Chester MD Real Estate & Homes for Sale

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Beds:
3
Baths:
3.00
Sq.Ft.:
2,789
Status:
Active
MLS#:
MDQA2014834
Type:
Single Family-Detached
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

Introducing the Kerr with a projected settlement date of January 2026. This home offers 3 bedrooms, 3 baths, and a spacious 3-car garage. Notable features include a home office, a screened patio, and a striking 1-story fireplace. The kitchen is beautifully appointed with a single oven, microwave, gas cooktop, range hood, dishwasher, French door refrigerator, pendant lights, and a tile backsplash, complemented by quartz countertops in both the kitchen and owner’s bath. The flooring showcases LVP throughout the main level and loft, with tile in all full baths. The owner’s bath highlights a walk-in shower with a seat, handheld shower wand, double sinks, and quartz countertops, creating a retreat-like experience. For a full list of features for this home, please contact our sales representatives. Photos are for illustrative purposes only and may not represent the exact home or finishes available. 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.

Beds:
2
Baths:
1.00
Sq.Ft.:
832
Status:
Active
MLS#:
MDQA2015064
Type:
Single Family-Detached
Subdivision:
Harbor View
Lot size:
0.28 Acres
Year built:
1952
Courtesy: RE/MAX Executive 443-274-1900
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ADDITIONAL INFORMATION

Discover this charming 2-bedroom, 1-bath home in Harbor View featuring beautiful wood floors, a brand-new roof, updated windows, and a spacious rear deck overlooking a large fenced backyard—perfect for relaxing or entertaining while enjoying the Island lifestyle. Ideally located near restaurants, shopping, and easy access to Route 50 for commuting. Come See!

Beds:
2
Baths:
3.00
Sq.Ft.:
2,010
Status:
Active
MLS#:
MDQA2015084
Type:
Single Family-Detached
Subdivision:
Four Seasons At Kent Island
Lot size:
0.16 Acres
Year built:
2025
Courtesy: KOVO Realty 240-375-5074
View additional info

ADDITIONAL INFORMATION

This stunning Taylor home offers an inviting open floor plan designed for both comfort and functionality. Featuring 2 bedrooms, 2.5 baths, and a spacious 3-car garage, this home perfectly blends everyday ease with elevated style. Highlights include a dedicated home office, a cozy screened patio for outdoor relaxation, and a dramatic 2-story stone fireplace that serves as the heart of the great room. The gourmet kitchen is equipped with a single oven, microwave, gas cooktop, range hood, dishwasher, French door refrigerator, pendant lighting, and a stylish tile backsplash. Elegant quartz countertops extend through the kitchen and owner’s bath. Luxury vinyl plank flooring enhances the main level, with tile in all full baths and the laundry room, and plush carpet in the extra suite and upstairs loft. The owner’s bath features a spacious shower with a seat and handheld shower wand, plus double sinks for convenience. For a full list of included features, please contact our sales representatives. Photos are for illustrative purposes only and may not represent the exact home or finishes available. 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.

Beds:
4
Baths:
3.00
Sq.Ft.:
1,482
Status:
Active
MLS#:
MDQA2015150
Type:
Single Family-Detached
Subdivision:
None Available
Lot size:
0.18 Acres
Year built:
2012
Courtesy: Jorge A. Zea 855-550-0528
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ADDITIONAL INFORMATION

Be the first to see this beautiful two-story house that has been tastefully renovated & upgraded. You will love open concept of living and dining area with a modern & charming electric fireplace; lots of natural lights, vaulted ceiling, beautifully refinished and stained wood floor, maintenance free deck with a lounge area and a firepit, private backyard with a spacious and comfortable lounge area. The kitchen is furnished with stainless steel appliances, 42” wood cabinets, and a new stainless-steel sink with accessories. Quality filtered water. The house was built in 2012. Recent (2022-2023) renovations and upgrades include: added 6‘’ bump wall with a built in electric 60” Touchstone fireplace (dual mode – flame and heat) and a high-quality Denon sound system; fully remodeled bathrooms; installed water filtration system (Charger Iron Breaker III) that supplies the whole house; refinished and stained oak wood floor, NEW - wood stairs treads, asphalt driveway, pavestone patio, LED light fixtures, ceiling fans with LED lights and remote/wall control, door hardware, light switches, vent grilles, stainless sink in the kitchen, Samsung EE laundry machine, window covering (curtains and blinds), paint - garage & all doors, wall paper and painted accent walls in bedrooms; built half wall (1st floor), added shelves in bedroom closets; LVP floor in the utility room; sum pump; outdoor entrance lights; landscaping (planted evergreen trees and sod). The air duct system was repaired and cleaned in December 2022. The house features 4 bedrooms and 2 ½ bathrooms. The primary bedroom is on the second level and features an ensuite bath. The second and third bedrooms are on the second level and share a hall full bath. There are main living area, dining, and kitchen on the second level. On the first level, there is fourth bedroom/living area with an ensuite half bath, and the utility room with oversized washer and dryer (Samsung). The attached 2 car garage. Shed in the backyard. House is very clean and well maintained. Pet and smoking free. Great central location. No HOA fees. Move in ready.

Beds:
2
Baths:
2.00
Sq.Ft.:
1,073
Status:
Active
MLS#:
MDQA2014698
Type:
Condo
Subdivision:
Bayside
Year built:
1996
Courtesy: Engel & Volkers Ocean City 443-292-6767
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ADDITIONAL INFORMATION

This is a highly sought-after location on Kent Island, known for its limited availability. Sellers have updated shiplap in the living room, paint throughout the house. This second-floor condo offers breathtaking views of the pond. You will enjoy an updated backsplash in the kitchen, featuring granite countertops and stainless steel appliances. Hardwood flooring is throughout the house. The private deck provides additional storage closet. The HVAC system is only 2 years old,, and the association is professional managed. The updated clubhouse features a well-equipped fitness center, a second-floor party room with a kitchen, a fireplace, and decks offering beautiful views. Tennis and pickleball enthusiasts will enjoy access to two dedicated courts. Water lovers will appreciate the close proximity to Castle Marina, which provides boat slips and amenities with direct access to the river and the bay. Trail enthusiasts will also value the connection to the scenic Cross Island Trail via Castle Marina Road—a picturesque path stretching from the Chesapeake Bay to Kent Narrows, ideal for walking, biking, and enjoying the waterfront surroundings.

Beds:
3
Baths:
2.00
Sq.Ft.:
1,728
Status:
Active
MLS#:
MDQA2015554
Type:
Single Family-Detached
Subdivision:
Harbor View
Lot size:
0.35 Acres
Year built:
1991
Courtesy: Coldwell Banker Realty 410-224-2200
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ADDITIONAL INFORMATION

Discover this beautifully updated 3-bedroom, 2 full and 1 half bathroom home located on a scenic 0.35-acre corner lot in the highly desirable Harbor View community, just two miles east of the Chesapeake Bay Bridge. Inside, enjoy a bright, modern kitchen with new countertops and backsplash, hardwood floors on the main and upstairs evels, and cathedral ceiling with skylights. Relax in the spacious lower-level family room plus a versatile bonus room/office/bedroom. Recent upgrades include a new roof (2019) with 50-year shingles, new windows, and a new vinyl pool liner with warranty. Step outside to your fully fenced back yard and private in-ground pool and deck, perfect for summer entertaining and relaxing. The community offers a one-acre community field with a pavilion and playground for events and gatherings. The location offers unbeatable convenience—just 20 minutes to Annapolis, 45 minutes to Baltimore, and 50–60 minutes to Washington, D.C. Enjoy the best of Kent Island living with easy access to Kent Narrows for waterfront dining, the Cross Island Trail (6.5 miles long) for walking and biking, and Queenstown Premium Outlets just five minutes away. This move-in-ready home offers the perfect blend of comfort, location, and lifestyle—don’t miss your chance to make it yours!

Beds:
2
Baths:
3.00
Sq.Ft.:
1,440
Status:
Active
MLS#:
MDQA2015054
Type:
Condo
Subdivision:
Queens Landing
Year built:
1999
Courtesy: Douglas Realty, LLC 410-255-3690
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ADDITIONAL INFORMATION

OPEN HOUSE SUN 12/7 11a-1p! Settlement possible for the Holidays & New Year! Enjoy low-maintenance living in the desirable waterfront community of Queen’s Landing, offering scenic views and direct access to the Chester River via Northeast Bay. This beautifully updated home features expansive pond and fountain views the moment you walk in, along with a brand new kitchen showcasing shaker-style cabinetry, quartz countertops, and stainless steel appliances. Brand new Living Room carpet. Upstairs offers two spacious en-suite bedrooms, including a primary suite with vaulted ceilings. A laundry area with brand new washer and dryer is conveniently located between the bedrooms. Light-filled interior with large windows and a screened-in porch perfect for relaxing evenings. Community amenities include a private marina, heated outdoor pool, renovated clubhouse, fitness center, tennis/pickleball courts, indoor racquetball, kayak launch/storage, and waterfront walking trails. Lawn care, snow removal, and exterior maintenance included. A boater’s dream and peaceful retreat—schedule your showing today!

Beds:
4
Baths:
4.00
Sq.Ft.:
n/a
Status:
Active
MLS#:
MDQA2014542
Type:
Single Family-Detached
Subdivision:
Harbor View
Lot size:
0.55 Acres
Courtesy: Keller Williams Flagship 410-729-7700
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ADDITIONAL INFORMATION

*****Immediate Delivery*****WATERFRONT DEEP WATER ****Schedule showoing today! 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 another deck on the rear of the home off the dining area if you're looking for more outdoor space. The third level features a laundry, three bedrooms including the spacious primary bedroom with updated bath and another stunning deck. The Blue Heron is a beautiful home and will serve a multitude of lifestyles. Explore your options today!

Beds:
4
Baths:
6.00
Sq.Ft.:
3,460
Status:
Active
MLS#:
MDQA2015546
Type:
Single Family-Detached
Subdivision:
Southwind
Lot size:
1 Acres
Year built:
1989
Courtesy: TTR Sotheby's International Realty 410-280-5600
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ADDITIONAL INFORMATION

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 and full bath accompany a spacious living area, ideal for extended family or guests. The heart of the home is a stunning, renovated kitchen featuring rich finishes, premium appliances, and an open layout perfect for gathering. Gleaming hardwood floors flow throughout, leading to a mahogany-lined library that exudes warmth and sophistication—a true sanctuary for work or quiet reflection. Outdoor living takes center stage with a screened porch that captures cooling Bay breezes and views of the pool and shimmering water beyond. Whether entertaining or simply savoring the stillness of the shoreline, every space in this home celebrates the beauty of the Chesapeake Bay lifestyle.

Beds:
2
Baths:
3.00
Sq.Ft.:
2,003
Status:
Active
MLS#:
MDQA2015222
Type:
Condo
Subdivision:
Four Seasons At Kent Island
Year built:
2021
Courtesy: Coldwell Banker Realty 410-263-8686
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ADDITIONAL INFORMATION

Love Where You Live! Experience resort-style living that blends comfort, luxury, and convenience—just steps from the waterfront. Enjoy peaceful mornings without the disruption of construction nearby. This highly sought-after first-floor condo is move-in ready and has been meticulously maintained, featuring numerous upgrades throughout. Step inside to an open, light-filled layout enhanced by crown molding, recessed lighting, and direct views of the lush greenspace with seasonal water glimpses. The gourmet kitchen and dining area are ideal for entertaining, offering a spacious island with seating, quartz countertops/bar, sleek wifi enabled appliances, and seamless flow into the living room. Unwind by the cozy fireplace or open the double sliding glass doors to your private patio—perfect for watching the sunrise, morning coffee, reading, or simply enjoying the peaceful natural setting. The owner’s suite offers both a walk-in and secondary closet, private patio access, and a luxurious en-suite bath with dual sinks and a spa-inspired frameless glass shower. The guest suite is bright and spacious, complete with its own en-suite bath, custom tilework, and large vanity. A bonus room with upgraded frosted glass doors provides the perfect space for a home office, workout area, or reading nook. Additional highlights include: LVP flooring throughout the entire home, interior access to a private one-car garage, and a secure storage unit. From your patio, take a stroll along the walking trail where you can take in the sights and sounds of nature to discover tranquil views and your kayak launch. The community also has direct access to the Kent Island Cross Island Trail. Many extra amenities to enjoy including: indoor heated pool, outdoor infinity pool, firepits, pickleball and tennis courts, dog park, and beautiful walking and biking trails. Live every day like you’re on vacation—this stunning condo offers the lifestyle you’ve been waiting for and is a must see to experience all of the upgrades!

Beds:
3
Baths:
3.00
Sq.Ft.:
2,066
Status:
Active
MLS#:
MDQA2015532
Type:
Single Family-Detached
Subdivision:
Clayborne Woods
Lot size:
0.17 Acres
Year built:
2000
Courtesy: Chaney Homes, LLC 443-249-7653
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ADDITIONAL INFORMATION

Step inside and see this meticulously cared for home! This home features a first floor primary bedroom with an ensuite full bath. Just 5 minutes from the Chesapeake Bay Bridge and all the beaches, parks, boat ramps, and waterfront venues you love to visit...right in your own neighborhood! This " Home Sweet Home" in Chester, Queen Anne's County, MD has been thoughtfully improved throughout, with luxury vinyl plank floors, kitchen with updated appliances & counter tops as well as a breakfast nook. The kitchen opens to a large family room with a cozy gas fireplace. The dining area overlooks the rear patio, where the owners have thoughtfully added a retractable awning. The rear yard offers plenty of privacy, backing to views of trees and nature. The upper level features 2 more bedrooms and another full bath. A garage with added parking pad provides storage for your vehicle plus additional storage as well. Updates within the last 5 years include: Roof, Appliances, Counter tops, Flooring, Hot Water Heater, and Furnace components. Don't miss seeing this home!

Beds:
3
Baths:
3.00
Sq.Ft.:
2,600
Status:
Active
MLS#:
MDQA2014528
Type:
Condo
Subdivision:
Four Seasons At Kent Island
Year built:
2023
Courtesy: Long & Foster Real Estate, Inc. 410-546-3211
View additional info

ADDITIONAL INFORMATION

Welcome to Luxury Condo Living at The Four Seasons at Kent Island, An active 55+ Community packed with tons of amenities . Move -in to this turn key luxury condo with plenty of natural light with "Perfect Fit" planation shutters and ample privacy on all windows and doors. The kitchen has a gourmet package including quartz countertops and a large island with space for barstool eating, subway tile backsplash, staggered cabinets, and stainless steel modern appliances. The great room has a seasonal view of the Chester River and a traditional electric fire place with shiplap accents fostering a feeling of warmth and tranquility. The primary bedroom/bathroom is spacious with two sizeable walk-in closets. The primary bedroom also includes attached sitting room with water-view and access to the balcony overlooking a pond that attracts wildlife. All bedrooms of this Severn Model offer custom closets designed and constructed by "Chesapeake Closets". The unit comes with a first floor assigned one car garage and an assigned climate-controlled storage closet. Come join the easy life! Call for your private showing!

Beds:
2
Baths:
2.00
Sq.Ft.:
1,073
Status:
Active
MLS#:
MDQA2015558
Type:
Condo
Subdivision:
Bayside
Year built:
1996
Courtesy: Maryland Residential Management Co 410-451-3300
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ADDITIONAL INFORMATION

Beautifully maintained first-floor condominium offering an open, inviting floor plan. This residence features two spacious bedrooms and one and a half bathrooms. The light-filled living and dining areas provide direct access to a patio, with storage closet. All kitchen appliances, stainless steel, only 1 year old, and counter tops updated. Both bathrooms remodeled in 2021. Washer & dryer brand new. Located in a highly desirable community of Bayside, offering exceptional amenities including scenic walking trails, a clubhouse with a party room, fitness center, swimming pool, and tennis courts. Conveniently situated near shopping, dining, and major commuter routes, this home offers the perfect blend of comfort, convenience, and resort-style living.

Beds:
2
Baths:
2.00
Sq.Ft.:
1,444
Status:
Active
MLS#:
MDQA2014504
Type:
Single Family-Detached
Subdivision:
Marling Farms
Lot size:
0.72 Acres
Year built:
1971
Courtesy: Coldwell Banker Waterman Realty 410-643-5005
View additional info

ADDITIONAL INFORMATION

Kent Island - Marling Farms - Brick Rancher - Waterviews of Crab Alley Bay - PRICE REDUCED - All on one level - Beautifully landscaped 3/4 acre lot that backs to trees - fenced patio area - 2 bedrooms with lots of windows and large closets - 2 full baths, one with a tub, one with a walkin shower - fabulous sunroom addition - quiet office area - updated kitchen with granite counters, newer cabinetry, beverage center with wine frig, large laundry area, large pantry closet, water conditioning system was just replaced, front load washer and dryer, money saving solar system in place (leased), gas fireplace in the living room with large mantle, large shed in backyard - 2 car garage with remote garage door openers and RV electric hookup. Marling Farms offers water access including a boat ramp and 4 beaches for residents to enjoy with playgrounds, pavilion, kayak storage, piers, ramp and breathtaking views. Residents enjoy walking and biking on the neighborhood streets. HOA fee is only $100 per year. This is the lifestyle you have been looking for. Visit today and don't miss out.

Beds:
4
Baths:
3.00
Sq.Ft.:
2,404
Status:
Active
MLS#:
MDQA2015450
Type:
Single Family-Detached
Subdivision:
Kirwans Landing
Lot size:
1.4 Acres
Year built:
1988
Courtesy: Coldwell Banker Realty 410-263-8686
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ADDITIONAL INFORMATION

BIG PRICE IMPROVEMENT. 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 kitchen with custom white cabinetry, granite countertops, and stainless steel appliances. The living room’s gas fireplace and the sun-filled sunroom overlooking the serene backyard create inviting spaces to relax and entertain. The dining room off the kitchen and an additional living room offer even more space. The spacious primary suite offers a quiet retreat with a seating area or office space and dual walk-in closets. Upstairs, you’ll find three additional bedrooms and a full bath. Additional upgrades include a new water heater, recently upgraded HVAC system with mini-split in the sunroom, new pool equipment, updated garage doors, owned Culligan water system, central vacuum, storage shed, two car garage perfect for storage, and more. Experience the best of Eastern Shore living — private, peaceful, and perfectly located in one of Kent Island’s most desirable waterfront communities.

Beds:
5
Baths:
4.00
Sq.Ft.:
3,036
Status:
Active
MLS#:
MDQA2014798
Type:
Single Family-Detached
Subdivision:
Chester
Lot size:
0.21 Acres
Courtesy: Long & Foster Real Estate, Inc. 301-945-9010
View additional info

ADDITIONAL INFORMATION

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 luxurious primary suite will provide sweeping water vistas and a spa-inspired bath with a 6’ tiled shower, double shower heads, and a built-in bench. Additional planned features include tile flooring in all bathrooms, bedroom-level laundry and an integrated 2-car garage. Outdoor living spaces will include an expansive back deck overlooking the water and a covered patio — perfect for peaceful mornings and sunrises over the shoreline. BONUS: Approx. 181 acres of conservation land lies on the other side of the shoreline! On a quiet waterfront lot surrounded by natural beauty, this home combines the craftsmanship of Laine Street Homes with the serenity of coastal living. Photos shown are of a completed home of the same floor plan.

Beds:
4
Baths:
3.00
Sq.Ft.:
1,840
Status:
Active
MLS#:
MDQA2013210
Type:
Single Family-Detached
Subdivision:
Clayborne Woods
Lot size:
0.16 Acres
Year built:
2001
Courtesy: Coldwell Banker Waterman Realty 410-643-5005
View additional info

ADDITIONAL INFORMATION

Don't miss this incredible opportunity to own a spacious 4-bedroom home in sought-after Clayborne Woods at an exceptional price! Picture yourself relaxing by the gas fireplace, enjoying outdoor fun in the fenced backyard, or working/playing in the flexible space featuring stylish French doors. This is a rare find and won't last long – schedule your private tour today before it's gone!

Beds:
3
Baths:
2.00
Sq.Ft.:
1,750
Status:
Active
MLS#:
MDQA2013798
Type:
Single Family-Detached
Subdivision:
Harbor View
Lot size:
0.28 Acres
Year built:
1988
Courtesy: Allfirst Realty, Inc. 443-320-1344
View additional info

ADDITIONAL INFORMATION

Great opportunity for a savvy investor to buy way below market value. This 3 brm 2 ba rancher, can easily be converted to a 4 brm. Needs work! Sold Strictly AS IS. Seller never occupied the property, therefore cannot guarantee accuracy in this listing, especially regarding utilities, well and sewer. Buyer must do their own due diligence before submitting an offer.

Beds:
3
Baths:
4.00
Sq.Ft.:
1,899
Status:
Active
MLS#:
MDQA2013646
Type:
Condo
Subdivision:
Bayside
Year built:
1998
Courtesy: Samson Properties 301-850-0255
View additional info

ADDITIONAL INFORMATION

You do not want to miss this opportunity to enjoy island living in this maintenance free, WATER VIEW-End UNIT! Come enjoy island living in the Bayside Community. Offering POND views from every window in this sought after end unit home complete with beautiful landscaping. Relax on your spacious deck overlooking the pond complete with 2 fountains or invite family and friends to enjoy a cookout on your ground level patio. Enter the ground level from the street, including a garage complete with storage shelves and door opener. Ground-level family room, or 4th bedroom, with sliding door access to patio and rear open space, also a half bath and laundry room. Main level has an open concept living, featuring hardwood flooring throughout a spacious combination living room/dining room with fireplace, crown moldings and 9ft. ceilings. An eat in kitchen with upgraded cabinets, appliances and granite countertops. Plantation shutters adorn the kitchen and tiled powder room windows. Living room has sliding doors opening to a large deck! Step out to a wonderful view of the pond and green open space, enjoy the moment. The upper level includes a spacious master suite with vaulted ceiling, walk-in closet and full bath with skylight. Two additional good-sized bedrooms with vaulted ceilings and another full bath complete this level. The exterior maintenance is taken care of by the Community Association along with the exterior shrubbery and mulch. Complete maintenance free living. The Bayside Community offers so many amenities including an outdoor pool, tennis courts and a recently renovated clubhouse complete with workout room and party room. Bayside is conveniently located near marinas, restaurants and the Cross Island Trail, perfect for walking, jogging or biking. This is the perfect place to enjoy life. Hurry!

Beds:
2
Baths:
2.00
Sq.Ft.:
1,913
Status:
Active
MLS#:
MDQA2014340
Type:
Single Family-Detached
Subdivision:
Four Seasons At Kent Island
Lot size:
0.13 Acres
Year built:
2019
Courtesy: Realty Navigator 410-643-3404
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ADDITIONAL INFORMATION

Welcome to Easy Living on the Eastern Shore! *** Discover the perfect blend of comfort, style, and resort-style living in this impeccably maintained, one-owner home — tucked into the highly sought-after, water-privileged 55+ community of Four Seasons at Kent Island. From the moment you walk in, you’ll notice the difference. The open-concept floor plan is thoughtfully designed and beautifully upgraded with custom finishes and designer lighting, setting the stage for elegant everyday living. *** At the heart of the home is a show-stopping kitchen—featuring a dramatic black quartz island, crisp white shaker-style cabinets, and ample prep space for casual meals or gourmet entertaining. The kitchen flows effortlessly into a warm and inviting family room anchored by a gas fireplace—perfect for cozy evenings or lively conversations. *** Need a little flex space? You’ve got it. A versatile bonus room makes the ideal office, craft room, guest space, or private retreat, bathed in natural light. Step out onto the custom-stamped concrete patio where you can sip morning coffee, host a happy hour, or just kick back and enjoy the quiet, watching the birds at the pond or the treelined backyard. *** But the real magic? The lifestyle. *** Four Seasons at Kent Island offers unmatched amenities that feel more like a vacation than a neighborhood. Think: *** - A stunning 24,000+ sq ft clubhouse . - Indoor and outdoor pools . - A waterfront pier with boat slips for visiting friends . - Fitness center, game room, chef’s kitchen, meeting spaces . - A full-time lifestyle director curating events, live music, and clubs . - All of this—just 20 minutes from Annapolis and right off Route 50 for easy getaways or guest visits. . - Low-maintenance, high-style, and built for enjoying every chapter of life to the fullest. . See why so many are choosing Four Seasons at Kent Island—and why this Donegal model might just be the one you’ve been looking for.

Beds:
5
Baths:
4.00
Sq.Ft.:
3,065
Status:
Active
MLS#:
MDQA2014334
Type:
Single Family-Detached
Subdivision:
Bentons Pleasure
Lot size:
0.53 Acres
Year built:
2002
Courtesy: Cummings & Co. Realtors 410-823-0033
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ADDITIONAL INFORMATION

PERFECT MULTI GENERATIONAL HOME!!!! 5 BEDROOMS! LIST PRICE ADJUSTED !!FANTASTIC HOME! THE COMPLETE PACKAGE AND THEN MORE! INGROUND GUNITE SALT WATER(LOW MAINTENANCE) POOL! TWO PRIMARY BEDROOM/BATH SUITES! BOTH WITH GIANT WALK IN CLOSETS! EACH PRIMARY BATH HAS A STEP IN SHOWER, DOUBLE STONE VANITY PLUS SOAKING TUB! THIS HOME HAS A TOTAL OF 5 BEDROOMS PLUS 3 AND ONE HALF BATHS! PLENTY OF SPACE FOR THE HOME OFFICE! THE OPEN KITCHEN IS FULLY UPDATED WITH ISLAND, STAINLESS STEEL DOUBLE OVENS, COOKTOP, DRAWER MICROWAVE, DISHWASHER,3 DOOR REFRIGERATOR, STATEMENT GRANITE, CUSTOM LIGHTING WITH DIMMERS. HEAT MONITORING DIRECTIONAL FAUCET. THE ADJACENT FAMILY ROOM FEATURES A GRANITE TRIMMED GAS FIREPLACE, TOWERING 19 FOOT CEILINGS, A UNIQUE WINDMILL STYLE CEILING FAN, AND DOUBLE TIERED WINDOWS FOR EXTRA LIGHT! THE HUGE 17X18 COVERED SCREENED PORCH IS RIGHT OFF THE KITCHEN AND FAMILY ROOM CREATING SUPER FLOW! A FEW STEPS DOWN FROM THE SCREENED PORCH THE NEW BUYER WILL FIND AN ATTRACTIVE CUSTOM PAVER PATIO AND THE INVITING IN GROUND POOL! THE REAR YARD IS SURROUNDED BY A LOW MAINTENANCE VINYL PRIVACY FENCE! OTHER FEATURES INCLUDE THE 2 CAR GARAGE WITH TONS OF SHELVING, AND A RINSE OFF SINK. THE REAR GARDEN SHED IS THE BEST EVER! ON THE INTERIOR CUSTOM WINDOW TREATMENTS, 2 INCH WHITE SHADES, LACE AND SHEER CURTAINS, WINE BAR, HUGE WALK IN CLOSETS(3), CUSTOM LIGHTING, CEILING FANS, CUSTOM CERAMIC TILE, RECENT LVP FLOORING & CARPET, MULTIPLE CONVENIENCE ITEMS, AND INCAPSULATED CRAWL SPACE HELP COMPLETE THE PACKAGE! OVER $150,000 OF RECENT IMPROVEMENTS & UPGRADES- LIST AVAILABLE. POOL EQUIPMENT INCLUDED! ONE YEAR HOME WARANTY AVAILABLE WITH ACCEPTABLE OFFER. A MUST SEE HOME !!! IMPROVEMENT LIST AND VALUES IN BRIGHT DOCS!

Beds:
3
Baths:
3.00
Sq.Ft.:
1,680
Status:
Active
MLS#:
MDQA2014278
Type:
Condo
Subdivision:
Queens Landing
Year built:
1984
Courtesy: RE/MAX Professionals 301-490-5400
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ADDITIONAL INFORMATION

This 1680 sq ft , 2 1/2 story townhome & this community have it all! It features many updates within the last year, and it shows beautifully! All It is "move-in ready",!.. The updates include a new main-level half bath & a new full bathroom on the top level, both have new flooring, ADA-compliant toilets, new vanity/sink & faucets, and paint. Interior doors are 6 panel colonial replaced in 2024! The main level features new SS appliances, including frig w/ icemaker, dishwasher, a convection range, new faucet, under sink disposal, and an additional, movable cabinet for storage & food prep. It has solid surface countertops. The dining area is right off the kitchen for easy access. The luxury vinyl plank flooring on the main level is neutral and works well with the wood-burning, corner fireplace. The private, cozy patio off the living room has a firepit, & decorative lighting makes you want to stay. See the "nighttime" picture! The seller selected this home because from the upper levels, there are water views on all 3 sides! You can even see water from the front door view. Their favorite is from the second-level balcony for a sunset view. The primary bedroom on the second level is large enough for a king bed, & has ample closets. It has access to a private loft area with skylights. The loft is currently a 3rd primary bedroom en suite!They converted a closet to a laundry room with a full-size washer & dryer, not stacked. The hall bath is also updated with an "easy clean" shower & handsome vanity. Going to the top level, which is currently the primary bedroom, with bath ensuite, you will notice the skylights and vaulted ceiling for a spacious look. The full bath is also new, with ada-complaint toilet, new vanity, mirror, , flooring, and paint. Queens Landing is a beautiful, waterfront condo community with a pool, clubhouse, tennis, pickleball, fishing, racketball, and even a community marina! Bring your kayak or boat! It's just a little over one hour from DC , Baltimore, and Wilmington.Being a condo, they cut the grass:-) All inspection items, balcony, fireplace, electrical, and clothes dryer vent have been completed, and are in the doc section of the MLS Bright. Come see !

Beds:
2
Baths:
1.00
Sq.Ft.:
764
Status:
Active
MLS#:
MDQA2014252
Type:
Single Family-Detached
Subdivision:
None Available
Lot size:
0.17 Acres
Year built:
1926
Courtesy: The Parker Group 302-217-6692
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ADDITIONAL INFORMATION

This property, situated on a 0.17-acre lot, offers a blank canvas for your vision. Located in Queen Anne's County, the existing structure presents endless possibilities for the right buyer. Take advantage of the spacious lot size, perfect for outdoor activities or future expansion plans. Buyers are encouraged to perform their own due diligence to verify property details. Please note that access to 1405 Little Creek Rd is via 104 Little Creek Ct, followed by a left turn. Do not use or enter any neighboring driveways or properties as they are privately owned and clearly marked with “No Trespassing” signs. For safety reasons, please respect these boundaries.

Beds:
6
Baths:
3.00
Sq.Ft.:
3,760
Status:
Active
MLS#:
MDQA2014244
Type:
Single Family-Detached
Subdivision:
Castle Marina
Lot size:
0.54 Acres
Year built:
1968
Courtesy: Douglas Realty, LLC 410-255-3690
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ADDITIONAL INFORMATION

Welcome home to spacious comfort and thoughtful design in this inviting six-bedroom, three-bath residence nestled on a quiet lane in Chester. With over 3,700 square feet of interior living space, there’s room here for everyone—and maybe even that home office or gym you’ve been dreaming about. Step inside to find an updated kitchen ready for your culinary adventures, featuring modern finishes and plenty of counter space. Two cozy fireplaces offer the perfect backdrop for relaxing winter evenings, and when the weather warms up, the outdoor spaces truly shine. Take a soak in the hot tub just off the deck and the primary bedroom, gather around the paver patio’s firepit with friends, or let kids and pets play safely in the fully fenced backyard. Located just a short stroll from the Cross Island Trailhead at Macum Creek, outdoor enthusiasts will love the access to beautiful trails and waterfront views. Whether you're walking, biking, or just enjoying nature, you’ll appreciate having this scenic gem mere steps from your front door. The layout balances privacy and openness, ideal for both entertaining and everyday living. The primary bedroom offers a quiet retreat, perfect for unwinding after a long day. With its generous square footage and array of features, this home offers flexibility for growing families, multi-generational living, or simply spreading out in style.

Beds:
2
Baths:
3.00
Sq.Ft.:
1,280
Status:
Active
MLS#:
MDQA2013968
Type:
Condo
Subdivision:
Queens Landing
Year built:
1998
Courtesy: RE/MAX Executive 443-274-1900
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ADDITIONAL INFORMATION

OPEN HOUSE, Saturday, August 2, from 11 am to 12 pm...Price Improvement...End Unit in Sought-After Queens Landing – A Waterfront Lifestyle Awaits! Don’t miss this spacious end unit in the highly desirable Queens Landing community! Featuring two primary bedroom suites with private baths, this home offers the perfect blend of comfort and functionality. The expansive kitchen is a chef’s dream, boasting granite countertops, stainless steel appliances, a breakfast bar, and plenty of table space—ideal for entertaining or everyday living. Relax in the sun-filled family room or unwind in the cozy sunroom, which opens to a semi-private paver patio—just steps from the water! Community amenities include: A resort-style in-ground pool overlooking the scenic Chester River Elegant clubhouse with party room and river views Fully equipped fitness center Tennis courts, walking paths, meeting room, and more Access to the marina for boating enthusiasts Queens Landing isn’t just a home—it’s a waterfront way of life. Live where others vacation!

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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

© BRIGHT, All Rights Reserved - The data relating to real estate for sale on this website appears in part through the BRIGHT Internet Data Exchange program, a voluntary cooperative exchange of property listing data between licensed real estate brokerage firms in which Xome Inc. participates, and is provided by BRIGHT through a licensing agreement. Some real estate firms do not participate in IDX and their listings do not appear on this website. Some properties listed with participating firms do not appear on this website at the request of the seller. The information provided by this website is for the personal, non-commercial use of consumers and may not be used for any purpose other than to identify prospective properties consumers may be interested in purchasing. Some properties which appear for sale on this website may no longer be available because they are under contract, have Closed or are no longer being offered for sale. Home sale information is not to be construed as an appraisal and may not be used as such for any purpose. BRIGHT MLS is a provider of home sale information and has compiled content from various sources. Some properties represented may not have actually sold due to reporting errors.



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

    $669,900
    14.5%
    change since last quarter
  • # Active listings

    92
    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