Chester, MD homes for sale & real estate

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ABOUT THIS HOME
Chester, MD Homes for Sale
Professional pictures coming! This roomy 2 bedroom, 2.5 bathroom end unit has been completely painted in a beautiful neutral shade and has new carpet throughout, as will be getting new flooring in the kitchen. A propane fireplace highlights the great room for cozy chilly nights! On warm days, enjoy relaxing in the enclosed patio/porch or just being outside. Being an end-unit it offers lots of privacy. Any and all assessments have been paid by the owner, so you are ready to go and to enjoy all the amenities that Queens Landing is known for. .. beautiful waterside pool, the club house with a party room, racquet ball court, exercise room, tennis courts, jogging trail, and more! Close to the cr

$349,000

2 beds2 baths1,280 sq ft

54-H Queen Caroline Ct, Chester, MD 21619

$505 HOA • Community pool • Built 1998

(410) 643-2244

ABOUT THIS HOME
Chester, MD Homes for Sale
Start the New Year as a resident of Gibson’s Grant! Discover over 4,100 sq. ft. of high-end, custom elegance in this exceptional Eastern Shore home—perfectly located in one of Chester’s most sought-after waterfront communities. With 6 bedrooms, 4.5 baths, and designer touches at every turn, this residence offers the space, craftsmanship, and lifestyle today’s buyers crave. Step inside the welcoming foyer and take in the three-story staircase, striking wrought-iron railings, and extensive architectural details including wainscoting, custom trim, and three-piece crown molding throughout. Rich hand-scraped wide-plank hardwoods lead you through thoughtfully designed spac

$915,000

6 beds4.5 baths4,165 sq ft

109 John Gibson Dr, Chester, MD 21619

7,500 sq ft lot • 3 garage spots • Community pool

(410) 224-2200

ABOUT THIS HOME
Chester, MD Homes for Sale
Discover a true waterfront treasure on . 54 acres with 110 feet of waterfront. This beautifully renovated 3-bedroom, 2.5 bath home offers an open-concept layout design to capture breathing taking water views that stretch endless across the horizon. Each evening brings magnificent, direct sunset views-- the kind that make you stop, breathe, and take it all in. New pier in 2020! Step inside to luxury plank flooring that flows throughout the home, complementing a bright, modern kitchen outfitted with brilliant white quartz countertops, all new stainless steel appliances, abundant white cabinetry, and generous workspace ideal for cooking and entertaining. The refined design continues into each

$1,100,000

3 beds2.5 baths1,830 sq ft

1704 Bayside Dr, Chester, MD 21619

0.54 acre lot • 2 garage spots • Built 1973

(703) 242-0005

ABOUT THIS HOME
Chester, MD Homes for Sale
WATERFRONT !!! Spectacular sunrise views on display over the Chester River from this cozy 1 bedroom, 1 bath condo in the popular community of Queens Landing. Known for its amenities, you are sure to enjoy living here whether as a full-time resident or just to have as a week-end getaway! Minutes from the Bay Bridge, you can be here without ever getting on route 50! Amenities are as follows: tennis courts, waterside pool, jogging path with easy access to the cross-island running/bike trail, racquet ball court, fitness center and more!! There is also a party room that you can use when you need more room to entertain guests! This condo unit has a very low condo fee of $189 per month! Not many o

$330,000

1 bed1 bath724 sq ft

10-B Queen Elizabeth Ct, Chester, MD 21619

$189 HOA • Community pool • Built 1983

(410) 643-2244

ABOUT THIS HOME
Chester, MD Homes for Sale
Exceptional value for this renovated 3-bedroom, 3.5-bath end-unit townhome in the premier Bayside waterfront community. Comparable properties in this Chester River community have recently sold for much more, making this an outstanding opportunity for buyers seeking turnkey condition with over $50,000 in premium upgrades. Welcome to Bayside living at its finest. This meticulously maintained home sits in one of Chester's most desirable waterfront communities, offering nearby water access for morning walks along the Chester River, resort-style outdoor pool for summer enjoyment, and professionally maintained grounds. Minutes from Route 50/301 for easy commuting, yet peacefully situated in a ser

$425,000

3 beds3.5 baths2,100 sq ft

807 Auckland Way, Chester, MD 21619

$680 HOA • Garage • Community pool

(855) 450-0442

Property at 162 Kirwans Landing Ln, Chester, MD 21619, 4 beds, 2.5 baths

$869,000

4 beds2.5 baths2,404 sq ft

162 Kirwans Landing Ln, Chester, MD 21619

(410) 263-8686

Property at 2907 Cox Neck Rd E, Chester, MD 21619, 4 beds, 5 baths

$1,899,000

4 beds5 baths3,460 sq ft

2907 Cox Neck Rd E, Chester, MD 21619

(410) 280-5600

Property at 117 Flycatcher Way, Chester, MD 21619, 3 beds, 3.5 baths

$1,400,000

3 beds3.5 baths2,930 sq ft

117 Flycatcher Way, Chester, MD 21619

(240) 375-5074

Property at 111 Flycatcher Way, Chester, MD 21619, 5 beds, 4.5 baths

$1,400,000

5 beds4.5 baths3,225 sq ft

111 Flycatcher Way, Chester, MD 21619

(240) 375-5074

Property at 1839 Harbor Dr, Chester, MD 21619, 4 beds, 2 baths

$375,000

4 beds2 baths2,035 sq ft

1839 Harbor Dr, Chester, MD 21619

(301) 970-2447

Property at 1870 Harbor Dr, Chester, MD 21619, 2 beds, 1 bath

$320,000

2 beds1 bath832 sq ft

1870 Harbor Dr, Chester, MD 21619

(443) 274-1900

Property at 202 Mchenny Ct, Chester, MD 21619, 3 beds, 2.5 baths

$825,000

3 beds2.5 baths2,520 sq ft

202 Mchenny Ct, Chester, MD 21619

(410) 224-2200

Property at 123 Flycatcher Way, Chester, MD 21619, 3 beds, 3 baths

$1,300,000

3 beds3 baths2,789 sq ft

123 Flycatcher Way, Chester, MD 21619

(240) 375-5074

Property at 1916 Stevens Dr, Chester, MD 21619, 3 beds, 2 baths

$495,000

3 beds2 baths1,728 sq ft

1916 Stevens Dr, Chester, MD 21619

(410) 224-2200

Property at 306 Teal Ct Unit C, Chester, MD 21619, 2 beds, 2 baths

$295,000

2 beds2 baths1,073 sq ft

306 Teal Ct Unit C, Chester, MD 21619

(410) 451-3300

Property at 203 Riverside Dr, Chester, MD 21619, 5 beds, 3.5 baths

$1,099,900

5 beds3.5 baths3,036 sq ft

203 Riverside Dr, Chester, MD 21619

(301) 945-9010

Property at 527 Warbler Way, Chester, MD 21619, 3 beds, 3 baths

$799,990

3 beds3 baths2,789 sq ft

527 Warbler Way, Chester, MD 21619

(240) 375-5074

Property at 127 Flycatcher Way, Chester, MD 21619, 2 beds, 2 baths

$1,100,000

2 beds2 baths1,993 sq ft

127 Flycatcher Way, Chester, MD 21619

(240) 375-5074

Property at 112 Chessie Ct, Chester, MD 21619, 3 beds, 2.5 baths

$519,900

3 beds2.5 baths2,066 sq ft

112 Chessie Ct, Chester, MD 21619

(443) 249-7653

Property at 30-C Queen Mary Ct, Chester, MD 21619, 2 beds, 2.5 baths

$339,900

2 beds2.5 baths1,440 sq ft

30-C Queen Mary Ct, Chester, MD 21619

(410) 255-3690

Property at 1221 Cox Nck, Chester, MD 21619, 4 beds, 2.5 baths

$519,900

4 beds2.5 baths1,482 sq ft

1221 Cox Nck, Chester, MD 21619

(855) 550-0528

Property at 906 Auckland Way, Chester, MD 21619, 3 beds, 3.5 baths

$520,000

3 beds3.5 baths2,076 sq ft

906 Auckland Way, Chester, MD 21619

(410) 673-3344

Property at 519 Warbler Way, Chester, MD 21619, 3 beds, 3 baths

$849,990

3 beds3 baths2,789 sq ft

519 Warbler Way, Chester, MD 21619

(240) 375-5074

Property at 1405 Little Creek Rd, Chester, MD 21619, 2 beds, 1 bath

$19,500

2 beds1 bath764 sq ft

1405 Little Creek Rd, Chester, MD 21619

(302) 217-6692

Property at 1906 Harbor Dr, Chester, MD 21619, 3 beds, 2 baths

$499,900

3 beds2 baths1,750 sq ft

1906 Harbor Dr, Chester, MD 21619

(240) 222-3200

Property at Harbor Dr, Chester, MD 21619, 3 beds, 2 baths

$499,900

3 beds2 baths1,250 sq ft

Harbor Dr, Chester, MD 21619

(410) 643-5005

Property at 1401 Calvert Rd, Chester, MD 21619, 2 beds, 2 baths

$454,900

2 beds2 baths1,444 sq ft

1401 Calvert Rd, Chester, MD 21619

(410) 643-5005

Property at 1757 Harbor Dr, Chester, MD 21619, 4 beds, 3.5 baths

$1,125,000

4 beds3.5 baths— sq ft

1757 Harbor Dr, Chester, MD 21619

(410) 729-7700

Property at 205 Anchor Ln, Chester, MD 21619, 6 beds, 3 baths

$535,000

6 beds3 baths3,500 sq ft

205 Anchor Ln, Chester, MD 21619

(443) 274-1900

Property at 201 Golden Eye Ct, Chester, MD 21619, 2 beds, 2 baths

$285,000

2 beds2 baths1,073 sq ft

201 Golden Eye Ct, Chester, MD 21619

(410) 673-3344

Property at 630 Warbler Way #12, Chester, MD 21619, 2 beds, 2.5 baths

$499,990

2 beds2.5 baths2,003 sq ft

630 Warbler Way #12, Chester, MD 21619

Listing provided by Zillow

Property at 630 Warbler Way #33, Chester, MD 21619, 2 beds, 2.5 baths

$644,990

2 beds2.5 baths1,900 sq ft

630 Warbler Way #33, Chester, MD 21619

Listing provided by Zillow

Property at 312 Teal Ct Unit F, Chester, MD 21619, 2 beds, 2 baths

$305,000

2 beds2 baths1,073 sq ft

312 Teal Ct Unit F, Chester, MD 21619

(443) 292-6767

Property at 3000 Herons Nest Way #11, Chester, MD 21619, 2 beds, 2.5 baths

$555,900

2 beds2.5 baths2,003 sq ft

3000 Herons Nest Way #11, Chester, MD 21619

(410) 263-8686

Property at 135 Nauset Ln, Chester, MD 21619, 3 beds, 3 baths

$814,900

3 beds3 baths2,399 sq ft

135 Nauset Ln, Chester, MD 21619

(855) 450-0442

Property at 1340 Queen Anne Dr, Chester, MD 21619, 3 beds, 2 baths

$459,900

3 beds2 baths1,248 sq ft

1340 Queen Anne Dr, Chester, MD 21619

(443) 274-1900

Property at 34-E Queen Anne Way, Chester, MD 21619, 2 beds, 2.5 baths

$469,000

2 beds2.5 baths1,104 sq ft

34-E Queen Anne Way, Chester, MD 21619

(301) 970-2447

Property at 630 Warbler Way #22, Chester, MD 21619, 2 beds, 2.5 baths

$565,990

2 beds2.5 baths1,900 sq ft

630 Warbler Way #22, Chester, MD 21619

Listing provided by Zillow

Property at 630 Warbler Way #32, Chester, MD 21619, 2 beds, 2.5 baths

$644,990

2 beds2.5 baths1,900 sq ft

630 Warbler Way #32, Chester, MD 21619

Listing provided by Zillow

Property at 154 Harrier Way, Chester, MD 21619, 2 beds, 2 baths

$639,450

2 beds2 baths1,900 sq ft

154 Harrier Way, Chester, MD 21619

(443) 274-1900

Property at 141 Switchgrass Way #34, Chester, MD 21619, 3 beds, 2.5 baths

$684,950

3 beds2.5 baths2,600 sq ft

141 Switchgrass Way #34, Chester, MD 21619

(443) 274-1900

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Average home prices near Chester, MD

Cities

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Chester, MD real estate trends

All Home Types trends in Chester, MD

Median Sale Price
# of Homes Sold
Median Days on Market

All Home Types

Median Sale Price (All Home Types)

$684,950

+13.2% YoY | Nov 2025

1 year
3 year
5 year

Based on Redfin calculations of home data from MLS and/or public records.

Location

Data

Nov 2025

Growth

% YoY

Chester, MD

$684,950

+13.2%

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