Chester, MD homes for sale & real estate

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ABOUT THIS HOME
Chester, MD Homes for Sale
Positioned in the heart of Chester’s marina district and just a few blocks from Castle Marina, this 3-bedroom, 2 full/2 half bath townhome brings you close to both nature and convenience. With a 1-car garage, this home is smartly designed across 3 levels with functionality and flow in mind. The main floor opens up to a large living space anchored by a fireplace and bathed in natural light. A sliding glass door leads to a generous deck where you can unwind or entertain while enjoying views of the landscaped yard. The kitchen is well-lit and offers plenty of cabinetry, connecting seamlessly to the dining and living areas. Upstairs, you'll find 3 carpeted bedrooms, including a primary su

$339,900

3 beds3 baths1,899 sq ft

206 Blenny Ln, Chester, MD 21619

$589 HOA • Garage • Community pool

(833) 335-7433

OPEN SAT, 1PM TO 3PM

ABOUT THIS HOME
Chester, MD Homes for Sale
Escape to the water — without the waterfront price. This Chester River–front townhome in Queens Landing is the perfect second home or low-maintenance retreat, all for under $500K. Enjoy sunrise water views from your private patio and balcony, and lock-and-leave peace of mind when you head back home. Inside, the layout is easy and functional with luxury vinyl plank flooring, a gas fireplace, and a bright kitchen featuring white shaker cabinets, granite counters, stainless steel appliances, and an induction cooktop. Upstairs offers vaulted ceilings, skylights, a riverfront primary suite with private balcony and en-suite bath, plus a versatile loft for guests or a home office. Fres

$480,000

2 beds2.5 baths1,680 sq ft

15-E Queen Anne Way Unit E, Chester, MD 21619

$505 HOA • Community pool • Built 1984

(443) 274-1900

NEW 27 HRS AGO

ABOUT THIS HOME
Chester, MD Homes for Sale
This is one of only two 3-bedroom condos on the market in Four Seasons with the immediate availability. Welcome to luxury condo living at Four Seasons at Kent Island, an active 55+ community packed with amenities. This is one of only two 3-bedroom condos on the market in Four Seasons with the immediate availability. No need to wait for a new condo to be built – you can move in now to 170 Harrier Way #34. This third floor Severn model (3 BR / 2 ½ Bath / 2,602 sqft) offers beautiful views of the Chester River and nearby tidal pool. Inside, sunshine fills the unit with light throughout the day and the numerous windows are treated with Hunter Douglas luxury blinds when you have h

$699,900

3 beds2.5 baths2,602 sq ft

170 Harrier Way #34, Chester, MD 21619

24 • 000 sq ft clubhouse • Upgraded package

(410) 263-3400

NEW CONSTRUCTION

ABOUT THIS HOME
Chester, MD Homes for Sale
The Tuscaloosa home offers a thoughtfully designed layout with elevated finishes throughout, with a projected settlement of April 2026. Featuring 2 bedrooms, 2.5 baths, and a 3-car garage, this home blends everyday functionality with timeless style. Standout features include a dedicated home office, a screened patio perfect for outdoor relaxation, and a shiplap-accented fireplace paired with ceiling beams that add warmth and architectural character to the great room. The kitchen is well-appointed with a single oven, microwave, gas cooktop, range hood, dishwasher, French door refrigerator, pendant lighting, and a tile backsplash, all finished with Quartz countertops that continue into the ow

$989,900

5 beds4.5 baths3,225 sq ft

110 Kinglet Ct, Chester, MD 21619

Screened patio • Quartz countertops • Ceiling beams

(240) 375-5074

NEW CONSTRUCTION

ABOUT THIS HOME
Chester, MD Homes for Sale
The Kerr on Lot 529 offers a well-balanced layout with thoughtfully selected finishes, scheduled for a March 2026 settlement. Featuring 3 bedrooms, 3 baths, and a 3-car garage, this home provides flexibility, functionality, and refined comfort throughout. Notable highlights include a dedicated home office, a screened patio for relaxed outdoor living, and a shiplap-accented fireplace that anchors the great room with warmth and character. These features make the home equally suited for everyday living and entertaining. The kitchen is fully equipped with a single oven, microwave, gas cooktop, range hood, dishwasher, French door refrigerator, pendant lighting, and tile backsplash, all complemen

$1,049,000

3 beds3 baths2,789 sq ft

141 Redstart Dr, Chester, MD 21619

Screened patio • Hardwood flooring • Quartz countertops

(240) 375-5074

Property at 4000 Herons Nest Way #22, Chester, MD 21619, 2 beds, 2.5 baths

$560,000

2 beds2.5 baths1,900 sq ft

4000 Herons Nest Way #22, Chester, MD 21619

(410) 224-3200

Property at 109 John Gibson Dr, Chester, MD 21619, 6 beds, 4.5 baths

$915,000

6 beds4.5 baths4,165 sq ft

109 John Gibson Dr, Chester, MD 21619

(410) 224-2200

Property at 1704 Bayside Dr, Chester, MD 21619, 3 beds, 2.5 baths

$1,100,000

3 beds2.5 baths1,830 sq ft

1704 Bayside Dr, Chester, MD 21619

(703) 242-0005

Property at 54-H Queen Caroline Ct, Chester, MD 21619, 2 beds, 2 baths

$349,000

2 beds2 baths1,280 sq ft

54-H Queen Caroline Ct, Chester, MD 21619

(410) 643-2244

Property at 807 Auckland Way, Chester, MD 21619, 3 beds, 3.5 baths

$425,000

3 beds3.5 baths2,100 sq ft

807 Auckland Way, Chester, MD 21619

(855) 450-0442

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 10-B Queen Elizabeth Ct, Chester, MD 21619, 1 bed, 1 bath

$330,000

1 bed1 bath724 sq ft

10-B Queen Elizabeth Ct, Chester, MD 21619

(410) 643-2244

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

$365,000

4 beds2 baths2,035 sq ft

1839 Harbor Dr, Chester, MD 21619

(301) 970-2447

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

$499,900

3 beds3.5 baths2,076 sq ft

906 Auckland Way, Chester, MD 21619

(410) 673-3344

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

$1,167,890

4 beds3.5 baths— sq ft

1757 Harbor Dr, Chester, MD 21619

(410) 729-7700

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

$499,900

4 beds2 baths1,750 sq ft

1906 Harbor Dr, Chester, MD 21619

(240) 222-3200

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

$449,900

3 beds2 baths1,248 sq ft

1340 Queen Anne Dr, Chester, MD 21619

(443) 274-1900

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 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 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 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 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 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 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 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 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 Tuscaloosa Plan, Chester, MD 21619, 5 beds, 4.5 baths

$847,990

5 beds4.5 baths3,225 sq ft

Tuscaloosa Plan, 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 132 Wheelhouse Way #43, Chester, MD 21619, 2 beds, 2.5 baths

$1,350,000

2 beds2.5 baths1,900 sq ft

132 Wheelhouse Way #43, Chester, MD 21619

Listing provided by Zillow

Property at 5-H Piney Narrows Rd, Chester, MD 21619

$49,000

— beds— baths960 sq ft

5-H Piney Narrows Rd, Chester, MD 21619

(410) 643-3033

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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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