Chester, MD homes for sale & real estate

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NEW 10 HRS AGOFLOOR PLAN

ABOUT THIS HOME
Chester, MD Homes for Sale
Absolutely Stunning Custom Home in Gibson’s Grant! Welcome to this beautifully appointed custom home featuring an open floor plan, wide-plank solid red oak hardwood flooring throughout the main level, and timeless architectural details. The main-level primary suite offers a private office/ possible sitting room, creating the perfect blend of comfort and functionality. The inviting kitchen features custom cabinetry, distinctive hardware, and a spacious pantry. The breakfast room opens to a sun-filled sunroom with custom brick pavers, privacy sheers, sliding doors, and skylights that welcome natural light throughout the day. A welcoming dining area with elegant wainscoting provides the

$915,000

4 beds3.5 baths3,424 sq ft

202 Claiborne St, Chester, MD 21619

Inviting kitchen • Custom cabinetry • Open floor plan

(410) 224-2200

3D WALKTHROUGH

ABOUT THIS HOME
Chester, MD Homes for Sale
OPEN HOUSE SUN OCT 11TH 12-2PM! It's rare to find a designer home on a 1.4 acre lot with an in-ground saltwater pool and direct waterfront access on Kent Island at this price tag. From the moment you arrive, the outdoor setting feels like a private resort. A sparkling saltwater pool is surrounded by a newly hardscaped stone terrace, mature lawn & landscaping, apple tree, fig tree, cypress tree, and even strawberries! The rear backs up to farmland creating a secluded, private feel. Walk out your front door, directly to the left of the house to access your own 90 foot pier extends out offering direct access to Kirwan Creek for small boats, kayaking, paddle boarding, fishing, crabbing, w

$1,199,900

5 beds3 baths3,000 sq ft

162 Kirwans Landing Ln, Chester, MD 21619

Updated kitchen • 90 foot pier • 1.4 acre lot

(443) 901-2200

3D WALKTHROUGH

ABOUT THIS HOME
Chester, MD Homes for Sale
Welcome to 2011 Stevens Drive — a completely renovated home offering exceptional one-level living with a spacious, open floor plan and a long list of thoughtful upgrades throughout. From top to bottom, this home has been transformed with modern finishes, new flooring, fresh paint, updated lighting, renovated bathrooms, and a beautifully redesigned kitchen. The oversized kitchen features quartz countertops, updated appliances, abundant cabinetry, and plenty of workspace, with a large laundry room conveniently located just off the kitchen. Just off the kitchen, a beautifully appointed private dining room provides an elegant space for entertaining and hosting gatherings. With its versati

$489,900

3 beds2 baths1,663 sq ft

2011 Stevens Dr, Chester, MD 21619

Private dining room • Oversized kitchen • Dramatic ceilings

(703) 378-8810

ABOUT THIS HOME
Chester, MD Homes for Sale
Nestled in the serene Harbor View subdivision, this Colonial-style home offers a perfect blend of luxury and comfort. The interior features elegant bamboo and ceramic tile flooring, enhancing the warm ambiance throughout. The gourmet kitchen is equipped with stainless steel appliances, including a dishwasher, electric oven/range, and refrigerator, making culinary adventures a delight. A charming wood-burning stove adds a touch of warmth to the living space, creating an inviting atmosphere for relaxation. Set on a generous 1.14-acre lot in a peaceful cul-de-sac, the landscaped grounds provide a tranquil retreat. Enjoy stunning water views of Cox Creek, just a short stroll away, where you can

$699,000

3 beds2.5 baths1,560 sq ft

2703 Sherman Dr, Chester, MD 21619

Landscaped grounds • Gourmet kitchen • Peaceful cul-de-sac

(410) 758-0333

3D WALKTHROUGH

ABOUT THIS HOME
Chester, MD Homes for Sale
Welcome to 223 Evelyne Street in Gibson’s Grant! Built by Koch Homes, this expanded Ashford model combines the convenience of a main-level primary bedroom with spacious living areas and an oversized garage with an enlarged family room above. Hardwood floors, plantation shutters throughout the home, and a beautiful stone-surround fireplace add warmth and timeless style. The spacious living room, kitchen, and dining area offer a welcoming setting for everyday living and entertaining, while a separate office provides a dedicated space for work or study. A beautiful Andersen sliding door opens to the deck and hardscaped patio, creating an inviting outdoor space for dining, relaxing, and g

$799,000

3 beds2.5 baths2,575 sq ft

223 Evelyne St, Chester, MD 21619

Separate office • Plantation shutters • Expanded family room

(703) 378-8810

Property at 231 Dominion Rd, Chester, MD 21619, 5 beds, 3 baths

$599,000

5 beds3 baths1,852 sq ft

231 Dominion Rd, Chester, MD 21619

(410) 643-2244

Property at 1-F Queen Victoria Ct, Chester, MD 21619, 2 beds, 2 baths

$400,000

2 beds2 baths1,260 sq ft

1-F Queen Victoria Ct, Chester, MD 21619

(410) 255-3690

Property at 117 Harrier Way, Chester, MD 21619, 3 beds, 2 baths

$790,000

3 beds2 baths2,331 sq ft

117 Harrier Way, Chester, MD 21619

(443) 274-1900

Property at 1509 Calvert Rd, Chester, MD 21619, 4 beds, 3 baths

$1,350,000

4 beds3 baths3,680 sq ft

1509 Calvert Rd, Chester, MD 21619

(410) 643-2244

Property at 111 Marshgrass Way #43, Chester, MD 21619, 2 beds, 2.5 baths

$744,900

2 beds2.5 baths1,900 sq ft

111 Marshgrass Way #43, Chester, MD 21619

(410) 643-2244

Property at 1616 Postal Rd, Chester, MD 21619, 5 beds, 2.5 baths

$635,000

5 beds2.5 baths2,818 sq ft

1616 Postal Rd, Chester, MD 21619

(410) 224-2200

Property at 117 Wright Rd, Chester, MD 21619, 3 beds, 2 baths

$412,000

3 beds2 baths1,337 sq ft

117 Wright Rd, Chester, MD 21619

(410) 255-3690

Property at 205 Dominion Ln, Chester, MD 21619, 3 beds, 2 baths

$300,000

3 beds2 baths1,160 sq ft

205 Dominion Ln, Chester, MD 21619

(888) 860-7369

Property at 402 Macum Creek Dr, Chester, MD 21619, 3 beds, 2.5 baths

$789,000

3 beds2.5 baths2,787 sq ft

402 Macum Creek Dr, Chester, MD 21619

(703) 378-8810

Property at 1010 Auckland Way, Chester, MD 21619, 3 beds, 3.5 baths

$595,000

3 beds3.5 baths2,100 sq ft

1010 Auckland Way, Chester, MD 21619

(410) 505-9700

Property at 326 Castle Marina Rd, Chester, MD 21619, 5 beds, 3.5 baths

$525,000

5 beds3.5 baths3,552 sq ft

326 Castle Marina Rd, Chester, MD 21619

(410) 643-5005

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 231 Evelyne St, Chester, MD 21619, 4 beds, 2.5 baths

$815,000

4 beds2.5 baths2,870 sq ft

231 Evelyne St, Chester, MD 21619

(410) 304-2250

Property at 107 Lee Rd, Chester, MD 21619, 3 beds, 1 bath

$330,000

3 beds1 bath960 sq ft

107 Lee Rd, Chester, MD 21619

(480) 462-5392

Property at 208 Widgeon Way, Chester, MD 21619, 3 beds, 3.5 baths

$599,900

3 beds3.5 baths2,100 sq ft

208 Widgeon Way, Chester, MD 21619

(410) 224-3200

Property at 34 Queen Anne Way Unit A, Chester, MD 21619, 2 beds, 2 baths

$570,000

2 beds2 baths1,380 sq ft

34 Queen Anne Way Unit A, Chester, MD 21619

(443) 274-1900

Property at 129 Wheelhouse Way #11, Chester, MD 21619, 2 beds, 2.5 baths

$585,000

2 beds2.5 baths2,003 sq ft

129 Wheelhouse Way #11, Chester, MD 21619

(443) 274-1900

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

$859,900

3 beds2 baths2,331 sq ft

320 Bayberry Dr, Chester, MD 21619

(410) 224-3200

Property at 228 Bayberry Dr, Chester, MD 21619, 2 beds, 2.5 baths

$665,000

2 beds2.5 baths1,993 sq ft

228 Bayberry Dr, Chester, MD 21619

(410) 544-4000

Property at 15-E Queen Anne Way Unit E, Chester, MD 21619, 2 beds, 2.5 baths

$539,000

2 beds2.5 baths1,680 sq ft

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

(410) 822-6665

Property at 8-E Piney Narrows Rd, Chester, MD 21619

$40,000

— beds— baths830 sq ft

8-E Piney Narrows Rd, Chester, MD 21619

(410) 822-6665

Property at 7-B Queen Victoria Way Unit B, Chester, MD 21619, 2 beds, 2.5 baths

$499,000

2 beds2.5 baths1,680 sq ft

7-B Queen Victoria Way Unit B, Chester, MD 21619

(703) 522-1940

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

$829,000

4 beds2.5 baths3,168 sq ft

113 Bentons Pleasure Rd, Chester, MD 21619

(410) 823-0033

Property at 1717 Harbor Dr, Chester, MD 21619, 3 beds, 2.5 baths

$1,250,000

3 beds2.5 baths2,742 sq ft

1717 Harbor Dr, Chester, MD 21619

(410) 476-2201

Property at 512 Auckland Way, Chester, MD 21619, 3 beds, 3 baths

$375,000

3 beds3 baths1,899 sq ft

512 Auckland Way, Chester, MD 21619

(410) 643-2244

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

$656,000

2 beds2 baths2,473 sq ft

118 Broadwater Dr, Chester, MD 21619

(443) 274-1900

Property at 53-E Queen Caroline Ct, Chester, MD 21619, 2 beds, 2.5 baths

$329,000

2 beds2.5 baths1,440 sq ft

53-E Queen Caroline Ct, Chester, MD 21619

(888) 860-7369

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

$2,625,000

3 beds2 baths2,000 sq ft

300 Woods Point Rd, Chester, MD 21619

(410) 827-8877

Property at 168 Redstart Dr, Stevensville, MD 21619, 2 beds, 2.5 baths

$769,900

2 beds2.5 baths2,014 sq ft

168 Redstart Dr, Stevensville, MD 21619

(410) 224-3200

Property at 205 Anchor Ln, Chester, MD 21619, 4 beds, 3 baths

$500,000

4 beds3 baths3,000 sq ft

205 Anchor Ln, Chester, MD 21619

(703) 378-8810

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

$1,125,000

4 beds4.5 baths4,413 sq ft

2855 Cox Neck Rd, Chester, MD 21619

(410) 304-2250

Property at 43-A Queen Neva Ct, Chester, MD 21619, 3 beds, 2.5 baths

$445,000

3 beds2.5 baths2,008 sq ft

43-A Queen Neva Ct, Chester, MD 21619

(410) 224-3600

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 510 Auckland Way, Chester, MD 21619, 3 beds, 2.5 baths

$410,000

3 beds2.5 baths1,899 sq ft

510 Auckland Way, Chester, MD 21619

(443) 292-6767

Property at 108 Blenny Ln, Chester, MD 21619, 3 beds, 2.5 baths

$369,900

3 beds2.5 baths1,899 sq ft

108 Blenny Ln, Chester, MD 21619

(410) 224-3200

Property at 54-D Queen Caroline Ct, Chester, MD 21619, 3 beds, 2.5 baths

$299,900

3 beds2.5 baths1,440 sq ft

54-D Queen Caroline Ct, Chester, MD 21619

(410) 643-4131

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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)

$568,750

+12.1% YoY | Aug 2026

1 year
3 year
5 year

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

Location

Data

Aug 2026

Growth

% YoY

Chester, MD

$568,750

+12.1%

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2348

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* Data from the last year

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