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$909,990
2 Beds ⋅ 3 Baths
Welcome to the Chester, a thoughtfully designed home offering 2 bedrooms, 2.5 baths, and a 1-car garage. Scheduled for settlement in December 2026, this home combines modern comfort with functional and stylish living spaces. The main living area features a dry bar and an electric fireplace, creating a warm and inviting atmosphere perfect for both relaxing and entertaining. A dedicated home office with lited French doors provides a private and elegant workspace. The kitchen is designed for both everyday living and convenience, featuring a single oven, microwave, gas cooktop with range hood, dishwasher, pendant lighting, tile backsplash, and quartz countertops. Luxury vinyl plank flooring flows throughout the home, with tile flooring in both full baths. The owner’s bath offers a walk-in shower with a seat and handheld shower wand, double sinks, and quartz countertops, creating a comfortable and functional 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.

102 Boatswain Way Unit 2943, Chester

Listing courtesy of Berkshire Hathaway HomeServices PenFed Realty - OP. Contact:

$809,990
2 Beds ⋅ 3 Baths
Welcome to the Chester, a thoughtfully designed home offering 2 bedrooms, 2.5 baths, and a 1-car garage. Scheduled for settlement in December 2026, this home combines modern comfort with functional and stylish living spaces. The main living area features a dry bar and an electric fireplace, creating a warm and inviting atmosphere perfect for both relaxing and entertaining. A dedicated home office with lited French doors provides a private and elegant workspace. The kitchen is designed for both everyday living and convenience, featuring a single oven, microwave, gas cooktop with range hood, dishwasher, pendant lighting, tile backsplash, and quartz countertops. Luxury vinyl plank flooring flows throughout the home, with tile flooring in both full baths. The owner’s bath offers a walk-in shower with a seat and handheld shower wand, double sinks, and quartz countertops, creating a comfortable and functional 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.

102 Boatswain Way Unit 2932, Chester

Listing courtesy of Berkshire Hathaway HomeServices PenFed Realty - OP. Contact:

$809,990
2 Beds ⋅ 3 Baths
Welcome to the Chester, a thoughtfully designed home offering 2 bedrooms, 2.5 baths, and a 1-car garage. Scheduled for settlement in December 2026, this home combines modern comfort with functional and stylish living spaces. The main living area features a dry bar and an electric fireplace, creating a warm and inviting atmosphere perfect for both relaxing and entertaining. A dedicated home office with lited French doors provides a private and elegant workspace. The kitchen is designed for both everyday living and convenience, featuring a single oven, microwave, gas cooktop with range hood, dishwasher, pendant lighting, tile backsplash, and quartz countertops. Luxury vinyl plank flooring flows throughout the home, with tile flooring in both full baths. The owner’s bath offers a walk-in shower with a seat and handheld shower wand, double sinks, and quartz countertops, creating a comfortable and functional 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.

102 Boatswain Way Unit 2933, Chester

Listing courtesy of Berkshire Hathaway HomeServices PenFed Realty - OP. Contact:

$699,990
2 Beds ⋅ 3 Baths
Welcome to the Chester, a thoughtfully designed home offering 2 bedrooms, 2.5 baths, and a 1-car garage. Scheduled for settlement in October 2026, this home combines modern comfort with functional living spaces. The heart of the home features a dry bar and an electric fireplace, creating a warm and inviting atmosphere. A dedicated home office with lited French doors provides a stylish and private workspace. The kitchen is designed for both everyday living and entertaining, featuring a single oven, microwave, gas cooktop with range hood, dishwasher, pendant lighting, tile backsplash, and quartz countertops. Luxury vinyl plank flooring flows throughout the home, with tile flooring in both full baths. The owner’s bath offers a walk-in shower with seat and handheld shower wand, double sinks, and quartz countertops for added convenience and style. 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.

110 Boatswain Way Unit 3042, Chester

Listing courtesy of Berkshire Hathaway HomeServices PenFed Realty - OP. Contact:

$439,900
4 Beds ⋅ 3 Baths
Seller incentive! Seller is willing to contribute toward a mortgage rate buy-down for the buyer with an acceptable offer. Welcome to 102 Sophie Lane in the sought-after Ellendale community of Stevensville! A beautiful end-unit townhome. Inside, you’ll find a functional layout that’s perfect for everyday living and entertaining, with inviting living spaces, a seamless flow throughout, and natural light that enhances the home’s warm and welcoming feel. The living room is highlighted by a stylish shiplap accent wall with an electric fireplace, creating a warm and inviting focal point. The kitchen features granite countertops and an island, while the composite rear deck provides the perfect space to relax, entertain, or enjoy your morning coffee. The bedroom closets are thoughtfully outfitted with custom California Closets® organization systems, offering both style and exceptional storage. Located in the amenity-rich Ellendale community, residents enjoy access to a community pool, piers, walking trails, playgrounds, and beautifully maintained common areas, creating the perfect setting for an active lifestyle and family-friendly living. Conveniently located just minutes from shopping, dining, schools, and with easy access to Route 50, this home offers the ideal balance of neighborhood charm and convenience. Don’t miss your opportunity to own this beautiful home in one of Kent Island’s most desirable communities!

102 Sophie Ln, Stevensville

Listing courtesy of Douglas Realty LLC. Contact:

$509,900
4 Beds ⋅ 3 Baths
**Priced to Sell!** Welcome to 427 Brookfield Drive, a move-in ready home in Centreville's sought-after NorthBrook community, offering the perfect blend of space, comfort, privacy, and energy efficiency. The backyard is made for gathering, with a newly created fire pit and cozy seating area - the perfect setting for crisp fall evenings, entertaining friends, or simply unwinding at the end of the day. Situated on a premium lot backing to White Marsh Park, this 4-bedroom, 2.5-bath home offers over 2,500 square feet of thoughtfully designed living space with no homes directly behind, providing peaceful views and a private backyard setting. The main level features a bright, open floor plan ideal for both everyday living and entertaining. The family room showcases vaulted ceilings and a cozy propane fireplace and flows seamlessly into the kitchen, complete with granite countertops, stainless steel appliances, a double oven, and center island. A dedicated home office/flex space and convenient half bath add versatility for today's lifestyle. Upstairs, the generously sized primary suite offers a private retreat with an en-suite bath and oversized walk-in closet. Three additional bedrooms, a full bath, and an upper-level laundry room provide the functionality buyers are looking for. Another standout feature is the home's energy-efficient solar panel system, helping reduce electricity costs while adding energy efficiency. Additional recent improvements include a new roof with transferable warranty (2023), luxury vinyl plank flooring (2024), new upper-level carpeting (2026), updated kitchen appliances, vinyl privacy fence (2022), new garage door (2024), freshly painted interior, resealed driveway, and newly created backyard fire pit and seating area (2026). Enjoy all that NorthBrook has to offer, including walking trails, a playground, soccer field, and pavilion. Conveniently located just minutes from Historic Centreville, the Centreville Wharf & Public Landing, local parks, restaurants, and shopping, and only 25 minutes from the Bay Bridge. If you've been searching for a well-maintained, energy-efficient home with modern updates, flexible living space, a private setting, and a backyard ready to enjoy this fall, 427 Brookfield Drive is a must-see.

427 Brookfield Dr, Centreville

Listing courtesy of Compass. Contact:

$749,000
4 Beds ⋅ 3 Baths
PRICED TO SELL - RARE OPPORTUNITY - Beautifully sited on a fabulous 1.03-acre lot in sought-after Prospect Bay Golf and Country Club, this spacious home offers the best of both water and golf course living. Enjoy lovely water views and stunning sunsets from several rooms or while relaxing on the wraparound front porch. From the rear of the home, take in peaceful Golf Course Views overlooking the newly renovated par-five 5th hole. Enjoy these views from the heated and cooled Florida room or from your adjoining deck with a remote controlled awning. Inside, gorgeous hardwood floors flow from the entry through the living and dining rooms. The bright kitchen features Brookhaven cabinets, Profile appliances and opens to the comfortable family room with a gas fireplace and sliders leading to the Florida ( or four seasons) room, creating an ideal layout for everyday living and entertaining. Upstairs, you’ll find four generously sized bedrooms, including a spacious primary suite with tray ceiling, a huge walk-in closet, and a large jetted tub, walk-in shower, and double vanities. The convenient second-level laundry room, two-car garage, storage shed, and oversized parking pad add to the home’s practicality. Select spaces have been refreshed with new interior paint and elegant crown molding (2025), adding a touch of sophistication and style. Recent improvements include Dual-Zone Hybrid HVAC (2024/2026): Customized upstairs/downstairs comfort with two brand-new 2026 Lennox HVAC units with heat pumps and smart thermostats, backed by a Navien tankless combi-boiler Installed in 2024 for ultra-efficient, multi-zone hydronic heating. The crawlspace has been newly encapsulated with an April Aire dehumidifier (2026). Although not a problem in Prospect Bay, you'll never have to worry about losing power as you have a Generac Generator just outside to take care of a power loss! As a Resident of Prospect Bay enjoy exceptional community amenities, including an 18 hole golf course, driving range, a members only restaurant & bar, clubhouse, swimming pool, boat ramp, tennis courts, basketball, pickleball, kayak racks, and a marina. The monthly HOA Fees INCLUDE Golf Membership and Greens Fees. So many activities for all including Book Club, Dine & Cruise, Movie Night for Kids, Garden Club, Line Dancing, etc . This home is just across the street from the boat ramp, marina and open water leading to the Bay! The perfect place to live and play!

116 Prospect Bay Dr W, Grasonville

Listing courtesy of Berkshire Hathaway HomeServices Homesale Realty. Contact:

$489,000
3 Beds ⋅ 2 Baths
Welcome to 103 Opera Court in the sought-after, active 55+ community of Symphony Village at Centerville. This expanded Vivaldi model features three bedrooms and two full bathrooms on an oversized corner lot across from parklands and with no home behind the paver patio. Pull up to your side loading garage and take the short path to the front door, with a quaint covered porch for slow evenings and watching nature go by. Once inside, the spacious foyer offers a dry bar with mini-fridge and architectural pillars lead to an open concept living space. You’re invited in by unobstructed views from the dining area through the living area into the family room extension with a vaulted ceiling and fireplace with marble surround. There is beautiful, engineered hardwood flooring throughout the public spaces. Unmatched natural light drenches the entire space which centers on the cozy gas fireplace for ease of use on the few chilly winter nights. The gourmet, open style kitchen features gorgeous cabinetry, granite countertops, stainless steel appliances, including double wall ovens that are sure to please any chef. The primary bedroom suite has brand new carpeting, a sitting area with vaulted ceiling, a tray ceiling above the bed for added drama, and double walk-in closets. The primary bath features separate vanities, a jetted soaking tub and a custom, walk-in tub. The second bedroom is down the hall from the entry and is adjacent to the second well-appointed full bath. The third bedroom, at the front of the home, is a perfect flex space and could be a bedroom, office, or studio. It also has wood floors and plenty of natural light. Tucked away at the center of the home is the laundry which is on the way to the two-car garage. The garage features a “sky basement” above, which is partially finished and can be used for storage. Outside the French doors in the family room is a paver patio, perfect for entertaining, dining alfresco or taking your morning coffee. For peace of mind and low utilities, this home also has solar panels and a whole house generator. The community takes care of the grounds, leaving you more time to relax and enjoy the peace and quiet and the many amenities! There are paths for walking or biking, including one leading to the local shopping center, pickleball and tennis courts, putting green, bocce ball courts and a resort style outdoor pool. The clubhouse features a concert hall, billiards room, fitness room, bar, party rooms, dining room, and an indoor heated pool open every day. Activities include classes to learn a variety of skills, social hour, arts and crafts, game and card nights, an artist guild with quarterly art shows and much more for the low HOA fee. The historic and charming town of Centerville is minutes away with wonderful restaurants and shops, and a wharf for boating, paddling or a picnic. Enjoy the slower pace of the eastern shore while remaining close to the ocean beaches and the city life across the Chesapeake Bay. This home has SO MANY UPGRADES and beautiful views – it’s a very special property.

103 Opera Ct, Centreville

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

$575,000
3 Beds ⋅ 3 Baths
NEW PRICE — A GREAT OPPORTUNITY IN PROSPECT BAY! Offering approximately 2,850 square feet of living space, this contemporary presents an opportunity to enjoy the Prospect Bay lifestyle at an attractive price point. Available for the first time since 1999, this well-loved home is ready for its next chapter. The spacious family room features a brick fireplace, cathedral ceiling and triple sliders opening to the deck and backyard. The kitchen offers lovely cabinetry, generous counter and storage space, and plenty of room for casual dining. Two bedrooms are conveniently located on the main level, along with a separate dining room and dedicated mudroom with laundry. Upstairs, the spacious primary suite offers privacy, while a loft overlooking the family room provides flexible space for a home office, sitting area, or additional living area. Oversized 2-car garage, plus deck overlooking the backyard. Located in Prospect Bay Golf & Country Club, where residents enjoy golf, swimming pool, tennis courts, boat ramp, and clubhouse with restaurant. Bring your ideas and make this home your own while enjoying all that Prospect Bay has to offer.

24 Fairway Is, Grasonville

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

$735,000
4 Beds ⋅ 4 Baths
335 S. Carolina Rd is ready for its 2nd owner! Potential income producing property, would make an amazing short term rental vacation property! Enjoy sprawling views of the Chesapeake Bay from every level. Only 3 years young, this home is beautifully appointed and move in ready. As you enter, the first floor opens to a living space with a slider that leads to your lush green back yard. There is also a full bathroom and bedroom. The second floor is where the magic is. Your living room with fireplace, kitchen and dining space are open for you to enjoy the spectacular water views from all angles. The third floor boasts 3 bedrooms and 2 full bathrooms including the waterside primary suite with its own private deck. Some special features include a bright open floor plan, balconies with water views, a gorgeous fire pit, and walkable to the Bay and beach. Also enjoy a widened driveway for extra parking spaces, a water softener system and storage shed. This home features 3 decks and a 2 car garage. Move in time to enjoy all that a beautiful Kent Island summer has to offer.

335 S Carolina Rd, Stevensville

Listing courtesy of Coldwell Banker Realty. Contact:

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

128 Allison Jane Dr, Stevensville

Listing courtesy of Mr. Lister Realty. Contact:

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

2000 Herons Nest Way Unit 401, Chester

Listing courtesy of Real Broker, LLC. Contact:

$197,500
Discover a rare opportunity to own a stunning piece of land. Spanning 0.35 acres, this property invites you to create your dream retreat, where luxury meets nature. The community offers exclusive amenities, including common grounds, a picnic area, and playgrounds, fostering a sense of connection and leisure. This land provides a canvas for your vision, whether it's a sophisticated residence or a peaceful getaway. Embrace an elevated lifestyle where outdoor adventures and relaxation harmoniously coexist. This is more than just land; it's an invitation to craft a sanctuary that reflects your aspirations.

Bay Drive, Stevensville

Listing courtesy of Rosendale Realty. Contact:

$825,000
4 Beds ⋅ 4 Baths
Situated on one of the largest lots in sought-after Gibson’s Grant, this 4-bedroom, 3.5-bath home offers space, flexibility, and room to grow. High ceilings and an open layout create an airy feel, with an oversized kitchen flowing seamlessly into the family room and a separate main-level office for work or quiet retreat. The main level also features a formal dining room and living room. Upstairs, the spacious primary suite features a sitting area, two walk-in closets, and en-suite bath, alongside three additional bedrooms and two full bathrooms. The unfinished walkout basement includes a rough-in for a future bath. Outside, enjoy a fenced backyard complete with a patio and built-in fire pit—perfect for gathering year-round. Community amenities include swimming pool, clubhouse, fitness center, walking trails, community pier, picnic area, and kayak launch. Centrally located on Kent Island. Only 5 minutes to the Bay Bridge.

232 Evelyne St, Chester

Listing courtesy of TTR Sotheby's International Realty. Contact:

$819,000
4 Beds ⋅ 3 Baths
Located in the waterfront community of Prospect Bay, residents enjoy golf, swimming pool, boat ramp, tennis courts, and a clubhouse with restaurant. Welcome to this much-loved home, beautifully situated on 1.03 acres with sunset water views on one side and golf course views on the other. Quality built with 2x6 construction, the home features hardwood flooring, Andersen windows, and abundant natural light. The kitchen offers maple cabinetry, a center island, table space, and an open layout connecting to the family room with fireplace and efficient wood-burning insert. Separate living and dining rooms feature bow windows showcasing the water views. A main-level fourth bedroom with built-ins currently serves as a home office. Upstairs, the spacious primary suite features water views, a large bath, and generous walk-in closet, along with two additional bedrooms and a full bath. Enjoy a screened porch overlooking the golf course, a 16' x 12' Amish-built shed, and an oversized two-car garage with workshop space and extensive storage. The large driveway and parking pad accommodate up to six vehicles. Additional storage is available in the walk-in attic. Recent updates include a washer, dryer, refrigerator, microwave, dishwasher, and Trane heat pumps less than two years old.

108 Prospect Bay Dr W, Grasonville

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

$487,500
4 Beds ⋅ 3 Baths
Cloverfields - Location, Location, Location! Welcome to a home that truly offers the best of convenience, community, and Eastern Shore living. Ideally situated just one mile from the Bay Bridge, this property places you within walking distance of all local schools—from pre-kindergarten through 12th grade—as well as the Cross Island Trail and Love Point Park, both just a 3-minute stroll away. Shopping, dining, and everyday conveniences are only minutes from your doorstep, making it easy to enjoy everything Kent Island has to offer while embracing the relaxed coastal lifestyle. Located in the highly desirable Cloverfield's community, residents enjoy exceptional amenities including a community pool, clubhouse, private beach, and marina—all included with the remarkably low HOA. Inside, you'll find a spacious and flexible floor plan offering 4–5 bedrooms and the option for a second-floor laundry area. Thoughtful updates and improvements throughout make this home truly move-in ready. Features include beautiful bamboo flooring, granite countertops, Andersen windows, fresh paint, new luxury vinyl plank flooring in the foyer and primary bathroom, and new carpet in the primary bedroom. Major improvements provide peace of mind for years to come. The front porch has been professionally repointed, the garage door is brand new, and the expansive 16' x 20' deck has recently been redecked—perfect for outdoor entertaining. Additionally, the crawl space has been professionally encapsulated, and a sump pump and dehumidifier have been installed. The heart of the home is the large kitchen, offering ample space for a dining table and everyday gathering. An open dining and living area creates the perfect setting for holidays, celebrations, and family get-togethers. From the welcoming beveled-glass entry door to the beautifully established perennial flower beds, every detail adds warmth and charm. This is more than just a house—it's a lifestyle. Come experience the perfect blend of comfort, convenience, and community in one of Kent Island's most sought-after neighborhoods.

606 Kimberly Way, Stevensville

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

$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 ⋅ 4 Baths
Welcome to Ellendale—where modern comfort meets Eastern Shore charm. This beautifully maintained 4-bedroom, 4 full bath townhome, built in 2023 by Baldwin Homes, offers a like-new feel with a spacious, light-filled layout and a 2-car garage. Designed for both everyday living and effortless entertaining, the home features stylish finishes throughout, plus a top-floor retreat complete with a private balcony and wet bar—perfect for relaxing evenings or hosting guests. As an added bonus, the seller is including several furnishings with the sale, making your move even easier. Included are the dining room table and chairs, kitchen counter stools, the living room TV, the leather sofa in the basement, the TV and console in the small bedroom, the bedroom furniture in the small bedroom, the bar set, as well as the outdoor fire pit and furniture. Nestled in the heart of Stevensville on Kent Island, you're just minutes from waterfront dining, boutique shopping, and historic Kent Narrows. With easy access to Route 50 and a quick drive to Annapolis, this home offers the perfect blend of convenience and coastal lifestyle.

322 Allison Jane Dr Unit H-4, Stevensville

Listing courtesy of Mr. Lister Realty. Contact:

$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:

$429,900
3 Beds ⋅ 2 Baths
*MAJOR PRICE IMPROVEMENT! 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! Seller will consider leasing the property to qualified tenants for $3000 per month plus $3000 security deposit.

109 Birch Rd, Stevensville

Listing courtesy of Five Star Real Estate. Contact:

$377,400
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:

$1,125,000
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:

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

1000 Herons Nest Way Unit 22, Chester

Listing courtesy of RE/MAX Executive. Contact:

$174,000
This prime residential land parcel, located in the desirable ROMANCOKE ON THE BAY subdivision in Stevensville, MD, offers a unique investment or building opportunity with significant potential for appreciation. Spanning 0.56 acres, this corner lot features wooded areas, providing both privacy and a natural aesthetic that enhances the property's overall appeal. Strategically positioned just about four blocks from the picturesque Eastern Bay, this lot benefits from proximity to water-oriented activities without the premium of direct waterfront ownership. Investors can capitalize on the growing demand for properties near water bodies, making this an attractive option for future development. The community amenities are a standout feature, including a boat ramp, clubhouse, picnic area, and jogging/walking paths. These facilities not only enhance the quality of life for residents but also increase the property's desirability to potential buyers or renters. With super low association fees, investors can enjoy the benefits of community amenities without the burden of high costs. The lot's corner location alongside the South Kent Island walking path provides ample privacy and accessibility, which can be advantageous for future residential building projects. The surrounding area is poised for growth, making this property an excellent long-term investment. As demand for residential properties near water continues to rise, this lot presents a compelling opportunity for those looking to enter the real estate market or expand their portfolio. In summary, this 0.56-acre corner lot in ROMANCOKE ON THE BAY is not just a piece of land; it's a strategic investment in a thriving community with abundant amenities and proximity to Eastern Bay. With the potential for appreciation and the appeal of a water-oriented lifestyle, this property is a must-consider for savvy investors looking to maximize their returns or those seeking to build their dream home.

Touhey Drive, Stevensville

Listing courtesy of Realty Navigator. Contact:

$995,000
5 Beds ⋅ 5 Baths
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:

$699,000
4 Beds ⋅ 3 Baths
Highly motived sellers enjoyed Prospect Bay and want you to as well--they just reduced again making it super attractive. Discover the charm of this beautifully renovated split-level home in the desirable Prospect Bay community. With 4 spacious bedrooms and 3 full baths, this residence boasts an inviting interior featuring upgraded countertops, LVP floors, and cozy exposed beams. The heart of the home is the combination kitchen/dining area, perfect for gatherings that can flow outside to the new expanded deck. With one bedroom, full bath and living room on lower level it could be the perfect in-law suite or college student apartment. Enjoy the serene 1.22-acre corner lot with firepit, trees perfect for hammock, backing to mature trees, offering a peaceful views. The community amenities include a pool, golf course, marina, community pool, tennis & pickleball courts and playgrounds, fostering a vibrant neighborhood spirit. Enjoy easy access to the Prospect Bay sanctuary for boating and fishing enthusiasts. Located in a friendly community with excellent schools and nearby parks, this home is perfect for those seeking comfort and convenience. BONUS: Outdoor Office with private entrance on back right corner of house. PLUS: Community has a few boat slips available for rent!

1 Bunker, Grasonville

Listing courtesy of Wilson Realty & Staging LLC. Contact:

$529,000
4 Beds ⋅ 4 Baths
NEW PRICE ....Welcome to 142 Harmony and this beautiful Beethoven model home featuring 4 bedrooms and 3 and one half bath. Situated on a lot that is just a short walk to the community club house, pools and all amenities, this home is designed with a beautiful brick front. As you enter, the floor inviting floor plan welcomes you with the living and dining area on the front of the home and stairs to the side to the upper level. Moving through you'll enter the very large family room with fireplace and the oversized gourmet kitchen with additional cabinets. The breakfast area off of the kitchen allows for relaxing views of the rear patio. The master suite is also located on the main level with master bath featuring a walk-in shower and a walk-in jetted tub. This suite also has two walk-in closets and additional stairs to the upper level. To complete the main level of the home is a half bath and laundry room with access to the garage which includes a sky basement for storage above. The second level of the home offers a very large additional area that can be utilized in many ways along with a carpeted walk-in storage area that can be utilized as a closet or utility room. To complete the upper level is a sitting room overlooking the family room below along with another bedroom and full bath. This home is move in ready and available for a quick settlement.

142 Harmony Way, Centreville

Listing courtesy of RE/MAX Executive. Contact:

$492,500
2 Beds ⋅ 3 Baths
Four Seasons @ Kent Island - 55+ Community - Reduced! * Turn-key & Lovely 2nd Floor Condo in Elevator Building with 1 Car Garage plus 1 Car Outdoor Parking and Private, Secure Indoor Storage Area. This Chester Model offers 1900 sf with pond view and winter water views of Macum Creek. Enter to find an expansive, open floor plan featuring a beautiful white Kitchen with quartz counters, propane gas cooktop with range hood, wall oven + microwave combo and a huge Island that accommodates plenty of bar seating. Spacious Bedroom suites each with private full baths and generous closet spaces. The Primary bath has His 'n Her's double sinks with Moen fixtures, comfort height vanities, large vanity mirrors, medicine cabinets and a walk-in tiled shower with seat. The Primary bedroom features 2 closets; one walk-in-closet and one generous wall closet, a ceiling fan and a single French door to access the balcony. The 2nd Bedroom is large enough to hold a traditional sized bedroom set and features a tub/shower combo in the bath. The open Great Room is large, bright and has serene pond views and winter water views of Macum Creek with oversized sliders to a covered balcony. You will love the convenient laundry room located off the foyer area that accommodates the included full-sized GE washer and dryer. Elevator down to the Lobby level to your private garage and a just a few steps down the corridor is your private, keyed storage closet. This condo building features a secure lobby entrance and is impeccably decorated and maintained. Additionally, the 2nd floor has a common Club Room/Meeting Room great for socializing with your neighbors or as additional entertainment space. It features Public Water, Public Sewer, individually metered propane gas heat and cooking. All residents have access to the community amenities which include a huge 24,000 sf Club House with Billiards Room, Casual Lounge Area, Fitness Center, Party and Meeting rooms, and fabulous Indoor Heated Pool & Spa. Outside awaits a resort-like Pool, Cabana House, Private Beach Area, Outdoor Concert Space, Pier for Fishing and taking in the magnificent Chester River views & Kayak launch and Walking Trails. Pickle Ball enthusiasts you are in luck as there are Tennis Courts and Pickle Ball Courts for all, and grand kids can be entertained at a small Playground Area. Come tour today and see why this is THE place to be in Kent Island for 55+ living!

4000 Herons Nest Way Unit 22, Chester

Listing courtesy of RE/MAX Leading Edge. Contact:

$529,000
3 Beds ⋅ 2 Baths
Seller will pay the capital contribution fee of $3240 with an acceptable contract. 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:

$595,000
3 Beds ⋅ 5 Baths
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: