Chester, MD Homes for Sale

40 of 57 homes•

Sort:

Chester, MD Home for Sale

Gorgeous 5 Bedroom 3 Full Bath single family home with a water view! Completely renovated and situated on a large . 87 acre lot. Open concept kitchen with White Shaker cabinets, granite counters, stainless steel appliances, peninsula with additional seating and LVP floors. Upper level with 3 generous bedrooms and primary bedroom with separate bath and luxury shower. Lower level with 2 bedrooms and large family room with plenty of natural light. Roof- 3 years new. Oversized driveway for multiple cars/RV parking and separate detached garage with electric. A Must See!

Photo of 237 Bentons Pleasure Rd, Chester, MD 21619

1 / 41

LISTED BY REDFIN

3D WALKTHROUGH

$515,000

5 Beds

3 Baths

2,184 Sq. Ft.

237 Bentons Pleasure Rd, Chester, MD 21619

Chester, MD Home for Sale

Private home office with elegant French doors. Spectacular gourmet kitchen with spacious island and designer cabinets. Charming dining area with convenient dry bar. Gorgeous great room with electric fireplace and slider to balcony. Luxurious owner's suite with triple windows and balcony access. Lavish owner's spa bath with split vanities .

Photo of 132 Wheelhouse Way, Unit 23, Chester, MD 21619

1 / 17

NEW 8 HRS AGO

$659,900

2 Beds

2.5 Baths

2,000 Sq. Ft.

132 Wheelhouse Way, Unit 23, Chester, MD 21619

Chester, MD Home for Sale

Welcome to 201 Gibson Circle in Chester, MD! This Stunning End unit townhome in the Desired Community of Gibsons Grant on the Chester River and Macum Creek is ready for you! Boasting a Contemporary Coastal design and immaculate condition, this property is a Perfect fit for anyone seeking a Stylish, Spacious Home to move right in and not have to do a thing! Abundant windows with Tons of Natural light offer a Bright and inviting atmosphere throughout. The surrounding plush Green Space creates a Peaceful setting, especially when enjoyed from the maintenance free, private side deck. Bring your rockers to enjoy the sprawling covered front porch. .. AND it is ALL about the decor on the porches he

Photo of 201 Gibson Cir, Chester, MD 21619

1 / 70

OPEN TODAY, 10AM TO 12PM

$599,900

3 Beds

2.5 Baths

2,650 Sq. Ft.

201 Gibson Cir, Chester, MD 21619

(443) 274-1900

201 Gibson Cir, Chester, MD 21619

Chester, MD Home for Sale

This property is so relaxing, you can sit on the deck and think of nothing, listening to the sound of the fountain in the lake and look out over the water, it is what everyone needs. This beauty has been completely updated and features Stainless Appliances with Granite Counters, Life Proof Flooring, Fresh Paint , HVAC in 2016 and a climate controlled One Car Garage with a floor you could eat off of. You literally have views from every room, from the upper deck AND the Walk out lower level patio. All this in sought after Bayside Community, near the Pool, Hot Tub, Fitness Room and Tennis Courts. The location can't be beat !!!

Photo of 212 Ringneck Ct, Chester, MD 21619

1 / 40

OPEN TODAY, 1PM TO 3PM

$399,000

3 Beds

2.5 Baths

1,747 Sq. Ft.

212 Ringneck Ct, Chester, MD 21619

(410) 643-2166

212 Ringneck Ct, Chester, MD 21619

Chester, MD Home for Sale

Kent Island Waterfront on Cox Creek!! Public Sewer available, road frontage is 45ft. This is a flag lot with opening on the waterfront of 108 ft. This property does not have a pier, so please do not go on pier. This is the perfect lot to build your dream home. The natural environment has wildlife and waterfowl and as well as good fishing and crabbing. If you want a piece of the shore-life this is the property you have been looking for.

1 / 8

$300,000

—Beds

—Baths

0.68 Acre (Lot)

Parks Rd, Chester, MD 21619

(410) 643-2244

Parks Rd, Chester, MD 21619

Chester, MD Home for Sale

This home is under construction and is estimating to be move in ready by October 2023! This particular home comes included with a fireplace and a dry bar. Welcome to a new luxury active adult 55+ community on Maryland's Chesapeake Bay. Discover the amenity-filled, resort-style experience within 45 miles of Washington DC and Baltimore. Residents can take advantage of the community's 24,000 sq. ft. clubhouse with indoor & outdoor pools, a state-of-the-art fitness center, and multiple tennis and pickleball courts. With a full-time lifestyle director on site the community also features a well-maintained calendar of activities such as walking club, indoor and outdoor yoga sessions, mahjon

1 / 18

NEW CONSTRUCTION

$659,900

2 Beds

2.5 Baths

2,000 Sq. Ft.

132 Wheelhouse Way #1923, Chester, MD 21619

(240) 375-5074

132 Wheelhouse Way #1923, Chester, MD 21619

Chester, MD Home for Sale

This is the waterfront dream home you’ve been waiting for! Are you looking for expansive bay views from your forever home or second home on the Eastern Shore? This 5 BR, 2.5 BA property with 110 feet of rip rapped waterfront delivers with 2.9 manicured acres (one of the largest lots in the community!) in the serene upscale community of Southwind. You will enjoy this secluded setting with wide sweeping water views surrounded by Crab Alley and Eastern Bay. Just steps down the back yard is the six-foot wide pier with both boat and jet ski lifts and a gorgeous custom salt-water pool surrounded by a pristine paver patio and walkways. Enjoy boating, jet skiing, fishing, crabbing or just

1 / 86

OPEN TODAY, 10AM TO 12PM

$2,100,000

5 Beds

2.5 Baths

3,716 Sq. Ft.

2861 Cox Neck Rd, Chester, MD 21619

(410) 224-2200

2861 Cox Neck Rd, Chester, MD 21619

Chester, MD Home for Sale

Welcome to Eastern Shore living at Bayside! This meticulously cared for three level water-view townhome overlooks Northeast Bay and the Chester River. Amazing open-concept floorplan allows for plenty of room to entertain indoors or outdoors. Main level boasts wood floors, rich paint, custom moldings, plantation shutters, gas fireplace, recessed lighting, and more. Bright and airy kitchen to include white cabinets, sleek appliances, granite counter-tops, paint, and lighting/fixtures. Enormous Primary Bedroom with private deck/balcony, large walk-in closet, and spa-like bathroom. Second bedroom suite with private bathroom and large closet. Third bedroom/loft has views of the Bay, vaulted cei

1 / 47

OPEN SUN, 1PM TO 3PM

$447,500

3 Beds

3.5 Baths

2,100 Sq. Ft.

915 Auckland Way, Chester, MD 21619

(410) 729-7700

915 Auckland Way, Chester, MD 21619

Chester, MD Home for Sale

Welcome to 2015 Stevens Drive!! Tucked away right off Route 50, this beautiful 3-bedroom, 3-bathroom split foyer home in Chester, Maryland, is a wonderful opportunity to enjoy comfortable living in a peaceful and welcoming community. Arriving to the property, you are greeted by a well-maintained front yard with lush greenery and raised flower beds, the split foyer design gives the home a distinctive look, with a welcoming front entrance. As you enter the home, in true split foyer style, you are greeted by stairs leading to the main level, as well as the lower level. Upstairs on the main level, you will find yourself greeted by a beautiful spacious, living room featuring large windows and a

1 / 43

$469,000

3 Beds

3 Baths

2,272 Sq. Ft.

2015 Stevens Dr, Chester, MD 21619

(410) 312-0000

2015 Stevens Dr, Chester, MD 21619

Chester, MD Home for Sale

Bridgepointe Townhome - this desirable Kent Island Community is located just off Rt. 50. Fabulous Two Story Townhome is ready for YOU! Inviting Front Porch and Foyer opens to Beautiful Kitchen with Breakfast Nook, Large Dining and Living Room includes Brilliant Hardwood Flooring. Bright Open Floor Plan. Sliding Door - opens to Large Deck w/ built in storage shed and Electronic Awning. Relax and enjoy the peaceful views. Second Floor includes Master Suite with Private Bathroom, Second Bedroom and Den (could be 3rd Bedroom) and Full Bath in Hall. NEW in 2023 Hot Water Heater, Dehumidifier in Crawl Space, Washer and Dryer. The Garage was converted into step down Family Room with French Doo

1 / 40

OPEN TODAY, 10AM TO 12PM

$360,000

3 Beds

2.5 Baths

1,302 Sq. Ft.

7003 Bridgepointe Dr, Chester, MD 21619

(410) 643-2166

7003 Bridgepointe Dr, Chester, MD 21619

1 / 35

OPEN SUN, 11AM TO 1PM

$355,000

2 Beds

2.5 Baths

1,312 Sq. Ft.

44-B Queen Neva Ct, Chester, MD 21619

(410) 814-2400

44-B Queen Neva Ct, Chester, MD 21619

Chester, MD Home for Sale

Lovely 2nd floor condo with private deck on lake. 2 bedroom / 2 new full bath, unit with ALL NEW appliances, new carpet, freshly painted.

1 / 6

$295,000

2 Beds

2 Baths

1,069 Sq. Ft.

513 Teal Ct Unit G, Chester, MD 21619

(410) 643-2244

513 Teal Ct Unit G, Chester, MD 21619

Chester, MD Home for Sale

The stunning 109 John Dabb Court, nestled within the highly sought-after waterfront community of Gibson's Grant and just a block away from the Chester River! Step onto the inviting porch and immediately embrace a sense of tranquility. This thoughtfully designed, newly built home (Koch Kingston 2019) seamlessly guides you through the living areas on the first floor, including a family room accompanied by a cozy fireplace, dining space, to an upgraded kitchen featuring premium appliances. Adding to the ease of living, a convenient first-floor bedroom and a full bathroom awaits. On the second level, discover 3 bedrooms and 2 bathrooms tailored for modern comfort. Through French doors, the prim

1 / 72

OPEN TODAY, 2PM TO 4PM

$875,000

4 Beds

3 Baths

2,920 Sq. Ft.

109 John Dabb Ct, Chester, MD 21619

(410) 729-7700

109 John Dabb Ct, Chester, MD 21619

Chester, MD Home for Sale

Welcome to your dream home in Chester, Maryland, located on Kent Island! This charming rancher offers the perfect blend of comfort and convenience with its one-level living design. The highlight of this home is the spacious bonus room off the kitchen, complete with a cozy pellet stove and electric heating elements for those cooler evenings. The recently remodeled kitchen boasts stainless steel appliances, giving it a modern and sleek touch. Natural light floods through the windows, creating a warm and inviting atmosphere throughout the house. The generously-sized driveway provides ample space for parking your camper or boat, making it a breeze to enjoy outdoor adventures. Additionally, the

1 / 33

$399,997

3 Beds

1 Bath

1,770 Sq. Ft.

2655 Cox Neck Rd, Chester, MD 21619

(410) 255-0000

2655 Cox Neck Rd, Chester, MD 21619

Chester, MD Home for Sale

This one-level Rambler, located in a waterfront community, sits on . 739 acres and has a water view of Crab Alley Creek. This home has no HOA and offers 3/ bedrooms, 2/ full baths, a living room, a family room with a wood-burning fireplace, an eat-in kitchen, and an oversized attached garage. The primary bedroom offers luxury vinyl plank flooring and a closet organizer system. The primary bedroom has tile flooring with a tile surround shower and a deep jetted tub. The hall full bath has new vinyl flooring and houses the washer and dryer. The other 2/ bedrooms offer large space and nice-sized closets with carpet flooring. The living room has plank flooring with recessed lights and is a nic

1 / 54

OPEN OCT 7, 1PM TO 3PM

$465,000

3 Beds

2 Baths

1,632 Sq. Ft.

205 Newtown Rd, Chester, MD 21619

(301) 843-5100

205 Newtown Rd, Chester, MD 21619

Chester, MD Home for Sale

* * * Sellers have found their home of choice! Bring us an Offer! * * * Welcome to Queens Landing in charming Chester, MD! This wonderful 3-level townhome boasts elegant Spanish-style architecture and is one of the most spacious models within the community. * * Key Features * * * * Brava Model with expansive 12x26 Loft: Enjoy the luxury of an expansive loft space, perfect for a home office, entertainment area, or additional living space. This unique feature adds versatility and ample room to tailor to your lifestyle. * * Remodeled Kitchen: The heart of this home features a thoughtfully remodeled kitchen with a pantry, Corian countertops, and wainscot detailing. Functionality meet

1 / 40

$395,000

3 Beds

2.5 Baths

1,680 Sq. Ft.

12-D Queen Anne Way Unit D, Chester, MD 21619

(410) 260-2800

12-D Queen Anne Way Unit D, Chester, MD 21619

Chester, MD Home for Sale

Price Adjustment of $10,000! Welcome to 1808 Chester Drive located in the Harbor View community on beautiful Kent Island. Step inside and you will fall in love with this One Level Living home located boasting approximately 1700 sq ft of living space and offering 3 Bedrooms + Den and 1.5 Bathrooms. The split floor plan offers privacy and generously sized bedrooms. The garage was converted to host the primary bedroom, plus a conditioned workshop/studio. The kitchen offers newer appliances, a breakfast bar, and slider to the HUGE backyard! In the - there are currently two sheds (1 with electric perfect for a man cave, she shed, office or gym), an above ground pool, firepit area, patio, and ple

1 / 44

$365,000

3 Beds

1.5 Baths

1,700 Sq. Ft.

1808 Chester Dr, Chester, MD 21619

(410) 729-7700

1808 Chester Dr, Chester, MD 21619

Chester, MD Home for Sale

2 Bedroom 2 1/2 bath townhouse in Queens Landing. Rear patio and Balcony overlook the lake and fountain. Hardwood floors on first level, wall to wall carpet on upper levels. Laundry closet on second floor. Community features pool, walking paths, tennis courts, gym, and clubhouse on the Chester River. Storage closets off balcony and patio. Enjoy numerous community amenities including a marina, swimming pool on the Chester River, tennis/pickle ball courts, clubhouse with social room, waterfront walking path, exercise room, and racquetball. New roof installed in 9/2020. New hot water heater, newer windows and doors. All assessments have been paid and no poly-pipes are present.

1 / 36

$379,000

2 Beds

2 Baths

1,660 Sq. Ft.

28-J Queen Mary Ct, Chester, MD 21619

(410) 213-7040

28-J Queen Mary Ct, Chester, MD 21619

Chester, MD Home for Sale

The Jenkins II model is a show stopper! This home showcases a Loft look. This home also features a screened patio and fireplace as well as upgraded shower. For a full list of features please see a sales representative. Welcome to a new luxury active adult 55+ community on Maryland's Chesapeake Bay. Discover the amenity-filled, resort-style experience within 45 miles of Washington DC and Baltimore. Residents can take advantage of the community's 24,000 sq. ft. clubhouse with indoor & outdoor pools, a state-of-the-art fitness center, and multiple tennis and pickleball courts. With a full-time lifestyle director on site the community also features a well-maintained calendar of activiti

1 / 55

NEW CONSTRUCTION

$659,900

2 Beds

2 Baths

2,019 Sq. Ft.

126 Merlin Dr, Chester, MD 21619

(240) 375-5074

126 Merlin Dr, Chester, MD 21619

Chester, MD Home for Sale

The Bernstein II model is a show stopper! This home includes a fireplace as well as an upgraded shower. This home features the Classic Look. For a full list of features please see a sales representative. Welcome to a new luxury active adult 55+ community on Maryland's Chesapeake Bay. Discover the amenity-filled, resort-style experience within 45 miles of Washington DC and Baltimore. Residents can take advantage of the community's 24,000 sq. ft. clubhouse with indoor & outdoor pools, a state-of-the-art fitness center, and multiple tennis and pickleball courts. With a full-time lifestyle director on site the community also features a well-maintained calendar of activities such as walkin

1 / 41

NEW CONSTRUCTION

$647,900

2 Beds

2 Baths

1,693 Sq. Ft.

122 Merlin Dr, Chester, MD 21619

(240) 375-5074

122 Merlin Dr, Chester, MD 21619

Chester, MD Home for Sale

The Kelly model is first floor living at its finest. This home features a screened patio, fireplace, upgraded shower and detailed trim in the foyer and primary bedroom. . For a full list of included features please consult a sales representative. Welcome to a new luxury active adult 55+ community on Maryland's Chesapeake Bay. Discover the amenity-filled, resort-style experience within 45 miles of Washington DC and Baltimore. Residents can take advantage of the community's 24,000 sq. ft. clubhouse with indoor & outdoor pools, a state-of-the-art fitness center, and multiple tennis and pickleball courts. With a full-time lifestyle director on site the community also features a well-main

1 / 41

NEW CONSTRUCTION

$744,900

2 Beds

2 Baths

2,013 Sq. Ft.

106 Merlin Dr, Chester, MD 21619

(240) 375-5074

106 Merlin Dr, Chester, MD 21619

Chester, MD Home for Sale

The Bernstein II model is a show stopper! This home features a fireplace as well as a screened patio. For a full list of features please see a sales representative. Welcome to a new luxury active adult 55+ community on Maryland's Chesapeake Bay. Discover the amenity-filled, resort-style experience within 45 miles of Washington DC and Baltimore. Residents can take advantage of the community's 24,000 sq. ft. clubhouse with indoor & outdoor pools, a state-of-the-art fitness center, and multiple tennis and pickleball courts. With a full-time lifestyle director on site the community also features a well-maintained calendar of activities such as walking club, indoor and outdoor yoga session

1 / 41

NEW CONSTRUCTION

$599,900

2 Beds

2 Baths

1,693 Sq. Ft.

136 Merlin Dr, Chester, MD 21619

(240) 375-5074

136 Merlin Dr, Chester, MD 21619

Chester, MD Home for Sale

Live in the resort-style community of Queen’s Landing! This WATER privileged end-unit home offers three bedrooms and two full baths on the main level, a loft, and multiple outdoor living opportunities to view the marina and watch spectacular sunsets. Enjoy numerous community amenities including a marina, swimming pool on the Chester River, tennis/pickle ball courts, clubhouse with social room, waterfront walking path, exercise room, and racquetball. The welcoming interior is introduced by beautiful glass panel doors with flanking windows illuminating the neutral color palette and hardwood floors. The spacious open concept living, dining, and kitchen provides unparalleled convenience c

1 / 44

3D WALKTHROUGH

$399,000

3 Beds

2 Baths

1,260 Sq. Ft.

2-A Queen Victoria Ct, Chester, MD 21619

(410) 465-1770

2-A Queen Victoria Ct, Chester, MD 21619

Chester, MD Home for Sale

KENT ISLAND - Hurry to Harbor View. This move in ready home features over 2,200 sq ft of well maintained space for you and your family. From the front covered porch you are welcomed into the spacious central foyer, which flows into the spacious kitchen and dining area filled with lots of natural light, upgrades galore, new appliances, and an exit to the fully fenced backyard oasis. Relax by the fire in the living room or hang out in the newly added family room which leads to the backyard with paver patio, large deck, shaded lawn, mature landscaping, vegetable garden, storage shed and garage/workshop. The upstairs offers 3 large bedrooms, 2 full baths and private office. Owners have made man

1 / 34

$479,000

3 Beds

2.5 Baths

2,238 Sq. Ft.

1852 Harbor Dr, Chester, MD 21619

(410) 643-5005

1852 Harbor Dr, Chester, MD 21619

Chester, MD Home for Sale

For Sale and For Rent. .. Welcome to this stunning property that seamlessly combines modern upgrades and convenience in a desirable location. This thoughtfully renovated 3-bedroom, 2-full bath home provides a comfortable and stylish living experience. With numerous updates completed in 2018, including the HVAC system, kitchen, roof, and the addition of a new septic system in 2019, this home is move-in ready and sure to impress. Upon entering, you'll be greeted by a well-designed floor plan that caters to easy living. The spacious and inviting kitchen is truly a showstopper, boasting modern appliances, beautiful countertops, and ample cabinetry. Whether you're a culinary enthusiast or simply

1 / 30

$350,000

3 Beds

2 Baths

1,104 Sq. Ft.

1435 Cox Neck Rd, Chester, MD 21619

(410) 729-7700

1435 Cox Neck Rd, Chester, MD 21619

Chester, MD Home for Sale

The Severn model is a spacious and airy 3 bedroom, 2.5 bath end-home unit boasting an expansive open floor plan with over 2600 square feet of luxurious living space. This home features a lavish gourmet kitchen and dining area, a huge great room with sliding door access to a large corner balcony. The centerpiece kitchen is equipped with GE Profile appliances and gas stove top, granite counters, an oversized kitchen island, and custom backsplash. The fantastic owner's suite has an adjoining sitting room with access to the balcony, an extravagant owner's spa bath and 2 walk-in closets. Two large secondary bedrooms are located in a separate wing of the home and each features a walk-in closet a

1 / 47

OPEN SUN, 1PM TO 4PM

$680,000

3 Beds

2.5 Baths

—Sq. Ft.

3000 Herons Nest Way #24, Chester, MD 21619

(443) 274-1900

3000 Herons Nest Way #24, Chester, MD 21619

Chester, MD Home for Sale

TO BE BUILT. This two-story, two-car garage center hall design is a great multi-generational home option for families looking to accommodate lots of varying needs under one roof! The Congressional features a formal dining room, breakfast area, main level owner's suite and laundry room, 4 bedrooms, 2.5 baths, mud room access from the garage, and much more. This plan offers numerous customization opportunities -- choose to finish dual owner's suites -- one on the main level and a second on the upstairs level, or, create a large rec/play area for kids/family. The options are endless and you'll love designing the home that meets your lifestyle needs!

1 / 29

NEW CONSTRUCTION

3D WALKTHROUGH

$689,900

4 Beds

2.5 Baths

—Sq. Ft.

Lot 52 Woods Rd, Chester, MD 21619

(410) 729-7700

Lot 52 Woods Rd, Chester, MD 21619

Chester, MD Home for Sale

One of our most popular designs, the Doral offers formal ( office space) and informal living areas with lots of room for the whole family to spread out. Your main level features a spacious family room and table space kitchen. Add a light-filled morning room off the rear or expand your space with plan extension. Upstairs, plans accommodate 4 nicely sized bedrooms, 2 full baths and large laundry area. Granite, luxury LVP hardwood flooring, tile baths and more. To be built. Time to personalize this home to your individual taste.

1 / 18

OPEN SUN, 12:30PM TO 2:30PM

$629,900

4 Beds

3 Baths

—Sq. Ft.

Lot 53 Woods Rd, Chester, MD 21619

(410) 729-7700

Lot 53 Woods Rd, Chester, MD 21619

Chester, MD Home for Sale

This waterfront home is located in the highly sought-after neighborhood of Marling Farms, a bayside community offering common areas, playgrounds, and parks. Scenic western facing garden environment for endless entertainment options on the water with an abundance of fishing, crabbing, and boating. Uniquely positioned deep lot on Crab Alley Bay with spacious lawn and expansive water views. Property has been modernized and extensively remodeled, 4 bedrooms, 3 full baths, and lots of storage. State of the art kitchen with new luxury grade appliances – stove, double oven, convection, warming drawer and wine/beverage cooler. Fresh decking on the boardwalk and dock equipped with water, shore

1 / 47

$1,395,000

4 Beds

3 Baths

3,003 Sq. Ft.

1642 Bayside Dr, Chester, MD 21619

(410) 280-5600

1642 Bayside Dr, Chester, MD 21619

Chester, MD Home for Sale

To be built. The Blue Heron is a new home design offered by Lacrosse Homes. The single family design features now one but TWO decks -- one from the second floor great room and the second from the third level primary bedroom suite. Take in all the beautiful sights and sounds of a Coastal Maryland lifestyle in this home built for entertaining and an enhanced lifestyle! There is room for everyone in this home, starting with a main level 2-car garage, rec room area, full bath & exercise/office -- this is your fun zone or whatever zone! The second level is light-filled and open with island kitchen featuring upgraded finishes, dining area, powder bath and great room with deck. You can ADD a

1 / 35

NEW CONSTRUCTION

$699,900

4 Beds

3.5 Baths

2,350 Sq. Ft.

Lot 9 Harbor Dr, Chester, MD 21619

(410) 729-7700

Lot 9 Harbor Dr, Chester, MD 21619

Chester, MD Home for Sale

Escape to Island Life this Summer and settle into your dream condo now! Available for immediate settlement! No reason to wait until 2024! MOVE THIS Summer! This stunning and immaculate condo is situated in the esteemed "Four Seasons at Kent Island, " a 55+ community in Chester, Maryland. Boasting three generously sized bedrooms and 2.5 bathrooms, this corner unit has everything you would ask for and more. Its top-of-the-line kitchen features upgraded cabinetry, granite countertops, and GE Profile stainless steel appliances, including a propane-powered cooktop, high-end Moen faucets, and fixtures throughout. Enjoy breathtaking views of the nature preserve area, Macum Creek, and sea

1 / 73

VIDEO TOUR

$674,999

3 Beds

2.5 Baths

2,602 Sq. Ft.

4000 Herons Nest Way #34, Chester, MD 21619

(410) 643-3404

4000 Herons Nest Way #34, Chester, MD 21619

Chester, MD Home for Sale

One of our most popular designs, the Doral offers formal ( office space) and informal living areas with lots of room for the whole family to spread out. Your main level features a spacious family room and table space kitchen. Add a light-filled morning room off the rear or expand your space with plan extension. Upstairs, plans accommodate 4 nicely sized bedrooms, 2 full baths and large laundry area. Granite, luxury LVP hardwwod flooring, tile baths and more. Furnished model available for tour. To be built. Time to personalize this home to your individual taste.

1 / 26

NEW CONSTRUCTION

$599,800

4 Beds

2.5 Baths

1,553 Sq. Ft.

Lot 8 Harbor Dr, Chester, MD 21619

(410) 729-7700

Lot 8 Harbor Dr, Chester, MD 21619

Chester, MD Home for Sale

This beautiful 3/4+ acre waterfront lot is READY to ROLL for you to secure a grading permit and building permit. The sewer tap fee is PAID. The Sellers are working to remove the phragmites to get back that beautiful Cox Creek view back. Out on the creek is 6'. .. yes, SIX FEET of water 170' from shore according to the Sellers. This is a rare and beautiful home site in a terrific neighborhood. Don't miss it!

1 / 6

$599,000

—Beds

—Baths

0.78 Acre (Lot)

Parcel 378, Lot 8 Benton's Pleasure Rd, Chester, MD 21619

(410) 643-5005

Parcel 378, Lot 8 Benton's Pleasure Rd, Chester, MD 21619

Chester, MD Home for Sale

You little slice of Cox Creek heaven! This 3/4+ acre lot will support a narrow design up to 28' in width. The Seller reports a 6' water depth at 170' from the shoreline. The sewer tap fee has been PAID and the lot is ready for you to file grading and building permits. Sellers are working to remove the phragmites.

1 / 8

$499,000

—Beds

—Baths

0.75 Acre (Lot)

Parcel 378, Lot 9, Benton's Pleasure Rd, Chester, MD 21619

(410) 643-5005

Parcel 378, Lot 9, Benton's Pleasure Rd, Chester, MD 21619

Chester, MD Home for Sale

A deep-water Cox Creek fixer with great "bones" isn't a home that comes up very often, but here it is! Do a little, or do a lot, as this is a true 1968 time AS-IS time capsule that feels solid under its beautiful hardwood floors. With 5+' water depth and a beautiful view of the creek, your investment will be solid either way. The home is connected to the original septic system, but a sewer tap with a PAID-FOR tap fee is available on-site. Don't miss this one as it is sure not to last long! Note that there is a plotted view lane on the property designed to protect the view of 310 Benton's Pleasure Rd that is included in the documents available to the Buyer. Two adjacent building lo

1 / 34

$999,000

4 Beds

2.5 Baths

2,793 Sq. Ft.

306 Benton's Pleasure Rd, Chester, MD 21619

(410) 643-5005

306 Benton's Pleasure Rd, Chester, MD 21619

Chester, MD Home for Sale

Convenient home office with elegant French doors. Fabulous gourmet kitchen with spacious island and designer cabinets. Delightful dining area with convenient dry bar, perfect for entertaining. Spectacular great room with electric fireplace and slider to balcony. Sophisticated owner's suite with triple windows and balcony access. Stylish owner's spa bath featuring split vanities. .

1 / 17

NEW CONSTRUCTION

$663,900

2 Beds

2.5 Baths

1,900 Sq. Ft.

111 Marshgrass Way, Unit 32, Chester, MD 21619

Chester, MD Home for Sale

Quick Move In! Move in by June 2023 and enjoy all the outdoor amenities the community has to offer. This Chester Model is located on the 4th floor of the condo building which offers sweeping views of the community and its surroundings. Features include a gourmet kitchen, fireplace and upgraded flooring including LVP and Ceramic Tiles. For a full list or to scheduled a tour please contact our sales consultants. Welcome to a new luxury active adult 55+ community on Maryland's Chesapeake Bay. Discover the amenity-filled, resort-style experience within 45 miles of Washington DC and Baltimore. Residents can take advantage of the community's 24,000 sq. ft. clubhouse with indoor & outdoor p

1 / 47

NEW CONSTRUCTION

$649,900

2 Beds

2.5 Baths

1,900 Sq. Ft.

200 Harrier Way #942, Chester, MD 21619

(240) 375-5074

200 Harrier Way #942, Chester, MD 21619

Chester, MD Home for Sale

This home is under construction and will be move in ready by late 2023/early 2024! This home is locateon the 3rd floor of the condo building and features a fireplace, dry bar, laundry cabinets and flooring upgrades. For a full list please contact our sales representatives. Welcome to a new luxury active adult 55+ community on Maryland's Chesapeake Bay. Discover the amenity-filled, resort-style experience within 45 miles of Washington DC and Baltimore. Residents can take advantage of the community's 24,000 sq. ft. clubhouse with indoor & outdoor pools, a state-of-the-art fitness center, and multiple tennis and pickleball courts. With a full-time lifestyle director on site the communit

1 / 48

NEW CONSTRUCTION

$663,900

2 Beds

2.5 Baths

2,200 Sq. Ft.

111 Marshgrass Way #32, Chester, MD 21619

(240) 375-5074

111 Marshgrass Way #32, Chester, MD 21619

Chester, MD Home for Sale

This home is under construction and will be move in ready by late fall of 2023! Welcome to a new luxury active adult 55+ community on Maryland's Chesapeake Bay. Discover the amenity-filled, resort-style experience within 45 miles of Washington DC and Baltimore. Residents can take advantage of the community's 24,000 sq. ft. clubhouse with indoor & outdoor pools, a state-of-the-art fitness center, and multiple tennis and pickleball courts. With a full-time lifestyle director on site the community also features a well-maintained calendar of activities such as walking club, indoor and outdoor yoga sessions, mahjong club, kayaking, pickleball and more. Kent Island life is about making frie

1 / 48

NEW CONSTRUCTION

$631,900

2 Beds

2.5 Baths

1,900 Sq. Ft.

119 Marshgrass Way #1232, Chester, MD 21619

(240) 375-5074

119 Marshgrass Way #1232, Chester, MD 21619

Chester, MD Home for Sale

The Bernstein II model is a show stopper! In the kitchen you will find an upgraded cabinet with stacked glass cabinets on top, quartz countertops and a smart cooking suite by GE. This home also features a fireplace as well as upgraded trim. For a full list of features please see a sales representative. Welcome to a new luxury active adult 55+ community on Maryland's Chesapeake Bay. Discover the amenity-filled, resort-style experience within 45 miles of Washington DC and Baltimore. Residents can take advantage of the community's 24,000 sq. ft. clubhouse with indoor & outdoor pools, a state-of-the-art fitness center, and multiple tennis and pickleball courts. With a full-time lifestyle

1 / 41

NEW CONSTRUCTION

$619,900

2 Beds

2 Baths

1,693 Sq. Ft.

131 Merlin Dr, Chester, MD 21619

(240) 375-5074

131 Merlin Dr, Chester, MD 21619

Viewing page 1 of 2(Download All)

1 2

Average home prices near Chester, MD

Cities

Stevensville homes for sale
$548,900

Zip Codes

Chester, MD real estate trends

Median Sale Price

(All Home Types)

$438,000

+29.6% YoY | Aug 2023

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

Location

Data

Aug 2023

Growth

% YoY

Chester, MD

$438,000

+29.6%

See more Chester, MD market insights

More to explore in Chester, MD

How to buy a house in Chester, MD

How Much House Can I Afford?

How to Buy a House in 10 Steps

First-Time Homebuyer's Guide

See more home buying guides

Living in Chester, MD

Schools
Climate
Things to do

Schools in Chester

Elementary schools

Middle schools

High schools

GreatSchools Rating

7/10 Bayside Elementary School Public • 3-5	438 Students	6 reviews
NR Kent Island Elementary School Public • PreK-2	462 Students	2 reviews

School data provided by GreatSchools. School service boundaries are intended to be used as reference only. To verify enrollment eligibility for a property, contact the school directly.

Redfin Real Estate Agents
in Chester

236

Deals in the Last Year

4.8

Avg. Customer Satisfaction

1767

Total Homes Closed

6 active Redfin Agents in Chester

Popular Markets in Maryland

Frequently Asked Questions

What is the median home price in Chester?

Homes for sale in Chester have a median listing price of $595K. Some of these homes are Hot Homes, meaning they're likely to sell quickly.

How often does Redfin update their new listings?

Most of our new listings in Chester are updated every 5 minutes so you can see new homes as soon as they come on the market. Learn More

What is transportation like in Chester?

Chester, Maryland, is known for its efficient transportation system, with a variety of options available for residents. The town experiences moderate traffic levels, making driving by car a convenient choice for many. Public transportation is also available, providing an alternative for those who prefer not to drive. Additionally, Chester is well-connected with nearby highways, making it easy to travel to and from the area.

What types of properties are available in Chester?

Chester, Maryland offers a variety of single-family home types, including ranch-style homes, colonial-style homes, and contemporary-style homes. These homes can be found throughout the town, with ranch-style homes typically built in the 1970s, colonial-style homes built in the 1980s, and contemporary-style homes built in the 1990s and early 2000s. To explore different property types for sale in Chester, Maryland, use the 'Home type' filter located above the active listings. Customize your search by selecting options like single-family homes, condos, townhomes, and more.

What is life like in Chester?

Chester, Maryland offers a tranquil living experience with its picturesque landscape and serene surroundings. The region boasts a mild climate, with comfortable temperatures throughout the year. Job opportunities in Chester are diverse, with a range of industries to explore. Residents can engage in a variety of recreational activities, such as exploring nature trails, enjoying water sports, and participating in community events. The region also offers a rich cultural scene, with opportunities to experience local art, music, and cuisine.

What are the schools and amenities like in Chester?

Chester, Maryland offers a variety of public amenities for its residents to enjoy. There is a selection of restaurants available, providing a range of culinary experiences. Outdoor enthusiasts will appreciate the presence of several parks in the area. For your daily needs, there are grocery stores conveniently located within the town. Additionally, the town features other amenities such as fitness centers, libraries, and more, all aimed at enhancing the quality of life for residents.

In the past month, 9 homes have been sold in Chester. In addition to houses in Chester, there were also 10 condos, 11 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. Redfin has a local office at 2001 S Street NW, Suite 200, Washington, D.C. 20009. 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.

Download the Redfin App on the Apple App Store

Download the Redfin App from the Google Play Store

Join us

Become an Agent

Get referrals

Careers

Find homes faster

About us

Why Redfin?

Community Impact

Diversity & Inclusion

Find us

Subsidiaries

Bay Equity Home Loans

Title Forward

Countries

United States

Canada

Updated January 2023: By searching, you agree to the Terms of Use, and Privacy Policy.

Do not sell or share my personal information.

REDFIN and all REDFIN variants, TITLE FORWARD, WALK SCORE, and the R logos, are trademarks of Redfin Corporation, registered or pending in the USPTO.

California DRE #01521930

NY Standard Operating Procedures

TREC: Info About Brokerage Services, Consumer Protection Notice

If you are using a screen reader, or having trouble reading this website, please call Redfin Customer Support for help at 1-844-759-7732.

REDFIN IS COMMITTED TO AND ABIDES BY THE FAIR HOUSING ACT AND EQUAL OPPORTUNITY ACT. READ REDFIN'S FAIR HOUSING POLICY AND THE NEW YORK STATE FAIR HOUSING NOTICE.

Chester, MD Homes for Sale

Average home prices near Chester, MD

Cities

Zip Codes

Chester, MD real estate trends

More to explore in Chester, MD

How to buy a house in Chester, MD

Living in Chester, MD

Schools in Chester

GreatSchools Rating

Redfin Real Estate Agents in Chester

Related Searches in Chester, MD

Popular Markets in Maryland

Frequently Asked Questions

What is the median home price in Chester?

How often does Redfin update their new listings?

What is transportation like in Chester?

What types of properties are available in Chester?

What is life like in Chester?

What are the schools and amenities like in Chester?

Redfin Real Estate Agents
in Chester