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$790,000
3 Beds ⋅ 2 Baths
Welcome to this beautifully upgraded Killarney model in Four Seasons at Kent Island, where one of the best features is **true one-level living with no steps**. Everything you need is conveniently located on one floor, including three true bedrooms, a dedicated laundry room, and an additional bump-out perfect for a home office or den. Unlike many Killarney models configured as two bedrooms with a loft, this home offers a true 3-bedroom layout without the need for stairs. 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. The spacious primary suite includes an Ultra Luxury Spa Bath with walk-in shower and dual vanities. Tray ceilings, a fireplace, and custom window treatments add to the home's appeal. The oversized garage offers extra space for a golf cart or additional storage. The $55,000 premium homesite is another standout, backing to the fairway with neighboring homes positioned a respectful distance away for added privacy and a wonderful sense of openness. An extensive hardscaped patio creates a beautiful outdoor living space for relaxing, dining, and entertaining. Four Seasons at Kent Island offers resort-style 55+ living with a 24,000-square-foot waterfront clubhouse on the Chester River, indoor and outdoor pools, fitness center, pickleball and tennis, walking trails, dog park, fishing pier, transient boat slips, waterfront Tiki Bar, and an active calendar of social events. **True one-level living with no steps, three bedrooms, a premium fairway setting, and exceptional outdoor space make this Killarney a rare find in Four Seasons.**

117 Harrier Way, Chester

Listing courtesy of RE/MAX Executive. Contact:

$1,199,900
5 Beds ⋅ 3 Baths
COMING SOON. It's rare to find a designer home on a 1.4 acre lot with an in-ground saltwater pool and direct waterfront access on Kent Island at this price tag. From the moment you arrive, the outdoor setting feels like a private resort. A sparkling saltwater pool is surrounded by a newly hardscaped stone terrace, mature lawn & landscaping, apple tree, fig tree, cypress tree, and even strawberries! The rear backs up to farmland creating a secluded, private feel. Walk out your front door, directly to the left of the house to access your own 90 foot pier extends out offering direct access to Kirwan Creek for small boats, kayaking, paddle boarding, fishing, crabbing, wildlife and sunset watching. Imagine walking outside, breathe in the fresh air with morning coffee in hand, walk across your beautiful flat yard, pick a fresh apple along the way, and step onto your own dock to enjoy the classic Chesapeake Bay lifestyle you've been craving. Moving inside the 3,000 square foot home, the original intent of the owner was to create coastal inspired retreat for anyone who walked through the front doors. Each space has been re-imagined with professional interior designer style throughout with coastal wallpaper, nautical colors, custom curtains, trim work, updated light fixtures and more. The main level heart of the home you'll find an updated kitchen (currently under construction for new light countertops, ceramic tile backsplash, and fresh hardware) with a sweet breakfast table nook. Off the kitchen is a dedicated dining room space with gorgeous wallpaper and updated lighting overlooking the backyard. Step down to the airy main living room centered by electric fireplace and opening to a stunning all window sunroom overlooking your backyard paradise.  The main level front room has been converted to functional main level bedroom and the bathroom was updated to a full main level bathroom. Upstairs, the oversized primary suite is designed as a true private retreat, complete with a dedicated lounge area and dreamy spa inspired bathroom. The stunning bath features a freestanding soaking tub, double vanity, large-format tile, and a beautiful tiled shower with dual shower heads. Three additional bedrooms including a custom-designed bunk room with a beautifully renovated hall full bathroom, while a dedicated laundry space off the upstairs hallway adds everyday convenience. The garage was converted into a recreational space (2026) similar to what could be offered by a "finished basement" with versatility to be additional living room, game room, playroom, gym, or easily converted back to the 2 car garage for covered parking. Notable system updates: insulated and added vapor barrier to crawlspace (2026), installed HVAC in garage (2026), main house HVAC (2020), added mini split in sunroom (2022), hot water heater (2022), full primary bathroom renovation (2026), kitchen updated (2026), main level bathroom (2026), hallway renovation bathroom (2026), refinished/stained hardwood floors (2026), newer pool equipment, painted brick on exterior with special masonry paint (2026), and much more (see full list). Nestled within in close-knit community of Kirwans Landing on Kent Island, you are surrounded by homes on large, manicured lots with a strong sense of pride to the overall appearance of the neighborhood. You are walking distance to the community marina with access to private boat slip in deep water. The neighborhood is an easy 5 min drive to Bay Bridge. This is a WOW property that you must see in person to appreciate how special it would be to call this your home. Living on Kent Island offers a waterfront, relaxed lifestyle with a little more space than other waterfront areas in Maryland.

162 Kirwans Landing Ln, Chester

Listing courtesy of Next Step Realty. Contact:

$769,900
2 Beds ⋅ 3 Baths
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.

168 Redstart Dr, Chester

Listing courtesy of RE/MAX Leading Edge. Contact:

$1,439,999
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:

$398,000
3 Beds ⋅ 2 Baths
Bring the boat. Leave the projects behind. Unbeatable value!!- this fully updated home sits on a double lot in a water-oriented community where waterfront parks and water access are just a short walk away. Inside, easy one-level living meets move-in-ready comfort: hardwood floors, a updated kitchen and two full baths, new windows and siding, an updated roof and HVAC, plus an encapsulated crawlspace. Spend your weekends on the water, come home to a yard with room to spread out, with HUGE deck begging to entertain with large fenced backyard. Unpack your bags and make it yours. The generous double lot leaves room to dream about a spacious outbuilding or future expansion. Matapeake school district. HURRY to claim!

624 Romancoke Rd, Stevensville

Listing courtesy of Chaney Homes, LLC. Contact:

$424,950
3 Beds ⋅ 4 Baths
Easy living and a convenient Kent Island location come together at 233 Keenan Way, an end-unit townhome in the sought-after Ellendale community. Offering three finished levels, 1,884 square feet of living space and a two-car garage, this light-filled home features a flexible floor plan designed for everyday living. The main level is bright and open, with abundant natural light enhanced by the additional windows of an end-unit location. The spacious kitchen features tile flooring, ample cabinetry and counter space, and a large center island with seating. Open to the dining area and adjacent living room with LVP flooring, the layout creates an easy flow for everyday living and entertaining. Step outside to the rear deck for grilling, dining al fresco or simply relaxing at the end of the day. Upstairs, two generously sized bedrooms each feature a private ensuite bath, offering the flexibility of dual primary suites. New carpet adds a fresh update to the upper level. The entry level provides an additional bedroom or flexible bonus space ideal for guests, a home office, fitness room or second living area. Life at Ellendale extends beyond the home, with community amenities including an outdoor pool, clubhouse, tot lot, fishing pier, kayak storage, boat storage and walking paths, with sidewalks and streetlights throughout the neighborhood. Located just minutes from the Bay Bridge and convenient to shopping, dining and everyday necessities at Kent Landing, 233 Keenan Way offers a great combination of space, community amenities and easy access to Annapolis, Baltimore, Washington, D.C. and the Eastern Shore.

233 Keenan Way, Stevensville

Listing courtesy of TTR Sotheby's International Realty. Contact:

$665,000
2 Beds ⋅ 3 Baths
Built in 2019, this coastal style cutie is BETTER than new & offers a bright open layout that includes 2 SPACIOUS BEDROOMS complete w/private ENSUITE BATHROOMS plus additional HOME OFFICE/DEN or spare bedroom & POWDER ROOM off foyer. There is a 22X10 BONUS storage space in the upgraded GARAGE LOFT/ “Sky-Basement” The stunning CHEF'S 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, huge CENTER ISLAND & 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 (also custom-finished) includes a built-in safe for keeping valuables & important documents. And the crowning touch? PLANTATION SHUTTERS throughout--ABSOLUTELY STUNNING---and UNDENIABLY ELEVATED! An OVERSIZED 2-CAR GARAGE complete w/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/retractable awning providing additional space for entertaining or simply relaxing & enjoying the outdoors. 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 (including 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 BALLROOM and various 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 exceptional community!

228 Bayberry Dr, Chester

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

$265,000
2 Beds ⋅ 2 Baths
Chesapeake Waterfront Lifestyle Without the Waterfront Price Tag! Welcome to a beautifully transformed retreat in Kent Cove, where easy coastal living meets the comfort and convenience of a thoughtfully updated home. This exceptional 2-bedroom, 1.5-bath townhouse offers a rare opportunity to enjoy water views, community water access, multiple docks, resort-style amenities, and expansive outdoor living—all in a peaceful Stevensville setting just one minute from Routes 301/50. From the moment you arrive, you'll notice that this isn't your typical townhouse. Extensively updated and lovingly maintained, the home received approximately $25,000 in improvements in 2018, including a complete kitchen renovation, updated bathrooms, new flooring throughout, stainless steel appliances, granite countertops, fresh paint, updated water-heater components, and a custom cabinet niche/coffee station in the dining area. An additional $3,000 in improvements was completed in 2026, keeping the home fresh and move-in ready. The heart of the outdoor experience is the new 8' x 22' Trex deck—a substantial private entertaining space designed for morning coffee, evening cocktails, outdoor dining, or simply enjoying the peaceful Kent Cove surroundings. A second front deck opens to a relaxing common area, while the semi-private common area behind the home creates an additional sense of privacy and space. And then there's the water. Enjoy water views and community access to the water, with three community docks providing opportunities to take in the scenery and enjoy the Eastern Shore lifestyle. Whether you're looking for a peaceful place to unwind after a long day, a weekend escape, or an easy-care home where you can enjoy the outdoors without the responsibilities of a larger property, Kent Cove delivers. The community's amenities add exceptional value and convenience. The $522 monthly HOA fee includes water and sewer, twice-weekly trash pickup, snow removal, maintenance of common areas, exterior townhouse maintenance, a community pool, and access to three docks. It's a lifestyle designed to let you spend less time maintaining a property and more time enjoying it. A detached one-car garage provides valuable storage and parking, while the two-level layout offers comfortable separation between living and private spaces. Best of all, you get the tranquility and character of Eastern Shore living while remaining incredibly convenient to major commuter routes. Routes 301/50 are just one minute away, putting the Bay Bridge, Annapolis, shopping, dining, and everything Stevensville has to offer within easy reach. Updated. Waterfront-oriented. Turnkey. Low maintenance. Convenient. If you've been waiting for an opportunity to enjoy the Kent Island lifestyle without taking on the price and upkeep of a detached waterfront home, this is the one to see. Come experience the views, the decks, the water, and the unique sense of community that make Kent Cove such a special place to call home.

15 Mariners Way Unit A-1, Stevensville

Listing courtesy of RE/MAX Plus. Contact:

$599,900
3 Beds ⋅ 4 Baths
KENT ISLAND WATERFRONT • GOURMET KITCHEN • TWO PRIVATE DECKS • LUXURIOUS PRIMARY SUITE • CLUBHOUSE + FITNESS CENTER • MARINA ACCESS Experience Kent Island waterfront living in this beautifully appointed townhome in sought-after Bayside of Chester. The open-concept interior offers abundant natural light, spacious living areas, and stylish finishes throughout. The gourmet kitchen is designed for both everyday living and entertaining, featuring generous cabinetry, ample counter space, and a large center island with seating that flows seamlessly into the dining and living areas. The spacious primary suite offers a walk-in closet and luxurious ensuite bath, while additional bedrooms and flexible spaces provide room for guests, a home office, or recreation. Enjoy TWO PRIVATE DECKS for outdoor dining, morning coffee, or relaxing in the peaceful surroundings. An attached garage, additional storage, and parking spaces across the street add convenience. Bayside amenities include a clubhouse, fitness center, pool, tennis courts, walking trails, and marina access. Castle Marina slips are available for short-term or annual rental, with select slips near Queens Landing potentially available for purchase. Close to waterfront dining, shopping, golf, and major commuter routes.

1012 Auckland Way, Chester

Listing courtesy of Redfin Corp. Contact:

$815,000
4 Beds ⋅ 3 Baths
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!

231 Evelyne St, Chester

Listing courtesy of Wilson Realty & Staging LLC. Contact:

$829,966
4 Beds ⋅ 3 Baths
THIS HOUSE HAS NOT BEEN BUILT YET! Timberlake Homes Design|Build provided the description of the home and features. Renderings/elevations are not community-specific and may show features/elements/materials that are not offered in your community of choice. Please see your sales manager to confirm the specific house type elevations available. BEECH - Discover this new design which offers farmhouse-Craftsman charm and a flexible, open layout. This design features a main-level owner’s suite, three upstairs bedrooms, and a convenient first-floor laundry off the two-car garage. The spacious great room flows into a large kitchen island and dining space perfect for entertaining, with stainless steel appliances and a walk-in pantry. Customize with an optional fifth bedroom, sunroom, or screened porch, and a versatile flex space perfect for a home office or playroom. The Beech is designed for comfort, versatility, and easy living. FEATURES include: Main level owner’s suite, Sunroom or screened porch, 4 – 5 bedrooms; 2.5-3.5 bathrooms. Starting from 2,827 base square feet, Island kitchen with stainless appliances, walk-in pantry, and breakfast area Four standard bedrooms, Second-level loft (customizable to a fifth bedroom), two buddy-bath options, owner’s-choice flex space on the main level. Please refer to builders website for more details. This prime residential land parcel, located in the desirable ROMANCOKE ON THE BAY subdivision in Stevensville, MD, offers a unique investment or building opportunity with significant potential for appreciation. Spanning 0.56 acres, this corner lot features wooded areas that provide both privacy and a natural aesthetic, enhancing the property's overall appeal. Strategically positioned just about four blocks from the picturesque Eastern Bay, this lot benefits from proximity to water-oriented activities without the premium of direct waterfront ownership. Investors can capitalize on the growing demand for properties near water bodies, making this an attractive option for future development. The community amenities are a standout feature, including a boat ramp, clubhouse, picnic area, and jogging/walking paths. These facilities not only enhance the quality of life for residents but also increase the property's desirability to potential buyers or renters. With super low association fees, investors can enjoy the benefits of community amenities without the burden of high costs. The lot's corner location along the South Kent Island walking path provides ample privacy and accessibility, which can be advantageous for future residential development. The surrounding area is poised for growth, making this property an excellent long-term investment. As demand for residential properties near water continues to rise, this lot presents a compelling opportunity for those looking to enter the real estate market or expand their portfolio. In summary, this 0.56-acre corner lot in ROMANCOKE ON THE BAY is not just a piece of land; it's a strategic investment in a thriving community with abundant amenities and proximity to Eastern Bay. With the potential for appreciation and the appeal of a water-oriented lifestyle, this property is a must-consider for savvy investors looking to maximize their returns or those seeking to build their dream home.

Touhey Drive, Stevensville

Listing courtesy of Realty Navigator. Contact:

$540,000
4 Beds ⋅ 3 Baths
Beautifully updated 4-bedroom, 3-full-bath split-level home offering flexible living space in a sought-after water-access community! Nearly every major update has already been completed, including a new roof in 2024, new HVAC in 2026, beautifully renovated kitchen and bathrooms, new flooring, fresh paint, and a newly fenced backyard. The upper level features three bedrooms and two full bathrooms, while the spacious lower level offers a separate au pair or guest suite with a fourth bedroom, full bathroom, second partial kitchen, and additional living space. This versatile layout is ideal for guests, extended family, a home office, or anyone looking for a little extra privacy. Outside, enjoy the newly fenced backyard with plenty of room to relax, entertain, or play. Located in a wonderful water-access community with amenities that make it easy to enjoy the Eastern Shore lifestyle. With so many recent improvements already completed, this home offers the perfect combination of updated interiors, flexible space, and a fantastic community setting!

807 Worcester Dr, Stevensville

Listing courtesy of Berkshire Hathaway HomeServices PenFed Realty. Contact:

$425,000
4 Beds ⋅ 2 Baths
Welcome to this adorable, move-in-ready 4BR/2BA Rancher, nestled on a sprawling manicured lot (including an in-ground sprinkler system) in a community with fantastic amenities, including a community pool and beach and marina access. Pull into the double-wide driveway, make your way to the covered front porch, and step inside your new home. The main living area offers a spacious open-concept floor plan with vaulted ceilings, creating an inviting sense of space and natural light throughout the softly painted interior. The large living room flows seamlessly into the dining area and kitchen, making this the perfect space for everyday living and entertaining.  The kitchen offers abundant cabinet and counter space, stainless steel appliances, and a separate pantry closet with convenient laundry. A sink positioned beneath the window provides a pleasant view while preparing meals and adds to the functionality of this inviting kitchen.  Down the hall, you’ll find three sizable secondary bedrooms that share a full bathroom, along with a spacious primary suite featuring a double closet and a private full bathroom. From the sliding glass doors in the dining room, step outside onto a large wood deck featuring a convenient roll-up awning that overlooks the expansive yard. The beautifully maintained outdoor space offers plenty of green space, two storage sheds, and abundant possibilities for gardening, entertaining, and more. This home is move-in ready and ideal for any new homeowner. Located near shopping, restaurants, and commuter routes, this adorable rancher offers the perfect combination of comfort, convenience, and outdoor space.

909 Petinot Pl, Stevensville

Listing courtesy of LPT Realty, LLC. Contact:

$349,900
3 Beds ⋅ 2 Baths
REDUCED!! Discover the desired WATERFRONT Chester River Beach Community! Just one block from the Boat landing with boat ramp, boat slips, playground, beach, pavilio , picnic area and kayak storage! This one level Rancher boasts 1,593 sqft. of living space and features an open floor plan. The large kitchen boasts an eat-in area with plenty of room for a large dining table for all to gather! The heart of the home is the cozy wood stove, creating a warm atmosphere in the family room. Enjoy three spacious bedrooms and two full baths, which includes the ensuite bath in the primary! Step outside to your huge backyard and enjoy nights under the stars or unwind and grill dinner in your own little courtyard! One car garage is perfect for storage along with an extensive driveway for ample parking. Just take a very short stroll to the community landing and indulge in fishing, crabbing, kayaking or simply soaking in the tranquil views and the BEST SUNSETS! NEW Furnace '24, NEW Hot Water Heater '25, NEW Dishwasher '25 and No Flood Zone here! Top-rated schools, nearby parks and Kent Island Cross Trail is just an added bonus! Close to Marinas, Waterfront Dining, the Narrows, Boutique Shopping this location is perfect for those seeking a vibrant lifestyle on the Shore! Easy on and off RT 50 for the commuter. Don't miss your opportunity to be in Chester River Beach at this great price!

815 Chester River Dr, Grasonville

Listing courtesy of RE/MAX Executive. Contact:

$599,900
4 Beds ⋅ 3 Baths
Welcome to 108 Margaret Drive, a spacious and unique Kent Island home situated on a private, level lot and offering a flexible floor plan, incredible 4-car drive-through garage, seller-owned solar system, and easy access to the area's waterfront recreation and amenities. The main level features hardwood floors throughout and a spacious living room highlighted by a wood-burning stove. The kitchen offers granite countertops, an induction range, newer dishwasher and microwave, a large pantry, reverse osmosis water filtration system, and space for casual dining. A large screened porch provides additional space to relax, dine, or entertain while enjoying the outdoors. Three bedrooms and two full baths are also located on the main level, including the primary suite with its own private bath. The hall bath is filled with natural light from a skylight, while a convenient laundry/mudroom with a newer washer and access to both the garage and exterior adds to the home's functional layout. Upstairs, an expansive loft is joined by a separate room that can serve as a fourth bedroom, home office, bonus room, or additional flex space, along with another full bath and ample storage. This versatile upper level provides plenty of options for guests, working from home, recreation, hobbies, or whatever best fits your needs. The upper-level heat pump was replaced in August 2026. One of the property's most distinctive features is the oversized 4-car drive-through garage, with access from both the front and rear. There's exceptional room for vehicles, boats, recreational equipment, a workshop, hobbies, and storage, an especially valuable feature for enjoying the Kent Island lifestyle. Another major benefit is the seller-owned solar energy system, with no solar lease or loan for the buyer to assume. This is an all-electric home with no separate gas or heating-oil bill, and the sellers have paid just $9.75 per month for electricity for the past 24 consecutive months, which is Delmarva Power's minimum monthly service charge. The system has historically produced more electricity than the sellers use, providing significant savings on electricity costs while excess production has typically resulted in money back to the sellers annually through net metering. Solar production records and electric bill history are available for buyer review. Outside, the private, level .44-acre lot provides plenty of usable yard space for entertaining, recreation, pets, gardening, or simply enjoying the outdoors. The location puts some of Kent Island's best recreational amenities within easy reach, including Romancoke Pier and Park, Matapeake Beach, Pier and Boat Ramp, and Blue Heron Golf Course. With its 4-car drive-through garage, remarkably low historical electric bills, flexible 4-bedroom layout, main-level living, private .44-acre lot, and proximity to the water, 108 Margaret Drive offers a combination of features that is truly hard to find.

108 Margaret Dr, Stevensville

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

$719,900
3 Beds ⋅ 4 Baths
Welcome to Oyster Cove Live the Oyster Cove lifestyle! Welcome to a beautifully maintained townhome in Oyster Cove, a gated waterfront community offering the perfect blend of elegance, convenience, and carefree living. Here, the grounds are maintained for you, giving you more time to enjoy the lifestyle you’ve worked for. Residents can take advantage of the community pool, waterfront surroundings, and peaceful, beautifully landscaped setting. Enjoy the best of Grasonville right outside your door—restaurants, shopping, marinas, entertainment, and everyday conveniences are all just minutes away and easily accessible by car, bike, or even a leisurely walk. Whether you’re looking for a full-time residence, a weekend retreat, or a low-maintenance home where you can simply lock the door and go, Oyster Cove offers an exceptional setting. This is more than a townhome—it’s a lifestyle. Come experience the charm, sophistication, and relaxed waterfront atmosphere of one of the area’s most desirable communities. This beautifully refreshed three-level townhouse is move-in ready and priced to sell at $719,900. Freshly painted throughout, featuring brand-new carpet and freshly refinished hardwood flooring, this home offers a clean, updated feel from the moment you walk in. Enjoy the spacious three-level layout with plenty of room for everyday living and entertaining. A private boat slip is included, adding exceptional value for boating and waterfront enthusiasts. Move right in and enjoy all that Oyster Cove has to offer. Don’t miss this opportunity to own a beautifully refreshed townhouse with a boat slip at an attractive price! Thoughtfully staged (virtual) to highlight the home's spacious rooms, functionality, and potential.

1202 Oyster Cove Dr, Grasonville

Listing courtesy of Coldwell Banker Waterman Realty. Contact:

$449,900
3 Beds ⋅ 3 Baths
Welcome to 227 Dorchester Road — a nicely updated 3-bedroom, 3-full-bath split foyer tucked on a private, fenced lot in the water-oriented community of Kent Island Estates. The main level features new LVP flooring, a bright kitchen with painted cabinetry, 3 bedrooms and 2 full baths, including a fully renovated primary bath with a custom tiled shower. The hall bath has also been refreshed with updated flooring and paint. The finished lower level offers fantastic flexible living space and was substantially renovated in 2023 with new drywall, electrical, flooring and paint, plus a cozy pellet stove and an existing third full bath. Outside, enjoy the fenced backyard, a large deck with access to the yard and eat-in dining area, a concrete patio and plenty of room for entertaining, gardening or play. There's even a chicken coop that conveys — and the chickens can convey too! The STEP sewer system was installed in 2018, taking one more major item off the list. And when you're ready to get out and enjoy Kent Island, the South Kent Island Trail runs right through the community, while nearby Romancoke Pier offers fishing, crabbing, picnicking and a small sandy beach for launching kayaks. Updated, comfortable and close to the water — this is Kent Island living! Check out the community website for more information on the associations and optional fees for access to the various amenities. The $20/year mandatory fee is for KIE road maintenance.

227 Dorchester Rd, Stevensville

Listing courtesy of RE/MAX Leading Edge. Contact:

$542,500
3 Beds ⋅ 3 Baths
**TWILIGHT OPEN HOUSE Thursday October 1st 5PM-7PM** There’s more here than meets the eye! This charming home may look like a classic rancher from the curb, but inside and out, it offers an impressive amount of flexibility. The main home features three bedrooms, two full bathrooms and an oversized family room overlooking the beautifully landscaped, fully fenced backyard with privacy fencing and a rear deck. But the real surprise is the separate studio-style bonus space with its own private entrance, full bathroom, stackable washer and dryer, refrigerator, cabinetry and countertop space. Whether you envision an in-law suite, work-from-home office, guest quarters or potential rental space, the possibilities are plenty. Outside, you’ll ALSO find a detached shed with concrete floors and electric, plus an extended driveway with double gates opening to an additional parking pad, perfect for a boat or camper. An encapsulated crawlspace and newer roof add extra peace of mind. Located in the community of Bay City, you’ll enjoy a neighborhood setting with water access, a playground with picnic area, PLUS just minutes from fine dining, restaurants, marinas, public parks, playgrounds and bike trails of Kent Island. Not to mention, easy access to the Chesapeake Bay Bridge or commuter bus stops.

404 Victoria Way, Stevensville

Listing courtesy of RE/MAX Executive. Contact:

$120,000
1 Beds ⋅ 1 Baths
SEASONAL LIVING ONLY! April through November! Great camper cooperative in the Kent Narrows! SEASONAL LIVING ONLY, from April through November! Enjoy a fantastic vacation getaway and the relaxed Eastern Shore lifestyle. This updated park model camper is ready for you to enjoy life at Beach Harbor. It is fully furnished, except for the large grey sectional. The camper sleeps at least 4, and depending on the sofas, it can accommodate 6-8 people. New sunroom, new roof, new siding, updated flooring, updated heat and A/C, new windows, extra parking, and golf cart conveys with full-price offer. The golf cart is in great condition and is newer. For park purposes, it is considered a 2-bedroom. Some photos are lighting-enhanced with AI. Must make an appointment to view. Owner to arrange for showings. Parking for showings is in the guest parking outside the gate. Cash or personal loan only. No mortgage financing available, cash or personal loan onlyu. Vacation rentals are allowed, but ONLY self-managed! The owner must register guests with the office. Rules do apply!

111 Beach Harbor Dr Unit 236-E, Grasonville

Listing courtesy of Realty Navigator. Contact:

$574,900
4 Beds ⋅ 4 Baths
Luxury homes rarely become available. This stunning end unit townhome offering 4 bedrooms, 3.5 bathrooms, and an impressive list of high end upgrades is available in sought after Ellendale Community. Filled with natural light, the open floor plan features hardwood floors, custom plantation shutters, elegant trim, and a built-in Bose surround sound system. The gourmet kitchen is equipped with stainless steel appliances, 42" soft close maple cabinetry, under cabinet & pendant lighting, and backsplash. Escape to the spacious primary suite with a tray ceiling and spa bath or unwind on the composite deck overlooking spectacular sunset views. Remodeled bathrooms, LED lighting throughout, central vacuum and an oversized 2 car garage with custom storage. Located just minutes from the Bay Bridge, you will also enjoy resort style community amenities including a pool, clubhouse, fishing pier, boat storage, and walking trails.

118 Amanda Frances Ln, Stevensville

Listing courtesy of RE/MAX Executive. Contact:

$719,990
2 Beds ⋅ 3 Baths
Welcome to Chester, a thoughtfully designed home offering 2 bedrooms, 2.5 baths, and a 1-car garage. Scheduled for settlement in May 2027, this home combines comfort, functionality, and stylish finishes for modern living. The main living area features an electric fireplace, creating a warm and inviting focal point, while a dry bar adds the perfect touch for entertaining. A dedicated home office with French doors provides a private and polished space for working from home, studying, or pursuing hobbies. The kitchen is designed for both everyday living and entertaining, featuring a single oven, microwave, gas cooktop, range hood, dishwasher, pendant lighting, tile backsplash, and quartz countertops. Laminate flooring flows throughout the home, with tile flooring in both full baths for added durability and style. The primary bath offers a relaxing retreat with a spacious shower featuring a built-in seat and handheld shower wand, along with a double-sink vanity and quartz countertops. 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.

736 Warbler Way Unit 2733, Chester

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

$595,000
4 Beds ⋅ 4 Baths
This charming 4-bedroom, 4-bathroom townhouse in the desirable Ellendale community offers a perfect blend of modern comfort and inviting warmth. Built in 2023, this Baldwin built home features an open floor plan with luxury vinyl plank flooring and carpet in the bedrooms, ideal for both relaxation and entertaining. The spacious kitchen features a large center island and high-quality appliances, including a built-in microwave and dishwasher, making meal prep a delight. Large Deck off dining/kitchen area, too! Enjoy evenings by the fireplace or step out onto the balcony and deck to soak in the serene views of the garden and open common area. Nearby parks and walking paths invite outdoor adventures, while excellent schools and convenient access to commuter lots and the airport ensure a seamless daily routine. With an attached garage and driveway parking, this home is a true gem in a vibrant neighborhood, ready to welcome you home.

314 Allison Jane Dr Unit H-2, Stevensville

Listing courtesy of Wilson Realty & Staging LLC. Contact:

$565,000
4 Beds ⋅ 4 Baths
Welcome to 624 Davol Road, a beautifully updated 4-bedroom, 3.5-bath home offering nearly 2,500 square feet in the sought-after Cloverfields community. Recent 2026 improvements include updated flooring, a renovated kitchen, new lighting and a new roof, creating a fresh, move-in-ready feel throughout. Outside, you’ll appreciate the garage, large parking pad and fenced backyard with plenty of space to relax, entertain or play. Cloverfields offers an incredible Eastern Shore lifestyle with a community pool, private beach, playgrounds and marina with boat slips available for rent when offered. Conveniently located just off the first exit over the Bay Bridge, the home provides easy access to nearby trails, shopping, dining and everything Kent Island has to offer. Coming soon — stay tuned for your opportunity to see this spacious, updated Cloverfields home!

624 Davol Rd, Stevensville

Listing courtesy of Samson Properties. Contact:

$835,000
3 Beds ⋅ 3 Baths
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

Listing courtesy of TTR Sotheby's International Realty. Contact:

$465,000
4 Beds ⋅ 4 Baths
LOOKING FOR AN INTEREST RATE THAT STARTS WITH A 5? If rising rates have you questioning whether you can afford to move, come see 101 Branta Lndg, Stevensville in the community of Ellendale! With an accepted offer by 9/30, the sellers are offering up to $10,000 toward a rate buydown. Ask your lender how - or call us! This beautifully updated end-unit townhome offers low-maintenance living with approximately $35,000 in improvements over the last 1-2 years. You have nothing to do here but unpack! Freshly painted throughout, it features new flooring in the main living area, kitchen countertops and appliances, an updated primary bath with walk-in shower, refreshed stone fireplace, and more. With 4 bedrooms, 4 bathrooms (2 half & 2 full), a 2-car garage, and a spacious deck, there’s plenty of room to live comfortably without the upkeep of a single-family home. As an end unit, you’ll also enjoy added privacy and natural light. Ellendale offers a pool, clubhouse, playground, walking trail, boat storage, and fishing pier with access to Thompson Creek for kayaking and paddleboarding. Plus, you’re minutes from waterfront dining, marinas, resorts, shopping, parks, the public beach, and schools, with the Chesapeake Bay Bridge just 2 minutes away. Updated. Low maintenance. Convenient. And ready for you to move right in. OPEN DAILY BY APPOINTMENT!!

101 Branta Lndg, Stevensville

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

$998,000
3 Beds ⋅ 3 Baths
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

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

$749,900
3 Beds ⋅ 2 Baths
Nestled within the prestigious Oyster Cove community, this exquisite 3rd floor Penthouse corner residence offers a harmonious blend of luxury and comfort, perfectly situated along the serene Kent Narrows/ Prospect bay. Served by elevator, the contemporary architectural style is complemented by high-end finishes throughout, including luxury vinyl plank flooring and elegant built-ins that enhance the open floor plan. Step inside to discover a spacious family room that seamlessly connects to a gourmet kitchen, featuring upgraded countertops and modern appliances, including a sleek electric range and a convenient dishwasher. The inviting breakfast area is perfect for casual dining, while the primary bath offers a private retreat with sophisticated fixtures. Enjoy the tranquility of river views from your porch, where you can unwind and soak in the picturesque surroundings. The property boasts deeded private 40 foot boat slip, ideal for boating enthusiasts, and a community pool for leisurely afternoons. Additional amenities include a gated entrance, ensuring privacy and security, along with beautifully maintained common grounds and walking paths. With three generously sized bedrooms and a cozy electric fireplace, this home is designed for both relaxation and entertaining. The community offers a wealth of recreational options, including tennis courts, pickle ball and picnic areas, enhancing the luxurious lifestyle that Oyster Cove provides. Experience the ultimate in waterfront living, where every detail has been thoughtfully curated for your enjoyment.

130 Oyster Cove Dr Unit 130, Grasonville

Listing courtesy of Coldwell Banker Waterman Realty. Contact: