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176 Flagstaff Way Unit 2433, Chester
$769,990
2 Beds ⋅ 3 Baths
The Chester at Lot 2433 offers a thoughtfully designed open-concept layout with a projected settlement date of August 2026, making it an excellent opportunity for buyers planning ahead. This home features 2 bedrooms, 2.5 baths, and a 1-car garage, delivering comfort, functionality, and efficient use of space. Standout features include a dedicated home office with lighted French doors, a dry bar ideal for entertaining, an electric fireplace for added ambiance, and a convenient storage room to keep everything organized. Luxury vinyl plank flooring runs throughout the home, with tile in both full baths for durability and easy maintenance. The kitchen is well-appointed with a single oven, microwave, gas cooktop, range hood, dishwasher, pendant lighting, and a tile backsplash, all complemented by quartz countertops. The owner’s bath features a shower with seat, handheld shower wand, double sinks, and quartz countertops, creating a comfortable and refined retreat. For a full list of features for this home, please contact our sales representatives. Photos are for illustrative purposes only and may not represent the exact home or finishes available.

176 Flagstaff Way Unit 2433, Chester

Listing courtesy of KOVO Realty. Contact:

Selling Office: KW Metro Center.

114 Cedar Rd, Chester
$491,023
3 Beds ⋅ 2 Baths
AGENTS - PLEASE VIEW AGENT REMARKS IN BRIGHT MLS. Discover your private sanctuary on this sprawling 1-acre lot. This meticulously maintained residence with over 3,000 SF of total living space blends modern comfort with rare functional space. Inside, you’ll find fresh updates and an expanded, bespoke master suite designed for total relaxation. The true highlight is the property’s versatility: beyond the sun-drenched, enclosed sunroom and expansive backyard, you’ll find a massive 25x40 detached outbuilding with a 10x16 garage door—a perfect home for an RV, boat, high-end gym, or professional workshop. With the rare benefit of public sewer and an oversized 3-door garage, this property offers an exclusive lifestyle opportunity that is as practical as it is impressive. blocks to the water and marinas between Cox and Crab Alley Creek! Offers may be entered ONLINE through Friday, July 17, 2026 at 5:00 pm. AT SELLER'S DISCRETION, AN OFFER MAY BE ACCEPTED AT ANY TIME.

114 Cedar Rd, Chester

Listing courtesy of Keller Williams Legacy. Contact:

Selling Office: Samson Properties.

313 Oak St, Centreville
$293,000
2 Beds ⋅ 1 Baths
Discover the charm of this delightful bungalow nestled in the heart of Centreville Heights. This beautifully maintained 2-bedroom, 1-bathroom home boasts hardwood floors that flow seamlessly throughout, creating a warm and inviting atmosphere. The eat-in kitchen is perfect for those early morning coffees or evening cocktails, including a cooktop, wall oven, dishwasher, and refrigerator, perfect for culinary enthusiasts. Step outside to enjoy your private deck, ideal for enjoy those beatiful mornings or evening gatherings. The spacious lot offers ample outdoor space, complemented by street lights that enhance the neighborhood's inviting ambiance. A convenient shed provides additional storage for your gardening tools or outdoor equipment. The interior features include an attic for extra storage, a cozy dining area, and energy-efficient double-hung windows that fill the home with natural light. The basement, equipped with a drainage system and sump pump, offers potential for additional living space or a workshop. Located in a vibrant community, this home is just minutes away from local parks, providing endless opportunities for outdoor activities and relaxation. The neighborhood is known for its friendly atmosphere and accessibility to essential public services. This property is not just a house; it's a place to create lasting memories. Embrace the lifestyle you've always wanted in Centreville Heights!

313 Oak St, Centreville

Listing courtesy of Cummings & Co. Realtors. Contact:

Selling Office: Eastern Shore Real Estate, LLC.

405 Quail Run Dr, Centreville
$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:

Selling Office: Benson & Mangold, LLC.

154 Bluebell Ct, Chester
$965,000
3 Beds ⋅ 3 Baths
Welcome to luxury, comfort, and effortless living in the highly sought-after first section of Four Seasons at Kent Island. Offering a floor plan no longer available in the community's newer sections, this exceptional home combines thoughtful design with upscale finishes throughout. A spacious foyer welcomes you into an open and inviting layout that is perfect for both everyday living and entertaining. At the heart of the home is a stunning gourmet kitchen featuring an oversized center island that naturally becomes the gathering place for family and friends. Whether hosting indoors or enjoying the outdoors, you'll appreciate the seamless flow to the screened porch and beautifully designed patio complete with a built-in fire pit. The private primary suite is a true retreat, highlighted by an elegant tray ceiling, an impressive custom walk-in closet system, and a luxurious en-suite bath featuring a spacious walk-in shower, dual vanities, and a dedicated built-in makeup vanity. The main level also offers a second bedroom, full bath, private home office, and convenient laundry room, providing the ease of one-level living. Upstairs, guests will enjoy their own private space with an additional living area, bedroom, and full bath and access to the conditioned sky garage which is great for storage. Attached two car garage with epoxy flooring and inside access. Beyond the home, enjoy the award-winning lifestyle Four Seasons at Kent Island is known for. Residents have access to an impressive 24,000-square-foot clubhouse featuring indoor and outdoor pools, a state-of-the-art fitness center, tennis and pickleball courts, dog parks, walking trails, and an active calendar of social events—all designed for exceptional 55+ living.

154 Bluebell Ct, Chester

Listing courtesy of Wilson Realty & Staging LLC. Contact:

Selling Office: Coldwell Banker Realty.

176 Flagstaff Way Unit 2424, Chester
$875,000
3 Beds ⋅ 3 Baths
The Severn, located on Lot 2424, is scheduled for a August 2026 settlement and offers a well-designed layout with 3 bedrooms, 2.5 baths, and a 1-car garage—perfect for low-maintenance living without sacrificing style. This home features a welcoming electric fireplace, a convenient dry bar for entertaining, and a dedicated storage room to keep everything organized. The kitchen is thoughtfully equipped with a gas cooktop, single oven, microwave, range hood, dishwasher, pendant lighting, and a tile backsplash, all paired with sleek quartz countertops. Throughout the home, LVP flooring provides durability and a cohesive look, with tile flooring in both full baths. The primary bath offers a relaxing retreat with a walk-in shower featuring a seat and handheld shower wand, dual sinks, and quartz countertops. For a full list of features for this home, please contact our sales representatives. Photos are for illustrative purposes only and may not represent the exact home or finishes available.

176 Flagstaff Way Unit 2424, Chester

Listing courtesy of KOVO Realty. Contact:

Selling Office: RE/MAX Executive.

132 Cecil Rd, Stevensville
$685,000
3 Beds ⋅ 3 Baths
Located at the end of a quiet road in the desirable Kent Island Estates community, this charming coastal retreat offers a rare blend of privacy, character, and captivating water views. Situated on nearly an acre and surrounded by mature landscaping and open space, the property provides a serene setting that embraces the beauty of Chesapeake Bay living. The home features three spacious bedrooms, including two conveniently located on the main level, and two and a half baths that balance timeless charm with comfortable everyday living. The upgraded kitchen offers quartz countertops, island with storage, stainless steel appliances, and overlooks the living room with vaulted ceilings. The sunroom is located on the other side of the kitchen, featuring new LVP flooring and plenty of natural light. Thoughtfully designed outdoor spaces invite year-round enjoyment, including a screened porch overlooking the fenced backyard, a recently stained second-level deck off the primary suite with views of Shipping Creek, and a custom stone fireplace with an adjoining BBQ area perfect for gathering with family and friends. Other exterior amenities include a freshly painted detached garage ideal for a workshop, gym, or additional storage, a separate storage shed, and a newly paved asphalt driveway. Additionally, the home features a freshly painted exterior and matching detached garage, refinished hardwood floors, upgraded luxury vinyl plank flooring in the sunroom, fresh interior paint, a tankless water heater, new well pump, and crawlspace encapsulation. Residents of Kent Island Estates enjoy an exceptional waterfront lifestyle with access to a community pier, public beach, private community beach, waterfront playground, and kayak and canoe launch, all within walking distance. Whether spending the day on the water, launching a kayak, or enjoying an evening by the fire, this community offers endless opportunities to experience the Chesapeake Bay. Ideally situated on Kent Island, the property is a short drive to local shopping, dining, marinas, and entertainment. Commuters will appreciate easy access to Route 50 and the Chesapeake Bay Bridge, providing convenient connections to Annapolis, Baltimore, Washington, D.C., Kent Narrows, and Delaware beaches. Combining scenic water views, thoughtful updates, and sought-after community amenities, this inviting retreat offers the perfect setting for full-time living or a relaxing coastal escape. Schedule your tour today!

132 Cecil Rd, Stevensville

Listing courtesy of Coldwell Banker Realty. Contact:

Selling Office: Redfin Corp.

517 Round Top Rd, Chestertown
$289,000
3 Beds ⋅ 1 Baths
An exceptional opportunity to own this Single Level 3 bedroom 1 full bathrooms Ranch Style Home at a GREAT price nestled on an adorable lot. No need to worry about climbing stairs, everything is located on one floor. the interior showcases contemporary finishes and a thoughtful layout that maximizes both style and functionality. The bathroom has been tastefully refreshed, the home has been freshly painted with LPV flooring and carpet throughout. This home offers the ultimate in conveniences local public and private golf courses outlets Close Proximity to the Chester River, fine dining and easy access to major highways. Don't miss out on the chance to create your dream space in this prime Chestertown location! NEW HVAC SYSTEM TO BE INSTALLED

517 Round Top Rd, Chestertown

Listing courtesy of Keller Williams Flagship. Contact:

Selling Office: Coldwell Banker Chesapeake Real Estate Company.

508 Paul Dr, Stevensville
$630,000
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:

Selling Office: Douglas Realty LLC.

13704 Main St, Queen Anne
$140,000
4 Beds ⋅ 1 Baths
Opportunity awaits in the quaint town of Queen Anne. This 4-bedroom, 1-bath farmhouse offers plenty of potential. The home features double side porches, off-street parking and classic farmhouse character, but is in need of updates and repairs. Previously used as a rental property for many years, this property could present an opportunity for an investor, contractor or buyer looking to restore and build equity. Property is served by a shared well with the adjoining property (13706 Main Street), which is also being offered for sale. Conveniently located less than 3/4 mile from Hillsboro Landing, providing access to Tuckahoe Creek for boating and fishing, and less than 5 miles from Tuckahoe State Park. Known for its 60-acre lake, the park offers boating, fishing, playgrounds, and over 20 miles of scenic hiking, biking, and equestrian trails.

13704 Main St, Queen Anne

Listing courtesy of Benson & Mangold, LLC. Contact:

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

13706 Main St, Queen Anne
$95,000
4 Beds ⋅ 1 Baths
Located in the small town of Queen Anne, this 4-bedroom, 1-bath farmhouse is in need of extensive repairs and renovation and is being sold as-is. The home was previously used as a rental property and offers an opportunity for investors, contractors or buyers looking for a project property with potential. Features include a covered front porch, off-street parking and a small storage shed. The property shares a well with the neighboring home, which is also available for purchase (13704 Main Street). Enjoy a location less than 3/4 mile from Hillsboro Landing with access to Tuckahoe Creek for boating and fishing and under 5 miles from Tuckahoe State Park. The park is known for its 60-acre lake, presenting fishing and boating opportunities, playgrounds, and more than 20 miles of hiking, biking, and equestrian trails.

13706 Main St, Queen Anne

Listing courtesy of Benson & Mangold, LLC. Contact:

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

403 Eagle Manor Dr, Church Hill
$629,900
4 Beds ⋅ 3 Baths
This beautifully maintained custom-built home in the desirable Eagle Manor community combines luxury finishes, thoughtful design, and over an acre of professionally landscaped privacy. Inside, you’ll find an open and airy floor plan featuring 4 bedrooms, 3 full baths, luxury vinyl plank flooring, custom moldings, shiplap accents, two fireplaces, and abundant natural light. The gourmet kitchen is designed for gathering with quartz countertops, a large center island, farmhouse sink, stainless steel appliances, and ample cabinetry. The first-floor primary suite offers a private retreat with a spacious walk-in closet, soaking tub, and walk-in shower. Generous secondary bedrooms and flexible living spaces provide room for guests, a home office, or multigenerational living. Step outside to enjoy your own backyard oasis featuring an oversized screened porch, professionally landscaped grounds, mature privacy plantings, a serene koi pond, irrigation system, and elegant wrought iron fencing. The expansive one-acre lot also offers plenty of room for a future pool. With more than $140,000 in seller improvements, this move-in-ready home offers exceptional quality and value that would be difficult to replicate at today’s construction costs. Conveniently located near Centreville, Chestertown, waterfront marinas, shopping, dining, and the Chesapeake Bay, this is an outstanding opportunity to enjoy the best of Maryland’s Eastern Shore. Schedule your private showing today and experience everything 403 Eagle Manor has to offer.

403 Eagle Manor Dr, Church Hill

Listing courtesy of Coldwell Banker Realty. Contact:

Selling Office: Coldwell Banker Chesapeake Real Estate Company.

2008 Bridgepointe Dr, Chester
$355,000
2 Beds ⋅ 2 Baths
Looking for more space than you might expect on Kent Island? This spacious end-unit home offers over 1,800 square feet with a flexible layout designed to give you plenty of room to make it your own. At the heart of the home, the oversized kitchen provides an abundance of cabinetry and countertop space, making it ideal for everyday living, entertaining, or anyone who simply appreciates having room to spread out. The open layout flows into a generously sized living area, while a conditioned sunroom surrounded by windows adds even more usable living space and leads to a large rear deck overlooking peaceful pond and fountain views. Two spacious bedrooms and two full bathrooms provide comfortable accommodations, while the converted garage creates valuable bonus space ready to adapt to your needs as a home office, den, hobby room, guest space or additional living area, with the option to return it to a traditional garage if desired. The end-unit location brings additional natural light and a more open feel, while multiple living spaces throughout the home offer flexibility that's increasingly hard to find. Conveniently located in Chester and close to everything Kent Island has to offer, this home combines generous square footage, a versatile floor plan and a peaceful outdoor setting with plenty of opportunity to make the space your own. Additional peace of mind with one year Home Warranty offer!!

2008 Bridgepointe Dr, Chester

Listing courtesy of RE/MAX Executive. Contact:

Selling Office: Coldwell Banker Realty.

176 Flagstaff Way Unit 2412, Chester
$589,990
2 Beds ⋅ 3 Baths
The Magothy at Lot 2412 delivers a thoughtfully designed layout with modern comforts and refined details, offering a projected settlement of August 2026. This inviting home features 2 bedrooms, 2.5 baths, and a 1-car garage, making it an ideal blend of style and functionality. Standout features include a dedicated home office with lighted French doors, a stylish dry bar perfect for entertaining, and a cozy electric fireplace that anchors the living space. The kitchen is well-appointed with a gas cooktop, single oven, microwave, range hood, dishwasher, pendant lighting, and a tile backsplash, all complemented by sleek Quartz countertops. Luxury vinyl plank flooring flows throughout the home, with tile in both full baths for durability and easy maintenance. The owner’s bath is designed for comfort, featuring a walk-in shower with seat, handheld shower wand, double sinks, and Quartz countertops, creating a spa-like retreat. For a full list of included features, please contact our sales representatives. Photos are for illustrative purposes only and may not represent the exact home or finishes available.

176 Flagstaff Way Unit 2412, Chester

Listing courtesy of KOVO Realty. Contact:

Selling Office: Unrepresented.

176 Flagstaff Way Unit 2411, Chester
$599,990
2 Beds ⋅ 3 Baths
The Magothy at Lot 2411 delivers a thoughtfully designed layout with modern comforts and refined details, offering a projected settlement of August 2026. This inviting home features 2 bedrooms, 2.5 baths, and a 1-car garage, making it an ideal blend of style and functionality. Standout features include a dedicated home office with lighted French doors, a stylish dry bar perfect for entertaining, and a cozy electric fireplace that anchors the living space. The kitchen is well-appointed with a gas cooktop, single oven, microwave, range hood, dishwasher, pendant lighting, and a tile backsplash, all complemented by sleek Quartz countertops. Luxury vinyl plank flooring flows throughout the home, with tile in both full baths for durability and easy maintenance. The owner’s bath is designed for comfort, featuring a walk-in shower with seat, handheld shower wand, double sinks, and Quartz countertops, creating a spa-like retreat. For a full list of included features, please contact our sales representatives. Photos are for illustrative purposes only and may not represent the exact home or finishes available.

176 Flagstaff Way Unit 2411, Chester

Listing courtesy of KOVO Realty. Contact:

Selling Office: Unrepresented.

252 Eareckson Ln, Stevensville
$1,720,000
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:

Selling Office: Benson & Mangold, LLC.

251 Opera Ct, Centreville
$437,000
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:

Selling Office: Blue Crab Realty LLC.

318 Wicomico Rd, Stevensville
$459,000
4 Beds ⋅ 2 Baths
Don’t miss the opportunity to own this charming 4-bedroom home featuring 2 recently renovated baths, a flexible office/den, and a BRAND NEW ROOF! The spacious kitchen with peninsula seating flows seamlessly into the dining area, creating the perfect gathering space for family and friends. The expansive family room is filled with natural light thanks to vaulted ceilings, skylights, and oversized windows that create an open and airy feel throughout. A screened-in porch adds even more living space to enjoy year-round, while the large deck, accessible from both the main living area and the primary suite, offers the perfect setting for morning coffee, evening entertaining, or simply relaxing at the end of the day. Located in the desirable Kent Island Estates community, this home offers the Eastern Shore lifestyle you’ve been searching for, complete with access to multiple beaches, a playground, and the Southern Kent Island Trail. Come experience all this home has to offer!

318 Wicomico Rd, Stevensville

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

Selling Office: Wilson Realty & Staging LLC.

204 Overture Way, Centreville
$515,000
2 Beds ⋅ 3 Baths
Welcome to effortless luxury in this beautifully maintained move-in-ready home located within a highly desirable 55+ resort-style community. From the moment you step inside, the high ceilings and custom architectural details elevate the entire space creating an atmosphere of refined elegance. The beautiful thoughtful layout maximizes comfort and convenience, allowing you to live effortlessly. Gleaming hardwood floors flow seamlessly through the main living areas, which feature two spacious bedrooms and two-and-a-half pristine bathrooms. Enjoy access to top tier community amenities while relaxing in a home crafted with unmatched care and quality. Recent care: Roof-late 2022, water heater replaced 2025; heat pump replaced 2022; updated appliances, coated garage flooring; gutter guard, finished sky basement. 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.

204 Overture Way, Centreville

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

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

102 Pine St, Crumpton
$339,900
3 Beds ⋅ 2 Baths
Open House Saturday May 30th 11am -1pm — Stop In and Take a Tour! New Price Alert!! Experience the simple pleasures of one-level living in this stylish rancher on a spacious 1/2 acre corner lot. Built just four years ago!! From morning coffee on the front porch to sunset boat rides on the Chester River (just a couple blocks away!), this home is designed for comfort and convenience. Step inside and you will see the well-designed open floor layout with beautiful LVP flooring, a sleek white kitchen boasting SS appliancNew Price Alert!!!es and granite countertops, a spacious living room and an adjoining dining area adorned with tons of natural light. The sleeping zone features a primary bedroom with an ensuite bathroom. there's also two additional bedrooms with a shared full bathroom and a separate laundry room. You’ll love the designer lighting, sun-drenched rooms, and the privacy of a fenced backyard. Within close proximity to shopping, dining and the delights of downtown Chestertown... Easy access to Route 301...20 minutes to Delaware...30 minutes to Bay Bridge...Why wait to build when you can own this nearly new and perfectly priced home?? Some images have been virtually staged and digitally enhanced.

102 Pine St, Crumpton

Listing courtesy of Clark & Co Realty, LLC. Contact:

Selling Office: Benson & Mangold, LLC.

702 Coon Box Rd, Centreville
$845,000
3 Beds ⋅ 3 Baths
Welcome to 702 Coon Box Road! This beautifully crafted 3 bedroom, 2.5 bath home offers almost 2,600 sq ft of refined living space on a 5+ acre serene private lot on the outskirts of the town of Centreville. The first floor boasts an open floor plan with a kitchen, dining room, and living room anchored by a stunning floor-to-ceiling stone fireplace, along with a convenient laundry room. The first floor primary suite impresses with a walk-in closet and a spa-like bath featuring a walk-in tile shower, soaking tub, and double vanities. Upstairs, two large bedrooms with walk-in closets and a versatile bonus room offer flexibility for any lifestyle. Outside, the 36x60 detached building, heated and cooled, is in a league of its own, featuring a professional shop, private office, finished recreation room with a custom bar, and a finished loft. Top it all off with a large paver patio and fire pit, and you have a property that truly has it all. Coming Soon! Contact me today for more information and to schedule your tour!

702 Coon Box Rd, Centreville

Listing courtesy of Clark & Co Realty, LLC. Contact:

Selling Office: Taylor Properties.

7013 Bridgepointe Dr, Chester
$350,000
3 Beds ⋅ 3 Baths
Adorable is the perfect word to describe this beautifully maintained townhome! Freshly painted and featuring a new roof and skylights (2025), this inviting home offers over 1,600 square feet of comfortable living space with three bedrooms, two full baths, and one-half bath. The main level showcases vaulted ceilings with skylights that fill the home with natural light, creating a bright and airy atmosphere. The open-air plan seamlessly connects the spacious living room and dining area, with room to comfortably accommodate four to six guests, making it ideal for both everyday living and entertaining. Step outside to the private porch overlooking a picturesque pond, where you can relax and enjoy the peaceful sound of the fountain. The main-level primary suite offers a walk-in closet, walk-in shower, and private access to the porch—your own tranquil retreat. The bright, open kitchen features abundant windows and space for a cozy breakfast table, creating the perfect spot to enjoy your morning coffee while taking in the views. Additional highlights include a one-car garage, convenient storage space off the porch, and low HOA fees compared to most communities. Ideally located just minutes from shopping, restaurants, churches, the Bay Bridge, and everyday conveniences, this charming townhome offers the perfect combination of comfort, style, and convenience. Don't miss the opportunity to make this wonderful home your own!

7013 Bridgepointe Dr, Chester

Listing courtesy of Coldwell Banker Realty. Contact:

Selling Office: Coldwell Banker Realty.

246 Upland Ln, Centreville
$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:

Selling Office: TTR Sotheby's International Realty.

125 Fawn Ln, Grasonville
$600,000
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:

Selling Office: Benson & Mangold, LLC.

202 Royston Shores Rd, Chestertown
$1,200,000
4 Beds ⋅ 3 Baths
Wake up to sweeping views of the Chester River and end each day with spectacular western sunsets from this exceptional waterfront. Situated on 0.61 acres with 169 feet +/- of waterfrontage and deep-water access, this 4-bedroom, 3-bath brick Cape Cod invites you to enjoy the very best of waterfront living. Unlike many waterfront properties, the level lot provides easy access from the home to the water and private pier—no steep banks or long flights of stairs to navigate. Whether you enjoy boating, kayaking, fishing, crabbing, or simply relaxing by the water, this property makes it easy to embrace the Eastern Shore lifestyle. Inside, you'll find more than 2,200 square feet of comfortable living space designed to capture the stunning river views. A charming four-season room with brick flooring and panoramic water views is the perfect place to enjoy your morning coffee year-round, while the screened porch is ideal for summer crab feasts and outdoor entertaining. At the heart of the home, a wood-burning brick fireplace that creates a warm and inviting atmosphere. The flexible floor plan includes a main-level bedroom and full bath, ideal for guests or one-level living. Upstairs, the primary suite serves as a peaceful retreat, featuring breathtaking river views, abundant natural light, and a private ensuite bath with double vanities and a tiled shower. Two additional generously sized bedrooms and another full bath provide ample space for family and visitors. Recent improvements include a new roof in 2020 and an electric vehicle charger installed in the attached garage in 2025. An irrigation system serves both the front and rear yards, and the property is located outside the flood plain, so flood insurance is not required. Tucked away near the end of a private road, this serene setting feels calm and peaceful while remaining just minutes from Chestertown's shops, restaurants, marina, and popular farmers market. Enjoy daily visits from eagles, ospreys, herons, owls, deer, and other wildlife, all from your own backyard. Whether you're searching for a full-time waterfront residence or the perfect weekend escape, this rare Chester River property offers the beauty, tranquility, and lifestyle that makes Maryland's Eastern Shore so special.

202 Royston Shores Rd, Chestertown

Listing courtesy of Cross Street Realtors LLC. Contact:

Selling Office: Coldwell Banker Chesapeake Real Estate Company.

458 Railroad Ave, Centreville
$345,000
3 Beds ⋅ 1 Baths
Welcome home to this charming 3-bedroom, 1-bath rancher nestled in the heart of Centreville! This cozy home offers an inviting open-concept living and dining area, an eat-in kitchen with updated appliances, and comfortable carpeted bedrooms. Enjoy relaxing on the perfect front porch or entertaining in the spacious, private backyard, complete with a new vinyl privacy fence. Additional updates include a new HVAC system installed in 2022, providing peace of mind for years to come. Conveniently located near schools, shopping, restaurants, and everyday amenities, this home combines comfort, convenience, and charm. Don't miss your opportunity to make this adorable rancher your new home! Interior pictures will be available on 6/4/26

458 Railroad Ave, Centreville

Listing courtesy of Benson & Mangold, LLC. Contact:

Selling Office: Unrepresented.

126 E Brook Dr, Centreville
$575,000
5 Beds ⋅ 3 Baths
Welcome to 126 E Brook Drive in North Brook. If you've been searching for a home that offers space, style, and flexibility, this stunning North Brook property delivers it all. From the moment you step inside, you'll be impressed by the beautifully updated high-end kitchen, thoughtfully designed with quality finishes, abundant cabinetry, and plenty of workspace for cooking, entertaining, and everyday living. The kitchen flows seamlessly into the main living areas, creating the open and inviting floor plan today's buyers are looking for. One of the home's most desirable features is the main-level bedroom, offering incredible flexibility for guests, multi-generational living, a private home office, or anyone seeking first-floor convenience. With five true bedrooms, everyone has room to spread out and enjoy their own private space. The generously sized bedrooms provide comfort and functionality, while the spacious layout offers the flexibility modern families need. The full basement, over 1,600 sq ft, presents endless possibilities, whether you're looking for additional living space, a recreation room, home gym, workshop, or simply exceptional storage. Step outside to enjoy the large deck, perfect for summer barbecues, morning coffee, or relaxing evenings overlooking the backyard. Located in the highly sought-after North Brook community, this home combines generous living space, thoughtful updates, and a prime Centreville location close to schools, parks, shopping, dining, and major commuter routes. Five true bedrooms. A main-level bedroom. A stunning kitchen. A full basement. And room for everyone. In today’s market, this alone is luxury in North Brook.

126 E Brook Dr, Centreville

Listing courtesy of RE/MAX Executive. Contact:

Selling Office: Allfirst Realty, Inc..

228 Merganser Dr, Chestertown
$42,000
Situated on a quiet road, this half-acre property offers a great opportunity to enjoy the Eastern Shore lifestyle. Community water access to the Chester River is located at the end of the road and includes a boat ramp, making it easy to enjoy boating, fishing, crabbing, or paddle boarding right nearby. Located within the Queen Anne’s County school district and just minutes from downtown Chestertown. A mobile home currently exists on the property and is believed to be approximately 60 years old. Buyer to verify condition and habitability of the mobile home or remove at buyer’s discretion. Seller has no knowledge or information regarding the mobile home. Original well and septic are present on the property; buyer to verify condition and functionality of both.

228 Merganser Dr, Chestertown

Listing courtesy of Benson & Mangold, LLC. Contact:

Selling Office: Unrepresented.

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