Chester MD Real Estate & Homes for Sale

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Beds:
2
Baths:
2.00
Sq.Ft.:
1,380
Status:
NEW LISTING
MLS#:
MDQA2018790
Type:
Townhouse
Subdivision:
QUEENS LANDING
Year built:
1987
Courtesy: RE/MAX Executive 443-274-1900
View additional info

ADDITIONAL INFORMATION

The view is the main event. Homes throughout Queens Landing sit at varying distances from the waterfront, and it is hard to get closer than this. Positioned directly along the Chester River, this end unit delivers huge, panoramic water views that immediately set it apart. The windows are perfectly positioned to take full advantage of the setting, giving you a front-row seat to passing boats, changing skies, and some of the most beautiful views on Kent Island. Inside, the home offers a bright, open floor plan with **dual primary suites**, including one conveniently located on the main level—no steps needed for everyday living. The layout ideal for guests, multigenerational living, or simply having a private retreat on each floor. The main level features luxury vinyl plank flooring, an updated kitchen with stainless steel appliances and granite countertops, and a separate bar area with a wine refrigerator. Shiplap accents bring in just the right amount of coastal character while keeping the space comfortable and inviting. Upstairs, the expanded loft has been thoughtfully enclosed, adding approximately 120 square feet of additional living space. There is plenty of room for a family room or media space along with a separate office, reading nook, or flex area. And even from the upper level, those incredible Chester River views remain front and center. Queens Landing offers a true waterfront lifestyle with a clubhouse, heated outdoor pool overlooking the marina and Chester River, fitness center, tennis and pickleball courts, and easy access to the Cross Island Trail. Restaurants, marinas, shopping, and everyday conveniences are nearby, with Route 50 providing easy access to Annapolis, Baltimore, Washington, D.C., and the beaches.

Beds:
6
Baths:
3.00
Sq.Ft.:
2,700
Status:
NEW LISTING
MLS#:
MDQA2018764
Type:
Single Family-Detached
Subdivision:
MARLING FARMS
Lot size:
0.34 Acres
Year built:
2007
Courtesy: Engel & Volkers Annapolis 443-292-6767
View additional info

ADDITIONAL INFORMATION

A rare financing opportunity: qualified buyers may be able to assume the seller’s existing loan at an interest rate of approximately 3%, and VA eligibility is not required. From the welcoming front porch overlooking the bay to the spacious backyard with two storage sheds, this home offers room to live, work and unwind. The kitchen features stainless steel appliances and granite countertops with abundant workspace, making it ideal for everyday living and entertaining. Upstairs, the primary suite feels like a true retreat with a separate sitting area, walk-in closets, dual vanities and an impressive oversized shower. A flexible water-view room on the main level provides the perfect setting for a home office or sixth bedroom. The paved driveway leads to an expansive garage with exceptional storage and workshop space, along with a 30-amp hookup for RV or boat shore power that can also accommodate EV charging. Located on beautiful Kent Island, Marling Farms is an amenity-rich waterfront community offering four beaches, a pavilion, community docks, playground and swing areas, a baseball field and a basketball court.

Beds:
n/a
Baths:
Sq.Ft.:
830
Status:
NEW LISTING
MLS#:
MDQA2018904
Type:
Other
Subdivision:
PINEY NARROWS
Lot size:
0.02 Acres
Year built:
1980
Courtesy: Benson & Mangold, LLC 410-822-6665
View additional info

ADDITIONAL INFORMATION

Looking to own your boat slip instead of paying a hefty lease that could increase year after year? Slip 8-E at Piney Narrows Yacht Haven offers an ownership opportunity in a convenient, community-oriented marina condominium. Measuring 50' x 18' with power, the slip is set beyond a large turnaround area that makes maneuvering easier for larger vessels, including sailboats and sportfish. Located in the heart of Kent Narrows, Piney Narrows Yacht Haven offers a community pool, picnic area with BBQ grill, Yachtsman’s Club lounge, fuel dock with gas and diesel, and complimentary pump-out with fuel purchase. Water, electricity, and Wi-Fi are included. Marina amenities also include winter bubbling at all dock facilities, climate-controlled heads and showers, two laundromats, parking for slip holders and guests, and an on-site canvas shop for new work and repairs. Enjoy convenient access to Kent Narrows restaurants, nearby trails, and popular cruising destinations. Whether you’re seeking a weekend getaway or a home port for the boating season, Slip 8-E offers a comfortable place to enjoy all that Kent Island and the Chesapeake Bay have to offer.

Beds:
4
Baths:
3.00
Sq.Ft.:
2,870
Status:
NEW LISTING
MLS#:
MDQA2018740
Type:
Single Family-Detached
Subdivision:
GIBSONS GRANT
Lot size:
0.13 Acres
Year built:
2011
Courtesy: Wilson Realty & Staging LLC 410-304-2250
View additional info

ADDITIONAL INFORMATION

This beautiful coastal Colonial home in Gibsons Grant offers a perfect blend of comfort and style. With 4 spacious bedrooms and 2.5 bathrooms, the open floor plan invites warmth and connection. Enjoy cooking up your favorite feast in the upgraded kitchen featuring an island, built-in appliances, and endless countertops. The family room, complete with a propane fireplace, is perfect for gatherings and gamed. Step outside to discover beautifully maintained common grounds, a community center, and a inground swimming pool. The neighborhood boasts walking paths, tennis courts, and picnic areas, ideal for outdoor enthusiasts. Located near the Chester River, residents can enjoy serene views and water access. With excellent schools and parks nearby, this community is perfect for those seeking an active lifestyle. Additional conveniences include lawn maintenance, snow removal, and trash services, ensuring a low-maintenance lifestyle. Experience the charm and vibrancy of this welcoming community-your new home awaits!

Beds:
2
Baths:
3.00
Sq.Ft.:
1,680
Status:
NEW LISTING
MLS#:
MDQA2018794
Type:
Townhouse
Subdivision:
QUEENS LANDING
Year built:
1983
Courtesy: RE/MAX Allegiance 703-522-1940
View additional info

ADDITIONAL INFORMATION

Welcome to 7B Queen Victoria Way at Queen’s Landing, a beautifully renovated waterfront residence w/ spectacular views of the marina basin, marina fairway, and Chester River. The largest residence in Building 7, this spacious 2-bedroom, 2½-bath home with loft offers three levels of living and combines the ease of condominium ownership with the space and feel of a townhome. The extensive renovation creates a fresh, modern, move-in-ready interior featuring an open main level, wide-plank luxury vinyl flooring, refreshed baths, and an updated kitchen with white cabinetry, quartz countertops, stainless-steel appliances, pantry storage, and an eating bar. The waterfront primary bedroom enjoys beautiful views, while the versatile loft is ideal for a home office, guest area, reading retreat, or second sitting room. Step directly from the kitchen onto the gated walk-out waterfront patio and enjoy exceptional water and marina views, outdoor dining, entertaining, or simply watching the boats come and go. Multiple outdoor living areas provide even more opportunities to enjoy the waterfront setting. Queen’s Landing amenities include a waterfront pool and clubhouse, tennis and pickleball courts, fitness and racquetball facilities, scenic walking paths, kayak storage and launch areas, and a full-service marina with slips for sail and power boats. Major renovation, generous living space, outstanding views, and the Queen’s Landing waterfront lifestyle come together at 7B Queen Victoria Way. Offering the best of both worlds---condominium ownership with space, privacy, and multi-level layout of a townhome.

Beds:
2
Baths:
3.00
Sq.Ft.:
2,000
Status:
NEW LISTING
MLS#:
MDQA2018826
Type:
Flat
Subdivision:
FOUR SEASONS AT KENT ISLAND
Year built:
2025
Courtesy: RE/MAX Executive 443-274-1900
View additional info

ADDITIONAL INFORMATION

Experience everything Four Seasons at Kent Island has to offer without the wait! Less than one year old, this beautifully maintained home shows like new and offers one of the most desirable locations in the community, with exceptional water views, ground-level living, and an easy walk to the clubhouse and resort-style amenities. Plus, the home is still under warranty with the builder. Inside, you'll find an open-concept floor plan filled with natural light and beautiful water views. The gourmet kitchen features quartz countertops, upgraded cabinetry, GE Café appliances including double wall ovens, stainless steel appliances, tile backsplash, and plenty of space for entertaining. Luxury vinyl plank flooring flows through the main living areas, and an electric fireplace adds a cozy touch to the living room. The primary suite offers water views, private patio access, a large walk-in closet, and a spacious ensuite bath. A second bedroom suite provides a comfortable space for guests, while the private office offers flexibility for working from home or additional living space. Other upgrades include approximately $8,000 in remote-controlled window treatments, a private walk-out patio, climate-controlled storage, and an attached one-car garage. Step outside and enjoy the convenience of ground-level access and the waterfront lifestyle that makes Four Seasons so special. The 24,000-square-foot Chester House clubhouse is just a short walk away and features indoor and outdoor pools, a fitness center, yoga studio, game rooms, library, gathering spaces, and more. Residents also enjoy pickleball, tennis, bocce, walking and biking trails, a kayak and paddleboard launch, fishing and boat pier, dog park, waterfront beach area, fire pits, tiki bar, and a full calendar of clubs, fitness classes, and social events. Located on Kent Island just minutes from the Bay Bridge, Four Seasons offers easy access to Annapolis, Baltimore, DC, and Maryland's Eastern Shore. Waterfront dining, boating, golf, shopping, and the Chesapeake Bay lifestyle are all close by. Why wait for new construction when you can move right into a nearly new home with upgrades already completed?

Beds:
2
Baths:
3.00
Sq.Ft.:
2,014
Status:
NEW LISTING
MLS#:
MDQA2018874
Type:
Single Family-Detached
Subdivision:
FOUR SEASONS AT KENT ISLAND
Lot size:
0.14 Acres
Year built:
2025
Courtesy: RE/MAX Leading Edge 410-224-3200
View additional info

ADDITIONAL INFORMATION

NEW LISTING in the Premiere 55+ Community of Four Seasons @ Kent Island * Offering This Lovely Taylor Model w 2/3 Bedrooms + 2.5 Baths and 3rd Car Tandem Garage * Gorgeous Light Colored Laminated Wood Flooring * Impressive Island w Bar Overhang/Counter Seating + Added Optional Bank of Cabinets w Bonus Counter Space * Pantry * Gas Cooking * Tile Backsplash * Under Cabinet Lighting. This Turn-Key Taylor Model Offers a Comfortable 2014 sf of Living Space with Large Volume Ceilings and Flowing Ever Popular Kitchen-to-Dining-to-Family Room Floor Plan at the Center of the Home. The Bedrooms are Flanked with the 2nd Bedroom with En Suite Full Bath + Walk-In Closet at the Front of the Home and a Rear Facing Primary Bedroom with Tray Ceiling, Triple Windows + Walk-In Closet and En Suite Full Bath with Substantial His 'n Her Vanities and Easy Walk-In Shower. Off the Foyer there is a Versatile Flex Room Accented with Sliding Barn Doors Which Serves Nicely as a Den/Office/Additional Sleeping Area for the Grandkids and Serviced by the Foyer Powder Room Across the Hall. Around the Corner is a Built-In Coat Drop Station and Separate Laundry Room with New Full-Sized Front-Loading Washer and Dryer. The Garage is Spectacular Offering Coveted Additional Parking for a 3rd Car/Golf Cart OR Use it as Additional Storage/Workshop Area. This Home is Propane Gas Heat, Central A/C, Rinnai Tankless Gas Water Heater and Public Water, Public Sewer. At a Mere 1 Year Old, This Home Feels Brand New and Has Been Lightly Lived In and Lovingly Maintained. It Offers an Immediate Move-In Scenario for the Lucky Buyer. Don't Wait for the Builder and Be in by the Holidays! AGENTS: We Are Agent Friendly and We Split Transfer Taxes and Recordation Fees with the Buyer and Offer a Re-Issue Rate on the Title Insurance + Survey to Pass On. The Community of Four Seasons Offers Unparalleled Amenities to Include a 24,000 sf Club House Situated on the Chester River and is Home to a Community Space Where Vibrant Activities are Available to its Vibrant Neighbors and Provides Resort Style Gym, Yoga, Billard's Room, Library, Ballroom and Indoor Pool w Hot Tub + Infinity Outdoor Pool, Cabana, Lounge Areas, Amphitheatre, Fishing Pier, Dog Park, Pickle Ball, Tennis, Bocce Ball + Tot Lot. Homeowners Get Included Grass Cutting, Fertilization + Pesticide Spraying and Lawn Irrigation as a Part of the $315 Monthly HOA Fee Allowing You to Spend More Time Enjoying and Less Time Maintaining! Located 20 Minutes to Historic Downtown Annapolis and to the Regional Anne Arundel Medical Center with an Outpatient Pavilion in Kent Island. It is 30 minutes to Baltimore/Washington International Airport and there are numerous local airport shuttle services offering door to door service making travel easy and stress free for you and your visiting guests. Kent Island Offers a Variety of Wonderful Restaurants Featuring Local Seafood Cuisine + Numerous Marinas and a Freedom Boat Club Location. Four Seasons @ Kent Island is a Wonderful Year-Round or 2nd Home Location for Those Envisioning a Nautically Inspired Lifestyle Combined with a Beautiful, Maintenance Free Home. 168 Redstart Dr is Waiting For You! Call Helpful Lister for More Info.

Beds:
3
Baths:
3.00
Sq.Ft.:
1,899
Status:
NEW LISTING
MLS#:
MDQA2018734
Type:
Townhouse
Subdivision:
BAYSIDE
Year built:
2001
Courtesy: Engel & Volkers Annapolis 443-292-6767
View additional info

ADDITIONAL INFORMATION

Welcome home to this beautifully updated end-unit townhome in the desirable Bayside community, facing a peaceful row of trees. This spacious three-level home offers an open, inviting layout, beautiful hardwood floors, and numerous recent updates. Enter from the main-level foyer into a spacious bonus room—perfect for a family room, home office, gym, or additional entertaining space. Step directly outside to the back deck, where you can enjoy grilling and entertaining while overlooking the large grassy common area. Upstairs, the open-concept main living level features a spacious living room with a gas fireplace and access to a second deck, a dining area, and an updated kitchen, all complemented by beautiful hardwood flooring. A convenient updated half bath completes this level. The top floor offers three generously sized bedrooms. The primary suite features a beautiful custom accent wall and an updated primary bath, creating a comfortable and stylish retreat. The updated hall bathroom serves the additional bedrooms. Recent major updates include a new HVAC system (2025) and a new hot water heater (2026). Condo replaced roof and skylight (2025) & power-washed exterior (9/2026). All providing added peace of mind for the next owner. Enjoy all that the Bayside community has to offer, including an outdoor pool, hot tub, tennis/pickleball courts, clubhouse with meeting/party room, and exercise room. The location is ideal for an active lifestyle, with a short walk to the Chester River, a local pub, the Cross Island Trail, and a marina. You'll also enjoy easy access to the Bay Bridge, restaurants, shopping, and all that Kent Island and Maryland's Eastern Shore have to offer. Move-in ready, beautifully updated, and perfectly situated—this Bayside townhome is ready to welcome you home!

Beds:
5
Baths:
3.00
Sq.Ft.:
2,818
Status:
NEW LISTING
MLS#:
MDQA2018784
Type:
Single Family-Detached
Subdivision:
NONE AVAILABLE
Lot size:
0.27 Acres
Year built:
2004
Courtesy: Coldwell Banker Realty 410-224-2200
View additional info

ADDITIONAL INFORMATION

This charming traditional home, offers a perfect blend of comfort and functionality. With 2,818 square feet of thoughtfully designed living space, this residence features five spacious bedrooms and two and a half bathrooms, ensuring ample room for relaxation and privacy. Step inside to discover a cozy family room with wood burning fireplace that seamlessly connects to the kitchen, creating an inviting space for gatherings and everyday living. The kitchen boasts a gorgeous quartz island, perfect for casual meals or entertaining guests as well as a tastefully designed formal dining room. As you move upstairs, you'll find four spacious bedrooms and 2 full bathrooms including a primary suite. Enjoy the luxury of a soaking tub in the primary bathroom, providing a serene escape after a long day. The 3rd floor features an oversized bedroom or recreation room. The possibilities are endless, create a home gym, theatre or gaming room or office space. Outside, the property features a side-entry garage with additional storage space, ensuring convenience and organization. The 0.27-acre lot provides a lovely fenced in outdoor area for gardening or simply enjoying the fresh air. This home is not just a place to live; it's a place to create lasting memories. Experience the perfect blend of style, comfort, and functionality in this delightful residence. Multi-use zoning allows your home business dreams to come true. Zoned residential and commercial.

Beds:
3
Baths:
4.00
Sq.Ft.:
2,100
Status:
NEW LISTING
MLS#:
MDQA2018726
Type:
Townhouse
Subdivision:
BAYSIDE
Year built:
2002
Courtesy: Berkshire Hathaway HomeServices Homesale Realty 410-505-9700
View additional info

ADDITIONAL INFORMATION

PANORAMIC CHESTER RIVER VIEWS! This fabulous END-UNIT townhome in Kent Island’s sought-after Bayside community offers a special WATERFRONT SETTING with sweeping views of the Chester River as it flows into the Chesapeake Bay. With approximately 2,100 square feet, an abundance of natural light, and water views from so many rooms, this home is all about enjoying the Eastern Shore lifestyle! Beautiful hardwood floors flow throughout the main level, where the kitchen, dining room and family room all take advantage of the spectacular water views. The modern kitchen opens to the living areas, while built-in bookcases and a gas fireplace add character and function to the family room. Step outside to one of two waterside decks and enjoy the ever-changing river views, passing boats and beautiful scenery. Upstairs, wake up each morning to endless WATER VIEWS from the Primary Suite, then step directly onto your private waterside deck with your morning coffee. Bedrooms feature the privacy and convenience of ensuite baths. A large upper-level Bonus Room with its own full bath provides wonderful flexibility—create a 3rd bedroom, spacious home office, a guest suite, den or whatever best fits your lifestyle. The views are even better from up here! Freshly painted and truly MOVE-IN READY, this light-filled end unit offers the combination everyone is looking for—beautiful interiors, flexible living space, two waterside decks and an exceptional location overlooking the Chester River. Bayside offers wonderful community amenities, including a swimming pool, party room, fitness center, tennis/pickleball courts and volleyball. The 38+ mile Cross Island Trail is just around the corner for walking, jogging and biking. You’re also conveniently located near restaurants, grocery shopping, outlet shopping and golf courses. Love boating? The marina bordering the community offers boat slips that may be available for rent or purchase, making it easy to enjoy everything the Chesapeake Bay and Eastern Shore have to offer. Come experience the Kent Island waterfront lifestyle—beautiful views, boating, recreation and convenience, all right outside your door!

Beds:
2
Baths:
3.00
Sq.Ft.:
2,003
Status:
NEW LISTING
MLS#:
MDQA2018848
Type:
Flat
Subdivision:
FOUR SEASONS AT KENT ISLAND
Year built:
2025
Courtesy: RE/MAX Executive 443-274-1900
View additional info

ADDITIONAL INFORMATION

Priced well below market value! The builder can not compete with this price. Welcome to one of the most desirable locations in Four Seasons at Kent Island, where luxury, convenience, and resort-style living come together in a way that few homes in the community can offer. This beautifully upgraded first-floor Magothy model is not only one of the closest residences to the Chester River, but also enjoys a premium location just one building away from the community clubhouse and only steps from the outdoor and indoor pools. One of the most unique advantages of this first-floor residence is its size. Unlike the second, third, and fourth-floor Magothy models, first-floor units offer approximately 100 additional square feet of living space, creating a more spacious and comfortable layout. Combined with more than $30,000 in post-purchase upgrades, this condo stands apart from the moment you walk through the door. By far the most impressive feature, however, is the extraordinary access to the waterfront. Step through your sliding glass doors and find yourself just moments from the Chester River. The peaceful setting allows you to enjoy water views, wildlife, and gentle river breezes from your private patio while offering one of the most coveted locations within the community. Whether you're taking a morning stroll along the shoreline or relaxing outdoors with a cup of coffee, the river feels like an extension of your backyard. Inside, luxury vinyl plank flooring flows throughout the home, complementing the bright, open floor plan filled with natural light from oversized windows and soaring ceilings. The gourmet kitchen is designed for both everyday living and entertaining, featuring a large center island, under-cabinet lighting, abundant cabinetry, and a custom dry bar area. The adjoining dining and living spaces create a seamless gathering area, highlighted by recessed lighting and a cozy electric fireplace. The spacious primary suite serves as a private retreat with dual closets and a beautifully upgraded bath featuring double vanities, custom tile work, a walk-in shower, and dual shower heads. A generous guest bedroom and adjacent full bath provide comfortable accommodations for family and visitors alike. Additional features include a private locked storage room, garage, custom finishes throughout, and a covered patio accented with stacked stone columns—an ideal place to unwind and enjoy the tranquil surroundings. With the clubhouse and pool just steps away, you'll enjoy unmatched convenience while still maintaining a peaceful and private setting. Residents of Four Seasons enjoy an exceptional resort-style lifestyle with a stunning clubhouse, indoor and outdoor pools, tennis and pickleball courts, fitness facilities, walking and biking trails, a community pier, and a full calendar of social activities coordinated by the community lifestyle director. Conveniently located near waterfront dining, marinas, golf courses, Annapolis, Baltimore, Washington, D.C., and BWI Airport, this is Eastern Shore living at its finest. Opportunities to own a first-floor waterfront-proximity unit in this location are exceptionally rare. With extra square footage, extensive upgrades, steps-to-the-pool convenience, and one of the closest locations in the community to the Chester River, this home offers a lifestyle that simply cannot be replicated.

Beds:
2
Baths:
3.00
Sq.Ft.:
1,680
Status:
NEW LISTING
MLS#:
MDQA2018746
Type:
Townhouse
Subdivision:
QUEENS LANDING
Year built:
1984
Courtesy: Benson & Mangold, LLC 410-822-6665
View additional info

ADDITIONAL INFORMATION

Located in the beautiful Queens Landing community, this Spanish-style waterfront townhouse offers a luxurious lifestyle with stunning river views. The interior boasts an open floor plan, featuring a combination dining and living area with recessed lighting and a corner gas fireplace. The kitchen is equipped with upgraded countertops and high-end appliances, including a built-in microwave and new additional cabinet and countertop space. Upstairs you will find 2 spacious bedrooms both with private balconies, 2 full bathrooms, and a large loft space above the primary bedroom. Outside you can enjoy your private balcony or relax on the patio, surrounded by beautifully landscaped grounds. The community amenities include an in-ground pool, tennis courts, walking trails, and access to the Chester River. Come tour this waterfront property today!

Beds:
1
Baths:
2.00
Sq.Ft.:
1,260
Status:
Active
MLS#:
MDQA2018696
Type:
Townhouse
Subdivision:
QUEENS LANDING
Year built:
1984
Courtesy: Chesapeake Real Estate Associates, LLC 410-643-4663
View additional info

ADDITIONAL INFORMATION

Enjoy waterfront living in the sought-after Queens Landing community! This Mediterranean style 1-bedroom, 1.5-bath end unit condo offers a unique layout with beautiful water views and multiple outdoor spaces designed to make the most of the setting. The first-level primary bedroom and full bath allow for convenient main-level living. The upper-level loft adds valuable flex space with a wood-burning fireplace, skylights, and an abundance of natural light making it the perfect space for a home office, sitting area, guest space, or cozy retreat. Step outside and choose your view, from the garden-style front patio to the waterside patio out back or the upper-level balcony overlooking the water. With inviting indoor spaces, plenty of natural light, and multiple places to relax outdoors, this condo offers an easy, low maintenance, Eastern Shore lifestyle in a beautiful waterfront community.

Beds:
2
Baths:
3.00
Sq.Ft.:
2,010
Status:
Active
MLS#:
MDQA2018806
Type:
Single Family-Detached
Subdivision:
FOUR SEASONS AT KENT ISLAND
Lot size:
0.16 Acres
Year built:
2026
Courtesy: Berkshire Hathaway HomeServices PenFed Realty - OP 410-208-3500
View additional info

ADDITIONAL INFORMATION

Welcome to the Taylor, a beautifully designed home offering 2 bedrooms, 2 baths, and a 3-car garage. This home combines an open-concept layout with thoughtful design for both comfort and functionality. The main living area features a cozy fireplace with mantel and hearth, creating a warm and inviting focal point. A dedicated home office provides a private space for productivity, while the screened patio extends the living area outdoors—perfect for entertaining or relaxing. The kitchen is equipped for both style and performance, featuring a single oven, microwave, gas cooktop with range hood, dishwasher, French door refrigerator, pendant lighting, tile backsplash, and quartz countertops. Quartz is also featured in the owner’s bath for a cohesive, elegant finish. Hardwood flooring flows throughout the foyer, extended foyer, HovHall, kitchen, dining area, great room, home office, bedrooms 2, the primary suite, loft, and second floor, while tile is featured in all full baths and the laundry room. The primary bath includes a walk-in shower with seat and handheld shower wand and a double-sink vanity for added convenience and luxury. 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:
3
Baths:
3.00
Sq.Ft.:
2,772
Status:
Active
MLS#:
MDQA2018804
Type:
Single Family-Detached
Subdivision:
FOUR SEASONS AT KENT ISLAND
Lot size:
0.16 Acres
Year built:
2026
Courtesy: Berkshire Hathaway HomeServices PenFed Realty - OP 410-208-3500
View additional info

ADDITIONAL INFORMATION

Welcome to the Kerr, a beautifully designed home offering 3 bedrooms, 3 baths, and a 3-car garage. This home combines an open-concept layout with thoughtful design for both comfort and functionality. The main living area features a cozy fireplace with mantel and hearth, creating a warm and inviting focal point. A dedicated home office provides a private space for productivity, while the screened patio extends the living area outdoors—perfect for entertaining or relaxing. The kitchen is equipped for both style and performance, featuring a single oven, microwave, gas cooktop with range hood, dishwasher, French door refrigerator, pendant lighting, tile backsplash, and quartz countertops. Quartz is also featured in the owner’s bath for a cohesive, elegant finish. Hardwood flooring flows throughout the foyer, extended foyer, HovHall, kitchen, dining area, great room, home office, bedrooms 2, the primary suite, loft, and second floor, while tile is featured in all full baths and the laundry room. The primary bath includes a walk-in shower with seat and handheld shower wand and a double-sink vanity for added convenience and luxury. 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:
3
Baths:
3.00
Sq.Ft.:
2,772
Status:
Active
MLS#:
MDQA2018802
Type:
Single Family-Detached
Subdivision:
FOUR SEASONS AT KENT ISLAND
Lot size:
0.16 Acres
Year built:
2026
Courtesy: Berkshire Hathaway HomeServices PenFed Realty - OP 410-208-3500
View additional info

ADDITIONAL INFORMATION

Welcome to the Kerr, a beautifully designed home offering 3 bedrooms, 3 baths, and a 3-car garage. This home combines an open-concept layout with thoughtful design for both comfort and functionality. The main living area features a cozy fireplace with mantel and hearth, creating a warm and inviting focal point. A dedicated home office provides a private space for productivity, while the screened patio extends the living area outdoors—perfect for entertaining or relaxing. The kitchen is equipped for both style and performance, featuring a single oven, microwave, gas cooktop with range hood, dishwasher, French door refrigerator, pendant lighting, tile backsplash, and quartz countertops. Quartz is also featured in the owner’s bath for a cohesive, elegant finish. Hardwood flooring flows throughout the foyer, extended foyer, HovHall, kitchen, dining area, great room, home office, bedrooms 2, the primary suite, loft, and second floor, while tile is featured in all full baths and the laundry room. The primary bath includes a walk-in shower with seat and handheld shower wand and a double-sink vanity for added convenience and luxury. 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:
3
Baths:
2.00
Sq.Ft.:
2,331
Status:
Active
MLS#:
MDQA2018766
Type:
Single Family-Detached
Subdivision:
FOUR SEASONS AT KENT ISLAND
Lot size:
0.14 Acres
Year built:
2021
Courtesy: RE/MAX Leading Edge 410-224-3200
View additional info

ADDITIONAL INFORMATION

Beds:
2
Baths:
3.00
Sq.Ft.:
1,440
Status:
Active
MLS#:
MDQA2018730
Type:
Townhouse
Subdivision:
QUEENS LANDING
Year built:
1998
Courtesy: EXP Realty, LLC 888-860-7369
View additional info

ADDITIONAL INFORMATION

Nestled in the community of Queens Landing, this townhome offers a blend of coastal charm and contemporary elegance with carefree living. Boat slips with provisioned boats when available through marina along with Kayaking and storage. With 1,440 square feet of thoughtfully designed living space, this home is a sanctuary of comfort and style. Step inside to discover an inviting open floor plan that seamlessly connects the living and dining areas, creating an ideal space for entertaining or quiet evenings at home. The family room, conveniently located off the kitchen, features an electric fireplace, providing a cozy ambiance for gatherings. On the second level, are two bedrooms both with their private full bath. The most recent upgrades include; New HVAC, new electric fireplace, new kitchen appliances (GE Profile), updated bathroom, new shower, new carpeting and painted throughout. The community amenities include access to an outdoor swimming pool, tennis courts, and pickleball courts, all designed for an active and social lifestyle. The clubhouse and fitness center provide additional opportunities for relaxation and recreation. This home is conveniently located off of 301/50 and minutes from the Bay Bridge for an easy commute. to Annapolis/DC or Baltimore. NOTE; Community upgrade for Fios internet in process and a line of new trees is going behind the home this fall for added privacy as per HOA

Beds:
2
Baths:
3.00
Sq.Ft.:
1,993
Status:
Active
MLS#:
MDQA2018728
Type:
Single Family-Detached
Subdivision:
FOUR SEASONS AT KENT ISLAND
Lot size:
0.13 Acres
Year built:
2019
Courtesy: Long & Foster Real Estate, Inc. 410-544-4000
View additional info

ADDITIONAL INFORMATION

Built in 2019, this coastal style cutie is BETTER than new & offers a bright open layout that includes 2 SPACIOUS BEDROOMS complete w/private ENSUITE BATHROOMS plus additional HOME OFFICE/DEN or spare bedroom & POWDER ROOM off foyer. There is a 22X10 BONUS storage space in the upgraded GARAGE LOFT/ “Sky-Basement” The stunning CHEF'S KITCHEN is the heart of this home & opens up to DINING AREA & GREAT ROOM. KITCHEN features upgraded CAFE by GE STAINLESS APPLIANCES, granite countertops, a plethora of custom 42" cabinets, huge CENTER ISLAND & PROFESSIONALLY appointed WALK-IN PANTRY. Dining area off kitchen flows seamlessly into the FAMILY/GREAT ROOM complete w/GAS FIREPLACE for cool fall evenings & SUNDAY-FUN-DAY Football gatherings! Enjoy the ease & luxury of a primary bath w/large CUSTOM WALK-IN SHOWER featuring built-in bench, & double vanities . Spacious walk-in closet (also custom-finished) includes a built-in safe for keeping valuables & important documents. And the crowning touch? PLANTATION SHUTTERS throughout--ABSOLUTELY STUNNING---and UNDENIABLY ELEVATED! An OVERSIZED 2-CAR GARAGE complete w/OPTIONAL 22x10 LOFT STORAGE offers a smart, tucked-away solution for everything you want close at hand-but out of sight. The meticulous exterior features a screened porch, & paver patio w/retractable awning providing additional space for entertaining or simply relaxing & enjoying the outdoors. The beautifully landscaped lot backs to trees and popular CROSS-ISLAND TRAIL as well as views of the scenic community water-features, & even has an invisible fence for your four-legged friend. The "Icing On The Cake" is definitely the ABUNDENT AMENITIES (including lawn-care!) covered by your reasonable monthly HOA dues....Stunning (WATERFRONT!) INDOOR & OUTDOOR SWIMMING POOLS, fitness center, DOG PARK, walking paths, fishing/crabbing pier, PICKLE & BOCCE BALL COURTS & SO MUCH MORE- there's always something to see & enjoy. The community also features a beautiful clubhouse with BALLROOM and various multi-purpose spaces for learning opportunities & social events. Located on the Chester River & Chesapeake Bay, you will be DAZZLED by the natural beauty of the area- -Of YOUR Community.... Literally a vacation without ever leaving town. Local medical facilities, shopping, restaurants & access to the DELMARVA beaches enhance the neighborhood's appeal, making it a wonderful place to call home. Experience the vibrant lifestyle and FRIENSHIPS & MEMORIES to be made in this exceptional community!

Beds:
3
Baths:
4.00
Sq.Ft.:
2,076
Status:
Active
MLS#:
MDQA2018742
Type:
Townhouse
Subdivision:
BAYSIDE
Year built:
2002
Courtesy: Redfin Corp 301-658-6186
View additional info

ADDITIONAL INFORMATION

KENT ISLAND WATERFRONT • GOURMET KITCHEN • TWO PRIVATE DECKS • LUXURIOUS PRIMARY SUITE • CLUBHOUSE + FITNESS CENTER • MARINA ACCESS Experience Kent Island waterfront living in this beautifully appointed townhome in sought-after Bayside of Chester. The open-concept interior offers abundant natural light, spacious living areas, and stylish finishes throughout. The gourmet kitchen is designed for both everyday living and entertaining, featuring generous cabinetry, ample counter space, and a large center island with seating that flows seamlessly into the dining and living areas. The spacious primary suite offers a walk-in closet and luxurious ensuite bath, while additional bedrooms and flexible spaces provide room for guests, a home office, or recreation. Enjoy TWO PRIVATE DECKS for outdoor dining, morning coffee, or relaxing in the peaceful surroundings. An attached garage, additional storage, and parking spaces across the street add convenience. Bayside amenities include a clubhouse, fitness center, pool, tennis courts, walking trails, and marina access. Castle Marina slips are available for short-term or annual rental, with select slips near Queens Landing potentially available for purchase. Close to waterfront dining, shopping, golf, and major commuter routes.

Beds:
3
Baths:
3.00
Sq.Ft.:
2,787
Status:
Active
MLS#:
MDQA2018418
Type:
Single Family-Detached
Subdivision:
GIBSONS GRANT
Lot size:
0.21 Acres
Year built:
2011
Courtesy: Samson Properties 703-378-8810
View additional info

ADDITIONAL INFORMATION

Welcome to 402 Macum Creek Drive, ideally situated along Macum Creek in the beautiful waterfront community of Gibson’s Grant. This thoughtfully designed Hartley model by Koch Homes offers three bedrooms, two-and-a-half baths, and an open floor plan perfect for everyday living and entertaining. A beautiful stone propane fireplace creates a warm and inviting focal point in the main living area. Double porches provide the perfect place to relax and take in breathtaking sunset views over the creek. Positioned on a desirable corner lot, the home also features a fenced backyard, spacious deck, and hardscape patio—ideal for outdoor dining, entertaining, or simply enjoying the peaceful surroundings. A rear-entry two-car garage with a large parking pad provides ample space for residents and guests. Gibson’s Grant is conveniently located near waterfront dining, shopping, and the Cross Island Trail, with easy access to the Bay Bridge for commuting or exploring all that the Eastern Shore has to offer. Experience the perfect blend of waterfront community living, everyday convenience, and the relaxed Shore lifestyle.

Beds:
2
Baths:
2.00
Sq.Ft.:
1,274
Status:
Active
MLS#:
MDQA2018584
Type:
Single Family-Detached
Subdivision:
NONE AVAILABLE
Lot size:
0.29 Acres
Year built:
1922
Courtesy: RE/MAX Executive 443-274-1900
View additional info

ADDITIONAL INFORMATION

Your Island Getaway Is Waiting! Dreaming of a cozy home where life feels a little more relaxed and every season brings something to look forward to? This charming 2/3-bedroom Island home may be just what you’ve been waiting for! Start your mornings—or wind down your evenings—on the inviting front porch, where you can swing with the little ones, rock to your favorite playlist, and enjoy the laid-back Island lifestyle. Inside the spacious living room features a wood stove, creating the perfect spot for cozy winter nights. The bright, well-appointed kitchen offers a center island, granite countertops, stainless steel appliances, abundant cabinetry, and a pantry—plenty of room for preparing family meals or entertaining friends. Just off the kitchen, the screened porch is ready for three-season enjoyment. Imagine crab feasts with family and friends, relaxing evenings, or cheering on your favorite team while enjoying the crisp fall air! Outside, the huge, privately fenced rear yard offers plenty of space for the kids to play, pets to roam, or everyone to gather. Multiple sheds provide convenient storage for all your crabbing, fishing, boating, and outdoor gear. Upstairs, you’ll find two spacious bedrooms plus a walk-up attic with endless possibilities. Use it for additional storage, a home office, hobby space—or transform it into an additional bedroom to suit your needs. Whether you’re looking for a year-round home, a weekend retreat, or your own slice of Island living, this one offers comfort, space, charm, and plenty of potential at a great price. PLUS...the boat ramp is just 2 mins away which means fresh seafood is what's for dinner! Come see it for yourself—this Island gem won’t last long!

Beds:
3
Baths:
3.00
Sq.Ft.:
2,742
Status:
Active
MLS#:
MDQA2018534
Type:
Single Family-Detached
Subdivision:
HARBOR VIEW
Lot size:
0.35 Acres
Year built:
2005
Courtesy: Chesapeake Real Estate Associates, LLC 410-476-2201
View additional info

ADDITIONAL INFORMATION

Discover exceptional waterfront living on picturesque Cox Creek. Beautifully renovated approximately four years ago, this move-in-ready home combines modern updates with the timeless appeal of Maryland's Eastern Shore. Offering 3 bedrooms, 2.5 baths, and a highly desirable main-level primary suite, the thoughtfully designed layout provides both comfort and functionality. Inside, you'll find a dedicated home office and stylish engineered hardwood and tile flooring throughout, creating a seamless and low-maintenance living space. Large windows invite natural light and showcase the home's tranquil waterfront setting. Outdoor living is just as impressive, featuring two maintenance-free decks, a patio ideal for grilling and entertaining, and a fenced backyard perfect for pets, play, or simply enjoying the beautiful surroundings. Whether hosting friends or relaxing with a morning coffee, this home offers multiple spaces to take in the peaceful water views. Boating enthusiasts will appreciate the private pier equipped with both water and electric service, while the pier decking was replaced last year, providing added value and peace of mind. Enjoy easy access to boating, fishing, crabbing, kayaking, and all the activities that make waterfront living so special. Conveniently located on Kent Island near shopping, dining, marinas, and commuter routes, this exceptional waterfront property offers the perfect blend of luxury, comfort, and Chesapeake Bay lifestyle. 3 Bedrooms 2.5 Baths Main-Level Primary Suite Separate Office Waterfront on Cox Creek Private Pier with Water & Electric New Pier Decking (2025) Two Maintenance-Free Decks Grilling Patio Fenced Backyard Renovated Approximately 4 Years Ago

Beds:
3
Baths:
3.00
Sq.Ft.:
1,302
Status:
Active
MLS#:
MDQA2018634
Type:
Townhouse
Subdivision:
BRIDGE POINTE
Year built:
1993
Courtesy: Rosendale Realty 410-758-0333
View additional info

ADDITIONAL INFORMATION

Low maintenance island living at its best! 6005 Bridgepointe Dr has a NEW ROOF, NEW A/C UNIT, freshly painted and ready for its new owners! All appliances new within the last two years, power washed & fresh paint on the deck with beautiful views of the pond. Easy access to RT50 - perfect for the commuter. Quiet neighborhood.

Beds:
3
Baths:
3.00
Sq.Ft.:
2,008
Status:
Active
MLS#:
MDQA2018494
Type:
Townhouse
Subdivision:
QUEENS LANDING
Year built:
1994
Courtesy: Anne Arundel Properties, Inc. 410-224-3600
View additional info

ADDITIONAL INFORMATION

Welcome to 43-A Queen Neva Court, a pristine 3-bedroom, 2.5-bath contemporary condo in the sought-after Queens Landing community. Offering more than 2,000 square feet of living space, the largest model in the community, this spacious end unit features an open, sunlit floor plan that is perfect for everyday living and entertaining. The oversized kitchen provides abundant workspace and storage, while the inviting living area is highlighted by a cozy fireplace. The generous primary suite includes a private bath with a soaking tub and separate shower. Step outside to your patio and enjoy peaceful pond views, added privacy, and the benefits of end-unit living. Queens Landing offers an amenity-rich lifestyle with a community pool, clubhouse, fitness center, tennis courts, and much more. This one is truly a 10/10!

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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

    N/A
  • # Active listings

    84
    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