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
Coastal elegance meets effortless waterfront living on the sunrise side of Prospect Bay. From the moment you arrive, this exceptional home feels special. Ideally positioned on a picturesque jut of land, the setting offers a bit of additional protection while showcasing beautiful, ever-changing water views and spectacular sunrises. A circular driveway leads to a charming courtyard entrance framed by lush perennial gardens. Inside, the views immediately take center stage. An open, coastal elegant floor plan bring the beauty of Prospect Bay into every living space. Coffered ceilings elevate the spacious family and dining rooms, while substantial crown molding and elegant finishes add timeless

$1,350,000

4 beds3 baths3,680 sq ft

1509 Calvert Rd, Chester, MD 21619

Large center island • Soft-close cabinets • Waterfront home

(410) 643-2244

NEW CONSTRUCTION

ABOUT THIS HOME
4 Bedroom Homes for Sale in Chester, MD
The Windermere combines all of the home design elements our purchasers love the most. On the main level you’ll love the open plan design with a huge kitchen with a9 foot island, breakfast/sunroom and family room! Formal living room/office and dining room, and two-story foyer complete the space. Upstairs 4 spacious bedrooms include an owner’s suite with spacious walk-in closet or choose the optional super bath and get two walk-in closets! A lower level offers numerous options for expanding your living space to suit your lifestyle. Placek Place is 1 minute to the brige. It offers The Eastern shore Way of Life. Close to pickle ball courts, walking trails, beaches and golf course. S

$777,900

4 beds2.5 baths— sq ft

105 Placeks Ln Ln, Stevensville, MD 21666

Open plan design • Breakfast sunroom • Family room

(410) 729-7700

ABOUT THIS HOME
4 Bedroom Homes for Sale in Chester, MD
This beautiful coastal Colonial home in Gibsons Grant offers a perfect blend of comfort and style. With 4 spacious bedrooms and 2.5 bathrooms, the open floor plan invites warmth and connection. Enjoy cooking up your favorite feast in the upgraded kitchen featuring an island, built-in appliances, and endless countertops. The family room, complete with a propane fireplace, is perfect for gatherings and gamed. Step outside to discover beautifully maintained common grounds, a community center, and a inground swimming pool. The neighborhood boasts walking paths, tennis courts, and picnic areas, ideal for outdoor enthusiasts. Located near the Chester River, residents can enjoy serene views and w

$815,000

4 beds2.5 baths2,870 sq ft

231 Evelyne St, Chester, MD 21619

Propane fireplace • Upgraded kitchen • Tennis courts

(410) 304-2250

FLOOR PLAN

ABOUT THIS HOME
4 Bedroom Homes for Sale in Chester, MD
A must see home! NEW LIST PRICE 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 & shel

$829,000

4 beds2.5 baths3,168 sq ft

113 Bentons Pleasure Rd, Chester, MD 21619

Oak cabinetry • Hot tub • Upgraded appliances

(410) 823-0033

ABOUT THIS HOME
4 Bedroom Homes for Sale in Chester, MD
Located in the prestigious Southwind community, a penisula between Crab Alley Bay & Cox Creek, this elegant contemporary ranch-style home offers an unparalleled lifestyle of luxury and comfort. Spanning over 4,400 sq. ft. of finished space, the interior boasts elegant marble flooring, complemented by crown moldings and built-ins that enhance its sophisticated charm. The gourmet kitchen, featuring upgraded countertops and a spacious island, flows seamlessly into the family room, perfect for entertaining. Relax in the primary suite with a lavish bath or unwind in the inviting family room by the fireplace with views out to Crab Alley. Three additional bedrooms (or two bedrooms and an off

$1,125,000

4 beds4.5 baths4,413 sq ft

2855 Cox Neck Rd, Chester, MD 21619

1.25 acre lot • 2 garage spots • Pool

(410) 304-2250

Property at 134 Richard Ingle Way, Chester, MD 21619, 4 beds, 3.5 baths

$739,000

4 beds3.5 baths2,185 sq ft

134 Richard Ingle Way, Chester, MD 21619

Property at 209 Harrier Way, Chester, MD 21619, 4 beds, 3 baths

$737,900

4 beds3 baths3,142 sq ft

209 Harrier Way, Chester, MD 21619

(410) 643-2244

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

$1,198,800

4 beds3.5 baths— sq ft

1757 Harbor Dr, Chester, MD 21619

(410) 729-7700

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 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 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

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

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ABOUT THIS HOME
4 Bedroom Homes for Sale in Chester, MD
With its charming white picket fence, inviting curb appeal, and timeless character, this delightful 4-bedroom, 2-full-bath Cape Cod feels like something straight out of a storybook! Nestled right in town, this home offers the perfect blend of small-town charm and everyday convenience. Enjoy being just a short stroll from local schools, the library, Love Point Park, the dog park, restaurants, coffee shops, the Kent Island Heritage Society, the Kent Island Federation of Arts, and so much more! Imagine morning coffee at your favorite local spot, afternoon walks through town, and enjoying everything this vibrant community has to offer right outside your door. Inside, you'll find a comfortable a

$479,500

4 beds2 baths1,560 sq ft

105 State St, Stevensville, MD 21666

Public sewer • Charming sunporch • White picket fence

(703) 378-8810

OPEN SAT, 9AM TO 11AMFLOOR PLAN

$650,000

4 beds2.5 baths2,540 sq ft

129 Anna Carol Dr, Stevensville, MD 21666

6,250 sq ft lot • 2 garage spots • Built 2018

(302) 539-0800

ABOUT THIS HOME
4 Bedroom Homes for Sale in Chester, MD
Love Point Area - Pristine home located on 1.43 acres with no HOA. This home offers you the opportunity to have space inside and outside. The property features an inground pool and screen porch for perfect outdoor entertaining. Privacy and still convenient to shopping and for commuting. The pride of ownership shows throughout this home and offers upgrades and open living space for entertaining. This property is in move in condition and ready for you to call home!

$849,000

4 beds3 baths2,368 sq ft

1413 Love Point Rd, Stevensville, MD 21666

Outdoor entertaining • Inground pool • Move in condition

(410) 643-2244

ABOUT THIS HOME
4 Bedroom Homes for Sale in Chester, MD
This charming farmhouse sits in the heart of downtown Stevensville! Zoned MULTI USE Residential/Commercial with a SHVC designation. Add your finishing touches and make this place a showstopper. Enjoy the cozy front porch and watch the parades with your own front row seats. Can be the perfect place to run a home business! Featuring 3 levels, this property feels much larger than it looks! Schedule your showing today.

$399,000

4 beds2 baths1,720 sq ft

400 Main St, Stevensville, MD 21666

3 levels • Cozy front porch • 0.29 acre lot

(410) 224-2200

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

$565,000

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

Property at 624 Davol Rd, Stevensville, MD 21666, 4 beds, 3.5 baths

$565,000

4 beds3.5 baths2,408 sq ft

624 Davol Rd, Stevensville, MD 21666

(703) 378-8810

Property at 310 Allison Jane Dr Unit H-1, Stevensville, MD 21666, 4 beds, 4.5 baths

$569,000

4 beds4.5 baths2,850 sq ft

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

(703) 378-8810

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

$625,000

4 beds2.5 baths2,708 sq ft

376 Web Foot Ln, Stevensville, MD 21666

(410) 643-2244

Property at 102 Sophie Ln, Stevensville, MD 21666, 4 beds, 2.5 baths

$429,900

4 beds2.5 baths1,880 sq ft

102 Sophie Ln, Stevensville, MD 21666

(410) 255-3690

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

$487,500

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 12 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 76 days and receive 1 offers. This map is refreshed with the newest listings in Chester every 15 minutes.

In the past month, 14 homes have been sold in Chester. In addition to houses in Chester, there were also 17 condos, 25 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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