Chester, MD homes for sale & real estate

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307 Skipper Ln, Chester, MD 21619
307 Skipper Ln, Chester, MD 21619
307 Skipper Ln, Chester, MD 21619
ABOUT THIS HOME
Chester, MD Homes for Sale
Welcome to Your Refreshing New Home with First-Floor Living! This beautifully updated residence offers the perfect blend of comfort and convenience with three spacious bedrooms and two full baths, all on the main level. The expansive primary suite features a private, fully updated bath for your relaxation. The gorgeous kitchen is a true standout, boasting quartz countertops, brand new stainless steel appliances, and a bright breakfast room ideal for casual dining. Enjoy entertaining in the formal dining room or unwind in the inviting family room with refinished hard wood floors and a cozy fireplace. Recent updates include, New roof, Luxury vinyl plank (LVP) flooring, refinished hardwoods, n

$525,000

3 beds2 baths1,795 sq ft

307 Skipper Ln, Chester, MD 21619

0.5 acre lot • Garage • Car-dependent

(410) 224-2200

NEW CONSTRUCTION

218 Switchgrass Way #32, Chester, MD 21619
218 Switchgrass Way #32, Chester, MD 21619
218 Switchgrass Way #32, Chester, MD 21619

$849,900

2 beds2.5 baths1,900 sq ft

218 Switchgrass Way #32, Chester, MD 21619

Car-dependent

Listing provided by Zillow

208 Ringneck Ct, Chester, MD 21619
208 Ringneck Ct, Chester, MD 21619
208 Ringneck Ct, Chester, MD 21619
ABOUT THIS HOME
Chester, MD Homes for Sale
208 Ringneck Court is a great home for the smart buyer! This three-level, 2 bedroom, 2 1/2 bathroom garage town-home, located in the coveted Bayside Condominium neighborhood, was updated within the past 3 years. As you enter the south-facing home, you'll notice that the floor plan is a bit different than others. .. the kitchen has been reconfigured to create an open concept design which is ideal for those who love to entertain or who don't want to be separated from family or friends while in the kitchen! The kitchen, living, and dining areas flow seamlessly with luxury vinyl plank flooring, neutral walls, and updated, coordinating lighting fixtures throughout the space. The contemporary k

$369,900

2 beds2.5 baths1,747 sq ft

208 Ringneck Ct, Chester, MD 21619

$589 HOA • Garage • Community pool

(410) 643-2244

129 Kirwans Landing Ln, Chester, MD 21619
129 Kirwans Landing Ln, Chester, MD 21619
129 Kirwans Landing Ln, Chester, MD 21619
ABOUT THIS HOME
Chester, MD Homes for Sale
Peaceful Coastal Living in One of Kent Island’s Most Sought-After Communities! Tucked away on 1.01 beautifully landscaped acres, this four bedroom, two full and one half bath porch front home, is a retreat unto itself and is located in one of Kent Island’s most exclusive and rarely available neighborhoods—complete with its own private marina just down the street. Inside, this stylish home offers a thoughtful layout designed for comfort and connection. The welcoming foyer with heated floors, for those off season cold winter evenings, leads to the sleek kitchen, featuring granite countertops and high-end stainless steel appliances. The adjacent wood burning stove that is sh

$997,000

4 beds2.5 baths2,630 sq ft

129 Kirwans Landing Ln, Chester, MD 21619

1.01 acre lot • $29 HOA • 8 garage spots

(443) 708-7074

558 Cross Creek Ct, Chester, MD 21619
558 Cross Creek Ct, Chester, MD 21619
558 Cross Creek Ct, Chester, MD 21619
ABOUT THIS HOME
Chester, MD Homes for Sale
Nestled in a highly desirable community, this stunning home offers over 2,500 sqft of spacious living on a large, wooded lot, ensuring privacy and tranquility. Move right into this freshly painted haven, featuring four generous bedrooms, including a luxurious primary suite with a massive walk-in closet and a spa-like ensuite bathroom—complete with a Jacuzzi tub and separate shower. Main Level Highlights: * * Brand-new Luxury Vinyl Tile (LVT) flooring * * Eat-in kitchen with ample space for gatherings * * Cozy family room with a gas fireplace * * Bonus room, perfect for an office or playroom * * Formal living and dining rooms for elegant entertaining * * Convenient half b

$559,850

4 beds2.5 baths2,558 sq ft

558 Cross Creek Ct, Chester, MD 21619

0.24 acre lot • $54 HOA • 2 garage spots

(703) 581-8605

Property at 242 Peregrine Dr, Chester, MD 21619, 4 beds, 3 baths

$715,000

4 beds3 baths3,151 sq ft

242 Peregrine Dr, Chester, MD 21619

(301) 423-0440

Property at 132 Claiborne St, Chester, MD 21619, 3 beds, 3.5 baths

$750,000

3 beds3.5 baths2,400 sq ft

132 Claiborne St, Chester, MD 21619

(301) 490-5400

Property at 202 Ringneck Ct, Chester, MD 21619, 2 beds, 2.5 baths

$374,900

2 beds2.5 baths1,956 sq ft

202 Ringneck Ct, Chester, MD 21619

(410) 822-1415

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

$535,000

3 beds3.5 baths2,100 sq ft

807 Auckland Way, Chester, MD 21619

(301) 760-2136

Property at 524 Warbler Way, Chester, MD 21619, 2 beds, 2 baths

$639,900

2 beds2 baths1,690 sq ft

524 Warbler Way, Chester, MD 21619

(240) 375-5074

Property at 206 Blenny Ln, Chester, MD 21619, 3 beds, 3 baths

$365,000

3 beds3 baths1,899 sq ft

206 Blenny Ln, Chester, MD 21619

(410) 643-2244

Property at 170 Harrier Way #22, Chester, MD 21619, 2 beds, 2.5 baths

$510,000

2 beds2.5 baths1,900 sq ft

170 Harrier Way #22, Chester, MD 21619

(410) 972-4000

Property at 1019 Dominion Rd, Chester, MD 21619, 1 bed, 1 bath

$369,000

1 bed1 bath1,008 sq ft

1019 Dominion Rd, Chester, MD 21619

(302) 360-0300

Property at 170 Harrier Way #34, Chester, MD 21619, 3 beds, 2.5 baths

$825,000

3 beds2.5 baths2,602 sq ft

170 Harrier Way #34, Chester, MD 21619

(410) 263-3400

Property at 1000 Herons Nest Way #32, Chester, MD 21619, 2 beds, 2 baths

$499,000

2 beds2 baths— sq ft

1000 Herons Nest Way #32, Chester, MD 21619

(443) 274-1900

Property at 170 Harrier Way #11, Chester, MD 21619, 2 beds, 2.5 baths

$545,000

2 beds2.5 baths2,003 sq ft

170 Harrier Way #11, Chester, MD 21619

Property at 1622 Bayside Dr, Chester, MD 21619, 4 beds, 2.5 baths

$1,299,900

4 beds2.5 baths3,000 sq ft

1622 Bayside Dr, Chester, MD 21619

(301) 745-5500

Property at 1000 Herons Nest Way #22, Chester, MD 21619, 2 beds, 2.5 baths

$515,000

2 beds2.5 baths1,900 sq ft

1000 Herons Nest Way #22, Chester, MD 21619

(443) 274-1900

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

$304,000

2 beds2.5 baths1,440 sq ft

30-C Queen Mary Ct, Chester, MD 21619

(410) 255-3690

Property at 2653 Cox Neck Rd, Chester, MD 21619, 3 beds, 2 baths

$389,000

3 beds2 baths1,560 sq ft

2653 Cox Neck Rd, Chester, MD 21619

(410) 228-2900

Property at 137 Warbler Way, Chester, MD 21619, 2 beds, 2 baths

$739,950

2 beds2 baths2,147 sq ft

137 Warbler Way, Chester, MD 21619

(443) 249-7653

Property at 201 Switchgrass Way #43, Chester, MD 21619, 2 beds, 2.5 baths

$784,900

2 beds2.5 baths1,900 sq ft

201 Switchgrass Way #43, Chester, MD 21619

Listing provided by Zillow

Property at 201 Switchgrass Way #33, Chester, MD 21619, 2 beds, 2.5 baths

$684,900

2 beds2.5 baths1,900 sq ft

201 Switchgrass Way #33, Chester, MD 21619

Listing provided by Zillow

Property at 201 Switchgrass Way #42, Chester, MD 21619, 2 beds, 2.5 baths

$784,900

2 beds2.5 baths1,900 sq ft

201 Switchgrass Way #42, Chester, MD 21619

Listing provided by Zillow

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

$649,400

2 beds2 baths1,900 sq ft

154 Harrier Way, Chester, MD 21619

(443) 274-1900

Property at 103 John Gibson Dr, Chester, MD 21619, 4 beds, 3 baths

$789,000

4 beds3 baths2,602 sq ft

103 John Gibson Dr, Chester, MD 21619

(443) 274-1900

Property at 7-C Queen Victoria Way Unit 7C, Chester, MD 21619, 1 bath

$254,750

— beds1 bath724 sq ft

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

(410) 643-3404

Property at 8-E Queen Victoria Way, Chester, MD 21619, 3 beds, 2.5 baths

$359,900

3 beds2.5 baths1,680 sq ft

8-E Queen Victoria Way, Chester, MD 21619

(240) 403-0400

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

Property at 7014 Bridgepointe Dr, Chester, MD 21619, 3 beds, 2.5 baths

$359,000

3 beds2.5 baths1,635 sq ft

7014 Bridgepointe Dr, Chester, MD 21619

(410) 544-4000

Property at 308 Dominion Rd, Chester, MD 21619, 3 beds, 2 baths

$334,900

3 beds2 baths1,280 sq ft

308 Dominion Rd, Chester, MD 21619

(681) 252-3002

Property at 1771 Harbor Dr, Chester, MD 21619, 5 beds, 2.5 baths

$750,000

5 beds2.5 baths2,564 sq ft

1771 Harbor Dr, Chester, MD 21619

(410) 224-2200

Property at 114 Addison Ct, Chester, MD 21619, 3 beds, 2.5 baths

$575,000

3 beds2.5 baths2,342 sq ft

114 Addison Ct, Chester, MD 21619

(410) 643-5005

Property at 170 Harrier Way #33, Chester, MD 21619, 2 beds, 2.5 baths

$499,950

2 beds2.5 baths1,900 sq ft

170 Harrier Way #33, Chester, MD 21619

(443) 274-1900

Property at 1501 Norman Rd, Chester, MD 21619, 4 beds, 2.5 baths

$671,400

4 beds2.5 baths— sq ft

1501 Norman Rd, Chester, MD 21619

(410) 729-7700

Property at Kerr Plan, Chester, MD 21619, 3 beds, 3 baths

$807,900

3 beds3 baths2,789 sq ft

Kerr Plan, Chester, MD 21619

Listing provided by Zillow

Property at Mykonos Plan, Chester, MD 21619, 4 beds, 3.5 baths

$872,900

4 beds3.5 baths3,512 sq ft

Mykonos Plan, Chester, MD 21619

Listing provided by Zillow

Property at Simone Plan, Chester, MD 21619, 4 beds, 3 baths

$691,900

4 beds3 baths2,791 sq ft

Simone Plan, Chester, MD 21619

Listing provided by Zillow

Property at Severn Plan, Chester, MD 21619, 3 beds, 2.5 baths

$559,990

3 beds2.5 baths2,602 sq ft

Severn Plan, Chester, MD 21619

Listing provided by Zillow

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

$836,900

5 beds4.5 baths3,225 sq ft

Tuscaloosa Plan, Chester, MD 21619

Listing provided by Zillow

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

$626,900

2 beds2 baths1,690 sq ft

Bernstein II Plan, Chester, MD 21619

Listing provided by Zillow

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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)

$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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