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206 Anchor Ln, Chester
$555,000
3 Beds ⋅ 2 Baths
KENT ISLAND ** CUSTOM RANCHER ** Welcome to the sought-after neighborhood of Castle Marina. There are No HOA or Association fees in this established community. You can walk to your boat in the marina, stroll to the local pub for dinner or hit the Cross Island Trail to get in your steps for the day. So close to all of the amenities Kent Island has to offer, yet tucked away behind Four Seasons, with mature landscaping and friendly neighbors. ** This single level home with 2,470 sq ft, offers plenty of living space and is perfect for entertaining. Beyond the welcoming foyer is the living room with large bay window, skylights and comforting wood stove, opening to the spacious kitchen with recently updated appliances, plenty of cabinetry and leads to the open dining room and heading out to the delightful sunroom, surrounded by windows and nestled in the landscaped back yard. The home offers a large primary bedroom with double closets and bathroom with double sink vanity and large tile shower. There are two more large bedrooms each with a skylight and oversized closets and a hall bath with double vanity and tiled tub/shower. Plus there is the Bonus Rom (guest room, homeschool room, craft room, gym, library or whatever you need it to be) with french doors for privacy and a separate laundry/mud room. ** Outside is a 2 car garage, concrete driveway, and large Amish built shed. All of this sits on a 1/2 acre landscaped, fenced yard with fig trees, magnolias, evergreens, crape mrytles and more. ** The owners have made all of the expensive updates within the past few years- New Roof 2017, New Water Heater 2019, New HVAC 2021, New Washer & Dryer 2022, New Shed 2024, New Garage Door 2026, New Windows 2026. ** The property is serviced by the public sewer system. Water is accessed by the private well and run through the homes water conditioning system. This home is built on a slab, so no wet, moldy crawl space to maintain. In 2019, the owners had the plumbing in the slab abandoned and all new plumbing run through the attic and walls with access throughout. ** If you are ready to live the Island Lifestyle in a low maintainence home in a great neighborhood with ameneties close by, call for your showing today.

206 Anchor Ln, Chester

Listing courtesy of Coldwell Banker Waterman Realty. Contact:

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

103 Meadowcroft Dr, Centreville
$555,000
4 Beds ⋅ 3 Baths
Welcome to 103 Meadowcroft Drive in the highly sought-after Northbrook community on Maryland’s Eastern Shore — where charm, comfort, and thoughtful upgrades come together beautifully. From the inviting covered front porch to the exceptional curb appeal, this home makes a memorable first impression. Inside, you’ll appreciate the plush carpeting, and stylish LVP flooring throughout the main level. Designed with both entertaining and everyday living in mind, the spacious floor plan offers versatile flex spaces to fit your lifestyle. The kitchen is a true centerpiece, featuring stainless steel appliances, a large pantry, island cooktop, wine and beverage coolers, and a dedicated coffee bar with sink for added convenience and abundant prep space. Just beyond, a stunning sunroom addition offers year-round enjoyment with cathedral ceilings, a ductless mini-split system, and cozy gas fireplace. Outdoor living is equally impressive with a maintenance-free deck, patio area, outdoor kitchen setup, and hot tub — creating the perfect setting for relaxing or hosting guests. Upstairs, the primary suite serves as a private retreat with vaulted ceilings, a spacious ensuite bath featuring a walk-in shower, jetted soaking tub, dual vanities, walk-in closet, and an adjoining sitting room for added comfort. Secondary bedrooms are generously sized and share a beautifully customized hall bath with dual sinks. Additional highlights include a 15x9 storage shed, conditioned 4-foot crawl space, and extensive garage shelving to meet all your storage needs. Residents of Northbrook enjoy community amenities including a playground, open field, pavilion, ponds, and walking paths — all conveniently located near schools, dining, shopping, and local boat ramps. This is a rare opportunity to enjoy Eastern Shore living at its finest. Professional Photos May 19

103 Meadowcroft Dr, Centreville

Listing courtesy of Chesapeake Real Estate Associates, LLC. Contact:

Selling Office: Realty Navigator.

105 Concerto Ave, Centreville
$555,000
4 Beds ⋅ 4 Baths
Price Drop in the sought after community of Symphony Village in Centreville 55+ Active Adult Community. This beautiful Beethoven model home consisting of 4 bedrooms and 3 and one half bath is awaiting it's next owner. As you enter this home, you'll notice the hardwood flooring, wainscoting, chair rail moldings, crown molding and trey ceiling. in the large living and dining areas with Retractable Shades in these rooms and the office. To the right, you'll find the office located on the front of the home and the staircase leading to the upper level of the home. As you make your way through, you'll enter the family room and the garden room with fireplace located on the rear of the home. You must take a moment to see the Gourmet Kitchen with granite counters, new induction cooktop 2025, new wall oven and microwave 2025, new range hood 2025, new garbage disposal 2025 and new refrigerator 2023. The oversized master suite, with his and her walk-in closets and master bath featuring split vanity sinks, walk-in shower and corner soaking tub, 2nd bedroom, full bath, half bath and laundry room complete the main level. The upper level features 2 large bedrooms, a sitting area and a Jack and Jill full bath. For additional storage there is a room sized closet also located on the upper level and a Sky Basement above the garage. To finish off this home, you must experience the rear paver patio, tree line for privacy and Retractable Awning installed in 2024.

105 Concerto Ave, Centreville

Listing courtesy of RE/MAX Executive. Contact:

Selling Office: Unrepresented.

325 Greenspring Rd, Queenstown
$555,000
3 Beds ⋅ 2 Baths
PRICE REDUCED- BRING ALL BUYERS A fantastic opportunity for buyers looking for exceptional value in a move-in ready home. The seller is very motivated! Property is just 10 minutes from the Bay Bridge IN QUEENSTOWN AND NO HOA!!! , This brand new custom rancher offers the perfect blend of country living and convenience. Surrounded by a peaceful rural setting ideal for deer and fowl hunters, this location also puts you close to prime outlet shopping, popular seafood restaurants, and a true boater’s paradise. Step inside to an open and modern floor plan featuring 3 large bedrooms, 2 full bathrooms, and a spacious drive-in garage. The large primary suite includes its own private full bath that is located on the opposite side of the house of the other 2 spacious bedrooms. The main living area flows seamlessly from the living room to the dining space and into the beautifully designed kitchen. The kitchen showcases new cabinetry, quartz countertops, a tiled backsplash, and a large island perfect for gatherings. Luxury vinyl plank flooring runs throughout the home, offering both durability and style. Enjoy a lush backyard ideal for outdoor fun, plus a welcoming front porch where you can relax and take in the quiet country landscape. A private driveway tucked off the main road provides added seclusion and charm. ***NO HOA***

325 Greenspring Rd, Queenstown

Listing courtesy of Berkshire Hathaway HomeServices PenFed Realty. Contact:

Selling Office: Douglas Realty LLC.

822 Kimberly Way, Stevensville
$555,000
4 Beds ⋅ 3 Baths
Discover a home you’ll never want to leave in this beautifully appointed 4-bedroom, 2.5-bath property located in the highly sought-after water-privileged community of Cloverfields. Designed with comfort and versatility in mind, the unique floor plan is ideal for multi-generational living. Choose between two spacious primary suites—one conveniently located on the main level with an attached luxury bath featuring a jetted tub, separate shower, and an expansive walk-in closet. The bright, open kitchen offers generous storage, granite countertops, and a gas range with dual ovens—perfect for home cooks and entertainers alike. Upstairs, you’ll find large secondary bedrooms along with a flexible bonus space ideal for an office, library, playroom, or gaming lounge. The second-floor laundry room shines with natural light and includes raised front-load machines, making everyday tasks more enjoyable. Enjoy peace of mind with major mechanical upgrades, including a brand-new hybrid HVAC system (2025) with a 10-year warranty, new gutter guards (2025), an insulated crawl space, a tankless water heater, and a propane pre-buy program—ensuring year-round efficiency and low-maintenance living. Step outside to your private retreat, where relaxation continues on the expansive deck—complete with real wood furniture that conveys—overlooking a fully fenced backyard with native landscaping, mature shade trees, and a stone fire pit. An oversized garage/workshop with a built-in workbench and an additional shed provide exceptional storage options for tools, lawn equipment, or even beach gear. Best of all, you’re just a short walk to the community beach, passing the neighborhood pool along the way. Cloverfields offers an array of amenities along the Chester River, including a community boat ramp, rentable boat slips, a netted swimming area, playground, clubhouse, and more—all for less than $17/month in HOA dues. Spend your mornings at the beach, your afternoons unwinding on the deck with a crab feast, and your evenings around the fire pit creating lifelong memories. This home offers the perfect blend of comfort, convenience, and the coveted Eastern Shore lifestyle.

822 Kimberly Way, Stevensville

Listing courtesy of RE/MAX One. Contact:

Selling Office: Wilson Realty & Staging LLC.

216 Blakefield Dr, Chestertown
$552,000
4 Beds ⋅ 3 Baths
The wait is over 216 Blakefield Drive is complete, ready for occupancy and you will not be disappointed. This is the last avaiable lot in this community so don't wait! Discover the charm of this stunning new construction home in the desirable Blakefield community, completed in 2025. This beautifully designed Colonial-style residence boasts 4 spacious bedrooms and 3 full bathrooms, offering ample space for relaxation and entertainment. The kitchen is a chef's dream, featuring an island, eat-in space, and modern appliances including a built-in microwave, dishwasher, electric oven/range, and refrigerator. Enjoy cozy breakfasts in the bright breakfast area or host formal dinners in the separate dining room. The luxurious touches continue with walk-in closets, a convenient upper-floor laundry, and a family room that flows effortlessly from the kitchen and a separate office making this a great option for those who work from home. A first floor bedroom is idea for a guest room, play room, in-law quarters and more. The home is adorned with luxury vinyl plank flooring and plush carpeting, creating a warm and welcoming atmosphere throughout. Set on a generous 1-acre lot that adjoins open space, this property offers a serene outdoor setting, perfect for enjoying nature or future landscaping projects. The side-entry attached garage provides easy access and additional storage. With its excellent condition and thoughtful design, this home is ready to embrace new memories. Experience the perfect blend of comfort and modern living in this exceptional property. Buy with ease when purchasing this new construction home. No HOA

216 Blakefield Dr, Chestertown

Listing courtesy of Chesapeake Real Estate Associates, LLC. Contact:

Selling Office: Anne Arundel Properties, Inc..

412 Bay City Rd, Stevensville
$551,000
4 Beds ⋅ 3 Baths
Welcome to 412 Bay City Road — where modern upgrade meets relaxed coastal living. This 4-bedroom, 3-bath beauty offers 2,000+ sq ft of thoughtfully curated space, a detached 2-car garage, and the peek-a-boo views of the Chesapeake Bay to keep your heart fluttering. Spread out on two levels, four full bedrooms and multiple outdoor living spaces. The kitchen boasts granite countertops and high end Kitchen Aid appliances (2021). Totally renovated Spa-inspired bathrooms make even weekday routines feel luxe with oversized tubs and floor to ceiling tiles. Newer/upgraded flooring throughout balances durability + aesthetic. The lower level is an amazing bonus for living on Kent Island! You will love having a second living space with a wood stove that heats the whole home, the beautiful laundry room with sink, 4th bedroom and a/ full bath. This space could easily be converted into an in-law suite! The 5 year old deck is made for gatherings, lazy sundowners, and soaking up ambient coastal energy. The fenced in yard offer two secure spaces. This thoughtful layout balances community + quiet zones that feel like home. Parking will never be an issue. There is a detached 2 car garage with it's own electric panel, plus an extended driveway that can accommodate nearly 10 vehicles, boats, or even a RV! If you’re ready for a home that checks the boxes (style, function, location, and charm), plus all new electrical and doors - make sure to come see 412 Bay City Road before it's SOLD. Bay City is a waterfront community offering amenities including boat ramp, pavilion and playgrounds for just $150/year. Public Sewer and Water. Matapeake School District.

412 Bay City Rd, Stevensville

Listing courtesy of Samson Properties. Contact:

Selling Office: RE/MAX Executive.

342 Wicomico Rd, Stevensville
$550,000
3 Beds ⋅ 2 Baths
Have you been waiting for your own slice of paradise to come on the market? Well, the wait is over. This home offers over 2,000 sqft of living space. The open concept gives you plenty of space to entertain or areas to have seperate quiet time. Step out back and an inviting pool is waiting for you to dive into. The liner is approx 3 years old so you should have years of worry free enjoyment. This home sits on nearly an acre with mature trees that give you plenty of privacy but with plenty of open space to host large gatherings. There is a great little tiki bar that gives you the feeling of being miles from home and on vacation every day. The community offers 2 waterside areas with great sunrises and sunsets. The Eastern Bay side has the best sunrises around with a picinic area in a park like setting, a place to launch your water toys and a playground for the young ones. The Chesapeake Bay side has a great beach area for launching your (fishing)kayak, paddleboard, etc or just chiil in the sand with your feet in the surf. If you're into fishing this is the spot. Some of the best sunsets you'll ever see. If this sounds like a place you would vacation to once a year just keep in mind this is the Kent Island lifestyle you can enjoy everyday. The epoxy floored garage has an interior entrace to the home to protect you from the elements. The gourmet kitchen has a workspace, an island and a countertop bar area that give guests space to be included in the kitchen activities but out of the way of the cook. There are 3 rooms to hang out in. One is a large sunroom that leads to the backyard with an inviting ingound pool . Another has a gas fireplace and the other has a woodstove that you can cozy up to in the winter months. There is a back up generator that is included just in case. There is an active community clubhouse that offers plenty of things to do. Including but not limited to parades, cook-offs, cook-outs, santa visits, Easter egg hunts, Halloween booths, yoga classes and much more. Volunteers are always appreciated so come and be part of something special. It does the psyche good.... The South Island Trail and Romancoke Pier are just outside the community. Shopping. public schools, multiple waterside resaurants and Bay Bridge access is very convenient. Well, what are you waiting for??? Make your appointment today!!!!!

342 Wicomico Rd, Stevensville

Listing courtesy of Rosendale Realty. Contact:

Selling Office: Keller Williams Flagship.

510 Symphony Way, Centreville
$550,000
4 Beds ⋅ 3 Baths
Welcome to Symphony Village in Centreville a 55+ Active Adult Community that HAS IT ALL! DON'T MISS THIS OPPORTUNITY! This thoughtfully maintained home offers over 3,190 square feet of living space as well a Sky Basement w/ 520 (approx.) square feet of additional storage space, Featuring 4 Bedrooms, 3 full baths, Roof 2019, Water Heater 2026, Washer/Dryer 2023, New Front Porch, Sidewalk plus drainage 2023, HVAC Units 2012, The Bright open main level includes Kitchen with extended granite countertops, stainless steel appliances, while the flowing layout includes hardwood floors, custom Blinds & Shades, and inviting living and dining areas. A GLORIOUS sunroom with wall-to-wall windows offers a tranquil retreat and opens onto a spacious Professionally Landscaped Patio, perfect for relaxing or hosting guests! The main level primary suite is a true retreat, featuring two walk-in closets, dual vanities, a soaking tub, and a walk-in shower Plus a fabulous Sitting Room/Office, Upstairs, a versatile loft provides the perfect setting for a Sports Bar area Etc., along with a guest bedroom complete with its own full bath and walk-in closet, Life in Symphony Village means more than just a beautiful home, it's a vibrant, welcoming community. Residents enjoy access to a clubhouse with social spaces, indoor and outdoor pools, a fitness center, pickleball and bocce courts, walking and hiking trails, and a full calendar of activities designed to keep you as active and engaged as you would like to be. Community HOA fee includes Partial Sprinkler system on your property! Conveniently located near Queenstown Premium Outlets and the charming downtown area of Centreville, you will also find yourself just a short drive from the waterfront towns of Chestertown, Easton, St. Michaels, Oxford and Annapolis. also, UMMS and UM Shore Regional Health are building a state-of-the-art medical center in Easton, set to open in 2028, This is more than a home, it is a LIFESTYLE .

510 Symphony Way, Centreville

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

Selling Office: RE/MAX One.

200 Schooner Way, Chester
$550,000
3 Beds ⋅ 4 Baths
Just minutes over the Chesapeake Bay Bridge, this beautifully maintained end-unit townhome in Bayside offers the perfect Eastern Shore escape. Spectacular water views overlooking Castle Harbor Marina, the home features multiple decks, updated finishes, and, if you choose Castle Harbor Marina, easy access to your boat slip, only steps away. With approximately 2,100 square feet on three finished levels, highlights include a gourmet kitchen with granite counters, a center island with prep sink, gas cooking, double ovens, an expanded great room with fireplace and hardwood floors, a spacious primary suite with a deck and sitting area, and a versatile top level with a great room, living area that has plenty of room for bunk beds and more. Water views again from your picture window. Community amenities include a clubhouse, pool, tennis courts, and volleyball courts.

200 Schooner Way, Chester

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

Selling Office: RE/MAX Leading Edge.

64 Long Creek Dr, Stevensville
$550,000
3 Beds ⋅ 3 Baths
Step into the perfect blend of comfort, space, and Eastern Shore charm at 64 Long Creek. Offering 1,804 square feet of thoughtfully designed living space on nearly 2 private acres, this 3-bedroom, 2.5-bath home delivers both functionality and style. Inside, you’ll find a comfortable, well-planned layout featuring a gas fireplace, formal living and dining rooms, and a cozy den just off the kitchen with eat-in table space. The kitchen shines with a New stove and dishwasher . A spacious mudroom includes a washer, dryer, utility sink, and exterior access—ideal for everyday convenience. One of the standout features is the 240 sq. ft. four-season sunroom, complete with a mini-split system for year-round heating and cooling—perfect for relaxing in any season. Step outside to a 390 sq. ft. deck, sealed for durability, along with a 10x12 patio—ideal for entertaining or enjoying peaceful outdoor living. The premium landscaping, filled with lush trees, creates a serene and private setting. Additional highlights include a partially furnished option (available upon request), a storage shed and a spacious attached double garage (696 sq. ft.) with a long paved driveway. The home is serviced by a private well and septic—and best of all, there are no HOA's. Location is everything, and this home delivers. Enjoy close proximity to the vibrant Kent Narrows, the Blue Heron Golf Course. Indulge in waterfront dining at top-rated seafood restaurants (5 min. away), explore nearby wineries, County boat ramps, visit the Elks lodge, or take in the breathtaking views of the Chesapeake Bay. Amazing Chesapeake Bay Sunrises/Sunsets and schools, shopping, restaurants all nearby and Annapolis is only minutes away. Just across the main road, the scenic Cross Island Trail invites you to start your mornings with a jog, enjoy leisurely bike rides, or take in tranquil waterfront strolls. This residence presents an ideal setting for those seeking a retreat from the bustle of everyday life. Whether you're searching for a full-time residence or a weekend retreat, this property offers the lifestyle you’ve been waiting for—privacy, convenience, and natural beauty all in one.

64 Long Creek Dr, Stevensville

Listing courtesy of Coldwell Banker Realty. Contact:

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

302 Rosin Dr, Chestertown
$550,000
5 Beds ⋅ 4 Baths
Nestled in the serene Chester Harbor community of Chestertown, MD, 302 Rosin Drive offers an idyllic waterfront lifestyle along the tranquil shores of Rosin Creek. Perched on an elevated lot with stunning vistas of Rosin Creek, this charming home blends classic Eastern Shore character with modern comforts. Imagine mornings with coffee overlooking the water, afternoons kayaking from your backyard and evenings just minutes from historic Chestertown's shops, dining, and Washington College. Seamless indoor-outdoor flow make this the ultimate retreat—perfect for entertaining with indoor and outdoor spaces. This home has a complete in-law-suite perfect for hosting guests, accommodating extended family, or creating a private home office with serene water views. This deceivingly large 5-bedroom, 4-bath home features; extensive landscaping, lovely gazebo and brand-new roof.

302 Rosin Dr, Chestertown

Listing courtesy of Cross Street Realtors LLC. Contact:

Selling Office: Cross Street Realtors LLC.

408 Laurens Way, Queen Anne
$550,000
3 Beds ⋅ 3 Baths
Welcome to 408 Laurens Way, located at the end of a quiet cul-de-sac in the heart of Queen Anne’s County. This beautifully maintained home offers nearly an acre of privacy, backing to open agricultural land. With approximately 2,400 square feet of living space, the property includes 3 bedrooms, 2.5 bathrooms, a spacious family room with a fireplace, a formal dining room, and an additional flex room that can serve as an office or den. Since purchasing, the sellers have made extensive updates, including a new roof, new HVAC system, fresh insulation and vapor barrier, new carpeting in all bedrooms, updated appliances, fresh interior paint, and more. The exterior features a thoughtfully designed hardscape, outbuildings, chicken coops, and plenty of outdoor space for recreation or gardening. The attached garage provides overhead attic storage with easy access. Experience the tranquility of Maryland’s Eastern Shore in this meticulously cared-for property, ready to welcome its next owner.

408 Laurens Way, Queen Anne

Listing courtesy of Realty One Group Performance, LLC. Contact:

Selling Office: Coldwell Banker Chesapeake Real Estate Company.

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.

47 Queen Anne Way, Chester
$549,500
2 Beds ⋅ 3 Baths
Enjoy resort style living every day in the gorgeous waterfront condo. Watch the sun & moon rise as you sip your favorite beverage. This sought after townhome/condo has extensive view of the Chester River & Eastern Neck Island. The owner has updated & made this place like no other. Soundproof quiet rock, custom barn doors throughout, gourmet kitchen with granite counters, soft close maple cabinets, Acacia wood floors, newer HVAC, remote full blind for back windows (heat & light senses), custom plantation blinds, bathrooms boasts stone walls, custom ceramic, jacuzzi tub, walk in shower, keypad entry door, remote awning that senses wind, hardscapes to enjoy the views and so much more! The cross island bike/hike trail is nearby along with restaurants, medical and shopping. Come check out this amazing place!

47 Queen Anne Way, Chester

Listing courtesy of Taylor Properties. Contact:

Selling Office: Non Subscribing Office.

12 Greenwood Shls, Grasonville
$549,000
3 Beds ⋅ 2 Baths
Enjoy easy one-level living in the highly desirable Prospect Bay community at 12 Greenwood Shoals. Set on just over an acre, this inviting three-bedroom, two-bath home offers the convenience of having all of your main living spaces on one level, paired with a peaceful setting in one of Grasonville’s most sought after golf and waterfront communities. Inside, a functional floor plan creates comfortable spaces for everyday living and entertaining with an open concept living room and kitchen that opens up to a large deck overlooking the backyard. The primary suite has a large closet and the two additional bedrooms offer plenty of space for guests or a home office. An oversized two-car garage offers exceptional additional space with room for storage, a golf cart, kayaks, canoes, or other outdoor gear - perfectly suited for the Prospect Bay lifestyle. A newer gutter system adds another thoughtful update to the home. Outside, the spacious fenced backyard is surrounded by mature trees, providing wonderful shade and creating a private, peaceful setting for relaxing, entertaining, pets, or play. Updated landscaping enhances the home’s curb appeal, while shallow water access from the property provides an ideal spot to launch a kayak or canoe and explore the surrounding waterways. Living in Prospect Bay means enjoying a lifestyle centered around recreation and community, with amenities including an 18-hole golf course, swimming pool, tennis and pickleball courts, clubhouse with restaurant and bar, marina, boat ramp, social activities, and more. Owner/Agent.

12 Greenwood Shls, Grasonville

Listing courtesy of Coldwell Banker Realty. Contact:

Selling Office: TTR Sotheby's International Realty.

114 Oyster Cove Dr Unit 1C, Grasonville
$549,000
2 Beds ⋅ 2 Baths
Welcome to Oyster Cove, where every day feels a little like vacation! This beautifully appointed first-level condo offers the perfect combination of comfort, convenience and Eastern Shore waterfront living. Step inside to gorgeous hardwood floors, a warm and inviting living area with an electric fireplace insert, and a beautifully finished kitchen featuring high-end granite countertops — even the backsplash is granite, creating a polished, upscale look. One of the best features of this home is its desirable first-level location. With minimal stairs and no need to wait for an elevator every time you come and go, everyday living is wonderfully easy. Step right outside your back door and enjoy lovely views of the water and boats. Imagine starting your mornings with coffee overlooking the marina and winding down in the evening with a cocktail while watching the sunset. It truly feels like being on vacation without ever leaving home. At Oyster Cove, there is plenty to enjoy without even leaving the neighborhood. Spend warm summer days at the community pool, meet friends for a game of pickleball, take a leisurely walk along the waterfront, watch the boats come and go, or simply relax and enjoy the peaceful marina setting. Bird and wildlife lovers will appreciate the frequent sightings of osprey, herons and even bald eagles. Whether you prefer being active or simply unwinding by the water, the community offers countless ways to enjoy the Eastern Shore lifestyle right outside your door. And for boating enthusiasts, there is an exciting additional opportunity: a separately deeded 40-foot boat slip is also available for purchase, giving you the option to keep your boat just steps from home and make the most of life on the Chesapeake Bay. Whether you're looking for a full-time residence, weekend getaway or an easy-to-maintain Eastern Shore retreat, this is a wonderful opportunity to enjoy the Oyster Cove lifestyle in one of the community's most convenient locations. Come see why life is just a little better by the water!

114 Oyster Cove Dr Unit 1C, Grasonville

Listing courtesy of RE/MAX Leading Edge. Contact:

Selling Office: Non Subscribing Office.

154 Encore Ct, Centreville
$549,000
3 Beds ⋅ 2 Baths
Welcome to this gorgeous home in Symphony Village at Centreville, an amenity-rich 55+ community offering an exceptional lifestyle just outside historic downtown Centreville. Situated on the largest and most premium lot in the neighborhood, this property enjoys a peaceful, private setting bordered by mature woods and a tranquil stream. The open concept home features a chef’s kitchen is the heart of the home, with beautiful Calcutta quartz counters, subway tile backsplash, stainless steel appliances including a gas range, abundant cabinetry, two pantries and recessed lighting. The kitchen opens seamlessly to the spacious family room, where a vaulted ceiling, gas fireplace, and French doors to the 20 x 25 deck create a warm and welcoming gathering space. A separate living room sits on the opposite side of the kitchen and flows into the dining area, offering plenty of room for both casual and formal entertaining. The spacious primary suite is a true retreat, highlighted by beautiful hickory wood floors, a lighted tray ceiling, sitting area with an arched window overlooking the woods, and two walk-in closets. The luxurious ensuite bathroom features separate vanities, a private water closet, and a glass-enclosed step-in shower. Designed for easy single-level living with a walkout basement, the home offers three bedrooms and two full bathrooms, while crown molding throughout adds an elegant finishing touch. Thoughtful updates include 2025 quartz countertops and a tankless water heater, 2024 heat pump and new stairs from the deck to the yard, 2023 roof, 2021 primary bathroom renovation, and 2020 appliances. The beautifully landscaped front and rear yards, mature trees, and covered front porch create an inviting first impression, while the backyard provides a serene retreat surrounded by nature.Enjoy the outdoors from the deck overlooking the wooded backdrop and stream, with convenient stairs leading directly to the yard. Symphony Village offers an impressive array of amenities and activities designed for active 55+ living. Ideally located just outside downtown Centreville, you'll have easy access to the Chester River, local dining and shopping, and Routes 301 and 50, making trips to the Delaware and Maryland beaches convenient in one direction and Baltimore and Washington, D.C. in the other. A rare opportunity to own the most desirable lot in Symphony Village and enjoy beautiful surroundings, exceptional updates, and an outstanding location. The fully outfitted laundry room offers custom shelving for exceptional organization and convenience. With its thoughtful layout, abundant natural light, wooded views, and generous gathering spaces, this home is perfectly suited for both relaxed living and entertaining family and friends.

154 Encore Ct, Centreville

Listing courtesy of Compass. Contact:

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

130 Opera Ct, Centreville
$549,000
4 Beds ⋅ 3 Baths
Huge price reduction.... 130 Opera Court in the sought after community of Symphony Village at Centreville. If you've been waiting for that home resting on an exceptional lot backing to an open area and woods, then this is the home you've been waiting for. The beautiful 4 bedroom, 3 full bath home is exceptional, move in ready and just waiting for you. As you enter the home, your eyes will be drawn to the bright open floorplan and the rear windows overlooking the large deck that expands across the entire rear of the home. On the right, you'll find the front guest bedroom/office, a second guest bedroom, full bath, laundry room and access to the garage and lower level of the home. Moving through the home, you'll pass through the large living area with double sided propane fireplace, mounted TV that conveys with the home and the relaxing area and dining area on the rear overlooking the large lot backing to beautiful woods. To the right is the gourmet kitchen with granite counters, appliances including a gas stove and under cabinet lighting. The expansive primary suite is a must see with French Doors leading to the balcony, his and her walk-in closets and the primary bath with a large walk-in corner shower. Moving to the lower level, you'll find a large family area, another guest bedroom, full bath, a massive amount of storage area and a workshop leading to the rear exterior of the home. This home rests on a premium wooded lot for your relaxation while enjoying the wildlife that the area has to offer.

130 Opera Ct, Centreville

Listing courtesy of RE/MAX Executive. Contact:

Selling Office: RE/MAX Executive.

726 Davol Rd, Stevensville
$549,000
3 Beds ⋅ 3 Baths
You are not going to want to miss 726 Davol! The Perfect Place to Call Home in Cloverfields! Welcome to this beautifully maintained 3-bedroom, 2.5-bath home offering 2,128 square feet of warm, inviting living space—perfectly designed for making lifelong memories. A versatile bonus room—currently used as playroom filled with laughter—can easily evolve with your needs as an optional 4th bedroom, dining room, or home office. From the moment you walk in, you’ll feel it—this is a home where life happens. With multiple living spaces, there’s room for everyone to spread out while still staying connected. The expansive primary suite offers a peaceful retreat, while the additional bedrooms on the 2nd story are well-sized providing extra comfort and space. The home has been thoughtfully updated with a new roof (2021), crawlspace and attic encapsulation (2025), fresh paint (2025), updated bathrooms (2025) & regraded sodded backyard with custom drainage system reflecting true pride of ownership throughout. The detached 2-car garage offers incredible flexibility, whether you envision a workshop, home gym, hangout space, or future in-law/rental suite. The expansive driveway isn’t just practical—it’s a place for riding bikes & shooting hoops while providing abundant parking for multiple vehicles, boats, or an RV. The real star of the show. Step outside and imagine the possibilities: a large, flat, fully fenced sodded backyard where pets can run freely, birthday parties come to life, and summer evenings are spent under the open sky. With no trees to limit your vision and a custom drainage system already in place, it’s truly a blank canvas for your dream outdoor space. Located in the sought-after Cloverfield’s community on one of the best roads in the neighborhood, low HOA fees and incredible amenities—pool days, beach outings, playground adventures, and a true sense of neighborhood connection. Even better, you’re just a short walk or bike ride to Love Point, Historic Stevensville, and Kent Island High School, with Route 50 minutes away for an easy commute.This isn’t just a house—it’s where your next chapter begins.

726 Davol Rd, Stevensville

Listing courtesy of RE/MAX Executive. Contact:

Selling Office: Coldwell Banker Realty.

331 Kidwell Ave, Centreville
$549,000
5 Beds ⋅ 3 Baths
Welcome to 331 Kidwell Avenue, a stunning colonial in the heart of Historic Centreville, Maryland, where timeless architecture meets modern comfort. Built in 1891, this beautifully updated home sits on a rare half-acre lot and offers over 2,700 square feet across four levels, all with NO HOA. The home’s exterior has been freshly painted, enhancing its classic curb appeal while preserving the character that makes historic homes so special. From the moment you step inside, you’re welcomed by a grand foyer highlighted by 10-foot ceilings, detailed custom trim work, and original hardwood floors that showcase the home’s historic charm. The updated kitchen features modern appliances, abundant built-in storage, and generous pantry space, making it both functional and inviting. Just off the kitchen is a sun-filled formal dining room and a spacious living area framed by beautiful custom trim, perfect for entertaining or everyday living. A half bath and mudroom complete the main level. Upstairs, elegant railings lead to the second floor where you’ll find four large bedrooms, a full hallway bathroom, and a convenient laundry area. The entire third level is dedicated to the primary suite, creating a private retreat with a massive walk-in closet, built-in storage, and an impressive ensuite bath featuring a stand-alone soaking tub, tiled shower, drying area, and vaulted ceilings. The lower level basement offers excellent storage space and houses the sump pump and updated HVAC systems. Step outside through the mudroom to enjoy the partially fenced backyard with mature trees and a beautiful flagstone patio, perfect for relaxing or entertaining. The property also includes a detached garage, a paved basketball court, and additional fenced yard space ideal for gardening or outdoor activities. Located within walking distance to Centreville High School, Centreville Middle School, and Kennard Elementary, this home also offers easy access to shopping, dining, the Queenstown Outlets, and major Eastern Shore destinations including Annapolis, Easton, St. Michaels, Kent Island, and the Delaware beaches. Historic charm. Modern updates. Space that’s nearly impossible to find in downtown Centreville. All that’s missing… is you.

331 Kidwell Ave, Centreville

Listing courtesy of RE/MAX Executive. Contact:

Selling Office: Brick and Quill Realty.

515 Bayside Dr, Stevensville
$546,000
5 Beds ⋅ 3 Baths
Welcome Home! Not all 5-bedroom homes are created equal—this one actually gives you the space you’ve been looking for. Every bedroom is surprisingly large, making this home stand out in a market full of tight layouts. A main-level bedroom offers added convenience, while the upstairs primary suite delivers a comfortable retreat with a walk-in closet and private bath. With two fireplaces and a layout that just feels easy to live in, this home is ready for its next chapter. And then there’s Bay City—a community people specifically love for water access, and that laid-back Eastern Shore feel… without giving up convenience to Annapolis and beyond. ✨ Move-in ready. Spacious where it counts. Property has a long driveway so that you can keep your boat right at home. Great location with easy access to parks, boat ramp and neighborhood pavilion. Easy access to Route 50, marinas, and local parks and trail- just across from Mowbray Park with sports fields, large playground equipment and updated pickle ball courts- perfect for the whole family!

515 Bayside Dr, Stevensville

Listing courtesy of Douglas Realty LLC. Contact:

Selling Office: Unrepresented.

101 Chestnut Ln, Queenstown
$545,000
5 Beds ⋅ 4 Baths
Enjoy the opportunity to create your own Eastern Shore retreat on 2 private acres surrounded by picturesque farmland. Conveniently located just a short drive from St. Michaels, Kent Island, and the Queenstown Premium Outlets, this spacious contemporary ranch home offers over 3,300 square feet of living space and exceptional potential. Priced accordingly, the property is being sold AS-IS and will benefit from repairs, updates, and cosmetic improvements, presenting an excellent opportunity for investors, renovators, or buyers looking to personalize a home to their tastes. With its desirable Eastern Shore location, substantial square footage, acreage and versatile outbuildings, this property offers the chance to create something truly special. The home features a flexible floor plan with a floor to ceiling stone fireplace in the family room, cathedral ceilings in family room, kitchen and primary bedroom, separate dining room, and eat-in kitchen with island. The previous owners' 2007 addition included 2 additional bedrooms and a full bath taking this home to a 5 Bedroom - 3.5 bath home and also converted the attached garage into a Rec Room all permitted with QA's County (see MLS docs). Outside, the property offers a variety of amenities ready for your TLC, including an in-ground pool (opened 2025 season pool pump is not operational), deck, a 30’ x 50’ pole barn built in 2020, and storage shed. The expansive grounds provide plenty of room for gardening, recreation, hobbies, or simply enjoying the peaceful rural setting and open views of the surrounding countryside. Bring your vision and discover the possibilities this unique country property has to offer.

101 Chestnut Ln, Queenstown

Listing courtesy of Cummings & Co. Realtors. Contact:

Selling Office: Samson Properties.

108 Meadowcroft Dr, Centreville
$545,000
4 Beds ⋅ 3 Baths
Here's is your chance to make it yours before someone else does! Welcome to 108 Meadowcroft Drive, Centreville Located in the highly sought-after NorthBrook community, this beautifully maintained home offers the perfect blend of space and comfort. Featuring 4 bedrooms, 2.5 baths, and over 3,200 square feet of living space, it sits on an oversized .28-acre lot with no homes directly behind. This is not your standard NorthBrook lot! Step inside to a thoughtfully designed main level with room for both everyday living and entertaining. You’ll find a formal living room and dining room, along with a warm and inviting family room anchored by a propane fireplace—perfect for cozy evenings. The open-concept kitchen flows seamlessly into the main living areas, while a dedicated study/den offers the ideal space for working from home or a quiet retreat. Upstairs, the spacious primary suite is a true escape, complete with a private sitting room, a well-appointed en-suite bath, and an oversized walk-in closet. Three additional generously sized bedrooms and a full bath provide ample space for family or guests. The upper-level laundry room adds everyday convenience. Enjoy outdoor living at its best with a charming covered front porch—perfect for morning coffee—and a large 16.5’ x 25.5’ rear deck ideal for entertaining or relaxing. A 10’ x 16’ shed offers additional storage for tools and outdoor essentials. Recent updates include a brand-new roof (2026) and a main-level furnace (2022), giving you added peace of mind. Located in the desirable North Brook community—featuring a playground, soccer field, pavilion, and scenic walking trails—this home is just minutes from Historic Centreville, the Centreville Wharf & Public Landing, parks, and local restaurants. Enjoy the charm of small-town living with the convenience of a quick 25-minute drive to the Bay Bridge. Spacious and move-in ready—108 Meadowcroft Drive is ready to welcome you home.

108 Meadowcroft Dr, Centreville

Listing courtesy of Compass. Contact:

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

422 N Brook Dr, Centreville
$545,000
4 Beds ⋅ 4 Baths
Not your typical North Brook home… and once you walk in, you’ll see exactly why. Nothing ordinary. Nothing plain. And absolutely not like any other North Brook home. From the moment you walk in, it’s clear this home was designed to stand out. Rich hardwood floors, upgraded designer lighting, and custom trim throughout create a polished, elevated feel that sets the tone for the entire home. The stunning kitchen is truly the heart of the home, featuring crisp white cabinetry, gorgeous countertops, upgraded appliances, and an open layout that flows seamlessly into the spacious living areas — perfect for entertaining or everyday living with style. Retreat to the gorgeous primary suite where thoughtful upgrades continue. Enjoy a spa-inspired bathroom with upgraded tile, double vanity, soaking tub, and a separate stand-up shower, plus a massive walk-in closet that delivers the space everyone wants. The fully finished basement expands your living space even more with recessed lighting and a convenient walk-up to the backyard — ideal for a rec room, home gym, guest suite, or all of the above. Perfectly tucked toward the back of the community, this home offers added privacy while still giving you full access to North Brook’s sought-after amenities, including walking paths, scenic ponds, playground, soccer field, and community pavilion. This is the one that stands out. This is the one that feels different. This is North Brook, but elevated. If you’ve been waiting for a North Brook home that truly stands apart, this is it.

422 N Brook Dr, Centreville

Listing courtesy of RE/MAX Executive. Contact:

Selling Office: Coldwell Banker Realty.

558 Cross Creek Ct, Chester
$542,500
4 Beds ⋅ 3 Baths
Nestled in a highly desirable community, this stunning home offers over 2,500 sqft of spacious living on a large, wooded lot, ensuring privacy and tranquility. Move right into this freshly painted haven, featuring four generous bedrooms, including a luxurious primary suite with a massive walk-in closet and a spa-like ensuite bathroom—complete with a Jacuzzi tub and separate shower. Main Level Highlights: ** Brand-new Luxury Vinyl Tile (LVT) flooring **Eat-in kitchen with ample space for gatherings ** Cozy family room with a gas fireplace **Bonus room, perfect for an office or playroom** Formal living and dining rooms for elegant entertaining **Convenient half bath and laundry room Outdoor Oasis: **Extra-large screened-in porch—ideal for relaxing or hosting **Private driveway leading to an attached 2-car garage

558 Cross Creek Ct, Chester

Listing courtesy of NetRealtyNow.com, LLC. Contact:

Selling Office: TTR Sotheby's International Realty.

272 Granny Branch Rd, Church Hill
$542,000
5 Beds ⋅ 4 Baths
Fantastic Opportunity! Experience the very best of country living in this spacious 5-bedroom home—with the potential for a 6th bedroom or office on the lower level! Enjoy sweeping views of farmland and open countryside, and start your mornings to the sound of a rooster crowing. This beautiful property sits on a full acre backing to farmland and includes: **An oversized 2-car garage **A large screened rear porch and expansive deck, perfect for entertaining or relaxing **A huge, eat-in country kitchen with plenty of space for family gatherings **Gas and Electric heating and a flexible floor plan to suit your needs Upstairs, a large playroom currently serves as a combined bedroom and recreation area—ideal as a playroom, library, in-home office, or studio. *** Come discover the charm, space, and tranquility this home has to offer!

272 Granny Branch Rd, Church Hill

Listing courtesy of Coldwell Banker Realty. Contact:

Selling Office: EXP Realty, LLC.

808 Cloverfields Dr, Stevensville
$540,000
4 Beds ⋅ 3 Baths
Welcome to 808 Cloverfields Drive! This gorgeous colonial sits on a double lot, has been meticulously maintained and is ready for its new owner! As you enter you're greeted by the formal living room to the right, and formal dining space to the left. The main level features a beautifully updated kitchen and open concept family room perfect for entertaining. A sprawling oversized deck off the kitchen can be enjoyed during all seasons. The backyard of your dreams awaits, with plenty of space for your gardens, activities and more. The two car garage has been recently refinished with speckled concrete. As you make your way upstairs, you'll find 4 bedrooms and 2 full baths, including the primary ensuite with a walk in closet, soaking tub and walk in shower. New roof in 2020 and new HVAC in 2023! Crawlspace encapsulated in 2016 w/ sump pump and dehumidifier. The desirable community of Cloverfields features a community pool that gives you all the Sandlot feels, community playgrounds, beach access, a boat launch and marina slips available. You can also take advantage of the community clubhouse for any of your entertainment needs.

808 Cloverfields Dr, Stevensville

Listing courtesy of Coldwell Banker Realty. Contact:

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

114 Addison Ct, Chester
$540,000
3 Beds ⋅ 3 Baths
Warm, comfy and ready to go! Might be the best way to describe the feel of this lovely 3 bedroom, 2-1/2 bath home in the terrific and convenient Claybourne Woods community. The "new" includes a brand new roof, kitchen cabinets, granite kitchen counters, kitchen sink and faucet, wood floors downstairs and main level carpeting. The rest of the home is move-in ready and was just professionally cleaned. The main bedroom suite is on the first floor and opens into the great room with its soaring ceilings and large windows. Just off the great room is a large multipurpose room that would make a nice home theater, home office or home gym! The new kitchen connects to the dining area and opens onto an enormous screen porch and deck- perfect for outdoor entertaining!! The remaining two bedrooms and full bath are at the top of a dramatic stairway. One of the best lots in the community. Come check out this beauty before it gets snapped up! Quick access to all shopping , restaurants and schools.

114 Addison Ct, Chester

Listing courtesy of Coldwell Banker Waterman Realty. Contact:

Selling Office: Coldwell Banker Waterman Realty.

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