Chester Homes with Jog/Walk Path Amenities

Chester Homes with Jog/Walk Path Amenities

Welcome to Chester, Maryland – a hidden gem nestled in the heart of Queen Anne's County, where picturesque landscapes meet a vibrant community spirit. This charming town is perfectly positioned along the scenic Chester River, offering residents a serene lifestyle amid nature's beauty. With its close-knit community, Chester boasts a warm and welcoming atmosphere, making it an ideal place for families, retirees, and anyone looking to enjoy the tranquility of small-town living.

One of the standout features of Chester is its commitment to outdoor living. Homes in this delightful area often come equipped with jog and walk path amenities, inviting residents to embrace an active lifestyle. Imagine starting your day with a refreshing jog along tree-lined paths or enjoying leisurely evening strolls with loved ones as the sun sets over the river. These amenities not only promote health and well-being but also foster a sense of community as neighbors come together to enjoy the great outdoors.

In addition to its recreational offerings, Chester is conveniently located near major highways, providing easy access to nearby cities and attractions. Whether you're looking to explore local shops, savor delicious dining options, or partake in seasonal events, Chester has something for everyone.

In summary, Chester, MD, is more than just a place to live; it’s a lifestyle choice. With beautiful homes featuring jog and walk path amenities, you can enjoy an active, fulfilling life surrounded by nature and community. Come discover the charm of Chester and experience the perfect blend of comfort and adventure!

Newest Chester Homes with Jog/Walk Path Amenities

$379,900
1 Beds ⋅ 2 Baths ⋅ MDQA2018696 MLS
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.

12 Queen Anne Way Unit #J, Chester
$789,000
3 Beds ⋅ 3 Baths ⋅ MDQA2018418 MLS
Professional Photos Coming Soon! 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.

402 Macum Creek Dr, Chester
$944,900
3 Beds ⋅ 3 Baths ⋅ MDQA2018566 MLS
Welcome to 275 Warbler Way, a beautifully upgraded Kerr model by K. Hovnanian in the sought-after 55+ Four Seasons at Kent Island community. Less than two years old and already through its one-year builder punch list, this home offers the ease of newer construction without the wait—plus thoughtful upgrades and finishes already in place. Situated on a premium corner lot, this impressive home features 3 bedrooms, a dedicated home office, a spacious second-floor loft and a 3-car garage, including a tandem bay with EV charger. Inside, custom details immediately set it apart, including decorative molding in the foyer and primary bedroom, upgraded chandeliers in the foyer and dining room, custom window shades and a beautiful stone propane fireplace. The kitchen showcases K. Hovnanian's upgraded Looks package with crisp white cabinetry and upgraded Thermador appliances, complemented by reverse osmosis at the kitchen sink and a whole-house water filtration system. Additional features include a Rinnai tankless water heater, two-zone HVAC with propane backup and a whole-home surge protector. Outdoor living is ready to enjoy with a paver patio, propane grill hookup, irrigation system and upgraded landscaping—no waiting for a new yard to grow in or projects to be completed. Best of all, the location puts the Four Seasons lifestyle right outside your door. Enjoy easy access to the community's pickleball courts, clubhouse, indoor and outdoor pools, fitness center, walking trails, pier, kayak launch and more. Why wait to build when you can move right into a nearly new Kerr with the premium lot, upgrades, landscaping and finishing touches already done? 275 Warbler Way delivers exceptional value and an easy, move-in-ready Eastern Shore lifestyle.

275 Warbler Way, Chester
$439,000
3 Beds ⋅ 4 Baths ⋅ MDQA2018508 MLS
Set along scenic Lake Amletto in the waterfront resort-style community of Queen’s Landing, this three-level garage townhome pairs updated interiors with relaxing water views and an impressive collection of community amenities. Neutral paint, wide-plank luxury vinyl plank flooring, new carpeting, and updates to the kitchen and bathrooms create a fresh, cohesive feel throughout. Step inside to a spacious living and dining room combination designed for easy everyday living and entertaining. The dining area flows into the updated kitchen, with a breakfast bar providing a natural transition between the spaces. Quartz countertops, stainless steel appliances, and a subway tile backsplash give the kitchen a polished look, while its open connection to the adjacent family room keeps the layout inviting and functional. A sliding glass door leads from the family room to the deck, where views of Lake Amletto create a peaceful backdrop for dining or unwinding outdoors. Upstairs, all three bedrooms feature vaulted ceilings that enhance the sense of space. The primary bedroom includes two closets and a stylish vanity area, along with a private water closet featuring a tiled tub and shower surround with a soaking tub. Two additional bedrooms share the hall bath, where a vaulted ceiling and statement light fixture lend an elevated feel. The lower level adds valuable flexibility with a recreation room and sliding glass door opening to the backyard. A separate laundry room is also located on this level, along with interior access to the attached one-car garage. Just inside the garage, a convenient drop zone helps keep everyday essentials organized, while the painted garage offers additional storage space. Beyond the home, Queen’s Landing delivers a true waterfront lifestyle along the Chester River on Kent Island. Residents enjoy a heated waterfront pool, clubhouse, fitness center, indoor racquetball court, tennis and pickleball courts, walking paths, kayak storage and launch areas, and a resident-only 62-slip marina. With Lake Amletto just outside and access to Kent Narrows, Eastern Bay, and the Chesapeake Bay nearby, this inviting home offers an ideal blend of updated comfort, water views, and resort-style living. Please note: photos depicting furniture have utilized virtual staging.

41 Queen Catherine Ct, Chester
$569,900
4 Beds ⋅ 3 Baths ⋅ MDQA2018296 MLS
OPEN SUNDAY 11AM-1PM. Kent Island Living at Its Best! Welcome to this stunning colonial-style home nestled in the desirable Clayborne Woods community in Chester. Offering 2,332 square feet of thoughtfully designed living space, this beautifully maintained residence blends elegance with modern updates and everyday comfort. From the inviting covered front porch with newly replaced fiberglass columns (2025) to the upgraded interior, every detail has been carefully considered. Step inside to a welcoming two-story foyer leading to a formal living room and separate dining area. The interior features LVP flooring (2020), ceramic tile, plush new carpet throughout the stairs/upper level (2026) and architectural details throughout including crown molding, chair rail, and wainscoting. The gourmet kitchen is the heart of the home, showcasing silestone countertops, stainless steel appliances, under-cabinet lighting, ceramic tile backsplash, a spacious island, and additional cabinetry and countertop space adjacent to the pantry. The separate breakfast area features a new sliding glass door (2025) leading to the private fenced backyard, complete with a Trex/Vinyl deck (2015), shed, extensive hardscape, and beautifully landscaped grounds. The inviting family room features a floor-to-ceiling stone gas/propane fireplace (2018) and adjacent office/storage area. Renovated main-level powder room with updated vanity and lighting (2020), laundry room with Closet America cabinetry and access to attached two-car garage with epoxy flooring (2024) and insulated, finished walls (2025). OWNER IS WILLING TO REMOVE STAIR LIFT TO UPPER LEVEL AND REPLACE WITH CARPET ON STAIRCASE. On the upper level, you'll find four generously sized bedrooms, including a spacious primary suite with a walk-in closet and private en-suite bathroom featuring dual granite vanities and a large walk-in shower. The renovated hall bathroom offers updated ceramic tile, a quartz vanity, and tub/shower combination. The second floor and stairway have also been freshly painted. Additional highlights include updated hallway, foyer, and kitchen lighting, brushed nickel door hardware and hinges throughout. The home also features 6" gutters and downspouts with gutter guards (2023), asphalt roof replaced in (2018), and driveway torn out and replaced/sealed (2024/2026). Clayborne Woods is a private neighborhood that offers a jog/walk path, community management, and trash service. Enjoy the best of Kent Island living with a location just minutes from the Chesapeake Bay Bridge, beaches, parks, boat ramps, marinas, waterfront dining, shopping, restaurants, and schools. This exceptional home combines comfort, convenience, thoughtful updates, and coastal charm. Come see for yourself what Kent Island living is all about!

233 Cross Creek Ct, Chester
$899,000
3 Beds ⋅ 3 Baths ⋅ MDQA2018244 MLS
Welcome to 148 Elinor Street, where timeless coastal style meets a beautifully reimagined interior in the sought-after waterfront community of Gibson’s Grant. This 3-bedroom, 2.5-bath Hartley model by Koch Homes underwent an extensive renovation in 2025, creating a truly turnkey home filled with thoughtful upgrades, designer finishes, and exceptional attention to detail. Step inside to refinished and newly stained hardwood floors, fresh designer paint, upgraded lighting, new interior doors with Emtek hardware, and a beautifully updated staircase. The dining room was opened to create a more connected, airy flow, while upgraded recessed lighting and Lutron Caséta switches add modern convenience throughout. The kitchen has been refreshed with new KitchenAid appliances, backsplash, under-cabinet lighting, updated fixtures and hardware, a new exhaust fan and disposal, instant hot water, and an enhanced pantry with pull-out storage. Just beyond, the mudroom adds both charm and function with brick flooring and Pottery Barn built-ins. The primary suite feels like a private retreat, featuring a completely renovated bath with a custom vanity, Kohler fixtures, and a luxurious BainUltra spa tub with chromatherapy lighting, along with added built-in closet storage. The guest bath and powder room have also been beautifully updated, while the laundry room features new cabinetry, luxury vinyl flooring, and a new GE washer and dryer. Outside, enjoy a private setting backing to trees and a quiet rear alley. Extensive professional landscaping, a drip irrigation system, landscape lighting, new pergola, and added deck railing create an inviting outdoor space for relaxing or entertaining. Even the garage has been thoughtfully upgraded with an EV charger, Elfa shelving, motion-detected lighting, fresh paint, and a GE refrigerator. Located in Gibson’s Grant, one of Kent Island’s most desirable waterfront communities, residents enjoy picturesque streets, walking trails, a community pool and clubhouse, waterfront pavilion, fishing pier, kayak launch, and beautiful views of Macum Creek and the Chester River. With its extensive 2025 renovation, private setting, and coveted Gibson’s Grant location, 148 Elinor Street offers the rare opportunity to enjoy an established coastal community with the feel and finish of a newly designed home.

148 Elinor St, Chester
$835,000
3 Beds ⋅ 3 Baths ⋅ MDQA2018120 MLS
Welcome to Four Seasons at Kent Island, where luxury waterfront living meets the ease of a premier 55+ lifestyle on the shores of the Chester River. Offering breathtaking, unobstructed water views and exceptional community amenities, this beautifully appointed three-bedroom, two-and-a-half-bath condominium is designed for those who appreciate comfort, elegance, and low-maintenance living. The light-filled, open-concept floor plan showcases luxury vinyl plank flooring throughout, recessed lighting, and expansive windows that capture stunning views of the Chester River from nearly every angle. The spacious living room is anchored by a cozy electric fireplace and flows seamlessly into the dining area and gourmet kitchen, creating the perfect space for entertaining or relaxing. The kitchen features stainless steel appliances, a gas cooktop, white cabinetry, generous countertop space, and an inviting layout that keeps everyone connected. Just beyond the living area, step onto the expansive waterside balcony and enjoy panoramic river views, morning coffee, spectacular sunsets, and endless opportunities to watch boats glide by. The luxurious primary suite is a private waterfront retreat, complete with direct balcony access, a spacious sitting area, two walk-in closets, and an elegant ensuite bath featuring dual vanities and a large walk-in shower. Two additional bedrooms provide comfortable accommodations for guests, a home office, or hobbies. Additional highlights include a beautifully crafted built-in bar, electric blinds, a large laundry room, a dedicated storage room, and an attached one-car garage with new epoxy speckled floor. Residents enjoy an exceptional resort-style lifestyle with amenities that include indoor and outdoor swimming pools, a fitness center, clubhouse, library, billiards room, hot tub, Bocce Ball, pickleball and tennis courts, picnic areas, tot lots, and a community pier overlooking the Chester River. Ideally located just minutes from shopping, dining, golf, marinas, and the Chesapeake Bay Bridge, this exceptional waterfront residence offers the perfect blend of luxury, convenience, and carefree Eastern Shore living.

201 Switchgrass Way Unit #34, Chester
$862,750
3 Beds ⋅ 2 Baths ⋅ MDQA2018158 MLS
THE SELLER WILL ACCEPT OFFERS WITH MOST FURNITURE INCLUDED. SOME SMALL DECORATIONS AND A FEW PICTURES ARE RESERVED. THE MOVING VAN IS ALREADY SCHEDULED. Be part of the fastest growing 55+ community on Maryland's Eastern Shore. Bayberry was the first street in Four Seasons Kent Island where construction in 2021 was superior to those today. 320 Bayberry Drive sits on a Premium Lot which abuts lands owned and maintained by the HOA. The developer is charging a Lot Premium of up to $400,000 for the extra space on remaining lots. The seller just completed $80,000 in renovations. Most of the Furniture can be purchased for below half of what it’s value. The optional sunroom area was completely finished as additional living space. There is a massive 256 square foot rear patio with low V lighting and two raised garden beds. Another HOA area is the rear buffer and beautifully landscaped. If they have a dog, the common area next to the home is almost the size of a building lot offering exceptional privacy. FSKI club house offers resort quality from the indoor pool and gym or the outside pool in summer months. FSKI also allows you golf carts! Don’t miss this opportunity to experience resort style living at Four Seasons Kent Island.

320 Bayberry Dr, Chester
$799,900
4 Beds ⋅ 3 Baths ⋅ MDQA2018144 MLS
Welcome to 313 Thomas White Boulevard in the sought-after waterfront community of Gibson's Grant on Kent Island. This beautifully maintained Koch-built home offers more than 3,200 square feet of thoughtfully designed living space with four bedrooms, two-and-a-half baths, and a flexible floor plan tailored to today's lifestyle. The main level features hardwood flooring,crown molding and refined architectural details throughout, a main-level home office, and a spacious family room anchored by a cozy gas fireplace. The gourmet kitchen is designed for both everyday living and entertaining, showcasing granite countertops, rich mahogany cabinetry, stainless steel appliances, double wall ovens, a center island, pantry, and a sunny breakfast area. Upstairs, the spacious primary suite offers a walk-in closet and a luxurious en-suite bath with a soaking tub and separate shower, while three additional bedrooms provide plenty of room for family and guests. Above the garage, an expansive bonus room offers endless possibilities for recreation, work, fitness, or guest accommodations, making it one of the home's most versatile spaces. Relax on the welcoming front porch where you can enjoy the neighborhood's charming streetscape and peaceful surroundings, or unwind in the screened porch overlooking the fenced backyard, an inviting space for morning coffee, outdoor dining, or relaxing. A rear-entry two-car garage adds everyday convenience while preserving the home's classic curb appeal. Located in one of Kent Island's premier waterfront neighborhoods, Gibson's Grant offers exceptional resort-style amenities, including a community pool, clubhouse, fitness center, walking trails, kayak launch, fishing pier, pavilion, playgrounds, picnic areas, and water access to Macum Creek and the Chester River. Just minutes from Route 50 and the Chesapeake Bay Bridge, this home provides an easy commute to Annapolis, Baltimore, Washington, D.C., and Maryland's Eastern Shore while offering the relaxed coastal lifestyle that makes Kent Island so desirable.

313 Thomas White Blvd, Chester
$998,000
3 Beds ⋅ 3 Baths ⋅ MDQA2017940 MLS
Welcome to this stunning 4th floor penthouse Severn condominium with serene bay views! This end unit looks out over the walking trails to the water and trees. The fabulous community center /pool / pier is a short 1 mile walk from your backyard.! This unit also has the largest garage space in the the building, plenty of room for one car and storage, a refrigerator etc. There is also an additional inside storage room. This 2600 Sq Ft home is flooded with natural light and has numerous quality upgrades including custom shiplap in most of the rooms, custom ceiling fans and dining room light fixture, custom built his and hers walk in closets. The primary bath has upgraded tile, shelving for more storage, mulitple shower heads and back and front lit vanity mirrors. The gourmet kitchen is designed to impress, featuring elegant quartz countertops,premium appliances and a Wolfe induction cooktop. The island has been upgraded with shiplap as well. Thoughtful upgrades continue throughout the entire home with custom blinds with remote control, a gas fireplace,9 FT ceilings with tray ceilings in the living room and primary suite. A wet bar has also been added to the dining area.The large primary bedroom comes complete with a sitting area/office with exceptional waterviews. It also offers custom designed his -and -her closets that provide both style and storage. This unique residence offers a peaceful setting where you can relax and enjoy the ever-changing waterfront vistas. Whether you are enjoying your morning coffee or entertaining guests, this home offers the perfect blend of sophistication, comfort, and low maintenance waterfront living. Residents enjoy an exceptional resort-style lifestyle with amenities that include indoor and outdoor swimming pools, a fitness center, clubhouse, library, billiards room, hot tub, Bocce Ball, pickleball and tennis courts, picnic areas, tot lots, and a community pier overlooking the Chester River. Ideally located just minutes from shopping, dining, golf, marinas, and the Chesapeake Bay Bridge, this exceptional waterfront residence offers the perfect blend of luxury, convenience, and carefree Eastern Shore living.

111 Marshgrass Way Unit #41, Chester
$749,000
4 Beds ⋅ 4 Baths ⋅ MDQA2017930 MLS
Experience the best of Kent Island living in this beautifully maintained coastal home, ideally situated in the highly desirable Water's Edge section of Gibson's Grant. Built in 2017, this exceptional residence enjoys unobstructed pond views from the welcoming covered front porch, where you can relax while watching blue herons and other native wildlife. Perfectly positioned just one block from the community's exceptional waterfront amenities, including the Chester River, clubhouse, pool, fitness center, kayak launch, fishing pier, and waterfront pavilion, this home offers the perfect blend of luxury, convenience, and the relaxed lifestyle of Maryland's Eastern Shore. Step inside to discover a bright, thoughtfully designed floor plan where beautiful flooring flows throughout the main level and abundant natural light fills every room. Designed for both everyday living and effortless entertaining, the main level offers exceptional versatility with a spacious flex room that is ideal as a home office, den, sitting room, or additional living space, along with a convenient powder room for guests. The heart of the home is the expansive open-concept living area, where the spacious family room, dining area, and beautifully appointed kitchen come together seamlessly. The kitchen features a large center island with abundant seating and workspace, while the family room is highlighted by a beautiful gas fireplace. Just beyond, the brand-new screened porch opens to your own private backyard oasis featuring a beautifully landscaped paver patio, a tranquil ornamental pond with a cascading waterfall, full privacy fencing perfect for pets, and an irrigation system to keep the grounds looking their best. Designed for the ease of first-floor living, the main level features a spacious primary suite privately situated at the rear of the home. The luxurious ensuite bath includes a relaxing Jacuzzi soaking tub, while a second main-level bedroom offers its own private full bath, making it ideal for guests or multigenerational living. The staircase to the upper level is thoughtfully tucked toward the rear of the home, enhancing the home's functional layout. Upstairs, you'll find two generously sized bedrooms and a beautifully appointed full bath, providing comfortable accommodations for family and guests. Completing the home is a spacious rear-entry two-car garage with plenty of room for parking and storage, plus a custom-built workspace perfect for DIY enthusiasts, hobbyists, or woodworking projects. An approximately four-foot-high conditioned crawl space with interior access provides exceptional additional storage. Recent improvements include a brand-new HVAC system, brand-new screened porch, one-year-old oven, and new washer and dryer, allowing you to move in with confidence. Residents of Gibson's Grant enjoy resort-style amenities, including a clubhouse, outdoor pool, fitness center, waterfront pavilion, kayak launch, fishing pier, water access, and direct access to the Cross Island Trail. Tucked behind a peaceful nature preserve just off Route 50, this sought-after waterfront community offers the perfect balance of tranquility and convenience. Located just moments from the Chesapeake Bay Bridge, the home provides an easy commute while placing you minutes from waterfront dining, marinas, shopping, parks, and local entertainment. Beautifully maintained, thoughtfully updated, and ideally located in one of Kent Island's most desirable neighborhoods, this exceptional home offers the perfect opportunity to embrace luxury coastal living on Maryland's Eastern Shore. Schedule your private showing today! Mortgage savings may be available for buyers of this listing.

134 Richard Ingle Way, Chester
$524,999
2 Beds ⋅ 3 Baths ⋅ MDQA2017860 MLS
NEW INCENTIVE — THE OWNERS WILL COVER YOUR $8,000 COMMUNITY BUY-IN WITH ACCEPTABLE OFFER! Move-in ready condo with zero wait! This meticulously maintained, first-floor Magothy shows like new, offering over 2,000 square feet of single-level living in the highly sought-after Four Seasons at Kent Island 55+ active-adult community. Enjoy the rare convenience of direct outdoor patio access and beautiful views from every window. The thoughtfully designed open-concept features two spacious bedrooms, each boasting a full bath and walk-in closet, plus direct patio access from the primary suite. The gourmet kitchen centers around a massive seating island with pendant lighting and a stylish dry bar. French doors open to a dedicated home office, while double sliding doors in the living room provide the entire space with natural light. Quartz countertops and seamless luxury vinyl plank flooring are found throughout the home. Complete with a private guest powder room, laundry room, climate-controlled storage, a one-car garage, and a beautifully appointed community room on the second floor, this condo delivers the low-maintenance lifestyle the community is known for. The award-winning 24,000 square foot Chester House clubhouse is the heart of the community, with indoor and outdoor pools, a fully equipped fitness center, yoga studio, demonstration kitchen, library, billiards and game room, and a grand ballroom. Outside, enjoy lighted tennis, pickleball, and bocce courts, a dog park, gas and wood-burning fire pits, a waterside tiki bar, and miles of walking and biking trails connecting to the Cross Island Trail. The 450-foot community pier on the Chester River, with boat slips plus canoe and kayak launch and storage, is a favorite for anyone who loves the water. Year-round clubs, classes, live entertainment and events can be found at the community clubhouse, and you’ll be minutes from Kent Island, shops, waterfront dining, and Queenstown Premium Outlets, with easy access to the Bay Bridge for Annapolis, Baltimore, and Washington D.C. Schedule your private showing today.

230 Switchgrass Way Unit #12, Chester
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