Chester MD Real Estate & Homes for Sale

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Beds:
3
Baths:
3.00
Sq.Ft.:
1,560
Status:
NEW LISTING
MLS#:
MDQA2018980
Type:
Single Family-Detached
Subdivision:
HARBOR VIEW
Lot size:
1.14 Acres
Year built:
1988
Courtesy: Rosendale Realty 410-758-0333
View additional info

ADDITIONAL INFORMATION

Nestled in the serene Harbor View subdivision, this Colonial-style home offers a perfect blend of luxury and comfort. The interior features elegant bamboo and ceramic tile flooring, enhancing the warm ambiance throughout. The gourmet kitchen is equipped with stainless steel appliances, including a dishwasher, electric oven/range, and refrigerator, making culinary adventures a delight. A charming wood-burning fireplace adds a touch of warmth to the living space, creating an inviting atmosphere for relaxation. Set on a generous 1.14-acre lot in a peaceful cul-de-sac, the landscaped grounds provide a tranquil retreat. Enjoy stunning water views of Cox Neck Creek, just a short stroll away, where you can indulge in boating and fishing activities. The property includes a private dock with multiple slips, perfect for water enthusiasts. Additional features include an attached garage, off-street parking, and a spacious deck that invites outdoor living. This home is not just a residence; it's a lifestyle, offering the perfect balance of luxury, nature, and community. Experience the exclusive charm of waterfront living in this property.

Beds:
3
Baths:
2.00
Sq.Ft.:
1,663
Status:
NEW LISTING
MLS#:
MDQA2018934
Type:
Single Family-Detached
Subdivision:
HARBOR VIEW
Lot size:
0.38 Acres
Year built:
2000
Courtesy: Samson Properties 703-378-8810
View additional info

ADDITIONAL INFORMATION

Welcome to 2011 Stevens Drive — a completely renovated home offering exceptional one-level living with a spacious, open floor plan and a long list of thoughtful upgrades throughout. From top to bottom, this home has been transformed with modern finishes, new flooring, fresh paint, updated lighting, renovated bathrooms, and a beautifully redesigned kitchen. The oversized kitchen features quartz countertops, updated appliances, abundant cabinetry, and plenty of workspace, with a large laundry room conveniently located just off the kitchen. Just off the kitchen, a beautifully appointed private dining room provides an elegant space for entertaining and hosting gatherings. With its versatility, this room could also serve as a sophisticated home office, library, or additional flex space to suit your lifestyle. The expansive living room is truly a showstopper, featuring dramatic 30-foot ceilings, recessed lighting, a fireplace, and an open, airy feel that makes the space perfect for both everyday living and entertaining. New LVP flooring flows throughout the entire home, complemented by all-new lighting fixtures and fresh paint throughout. The spacious primary suite offers a private retreat with a walk-in closet, a beautifully updated bathroom with a double quartz vanity, and a rare feature — direct access to the rear deck. Step outside from the primary suite and enjoy views overlooking the peaceful, wooded rear yard. Two additional bedrooms provide plenty of flexibility, including an oversized bedroom with its own walk-in closet. Both bathrooms have been completely updated with new vanities and quartz countertops. Additional improvements include a brand-new roof with a 30-year warranty, an oversized two-car attached garage, abundant storage, and thoughtful updates throughout. With its expansive living spaces, impressive ceiling height, renovated kitchen and baths, private wooded setting, and exceptional primary suite, 2011 Stevens Drive delivers refined, turnkey one-level living at its finest.

Beds:
5
Baths:
3.00
Sq.Ft.:
1,852
Status:
NEW LISTING
MLS#:
MDQA2018862
Type:
Flat
Subdivision:
CHESTER
Lot size:
0.48 Acres
Year built:
1946
Courtesy: Long & Foster Real Estate, Inc. 410-643-2244
View additional info

ADDITIONAL INFORMATION

A rare opportunity to own a property that combines comfortable living with income-producing potential. The primary residence features 2 bedrooms, 1 full bathroom, and a full basement, offering ample storage and living space. Behind the main home is a separate building with two additional rental units. The lower-level unit is a cozy 1-bedroom efficiency apartment, while the upper-level unit offers 2 bedrooms and 1 full bathroom, providing excellent options for rental income or multi-generational living. Situated on approximately one-half acre in Chester, this property offers a convenient location close to shopping, dining, and everyday amenities. Whether you're looking to offset your mortgage with rental income or invest in a versatile property, this unique opportunity is not to be missed.

Beds:
3
Baths:
4.00
Sq.Ft.:
2,100
Status:
NEW LISTING
MLS#:
MDQA2018920
Type:
Townhouse
Subdivision:
BAYSIDE
Year built:
1999
Courtesy: RE/MAX Leading Edge 410-224-3200
View additional info

ADDITIONAL INFORMATION

New Listing! Bayside Condos * End Unit with Garage * Direct Water Views * Direct View of Castle Harbor Marina * Best Location in the Community* Potential to See Your Boat From Your Window * Many Upgrades * Renovated Kitchen * Renovated Primary Bath * Balcony Off Primary w Water Views * Large Walk-In Closet * Dramatic Ship Lap Accent Wall * Waterside Double Width Deck * Dual Zoned HVAC * Community Pool, Hot Tub, Tennis, Volleyball, Exercise Room and On-Site Property Manager * Condo Dues Cover Roof, Siding, Gutters, Lawn Care, Grass Cutting, Pest Control * Public Water, Public Sewer * Gas Fireplace * Convenient Chester Location Close To Shopping and Grocery

Beds:
3
Baths:
4.00
Sq.Ft.:
1,899
Status:
NEW LISTING
MLS#:
MDQA2018750
Type:
Townhouse
Subdivision:
BAYSIDE
Year built:
2001
Courtesy: Long & Foster Real Estate, Inc. 410-643-2244
View additional info

ADDITIONAL INFORMATION

Nestled in the prestigious Bayside community, this exquisite townhouse that was just updated and renovated in 2026 offers a harmonious blend of luxury and comfort, perfect for those seeking an elevated lifestyle. With renovations completed in 2026, this home boasts modern elegance and thoughtful design throughout its 1,899 square feet. Newer roof, HVAC and hot water heater. Step inside to discover a warm and inviting interior with all new luxury vinyl plank and ceramic tile flooring, featuring a floor plan that seamlessly connects the kitchen and living areas. The family room, conveniently located off the kitchen, is adorned with an electric fireplace, creating a cozy focal point for relaxation. The gourmet kitchen is a chef's dream that includes new quartz countertops, backsplash, new stainless steel appliances, built-in microwave, and a cooktop that promises culinary excellence. Ample storage and a spacious layout make meal preparation a delight. The home features three generously sized bedrooms, each designed with comfort in mind, including an updated primary suite with an luxurious walk-in shower, quartz countertops and new tile flooring. Enjoy the convenience of a fully finished basement with a walkout level, providing additional living space and easy access to the outdoors. The basement also includes garage access, ensuring practicality and ease of living. Step outside to your private deck, where the Chester River is just a short stroll away. The community offers an array of amenities, including a sparkling outdoor pool, tennis courts, and a clubhouse, fostering a vibrant social atmosphere. For those who enjoy an active lifestyle, bike trails and exercise rooms are readily available. Parking is a breeze with an attached garage and additional off-street spaces, ensuring ample room for guests. The meticulously maintained grounds, with included lawn care and snow removal, allow you to enjoy your surroundings without the hassle of upkeep. This property is not just a home; it's a lifestyle. Experience the tranquility of riverfront living while being part of a community that values both leisure and luxury. Embrace the opportunity to make this stunning townhouse your own and indulge in the exclusive lifestyle it offers.

Beds:
2
Baths:
3.00
Sq.Ft.:
1,900
Status:
NEW LISTING
MLS#:
MDQA2018944
Type:
Flat
Subdivision:
FOUR SEASONS AT KENT ISLAND
Year built:
2026
Courtesy: Berkshire Hathaway HomeServices PenFed Realty - OP 410-208-3500
View additional info

ADDITIONAL INFORMATION

Welcome to the Chester, a thoughtfully designed home offering 2 bedrooms, 2.5 baths, and a 1-car garage. This home combines modern comfort with functional and stylish living spaces. The main living area features a dry bar and an electric fireplace, creating a warm and inviting atmosphere perfect for both relaxing and entertaining. A dedicated home office with lited French doors provides a private and elegant workspace. The kitchen is designed for both everyday living and convenience, featuring a single oven, microwave, gas cooktop with range hood, dishwasher, pendant lighting, tile backsplash, and quartz countertops. Luxury vinyl plank flooring flows throughout the home, with tile flooring in both full baths. The owner’s bath offers a walk-in shower with a seat and handheld shower wand, double sinks, and quartz countertops, creating a comfortable and functional retreat. 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.

Beds:
3
Baths:
3.00
Sq.Ft.:
2,602
Status:
NEW LISTING
MLS#:
MDQA2018942
Type:
Flat
Subdivision:
FOUR SEASONS AT KENT ISLAND
Year built:
2026
Courtesy: Berkshire Hathaway HomeServices PenFed Realty - OP 410-208-3500
View additional info

ADDITIONAL INFORMATION

Welcome to the Severn, a beautifully designed home offering 3 bedrooms, 2.5 baths, and a 1-car garage. Scheduled for settlement in March 2027, this home blends modern comfort with functional living spaces. The main living area features a dry bar and an electric fireplace, creating a warm and inviting setting for everyday living and entertaining. The owner’s suite includes a private sitting room and large walk-in closets, offering a spacious and relaxing retreat. The kitchen is designed for both style and convenience, featuring a single oven, microwave, gas cooktop with range hood, dishwasher, pendant lighting, tile backsplash, and quartz countertops. Laminate flooring flows throughout the home, with tile flooring in both full baths. The owner’s bath is thoughtfully designed with a walk-in shower featuring a seat and handheld shower wand, double sinks, and quartz countertops for added comfort and functionality. 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.

Beds:
2
Baths:
3.00
Sq.Ft.:
1,900
Status:
NEW LISTING
MLS#:
MDQA2018854
Type:
Apartment
Subdivision:
FOUR SEASONS AT KENT ISLAND
Year built:
2024
Courtesy: Long & Foster Real Estate, Inc. 410-643-2244
View additional info

ADDITIONAL INFORMATION

Every season brings a new perspective from this exceptional top-floor penthouse at Four Seasons at Kent Island. Set within one of the Eastern Shore’s premier 55+ communities, this beautifully appointed residence offers Chester River views from every room, creating a remarkable backdrop from sunrise through sunset. Gently enjoyed as a seasonal retreat, the home reflects a refined coastal aesthetic with custom shiplap accent walls, curated designer lighting, elegant trimmed tray ceilings, and every premium builder upgrade offered. These include GE Monogram appliances, quartz countertops, LVP flooring, gas fireplace, and dry bar cabinets with top shelf glass doors. The sophisticated open-concept design seamlessly connects the spacious living room, gracious dining area, and chef-inspired kitchen, creating an inviting setting for entertaining or simply relaxing.  Beyond the residence, Four Seasons at Kent Island offers an exceptional resort-style lifestyle. Enjoy the heated indoor and outdoor pools, scenic Chester River walking trails just steps from the property, and a vibrant Clubhouse featuring fitness and exercise classes, pickleball, tennis and bocce courts. wellness lectures, mahjong and other board games, numerous social gatherings, and an array of activities designed to bring neighbors together. With the ease of low-maintenance condo living, beautiful waterfront surroundings, convenient access to local marinas, and easy connectivity to the Bay Bridge and points beyond, this penthouse captures the very best of the Eastern Shore lifestyle—elevated, effortless, and truly exceptional

Beds:
3
Baths:
1.00
Sq.Ft.:
960
Status:
NEW LISTING
MLS#:
MDQA2018842
Type:
Single Family-Detached
Subdivision:
NONE AVAILABLE
Lot size:
0.17 Acres
Year built:
1984
Courtesy: Open Door Brokerage, LLC 480-462-5392
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ADDITIONAL INFORMATION

107 Lee Rd is a one-story Chester home with a streamlined layout and a fully fenced backyard. The kitchen provides ample counter space, white cabinetry, a refrigerator, a range, and a nearby utility nook. The main living area has windows and an open connection to the kitchen, creating flexible space for dining and everyday use. The primary bedroom includes two windows and closet storage, while the bathroom has a vanity and a tub-shower combination. A dedicated laundry area includes a washer and dryer. The broad backyard contains a storage shed, completing this residence with practical interior organization and useful outdoor storage.

Beds:
4
Baths:
3.00
Sq.Ft.:
3,680
Status:
NEW LISTING
MLS#:
MDQA2018902
Type:
Single Family-Detached
Subdivision:
MARLING FARMS
Lot size:
0.49 Acres
Year built:
1966
Courtesy: Long & Foster Real Estate, Inc. 410-643-2244
View additional info

ADDITIONAL INFORMATION

Coastal elegance meets effortless waterfront living on the sunrise side of Prospect Bay. From the moment you arrive, this exceptional home feels special. Ideally positioned on a picturesque jut of land, the setting offers a bit of additional protection while showcasing beautiful, ever-changing water views and spectacular sunrises. A circular driveway leads to a charming courtyard entrance framed by lush perennial gardens. Inside, the views immediately take center stage. An open, coastal elegant floor plan bring the beauty of Prospect Bay into every living space. Coffered ceilings elevate the spacious family and dining rooms, while substantial crown molding and elegant finishes add timeless character throughout. The expansive kitchen is as beautiful as it is functional, featuring a 9-foot island with seating, stainless steel appliances, wine cooler, accent lighting, soft-close cabinetry and drawers, and a pantry. And the views? Simply fabulous. Large sliders open to the heated and cooled sunroom, where walls of windows create a spectacular connection to the water. Designed for both entertaining and relaxing, this may quickly become your favorite room in the house. The custom bar is an exceptional conversation piece, crafted with mahogany and other wood from a 1963 Chris-Craft. The primary suite offers a private retreat with water views and direct access to the waterside patio. A generous, customized walk-in closet leads to the beautifully appointed primary bath, featuring double sinks, a private water closet, and an extraordinary L-shaped tiled walk-in shower with showerheads on two walls. Two bedrooms are thoughtfully positioned on the opposite wing of the home with 1 additional bed and full bath on primary wing. Outside, waterfront living truly comes alive. Enjoy morning coffee and evening gatherings on the Trex deck, or head down to the private pier where two boat lifts await, including an impressive 12,000-pound lift. A spacious shed provides convenient additional storage. And the community setting adds even more to the lifestyle, with a boat ramp, waterfront children's playground, picnic area, and kayak launch—all offering easy ways to get outside and enjoy. This home is designed for waterfront living.

Beds:
3
Baths:
2.00
Sq.Ft.:
1,337
Status:
NEW LISTING
MLS#:
MDQA2018892
Type:
Single Family-Detached
Subdivision:
PRICE
Lot size:
0.26 Acres
Year built:
2003
Courtesy: Douglas Realty, LLC 410-255-3690
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ADDITIONAL INFORMATION

Nestled up to vast farm land, this exquisite ranch-style home offers a perfect blend of comfort and sophistication.This residence boasts a well-maintained exterior with charming vinyl siding, inviting you into a space that feels both warm and welcoming. Step inside to discover an open floor plan that seamlessly integrates the kitchen and living areas, creating an ideal setting for both relaxation and entertaining. The luxury vinyl plank flooring flows gracefully throughout, providing a stylish yet durable foundation for your daily life. Natural light pours in, accentuating the spaciousness and warmth of the home. The heart of this residence is undoubtedly the modern kitchen, equipped with SS Appliances that cater to your culinary aspirations. Featuring an electric oven/range, a sleek microwave, and a dishwasher, this kitchen is designed for both functionality and elegance. The refrigerator offers ample storage for all your gourmet ingredients, making meal preparation a delight. With 3 bedrooms and 2 full bathrooms, this home provides plenty of space for comfort and privacy. Updated Ceiling Fans and Lights throughout the home ensure a refreshing atmosphere year-round. Brand New Roof and Water Heater Installed 2024. Step outside to enjoy the inviting patio, new fence, perfect for morning coffee or evening gatherings under the stars. The expansive 0.26-acre lot offers plenty of room for outdoor activities, gardening, or simply enjoying the tranquility of your surroundings. Parking is a breeze with an attached garage and additional driveway space for guests. The gravel driveway adds a rustic charm while ensuring easy access. This property is not just a house; it's a lifestyle. Experience the joy of living in a well-appointed home that combines modern conveniences with a cozy atmosphere. Whether you're hosting friends or enjoying a quiet evening, this residence is designed to meet your every need. Embrace the opportunity to make this beautiful home your own and enjoy the exclusive lifestyle it offers. Sale of this Home is Contingent upon Sellers finding their home of choice.

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:
Active
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:
Active
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:
Active
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:
Active
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:
Active
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:
Active
MLS#:
MDQA2018734
Type:
Townhouse
Subdivision:
BAYSIDE
Year built:
2001
Courtesy: Engel & Volkers Annapolis 443-292-6767
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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:
Active
MLS#:
MDQA2018784
Type:
Single Family-Detached
Subdivision:
NONE AVAILABLE
Lot size:
0.27 Acres
Year built:
2004
Courtesy: Coldwell Banker Realty 410-224-2200
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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:
Active
MLS#:
MDQA2018726
Type:
Townhouse
Subdivision:
BAYSIDE
Year built:
2002
Courtesy: Berkshire Hathaway HomeServices Homesale Realty 410-505-9700
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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:
Active
MLS#:
MDQA2018848
Type:
Flat
Subdivision:
FOUR SEASONS AT KENT ISLAND
Year built:
2025
Courtesy: RE/MAX Executive 443-274-1900
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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:
Active
MLS#:
MDQA2018746
Type:
Townhouse
Subdivision:
QUEENS LANDING
Year built:
1984
Courtesy: Benson & Mangold, LLC 410-822-6665
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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
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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
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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.

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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 21619 Real Estate

Chester is located in Maryland. Chester, Maryland 21619has a population of 4,371. Chester 21619 is less family-centric than the surrounding county with 23.42% 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 21619 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 21619 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

    $703,495
    14.5%
    change since last quarter
  • # Active listings

    98
    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 21619

Zip Code City
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