Chester, MD homes for sale & real estate

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3D WALKTHROUGH

1033 Dundee Ct #5, Chester, MD 21619
1033 Dundee Ct #5, Chester, MD 21619
1033 Dundee Ct #5, Chester, MD 21619
ABOUT THIS HOME
Chester, MD Homes for Sale
Welcome to easy Eastern Shore living in this beautifully renovated 3 Bedroom, 2.5 Bath Townhouse Condo with water privileges, just minutes from the Bay Bridge! Updated top to bottom in 2023, this home is truly move-in ready! Enjoy peaceful mornings on the spacious screened-in porch, complete with bonus storage space, and spend afternoons at the community pier on scenic Piney Creek—perfect for launching your kayak or canoe! Inside, you’ll find new premium laminate flooring, new carpet, fresh paint, updated light fixtures & ceiling fans, renovated bathrooms, and a stylish kitchen with new stainless steel appliances. Major updates include new HVAC, new water conditioner, con

$365,000

3 beds2.5 baths1,360 sq ft

1033 Dundee Ct #5, Chester, MD 21619

$230 HOA • Car-dependent

(443) 215-4663

NEW 23 HRS AGO

121 Wheelhouse Way #11, Chester, MD 21619
121 Wheelhouse Way #11, Chester, MD 21619
121 Wheelhouse Way #11, Chester, MD 21619
ABOUT THIS HOME
Chester, MD Homes for Sale
Discover K. Hovnanian's® Four Seasons at Kent Island, a lively community of new condominiums in Chester, MD. Make your move to this active adult 55+ community on Maryland's Chesapeake Bay, offering island-living with new waterfront condos with resort-style amenities. Choose from 3, single-story floorplans of up to 2,602 sq. ft. , 3 beds, 2.5 baths, and a 1-car garage. Select plans feature a balcony or porch, to enjoy your waterfront views. Residents can enjoy the clubhouse, resort-style pool, modern fitness center, spacious dog park, open-air amphitheater, fishing and boating pier, tennis and pickleball courts, and so much more, with a schedule of activities organized by the full-time l

$539,900

2 beds2.5 baths2,003 sq ft

121 Wheelhouse Way #11, Chester, MD 21619

Car-dependent

Listing provided by Zillow

COMING SOON

223 Broadwater Dr, Chester, MD 21619
223 Broadwater Dr, Chester, MD 21619
223 Broadwater Dr, Chester, MD 21619

$849,500

3 beds3 baths2,745 sq ft

223 Broadwater Dr, Chester, MD 21619

6,100 sq ft lot • $305 HOA • 2 garage spots

(443) 274-1900

COMING SOON

104 Woods Rd, Chester, MD 21619
104 Woods Rd, Chester, MD 21619
104 Woods Rd, Chester, MD 21619
ABOUT THIS HOME
Chester, MD Homes for Sale
FANTASTIC HOME! THE COMPLETE PACKAGE AND THEN MORE! TWO PRIMARY BEDROOM/BATH SUITES! BOTH WITH GIANT WALK IN CLOSETS! EACH PRIMARY BATH HAS A STEP IN SHOWER, DOUBLE STONE VANITY PLUS SOAKING TUB! THIS HOME HAS A TOTAL OF 5 BEDROOMS PLUS 3 AND ONE HALF BATHS! PLENTY OF SPACE FOR THE HOME OFFICE! THE OPEN KITCHEN IS FULLY UPDATED WITH ISLAND, STAINLESS STEEL DOUBLE OVENS, COOKTOP, DRAWER MICROWAVE, DISHWASHER, 3 DOOR REFRIGERATOR, STATEMENT GRANITE, CUSTOM LIGHTING WITH DIMMERS. HEAT MONITORING DIRECTIONAL FAUCET. THE ADJACENT FAMILY ROOM FEATURES A GRANITE TRIMMED GAS FIREPLACE, TOWERING 19 FOOT CEILINGS, A UNIQUE WINDMILL STYLE CEILING FAN, AND DOUBLE TIERED WINDOWS FOR EXTRA LIGHT! THE HU

$805,000

5 beds3.5 baths3,065 sq ft

104 Woods Rd, Chester, MD 21619

0.53 acre lot • 2 garage spots • Pool

(410) 823-0033

121 John Gibson Dr, Chester, MD 21619
121 John Gibson Dr, Chester, MD 21619
121 John Gibson Dr, Chester, MD 21619
ABOUT THIS HOME
Chester, MD Homes for Sale
Welcome home to 121 John Gibson Drive in the waterfront community of Gibson's Grant on Kent Island. This beautifully maintained 4-bedroom, 2.5-bath home offers the perfect blend of charm, functionality, and comfort. Step inside to discover a bright and open floor plan featuring a cozy gas fireplace, ideal for relaxing evenings or entertaining guests. The heart of the home is the gorgeous offering a newly renovated kitchen, complete with a butler’s pantry—perfect for hosting, storage, and everyday ease. Whether you're whipping up a meal or sharing drinks with friends, this space is designed to impress. Upstairs you will find four spacious bedrooms to provide plenty of comfort for

$825,000

4 beds2.5 baths2,760 sq ft

121 John Gibson Dr, Chester, MD 21619

7,673 sq ft lot • $269 HOA • 2 garage spots

(410) 729-7700

Property at 9-B Queen Victoria Way, Chester, MD 21619, 3 beds, 2.5 baths

$475,000

3 beds2.5 baths1,680 sq ft

9-B Queen Victoria Way, Chester, MD 21619

(301) 490-5400

Property at 203 Barren Ridge Rd, Chester, MD 21619, 3 beds, 1.5 baths

$515,000

3 beds1.5 baths2,072 sq ft

203 Barren Ridge Rd, Chester, MD 21619

(443) 318-8800

Property at 509 Warbler Way, Chester, MD 21619, 2 beds, 2 baths

$714,900

2 beds2 baths1,993 sq ft

509 Warbler Way, Chester, MD 21619

(240) 375-5074

Property at 314 Thomas White Blvd, Chester, MD 21619, 4 beds, 3.5 baths

$789,000

4 beds3.5 baths2,400 sq ft

314 Thomas White Blvd, Chester, MD 21619

(410) 729-7700

Property at 162 Kirwans Landing Ln, Chester, MD 21619, 4 beds, 2.5 baths

$1,195,000

4 beds2.5 baths2,404 sq ft

162 Kirwans Landing Ln, Chester, MD 21619

(410) 280-5600

Property at 315 Cross Creek Ct, Chester, MD 21619, 4 beds, 2.5 baths

$585,000

4 beds2.5 baths2,374 sq ft

315 Cross Creek Ct, Chester, MD 21619

(410) 643-2244

Property at 255 Sailcloth Way, Chester, MD 21619, 4 beds, 4 baths

$950,000

4 beds4 baths3,450 sq ft

255 Sailcloth Way, Chester, MD 21619

(410) 729-7700

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 204 Skipper Ln, Chester, MD 21619, 6 beds, 3 baths

$650,000

6 beds3 baths3,760 sq ft

204 Skipper Ln, Chester, MD 21619

(410) 255-3690

Property at 121 Wheelhouse Way #21, Chester, MD 21619, 3 beds, 2.5 baths

$719,900

3 beds2.5 baths2,602 sq ft

121 Wheelhouse Way #21, Chester, MD 21619

Listing provided by Zillow

Property at 121 Wheelhouse Way #42, Chester, MD 21619, 2 beds, 2.5 baths

$779,900

2 beds2.5 baths1,900 sq ft

121 Wheelhouse Way #42, Chester, MD 21619

Listing provided by Zillow

Property at 330 Macum Creek Dr, Chester, MD 21619, 4 beds, 3.5 baths

$1,050,000

4 beds3.5 baths3,949 sq ft

330 Macum Creek Dr, Chester, MD 21619

(410) 263-8686

Property at 54-A Queen Caroline Ct, Chester, MD 21619, 2 beds, 2.5 baths

$450,000

2 beds2.5 baths1,280 sq ft

54-A Queen Caroline Ct, Chester, MD 21619

(443) 274-1900

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

$479,900

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 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 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

$469,000

2 beds2.5 baths1,104 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

$540,000

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

$385,000

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

$529,250

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

$566,000

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

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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)

$520,000

-26.8% YoY | Jun 2025

1 year
3 year
5 year

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

Location

Data

Jun 2025

Growth

% YoY

Chester, MD

$520,000

-26.8%

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