Chester, MD homes for sale & real estate

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NEW 31 HRS AGO

31-C Queen Anne Way, Chester, MD 21619
31-C Queen Anne Way, Chester, MD 21619
31-C Queen Anne Way, Chester, MD 21619
ABOUT THIS HOME
Chester, MD Homes for Sale
Welcome to 31-C Queen Anne Way, a beautifully updated two-bedroom, 1.5-bath located in Condo located in the desirable waterfront community of Queens Landing. This well-maintained unit offers 1,104 square feet of thoughtfully designed living space spread across the second and third levels. Enjoy unobstructed views of Lake Amletto and the community water tower, along with partial but striking views of the Chester River, creating a peaceful and inviting atmosphere. Recent updates include a newly replaced rear deck, newer windows and doors, and a spacious, enlarged primary bedroom. The kitchen features granite countertops, shaker-style cabinetry, and stainless steel appliances. The engineered

$334,900

2 beds1.5 baths1,104 sq ft

31-C Queen Anne Way, Chester, MD 21619

$303 HOA • Community pool • Car-dependent

(410) 643-3404

OPEN SAT, 11AM TO 1PMVIDEO TOUR

224 Bayberry Dr, Chester, MD 21619
224 Bayberry Dr, Chester, MD 21619
224 Bayberry Dr, Chester, MD 21619
ABOUT THIS HOME
Chester, MD Homes for Sale
Discover the charm of this meticulously maintained, one-owner Donegal model nestled in the highly desirable, water-privileged 55+ community of Four Seasons at Kent Island. This stunning single-family home features an expansive open-concept layout, enhanced with designer lighting and custom finishes that elevate the home's ambiance. Step into a spacious kitchen that serves as the heart of the home, featuring a beautiful black quartz island, elegant white shaker cabinets, and ample space designed for entertaining. It flows seamlessly into a cozy family room with a welcoming gas fireplace, creating the perfect setting for gatherings with friends and family. A versatile bonus room offers endles

$619,900

2 beds2 baths1,913 sq ft

224 Bayberry Dr, Chester, MD 21619

5,692 sq ft lot • $305 HOA • 2 garage spots

(410) 643-3404

COMING SOON

133 Henry Stoupe Way, Chester, MD 21619
133 Henry Stoupe Way, Chester, MD 21619
133 Henry Stoupe Way, Chester, MD 21619
ABOUT THIS HOME
Chester, MD Homes for Sale
PHOTOS COMING SOON!! Welcome to your dream home in the sought-after waterfront community of Gibson’s Grant! Situated on one of the largest corner lots in the neighborhood, this spacious 6-bedroom, 4.5-bathroom home offers over 3,500 square feet of beautifully designed living space — perfect for comfortable everyday living and effortless entertaining. Step into your own backyard oasis featuring a 520 sq ft saltwater swimming pool, stunning hardscaping, and a removable safety fence for peace of mind. The privately fenced yard offers both beauty and function, creating the ideal setting for summer fun and outdoor gatherings. Inside, you’ll love the renovated kitchen (2022), bo

$975,000

6 beds4.5 baths3,541 sq ft

133 Henry Stoupe Way, Chester, MD 21619

9,879 sq ft lot • $269 HOA • 3 garage spots

(410) 729-7700

COMING SOON

330 Macum Creek Dr, Chester, MD 21619
330 Macum Creek Dr, Chester, MD 21619
330 Macum Creek Dr, Chester, MD 21619
ABOUT THIS HOME
Chester, MD Homes for Sale
COMING SOON IN GIBSON'S GRANT! Move in ready with custom upgrades throughout, 330 Macum Creek Drive offers luxury living in one of Kent Island’s most sought after communities. A few highlights of the property include a main level primary with custom closets, finished room over the garage with a full bathroom, open concept kitchen and living space, custom butler's pantry, bonus living space with fireplace, two additional bedrooms with bathroom upstairs, a four season room, the custom outdoor kitchen of your dreams, and so much more. Professional photos and additional information on this stunning home coming soon. Gibson's Grant is one of the most desirable waterfront communities on the

$1,050,000

4 beds3.5 baths3,949 sq ft

330 Macum Creek Dr, Chester, MD 21619

7,260 sq ft lot • $269 HOA • 2 garage spots

(410) 263-8686

COMING SOON

162 Kirwans Landing Ln, Chester, MD 21619
162 Kirwans Landing Ln, Chester, MD 21619
162 Kirwans Landing Ln, Chester, MD 21619
ABOUT THIS HOME
Chester, MD Homes for Sale
Welcome to 162 Kirwans Landing Lane, a beautifully updated home located in the water-privileged community of Kirwans Landing. Set on 1.4 acres, this 4-bedroom, 2.5-bath property offers a perfect blend of comfort and outdoor living. Inside, you’ll find hardwood floors, a renovated kitchen, and a bright, airy sunroom ideal for year-round enjoyment. The backyard is a true retreat—featuring a private pool, an expansive patio, and extensive hardscaping surrounded by lush landscaping. A 90-foot private pier provides direct water access, and residents also enjoy use of the community marina. A rare offering with lifestyle and location in mind.

$1,195,000

4 beds2.5 baths2,404 sq ft

162 Kirwans Landing Ln, Chester, MD 21619

1.4 acre lot • $29 HOA • 2 garage spots

(410) 280-5600

Property at 2723 Cox Neck Rd, Chester, MD 21619, 4 beds, 2.5 baths

$499,900

4 beds2.5 baths1,600 sq ft

2723 Cox Neck Rd, Chester, MD 21619

(410) 643-2244

Property at 25-E Queen Elizabeth Ct, Chester, MD 21619, 3 beds, 2.5 baths

$569,000

3 beds2.5 baths1,680 sq ft

25-E Queen Elizabeth Ct, Chester, MD 21619

(240) 630-8689

Property at 201 Switchgrass Way #1443, Chester, MD 21619, 2 beds, 2.5 baths

$784,900

2 beds2.5 baths1,900 sq ft

201 Switchgrass Way #1443, Chester, MD 21619

(240) 375-5074

Property at 201 Switchgrass Way #1442, Chester, MD 21619, 2 beds, 2.5 baths

$784,900

2 beds2.5 baths1,900 sq ft

201 Switchgrass Way #1442, Chester, MD 21619

(240) 375-5074

Property at 201 Switchgrass Way #1433, Chester, MD 21619, 2 beds, 2.5 baths

$684,900

2 beds2.5 baths1,900 sq ft

201 Switchgrass Way #1433, Chester, MD 21619

(240) 375-5074

Property at 211 Switchgrass Way #1531, Chester, MD 21619, 3 beds, 2.5 baths

$739,900

3 beds2.5 baths2,602 sq ft

211 Switchgrass Way #1531, Chester, MD 21619

(240) 375-5074

Property at 218 Switchgrass Way #1732, Chester, MD 21619, 2 beds, 2.5 baths

$849,900

2 beds2.5 baths1,900 sq ft

218 Switchgrass Way #1732, Chester, MD 21619

(240) 375-5074

Property at 164 Redstart Dr, Chester, MD 21619, 3 beds, 3 baths

$889,900

3 beds3 baths2,789 sq ft

164 Redstart Dr, Chester, MD 21619

(240) 375-5074

Property at 327 Kingfisher Ln, Chester, MD 21619, 5 beds, 4.5 baths

$999,900

5 beds4.5 baths3,225 sq ft

327 Kingfisher Ln, Chester, MD 21619

(240) 375-5074

Property at 1872 Harbor Dr, Chester, MD 21619, 3 beds, 2 baths

$510,000

3 beds2 baths1,486 sq ft

1872 Harbor Dr, Chester, MD 21619

(410) 778-3779

Property at Munich ESP Plan, Chester, MD 21619, 4 beds, 3.5 baths

$869,900

4 beds3.5 baths3,601 sq ft

Munich ESP Plan, Chester, MD 21619

Listing provided by Zillow

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

$299,000

3 beds2 baths1,750 sq ft

1906 Harbor Dr, Chester, MD 21619

(443) 320-1344

Property at 412 Hanna Ct, Chester, MD 21619, 4 beds, 2.5 baths

$485,000

4 beds2.5 baths1,840 sq ft

412 Hanna Ct, Chester, MD 21619

(410) 321-1833

Property at 132 Wheelhouse Way #21, Chester, MD 21619, 3 beds, 2.5 baths

$1,099,000

3 beds2.5 baths2,602 sq ft

132 Wheelhouse Way #21, Chester, MD 21619

(410) 729-7700

Property at 204 Teal Ct Unit B, Chester, MD 21619, 2 beds, 2 baths

$295,000

2 beds2 baths1,073 sq ft

204 Teal Ct Unit B, Chester, MD 21619

(703) 581-8605

Property at 312 Blenny Ln, Chester, MD 21619, 3 beds, 3 baths

$479,000

3 beds3 baths1,899 sq ft

312 Blenny Ln, Chester, MD 21619

(301) 850-0255

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

$499,000

2 beds2.5 baths1,586 sq ft

34-E Queen Anne Way, Chester, MD 21619

(301) 970-2447

Property at 190 Harrier Way #11, Chester, MD 21619, 2 beds, 2.5 baths

$560,000

2 beds2.5 baths2,003 sq ft

190 Harrier Way #11, Chester, MD 21619

(443) 274-1900

Property at 108 Bodys Neck Rd, Chester, MD 21619, 3 beds, 2.5 baths

$499,900

3 beds2.5 baths1,791 sq ft

108 Bodys Neck Rd, Chester, MD 21619

(410) 643-3404

Property at 2707 Cox Neck Rd, Chester, MD 21619, 3 beds, 2.5 baths

$434,900

3 beds2.5 baths1,568 sq ft

2707 Cox Neck Rd, Chester, MD 21619

(410) 255-3690

Property at 35-F Queen Anne Way, Chester, MD 21619, 2 beds, 2.5 baths

$354,900

2 beds2.5 baths1,440 sq ft

35-F Queen Anne Way, Chester, MD 21619

(410) 643-2244

Property at 24-D Queen Elizabeth Ct, Chester, MD 21619, 2 beds, 2.5 baths

$549,000

2 beds2.5 baths1,680 sq ft

24-D Queen Elizabeth Ct, Chester, MD 21619

(410) 260-0202

Property at 413 Dominion Rd, Chester, MD 21619, 3 beds, 2 baths

$399,000

3 beds2 baths1,346 sq ft

413 Dominion Rd, Chester, MD 21619

(410) 643-5005

Property at Magothy Plan, Chester, MD 21619, 2 beds, 2.5 baths

$474,990

2 beds2.5 baths2,003 sq ft

Magothy Plan, Chester, MD 21619

Listing provided by Zillow

Property at Chester Plan, Chester, MD 21619, 2 beds, 2.5 baths

$474,990

2 beds2.5 baths1,900 sq ft

Chester Plan, Chester, MD 21619

Listing provided by Zillow

Property at 49-C Queen Guinevere Way, Chester, MD 21619, 2 beds, 2.5 baths

$529,500

2 beds2.5 baths1,600 sq ft

49-C Queen Guinevere Way, Chester, MD 21619

(410) 643-3404

Property at Franklin Plan, Chester, MD 21619, 3 beds, 3.5 baths

$844,900

3 beds3.5 baths2,930 sq ft

Franklin Plan, Chester, MD 21619

Listing provided by Zillow

Property at Taylor Plan, Chester, MD 21619, 2 beds, 2.5 baths

$740,900

2 beds2.5 baths2,010 sq ft

Taylor Plan, Chester, MD 21619

Listing provided by Zillow

Property at Jenkins II Plan, Chester, MD 21619, 2 beds, 2 baths

$659,900

2 beds2 baths1,993 sq ft

Jenkins II Plan, Chester, MD 21619

Listing provided by Zillow

Property at Kelly Plan, Chester, MD 21619, 2 beds, 2 baths

$762,900

2 beds2 baths2,143 sq ft

Kelly Plan, Chester, MD 21619

Listing provided by Zillow

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

$575,000

5 beds3 baths3,500 sq ft

205 Anchor Ln, Chester, MD 21619

(443) 274-1900

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) 643-3404

Property at 112 Harbour Sound Dr, Chester, MD 21619, 3 beds, 3.5 baths

$539,500

3 beds3.5 baths2,131 sq ft

112 Harbour Sound Dr, Chester, MD 21619

(410) 349-1207

Property at 516 Warbler Way, Chester, MD 21619, 2 beds, 2 baths

$684,900

2 beds2 baths1,993 sq ft

516 Warbler Way, Chester, MD 21619

(240) 375-5074

Property at 28-28E Queen Mary Ct, Chester, MD 21619, 3 beds, 2.5 baths

$365,000

3 beds2.5 baths1,680 sq ft

28-28E Queen Mary Ct, Chester, MD 21619

(301) 850-0255

Property at 326 Hanna Ct, Chester, MD 21619, 4 beds, 2.5 baths

$425,000

4 beds2.5 baths1,840 sq ft

326 Hanna Ct, Chester, MD 21619

(410) 643-5005

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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)

$585,000

+1.7% YoY | May 2025

1 year
3 year
5 year

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

Location

Data

May 2025

Growth

% YoY

Chester, MD

$585,000

+1.7%

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