Chester Real Estate, Homes and Condos for sale

All Chester homes currently listed for sale in Chester as of 03/23/2019 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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$1,595,000
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. Motivated sellers."
* LISTED OVER 120 DAYS 
$1,424,000
2867 COX NECK RD, Chester MD 21619
3
BEDS
4
BATHS
6,068
SQFT
$235
$/SQFT
2.40
ACRES
1999
BUILT
"TRUSTEE SALE ! MUST SELL! One level living at it's finest. Breath taking water views of Eastern Bay. This home boasts just over 6,000 square feet of living space, with 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!"
* PRICE LOWERED - $1,499,000 TO $1,424,000  * SHORT SALE 
$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."
* LISTED OVER 120 DAYS  * PRICE LOWERED - $849,900 TO $824,900 
$779,000
114 PARKS RD, Chester MD 21619
6
BEDS
6
BATHS
3,294
SQFT
$236
$/SQFT
1.55
ACRES
1991
BUILT
"Two Waterfront Houses. Beautiful Views of Cox Creek, Nature is abundant on this property, boardwalk to private pier on Cox Creek where you can enjoy boating, crabbing, or just relaxing on the pier and taking in the sites. Two Homes on property provide room for everyone featuring a total of Six Bedrooms and 4 Full and 2 Half Baths, Hardwood Floors, 3 Fireplaces AND a outdoor Firepit and Game Room and Wet Bar with AWESOME Waterview for gatherings. Both Main House and Guest House are impeccably updated and ready for occupancy."
$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,"
$630,000
102 JOHN DABB CT, Chester MD 21619
5
BEDS
3
BATHS
2,837
SQFT
$222
$/SQFT
0.18
ACRES
2016
BUILT
"Your Search is Over...THIS IS IT!!! You'll Drool Over this Gibson's Grant, Koch Built- Generously-Sized Colonial at Over 2800 sq ft, 4 Upper-Level BR's, Optional 5th BR/Office/Den Above Garage, WOW Kitchen- White Cabinets Contrasted by Espresso Island w/ Gleaming Granite Counters & High-End Stainless Appliances, Corner, Fenced Lot w/ Great-Sized Yard Just Steps From Community Clubhouse & Pool! Chester River Views- AMAZING Amenities- HURRY to this one, Before Your Competition Does! Recent Appraisal in Hand @ $630K!"
$599,000
127 CEDAR RD, Chester MD 21619
4
BEDS
4
BATHS
3,400
SQFT
$176
$/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."
* NEW LISTING 
$598,190
248 BAYBERRY DR, Chester MD 21619
3
BEDS
4
BATHS
2,868
SQFT
$209
$/SQFT
0.15
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, screened porch, 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. Available end of April. Call our office for more information. Photo likeness."
$574,900
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"
* LISTED OVER 120 DAYS  * PRICE LOWERED - $594,900 TO $574,900 
$574,000
127 HOPKINS RD, Chester MD 21619
4
BEDS
3
BATHS
2,800
SQFT
$205
$/SQFT
0.92
ACRES
2019
BUILT
"Lovely 0.92 acre homesite with WATER VIEWS in Benton's Pleasure! Listing is for base price on a to be built Madison 2 by Whitehall Building & Co. which can be customized! Other plans/options available. Construction to permanent financing required. $10k towards options with use of preferred lender/title."
* PRICE LOWERED - $585,000 TO $574,000 
$559,000
126 HENRY STOUPE WAY, Chester MD 21619
4
BEDS
3
BATHS
2,700
SQFT
$207
$/SQFT
0.13
ACRES
2010
BUILT
"NEWLY LISTED!! This Gibson's Grant NV-Built Home Boasts 2700 sq ft, Open Floor-Plan, 2-Car Garage, 4 Upper-Level Bedrooms, Inviting Foyer with Ample Natural Light- Large Kitchen/Dining/Family Room- Steps Away from Unbeatable Community Amenities: Pool, Clubhouse, Fitness Center, Pier & More! 5 Mins from Bay Bridge- Priced to SELL... Hurry to This One!"
$539,000
101 HENRY STOUPE WAY, Chester MD 21619
4
BEDS
3
BATHS
2,620
SQFT
$206
$/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!"
* LISTED OVER 120 DAYS  * PRICE LOWERED - $549,999 TO $539,000 
$534,990
316 BAYBERRY DR, Chester MD 21619
2
BEDS
2
BATHS
2,597
SQFT
$206
$/SQFT
0.17
ACRES
2019
BUILT
"To be build home in long awaited 55+ Four Seasons Community at Kent Island! The San Sebastian features an inviting foyer, 2 bedrooms, 2 baths, home office and large kitchen with huge island. Granite countertops, engineered wood in foyer and kitchen, Stainless Steel appliances are some of the designer features this home includes in addition to many more choices you can pick from to make it your own. Price shown is base lot premium may apply. Call our office for more information. Photos are from our model and shows additional upgrades."
$524,388
144 AMBASSADOR LN, Chester MD 21619
2
BEDS
2
BATHS
2,002
SQFT
$262
$/SQFT
0.14
ACRES
2019
BUILT
"Beautiful main living open floor plan home in long awaited 55+ Four Seasons Community at Kent Island! The Ibiza features 2 bedrooms, 2 baths, home office and attic storage. Designer features include white cabinets, quartz countertops, luxury vinyl floors in common areas, Gourmet kitchen with Stainless Steel appliances. This home will be ready June 2019. Call our office for more information. Photos are from our model and shows additional upgrades."
* NEW LISTING 
$509,243
135 AMBASSADOR LN, Chester MD 21619
2
BEDS
2
BATHS
1,689
SQFT
$302
$/SQFT
0.13
ACRES
2019
BUILT
"Beautiful main living open floor plan home in long awaited 55+ Four Seasons Community at Kent Island! The Donegal features 2 bedrooms, 2 baths, home office and large kitchen. Designer features include quartz countertops, luxury vinyl floors in common areas, Gourmet kitchen with Stainless Steel appliances. This home will be ready June 2019. Call our office for more information. Photos are from our model and shows additional upgrades."
* NEW LISTING 
$509,000
121 HENRY STOUPE WAY, Chester MD 21619
3
BEDS
3
BATHS
2,320
SQFT
$219
$/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  * PRICE LOWERED - $520,000 TO $509,000 
$502,120
232 BAYBERRY DR, Chester MD 21619
2
BEDS
2
BATHS
1,993
SQFT
$252
$/SQFT
0.13
ACRES
2019
BUILT
"Beautiful main living open floor plan home in long awaited 55+ Four Seasons Community at Kent Island! The Barbuda features 2 bedrooms, 2 baths, home office and attic storage. Designer features include quartz countertops, luxury vinyl floors in common areas, Gourmet kitchen with Stainless Steel appliances. This home will be ready June 2019. Call our office for more information. Photos are from our model and shows additional upgrades."
* NEW LISTING 
$475,000
326 CASTLE MARINA RD, Chester MD 21619
5
BEDS
4
BATHS
2,920
SQFT
$163
$/SQFT
0.39
ACRES
1972
BUILT
"Absolutely stunning colonial with $150K in recent renovations. Awesome & convenient location & only blocks to the water, marina, shopping, restaurants, parks, cross island trail & more. No HOA/restrictions! Relax in the in-ground pool with slide, roast marshmallows or have a cook out/party in the full fenced back yard. This house is larger than it looks & boasts 5BR's, gorgeous ceramic & hardwood floors through-out the first floor & 2nd floor. Gourmet kitchen with granite counters, double oven, gas 5+ burner stove, 2 FPs, paved driveway, WIC, 2 Master bedrooms (one on 1st floor), 2 Jacuzzi tubs, second floor balcony & so much more. Come check it out & you will fall in love. Owner will consider all offers!"
$469,000
407 SWAN COVE LN, Chester MD 21619
2
BEDS
2
BATHS
2,254
SQFT
$208
$/SQFT
1978
BUILT
"WATERFRONT condo on Kent Island in small private area (just 12 units). Witness the unobstructive and magnificent sunsets every evening from every room. This home features first floor living all on one level with two bedrooms, two full baths, open floor plan living area with fireplace, open kitchen and dining area. The sun room leads to the large deck with awning. Perfect for entertaining and watching the abundant wildlife. The versatile 600 sf finished basement with fireplace & plenty of closet space makes a great rec room, guest room, or office with access to front parking area and the garage. Just a few steps off the deck is the pier and slip with an 8,000 lb lift. The cove yields lots of crabs and fish all season long. Just a short stroll will take you to Ferry Point Park for sand in your toes or the Cross Island Trail. Enjoy the Narrows by boat or foot. This low maintenance lifestyle is like being on vacation every day of the year. The monthly condo fees are only $250 and include homeowners and flood insurance as well as lawn care, trash removal, and more."
$463,990
140 AMBASSADOR LANE, Chester MD 21619
2
BEDS
2
BATHS
2,116
SQFT
$219
$/SQFT
0.15
ACRES
2019
BUILT
"To be build home in long awaited 55+ Four Seasons Community at Kent Island! The Killarney features, 2 bedrooms, 2 baths, home office and large kitchen with huge island. Granite countertops, engineered wood in foyer and kitchen, Stainless Steel appliances are some of the designer features this home includes in addition to many more choices you can pick from to make it your own. Price shown is base lot premium may apply. Call our office for more information. Photos are from our model and shows additional upgrades."
$445,520
244 BAYBERRY DR, Chester MD 21619
3
BEDS
2
BATHS
1,747
SQFT
$255
$/SQFT
0.13
ACRES
2019
BUILT
"Community Grand Opening!!! Beautiful open floor plan home in long awaited 55+ Four Seasons Community at Kent Island! The Donegal features 3 bedrooms and 2 baths, screened porch, attic storage and gourmet kitchen. Granite countertops, decorative backsplash, engineered wood in common areas and Stainless Steel appliances are some of the beautiful designer features this home has. All incentives have been applied to the listing price and it must close by end of April. Call our office for more information. Photo likeness."
$431,990
312 BAYBERRY DR, Chester MD 21619
2
BEDS
2
BATHS
1,689
SQFT
$256
$/SQFT
0.13
ACRES
2019
BUILT
"Beautiful to be build home in long awaited 55+ Four Seasons Community at Kent Island! The Donegal features 2 bedrooms, 2 baths, home office and large kitchen. Granite countertops, engineered wood in foyer and kitchen, Stainless Steel appliances are some of the designer features this home includes in addition to many more choices you can pick from to make it your own. Price shown is base lot premium may apply. Call our office for more information. Photos are from our model and shows additional upgrades."
$424,900
1908 STEVENS DR, Chester MD 21619
4
BEDS
3
BATHS
1,946
SQFT
$218
$/SQFT
0.36
ACRES
1994
BUILT
"NEW PRICE! Almost $15K!! Immaculate and Beautiful Home on Kent Island in Chester! Spacious Colonial boasting 4 Bedrooms, 2.5 Baths, Upgraded Open Kitchen complete with NEW Soft Close cabinets, New Silestone Counters & Kitchen Island! Gleaming Hardwoods in the Formal Dining Room, NEW Gray Carpet in LR & Stairs & a Pellet Stove to warm you up in the Great Room! Check out the NEW 50 Year Architectural Shingle Roof, the Newer Hot Water Heater & Carrier Furnace System.. all of your Big Ticket Items are done here!! Enjoy the covered Front Porch- plenty of space for your rocking chairs! Oversized 2 Car Garage w/Car Port for Lots of toys and BOATS!! Oh...and get ready for Summer Entertaining with the Sprawling 2-tiered Deck & Built-in Solar lighting, Awning, In-Ground Pool and the Patio Fire-pit area! You never have to leave! Neighborhood Park/Playground just at the end of this dead-end street! Close to all Schools, Library, County Parks, Boat ramps, Marina's, Beaches, Restaurants, Shopping, Bike/running Trails with easy commute to Annapolis, Baltimore & DC. Perfect Spot! Will not last long!! Come see what Eastern Shore Living is ALL about! 100% USDA Financing & No HOA Restrictions here!"
* PRICE LOWERED - $439,000 TO $424,900 
$397,000
102 BROWN RD, Chester MD 21619
4
BEDS
3
BATHS
2,160
SQFT
$184
$/SQFT
0.94
ACRES
1995
BUILT
"OPEN Sat. 3-23 12:30-1:30pm 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!"
* LISTED OVER 120 DAYS  * PRICE LOWERED - $398,000 TO $397,000 
 
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