Homes with a View for Sale in Chester, MD

18 homes

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COMING SOON

$330,000

1 bed1 bath724 sq ft

10-B Queen Elizabeth Ct, Chester, MD 21619

$189 HOA • Community pool • Built 1983

(410) 643-2244

VIDEO TOUR

ABOUT THIS HOME
Home with View for sale in Chester, MD:
Set within Southwind, one of Kent Island’s most sought-after waterfront communities, this exceptional residence offers an elegant blend of craftsmanship and comfort with 10 foot ceilings and beautiful crown molding. Perfectly sited on an acre overlooking Crab Alley Bay and Eastern Bay, the home’s peaceful setting is enhanced by sweeping water views, mature landscaping, and a private waterside pool that invites year-round enjoyment. Inside, timeless design meets modern refinement. The first-floor primary suite provides a serene retreat, joined by two additional guest suites on the main level—each with its own ensuite bath for privacy and comfort. Upstairs, a fourth bedroom

$1,899,000

4 beds5 baths3,460 sq ft

2907 Cox Neck Rd E, Chester, MD 21619

1 acre lot • 2 garage spots • Pool

(410) 280-5600

ABOUT THIS HOME
Home with View for sale in Chester, MD:
Discover exceptional living on an oversized fenced lot in the sought-after community of Gibson’s Grant on Kent Island. This beautifully maintained home offers a rare combination of space, versatility, and thoughtful upgrades—inside and out. A welcoming front porch overlooks a peaceful community green space, setting the tone for the charm found throughout. Step inside to hardwood floors spanning the main level, where a cozy living room with a propane fireplace flows seamlessly into the open kitchen and dining area. The kitchen features stainless steel appliances, a pantry, and convenient access to the laundry room and main-level half bath. Just off the dining area, enjoy the thre

$659,000

2 beds3.5 baths2,400 sq ft

132 Claiborne St, Chester, MD 21619

Outdoor pool • Three season room • Fitness center

(410) 263-8686

ABOUT THIS HOME
Home with View for sale in Chester, MD:
Private Waterfront Living in Kirwans Landing! Nestled on 1.4 acres in the water-privileged community of Kirwans Landing, this property offers the perfect blend of privacy, comfort, and resort-style outdoor living. Step outside to your own outdoor oasis, complete with a saltwater pool, spacious deck, and beautifully hardscaped patio surrounded by mature landscaping. A private 90-foot pier, tucked off to the side of the property, provides the ideal spot for boating, fishing, paddle boarding, or simply soaking in the peaceful water views. You will also enjoy access to the community marina, just a short ride away. Inside, the home features hardwood floors throughout and a bright, updated kitch

$949,000

4 beds2.5 baths2,404 sq ft

162 Kirwans Landing Ln, Chester, MD 21619

1.4 acre lot • 2 garage spots • Pool

(410) 263-8686

NEW CONSTRUCTION

ABOUT THIS HOME
Home with View for sale in Chester, MD:
To-be-built 5BR, 3.5BA waterfront home by Laine Street Homes — now under construction and perfectly positioned to capture breathtaking sunrises over the waterfront of Crab Alley Creek. Thoughtfully designed for modern coastal living, this home will offer panoramic water views from the main level and the primary suite, filling the interior with natural light and scenic beauty. The bright layout will feature 7” plank flooring, a gas fireplace, and a first-floor guest suite. The gourmet kitchen will include shaker-style cabinetry, quartz countertops, an oversized island, and premium ZLINE stainless appliances — ideal for entertaining while overlooking the water. Upstairs, the

$1,099,900

5 beds3.5 baths3,036 sq ft

203 Riverside Dr, Chester, MD 21619

Waterfront home • Gourmet kitchen • Oversized island

(301) 945-9010

Property at 906 Auckland Way, Chester, MD 21619, 3 beds, 3.5 baths

$520,000

3 beds3.5 baths2,076 sq ft

906 Auckland Way, Chester, MD 21619

(410) 673-3344

Property at 1401 Calvert Rd, Chester, MD 21619, 2 beds, 2 baths

$454,900

2 beds2 baths1,444 sq ft

1401 Calvert Rd, Chester, MD 21619

(410) 643-5005

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

$339,900

2 beds2.5 baths1,440 sq ft

30-C Queen Mary Ct, Chester, MD 21619

(410) 255-3690

Property at 2865 Cox Neck Rd, Chester, MD 21619, 4 beds, 3.5 baths

$2,259,000

4 beds3.5 baths5,122 sq ft

2865 Cox Neck Rd, Chester, MD 21619

(410) 721-1500

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

$1,125,000

4 beds3.5 baths— sq ft

1757 Harbor Dr, Chester, MD 21619

(410) 729-7700

Property at 312 Teal Ct Unit F, Chester, MD 21619, 2 beds, 2 baths

$305,000

2 beds2 baths1,073 sq ft

312 Teal Ct Unit F, Chester, MD 21619

(443) 292-6767

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

$399,000

3 beds2.5 baths1,680 sq ft

9-B Queen Victoria Way, Chester, MD 21619

(301) 490-5400

Property at 141 Switchgrass Way #34, Chester, MD 21619, 3 beds, 2.5 baths

$684,950

3 beds2.5 baths2,600 sq ft

141 Switchgrass Way #34, Chester, MD 21619

(443) 274-1900

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 132 Wheelhouse Way, Chester, MD 21619, 2 beds, 2.5 baths

$1,350,000

2 beds2.5 baths1,900 sq ft

132 Wheelhouse Way, Chester, MD 21619

(240) 375-5074

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

$740,000

3 beds2.5 baths2,602 sq ft

170 Harrier Way #34, Chester, MD 21619

(410) 263-3400

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

$488,000

2 beds2.5 baths1,900 sq ft

1000 Herons Nest Way #22, Chester, MD 21619

(443) 274-1900

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ABOUT THIS HOME
Home with View for sale in Chester, MD:
Discover a home created with intention, balance, and timeless simplicity. Tastefully renovated from top to bottom, this Japandi-style residence brings together the warmth of Scandinavian comfort with the refined serenity of Japanese design, resulting in a space that feels peaceful, functional, and thoughtfully upgraded with every detail in mind. Enjoy your updated home knowing that you will never have to worry about exterior maintenance of the home as this is covered by the community. The living area has large windows that invite natural light to fill the space. An electronic blackout drapery system can control the floor-to-ceiling doors and windows. The electric fireplace and wood hearth c

$599,999

2 beds2.5 baths1,504 sq ft

730 Thompson Creek Rd, Stevensville, MD 21666

Electric fireplace • Bespoke appliances • $570 HOA

(410) 312-0000

ABOUT THIS HOME
Home with View for sale in Chester, MD:
DEEDED BOAT SLIP - Seller offering a 2-1 buy down -✨ What’s a 2-1 Buydown? ✨ It’s a temporary mortgage rate reduction that lowers your payment for the first two years. ✔️ Year 1: Rate is 2% lower ✔️ Year 2: Rate is 1% lower . Year 3+: Back to your original fixed rate 💰 This means lower monthly payments upfront and an easier transition into homeownership. -LIVE EVERYDAY LIKE YOUR ON VACATION in this completely renovated, designer-inspired two-level end-unit water view townhome offering 2 bedrooms, 2.5 baths, and 2,031 sq ft of coastal luxury! Shows like a model home—every detail has been thoughtfully curated. Enjoy breathtaking sunsets from one of the three private decks.

$580,000

2 beds2.5 baths2,031 sq ft

112 Bayview, Grasonville, MD 21638

$650 HOA • Garage • Community pool

(410) 643-2244

ABOUT THIS HOME
Home with View for sale in Chester, MD:
WATERFRONT (20 acres) located on the Northern section of Kent Island, in the area of larger acreage estates, the "Pink House" provides a peaceful respite from the rush of the world. As easy 5 minute drive from the Chesapeake Bay Bridge the home offers access to the western shore metro areas. With over a 1000' of protected shoreline fronting along the broad, open waters of the Chester River the has 100'+ pier offers 4' MLW. A waterfowl hunter's delight you'll find a blind on the pier and one offshore as well. A generously proportioned inground pool with an expansive apron for lounging and dining is a focal point between the house and the river. An outdoor kitchen, huge deck and a

$2,895,000

4 beds4.5 baths6,361 sq ft

220 Old Steamship Rd, Stevensville, MD 21666

20.69 acre lot • 8 parking spots • Pool

(410) 643-2244

ABOUT THIS HOME
Home with View for sale in Chester, MD:
This boater's paradise demonstrates the perfect blend of luxury and convenience. The property boasts three floors of sweeping waterfront views all easily accessed via your own private elevator. High end finishes can be found throughout and the home has been impeccably maintained. The first floor feels inviting with the fireplace, open kitchen, and guest bedroom with ensuite full bathroom currently being used as an office. The second floors wows you with 3 spacious bedrooms including the primary that has a walkout balcony for quiet evenings staring out over the water. The top floor provides yet another entertaining or living space with a wet bar, full bathroom, and a walk out balcony. Outdoo

$950,000

4 beds4 baths2,653 sq ft

110 Channel Marker Way #203, Grasonville, MD 21638

Waterfront views • Wet bar • Walkout balcony

(410) 778-0330

NEW CONSTRUCTION

ABOUT THIS HOME
Home with View for sale in Chester, MD:
The Chester blends modern design with everyday comfort in a thoughtfully designed layout perfect for both work and relaxation. Featuring 2 bedrooms, 2.5 baths, and a 1-car garage, this home offers stylish finishes and smart functionality throughout. Standout features include a home office with lited French doors, an electric fireplace that adds warmth and ambiance, and a convenient dry bar for entertaining or casual gatherings. The kitchen is beautifully equipped with a single oven, microwave, gas cooktop, range hood, dishwasher, pendant lighting, and tile backsplash, all complemented by quartz countertops for a polished look. Laminate flooring runs throughout the main living areas, with ti

$654,900

2 beds2.5 baths1,900 sq ft

630 Warbler Way #2233, Chester, MD 21619

Quartz countertops • Laminate flooring • Dry bar

(240) 375-5074

NEW CONSTRUCTION

ABOUT THIS HOME
Home with View for sale in Chester, MD:
The Chester blends modern design with everyday comfort in a thoughtfully designed layout perfect for both work and relaxation. Featuring 2 bedrooms, 2.5 baths, and a 1-car garage, this home offers stylish finishes and smart functionality throughout. Standout features include a home office with lited French doors, an electric fireplace that adds warmth and ambiance, and a convenient dry bar for entertaining or casual gatherings. The kitchen is beautifully equipped with a single oven, microwave, gas cooktop, range hood, dishwasher, pendant lighting, and tile backsplash, all complemented by quartz countertops for a polished look. Laminate flooring runs throughout the main living areas, with ti

$654,900

2 beds2.5 baths1,900 sq ft

630 Warbler Way #2232, Chester, MD 21619

Double sinks • Quartz countertops • Dry bar

(240) 375-5074

Property at 346 Narrows Pointe Dr, Grasonville, MD 21638, 3 beds, 3.5 baths

$1,310,000

3 beds3.5 baths3,000 sq ft

346 Narrows Pointe Dr, Grasonville, MD 21638

(410) 505-9700

Property at 630 Warbler Way #2224, Chester, MD 21619, 2 beds, 2.5 baths

$724,900

2 beds2.5 baths2,602 sq ft

630 Warbler Way #2224, Chester, MD 21619

(240) 375-5074

Property at 630 Warbler Way #2222, Chester, MD 21619, 2 beds, 2.5 baths

$574,900

2 beds2.5 baths1,900 sq ft

630 Warbler Way #2222, Chester, MD 21619

(240) 375-5074

Property at 426 Narrows Pointe Dr, Grasonville, MD 21638, 3 beds, 3.5 baths

$1,349,900

3 beds3.5 baths2,860 sq ft

426 Narrows Pointe Dr, Grasonville, MD 21638

(888) 860-7369

Property at 10 Genevieve Ct, Stevensville, MD 21666, 3 beds, 2.5 baths

$470,000

3 beds2.5 baths2,232 sq ft

10 Genevieve Ct, Stevensville, MD 21666

(410) 758-0333

Property at 522 Narrows Pointe Dr, Grasonville, MD 21638, 3 beds, 3.5 baths

$1,395,000

3 beds3.5 baths3,000 sq ft

522 Narrows Pointe Dr, Grasonville, MD 21638

(410) 505-9700

Property at 312 Topside Dr #223, Stevensville, MD 21666, 3 beds, 3 baths

$665,000

3 beds3 baths2,844 sq ft

312 Topside Dr #223, Stevensville, MD 21666

(410) 429-7425

Property at 200 Bridgeview Ln, Stevensville, MD 21666, 8 beds, 8.5 baths

$14,950,000

8 beds8.5 baths20,013 sq ft

200 Bridgeview Ln, Stevensville, MD 21666

(410) 280-5600

Homes with a View for Sale in Chester

There are currently 18 homes with a view homes for sale in Chester at a median listing price of $550K. 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 75 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 16 condos, 12 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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