Chester, Maryland Homes For Sale & Real Estate

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Real Estate Homes For Sale In Chester, MD

Welcome to Bayside  Condos where luxury meets affordability on Kent Island. This 2 bedroom, 2 bath villa home offers over 1,000 sq ft of single level living, 2 balconies with expansive views above the trees, large rooms and lots of closets.  A new....

CHESTER Homes |

MLS #MDQA2009758

Condominium

$269,900 | Active Home listing

2 Beds | 2 Baths | 1,069 Sqft | 0 Acres Lot

115 BUFFLEHEAD COURT, 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

$940,000 | 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
Discover the perfect blend of beachy charm and modern convenience with this 2-bedroom, 1.5-bathroom condo located in the popular waterfront community of Queens Landing. Boasting 1,104 square feet of thoughtfully designed living space on the second....

CHESTER Homes |

MLS #MDQA2009686

Condominium

$337,500 | Active Home listing

2 Beds | 2 Baths | 1,104 Sqft | 0 Acres Lot

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

Condo Unit Details & Photos
Hurry...Priced right and huge bedrooms!  4 Brs, 2.5 Baths, home backs to tree in sought-after community..

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
*OPEN HOUSE 5/19/2024 12-3:00pm* Direct waterfront on the Chester River,  505 Swan Cove Ln presents an exquisite first floor,  west facing retreat offering the perfect blend of elegance, comfort, and natural beauty. This captivating property....

CHESTER Homes |

MLS #MDQA2009694

Condominium

$600,000 | Active Home listing

2 Beds | 2 Baths | 1,990 Sqft | 0 Acres Lot

505 SWAN COVE LANE, CHESTER, MD 21619 QUEEN ANNES County

Condo Unit Details & Photos
Why Wait to Build Your Dream Home?
This is located in Phase 1 of the development, which is complete.
No Thru Traffic. No Construction Noise.
You WILL NOT have to spent thousands of dollars on the following upgrades. We already have them!
Luxury....

CHESTER Homes |

MLS #MDQA2009672

Single Family Residence

$819,000 | Active Home listing

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

224 SALTWORKS DRIVE, CHESTER, MD 21619 QUEEN ANNES County

Real Estate Details & Photos
Welcome to Bayside luxury living at its finest! This stunning three-bedroom townhome offers the perfect blend of elegance and convenience. 
Inside, you'll find a spacious light filled main level with an open floating staircase, a large living area....

CHESTER Homes |

MLS #MDQA2009450

Condominium

$345,900 | Active Home listing

3 Beds | 3 Baths | 1,788 Sqft | 0 Acres Lot

305 SCHOONER WAY, CHESTER, MD 21619 QUEEN ANNES County

Condo Unit Details & Photos
This is an outstanding opportunity for anyone looking for a peaceful escape to an idyllic island lifestyle this summer. The beautiful condo is located in the renowned

CHESTER Homes |

MLS #MDQA2009540

Condominium

$649,900 | Active Home listing

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

4000 HERONS NEST WAY, CHESTER, MD 21619 QUEEN ANNES County

Condo Unit Details & Photos
A small but mighty space that gives you everything you need living room, Kitchen, bathroom, primary bedroom, outdoor living storage and closet to store.
A delightful condo nestled in a waterfront community with a plethora of amenities. The....

CHESTER Homes |

MLS #MDQA2009434

Condominium

$215,000 | Active Home listing

1 Beds | 1 Baths | 724 Sqft | 0 Acres Lot

3 QUEEN VICTORIA COURT, CHESTER, MD 21619 QUEEN ANNES County

Condo Unit 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

$585,000 | 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
$25,000 Price improvement! The perfect opportunity to enjoy waterfront living in your full time residence or vacation home. Light filled contemporary with vaulted ceilings and loads of windows offering water views of Crab Alley Bay. Relax on the....

CHESTER Homes |

MLS #MDQA2008932

Single Family Residence

$724,900 | Active Home listing

2 Beds | 2 Baths | 1,971 Sqft | 1 Acres Lot

1308 SAINT MARYS ROAD, CHESTER, MD 21619 QUEEN ANNES County

Real Estate 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
Experience the ease of low-maintenance living and the relaxation of a vacation getaway in this stunning 1,440 sqft, 2-bedroom, 2.5-bathroom townhome in the coveted water-privileged community of Queens Landing on Kent Island. Tucked away at Lake....

CHESTER Homes |

MLS #MDQA2009306

Townhouse

$377,500 | Active Home listing

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

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

Townhouse Details & Photos
Wonderful and well maintained home in Gibson's Grant. This 3 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 the Chester River and Macum Creek.  There is a....

CHESTER Homes |

MLS #MDQA2009220

Single Family Residence

$699,900 | Active Home listing

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

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

Real Estate 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!! This 2 bed, 2.5 bath townhome located in the charming Waterfront community of Queens Landing on Kent Island offers low-maintenance, affordable living and....

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
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+337111831

Townhouse

$1,115,000 | Active Home listing

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

224 Switchgrass Way, Unit 31, Chester, MD 21619

Townhouse 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! Immediate Delivery!!! Shows Like a Model!!! The Severn design is a spacious....

CHESTER Homes |

MLS #MDQA2008690

Condominium

$689,700 | 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
PRICE IS FOR BOTH 1007 AND 1009 DOMINION ROAD TO MAKE OVER AN ACRE OF WATERFRONT!

Call  your builder, draw up plans, and make this  waterfront lot your little piece of paradise! It’s  a  boaters dream with a large pier on Kirwins Creek 3ft  MLW....

CHESTER Homes |

MLS #MDQA2008770

Single Family Residence

$399,987 | Active Home listing

2 Beds | 1 Baths | 832 Sqft | 1 Acres Lot

1007 DOMINION ROAD, CHESTER, MD 21619 QUEEN ANNES County

Real Estate 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
Brand new septic system (2023) New Roof (2022) Home is being sold as-is.  ***See uploaded documents for information on potential for marsh boardwalk/pier***Escape to your private waterfront oasis on 16+ acres on Kent Island. Sitting at the mouth....

CHESTER Homes |

MLS #MDQA2008288

Single Family Residence

$985,000 | Active Home listing

3 Beds | 3 Baths | 0 Sqft | 16 Acres Lot

121 GUNNERS REST LN, CHESTER, MD 21619 QUEEN ANNES County

Real Estate Details & Photos
Move in Ready Townhome in the waterfront, amenity rich community of Queens Landing!  This two bedroom, 2- and one-half bath home is ready for new owners! The main level offers a family room w/gas fireplace, kitchen with granite counters, a living....

CHESTER Homes |

MLS #MDQA2008282

Condominium

$349,000 | Active Home listing

2 Beds | 3 Baths | 1,312 Sqft | 0 Acres Lot

45 QUEEN NEVA 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+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

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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