Refine Search
Map
Sort by
$629,900
3 Beds ⋅ 2 Baths
Gorgeous house on River Rd in the Queen Anne's County side of Chestertown. 3 total bedrooms and 2.5 baths. The main bedroom is on the first floor. Stunning sun room, patio and pool. 2 car garage. Living room and den.

201 River Rd, Chestertown

Listing courtesy of Coldwell Banker Chesapeake Real Estate Company. Contact:

$445,000
2 Beds ⋅ 2 Baths
Nestled in the award-winning Symphony Village Active Adult 55+ community, this beautifully maintained contemporary home offers the perfect balance of comfort, functionality, and space for both everyday living and entertaining. Designed for convenient main-level living, this move-in ready home features a spacious primary suite with dual walk-in closets and an en-suite bath complete with a soaking tub. A second bedroom, full bath, and versatile den/library provide ample space for guests or hobbies. The thoughtfully designed floor plan also includes a formal living room, dining room, laundry room with utility sink, and dedicated office/workstation area. At the heart of the home, the eat-in kitchen also offers bar seating and opens seamlessly to the inviting family room with a cozy gas fireplace, creating an ideal gathering space. Step outside to enjoy exceptional outdoor living beneath a motorized retractable awning overlooking a beautifully designed, lighted 11x39 paver patio—perfect for dining al fresco, entertaining friends, or simply relaxing in a peaceful setting. The attached two-car garage includes an additional refrigerator and storage closet. Recent updates include a newer HVAC system for added peace of mind. Residents of Symphony Village enjoy an impressive array of resort-style amenities, including indoor and outdoor swimming pools, a fitness center, clubhouse, game room, tennis and pickleball courts, bocce courts, a putting green, scenic walking trails, picnic areas, and a vibrant calendar of social activities, clubs, classes, and community events. Ideally located just minutes from downtown Centreville, you'll enjoy easy access to local restaurants, waterfront recreation and boating on the Chesapeake Bay, as well as nearby Chestertown, Easton, and Annapolis. Maryland and Delaware beaches are also within a convenient drive, making this an exceptional place to call home.

251 Opera Ct, Centreville

Listing courtesy of Keller Williams Flagship. Contact:

$650,000
3 Beds ⋅ 3 Baths
Contemporary home in Prospect Bay offering approximately 2,850 square feet of living space and available for the first time since 1999. Features 3 bedrooms, including 2 on the main level, and 2.5 baths. The family room includes a fireplace and triple sliders leading to the deck. Spacious primary suite. Loft overlooking the family room, ideal for a home office, sitting area, or additional living space. Separate dining room and dedicated mudroom with laundry. Complete with a 2-car garage and deck overlooking the backyard. Located in Prospect Bay Golf and Country Club. Club amenities include: golf, a swimming pool, boat ramp, tennis courts and a clubhouse with restaurant.

24 Fairway Is, Grasonville

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

$510,000
3 Beds ⋅ 2 Baths
This amazing home on a gorgeous perimeter lot located within easy walking distance of the clubhouse will delight. A welcoming front porch greets you, and beyond that a spacious foyer with a convenient coat closet and a view of the entire living area, which is designed to optimize the space for an open airy layout. Remodeled kitchen with quartz countertops, custom added glass-fronted island cabinets, newer stainless appliances, timed up-lighting over the cabinets - these are just the beginning of the many upgrades in this home. The primary bedroom has new blinds and a ceiling fan, two large closets, a linen closet and neutral cozy carpeting. The en suite bathroom has quartz countertops, new flooring, new mirrors and lights, plus a completely rebuilt shower with a treated door for easy care. The guest bedroom has a ceiling fan, carpeted floor and a sizable closet. The hall bathroom has an upgraded vanity, new lights and mirror. The light-filled third bedroom makes a great office and has a deep closet for storage. The main living area flooring is American Cherry engineered hardwood, and the custom window shutters provide energy efficient elegance. The three-sided propane fireplace is operated with the flip of a switch. Crown molding is installed throughout the house. Large storage cabinets in the garage convey. The pièce de résistance is the back garden. Many trees, perennial plantings, an awning to keep you cool, large patio, and an overall atmosphere of peace and quiet will surround you. The HVAC system has been replaced, in addition to all the appliances, and the roof is one year old. The Symphony Village community is well established, with mature trees throughout, and an impressive clubhouse with many amenities, including a concert hall for the many events organized by the various committees. The main gathering area is bright and welcoming, and is the location for semi-monthly social hours where you bring a dish to share and get to meet your neighbors. Several groups with varied interests meet in the clubhouse on a regular basis, and you might walk through the clubhouse and see folks learning to paint in the craft room, others playing pool, some playing mahjong in the concert hall, or committee meetings to keep things humming along. You can walk outside to the covered patio area and the pool beyond, where residents enjoy holiday picnics, quiet evening time, and fun with the kids during the day. The indoor pool is open every day from early morning until late at night, and you can show up for water aerobics every weekday morning at 9:00A.M. Currently there are Spanish classes offered, in addition to soul line dancing, and at any time you can learn how to play bridge or hand and foot, so there is plenty to keep everyone busy. However, there is no requirement to participate in any activities, and you can live a quiet life in Symphony Village enjoying retirement or still working. There are many areas to walk in around the neighborhood, and in the clubhouse grounds is a pergola to sit and  watch the world go by, a kids' playground, a picnic area, bocce, a putting green (and active league) and a trail leading to Dunkin' Donuts and the shopping center just minutes away.

169 Symphony Way, Centreville

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

$624,900
4 Beds ⋅ 3 Baths
Perfectly situated on the scenic Eastern Shore of Maryland, just outside the historic town of Centreville, this stunning traditional home in the desirable Hollingsworth community offers an unparalleled lifestyle that combines suburban convenience with small-town charm. Located just 30 minutes from the William Preston Memorial (Chesapeake Bay) Bridge, this property provides an easy commute to Annapolis and the Western Shore, while keeping you just 35 minutes from historic Chestertown, 40 minutes from Easton, and a quick 40-to-45-minute drive to the Delaware line. Centreville itself is steeped in American heritage, serving as the Queen Anne's County seat since the 18th century and boasting the oldest courthouse in continuous use in Maryland, complete with the famous bronze statue of Queen Anne. With 2,909 square feet of thoughtfully designed, move-in-ready living space, this residence seamlessly blends timeless architectural appeal with modern features. Step inside to find a warm and inviting atmosphere, accentuated by beautiful custom built-ins and elegant recessed lighting that enhances the home's spaciousness. The open-concept main living area features a cozy gas fireplace, perfect for chilly evenings, while rich wood floors add a touch of timeless sophistication throughout. The seamless flow connects the living room to the dining area, making this open layout an entertainer's dream. The heart of the home is the well-appointed kitchen, fully equipped with modern appliances, including a built-in microwave, dishwasher, electric oven/range, and refrigerator—designed for both everyday functionality and style. This spacious home boasts four generous bedrooms, providing ample space for relaxation, privacy, or a dedicated home office. The master suite is a true retreat, featuring a private en-suite bathroom that combines convenience with comfort. With two full bathrooms and an additional half bath, morning routines will be a breeze for everyone. Step outside to enjoy the expansive 1.25-acre lot, a rare find on the Eastern Shore where outdoor living truly comes to life. The classic wrap-around porch and private patio areas invite you to unwind and soak in the serene surroundings, making it the perfect setting for summer barbecues, crabbing feasts, or quiet evenings under the stars. Located in the peaceful Hollingsworth neighborhood, residents benefit from a quiet community atmosphere just minutes from the Corsica River waterfront, local boat ramps, and vibrant downtown spots like local craft breweries and distilleries. Enjoy nearby parks with recreational opportunities for all ages, as well as access to top-rated Queen Anne's County schools that prioritize education and community involvement. Complete with a side-entry attached garage and an oversized driveway with ample parking space, this property is more than just a place to live—it's an Eastern Shore lifestyle. Don't miss the opportunity to tour this beautiful 4-bedroom home on acreage and experience all that Centreville has to offer!

246 Upland Ln, Centreville

Listing courtesy of Realty Navigator. Contact: 4106433404
$334,900
2 Beds ⋅ 1 Baths
Welcome home to this charming two-bedroom cottage in the water-privileged community of Kent Island Estates, where affordability meets coastal charm! Enjoy a relaxed lifestyle with nearby water access, community amenities, and all the comforts of a cozy home. Featuring beautiful Pine and Red Oak flooring, a cozy pellet stove, and a custom-milled barn door (BR), this home is full of warmth and character. Step outside to an inviting outdoor living space with a fenced backyard, spacious patio and two storage sheds for extra storage. A rare opportunity to own an affordable slice of waterfront community living, whether you're seeking a full-time residence, weekend getaway, or investment property. Outdoor enthusiasts will appreciate being just steps from the South Island Trail, a scenic 7-mile trail stretching from Matapeake State Park to the Romancoke Fishing Pier, offering endless opportunities for walking, running, and biking. Conveniently located just minutes from Blue Heron Golf Course, waterfront dining, marinas, and all that Kent Island has to offer. Paid members of Kent Island Estates enjoy access to two private waterfront parks and a community beach along the Chesapeake Bay, perfect for soaking in stunning sunsets, fishing, kayaking, or simply embracing the waterfront lifestyle. Kent Island Estates has a Voluntary HOA $30/year and Beach/Recreation Fee $40/year. Mandatory Fee is $10 /Year for Roads Maintenance Don't miss your chance to enjoy the best of Eastern Shore living at an exceptional value!

103 Oregon Rd, Stevensville

Listing courtesy of Rosendale Realty. Contact: 4107580333
$1,395,000
5 Beds ⋅ 4 Baths
Set along the peaceful shores of Chews Creek, this beautifully renovated waterfront home delivers the quintessential Eastern Shore lifestyle, where spectacular sunsets, endless water views, and effortless indoor-outdoor living take center stage. Thoughtfully updated throughout, the home offers five bedrooms and four full baths with a layout designed for both comfortable everyday living and exceptional entertaining. Hardwood floors flow throughout the main level, while abundant natural light and an open floor plan create a bright, inviting atmosphere. At the heart of the home, the gourmet kitchen features a large center island, Silestone countertops, Sub-Zero refrigerator, Viking gas cooktop, Miele built-in espresso maker, beverage refrigerator, nugget ice maker, stainless steel appliances, and ample space for gathering with all your guests. The kitchen opens seamlessly to the living and entertaining spaces, all oriented to capture beautiful water views. The main level offers tremendous versatility with a first-floor bedroom, dedicated office space, formal dining room accented by designer wallpaper, and an elegant living room with fireplace. A spacious waterside family room provides the perfect setting to relax, entertain, and enjoy the ever-changing waterfront scenery. Upstairs, the waterside primary suite serves as a private retreat overlooking the creek. Additional guest accommodations include generously sized bedrooms and a large bunk room ideal for hosting family and friends. Beautifully renovated baths feature custom tile work, dual vanities, and oversized walk-in showers. Outdoor living is equally impressive. A large waterside deck overlooks the heated and cooled salt-water swimming pool, creating a resort-like setting for summer gatherings. The outdoor amenities also feature a private outdoor spa/hot tub for year-round enjoyment. Professionally landscaped grounds, mature plantings, and multiple outdoor entertaining areas enhance the property’s relaxed waterfront lifestyle. Additional highlights include a detached two-car garage with an additional office space/bonus room,, roof less than ten years old, updated finishes throughout, and a setting that showcases some of the most breathtaking sunset views on Maryland’s Eastern Shore. Whether enjoying a quiet evening by the pool, entertaining guests on the deck, or watching the sun disappear over the water, this exceptional waterfront property offers a rare opportunity to experience Kent Island living at its finest.

115 Nw Creek Dr, Stevensville

Listing courtesy of TTR Sotheby's International Realty. Contact: (410) 280-5600
$7,995,000
8 Beds ⋅ 10 Baths
Set on 20 private waterfront acres with over 800 feet of shoreline along the Chesapeake Bay, this extraordinary estate offers a rare opportunity to own one of Maryland’s most impressive legacy properties. Behind a gated entrance and winding tree-lined drive, the residence combines timeless architecture, exceptional craftsmanship, and resort-inspired amenities designed for both grand entertaining and everyday enjoyment. The shoreline is simply remarkable, featuring riprap protection, a private pier with lifts, sandy beach areas, water and electric service, and panoramic Bay views that deliver spectacular sunsets year-round. Whether enjoying a quiet morning by the water, setting out for a day on the Bay, or gathering with family and friends for an evening by the fire, every aspect of the property has been thoughtfully designed to embrace the waterfront lifestyle. Inside, over 15,000 square feet of finished living space showcases Brazilian cherry flooring, handcrafted millwork, coffered ceilings, custom paneling, seven fireplaces, and beautifully curated living spaces throughout. The gourmet kitchen serves as the heart of the home, featuring premium appliances, an oversized island, sunlit breakfast room, and a fully equipped butler’s pantry designed for seamless entertaining. The residence offers two luxurious primary suites, including a main-level retreat with fireplace, spa-inspired bath, private office, and direct access to the waterfront. Multiple ensuite guest bedrooms, a theater room, game room, exercise suite, expansive third-floor recreation space, and a private apartment above the garage provide exceptional flexibility for hosting family and guests. Outdoor amenities rival those of a private resort. Enjoy a saltwater pool and spa, covered poolside entertaining pavilion with outdoor kitchen and fireplace, regulation tennis and pickleball court, expansive patios and terraces, fire pit, pond with fountain, playground, and extensive professional landscaping that creates a setting of complete privacy and tranquility. This is more than a home—it is a Chesapeake Bay estate designed for generations to gather, celebrate, and create lasting memories. A rare offering where luxury, privacy, recreation, and waterfront living come together on an extraordinary scale.

7328 Kent Point Rd, Stevensville

Listing courtesy of TTR Sotheby's International Realty. Contact: (410) 280-5600
$595,000
2 Beds ⋅ 3 Baths
Beautiful fourth-floor condo offering nearly 2,000 square feet of living space, featuring two bedrooms, a home office, two full baths, and a half bath. Enjoy morning sun from the oversized porch, a spacious living room, and an open-concept layout designed for comfort and entertainment. Highlights include luxury flooring, a fireplace, and a beautifully appointed kitchen with an oversized center island and quartz countertops stainless steel appliances and much more. This unit also includes a one-car garage and private storage space. The community offers unparalleled amenities and gorgeous water views, creating the perfect Chesapeake Bay lifestyle. Enjoy walking trails, outdoor tennis courts, indoor and outdoor pools, and a 23,000-square-foot clubhouse with outdoor spaces, a ballroom, test kitchen, outdoor bar, and community pier, views of the Chester River.

1000 Herons Nest Way Unit #43, Chester

Listing courtesy of Coldwell Banker Realty. Contact: kelly.thompson@cbmove.com
$399,500
3 Beds ⋅ 2 Baths
Welcome to 2645 Cox Neck Road, a move-in ready home in the desirable Harbor View Community of Chester. Offering 3 bedrooms, 1.5 baths, and situated on a spacious .34-acre lot, this well-maintained property combines comfort, convenience, and exceptional value at $399,500. Inside, you'll find a bright and inviting floor plan featuring a kitchen with a stylish tile backsplash, ample cabinetry, and luxury vinyl plank flooring. Thoughtfully maintained and updated over the years, this home offers peace of mind with a roof replaced within the last five years, replacement windows, siding, storm doors, and sliding glass door, as well as a recently replaced well pressure tank. Fresh interior paint and included appliances, including the washer and dryer, make moving in easy. Outdoor living is equally appealing with a charming front patio perfect for morning coffee and a large rear patio ideal for entertaining, grilling, or relaxing with family and friends. The beautifully maintained yard offers plenty of space for gardening, outdoor activities, or simply enjoying the outdoors. Two storage sheds provide ample room for tools, lawn equipment, and recreational gear. Located just minutes from Kent Island's popular restaurants, shopping, marinas, parks, and the Cross Island Trail, this home offers convenient access to everything the Eastern Shore lifestyle has to offer. Commuters will appreciate being less than 10 minutes from the Chesapeake Bay Bridge, while Harbor View residents enjoy a strong sense of community with neighborhood gatherings, holiday celebrations, yard sales, and other neighborhood events throughout the year. Whether you're searching for your first home, looking to downsize, or seeking a move-in ready property in a convenient Kent Island location, 2645 Cox Neck Road is an opportunity you won't want to miss.

2645 Cox Neck Rd, Chester

Listing courtesy of Compass. Contact: (410) 429-7425
$999,000
4 Beds ⋅ 3 Baths
Farm Compound., with three homes! Each home is independent with separate addresses, all on 48 acres. The lands include woods and a pond. The primary home is 2800 square feet just recently remodeled. Open concept living all the rooms are very spacious with a kitchen with tons of storage and lots of counter space. There is an office space as well so many options to use as additional bedrooms or hobby room. A laundry area that is a room not a closet. The HVAC system was just replaced on the main home, as many other features of this house. Number two house was just put on the property in 2025, Clayton Holmes three bedrooms two baths would make a wonderful in-laws house or a rental. Number three house sits to the back of the property again is its own separate structure, is a remodled single wide. Would make an excellent income, Property or a caretaker residence. This property offers so many options it’s unlimited. It also includes a 30 x 50 insulated pole barn with a concrete floor electric separate meter and pitcher pump. Two pasture areas exist with shelter for live stock they currently have goats. This is a absolutly one of a kind property if you want to have a Equine center lots of room to build a indoor arena or to raise livestock. The entire family can live here and have there own house. Would be an excellent Equine center good pastures building could be converted to stalls. The current owners have greatly improved the property it is now waiting for the next care takers to see what they do with this special property and its new use.

420 Duhamel Corner Rd, Marydel

Listing courtesy of Benson & Mangold, LLC.. Contact: (410) 479-0777
$1,350,000
5 Beds ⋅ 2 Baths
The locals called it Keister's Folly. In the mid-1940s, Dr. Keister built a barn on Kent Island overlooking Cox Creek, hoping to raise Black Angus cattle on 25 acres. The acreage was too small for the endeavor — but the barn he built was extraordinary. In the early 1960s, the developer of the Harbor View community converted it into a residence. The current owners' family purchased it in 1965 and has invested over $400,000 in improvements across sixty years of devoted stewardship. This property has never been publicly offered for sale — until now. Situated on 1.65 acres with 205 feet of protected waterfront on Cox Creek, this is one of the largest privately held waterfront parcels remaining in Harbor View. The 75-foot private pier extends into navigable tidal water with approximately 3.5 feet at mean low tide and two boat slips. Shoreline reinforced with professional rip-rap. Maps show Flood Zone X — outside 100-year and 500-year floodplains - buyer and agent should verify. The home offers 3,456 sq ft of living space across two levels including 700+ sq ft of unfinished second and third-level expansion space. Five bedrooms, two full baths. The upper-level primary suite features hardwood floors, panoramic water views, attached full bath, walk-in closet, private coffee bar with refrigerator, and a deck overlooking the creek. Updated kitchen with granite countertops, upgraded cabinetry, and high-end appliances, improvements throughout honor the building's barn heritage. Solid block construction. 200-amp electrical. Well water, public sewer. New Roof will be installed prior to settlement. Ideal for those who are seeking genuine Chesapeake waterfront with privacy, deep water access, and a property unlike anything else on the market. Be sure to download the Home Profile in the documents section for more details on the home including the history of the home.

2513 Cecil Dr, Chester

Listing courtesy of Real Broker, LLC - Chester. Contact: 8554500442
$579,900
5 Beds ⋅ 3 Baths
Open house this Sunday, June 28th 1:30pm-3pm! Please join us!! Five bedrooms, move-in ready condition, a hot tub, and an incredible Eastern Shore location—all for under $600,000!! Experience the best of Maryland’s Eastern Shore lifestyle in this beautifully maintained 5-bedroom home, perfectly situated in a quiet cul-de-sac just minutes from the water. Whether you’re launching the boat for a day on the Chesapeake, exploring nearby trails, grabbing coffee at the beloved Dessert First Dockside Coffee, or enjoying fresh local seafood at one of the area’s waterfront restaurants, you’ll love having it all right at your fingertips. Inside, you’ll immediately appreciate how exceptionally well cared for this home is, it feels almost new!!! Fresh updates include brand-new carpet and newly painted living spaces, creating a clean, bright, move-in ready feel throughout. The spacious kitchen features updated countertops, propane cooking, and an island that opens to the heart of the home. Gather around the cozy pellet stove in the family room or retreat to the versatile third-floor bonus space, perfect as a 5th bedroom, home office, playroom, guest suite, or whatever fits your lifestyle. Step outside to your own private retreat, complete with a spacious patio and hot tub ideal for relaxing or entertaining. Private driveway with additional overflow and guest parking available!!! With generous living space, thoughtful updates, and an unbeatable location just minutes from marinas, boat ramps, waterfront dining, and the Bay Bridge, this home delivers everything buyers love about Eastern Shore living, without sacrificing convenience. You won't want to miss this one!

125 Fawn Ln, Grasonville

Listing courtesy of Coldwell Banker Realty. Contact: 4102638686
$699,500
5 Beds ⋅ 4 Baths
Welcome to 216 Brix Dr. — Where Modern Luxury Meets Eastern Shore Charm Prepare to be impressed by this beautifully renovated 5-bedroom, 3.5-bath home in the sought-after community of Church Hill. Thoughtfully updated from top to bottom, this exceptional residence offers generous living space, stylish finishes, and the peaceful lifestyle the Eastern Shore is known for. Step inside to discover a bright, open interior featuring brand-new luxury vinyl plank flooring throughout the main level, plush new carpeting upstairs, and fresh paint throughout, creating a crisp, contemporary feel that's completely move-in ready. At the heart of the home, the stunning gourmet kitchen is designed to impress, boasting brand-new stainless steel appliances, an oversized center island, abundant cabinetry, and expansive counter space—perfect for entertaining, hosting holidays, or everyday living. A rare and highly desirable feature, this home offers two spacious primary suites—one on the main level and another upstairs—providing incredible flexibility for multi-generational living, extended guests, or a private owner's retreat. Outside, enjoy the convenience of an oversized three-car garage, a blacktop driveway, and a peaceful backyard backing to mature woods, creating a private setting for relaxing evenings, outdoor gatherings, or simply enjoying nature. Beyond the home itself, residents enjoy access to community walking trails and water access, allowing you to fully embrace the outdoor lifestyle and scenic beauty that make the Eastern Shore so desirable. Ideally located, this home is approximately 10 minutes from the historic waterfront towns of Centreville and Chestertown, where you'll enjoy charming boutiques, locally owned restaurants, marinas, waterfront parks, and year-round community events. Combining modern updates, spacious living, desirable community amenities, and an unbeatable location, this exceptional property offers the very best of Eastern Shore living. Don't miss your opportunity to make this stunning home your own—schedule your private tour today!

216 Brix Dr, Church Hill

Listing courtesy of CR Realty. Contact: 4104900460
$569,000
4 Beds ⋅ 3 Baths
Absolutely Charming Eastern Shore Home with Beautiful Farm Views! Experience the peaceful charm of Queenstown living in this beautifully updated home situated on a gorgeous .83 acre lot surrounded by the natural beauty of Maryland’s Eastern Shore. Enjoy the slower pace of life with open farmland views, plenty of outdoor space, and a setting that feels away from the congestion while still being convenient to nearby shopping, restaurants, waterfront areas, and commuter routes. The welcoming front porch is the perfect place to relax and take in the scenic farm views, while the screened porch overlooking the backyard provides another wonderful space to enjoy the outdoors. Inside, this home is full of warmth and character with luxury vinyl plank flooring throughout the main level and thoughtful updates throughout. The upgraded kitchen features white cabinetry, stainless steel appliances, and a convenient laundry room nearby. The inviting family room offers a cozy wood burning fireplace, creating a comfortable gathering space. A main level office with a beautiful French door entry offers flexibility and could also serve as an additional bedroom, guest space, or hobby room. Upstairs, you will find three spacious bedrooms with fresh carpeting, including the impressive primary suite featuring a large ensuite bathroom, walk-in shower, dual sink vanity, and generous closet space. The additional bathrooms have also been beautifully updated. With abundant parking, nearly an acre of land, peaceful surroundings, and views that capture the best of Eastern Shore living, this Queenstown charmer is truly a special place to call home.

223 Overlook Dr, Queenstown

Listing courtesy of Douglas Realty LLC. Contact: (410) 255-3690
$335,000
4 Beds ⋅ 2 Baths
Some homes simply have a feeling you can't recreate, and this is one of them. Rich in character and timeless craftsmanship, this beautifully maintained home blends historic charm with thoughtful updates, creating a warm and inviting place you'll love coming home to. Original hardwood floors, glass doorknobs, skeleton keys, classic swinging doors, and elegant architectural details tell the story of a home built to stand the test of time, while an updated bathroom and refreshed kitchen provide the comforts of everyday living. Designed with both gathering and quiet moments in mind, the spacious layout offers generously sized rooms filled with natural light. The oversized screened porch is the perfect extension of the home, inviting you to enjoy morning coffee, evening conversations, or simply unwind while overlooking the expansive backyard with plenty of room for gardening, entertaining, pets, or play. A full unfinished basement offers abundant storage and room for future possibilities. Located in the heart of Church Hill, this is more than just a house. It's an opportunity to own a home filled with warmth, history, and character that's becoming increasingly difficult to find.

104 Walnut St, Church Hill

Listing courtesy of RE/MAX Executive. Contact: 4432741900
$469,900
4 Beds ⋅ 2 Baths
Welcome home! This spacious 4 bedroom, 2 full bath home of over 2,000 sq ft is located on a quiet, dead end road in a serenely wooded area of the community. Enjoy the tranquility of your backyard on the brand new deck with vinyl rails and steps to grade. Under the deck, there is a patio for a second outdoor entertaining area. Along the rear of the property, you will find a massive 32'x28' concrete slab where a detached outbuilding once stood and could be rebuilt!!! It also functions as a 3rd area of seating or outdoor living space with plenty of versatility! A short walk down the road, the South Island Trail intersects. You can head south to enjoy the wide open water of the Eastern Bay from the Romancoke Fishing Pier where you can fish and crab til your heart's content. Or you can head north and visit the Nemo Equestrian Trail or Blue Heron Golf Course. There are over 7 miles of trails accessible a short walk from this home's front door! Now saving the best for last, the home has had nearly all the hard work done for you! It features newer siding (2025), windows, roof (50 yr shingles with transferrable warranty), HVAC (2024), 80 gallon high efficieny water heater (with heat pump), flooring, paint, bathrooms, and last but not least; a gorgeous kitchen renovation that competes with houses worth twice as much as this home! The spacious floor plan is open on the kitchen level with a large dining area or potential family room off the kitchen. This area naturally flows to the back deck mentioned before. Back inside however, there is another large vesatile gathering space below the kitchen which gives the home multiple communal living spaces on separate floors. This allows for plentiful options and lets everyone spread out. The bathrooms have been generously renovated for your enjoyment. A spacious laundry/mud room is located on the entry level. This property is a great blend of indoor and outdoor living space that is tough to beat at this price point! Call today to come visit this home and see it for yourself firsthand!

121 Margaret Dr, Stevensville

Listing courtesy of Coldwell Banker Waterman Realty. Contact: (410) 643-5005
$649,000
3 Beds ⋅ 1 Baths
Welcome to your dream coastal retreat in the highly sought-after Chester River Beach community of Grasonville, Maryland. This beautiful, luxurious bayside property is a single-story rancher that offers the perfect blend of modern upgrades, breathtaking views of the Bay and relaxed coastal living in a vibrant and lively neighborhood that is perfect for boating enthusiasts, crabbing, and fishing. This fully remodeled three bedroom, one full bath home sits on one of the largest corner lots and has been thoughtfully updated from top to bottom with high end finishes and brand new systems throughout. Enjoy peace of mind with newly installed roof, vinyl siding, flooring, central air conditioning system with heat pump, new well tank, and water heater. Next on the list is a completely renovated bathroom featuring a state of the art smart bidet toilet with heated seat, and automated micro bubble cleansing technology bringing spa like comfort to your everyday routine. After enjoying the beach, boating, fishing or swimming, relax in the spacious brand new shower. Gorgeous coastal style kitchen designed with two spacious islands, providing ample prep space, including breakfast bar seating perfect for entertaining family and guests. Amenties showcasing high end cabinetry, ceramic tile backsplash, wall mounted retractable pot filler, smart appliances including flat top range, stainless double door refrigerator, double oven, and farm sink sink as well as other highend features! The home also includes convenient laundry with a new washer and dryer, offering everyday ease and functionality. Enjoy breathtaking water views filling the space with natural light and creating a serene coastal atmosphere through two newly installed bay windows. Additional features include a cozy working fireplace, sliding patio door leading to a newly constructed deck with additional views of the bay, off-street parking, and a spacious detached garage equipped with electrical service. The home also includes a full, easily accessible attic, providing plenty of storage and potential to include additional living space! The property includes access to private boat docks, boat ramps, and private managed beach just a few steps away. Residents also enjoy a community park, entertainment pavilion with stunning waterfront views, along with convenient access to nearby shopping malls, restaurants, and grocery stores. Boat directly to many waterfront bars and boating restaurants making every day feel like a vacation. Whether you're looking for a full-time residence or a weekend getaway, this move-in-ready Chester River Beach home delivers the very best of Eastern Shore bay-front living.

801 Chester River Dr, Grasonville

Listing courtesy of HomeZu by Simple Choice. Contact: (855) 885-4663
$609,900
4 Beds ⋅ 3 Baths
**Price Improvement** OVER 5 ACRES. NO HOA. JUST MINUTES FROM US301. That’s a combination that’s becoming increasingly difficult to find. Welcome to 913 Clark Corners Rd, where 5.42 ACRES of partially wooded land offer the freedom to live your way! Whether you’re dreaming of horses, chickens, gardening, recreational activities, frequent sightings of deer, birds, owls, and other wildlife, or simply room to breathe, this property delivers the space and flexibility today’s buyers are searching for. Inside, you’ll find a thoughtfully updated home featuring a fully renovated kitchen with quartz countertops, 42” soft-close white cabinetry, stainless steel appliances, recessed lighting, a large center island with seating, and luxury vinyl plank flooring that flows seamlessly into the spacious family room with a gas fireplace. The main level also boasts engineered hardwood floors and offers formal living and dining rooms, an updated powder room, and a renovated laundry/mud room with additional cabinetry, countertop workspace, and valuable pantry storage. Upstairs, the spacious primary suite includes a walk-in closet and private bath, while three additional bedrooms and a full hall bath provide room for family, guests, hobbies, or a home office. Outside, enjoy a welcoming wraparound front porch that’s perfect for relaxing and taking in the peaceful surroundings, along with a rear deck, partially fenced backyard, large storage shed, mature landscaping, permanent Govee front exterior lighting, and a blend of open yard and wooded acreage that creates a setting rarely found at this price point. Above the garage, the unfinished attic space provides exceptional storage and potential future possibilities, subject to buyer verification of county requirements and approvals. Whether you’re looking for room to grow, room to roam, or simply room to breathe, this property delivers. To make this opportunity even more appealing, sellers are offering a 2-YEAR HOME WARRANTY (up to $2,000) with an acceptable offer—adding extra peace of mind to a property that already offers space, flexibility, and freedom.

913 Clark Corners Rd, Centreville

Listing courtesy of Coldwell Banker Waterman Realty. Contact: (410) 643-5005
$649,900
4 Beds ⋅ 3 Baths
Seller is offering buyer incentives! With an acceptable offer, the seller is willing to contribute toward an interest rate buy-down or other closing cost assistance—helping make homeownership more affordable in today's market. Now offered at $649,900, this beautifully maintained, energy-efficient home presents an exceptional value on 1.37 unrestricted acres just minutes from Centreville. Featuring 42 owned (not leased) solar panels, private well and septic, unrestricted acreage free of HOA and CC&R restrictions, and the added benefit of county living just outside the Centreville town limits, this property offers the privacy, flexibility, and lower monthly ownership costs today's buyers are searching for. Offering over 2,600 square feet of living space, the home features a spacious family room with propane fireplace, a bright kitchen with stainless steel appliances and tile backsplash, formal and informal living areas, mudroom, laundry room, and half bath. Upstairs, the primary suite includes a walk-in closet and en-suite bath, while three additional bedrooms, a full bath, and a large bonus room provide flexible space for a home office, gym, media room, or guest accommodations. Enjoy peaceful Eastern Shore living from the welcoming front porch or maintenance-free rear deck overlooking your private backyard. Recent improvements include an encapsulated crawl space (2026), fresh interior paint (2026), repaved driveway (2026), updated kitchen appliances (2025-2026), new heat pump (2024), new well pump and expansion tank (2024), Thompson Creek replacement windows (2021), updated sliding glass door (2021), and a whole-house water filtration system with reverse osmosis. Conveniently located near Historic Centreville, shopping, dining, parks, the Centreville Wharf & Public Landing, and just a short drive to the Bay Bridge, this property offers a rare combination of acreage, privacy, energy efficiency, and convenience in desirable Queen Anne's County.

988 White Marsh Rd, Centreville

Listing courtesy of Compass. Contact: (410) 429-7425
$97,500
6.11 wooded acres in the country! Loaded with wildlife! Large secluded pond. Surrounded by large track of woods. Hunters Dream!

1031 Peters Corner Rd, Sudlersville

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

$589,000
1 Beds ⋅ 2 Baths
The luxury of living here is not in the square footage. It is in the untouched beauty of the river and constant exposure to nature. A charming oasis on the Chester River with 3 outbuildings all with the most amazing view. Magnificent plantings around the property. A duck blind for hunting. Private dock with lift. Historical ferry road is yours! The house was completely renovated in 2011. It's all so charming and extremely well kept. Roughly a quarter mile of waterfront. BAT septic system only approved for 1 bedroom. You cannot expand the house.

114 Front St, Crumpton

Listing courtesy of Coldwell Banker Chesapeake Real Estate Company. Contact:

$1,700,000
7 Beds ⋅ 6 Baths
Set on more than six private acres in one of Kent Island’s most desirable locations, this exceptional estate offers a rare blend of luxury, scale, and refined livability. Encompassing approximately 5,680 square feet, the residence has been thoughtfully elevated through extensive improvements, resulting in a truly turnkey offering in a setting defined by privacy, presence, and the freedom of no HOA restrictions, including the ability to keep livestock. At the heart of the home, a spectacular chef’s kitchen sets the tone for both everyday living and elevated entertaining. Custom cabinetry frames a suite of premium Viking and Miele appliances, complemented by an oversized refrigerator and freezer, multiple ovens, dual dishwashers, beverage refrigeration, a dedicated ice maker, and a walk-in pantry. This is a space designed to perform just as well for quiet evenings as it does for large gatherings. A soaring two-story family room anchors the main level, filled with natural light and centered around a newly installed pellet stove insert. The main-level primary suite serves as a private retreat, featuring a fully reimagined spa-inspired bath with a steam shower, soaking tub, and bespoke cabinetry. Across three finished levels, seven bedrooms provide remarkable flexibility for multi-generational living, guests, home offices, or creative pursuits. Throughout the home, refreshed interiors, custom built-ins, and thoughtful updates contribute to a cohesive sense of comfort and refinement. Outdoors, the property unfolds like a private resort. An expansive patio, gazebo, curated landscaping, and swimming pool create an effortless setting for entertaining or quiet relaxation. The surrounding acreage enhances the sense of seclusion, with space for recreation, gardening, livestock, or simply enjoying the quiet rhythm of estate living. The detached two-story garage extends the property’s versatility, with a dedicated fitness studio above and generous space below for vehicles, equipment, hobbies, or future expansion. What truly distinguishes the property is the quiet confidence of what has already been accomplished. Comprehensive improvements to core systems and infrastructure ensure a level of reliability and peace of mind rarely found in homes of this scale, allowing the next owner to simply arrive and enjoy. Despite its private and pastoral setting, the estate remains just minutes from Route 50, providing convenient access to Annapolis, Baltimore, Washington, D.C., and the Eastern Shore. Positioned near the highly regarded Matapeake school campus, it offers a rare combination of seclusion, accessibility, and everyday convenience. Rarely does a property combine acreage, scale, and refinement in such a complete way. This is more than a home. It is a private Kent Island estate designed for living well, entertaining effortlessly, and enjoying space without compromise.

102 Little Neck Rd, Stevensville

Listing courtesy of HomeSource Pro Real Estate. Contact: (443) 454-1470
$549,900
3 Beds ⋅ 2 Baths
Coming soon — brand new construction opportunity! This thoughtfully designed ranch-style home will be breaking ground soon and offers the chance to secure a brand-new home before construction begins. Featuring convenient one-level living, this home will include an open floor plan with vaulted ceilings and quality finishes throughout. The kitchen is planned to feature quartz countertops, stainless steel appliances, a center island, and ample cabinet space, opening to the spacious living and dining areas—ideal for everyday living and entertaining. The primary suite is designed as a private retreat with a spacious bedroom, walk-in closet, and ensuite bath featuring a double vanity and oversized shower. Additional bedrooms provide flexibility for guests, family, or a home office. Other highlights include a dedicated laundry room, generous storage, and an attached 2-car garage. Situated on a spacious lot, buyers may have the opportunity to make selections depending on the stage of construction. Get in early and make this upcoming new construction home yours before it’s built!

Baltimore Dr, Stevensville

Listing courtesy of Coldwell Banker Waterman Realty. Contact: (410) 643-5005
$750,000
4 Beds ⋅ 4 Baths
335 S. Carolina Rd is ready for its 2nd owner! Enjoy sprawling views of the Chesapeake Bay from every level. Only 3 years young, this home is beautifully appointed and move in ready. As you enter, the first floor opens to a living space with a slider that leads to your lush green back yard. There is also a full bathroom and bedroom. The second floor is where the magic is. Your living room with fireplace, kitchen and dining space are open for you to enjoy the spectacular water views from all angles. The third floor boasts 3 bedrooms and 2 full bathrooms including the waterside primary suite with its own private deck. Some special features include a bright open floor plan, balconies with water views, a gorgeous fire pit, and walkable to the Bay and beach. Also enjoy a widened driveway for extra parking spaces, a water softener system and storage shed. This home features 3 decks and a 2 car garage. Move in time to enjoy all that a beautiful Kent Island summer has to offer.

335 S Carolina Rd, Stevensville

Listing courtesy of Coldwell Banker Realty. Contact: kelly.thompson@cbmove.com
$650,000
3 Beds ⋅ 3 Baths
Have a fun-filled summer right in your own backyard! The heated pool is open and ready to enjoy, while the open-concept floor plan seamlessly connects the cozy great room, dining area, and updated kitchen, creating the perfect space for entertaining. Extensive & impressive thoughtful renovations. A wood-burning fireplace adds warmth on cool fall and winter evenings. A spacious bonus room with its own private side entrance offers endless possibilities, including a potential 4th bedroom or recreation room, while the upper-level loft provides even more flexible living space. The large rear shed has been thoughtfully divided into a climate-controlled office with year-round heating and air conditioning plus a separate storage area for lawn equipment, pool supplies, and outdoor gear. Recent updates include crisp white soft-close kitchen cabinets & glide shelves, Quartz countertops, refreshed bathrooms have new vanities with Quartz tops Kohler fixtures & beautiful shower tiles, Everlife luxury vinyl flooring through out. New siding, Architectural Roof/gutters & downspouts, fresh interior paint, recessed lighting throughout, new ceiling fans, and new window blinds. Primary Bedroom with on-suite bath & custom closet system. Step outside to a fenced backyard featuring a patio shaded by a sun sail, perfect for relaxing or entertaining. Located just one short block from community open space along the Chesapeake Bay, you'll enjoy easy access to a playground, pavilion, and boat ramp & kayak launch. Whether you're enjoying the pool in summer or gathering around the fireplace in winter, this home is ready to be enjoyed year-round.

508 Paul Dr, Stevensville

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

$565,900
2 Beds ⋅ 3 Baths
Nestled in the charming community of Gibsons Grant, this exquisite townhouse offers a luxurious lifestyle with a perfect blend of comfort and elegance. Built in 2009, this Colonial-style residence spans 2,048 square feet and features two spacious bedrooms , with a another room that could be used for a 3rd bedroom and two and a half bathrooms, making it an ideal retreat for those seeking both style and functionality. Step inside to discover a thoughtfully designed interior that boasts hardwood and pine flooring, creating a warm and inviting atmosphere throughout. The combination kitchen and dining area is perfect for entertaining, featuring ample space for gatherings and culinary creations. Natural light floods the home, enhancing the inviting ambiance and highlighting the quality craftsmanship that defines this property. One year old HVAC and four year old hot water heater. The outdoor spaces are equally impressive, with a charming deck and porch that invite you to relax and enjoy the serene surroundings. Imagine sipping your morning coffee while taking in the gentle sounds of nature or hosting evening gatherings under the stars. The community pool and recreational facilities provide additional opportunities for leisure and relaxation, ensuring that every day feels like a vacation. Located just blocks from the Chester River, this property offers water-oriented living at its finest. Enjoy easy access to the river, perfect for kayaking or leisurely strolls along the waterfront. The community amenities, including a clubhouse, exercise room, and jogging paths, cater to an active lifestyle, while the meticulously maintained common grounds provide a picturesque backdrop for your daily activities. Parking is a breeze with a detached garage that offers additional storage space, ensuring that your home remains clutter-free. The association fee includes lawn care, snow removal, and trash services, allowing you to spend more time enjoying the luxurious lifestyle this community has to offer. Gibsons Grant is not just a place to live; it's a lifestyle choice that embraces the beauty of nature while providing modern conveniences. With its prime location, high-end features, and a strong sense of community, this townhouse is a rare gem that promises to be a cherished home for years to come. Experience the perfect blend of luxury and comfort in this stunning property, where every detail has been designed with your enjoyment in mind.

115 Gibson Cir, Chester

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

$2,000,000
5 Beds ⋅ 4 Baths
The waterfront dream home you've been waiting for... the one everyone else will wish they had bought first. This quintessential Kent Island waterfront estate captures everything buyers love about Eastern Shore living. Perfectly positioned on 1.99 private acres just minutes from the Bay Bridge, this exceptional property offers over 3300 SF in main house, and another 450 SF+/- guest space w/ full bath atop detached garage! Designed for effortless waterfront living and entertaining. The main residence features 5 bedrooms and 4 full baths, including a desirable main-level bedroom and full bath, while the detached two-car garage is topped by a private guest suite and full bath—ideal for visitors, extended family, or a private home office retreat. Step outside and discover the lifestyle you've been dreaming about. A private pier, sparkling waterfront pool, expansive covered porch, and beautiful Ipe decking create a resort-like setting where every day feels like a vacation. Southern Eastern Bay views provide the perfect backdrop for boating adventures, summer gatherings, quiet mornings with coffee, and unforgettable sunsets. This is more than a home—it's a waterfront destination. A place where memories are made, boats are launched, friends linger longer, and every season brings a new reason to fall in love with life on the water. Extremely well-maintained with polished updates, to include: Anderson windows (2024 & 2020), refreshed dock & boat lift (8K lb capacity), Additional pilings for guest boat tie-up. Whole-house generator w/1000 Gallon OWNED tank, tankless water heater, fully encapsulated crawlspace, Sub-zero refrigerator & Wolf gas stove, Pool pumps, filter (2020-2023) & new liner (2024). One look and you'll understand why there is nothing like this beauty on market!

252 Eareckson Ln, Stevensville

Listing courtesy of Chaney Homes, LLC. Contact: (410) 739-0242
$650,000
3 Beds ⋅ 3 Baths
Welcome to Ellendale—where modern comfort meets Eastern Shore charm. This beautifully maintained 3-bedroom, 2 full and 1 half bath home, built in 2018 by Baldwin Homes, offers the feel of new construction with a spacious, light-filled layout, a desirable first-floor primary suite, and a 2-car garage. Designed for both everyday living and effortless entertaining, the home features stylish finishes throughout, along with two added Mitsubishi mini-split systems for enhanced comfort and energy efficiency. Step outside to enjoy the fully fenced backyard and stone patio, creating the ideal setting for outdoor dining, gatherings, or quiet mornings with a cup of coffee. An in-ground lawn sprinkler system helps keep the yard lush and beautifully maintained with ease throughout the seasons. Nestled in the sought-after Ellendale community in Stevensville on Kent Island, you're just minutes from waterfront dining, boutique shopping, and the attractions of Kent Narrows. With convenient access to Route 50 and an easy commute to Annapolis, this home offers the perfect blend of comfort, convenience, and coastal living.

128 Allison Jane Dr, Stevensville

Listing courtesy of Mr. Lister Realty. Contact: (410) 486-5478
$599,000
3 Beds ⋅ 2 Baths
Enjoy carefree WATERFRONT living in this Beautifully UPDATED Condo in the sought-after Oyster Cove Community! Offering 3 bedrooms and 2 full bathrooms, this light-filled, one-level residence features an open floor plan designed for easy living and entertaining! Stunning wide plank wood flooring flows throughout the main living areas, complemented by newer stone countertops, fresh interior custom paint throughout and NEW carpet in the bedrooms. The spacious living and dining areas open to a Waterfront Deck where you can relax and enjoy breathtaking Sunsets over Eastern Bay and The Narrows. The thoughtfully designed layout offers generous bedroom sizes and two updated baths. Recent exterior improvements include new siding and new windows. Oyster Cove residents enjoy an exceptional Waterfront lifestyle with access to two Marinas, Swimming Pool, two Tennis Courts, a walking/jogging path and a Clubhouse with a fitness room. Conveniently located within walking distance to many restaurants, coffee spots, ice cream parlors, shops and popular dock bars!! Hop on the Kent Island Cross Trail for a bike ride throughout the Island! Just minutes from the Chesapeake Bay Bridge, this is Eastern Shore living at its finest!

116 Oyster Cove Dr Unit #1D, Grasonville

Listing courtesy of RE/MAX Executive. Contact: 4432741900