Chester MD Real Estate

The town of Chester is located on Kent Island, the largest island in the Chesapeake Bay. From condos and townhomes to waterfront homes and estates, you’ll find a variety of real estate in Chester. Browse current Queen Anne's County real estate listings in Chester MD below.

Search Kent Island Real Estate in Chester MD

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1118 Main St Chester MD 21619

MLS Number MDQA140544

  • Commercial
  • Address 1118 Main St
  • Year Built 1978
  • Acreage 2.31
  • Property SubType Other

Updated micro brewery with elaborate stage for live entertainment. Income producing property with seating for 150+ with future plans for a restaurant (class B license).

Listed by Re/Max Advantage Realty

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$/month over payments
Federal 30-year interest rate: 3.75% last updated on Jul 11, 2019
* All Figures are estimates. Check with your bank or proposed mortgage company for actual interest rates.
This product uses the FRED® API but is not endorsed or certified by the Federal Reserve Bank of St. Louis.

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1605 Calvert Rd Chester MD 21619

Price$1,700,000

Est. Mortgage: $/month

MLS Number MDQA139522

  • Single Family
  • Address 1605 Calvert Rd
  • Bathroom 4
  • Bedrooms 5
  • Square Feet 4271

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 by Chaney Homes, LLC

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$/month over payments
Federal 30-year interest rate: 3.75% last updated on Jul 11, 2019
* All Figures are estimates. Check with your bank or proposed mortgage company for actual interest rates.
This product uses the FRED® API but is not endorsed or certified by the Federal Reserve Bank of St. Louis.

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2886 Cox Neck Rd Chester MD 21619

Price$1,650,000

Est. Mortgage: $/month

Pending

MLS Number MDQA139730

  • Single Family
  • LocationType Bayfront
  • Address 2886 Cox Neck Rd
  • Bathroom 6
  • Bedrooms 4

Incomparable point of land...expansive waterfront! Private Beach! Beautiful new wide plank hardwoods and hardwood on staircase! New neutral carpeting in first floor Owner's Suite. Freshly painted at main living areas and gorgeous deep, intricate trim! Fantastic open floor plan encompasses soaring two story Great Room with walls of windows overlooking your private inground pool, extensive hardscape & terracing, your private pier with boat lift and your own Sandy Beach! Home is majestically sited in a lush culdesac in a parklike setting on the Premium site in Southwind on Eastern Bay! Ensuite Guest Bedrooms feature private waterfront balconies. Main level vast Owner's Suite plus office/loft and three bedrooms and a stunning den w/built-ins upstairs that boast their own waterfront deck. Front and back stairs plus a full bath accessible from the pool at the main level. The large kitchen offers a lovely built-in banquette and a wonderful custom desk with a hutch. You will love the very generous walk in pantry, and the game room or billiard room that is adjacent to the kitchen features a second access to the waterfront porch for easy entertaining! This is an extraordinary custom home with every custom detail well thought out by an interior decorator. The exquisite two-story master's suite is a WOW! There is a superb ultra luxury marble master bath with two full walls of his and her vanities and countertops, a waterfront whirlpool (yep!), a large separate shower and his and her walk around closets. The entry is made under a full portico and lush landscaping is displayed through-out this distinguished property. This is a lavish property you won't see often.

Listed by Long & Foster Real Estate, Inc.

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$/month over payments
Federal 30-year interest rate: 3.75% last updated on Jul 11, 2019
* All Figures are estimates. Check with your bank or proposed mortgage company for actual interest rates.
This product uses the FRED® API but is not endorsed or certified by the Federal Reserve Bank of St. Louis.

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1810 Main St Chester MD 21619

MLS Number MDQA139716

  • Commercial
  • LocationType Business District
  • Address 1810 Main St
  • Year Built 2004
  • Acreage 0.96

Investor Alert!!! Here's Your Money Maker....Mini shopping center with 5 store fronts & 5 second floor apartments, fully occupied, high traffic area, low low vacancy rate, plenty of parking (paved 1 year ago), new composite/trex decking, new commercial road front signage and more... Low maintenance, public water & sewer, easy access to Route 50 & only 5 min to Bay Bridge....

Listed by Clark & Co Realty, LLC

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$/month over payments
Federal 30-year interest rate: 3.75% last updated on Jul 11, 2019
* All Figures are estimates. Check with your bank or proposed mortgage company for actual interest rates.
This product uses the FRED® API but is not endorsed or certified by the Federal Reserve Bank of St. Louis.

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0 Main St Chester MD 21619

Price$1,400,000

MLS Number 1000319486

  • Commercial
  • Address 0 Main St
  • Year Built 1987
  • Acreage 2
  • Property SubType Office

Offering an opportunity to buy two acres of Town Center (TC) zoned land with frontage. Approximately one acre of the property is improved with 8,126 square feet of 100% occupied professional office and retail uses, leaving one acre for immediate development. In whole or in part, the site is well suited to the myriad uses that will be spawned in the area surrounding Four Seasons at Kent Island.

Listed by SVN/Miller Commercial Real Estate

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$
%
$/month over payments
Federal 30-year interest rate: 3.75% last updated on Jul 11, 2019
* All Figures are estimates. Check with your bank or proposed mortgage company for actual interest rates.
This product uses the FRED® API but is not endorsed or certified by the Federal Reserve Bank of St. Louis.

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2838 Cox Neck Rd Chester MD 21619

Price$1,399,999

Est. Mortgage: $/month

MLS Number 1002054676

  • Single Family
  • LocationType Creek/Stream
  • Address 2838 Cox Neck Rd
  • Bathroom 4
  • Bedrooms 4

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 by RE/MAX Executive

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$
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$/month over payments
Federal 30-year interest rate: 3.75% last updated on Jul 11, 2019
* All Figures are estimates. Check with your bank or proposed mortgage company for actual interest rates.
This product uses the FRED® API but is not endorsed or certified by the Federal Reserve Bank of St. Louis.

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228 Bentons Pleasure Rd Chester MD 21619

Price$1,199,000

Est. Mortgage: $/month

MLS Number MDQA137238

  • Single Family
  • Bathroom 4
  • Bedrooms 4
  • Square Feet 3519
  • Year Built 2005

This artfully designed 4 bedroom, 3.5 bathroom residence 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 by TTR Sotheby's International Realty

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$
%
$/month over payments
Federal 30-year interest rate: 3.75% last updated on Jul 11, 2019
* All Figures are estimates. Check with your bank or proposed mortgage company for actual interest rates.
This product uses the FRED® API but is not endorsed or certified by the Federal Reserve Bank of St. Louis.

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2813 Cox Neck Rd Chester MD 21619

Price$1,175,000

Est. Mortgage: $/month

MLS Number MDQA139390

  • Single Family
  • Address 2813 Cox Neck Rd
  • Bathroom 4
  • Bedrooms 5
  • Square Feet 3694

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, superior construction with 2"X 4"~ interior walls and 4"X 6" exterior walls, room for a pool (Verify with County). Far away but so close to everything you need - just 5 minutes to the Bay Bridge and 20 minutes to Annapolis, easy commute to Baltimore or DC.

Listed by RE/MAX Executive

$
$
%
$/month over payments
Federal 30-year interest rate: 3.75% last updated on Jul 11, 2019
* All Figures are estimates. Check with your bank or proposed mortgage company for actual interest rates.
This product uses the FRED® API but is not endorsed or certified by the Federal Reserve Bank of St. Louis.

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2867 Cox Neck Rd Chester MD 21619

Price$1,150,000

Est. Mortgage: $/month

MLS Number MDQA140280

  • Single Family
  • Address 2867 Cox Neck Rd
  • Bathroom 4
  • Bedrooms 3
  • Square Feet 6068

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!

Listed by A Real Estate Advantage

$
$
%
$/month over payments
Federal 30-year interest rate: 3.75% last updated on Jul 11, 2019
* All Figures are estimates. Check with your bank or proposed mortgage company for actual interest rates.
This product uses the FRED® API but is not endorsed or certified by the Federal Reserve Bank of St. Louis.

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213 Parks Rd Chester MD 21619

Price$1,150,000

Est. Mortgage: $/month

MLS Number MDQA140448

  • Single Family
  • Address 213 Parks Rd
  • Bathroom 4
  • Bedrooms 5
  • Square Feet 4000

213 Parks Road is a coastal-style custom-built waterfront home on Cox Creek with a private pier. This turn-key home, built in 2005, has a unique one-of-a-kind setting with views of local winery and protected creek. Nature enthusiasts will not be disappointed with the abundance of natural vegetation and native wildlife that surround this stunning home. Enjoy boating on the creek or take a short ride to the Bay ~ many enjoyable boating options. As you enter the two-story open foyer you are immediately greeted by the custom oak wood staircase, to the second level and the gorgeous hardwood floors. Through the foyer is the great room with an appealing open floor plan and a wall of windows to enjoy the views. The living space is accented by the marble-surround gas-fireplace that has a unique wood mantel with intricate detail. The gourmet chef~s kitchen has 42~ York Towne Maple Cabinets with copper hardware, Soapstone countertops, top-of-the-line appliances, stone kitchen sink, reverse osmosis water system, under counter lighting, tile backsplash, and HUGE waterviews. Just off the kitchen is the dining space that also enjoys big views. Down the hall is a mud room, coffee and tea room, and sitting room that is situated along the waterside of the home. The master bedroom suite is located on the other side of the living space and is truly set up for luxury with hardwood flooring, two walk-in closets, master bathroom with ceramic tile floor, double sink vanity, and linen closet, and waterviews. This room is currently being used as a home gym and shows you that the possibilities with this space are endless! Also on this level is a living room, just off the foyer, and a half bathroom. The upper level of the home has three bedrooms that share a full bathroom. There is also a separate in-law apartment suite that is currently set up as a Master Bedroom wing. This space can be accessed from inside the home but also has an outdoor entrance option. There is a full kitchen with eat-in dining space, living space, laundry room, separate heating and air conditioning system, a private full bathroom and spacious bedroom. The natural light in this space is abundant and the views are expansive and since this space connects to the main home through one of the upper level bedrooms, you could easily make this a 2 bedroom apartment. There are so many ~extras~ that you will notice as you tour this amazing home. There is custom crown and chair moldings, nine foot ceilings on first floor, covered waterside deck, extensive hardscaping, 10,000lb boat lift, jet-ski lift, and so much more. The attached two-car garage has stair accessible upper level storage in addition to the pull down attic space that is floored and the storage shed. Some of the details that you may not see are the 50 year Timberline Architectural roof, insulated vinyl siding, whole house commercial water treatment system, encapsulated crawl space with sump pump and breathtaking sunsets.

Listed by Long & Foster Real Estate, Inc.

$
$
%
$/month over payments
Federal 30-year interest rate: 3.75% last updated on Jul 11, 2019
* All Figures are estimates. Check with your bank or proposed mortgage company for actual interest rates.
This product uses the FRED® API but is not endorsed or certified by the Federal Reserve Bank of St. Louis.

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200 Drake Ln Chester MD 21619

Price$1,050,000

Est. Mortgage: $/month

Pending

MLS Number MDQA140312

  • Single Family
  • Address 200 Drake Ln
  • Bathroom 4
  • Bedrooms 4
  • Square Feet 3839

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.

Listed by Benson & Mangold, LLC

$
$
%
$/month over payments
Federal 30-year interest rate: 3.75% last updated on Jul 11, 2019
* All Figures are estimates. Check with your bank or proposed mortgage company for actual interest rates.
This product uses the FRED® API but is not endorsed or certified by the Federal Reserve Bank of St. Louis.

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328 Benton Pleasure Rd Chester MD 21619

Price$939,000

Est. Mortgage: $/month

Open House

MLS Number MDQA140316

  • Single Family
  • Next Open House: Sat 20th 11:00 am - 1:00 pm
  • LocationType Creek/Stream
  • Bathroom 3
  • Bedrooms 3

***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!

Listed by Coldwell Banker Waterman Realty

$
$
%
$/month over payments
Federal 30-year interest rate: 3.75% last updated on Jul 11, 2019
* All Figures are estimates. Check with your bank or proposed mortgage company for actual interest rates.
This product uses the FRED® API but is not endorsed or certified by the Federal Reserve Bank of St. Louis.

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Copyright 2019 BRIGHT, All Rights Reserved.  Information Deemed Reliable But Not Guaranteed. The data relating to real estate for sale on this website appears in part through the BRIGHT Internet Data Exchange program, a voluntary cooperative exchange of property listing data between licensed real estate brokerage firms in which Chuck Mangold participates, and is provided by BRIGHT through a licensing agreement. The information provided by this website is for the personal, non-commercial use of consumers and may not be used for any purpose other than to identify prospective properties consumers may be interested in purchasing.Data last updated July 16, 2019. Some properties which appear for sale on this website may no longer be available because they are under contract, have Closed or are no longer being offered for sale.

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