Chester Real Estate, Homes and Condos for sale

All Chester homes currently listed for sale in Chester as of 02/23/2020 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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$1,590,000
2888 COX NECK RD, Chester MD 21619
4
BEDS
4
BATHS
3,539
SQFT
$449
$/SQFT
2.90
ACRES
1993
BUILT
"Broad water views and light fill this elegant contemporary located in the desirable community of Southwind. This custom built home has an outstanding floor plan offering 3539' of living space. Walls of glass surround the waterside 2 story family room which is open to the gourmet kitchen with Granite counter tops, stainless appliances and island. The kitchen is large enough for a comfy table and chairs. There is a separate dining room too. Upstairs are 4 bedrooms and 3 full baths. Two bedrooms are connected with Jack and Jill bath. The third bedroom has an attached bath with hallway entrance. Lovely master suite is spacious with sitting room, huge bath, his and her walk in closets and waterside 32 x 14 private deck. Hardwoods and water views throughout. Exterior shower enclosure and 3 car garage. Located at end of community in cul de sac for more privacy and steps from clubhouse, tennis cts and community water features."
$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 theater, run a home business or much more. Watch the beautiful sunrises, kayak and take your boat out for a spin from your pier. Set up for outdoor 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. Hardwood floors, granite counters, formal dining area - it's all here! 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. Motivated sellers."
* PRICE LOWERED - $1,499,000 TO $1,399,999 
$1,325,000
609 SERENITY LN, Chester MD 21619
4
BEDS
5
BATHS
4,407
SQFT
$301
$/SQFT
3.10
ACRES
2018
BUILT
"Ohhh MY!! DREAM HOMES Like THIS Don't Come to Market Often... Better Hurry! Custom-Built Craftsman Boasting Over 4400 SF Perfectly Perched Upon 3.1 Acres on Crab Alley Bay! Protected Waterfront Living with Ease of Navigation- Perfect Combo! Every. Single. Desire. Answered Here! THIS is the Home You've Worked For! Entertain Like a Master! In-Ground Gunite Salt-Water Pool, w/ Waterfall! Large Patio Overlooking Water's Edge & Private Pier! Fishing, Crabbing, Hunting- From Your Backyard! Inside, A Gourmet Kitchen Straight from the Magazines! White & Bright Custom Cabinetry, Gleaming Granite, Shiny Stainless Appliances Including Cooktop & Hood, Wall-Oven & Wine Fridge! A Chef's Delight! Large Pantry, Oversized Breakfast Bar & Breakfast Room with Shiplap Ceilings, Exposed Beam & 360-Degree WaterViews Opens to Huge Covered Porch- Extended Outdoor Living Space! This Home Was Built to Entertain! AMAZING Flow, Natural Light & Attention to Detail! Soaring 2-Story Ceilings in Family Room are Anchored by Stacked Stone Wood-Burning Fireplace for Cozy Nights! Main-Level Master Suite Rivals a 5-Star Hotel! Simply FABULOUS Master Bath! Coastal Touches with High-End Finishes- Soaking Tub, Double Vanity w/ Ample Storage & 2-Person Shower! Upstairs, 3 Spacious Bedrooms Suites Make Privacy & Spreading Out a Breeze! Each Bedroom with Full Bath Attached! Large Den Overlooks Family Room & Leads to HUGE Walk-in-Storage Room! Attached 3-Car OverSized Garage! Private, Peaceful Location Just 10 Mins From Bay Bridge- 1-Hr DC! Easy Boating to Chesapeake Bay, Kent Narrows & St Michaels! Discover What 'Eastern Shore Waterfront Living' is All About! Claim This Gem Soon & Start Planning the Pool Parties & Boating Trips...Before Your Competition Does!"
* PRICE LOWERED - $1,385,000 TO $1,325,000 
$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's 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. 1 perfect acre, room for a pool and only 5 min to the Bay Bridge."
* NEW LISTING 
$1,075,000
228 BENTONS PLEASURE RD, Chester MD 21619
4
BEDS
4
BATHS
3,571
SQFT
$301
$/SQFT
0.61
ACRES
2005
BUILT
"JUST LISTED!! Summer IS Coming... Better Hurry to. This GORGEOUS Custom-Built Kent Island WATERFRONT! It's what 'Island Living' is All About! Private Pier, w/ Boat Lift & Jet Ski Lift Just Begging For Playtime! Boating, Jet Ski, Crabbing, Fishing- all from your back door! Your Private Island Oasis! Million-Dollar Sunsets & SPACE! Boasting Over 3200 sq ft of Exquisite Craftsmanship, Millwork & Style- the Open, Generously Sized Floor-Plan Affords Something for All! Inviting, 2-Story Foyer Greets Guests, Leading to Spacious Family Room w/ Wall of French Doors to Stunning Waterfront Views! Stacked Stone Gas Fireplace is one of FOUR for Cozy Nights! Gourmet Kitchen w/ Gleaming Granite, Custom Cabinetry & Large Breakfast Bar Opens to Morning Room w/ Table Space for Waterfront Dining! Main-Level Master Suite w/ Fireplace & Sliders to Private Waterfront Patio! Spa-Like Master Bath & Huge Walk-in-Closet! Main-Level Den w/ Fireplace & Built-Ins Makes Perfect Office or Tucked-in Sanctuary! 3 Upper-Level Bedrooms Each Attached to Full Bath are accessed over Catwalk w/ Inescapable Water-Views! Private Waterfront Balcony off 2nd Bedroom will have Guests Never Wanting to Leave! Large Private Bath & Fireplace. Jack-and-Jill shared Full Bath for Large 3rd/4th Bedrooms. Ample Storage! Over-Sized 2-Car Garage, Walk-in-Storage Room Above & Generously-Sized Closets Throughout! 10 Mins from Bay Bridge- 1-Hr DC. 20 Mins by Boat to St Michaels! Claim this Stylish Beauty Soon... Before your competition is living YOUR Waterfront Dream!"
* NEW LISTING 
$949,900
328 BENTONS PLEASURE RD, Chester MD 21619
3
BEDS
3
BATHS
1,725
SQFT
$551
$/SQFT
1.55
ACRES
1953
BUILT
"This truly special waterfront home has been the joy of the Owners (and theirextended family) for more than 30 years. One visit and you will know why- It is what everyoneDREAMS about when they imagine their perfect Shore Home. Placed with a commanding view ofCox Creek (and truly spectacular sunsets), this 3 Bedroom, 2-1/2 bath gem was designed tocelebrate 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 anenormous screened porch that connects to the wonderful gourmet kitchen. It opens onto acovered porch that has steps to a slate tile patio (partially heated along with the steps and frontsidewalk!). The expansive yard sits well above the flood plain and has some mature trees thatshade 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 andwatersports await! There is truly nothing quite like it! *Recent appraisal by May and Assoc.indicate $1M valuation!"
$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 
$825,000
1521 CALVERT RD, Chester MD 21619
4
BEDS
3
BATHS
2,925
SQFT
$282
$/SQFT
0.87
ACRES
1992
BUILT
"Quality, custom construction with panoramic waterviews, large site, and state-of-the art systems. Features include...geothermal two-zone HVAC, 2x6 construction, 10' ceilings and vaulted ceilings on first floor, large laundry/mudroom, basement, lighted and concrete-floored crawl spaces. Large first-floor master suite with expansive bath and walk-in closet. Formal living and dining area, large eat-in kitchen, family room, screen porch, and greenhouse. Waterviews from most rooms, private pier with slip, greenhouse, screen porch, and large deck. Priced below appraised value. Situated on almost an acre, the property offers privacy and an adjacent picnic area with a boat ramp and kayak storage."
* NEW LISTING 
$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!"
$699,900
115 CEDAR RD, Chester MD 21619
5
BEDS
4
BATHS
4,275
SQFT
$164
$/SQFT
0.84
ACRES
2006
BUILT
"OPEN HOUSE, Saturday February 29th 12-2PM. Spectacular Custom Built Home - Bentons Pleasure Kent Island - Detailed upgrades and features on this truly amazing home - Here are just a few - Attached 3 car Garage, Detached 2 story Garage (with Heat and AC), TWO Rinnai HWH systems, FOUR Zoned HVAC Units, Kitchen was Friels Kitchen and Bath FEATURED Kitchen for 2 years - if that gives you an idea of how amazing it is!!! Bonus Room above Garage with additional Bedroom! Master Suite with incredible Master Bath (Shower has dual heads and jets in wall,) Catherdral Ceiling and skylights. Second Master on 2nd Floor with private Full Bath! First Floor Bedroom or Office. Formal Dining Room. Living Room with Cozy Gas Fireplace. Sunroom with beautiful tile floor, Cathedral pine ceiling, 8' wide sliding door opens to sensational outdoor living space!"
$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!"
$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
"Gorgeous Gibson's Grant home with all the perks! Main level master suite has walk-in closet and ensuite bath (jetted tub, separate shower, dual vanities, marble countertop, and w/c). The room above the garage has been finished, complete with built-ins and a wet bar. Open kitchen with stainless steel appliances, island with bar seating, bar, white granite counters, and a white farmhouse sink. The fenced yard has professionally designed landscape and hardscape, including a fire pit, and a shed. Plantation shutters, California Closets, custom front door with stained glass, fireplace, generous wood floors, custom glass shower doors, ceiling fans, and more.. Over $140,000 in upgrades and options. Don't wait for new construction when you could be relaxing on the spacious front porch this Spring, enjoying the water views and breeze."
$624,900
151 JOHN GIBSON DR, Chester MD 21619
5
BEDS
4
BATHS
3,856
SQFT
$162
$/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 - $634,900 TO $624,900 
$616,000
2912 COX NECK RD E, Chester MD 21619
4
BEDS
4
BATHS
3,659
SQFT
$168
$/SQFT
1.51
ACRES
1999
BUILT
"3600 square foot custom designed timber frame home with great water views. Architects Finelli & Gray designed a spacious and elegant wooden home with a cupola, expansive windows, a grand fireplace, and solid wood beams throughout resulting in a unique craftsman feel. With 1.5 acres of land, views of the Eastern Bay and neighborhood beach, tennis and launch ~ this home is a nature lovers dream."
$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."
$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."
$599,900
123 BENTONS PLEASURE RD, Chester MD 21619
4
BEDS
3
BATHS
2,791
SQFT
$215
$/SQFT
1.00
ACRES
2002
BUILT
"Do not miss this gorgeous, custom-built home in Benton's Pleasure that sits on a One Acre Lot. This stone-front home boasts a gourmet kitchen and open floor plan making it an entertainer's dream. The gourmet kitchen features stainless steel appliances, including a double oven. Just off the eat-in kitchen, through the brand new sliding glass door is a large Trex deck, increasing your entertaining space. Just off the deck sits the pristine in-ground pool, perfect for cooling off in the summer. The second level includes a spacious master suite with a five piece bath and a walk-in closet. Watch your favorite movie or favorite sports teams on your new projection screen in the large media room. Countless upgrades have been done throughout the home to make it energy efficient and saves on utility bills, including solar panels and a tankless water heater. Many of the major systems have been been upgraded (Furnace in 2016 and water softener and reverse osmosis system in 2019). This home is already built and has all of the upgrades for you to enjoy. Come see for yourself."
$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!"
$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."
$589,000
215 MCGUCKIN ST, Chester MD 21619
4
BEDS
3
BATHS
2,914
SQFT
$202
$/SQFT
0.13
ACRES
2008
BUILT
"$11k Price Improvement! Welcome Home! This one is a RARE find in Gibson's Grant - You will never have a neighbor across the street - just the peace of the protected pond view from your front porch on one of the only dead end streets in the community! This sought after model boasting nearly 3,000 sq ft of living space, 4 Upper Level Bedrooms 2. 5 baths with ATTACHED 2 car garage. You'll love preparing meals in the gourmet kitchen with Viking gas stove, double ovens, double pantry, stainless steel appliances, granite counters, glass tile back splash and an island made for entertaining. The family room is complete with a gas fireplace and newer plush carpet. The main floor offers a formal living, dining and separate office with custom built-ins. Ask about the secret room! Upstairs you will find more water views, a full size laundry room with utility sink, 4 bedrooms and 2 full baths, including the master suite with tray ceiling, large corner tub, double vanity, separate shower and wash closet. The home offers dual zone HVAC with two newer units. The over sized 2 car garage is attached with a driveway for 2 additional cars. The backyard is fully fenced and is the perfect combination of grass and paved patio to enjoy grilling and outdoor dining! Gibson's Grant is a waterfront community on Kent Island offering first class amenities including outdoor heated pool, fishing/crabbing pier, kayak launch, clubhouse, gym and pavilions! Located on the cross island trail, close to shopping and dining, marinas & beaches! Easy access to 50 and only minutes to the Chesapeake Bay Bridge!"
* PRICE LOWERED - $600,000 TO $589,000 
 
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