Four Seasons At Kent Island Real Estate

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.

830 Warbler Way Unit 2843, Chester

Listing courtesy of Berkshire Hathaway HomeServices PenFed Realty - OP. Contact:

$744,900

2 Beds ⋅ 3 Baths

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, electric 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

111 Marshgrass Way Unit 43, Chester

Listing courtesy of Long & Foster Real Estate, Inc.. Contact:

$790,000

3 Beds ⋅ 2 Baths

Welcome to this beautifully upgraded Killarney model in Four Seasons at Kent Island, offering true one-level living with no steps, three spacious bedrooms, and the largest garage offered in the community. Unlike many Killarney models featuring two bedrooms and a loft, this home offers three true bedrooms, a dedicated laundry room, and an additional bump-out ideal for a home office or den. The open-concept interior features an Ultra Gourmet Kitchen with quartz countertops, upgraded cabinetry and appliances, double wall ovens, a French-door refrigerator, and a large center island perfect for entertaining. The spacious primary suite includes an Ultra Luxury Spa Bath with a walk-in shower and dual vanities. Tray ceilings, a fireplace, and custom window treatments add to the home's appeal. The oversized garage provides exceptional space for vehicles, a golf cart, and additional storage. Situated on a $55,000 premium homesite, the property enjoys a spacious backyard with generous separation from neighboring homes, offering a wonderful sense of privacy. An expansive custom hardscaped patio creates the perfect setting for outdoor dining, entertaining, and relaxation. Four Seasons at Kent Island offers resort-style 55+ living along the Chester River, featuring a 24,000-square-foot waterfront clubhouse, indoor and outdoor pools, a fitness center, pickleball and tennis courts, walking trails, a dog park, fishing pier, transient boat slips, waterfront Tiki Bar, and an active social calendar. With its desirable floor plan, premium homesite, exceptional garage space, and extensive upgrades, this Killarney presents a rare opportunity to enjoy the best of Four Seasons living.

117 Harrier Way, Chester

Listing courtesy of RE/MAX Executive. Contact:

$749,900

2 Beds ⋅ 3 Baths

NEW PRICE! Reduced! Gorgeous All On One Level Home in 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 * Walkable to Clubhouse * 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 and a Friendly, Neighborly Environment That All Enjoy and Gather at 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.

168 Redstart Dr, Chester

Listing courtesy of RE/MAX Leading Edge. Contact:

$1,399,000

3 Beds ⋅ 3 Baths

Experience exceptional waterfront living in this stunning 3-bedroom, 2.5-bath condominium offering what are arguably the best views in the community. Positioned to capture breathtaking panoramic views of the Chester River, this home provides a front-row seat to beautiful sunrises, and the peaceful beauty of the Chesapeake Bay lifestyle. The spacious primary suite is a true retreat featuring a private sitting room, walk-in closet, and a luxurious en-suite bath. The open-concept design showcases the incredible water views throughout the main living spaces, creating the perfect backdrop for everyday living and entertaining. One of the most desirable locations in the community, this home offers protected water views with no expected future obstruction, allowing you to enjoy the scenery for years to come. Enjoy the convenience of being able to walk to the community pool and amenities without having to drive to the clubhouse. Additional features include a one-car garage with an additional storage room, plus private driveway parking, providing both convenience and storage. Enjoy the ease of maintenance-free waterfront living in one of Kent Island's premier communities, with easy access to marinas, waterfront dining, shopping, and the Bay Bridge.

129 Wheelhouse Way Unit 21, Chester

Listing courtesy of Rise Real Estate, LLC. Contact:

$585,000

2 Beds ⋅ 3 Baths

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.

129 Wheelhouse Way Unit 11, Chester

Listing courtesy of RE/MAX Executive. Contact:

$549,950

2 Beds ⋅ 3 Baths

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?

630 Warbler Way Unit 12, Chester

Listing courtesy of RE/MAX Executive. Contact:

$969,990

2 Beds ⋅ 3 Baths

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.

118 Kinglet Ct, Chester

Listing courtesy of Berkshire Hathaway HomeServices PenFed Realty - OP. Contact:

$999,990

3 Beds ⋅ 3 Baths

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.

114 Kinglet Ct, Chester

Listing courtesy of Berkshire Hathaway HomeServices PenFed Realty - OP. Contact:

$689,990

2 Beds ⋅ 3 Baths

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.

830 Warbler Way Unit 2833, Chester

Listing courtesy of Berkshire Hathaway HomeServices PenFed Realty - OP. Contact:

$859,900

3 Beds ⋅ 2 Baths

320 Bayberry Dr, Chester

Listing courtesy of RE/MAX Leading Edge. Contact:

$665,000

2 Beds ⋅ 3 Baths

Immediate Occupancy-Be HOME for the HOLIDAYS! Built in 2019, this coastal style cutie is BETTER than new & offers a bright open layout that includes 2 SPACIOUS BEDROOMS complete w/ brand new carpet & beautiful custom ENSUITE BATHROOMS plus additional HOME OFFICE/DEN or spare bedroom & POWDER ROOM off foyer. The open concept 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, an expansive CENTER ISLAND perfect for gathering & entertaining & 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 includes high ceilings & a built-in safe for keeping valuables & important documents. Elevated custom PLANTATION SHUTTERS throughout. An OVERSIZED 2-CAR GARAGE complete w/upgraded EPOXY FLOOR & 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/remote operated RETRACTABLE AWNING providing additional space for entertaining or simply relaxing & enjoying the outdoors. HOA provided LAWN CARE & IRRIGATION plus GUTTER Guards offer the added benefit of reduced exterior maintenance, making home ownership that much easier and worry-free. 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 (did I mention 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 GYM, BALLROOM, Learning Kitchen, stocked LIBRARY w/fireplace & various other 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 TOTAL PACKAGE community.

228 Bayberry Dr, Chester

Listing courtesy of Long & Foster Real Estate, Inc.. Contact:

Four Seasons At Kent Island Real Estate

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