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224 Bayberry Dr, Chester
$550,000
2 Beds ⋅ 2 Baths
Welcome to Easy Living on the Eastern Shore! *** Discover the perfect blend of comfort, style, and resort-style living in this impeccably maintained, one-owner home — tucked into the highly sought-after, water-privileged 55+ community of Four Seasons at Kent Island. From the moment you walk in, you’ll notice the difference. The open-concept floor plan is thoughtfully designed and beautifully upgraded with custom finishes and designer lighting, setting the stage for elegant everyday living. *** At the heart of the home is a show-stopping kitchen—featuring a dramatic black quartz island, crisp white shaker-style cabinets, and ample prep space for casual meals or gourmet entertaining. The kitchen flows effortlessly into a warm and inviting family room anchored by a gas fireplace—perfect for cozy evenings or lively conversations. *** Need a little flex space? You’ve got it. A versatile bonus room makes the ideal office, craft room, guest space, or private retreat, bathed in natural light. Step out onto the custom-stamped concrete patio where you can sip morning coffee, host a happy hour, or just kick back and enjoy the quiet, watching the birds at the pond or the treelined backyard. *** But the real magic? The lifestyle. *** Four Seasons at Kent Island offers unmatched amenities that feel more like a vacation than a neighborhood. Think: *** - A stunning 24,000+ sq ft clubhouse . - Indoor and outdoor pools . - A waterfront pier with boat slips for visiting friends . - Fitness center, game room, chef’s kitchen, meeting spaces . - A full-time lifestyle director curating events, live music, and clubs . - All of this—just 20 minutes from Annapolis and right off Route 50 for easy getaways or guest visits. . - Low-maintenance, high-style, and built for enjoying every chapter of life to the fullest. . See why so many are choosing Four Seasons at Kent Island—and why this Donegal model might just be the one you’ve been looking for.

224 Bayberry Dr, Chester

Listing courtesy of Realty Navigator. Contact:

Selling Office: Coldwell Banker Realty.

630 Warbler Way Unit 2211, Chester
$524,900
2 Beds ⋅ 3 Baths
Magothy || Available April 2026 This thoughtfully designed 2 bed, 2.5 bath home with a 1-car garage combines functionality with style. A welcoming home office with lited French doors offers the perfect space to work or study, while the electric fireplace creates a cozy focal point. Entertain with ease thanks to a convenient dry bar just steps from the kitchen. The kitchen is appointed with a gas cooktop, range hood, single oven, microwave, dishwasher, pendant lighting, and a tile backsplash, all complemented by quartz countertops. Durable laminate flooring flows throughout the home, with tile in both full baths. The owner’s bath is designed for relaxation, featuring a walk-in shower with seat and handheld wand, double sinks, and quartz countertops. 📸 Photos are for illustrative purposes only. Features and finishes may vary. For a full list of included features, please contact our sales representatives.

630 Warbler Way Unit 2211, Chester

Listing courtesy of KOVO Realty. Contact:

Selling Office: Non Subscribing Office.

121 Wheelhouse Way Unit 2111, Chester
$524,900
2 Beds ⋅ 3 Baths
This Magothy condo offers low-maintenance luxury with a smart layout and designer features. With 2 bedrooms, 2.5 bathrooms, a 1-car garage, and a dedicated home office with French doors, it’s the perfect mix of comfort and versatility. Enjoy cozy evenings by the electric fireplace or entertaining at the built-in dry bar. The kitchen includes quartz countertops, a gas cooktop, range hood, tile backsplash, and stylish pendant lighting. Laminate flooring runs throughout the home, with tile in both full baths. The primary bath features a walk-in shower with seat and handheld shower wand, double sink, and quartz countertops. For a full list of features for this home, please contact our sales representatives. Photos may be of a similar home and used for representation purposes only.

121 Wheelhouse Way Unit 2111, Chester

Listing courtesy of KOVO Realty. Contact:

Selling Office: Compass.

121 Wheelhouse Way Unit 2112, Chester
$520,900
2 Beds ⋅ 3 Baths
Experience stylish, low-maintenance living in this thoughtfully designed 2-bedroom, 2.5-bath Magothy condo, and curated finishes throughout. An open-concept layout, ample natural light, and elevated design features make this home ideal for both everyday life and entertaining. Enjoy standout elements like a dry bar, electric fireplace, and a dedicated home office with French doors, offering the perfect blend of functionality and charm. The kitchen impresses with quartz countertops, a tile backsplash, pendant lighting, and a full suite of GE stainless steel appliances—including a single oven, microwave, gas cooktop, and French door refrigerator. Laminate flooring runs throughout the main living areas, while tile flooring enhances both full baths. The primary suite is a retreat in itself, featuring a double-sink quartz vanity, shower with seat and handheld wand, and designer finishes throughout. For a full list of features for this home, please contact our sales representatives. Photos are for display purposes only and may not reflect actual finishes or selections.

121 Wheelhouse Way Unit 2112, Chester

Listing courtesy of KOVO Realty. Contact:

Selling Office: Samson Properties.

190 Harrier Way Unit 11, Chester
$520,000
2 Beds ⋅ 3 Baths
Luxury 55+ Living at Four Seasons on Kent Island – Move-In Ready & Priced to Sell! Welcome to the resort-style lifestyle of Four Seasons on Kent Island, an amenity-rich 55+ waterfront community where luxury, comfort, and convenience meet. Inside, you'll find open-concept layouts filled with natural light, gourmet kitchens with quartz countertops, GE Profile stainless steel appliances, custom cabinetry, and designer touches like pendant lighting and tile backsplashes. Primary suite includes walk-in closets, ensuite bath, and sitting areas with water views and private patio access. Additional features include cozy fireplaces, a large guest bedroom, private walk out patio, climate-controlled storage room, and attached 1-car garage. Step outside to enjoy ground-floor access. Whether relaxing in your private space or mingling with neighbors, every detail has been designed for comfort and community. Unrivaled Amenities Include: 24,000 sq. ft. clubhouse with indoor & outdoor pools State-of-the-art fitness center, yoga studio, and locker rooms Game rooms, library, and multiple gathering areas with kitchens Waterfront resort-style pool, beach lounge with fire pits, and performance stage Miles of walking & biking trails, kayak/paddleboard launch, and boat pier Tennis, pickleball, bocce ball, basketball, playgrounds, and a dog park Dozens of clubs, fitness classes, and social events coordinated by a full-time lifestyle director Located just minutes from the Bay Bridge with easy access to Annapolis, DC, Baltimore, and the beaches, Four Seasons at Kent Island offers the best of Maryland’s Eastern Shore living. Waterfront dining, golf, shopping, and miles of scenic trails await just outside your door. Priced to sell with quick settlement available—schedule your private tour today and start your next adventure in luxury island living!

190 Harrier Way Unit 11, Chester

Listing courtesy of RE/MAX Executive. Contact:

Selling Office: Chesapeake Real Estate Associates, LLC.

630 Warbler Way Unit 2222, Chester
$514,990
2 Beds ⋅ 3 Baths
Chester|| Available May 2026 This home offers 2 bedrooms, 2.5 baths, and a 1-car garage. Standout features include a dry bar, an electric fireplace, and a dedicated home office with lited French doors. The kitchen is thoughtfully designed with a single oven, microwave, gas cooktop, range hood, dishwasher, pendant lights, and a tile backsplash, all accented by quartz countertops. The flooring includes durable laminate throughout most of the home with tile in both full baths. The owner’s bath showcases a walk-in shower with a seat, a handheld shower wand, dual sinks, and quartz countertops for a spa-like finish. 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.

630 Warbler Way Unit 2222, Chester

Listing courtesy of KOVO Realty. Contact:

Selling Office: RE/MAX Executive.

630 Warbler Way Unit 2212, Chester
$499,990
2 Beds ⋅ 3 Baths
Magothy || Available April 2026 This 2 bed, 2.5 bath home with a 1-car garage is designed with both comfort and convenience in mind. A dedicated home office with lited French doors makes working from home easy, while the electric fireplace adds warmth and charm. The addition of a dry bar creates the perfect spot for entertaining. The kitchen is beautifully appointed with a gas cooktop, range hood, single oven, microwave, dishwasher, tile backsplash, and pendant lighting, all complemented by elegant quartz countertops. Throughout the main living spaces, you’ll find durable laminate flooring, with tile in both full baths. The owner’s bath features a walk-in shower with seat and handheld wand, double sinks, and quartz countertops for a spa-like experience. 📸 Photos are for illustrative purposes only. Features and finishes may vary. For a full list of included features, please contact our sales representatives.

630 Warbler Way Unit 2212, Chester

Listing courtesy of KOVO Realty. Contact:

Selling Office: Unrepresented.

170 Harrier Way Unit 11, Chester
$499,000
2 Beds ⋅ 3 Baths
Move-In Ready 2-Bedroom Condo in Four Seasons at Kent Island! Discover this stunning 2-bedroom, 2.5-bath condo in the sought-after 55+ community of Four Seasons at Kent Island! Completely move-in ready, this home boasts a gourmet kitchen, a formal dining area, and a cozy family room, all enhanced by luxurious finishes throughout. The spacious primary bedroom features a full ensuite bath, while the guest bedroom includes a ceiling fan for added comfort. Enjoy ground-floor access to a private patio—perfect for relaxing outdoors and viewing the local wildlife including herons, birds, rabbit and deer. Additional highlights include a one-car garage, a private balcony, and a larger hall closet and guest bath compared to similar models. ***Redfin powered by Rocket Mortgage Preferred Pricing*** Enjoy with a 1% lower interest rate for your initial year or potential savings of up to $6,000 on your closing costs when you finance with Rocket Mortgage*** Experience resort-style living with amazing community amenities, including a clubhouse, fitness center, walking trails, and waterfront views. This one won’t last—schedule your tour today!

170 Harrier Way Unit 11, Chester

Listing courtesy of Redfin Corp. Contact:

Selling Office: Long & Foster Real Estate, Inc..

170 Harrier Way Unit 22, Chester
$499,000
2 Beds ⋅ 3 Baths
For a limited time, the seller is offering $4,000 toward the capital contribution fee—an incredible opportunity to move into the sought-after Four Seasons at Kent Island lifestyle just in time for warmer days on the Chesapeake Bay. This beautifully maintained, turnkey condo offers the perfect blend of comfort and sophistication. The thoughtfully designed floor plan features two spacious bedrooms, two full baths, a stylish powder room, and a private office or den with elegant French doors—ideal for working from home or hosting guests. The chef’s kitchen is equipped with gas cooking, a range hood, quartz countertops, a breakfast bar, and stainless-steel GE Profile appliances, seamlessly opening to the main living area for easy entertaining. A separate laundry/utility room includes a full-size washer and dryer. Additional highlights include abundant storage, a private interior storage room, a one-car garage within the building, and secure key-code entry. Residents enjoy access to the impressive 24,000-square-foot clubhouse featuring indoor and outdoor pools, outdoor bar areas, fire pits, a fitness center, library, and game room. The community also offers 4.3 miles of walking trails, lighted pickleball and tennis courts, bocce, a dog park, and an outdoor amphitheater for concerts and movie nights. Conveniently located near Route 50 with easy access to Annapolis, Baltimore, Washington, D.C., and area beaches, this home offers resort-style living with everyday convenience.

170 Harrier Way Unit 22, Chester

Listing courtesy of Keller Williams Select Realtors of Annapolis. Contact:

Selling Office: Compass.

1000 Herons Nest Way Unit 23, Chester
$480,000
2 Beds ⋅ 3 Baths
Welcome to 1000 Herons Nest Way #23, an exceptional former model home located in the first phase of condominiums within the highly desirable Four Seasons at Kent Island. This beautiful 2-bedroom, 2.5-bath residence combines designer finishes, thoughtful upgrades, and a peaceful natural setting to create the perfect low-maintenance retreat. From the moment you enter, you'll appreciate the bright, open floor plan, gorgeous luxury vinyl plank flooring, and the seamless flow between the kitchen, dining, and living spaces—ideal for entertaining while still offering comfortable, defined living areas. The gourmet kitchen opens effortlessly into the main living space, while the dedicated home office features custom built-in cabinetry, display shelving, and accent lighting, creating an inviting workspace or library. Throughout the home you'll find quality upgrades including plantation shutters in both bedrooms, custom closet organization systems, ceiling fans, and a built-in wireless audio system with a Samsung Frame TV, blending everyday comfort with modern convenience. The spacious primary suite offers a relaxing escape, while the thoughtfully designed split-bedroom layout provides privacy for overnight guests. One of this home's most captivating features is the private balcony overlooking protected wooded surroundings, where you'll enjoy peaceful mornings with coffee while watching deer, birds, and the abundant wildlife that make Kent Island so special. Just outside your door, enjoy convenient access to the Cross Island Trail, nearby Macum Creek, and community kayak storage—perfect for embracing the Eastern Shore lifestyle. Residents of Four Seasons at Kent Island enjoy a truly carefree lifestyle with exterior maintenance, landscaping, and common areas maintained by the HOA, making it easy to lock the door and travel without worry. Resort-style amenities include a stunning clubhouse, indoor and outdoor pools, fitness center, pickleball and tennis courts, walking trails, and an active calendar of clubs and social events. Beautifully upgraded, impeccably maintained, and ideally situated, this former model home offers a rare opportunity to enjoy resort-style living surrounded by the natural beauty of Kent Island.

1000 Herons Nest Way Unit 23, Chester

Listing courtesy of Samson Properties. Contact:

Selling Office: Redfin Corp.