4 Bedroom homes for sale & real estate in Chester, MD

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ABOUT THIS HOME
4 Bedroom Homes for Sale in Chester, MD
Kent Island Living at Its Best! Welcome to this stunning colonial-style home nestled in the desirable Clayborne Woods community in Chester. Offering 2,332 square feet of thoughtfully designed living space, this beautifully maintained residence blends elegance with modern updates and everyday comfort. From the inviting covered front porch with newly replaced fiberglass columns (2025) to the upgraded interior, every detail has been carefully considered. Step inside to a welcoming two-story foyer leading to a formal living room and separate dining area. The interior features LVP flooring (2020), ceramic tile, plush new carpet throughout the stairs/upper level (2026) and architectural details

$569,900

4 beds2.5 baths2,332 sq ft

233 Cross Creek Ct, Chester, MD 21619

Covered front porch • Plush new carpet • Fiberglass columns

(301) 340-8700

FLOOR PLAN

ABOUT THIS HOME
4 Bedroom Homes for Sale in Chester, MD
A must see home! Super floor plan! Wonderful hardwood floors! Custom fixtures and finishes throughout! The best Family/Great room ever with floor to ceiling fireplace with vaulted ceilings plus outside access to stone patio w/ hot tub. Wonderful kitchen featuring oak cabinetry, upgraded appliances, crown moldings, tile & granite backsplash & countertops and eat in breakfast area. Formal Dining room, main level fourth bedroom or office with half bath and exterior entrance, perfect for occasional client or guest. Large 17x13 1st level Living Rm with hardwoods & display center. Inside entrance to the four car garage with additional built-in storage & shelving! Upper lev

$868,000

4 beds2.5 baths3,168 sq ft

113 Bentons Pleasure Rd, Chester, MD 21619

Oak cabinetry • Hot tub • Upgraded appliances

(410) 823-0033

OPEN THU, 10AM TO 1PM

ABOUT THIS HOME
4 Bedroom Homes for Sale in Chester, MD
Welcome Home!!! Open DAILY by Appointment! * * * If you're looking for the ease of primarily one-level living with flexible space for guests and hobbies, 209 Harrier Way offers the best of both worlds. * * * Barely lived in and offering over $75,000 in builder upgrades, this home still feels like new, allowing you to move right in without the wait or additional costs of new construction (i. e. transfer tax split, etc). Designed for easy everyday living, the Simone model offers the convenience of having the majority of the home's daily living spaces on the main level. The gourmet kitchen, dining and living areas, screened porch, primary suite, second bedroom, office, full bath, and lau

$747,900

4 beds3 baths3,142 sq ft

209 Harrier Way, Chester, MD 21619

Community amenities • Gourmet kitchen • Screened porch

(410) 643-2244

FLOOR PLAN

$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

LISTED BY REDFIN3D WALKTHROUGH

ABOUT THIS HOME
4 Bedroom Homes for Sale in Chester, MD
Experience the best of Kent Island living in this beautifully maintained coastal home, ideally situated in the highly desirable Water's Edge section of Gibson's Grant. Built in 2017, this exceptional residence enjoys unobstructed pond views from the welcoming covered front porch, where you can relax while watching blue herons and other native wildlife. Perfectly positioned just one block from the community's exceptional waterfront amenities, including the Chester River, clubhouse, pool, fitness center, kayak launch, fishing pier, and waterfront pavilion, this home offers the perfect blend of luxury, convenience, and the relaxed lifestyle of Maryland's Eastern Shore. Step inside to discover

$749,000

4 beds3.5 baths2,185 sq ft

134 Richard Ingle Way, Chester, MD 21619

Covered front porch • Waterfront amenities • Gas fireplace

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 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 232 Evelyne St, Chester, MD 21619, 4 beds, 3.5 baths

$825,000

4 beds3.5 baths3,312 sq ft

232 Evelyne St, Chester, MD 21619

(410) 673-3344

Property at 208 Blenny Ln, Chester, MD 21619, 4 beds, 3 baths

$374,900

4 beds3 baths1,899 sq ft

208 Blenny Ln, Chester, MD 21619

(443) 274-1900

Property at 1757 Harbor Dr, Chester, MD 21619, 4 beds, 3.5 baths

$1,294,800

4 beds3.5 baths— sq ft

1757 Harbor Dr, Chester, MD 21619

(410) 729-7700

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

$883,990

4 beds3.5 baths3,601 sq ft

Munich ESP Plan, Chester, MD 21619

Listing provided by Zillow

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

$701,990

4 beds3 baths2,791 sq ft

Simone Plan, Chester, MD 21619

Listing provided by Zillow

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

$886,990

4 beds3.5 baths3,512 sq ft

Mykonos Plan, Chester, MD 21619

Listing provided by Zillow

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ABOUT THIS HOME
4 Bedroom Homes for Sale in Chester, MD
Luxury homes rarely become available. This stunning end unit townhome offering 4 bedrooms, 3.5 bathrooms, and an impressive list of high end upgrades is available in sought after Ellendale Community. Filled with natural light, the open floor plan features hardwood floors, custom plantation shutters, elegant trim, and a built-in Bose surround sound system. The gourmet kitchen is equipped with stainless steel appliances, 42" soft close maple cabinetry, under cabinet & pendant lighting, and backsplash. Escape to the spacious primary suite with a tray ceiling and spa bath or unwind on the composite deck overlooking spectacular sunset views. Remodeled bathrooms, LED lighting throughou

$574,900

4 beds3.5 baths2,331 sq ft

118 Amanda Frances Ln, Stevensville, MD 21666

Open floor plan • End unit townhome • Gourmet kitchen

(443) 274-1900

ABOUT THIS HOME
4 Bedroom Homes for Sale in Chester, MD
This charming 4-bedroom, 4-bathroom townhouse in the desirable Ellendale community offers a perfect blend of modern comfort and inviting warmth. Built in 2023, this Baldwin built home features an open floor plan with luxury vinyl plank flooring and carpet in the bedrooms, ideal for both relaxation and entertaining. The spacious kitchen features a large center island and high-quality appliances, including a built-in microwave and dishwasher, making meal prep a delight. Large Deck off dining/kitchen area, too! Enjoy evenings by the fireplace or step out onto the balcony and deck to soak in the serene views of the garden and open common area. Nearby parks and walking paths invite outdoor adve

$595,000

4 beds4 baths2,471 sq ft

314 Allison Jane Dr Unit H-2, Stevensville, MD 21666

Large deck • Open floor plan • Large center island

(410) 304-2250

3D WALKTHROUGH

ABOUT THIS HOME
4 Bedroom Homes for Sale in Chester, MD
Welcome to 624 Davol Road, a beautifully updated 4-bedroom, 3.5-bath home offering nearly 2,500 square feet in the sought-after Cloverfields community. Recent 2026 improvements include updated flooring, a renovated kitchen, new lighting and a new roof, creating a fresh, move-in-ready feel throughout. Outside, you’ll appreciate the garage, large parking pad and fenced backyard with plenty of space to relax, entertain or play. Cloverfields offers an incredible Eastern Shore lifestyle with a community pool, private beach, playgrounds and marina with boat slips available for rent when offered. Conveniently located just off the first exit over the Bay Bridge, the home provides easy access

$575,000

4 beds3.5 baths2,408 sq ft

624 Davol Rd, Stevensville, MD 21666

New lighting • Community pool • Renovated kitchen

(703) 378-8810

ABOUT THIS HOME
4 Bedroom Homes for Sale in Chester, MD
Welcome Home to 729 Kimberly Way, nestled in the highly sought-after waterfront community of Cloverfields on Kent Island—where thoughtful updates, exceptional outdoor living, and versatile bonus space combine to create a home you’ll be proud to call your own. This beautifully maintained 4-bedroom, 2-bath raised rancher welcomes you with mature landscaping, vibrant flower beds, a spacious half-circle driveway, and outstanding curb appeal. The extended driveway leads to an oversized detached garage with generous storage above, offering endless potential to be finished into additional workspace, a private office, hobby room, or the perfect retreat to fit your lifestyle. Step into y

$589,000

4 beds2 baths2,376 sq ft

729 Kimberly Way, Stevensville, MD 21666

Backyard oasis • Two-tier deck • Updated kitchen

(703) 378-8810

ABOUT THIS HOME
4 Bedroom Homes for Sale in Chester, MD
Welcome to this like-new, impeccably maintained stone front end-unit townhome offering four finished levels of thoughtfully designed living space, 4/5 bedrooms, 4.5 bathrooms, and numerous custom upgrades throughout. Perfectly located just one mile from the Chesapeake Bay Bridge, this stunning home combines modern luxury with the convenience of Eastern Shore living. You are welcomed to the home by a partial wrap around porch, ideal for decorating and offers coverage for deliveries. Inside you will discover a beautifully updated interior with all four levels of stairs completely renovated with new flooring (2026), representing a $10,000 investment, luxury vinyl plank flooring, new carpet in

$605,000

4 beds4.5 baths2,850 sq ft

222 Jessica Lyn Ave Unit G5, Stevensville, MD 21666

Quartz countertops • Private balcony • Gourmet kitchen

(410) 647-8000

ABOUT THIS HOME
4 Bedroom Homes for Sale in Chester, MD
Like new and loaded with upgrades, this stunning end-unit Baldwin townhome is just three years young and offers the perfect blend of style, space, and convenience. Featuring 4 bedrooms, 4 full baths, and 1 half bath, this spacious home was thoughtfully designed for modern living. The heart of the home is the bright white gourmet kitchen complete with quartz countertops, abundant cabinetry, a large center island, and an expanded kitchen/dining bump-out that creates an open and inviting space for entertaining. The adjoining living areas boasts a shiplap focal wall with fireplace and is filled with natural light thanks to the premium end-unit location. Retreat to the luxurious owner's suite w

$585,000

4 beds4.5 baths2,850 sq ft

310 Allison Jane Dr Unit H-1, Stevensville, MD 21666

Outdoor pool • Quartz countertops • Rooftop deck

(703) 378-8810

Property at 376 Web Foot Ln, Stevensville, MD 21666, 4 beds, 2.5 baths

$635,000

4 beds2.5 baths2,708 sq ft

376 Web Foot Ln, Stevensville, MD 21666

(410) 643-2244

Property at 220 Creeks End Ln, Stevensville, MD 21666, 4 beds, 2.5 baths

$659,900

4 beds2.5 baths2,840 sq ft

220 Creeks End Ln, Stevensville, MD 21666

(410) 255-0004

Property at 715 Warbler Way, Chester, MD 21619, 4 beds, 3 baths

$809,990

4 beds3 baths2,791 sq ft

715 Warbler Way, Chester, MD 21619

(410) 208-3500

Property at 121 Eareckson Ln, Stevensville, MD 21666, 4 beds, 2.5 baths

$850,000

4 beds2.5 baths2,141 sq ft

121 Eareckson Ln, Stevensville, MD 21666

(410) 643-2244

Property at 324 Web Foot Ln, Stevensville, MD 21666, 4 beds, 2.5 baths

$619,900

4 beds2.5 baths2,208 sq ft

324 Web Foot Ln, Stevensville, MD 21666

(410) 758-0333

Property at 205 Jessica Lyn Ave Unit F-20, Stevensville, MD 21666, 4 beds, 3.5 baths

$489,900

4 beds3.5 baths2,280 sq ft

205 Jessica Lyn Ave Unit F-20, Stevensville, MD 21666

(301) 870-7653

Property at 412 Main St, Stevensville, MD 21666, 4 beds, 2 baths

$699,000

4 beds2 baths3,018 sq ft

412 Main St, Stevensville, MD 21666

(703) 242-0005

Property at 303 Creeks End Ln, Stevensville, MD 21666, 4 beds, 2.5 baths

$649,900

4 beds2.5 baths2,564 sq ft

303 Creeks End Ln, Stevensville, MD 21666

(703) 570-7307

Property at 606 Kimberly Way, Stevensville, MD 21666, 4 beds, 2.5 baths

$499,900

4 beds2.5 baths1,704 sq ft

606 Kimberly Way, Stevensville, MD 21666

(410) 643-2244

Property at 322 Allison Jane Dr Unit H-4, Stevensville, MD 21666, 4 beds, 4 baths

$595,000

4 beds4 baths2,630 sq ft

322 Allison Jane Dr Unit H-4, Stevensville, MD 21666

(410) 486-4504

Property at 233 Nichols Manor Dr, Stevensville, MD 21666, 4 beds, 2.5 baths

$699,800

4 beds2.5 baths2,300 sq ft

233 Nichols Manor Dr, Stevensville, MD 21666

(410) 729-7700

Property at 107 Petrie Way, Stevensville, MD 21666, 4 beds, 4 baths

$2,375,000

4 beds4 baths3,280 sq ft

107 Petrie Way, Stevensville, MD 21666

(410) 280-5600

4 Bedroom Homes for Sale in Chester

There are currently 13 4 bedroom homes in Chester. Some of these homes are "Hot Homes," meaning they're likely to sell quickly. Most homes for sale in Chester stay on the market for 77 days and receive 1 offers. This map is refreshed with the newest listings in Chester every 15 minutes.

In the past month, 15 homes have been sold in Chester. In addition to houses in Chester, there were also 17 condos, 21 townhouses, and 0 multi-family units for sale in Chester last month. Find your dream home in Chester using the tools above. Use filters to narrow your search by price, square feet, beds, and baths to find homes that fit your criteria. Our top-rated real estate agents in Chester are local experts and are ready to answer your questions about properties, neighborhoods, schools, and the newest listings for sale in Chester. Our Chester real estate stats and trends will give you more information about home buying and selling trends in Chester. If you're looking to sell your home in the Chester area, our listing agents can help you get the best price. Redfin is redefining real estate and the home buying process in Chester with industry-leading technology, full-service agents, and lower fees that provide a better value for Redfin buyers and sellers.

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