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$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:

$994,000
5 Beds ⋅ 3 Baths
Welcome to this stunning custom home overlooking the 10th green in the prestigious Prospect Bay community. Situated on a beautiful one-acre lot, this residence offers over 3,000 square feet of living space with 4-5 bedrooms and an ideal floor plan for everyday living and entertaining. The dramatic two-story foyer welcomes you into a thoughtfully designed home featuring elegant architectural details, including tray and vaulted ceilings. The bright kitchen features abundant cabinetry, a center island, pantry, and sunny morning room, plus a separate formal dining room. Open to the kitchen, the inviting family room offers bamboo flooring, a gas fireplace, custom built-ins, and access to the expansive deck overlooking the backyard and golf course. The spacious primary bedroom includes a large walk-in closet and private bath with a soaking tub, dual vanities, and a walk-in shower. Four additional bedrooms provide flexibility for guests, a home office, or multigenerational living, including one bedroom conveniently located on the main level.  Enjoy the best of Eastern Shore living with outdoor spaces designed for relaxing and entertaining. Barbecue on the large deck or gather with family and friends for a traditional Maryland crab feast in the screened gazebo while taking in peaceful golf course views. Additional highlights include a three-car garage, oversized parking pad, main level heat pump replaced in 2021, and crawl space encapsulated in 2025. Prospect Bay residents enjoy outstanding resort-style amenities, including an 18-hole championship golf course, clubhouse restaurant, swimming pool, tennis and pickleball courts, boat ramp, pro shop, and an active social calendar. Ideally located just minutes from the Chesapeake Bay Bridge, this lovely home offers the perfect combination of golf, boating, and relaxed coastal living.

14 Fairway Is, Grasonville

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

$549,900
3 Beds ⋅ 2 Baths
Symphony Village a premier 55 plus active adult community which is well desired and nicely located just on the edge of Centreville. If you are looking for the perfect 55 plus community this is it! Active adults loving life and enjoying the community this neighborhood provides from Happy Hours, Pools, events, pickleball, the gym and more. You will always see neighbors walking, riding bikes and enjoying life in the Village! This home is one of the few which gives you privacy out back backing to the woods offering you complete peace. Relax on your back patio and watch the wildlife, listen to the birds, drink your coffee, grill or have nice gatherings with your friends. This amazing and well kept home is ready for a new owner and you will not be disappointed! Offering 3 nice sized bedrooms an d2 full bathrooms with a nice open concept this floor plan allows you the option to set it up how you choose. Offering a ton of natural lighting with all of the windows this home exudes fresh and airy feelings. The kitchen has a ton of cabinets perfect for the person who loves to cook and plenty of space for your kitchen table. You will enjoy the gas fireplace all winter long as it is a great feature. The garage offers 2 parking spaces and a huge room above the garage with ample storage. This neighborhood's HOA includes lawn care, trash, snow removal, and the FANTASTIC Club house! Come and take a look and see why everyone loves Symphony Village! You will want to live here too!

126 Encore Ct, Centreville

Listing courtesy of EXP Realty, LLC. Contact: 8888607369
$5,900,000
7 Beds ⋅ 9 Baths
Designed to rival a private resort, this waterfront estate was built for celebrating with family and friends. Sweeping Chesapeake views set the stage for every gathering. The waterfront pool features a cascading rock waterfall, a tucked in bench, and a generous sun shelf, all overlooked by a pool house with a covered summer kitchen, bar, seating area, and full bath with AC. A curated firepit lounge, expansive patios and balconies, and a screened waterside porch bring indoor and outdoor living together for every occasion. At the shoreline, life on the Bay begins, with an expansive private beach perfect for wading, sandcastles, and quiet evenings by the water. The newly expanded L shaped pier stretches 260 feet and is engineered for serious boating, with dockage for a large yacht, 24,000 lb. and 10,000 lb. lifts, electric, R/O water, dual pedestals, and decorative lighting. Protected waters offer calm conditions for docking, fishing, crabbing, and watersports, with direct Bay access and easy cruising to Annapolis, St. Michaels, and beyond. A circular driveway centered by a gorgeous fountain leads to the entry, where a stunning two story foyer and grand staircase greet you, framed by spectacular water views. The great room features a soaring wall of glass and a fireplace, opening to a chef's kitchen appointed with Wolf and Sub Zero appliances, custom cabinetry, a conversation bar, pantry, and breakfast nook. The dining room seats twelve or more, ready for every holiday feast. The primary suite is a private waterfront retreat, with a sitting area beneath a domed ceiling, a fireplace, custom built ins, and a spa bath with heated floors, a jetted soaking tub, and a multi head shower. The waterfront game room offers a fireplace, wet bar, and large TV, while the private theater seats eight in front of a 100 inch screen, making this home the destination for family and friends year round. Upstairs, five architecturally unique bedrooms, three ensuite, include private waterfront balconies and a large activity room opening to a deck overlooking the pool, dock, creek, and bay. A fully equipped in law suite offers its own kitchen, living area, bedroom, fireplace, and attached two car garage, while a separate heated and cooled four car garage with porcelain tile and custom cabinetry serves as studio, workshop, or gym. Six fireplaces, Anderson and Palladian windows, tankless water heaters, a whole house water softener and reverse osmosis system, a 60KW whole house generator, and fiberoptic 2.5GB internet with seventeen access points bring comfort and connectivity throughout. Fully app based control manages lighting, HVAC, security, pool, spa, generator, music, locks, and network, inside and out. Tucked along a quiet private road with easy access to the Bay Bridge, Annapolis, and Washington D.C., this is waterfront vacation living designed to be experienced every day. Serenity Lane describes how you feel, not just where you are. Welcome home.

330 Serenity Ln, Chester

Listing courtesy of TTR Sotheby's International Realty. Contact: (410) 280-5600
$999,000
4 Beds ⋅ 3 Baths
Big reduction Three Homes! With each independent and separate addresses, all on 48 acres. The lands include woods and a pond. The primary home is 2800 square feet just recently remodeled. Open concept living all the rooms are very spacious with a kitchen with tons of storage and lots of counter space. There is an office space as well so many options to use as additional bedrooms or hobby room. A laundry area that is a room not a closet. The HVAC system was just replaced on the main home, as many other features of this house. Number two house was just put on the property in 2025, Clayton Holmes three bedrooms two baths would make a wonderful in-laws house or a rental. Number three house sits to the back of the property again is its own separate structure, is a remodled single wide. Would make an excellent income, Property or a caretaker residence. This property offers so many options it’s unlimited. It also includes a 30 x 50 insulated pole barn with a concrete floor electric separate meter and pitcher pump. Two pasture areas exist with shelter for live stock they currently have goats. This is a absolutly one of a kind property if you want to have a Equine center lots of room to build a indoor arena or to raise livestock. The entire family can live here and have there own house. The current owners have greatly improved the property it is now waiting for the next care takers to see what they do with this special property and its new use.

420 Duhamel Corner Rd, Marydel

Listing courtesy of Benson & Mangold, LLC.. Contact: (410) 479-0777
$649,900
4 Beds ⋅ 3 Baths
Welcome to life on Kent Island in the sought-after Cox Creek Landing community—where coastal charm meets everyday convenience. With water access on the community pier and available BOAT SLIP EASEMENT WITH BOAT LIFT! CCL neighborhood is perfect for embracing the Chesapeake Bay lifestyle, all just minutes from shopping, dining, and local amenities. From the moment you arrive, the inviting front porch sets the tone—an ideal spot to relax with a morning coffee or unwind in the evening while enjoying the peaceful surroundings. Inside, the home is thoughtfully designed for both comfort and functionality. The main level features a desirable first-floor primary suite with a full bath, along with an additional half bath for guests. A private home office with elegant glass doors provides the perfect space for remote work or quiet retreat. The heart of the home is the open-concept kitchen and family room, where vaulted ceilings create an airy, inviting atmosphere. Just beyond, a sun-filled morning room offers the perfect place to start your day, overlooking the beautifully landscaped backyard. Step outside to a brick patio surrounded by lush, mature landscaping, creating a private outdoor oasis ideal for entertaining or relaxing. A side-load two-car garage adds both curb appeal and practicality. Upstairs, you’ll find an additional three generously sized bedrooms and a full bath, offering ample space for all with 4 bedrooms throughout. This home perfectly blends style, space, and location—offering a rare opportunity to enjoy the best of Kent Island living in a waterfront-access community.

303 Creeks End Ln, Stevensville

Listing courtesy of Paul Wesley Real Estate. Contact: 7032822709
$485,000
4 Beds ⋅ 2 Baths
Lovely 4 bedroom rancher with big, fenced backyard on cul de sac in Stevensville neighborhood of Cloverfields on Kent Island. Community pool, beach, clubhouse, playground, and boat marina. Very large primary bedroom addition, big living room, large kitchen-dining combo area, nice outdoor deck off kitchen, two large outbuildings in backyard and plenty of room for garden, fire pit, volleyball etc.

15 Dixon Ct, Stevensville

Listing courtesy of Cottage Street Realty LLC. Contact:

$2,850,000
5 Beds ⋅ 5 Baths
Set on Forty Five picturesque acres of prime agricultural land with extensive tillable acreage, this exceptional Five bedroom, Four and one half bath brick colonial blends timeless design with modern versatility and waterfront charm. Privately situated on a quiet cove just off the mouth of the Chester River, the property offers a rare combination of space, functionality, and lifestyle appeal. Inside, the home features a thoughtfully designed layout ideal for both everyday living and entertaining. A main-level en-suite provides excellent flexibility for multi-generational living or private guest quarters, while an additional upper-level en-suite enhances comfort and convenience for visitors. The spacious primary suite serves as a true retreat, complemented by well-proportioned secondary bedrooms and multiple full baths. Refined living spaces include a formal dining room, a dedicated home office perfect for remote work, and an inviting screened porch overlooking the water—an ideal setting to relax and take in the tranquil views. The nearly fully finished basement expands your living options with generous space for recreation, hobbies, or a workshop. Recent upgrades—including a new roof and septic system—offering peace of mind, while the 2-zone HVAC system ensures efficient year-round comfort. Outdoors, enjoy the in-ground pool surrounded by a patio, perfect for entertaining or unwinding, along with open acreage that offers endless possibilities for farming, equestrian use, or a private rural lifestyle. Complete with a Twocar garage and located in a highly desirable waterfront setting, this property presents a rare opportunity to own a versatile estate that balances luxury living, scenic beauty, and agricultural potential.

1810 Love Point Rd, Stevensville

Listing courtesy of Monument Sotheby's International Realty. Contact: (410) 525-5435
$799,900
4 Beds ⋅ 3 Baths
To be built, brand new colonial featuring 4 bedrooms, 2.5 baths, two car garage. STANDARD FEATURES include LVP flooring, quartz countertops, stainless steel appliances, and more! Model home can be seen at 307 Columbia (different model but same builder). Pictures do show options

Queens Colony High Rd, Stevensville

Listing courtesy of Coldwell Banker Waterman Realty. Contact: (410) 643-5005
$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:

$595,000
4 Beds ⋅ 3 Baths
OPEN HOUSE Sun July 26, 1-3. Amazing new price!! Welcome to one of the best values in the Centreville area. Nestled on a beautiful 1.5 acre lot that boasts NO HOA/restrictions, this custom built 3200+sqft retreat is designed for everyday comfort and unforgettable entertaining. You will love the 12x14 screened in porch, front wrap around porch & the huge fenced in backyard where you can store your toys in the 2 story 12x20 shed or larger 12x28 shed. Custom finished 20’x20’ rec room on the first floor that has potential to be made into a garage if needed. This home has been extensively improved throughout with fresh paint, new carpet, updated hardware, refinished hardwood floors, granite kitchen counters, upgraded lighting and thoughtful custom touches in nearly every room. The heart of the home is the gourmet kitchen with granite counters, gas stove and stainless steel appliances that overlooks the beautiful back yard. Other impressive features include an alarm system, 1st floor separate office, separate living room, separate family room, separate dining room, fiber optic internet, hardwood floors, household humidifier, water conditioner, primary bedroom with huge sitting area and laundry room on 2nd floor, fireplace and so much more. Reduced over $50K to cover a garage. Top it off with a home warranty and this is what you have been looking for.

337 Roe Ingleside Rd, Centreville

Listing courtesy of Taylor Properties. Contact:

$1,995,000
4 Beds ⋅ 4 Baths
Waterfront living in Queenstown with sought-after southeastern exposure and 7 ft MLW, offering ideal conditions for boating and enjoying life on the water. Set on a beautifully landscaped, high-elevation lot, the property provides both privacy and peace of mind, with mature plantings, manicured grounds, and a paved driveway that creates a welcoming approach. This 4-bedroom, 3.5-bath home spans approximately 3,400± sq ft and is thoughtfully designed with a spacious, functional layout, including a first-floor bedroom and multiple living areas that capture natural light and water views throughout. The home features a bright sunroom overlooking the water, a partially finished basement for added flexibility, and a second-floor primary suite with a private balcony—perfect for taking in peaceful morning views. Outdoor living is equally impressive, with multiple areas designed for entertaining and relaxation. An expansive brick hardscaped patio anchors the backyard, offering seamless indoor-outdoor flow and the perfect setting for gatherings, dining, or quiet evenings by the water. The private dock, complete with a 12,000 lb boat lift, provides easy access for boating, with a quick run to the restaurants at Kent Narrows and the historic charm of St. Michaels. Additional highlights include a two-car garage and well-proportioned living spaces that offer both comfort and versatility. Conveniently located just minutes from Route 50 and the Bay Bridge, this property offers an ideal balance of waterfront lifestyle and accessibility. A strong waterfront offering in a desirable Queenstown location, combining elevation, views, and effortless boating access.

377 Hemsley Dr, Queenstown

Listing courtesy of Benson & Mangold, LLC. Contact: 4108226665
$524,900
4 Beds ⋅ 3 Baths
Dreaming of a peaceful, private rural retreat near the Chesapeake Bay. This beautifully maintained 4-bedroom, 2.5-bath Colonial offers the perfect blend of comfort, space, and outdoor living—all set on just over an acre of level, manicured land. Enjoy your own private backyard oasis featuring a fully fenced 36' x 16' in-ground saltwater pool—perfect for relaxing or entertaining. The screened 3-season porch provides a tranquil space to unwind, while the cozy wood-burning fireplace and Bose surround sound system make the family room ideal for year-round enjoyment. Inside, you'll find a traditional layout with a spacious family room, separate living room, and formal dining room. The kitchen is enhanced with a reverse osmosis water system and instant hot water for added convenience and everyday luxury. The primary bedroom includes charming under-the-eaves storage, offering both character and functionality. Major updates provide peace of mind, including a new roof and gutters (2024), hot water heater (2023), and a 4-ton HVAC system (2021). Complete with an exterior shed and plenty of open space, this property delivers the privacy of country living with convenient access to the Chesapeake Bay.

112 Lently Farm Ln, Centreville

Listing courtesy of HomeSmart. Contact: 3013524065
$585,000
4 Beds ⋅ 4 Baths
A standout offering in North Brook, this exceptional home, built in 2018, delivers 3,508 finished square feet of beautifully upgraded living space with 4 bedrooms and 3.5 baths. Showcasing over $100,000 in builder enhancements, this home reflects exceptional attention to detail throughout with a high-end level of finishes. From the moment you arrive, the inviting front porch sets a warm and welcoming tone. Step inside to discover a thoughtfully designed layout enhanced by an abundance of tall windows that fill the home with natural light, all complemented by custom blinds throughout. The heart of the home is the spacious gourmet kitchen, featuring a large island and breakfast bar—ideal for both everyday living and entertaining. Just off the kitchen, the morning room offers a bright and versatile space that can serve as a separate living or dining area, complete with a cathedral ceiling and direct access to the backyard, creating a seamless indoor-outdoor connection. The fully finished basement provides additional flexible living space, perfect for recreation, guests, or a home office. Upstairs, you’ll find a spacious primary suite with a spa-like bath, along with generously sized secondary bedrooms that offer comfort and flexibility for family or guests. Step outside to a backyard designed for entertaining and fun. Enjoy summer days in your in-ground, heated saltwater gunite pool with waterfall, surrounded by a composite deck, extensive hardscaping, and a fully fenced yard. A beautifully designed paver walkway leads to a custom Amish-built shed, completing this impressive outdoor retreat. Located in a vibrant community with trails, playgrounds, and easy access to Rt. 301, North Brook offers a playground, soccer field, pavilion, walking paths, ponds, and wooded areas to explore. Just moments from historic downtown Centreville, you’ll enjoy unique restaurants and shops, local events, arts and entertainment, and a variety of outdoor activities. Mortgage savings may be available for buyers of this listing.

131 Fair Brook Way, Centreville

Listing courtesy of Redfin Corp. Contact: 3016586186
$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:

$969,000
4 Beds ⋅ 3 Baths
STUNNING NEW CONSTRUCTION – Experience the pinnacle of modern luxury in this exquisite "Farmhouse Chic" masterpiece, perfectly situated in a highly coveted Kent Island community near the shores of the Chesapeake Bay. Offering over 2,600 square feet of meticulously crafted living space, this residence features 4 spacious bedrooms, 2.5 designer baths, and a versatile retreat living space tailored for contemporary life, with optional 5th and 6th bedrooms. Covell Signature Homes provides well-crafted homes specified to fit YOUR needs! Act soon and you can DESIGN YOUR DREAM HOME the way YOU want it, with all the finishes, options and features that work for YOUR life. The home’s striking exterior sets the stage for the upscale finishes found within. Step inside to an expansive open-concept Great Room and a gourmet kitchen designed for the culinary enthusiast, complete with high-end stainless-steel appliances, premium countertops, and a massive island perfect for entertaining. Durable, luxury vinyl plank flooring flows seamlessly throughout the main areas, leading to a dedicated private study—the ideal sanctuary for a home office or library - or an optional 5th bedroom. Retreat to the upper level where the additional living area provides a second gathering spot, while the primary suite offers a spa-like escape. The retreat living space can also convert to a 5th or 6th bedroom. Every inch of this home reflects a commitment to quality and style, blending rustic farmhouse charm with sophisticated, high-end details. The lifestyle is equally unmatched. Located in a premier water-access community, you can keep your boat at the Queen Anne Marina, enjoy a round of golf at the adjacent Blue Heron Golf Course, or explore the island’s famous waterfront dining just minutes away. This is more than a home; it is an incredible opportunity to own a piece of the Kent Island dream!

416 5 Farms Dr, Stevensville

Listing courtesy of Coldwell Banker Realty. Contact: 4102638686
$999,000
5 Beds ⋅ 5 Baths
Welcome to luxury coastal living in the highly desirable Four Seasons at Kent Island 55+ community in Chester. Built in 2025, this practically new home offers the perfect blend of elegance, comfort, and convenience — without the wait for new construction. Ideally situated on coveted Kingfisher Lane, this exceptional Tuscaloosa model offers over 3,200 square feet of beautifully designed living space with 5 bedrooms and 4.5 baths. The upgraded stone-and-shake exterior creates stunning curb appeal, while the covered front porch offers peaceful peek-a-boo water views — the perfect place to enjoy your morning coffee at sunrise. Inside, the open-concept main level showcases a thoughtfully upgraded interior with classic cabinetry, glass display cabinets, and professional-grade GE appliances in the kitchen. The spacious living area is anchored by a dramatic stone gas fireplace, while custom wall detailing and molding upgrades in the foyer and primary suite add warmth and sophistication throughout the home. Norman shutters on every window, upgraded carpet with premium padding, and carefully selected finishes elevate every room. The main-level primary suite offers a private retreat with elegant trim details and a spa-inspired en suite bath featuring a luxurious soaking tub designed for relaxation. Additional upgrades include a screened porch for outdoor enjoyment, epoxy garage flooring, painted garage walls, and a dedicated EV charging station for modern convenience. Located just a short distance from the community dog park, playground, pickleball and tennis courts, and the state-of-the-art clubhouse, this home offers not only exceptional design but also an unmatched lifestyle. Residents of Four Seasons at Kent Island enjoy resort-style amenities including indoor and outdoor pools, a fitness center, walking trails, social spaces, and activities designed to support an active and vibrant coastal lifestyle. All of this is ideally located just minutes from the Chesapeake Bay Bridge, offering convenient access to Washington and Baltimore, while also being close to shopping at the Queenstown Premium Outlets and an array of local waterfront dining and everyday conveniences.

233 Kingfisher Ln, Chester

Listing courtesy of Samson Properties. Contact: 7033788810
$382,400
3 Beds ⋅ 1 Baths
Move-in ready rancher in Cloverfields, one of Kent Island’s desirable water-oriented communities with access to an impressive list of neighborhood amenities. This 3-bedroom home offers comfortable one-level living with updated flooring, fresh paint, a renovated bathroom, generous bedroom closet space, and a bright living area that feels clean, practical, and easy to maintain. There is professionally installed alarm and camera system, and the seller is including one free year of monitoring for the new owner. Outside, the .35 acrre lot offers a large yard with mature trees and plenty of space for outdoor living, gardening, play, pets, or future improvements. The real standout is the Cloverfields lifestyle. Community amenities include a beach, marina with rental slips, boat ramp, fishing pier, swimming pool, kiddie pool, clubhouse, playgrounds, basketball court, picnic areas, grills, pavilions, and more. Enjoy Eastern Shore living with everyday convenience, just minutes from the Chesapeake Bay Bridge, shopping, restaurants, dock bars, parks, and The Cross Island Trail. Whether you want a primary residence, weekend retreat, or an easy-to-maintain home close to the water, this property offers a rare combination of value, location, and community amenities on Kent Island. Schedule your showing and come see why Cloverfields is such a special place to call home.

920 Cloverfields Dr, Stevensville

Listing courtesy of Benson & Mangold, LLC.. Contact: (410) 479-0777
$749,000
3 Beds ⋅ 2 Baths
Positioned directly on holes 1 and 9 of the prestigious Cove Creek Club golf course, this beautifully maintained home offers a rare opportunity to enjoy true golf course living on Maryland’s Eastern Shore. Located within one of Kent Island’s most sought-after gated waterfront communities, this property combines scenic fairway views, resort-style amenities, and low-maintenance luxury living, all just minutes from the Bay Bridge. Set on approximately one acre, this 3-bedroom, 2-bath home is thoughtfully designed for both comfortable everyday living and effortless entertaining. The community’s private USGA-rated golf course, designed by renowned architect Lindsay Ervin, winds through rolling fairways and waterfront landscapes, creating one of the most unique golf and boating communities on the Eastern Shore. The course itself is known for its distinctive layout, offering 18-hole play through creative tee placements across 9 beautifully maintained holes. Inside the home, you’re welcomed by a formal living room, while a second living space opens seamlessly into the kitchen and dining area. The gourmet kitchen features a Viking 5-burner stove, generous prep space, and an ideal setup for gatherings after a day on the course or water. A dedicated office/library with custom built-in cabinetry creates the perfect work-from-home space or quiet retreat overlooking the peaceful surroundings. Above the attached two-car garage, a fully conditioned bonus room offers flexible living space ideal for guests, a home gym, media room, or additional lounge area. Step outside and enjoy a fenced backyard with direct golf course ambiance and easy access to the clubhouse, marina, and waterfront amenities that make Cove Creek Club so desirable. To make enjoying the community even easier, a Club Car golf cart conveys with the property, perfect for cruising to the clubhouse, golf course, marina, or private beach. Residents enjoy access to: • Private golf course • Clubhouse • Marina & boat ramp • Private beach • Tennis courts • Waterfront walking areas • Lawn maintenance included • Well & septic maintenance covered by the community for this property This is more than just a home, it’s a lifestyle built around golf, boating, waterfront living, and the relaxed elegance that makes Kent Island so special.

301 Penny Dr, Stevensville

Listing courtesy of Samson Properties. Contact: 7033788810
$559,000
3 Beds ⋅ 3 Baths
Welcome to this beautifully maintained 3-bedroom, 2.5-bathroom home in the Waterman’s Cove community in Chester. Nestled on a quiet street along scenic Cox Creek, this charming property offers the perfect blend of comfort, style, and convenience. An inviting front porch welcomes you home, while water views greet you upon arrival and can also be enjoyed from the spacious rear composite deck, built by Lundberg Builders, perfect for relaxing or entertaining. The home sits adjacent to community open space, offering added privacy with no direct neighbor next door. Inside, you’ll find hardwood flooring and an open-concept layout designed for modern living. The living room flows seamlessly into the dining area and kitchen, which features granite countertops, stainless steel appliances, and a beautiful tile backsplash. Sliding doors off the dining area lead to the composite deck and a lush, partially fenced yard, creating an ideal space for indoor-outdoor living. The kitchen also provides convenient interior access to the attached one-car garage. Upstairs, the primary suite offers a well-appointed bath, two additional bedrooms, a second full bath, and a laundry room for added convenience. Located just one mile from Route 50 on Cox Neck Road, this home offers quick access to shopping, dining, commuter routes to Washington DC and Baltimore, and the Chesapeake Bay Bridge. The intimate Waterman’s Cove community consists of just nine homes, with HOA services that include lawn care and trash removal - making for easy, low-maintenance living. Enjoy the peaceful lifestyle of Maryland’s Eastern Shore, with water views and privacy in a highly convenient location.

126 Watermans Cove Ln, Chester

Listing courtesy of Coldwell Banker Realty. Contact: 4102638686
$672,800
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. and you can customize your lower level rec area to suit your needs. Located just a short walk to the waterfront, the community features a boat launch, pavillion, playground, and bayfront recreational area. Move in ready with versatile living spaces and a thoughtful layout.

323 Chenowith Dr, Stevensville

Listing courtesy of Keller Williams Flagship. Contact:

$699,800
4 Beds ⋅ 3 Baths
One of our most popular designs, The New 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. and you can customize your lower level rec area to suit your needs. There is a community beach, a pool and rental slips for the boat. Additionally, there is a playground and tot lot. A great place to claim the Eastern Shore Way of Life. As part of the Cloverfield Home Association, residents enjoy an array of community amentities that elevate the lifestyle: a sparkling pool for summer fun, a private community beach where you can dip your toes in the sand, a playground and tot lot, a marina that has boat rental slips available, and additiaonl recreational spaces that make this neighborhood one of the most sought after on the Eastern Shore. With an easy commute to anywhere on the Eastern Shore, as well as quick access to Annapolis and even Washington DC. This location blends convenience with coastal charm.

233 Nichols Manor Dr, Stevensville

Listing courtesy of Keller Williams Flagship. Contact:

$1,195,000
4 Beds ⋅ 5 Baths
Located in the prestigious Southwind community, a penisula between Crab Alley Bay & Cox Creek, this elegant contemporary ranch-style home offers an unparalleled lifestyle of luxury and comfort. Spanning over 4,400 sq. ft. of finished space, the interior boasts elegant marble flooring, complemented by crown moldings and built-ins that enhance its sophisticated charm. The gourmet kitchen, featuring upgraded countertops and a spacious island, flows seamlessly into the family room, perfect for entertaining. Relax in the primary suite with a lavish bath or unwind in the inviting family room by the fireplace with views out to Crab Alley. Three additional bedrooms (or two bedrooms and an office) and two baths round out the main level that offers sweeping scenic views from every vantage point. Step outside to discover a private oasis on 1.25 acres, complete with extensive hardscaping, a heated in-ground pool, and a soothing hot tub. Enjoy picturesque water views out the front and back, with access for kayaking and boating. The community amenities, including a beach, clubhouse, and tennis courts, elevate your living experience. This home is not just a residence; it's a lifestyle waiting to be embraced and enjoyed. Start living your best 'Shore Life' at 2855 Cox Neck Rd.

2855 Cox Neck Rd, Chester

Listing courtesy of Wilson Realty & Staging LLC. Contact: 4103042250
$337,500
3 Beds ⋅ 2 Baths
Motivated Seller!!! Loan is assumable for a qualified veteran. Opportunity to own a beautiful rancher on 0.46 ac in the town of Crumpton. This home was built in 2021. It has been maintained, and kept meticulously. It compares nicely to new construction. The front porch welcomes you to a well-designed open concept 3 BR, 2 full bathrooms home. Natural light illuminates the living space. There is no shortage of amenities: an updated, modern kitchen with SS appliances, under cabinet lighting, granite countertops, whole house sprinkler system. The laundry room adjoins the kitchen. This home offers plenty of room for all of your outdoor activities. It's two blocks to the boat ramp (Chester River). Easy commute to Route 301, Chestertown, Middletown, and the Bay Bridge. This is a one of a kind listing. Don't wait. Schedule your showings today!

209 3rd St, Crumpton

Listing courtesy of EXP Realty, LLC. Contact: 8885434829
$365,000
3 Beds ⋅ 2 Baths
Practically brand new and just 2 years young with access to the Chester River, this beautifully maintained home is perfectly situated in a desirable water-oriented community—offering the best of Eastern Shore living! Located in the Queen Anne’s County school district and just minutes from downtown Chestertown, you’ll love the convenience paired with the peaceful setting. Enjoy easy access to the Chester River—you can drive your boat to the community ramp at the end of the street, or even take a nice short walk down to the water, to spend your days crabbing, fishing, kayaking, or simply soaking in the waterfront lifestyle. Inside, this 3-bedroom, 2 full bath home features durable and stylish LVP flooring throughout and a thoughtfully designed split floor plan. The spacious primary suite is privately situated on one side of the home and offers a walk-in shower, dual vanity, and a beautifully appointed bath. On the opposite side, you’ll find two additional bedrooms and a full bath with a tub/shower combo—ideal for guests or flexible living. The kitchen and living room are centrally located, creating an inviting and functional space for everyday living and entertaining. A standout bonus—an unfinished upstairs area of 544 additional SF, already in place and ready for your vision! Use it for storage now or finish it off for additional bedrooms, a home office, or recreation space. Step outside and enjoy both a charming front porch—perfect for morning coffee—and a massive back deck ideal for entertaining, grilling, or simply relaxing while taking in the peaceful surroundings. The generously sized yard with mature trees offers both privacy and room to enjoy the outdoors. Even more exciting—the county has indicated plans to pave the road in the near future. Added perk: fiber optic Talkie Internet is already available at the property, making working from home or streaming a breeze. Move-in ready, full of potential, and located in a charming waterfront community—this one checks all the boxes!

240 Merganser Dr, Chestertown

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

$4,700,000
6 Beds ⋅ 6 Baths
Welcome to 200 Wye Road, an exceptional waterfront estate set on over two private acres along the Wye River, directly across from the protected natural beauty of Wye Island. Here, scale, setting, and thoughtful design converge to create a truly elevated Eastern Shore lifestyle. Spanning more than 8,100 square feet across three finished levels, the residence offers a refined yet highly livable floor plan designed to capture water views from nearly every room. Expansive living spaces, a formal dining room with handpainted custom wallpaper from the U.K., and a reimagined gourmet kitchen create an environment equally suited for everyday living and large-scale entertaining. The kitchen has been thoughtfully redesigned with updated cabinetry, statement lighting, and a full suite of premium appliances, including Wolf, Sub-Zero, and Bosch. The home offers exceptional flexibility, including an optional first-floor primary suite, a dedicated home gym, two laundry rooms, and an oversized mudroom designed for seamless day-to-day living. Two wood-burning fireplaces add warmth and character, enhancing the home’s sense of comfort and timeless appeal. The primary suite serves as a private retreat, complete with two walk-in closets and a fully renovated, spa-inspired bath featuring heated flooring, a soaking tub, a glass-enclosed shower, and its own gas fireplace, delivering a level of comfort and detail rarely found. Since 2024, the property has undergone extensive upgrades that enhance both performance and long-term value, including a new Owens Corning roof with a transferable warranty, three fully replaced Trane HVAC systems, a whole-home water filtration system, and comprehensive renovations throughout the bathrooms and interior spaces. Outdoor living is where the property truly distinguishes itself. A newly renovated 20x40 waterfront pool with a pebble finish and automatic cover anchors the setting, complemented by expansive hardscaping, manicured grounds, and multiple areas designed for entertaining or quiet relaxation. The shoreline has been improved with 250 feet of stone rip rap, and the deep-water dock is outfitted with new electrical service and lighting, featuring a new 25,000 lb boat lift and a 12,000 lb one along with two additional slips, providing effortless access to the Wye River and beyond. Whether enjoying sunrise coffee on the screened porch, hosting summer gatherings by the pool, or heading out by boat to St. Michaels or the Kent Narrows, this property offers a lifestyle defined by ease, privacy, and connection to the water. Conveniently located in Queenstown, just minutes from shopping, dining, and Route 50, with easy access to Annapolis and Easton, 200 Wye Road represents a rare opportunity to own a turnkey waterfront estate in one of the Eastern Shore’s most sought-after settings.

200 Wye Rd, Queenstown

Listing courtesy of TTR Sotheby's International Realty. Contact: (410) 280-5600
$424,000
3 Beds ⋅ 3 Baths
Cloverfields - This 3 bedroom 2 1/2 bath home is move in ready and updated with new carpet, paint, vinyl flooring, new bathroom cabinets and kitchen. The community offer pool, beach, boat ramp, play area and community club house. This is the perfect home to have just in time for summer and use all the community benefits.

729 Davol Rd, Stevensville

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

$569,000
5 Beds ⋅ 3 Baths
Nestled in a peaceful country setting in Queenstown, Maryland, this spacious 5-bedroom, 2.5-bath Colonial offers the perfect blend of privacy, comfort, and room to grow. Located in the heart of Queen Anne's County on Maryland's Eastern Shore, this beautiful home combines the tranquility of country living with the convenience today's buyers are searching for. Designed with everyday living and entertaining in mind, the home features generous living spaces filled with natural light. The large kitchen provides plenty of room for meal preparation and gathering with family and friends, while the adjoining family room with a cozy fireplace creates a warm and inviting atmosphere. Just off the family room, the screened-in porch offers the perfect space for outdoor dining, morning coffee, or relaxing while enjoying peaceful country views. The main level includes a versatile fifth bedroom, making it ideal for guests, multigenerational living, a private home office, or a flex space to fit your lifestyle. Upstairs, you'll find a spacious primary suite with an ensuite bath, along with three additional generously sized bedrooms and a newly renovated full bathroom. A finished bonus room over the two-car garage provides even more flexible living space—perfect for a home office, playroom, media room, home gym, or recreation area. Step outside to a fully fenced backyard that's ideal for pets, children, and outdoor entertaining. Backing to open farmland with no homes behind, the property offers exceptional privacy and scenic views rarely found in today's market. Additional highlights include a two-car attached garage, ample storage, and a functional floor plan designed for modern living. Conveniently located just minutes from the Queenstown Premium Outlets, Route 301, waterfront restaurants, marinas, and the many attractions of Maryland's Eastern Shore, this home also offers an easy commute to Annapolis, the Chesapeake Bay Bridge, and Delaware beaches. If you're searching for a spacious Queenstown home for sale with flexible living spaces, country charm, and a prime location, this exceptional property is one you won't want to miss.

306 Overlook Dr, Queenstown

Listing courtesy of Coldwell Banker Realty. Contact: kelly.thompson@cbmove.com
$520,000
4 Beds ⋅ 3 Baths
Welcome to this charming home nestled in the quaint town of Ingleside, MD, offering the perfect blend of comfort, space, and peaceful country living. Situated on a generous .70 acre lot, this 2 1/2 story residence provides room to grow, and enjoy the beauty of it’s serene surroundings. Inside, you’ll find 4 spacious bedrooms, 2 full baths and 1 half bath, thoughtfully designed for both everyday living and entertaining. The kitchen features sleek stainless steel appliances, self closing cabinetry, and a cozy eat-in area, while a separate formal dining room provides the perfect setting for gatherings and special occasions. Luxury Vinyl Plank flooring runs throughout the main living area, offering durability and style, with soft carpeting in the bedrooms for added comfort. The primary suite includes a private en-suite bath with a walk in shower, creating a relaxing retreat at the end of the day. The versatile fourth bedroom on the third floor offers endless possibilities- ideal as a playroom, home office, or private getaway space. Step outside to a large rear deck with IPE decking, overlooking a fully fenced backyard, perfect for pet, children, or simply enjoying the outdoors. Additional features include an encapsulated crawl space for improved energy efficiency and moisture control, a spacious storage shed, and a chicken coop with chickens that can convey with the property if desired. Perfect for those looking to embrace a bit of country living. This property offers the tranquility of rural life with all the comforts of home, don’t miss your opportunity to make it yours.

2649 Roberts Station Rd, Ingleside

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

$1,049,500
5 Beds ⋅ 5 Baths
Price Reduced $50K – Check out the Virtual Tour! Exceptional Value in Four Seasons at Kent Island Why wait to build? This less-than-one-year-old Tuscaloosa model on sought-after Kingfisher Lane delivers the upgrades, location, and efficiency buyers are chasing—without the timeline or added expense. Positioned just across from the Chester River, enjoy peekaboo water views from the covered front porch and even a sightline to the clubhouse. Inside, the home is bright, open, and thoughtfully designed with 5 bedrooms and 4.5 baths, offering flexibility for guests, work-from-home space, or multigenerational living. It shows like new—but lives better—because everything has already been elevated beyond builder grade. Over $70,000 in post-builder upgrades, including: • Owned solar system (10kW+) providing substantial energy savings • Custom closet systems throughout the home • Custom window treatments already installed • Premium Café Series appliances • Tankless water heater • Upgraded lighting and fixtures • Additional high-end finishes and improvements throughout The spacious floor plan offers room for everyone, while the oversized garage provides ample storage for vehicles, golf carts, and all the gear that comes with Eastern Shore living. Life in Four Seasons at Kent Island is about more than the home itself. Residents enjoy resort-style amenities including a stunning clubhouse, indoor and outdoor pools, fitness center, pickleball courts, walking trails, kayak launch, fishing pier, and an active social calendar designed for a vibrant lifestyle. With immediate availability, extensive upgrades already completed, and one of the community's most desirable locations, this home represents an opportunity that's becoming increasingly difficult to find. Add in the recent $50,000 price reduction, and this is one of the best values currently available in Four Seasons at Kent Island. Don't miss your chance to enjoy nearly new construction, energy-efficient living, and the Chesapeake Bay lifestyle you've been waiting for.

215 Kingfisher Ln, Chester

Listing courtesy of RE/MAX Executive. Contact: 4432741900