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$529,000
3 Beds ⋅ 3 Baths
Welcome to resort-style living in this beautifully appointed home nestled in the back of a desirable 55+ community, offering serene pond views and exceptional amenities. Rich cherry hardwood flooring flows throughout the main living areas, including the formal living and dining rooms, creating warmth and elegance from the moment you enter. The gourmet eat-in kitchen is a true highlight, featuring granite countertops, stainless steel appliances, and an open layout that seamlessly connects to the family room—perfect for everyday living and entertaining. Relax by the cozy gas fireplace or step outside to the private patio overlooking the tranquil pond for peaceful outdoor enjoyment.This home offers three spacious bedrooms and two full baths, including a luxurious primary suite with a large walk-in shower, soaking tub, and generous closet space. A custom built-in buffet with glass cabinetry adds both beauty and functionality, while the separate laundry room and two-car garage provide everyday convenience. Enjoy unparalleled community amenities including indoor and outdoor pools, billiards room, meeting room, bar, bocce ball and tennis courts, and a tot lot—everything you need for an active and social lifestyle. This exceptional home combines comfort, style, and resort-like living in a prime setting.

125 Encore Ct, Centreville

Listing courtesy of Rosendale Realty. Contact: 4107580333
$349,900
2 Beds ⋅ 2 Baths
NEW CONSRUCTION. 2 BEDROOM 2 BATH RANCHER LOADED WITH UPGRADES. PICTURES ARE FROM PREVIOUS MODEL BUT FINISHES STILL THE SAME JUST DIFFRENT COLORS. COME SEE FOR YOURSELF. LOADED WITH UPGRADES. WHY BUILD WHEN YOU CAN JUST MOVE IN. UPGRADED LIGHTING PACKAGE, TRAY CEILING, CUSTOME 2 COLOR PAINT, UPGRADED TRIM, THE LIST JUST GOES AND GOES.

114 W Main St W Main, Sudlersville

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

$470,000
3 Beds ⋅ 3 Baths
New and improved price! This beautifully updated and well maintained home delivers exceptional value in the highly desirable Harbor View community—just two miles east of the Chesapeake Bay Bridge. Set on a picturesque 0.35‑acre corner lot, this 3‑bedroom, 2 full and 1 half bath home blends comfort, quality, and an unbeatable location. Inside, you’ll love the bright, updated kitchen featuring new countertops and backsplash, complemented by hardwood floors on the main and upper levels. A dramatic cathedral ceiling with skylights fills the home with natural light, creating an open and welcoming atmosphere. The spacious lower‑level family room offers a cozy retreat, while a flexible bonus room is perfect for a home office, guest room, or additional sleeping space. *Recent improvements add peace of mind and long‑term value, including a new roof (2019) with 50‑year shingles, new stove and hot water heater, and a new vinyl pool liner with a lifetime warranty. *Enjoy peace of mind with brand-new Pella tilt-in windows installed throughout the home in 2025, combining style, convenience, and energy efficiency. The pool is also equipped with a new robotic cleaner, making maintenance simple and hassle-free. The pool is open! Step outside to a fully fenced backyard oasis featuring a private in‑ground pool and deck— ready for summer entertaining or relaxing at home. Residents also enjoy access to the Harbor View community’s one‑acre field with pavilion and playground, perfect for gatherings and outdoor fun. Conveniently located just 20 minutes to Annapolis, 45 minutes to Baltimore, and under an hour to Washington, D.C., this home also offers easy access to Kent Narrows waterfront dining, the 6.5‑mile Cross Island Trail, and Queenstown Premium Outlets just minutes away. With updated features, transferable warranties, and a refreshed price, this home is move‑in ready and offers an outstanding opportunity to enjoy the best of Kent Island living. Schedule your showing today—this one is not to be missed.

1916 Stevens Dr, Chester

Listing courtesy of Coldwell Banker Realty. Contact: kelly.thompson@cbmove.com
$949,500
5 Beds ⋅ 3 Baths
Welcome to 530 Kennersley Farm Lane, nestled in the private waterfront community of Kennersley Farm. Set on 5 private acres along Island Creek, this property offers lots of privacy and nature. A long, tree-lined driveway leads you past mature landscaping and ample parking, where you can see views of the water. Inside, there is beautiful flooring and a bright, open layout. The kitchen features granite countertops, a center island, upgraded GE Profile appliances, and an eat-in area overlooking the in-ground pool and Island Creek. The primary suite, located on the first floor, is a true retreat with a huge walk-in closet, featuring a soaking tub, dual granite vanity, and tile shower. This room could also be used as an office, or second living area. The huge plus is the conveniently located laundry room located on the first floor. Upstairs, find three spacious bedrooms, two full baths, and a bonus room over the garage that can serve as a fifth bedroom, media room, or office. The unfinished walkout basement provides plenty of storage and potential for future living space. Outside, enjoy your private backyard with an in-ground pool, hot tub, patio, pool shed, and sweeping water views. You are surrounded by trees for tons of privacy. As a resident of Kennersley Farm, you’ll also have access to the community marina with pool and boat slips. Conveniently located near Centreville, Chestertown, beaches, restaurants, and shopping, this home offers so much and more. Your waterfront dream home awaits!!

530 Kennersley Farm Ln, Church Hill

Listing courtesy of Coldwell Banker Realty. Contact: (717) 735-8400
$714,900
4 Beds ⋅ 3 Baths
Welcome to Meadow Creek Estate homes on acre plus homesites with plenty of room for a pool and separate garage. In the county but close to downtown Centreville. Centreville offers restaurants stores, parks and schools. 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 oversized table space kitchen. Add a light-filled morning room off the rear or expand your space with plan extensions. Choose a two or three-car garage for this plan. Upstairs accommodates four nicely sized bedrooms and you can customize your lower level rec area to suit your needs.

116 Pasture Ct, Centreville

Listing courtesy of Keller Williams Flagship. Contact:

$779,900
4 Beds ⋅ 3 Baths
Welcome to Meadow Creek. Estate homes on acre plus homesites with plenty of room for a pool and a separate garage. In the country but close to downtown Centreville. Centreville offers restaurants, grocery stores, parks and schools. Exuding a quiet elegance, the Merion by Lacrosse Homes is a new single family home design featuring a modern take on the classic center hall colonial design. Highlights of this comfortable home include a main level study for an ideal work from home set-up, chef’s island kitchen with tons of cabinetry and food prep space and a spacious light-filled causal eating area. the stairs are tucked to the rear of the home creating oversized living and dining rooms as well as a spacious great room. Add a morning room to the main level to further expand your living space. Upstairs, enjoy four bedrooms including a large owners suite with deluxe bath, laundry room with linen storage, and three nicely sized secondary bedrooms. Customize your lower level (site specific) with a recreation room, media space, den, bath and more.

415 Twin Meadows Farm Ln, Centreville

Listing courtesy of Keller Williams Flagship. Contact:

$320,000
3 Beds ⋅ 2 Baths
Three bedroom one-floor living on a spacious lot in Chester Harbor! Over half an acre of nicely shaded yard space, and a short distance to the public beach on Mill Creek. 3 bedrooms and 1.5 bathrooms, open living and dining space, large sunroom/ porch with wood-burning stove, and an additional wood stove in the living room. Outside there's a small storage shed and a larger workshop/shed next to the asphalt driveway. The sunroom leads to a deck overlooking the large yard. Great community with water access. Quick ten minutes into Chestertown, and less than an hour to Middletown DE or Annapolis.

222 Dutchess Rd, Chestertown

Listing courtesy of Gunther-McClary Real Estate. Contact:

$662,550
4 Beds ⋅ 3 Baths
Welcome to The Corsica, a beautifully designed two-story home offering 1,664 square feet of well-planned living space. With 4 bedrooms and 2.5 bathrooms, this layout is ideal for anyone seeking both functionality and modern style. Step inside to an inviting open-concept Kitchen, Eating, & Great Room, perfect for entertaining or relaxing with loved ones. The kitchen features an attached large island overlooking the spacious living area, ensuring you’re always part of the conversation. Natural light fills the space, creating a warm and welcoming atmosphere for everyday living. Convenience meets practicality with the Mud/Laundry Room located just off the garage, providing a seamless transition from outdoor activity to the home’s main living areas which is perfect for busy mornings or returning from weekend adventures. Upstairs, you’ll find four comfortable bedrooms, including a private primary suite with a full bath and walk-in closet. Three additional bedrooms share a second full bathroom, offering flexibility for guests, family, or a home office. An optional 16' x 12' rear deck expands your living space outdoors and is ideal for dining or enjoying quiet evenings surrounded by nature. Charming curb appeal, efficient design, and thoughtful flow make The Corsica the perfect place to call home. Some of the standout features include: maintenance free vinyl siding, CertainTeed roof shingles, luxury vinyl plank floors, all wood constructed cabinets with soft close, kitchen granite countertops, an open concept floor plan, and a convenient mud room. Finally, the house will be constructed by Paquin Design Build, an Eastern Shore Local Custom Home Builder.

Grasonville Cemetery Rd Unit #LOT 2, Grasonville

Listing courtesy of EXP Realty, LLC. Contact: 8888607369
$664,650
4 Beds ⋅ 2 Baths
Welcome to the Syberry, a thoughtfully designed single-story home offering 1,710 square feet of modern comfort and convenience. This 4-bedroom, 2-bathroom layout blends open-concept living with functional flow, perfect for today’s lifestyle. At the heart of the home, the spacious Kitchen, Eating, & Great Room create an inviting open area ideal for entertaining and family gatherings. Large windows fill the space with natural light, while the kitchen’s central island provides plenty of prep and seating space to keep everyone connected. The private primary suite offers a peaceful retreat, complete with a generous walk-in closet and en-suite bath. Three additional bedrooms provide flexible options for family, guests, or a home office. From the one car garage, a convenient Mud/Laundry Room connects directly to the main living area, keeping daily routines organized and tidy. An optional 16' x 12' rear deck expands your living space outdoors, perfect for morning coffee or evening relaxation. With its timeless exterior, open interior design, and practical layout, the Syberry delivers the ideal balance of comfort, efficiency, and charm all in a single-level home built for the way you live. Some of the standout features include: maintenance free vinyl siding, CertainTeed roof shingles, luxury vinyl plank floors, all wood constructed cabinets with soft close, kitchen granite countertops, open concept floor plan, garage with shop/storage, convenient Mud Room, and a covered front porch. Finally, the house will be constructed by Paquin Design Build, an Eastern Shore Local Custom Home Builder.

Grasonville Cemetery Rd Unit #LOT 1, Grasonville

Listing courtesy of EXP Realty, LLC. Contact: 8888607369
$679,000
3 Beds ⋅ 2 Baths
Tucked on a private 1-acre corner lot in the desirable Cove Creek community, this home offers 3 bedrooms, 2 baths, and 1,538 square feet of single-level living. Following a complete renovation, every detail has been refreshed—pairing modern updates with a light-filled open floor plan. Expansive windows and vaulted ceilings create a bright, airy feel, while the family room’s wood-burning fireplace adds warmth and charm. The first-floor primary suite is a true retreat with a spacious walk-in closet and en suite bath featuring a dual-sink vanity. Two additional bedrooms provide flexibility, while a new roof and updated energy systems deliver comfort and efficiency. Outdoor living is equally inviting with a large back deck and porch overlooking mature landscaping, plus a two-car garage for convenience. Residents of Cove Creek enjoy resort-like amenities including an 18-hole golf course, clubhouse, tennis and basketball courts, bocce courts, marina, private beach, exercise facility, and miles of walking trails. Whether as a full-time residence or a weekend retreat, 102 Golf Ct blends the ease of a total renovation with the amenities of a true resort community.

102 Golf Ct, Stevensville

Listing courtesy of Benson & Mangold, LLC. Contact: 4108226665
$1,745,000
4 Beds ⋅ 4 Baths
The San Domingo offers nearly 3,500 sq. ft. of thoughtfully designed living space, blending timeless architecture with the waterfront lifestyle of Maryland’s Eastern Shore. Set on a .869-acre lot with 78 feet of direct Corsica River frontage, this 4-bedroom, 3.5-bathroom home pairs elegant design with the natural beauty of its surroundings. The main level is designed for connection and comfort, featuring a gourmet kitchen, spacious dining area, and multiple gathering rooms that open seamlessly to the outdoors. Large windows frame sweeping river views, filling the home with natural light. A detached garage preserves the home’s curb appeal and sightlines, creating a private courtyard feel while adding functional storage and parking. Upstairs, four spacious bedrooms and three full bathrooms provide a private retreat for family and guests. The luxurious primary suite offers serene water views, a spa-inspired bath, and generous closet space, while the additional bedrooms deliver flexibility for family, guests, or home office needs. Outdoor living is central to the San Domingo’s design. Expansive decks and porches extend the living space to the waterfront, creating the perfect setting for morning coffee, sunset entertaining, or simply enjoying the quiet beauty of the Corsica River. With direct access to the water for boating, crabbing, and fishing, your backyard becomes a private gateway to the Chesapeake Bay lifestyle. With its approved perc test and build-ready status, this rare package allows you to secure a prime waterfront lot and bring to life a home crafted for modern coastal living. Here, every detail is designed to balance elegance, functionality, and the unparalleled setting of the Corsica River.

N Hibernia Rd, Centreville

Listing courtesy of TTR Sotheby's International Realty. Contact: (410) 280-5600
$424,990
6 Beds ⋅ 2 Baths
Seller has found a property out of state, so all reasonable offers will be considered...Step back in time—without sacrificing a single modern comfort—in this colonial masterpiece, where historic elegance and thoughtful renovations come together in perfect harmony. Nestled in the picturesque and walkable heart of Queenstown, this 6-bedroom, 2-bath showstopper is more than just a home—it's an opportunity. Zoned Town Center, this unique property offers endless potential: a gorgeous private residence, charming bed & breakfast, lucrative Airbnb (conservative est. of $50k/year for 4 months), or even the chance to live where you work—all in one of Maryland’s most charming small towns. Spread across three character-filled stories, you’ll find original architectural features that include four fireplaces (2 for decoration only)—in the primary bedroom, dining room, living room (gas FP), and kitchen (gas FP) —each adding ambiance to every corner. The sunroom/screened porch is your private sanctuary, ideal for morning coffee, evening wine, watching the rain or simply soaking in the serenity. Recent updates blend seamlessly with the home's historic soul: Newly sealed metal roof Stainless steel appliances Anderson replacement windows Upgraded insulation Modern conveniences throughout All this, while the home retains its authentic charm and integrity. Even better...The property is not in a flood zone—a rare bonus! Enjoy easy, STRESS-FREE commute to DC & Balt. via the commuter buses, easy access to Route 301, while being just minutes from Queenstown Premium Outlets, Queenstown Harbor Links Golf Course, and local water access including a town beach, kayak launch, and visitor boat dockage. And to top it off, the seller is including a one-year home WARRANTY for peace of mind! This is more than a home—it’s a lifestyle, a business opportunity, and a rare piece of Maryland’s history. Don’t miss your chance to own this extraordinary gem!

100 Wall St, Queenstown

Listing courtesy of RE/MAX Executive. Contact: 4432741900
$689,900
4 Beds ⋅ 3 Baths
Welcome to Meadow Creek. Estate homes on acre plus homesites with plenty of room for a pool and a separate garage. In the country but close to downtown Centreville. Centreville offers restaurants, grocery stores, parks and schools. The Windermere combines all of the home design elements our purchasers love the most. On the main level you’ll love the open plan design with a huge kitchen, breakfast/sunroom and family room! Formal living (office) and dining rooms, and two-story foyer complete the space. Upstairs 4 spacious bedrooms include a primary suite with spacious walk-in closet or choose the optional super bath and get two walk-in closets! A lower level offers numerous options for expanding your living space to suit your lifestyle.**Special offer Construction financing*** Models shown with options

325 Twin Meadows Farm Ln, Centreville

Listing courtesy of Keller Williams Flagship. Contact:

$973,607
4 Beds ⋅ 4 Baths
Welcome to Meadow Creek. Estate homes on acre plus homesites with plenty of room for a pool and a separate garage.. In the county but close to downtown Centreville. Centreville offers restaurants, grocery stores, parks and schools. AMAZING BRAND NEW HOME - This stunning 5 bedroom, 3 full bathroom residence offers 3,702 sq ft of finished space. The main-level showcases 9-foot ceilings and LVP hardwood floors throughout, complemented by a gourmet kitchen with stainless steel appliances, 42-inch maple cabinets, and granite countertops. A spacious great room centers around an inviting gas fireplace, while the main level also includes a formal dining room, living room, 6th bedroom/den/office option, full bathroom, and conveniently located laundry room near the garage entrance. The upper-level is thoughtfully designed with 5 bedrooms and 3 full bathrooms. The expansive primary suite features a bonus room perfect for an office, gym, or reading room, along with a luxurious bathroom showcasing a quartz double bowl vanity, ceramic tile throughout, soaking tub and and large glass shower. A secondary suite bedroom and bath and located down the hall, with three additional bedrooms and a full bathroom completing this level. The home includes a 1,717sq ft unfinished basement with 8-foot walls ready for customization. The builder is offering $5,000 in settlement assistance when using preferred title company (Newlyn Title Assurance co., Inc.) and Lender (Redwood Mortgage Services). This exceptional home is constructed by an established Maryland builder, Lacrosse Homes, with over 30 years of experience in delivering quality homes.

104 Pasture Ct, Centreville

Listing courtesy of Keller Williams Flagship. Contact:

$595,000
8 Beds ⋅ 3 Baths
Discover the charm of the Blue Lantern Inn in the quaint, historic town of Centreville on Maryland's Eastern Shore. Built in the 1800s, this property offers over 6000 sq ft of living space, featuring four bedrooms, two full baths and living room with a fireplace. A 3 minute drive to Centreville Landing for boating, fishing and crabbing on the Corsica River. Walking distance to restaurants. Approximately 42 minutes to Annapolis, 30 minutes to Easton,1 hour 8 minutes to Baltimore and less than 2 hours from Ocean City and Rehoboth, DE. Property is 'AS IS" -Seller to make no repairs.

112 S Commerce St, Centreville

Listing courtesy of Keller Williams Select Realtors of Easton. Contact: 4106907356
$1,294,800
4 Beds ⋅ 4 Baths
*****Immediate Delivery*****WATERFRONT DEEP WATER ****Schedule showoing today! New Home, New Pier, New Pool!!!!!The Blue Heron is a new home design offered by Lacrosse Homes. The single family design features now one but TWO decks -- one from the second floor great room and the second from the third level primary bedroom suite. Take in all the beautiful sights and sounds of a Coastal Maryland lifestyle in this home built for entertaining and an enhanced lifestyle! There is room for everyone in this home, starting with a main level 2-car garage, rec room area, full bath & exercise/office -- this is your fun zone or whatever zone! The second level is light-filled and open with island kitchen featuring upgraded finishes, dining area, powder bath and great room with deck. You can ADD another deck on the rear of the home off the dining area if you're looking for more outdoor space. The third level features a laundry, three bedrooms including the spacious primary bedroom with updated bath and another stunning deck. The Blue Heron is a beautiful home and will serve a multitude of lifestyles. Explore your options today!

1757 Harbor Dr, Chester

Listing courtesy of Keller Williams Flagship. Contact:

$19,500
2 Beds ⋅ 1 Baths
This property, situated on a 0.17-acre lot, offers a blank canvas for your vision. Located in Queen Anne's County, the existing structure presents endless possibilities for the right buyer. Take advantage of the spacious lot size, perfect for outdoor activities or future expansion plans. Buyers are encouraged to perform their own due diligence to verify property details. Please note that access to 1405 Little Creek Rd is via 104 Little Creek Ct, followed by a left turn. Do not use or enter any neighboring driveways or properties as they are privately owned and clearly marked with “No Trespassing” signs. For safety reasons, please respect these boundaries.

1405 Little Creek Rd, Chester

Listing courtesy of The Parker Group. Contact: 3022176692
$699,900
3 Beds ⋅ 5 Baths
Open House July 21, 2026, 4 PM to 7 PM. Welcome to 371 Overture Way, nestled in the serene 55+ active adult community of Symphony Village in Centreville, where comfort, convenience, and connection come together beautifully. This thoughtfully maintained home offers over 6,000 square feet of living and storage space, featuring 3 spacious bedrooms, 4 full baths, and 1 half bath, along with a new roof installed in 2023 for added peace of mind. The attached two-car garage includes a durable epoxy-coated floor and stairs to generous overhead storage, perfect for keeping everything organized without sacrificing living space. Designed with ease and everyday enjoyment in mind, the bright, open main level showcases a gourmet kitchen with extended granite countertops, stainless steel appliances, and a Jenn Air gas stove, ideal for both casual meals and entertaining. The adjoining breakfast nook provides ample cabinetry and prep space, while the flowing layout includes hardwood floors, custom plantation shutters, and inviting living and dining areas. A sun-filled sunroom with wall-to-wall windows offers a tranquil retreat and opens onto a spacious deck, perfect for relaxing or hosting guests while enjoying the private wooded backdrop. The main level primary suite is a true retreat, featuring two walk-in closets, dual vanities, a soaking tub, and a walk-in shower, offering comfort and convenience all in one space. Upstairs, a versatile loft provides the perfect setting for a sitting area or home office, along with a guest bedroom complete with its own full bath and walk-in closet - ideal for visiting family and friends. The fully finished lower level expands your living space even further, with a family room featuring a fireplace, room for a game table, and a walkout to a beautifully paved patio. Two additional bonus rooms, a full bath, and an oversized storage area with a workbench, refrigerator, and freezer make this level both functional and flexible. Life in Symphony Village means more than just a beautiful home, it's a vibrant, welcoming community. Residents enjoy access to a clubhouse with social spaces, indoor and outdoor pools, a fitness center, pickleball and bocce courts, walking and hiking trails, and a full calendar of activities designed to keep you as active and engaged as you would like to be. Conveniently located near Queenstown Premium Outlets and the charming downtown area of Centreville, you will also find yourself just a short drive from the waterfront towns of Chestertown, Easton, St. Michaels, and Annapolis. This is more than a home, it is a lifestyle designed for comfort, connection, and ease. Come experience all that 371 Overture Way has to offer!

371 Overture Way, Centreville

Listing courtesy of Coldwell Banker Realty. Contact: 4102638686
$1,375,000
4 Beds ⋅ 5 Baths
BEAUTIFUL 21 ACRE WATERFRONT ESTATE WITH OVER 400' OF WATER FRONTAGE AND SEPARATELY DEEDED DEEP WATER SLIP IS INCLUDED, SLIP #16 AT THE FAR LEFT END OF THE PIER RIGHT ACROSS THE STREET! APPROXIMATELY 6 CLEARED ACRES AND 15 WOODED ACRES. SPECTACULAR 3-STORY HOME WITH 4 LARGE BEDROOMS W/ENSUITE BATHROOMS. RECENT TOP QUALITY GOURMET KITCHEN RENOVATION W/GAS COOKTOP. IT'S AWESOME! ATTACHED 2-CAR GARAGE AND A MONSTROUS DETACHED GARAGE WITH ROOM FOR 6 MORE CARS. PLENTY OF STORAGE. BEAUTIFUL, PRIVATE INGROUND GUNITE POOL. CALL LISTING AGENT FOR MANY MORE AMENITIES. READ HOA DOCS IN DISCLOSURES. TRY TO GIVE 1-2 DAYS SHOWING NOTICE, PLEASE.

105 Port Ct, Grasonville

Listing courtesy of Douglas Realty LLC. Contact: (410) 255-3690
$439,900
3 Beds ⋅ 2 Baths
PRICE Improvement...Discover the charm of this fully updated ranch in a serene, water-privileged community! With a spacious yard and an inviting open floor plan, this home features a stunning new kitchen complete with a large white granite island, sleek white cabinets, and stainless steel appliances. Sunlight floods the dining area through new sliding doors, while the generous living room is accented with stylish shiplap walls. There's Nothing Like NEW! Step onto the new flooring that leads you to three roomy bedrooms and two beautifully renovated full baths. Every detail has been attended to, with all-new windows, siding, plumbing, fixtures, electrical panel, light switches, septic work, water heater, doors, drywall, and a new HVAC system. With a recent roof and a dehumidified crawl space featuring a vapor barrier, this home is move-in ready—no worries, just settle in! The community enhances your lifestyle with access to four beaches, three boat ramps, a playground, ball fields, a basketball court, a picnic pavilion, a fishing pier, and plenty of opportunities for gatherings. This is the perfect place to create lasting memories!

1340 Queen Anne Dr, Chester

Listing courtesy of RE/MAX Executive. Contact: 4432741900