Gourmet kitchen with granite, stainless steel and hardwoods. Great room with stone fireplace. Master suite has a large tub and walk-in shower. Easy access to Cross Island Nature Trail, 20-minute drive to Annapolis. The community center features pool, fitness center, Chester Riverside Pavilion and fishing/crabbing pier."
* PRICE LOWERED - $690,000 TO $675,000 
$650,000
1834 SAINT MARYS RD, Chester MD 21619
2
BEDS
3
BATHS
2,236
SQFT
$291
$/SQFT
0.49
ACRES
1974
BUILT
"Great waterfront with panoramic views and pier. Expandable space in attic. Updated baths, granite counters, almost new appliances,mahogany flooring,"
$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 
$634,999
109 JOHN GIBSON DR, Chester MD 21619
6
BEDS
5
BATHS
4,165
SQFT
$152
$/SQFT
0.17
ACRES
2010
BUILT
"THE ONE You Have Waited for in Gibson's Grant Just Came to Market... Over 4100 sq ft Total, of High-End, Custom Elegance!! SIX Bedrooms, 4.5 Baths, Designer Touches at Every Turn!! Southern Charm Meets Contemporary Elegance- Welcoming Foyer Opens to 3-Story Staircase, Sitting Room, Private Office, & Dining Room- You'll Drool Over the Wide Plank Flooring, Custom Moldings, Bright & White Gourmet Kitchen with Gleaming Granite, Stainless Appliances, Custom Lighting, Built-Ins, Walk-Ins & SPACE... Bring Your Crew AND Stuff! 3-Car Oversized Garage with Finished Bedroom AND Full Bath Above! Extensive Hardscaping Makes for Turn-Key Living Close to Work & Play! Walk to Community Pool, Clubhouse, Gym, Pier, Playground, Bocce Ball & Cross-Island Bike/Walking Trail! 5 mins from Bay Bridge! FANTASTIC VALUE in Gibson's Grant- Rare Opportunity... Claim this Stunning Home Before Your Competition Does!"
$629,000
2912 COX NECK RD E, Chester MD 21619
4
BEDS
4
BATHS
3,659
SQFT
$172
$/SQFT
1.51
ACRES
1999
BUILT
"Looking for a well built Custom Post & Beam home to make your own? Here's your chance, a rare opportunity with water view & water access. Hardwoods, Tile, 4 bedrooms, 3.5 baths, freshly painted interior & exterior. Wide open lot 1.5 acres & the exterior of the house has that coastal feel! Located in the Up- Scaled community of Southwind. This community has a boat launch & storage, tennis court small club house. Minutes to Restaurants, shopping & Bridge. This house is a custom designed timber frame house. In 1997, the architects, Finelli & Gray of New Hope PA, were contracted by the original owner to design a ~light spacious and elegant~ wooden home for their family. The result home features a main house with open spaces, real wood floors and ceilings, and a craftsman feel.The frame itself was custom crafted by Lancaster County Timber Frames (https://lancotf.com/) out of Hemlock. No metal bolts or plates are used in the frame, only joinery - which adds to the craftsmanship of the house. A premier frame builder, Lancaster County Timber Frames are known not only for residential, but also commercial structures like breweries, wineries and even the Gettysburg National Battlefield Museum (https://bit.ly/2w6pzpI) Unlike a normal home built with 2 by 4s, the house gets its structural integrity from the huge beams. Each vertical beam is supported by it's own pier in the foundation and this makes this house extremely solid. On the outside of the frame is covered by Structurally Integrated Panels (https://bit.ly/2wbxC4E). Using SIPs makes the house almost airtight and very efficient to cool/heat."
* PRICE LOWERED - $655,000 TO $629,000 
$600,000
184 EVELYNE ST, Chester MD 21619
3
BEDS
3
BATHS
2,437
SQFT
$246
$/SQFT
0.13
ACRES
2013
BUILT
"Main-Level Master Suite in Coveted Gibson's Grant!! High End Finishes Throughout! Over 2400 sq ft, 2 HUGE Upper-Level Bedrooms, Finished Room Over Garage for Large Bonus Space! Attached 2-Car Garage, Inviting Front Porch for Sippin' & Relaxin'! Desireable Community Amenities: Pool, Stylish Clubhouse, Pier, Playground, Bocce Ball & More! LOW HOA Dues!! 5 mins from Bay Bridge- HURRY to this One Before Your Competition Does!"
$599,894
124 CAVALIER CT, Chester MD 21619
3
BEDS
4
BATHS
2,862
SQFT
$210
$/SQFT
0.14
ACRES
2019
BUILT
"Beautiful open floor plan home in long awaited 55+ Four Seasons Community at Kent Island! The Lille Loft features 3 bedrooms and 3 baths, covered patio, spacious loft and gourmet kitchen. Granite countertops, decorative backsplash, luxury vinyl in common areas and Stainless Steel appliances are some of the beautiful designer features this home has. Call our office for more information. Photo likeness."
* PRICE LOWERED - $601,034 TO $599,894 
$599,000
126 MCHENNY CT, Chester MD 21619
3
BEDS
3
BATHS
2,220
SQFT
$270
$/SQFT
0.13
ACRES
2010
BUILT
"RARE Gibson's Grant Offering!!! COVETED WaterView Location on Dead-End Street! MAIN-LEVEL MATER SUITE with French Doors onto Private Deck & Screened Porch Overlooking Fenced Yard & Detached 2- Car Rear-Entry Garage w/ Covered Entry to House! STUNNING Open Floor-Plan... THIS is the 'WOW Factor' Home! Custom Built with All the Bells & Whistles! Begging to Entertain w/ Great Flow, Soaring Ceilings, & Abundance of Natural Light! Loft Area on 2nd Level Captivates Peaceful WaterViews & Boasts Large 2nd & 3rd Bedrooms & Guest Bath! Wide Plank Hardwoods, Gleaming Granite, High- End Cabinetry, Impeccably Maintained! 5 mins from Bay Bridge, 20 mins from Annapolis! 1-Hr to DC- You Can Still Still 'Smell the New' Here.. Come Claim this Gem Before Your Competition Does!Curious? Take the Tour Now! https://my.matterport.com/show/?m=BWCbqH3JXXD"
* PRICE LOWERED - $625,000 TO $599,000 
$575,000
127 CEDAR RD, Chester MD 21619
4
BEDS
4
BATHS
3,400
SQFT
$169
$/SQFT
0.54
ACRES
2006
BUILT
"Benton's Pleasure This Custom built Contemporary home shows the pride of ownership. The home features 4 Bedrooms 4 full baths. Which include two master suites. The downstairs den could easily be converted into a first floor master suite as well. The additional bedrooms have a Jack and Jill bath. Eat in kitchen with granite counter tops and a large center island. Also, featuring formal dining and living room. Wonderful open floor plan and great for entertaining, two story great room and home features many upgrades. The crawl space and garage are conditioned. This is the home you have been looking for."
* PRICE LOWERED - $589,000 TO $575,000 
 
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