Chester, MD homes for sale & real estate

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ABOUT THIS HOME
Chester, MD Homes for Sale
Discover the extraordinary waterfront oasis of 2702 Sherman Dr. in Chester. This remarkable residence, featuring 5 bedrooms, 2 full bathrooms, and 2 half bathrooms, has undergone a stunning renovation, creating a haven of luxury and serenity on a peaceful street. Every detail of this home has been impeccably updated, from the oversized windows to the modernized bathrooms. However, the true centerpiece is the fully equipped gourmet kitchen, a masterpiece of design. A magnificent 10-foot Quartz center island takes center stage, surrounded by pristine cabinets, state-of-the-art appliances, and exquisite marble countertops. To top it off, the kitchen also boasts its own wet bar with a built-in

$989,000

5 beds3 baths2,752 sq ft

2702 Sherman Dr, Chester, MD 21619

Private pier • Oversized windows • Open-concept layout

(703) 378-8810

ABOUT THIS HOME
Chester, MD Homes for Sale
Bay Views, Space & Instant Potential! Rare end-unit condo in Queens Landing featuring 1 bedroom + spacious loft, 2 full baths, and a loft balcony with stunning Northeast Bay views. Enjoy an open, airy floor plan with dramatic cathedral ceilings, abundant storage, a large front porch, and two private patios—one off the primary bedroom and one off the living room. Tranquil, relaxing, and full of possibilities, this home needs updating but offers an incredible opportunity to build equity and make it your own. A true hidden gem at an exceptional price—don’t miss it!

$289,900

1 bed2 baths1,260 sq ft

23 Queen Victoria Way Unit 23J, Chester, MD 21619

$480 HOA • 2 parking spots • Community pool

(443) 627-2900

ABOUT THIS HOME
Chester, MD Homes for Sale
Welcome to 214 Bayberry at Four Seasons on Kent Island. Step into refined elegance and low-maintenance, luxury main-level living with this stunning Killarney model. This single family home with 10 foot ceilings blends style, comfort, and functionality, in Kent Island's premier 55+ resort-style community. Enjoy the convenience of a thoughtfully designed main level home featuring a spacious primary suite, guest bedroom, and a private home office - perfect for working from home or hosting visitors in a den setting. The Gourmet Kitchen is special, boasting upgraded appliances, expansive quartz counter tops, custom cabinetry, double wall ovens, stainless steel refrigerator with French doors, and

$924,000

3 beds3 baths2,745 sq ft

214 Bayberry Dr, Chester, MD 21619

Spa style bathroom • Screened-in porch • Gourmet kitchen

(410) 822-6665

$825,000

4 beds2.5 baths3,291 sq ft

313 Thomas White Blvd, Chester, MD 21619

6,098 sq ft lot • 2 garage spots • Community pool

(443) 906-3848

$300,000

2 beds2 baths1,100 sq ft

509 Teal Ct Unit E, Chester, MD 21619

$504 HOA • Community pool • Built 1996

(443) 274-1900

Property at 118 Broadwater Dr, Chester, MD 21619, 2 beds, 2 baths

$660,000

2 beds2 baths2,473 sq ft

118 Broadwater Dr, Chester, MD 21619

(443) 274-1900

Property at 201 Switchgrass Way #34, Chester, MD 21619, 3 beds, 2.5 baths

$859,500

3 beds2.5 baths2,602 sq ft

201 Switchgrass Way #34, Chester, MD 21619

(410) 280-5600

$389,900

3 beds2.5 baths1,899 sq ft

108 Blenny Ln, Chester, MD 21619

(410) 224-3200

Property at 209 Harrier Way, Chester, MD 21619, 4 beds, 3 baths

$747,900

4 beds3 baths3,142 sq ft

209 Harrier Way, Chester, MD 21619

(410) 643-2244

Property at 532 Cross Creek Ct, Chester, MD 21619, 4 beds, 2.5 baths

$555,000

4 beds2.5 baths2,486 sq ft

532 Cross Creek Ct, Chester, MD 21619

(410) 643-2244

Property at 134 Richard Ingle Way, Chester, MD 21619, 4 beds, 3.5 baths

$749,000

4 beds3.5 baths2,185 sq ft

134 Richard Ingle Way, Chester, MD 21619

Property at 302 Merganser Ct Unit A, Chester, MD 21619, 2 beds, 2 baths

$299,900

2 beds2 baths1,073 sq ft

302 Merganser Ct Unit A, Chester, MD 21619

(410) 729-7700

Property at 1609 Crab Alley Dr, Chester, MD 21619, 3 beds, 1.5 baths

$345,000

3 beds1.5 baths1,080 sq ft

1609 Crab Alley Dr, Chester, MD 21619

(703) 570-7307

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

$989,800

5 beds3.5 baths3,036 sq ft

203 Riverside Dr, Chester, MD 21619

(301) 945-9010

Property at 300 Woods Point Rd, Chester, MD 21619, 3 beds, 2 baths

$2,840,000

3 beds2 baths1,704 sq ft

300 Woods Point Rd, Chester, MD 21619

(410) 827-8877

Property at 2004 Bridgepointe Dr, Chester, MD 21619, 3 beds, 2 baths

$374,900

3 beds2 baths1,524 sq ft

2004 Bridgepointe Dr, Chester, MD 21619

(443) 274-1900

Property at 113 Bentons Pleasure Rd, Chester, MD 21619, 4 beds, 2.5 baths

$868,000

4 beds2.5 baths3,168 sq ft

113 Bentons Pleasure Rd, Chester, MD 21619

(410) 823-0033

Property at 205 Anchor Ln, Chester, MD 21619, 5 beds, 3 baths

$535,000

5 beds3 baths3,000 sq ft

205 Anchor Ln, Chester, MD 21619

(703) 378-8810

Property at 320 Bayberry Dr, Chester, MD 21619, 3 beds, 2 baths

$897,750

3 beds2 baths2,331 sq ft

320 Bayberry Dr, Chester, MD 21619

(410) 486-4504

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

$1,200,000

5 beds4.5 baths3,225 sq ft

111 Flycatcher Way, Chester, MD 21619

(410) 208-3500

Property at 315 Bentons Pleasure Rd, Chester, MD 21619, 3 beds, 2 baths

$629,900

3 beds2 baths1,688 sq ft

315 Bentons Pleasure Rd, Chester, MD 21619

(866) 987-3937

Property at 6010 Bridgepointe Dr, Chester, MD 21619, 3 beds, 2 baths

$380,000

3 beds2 baths1,885 sq ft

6010 Bridgepointe Dr, Chester, MD 21619

(410) 758-0333

Property at 230 Switchgrass Way #12, Chester, MD 21619, 2 beds, 2.5 baths

$525,000

2 beds2.5 baths2,003 sq ft

230 Switchgrass Way #12, Chester, MD 21619

(855) 450-0442

Property at 205 Riverside Dr, Chester, MD 21619, 3 beds, 2 baths

$749,000

3 beds2 baths1,524 sq ft

205 Riverside Dr, Chester, MD 21619

(443) 292-6767

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

$1,200,000

3 beds3.5 baths2,930 sq ft

117 Flycatcher Way, Chester, MD 21619

(410) 208-3500

Property at 233 Peregrine Dr, Chester, MD 21619, 4 beds, 3 baths

$724,999

4 beds3 baths3,151 sq ft

233 Peregrine Dr, Chester, MD 21619

(410) 758-0333

Property at 124 Riverside Dr, Chester, MD 21619, 4 beds, 2.5 baths

$499,000

4 beds2.5 baths1,979 sq ft

124 Riverside Dr, Chester, MD 21619

(866) 987-3937

Property at 121 Merlin Dr, Chester, MD 21619, 2 beds, 2 baths

$719,900

2 beds2 baths2,118 sq ft

121 Merlin Dr, Chester, MD 21619

(410) 263-8686

Property at 1000 Herons Nest Way #23, Chester, MD 21619, 2 beds, 2.5 baths

$490,000

2 beds2.5 baths— sq ft

1000 Herons Nest Way #23, Chester, MD 21619

(703) 378-8810

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

$1,100,000

3 beds3 baths2,789 sq ft

123 Flycatcher Way, Chester, MD 21619

(410) 208-3500

Property at 2855 Cox Neck Rd, Chester, MD 21619, 4 beds, 4.5 baths

$1,195,000

4 beds4.5 baths4,413 sq ft

2855 Cox Neck Rd, Chester, MD 21619

(410) 304-2250

Property at 1012 Auckland Way, Chester, MD 21619, 3 beds, 3.5 baths

$599,900

3 beds3.5 baths2,076 sq ft

1012 Auckland Way, Chester, MD 21619

Property at 111 Marshgrass Way #41, Chester, MD 21619, 3 beds, 2.5 baths

$998,000

3 beds2.5 baths— sq ft

111 Marshgrass Way #41, Chester, MD 21619

(410) 770-3600

Property at 2513 Cecil Dr, Chester, MD 21619, 5 beds, 2 baths

$1,350,000

5 beds2 baths2,700 sq ft

2513 Cecil Dr, Chester, MD 21619

(855) 450-0442

Property at 330 Serenity Ln, Chester, MD 21619, 7 beds, 8 baths

$5,400,000

7 beds8 baths10,667 sq ft

330 Serenity Ln, Chester, MD 21619

(410) 280-5600

Property at 323 Kingfisher Ln, Chester, MD 21619, 5 beds, 4.5 baths

$974,990

5 beds4.5 baths3,225 sq ft

323 Kingfisher Ln, Chester, MD 21619

(410) 208-3500

Property at 108 Price Rd, Chester, MD 21619, 3 beds, 2 baths

$216,000

3 beds2 baths1,160 sq ft

108 Price Rd, Chester, MD 21619

(410) 320-6785

Property at 115 Gibson Cir, Chester, MD 21619, 2 beds, 2.5 baths

$565,900

2 beds2.5 baths2,048 sq ft

115 Gibson Cir, Chester, MD 21619

(410) 643-2244

Property at 540 Warbler Way, Chester, MD 21619, 3 beds, 3 baths

$929,990

3 beds3 baths2,789 sq ft

540 Warbler Way, Chester, MD 21619

(410) 208-3500

Property at 265 Evelyne St, Chester, MD 21619, 3 beds, 2.5 baths

$620,000

3 beds2.5 baths2,119 sq ft

265 Evelyne St, Chester, MD 21619

(703) 378-8810

Property at 106 Bodys Neck Rd, Chester, MD 21619, 3 beds, 2.5 baths

$435,000

3 beds2.5 baths1,595 sq ft

106 Bodys Neck Rd, Chester, MD 21619

(410) 643-3404

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Average home prices near Chester, MD

Cities

Zip Codes

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)

$442,259

-29.2% YoY | Jun 2026

1 year
3 year
5 year

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

Location

Data

Jun 2026

Growth

% YoY

Chester, MD

$442,259

-29.2%

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