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230 Long Point Rd, Stevensville
$500,000
4 Beds ⋅ 3 Baths
Brand new FOUR BEDROOM home with GARAGE and peek-a-boo WATERVIEWS for UNDER $500,000!!! Fully fenced backyard! One block from the community boat ramp, pier, clubhouse, playgroud, waterfront property. LVP flooring throughout the entire first floor. Quartz countertops in kitchen. Stainless steel appliances, LED lights, and hardwood staircase. Custom railings at interior steps. Laundry room upstairs with LVP. LVP in upstair bathrooms. Designer fixtures! Massive usable space in the backyard. A short walk to the Romancoke Fishing Pier and an even shorter walk to the community waterfront park. Minor summer waterviews from master bedroom and other front bedroom. Winter waterviews will be better!!! This house will not last long. One year warranty!

230 Long Point Rd, Stevensville

Listing courtesy of Coldwell Banker Waterman Realty. Contact:

Selling Office: Berkshire Hathaway HomeServices PenFed Realty.

2032 Pondtown Rd, Chestertown
$365,000
3 Beds ⋅ 2 Baths
Meticulously maintained and full of charm, this delightful three-bedroom, two-bath rambler is perfectly situated on an oversized double lot, offering both comfort and exceptional outdoor space. From the moment you arrive, you’ll appreciate the care and attention this home has received, making it truly move-in ready. Step inside to a bright and inviting open floor plan designed for easy living and entertaining. The spacious living room features a soaring cathedral ceiling and a ceiling fan, creating an airy and welcoming atmosphere. This space flows seamlessly into the kitchen and dining area, allowing for effortless gatherings with family and friends. The dining area is enhanced by a beautiful custom chair rail molding detail that adds character and elegance, while sliding glass doors provide abundant natural light and direct access to the backyard, perfect for indoor-outdoor living. The kitchen is both functional and stylish, offering warm wood cabinetry, recessed lighting, and a vaulted ceiling that adds to the home’s open and spacious feel. The bedroom area includes a comfortable primary suite complete with a private ensuite bath, along with two additional bedrooms, each featuring ceiling fans for year-round comfort. A well-appointed hall bath conveniently serves the two additional bedrooms, providing both functionality and privacy for family members or guests. Step outside and discover an incredible backyard retreat that truly sets this property apart. Fully enclosed with a privacy fence, the expansive yard offers plenty of room to relax, play, or entertain. Enjoy evenings on the patio, stroll along the walking paths, or unwind under the beautiful gazebo. A cozy fire pit creates the perfect gathering spot for cooler nights. One of the standout features of this property is the impressive three-bay workshop with electric, ideal for hobbyists, craftsmen, or anyone in need of substantial workspace and storage. With its thoughtful updates, inviting layout, and exceptional outdoor amenities, this home offers a rare opportunity to enjoy both comfort and versatility in a peaceful setting.

2032 Pondtown Rd, Chestertown

Listing courtesy of Northrop Realty. Contact:

Selling Office: Coldwell Banker Chesapeake Real Estate Company.

226 Ash Wood Dr, Church Hill
$560,000
4 Beds ⋅ 4 Baths
Amazing price on this beautifully upgraded, nearly-new home in Church Hill Hunt! Welcome to 226 Ash Wood Drive, a thoughtfully designed home built less than two years ago that offers all the benefits of new construction—without the wait. Located in the desirable Church Hill Hunt community, this move-in ready home combines modern finishes, smart home features, and comfortable everyday living. Step inside to sun-filled spaces, recessed lighting throughout, and an open-concept layout designed for both entertaining and daily life. The main level features durable LVP flooring and a welcoming family room anchored by a cozy propane fireplace, flowing seamlessly into the gourmet kitchen and dining area. The kitchen shines with quartz countertops, upgraded soft-close cabinetry, a glass tile backsplash, and modern finishes that continue throughout the bathrooms. A private study with glass office doors provides the perfect space for working from home or quiet retreat, while the main level also offers a functional mudroom and convenient half bath. Upstairs you’ll find four spacious bedrooms, including a luxurious primary suite with a large walk-in closet and a spa-inspired bath featuring quartz counters and a tiled shower. The guest full bathroom includes a dual vanity and tiled shower, offering comfort and convenience for family or visitors. The finished basement with a full bath adds valuable additional living space—ideal for a rec room, home gym, media space, or hosting guests—while still providing plenty of storage. Outdoor living is just as inviting. Relax on the full front porch or enjoy the fully fenced backyard featuring an expansive 36' x 15' patio, perfect for entertaining, gatherings, or peaceful afternoons outdoors. This home is loaded with comfort, efficiency, and technology upgrades, including an EV charger in the side-entry garage, tankless water heater, water softener, constant-pressure well pump, fresh air exchanger (HRV), and Ecobee WiFi thermostat. A built-in technology package with internet and HDMI hookups in common living areas makes modern living seamless and connected. Ideally located next to Church Hill Park, the home offers a connecting walking trail just steps away, making it easy to enjoy the outdoors. Church Hill Hunt is conveniently located near Route 301, providing easy access to the Bay Bridge or a quick drive north toward Middletown, making commuting and travel simple. Meticulously maintained and thoughtfully upgraded, this exceptional home offers the space, features, and location today’s buyers are looking for. Schedule your private showing and see everything 226 Ash Wood Drive has to offer.

226 Ash Wood Dr, Church Hill

Listing courtesy of Compass. Contact:

Selling Office: Chesapeake Real Estate Associates, LLC.

326 S Carolina Rd, Stevensville
$560,000
3 Beds ⋅ 3 Baths
Welcome to island living in the sought-after Kent Island Estates—where sun, sand, and waterfront lifestyle are part of your everyday routine. This beautifully updated 3-bedroom, 2.5-bath home is ideally located just steps from the community beach, offering the perfect blend of comfort, space, and coastal charm. Inside, you’re greeted by a bright, open-concept layout filled with natural light, complemented by high ceilings, updated fixtures, and durable LVP flooring throughout the entire first floor—perfect for easy maintenance after beach days. The spacious living area flows effortlessly into a beautifully updated kitchen featuring brand-new granite countertops, 42” wood cabinetry, and plenty of room to gather and entertain. Upstairs, enjoy new carpet throughout and retreat to a fully renovated primary suite designed for relaxation. The spa-like bath includes a separate jacuzzi tub, walk-in shower, and private water closet—your own personal escape after a day on the Bay. Step outside and embrace the lifestyle that makes Kent Island so special. The expansive rear deck overlooks one of the largest lots in Kent Island Estates, creating the perfect setting for entertaining or unwinding under the coastal sky. The backyard is ready for memorable evenings with a permanent charcoal grill and fire pit—ideal for summer cookouts, crisp fall nights, and gathering with friends and family. The home’s exterior is just as impressive, featuring a brand-new oversized half-circle driveway offering abundant parking—perfect for hosting guests, multiple vehicles, or boat storage. There’s also ample space to expand with room for a detached pole building or workshop, giving you flexibility to match your lifestyle. The oversized attached 2-car garage (28x28) with 12-foot ceilings and 9-foot doors provides plenty of space for vehicles, boats, or all your beach and boating gear. Major system updates provide peace of mind, including a new roof within the last 4 years, updated heat pumps, and a top-of-the-line whole-house water treatment system with UV filtration, offering enhanced water quality throughout the home. Adding even more appeal, this property features a proven 3-year track record as a successful Airbnb, offering an incredible opportunity for income potential in a highly desirable waterfront community. Located just minutes from the Romancoke Fishing and Crabbing Pier, Kentmorr Marina & Restaurant, and popular beach and dock bars, you’ll have easy access to some of the best waterfront dining, nightlife, and outdoor recreation the Eastern Shore has to offer. With access to multiple community beaches and everything island living brings—this is more than a home, it’s a lifestyle.

326 S Carolina Rd, Stevensville

Listing courtesy of Samson Properties. Contact:

Selling Office: Samson Properties.

255 Redstart Dr, Chester
$780,000
4 Beds ⋅ 3 Baths
The Simone is a beautifully designed home with a projected settlement of May 2026, offering the space and features you are looking for. With 4 bedrooms, 3 full baths, and a 2-car garage, this home balances everyday comfort with thoughtful design details. A dedicated home office provides the perfect space for remote work or study, while the great room is anchored by a striking two-story shiplap fireplace with a granite surround, creating a warm and inviting focal point. The kitchen is well-appointed with a gas cooktop, single oven, microwave, range hood, dishwasher, French-door refrigerator, and pendant lighting, complemented by a tile backsplash and quartz countertops that continue into the owner’s bath. LVP flooring flows through the foyer, kitchen, dining area, great room, owner’s suite, and bedroom two, while tile finishes the full baths and laundry room. Plush carpeted spaces in the loft, second floor, and additional bedrooms add comfort where it counts. The owner’s bath features a spa-like shower with seating, a handheld wand, and double sinks for added convenience. 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. Welcome to a new luxury active adult 55+ community on Maryland's Chesapeake Bay. Discover the amenity-filled, resort-style experience within 45 miles of Washington DC and Baltimore. Residents can take advantage of the community's 24,000 sq. ft. clubhouse with indoor & outdoor pools, a state-of-the-art fitness center, and multiple tennis and pickleball courts. With a full-time lifestyle director on site the community also features a well-maintained calendar of activities such as walking club, indoor and outdoor yoga sessions, mahjong club, kayaking, pickleball and more. Kent Island life is about making friends and enjoying the company of people who have worked hard and now want to enjoy all that a luxury 55+ community has to offer. Located steps from the water and minutes from Annapolis, the location also offers quick access to Rt. 50. Enjoy the convenience of nearby dining and shopping options together with the quaint charm of a small town.

255 Redstart Dr, Chester

Listing courtesy of KOVO Realty. Contact:

Selling Office: Unrepresented.

630 Warbler Way Unit 2233, Chester
$599,900
2 Beds ⋅ 3 Baths
The Chester blends modern design with everyday comfort in a thoughtfully designed layout perfect for both work and relaxation. Featuring 2 bedrooms, 2.5 baths, and a 1-car garage, this home offers stylish finishes and smart functionality throughout. Standout features include a home office with lited French doors, an electric fireplace that adds warmth and ambiance, and a convenient dry bar for entertaining or casual gatherings. The kitchen is beautifully equipped with a single oven, microwave, gas cooktop, range hood, dishwasher, pendant lighting, and tile backsplash, all complemented by quartz countertops for a polished look. Laminate flooring runs throughout the main living areas, with tile in both full baths for easy maintenance. The owner’s bath features a walk-in shower with seat and handheld shower wand, double sinks, and elegant quartz countertops, creating a relaxing retreat. For a full list of included features, please contact our sales representatives. Photos are for illustrative purposes only and may not represent the exact home or finishes available.

630 Warbler Way Unit 2233, Chester

Listing courtesy of KOVO Realty. Contact:

Selling Office: Unrepresented.

219 Songbird Ln, Centreville
$848,000
4 Beds ⋅ 4 Baths
New Construction in Willow Branch Community – Only 5 Lots Left! Build your dream home with Mike’s Custom Homes in the sought-after Willow Branch Community in Centreville, MD! Choose from three stunning models or bring your own custom floor plan to create the perfect home tailored to your needs. Nestled in a serene setting with spacious lots, high-quality craftsmanship, and modern finishes, these homes offer the best of Eastern Shore living. Don’t miss this opportunity to build in a prime location with easy access to local amenities, schools, and major routes. Secure your lot today—contact us for more details! *Photos are of a previously sold model and may feature options that are upgrades. *Additional lot premium fees will apply

219 Songbird Ln, Centreville

Listing courtesy of Coldwell Banker Realty. Contact:

Selling Office: Samson Properties.

129 Thicket Ct, Centreville
$865,000
4 Beds ⋅ 4 Baths
New Construction in Willow Branch Community - Only 5 Lots Left! Build your dream home with Mike's Custom Homes in the sought after Willow Branch Community in Centreville, MD! Choose from three stunning models or bring your own custom floor plan to create the perfect home tailored to your needs. Nestled in a serene setting with spacious lots, high-quality craftmanship, and modern finishes, these homes offer the best of the Eastern Shore living. Don't miss this opportunity to build in a prime location with easy access to local amenities, schools and major routes. Secure your lot today - contact us for more details! **Photos are of a previously sold model and may feature options that are upgrades. *Additional lot premium fees will apply.

129 Thicket Ct, Centreville

Listing courtesy of Coldwell Banker Realty. Contact:

Selling Office: Benson & Mangold, LLC.

313 Wye Rd, Queenstown
$1,600,000
5 Beds ⋅ 6 Baths
Experience a true “wow” moment the instant you arrive at this meticulously maintained estate in the exclusive Bennett Point community, set on a private street with views of the renowned Wye River. Step into the grand foyer and be greeted by soaring ceilings, elegant columns, lighted niches, graceful arches, and a stunning curved staircase. The home opens into a formal dining room perfect for entertaining, flowing seamlessly into a dramatic two-story family room with a wall of windows overlooking the patio, saltwater Gunite pool, fenced backyard, and barn. A floor-to-ceiling stone gas fireplace anchors the space—ideal for cozy winter nights or gathering for the big game. The open-concept layout continues into a chef’s dream kitchen, featuring granite countertops, abundant Merillat Masterpiece solid cherry cabinetry, and premium appliances including a Sub-Zero refrigerator/freezer, commercial-grade Viking cooktop with hood and pot filler, double wall ovens, built-in microwave, beverage cooler, dishwasher, and ice maker. A spacious island, built-in desk, appliance cabinet, hidden cutting board, and corner pantry make this kitchen as functional as it is beautiful. The main level offers two luxurious owner’s suites. The primary suite includes a wet bar, private sitting area, dual walk-in closets, and a spa-inspired bath with heated soaking tub, dual-head shower, travertine floors, and marble countertops. The second suite features a gas fireplace, built-in desk, and an accessible ensuite bath with roll-in shower and elegant finishes—ideal for multi-generational living or guests. A main-level laundry room adds everyday convenience. Throughout the home, you’ll find rich teak flooring, tray ceilings, and abundant recessed lighting. Upstairs, three spacious bedrooms each feature private ensuite baths, along with a large game room. A generous unfinished third level offers endless possibilities for expansion, including an au pair suite or additional bedrooms. Outdoor living is equally impressive. Enjoy the fenced saltwater pool with water feature, a screened porch with Easy-Breeze windows for year-round use, and a beautifully maintained yard with underground irrigation, vegetable garden, and whole-house generator. The conditioned crawl space adds efficiency and peace of mind. Equestrian enthusiasts will appreciate the adjacent horse training facility with covered arena. The property includes a 3-stall barn with heat sensor, two pastures, dry lot, heated water, electric, and vinyl fencing—perfect for year-round care and riding. This exceptional property offers luxury, functionality, and lifestyle—all in one remarkable setting.

313 Wye Rd, Queenstown

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

Selling Office: Coldwell Banker Realty.

1901 Cox Neck Rd, Chester
$2,350,000
4 Beds ⋅ 5 Baths
Nestled on nearly seven private acres along the protected waters of Crab Alley Bay, this extraordinary waterfront estate offers breathtaking views, serene surroundings, and exceptional living across three spacious levels. Designed for both comfort and elegance, the home features a dramatic wall of windows overlooking the pool and waterfront, filling the interior with natural light. The lush property includes two ponds and wetlands that attract abundant wildlife, creating a peaceful, ever-changing natural setting. Inside, the home is beautifully appointed with a new gourmet kitchen featuring granite countertops and a walk-in pantry, along with cherry and maple floors, a new roof, an updated primary bath, and an additional renovated full bath. Generously scaled living and sitting rooms on every level provide abundant space for entertaining or quiet retreat. The residence includes four oversized bedrooms, four full baths, a workout room, extensive storage, and a four-car garage. Each level is enhanced by its own gas fireplace, adding warmth and ambiance throughout the home. Beautifully maintained gardens and mature trees frame stunning sunrises and make the waterfront setting feel remarkable every day. Great location on Kent Island close to shopping and commute.

1901 Cox Neck Rd, Chester

Listing courtesy of Coldwell Banker Realty. Contact:

Selling Office: Cummings & Co. Realtors.

630 Warbler Way Unit 2232, Chester
$612,500
2 Beds ⋅ 3 Baths
The Chester blends modern design with everyday comfort in a thoughtfully designed layout perfect for both work and relaxation. Featuring 2 bedrooms, 2.5 baths, and a 1-car garage, this home offers stylish finishes and smart functionality throughout. Standout features include a home office with lited French doors, an electric fireplace that adds warmth and ambiance, and a convenient dry bar for entertaining or casual gatherings. The kitchen is beautifully equipped with a single oven, microwave, gas cooktop, range hood, dishwasher, pendant lighting, and tile backsplash, all complemented by quartz countertops for a polished look. Laminate flooring runs throughout the main living areas, with tile in both full baths for easy maintenance. The owner’s bath features a walk-in shower with seat and handheld shower wand, double sinks, and elegant quartz countertops, creating a relaxing retreat. For a full list of included features, please contact our sales representatives. Photos are for illustrative purposes only and may not represent the exact home or finishes available.

630 Warbler Way Unit 2232, Chester

Listing courtesy of KOVO Realty. Contact:

Selling Office: Unrepresented.

154 Longfellow Dr, Chestertown
$300,000
3 Beds ⋅ 1 Baths
Located in the water-oriented community of Chester Harbor just outside of historic Chestertown, 154 Longfellow Drive offers the ideal blend of convenience and Eastern Shore living. This single-level home is situated on a cleared and fenced 0.34 acre-parcel and a voluntary HOA fee provides access to the community boat ramp and waterfront park. Less than a mile and a half from Route 213, enjoy efficient commuting and quick access to Chestertown, Church Hill, Centreville, Easton, and Kent Island. Inside the home, enjoy an updated full bath, a new HVAC system and well pump, a six year old septic system (flushed in 2025), as well as a large, partially finished basement - perfect for storage.

154 Longfellow Dr, Chestertown

Listing courtesy of Cross Street Realtors LLC. Contact:

Selling Office: CR Realty.

630 Warbler Way Unit 2223, Chester
$559,900
2 Beds ⋅ 3 Baths
Introducing the Chester Lot 2223, projected to settle in May 2026. This beautiful home offers 2 bedrooms, 2.5 baths, and a 1-car garage. Interior highlights include a dry bar, electric fireplace, and a dedicated home office with lited French doors. The kitchen features a single oven, microwave, gas cooktop, range hood, dishwasher, pendant lights, tile backsplash, and Quartz countertops, creating a functional and stylish space. Laminate floors extend throughout the home except for tile in the two full baths. The owner’s bath includes a shower with seat, handheld shower wand, double sinks, and quartz countertops for a polished, upscale feel. 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.

630 Warbler Way Unit 2223, Chester

Listing courtesy of KOVO Realty. Contact:

Selling Office: Unrepresented.

1000 Chesapeake Dr, Stevensville
$714,280
5 Beds ⋅ 3 Baths
GREAT OPPORTUNITY! Custom-Built Home – with room to Grow! This beautifully updated custom-built residence offers nearly 4,000 sq. ft. of living space with large, light-filled rooms designed for both comfort and entertaining. Featuring five bedrooms and 2.5 baths, the home has been freshly painted and updated with new carpet. Another game changer is not just the space this home offers but a new kitchen with white cabinets granite, and appliances, new re-freshen bathrooms vanities, Luxury vinyl flooring and much more. The open-air floor plan includes a welcoming family room, breakfast area, and kitchen, along with formal living room and dining rooms for more traditional gatherings. A two-car garage and ample driveway parking add convenience, while the corner lot provides plenty of space for a pool, play area, or expanded outdoor living. The third floor is a true standout—perfect for a movie theater, game room, or bonus living space, with generous storage options as well. Located just a short walk to the waterfront, the community features a boat launch, pavilion, playground, and bayfront recreational area. Move-in ready with versatile living spaces and a thoughtful layout, this home at 1000 Chesapeake Drive is ready for your personal touch.

1000 Chesapeake Dr, Stevensville

Listing courtesy of Coldwell Banker Realty. Contact:

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

64 Long Creek Dr, Stevensville
$550,000
3 Beds ⋅ 3 Baths
Step into the perfect blend of comfort, space, and Eastern Shore charm at 64 Long Creek. Offering 1,804 square feet of thoughtfully designed living space on nearly 2 private acres, this 3-bedroom, 2.5-bath home delivers both functionality and style. Inside, you’ll find a comfortable, well-planned layout featuring a gas fireplace, formal living and dining rooms, and a cozy den just off the kitchen with eat-in table space. The kitchen shines with a New stove and dishwasher . A spacious mudroom includes a washer, dryer, utility sink, and exterior access—ideal for everyday convenience. One of the standout features is the 240 sq. ft. four-season sunroom, complete with a mini-split system for year-round heating and cooling—perfect for relaxing in any season. Step outside to a 390 sq. ft. deck, sealed for durability, along with a 10x12 patio—ideal for entertaining or enjoying peaceful outdoor living. The premium landscaping, filled with lush trees, creates a serene and private setting. Additional highlights include a partially furnished option (available upon request), a storage shed and a spacious attached double garage (696 sq. ft.) with a long paved driveway. The home is serviced by a private well and septic—and best of all, there are no HOA's. Location is everything, and this home delivers. Enjoy close proximity to the vibrant Kent Narrows, the Blue Heron Golf Course. Indulge in waterfront dining at top-rated seafood restaurants (5 min. away), explore nearby wineries, County boat ramps, visit the Elks lodge, or take in the breathtaking views of the Chesapeake Bay. Amazing Chesapeake Bay Sunrises/Sunsets and schools, shopping, restaurants all nearby and Annapolis is only minutes away. Just across the main road, the scenic Cross Island Trail invites you to start your mornings with a jog, enjoy leisurely bike rides, or take in tranquil waterfront strolls. This residence presents an ideal setting for those seeking a retreat from the bustle of everyday life. Whether you're searching for a full-time residence or a weekend retreat, this property offers the lifestyle you’ve been waiting for—privacy, convenience, and natural beauty all in one.

64 Long Creek Dr, Stevensville

Listing courtesy of Coldwell Banker Realty. Contact:

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

115 Masters Way, Grasonville
$800,000
4 Beds ⋅ 4 Baths
Great price improvement! Welcome to The Enclave at Prospect Bay, where this former model home showcases the sought-after “Pebble Beach” floor plan with thoughtful upgrades and timeless details, backing directly to the 18-hole golf course. Designed for both everyday living and entertaining, the home features three first floor bedrooms, three and a half bathrooms, and a spacious walk-up “sky basement” with a full bath—ideal as a fourth bedroom, office, or media room. The chef’s kitchen offers Quartz countertops, wall oven, cooktop, ceramic tile backsplash, pantry, and a large island that opens to the dining area and family room.  There is a bonus coffee or wine bar with mini fridge, stylish glass cabinets, and additional storage located off the kitchen. In the living room, a custom fireplace with built-ins creates a warm focal point, while expansive windows and plantation shutters throughout the home invite natural light. The main-level primary suite includes a spa-like bath with dual vanities, a walk-in shower, and private water closet. Two additional bedrooms and a versatile bonus room provide flexible living space. Step outside to a spacious patio overlooking the 11th hole—perfect for entertaining or simply enjoying the views. The fenced yard is beautifully landscaped with flourishing gardens and an in-ground sprinkler system, while the HOA maintains the yard for a low-maintenance lifestyle. Additional highlights include a mudroom/laundry room off the two-car garage and efficient upgrades such as the Rinnai tankless water heater. Living in Prospect Bay means access to an array of community amenities including an 18-hole golf course, clubhouse with dining, marina, pool, tennis and pickleball courts, and year-round social activities. Here, every day feels like a vacation.

115 Masters Way, Grasonville

Listing courtesy of Coldwell Banker Realty. Contact:

Selling Office: Unrepresented.

635 Davol Rd, Stevensville
$417,500
3 Beds ⋅ 2 Baths
Lovely custom-built one-level rancher home located in the sought-after and desirable, water-oriented Cloverfields community. This spacious one-level home offers a large primary bedroom with a walk-in closet and an en-suite bath featuring a walk-in shower with grab bar and a double-sink vanity. It has two additional bedrooms and a hallway full bathroom with tub. The inviting living room showcases a large front window with a half-moon transom that fills the space with natural light. A charming country kitchen includes a generous cabinet pantry and opens to a dining room with a beautiful built-in corner cabinet. Just off the kitchen, enjoy a large screened-in porch—perfect for relaxing or entertaining. Additional features include a two-car garage with built-in shelving, a large paved driveway and an attractive newer white privacy fence surrounding the spacious yard. The fencing requires no repainting, and the property line extends beyond the back fence. Residents of Cloverfields enjoy outstanding community amenities just minutes away: clubhouse, swimming pool and kiddie pool, beach, pavilions, grills, boat ramp, marina with rental slips, fishing pier, basketball courts, horseshoe pits and playgrounds. This ideal location offers easy access to Routes 50 and 301, Annapolis, Fort Meade, Washington, DC, Baltimore, Easton and more. Close to restaurants, shopping, schools, parks, walking and biking trails—including the Cross Island Trail—and countless recreational activities. ADA features include Hallway is est. 48" wide, front door est 36" wide, hallway door to garage is est 32". The home is selling "as is" and priced to allow the next owner to add personal touches or updates as desired. The gas fireplace has been closed off; it is thought it could be reopened if the new owner chooses, but buyers should verify.

635 Davol Rd, Stevensville

Listing courtesy of Blackwell Real Estate, LLC. Contact:

Selling Office: Omnia Real Estate LLC.

3021 Bennett Point Rd, Queenstown
$2,800,000
5 Beds ⋅ 6 Baths
Set on more than five tranquil acres with deep water and over 900 feet plus of protected shoreline, this custom-built waterfront residence new finished square footage 7,129 feet offers timeless design, enduring quality, and a setting unlike any other. With five full en-suites and newly finished spaces for a second family room & kitchenette, it provides flexibility for multi-generational living or exceptional guest accommodation. Originally built in 1981 and completely reimagined in 2006, every detail reflects craftsmanship and artistry. A gated entry and private drive lined with seasonal blooms lead to a circular drive and covered brick porch, where glass entry doors open to reveal soaring vaulted ceilings, skylights, and a wall of windows framing the breathtaking Wye River views. Throughout the home, custom cherry millwork elevates fireplaces, built-ins, and displays with warmth and richness. At the heart of the open floor plan, the gourmet kitchen is outfitted with Alder cabinetry, Sub-Zero refrigeration, three wall ovens, a five-burner cooktop with grill, and a warming oven—designed for both entertaining and everyday living. Formal dining beneath a vaulted ceiling, casual meals at the breakfast bar, or dining al-frescos on the composite deck all capture sweeping water views. Outdoors, cascading deck stairs open to a lush lawn and private pier with boat lift in deep water, offering endless opportunities for boating, kayaking, and sunrise views. Inside, thoughtfully designed spaces accommodate every lifestyle need. A professional office with private entry is ideal for working from home, while a separate en-suite suite with private stair access provides perfect quarters for guests or an au pair. The main-level primary suite features soaring ceilings, panoramic river views, and a spa-inspired bath with onyx floors, jetted tub, walk-in shower, and dual vanities. Upstairs, two additional en-suites and a cedar closet complete the private wing. The walk-out lower level expands the living experience with a recreation room, gas fireplace, full daylight windows, a full bath, and covered patio access. Flex rooms, abundant storage, and a generously sized workshop/studio make the home as practical as it is luxurious. In addition, there is 776 sq. in basement that could be finished if necessary or used as storage.

3021 Bennett Point Rd, Queenstown

Listing courtesy of Coldwell Banker Realty. Contact:

Selling Office: TTR Sotheby's International Realty.

108 Holly Ct, Stevensville
$1,375,000
4 Beds ⋅ 3 Baths
Waterfront, living on Kent Island! This waterfront home is in a great location, Queen Anne Colony community and sits nearly an acre at the end of a quiet cul-de-sac. With over 180 feet of waterfront on Price Creek, you’ll enjoy protected deep water and quick access to the Chesapeake Bay, making it a true boater’s paradise. The home is in excellent condition and features 4 bedrooms and 3 full baths. The open-concept main living area is perfect for entertaining while taking in the beautiful water views. Additional living space includes a cozy den for quiet relaxation. The primary suite offers water views, a spacious walk-in closet, and a private bath with double vanities. In addition to the location and condition this home is all one level living, so this could be your home forever, age in place. Beautiful new exterior finishings provide great curb appeal. Fish and crab right from your private pier with a deep-water slip or spend the afternoon relaxing by the pool after a day on the water. Entertain family and friends on the screened porch, launch kayaks from your private ramp, or simply enjoy the peaceful waterfront views. Conveniently located just minutes from the Bay Bridge, this property is ideal for a weekend getaway or full-time residence with easy commutes to DC, and Annapolis. Enjoy nearby Blue Heron Golf Course and the Cross Island Trail located just outside the community.

108 Holly Ct, Stevensville

Listing courtesy of Coldwell Banker Realty. Contact:

Selling Office: Unrepresented.

331 Kidwell Ave, Centreville
$549,000
5 Beds ⋅ 3 Baths
Welcome to 331 Kidwell Avenue, a stunning colonial in the heart of Historic Centreville, Maryland, where timeless architecture meets modern comfort. Built in 1891, this beautifully updated home sits on a rare half-acre lot and offers over 2,700 square feet across four levels, all with NO HOA. The home’s exterior has been freshly painted, enhancing its classic curb appeal while preserving the character that makes historic homes so special. From the moment you step inside, you’re welcomed by a grand foyer highlighted by 10-foot ceilings, detailed custom trim work, and original hardwood floors that showcase the home’s historic charm. The updated kitchen features modern appliances, abundant built-in storage, and generous pantry space, making it both functional and inviting. Just off the kitchen is a sun-filled formal dining room and a spacious living area framed by beautiful custom trim, perfect for entertaining or everyday living. A half bath and mudroom complete the main level. Upstairs, elegant railings lead to the second floor where you’ll find four large bedrooms, a full hallway bathroom, and a convenient laundry area. The entire third level is dedicated to the primary suite, creating a private retreat with a massive walk-in closet, built-in storage, and an impressive ensuite bath featuring a stand-alone soaking tub, tiled shower, drying area, and vaulted ceilings. The lower level basement offers excellent storage space and houses the sump pump and updated HVAC systems. Step outside through the mudroom to enjoy the partially fenced backyard with mature trees and a beautiful flagstone patio, perfect for relaxing or entertaining. The property also includes a detached garage, a paved basketball court, and additional fenced yard space ideal for gardening or outdoor activities. Located within walking distance to Centreville High School, Centreville Middle School, and Kennard Elementary, this home also offers easy access to shopping, dining, the Queenstown Outlets, and major Eastern Shore destinations including Annapolis, Easton, St. Michaels, Kent Island, and the Delaware beaches. Historic charm. Modern updates. Space that’s nearly impossible to find in downtown Centreville. All that’s missing… is you.

331 Kidwell Ave, Centreville

Listing courtesy of RE/MAX Executive. Contact:

Selling Office: Brick and Quill Realty.

708 Church Hill Rd, Centreville
$365,000
3 Beds ⋅ 2 Baths
Charming one-level home featuring refinished hardwood floors, fresh paint, Updated Kitchen 2020, Updated Bath 2022, New Roof 2020, New AC 2021, Newer Boiler Heat, New Deck, New Gutters and a 50 amp service for electric cars This well-maintained property offers a spacious yard complete with storage sheds and ample off-street parking. Ideally located just outside the charming town of Centreville, you’ll enjoy the best of small-town living with convenient access to local restaurants, waterfront parks, and a public boat ramp perfect for kayaking or enjoying scenic walks along the water. An easy drive to Annapolis, Easton, St. Michaels, and Delaware makes this home a perfect blend of peaceful living and accessibility.

708 Church Hill Rd, Centreville

Listing courtesy of Coldwell Banker Realty. Contact:

Selling Office: Chesapeake Real Estate Associates, LLC.

129 Sailcloth Way, Chester
$764,900
3 Beds ⋅ 2 Baths
Welcome to 129 Sailcloth Way in the resort-style community of Four Seasons at Kent Island! This beautifully upgraded Kilarney model offers over 2300 square feet of single-level living, an open layout, and designer finishes throughout. Move-in ready and available now - no need to wait months for new construction. Inside, you'll find a spacious gourmet kitchen with GE Profile appliances, gas cooktop, double oven, quartz countertops and backsplash, a large island, under-cabinet lighting, and a convenient wine bar. The kitchen flows seamlessly into the bright dining area and the expansive great room with a gas fireplace, creating the perfect space for everyday living and entertaining. This home includes 2 bedroom, 2 full baths, and a flex room idea for a home office or a third bedroom. The impressive owner's suite features a walk-in closet, and a private bath with a quartz-topped double vanity. Additional upgrades include custom window treatments, upgraded lighting, and an oversize garage that is insulated, as well as a finished and insulated attic - all already installed, saving you thousands compared to new construction. Four Seasons at Kent Island offers exceptional amenities, including a brand-new 24,000 sq. ft. clubhouse overlooking the Chester River, outdoor infinity pool, indoor pool, fitness center, game room, library, fire pits, Tiki bar, walking paths, pickleball and tennis courts, bocce, dog park, amphitheater, and pier with transient boat slips. A full-time lifestyle director coordinates daily activities, clubs, classes and community events year-round. Experience true resort-style living on Kent Island!

129 Sailcloth Way, Chester

Listing courtesy of RE/MAX Executive. Contact:

Selling Office: Taylor Properties.

204 Overture Way, Centreville
$485,000
2 Beds ⋅ 2 Baths
Welcome to 204 Overture Way—where easy living meets thoughtful design in the sought-after 55+ community of Symphony Village. This impeccably maintained, one-owner rancher offers 2 bedrooms, 2.5 bathrooms, and a layout that lives effortlessly. From the moment you step inside, you’ll notice the gleaming hardwood floors, high ceilings, and custom details that elevate the entire home. The open floor plan provides both flow and flexibility. A formal living room seamlessly connects to the dining room while a private study just off the living space offers the ideal spot for a home office or potential third bedroom. The kitchen opens to an oversized great room centered around a cozy propane fireplace, creating a warm and inviting space for everyday living. Sliding doors lead to a patio, extending your living space outdoors. The spacious primary suite is designed as a true retreat, complete with two walk-in closets, a linen closet, and a well-appointed en-suite bath featuring dual vanities, a soaking tub, and a walk-in shower. A generously sized guest bedroom with its own walk-in closet and a full hall bath provides comfort and privacy for visitors. Storage is abundant throughout, including extensive closet space and a bonus attic area above the garage—perfect for additional storage or future flex space. Living in Symphony Village means enjoying a vibrant, amenity-rich lifestyle with a clubhouse, pool, fitness center, bocce courts, putting green, walking and biking trails, plus a full calendar of social events and classes. Conveniently located just off Routes 301 and 213, and only 20 minutes to the Bay Bridge, this home offers the perfect balance of peaceful community living with easy access to everything you need. Move-in ready and meticulously cared for—this is the one you’ve been waiting for.

204 Overture Way, Centreville

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

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

1921 Harbor Dr, Chester
$519,900
3 Beds ⋅ 3 Baths
Just completed brand new home! Energy efficient! The comfort of knowing that everything is new! One year warranty included! The fully finished daylight basement offers additional space for recreation or relaxation, enhancing the home's versatility. Composite deck, paved driveway, LVP flooring throughout, stainless steel appliances, and may other upgrades are found at this home. All you have to do is move in! There are no projects that need to be done except for putting your personal touch on making this new construction house, your home! Nestled in a vibrant neighborhood, residents enjoy easy access to local park/playground. Walk around the neighborhood and catch plenty of creek views as the community is situated on Cox Creek. This property features an attached garage and a gracious amount of off-street parking for convenience. Embrace the warmth and comfort of this exceptional home, where community spirit and modern living harmoniously blend.

1921 Harbor Dr, Chester

Listing courtesy of Coldwell Banker Waterman Realty. Contact:

Selling Office: Redfin Corp.

7 Mariners Way Unit #2, Stevensville
$255,000
2 Beds ⋅ 2 Baths
This charming 2 bedroom 1.5 bathroom condo located in a waterfront community which provides direct access to Thompson Creek which flows into Cox Creek offering fishing, crabbing and boating just steps away. This unit has new carpet upstairs,brand new stainless steel appliances in kitchen with tile floors. Beautiful hard wood floors in living area. Unit offers a one car garage.,additional off street parking and overflow area for guest parking.The community boasts a inground pool overlooking the creek, clubhouse and picnic area perfect for social gatherings. HOA fees also cover water,sewer and trash costs. Close to shopping, food, schools, parks, Kent Island Trail and Bay bridge. Home warranty provided. Slips are assigned by unit number and available for use only after purchase by unit owner. The current assigned slip located on Dock A is transferable for a one time fee of $3000.00

7 Mariners Way Unit #2, Stevensville

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

Selling Office: EXP Realty, LLC.

620 Old Love Point Rd, Stevensville
$470,000
4 Beds ⋅ 3 Baths
Seller is open to considering creative offers and/or credits; reach out to Listing Agent with any questions - Over *2,600sqft* of living space located in the desirable Cloverfields community. Enjoy being near the water and having access to the many community amenities, including a community pool, playgrounds, and gathering areas. This home boasts 4 large bedrooms and 3 full bathrooms; 2-bedrooms and 2 full baths on the upper floor and 2-bedrooms and a full bathroom on the main entry level giving this home great possibilities. With one step to enter the main level and plumbing stubs, lower level living is an explorable possibility. An oversized driveway provides ample space for multiple vehicles and direct access to the fully fenced in backyard where you’ll find plenty of open space as well as a shed wired with electric giving additional possibilities. Please reach out with any questions and lets see how this home will work for you.

620 Old Love Point Rd, Stevensville

Listing courtesy of Berkshire Hathaway HomeServices PenFed Realty. Contact:

Selling Office: Taylor Properties.

716 Cloverfields Dr, Stevensville
$557,620
4 Beds ⋅ 2 Baths
Welcome home to this beautifully maintained 4-bedroom, 2-bath residence offering the ease of main-level living and a thoughtfully designed open floor plan. The spacious layout features a primary suite plus two additional bedrooms on the main level, with a fourth bedroom perfect for guests, a home office, or flex space. The heart of the home is the stunning, updated kitchen—complete with stainless steel appliances, quartz countertops, a stylish tile backsplash, and an oversized island with abundant seating, ideal for entertaining or casual dining. The kitchen flows seamlessly into the bright family room, highlighted by a cozy gas fireplace and 9-foot ceilings that enhance the open, airy feel. Luxury vinyl plank floors add warmth and elegance throughout the main living areas, while plush carpet (just 3 years old) provides comfort in the bedrooms. Additional features include a convenient laundry room, encapsulated crawlspace for added efficiency, and a 2-car garage. Step outside to relax or entertain on the deck overlooking your backyard. Located in a vibrant, amenity-rich community, residents enjoy access to a pool, clubhouse, playground, basketball courts, private beach, boat ramp, and marina with slips—perfect for embracing an active and coastal lifestyle.

716 Cloverfields Dr, Stevensville

Listing courtesy of Rosendale Realty. Contact:

Selling Office: RE/MAX Executive.

220 Old Steamship Rd, Stevensville
$1,950,000
4 Beds ⋅ 5 Baths
WATERFRONT (20 acres) located on the Northern section of Kent Island, in the area of larger acreage estates, the "Pink House" provides a peaceful respite from the rush of the world. As easy 5 minute drive from the Chesapeake Bay Bridge the home offers access to the western shore metro areas. NO SUBDIVISION POTENTIAL With over a 1000' of protected shoreline fronting along the broad, open waters of the Chester River the has 100'+ pier offers 4' MLW. A waterfowl hunter's delight you'll find a blind on the pier and one offshore as well. A generously proportioned inground pool with an expansive apron for lounging and dining is a focal point between the house and the river. An outdoor kitchen, huge deck and a screened gazebo invite spending time outdoors. A conservatory suitable for greenhouse functions or outdoor dining under cover is reminiscent of older European estate gardens. Established landscaping with unique plants surround the home and outdoor spaces. The residence is a blend of eclectic flair and flowing functionality. Designed to maximize views, the generous square footage offers a main level owners suite and three upper en-suites. Many custom features such as the designer counter tops and backsplash in the kitchen, hint at the uniqueness of this home. The "Pink House" offers secluded acreage at the end of a tree lined circular driveway. With some needed renovations and designer touches this home has the potential to be a showplace! CRAB this opportunity to own one of Kent Islands finer properties along the Chester River.

220 Old Steamship Rd, Stevensville

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

Selling Office: Non Subscribing Office.

216 La Gorce Dr, Stevensville
$475,000
3 Beds ⋅ 2 Baths
Rare opportunity to own a private Kent Island retreat offering the space, seclusion, and convenience rarely found this close to the Bay Bridge and Rt. 50. Tucked away on a road with only four homesites total, this 3-bedroom, 2-bath rancher sits on an exceptional 0.83-acre lot surrounded by woods on three sides. With over 1,600 sq ft of one-level living, the open floor plan flows seamlessly through the updated kitchen, dining room, and family room. The kitchen features granite countertops, 42-inch cherry cabinets, L-shaped island with seating & hardwood floors. Floor-to-ceiling windows fill the main living areas with natural light and overlook the front yard, wooded setting, and newly refreshed gravel driveway. The oversized screened porch is a standout feature, complete with a custom built-in bench and room for a full patio dining set—perfect for summer crab feasts, outdoor dining, and relaxing bug-free evenings. The spacious primary bedroom offers a walk-in closet plus two additional closets. Both bathrooms have been updated with tile floors and tiled surrounds, including a walk-in shower in the primary bath. Two additional sizable bedrooms with ample closet space complete the interior. Recent updates include a new heat pump, hot water heater, fresh paint throughout, and new carpet in the main living spaces and bedrooms. An oversized storage shed with overhang adds extra storage and functionality. Love to run, walk, or bike? You’re in luck—the Cross Island Trail is just steps away at the end of the street! Privacy, convenience, and a homesite that's nearly impossible to replicate for this location & price —this is Kent Island living at its best!

216 La Gorce Dr, Stevensville

Listing courtesy of Coldwell Banker Waterman Realty. Contact:

Selling Office: Real Broker, LLC - Annapolis.

136 Hilltop Dr, Chestertown
$376,000
3 Beds ⋅ 2 Baths
Immaculate 3-bedroom, 2-bath home set on a breathtaking, oversized lot with exquisite mature landscaping and a truly picturesque setting. Surrounded by lush greenery and stunning trees, including a graceful willow, this property offers a serene, park-like atmosphere, with views from nearly every window resembling beautiful landscape artwork. Inside, the home features a bright, open floor plan designed for modern living. A spacious family room flows seamlessly into the generous kitchen, while a separate dining room remains open to the main living areas—perfect for everyday living and entertaining. The kitchen is highlighted by beautiful French doors leading to the back patio, offering easy access for cooking, grilling, and hosting—perfect for summer barbecues and outdoor entertaining. Palladium windows throughout enhance the home with natural light and showcase the spectacular views. The thoughtfully designed layout offers a private primary suite on one side of the home with its own attached bath. Just off the kitchen and near the primary bedroom is a separate laundry room for added convenience. Two additional bedrooms are situated on the opposite side and share a well-appointed full hall bath. Additional features include fresh paint throughout, a side-entry one-car garage, and an extra-large driveway providing ample off-street parking. Tucked away on a quiet cul-de-sac with no through traffic, this home offers a rare combination of privacy, beauty, and tranquility.

136 Hilltop Dr, Chestertown

Listing courtesy of Northrop Realty. Contact:

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

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