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$449,000
3 Beds ⋅ 2 Baths
Fantastic Eastern Bay waterview from this wonderful Kent Island, 3 bedroom, 1.5 bathroom Ranch/Rambler in Romancoke on the Bay, with a near half acre. This cute home will surprise you with how spacious it is on the inside! Stepping in the front door, you'll notice the LVP flooring throughout the entire space. The front living area is quiet and cozy and faces the Eastern Bay water view! The open kitchen has stainless steel appliances and opens to the spacious dining room. Off the dining room you'll find the fantastic great room, perfect for large gatherings and plenty of cozy furniture. The sliders in the great room lead to a covered deck and patio centered on the fully fenced backyard. A stone pathway leads to a shed with electric. Back inside, down the hall from the kitchen is the remodeled full bath and the 3 bedrooms, two of which connect to a half bath. The property also offers an oversized attached single car garage, a fully encapsulated crawlspace, fresh paint throughout, established sunny raised garden beds, beautifully green spacious back yard (one side is fully treelined) and a circle driveway out front providing plenty of parking. Last but not least, the wide-open water view visible from the living room and two bedrooms! Romancoke on the Bay has wonderful amenities, including a Community Center that hosts regular events and can be rented out, a Boat Ramp, a Pier, a Beach and a Tot-Lot, all located right at the end of Allegany Rd. The Romancoke Pier is just up the street and so is the start of the South Island Trail which runs for miles through the trees and fields of Southern Kent Island. A list of updates follows. Don't miss this one! It is a perfect gem on Kent Island! Crawlspace encapsulated 2025, New sump pump 2025, New well pump 2026, New roof 2013, New HVAC 2013, SKI Sewer connected, New hot water heater 2016, New appliances 2016, Full bathroom renovation 2017

202 Allegany Rd, Stevensville

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

$998,000
3 Beds ⋅ 3 Baths
Welcome to this stunning 4th floor penthouse Severn condominium with serene bay views! This end unit looks out over the walking trails to the water and trees. The fabulous community center /pool / pier is a short 1 mile walk from your backyard.! This unit also has the largest garage space in the the building, plenty of room for one car and storage, a refrigerator etc. There is also an additional inside storage room. This 2600 Sq Ft home is flooded with natural light and has numerous quality upgrades including custom shiplap in most of the rooms, custom ceiling fans and dining room light fixture, custom built his and hers walk in closets. The primary bath has upgraded tile, shelving for more storage, mulitple shower heads and back and front lit vanity mirrors. The gourmet kitchen is designed to impress, featuring elegant quartz countertops,premium appliances and a Wolfe induction cooktop. The island has been upgraded with shiplap as well. Thoughtful upgrades continue throughout the entire home with custom blinds with remote control, a gas fireplace,9 FT ceilings with tray ceilings in the living room and primary suite. A wet bar has also been added to the dining area.The large primary bedroom comes complete with a sitting area/office with exceptional waterviews. It also offers custom designed his -and -her closets that provide both style and storage. This unique residence offers a peaceful setting where you can relax and enjoy the ever-changing waterfront vistas. Whether you are enjoying your morning coffee or entertaining guests, this home offers the perfect blend of sophistication, comfort, and low maintenance waterfront living.

111 Marshgrass Way Unit #41, Chester

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

$1,500,000
4 Beds ⋅ 3 Baths
Waterfront on the Corsica River—opportunities like this don't come along every day! Proudly positioned on a spectacular 2-acre lot with approximately 540 feet of shoreline, this exceptional 4-bedroom, 3-bath home offers breathtaking panoramic views and an unmatched waterfront lifestyle. Located at the end of a quiet cul-de-sac in the established community of Corsica Landing Estates, just outside Centreville town limits, you'll enjoy the benefits of no town taxes or HOA fees. Mature landscaping and thoughtfully designed hardscaping create a private setting that perfectly complements the expansive river views. Designed for entertaining, the backyard is truly a waterfront oasis. Enjoy the in-ground concrete pool with diving board, a spacious hot tub housed in its own versatile room for year-round enjoyment, and a 145-foot private dock with approximately 6 feet of mean low water, complete with electric, water, two boat lifts, and a floating dock. Whether you prefer relaxing in the sun or unwinding in the shade, the beautifully landscaped outdoor living spaces have something for everyone, including an expansive 47.5' x 18' Trex deck with two pergola-like covered cooking and dining areas and a spacious waterside patio. Inside, the home offers comfortable living with generous spaces throughout. The eat-in kitchen features granite countertops, stainless steel appliances, including a new oversized refrigerator, and a separate wet bar with wine refrigerator and wine rack. The main level also includes a spacious living room with a wood-burning fireplace, an oversized formal dining room, a home office with custom built-ins and a large bay window, a full bath, and a convenient laundry/mudroom. One of the home's standout features is the incredible waterside sunroom, filled with natural light from walls of windows and offering spectacular views of the pool and river. Complete with a beautiful stone propane fireplace and ceiling fans, it's the perfect place to relax in every season. The spacious primary suite includes hardwood flooring, a walk-in closet, dual vanities, a walk-in shower, and direct access to a large 18.5' x 24' bonus room above the garage. With its own private staircase from the attached two-car garage, this flexible space is ideal for a guest suite, recreation room, fitness area, studio, or additional home office. Next to the garage is an attached exterior storage/utility room which provides even more convenience. THE FINISHED LIVING AREA SQUARE FOOTAGE FOR THIS HOME IS LARGER THAN THE ASSESSMENT OFFICE REPRESENTS AND THE GOOGLE SATELLITE IMAGE MAP DOES NOT REFLECT ALL OF THE PROPERTY. PLEASE SEE DEEDS AND MAPS ATTACHED IN THE DOCUMENTS. Numerous updates have been completed over the years, including the HVAC system and ductwork, roof, triple-pane windows and sunroom doors with a lifetime warranty. The pool was renovated in 2016, with a new pool pump and skimmer pipe installed in 2023 and a new pool motor in 2026. The well pump was replaced and lowered in 2007, offering additional peace of mind. Whether you're searching for a full-time waterfront residence, the ultimate family gathering place, or a home designed for entertaining, this remarkable property delivers. With boating, fishing, kayaking, swimming, and unforgettable sunsets right from your backyard—and a county boat ramp, playground, and pavilion just minutes away—there's still plenty of summer left to enjoy. Schedule your private tour today and experience everything this extraordinary Corsica River property has to offer. Located within an hour to Baltimore, Washington, DC or Delaware. Stay Tuned For Professional Photos Coming Soon !

405 Quail Run Dr, Centreville

Listing courtesy of Benson & Mangold, LLC. Contact: (443) 988-0483
$60,000
Vacant lot ready for your own choice of residence. Walking distance to the Chester River community access by boat or just enjoy the waterfront on the community deck.

233 Merganser Dr, Chestertown

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

$199,900
3 Beds ⋅ 2 Baths
Nestled along the water's edge, this waterfront opportunity offers a canvas to create your own Eastern Shore retreat. Whether you choose to renovate the existing 3BR cottage or build on the existing foundation there is plenty of potential. Buyer to confirm building restrictions with the county. This property features a new deep well, new well pump, and new septic holding tanks in 2026. The existing interior of the home has been taken down to the framing and includes 100-amp electrical service, providing a solid starting point for your vision. Outdoor enthusiasts will enjoy everything this property has to offer. Fish for perch, bass, catfish, and snakeheads, or spend the day crabbing from your shoreline. Waterfowl hunters will enjoy the existing duck blind, while everyone will appreciate the stunning sunsets overlooking the water. Whether you're looking for a peaceful weekend escape, a hunting and fishing camp, or the site of your future waterfront cottage, this property offers an opportunity that's becoming increasingly difficult to find.

220 Kirbys Landing Rd, Millington

Listing courtesy of Select Land & Homes, LLC. Contact: (410) 708-0956
$899,000
3 Beds ⋅ 3 Baths
Escape to your own private Eastern Shore sanctuary! Nestled on 15.39 acres in Stevensville, 225 Batts Neck Road offers the ultimate blend of coastal convenience and secluded mountain-getaway. This stunning 3BR/2.5BA post-and-beam cabin welcomes you with a classic wrap-around porch and a cozy interior featuring a wood-burning stove—complete with a second fireplace rough-in for the upstairs lofted primary suite. The expansive layout includes an amazing living room and game area designed for hosting memorable family gatherings. The 15+ acres are an outdoor enthusiast's dream, featuring established walking and ATV trails, along with cleared open areas perfect for camping and firepits. Whether you are looking for a premier hunting retreat, a weekend getaway, or a permanent homestead with the potential to build a second home, this unique acreage delivers. Enjoy the best of the Eastern Shore: less than 2 miles from Matapeake Beach, 2.5 miles from Kentmorr Marina, and 4 miles from Bay Bridge Marina. Best of all, you are just 4 miles from the Bay Bridge for a seamless commute to Annapolis, Baltimore, or DC!

225 Batts Neck Rd, Stevensville

Listing courtesy of Real Broker, LLC - Annapolis. Contact: 8554500442
$510,000
3 Beds ⋅ 2 Baths
Welcome to 103 Opera Court in the sought-after, active 55+ community of Symphony Village at Centerville. This expanded Vivaldi model features three bedrooms and two full bathrooms on an oversized corner lot across from parklands and with no home behind the paver patio. Pull up to your side loading garage and take the short path to the front door, with a quaint covered porch for slow evenings and watching nature go by. Once inside, the spacious foyer offers a dry bar with mini-fridge and architectural pillars lead to an open concept living space. You’re invited in by unobstructed views from the dining area through the living area into the family room extension with a vaulted ceiling and fireplace with marble surround. There is beautiful, engineered hardwood flooring throughout the public spaces. Unmatched natural light drenches the entire space which centers on the cozy gas fireplace for ease of use on the few chilly winter nights. The gourmet, open style kitchen features gorgeous cabinetry, granite countertops, stainless steel appliances, including double wall ovens that are sure to please any chef. The primary bedroom suite has brand new carpeting, a sitting area with vaulted ceiling, a tray ceiling above the bed for added drama, and double walk-in closets. The primary bath features separate vanities, a jetted soaking tub and a custom, walk-in tub. The second bedroom is down the hall from the entry and is adjacent to the second well-appointed full bath. The third bedroom, at the front of the home, is a perfect flex space and could be a bedroom, office, or studio. It also has wood floors and plenty of natural light. Tucked away at the center of the home is the laundry which is on the way to the two-car garage. The garage features a “sky basement” above, which is partially finished and can be used for storage. Outside the French doors in the family room is a paver patio, perfect for entertaining, dining alfresco or taking your morning coffee. For peace of mind and low utilities, this home also has solar panels and a whole house generator. The community takes care of the grounds, leaving you more time to relax and enjoy the peace and quiet and the many amenities! There are paths for walking or biking, including one leading to the local shopping center, pickleball and tennis courts, putting green, bocce ball courts and a resort style outdoor pool. The clubhouse features a concert hall, billiards room, fitness room, bar, party rooms, dining room, and an indoor heated pool open every day. Activities include classes to learn a variety of skills, social hour, arts and crafts, game and card nights, an artist guild with quarterly art shows and much more for the low HOA fee. The historic and charming town of Centerville is minutes away with wonderful restaurants and shops, and a wharf for boating, paddling or a picnic. Enjoy the slower pace of the eastern shore while remaining close to the ocean beaches and the city life across the Chesapeake Bay. This home has SO MANY UPGRADES and beautiful views – it’s a very special property.

103 Opera Ct, Centreville

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

$499,000
4 Beds ⋅ 3 Baths
NEW PRICE—An Unbelievable Value on Kent Island! Built in 2020, this gorgeous, like-new home offers approximately 1,974 square feet of beautifully maintained living space, a spacious yard backing to trees, and a desirable Kent Island location. An assumable VA loan at an attractive 2.75% interest rate may be available to qualified buyers, subject to lender and VA approval. Fresh interior paint and new carpeting throughout make this home truly move-in ready. The spacious living and dining areas provide plenty of room for everyday living and entertaining, while the inviting fireplace adds warmth and character. The kitchen features a breakfast bar, granite, pantry, abundant cabinetry, and generous storage. The spacious owner’s suite offers two walk-in closets and a private en-suite bath, creating a comfortable retreat. Step outside to enjoy the private backyard backing to trees, ideal for relaxing, entertaining, or enjoying peaceful evenings outdoors. Ccnvenient access to nearby boat ramps. Ideally located near shopping, dining, golf, pickleball, waterfront parks, walking trails, beaches, a dog beach, marinas, boat storage, Queenstown Premium Outlets, and popular local restaurants and entertainment. Experience the best of Kent Island living in this beautifully updated home. Some rooms have been virtually staged, including the owner’s suite, living room, and dining room.

124 Riverside Dr, Chester

Listing courtesy of Douglas Realty LLC. Contact: (866) 987-3937
$669,900
3 Beds ⋅ 2 Baths
Welcome to your private Eastern Shore oasis at 116 Mallard Drive, Stevensville, MD 21666! This beautifully maintained and recently updated Cape Cod home sits on a rare 1.1-acre lot in a quiet, private neighborhood on Kent Island — one of the hardest-to-find lot sizes in this desirable area. Enjoy serene, protected views of Mallard Pond, where you can watch ducks glide across the water, sip morning coffee on the screened porch, and truly experience peaceful Kent Island living at its finest. Boasting 1,976 square feet of above-grade living space (built in 2000), this 3-bedroom, 2-bath home features thoughtful updates throughout. Enjoy new LVP flooring and carpet, a bright open-concept main level perfect for everyday living and entertaining, and a stunning kitchen with granite countertops and all new appliances. The spacious primary suite includes a luxurious soaking tub and walk-in closet, while two additional bedrooms and a full bath complete the main level. A 2-car garage and newer furnace add convenience and peace of mind. The standout feature is the large unfinished attic with electrical wiring and HVAC already extended — substantial, flexible space ready for your vision. Easily finish into additional bedrooms, a home office, playroom, or family suite. Outside, the expansive 1.1-acre lot delivers exceptional privacy and natural beauty, bordered by community-owned preserved woodlands and Mallard Pond that ensure your views remain undisturbed for years to come. Enjoy the screened porch overlooking the pond, low-maintenance exterior, low HOA fees of only $17 per month, and the incredible location on Kent Island — walk or bike to the public golf course, Kent Island Trail, waterfront parks, piers, and just minutes from Chesapeake Bay adventures, shopping, and dining. This updated home combines solid construction, modern finishes, low monthly costs, and a truly rare 1.1-acre private setting. Whether you’re looking for a peaceful full-time residence or a lifestyle property with room to grow, 116 Mallard Drive is a standout opportunity on Kent Island. Don’t miss it!

116 Mallard Dr, Stevensville

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

$599,000
4 Beds ⋅ 3 Baths
Welcome to 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: 4432741900
$850,000
4 Beds ⋅ 3 Baths
Nestled within the serene enclave of Goose Point Estates, this exquisite one level living home offers a harmonious blend of luxury and comfort, perfect for those seeking an elevated lifestyle. This residence boasts a modern aesthetic while retaining its timeless charm. Step inside to discover a spacious 2,141 square feet of meticulously designed living space. The interior features a warm palette complemented by rich hardwood flooring and plush carpeting, creating an inviting atmosphere throughout. Crown moldings and chair railings add a touch of elegance, while recessed lighting and skylights bathe the space in natural light. The heart of the home is undoubtedly the gourmet kitchen, equipped with upgraded countertops and ample table space for casual dining. High-end appliances, including a self-cleaning oven, built-in microwave, and energy-efficient dishwasher, make cooking a delight. The adjacent family room, complete with a charming wood-burning fireplace, provides a perfect retreat for relaxation. This residence features four generously sized bedrooms, including a main-level bedroom for convenience. The luxurious master suite offers a walk-in closet and a spa-like bathroom with a stall shower included with a hot tub, ensuring a private oasis for unwinding after a long day. Outside, the property is equally impressive, set on a sprawling 2.4-acre lot surrounded by lush trees and serene woods, providing a tranquil backdrop for outdoor living. Enjoy evenings under the stars in the hot tub or host gatherings with friends in the beautifully landscaped yard. The exterior is adorned with thoughtful features such as bump-outs, exterior lighting, and flood lights, enhancing both functionality and aesthetics. Additional highlights include a spacious attached garage with extra storage, main-floor laundry for added convenience, and a water treatment system for peace of mind. This home is not just a residence; it's a lifestyle choice, offering a perfect blend of luxury, comfort, and nature. Experience the best of both worlds in this exceptional property, where modern amenities meet the tranquility of nature, creating a perfect sanctuary to call home. Goose Point Estates is just minutes away from route 50 and the Chesapeake Bay Bridge but far enough away from all the traffic.

121 Eareckson Ln, Stevensville

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

$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
$700,000
3 Beds ⋅ 3 Baths
Newly adjusted price. Rarely available, this luxurious Severn penthouse in Four Seasons at Kent Island offers the perfect blend of waterfront beauty, comfort, and resort-style living. Built in 2020 and meticulously maintained, the home features an open-concept design filled with natural light and stunning views of Macum Creek and the Chester River. The gourmet kitchen is the heart of the home, showcasing a large island, premium appliances, and picturesque water views. Three spacious bedrooms, two-and-a-half baths, and inviting living spaces provide comfort and flexibility for everyday living and entertaining. Enjoy spectacular sunrises, abundant wildlife, and peaceful water views from your private balcony. Just steps away, you'll find creekside trails, kayak launches, picnic areas, and direct access to the natural beauty that makes Kent Island so special. Located in desirable Phase One, this penthouse offers enhanced privacy, mature surroundings, and freedom from nearby construction. Additional features include an oversized attached garage with interior access and a secure storage room. Residents enjoy access to Four Seasons' exceptional amenities, including a 24,000-square-foot clubhouse, indoor and outdoor pools, fitness center, pickleball and tennis courts, fishing pier, kayak launches, dog parks, walking trails, tiki bar, and more.

2000 Herons Nest Way Unit #401, Chester

Listing courtesy of Real Broker, LLC. Contact: 8504500442
$362,500
2 Beds ⋅ 3 Baths
Welcome to 1302 Marion Quimby Dr. Nestled in the serene Thompson Creek community, this charming townhouse with a new HVAC and hot water heater offers a perfect blend of comfort and modern living. With 1,161 square feet of thoughtfully designed space, this home features two spacious bedrooms and two and a half bathrooms, making it an ideal retreat for those seeking tranquility and convenience. Step inside to discover an inviting open floor plan that seamlessly connects the living, dining, and kitchen areas. The contemporary design is enhanced by plush brand new carpeting and elegant ceramic tile flooring, creating a warm and welcoming atmosphere. The living room is anchored by a cozy fireplace, complete with glass doors and a stylish mantel, perfect for those chilly evenings spent at home. The kitchen is a culinary delight, featuring ample table space for casual dining and modern appliances, including a dishwasher, microwave, and electric oven/range. Whether you're preparing a gourmet meal or enjoying a quick breakfast, this kitchen is designed to meet your needs. Retreat to the primary suite, which boasts an en-suite bathroom for added privacy and convenience. Thoughtful window treatments throughout the home allow for natural light while maintaining a sense of intimacy. Step outside to enjoy the beautiful exterior features, including a charming balcony and deck over-looking Thompson Creek and gorgeous water views and sunsets, perfect for sipping your morning coffee or unwinding after a long day. The community amenities are a true highlight, offering access to a refreshing outdoor pool, tennis courts, and scenic jog/walk paths that wind through beautifully landscaped grounds. The property is situated on the banks of Thompson Creek, providing stunning views of the water, lush pastures, and surrounding trees. Imagine relaxing on your deck while listening to the gentle sounds of the creek, creating a peaceful oasis right at your doorstep. With unassigned off-street parking and a well-maintained community that includes exterior building maintenance, management, and trash services, this home offers both convenience and peace of mind. Experience the perfect blend of comfort, community, and natural beauty in this delightful townhouse. Whether you're looking for a weekend getaway or a permanent residence, this property is sure to meet your needs and exceed your expectations.

1302 Marion Quimby Dr, Stevensville

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

$4,995,000
5 Beds ⋅ 5 Baths
Architect-designed contemporary waterfront home on nearly 18 private acres across two parcels with approximately 1,400 feet of shoreline on Greenwood Creek. Positioned to capture 180-degree western views, the property offers privacy, deep water, and a setting that is increasingly difficult to find on Maryland’s Eastern Shore. A custom pivoting front door creates a striking first impression and sets the tone for the home's thoughtful design. The home was designed to take advantage of the surrounding water and landscape, with floor-to-ceiling windows, open gathering spaces, and strong indoor-outdoor connections throughout. The kitchen opens to the main living areas and features a glass accordion door that connects directly to the screened porch, creating a seamless transition between indoor and outdoor spaces. The layout flows easily between the kitchen, dining areas, family room, porch, and pool area, making the home equally well suited for everyday living and entertaining. The primary suite is set apart from the rest of the home by a glass-enclosed walkway and includes a private office, large dressing room, en-suite bath, and private porch access. In addition to the primary suite, the main level includes three additional bedrooms, each with access to a private bathroom. The finished lower level includes a home theater, billiards room, bar area, workout room, additional bedroom and full bathroom, along with unfinished basement space for storage. Outdoor features include a solar-heated pool, private beach, and deep-water pier with two boat lifts. The protected shoreline and direct access to Eastern Bay make this an ideal property for boating and waterfront living. A three-bay outbuilding with workshop space and additional storage provides room for equipment, hobbies, or car and boat storage. Located just outside Queenstown, the property is convenient to Easton, Annapolis, Washington D.C., Baltimore, and Philadelphia while offering the privacy and pace of the Eastern Shore.

2800 Bennett Point Rd, Queenstown

Listing courtesy of TTR Sotheby's International Realty. Contact: 4106733344
$599,900
3 Beds ⋅ 3 Baths
Recently Reduced and Ready for Its New Owner! Experience the best of Eastern Shore living at 1024 Avalon Court, where spacious design, natural light, and a peaceful setting come together beautifully. Perfectly positioned on a desirable lot with views of the community pond area and protected woodlands, this exceptional residence offers a wonderful blend of privacy, comfort, and everyday convenience. From the inviting exterior with stone accents and a two car garage to the open interior layout and exceptional outdoor living spaces, this home is designed for easy living and effortless entertaining. Step inside to a welcoming foyer with neutral paint and a bright, airy feel that continues throughout the main level. The thoughtfully designed floor plan offers excellent flexibility with formal living and dining areas, generous open gathering spaces, and seamless flow between rooms. Expansive windows bring in beautiful natural light while framing peaceful rear views, creating a warm and inviting atmosphere throughout the home. The heart of the home is the open concept kitchen and family room area, ideal for both everyday living and entertaining. The kitchen features abundant cabinetry, granite counters, stainless steel appliances, recessed lighting, a center island cooktop, and direct connection to the surrounding living spaces. The spacious family room offers a cozy fireplace and easy access to the private screened porch and large raised concrete patio, two standout features rarely found in this community. Both outdoor spaces overlook the community pond area and protected woodlands, creating a private and peaceful backdrop for relaxing, dining, and entertaining. The home continues with spacious bedrooms, including a large main level owner’s suite with generous closet space and a private bath featuring dual vanities, a soaking tub, and separate shower. This main level suite offers excellent flexibility for multigenerational living, guests, or those seeking everyday convenience. Additional bedrooms on the upper level provide comfortable space for family, guests, home office needs, hobbies, or recreation. Outdoor living is truly a highlight, with multiple areas to enjoy the serene wooded setting. The private screened porch is perfect for morning coffee, quiet evenings, or relaxing without the elements, while the oversized raised concrete patio offers wonderful space for grilling, entertaining, or simply enjoying the peaceful rear views. Additional highlights include flexible living spaces, a heated and air conditioned two car garage with amazing storage, and a peaceful rear setting rarely found in such a convenient location. Ideally positioned with easy access to major commuter routes including Routes 50 and 301, this exceptional residence offers convenient access to Downtown Annapolis, Washington, D.C., Baltimore, Kent Island, the Bay Bridge, Middletown, Dover, NSA, Fort Meade and Dover Air Force Base. Enjoy great local amenities including restaurants, shopping, recreation, and all the lifestyle conveniences that make the Eastern Shore so desirable. Don’t miss out on this incredible opportunity!

1024 Avalon Ct, Stevensville

Listing courtesy of Berkshire Hathaway HomeServices PenFed Realty. Contact:

$675,000
3 Beds ⋅ 3 Baths
High End & High Efficiency! Sustainable living meets timeless craftsmanship in this incredible custom-built Nexus home. If you’ve been dreaming of a property that blends luxury, efficiency, privacy, and intentional design… this is it. Situated on an acre with NO HOA, this craftsman-style beauty was thoughtfully designed for both comfort and energy efficiency with features rarely found together in one home: Owned Solar Panels Brand New Geothermal Heating System Electric Vehicle Charging Plug-Ins Hardiboard Plank Siding for durability and timeless curb appeal Inside, the details shine: ✨ Beautiful custom moldings ✨ Updated kitchen with high-end appliances & countertops ✨ Warm, elevated finishes throughout ✨ Spaces that feel both elegant and grounded Outside is where this home truly becomes a lifestyle: 🌿 Covered porches for slow mornings and evening unwinds 🔥 Hardscaped patios perfect for entertaining ⚽️ Wide open green space for gardening, soccer games, pets, or simply breathing a little deeper An almost net-zero home with privacy, style, and functionality like this is incredibly rare.

103 Beech Tree Ln, Centreville

Listing courtesy of Samson Properties. Contact: 7033788810
$548,000
3 Beds ⋅ 3 Baths
NOE: THIS HOME OFFERS OVER 3,630 Sq Ft of Finished Space including the Professionally Finished dWalkout Basement! This stunning home as been refreshed and is ready to be your retreat from the fast lane of life! You won’t find a home at Symphony Village with more desirable features than this spacious home backing to acres of preserved woodlands and paved walking trails. Come through the front door into the foyer... Step into a huge great room offering flexible living /dining/ entertaining space, a beautiful kitchen with breakfast bar that opens to a Morning room with cathedral ceilings and a grand arched palladian window overlooking the woods. You will enjoy relaxing in the spacious family room featuring a gas fireplace or step out to the fully finished 3-Season room and just enjoy watching nature bloom before your eyes. Also on the main level, you will find the primary bedroom with "His & Hers" walk-in closets and a spacious private bath with soaking tub and a walk-in shower as well as a 2nd Bedroom bedroom with another full bath. A large mud room/laundry room is conveniently located just inside entry from the garage. Only a relatively small number of homes in Symphony Village offer a full basement...this one offers a FULLY FINISHED FULL BASEMENT with a walkout exit to the private rear yard, and a custom Patio backing to acres of wooded open space and walk/jogging paths. The lower level includes a third bedroom, full bath, a hobby room, utility room PLUS an enormous Flex Room that is the perfect finished space for your theatre room, billiard room, party room, playroom or even your own ,private gym!Are you looking for plenty of storage? The "Sky Basement" on the upper floor provides plenty of additional storage and is also nicely finished. Oversized 2 car garage. This home is one of only a small number of homes featuring a full finished walk out basement! Symphony Village in Centreville, Maryland is a popular 55+ active adult community known for its clubhouse, indoor & outdoor pools, tennis/pickle ball courts, walking paths, fitness center, party room, beautiful community bar for gathering with friends and other social amenities. Come take a tour and you'll find your home!

107 Overture Way, Centreville

Listing courtesy of Chaney Homes, LLC. Contact: (410) 739-0242
$364,900
3 Beds ⋅ 3 Baths
Nestled in the heart of Kent Island, this charming 3 Bedroom, 2 Full Bathroom townhome with Bonus Room, offers the perfect blend of comfort, convenience, and peaceful surroundings. Located in the desirable Bridgepointe community, this home features major updates including a newer roof, HVAC system, and water heater providing peace of mind for years to come. Enjoy a private backyard setting that backs to mature trees, creating a serene outdoor retreat, while being just steps from the community lake, walking paths, and boat parking lot! Inside, the functional layout offers spacious living areas, comfortable bedrooms, and plenty of natural light throughout. Whether you're looking for a primary residence, weekend getaway, or low-maintenance lifestyle near the Chesapeake Bay, this Kent Island gem is ideally situated close to shopping, dining, marinas, and commuter routes. Schedule your tour today!

5011 Bridgepointe Dr, Chester

Listing courtesy of Keller Williams Realty Centre. Contact: 4103120000
$950,000
5 Beds ⋅ 5 Baths
WOW! This one is an absolute 11 on a scale of 1–10! Thoughtfully updated with stylish, on-trend finishes throughout, this property is truly exceptional from top to bottom. From the moment you step onto the covered front porch and into the dramatic two-story foyer, you’ll feel the difference. A private dining room sits to one side while two spacious main-level offices on the other make balancing work and home life effortless. And YES—high-speed internet is available through Talkie Fiber! At the heart of the home is a bright and beautiful gourmet kitchen featuring stainless steel appliances, a full refrigerator and full freezer, center island seating, and the kind of layout that naturally becomes the gathering place for everyone. The adjoining living room is warm and inviting, anchored by a fireplace and framed by oversized windows that flood the space with natural light while overlooking the picturesque backyard. Upstairs, you’ll find a magazine-worthy laundry room along with three spacious bedrooms and two beautifully updated full baths. The primary suite was designed to feel like a true personal retreat—complete with vaulted ceilings, a private deck overlooking the grounds, and plenty of natural light. Start your mornings with coffee in the fresh air or unwind at the end of the day under the stars. The luxurious ensuite bath features a soaking tub, separate shower, double vanity, and soaring ceilings that make the space feel spa-like. And just when you think it can’t get any better… there’s approximately 1,800 additional square feet of finished living space in the lower level! Complete with a private movie theater with seating for eight, bedroom, full bath, family room, kitchenette, and private entrance, the lower level offers incredible flexibility for guests, multi-generational living, or an in-law suite. Situated on nearly 1.5 acres surrounded by mature trees, this property offers the peaceful privacy of your own backyard oasis. The in-ground pool with landscaping, fire pit, multiple lounging areas, and glowing string lights create the perfect setting for entertaining family and friends all summer long. And tucked beyond it all? A beach volleyball court and horseshoe pit that make this property feel like your own private resort. PLUS: (As if all that wasn't enough) There is a whole house Generac to ensure you never lose power AND a 46,000 Enphase Solar (owned--no lease takeover!!) that saves BIG on electric and also returns Solar Renewable Energy Credits (SREC). Brand New Roof, too! Sound too good to be true? It’s not… unless you wait too long. This GEM is guaranteed to turn heads the moment it hits the market—so be ready!

218 Upland Ln, Centreville

Listing courtesy of Wilson Realty & Staging LLC. Contact: 4103042250
$689,900
4 Beds ⋅ 3 Baths
One of our most popular designs, the Doral offers formal and informal living areas with lots of room for the whole family to spread out. Your main level features a dining/den/flex space as well as a spacious family room and kitchen, breakfast area that flows to the spacious family room.. Add a light-filled morning room off the rear or expand your space with plan extensions. . Upstairs accommodates four nicely sized bedrooms, including aprimary suite with a massive closet area. Located just a short walk to the waterfront, the community features a boat launch, pavillion, playground, and bayfront recreational area.

114 Queens Colony High Rd, Stevensville

Listing courtesy of Keller Williams Flagship. Contact:

$135,000
Nestled in one of the most beautiful and peaceful areas of Queen Anne’s County, this serene wooded lot has already been perc approved and offers the perfect blend of privacy and convenience. The lot is surrounded by mature trees and feels secluded and tranquil while still being just 9 minutes from Historic Chestertown. Convenient access to Routes 213 and 544 makes travel to Centreville, Easton, and Middletown easy. Quotes are already available for septic installation, well installation, and clearing of the existing structure and brush.

109 2nd St, Chestertown

Listing courtesy of Cross Street Realtors LLC. Contact: 4434803453
$589,000
3 Beds ⋅ 3 Baths
Set on a splendid site backing to open space and woods, this dramatic Gershwin model with a solarium extension and loft will delight you. As you walk through the living and dining room and on to the kitchen and family room, the floor-to-ceiling stone fireplace in the solarium will  draw your eye, with a half round window high on the wall above. Several transom windows add to the natural light flowing into the house. An office opposite the living/dining room could become an additional bedroom, with easy access to the hall bathroom, or a hobby room, music or reading room. Rich hardwood flooring through the formal  area and kitchen, with carpeting in other areas and bedrooms. The gourmet kitchen has granite countertops, cherry cabinets, an electric cooktop and double oven plus microwave, large refrigerator and dishwasher. Several appliances have been replaced. The en suite primary bedroom has two closets, and the bathroom has a soaking tub, double vanity and a large shower with a seat. The guest bedroom is located in a separate hallway with an adjacent bathroom. On the upper floor is a second family room, bathroom and spacious bedroom with a large closet. Over the garage is the sky basement generally used for storage, with attic access. The custom patio overlooks the woods, and a feeling of serenity descends as you enjoy the view and the birdsong. 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.

106 Encore Ct, Centreville

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

$459,900
3 Beds ⋅ 2 Baths
*BACK ON THE MARKET - BUYER HOME SALE CONTINGENCY FELL THROUGH! Welcome to this beautifully renovated and remodeled 3-bedroom, 2-bath home offering the perfect blend of modern style, comfort, and location. Designed with today’s lifestyle in mind, this home features a bright open floor plan with spacious living and dining areas that flow seamlessly into the stunning gourmet kitchen. The kitchen is a true showstopper with elegant quartz countertops, a large center island, and ample space for cooking, gathering, and entertaining. Both full bathrooms have been tastefully updated with ceramic tile finishes and brand-new high-end vanities. The spacious primary suite offers a private retreat with its own en-suite bathroom for added comfort and convenience. Step outside to enjoy the level front and backyard spaces, ideal for outdoor entertaining, gardening, play, or simply relaxing. Located just one block from the Chesapeake Bay, you’ll love the nearby neighborhood waterfront park featuring picnic areas and fishing access. Conveniently situated for commuters, this home offers easy access to the Eastern Shore beaches, Washington, DC, and Baltimore—making it the perfect place to enjoy coastal living with city convenience. Don’t miss this exceptional opportunity!

109 Birch Rd, Stevensville

Listing courtesy of Five Star Real Estate. Contact:

$349,900
22.49 wooded acres on Romancoke Rd in Queen Anne’s County, MD, located 8 miles south of Stevensville. Features include mature pines, trail system, strong deer and turkey presence, and extensive road frontage thru two separate entrance pts. Close to Chesapeake Bay boat access and less than 8 miles to the Bay Bridge. Property has not been perc tested; all uses subject to buyer due diligence. Schedule an appointment for a private tour.

Romancoke Rd, Stevensville

Listing courtesy of Whitetail Properties Real Estate, LLC. Contact:

$485,000
2 Beds ⋅ 3 Baths
BACK on the MARKET. GREAT OPPORTUNITY at THIS PRICE. This Chester model has scenic, seasonal views of Macum Creek, beautiful sunrises, and an incredible display of wildlife in all seasons. Easy walk to Kayak launch and creek. With nearly 2000 square feet of open living space this home has a great layout for entertaining family and friends. The spacious great room, adjacent to the dining area and kitchen, provide an open area for gatherings. The gourmet kitchen is equipped with upgrades from the stunning kitchen island with quartz counter tops, beautiful upgraded cabinetry to the GE Profile appliances. This kitchen is designed for everyday living as well as hosting the occasional dinner party. The primary bedroom, is a separate self-contained suite complete with two closets and a luxury owners' bath that includes double sinks, and quartz countertops. The bright and airy 2nd bedroom is also a separate suite with a full bath and an oversized walk-in closet. In addition to the two bedrooms, there is a home office with stylish French Doors and a powder room for guests. The separate laundry room is equipped with a GE washer and dryer. This home also has a garage with adjoining driveway/parking space and large personal storage room which is a few short steps from the elevator. This home is just a short walk to resident kayak racks with launch access to the Chester River. KEEP IN MIND THIS CHESTER MODEL, WITH PLENTY OF FEATURES AND UPGRADES INCLUDED, IS MOVE-IN READY AND PRICED TO SELL***** Award-winning 24,000 Square Foot Clubhouse with Stunning Chester River Views! Fantastic amenities include 4.3 miles of walking trails throughout the community, outdoor infinity pool, indoor pool with on-duty lifeguard, fitness center, library, game room, gas and wood burning fire pits, Tiki bar equipped with refrigerators, sinks and television monitors, pier with transient boat slips, walking paths that link to the Cross Island Trail, lighted pickle ball courts, tennis courts, bocce, dog park, and an outdoor amphitheater for live music and movie nights. The community lifestyle director will keep you busy with daily activities such as yoga, a variety of exercise classes and an assortment of clubs including biking, billiards, book club, baking, mahjong, environmental club, trivia night and more. In addition to the weekly and monthly activities, residents can enjoy crab feasts, oyster roasts, and holiday gatherings throughout the year. This development is an unrivaled, amenity-filled, resort-style experience with convenient access to Annapolis, DC, Baltimore, and BWI. Kent Island offers multiple dining and shopping options, a nearby outlet mall, and a 6.5 mile cross-island trail surrounded by views of the Chester River.

1000 Herons Nest Way Unit #22, Chester

Listing courtesy of RE/MAX Executive. Contact: 4432741900
$769,000
4 Beds ⋅ 3 Baths
Discover the charm of this beautifully renovated split-level home in the desirable Prospect Bay community. With 4 spacious bedrooms and 3 full baths, this residence boasts an inviting interior featuring upgraded countertops, LVP floors, and cozy exposed beams. The heart of the home is the combination kitchen/dining area, perfect for gatherings that can flow outside to the new expanded deck. With one bedroom, full bath and living room on lower level it could be the perfect in-law suite or college student apartment. Enjoy the serene 1.22-acre corner lot with firepit, trees perfect for hammock, backing to mature trees, offering a peaceful views. The community amenities include a pool, golf course, marina, community pool, tennis & pickleball courts and playgrounds, fostering a vibrant neighborhood spirit. Enjoy easy access to the Prospect Bay sanctuary for boating and fishing enthusiasts. Located in a friendly community with excellent schools and nearby parks, this home is perfect for those seeking comfort and convenience. BONUS: Outdoor Office with private entrance on back right corner of house. PLUS: Community has a few boat slips available for rent!

1 Bunker, Grasonville

Listing courtesy of Wilson Realty & Staging LLC. Contact: 4103042250
$850,000
1 Beds ⋅ 2 Baths
This Tidewater Cape sits on the point of 13.78 acres and is surrounded by the tidal waters of the Chester River. Built to be a summer home by a father and son in 1950, this home is filled with character and charm. Drive through the woods and catch glimpses of the river to your left. Moments later, the trees open to the homesite, and then notice there is water to your right as well, showcasing the point setting. Cute and cozy from the moment you see it, but this home’s full presence is best appreciated from the rear, where the three-story Tidewater elevation stands proud and timeless. Loved and enjoyed by several generations, the home offers hardwood floors throughout the main and second levels, beautiful built-ins and gorgeous hardwood details throughout. Outdoor living includes a main-level porch and lower-level patio, perfect for taking in the peaceful surroundings. Two outbuildings are located along the shoreline: a one-car garage and a workshop with electric, they offer flexible storage and workspace. There could be potential for subdividing a lot, but buyers to verify all possibilities with the county. Pier/dock conveys As-Is — do not walk on dock. Do Not Enter Property without an appointment.

200 Powers Ln, Millington

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

$724,500
5 Beds ⋅ 4 Baths
Price improvement! Motivated sellers. This custom built home offers the perfect opportunity to live just minutes away from the Chesapeake Bay Bridge and Route 50, offering partial water views and a layout designed for both everyday living and effortless entertaining. The main level features 12 foot ceilings and oversized 6 foot windows that create bright, open living spaces. A vaulted morning room transitions seamlessly into a sunroom, providing flexible space for dining, relaxing, or working from home. The gourmet eat-in kitchen offers granite countertops, a substantial center island, pantry, and an open-concept design that opens into the family room and sunroom. The primary suite is generously sized, featuring a tray ceiling and a well-designed bath with custom tile shower and double vanity. The remaining four bedrooms share two jack-and-jill style bathrooms offering convenience for family and guests. Outdoor living is equally appealing, with an 800-square-foot wraparound deck ideal for entertaining. The property also offers space for a potential in-ground pool (buyer to verify with Planning & Zoning). Additional features include custom hardwood and tile flooring run throughout, tailored Roman blinds and wood shutters, new HVAC system, finished garage, and dedicated laundry room with new washer, dryer, and utility sink. A rare 1,820-square-foot crawl space with 4-foot ceilings, finished concrete floor, and indoor access provides plenty of additional storage. Built by local builder Lacrosse Homes with numerous upgrades, this well-maintained home offers immediate value in one of the most popular areas on the Eastern Shore - all with no HOA. Schedule your tour today.

1868 Roberta Dr, Chester

Listing courtesy of Coldwell Banker Realty. Contact: 4102638686
$2,495,000
5 Beds ⋅ 4 Baths
Price improvement. Welcome home to this stunning waterfront property in Cove Creek Club on Kent Island. Cove Creek is a Golfer's Paradise! This remarkable five bedroom, four bathroom home offers an unparalleled blend of privacy, elegance, and panoramic coastal beauty all located on your very own private peninsula. With an impressive 566 feet of protected shoreline where Tanner’s Creek converges with Cove Creek, opening directly to the Eastern Bay, this southern-facing residence offers breathtaking water views from nearly every room. Upon entering, you’re greeted by a dramatic two-story foyer with soaring vaulted and coffered ceilings that set an immediate tone of refinement, drawing the eye straight through to the large backyard and shimmering water views beyond. The thoughtfully designed main level features high ceilings throughout and a serene primary suite with views of the pool and waterfront. The primary retreat offers a custom walk-in closet with built-ins, tray ceiling, and a spa-inspired bath with dual vanities, private water closet, soaking tub, expansive walk-in shower, and plantation shutters for added privacy. Upstairs, enjoy a recreation room with wide angle water views and balcony perfect for enjoying sunsets while playing a game of pool or darts. Four additional bedrooms can be found here as well, two on either side of the home sharing jack-and-jill style bathrooms with private closets. Designed for effortless entertaining and elevated everyday living, the open-concept living and dining spaces flow seamlessly from the beautifully updated kitchen. Here, refined finishes include soft-close cabinetry, granite countertops, a marble backsplash, center island, walk-in pantry, stainless-steel appliances, gas cooktop, wine refrigerator, and warming drawer. The kitchen opens to an inviting living room with sliding doors to access the outdoor living area. Outside you’ll find extensive hardscaping with a built-in grill, granite countertops, and a granite dining table seating eight, perfect for hosting refined waterfront gatherings. The resort-style backyard is a private sanctuary, featuring a sparkling pool and a private pier equipped with three boat lifts—ideal for boating, paddle boarding, crabbing, or simply enjoying sunsets accompanied by visits from blue herons and bald eagles. Professionally designed landscaping offers year-round color with mature plantings all complemented by a lush, level lawn maintained by a multi-zone irrigation system. Additional highlights include a spacious three-car garage with room for vehicles, golf carts, and storage, along with premium finishes throughout that reflect timeless craftsmanship and meticulous attention to detail. As a resident of Cove Creek, enjoy access to an exceptional array of private amenities including a USGA-rated golf course, deep-water marina, private beach, clubhouse, fitness center, tennis, pickleball, and bocce courts, boat ramp and storage yard, as well as miles of scenic walking and biking trails - all located on Kent Island, just minutes from the Chesapeake Bay Bridge and Route 50.

137 Tanners Point Dr, Stevensville

Listing courtesy of Coldwell Banker Realty. Contact: 4102638686