Chester MD Real Estate & Homes for Sale

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Beds:
4
Baths:
3.00
Sq.Ft.:
1,682
Status:
Active
MLS#:
MDQA2013142
Type:
Residential
Subdivision:
Harbor View
Lot size:
0.34 Acres
Year built:
1984
Courtesy: Sell Your Home Services 888-219-3009
View additional info

ADDITIONAL INFORMATION

Welcome to 1903 Churchill Lane, Chester, MD 21619! This spacious 4-bedroom, 3-bath home is full of potential and located in one of Kent Island’s most sought-after neighborhoods. Offering a generous floor plan, this property is ideal for buyers looking to customize and renovate to their personal taste. The home features owned solar panels with a remaining balance—an energy-efficient investment that can pay off in the long run. While the property does need work, it presents a fantastic opportunity to build equity in a prime location. Nestled in a quiet, well-established community, you’ll enjoy the charm and convenience of life on Maryland’s Eastern Shore. Don’t miss your chance to create your dream home in a great neighborhood. Being sold as-is.

Beds:
3
Baths:
4.00
Sq.Ft.:
2,100
Status:
Active
MLS#:
MDQA2012022
Type:
Condo
Subdivision:
Bayside
Year built:
2000
Courtesy: Samson Properties 301-760-2136
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ADDITIONAL INFORMATION

Waterside Living on Kent Island! Discover the perfect blend of comfort and convenience in this spacious 3-bedroom, 3.5-bathroom condo located on Kent Island, in the Bayside Condominiums waterside community. This 3-level condo offers a wonderful combination of space, style, and serene coastal living. The open-concept main floor features a freshly painted, inviting living room with a cozy gas fireplace, sliding doors that open to a large deck, creating the perfect oasis for morning coffee, grilling or evening relaxation. The house chef will absolutely love the modern kitchen equipped with stainless steel appliances, granite countertops, a vented cooktop, and ample cabinet space. The main floor also includes a convenient half bath. The second level has two, en-suite bedrooms, including the luxurious primary suite, complete with a private balcony, walk-in closet, and spa-like ensuite bath featuring a jacuzzi soaking tub. A second spacious en-suite bedroom and laundry are also located on this level. The third level is a retreat of its own, featuring an oversized en-suite bedroom with plenty of space to create a cozy sitting area, home office, or flex space tailored to your needs. Bayside Condominiums offers resort-style living with amenities such as a pool, clubhouse, fitness center, volleyball court, tennis courts, a gym, clubhouse and meeting room. You will also want to take advantage of walking trails. waterfront dining, shopping, and nearby marinas. Just minutes from the Chesapeake Bay Bridge, this home is ideal for commuters or those seeking a tranquil getaway. Don’t miss your opportunity to own this exceptional home in one of Kent Island’s most desirable communities. Schedule your private tour today!

Beds:
2
Baths:
3.00
Sq.Ft.:
2,032
Status:
Active
MLS#:
MDQA2013034
Type:
Residential
Subdivision:
Gibsons Grant
Lot size:
0.11 Acres
Year built:
2011
Courtesy: RE/MAX Executive 443-274-1900
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ADDITIONAL INFORMATION

MUST SEE this Stunning End Unit Townhome in the Desired Community of Gibsons Grant which is located on the Chester River and Macum Creek! The Craftsman Style Beauty is a Perfect fit for anyone seeking a Spacious Home to move right into and not have to do a thing! Bring your Rockers to sit back and relax on the sprawling covered front porch... AND it is ALL about the porches here in Gibsons Grant! Step inside to be greeted by the lengthy Foyer with Gleaming Hardwood Floors that flow into the open concept of the Family Room complete with, Gas Fireplace, Mantel, Built-In Bookcases and a Beautiful Gourmet Kitchen with a coffered ceiling! Enjoy your daily meals on the large 2-tiered Granite Island with updated pendant lighting. The Kitchen has newer energy-efficient Matte Stainless Appliances, Ceramic Tile Backsplash, 42" Cabinets, lots of counter space, double sink and ample recessed lighting. Main level offers a home office space with french doors that could be used as another bedroom, home gym, playroom & more! Two Large Bedrooms upstairs to include the Primary ensuite with a custom walk-in closet and dual vanity sinks, along with a LOFT area space that can serve as another bedroom, if needed! With a sizable 2,032 square feet of living space, this Home provides more room than many single-family homes in the Community! Maintenance free wood decking on the side screened porch adds additional living space to enjoy through most of the year and the perfect spot to take in your morning coffee, afternoon cocktail, evening Sunset or having guests over to enjoy a good 'ol Eastern Shore crab feast! Privacy Fence and custom Brick-paved side courtyard add a touch of elegance to the outdoor space. Storage will never be a problem thanks to the poured concrete floor crawl space (with a new air circulating system) and the oversized 2 Car Garage! Peace of mind comes with the NEW HVAC in 2024, complete with Ultraviolet Light Purification System. Community Amenities are plentiful on the 55 Acre Waterfront development to include, Ponds, Open Space, Life-Guarded Pool, Party Room, Gym (with NEW equipment), Meeting Room, Kayak Storage, Waterfront Pavilion, Grilling Area, Fire-Pit in the Happy Hour Space, Walking Trails, Dog Stations and a Private Fishing & Crabbing Pier!

Beds:
3
Baths:
3.00
Sq.Ft.:
2,602
Status:
Active
MLS#:
MDQA2013136
Type:
Condo
Subdivision:
Four Seasons At Kent Island
Year built:
2024
Courtesy: KOVO Realty 240-375-5074
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ADDITIONAL INFORMATION

Stylish Comfort & Thoughtful Design – Severn Ready for June 2025 move-in, the Severn offers a refined take on condo living with 3 bedrooms, 2.5 baths, and a 1-car garage—all wrapped in elegant, low-maintenance style. The open-concept layout features laminate flooring throughout, with tile in both full baths, creating a clean and cohesive flow from room to room. At the heart of the home, the kitchen shines with quartz countertops, pendant lighting, tile backsplash, and a full suite of stainless appliances including a single oven, gas cooktop, microwave, range hood, and dishwasher—all perfect for everyday cooking and entertaining. Enjoy cozy evenings in front of the electric fireplace, or mix and mingle at the built-in dry bar. The primary suite is a true retreat, featuring a sitting room, large walk-in closets, and a luxurious bath complete with a shower with seat, handheld shower wand, double sinks, and quartz countertops. This home was built for both comfort and convenience, with elevated features that set it apart. For a full list of included features, 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 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 friends and enjoying the company of people who have worked hard and now want to enjoy all that a luxury 55+ community has to offer. Located steps from the water and minutes from Annapolis, the location also offers quick access to Rt. 50. Enjoy the convenience of nearby dining and shopping options together with the quaint charm of a small town. *Photos are of similar home as this home is to be built.

Beds:
2
Baths:
2.00
Sq.Ft.:
1,690
Status:
Active
MLS#:
MDQA2013134
Type:
Residential
Subdivision:
Four Seasons At Kent Island
Lot size:
0.16 Acres
Year built:
2025
Courtesy: KOVO Realty 240-375-5074
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ADDITIONAL INFORMATION

Easy Living Meets Timeless Style – Bernstein II, Lot 604 Available for settlement in Summer 2025, the Bernstein II is a beautifully designed 2-bedroom, 2-bath home offering low-maintenance, single-level living with thoughtful upgrades throughout. Step inside to find Luxury Vinyl Plank flooring flowing throughout the main living areas, creating a warm, cohesive space that’s both stylish and durable. The two full baths feature tile flooring, including the primary bath, which boasts a spacious shower with a built-in seat, handheld shower wand, double sinks, and quartz countertops for a refined finish. In the kitchen, you'll find everything the home chef needs—single oven, gas cooktop, range hood, microwave, dishwasher, and a French door refrigerator—all enhanced by pendant lighting, a tile backsplash, and a smart layout that opens to the main living area. A 2-car garage adds convenience, and the overall design offers the perfect blend of comfort and functionality for everyday living or lock-and-leave ease. PHOTOS ARE FOR DISPLAY PURPOSES ONLY AND LAYOUT MAY VARY. For a full list of features, 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 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 friends and enjoying the company of people who have worked hard and now want to enjoy all that a luxury 55+ community has to offer. Located steps from the water and minutes from Annapolis, the location also offers quick access to Rt. 50. Enjoy the convenience of nearby dining and shopping options together with the quaint charm of a small town. *pictures are representative of a similar home.

Beds:
3
Baths:
3.00
Sq.Ft.:
2,283
Status:
Active
MLS#:
MDQA2013054
Type:
Residential
Subdivision:
Harbor View
Lot size:
0.23 Acres
Year built:
1997
Courtesy: EXP Realty, LLC 888-860-7369
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ADDITIONAL INFORMATION

You’ve been waiting for this!! Beautiful Cape Cod with spacious wrap around porch! Upon entering, you will be greeted with hardwood floors throughout most of the main level. The focal point once inside is the beautiful open family room with a wood burning fireplace with stacked stone soaring to the vaulted ceiling and two ceiling fans when cooling off in the warmer months! The gourmet kitchen opens up into the dining area as well as the family room so that you can stay in the mix when entertaining! Not only is the kitchen a grand size, but it also has not only an island with seating but also an additional breakfast bar! Granite countertops top off what is every cook’s dream including gas cooking! The Primary Bedroom on the main level is spacious and you will love the sliders to the wrap around porch which overlooks the open space with trees as far as you can see! The Primary Bath was just recently renovated with a fabulous jetted stand alone tub as well as a fantastic walk in shower and beautiful tile plank flooring. The Primary Bedroom closet is in the process of being renovated as well with custom shelving and should be completed prior to listing becoming Active. Laundry room on main level that doubles as a mud room off the two car garage! A favorite of mine is that there is an enormous bonus room above the garage that is a great office/hobby room or den. **Stairs to office/hobby room is in laundry room.** Cannot be counted as bedroom because there is no closet but it’s a fantastic surprise room. Seller is offering a home warranty! Quick settlement possible. **Please click on pink video icon to see floor plan, video and more details!** Call listing agent with any questions.

Beds:
3
Baths:
2.00
Sq.Ft.:
2,134
Status:
Active
MLS#:
MDQA2012806
Type:
Residential
Subdivision:
Gibsons Grant
Lot size:
0.14 Acres
Year built:
2013
Courtesy: Keller Williams Flagship 410-729-7700
View additional info

ADDITIONAL INFORMATION

Welcome to 194 Evelyne Street, located in the sought-after waterfront community of Gibson's Grant! Get ready to embrace the laid-back, coastal lifestyle you’ve always dreamed of—right from the comfort of home. If you've been searching for the ease and comfort of one-level living, your search ends here! This beautifully crafted Stanford model by Koch Homes offers just over 2,000 square feet of thoughtfully designed living space, with 3 bedrooms and 2 bathrooms. The home features fresh paint—just waiting for your personal touches to make it uniquely yours. Step inside and you’ll be greeted by an open-concept layout that’s perfect for entertaining friends or simply relaxing in your own coastal retreat. The gourmet kitchen is a chef’s dream, complete with a spacious island, granite countertops, stainless steel appliances, and a Sub-Zero refrigerator. The primary bedroom is a true escape, with a generous layout that includes an attached owner’s suite—ideal for a reading nook, home office, or cozy sitting area. The spa-like ensuite bath features dual vanities, a soaking tub, and a separate shower to melt the day away. Enjoy the convenience of the rear-facing 2-car garage. This home is located on a corner lot so it’s quick and easy access from the alley to your garage! Outside, experience the peaceful surroundings of Gibson’s Grant, where charm and community meet the Chesapeake Bay. Take a stroll along scenic walking paths, unwind on the private fishing pier, or explore the Cross Island Trail just steps from your door. The community also offers a clubhouse with fitness center, a resort-style pool, kayak launch & storage, playground, and more! With easy access to Rt 50, and just minutes from waterfront dining, marinas, golf courses, and the Bay Bridge, this location truly has it all. Don’t miss your chance to make 194 Evelyne Street your year-round coastal haven. Schedule your private tour today and step into the lifestyle you deserve!

Beds:
4
Baths:
3.00
Sq.Ft.:
2,658
Status:
Active
MLS#:
MDQA2013062
Type:
Residential
Subdivision:
Marling Farms
Lot size:
0.92 Acres
Year built:
2018
Courtesy: Wilson Realty & Staging LLC 410-304-2250
View additional info

ADDITIONAL INFORMATION

Buyers get ready! This custom built home is a SHOW STOPPER! In excellent condition This custom-built stunner offers nearly 2,700 SF of beautifully finished space, an open-concept floor plan, and all the on-trend finishes you’ve been dreaming of. Spacious eat-in kitchen with a huge center island that flows right into the dining area – perfect for everyday living and entertaining. Plus a veratile main level home office/playroom/guest bedroom adds flexibility to fit your needs. Four upper level bedrooms and 2 baths which includes private primary suite with dual closets and a super bath. All outlets are tamper proof and kitchen outlets include USB ports. Main level HVAC has air purifier built in. Step out to the multilevel decks for great entertaining space that leads to a custom patio with fireplace--your new GO TO destination! And located in the water access community of Marling Farms on nearly 1 full acre with fenced back yard and cozy outside fireplace. The only thing you need to do is pack! Don't let this one slip away or you will regret it!

Beds:
3
Baths:
4.00
Sq.Ft.:
1,899
Status:
Active
MLS#:
MDQA2013078
Type:
Condo
Subdivision:
Bayside
Year built:
1999
Courtesy: Long & Foster Real Estate, Inc. 410-643-2244
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ADDITIONAL INFORMATION

This town home has a 1 car garage and offers 1900' of space with interesting options on the first floor. Family room w/fp is connected to bright kitchen. Large Deck with slight pond views. 3 Bedrooms (Primary w/bath). 2 full and 2 half Bathrooms. Bright home ready for your touches. New flooring on main level. Newer carpet on 3rd level. HVAC is newer. Fabulous community with Club House, pool, tennis ct, exercise room plus! Only 3 minutes or less to Bay Bridge for commuting.

Beds:
2
Baths:
3.00
Sq.Ft.:
1,900
Status:
Active
MLS#:
MDQA2012922
Type:
Condo
Subdivision:
Four Seasons At Kent Island
Year built:
2022
Courtesy: Keller Williams Select Realtors of Annapolis 410-972-4000
View additional info

ADDITIONAL INFORMATION

Stunning condo with breathtaking views of the Chester River! This turnkey unit features two spacious bedrooms, two full bathrooms, and a versatile office or den with French doors. The chef-inspired kitchen boasts gas cooking, a range hood, quartz countertops, and a breakfast bar. Enjoy the convenience of a separate laundry room with a full-size washer and dryer. Additional storage is available with a one-car garage and a large lockable storage room. Secure building with key code access. The brand-new, 24,000 square-foot clubhouse offers both indoor and outdoor pools, an outdoor bar area, and numerous fire pits with seating. The community is packed with amenities, including 4.3 miles of walking trails, a fitness center, library, game room, and lighted pickleball courts. You’ll also find tennis courts, bocce, a dog park, and an outdoor amphitheater for live music and movie nights. Conveniently located near Route 50, this home offers easy access to the beach, Annapolis, Baltimore, and Washington, D.C.

Beds:
2
Baths:
3.00
Sq.Ft.:
1,900
Status:
Active
MLS#:
MDQA2013032
Type:
Condo
Subdivision:
Four Seasons At Kent Island
Year built:
2022
Courtesy: Redfin Corp 301-658-6186
View additional info

ADDITIONAL INFORMATION

Welcome to Four Seasons at Kent Island, a premier 55+ waterfront community offering luxury, lifestyle, and leisure. This beautifully maintained 3rd floor Chester model features 2 spacious bedrooms plus a den/office, 2.5 baths, and serene pond views with a fountain—creating a picturesque, peaceful setting in every season. Inside, enjoy a light-filled open-concept floorplan with a gourmet kitchen boasting high-end appliances, a cozy living area with a modern fireplace, and oversized bedroom windows offering year-round peek-a-boo views of the Chester River. Elegant French doors open to a versatile den/office, while double sliding glass doors lead to a private, covered balcony where you can sip morning coffee and watch deer, herons, egrets, or distant sailboats drift by. Thoughtful upgrades include custom coastal-toned paint, walk-in closet organizers, built-in drawers in the primary suite, and a spacious laundry room with cabinetry. Additional conveniences include a dedicated climate-controlled storage closet on the first floor, an attached one-car garage with Gladiator cabinets, a ceiling fan on the balcony, and an energy-efficient interior location for lower utility costs—all with weather-free access to the interior mail room. Enjoy resort-style amenities such as an indoor lap pool, a stunning outdoor beach-entry infinity pool overlooking the Chester River, a well-equipped clubhouse with a gym, gathering rooms, a book-share library, and a game room. Explore miles of scenic walking and biking trails—including direct access to the 6.5-mile Cross Island Trail—and take advantage of the kayak/paddleboard launch and storage, tennis, bocce, and pickleball courts, multiple outdoor fire pits (wood-burning on the inland sandy beach and gas on the patio), and a vibrant calendar of community events, clubs, food trucks, and socials. Ideally located near Annapolis, Washington D.C., BWI Airport, and the charming towns of St. Michaels, Chestertown, and Tilghman Island—this is Eastern Shore living at its finest.

Beds:
3
Baths:
3.00
Sq.Ft.:
2,453
Status:
Active
MLS#:
MDQA2012962
Type:
Residential
Subdivision:
Four Seasons At Kent Island
Lot size:
0.14 Acres
Year built:
2021
Courtesy: Coldwell Banker Realty 410-543-4545
View additional info

ADDITIONAL INFORMATION

Welcome to your dream home situated on a coveted premium lot that backs to the woods giving you endless views of wildlife. The first-floor living is ideal for all homeowners and offers you a large primary bedroom, an office/2nd bedroom and a completely open concept on the main level. The kitchen boasts custom cabinets, stainless steel appliances, double oven, gas range with exhaust hood and custom quartz countertops coupled with an oversized island with a waterfall edge. The living and dining areas offer custom built ins next to the gas fireplace and between the two wine fridges. Let's not forget about the numerous upgraded light fixtures throughout the entire home including all new ceiling fans, recess lighting, and pendant lights over the island and dining table. The first floor offers you beautiful luxury vinyl plank flooring and 9 foot ceilings along with one of three full bathrooms. The primary bedroom provides you with a large en suite bathroom with a custom walk-in shower, dual vanity sink, and walk in closet with custom built shelving. The upstairs gives you a large space to do with what you please, along with the third bedroom and full bathroom. As we make our way outside, you can't help but notice the immaculate stone patio that was custom built to give you a sense of your own private oasis. The patio boasts a gas firepit, a built-in grill and custom lighting that provides you with that calming glow for when you're relaxing at night. The backyard backs to the woods, so you won't have to worry about neighbors behind you either. Schedule a tour now before it's too late...

Beds:
1
Baths:
1.00
Sq.Ft.:
1,008
Status:
Active
MLS#:
MDQA2013042
Type:
Residential
Subdivision:
None Available
Lot size:
0.46 Acres
Year built:
2005
Courtesy: Keller Williams Realty 302-360-0300
View additional info

ADDITIONAL INFORMATION

Waterfront Opportunity Awaits on Kirwans Creek! Imagine the possibilities! This charming cape cod home offers an incredible chance to create your own waterfront retreat on the Kirwans Creek. Situated on a desirable lot with direct water access, this property boasts a comfortable main level and an expansive, unfinished second floor brimming with potential. The main level welcomes you with a traditional floor, plan including a cozy living room, a functional kitchen, comfortable bedroom with water views and a full bathroom. Upstairs, discover a blank canvas. The unfinished second floor presents a unique opportunity to customize the space to your exact needs and desires. Envision additional bedrooms, a spacious primary suite with breathtaking water views, a home office, a recreation room – the possibilities are endless! Step outside to discover a front porch, a large gravel driveway, a huge side & backyard and an outbuilding. Enjoy the ease of single level living while taking in the tranquil scenery of the creek perfect for potential outdoor activities, e.g., boating, kayaking, paddleboarding, fishing, crabbing or simply relaxing by the water. Conveniently located near shopping, restaurants, parks and marinas. Don’t miss this fantastic opportunity to be on the water!

Beds:
3
Baths:
1.00
Sq.Ft.:
1,428
Status:
Active
MLS#:
MDQA2013006
Type:
Residential
Subdivision:
None Available
Lot size:
0.28 Acres
Year built:
1952
Courtesy: Keller Williams Realty 302-360-0300
View additional info

ADDITIONAL INFORMATION

This delightful brick home offers the perfect blend of comfortable living and direct access to the beautiful waters of Kirwan Creek. This home features three bedrooms, one bathroom, family room, kitchen and dining room. Enjoy picturesque nature views and water views from your backyard patio. Boaters will appreciate the large, fixed dock as well as the floating docks which are prefect for launching kayaks, paddle boards, jet skis and boats. Imagine spending your days boating, fishing, crabbing, or simply soaking in the tranquil beauty of Kirwans Creek from your own backyard. This location would make a great second home or vacation rental. Convenient to shops, restaurants, parks and marinas. Don’t miss this incredible opportunity!

Beds:
3
Baths:
3.00
Sq.Ft.:
1,760
Status:
Active
MLS#:
MDQA2013004
Type:
Condo
Subdivision:
Queens Landing
Year built:
1985
Courtesy: RE/MAX Executive 443-274-1900
View additional info

ADDITIONAL INFORMATION

Waterfront Living at Its Finest in Queen’s Landing! Welcome to this stunning 3-bedroom, 2.5-bath, plus loft- townhome, perfectly positioned in the heart of the coveted waterfront community of Queen’s Landing. Beautifully renovated with attention to detail, this home offers expansive panoramic water views that can be enjoyed from every room. Just steps from your front door, you’ll find the waterfront community pool and the private marina, where you can keep an eye on your boat right from the house. Whether you’re enjoying a quiet sunrise on your balcony, heading out for a day on the water, or taking a dip in the pool, this home delivers the ultimate Eastern Shore lifestyle. Queen’s Landing is packed with amenities, including a clubhouse, fitness center, tennis and pickleball courts, walking trails, and scenic waterfront picnic areas. It’s also just minutes from the Bay Bridge and only a short drive to historic Annapolis, offering the perfect blend of resort-style living with commuter convenience. This is more than just a home—it’s a waterfront retreat, a boater’s dream, and a rare opportunity to own in one of the most picturesque and amenity-rich communities on the Chesapeake Bay.

Beds:
3
Baths:
3.00
Sq.Ft.:
2,602
Status:
Active
MLS#:
MDQA2012790
Type:
Condo
Subdivision:
Four Seasons At Kent Island
Year built:
2022
Courtesy: Long & Foster Real Estate, Inc. 410-263-3400
View additional info

ADDITIONAL INFORMATION

Welcome to luxury condo living at Four Seasons at Kent Island, an active 55+ community packed with amenities. No need to wait for a new condo to be built – you can move in now to 170 Harrier Way #34. This third floor Severn model (3 BR / 2 ½ Bath / 2,602 sqft) offers beautiful views of the Chester River and nearby tidal pool. Inside, sunshine fills the unit with light throughout the day and the numerous windows are treated with Hunter Douglas luxury blinds when you have had enough sun. The home offers an open concept layout. The kitchen includes the upgraded package which includes stainless steel GE Profile appliances (including refrigerator, gas stove, oven, microwave, refrigerator, and dishwasher), a gourmet island with quartz countertop, pendant lighting, staggered cabinets, backsplash, and dry bar. The great room offers water views and added tranquility with an Allusion 60” fireplace. The master bedroom is spacious and includes two sizable walk-in closets and includes a sitting room with water views along with patio access. Both guest rooms are spacious and offer ample closet space. On the first floor, the unit includes a private 1-car garage along with a climate-controlled storage room. The gem of the community is its 24,000 sq. ft. clubhouse that includes indoor & outdoor pools, a state-of-the-art fitness center, a yoga studio, locker rooms, a game room, a library, three large social gathering areas with TVs and kitchens. Outside of the clubhouse is a resort-style pool with direct views of the Chester River, a beach area with fire pits, a patio with gas fire pits, a bar area, a performance stage, miles of walking and biking trails, tennis courts, pickleball courts, basketball, bocce ball, children’s playground, dog park, kayak/paddleboard launch area with storage racks, boat pier for visitors, and much more. There are numerous clubs, fitness sessions, and events to join and start interacting with your neighbors right away. A sampling includes cooking club, book club, yoga, pilates, cross-fit, strength training, golf, pickleball, line dancing, aqua fitness, cards, billiards, and many more. With a full-time lifestyle director on site at the clubhouse, there is no reason to leave home. However, if you do, Four Seasons offers convenient access to Route 50, Annapolis, DC, Baltimore, BWI airport, and the Eastern Shore and beaches. Kent Island itself offers amazing waterfront dining options, shopping, the nearby Queenstown outlets, world class boating, the Blue Heron county golf course, and miles of cross-island biking trail surrounded by views of the Chester River and Chesapeake Bay. What are you waiting for? Start living the luxury island life today!

Beds:
2
Baths:
2.00
Sq.Ft.:
n/a
Status:
Active
MLS#:
MDQA2013002
Type:
Condo
Subdivision:
Four Seasons At Kent Island
Lot size:
0.04 Acres
Year built:
2020
Courtesy: RE/MAX Executive 443-274-1900
View additional info

ADDITIONAL INFORMATION

Motivated Seller – Priced to Sell! Quick Settlement Possible! Enjoy low-maintenance living in the amenity-rich, 55+ community of Four Seasons on Kent Island. This 2-bedroom, 2-bath home offers comfortable one-level living with an open layout, perfect for entertaining or relaxing. The property includes a 1-car garage with additional storage units—ideal for keeping your home organized and clutter-free. Priced to sell and move-in ready, this home is a fantastic opportunity to get into one of Kent Island’s most desirable waterfront communities. The seller is motivated and prepared for a quick settlement—bring all offers! Four Seasons offers resort-style amenities including a stunning clubhouse, indoor and outdoor pools, fitness center, walking and biking trails, pickleball courts, and a full calendar of activities. Just minutes from the Bay Bridge, with easy access to Annapolis and all the charm of Maryland’s Eastern Shore. Don’t miss out—schedule your private showing today!

Beds:
4
Baths:
3.00
Sq.Ft.:
2,106
Status:
Active
MLS#:
MDQA2012426
Type:
Residential
Subdivision:
Clayborne Woods
Lot size:
0.23 Acres
Year built:
2001
Courtesy: Long & Foster Real Estate, Inc. 410-643-2244
View additional info

ADDITIONAL INFORMATION

Do not miss! Clayborne Woods is a private community with one way in and one way out! Neighbors describe it as close knit, friendly, and a place they do not want to leave! This home sits on a prime lot in the neighborhood, with wooded views from almost every side, affording you the Eastern Shore serene living you come here to get! As you enter this home, you'll notice it's warm tones throughout. Lovely hardwood floors through the main living area. The family room offers vaulted ceilings and a wood burning fireplace to keep you cozy in the cooler months! It opens to the dining area which provides amazing bay windows. The kitchen is modern with granite countertops, light colored cabinets, stainless steel appliances, and a breakfast nook! The primary suite located on the main level offers vaulted ceilings, tons of natural light, and direct access to your deck and backyard. The updated en-suite bathroom offers a soaking tub and separate shower. 2nd bedroom is located on the main level as well. 3rd and 4th bedrooms are located on the 2nd level along with a full bath. Medium size landing space / loft, serves as a reading nook, or extra space for a desk, toys, or other things, it's versatile. Do not miss this lovely home! Come see it today!

Beds:
2
Baths:
3.00
Sq.Ft.:
1,900
Status:
Active
MLS#:
MDQA2012984
Type:
Condo
Subdivision:
Four Seasons At Kent Island
Year built:
2022
Courtesy: RE/MAX Executive 443-274-1900
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ADDITIONAL INFORMATION

This beautifully appointed home offers the perfect blend of elegance, comfort, and convenience in one of Maryland's most desirable 55+ communities. Step into a bright, open floor plan featuring a gourmet kitchen complete with stainless steel energy-efficient appliances, custom tile backsplash, and quartz countertops. The spacious dining area flows into a great room with a cozy fireplace, and access to the balcony. From the balcony, like the views from both bedrooms, you’ll enjoy dramatic sunrises over the Chester River and a variety of wildlife all year long. With nearly 2000 square feet of open living space on one floor this coastal condominium has a great layout for entertaining family and friends. The primary bedroom has a luxury owner’s bath with quartz counter tops, double sink, ceramic tile floors, and a spacious walk-in closet, by Closet America. The bright and airy 2nd bedroom is a separate suite with a full bath and another oversized walk-in closet. In addition to the two bedrooms, you have a home office with stylish French Doors, that can also be used as a den, or third bedroom. Rounding out this space is a fully equipped laundry room with a GE washer and dryer and built-in cabinets. Whether you're savoring the views with your morning coffee or entertaining in your stunning chef's kitchen, this home is a rare opportunity to experience the best of Eastern Shore living. Other features include a garage with adjoining driveway/parking space and large personal storage room which is a few short steps from the elevator. This unit is just a short walk to resident kayak racks with launch access to the Chester River. KEEP IN MIND THIS CHESTER MODEL IS MOVE-IN READY WITH PLENTY OF HIGH-END DESIGNER FEATURES AND UPGRADES ALREADY INCLUDED***** You will have complete access to the 24,000 square foot Clubhouse with spectacular Chester River Views! Fantastic amenities include 4.3 miles of walking trails throughout the community, outdoor infinity pool, indoor pool with on-duty lifeguard, fitness center, library, spacious exercise rooms for yoga, and opportunities for personal training sessions. There is a game room, gas and wood burning fire pits, Tiki bar equipped with refrigerators, sinks and television monitors, pier with transient boat slips, walking paths that link to the Cross Island Trail, lighted pickle ball courts, tennis courts, bocce, dog park, and an outdoor amphitheater for live music and movie nights. The community lifestyle director will keep you busy with social events, and daily activities such as yoga, a variety of clubs, including biking, billiards, book club, baking, mahjong, environmental club, trivia night and more. In addition to the weekly and monthly activities, residents can enjoy crab feasts, oyster roasts, and holiday gatherings throughout the year. This development is an unrivaled, amenity-filled, resort-style experience with convenient access to Annapolis, DC, Baltimore, and BWI. Kent Island offers multiple dining and shopping options, a nearby outlet mall, and a 6.5 mile cross-island trail surrounded by views of the Chester River.

Beds:
3
Baths:
3.00
Sq.Ft.:
2,250
Status:
Active
MLS#:
MDQA2012848
Type:
Residential
Subdivision:
Chester
Lot size:
0.75 Acres
Year built:
1991
Courtesy: RE/MAX Realty Services 301-652-0400
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ADDITIONAL INFORMATION

Welcome to this beautifully maintained home in a quiet Chester neighborhood, just one house off the water. Situated on a spacious 0.75-acre lot, this recently updated home has been freshly painted and is move-in ready. The main level features a spacious kitchen with granite countertops, stainless steel appliances, an island with additional storage, and elegant cabinetry. The open dining area flows into a large family room with vaulted ceilings and a charming fireplace—perfect for relaxing or entertaining. There’s also a bonus room ideal for a den, home office, or study, along with a convenient half bath. Stylish luxury vinyl flooring runs throughout the entire main level. Step outside to a generous deck—accessible from both the kitchen and family room—where you can entertain or unwind while enjoying the peaceful water view through the trees. A newly added huge shed in the backyard offers excellent storage or potential workshop space. Upstairs, the primary bedroom includes its own private bath, along with two additional well-sized bedrooms and another full bath. All bathrooms were recently updated, and the upper-level carpeting remains in great condition. Located just a stone’s throw from water access to Cox Creek and close to local restaurants and shopping, this home offers the perfect balance of tranquility and convenience. Come experience the charm and comfort of this Eastern Shore gem!

Beds:
2
Baths:
3.00
Sq.Ft.:
2,003
Status:
Active
MLS#:
MDQA2012944
Type:
Condo
Subdivision:
Four Seasons At Kent Island
Year built:
2022
Courtesy: Redfin Corp 301-658-6186
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ADDITIONAL INFORMATION

Move-In Ready 2-Bedroom Condo in Four Seasons at Kent Island! Discover this stunning 2-bedroom, 2.5-bath condo in the sought-after 55+ community of Four Seasons at Kent Island! Completely move-in ready, this home boasts a gourmet kitchen, a formal dining area, and a cozy family room, all enhanced by luxurious finishes throughout. The spacious primary bedroom features a full ensuite bath, while the guest bedroom includes a ceiling fan for added comfort. Enjoy ground-floor access to a private patio—perfect for relaxing outdoors. Additional highlights include a one-car garage, a private balcony, and a larger hall closet and guest bath compared to similar models. Experience resort-style living with amazing community amenities, including a clubhouse, fitness center, walking trails, and waterfront views. This one won’t last—schedule your tour today!

Beds:
2
Baths:
3.00
Sq.Ft.:
1,104
Status:
Active
MLS#:
MDQA2012916
Type:
Condo
Subdivision:
Queens Landing
Year built:
1983
Courtesy: Cummings & Co. Realtors 410-823-0033
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ADDITIONAL INFORMATION

Welcome to this beautiful 3 level Lake Front condominium. This unit offers a breathtaking panoramic lake view coupled with a partial water view of the scenic Chester River. The new owner's will love the "amenity rich" sought after community of Queens Landing. This waterfront community offers a Private Marina, Renovated Clubhouse , River Front Pool, Fitness Center, indoor Racketball , 4 new Pickle Ball courts, waterfront walking/jogging path, Kayak launch and more.... The interior has many recent upgrades to include; Roof, D/W, HVAC, water heater, New Stove and renovated Deck area. Family Room with Fireplace & walkout to lakeview rear deck. Property is priced to sell and is awaiting it's new owner. Easy to Show and existing furniture is negotiable if new buyer would like any of the items to remain. Please note: Tax record interior square footage may be incorrect.

Beds:
3
Baths:
4.00
Sq.Ft.:
3,514
Status:
Active
MLS#:
MDQA2012918
Type:
Residential
Subdivision:
Four Seasons At Kent Island
Lot size:
0.18 Acres
Year built:
2021
Courtesy: RE/MAX Executive 443-274-1900
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ADDITIONAL INFORMATION

Experience Kent Island living at its finest in this upgraded luxurious San Sebastian model in the prestigious Four Seasons community. Featuring an open floor plan with 10’ ceilings, designer finishes, newly renovated enclosed four-season porch and patio overlooking a gorgeous premium lot, this residence provides an ideal setting for both entertaining and everyday comfort. Arriving home, manicured landscaping and a charming front walkway leads to your formal entry. Inside, a grand foyer with an open, airy layout sets the tone for the rest of the home. This space effortlessly blends elegance and warmth, offering an inviting first impression with plenty of room to greet guests in style. The gourmet kitchen features an oversized center island with quartz countertop highlighted with upgraded recessed and pendant lighting, stainless steel appliances including a SMART programmable range, hood and double oven, and a big walk-in pantry. This kitchen is a chef’s delight. The great room is truly just that… a GREAT room! The custom designer blinds, electric fireplace with marble mantle, Bose Surround Sound Theater system, with French doors leading to the newly converted four-seasons room, this area was designed with all the comforts of an inviting, casual, comfortable living area. The primary bedroom with a spa-inspired bath includes a 14’ walk-in shower, double sink vanity and custom closet. A guest bedroom en-suite on this same level is perfect for visiting family or out-of-town guests. Rounding out the main floor is the home office, fully functional laundry room and a bonus dry bar complete with quartz countertop and glass front cabinets. The “must see” 2nd floor loft (32x14) is where you’ll find your 3rd bedroom and full bath, extra family & game room and spacious sky basement, perfect for all your storage needs. The inside of this home is gorgeous and “over the top” with details, but the real jewel to this property is the backyard oasis that the owner has created – a true resort like setting, perfect for relaxing or entertaining year-round. Enjoy the luxurious hot tub, just steps from the spacious 40x18 patio featuring built-in grilling space, sleek marble countertops, and a portable fire pit for cozy evenings under the stars. A fully furnished four-seasons room, equipped with a high-efficiency Mitsubishi split unit, offers a comfortable indoor-outdoor experience in any weather. All patio furniture conveys with the sale, making this outdoor oasis move-in ready. KEEP IN MIND THIS SAN SEBASTIAN MODEL IS MOVE-IN READY WITH PLENTY OF HIGH-END DESIGNER FEATURES AND UPGRADES ALREADY INCLUDED FOR IMMEDIATE DELIVERY. Award winning 24,000 Square Foot Clubhouse with Stunning Chester River Views! Fantastic amenities include 4.3 miles of walking trails throughout the community, outdoor infinity pool, indoor pool with on-duty lifeguard, fitness center, library, game room, gas and wood burning fire pits, Tiki bar equipped with refrigerators, sinks and television monitors, pier with transient boat slips, walking paths that link to the Cross Island Trail, lighted pickle ball courts, tennis courts, bocce, dog park, and an outdoor amphitheater for live music and movie nights. The community lifestyle director will keep you busy with daily activities such as yoga, a variety of exercise classes and an assortment of clubs including biking, billiards, book club, baking, mahjong, environmental club, trivia night and more. In addition to the weekly and monthly activities, residents can enjoy crab feasts, oyster roasts, and holiday gatherings throughout the year. This development is an unrivaled, amenity-filled, resort-style experience with convenient access to Annapolis, DC, Baltimore, and BWI. Kent Island offers multiple dining and shopping options, a nearby outlet mall, and a 6.5 mile cross-island trail surrounded by views of the Chester River.

Beds:
4
Baths:
3.00
Sq.Ft.:
3,000
Status:
Active
MLS#:
MDQA2012740
Type:
Residential
Subdivision:
Marling Farms
Lot size:
0.41 Acres
Year built:
2009
Courtesy: Sullivan Select, LLC. 301-745-5500
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ADDITIONAL INFORMATION

Eastern Shore Luxury with Sweeping Bay Views Every room tells a story in this impeccably crafted waterfront residence, where panoramic bay views take center stage and luxury lives in the details. Thoughtfully designed with a custom floorplan and built to the highest standards, this home feels like new — a true showcase of elegance, comfort, and craftsmanship. Step into a bright and airy open-concept layout, ideal for both everyday living and upscale entertaining. The gourmet kitchen is a chef’s dream, featuring rich, exotic granite countertops, premium appliances, and bespoke cabinetry. Throughout the home, high-end finishes, spa-inspired baths, and generous natural light elevate every space. Enjoy the flexibility of a first floor primary suite with unobstructed views of the bay. The adjoining primary bath is luxurious and tempts you to take a spa day! The finished garage offers built-ins and meticulous organization — a rare luxury in itself. Outside, your private pier (2011) invites you to embrace the waterfront lifestyle — boat, crab, or unwind with endless views. Just 25 minutes from Annapolis, this is Eastern Shore living at its finest: timeless, tranquil, and truly exceptional.

Beds:
2
Baths:
2.00
Sq.Ft.:
1,260
Status:
Active
MLS#:
MDQA2012896
Type:
Condo
Subdivision:
Queens Landing
Year built:
1985
Courtesy: RE/MAX Leading Edge 410-224-3200
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ADDITIONAL INFORMATION

NEW LISTING! Kent Island - Queens Landing - Waterfront Community - Popular and Rarely Available End Unit, Loft Model Loved for its Very Contemporary, Open Floor Plan with Vaulted Ceilings, Skylights and Large Loft with Balcony. This Model, Known as The Adriatic, Offers 1260 sq ft with a Primary Bedroom on the Main Level with Adjoining Full Bath, Spacious Great Room/Kitchen combo and Large Loft Space Above with Cozy Fireplace, 2nd Full Bath and Adjoining Balcony. The Great Room is expansive and bright and has 2-story ceilings with 2 skylights. There is a staircase along one side of the room leading up to the Loft which is a spacious and versatile area offering life style options as it could be used as either an additional Bedroom (shown here) OR as living area. This home has been updated with luxury vinyl plank flooring through out the main level and new carpet in the Loft and is in overall pristine condition with quality improvements. The Kitchen has been completely and thoughtfully renovated capturing the contemporary and nautical spirit of the area and features sleek white cabinets with modern brushed nickel hardware and a sprinkling of strategically placed glass fronts giving it interest and style. There is an expansive quartz countertop offering ample prep space and serving area and a suite of top of the line GE Cafe appliances. It is styled with a modern stainless steel and glass hood vent and microwave built-in to cabinets below and interesting tile back splash. There are 3 patio/porch areas to enjoy - one accessed by a slider off the Great Room, one off the Primary Bedroom and one off the covered front porch which overlooks a large front lawn. and garden space. Queens Landing offers many community amenities allowing you to enjoy living near the Bay and Chester River. Homeowners have access to a secure Clubhouse with On-Site Property Manager, upper level Party Room which is available for private functions and equipped with a full kitchen and has stunning water views, Fitness Center, Racquetball, Waterfront Sun Room/Game Room. The Outdoor Pool is the best on the Island situated overlooking the jetty to Castle Harbor Marina and you can relax at the pool and see the boats as they enter and exit the Chester River. You'll enjoy additional amenities like the tennis courts, kayak launch with storage, lovely waterside waking path and boat slips for lease or purchase as they become available on a first come, first served basis. This lovely condo is more than a residence, it's a lifestyle choice and the opportunity to put the hustle and bustle of everyday life behind you. Close by you have any number of restaurants offering a diversity of casual crabs to fine cuisine, music venues, marinas, shopping and extensive walking trails maintained by the county. This is a smart purchase for the discerning buyer as this level of included amenities is usually accompanied by bigger price tag properties and the taxes and maintenance are very reasonable. Come and enjoy the Kent Island lifestyle today!

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Andrea Conner, Maryland License 667140, Xome Inc., License 667140, [email protected], 844-400-XOME (9663), 750 State Highway 121 Bypass, Suite 100, Lewisville, TX 75067
Andrea Conner, D.C. License BR200200783, Xome Inc., License CO98372739, [email protected], 844-400- 9663, 750 State Highway 121 Bypass, Suite 100, Lewisville, TX 75067
Andrea Conner, PA License # RM425337, Xome Inc., PA License #RB067821, [email protected], 844-400-XOME (9663), 750 State Highway 121 Bypass, Suite 100, Lewisville, TX 75067
Andrea Conner, NJ License # 1758875, Xome Inc. NJ License # 2326449, [email protected], 844-400-XOME (9663), 750 State Highway 121 Bypass, Suite 100, Lewisville, TX 75067

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Chester Real Estate

Chester is located in Maryland. Chester, Maryland has a population of 4,371. Chester is less family-centric than the surrounding county with 25.7% of the households containing married families with children. The county average for households married with children is 31.88%.

The median household income in Chester, Maryland is $84,835. The median household income for the surrounding county is $99,597 compared to the national median of $69,021. The median age of people living in Chester is 43.9 years.

Chester Weather

The average high temperature in July is 87 degrees, with an average low temperature in January of 28.3 degrees. The average rainfall is approximately 46.2 inches per year, with 12.7 inches of snow per year.

Chester Map

Chester Real Estate Market Conditions

  • Median sales price

    $657,950
    14.5%
    change since last quarter
  • # Active listings

    77
    30-day change

Chester Schools and Demographics

Education near Chester, MD

City County
High School Graduates 92.01 92.87
College Degree - 2 year 9.35 7.89
College Degree - 4 year 31.36 36.96
Graduate Degree 8.55 10.55
Expenditures per Student 15,198 15,198
Students per Teacher 14.4 14.4

Elementary Schools near Chester, MD

Grades Students P/T Ratio ZIP
Bayside Elementary School 03 - 05 402 16.1 21666
Cape St. Claire Elementary KG - 05 646 15.9 21409
Grasonville Elementary School PK - 05 494 15.9 21638
Kent Island Elementary School PK - 02 469 16.2 21666
Matapeake Elementary School PK - 05 493 15.4 21666
Rock Hall Elementary School PK - 05 187 14.3 21661
Windsor Farm Elementary School KG - 05 608 17 21409

Middle Schools near Chester, MD

Grades Students P/T Ratio ZIP
Matapeake Middle School 06 - 08 416 15.4 21666
Stevensville Middle School 06 - 08 474 13.5 21666

High Schools near Chester, MD

Grades Students P/T Ratio ZIP
Broadneck High School 09 - 12 2,104 18.4 21409
Kent Island High School 09 - 12 1,194 15.5 21666

Demographics near Chester, MD

City County
Neighborhood Type Small town
Population 4,371 49,702
Population Density 835 134
Median Age 43.9 44.7
People per Household 2.4 2.6
Median Household Income 84,835 99,597
Average Income per Capita 53,406 49,178

Real estate near Chester