Chester MD Real Estate, Homes, Condos for Sale

Check out the Virtual Tour! Exceptional Value in Four Seasons at Kent Island Why wait to build? This less-than-one-year-old Tuscaloosa model on sought-after Kingfisher Lane delivers the upgrades, location, and efficiency buyers are chasing—without the timeline or added expense. Positioned just across from the Chester River, enjoy peekaboo water views from the covered front porch and even a sightline to the clubhouse. Inside, the home is bright, open, and thoughtfully designed with 5 bedrooms and 4.5 baths, offering flexibility for guests, work-from-home space, or multigenerational living. It shows like new—but lives better—because everything has already been elevated beyond builder grade. Over $70,000 in post-builder upgrades, including: • Owned solar system (10kW+) providing substantial energy savings • Custom closet systems throughout the home • Custom window treatments already installed • Premium Café Series appliances • Tankless water heater • Upgraded lighting and fixtures • Additional high-end finishes and improvements throughout The spacious floor plan offers room for everyone, while the oversized garage provides ample storage for vehicles, golf carts, and all the gear that comes with Eastern Shore living. Life in Four Seasons at Kent Island is about more than the home itself. Residents enjoy resort-style amenities including a stunning clubhouse, indoor and outdoor pools, fitness center, pickleball courts, walking trails, kayak launch, fishing pier, and an active social calendar designed for a vibrant lifestyle. With immediate availability, extensive upgrades already completed, and one of the community's most desirable locations, this home represents an opportunity that's becoming increasingly difficult to find. Add in the recent $50,000 price reduction, and this is one of the best values currently available in Four Seasons at Kent Island. Don't miss your chance to enjoy nearly new construction, energy-efficient living, and the Chesapeake Bay lifestyle you've been waiting for.

215 Kingfisher Ln, Chester

Listing courtesy of RE/MAX Executive. Contact:

$969,990

3 Beds ⋅ 3 Baths

Welcome to the Severn, a beautifully designed home offering 3 bedrooms, 2.5 baths, and a 1-car garage. Scheduled for settlement in December 2026, 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.

102 Boatswain Way Unit 2934, Chester

Listing courtesy of KOVO Realty. Contact:

$599,990

2 Beds ⋅ 3 Baths

Welcome to the Magothy, a thoughtfully designed home offering 2 bedrooms, 2.5 baths, and a 1-car garage. Scheduled for settlement in December 2026, 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 stylish workspace. The kitchen is designed for 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.

102 Boatswain Way Unit 2912, Chester

Listing courtesy of KOVO Realty. Contact:

$799,990

2 Beds ⋅ 3 Baths

Welcome to the Chester, a thoughtfully designed home offering 2 bedrooms, 2.5 baths, and a 1-car garage. Scheduled for settlement in October 2026, this home combines modern comfort with functional living spaces. The heart of the home features a dry bar and an electric fireplace, creating a warm and inviting atmosphere. A dedicated home office with lited French doors provides a stylish and private workspace. The kitchen is designed for both everyday living and entertaining, 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 seat and handheld shower wand, double sinks, and quartz countertops for added convenience and style. 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.

110 Boatswain Way Unit 3043, Chester

Listing courtesy of KOVO Realty. Contact:

$492,500

2 Beds ⋅ 3 Baths

Four Seasons @ Kent Island - 55+ Community - Reduced! * Turn-key & Lovely 2nd Floor Condo in Elevator Building with 1 Car Garage plus 1 Car Outdoor Parking and Private, Secure Indoor Storage Area. This Chester Model offers 1900 sf with pond view and winter water views of Macum Creek. Enter to find an expansive, open floor plan featuring a beautiful white Kitchen with quartz counters, propane gas cooktop with range hood, wall oven + microwave combo and a huge Island that accommodates plenty of bar seating. Spacious Bedroom suites each with private full baths and generous closet spaces. The Primary bath has His 'n Her's double sinks with Moen fixtures, comfort height vanities, large vanity mirrors, medicine cabinets and a walk-in tiled shower with seat. The Primary bedroom features 2 closets; one walk-in-closet and one generous wall closet, a ceiling fan and a single French door to access the balcony. The 2nd Bedroom is large enough to hold a traditional sized bedroom set and features a tub/shower combo in the bath. The open Great Room is large, bright and has serene pond views and winter water views of Macum Creek with oversized sliders to a covered balcony. You will love the convenient laundry room located off the foyer area that accommodates the included full-sized GE washer and dryer. Elevator down to the Lobby level to your private garage and a just a few steps down the corridor is your private, keyed storage closet. This condo building features a secure lobby entrance and is impeccably decorated and maintained. Additionally, the 2nd floor has a common Club Room/Meeting Room great for socializing with your neighbors or as additional entertainment space. It features Public Water, Public Sewer, individually metered propane gas heat and cooking. All residents have access to the community amenities which include a huge 24,000 sf Club House with Billiards Room, Casual Lounge Area, Fitness Center, Party and Meeting rooms, and fabulous Indoor Heated Pool & Spa. Outside awaits a resort-like Pool, Cabana House, Private Beach Area, Outdoor Concert Space, Pier for Fishing and taking in the magnificent Chester River views & Kayak launch and Walking Trails. Pickle Ball enthusiasts you are in luck as there are Tennis Courts and Pickle Ball Courts for all, and grand kids can be entertained at a small Playground Area. Come tour today and see why this is THE place to be in Kent Island for 55+ living!

4000 Herons Nest Way Unit 22, Chester

Listing courtesy of RE/MAX Leading Edge. Contact:

$460,000

2 Beds ⋅ 3 Baths

This highly sought-after first-floor condo offers the opportunity to own a fully upgraded 2,003 square foot Four Seasons Condo without waiting for new construction. Just steps from the waterfront and features an open, light-filled floor plan enhanced by crown molding, recessed lighting, and beautiful views of lush greenspace with seasonal water glimpses. The gourmet kitchen and dining area are designed for both everyday living and entertaining, featuring a spacious island with seating, quartz countertops, breakfast bar, sleek Wi-Fi-enabled appliances and a seamless flow into the inviting living room. Enjoy peaceful mornings, beautiful natural surroundings, and the rare opportunity to settle into a community without the noise and disruption of nearby construction. A price improvement makes this beautifully upgraded condo one of the best values in the entire community. Offering approximately $55,000 in owner upgrades, this home truly shows like a model—and unlike new construction, there is no waiting. This meticulously maintained residence is move-in ready and available for immediate occupancy. Relax by the cozy fireplace or open the double sliding glass doors and step onto your private patio—the perfect place to enjoy your morning coffee, watch the sunrise, curl up with a good book, or simply take in the peaceful natural setting. The spacious owner’s suite offers a walk-in closet plus a secondary closet, private patio access, and a luxurious en-suite bath featuring dual vanities and a spa-inspired frameless glass shower. The bright and generously sized guest suite includes its own en-suite bath with custom tilework and a large vanity, providing comfort and privacy for family and guests. A versatile bonus room with upgraded frosted glass doors offers endless possibilities as a home office, fitness space, reading room, or quiet retreat. Additional highlights include LVP flooring throughout the entire home, interior access to a private one-car garage, and a secure storage unit. From your private patio, enjoy a stroll along the community walking trail, surrounded by nature and peaceful views, leading to a tranquil waterfront setting featuring a paddle board and kayak launch. The resort-style amenities continue throughout the community, including an indoor heated pool, outdoor infinity pool, firepits, pickleball and tennis courts, dog park, and beautiful walking and biking trails. Residents also enjoy direct access to the Kent Island Cross Island Trail, making it easy to explore the area by foot or bike. Live every day like you’re on vacation! With approximately $55,000 in owner inspired upgrades, a prime first-floor location, private garage, beautiful natural views, and an impressive collection of resort-style amenities, this exceptional condo offers the lifestyle you've been waiting for. A must-see to truly appreciate all this home has to offer! Water and sewer fees are already included in the owner’s monthly COA fee.

3000 Herons Nest Way Unit 11, Chester

Listing courtesy of Coldwell Banker Realty. Contact:

$674,900

4 Beds ⋅ 3 Baths

The Windermere combines all of the home design elements our purchasers love the most. On the main level is an open plan design with a huge kitchen, breakfast/sunroom and family room! Formal living and dining rooms, and two-story foyer complete the space. Upstairs you will find 4 spacious bedrooms to include an owner's suite with spacious walk-in closet or choose the optional super bath and get two walk-in closets! A lower level offers numerous options for expanding your living space to suit your lifestyle.

Lot 6 Norman, Chester

Listing courtesy of Keller Williams Flagship. Contact:

$1,198,800

4 Beds ⋅ 4 Baths

*****Immediate Delivery*****WATERFRONT ****Schedule showoing today! New Home, New Pier,The Blue Heron is a new home design offered by Lacrosse Homes. The single family design features now one but TWO decks -- one from the second floor great room and the second from the third level primary bedroom suite. Take in all the beautiful sights and sounds of a Coastal Maryland lifestyle in this home built for entertaining and an enhanced lifestyle! There is room for everyone in this home, starting with a main level 2-car garage, rec room area, full bath & exercise/office -- this is your fun zone or whatever zone! The second level is light-filled and open with island kitchen featuring upgraded finishes, dining area, powder bath and great room with deck. You can ADD another deck on the rear of the home off the dining area if you're looking for more outdoor space. The third level features a laundry, three bedrooms including the spacious primary bedroom with updated bath and another stunning deck. The Blue Heron is a beautiful home and will serve a multitude of lifestyles. Explore your options today!

1757 Harbor Dr, Chester

Listing courtesy of Keller Williams Flagship. Contact:

$19,500

2 Beds ⋅ 1 Baths

This property, situated on a 0.17-acre lot, offers a blank canvas for your vision. Located in Queen Anne's County, the existing structure presents endless possibilities for the right buyer. Take advantage of the spacious lot size, perfect for outdoor activities or future expansion plans. Buyers are encouraged to perform their own due diligence to verify property details. Please note that access to 1405 Little Creek Rd is via 104 Little Creek Ct, followed by a left turn. Do not use or enter any neighboring driveways or properties as they are privately owned and clearly marked with “No Trespassing” signs. For safety reasons, please respect these boundaries.

1405 Little Creek Rd, Chester

Listing courtesy of The Parker Group. Contact:

$275,000

Kent Island Waterfront on Cox Creek!! Public Sewer available, road frontage is 45ft. This is a flag lot with opening on the waterfront of 108 ft. This property does not have a pier, so please do not go on pier. This is the perfect lot to build your dream home. The natural environment has wildlife and waterfowl and as well as good fishing and crabbing. If you want a piece of the shore-life this is the property you have been looking for. Seller will consider holding a note for purchaser.

Parks Road, Chester

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

$600,000

2 Beds ⋅ 2 Baths

Nestled along the serene shores of the Chester River, 505 Swan Cove Ln presents an exquisite west facing waterfront retreat offering the perfect blend of elegance, comfort, and natural beauty. This captivating property seamlessly combines modern luxury with the tranquility of waterfront living, providing an unparalleled lifestyle experience. With a short walk, discover any of the restaurants, bars, shops, or marinas that the Kent Narrows has to offer. Or sit out on the porch and watch the wildlife that frequent the property from the neighboring nature preserve. Property includes 2 bed 2 bath, large office (could be 3rd bedroom), attached garage, open kitchen, private slip on the community pier and most importantly big water views from almost everywhere! Tax record is incorrect, condo is 1990 square feet, per the original blueprint.

505 Swan Cove Ln, Chester

Listing courtesy of EXIT On The Bay. Contact:

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