Chester, Maryland Homes For Sale & Real Estate

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Real Estate Homes For Sale In Chester, MD

*Open House Saturday 6/29 from 1 to 3pm and Sunday 6/30 from 10am-12pm*  Nestled in the desired Waterfront privileged Neighborhood of Marling Farms , this stunning 4 BR (w/Main Level Primary), 2 BA, 2-level Coastal Home epitomizes modern luxury....

CHESTER Homes |

MLS #MDQA2010024

Single Family Residence

$569,000 | Active Home listing

4 Beds | 2 Baths | 2,208 Sqft | 0 Acres Lot

1600 CHESTER ROAD, CHESTER, MD 21619 QUEEN ANNES County

Real Estate Details & Photos
FABULOUS renovations on this gorgeous  3 bedroom, 2 bath home. Hardwood floors thru out, New carpet in the office. Lovely galley kitchen with stainless appliances, ceramic backsplash and leathered granite counters. Updated bathes with designer....

CHESTER Homes |

MLS #MDQA2010100

Single Family Residence

$589,900 | Active Home listing

3 Beds | 2 Baths | 0 Sqft | 0 Acres Lot

1303 SAINT MARYS DRIVE RD #1303, CHESTER, MD 21619 QUEEN ANNES County

Real Estate Details & Photos
Welcome to Four Seasons at Kent Island resort living at its finest, where unparalleled active living meets luxury and convenience. This premier community offers resort-style amenities, including a swimming pool, tennis and pickleball courts, and....

CHESTER Homes |

MLS #MDQA2010046

Apartment

$549,000 | Active Home listing

2 Beds | 3 Baths | 2,003 Sqft | 0 Acres Lot

2000 HERONS NEST WAY, CHESTER, MD 21619 QUEEN ANNES County

Apartment Details & Photos
Welcome to 105 Pilot Ct. in Chester, MD! Located within the sought after community of Castle Marina, this wonderfully updated and renovated 5 bedroom, 3 full bath split level home features 5 bedrooms offers a blend of serene suburban living with....

CHESTER Homes |

MLS #MDQA2010004

Single Family Residence

$570,000 | Active Home listing

5 Beds | 3 Baths | 2,726 Sqft | 1 Acres Lot

105 PILOT COURT, CHESTER, MD 21619 QUEEN ANNES County

Real Estate Details & Photos
**Wonderful Waterfront Town Home w/out the High Taxes**Three Full Levels of Living on the Chester River!**Open Lower Level has the Living Room Facing the Water**Updated Kitchen w/Granite Counters and SS Appliances**Double Oven and Gas Cook....

CHESTER Homes |

MLS #MDQA2010022

Condominium

$595,000 | Active Home listing

4 Beds | 4 Baths | 0 Sqft | 0 Acres Lot

1006 AUCKLAND WAY, CHESTER, MD 21619 QUEEN ANNES County

Condo Unit Details & Photos
Located in the amenity rich Four Seasons at Kent Island, this ORIGINAL-OWNER property has been meticulously taken care of with many special, unique additions having been made!  An open concept great room introduces a decorator neutral paint....

CHESTER Homes |

MLS #MDQA2010014

Single Family Residence

$875,000 | Active Home listing

3 Beds | 3 Baths | 0 Sqft | 0 Acres Lot

171 SPINNAKER WAY, CHESTER, MD 21619 QUEEN ANNES County

Real Estate Details & Photos
OPEN HOUSE, Sat, June 29 from 2:30 - 4 pm...Welcome to your dream home! Nestled in a charming community, this exquisite 5-bedroom sanctuary boasts luxurious features and thoughtful design elements, ensuring comfort and elegance at every turn.

As....

CHESTER Homes |

MLS #MDQA2009856

Single Family Residence

$650,000 | Active Home listing

5 Beds | 3 Baths | 3,103 Sqft | 0 Acres Lot

1326 QUEEN ANNE DRIVE, CHESTER, MD 21619 QUEEN ANNES County

Real Estate Details & Photos
Imagine waking up every day in a home that combines the ease of low-maintenance living with the relaxation of a vacation getaway. This dream can become your reality with this stunning 1,440 sqft, 2-bedroom, 2.5-bathroom townhome nestled in the....

CHESTER Homes |

MLS #MDQA2009956

Condominium

$364,900 | Active Home listing

2 Beds | 3 Baths | 1,440 Sqft | 0 Acres Lot

37 QUEEN ANNE WAY, CHESTER, MD 21619 QUEEN ANNES County

Condo Unit Details & Photos
TONS OF EQUITY!!! SELLER IS HIGHLY MOTIVATED!!

Wonderful and well maintained home in Gibson's Grant. This 3/4 Bedroom, 3 Full Bath with Loft Home is 5 Minutes off of Route 50 but has a resort lifestyle.  The Community is located on the shores of....

CHESTER Homes |

MLS #MDQA2009908

Single Family Residence

$599,900 | Active Home listing

4 Beds | 3 Baths | 2,464 Sqft | 0 Acres Lot

104 JOHN GIBSON DRIVE, CHESTER, MD 21619 QUEEN ANNES County

Real Estate Details & Photos
This beautiful Bayside waterfront boasts an open floor plan with gorgeous views. Some of the wonderful highlights include a spacious granite  kitchen, living room with built-ins, hardwood floors and garage. Master bedroom has walk-in closet and....

CHESTER Homes |

MLS #MDQA2009726

Condominium

$579,950 | Active Home listing

3 Beds | 4 Baths | 2,172 Sqft | 0 Acres Lot

703 BLENNY LANE, CHESTER, MD 21619 QUEEN ANNES County

Condo Unit Details & Photos
Welcome to your dream retreat in the heart of a vibrant bayside community! This stunning three-level villa offers breathtaking views of the serene Chester River, ensuring a tranquil ambiance throughout. Step inside to discover a modern haven....

CHESTER Homes |

MLS #MDQA2008972

Condominium

$475,000 | Active Home listing

3 Beds | 4 Baths | 2,112 Sqft | 0 Acres Lot

603 AUCKLAND WAY, CHESTER, MD 21619 QUEEN ANNES County

Condo Unit Details & Photos
Absolutely impeccable 4 bedroom plus office home in the water access community of Gibson’s Grant with outdoor living space including front porch, rear deck and paver patio.  Recently remodeled and upgraded with high-end appliances and finishes....

CHESTER Homes |

MLS #MDQA2009768

Single Family Residence

$895,000 | Active Home listing

4 Beds | 3 Baths | 2,856 Sqft | 0 Acres Lot

239 CLAIBORNE STREET, CHESTER, MD 21619 QUEEN ANNES County

Real Estate Details & Photos
OPEN HOUSE, Sat, June 29 from 10-11:30am Wow! Priced to Sell!! Situated in a picturesque community known for its manicured yards and welcoming atmosphere, this attractive colonial home with a 2-car garage features 4 oversized bedrooms and 2.5....

CHESTER Homes |

MLS #MDQA2009522

Single Family Residence

$555,000 | Active Home listing

4 Beds | 3 Baths | 2,356 Sqft | 0 Acres Lot

518 CROSS CREEK COURT, CHESTER, MD 21619 QUEEN ANNES County

Real Estate Details & Photos
WELCOME HOME TO FOUR SEASONS - KENT ISLAND. This magnificent condo property offers turn-key luxury and a serene resort lifestyle in one of the fastest growing desired communities on the Eastern Shore of Maryland. The meticulousy maintained 2nd....

CHESTER Homes |

MLS #MDQA2009632

Condominium

$599,900 | Active Home listing

2 Beds | 3 Baths | 1,900 Sqft | 0 Acres Lot

3000 HERONS NEST WAY, CHESTER, MD 21619 QUEEN ANNES County

Condo Unit Details & Photos
Why Wait to Build Your Dream Home! This Kent Island Home in Four Seasons is available immediately.
Yard Maintenance included in HOA. 
You WILL NOT have to spend THOUSANDS of dollars on the following upgrades. We already have them!
Luxury Spa Bath,....

CHESTER Homes |

MLS #MDQA2009672

Single Family Residence

$798,500 | Active Home listing

3 Beds | 2 Baths | 2,597 Sqft | 0 Acres Lot

224 SALTWORKS DRIVE, CHESTER, MD 21619 QUEEN ANNES County

Real Estate Details & Photos
Welcome to your dream waterfront retreat! This exquisite 3-level, 3-bedroom, 2.5-bathroom condo offers breathtaking water views from every window.  Enjoy your days and nights overlooking the boating acitivty from the marina and Chester River.....

CHESTER Homes |

MLS #MDQA2009338

Condominium

$579,000 | Active Home listing

3 Beds | 3 Baths | 1,680 Sqft | 0 Acres Lot

23 QUEEN VICTORIA WAY, CHESTER, MD 21619 QUEEN ANNES County

Condo Unit Details & Photos
K Hovnanian's Four Seasons at Kent Island is an active 55+ community on Maryland's Chesapeake Bay, offering island resort-style and maintenance-free living at its finest! Shows Like a Model!!! The Severn design is a spacious and airy 3 bedroom,....

CHESTER Homes |

MLS #MDQA2009170

Condominium

$736,000 | Active Home listing

3 Beds | 3 Baths | 2,600 Sqft | 0 Acres Lot

141 SWITCHGRASS WAY, CHESTER, MD 21619 QUEEN ANNES County

Condo Unit Details & Photos
Welcome home to island living in this great three bedroom two full and two half bath townhouse with a garage. Walk in from the front door or garage to new LVP flooring downstairs, a fine family room to the back with a slider to the patio, a half....

CHESTER Homes |

MLS #MDQA2009354

Condominium

$385,000 | Active Home listing

3 Beds | 4 Baths | 0 Sqft | 0 Acres Lot

206 BLENNY LN, CHESTER, MD 21619 QUEEN ANNES County

Condo Unit Details & Photos
This house is large and in charge, over 3900 sq feet and 3 levels of living space and it is waiting for new owners. From the spacious kitchen with granite counters, tons of cabinets, downdraft stove, and  separate formal dining room. *Corner lot....

CHESTER Homes |

MLS #MDQA2009136

Single Family Residence

$749,989 | Active Home listing

5 Beds | 5 Baths | 3,900 Sqft | 1 Acres Lot

203 SKIPPER LANE, CHESTER, MD 21619 QUEEN ANNES County

Real Estate Details & Photos
With this MAJOR PRICE IMPROVEMENT, you can save even more while adding your personal touch!! Make an Offer!! This 2 bed, 2.5 bath townhome located in the charming Waterfront community of Queens Landing on Kent Island offers low-maintenance,....

CHESTER Homes |

MLS #MDQA2009022

Condominium

$319,000 | Active Home listing

2 Beds | 3 Baths | 1,280 Sqft | 0 Acres Lot

53 QUEEN CAROLINE COURT, CHESTER, MD 21619 QUEEN ANNES County

Condo Unit Details & Photos
Open floorplan with plenty of room for your family. Wonderful gourmet kitchen and formal dining area. Private home office for your personal space. Large great room off balcony with large windows to capture the day. Luxurious owners suite with spa....

Chester Townhome |

MLS #337070000+337111842

Townhouse

$1,004,000 | Active Home listing

2 Beds | 3 Baths | 1,900 Sqft | 0 Acres Lot

224 Switchgrass Way, Unit 42, Chester, MD 21619

Townhouse Details & Photos
Open floorplan with plenty of room for your family. Wonderful gourmet kitchen and formal dining area. Private home office for your personal space. Large great room off balcony with large windows to capture the day. Luxurious owners suite with spa....

Chester Townhome |

MLS #337070000+337111843

Townhouse

$1,006,000 | Active Home listing

2 Beds | 3 Baths | 1,900 Sqft | 0 Acres Lot

224 Switchgrass Way, Unit 43, Chester, MD 21619

Townhouse Details & Photos
Why wait for new home to be built. Immediate occupancy for this popular Severn model. Price reduced for quick sale.  No steps. No exterior maintenance. One car garage. Plenty of additional parking.
Designer light fixtures, custom window....

CHESTER Homes |

MLS #MDQA2008690

Condominium

$677,600 | Active Home listing

3 Beds | 3 Baths | 2,600 Sqft | 0 Acres Lot

3000 HERONS NEST WAY, CHESTER, MD 21619 QUEEN ANNES County

Condo Unit Details & Photos
Expansive end home condominium with 3 bedrooms. Lavish gourmet kitchen and formal dining area. Huge great room with large corner balcony. Fantastic owners suite and sitting room with access to balcony. Extravagant owners spa bath with two walk-in....

Chester Townhome |

MLS #337070000+337152021

Townhouse

$899,900 | Active Home listing

3 Beds | 3 Baths | 2,602 Sqft | 0 Acres Lot

129 Wheelhouse Way, Unit 21, Chester, MD 21619

Townhouse Details & Photos
Open airy floorplan on the first floor with private patio. Large gourmet kitchen and dining area, great for entertaining. Wonderful home office for your telecommuting needs. Sumptuous owners suite with spa bath . Fantastic great room with large....

Chester Townhome |

MLS #337070000+337152011

Townhouse

$709,900 | Active Home listing

2 Beds | 3 Baths | 2,003 Sqft | 0 Acres Lot

129 Wheelhouse Way, Unit 11, Chester, MD 21619

Townhouse Details & Photos
Wow!  A Waterfront with one floor living under $900k!  Crab Alley Bay on Kent Island offers stunning views of wildlife, including ducks, swans, and geese. The residence showcases an open floor plan with over 2,000 sf and three distinct living....

CHESTER Homes |

MLS #MDQA2008458

Single Family Residence

$829,000 | Active Home listing

3 Beds | 2 Baths | 2,000 Sqft | 0 Acres Lot

1518 SAINT MARYS ROAD, CHESTER, MD 21619 QUEEN ANNES County

Real Estate Details & Photos
Open floorplan with plenty of room for your family. Wonderful gourmet kitchen and formal dining area. Private home office for your personal space. Large great room off balcony with large windows to capture the day. Luxurious owners suite with spa....

Chester Townhome |

MLS #337070000+337111623

Townhouse

$589,900 | Active Home listing

2 Beds | 3 Baths | 1,900 Sqft | 0 Acres Lot

212 Switchgrass Way, Unit 23, Chester, MD 21619

Townhouse Details & Photos
Secluded bedroom 2 & bath off foyer for overnight guests. Stylish home office off foyer for working from home. Open & airy great room with adjacent dining area. Striking kitchen with island & tons of cabinet space. Luxurious primary suite with....

Chester Homes |

MLS #337020000+A865

Single Family Residence

$685,900 | Active Home listing

2 Beds | 2 Baths | 2,041 Sqft | 0 Acres Lot

131 Flycatcher Way, Chester, MD 21619

Real Estate Details & Photos
Formal dining room off foyer for entertaining guests. Stylish kitchen with plenty of cabinet space and large island. Open and airy great room with slider to covered patio. Luxurious primary suite with triple windows. Private primary bath with....

Chester Homes |

MLS #337020000+B225

Single Family Residence

$789,900 | Active Home listing

3 Beds | 4 Baths | 2,963 Sqft | 0 Acres Lot

131 Flycatcher Way, Chester, MD 21619

Real Estate Details & Photos
Extra Suite Plus for multi-generational living. Striking kitchen with large center island and corner pantry. Spacious great room with tons of windows for natural sun light. Luxurious primary suite with oversized walk-in closet. Relaxing primary....

Chester Homes |

MLS #337020000+D134

Single Family Residence

$814,900 | Active Home listing

4 Beds | 4 Baths | 3,570 Sqft | 0 Acres Lot

131 Flycatcher Way, Chester, MD 21619

Real Estate Details & Photos
Private home office off foyer for working from home. Formal dining room off foyer for entertaining guests. Open and airy floorplan with spacious great room. Striking kitchen with large center island. Luxurious primary suite with oversized walk-in....

Chester Homes |

MLS #337020000+D135

Single Family Residence

$817,900 | Active Home listing

4 Beds | 4 Baths | 3,472 Sqft | 0 Acres Lot

131 Flycatcher Way, Chester, MD 21619

Real Estate Details & Photos
Extra Suite with full bath for overnight guests. Private home office off foyer for working from home. Spacious great room with adjacent dining area. Beautiful kitchen with large center island. Luxurious primary suite with oversized walk-in closet.....

Chester Homes |

MLS #337020000+D192

Single Family Residence

$781,900 | Active Home listing

5 Beds | 5 Baths | 3,210 Sqft | 0 Acres Lot

131 Flycatcher Way, Chester, MD 21619

Real Estate Details & Photos
Extra Suite perfect for overnight guests. Private home office off foyer for working from home. Spacious great room with slider to covered patio. Stylish kitchen with island and large pantry. Luxurious primary suite with triple windows. Relaxing....

Chester Homes |

MLS #337020000+D228

Single Family Residence

$752,900 | Active Home listing

3 Beds | 3 Baths | 2,809 Sqft | 0 Acres Lot

131 Flycatcher Way, Chester, MD 21619

Real Estate Details & Photos
Private bedroom 2 located off foyer for overnight guests. Striking kitchen with large island and plenty of counter space. Open and airy great room with slider to covered patio. Convenient covered patio with screened patio option. Luxurious primary....

Chester Homes |

MLS #337020000+D237

Single Family Residence

$666,900 | Active Home listing

4 Beds | 3 Baths | 2,791 Sqft | 0 Acres Lot

131 Flycatcher Way, Chester, MD 21619

Real Estate Details & Photos
Private home office for working from home. Spacious great room with slider to covered patio. Beautiful kitchen with large island and roomy pantry. Luxurious primary suite with triple windows. Relaxing primary bath with spacious shower and walk-in....

Chester Homes |

MLS #337020000+D238

Single Family Residence

$707,900 | Active Home listing

2 Beds | 2 Baths | 2,166 Sqft | 0 Acres Lot

131 Flycatcher Way, Chester, MD 21619

Real Estate Details & Photos
Elegant foyer welcoming guests to your home. Convenient single-story living. Kitchen with spacious pantry and oversized island. Open-concept great room and dining area adjacent to kitchen. Private primary suite with large walk-in closet and spa....

Chester Homes |

MLS #337020000+D262

Single Family Residence

$601,900 | Active Home listing

2 Beds | 2 Baths | 1,693 Sqft | 0 Acres Lot

131 Flycatcher Way, Chester, MD 21619

Real Estate Details & Photos
Private home office for working from home. Stylish kitchen with large center island and spacious pantry. Spacious great room with slider to covered patio. Luxurious primary suite with oversized walk-in closet. Palatial primary bath with split....

Chester Homes |

MLS #337020000+D263

Single Family Residence

$631,900 | Active Home listing

2 Beds | 2 Baths | 1,996 Sqft | 0 Acres Lot

131 Flycatcher Way, Chester, MD 21619

Real Estate Details & Photos
Open floorplan with plenty of room for your family. Wonderful gourmet kitchen and formal dining area. Private home office for your personal space. Large great room off balcony with large windows to capture the day. Luxurious owners suite with spa....

Chester Townhome |

MLS #337070000+B796

Townhouse

$459,990 | Active Home listing

2 Beds | 3 Baths | 1,900 Sqft | 0 Acres Lot

131 Flycatcher Way, Chester, MD 21619

Townhouse Details & Photos
Open airy floorplan on the first floor with private patio. Large gourmet kitchen and dining area, great for entertaining. Wonderful home office for your telecommuting needs. Sumptuous owners suite with spa bath . Fantastic great room with large....

Chester Townhome |

MLS #337070000+B797

Townhouse

$459,990 | Active Home listing

2 Beds | 3 Baths | 2,003 Sqft | 0 Acres Lot

131 Flycatcher Way, Chester, MD 21619

Townhouse Details & Photos

Chester, MD Real Estate Home Trends

Queen Anne's County Buy Statistics

  • Total Housesolds
  • 19,351
  • Median Home Value
  • $421,900
  • Median Housing Costs
  • $2,365
  • Median Household Income
  • $108,332
  • Median Real Estate Taxes
  • $Not Available
  • Homes With Primary Mortgage Only
  • Not Available%
    • Homes With Second Mortgage
    • Not Available%
    • Homes With Home Equity Mortgage Only
    • Not Available%

    Chester Types of Homes for Sale

    Chester Real Estate Listings

    Chester, MD Homes Prices

    • Total Housesolds
    • 19,351
    • Median Home Value
    • $411,900
    • Median Housing Costs
    • $2,097
    • Median Household Income
    • $94,991
    • Average Household Income
    • $125,876
    • Median Real Estate Taxes
    • $3,857
    • Homes With Primary Mortgage Only
  • 86.9%
    • Homes With Second Mortgage
    • 10.6%
    • Homes With Home Equity Mortgage Only
    • 2.5%
    • Total Population
    • 6,164,660
    • Median Age
    • 39.7
    • Male To Female Ratio
    • 95.1
    • Average Household Size
    • 2.76
    • Median Rent For House
    • $1,550
    • Owner-Occupied House Units
    • 67.7%
    • Renters Occupied House Units
    • 32.3%

    Real Estate Home Mortgage Loan Rates Chester Maryland

    Home loan finance mortgage calculator to find Maryland real estate payment calculations

    Housing Calculator Affordability

    About Chester

    • Chester has total households of 19,351 with a real estate for sale median home value of $421,900 compared to the state median home price of $411,900. The median real estate taxes paid are $Not Available and the household income is $108,332. Not Available% of Chester homes with a mortgage have no second mortgage or home equity line of credit. Chester Maryland home types of MLS housing to buy including single family homes, condos, townhomes, residential studio, apartment, townhouse, and multi-family houses.

    Chester Neighborhoods

    What Zip Codes in Chester have homes for sale listing?

    City neighborhood housing zip codes have MLS listing homes for sale within Chester, MD for buyers: 21619, 21666.

    Chester Local Economy & Job Opportunities

    The median household income is 108,332 and the median state household income is 94,991. The average household income is 125,876 in Maryland.

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