Your Complete Real Estate Guide

Chester Real Estate, Homes and Condos for sale

All Chester homes currently listed for sale in Chester as of 09/17/2019 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!"
* LISTED OVER 120 DAYS 
$1,400,000
2903 COX NECK RD E, Chester MD 21619
5
BEDS
4
BATHS
5,328
SQFT
$263
$/SQFT
1.10
ACRES
1995
BUILT
"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, freshly painted through-out, Tile & Hardwood, 5 bedrooms & 3.5 baths. Use your flex space on the third floor for , exercise room, home threater, run a home business or much more. Watch the beautiful sunrises, kayak, take your boat out for a spin from your pier. Set up for out door living with a beautiful built in pool, large screened porch."
$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."
* LISTED OVER 120 DAYS  * 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."
$1,175,000
2813 COX NECK RD, Chester MD 21619
5
BEDS
4
BATHS
3,694
SQFT
$318
$/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 two and a half story 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, one of granite and the other a brand new oversized center island that is covered in Quartz and is IMPRESSIVE ! This kitchen offers 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. En suite bath is beautiful with walk in shower, luxurious oversized bathtub and double vanities with brand new Quartz countertops. 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 brand new Trex decking and expansive custom paver patio area with firepit ~ 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, Beautiful hardwood floors throughout both 1st and 2nd floors, 2nd floor boasts 5 hand scraped hardwood floors installed in 2018, Anderson windows, Dual Zone Trane Heat/AC, 2 car attached garage, lots of extra storage space with pull down stairs to an extra-large full size attic and another large attic space easily accessed by a door, super"
* LISTED OVER 120 DAYS  * PRICE LOWERED - $1,195,000 TO $1,175,000 
$1,139,000
228 BENTONS PLEASURE RD, Chester MD 21619
4
BEDS
4
BATHS
3,519
SQFT
$324
$/SQFT
0.61
ACRES
2005
BUILT
"This artfully designed, 4 bedroom, 3.5 bathroom waterfront home boasts over 3,500 square ft. 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!"
* LISTED OVER 120 DAYS  * PRICE LOWERED - $1,199,000 TO $1,139,000 
$949,000
2839 COX NECK RD, Chester MD 21619
3
BEDS
3
BATHS
2,664
SQFT
$356
$/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."
$939,000
328 BENTON PLEASURE RD, Chester MD 21619
3
BEDS
3
BATHS
1,725
SQFT
$544
$/SQFT
1.55
ACRES
1953
BUILT
"***Reduced!!*** 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! *Recent appraisal by May and Assoc. indicate $1M valuation!"
* PRICE LOWERED - $989,000 TO $939,000 
$924,990
0 CHESTER WAY, Chester MD 21619
4
BEDS
4
BATHS
3,516
SQFT
$263
$/SQFT
0.10
ACRES
"You do not want to miss out building a new Koch Home in Gibson's Grant! Final section now available. Build a Kingston 3 story on this beautiful homesite with views to Chester River. Limited availability left!! HOME TO BE BUILT. PICTURES FROM KINGSTON 3 STORY MODEL HOME. Ask about special developer incentive on homesite 60."
$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
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 will be complete in 30 days or less!"
$739,000
1900 BAYSIDE DR, Chester MD 21619
3
BEDS
3
BATHS
2,588
SQFT
$286
$/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. 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!"
* PRICE LOWERED - $749,999 TO $739,000 
$724,900
1610 MIDWAY RD, Chester MD 21619
5
BEDS
3
BATHS
3,861
SQFT
$188
$/SQFT
0.88
ACRES
2018
BUILT
"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!"
$699,999
114 PARKS RD, Chester MD 21619
6
BEDS
6
BATHS
3,294
SQFT
$213
$/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."
* PRICE LOWERED - $725,000 TO $699,999 
$695,000
1741 HARBOR DR., Chester MD 21619
4
BEDS
2
BATHS
2,040
SQFT
$341
$/SQFT
0.47
ACRES
1956
BUILT
"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!"
* LISTED OVER 120 DAYS  * PRICE LOWERED - $725,000 TO $695,000 
$676,990
0 ELINOR ST, Chester MD 21619
4
BEDS
3
BATHS
2,907
SQFT
$233
$/SQFT
0.12
ACRES
"You do not want to miss out building a new Koch Home in Gibson's Grant! Final section now available. Build a Kingston 2 story on this beautiful homesite. Limited availability left!! HOME TO BE BUILT. PICTURES FROM KINGSTON 3 STORY MODEL HOME."
$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."
* LISTED OVER 120 DAYS  * PRICE LOWERED - $695,000 TO $649,900 
$639,900
151 JOHN GIBSON DR, Chester MD 21619
5
BEDS
4
BATHS
3,856
SQFT
$166
$/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!"
* LISTED OVER 120 DAYS  * PRICE LOWERED - $649,900 TO $639,900 
$635,000
203 JOHN GIBSON DR, Chester MD 21619
4
BEDS
4
BATHS
3,756
SQFT
$169
$/SQFT
0.20
ACRES
2009
BUILT
"On a Corner Lot, first time this NVR model has come up for resale in Gibson's Grant. This wide open floor plan model won't last long! Over $75K in updates in 2019 alone. Updates include: New wood floors, white quartz counter-tops, Hue under and above interchangeable 5 color cabinet lighting package, Stainless steel appliances, luxury carpeting in bedrooms, custom closets in master and guest bedroom, white subway tile back-splash, reclaimed wood accent walls, whole house painted, new hot water heater, new top load washer and dryer, updated fireplace, Sealed and painted 3 Car garage floor, custom paver patio and landscaping with custom high end lighting in front and backyards, LED lighting throughout, Nest thermostat x2 , Nest smoke detectors, Nest Camera and keyless entry to front and back doors, and custom plantation shutters throughout. So many other upgrades you need to come see for yourself!!!! For those who love to entertain, this home is for you. Come make this coastal dream home yours!"
* NEW LISTING 
$630,000
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."
$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."
* LISTED OVER 120 DAYS  * PRICE LOWERED - $655,000 TO $629,000 
$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
"Quick Move-in Home currently under construction. 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. Available October 2019. Photos are from our model and shows additional upgrades."
* PRICE LOWERED - $613,190 TO $595,854 
$585,000
184 EVELYNE ST, Chester MD 21619
3
BEDS
3
BATHS
2,437
SQFT
$240
$/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!"
* PRICE LOWERED - $600,000 TO $585,000 
 
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